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

The macro \verb/\pyridinev/ and the related macros are 
used to draw six-membered heterocyclic compounds 
of vertical type (hetarom.sty).  
Each of these commands typesets heterocycles with the specific 
arrangement of heteroatoms on its skeleton. 
The formats of these commands are as follows: 
\begin{verbatim}
\pyridinev[BONDLIST]{SUBSLIST}
\pyrazinev[BONDLIST]{SUBSLIST}
\pyrimidinev[BONDLIST]{SUBSLIST}
\pyridazinev[BONDLIST]{SUBSLIST}
\triazinev[BONDLIST]{SUBSLIST}
\end{verbatim}
% ************************
% * pyridine derivatives *
% *  (vertical type)     *
% ************************
By using the command \verb/\pyridinev/ as an example, 
the mode of locant numbering 
for designating substitution positions 
is shown as follows along with the bond descriptors 
for assigning inner double bonds: 
\begin{xymspec}
\pyridinev{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)}}
\qquad
\begin{picture}(800,880)(0,0)
\put(0,0){\pyridinev[H]{1Sb==1Sb(l);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)}}
\put(0,0){\sxloocant{{\lower1ex\hbox{1}}}{2}{3}{4}{5}{6}}
\put(0,0){\bdlocant}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

The optional argument BONDLIST specifies bonds to be 
doubled as shown in Table \ref{tt:b1}.  
Since a specific character is assigned 
to a specific bond of each heterocycle, the concrete meaning of 
the character is different from one heterocycle to another. 
However, the methodology is common in drawing all 
heterocycles so that the commands of \XyMTeX{} are easy to use. 
\begin{table}[hpbt]
\caption{Argument BONDLIST for commands {\tt$\backslash$pyridinev}, 
{\em etc.}}
\label{tt:b1}
\begin{center}
\begin{tabular}{ll}
\hline
Character & \multicolumn{1}{c}{Printed structure} \\
\hline
     none or r  &  pyridine (right-handed) \\
     l          &  pyridine (left-handed) \\
     H or [~]    &  fully saturated ring \\
     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  \\
     $\{n+\}$   & plus at the $n$-nitrogen atom ($n$ = 1 to 6) \\
\hline
\end{tabular}
\end{center}
\end{table}

The argument SUBSLIST shows 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}
\pyridinev{2==Cl;6==Cl;4==F}
\pyrazinev{2==Cl;6==Cl}
\pyrimidinev{2==Cl;6==Cl;4==F}
\pyridazinev{6==Cl;4==F}
\triazinev{2==Cl;6==Cl;4==F}
\end{verbatim}
produce the following structures: 
\begin{center}
\pyridinev{2==Cl;6==Cl;4==F}\qquad
\pyrazinev{2==Cl;6==Cl}\qquad
\pyrimidinev{2==Cl;6==Cl;4==F}

\pyridazinev{6==Cl;4==F}\qquad
\triazinev{2==Cl;6==Cl;4==F}
\end{center}

It should be noted that the default setting of the BONDLIST is 
to depict a fully unsaturated ring (usually an aromatic ring). 
By setting an appropriate character string, 
a sigle macro is used to typeset 
both partially saturated and unsaturated derivatives. 
Moreover, a fully saturated ring can be obtained 
by setting a null argument or H in BONDLIST. 
This specification can be illustrated with the following examples. 
\begin{verbatim}
\pyridinev[be]{1==H;2==Cl;6==Cl;4D==O}\qquad
\pyridinev[ce]{1==H;4==Cl;6==Cl;2D==O}\qquad
\triazinev[H]{2D==O;4D==O;6D==O;1==H;3==H;5==H}
\end{verbatim}
produce the following structures: 
\begin{center}
\pyridinev[be]{1==H;2==Cl;6==Cl;4D==O}\qquad
\pyridinev[ce]{1==H;4==Cl;6==Cl;2D==O}\qquad
\triazinev[H]{2D==O;4D==O;6D==O;1==H;3==H;5==H}
\end{center}

In order to depict a charge on a nitrogen, 
you write the statements, for example: 
\begin{verbatim}
\pyridinev[r{1+}]{1==H;2==Cl;6==Cl;4==F}\qquad
\pyrazinev[l{1+}{4+}]{1==H;4==H;2==Cl;6==Cl}
\end{verbatim}
Then you obtain the following structures: 
\begin{center}
\pyridinev[r{1+}]{1==H;2==Cl;6==Cl;4==F}\qquad
\pyrazinev[l{1+}{4+}]{1==H;4==H;2==Cl;6==Cl}
\end{center}
In these cases, a character `r' or `l' should be added to 
the argument BONDLIST, since the defaults are 
hidden by writing other characters in the BONDLIST. 

