%xymcarb.tex %Copyright (C) 1993, Shinsaku Fujita, All rights reserved. %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% %This file is a part of xymtex.tex that is the manual of the macro %package `XyMTeX' for drawing chemical structural formulas. %This file is not permitted to be translated into Japanese and any other %languages. \typeout{``xymcarb.tex''---% This file is a part of xymtex.tex that is the manual of the macro % package `XyMTeX'. 1993/12/1 S. Fujita} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \chapter{Introduction} \section{Backgrounds} The text formatter \TeX{} developed by Knuth \cite{knuth} is widely used in preparing manuscripts of scientific papers and in the typesetting processes of several scientific journals and books (for a recent example, see \cite{bcsj}). In particular, \LaTeX{}, a \TeX{} macro package that was released by Lamport \cite{lamport}, has expanded the society of \TeX{} users because of plainness. Since the beginning of its history, \TeX{} (\LaTeX{}) places special emphasis on mathematics typesetting. Hence, it has been accepted by scientists who have to write mathematic equations. In contrast, the \TeX{}/\LaTeX{} typesetting is less popular in chemistry than in mathematics and other fields. One of the reasons is that there are few \TeX{}/\LaTeX{} utilities for typesetting chemical structural diagrams. Although \LaTeX{} provides us with a picture enviroment for drawing simple figures, its original commands are so primitive as to be directly applied to the drawing of structural formulas. Hence, the commands should be combined to produce more convenient macros. Pioneering works by Haas and O'Kane \cite{haas} and by Ramek \cite{ramek} have provided such macros that allow us to typeset structural formulas. The macros of the former approach are available in the public domain, being named Chem\TeX{}. Although they are easier to use than the original picture environment of \LaTeX{}, they still have some items to be improved. The most inconvenient item is the incapability of accommodating 10 or more substituents. It stems from the fact that one argument is used to assign one substituent (or one object) in each of the macros of Haas-O'kane's approach. Note that the direct usage of arguments enables us only to assign 9 or less substituents, because a macro in \TeX{}/\LaTeX{} is capable of taking 9 or less arguments. For example, the \verb/\steroid/ macro reported for typesetting a steroid skeleton takes 9 arguments \cite{haas}: \begin{verbatim} \steroid{A1}{A2}{A3}{A4}{A5}{A6}{A7}{A8}{A9} \end{verbatim} where Argument 1 (\verb/A1/) can take `D' (a second bond between positions 1 and 2), `Q' (no action), or `R$^{11}$' (a substituent on position 11 and the corresponding double bond); Argument 2 (\verb/A2/) can take `D' (a second bond between positions 3 and 4), `Q' (no action), or `R$^{3}$' (a substituent on position 3 and the corresponding double bond); Argument 3 (\verb/A3/) can take `Q' (no action), or `R$^{3}$' (a substituent on position 3 and the corresponding single bond); and so on. Through the total statement of arguments, only six substituents are specified, while the skeleton have 20 or more substitution positions to be considered. Moreover, the specification of the arguments is not systematic, since so many functions are included into the macro within the restriction of the direct usage of arguments. \begin{enumerate} \item One argument (Argument 2) specifies objects of two different categories {\em e.g.,} inner double bonds and outer double bonds. \item Arguments 2 and 3 specify a substituent attaching to the same position (position 3). \item It is difficult without a reference manual to differentiate between one argument for specifying bonds and another argument for specifying substituents. \item The argument `Q' is selected to show no modification because this character is hardly ever found in a chemical structure formula. However, the use of this character may become necessary in future. Such explicit description of `no action' should be avoided. \end{enumerate} As a result, the formats and contents of arguments are different from one argument to another and from one macro to another such that a typical \TeX{} user, a secretary or a chemist author, may give up to memorize such macros. Hence, more systematic and convenient macros are desirable in order to spread the typesetting of chemical structures with \TeX{}/\LaTeX{}. The present package \XyMTeX{} involves convenient macros for typesetting chemical structural formulas \cite{fujita1}. These macros are based on techniques in which inner bonds, substituents and hetero-atoms on a skeleton are separately assigned without such limitation of numbers. The package \XyMTeX{}\footnote{%%%%%%%%% The present manual on \protect\XyMTeX{} is not permitted to be translated into Japanese and any other languages.} will be a more versatile tool if it is coupled with the macros which the author has released in a book \cite{fujita2}. %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \section{The Name of the Package} The word `chemistry' stems from an Arabian root `alchemy', which is, in turn, considered to come from Greek, $\chi\upsilon\mu\epsilon{\mathaccent 19\iota}\bar{\alpha}$. %(pronunciation: chum\'{e}i\bar{a}). The \XyM{} of the name \XyMTeX{} is an uppercase form of $\chi\upsilon\mu$. This conforms to a rule of coinage, because the name \TeX{} is also a word of Greek origin ($\tau\epsilon\chi$). The pronuncialtion of \XyMTeX{} is recommended to be `kh\'{y}mtekh', in which the `kh' sound may be a Russian `kh' or more simply an English `k' and the symbol `y' is expected to be pronounced like a German `\"{u}'. The logo \XyMTeX{} is defined as being either of the following statements. The second one has been adopted throughout the present manual.\footnote{%%%%%%%%%%%%%%%%%%%%%%%%%%%%% Definition 2 is adopted in the manual because of simplicity. The methodology used in Definition 1 is applicable to a wide variety of cases in which font sizes have to be changed.}%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \begin{verbatim} %%%XyMTeX Logo: Definition 1%%% \newcount\TestCount \def\XyM{\ifnum\fam=-1\relax\fam=0\relax\fi\TestCount=\fam% X\kern-.30em\smash{\raise.50ex\hbox{$\fam\TestCount\Upsilon$}}% \kern-.30em{M}} \def\XyMTeX{\XyM\kern-.1em\TeX} %%%XyMTeX Logo: Definition 2%%% \def\UPSILON{\char'7} \def\XyM{X\kern-.30em\smash{\raise.50ex\hbox{\UPSILON}}\kern-.30em{M}} \def\XyMTeX{\XyM\kern-.1em\TeX} \end{verbatim} When such a raised Greek letter as the `\UPSILON' is not available, \XyMTeX{} may be referred to by typing `{\tt XyMTeX}'. %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \section{Requirements} The macro package \XyMTeX{} runs within \LaTeX{}, since it is based on the picture environment of \LaTeX{}. Big\LaTeX{} should be used because \XyMTeX{} requires a considerable resource of memory. It also requires an option file `epic.sty' developed by Podar \cite{podar}, because the \verb/\dottedline/ command of epic is used in the macros. For example, a manuscript file should begin with such a statement as follows: \begin{verbatim} \documentstyle[epic,carom,hetarom]{article} \end{verbatim} wherein `carom' and `hetarom' are style files contained in the package \XyMTeX{}. %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \chapter{The Construction of \protect\XyMTeX{}} \section{Overview} \XyMTeX{} contains style files listed in Table \ref{tt:a1} and their documents. The style file `chemstr.sty' is the basic file that is automatically read within any other style file of \XyMTeX{}. It contains macros for internal use, {\em e.g.