%xymhetg.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{``xymhetg.tex''---
This file is a part of xymtex.tex that is the manual of the macro %
package `XyMTeX'. 1993/12/1 S. Fujita}
%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\chapter{Heterocycles with Fused Six- and Five-Membered Rings}
\section{Drawing Vertical Forms}
\subsection{Commands for Specified Use}

\XyMTeX{} involves macros for drawing representative 
fused N-heterocycles that consist of a six- and a five-membered ring. 
These have the following formats (hetarom.sty). 
\begin{verbatim}
   \indolev[BONDLIST]{SUBSLIST}
   \isoindolev[BONDLIST]{SUBSLIST}
   \purinev[BONDLIST]{SUBSLIST}
\end{verbatim}
Macros for drawing fused N,O-heterocycles 
are also available (hetarom.sty). 
They are the same formats of arguments. 
\begin{verbatim}
   \benzofuranev[BONDLIST]{SUBSLIST}
   \isobenzofuranev[BONDLIST]{SUBSLIST}
   \benzoxazolev[BONDLIST]{SUBSLIST}
\end{verbatim}
The locant numbering is common in these commands as 
shown in the following diagram:
\begin{xymspec}
\indolev{1==1(lr);2==2(r);3==3(r);4==4(lr);5==5(l);6==6(l);%
7==7(lr)}%
\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(1000,1000)(0,0)
\put(0,0){\indolev[H]{%
1Sb==1;1Sa==1Sa(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);%
7Sb==7Sb(l);7Sa==7;%
8==8;9==9}}
%\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{d}{j}{h}{g}{f}{e}}
\put(342,0){\bdloocant{{\kern-10pt\lower1ex\hbox{c}}}{b}{a}{i}{}{}}}
\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 optional argument BONDLIST specifies edges with a double bond 
(Table \ref{tt:f2}).
\begin{table}[hpbt]
\caption{Argument BONDLIST for commands {\tt$\backslash$indolev} 
and others}
\label{tt:f2}
\begin{center}
\begin{tabular}{ll|ll}
\hline
Character & \multicolumn{1}{c|}{Printed structure} &
Character & \multicolumn{1}{c}{Printed structure} \\
\hline
           none or r  &  aromatic six-membered ring & 
           H or []    &  fully saturated form \\
     a    &  1,2-double bond     & b    &  2,3-double bond \\
     c    &  3,3a-double bond    & d    &  4,3a-double bond \\
     e    &  4,5-double bond     & f    &  5,6-double bond \\
     g    &  6,7-double bond     & h    &  7,7a-double bond \\
     i    &  1,7a-double bond    & j    &  3a,4a-double bond \\
     A  &  
    \multicolumn{2}{l}{aromatic circle (six-membered ring)} 
            & \\
     B  &  
    \multicolumn{2}{l}{aromatic circle (five-membered ring)} 
            & \\
 $\{n+\}$   &  
    \multicolumn{2}{l}{plus at the $n$-nitrogen atom ($n$ = 1 to 9)} 
            & \\
\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 7. 
Sibstitution on  8 (3a position) or 9 (7a position) can 
be assigned in the same way. 

\medskip
\noindent
Example:
\begin{verbatim}
   \indolev{1==H;2==COOH}\qquad
   \isoindolev{2==H;1==CN;3==CN}\qquad
   \purinev{3==H}
\end{verbatim}
produce the following structures: 
\begin{center}
   \indolev{1==H;2==COOH}\qquad
   \isoindolev{2==H;1==CN;3==CN}\qquad
   \purinev{3==H}
\end{center}

\medskip
\noindent
Example:
\begin{verbatim}
   \benzofuranev{2==COOH}\qquad
   \isobenzofuranev{1==Ph;3==Ph}\qquad
   \benzoxazolev{2==CH$_{3}$;5==HO}
\end{verbatim}
produce the following structures: 
\begin{center}
   \benzofuranev{2==COOH}\qquad
   \isobenzofuranev{1==Ph;3==Ph}\qquad
   \benzoxazolev{2==CH$_{3}$;5==HO}
\end{center}