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\subsection{Commands for General Use}
The command \verb/\sixheterov/ is a general macro used to draw 
six-memered heterocyclic derivatives of vertical type (hetarom.sty). 
It is especially useful to draw heterocyclic compounds 
having other skeletal atoms than nitrogen atoms. 
The format of this command is as follows: 
\begin{verbatim}
   \sixheterov[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% *************************
% * sixhetero derivatives *
% *  (vertical type)      *
% *************************
% The following numbering is adopted in this macro. 
%
%          1
%          * 
%     6  *   *  2
%       |     |
%       |     |
%     5  *   *  3
%          *
%          4 <===== the original point
%
%  
Locant numbers for designating substitution positions 
and characters for bond-description 
are shown in the following diagram: 
\begin{xymspec}
\begin{picture}(800,880)(0,0)
\put(0,0){\sixheterov[H]{1==1;2==2;3==3;4==4;5==5;6==6}%
{1Sb==1Sb(l);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)}}
%\put(0,0){\sxloocant{{\lower1ex\hbox{1}}}{2}{3}{4}{5}{6}}
\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 because of the lack of 
spaces to print otherwise. 

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 specified by the character. 
The bond-specification is rather arbitrary in some cases but 
conforms to chemical conventions as faithfully as possible 
if such conventions are presence (Table \ref{tt:b2}). 
Since the default prints a fully unsaturated form, 
an option argument [H] should be written to typeset a saturated form.
\begin{table}[hpbt]
\caption{Argument BONDLIST for commands {\tt$\backslash$sixheterov} 
and {\tt$\backslash$sixheterovi}} 
\label{tt:b2}
\begin{center}
\begin{tabular}{ll}
\hline
Character & \multicolumn{1}{c}{Printed structure} \\
\hline          
       none or r  &  sixhetero (right-handed) \\
       l          &  sixhetero (left-handed) \\
       H or []    &  fully saturated form \\
       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  \\
       $\{n+\}$   &  plus at the $n$-nitrogen atom ($n$ = 1 to 6) \\
\hline
\end{tabular}
\end{center}
\end{table}

The augument ATOMLIST is a list of heteroatoms, 
{\em e.g.}, 1==N for a nitrogen atom at 1-position. 
It should be emphasized that, in order to typeset a heteroatom 
at a given position, the edges incident to the heteroatom 
are automatically truncated to 
put space for printing the heteroatrom.  
Compare the following examples. 

The argument SUBSLIST for this macro takes a general format, 
in which the modifiers listed in Table \ref{tt:a2} are used. 

\medskip
\noindent
Example:
\begin{verbatim}
\sixheterov[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad
\sixheterov[b]{1==O}{}\qquad
\sixheterov[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad
\sixheterov[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}
\end{verbatim}
produce
\begin{center}
\sixheterov[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad
\sixheterov[b]{1==O}{}\qquad
\sixheterov[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad
\sixheterov[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}
\end{center}

It should be noted that the same compound can be drawn 
in different ways. This fact is obvious because 
all the commands, \verb/\pyridinev/, 
\verb/\pyrazinev/, 
\verb/\pyrimidinev/, 
\verb/\pyridazinev/, and
\verb/\triazinev/, are based on the macro 
\verb/\sixheterov/. 