}, common commands for bond-setting and atom-setting. The other style files contain macros for users. \begin{table}[hpbt] \caption{Style Files of \protect\XyMTeX{}} \label{tt:a1} \begin{center} \begin{tabular}{lp{10cm}} \hline style name & \multicolumn{1}{c}{included functions} \\ \hline aliphat.sty & macros for drawing aliphatic compounds \\ carom.sty & macros for drawing vertical and horizontal types of carbocyclic compounds \\ lowcycle.sty & macros for drawing five-or-less-membered carbocyles. \\ ccycle.sty & macros for drawing bicyclic compounds etc. \\ hetarom.sty & macros for drawing vertical types of heterocyclic compounds \\ hetaromh.sty & macros for drawing horizontal types of heterocyclic compounds \\ hcycle.sty & macros for drawing pyranose and furanose derivatives \\ chemstr.sty & basic commands for atom- and bond-typesetting \\ locant.sty & commands for printing locant numeres \\ \hline \end{tabular} \end{center} \end{table} These files are designed to be option style files used within \LaTeX{}. The complete list of the \XyMTeX{} commands is shown in Appendix A. %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \section{General Conventions} \subsection{User Commands for Specified Use and for General Use} \XyMTeX{} user commands are classified into two types, {\em i.e.}, commands for specified use and those for general use. Specified user commands of \XyMTeX{} are used to draw a narrow range of structures. More precisely speaking, they are short-cut commands of general user commands with a specific bond pattern for drawing carbocycles or with a specific pattern of skeletal hetero-atoms for drawing heterocycles. They take such general forms as follows: \begin{center} \begin{tabular}{ll} \verb/\Sformb[OPT]{SUBSLIST}/ & for drawing carbocycles \\ \verb/\Sformd[BONDLIST]{SUBSLIST}/ & for drawing heterocycles \\ \end{tabular} \end{center} where \verb/\Sformb/ and \verb/\Sformd/ may be approriate command names. These are selected from chemical names that represent the compound-group names to be typeset. In accord with \LaTeX{} conventions, an argument in brackets is an option. The command \verb/\Sformb/ typesets a carbocyclic compound with a specific bond pattern which may be altered by the optional argument OPT. The command \verb/\Sformd/ prints a heterocyclic compound with a specific atom pattern on its skeleton.\footnote{%%%%%%%%%%%%%%%%%%%%%% If we take a strictly systematic approach, the {\tt $\backslash$Sformd} should be designed to take an option argument OPT instead of the BONDLIST. However, a simple format of the OPT cannot be designed because heterocyclic compounds take a wide variety of bond patterns.}%%%%%%%%%% For example, \verb/\bzdrv[OPT]{SUBSLIST}/ is a command for the specified use of drawing benzene derivatives, where the stem `\verb/\bzdr/ without a suffix `v' is an abbreviation of `benzene derivative'. The command \verb/pyridinev[BONDLIST]{SUBSLIST}/ is a command for drawing pyridine derivatives, in which the nitrogen atom on the pyridine ring is automatically typeset. On the other hand, more elaborate commands for general use can be used within \XyMTeX{}. They are designed to have a variable set of skeletal heteroatoms in accord with our designation so that they cover a wide range of structures. They have general formats as follows. \begin{center} \begin{tabular}{ll} \verb/\Sforma[BONDLIST]{SUBSLIST}/ & for drawing carbocycles \\ \verb/\Sformc[BONDLIST]{ATOMLIST}{SUBSLIST}/ & for drawing heterocycles \\ \end{tabular} \end{center} where \verb/\Sforma/ and \verb/\Sformc/ may be approriate command names. The command \verb/\Sforma/ for general use generates a carbocyclic structure, in which its individual bonds can be independently altered by means of BONDLIST. The command \verb/\Sformd/ prints a heterocyclic compound so that individual atoms on its skeleton can be independently typeset through ATOMLIST. For example, \verb/\cyclohexanev[BONDLIST]{SUBSLIST}/ is a command for the general use of drawing cyclohexane derivatives, by which six-membered carbocyles of any unsaturation level can be typeset. The command \verb/sixheterov[BONDLIST]{ATOMLIST}{SUBSLIST}/ is a command for drawing six-membered heterocyclic compounds, which may have any set of skeletal hetero-atoms (ATOMLIST) and any set of unsaturation (BONDLIST). %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \subsection{Suffix and Arguments} Most user commands of \XyMTeX{} are suffixed with `v', `vi', `h` and `hi'. The suffix `v' means that the command prints a structural formula of vertical form. The suffix `h' means that the command typesets a structural formula of horizontal form. When alternative orientations are possible, \XyMTeX{} commands are differentiated by an additional suffix `i'. The specification of each argument in a \XyMTeX command is based on list-treating macros \cite{fujita1}. Thus, items to be specified are listed sequentially with or without appropriate delimeters. The argument SUBSLIST lists substituents with bonds. The argument \{1==Cl;3D==O;$\ldots$\}, for example, means that position 1 takes a chlorine atom (Cl) through a single bond, position 3 takes an oxygen atom (O) through a double bond, and so on. Thus, a character string before every semicolon represents a mode of substitution, where a locant number with a bond modifier is separated from a substituent by means of a double equality symbol (==). Each bond modifier consists of one or two characters listed in Table \ref{tt:a2}. % This specification is changed 1993/11/20 S. Fujita %\footnote{%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% %In our paper \cite{fujita1}, %we have adopted A (and $\alpha$) to designate the left-hand substituent %and B (and $\beta$) to designate the right-hand substituent of each %position. This rule may provide serious confusions, %although the alignment A to B is normal (from left to right). %Hence, the notations A ($\alpha$) and B ($\beta$) have now been changed %to be inverse as compared with the counterparts reported. %This change is harmony with chemical conventions especially %with respect to stereochemisty of cyclic compounds.}%%%%%%%%%%%%%%%%%%%%% The diagrams below Table \ref{tt:a2} illustrate these bond modifiers by using a cyclohexane skeleton (\verb/\cyclohexanev/). \begin{table}[hpbt] \caption{Locant numbering and bond modifiers for SUBSLIST} \label{tt:a2} \begin{center} \begin{tabular}{lp{10cm}} \hline Bond Modifiers & \multicolumn{1}{c}{Printed structures} \\ \hline $n$D & exocyclic double bond at $n$-atom \\ $n$ or $n$S & exocyclic single bond at $n$-atom \\ $n$A & alpha single bond at $n$-atom \\ $n$B & beta single bond at $n$-atom \\ $n$SA & alpha single bond at $n$-atom (dotted line) \\ $n$SB & beta single bond at $n$-atom (boldface) \\ $n$Sa & alpha (not specified) single bond at $n$-atom \\ $n$Sb & beta (not specified) single bond at $n$-atom \\ \hline \end{tabular} \end{center} \vspace*{1cm} \begin{center} \cyclohexanev{1==1;2==2;3==3;4==4;5==5;6==6} \qquad \cyclohexanev{1A==1A;2A==2A;3A==3A;4A==4A;5A==5A;6A==6A} \qquad \cyclohexanev{1B==1B;2B==2B;3B==3B;4B==4B;5B==5B;6B==6B} \vspace*{1cm} \cyclohexanev{1Sa==1Sa;1Sb==1Sb;% 2Sa==2Sa;2Sb==2Sb;3Sa==3Sa;3Sb==3Sb;% 4Sa==4Sa;4Sb==4Sb;5Sa==5Sa;5Sb==5Sb;% 6Sa==6Sa;6Sb==6Sb} \qquad\qquad \cyclohexanev{1SA==1SA;1SB==1SB;% 2SA==2SA;2SB==2SB;3SA==3SA;3SB==3SB;% 4SA==4SA;4SB==4SB;5SA==5SA;5SB==5SB;% 6SA==6SA;6SB==6SB} \end{center} \end{table} The optional argument OPT of \verb/\Sformb/ contains a string of one or two characters for giving a pattern of double bonds ({\em e.g.