%%%%%%
Macros for drawing fused N-heterocycles of inverse vertical type have 
the following formats (hetarom.sty). 
\begin{verbatim}
   \indolevi[BONDLIST]{SUBSLIST}
   \isoindolevi[BONDLIST]{SUBSLIST}
   \purinevi[BONDLIST]{SUBSLIST}
\end{verbatim}
Macros for drawing fused N,O-heterocycles of inverse vertical type have 
the following formats.  They are also contained in the style file 
`hetarom.sty'.
\begin{verbatim}
   \benzofuranevi[BONDLIST]{SUBSLIST}
   \isobenzofuranevi[BONDLIST]{SUBSLIST}
   \benzoxazolevi[BONDLIST]{SUBSLIST}
\end{verbatim}
They are the counterparts of the commands without suffix `i' 
described above. 
The locant numbering is common in these commands as 
shown in the following diagram:
\begin{xymspec}
\indolevi{1==1(lr);2==2(r);3==3(r);4==4(lr);5==5(l);6==6(l);%
7==7(lr)}%
\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(1000,1000)(0,0)
\put(0,0){\indolevi[H]{%
1Sb==1;1Sa==1Sa(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);%
7Sb==7Sb(l);7Sa==7;%
8==8;9==9}}
{\footnotesize
\put(0,0){\bdloocant{h}{j}{d}{e}{f}{g}}
\put(342,0){\bdloocant{a}{b}{{\kern-10pt\raise1ex\hbox{c}}}{}{}{i}}}
\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 optional argument BONDLIST is used in a usual way (Table \ref{tt:f2}).

\medskip
\noindent
Example:
\begin{verbatim}
   \indolevi{1==H;2==COOH}\qquad
   \isoindolevi{2==H;1==CN;3==CN}\qquad
   \purinevi{3==H}
\end{verbatim}
produce the following structures: 
\begin{center}
   \indolevi{1==H;2==COOH}\qquad
   \isoindolevi{2==H;1==CN;3==CN}\qquad
   \purinevi{3==H}
\end{center}

\medskip
\noindent
Example:
\begin{verbatim}
   \benzofuranevi{2==COOH}\qquad
   \isobenzofuranevi{1==Ph;3==Ph}\qquad
   \benzoxazolevi{2==CH$_{3}$;5==HO}
\end{verbatim}
produce the following structures: 
\begin{center}
   \benzofuranevi{2==COOH}\qquad
   \isobenzofuranevi{1==Ph;3==Ph}\qquad
   \benzoxazolevi{2==CH$_{3}$;5==HO}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\subsection{Commands for General Use}

Macros for specified use such as \verb/\indolev/ are 
short-cut commands based on a general command \verb/\nonaheterov/. 
Such a general command enables us to draw a further variety of 
heterocyclic compounds. 
It has the following format, the definition of which 
is contained also in hetarom.sty.
\begin{verbatim}
   \nonaheterov[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% **************************
% * nonahetero derivatives *
% *  (vertical type)       *
% **************************
% The following numbering is adopted in this macro. 
%
%          4
%          *  3a(8) 
%     5  *   * _____  3
%       |     |     |
%       |     |     |
%     6  *   * *   *  2
%          *  7a *
%          7 (9) 1
%          ^
%          |
%          the original point
%
Locant numbers (1--9) and bond descriptors (a--j) are defined 
as shown in the following diagram:
\begin{xymspec}
\begin{picture}(1000,1000)(0,0)
\put(0,0){\nonaheterov[H]{1==1;2==2;3==3;4==4;5==5;%
6==6;7==7;8==8;9==9}{%
1Sb==1;1Sa==1Sa(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);%
7Sb==7Sb(l);7Sa==7;%
8==8;9==9}}
%\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{d}{j}{h}{g}{f}{e}}
\put(342,0){\bdloocant{{\kern-10pt\lower1ex\hbox{c}}}{b}{a}{i}{}{}}}
\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 optional argument BONDLIST is used to specify double bonds 
as shown in Table \ref{tt:f2}.

The argument ATOMLIST takes a usual format with respect to 
heteroatoms attached to $n$ = 1 to 7, {\em e.g.}, 
1==N for a nitrogen atom at 1-position.  
Hetero atoms at 3a- and 7a-positions are 
represented as to be 3a==N (or 8==N) for a nitrogen at 3a-position, 
7a==N (or 9==N) for at a nitrogen at 7a-position, and so on.
The augument SUBSLIST takes a usual format except that 
the locant numbers 3a and 7a are replaced by 8 and 9. 