\medskip
\noindent
Example:
\begin{verbatim}
\pyridinev[H]{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}\qquad 
\raisebox{1.5cm}{\em vs.} \qquad
\sixheterov[H]{1==N}{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$} \par
\bigskip
\pyridinev[be]{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}\qquad 
\raisebox{1.5cm}{\em vs.} \qquad
\sixheterov[be]{1==N}{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}
\end{verbatim}
produce
\begin{center}
\pyridinev[H]{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}\qquad 
\raisebox{1.5cm}{\em vs.} \qquad
\sixheterov[H]{1==N}{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$} \par
\bigskip
\pyridinev[be]{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}\qquad 
\raisebox{1.5cm}{\em vs.} \qquad
\sixheterov[be]{1==N}{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}
\end{center}

The command \verb/\sixheterovi/ is a general macro used to draw 
six-memered heterocyclic derivatives of 
inverse vertical type (hetarom.sty). 
The format of this command is as follows: 
\begin{verbatim}
   \sixheterovi[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% **********************************
% * sixhetero derivatives          *
% *  (vertical type, inverse type) *
% **********************************
% The following numbering is adopted in this macro. 
%
%          4
%          * 
%     5  *   *  3
%       |     |
%       |     |
%     6  *   *  2
%          *
%          1 <===== the original point
%
Locant numbers (1--6) for designating substitution positions 
and bond descriptors (a--f) 
are shown in the following diagram: 
\begin{xymspec}
\begin{picture}(800,880)(0,0)
\put(0,0){\sixheterovi[H]{1==1;2==2;3==3;4==4;5==5;6==6}%
{1Sb==1Sb(l);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)}}
%\put(0,0){\sxloocant{{\lower1ex\hbox{1}}}{2}{3}{4}{5}{6}}
\put(0,0){\bdlocant}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

The following examples are the ones in which 
the \verb/\sixheterov/ commands in the above examples 
are replaced by \verb/\sixheterovi/. 

\medskip
\noindent
Example:
\begin{verbatim}
\sixheterovi[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad
\sixheterovi[b]{1==O}{}\qquad
\sixheterovi[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad
\sixheterovi[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}
\end{verbatim}
produce
\begin{center}
\sixheterovi[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad
\sixheterovi[b]{1==O}{}\qquad
\sixheterovi[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad
\sixheterovi[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}
\end{center}

The commands \verb/\sixheterov/ and \verb/\sixheterovi/ 
can yield the equivalent results if the modes of numbering are altered 
in ATOMLIST and SUBSLIST. 
For example, the following two statements 
\begin{verbatim}
\sixheterov[H]{4==S}{1D==O} \qquad
\sixheterovi[H]{1==S}{4D==O} 
\end{verbatim}
produce the same strucure as follows. 
\begin{center}
\sixheterov[H]{4==S}{1D==O} \qquad
\sixheterovi[H]{1==S}{4D==O} 
\end{center}
However, the latter is preferred to the former 
because the numbering of the ring atoms 
comforms to the chemical nomenclature.  This is the reason why 
we have made such macros of inverse type.

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\section{Drawing Horizontal Forms of Six-Membered Heterocycles}
\subsection{Commands for Specified Use}

The macro \verb/\pyridineh/ and the related macros are 
used to draw six-membered heterocyclic compounds 
of horizontal type (hetaromh.sty). 
The formats of these commands are as follows: 
\begin{verbatim}
\pyridineh[BONDLIST]{SUBSLIST}
\pyrazineh[BONDLIST]{SUBSLIST}
\pyrimidineh[BONDLIST]{SUBSLIST}
\pyridazineh[BONDLIST]{SUBSLIST}
\triazineh[BONDLIST]{SUBSLIST}
\end{verbatim}
% ************************
% * pyridine derivatives *
% *  (horizontal type)   *
% ************************
The following diagrams show the numbering 
for designating substitution positions as well as 
the bond specification for placing double bonds:
\begin{xymspec}
\pyridineh{1==1(l);2==2(lr);3==3(lr);4==4(r);5==5(lr);6==6(lr)}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(800,880)(0,0)
\put(0,0){\pyridineh[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(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 macro can be used to typeset 
both saturated and unsaturated derivatives. 
For example, the statements, 
\begin{verbatim}
\pyridineh{2==Cl;6==Cl;4==F}
\pyrazineh{2==Cl;6==Cl}
\pyrimidineh{2==Cl;6==Cl;4==F}
\pyridazineh{6==Cl;4==F}
\triazineh{2==Cl;6==Cl;4==F}
\end{verbatim}
produce the following structures: 
\begin{center}
\pyridineh{2==Cl;6==Cl;4==F}\qquad
\pyrazineh{2==Cl;6==Cl}\qquad
\pyrimidineh{2==Cl;6==Cl;4==F}