}, `r' for a right-hand set of aromatic double bonds `l' for a left-hand set of aromatic double bonds, and `c' for an aromatic circle for the macro \verb/\bzdrv/). Since the argument OPT is an option, a default set of bonds is used when omitted. The optional argument BONDLIST contains a character string, each character of which is used for assigning a specific inner double bond ({\em e.g.}, `a', `b', $\ldots$ for the double bonds of a given bond-numbering). Since the argument BONDLIST is an option, a default is used when omitted: the commands \verb/\Sformd/ and \verb/\Sformc/ (for drawing heterocycles) typeset default sets of bonds, while most \verb/Sforma/ commands (for drawing carbocycles) print fully saturated skeletons. The argument ATOMLIST ({\em e.g.}, \{1==O;4==O\}) contains hetero atoms and their positions on the ring structure to be printed: this example argument produces a dioxane skeleton, when used in command \verb/\sixheterov/. %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \chapter{Six-Membered Carbocycles} \section{Drawing Benzene Derivatives} \subsection{Vertical Forms of Benzene Derivatives} The macro \verb/\bzdrv/ is used to draw benzene derivatives of vertical type (carom.sty). The format of this command is as follows: \begin{verbatim} \bzdrv[OPT]{SUBSLIST} \end{verbatim} % **************************************** % * benzene and benzoquinone derivatives * % * (vertical type) * % **************************************** The name and arguments of this command conform to the general conventions described in the preceding chapter. Locant numbers for designating substitution positions in the SUBSLIST are represented by the following diagram: \begin{xymspec} \bzdrv{1==1(lr);2==2(r);3==3(r);4==4(lr);5==5(l);6==6(l)} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} in which a character set in parentheses represent the handedness of each position. In accord with the default definitons of the macro \verb/bzdrv/, each of the right-handed positions (2 and 3) is designed to take only a right-handed substituent, while each of the left-handed positions (5 and 6) is to take only a left-handed substituent. Such positions (designated with the letter `r' or `l') are referred to as `oriented' positions in this manual. In contrast, the top (and also the bottom) position of a benzene ring (designated with the string `lr') can accommodate a substituent of both handedness. It is referred to as a `double-sided' position in this manual. Although the default definition is to put a right-handed moiety, a left-handed substituent can be printed by means of the macro \verb/\lmoiety/. The symbols $\bullet$ and $\circ$ in the diagram respectively represent the reference point and the inner origin of the macro. These will be described in detail in Chapter 14. The optional argument OPT specifying a bond pattern are shown in Table \ref{tt:a3}. Thereby, a wide variety of bond patterns (such as two patterns of benzene double bonds as well as an aromatic circle) can be depicted. \begin{table}[hpbt] \caption{Argument OPT for commands {\tt$\backslash$ bzdrv} and {\tt$\backslash$ bzdrh}} \label{tt:a3} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline none or r & right-handed set of double bonds \\ l & left-handed set of double bonds \\ c & aromatic circle\\ \hline p or pa & $p$-benzoquinone (A) (Oxygen atomes at 1,4-positions)\\ pb & $p$-benzoquinone (B) (Oxygen atomes at 2,5-positions)\\ pc & $p$-benzoquinone (C) (Oxygen atomes at 3,6-positions)\\ \hline o or oa & $o$-benzoquinone (A) (Oxygen atomes at 1,2-positions)\\ ob & $o$-benzoquinone (B) (Oxygen atomes at 2,3-positions)\\ oc & $o$-benzoquinone (C) (Oxygen atomes at 3,4-positions)\\ od & $o$-benzoquinone (D) (Oxygen atomes at 4,5-positions)\\ oe & $o$-benzoquinone (E) (Oxygen atomes at 5,6-positions)\\ of & $o$-benzoquinone (F) (Oxygen atomes at 1,6-positions)\\ \hline \end{tabular} \end{center} \end{table} The argument SUBSLIST is used to specify each substituent with a locant number and a bond modifier shown in Table \ref{tt:a2}, in which $n$ is an arabic numeral between 1 and 6. For example, the statements, \begin{verbatim} \bzdrv{1==Cl;2==F} \bzdrv[c]{1==Cl;4==F;2==CH$_{3}$}\qquad \bzdrv[pa]{1D==O;4D==O;6==H$_{3}$C} \bzdrv[oa]{1D==O;2D==N--SO$_{2}$CH$_{3}$;4==OCH$_{3}$;5==H$_{3}$C} \end{verbatim} produce the following structures: \begin{center} \bzdrv{1==Cl;2==F} \bzdrv[c]{1==Cl;4==F;2==CH$_{3}$}\qquad \bzdrv[pa]{1D==O;4D==O;6==H$_{3}$C} \bzdrv[oa]{1D==O;2D==N--SO$_{2}$CH$_{3}$;4==OCH$_{3}$;5==H$_{3}$C} \end{center} In order to designate the handedness of a substituent explicitly, you can use \verb/\rmoiety/ or \verb/\lmoiety/ commands. Thus, the statements, \begin{verbatim} \bzdrv[pa]{1D==O;4D==\lmoiety{CH$_{3}$SO$_{2}$--N};2==CH$_{3}$} \bzdrv[pa]{1D==\rmoiety{O};4D==\rmoiety{N--SO$_{2}$CH$_{3}$};2==CH$_{3}$} \end{verbatim} produce the following structures with left-handed and right-handed methanesulfonimido groups. \begin{center} \bzdrv[pa]{1D==O;4D==\lmoiety{CH$_{3}$SO$_{2}$--N};2==CH$_{3}$} \bzdrv[pa]{1D==\rmoiety{O};4D==\rmoiety{N--SO$_{2}$CH$_{3}$};2==CH$_{3}$} \end{center} The macro \verb/bzdrv/ is used also to draw benzoquinone monoacetals and diacetals. The handedness of a substituent attached at such a tetrahedral position is determined in the light of chemical conventions. For example, \begin{verbatim} \bzdrv[pa]{1D==O;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$;2==NH--SO$_{2}$CH$_{3}$} \qquad \qquad \bzdrv[pa]{1Sb==CH$_{3}$O;1Sa==OCH$_{3}$;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$} \end{verbatim} produce the following structures. \begin{center} \bzdrv[pa]{1D==O;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$;2==NH--SO$_{2}$CH$_{3}$} \qquad \qquad \bzdrv[pa]{1Sb==CH$_{3}$O;1Sa==OCH$_{3}$;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \subsection{Horizontal Forms of Benzene Derivatives} You can use the macro \verb/\bzdrh/ to draw benzene derivatives of horizontal type (carom.sty). The format of this command is as follows: \begin{verbatim} \bzdrh[OPT]{SUBSLIST} \end{verbatim} The formats of the arguments are the same as those of \verb/\bzdrv/ (Tables \ref{tt:a2} and \ref{tt:a3}). The locant numbering and the handedness of substitution are designed as follows: \begin{xymspec} \bzdrh{1==1(l);2==2(lr);3==3(r);4==4(r);5==5(r);6==6(lr)} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} For example, the diagrams: \begin{center} \bzdrh[pa]{4D==O;1D==CH$_{3}$SO$_{2}$--N;3==CH$_{3}$} \qquad \bzdrh[pa]{1D==O;4D==N--SO$_{2}$CH$_{3}$;2==CH$_{3}$} \end{center} are typeset by inputting the statements: \begin{verbatim} \bzdrh[pa]{4D==O;1D==CH$_{3}$SO$_{2}$--N;3==CH$_{3}$} \qquad \bzdrh[pa]{1D==O;4D==N--SO$_{2}$CH$_{3}$;2==CH$_{3}$} \end{verbatim} It should be noted the the commands \verb/\bzdrv/ and \verb/\bzdrh/ are based respectively on the commands \verb/\cyclohexanev/ and \verb/\cyclohexaneh/ that will be described in the next section. Hence, structures drawn with the former set of commands can be also drawn with the latter set of commands. %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \section{Drawing Cyclohexane Derivatives} \subsection{Vertical Forms of Cyclohexane Derivatives} The macro \verb/\cyclohexanev/ is used to draw cyclohexane derivatives of vertical type (carom.sty). The format of this command is as follows: \begin{verbatim} \cyclohexanev[BONDLIST]{SUBSLIST} \end{verbatim} % *************************** % * cyclohexane derivatives * % * (vertical type) * % *************************** % The following numbering is adopted in this macro. % % 1 % * % 6 * * 2 % | | % | | % 5 * * 3 % * % 4 <===== the original point Locant numbers (1--6) for designating substitution positions and characters (a--f) for showing bonds to be doubled are represented by the following diagram: \begin{xymspec} \begin{picture}(800,880)(0,0) \put(0,0){\cyclohexanev{1Sb==1Sb(l);1Sa==1Sb(r);% 2Sb==2Sb(r);2Sa==2Sa(r);3Sb==3Sb(r);3Sa==3Sa(r);% 4Sb==4Sb(l);4Sa==4Sa(r);5Sb==5Sb(l);5Sa==5Sa(l);% 6Sb==6Sb(l);6Sa==6Sa(l)}} \put(0,0){\sxlocant} \put(0,0){\bdlocant} \end{picture} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} Each character set in parentheses represents the handedness of the corresponding position, which is fixed in this type of macros. The option argument BONDLIST is an character string in a pair of brackets, where each character indicates the presence of a double bond at the edge corresponding to the character. The bond-correspondence is rather arbitrary in some cases but conforms to chemical conventions as faithfully as possible if such conventions are presence (Table \ref{tt:a4}). \begin{table}[hpbt] \caption{Argument BONDLIST for commands {\tt$\backslash$cyclohexanev} and {\tt$\backslash$cyclohexaneh}} \label{tt:a4} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline none & cyclohexane \\ a & 1,2-double bond \\ b & 2,3-double bond \\ c & 4,3-double bond \\ d & 4,5-double bond \\ e & 5,6-double bond \\ f & 6,1-double bond \\ A & aromatic circle \\ \hline \end{tabular} \end{center} \end{table} The argument SUBSLIST for this macro takes a general format, in which the modifiers listed in Table \ref{tt:a2} are used. Suppose you input the commands: \begin{verbatim} \cyclohexanev{2D==O;1Sb==H$_{3}$C;1Sa==CH$_{3}$;% 3Sb==CH$_{3}$;3Sa==CH$_{3}$} \qquad\qquad \cyclohexanev[b]{1D==O;5Sb==CH$_{3}$;5Sa==CH$_{3}$} \end{verbatim} The first example illustrates the case that \verb/\cyclohexanev/ accompanies no optional argument. On the other hand, the second one take [b] as an optional BONDLIST, which prints an inner bond between 2 and 3 positions. Thus, you can obtain the following diagrams: \medskip \begin{center} \cyclohexanev{2D==O;1Sb==H$_{3}$C;1Sa==CH$_{3}$;% 3Sb==CH$_{3}$;3Sa==CH$_{3}$} \qquad\qquad \cyclohexanev[b]{1D==O;5Sb==CH$_{3}$;5Sa==CH$_{3}$} \end{center} Since the macro \verb/\cyclohexanev/ is the basis of the macro \verb/\bzdrv/, structural formulas depicted with the latter command can also be written by the former one. For example, the quinone acetals described above are also typeset by the following statements. \begin{verbatim} \cyclohexanev[be]{1D==O;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$;2==NH--SO$_{2}$CH$_{3}$} \qquad \qquad \cyclohexanev[be]{1Sb==CH$_{3}$O;1Sa==OCH$_{3}$;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$} \end{verbatim} These commands are completely equivalent to those describe above and produce the following structures. \begin{center} \cyclohexanev[be]{1D==O;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$;2==NH--SO$_{2}$CH$_{3}$} \qquad \qquad \cyclohexanev[be]{1Sb==CH$_{3}$O;1Sa==OCH$_{3}$;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$} \end{center} For the purpose of depicting the stereochemisty of a cyclohexane ring, input the following: \begin{verbatim} \cyclohexanev{2B==CH$_{3}$;3B==CH$_{3}$}\qquad\qquad \cyclohexanev{2B==CH$_{3}$;3A==CH$_{3}$} \end{verbatim} Thereby, you can obtain: \begin{center} \cyclohexanev{2B==CH$_{3}$;3B==CH$_{3}$}\qquad\qquad \cyclohexanev{2B==CH$_{3}$;3A==CH$_{3}$} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \subsection{Horizontal Forms of Cyclohexane Derivatives} The macro \verb/\cyclohexaneh/ is used to draw cyclohexane derivatives of horizontal type (carom.sty). The format of this command is as follows: \begin{verbatim} \cyclohexaneh[BONDLIST]{SUBSLIST} \end{verbatim} % *************************** % * cyclohexane derivatives * % * (horizontal type) * % *************************** % The following numbering is adopted in this macro. % % 2 3 % ----- % * * % the original point ===> 1 * * 4 % (0,0) * * % ----- % 6 5 Locant numbers for designating substitution positions are represented by the following diagram: \begin{xymspec} \begin{picture}(800,880)(0,0) \put(0,0){\cyclohexaneh{1Sb==1Sb(l);1Sa==1Sb(l);% 2Sb==2Sb(l);2Sa==\lmoiety{2Sa(lr)};3Sb==3Sb(r);3Sa==3Sa(lr);% 4Sb==4Sb(r);4Sa==4Sa(r);5Sb==5Sb(r);5Sa==5Sa(lr);% 6Sb==6Sb(l);6Sa==\lmoiety{6Sa(lr)}}} \put(0,0){\sxlocnth} \put(0,0){\bdlocnth} \end{picture} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} Each character set in parentheses represents the handedness of the corresponding position, which is fixed in this type of macros. The SUBSLIST and the BONDLIST format are shown in Table \ref{tt:a2} and \ref{tt:a4}, respectively. \medskip \noindent Example: \begin{verbatim} \cyclohexaneh{3D==O;5D==O;1Sb==CH$_{3}$;1Sa==CH$_{3}$;% 4==CH$_{2}$CO$_{2}$H}\qquad\qquad \cyclohexaneh{4D==CH$_{2}$;3SB==CH$_{3}$;3SA==H} \end{verbatim} These commands produce: \begin{center} \cyclohexaneh{3D==O;5D==O;1Sb==CH$_{3}$;1Sa==CH$_{3}$;% 4==CH$_{2}$CO$_{2}$H}\qquad\qquad \cyclohexaneh{4D==CH$_{2}$;3SB==CH$_{3}$;3SA==H} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \chapter{Carbocycles with Fused Six-Membered Rings} \section{Drawing Naphthalene Derivatives} \subsection{Vertical Forms of Naphthalene Derivatives} The macro \verb/\naphdrv/ is used to draw naphthalene derivatives of vertical type (carom.sty) as well as various naphthoquinone derivatives. The format of this command is as follows: \begin{verbatim} \naphdrv[OPT]{SUBSLIST} \end{verbatim} % ********************************************** % * naphthalene and naphthoquinone derivatives * % * (vertical type) * % ********************************************** Locant numbers for designating substitution positions are represented by the following diagram: \begin{xymspec} \naphdrv{1==1(lr);2==2(r);3==3(r);4==4(lr);5==5(lr);6==6(l);% 7==7(l);8==8(lr)} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses. The optional argument OPT is used to specify a bond pattern as shown in Table \ref{tt:a5}. \begin{table}[hpbt] \caption{Argument OPT for commands {\tt$\backslash$naphdrv} and {\tt$\backslash$naphdrh}} \label{tt:a5} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline none & naphthalene \\ A & aromatic circle \\ \hline p or pa & 1,4-quinone (A) left aromatic, right quinone \\ pb & 1,4-quinone (B) right aromatic, left quinone \\ \hline o or oa & $o$-quinone (A) (Oxygen atomes at 1,2-positions)\\ ob & $o$-quinone (B) (Oxygen atomes at 2,3-positions)\\ oc & $o$-quinone (C) (Oxygen atomes at 