\medskip
\noindent
Example:
\begin{verbatim}
 \nonaheterov[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}
 \nonaheterov[bjge]{1==N;5==N;7==N}%
  {1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}
 \nonaheterov[bjge]{1==S;2==N}{3==Cl}
\end{verbatim}
produce the following structures: 
\begin{center}
 \nonaheterov[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}
 \nonaheterov[bjge]{1==N;5==N;7==N}%
  {1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}
 \nonaheterov[bjge]{1==S;2==N}{3==Cl}
\end{center}

The inverse conterpart \verb/\nonaheterovi/ has 
the following format:
\begin{verbatim}
   \nonaheterovi[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% **********************************
% * nonahetero derivatives         *
% *  (vertical type, inverse type) *
% **********************************
% The following numbering is adopted in this macro. 
%
%          7(10) 1
%          * 7a  *
%     6  *   * *   *  2
%       |     |     |
%       |     |_____|
%     5  *   *        3
%          *  3a(8) 
%          4 
%          ^
%          |
%          the original point
%
%  
Locant numbering is usually defined 
as shown in the following diagram:
\begin{xymspec}
\begin{picture}(1000,1000)(0,0)
\put(0,0){\nonaheterovi[H]{1==1;2==2;3==3;4==4;5==5;%
6==6;7==7;8==8;9==9}{%
1Sb==1;1Sa==1Sa(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);%
7Sb==7Sb(l);7Sa==;%
8==8;9==9}}
{\footnotesize
\put(0,0){\bdloocant{h}{j}{d}{e}{f}{g}}
\put(342,0){\bdloocant{a}{b}{{\kern-10pt\raise1ex\hbox{c}}}{}{}{i}}}
\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 same format of the optional argument BONDLIST is used
as shown in Table \ref{tt:f2}.

\medskip
\noindent
Example:
\begin{verbatim}
 \nonaheterovi[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}
 \nonaheterovi[bjge]{1==N;5==N;7==N}%
  {1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}
 \nonaheterovi[bjge]{1==S;2==N}{3==Cl}
\end{verbatim}
produce the following structures: 
\begin{center}
 \nonaheterovi[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}
 \nonaheterovi[bjge]{1==N;5==N;7==N}%
  {1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}
 \nonaheterovi[bjge]{1==S;2==N}{3==Cl}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\section{Drawing Horizontal Forms}
\subsection{Commands for Specified Use}

Macros for drawing N-heterocycles of horizontal type have 
the following formats (hetaromh.sty). 
\begin{verbatim}
   \indoleh[BONDLIST]{SUBSLIST}
   \isoindoleh[BONDLIST]{SUBSLIST}
   \purineh[BONDLIST]{SUBSLIST}
\end{verbatim}
Macros for drawing N,O-heterocycles are available by 
setting the option style file `hetaromh.sty'. 
They have the following formats. 
\begin{verbatim}
   \benzofuraneh[BONDLIST]{SUBSLIST}
   \isobenzofuraneh[BONDLIST]{SUBSLIST}
   \benzoxazoleh[BONDLIST]{SUBSLIST}
\end{verbatim}
Locant numbers for designating substitution positions 
are represented by the following diagram: 
\begin{xymspec}
\indoleh{1==1(r);2==2(lr);3==3(lr);4==4(l);5==5(lr);6==6(lr);7==7(r)}%
\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shiftiii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(1000,1200)(0,0)
\put(0,0){\indoleh[H]{%
1Sb==1Sb(r);1Sa==1Sa(r);2Sb==2Sb(r);2Sa==2Sa(lr);%
3Sb==3Sb(l);3Sa==\lmoiety{3Sa(lr)};4Sb==4Sb(l);4Sa==4Sa(l);%
5Sb==5Sb(l);5Sa==\lmoiety{5Sa(lr)};6Sb==6Sb(r);6Sa==6Sa(lr);%
7Sb==7Sb(r);7Sa==7Sa(r);8==8;9==9}}%
{\footnotesize
\put(160,58){\bdloocnth{d}{j}{h}{g}{f}{e}}
\put(160,402){\bdloocnth{{\lower10pt\hbox{c}\kern-.8em}}{b}{a}{i}{}{}}}%
 %%400-240=160
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shiftiii) \\
                   $\bullet$: (\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 BONDLIST specifies double bonds 
by using chracters selected from Table \ref{tt:f1}. 