\pyridazineh{6==Cl;4==F}\qquad
\triazineh{2==Cl;6==Cl;4==F}
\end{center}

The macro \verb/\pyridinehi/ and the related macros are 
used to draw six-membered heterocyclic compounds 
of inverse horizontal type (hetarom.sty). 
The formats of these commands are as follows: 
\begin{verbatim}
\pyridinehi[BONDLIST]{SUBSLIST}
\pyrazinehi[BONDLIST]{SUBSLIST}
\pyrimidinehi[BONDLIST]{SUBSLIST}
\pyridazinehi[BONDLIST]{SUBSLIST}
\triazinehi[BONDLIST]{SUBSLIST}
\end{verbatim}
% *********************************
% * pyridine derivatives          *
% *  (horizontal type, inverse)   *
% *********************************
The numbering 
for designating substitution positions
and the bond specification are shown in 
the following diagrams:
\begin{xymspec}
\pyridinehi{1==1(r);2==2(lr);3==3(lr);4==4(l);5==5(lr);6==6(lr)}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(800,880)(0,0)
\put(0,0){\pyridinehi[H]{%
4Sb==4Sb(l);4Sa==4Sa(l);%
3Sb==3Sb(l);3Sa==\lmoiety{3Sa(lr)};2Sb==2Sb(r);2Sa==2Sa(lr);%
1Sb==1Sb(r);1Sa==1Sa(r);6Sb==6Sb(r);6Sa==6Sa(lr);%
5Sb==5Sb(l);5Sa==\lmoiety{5Sa(lr)}}}
%\put(0,0){\sxlocnth}
\put(0,0){\bdloocnth{c}{b}{a}{f}{e}{d}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}
Each macro can typeset both saturated and unsaturated derivatives, where 
the default produces a fully unsaturated (aromatic) one. 
For example, the statements, 
\begin{verbatim}
\pyridinehi{2==Cl;6==Cl;4==F}
\pyrimidinehi{2==Cl;6==Cl;4==F}
\pyridazinehi{6==Cl;4==F}
\triazinehi{2==Cl;6==Cl;4==F}
\end{verbatim}
produce the following structures: 
\begin{center}
\pyridinehi{2==Cl;6==Cl;4==F}\qquad
\pyrimidinehi{2==Cl;6==Cl;4==F}\qquad
\pyridazinehi{6==Cl;4==F}\qquad
\triazinehi{2==Cl;6==Cl;4==F}
\end{center}

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

The macro \verb/\sixheteroh/ is a general user command for drawing 
six-membered heterocycles of horizontal type (hetaromh.sty). 
The format of this command is as follows: 
\begin{verbatim}
   \sixheteroh[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% *************************
% * sixhetero 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 
as well as bond descriptors are shown in the following diagram: 
\begin{xymspec}
\begin{picture}(800,880)(0,0)
\put(0,0){\sixheteroh[H]{1==1;2==2;3==3;4==4;5==5;6==6}%
{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\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:b2}, respectivey. 

\medskip
\noindent
Example:
\begin{verbatim}
\sixheteroh[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad
\sixheteroh[b]{1==O}{}\qquad
\sixheteroh[H]{3==O;5==O}{4D==O;6B==CH$_{2}$I;2B==CH$_{3}$}\qquad
\sixheteroh[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}
\end{verbatim}
produce 
\begin{center}
\sixheteroh[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad
\sixheteroh[b]{1==O}{}\qquad
\sixheteroh[H]{3==O;5==O}{4D==O;6B==CH$_{2}$I;2B==CH$_{3}$}\qquad
\sixheteroh[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}
\end{center}