3,4-positions)\\ od & $o$-quinone (D) (Oxygen atomes at 4,5-positions)\\ oe & $o$-quinone (E) (Oxygen atomes at 5,6-positions)\\ of & $o$-quinone (F) (Oxygen atomes at 1,6-positions)\\ \hline q or qa & 2,6-quinone (A) \\ qb & 2,6-quinone (B) (actually 3,7-positons) \\ qc & 1,5-quinone (C) \\ qd & 1,5-quinone (D) (actually 4,8-positions) \\ qe & 1,7-quinone (E) \\ qf & 1,7-quinone (F) (actually 2,8-positions) \\ qg & 1,7-quinone (G) (actually 4,6-positions) \\ qh & 1,7-quinone (H) (actually 3,5-positions) \\ \hline P or Pa &: 1,4,5,8-quinone (A) \\ Pb & 1,2,5,8-quinone (B) \\ \hline Q & 1,2,3,4-quinone \\ \hline O or Oa & 1,2,5,6-quinone (A) \\ Ob & 1,2,7,8-quinone (B) \\ Oc & 1,2,3,5-quinone (C) \\ Od & 1,2,3,7-quinone (D) \\ \hline \end{tabular} \end{center} \end{table} The argument SUBSLIST is used to specify each substituent with a locant number and a bond modifier shown in Table \ref{tt:a2}, in which $n$ is an arabic numeral between 1 and 8. \medskip \noindent Example: \begin{verbatim} \naphdrv{1==CH$_{2}$CH=CH$_{2}$;2==OH} \qquad \naphdrv{6==H$_{3}$C;2==COCH$_{2}$CH$_{2}$COOH} \hskip1.5cm \naphdrv[o]{1Sb==Cl;1Sa==Cl;2D==O} \end{verbatim} These commands produce: \begin{center} \naphdrv{1==CH$_{2}$CH=CH$_{2}$;2==OH} \qquad \naphdrv{6==H$_{3}$C;2==COCH$_{2}$CH$_{2}$COOH} \hskip1.5cm \naphdrv[o]{1Sb==Cl;1Sa==Cl;2D==O} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \subsection{Horizontal Forms of Naphthalene Derivatives} The macro \verb/\naphdrh/ is used to draw naphthalene derivatives of horizontal type (carom.sty) as well as various naphthoquinone derivatives. The format of this command is as follows: \begin{verbatim} \naphdrh[OPT]{SUBSLIST} \end{verbatim} The format of the argument OPT is the same as that of \verb/\naphdrv/ (Tables \ref{tt:a5}). The format of the argument SUBSLIST is the same as collected in Tables \ref{tt:a2}. The locant numbering and the handedness of substitution are designed as follows: \begin{xymspec} \naphdrh{1==1(l);2==2(r);3==3(r);4==4(r);5==5(r);6==6(r);% 7==7(r);8==8(l)} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} \medskip \noindent Example: \begin{verbatim} \naphdrh{4==NH$_{2}$;5==SO$_{3}$H}\qquad \naphdrh{5==N=NC$_{6}$H$_{4}$SO$_{3}$Na;6==OH} \end{verbatim} These commands produce: \begin{center} \naphdrh{4==NH$_{2}$;5==SO$_{3}$H}\qquad \naphdrh{5==N=NC$_{6}$H$_{4}$SO$_{3}$Na;6==OH} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \section{Drawing Tetraline Derivatives} \subsection{Vertical Forms of Tetraline Derivatives} The macro \verb/\tetralinev/ is used to draw tetraline derivatives of vertical type (carom.sty) as well as various naphthoquinone derivatives. The format of this command is as follows: \begin{verbatim} \tetralinev[OPT]{SUBSLIST} \end{verbatim} % ********************************************** % * naphthalene and naphthoquinone derivatives * % * (vertical type) * % ********************************************** Locant numbers for designating substitution positions are represented by the following diagram: \begin{xymspec} \tetralinev{1Sb==1Sb(l);1Sa==1Sa(r);2Sb==2Sb(r);2Sa==2Sa(r);% 3Sb==3Sb(r);3Sa==3Sa(r);4Sb==4Sb(l);4Sa==4Sa(r);% 5==\lmoiety{5(lr) };6==6(l);7==7(l);8==\lmoiety{8(lr) }} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses. The optional argument OPT is used to specify a bond pattern as shown in Table \ref{tt:a6}. \begin{table}[hpbt] \caption{Argument OPT for commands {\tt$\backslash$tetralinev} and {\tt$\backslash$tetralineh}} \label{tt:a6} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline none & tetraline \\ A & aromatic circle \\ e or ea & 1,2-double bond \\ eb & 2,3-double bond \\ ec & 3,4-double bond \\ \hline \end{tabular} \end{center} \end{table} A bond modifier in the argument SUBSLIST for $n=1$ to $4$ can be one of the bond modifiers shown in Table \ref{tt:a2}, which allows $\alpha$- or $\beta$-orientation. On the other hand a bond modifier in the argument SUBSLIST for $n=5$ to $8$ should be vacant. If there appears the overcrowding between 1- and 8-substituent or between 4- and 5-substituent, the bond modifier 5Sb or 8Sb is allowed to avoid such overcrowding. \medskip \noindent Example: \begin{verbatim} \tetralinev{1Sb==H$_{3}$C;1Sa==CH$_{3}$;% 4Sb==H$_{3}$C;4Sa==CH$_{3}$;7==Br}\qquad \tetralinev[ea]{1==CH$_{2}$OSi(CH$_{3}$)$_{2}$C(CH$_{3}$)$_{3}$; 2==C$_{2}$H$_{5}$;5==OCH$_{3}$;6==O=CH}\qquad \tetralinev{3D==NOH;4Sb==H$_{3}$C;4Sa==CH$_{3}$;5Sb==Cl} \end{verbatim} These commands produce: \begin{center} \tetralinev{1Sb==H$_{3}$C;1Sa==CH$_{3}$;4Sb==H$_{3}$C;% 4Sa==CH$_{3}$;7==Br} \qquad \tetralinev[ea]{1==CH$_{2}$OSi(CH$_{3}$)$_{2}$C(CH$_{3}$)$_{3}$; 2==C$_{2}$H$_{5}$;5==OCH$_{3}$;6==O=CH}\qquad \tetralinev{3D==NOH;4Sb==H$_{3}$C;4Sa==CH$_{3}$;5Sb==Cl} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \subsection{Horizontal Forms of Tetraline Derivatives} The \verb/\tetralineh/ is the horizontal counterpart of the command \verb/\tetralinev/: \begin{verbatim} \tetralineh[OPT]{SUBSLIST} \end{verbatim} % ************************* % * tetraline derivatives * % * (horizontal type) * % ************************* Locant numbers for designating substitution positions are represented by the following diagram: \begin{xymspec} \tetralineh{1Sb==1Sb(l);1Sa==1Sa(l);2Sb==2Sb(l);2Sa==\lmoiety{2Sa(lr)};% 3Sb==3Sb(r);3Sa==3Sa(r);4Sb==4Sb(r);4Sa==4Sa(r);% 5==5(r);6==6(r);7==\lmoiety{7(lr)};8==8(l)} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses. The optional argument OPT is used to specify a bond pattern as shown in Table \ref{tt:a6}. The argument SUBSLIST is the same as that of \verb/\tetralinev/. \medskip \noindent Example: \begin{verbatim} \tetralineh[eb]{1D==O;4D==O;5==OH} \qquad \tetralineh[eb]{1SB==H$_{3}$C;1SA==H;4SB==CH$_{3}$;4SA==H} \end{verbatim} These commands produce: \begin{center} \tetralineh[eb]{1D==O;4D==O;5==OH} \qquad \tetralineh[eb]{1SB==H$_{3}$C;1SA==H;4SB==CH$_{3}$;4SA==H} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \section{Drawing Decaline Derivatives} \subsection{Vertical Forms of Decaline Derivatives} The macro \verb/\decalinev/ is used to draw decaline derivatives of vertical type (carom.sty). The format of this command is as follows: \begin{verbatim} \decalinev[BONDLIST]{SUBSLIST} \end{verbatim} % ************************ % * decaline derivatives * % * (vertical type) * % ************************ % The following numbering is adopted in this macro. % % 8 (0G)1 % * 8a * % 7 * * * * 2 % | | | % | | | % 6 * * * * 3 % * 4a * % 5 (0F)4 % ^ % | % the original point % Locant numbers for designating substitution positions and characters for showing bonds to be doubled are represented by the following diagram: {\origpttrue \begin{center} \begin{picture}(1000,1000)(0,0) \put(0,0){\decalinev{% 1Sb==1;1Sa==1Sa(r);2Sb==2Sb(r);2Sa==2Sa(r);% 3Sb==3Sb(r);3Sa==3Sa(r);4Sb==4;4Sa==4Sa(r);% 5Sb==5Sb(l);5Sa==5;6Sb==6Sb(l);6Sa==6Sa(l);% 7Sb==7Sb(l);7Sa==7Sa(l);8Sb==8Sb(l);8Sa==8;% 0F==0F;0G==0G}} \put(553,940){\hbox to0pt{\hss Sa(r)}} \put(593,940){\hbox to0pt{Sb(l)\hss}} \put(553,-100){\hbox to0pt{\hss Sa(r)}} \put(593,-100){\hbox to0pt{Sb(l)\hss}} {\footnotesize \put(0,0){\bdloocant{i}{k}{e}{f}{g}{h}} \put(342,0){\bdloocant{a}{b}{c}{d}{}{j}}} \end{picture} \qquad\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{center} } The handedness for each oriented or double-sided position is shown with a character set in