\medskip
\noindent
Example:
\begin{verbatim}
   \indoleh{1==H;2==COOH}\qquad
   \isoindoleh{2==H;1==CN;3==CN}\qquad
   \purineh{3==H}
\end{verbatim}
produce the following structures: 
\begin{center}
   \indoleh{1==H;2==COOH}\qquad
   \isoindoleh{2==H;1==CN;3==CN}\qquad
   \purineh{3==H}
\end{center}

\medskip
\noindent
Example:
\begin{verbatim}
   \benzofuraneh{2==COOH}\qquad
   \isobenzofuraneh{1==Ph;3==Ph}\qquad
   \benzoxazoleh{2==CH$_{3}$;5==HO}
\end{verbatim}
produce the following structures: 
\begin{center}
   \benzofuraneh{2==COOH}\qquad
   \isobenzofuraneh{1==Ph;3==Ph}\qquad
   \benzoxazoleh{2==CH$_{3}$;5==HO}
\end{center}

The macro \verb/\indolehi/ is used to draw 
inodele derivatives of inverse horizontal type (hetaromh.sty). 
Macros for drawing other fused heterocycles are also defined in 
the hetaromh.sty. 
The format of these commands is as follows: 
\begin{verbatim}
   \indolehi[BONDLIST]{SUBSLIST}
   \isoindolehi[BONDLIST]{SUBSLIST}
   \purinehi[BONDLIST]{SUBSLIST}
   \benzofuranehi[BONDLIST]{SUBSLIST}
   \isobenzofuranehi[BONDLIST]{SUBSLIST}
   \benzoxazolehi[BONDLIST]{SUBSLIST}
\end{verbatim}
Locant numbers for designating substitution positions 
and characters for describing bonds to be doubled 
are shown in the following diagram: 
\begin{xymspec}
\indolehi{1==1(l);2==2(lr);3==3(lr);4==4(r);5==5(lr);6==6(lr);%
7==7(l)}
\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shiftiii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(1000,1200)(0,0)
\put(0,0){\indolehi[H]{%
1Sb==1Sb(l);1Sa==1Sa(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(r);6Sb==6Sb(r);6Sa==\lmoiety{6Sa(lr)};%
7Sb==7Sb(l);7Sa==7Sa(l);8==8;9==9}}
{\footnotesize
\put(160,58){\bdloocnth{h}{i}{d}{e}{f}{g}}
\put(160,402){\bdloocnth{a}{b}{{\kern-.7em\lower10pt\hbox{c}}}{}{}{i}}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shiftiii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

\medskip
\noindent
Example:
\begin{verbatim}
   \indolehi{1==H;2==COOH}\qquad
   \isoindolehi{2==H;1==NC;3==CN}\qquad
   \purinehi{3==H}
\end{verbatim}
produce the following structures: 
\begin{center}
   \indolehi{1==H;2==COOH}\qquad
   \isoindolehi{2==H;1==NC;3==CN}\qquad
   \purinehi{3==H}
\end{center}

\medskip
\noindent
Example:
\begin{verbatim}
   \benzofuranehi{2==COOH}\qquad
   \isobenzofuranehi{1==Ph;3==Ph}\qquad
   \benzoxazolehi{2==CH$_{3}$;5==OH}
\end{verbatim}
produce the following structures: 
\begin{center}
   \benzofuranehi{2==COOH}\qquad
   \isobenzofuranehi{1==Ph;3==Ph}\qquad
   \benzoxazolehi{2==CH$_{3}$;5==OH}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\subsection{Commands for General Use}