The macro \verb/\sixheterohi/ is used to draw 
six-membered hetrocycles of inverse horizontal type (hetaromh.sty). 
The format of this command is as follows: 
\begin{verbatim}
   \sixheterohi[BONDLIST]{ATOMLIST}{SUBSLIST}          
\end{verbatim}
% **********************************
% * sixhetero derivatives          *
% *  (horizontal type, inverse)    *
% **********************************
% The following numbering is adopted in this macro. 
%
%                                2      3
%                                 -----
%                               *       *
%   the original point ===> 1 *           * 4
%          (0,0)                *       *
%                                 -----
%                                6      5
The following diagram shows 
locant numbers (1--6) for designating substitution positions 
along with bond descriptors (a--f) for setting double bonds.  
\begin{xymspec}
\begin{picture}(800,880)(0,0)
\put(0,0){\sixheterohi[H]{1==1;2==2;3==3;4==4;5==5;6==6}%
{4Sb==4Sb(l);4Sa==4Sa(l);%
3Sb==3Sb(l);3Sa==\lmoiety{3Sa(lr)};2Sb==2Sb(r);2Sa==2Sa(lr);%
1Sb==1Sb(r);1Sa==1Sa(r);6Sb==6Sb(r);6Sa==6Sa(lr);%
5Sb==5Sb(l);5Sa==\lmoiety{5Sa(lr)}}}
%\put(0,0){\sxlocnth}
\put(0,0){\bdloocnth{c}{b}{a}{f}{e}{d}}
\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 Table \ref{tt:b2}, respectivey. 

\medskip
\noindent
Example:
\begin{verbatim}
\sixheterohi[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad
\sixheterohi[b]{1==O}{}\qquad
\sixheterohi[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad
\sixheterohi[H]{3==S;5==S}{4Sa==Me$_{3}$Si;4Sb==Li}
\end{verbatim}
produce 
\begin{center}
\sixheterohi[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad
\sixheterohi[b]{1==O}{}\qquad
\sixheterohi[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad
\sixheterohi[H]{3==S;5==S}{4Sa==Me$_{3}$Si;4Sb==Li}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\chapter{Five- or Lower-Membered Heterocycles}
\section{Drawing Vertical Forms of Five-Membered Heterocycles}
\subsection{Commands for Specified Use}

The macro \verb/\pyrrolev/ and the related macros 
typeset five-membered heterocyclic compounds 
of vertical type (hetarom.sty). 
The formats of these commands are as follows: 
\begin{verbatim}
   \pyrrolev[BONDLIST]{SUBSLIST}
   \pyrazolev[BONDLIST]{SUBSLIST}
   \imidazolev[BONDLIST]{SUBSLIST}
   \isoxazolev[BONDLIST]{SUBSLIST}
   \oxazolev[BONDLIST]{SUBSLIST}
\end{verbatim}
% ***********************************
% * pyrrole derivatives  and others *
% *  (vertical type)                *
% ***********************************
The following diagrams show the numbering 
for designating substitution positions as well as 
the bond specification for writing double bonds:
\begin{xymspec}
\pyrrolev{1==1(lr);2==2(r);3==3(r);4==4(l);5==5(l)}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(800,880)(0,0)
\put(0,0){\pyrrolev[H]{1Sb==1Sb(l);1Sa==1Sa(r);%
2Sb==2Sb(r);2Sa==2Sa(r);3Sb==3Sb(r);3Sa==3Sa(r);%
4Sb==4Sb(l);4Sa==4Sa(l);5Sb==5Sb(l);5Sa==5Sa(l)}}%
\put(0,0){\sxloocant{}{3}{2}{{\raise1ex\hbox{1}}}{5}{4}}
\put(0,0){\bdloocant{{\kern-10pt\lower1ex\hbox{c}}}{b}{a}{d}{e}{}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