parentheses. The option argument BONDLIST is based on the assignment of characters (a--k) to respective bonds as shown in the above diagram. A bond modifier in the argument SUBSLIST for $n=1\mbox{--}8$ can be one of bond modifiers shown in Table \ref{tt:a2}. The substitution at the bridgehead positions is designated as shown in Table \ref{tt:a7}. \begin{table}[hpbt] \caption{SUBSLIST for bridgehead positions in {\tt$\backslash$decalinev} and {\tt$\backslash$decalineh}} \label{tt:a7} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline 0FA & alpha single bond at 8a \\ 0FB & beta single bond at 8a\\ 0FU & unspecified single bond at 8a\\ 0GA & alpha single bond at 4a \\ 0GB & beta single bond at 4a\\ 0GU & unspecified single bond at 4a\\ \hline \end{tabular} \end{center} \end{table} \medskip \noindent Example: \begin{verbatim} \decalinev{1D==O;0FB==H;0GA==H} \qquad \decalinev{1B==CH$_{2}$OSiR$_{3}$;3D==O;4A==COOCH$_{3}$;% 0FB==CH$_{3}$;0GA==H} \end{verbatim} These commands produce: \begin{center} \decalinev{1D==O;0FB==H;0GA==H} \qquad \decalinev{1B==CH$_{2}$OSiR$_{3}$;3D==O;4A==COOCH$_{3}$;% 0FB==CH$_{3}$;0GA==H} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \subsection{Horizontal Forms of Decaline Derivatives} The macro \verb/\decalineh/ (carom.sty) is the horizotal counterpart of \verb/\decalinev/. The format and the assignment of BONDLIST and SUBSLIST of the former macro are the same as the latter (see Tables \ref{tt:a2} and \ref{tt:a7}). \begin{verbatim} \decalineh[BONDLIST]{SUBSLIST} \end{verbatim} % ************************ % * decaline derivatives * % * (horizontal type) * % ************************ % The following numbering is adopted in this macro. % % 2 3 % ----- % * * % 1 * * 4 % * * % 8a (0G) ----- 4a (0F) % * * % the original point ===> 8 * * 5 % (0,0) * * % ----- % 7 6 Locant numbers for designating substitution positions are represented by the following diagram: \begin{xymspec} \begin{picture}(1000,1200)(0,0) \put(0,0){\decalineh{% 1Sb==1Sb(l);1Sa==1Sa(l);2Sb==2Sb(l);2Sa==\lmoiety{2Sa(lr)};% 3Sb==3Sb(r);3Sa==3Sa(r);4Sb==4Sb(r);4Sa==4Sa(r);% 5Sb==5Sb(r);5Sa==5Sa(r);6Sb==6Sb(r);6Sa==6Sa(r);% 7Sb==7Sb(l);7Sa==\lmoiety{7Sa(lr)};8Sb==8Sb(r);8Sa==8Sa(l);% 0F==0F(l);0G==0G(r)}} {\footnotesize \put(0,0){\bdloocnth{i}{k}{e}{f}{g}{h}} \put(0,342){\bdloocnth{a}{b}{c}{d}{}{j}}} \end{picture} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses. \medskip \noindent Example: \begin{verbatim} \decalineh{1D==O;0FA==H;0GB==H} \qquad\qquad \decalineh{1B==R$_{3}$SiOCH$_{2}$;3D==O;4A==COOCH$_{3}$;% 0FB==CH$_{3}$;0GA==H} \end{verbatim} These commands produce: \begin{center} \decalineh{1D==O;0FA==H;0GB==H} \qquad\qquad \decalineh{1B==R$_{3}$SiOCH$_{2}$;3D==O;4A==COOCH$_{3}$;% 0FB==CH$_{3}$;0GA==H} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \chapter{Fused Tricyclic Carbocycles and Steroids} \section{Drawing Anthracene Derivatives} \subsection{Command for Specified Use} The macro \verb/\anthracenev/ is used to draw anthracene derivatives of vertical type (carom.sty) as well as various quinone derivatives. The format of this command is as follows: \begin{verbatim} \anthracenev[OPT]{SUBSLIST} \end{verbatim} % ******************************************** % * anthracene and anthraquinone derivatives * % * (vertical type) * % ******************************************** Locant numbers for designating substitution positions are represented by the following diagram: \begin{xymspec} \anthracenev{1==1(lr);2==2(r);3==3(r);4==4(lr);5==5(lr);6==6(l);% 7==7(l);8==8(lr);9==9(lr);{{10}}==10(lr)} \qquad\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses. The optional argument OPT is used to specify a bond pattern as shown in Table \ref{tt:a8}. \begin{table}[hpbt] \caption{Argument OPT for commands {\tt$\backslash$anthracenev}} \label{tt:a8} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline none or r & right-handed double bonds \\ l & left-handed double bonds \\ A & aromatic circle \\ \hline p or pa & 9,10-anthraquinone (A) \\ pA & 9,10-anthraquinone (circle type) \\ \hline o & 1,2-anthraquinone (A) \\ oa & 1,2-anthraquinone (A') \\ oA & 1,2-anthraquinone (circle type) \\ ob & 2,3-antharquinone (B) \\ oc & 1,2-anthraquinone (C) \\ \hline q & 1,4-anthraquinone (A) \\ qa & 1,4-anthraquinone (A') \\ qA & 1,4-anthraquinone (circle type) \\ \hline \end{tabular} \end{center} \end{table} The argument SUBSLIST is used to specify each substituent with a locant number and a bond modifier shown in Table \ref{tt:a2}, in which $n$ is an arabic numeral between 1 and 10. \medskip \noindent Example: \begin{verbatim} \anthracenev[pa]{9D==O;{{10}D}==O;2==COOH}\hskip1.5cm \anthracenev[pA]{9D==O;{{10}D}==O;2==COOH} \end{verbatim} These commands produce: \begin{center} \anthracenev[pa]{9D==O;{{10}D}==O;2==COOH}\hskip1.5cm \anthracenev[pA]{9D==O;{{10}D}==O;2==COOH} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \subsection{Command for General Use} The macro \verb/\hanthracenev/ (carom.sty) is a more general macro than \verb/anthracenev/, where the latter is actually a short-cut command of the former. The format of this command is as follows: \begin{verbatim} \hanthracenev[BONDLIST]{SUBSLIST} \end{verbatim} % *********************************** % * perhydro anthracene derivatives * % * (vertical type) * % *********************************** Locant numbers (1--12) for designating substitution positions and bond descriptors (a--p) are represented by the following diagram: \begin{xymspec} \begin{picture}(1500,1300)(0,-200) {\footnotesize \put(0,0){\hanthracenev{% 1Sb==1;1Sa==1Sa(r);2Sb==2Sb(r);2Sa==2Sa(r);% 3Sb==3Sb(r);3Sa==3Sa(r);4Sb==4;4Sa==4Sa(r);% 5Sb==5Sb(l);5Sa==5;6Sb==6Sb(l);6Sa==6Sa(l);% 7Sb==7Sb(l);7Sa==7Sa(l);8Sb==8Sb(l);8Sa==8;% 9Sb==9;9Sa==9;{{10}Sb}==10;{{10}Sa}==10;% {{11}F}==11F;{{11}G}==11G;{{12}F}==12F;{{12}G}==12G}} \put(553,940){\hbox to0pt{\hss Sa}} \put(553,1040){\hbox to0pt{\hss (r)}} \put(593,940){\hbox to0pt{Sb\hss}} \put(593,1040){\hbox to0pt{(l)\hss}} \put(553,-100){\hbox to0pt{\hss Sa}} \put(553,-200){\hbox to0pt{\hss (r)}} \put(593,-100){\hbox to0pt{Sb\hss}} \put(593,-200){\hbox to0pt{(l)\hss}} % \put(895,940){\hbox to0pt{\hss Sa}} \put(895,1040){\hbox to0pt{\hss (r)}} \put(935,940){\hbox to0pt{Sb\hss}} \put(935,1040){\hbox to0pt{(l)\hss}} \put(895,-100){\hbox to0pt{\hss Sa}} \put(895,-200){\hbox to0pt{\hss (r)}} \put(935,-100){\hbox to0pt{Sb\hss}} \put(935,-200){\hbox to0pt{(l)\hss}} } {\footnotesize \put(0,0){\bdloocant{k}{p}{g}{h}{i}{j}} \put(342,0){\bdloocant{m}{o}{e}{f}{}{l}} \put(684,0){\bdloocant{a}{b}{c}{d}{}{n}}} \end{picture} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses. The option argument BONDLIST is based on the assignment of characters (a--p) to respective bonds as shown in the above diagram and Table \ref{tt:a9}. \begin{table}[hpbt] \caption{Argument BONDLIST for commands {\tt$\backslash$hanthracenev}} \label{tt:a9} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline none & perhydro-anthracene \\ a & 1,2-double bond \\ b & 2,3-double bond \\ c & 3,4-double bond \\ d & 4,4a-double bond \\ e & 10,4a-double bond \\ f & 10,10a-double bond \\ g & 5,10a-double bond \\ h & 5,6-double bond \\ i & 6,7-double bond \\ j & 8,7-double bond \\ k & 8,8a-double bond \\ l & 9,8a-double bond \\ m & 9,9a-double bond \\ n & 1,9a-double bond \\ o & 4a,9a-double bond \\ p & 10a,8a-double bond \\ A & right aromatic circle \\ B & central aromatic circle \\ C & left aromatic circle \\ \hline \end{tabular} \end{center} \end{table} A bond modifier in the argument SUBSLIST for $n=1\mbox{--}10$ is selected from those shown in Table \ref{tt:a2}. The substitution at the bridgehead positions is designated as shown in Table \ref{tt:a10}. \begin{table}[hpbt] \caption{SUBSLIST for bridgehead positions in {\tt$\backslash$hanthracenev}} \label{tt:a10} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline 11FA & alpha single bond at 9a \\ 11FB & beta single bond at 9a \\ 11FU & unspecified single bond at 9a \\ 11GA & alpha single bond at 4a \\ 11GB & beta single bond at 4a \\ 11GU & unspecified single bond at 4a \\ \hline 12FA & alpha single bond at 8a \\ 12FB & beta single bond at 8a \\ 12FU & unspecified single bond at 8a \\ 12GA & alpha single bond at 10a \\ 12GB & beta single bond at 10a \\ 12GU & unspecified single bond at 10a \\ \hline \end{tabular} \end{center} \end{table} \medskip \noindent Example: \begin{verbatim} \hanthracenev[C]{5==\lmoiety{CH$_{3}$O};% 8==\lmoiety{CH$_{3}$O};9==CN;{{10}D}==O}\qquad \hanthracenev[hjp]{{{11}FA}==H;{{11}GA}==H;1A==OBz;4B==OH;2D==O} \end{verbatim} These commands produce: \begin{center} \hanthracenev[C]{5==\lmoiety{CH$_{3}$O};% 8==\lmoiety{CH$_{3}$O};9==CN;{{10}D}==O}\qquad \hanthracenev[hjp]{{{11}FA}==H;{{11}GA}==H;1A==OBz;4B==OH;2D==O} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \section{Drawing Phenanthrene Derivatives} \subsection{Command for Specified Use} The macro \verb/\phenanthrenev/ is used to draw phenanthrene derivatives of vertical type (carom.sty) as well as various quinone derivatives. The format of this command is as follows: \begin{verbatim} \phenanthrenev[OPT]{SUBSLIST} \end{verbatim} % ********************************* % * phenanthrene and derivatives * % * (vertical type) * % ********************************* Locant numbers for designating substitution positions are represented by the following diagram: \begin{xymspec} \phenanthrenev{1==1(r);2==2(r);3==3(lr);4==4(l);5==5(lr);6==6(l);% 7==7(l);8==8(lr);9==9(lr);{{10}}==10(r)} \qquad\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses. The optional argument OPT is used to specify a bond pattern as shown in Table \ref{tt:a11}. \begin{table}[hpbt] \caption{Argument OPT for commands {\tt$\backslash$phenanthrenev}} \label{tt:a11} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline none or r & right-handed double bonds \\ A & aromatic circle \\ \hline p or pa & 1,4-quinone (A) \\ pA & 1,4-quinone (circle type) \\ \hline o or oa & 1,2-quinone (A) \\ oA & 1,2-quinone (circle type) \\ ob & 2,3-quinone (B) \\ oc & 3,4-anthraquinone (C) \\ \hline q or qa & 9,10-quinone \\ qA & 9,10-quinone (circle type) \\ \hline \end{tabular} \end{center} \end{table} The argument SUBSLIST is employed to specify each substituent with a locant number and a bond modifier shown in Table \ref{tt:a2}, in which $n$ is seledted to be an arabic numeral between 1 and 10. \medskip \noindent Example: \begin{verbatim} \phenanthrenev[q]{9D==O;{{10}D}==O;2==COOH}\hskip1.5cm \phenanthrenev[qA]{9D==O;{{10}D}==O;2==COOH} \end{verbatim} These commands produce: \begin{center} \phenanthrenev[q]{9D==O;{{10}D}==O;2==COOH}\hskip1.5cm \phenanthrenev[qA]{9D==O;{{10}D}==O;2==COOH} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \subsection{Command for General Use} The macro \verb/\hphenantherev/ (carom.sty) is a more general macro than \verb/phenanthrenev/, where the latter is a short-cut command based on the former. The format of this command is as follows: \begin{verbatim} \hphenanthrenev[BONDLIST]{SUBSLIST} \end{verbatim} % ************************************* % * perhydro phenanthrene derivatives * % * (vertical type) * % ************************************* Locant numbers (1--12) for designating substitution positions and bond descriptors (a--p) are represented by the following diagram: \begin{xymspec} \begin{picture}(1500,1600)(0,-200) {\footnotesize \put(0,0){\hphenanthrenev{% 1Sb==1Sb(r);1Sa==1Sa(r);2Sb==2Sb(r);2Sa==2Sa(r);% 3Sb==3Sb(l);3Sa==3Sa(r);4Sb==4a(l);4Sa==4;% 5Sb==5Sb(l);5Sa==5;6Sb==6Sb(l);6Sa==6Sa(l);% 7Sb==7Sb(l);7Sa==7Sa(l);8Sb==8Sb(l);8Sa==8;% 9Sb==9;9Sa==9Sa(r);{{10}Sb}==10Sb(r);{{10}Sa}==10Sa(r);% {{11}F}==;{{11}G}==11G;{{12}F}==;{{12}G}==12G}} \put(553,-100){\hbox to0pt{\hss Sb}} \put(553,-200){\hbox to0pt{\hss (r)}} \put(593,-100){\hbox to0pt{Sb\hss}} \put(593,-200){\hbox to0pt{(l)\hss}} } {\footnotesize \put(0,0){\bdloocant{f}{p}{j}{i}{h}{g}} \put(342,0){\bdloocant{o}{m}{l}{k}{}{e}} \put(513,303){\bdloocant{b}{a}{n}{}{d}{c}}} \end{picture} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses, where the designation of overcrowded positions is abbreviated. The option argument BONDLIST is based on the assignment of characters (a--p) to respective bonds as shown in the above diagram and Table \ref{tt:a12}. \begin{table}[hpbt] \caption{Argument BONDLIST for commands {\tt$\backslash$hphenanthrenev}} \label{tt:a12} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline none & perhydro-phenanthrene \\ a & 1,2-double bond \\ b & 2,3-double bond \\ c & 3,4-double bond \\ d & 4,4a-double bond \\ e & 4a,4b-double bond \\ f & 4b,5-double bond \\ g & 5,6-double bond \\ h & 6,7-double bond \\ i & 7,8-double bond \\ j & 8,8a-double bond \\ k & 8a,9-double bond \\ l & 9,10-double bond \\ m & 10,10a-double bond \\ n & 1,10a-double bond \\ o & 4a,10a-double bond \\ p & 4b,8a-double bond \\ A & right aromatic circle \\ B & central aromatic circle \\ C & left aromatic circle \\ \hline \end{tabular} \end{center} \end{table} A bond modifier in the argument SUBSLIST for $n=1\mbox{--}10$ can be one of bond modifiers shown in Table \ref{tt:a2}. The substitution at the bridgehead positions is similar to that designated in Table \ref{tt:a10} for \verb/\hanthracenev/. \medskip \noindent Example: \begin{verbatim} \hphenanthrenev[acgikm]{{{11}F}=={\kern-3em\raise1ex\hbox{H}};% {{12}F}==\lmoiety{H~~}}\hskip1.5cm \hphenanthrenev[acoj]{7D==O;{{12}FB}==} \end{verbatim} These commands produce: \begin{center} \hphenanthrenev[acgikm]{{{11}F}=={\kern-3em\raise1ex\hbox{H}};% {{12}F}==\lmoiety{H~~}}\hskip1.5cm \hphenanthrenev[acoj]{7D==O;{{12}FB}==} \end{center} %%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%% \section{Drawing Steroid Derivatives} The macro \verb/\steroid/ (carom.sty) typsets a steroid derivative without the side chain. The format of this command is as follows: \begin{verbatim} \steroid[BONDLIST]{SUBSLIST} \end{verbatim} % *********************** % * steroid derivatives * % *********************** Locant numbers (1--17) for designating substitution positions and bond descriptors (a--t) are represented by the following diagram: \begin{xymspec} \begin{picture}(1500,1600)(0,-200) {\footnotesize \put(0,0){\steroid{% 1Sb==1Sb(l);1Sa==1;2Sb==2Sb(l);2Sa==2Sa(l);% 3Sb==3Sb(l);3Sa==3Sa(l);4Sb==4Sb(l);4Sa==4;% 5==5;6Sb==6;6Sa==6Sa(r);7Sb==7Sb(r);7Sa==7Sa(r);8==8;9==9;% {{10}}==10;{{11}Sb}==11Sb(l);{{11}Sa}==11;% {{12}Sa}==12;{{12}Sb}==12Sb(l);{{13}}==13;{{14}}==14;% {{15}Sa}==15Sa(r);{{15}Sb}==15Sb(r);% {{16}Sa}==16Sa(r);{{16}Sb}==16Sb(r);% {{17}Sa}==17Sa(r);{{17}Sb}==17}}}% {\footnotesize \put(0,0){\bdloocant{j}{k}{d}{c}{b}{a}} \put(342,0){\bdloocant{h}{g}{f}{e}{}{i}} \put(513,303){\bdloocant{n}{o}{p}{}{l}{m}} \put(855,303){\bdloocant{s}{r}{}{}{}{t}} \put(1255,603){q}} \end{picture} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses, where