Macros for specified use such as \verb/\indoleh/ are 
based on a general command \verb/\nonaheteroh/. 
This command enable us to draw a further variety of 
heterocyclic compounds. 
This macro has 
the following format which is contained also in hetaromh.sty.
\begin{verbatim}
   \nonaheteroh[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% **************************
% * nonahetero derivatives *
% *  (horizontal type)     *
% **************************
% The following numbering is adopted in this macro. 
%
%           3   2
%
%                  1           (*1 origin)
%
%       (8)3a   7a(9)
%
%       4          7
%
%           5   6
%   ____                     ____
%  |cf.                          |
%  |        4 (8)               |
%  |        *  3a                |
%  |   5  *   * -----  3         |
%  |     |     |     |           |
%  |     |     |     |           |
%  |   6  *   * *   *  2         |
%  |        *  7a *              |
%  |        7 (9) 1              |
%  |        ^                    |
%  |        |                    |
%  |        the original point   |
%  |____                     ____|
The locant numbering is common in these commands as 
shown in the following diagram:
\begin{xymspec}
\begin{picture}(1000,1200)(0,0)
\put(0,0){\nonaheteroh[H]{1==1;2==2;3==3;4==4;5==5;%
6==6;7==7;8==8;9==9}{%
1Sb==1Sb(r);1Sa==1Sa(r);2Sb==2Sb(r);2Sa==2Sa(lr);%
3Sb==3Sb(l);3Sa==\lmoiety{3Sa(lr)};4Sb==4Sb(l);4Sa==4Sa(l);%
5Sb==5Sb(l);5Sa==\lmoiety{5Sa(lr)};6Sb==6Sb(r);6Sa==6Sa(lr);%
7Sb==7Sb(r);7Sa==7Sa(r);8==8;9==9}}%
{\footnotesize
\put(160,58){\bdloocnth{d}{j}{h}{g}{f}{e}}
\put(160,402){\bdloocnth{{\lower10pt\hbox{c}\kern-.8em}}{b}{a}{i}{}{}}}%
 %%400-240=160
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shiftiii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}
The handedness for each oriented or double-sided position 
is shown with a character set in parentheses. 
Characters listed in Table \ref{tt:f2} are also used to specify 
double bonds by setting them into the optional argument BONDLIST. 

The argument ATOMLIST takes a usual format with respect to 
heteroatoms attached to $n$ = 1 to 7, {\em e.g.}, 
1==N for a nitrogen atom at 1-position.  
Hetero-atoms at 3a- and 7b-positions are 
represented as to be 3a==N (or 8==N) for a nitrogen at 3a-position, 
7a==N (or 9==N) for at a nitrogen at 7a-position, and so on.
The augument SUBSLIST takes a usual format except that 
the locant numbers 3a and 7a are replaced by 8 and 9. 

\medskip
\noindent
Example:
\begin{verbatim}
 \nonaheteroh[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}
 \nonaheteroh[bjge]{1==N;5==N;7==N}%
  {1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}
 \nonaheteroh[bjge]{1==S;2==N}{3==Cl}
\end{verbatim}
produce the following structures: 
\begin{center}
 \nonaheteroh[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}
 \nonaheteroh[bjge]{1==N;5==N;7==N}%
  {1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}
 \nonaheteroh[bjge]{1==S;2==N}{3==Cl}
\end{center}

The inverse conterpart \verb/\nonaheterohi/ 
are also available by setting `hetaromh.sty'. 
Its format is: 
\begin{verbatim}
   \nonaheterohi[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% ************************************
% * nonahetero derivatives           *
% *  (horizontal type, inverse type) *
% ************************************
% The following numbering is adopted in this macro. 
%
%
%           2   3
%
%        1       
%
%       (9)7a   3a(8)
%
%       7          4
%
%           6   5
%   ____                     ____
%  |cf.                          |
%  |        7 (9) 1              |
%  |        *  7a *              |
%  |   6  *   * *   *  2         |
%  |     |     |     |           |
%  |     |     |     |           |
%  |   5  *   * -----  3         |
%  |        *  3a                |
%  |        4 (8)                |
%  |        ^                    |
%  |        |                    |
%  |        the original point   |
%  |____                     ____|
%
Its locant numbering is common with the normal counterpart 
as shown in the following diagram:
\begin{xymspec}
\begin{picture}(1000,1200)(0,0)
\put(0,0){\nonaheterohi[H]{1==1;2==2;3==3;4==4;5==5;%
6==6;7==7;8==8;9==9}{%
1Sb==1Sb(l);1Sa==1Sa(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(r);6Sb==6Sb(r);6Sa==\lmoiety{6Sa(lr)};%
7Sb==7Sb(l);7Sa==7Sa(l);8==8;9==9}}
{\footnotesize
\put(160,58){\bdloocnth{h}{i}{d}{e}{f}{g}}
\put(160,402){\bdloocnth{a}{b}{{\kern-.7em\lower10pt\hbox{c}}}{}{}{i}}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shiftiii) \\
                   $\bullet$: (\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 BONDLIST uses 
characters listed in Table \ref{tt:f2} so as to specify double bonds. 