Each of the macros is capable of typesetting 
both saturated and unsaturated derivatives. 
The optional argument BONDLIST specifies bond to be doubled 
as shown in Table \ref{tt:b3}. 
The default setting is to produce a fully unsaturated ring; 
on the other hand a null augument or H in BONDLIST produces 
a fully saturated ring. 
\begin{table}[hpbt]
\caption{Argument BONDLIST for commands {\tt$\backslash$pyrrolev}, 
{\em etc.}}
\label{tt:b3}
\begin{center}
\begin{tabular}{ll}
\hline
Character & \multicolumn{1}{c}{Printed structure} \\
\hline
     none       &  mother nucleus \\
     H or [~]   &  fully saturated form \\
     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 \\
     A          &  aromatic circle  \\
     $\{n+\}$   &  plus at the $n$-nitrogen atom ($n$ = 1 to 5) \\
\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 5. 
For example, the statements, 
\begin{verbatim}
\pyrrolev{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad
\pyrazolev{1==H;3==Ph;5==Ph}\qquad
\imidazolev{1==H;2==CH$_{3}$}

\isoxazolev{3==CH$_{3}$}\qquad
\oxazolev{2==CH$_{3}$}
\end{verbatim}
produce the following structures: 
\begin{center}
\pyrrolev{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad
\pyrazolev{1==H;3==Ph;5==Ph}\qquad
\imidazolev{1==H;2==CH$_{3}$}

\isoxazolev{3==CH$_{3}$}\qquad
\oxazolev{2==CH$_{3}$}
\end{center}

The macro \verb/\pyrrolevi/ and the related macros are 
used to draw five-membered heterocyclic compounds 
of inverse vertical type (hetarom.sty). 
The formats of these commands are as follows: 
\begin{verbatim}
   \pyrrolevi[BONDLIST]{SUBSLIST}
   \pyrazolevi[BONDLIST]{SUBSLIST}
   \imidazolevi[BONDLIST]{SUBSLIST}
   \isoxazolevi[BONDLIST]{SUBSLIST}
   \oxazolevi[BONDLIST]{SUBSLIST}
\end{verbatim}
% ***********************************
% * pyrrole derivatives  and others *
% *  (vertical type, inverse)       *
% ***********************************
The locant numbering  and the bond specification 
are shown in the following diagrams. 
\begin{xymspec}
\pyrrolevi{1==1(lr);2==2(r);3==3(r);4==4(l);5==5(l)}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(800,880)(0,0)
\put(0,0){\pyrrolevi[H]{1Sb==1Sb(l);1Sa==1Sa(r);%
2Sb==2Sb(r);2Sa==2Sa(r);3Sb==3Sb(r);3Sa==3Sa(r);%
4Sb==4Sb(l);4Sa==4Sa(l);5Sb==5Sb(l);5Sa==5Sa(l)}}%
\put(0,0){\sxloocant{{\lower1ex\hbox{1}}}{2}{3}{}{4}{5}}
\put(0,0){\bdloocant{a}{b}{{\kern-10pt\raise1ex\hbox{c}}}{}{d}{e}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

The arguments BONDLIST and SUBSLIST have the same 
formats as above (Tables \ref{tt:b3} and \ref{tt:a2}). 

\medskip
\noindent
Example:
\begin{verbatim}
\pyrrolevi{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad
\pyrazolevi{1==H;3==Ph;5==Ph}\qquad
\imidazolevi{1==H;2==CH$_{3}$}\par
\isoxazolevi{3==CH$_{3}$}\qquad
\oxazolevi{2==CH$_{3}$}
\end{verbatim}
produce the following structures: 
\begin{center}
\pyrrolevi{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad
\pyrazolevi{1==H;3==Ph;5==Ph}\qquad
\imidazolevi{1==H;2==CH$_{3}$}\par
\isoxazolevi{3==CH$_{3}$}\qquad
\oxazolevi{2==CH$_{3}$}
\end{center}