the designation of overcrowded positions is abbreviated. The option argument BONDLIST is based on the assignment of characters (a--t) to respective bonds as shown in the above diagram and Table \ref{tt:a13}. \begin{table}[hpbt] \caption{Argument BONDLIST for commands {\tt$\backslash$steroid}} \label{tt:a13} \begin{center} \begin{tabular}{ll|ll} \hline Character & \multicolumn{1}{c|}{Printed structure} & Character & \multicolumn{1}{c}{Printed structure} \\ \hline none& steroid skeleton && \\ a & 1,2-double bond & b & 2,3-double bond \\ c & 3,4-double bond & d & 4,5-double bond \\ e & 6,5-double bond & f & 6,7-double bond \\ g & 7,8-double bond & h & 9,8-double bond \\ i & 9,10-double bond & j & 1,10-double bond \\ k & 5,10-double bond & l & 9,11-double bond \\ m & 12,11-double bond & n & 12,13-double bond \\ o & 14,13-double bond & p & 8,14-double bond \\ q & 14,15-double bond & r & 15,16-double bond \\ s & 17,16-double bond & t & 17,13-double bond \\ A & aromatic A ring & B & aromatic B ring \\ C & aromatic C ring && \\ \hline \end{tabular} \end{center} \end{table} A bond modifier in the argument SUBSLIST for $n=1\mbox{--}17$ (except fused positions) is selected from the list of bond modifiers (Table \ref{tt:a2}). The substitution at the fused positions ($n$ = 5,8,9,10,13 and 14) is similarly designated as for fused bicylic or tricyclic compounds (Table \ref{tt:a14}). \begin{table}[hpbt] \caption{SUBSLIST for fused positions in {\tt$\backslash$steroid}} \label{tt:a14} \begin{center} \begin{tabular}{ll} \hline Character & \multicolumn{1}{c}{Printed structure} \\ \hline $n$ or $n$S & exocyclic single bond at n-atom \\ $n$A & alpha single bond at n-atom (boldface) \\ $n$B & beta single bond at n-atom (dotted line) \\ $n$U & unspecified single bond at n-atom \\ \hline \end{tabular} \end{center} \end{table} \medskip \noindent Example: \begin{verbatim} \steroid[ackhf]{{{13}B}==\lmoiety{H$_{3}$C};{{14}A}==H}\hskip1cm \steroid[d]{3D==O;9A==Br;{{11}D}==O;% {{17}B}==COCH$_3$;{{14}A}==H;% {{13}B}==\lmoiety{H$_3$C};{{10}B}==\lmoiety{H$_3$C}} \end{verbatim} These commands produce: \begin{center} \steroid[ackhf]{{{13}B}==\lmoiety{H$_{3}$C};{{14}A}==H}\hskip1cm \steroid[d]{3D==O;9A==Br;{{11}D}==O;% {{17}B}==COCH$_3$;{{14}A}==H;% {{13}B}==\lmoiety{H$_3$C};{{10}B}==\lmoiety{H$_3$C}} \end{center} In order to avoid the overcrowding of substitution, you can use \TeX{} primitive commands such as \verb/\raise/ and \verb/\kern/. \medskip \noindent Example: \begin{verbatim} \steroid[fhm]{3A==HO;5B==H;{{10}B}==\lmoiety{H$_{3}$C};% {{13}B}==\lmoiety{H$_{3}$C};% {{14}A}==H;{{17}B}==\raise.5ex\hbox{COCH$_{3}$};% {{17}SA}=={\kern.5em\lower1.5ex\hbox{H}}} \end{verbatim} These commands produce: \begin{center} \steroid[fhm]{3A==HO;5B==H;{{10}B}==\lmoiety{H$_{3}$C};% {{13}B}==\lmoiety{H$_{3}$C};% {{14}A}==H;{{17}B}==\raise.5ex\hbox{COCH$_{3}$};% {{17}SA}=={\kern.5em\lower1.5ex\hbox{H}}} \end{center} The macro \verb/\steroidchain/ (carom.sty) is to draw a steroid derivative with the side chain. The format of this command is as follows: \begin{verbatim} \steroidchain[BONDLIST]{SUBSLIST} \end{verbatim} % ************************************** % * steroid derivatives having a chain * % ************************************** Locant numbers for designating substitution positions and bond descriptors for the side chain are represented by the following diagram: \begin{xymspec} \begin{picture}(1500,1600)(0,0) {\footnotesize \put(0,0){\steroidchain{% {{20}Sa}==20Sa(l);{{20}Sb}==20Sb(l);% {{22}Sa}==22Sa(r);{{22}Sb}==\lmoiety{22Sb(lr)};% {{23}Sa}==23;{{23}Sb}==23Sb(r);% {{24}Sa}==24Sa(r);{{24}Sb}==24;% {{25}}==25}}}% {\footnotesize \put(1026,606){\bdloocant{Zc}{Zd}{}{}{Za}{Zb}} \put(1697,853){Ze} \put(1900,1003){Zf}\put(1900,853){Zg}} \end{picture} \qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\ $\bullet$: (\the\noshift,\the\noshift)}} \end{xymspec} The handedness for each oriented or double-sided position is shown with a character set in parentheses, where the designation of overcrowded positions is abbreviated. The option argument BONDLIST is based on the assignment of characters (a--t) to respective bonds as shown in the above diagram and Table \ref{tt:a13}. The locant-numbering of chain carbons is also designated with the BONDLIST in the form of two-character indicators (Za--Zg) as collected in Table \ref{tt:a15}. \begin{table}[hpbt] \caption{Argument BONDLIST for chain carbons ({\tt$\backslash$steroidchain})} \label{tt:a15} \begin{center} \begin{tabular}{ll|ll} \hline Character & \multicolumn{1}{c|}{Printed structure} & Character & \multicolumn{1}{c}{Printed structure} \\ \hline Z & no action && \\ Za & 17,20-double bond & Zb & 20,22-double bond \\ Zc & 22,23-double bond & Zd & 23,24-double bond \\ Ze & 24,25-double bond & Zf & 25,26-double bond \\ Zg & 25,27-double bond & & \\ \hline \end{tabular} \end{center} \end{table} A bond modifier in the argument SUBSLIST for $n=1\mbox{--}25$ (except fused positions and terminal positions not to be specified, {\em e.g.}, 18) can be one of bond modifiers shown in Table \ref{tt:a2}. On the other hand, a bond modifier in the argument SUBSLIST for $n$ = 5, 8, 9, 10, 13, 14, or 25 (fused positions {\em etc.}) can be selected from bond modifiers shown in Table \ref{tt:a14}. For example, the \verb/\steroidchain/ macro prints (24$R$)-24-methyl-5$\alpha$-cholestan-3$\beta$-ol (campestanol) and 5$\alpha$-lanostane only by replacing substituents in argument SUBSLIST. Thus, the statements \begin{verbatim} \steroidchain{3B==HO;5A==H;{{10}B}==\lmoiety{H$_3$C};9A==H;8B==H;% {{17}SA}==\lower1ex\hbox{ H};{{13}B}==\lmoiety{H$_3$C};{{14}A}==H;% {{20}SA}==H$_3$C;{{20}SB}==H;{{24}SA}==CH$_3$;{{24}SB}==H} \steroidchain{4SB==\lmoiety{H$_3$C};4SA==CH$_3$;5A==H;% {{17}SA}==\lower1ex\hbox{ H};% {{10}B}==\lmoiety{H$_3$C};9A==H;8B==H;{{13}B}==\lmoiety{H$_3$C};% {{14}A}==CH$_3$;{{20}SA}==\lmoiety{H$_3$C};{{20}SB}==H} \end{verbatim} typeset the following structural diagrams: \begin{center} \steroidchain{3B==HO;5A==H;{{10}B}==\lmoiety{H$_3$C};9A==H;8B==H;% {{17}SA}==\lower1ex\hbox{ H};{{13}B}==\lmoiety{H$_3$C};{{14}A}==H;% {{20}SA}==H$_3$C;{{20}SB}==H;{{24}SA}==CH$_3$;{{24}SB}==H} \steroidchain{4SB==\lmoiety{H$_3$C};4SA==CH$_3$;5A==H;% {{17}SA}==\lower1ex\hbox{ H};% {{10}B}==\lmoiety{H$_3$C};9A==H;8B==H;{{13}B}==\lmoiety{H$_3$C};% {{14}A}==CH$_3$;{{20}SA}==\lmoiety{H$_3$C};{{20}SB}==H} \end{center} The following example of drawing cucurbitacin I illustrates the designation of double bonds in the side chain. Thus, a single macro is capable of covering a wide variety of derivatives by altering the description in arguments BONDLIST and SUBSLIST. \begin{verbatim} \steroidchain[ae{Zd}]{2==HO;3D==O;4Sb==\lmoiety{H$_3$C};4Sa==CH$_3$;% 9Sa==CH$_{3}$;{{11}D}==O;{{13}}==\lmoiety{H$_3$C};% {{14}}==CH$_3$;{{20}Sa}==\lmoiety{H$_3$C};{{20}Sb}==HO;% {{16}Sa}==OH;{{22}D}==O;{{25}}==OH} \end{verbatim} produces \begin{center} \steroidchain[ae{Zd}]{2==HO;3D==O;4Sb==\lmoiety{H$_3$C};4Sa==CH$_3$;% 9Sa==CH$_{3}$;{{11}D}==O;{{13}}==\lmoiety{H$_3$C};% {{14}}==CH$_3$;{{20}Sa}==\lmoiety{H$_3$C};{{20}Sb}==HO;% {{16}Sa}==OH;{{22}D}==O;{{25}}==OH} \end{center} \endinput % 1993/11/24/ (Version 1.00) Copyright (C) by Shinsaku Fujita % All rights reserved.