\medskip
\noindent
Example:
\begin{verbatim}
 \nonaheterohi[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}
 \nonaheterohi[bjge]{1==N;5==N;7==N}%
  {1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}
 \nonaheterohi[bjge]{1==S;2==N}{3==Cl}
\end{verbatim}
produce the following structures: 
\begin{center}
 \nonaheterohi[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}
 \nonaheterohi[bjge]{1==N;5==N;7==N}%
  {1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}
 \nonaheterohi[bjge]{1==S;2==N}{3==Cl}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\chapter{Building Blocks}
\section{Six-Membered Blocks}
The macro \verb/\sixunitv/ provides a six-membered fragment 
that can be fused to another ring structure, 
producing a new ring system. 
\begin{verbatim}
   \sixunitv[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}
\end{verbatim}
% **********************
% * six-membered unit  *
% *  (vertical type)   *
% **********************
%
%          1
%          *  
%     6  *   *  2
%       |     |
%       |     |
%     5  *   *  3
%          *
%          4 <===== the original point
%
The modes of numbering for positions and for edges are the same as 
those of \verb/\sixheterov/.  Hence, 
the arguments BONDLIST, ATOMLIST, and SUBSLIST are 
written in the same way.  
The argument OMIT indicates bonds to be deleted, where 
characters are selected from the table prepared for the BONDLIST of 
\verb/\sixheterov/. 
%  
%     BONDLIST = 
%
%           none       :  fully saturated
%           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
%           {n+}       :  plus at the n-nitrogen atom (n = 1 to 4)
%
%     ATOMLIST: list of heteroatoms (max 6 atoms)
%
%       for n = 1 to 6
%
%           n          : Hetero atom, e.g. N, O, etc. at n-position, 
%                        e.g. 1==N for N at 1-position
%
%     SUBSLIST: list of substituents (max 6 substitution positions)
%
%       for n = 1 to 6 
%
%           nD         :  exocyclic double bond at n-atom
%           n or nS    :  exocyclic single bond at n-atom
%           nA         :  alpha single bond at n-atom
%           nB         :  beta single bond at n-atom
%           nSA        :  alpha single bond at n-atom (boldface)
%           nSB        :  beta single bond at n-atom (dotted line)
%           nSa        :  alpha (not specified) single bond at n-atom
%           nSb        :  beta (not specified) single bond at n-atom
%
%     OMIT:  one bond omitted (a, b, c, d, e, or f)
%
It should be noted that the assignment of a null argument to 
ATOMLIST produces a carbocyclic building block. 

\medskip
\noindent
Example:
\begin{verbatim}
   \sixunitv[b]{1==N}{1==H;2==Cl}{d} \qquad
   \sixunitv[b]{}{1D==O;2==Cl}{d}
\end{verbatim}
produce the following structures: 
\begin{center}
   \sixunitv[b]{1==N}{1==H;2==Cl}{d} \qquad
   \sixunitv[b]{}{1D==O;2==Cl}{d}
\end{center}

The macro \verb/\sixunith/ is the horizontal counterpart of 
\verb/\sixunitv/.  
It produces a six-membered fragment of horizontal type, 
\begin{verbatim}
   \sixunith[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}
\end{verbatim}
% **********************
% * six-membered unit  *
% *  (horizontal type) *
% **********************
%
%                                   b
%                                2      3  
%                            a    -----    c
%                               *       *
%   the original point ===> 1 *           * 4
%          (0,0)                *       *  d
%                            f    -----
%                                6      5 
%                                   e
%