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

The command \verb/\fiveheterov/ is a general macro used to draw 
five-memered heterocyclic derivatives of vertical type (hetarom.sty). 
The format of this command is as follows: 
\begin{verbatim}
   \fiveheterov[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% **************************
% * fivehetero derivatives *
% *  (vertical type)       *
% **************************
% The following numbering is adopted in this macro. 
%
%     4  _____  3
%       |     |
%       |     |
%     5  *   *  2
%          *
%          1 <===== the original point
%
Locant numbers for designating substitution positions 
and bond descriptors for setting double bonds 
are represented by the following diagram: 
\begin{xymspec}
\begin{picture}(800,880)(0,0)
\put(0,0){\fiveheterov[H]{1==1;2==2;3==3;4==4;5==5;6==6}%
{1Sb==1Sb(l);1Sa==1Sa(r);%
2Sb==2Sb(r);2Sa==2Sa(r);3Sb==3Sb(r);3Sa==3Sa(r);%
4Sb==4Sb(l);4Sa==4Sa(l);5Sb==5Sb(l);5Sa==5Sa(l)}}%
%\put(0,0){\sxloocant{}{3}{2}{{\raise1ex\hbox{1}}}{5}{4}}
\put(0,0){\bdloocant{{\kern-10pt\lower1ex\hbox{c}}}{b}{a}{e}{d}{}}
\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 a character string 
in a pair of brackets, where each character 
indicates the presence of a double bond 
at the edge specified by the character (Table \ref{tt:b4}). 
\begin{table}[hpbt]
\caption{Argument BONDLIST for commands {\tt$\backslash$fiveheterov} 
and {\tt$\backslash$fiveheterovi}} 
\label{tt:b4}
\begin{center}
\begin{tabular}{ll}
\hline
Character & \multicolumn{1}{c}{Printed structure} \\
\hline          
       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 \\
       A          &  aromatic circle  \\
       $\{n+\}$   &  plus at the $n$-nitrogen atom ($n$ = 1 to 6) \\
       $\{0+\}$   &  plus (or minus) at the center \\
\hline
\end{tabular}
\end{center}
\end{table}

Since the default of BONDLIST prints a fully saturated form, 
the \verb/\fiveheterov/ requires no option argument [H] 
in contrast to \verb/\sixheterov/. 

The argument SUBSLIST for this macro takes a general format, 
in which the modifiers listed in Table \ref{tt:a2} are used. 

\medskip
\noindent
Example:
\begin{verbatim}
\fiveheterov{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad
\fiveheterov[b]{1==O}{}\qquad
\fiveheterov{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad
\fiveheterov{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}
\end{verbatim}
produce
\begin{center}
\fiveheterov{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad
\fiveheterov[b]{1==O}{}\qquad
\fiveheterov{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad
\fiveheterov{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}
\end{center}

The macro \verb/\fiveheterovi/ is employed 
to draw five-membered heterocyclic compounds 
of inverse vertical type (hetarom.sty). 
The format of this command is as follows: 
\begin{verbatim}
   \fiveheterovi[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% *****************************
% * fivehetero derivatives    *
% *  (vertical type, inverse) *
% *****************************
% The following numbering is adopted in this macro. 
%
%          1
%          * 
%     6  *   *  2
%       |     |
%       |_____|
%     4         3
%          *
%        (0,0) <===== the original point
%
The following diagram shows the numbering 
for designating substitution positions:
\begin{xymspec}
\begin{picture}(800,880)(0,0)
\put(0,0){\fiveheterovi[H]{1==1;2==2;3==3;4==4;5==5;6==6}%
{1Sb==1Sb(l);1Sa==1Sa(r);%
2Sb==2Sb(r);2Sa==2Sa(r);3Sb==3Sb(r);3Sa==3Sa(r);%
4Sb==4Sb(l);4Sa==4Sa(l);5Sb==5Sb(l);5Sa==5Sa(l)}}%
%\put(0,0){\sxloocant{{\lower1ex\hbox{1}}}{2}{3}{}{4}{5}}
\put(0,0){\bdloocant{a}{b}{{\kern-10pt\raise1ex\hbox{c}}}{}{d}{e}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

The optional argument BONDLIST specifies double bonds 
as shown in Table \ref{tt:b4}, where any combination of 
characters (a--d) enables us to draw 
both saturated and unsaturated derivatives. 

The argument SUBSLIST specifies 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 5. 