\medskip
\noindent
Example:
\begin{verbatim}
   \sixunith[b]{1==N}{1==H;2==Cl}{d} \qquad
   \sixunith[b]{}{1D==O;2==Cl}{d}
\end{verbatim}
produce the following structures: 
\begin{center}
   \sixunith[b]{1==N}{1==H;2==Cl}{d} \qquad
   \sixunith[b]{}{1D==O;2==Cl}{d}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\section{Five-Membered Blocks}
 
The macro \verb/\fiveunitv/ 
produces a five-membered fragment that can be fused to another 
ring structure to produce a new ring system. 
\begin{verbatim}
   \fiveunitv[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}
\end{verbatim}
% **********************
% * five-membered unit *
% *  (vertical type)   *
% **********************
%
%     4 _______ 3
%       |     |
%       |     |
%     5  *   *  2
%          *
%          1 <===== the original point
%
%
%  
%     BONDLIST: list of inner double bonds 
%
%           a          :  1,2-double bond
%           b          :  2,3-double bond
%           c          :  4,3-double bond
%           d          :  4,5-double bond
%           e          :  5,1-double bond
%           {n+}       :  plus at the n-nitrogen atom (n = 1 to 4)
%
%     ATOMLIST: list of heteroatoms (max 5 atoms)
%
%       for n = 1 to 5
%
%           n          : Hetero atom, e.g. N, O, etc. at n-position
%                        e.g. 1==N for N at 1-position
%
%     SUBSLIST: list of substituents (max 5 substitution positions)
%
%       for n = 1 to 5 
%
%           nD         :  exocyclic double bond at n-atom
%           n or nS    :  exocyclic single bond at n-atom
%           nA         :  alpha single bond at n-atom
%           nB         :  beta single bond at n-atom
%           nSA        :  alpha single bond at n-atom (boldface)
%           nSB        :  beta single bond at n-atom (dotted line)
%           nSa        :  alpha (not specified) single bond at n-atom
%           nSb        :  beta (not specified) single bond at n-atom
%
%     OMIT:  one bond omitted (a, b, c, d, e, or f)
%
The numbering of positions and the designation of edges are the same as 
those of \verb/\fiveheterov/.  Hence, 
the arguments BONDLIST, ATOMLIST, and SUBSLIST are 
written in the same way.  
The argument OMIT indicates bonds to be deleted.  
It is a list of the same format as the BONDLIST of \verb/\fiveheterov/. 

\medskip
\noindent
Example:
\begin{verbatim}
   \fiveunitv[b]{1==N}{1==H;2==Cl}{d} \qquad
   \fiveunitv[b]{}{1D==O;2==Cl}{d}
\end{verbatim}
produce the following structures: 
\begin{center}
   \fiveunitv[b]{1==N}{1==H;2==Cl}{d} \qquad
   \fiveunitv[b]{}{1D==O;2==Cl}{d}
\end{center}

The macro \verb/\fiveunitvi/ 
produces a five-membered fragment of inverse type that can be fused to another 
ring structure to produce a new ring system. 
\begin{verbatim}
   \fiveunitvi[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}
\end{verbatim}
% ************************************
% * five-membered unit               *
% *  (vertical type, inverse type)   *
% ************************************
%
%          1
%          * 
%     6  *   *  2
%       |     |
%       |_____|
%     4         3
%          *
%        (0,0) <===== the original point
%

\medskip
\noindent
Example:
\begin{verbatim}
   \fiveunitvi[b]{1==N}{1==H;2==Cl}{d} \qquad
   \fiveunitvi[b]{}{1D==O;2==Cl}{d}
\end{verbatim}
produce the following structures: 
\begin{center}
   \fiveunitvi[b]{1==N}{1==H;2==Cl}{d} \qquad
   \fiveunitvi[b]{}{1D==O;2==Cl}{d}
\end{center}

The macro \verb/\fiveunith/ 
is a five-membered fragment of horizontal type that can be fused to another 
ring structure to produce a new ring system. 
\begin{verbatim}
   \fiveunith[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}
\end{verbatim}
% **********************
% * five-membered unit *
% *  (horizontal type) *
% **********************
%
%     3  _____  2
%       |       *
%       |         * 1 <===== the original point
%       |       *
%     4  -----  5
%
\medskip
\noindent
Example:
\begin{verbatim}
   \fiveunith[b]{1==N}{1==H;2==Cl}{d} \qquad
   \fiveunith[b]{}{1D==O;2==Cl}{d}
\end{verbatim}
produce the following structures: 
\begin{center}
   \fiveunith[b]{1==N}{1==H;2==Cl}{d} \qquad
   \fiveunith[b]{}{1D==O;2==Cl}{d}
\end{center}

The macro \verb/\fiveunithi/ is the inverse counterpart 
of \verb/\fiveunith/.  It produces 
a five-membered fragment of another horizontal type 
so that it can be fused to another 
ring structure to produce a new ring system. 
\begin{verbatim}
   \fiveunithi[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}
\end{verbatim}
% ************************************
% * five-membered unit               *
% *  (horizontal type, inverse type) *
% ************************************
%
%                       2  -----  3
%                        *       |
% the original point 1 *         |
%                        *       |
%                           _____|
%                        5        4
%
\medskip
\noindent
Example:
\begin{verbatim}
   \fiveunithi[b]{1==N}{1==H;2==Cl}{d} \qquad
   \fiveunithi[b]{}{1D==O;2==Cl}{d}
\end{verbatim}
produce the following structures: 
\begin{center}
   \fiveunithi[b]{1==N}{1==H;2==Cl}{d} \qquad
   \fiveunithi[b]{}{1D==O;2==Cl}{d}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\section{Setting Locant Numbers}

The \verb/\bdloocant/ prints six characters on the edges of 
a six-membered ring of vertical type (locant.sty). 
\begin{verbatim}
\bdloocant{#1}{#2}{#3}{#4}{#5}{#6}
\end{verbatim}
On the other hand, the \verb/\bdloocnth/ prints 
six characters on the edges of 
a six-membered ring of horizontal type. 
\begin{verbatim}
\bdloocnth{#1}{#2}{#3}{#4}{#5}{#6}
\end{verbatim}

\medskip
\noindent
Example:
\begin{verbatim}
\bdloocant{a}{b}{c}{d}{e}{f} \qquad
\bdloocnth{a}{b}{c}{d}{e}{f}
\end{verbatim}
produce the following structures: 
\begin{center}
\bdloocant{a}{b}{c}{d}{e}{f} \qquad
\bdloocnth{a}{b}{c}{d}{e}{f}
\end{center}

The \verb/\sxloocant/ prints six characters on the vertices of 
a six-membered ring of vertical type. 
\begin{verbatim}
\sxloocant{#1}{#2}{#3}{#4}{#5}{#6}
\end{verbatim}
On the other hand, the \verb/\sxloocnth/ prints 
six characters on the vertices of 
a six-membered ring of horizontal type. 
\begin{verbatim}
\sxloocnth{#1}{#2}{#3}{#4}{#5}{#6}
\end{verbatim}

\medskip
\noindent
Example:
\begin{verbatim}
\sxloocant{1}{2}{3}{4}{5}{6} \qquad
\sxloocnth{1}{2}{3}{4}{5}{6} 
\end{verbatim}
produce the following structures: 
\begin{center}
\sxloocant{1}{2}{3}{4}{5}{6} \qquad
\sxloocnth{1}{2}{3}{4}{5}{6} 
\end{center}

These commands can be used by combining with 
a structure-drawing macro in a picture environment 
to show the locant numbering of the structure. 

\medskip
\noindent
Example:
\begin{verbatim}
\begin{picture}(1000,1000)(0,0)
\put(0,0){\sxloocant{1}{2}{3}{4}{5}{6}}
\put(0,0){\bdloocant{a}{b}{c}{d}{e}{f}}
\put(0,0){\bzdrv[c]{1==OH;2==C(CH$_{3}$)$_{3}$;4==OH}}
\end{picture}
\end{verbatim}
produces the following structure: 
\begin{center}
\begin{picture}(1000,1000)(0,0)
\put(0,0){\sxloocant{1}{2}{3}{4}{5}{6}}
\put(0,0){\bdloocant{a}{b}{c}{d}{e}{f}}
\put(0,0){\bzdrv[c]{1==OH;2==C(CH$_{3}$)$_{3}$;4==OH}}
\end{picture}
\end{center}

\endinput

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%