\medskip
\noindent
Example:
\begin{verbatim}
\fiveheterovi{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad
\fiveheterovi[b]{1==O}{}\qquad
\fiveheterovi{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad
\fiveheterovi{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}
\end{verbatim}
produce
\begin{center}
\fiveheterovi{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad
\fiveheterovi[b]{1==O}{}\qquad
\fiveheterovi{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad
\fiveheterovi{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\section{Drawing Horizontal Forms of Five-Membered Heterocycles}
\subsection{Commands for Specified Use}

The macro \verb/\pyrroleh/ and the related macros are 
used to draw five-membered heterocyclic compounds 
of horizontal type (hetaromh.sty). 
The formats of these commands are as follows: 
\begin{verbatim}
   \pyrroleh[BONDLIST]{SUBSLIST}
   \pyrazoleh[BONDLIST]{SUBSLIST}
   \imidazoleh[BONDLIST]{SUBSLIST}
   \isoxazoleh[BONDLIST]{SUBSLIST}
   \oxazoleh[BONDLIST]{SUBSLIST}
\end{verbatim}
% ***********************************
% * pyrrole derivatives  and others *
% *  (horizontal type)              *
% ***********************************
%
The following diagrams show the numbering 
for designating substitution positions: 
\begin{xymspec}
\pyrroleh{1==1(r);2==2(r);3==3(lr);4==4(lr);5==5(r)}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(800,880)(0,0)
\put(0,0){\pyrroleh[H]{1Sb==1Sb(r);1Sa==1Sa(r);%
2Sb==2Sb(r);2Sa==2Sa(lr);3Sa==\lmoiety{3Sa(lr)};3Sb==3Sb(l);%
4Sb==4Sb(l);4Sa==\lmoiety{4Sa(lr)};5Sb==5Sb(r);5Sa==5Sa(lr)}}
%\put(0,0){\sxloocnth}
\put(0,0){\bdloocnth{{\lower10pt\hbox{c}\kern-.8em}}{b}{a}{e}{d}{}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

For BONDLIST, see Table \ref{tt:b4}.  
For example, the statements, 
\begin{verbatim}
\pyrroleh{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad
\pyrazoleh{1==H;3==Ph;5==Ph}\qquad
\imidazoleh{1==H;2==CH$_{3}$} \par
\isoxazoleh{3==CH$_{3}$}\qquad
\oxazoleh{2==CH$_{3}$}
\end{verbatim}
produce the following structures: 
\begin{center}
\pyrroleh{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad
\pyrazoleh{1==H;3==Ph;5==Ph}\qquad
\imidazoleh{1==H;2==CH$_{3}$} \par
\isoxazoleh{3==CH$_{3}$}\qquad
\oxazoleh{2==CH$_{3}$}
\end{center}

The macro \verb/\pyrrolehi/ and the related macros are 
used to draw five-membered heterocyclic compounds 
of inverse horizontal type (hetaromh.sty). 
The format of this command is as follows: 
\begin{verbatim}
   \pyrrolehi[BONDLIST]{SUBSLIST}
   \pyrazolehi[BONDLIST]{SUBSLIST}
   \imidazolehi[BONDLIST]{SUBSLIST}
   \isoxazolehi[BONDLIST]{SUBSLIST}
   \oxazolehi[BONDLIST]{SUBSLIST}
\end{verbatim}
% *************************************
% * pyrrole derivatives  and others   *
% *  (horizontal type, inverse)       *
% *************************************
%
The locant numbering for designating substitution positions and 
the bond specification for setting double bonds are shown in 
the following diagram: 
\begin{xymspec}
\pyrrolehi{1==1(l);2==2(lr);3==3(r);4==4(r);5==5(lr)}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(800,880)(0,0)
\put(0,0){\pyrrolehi[H]{%
4Sb==4Sb(r);4Sa==4Sa(r);%
3Sb==3Sb(r);3Sa==3Sa(r);2Sb==2Sb(l);2Sa==\lmoiety{2Sa(lr)};%
1Sb==1Sb(l);1Sa==1Sa(l);5Sb==5Sb(l);5Sa==\lmoiety{5Sa(lr)}}}%
%\put(0,0){\sxlocnth}
\put(0,0){\bdloocnth{a}{b}{{\kern-.5em\lower10pt\hbox{c}}}{}{d}{e}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

For example, the statements, 
\begin{verbatim}
\pyrrolehi{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad
\pyrazolehi{1==H;3==Ph;5==Ph}\qquad
\imidazolehi{1==H;2==CH$_{3}$}\par
\isoxazolehi{3==CH$_{3}$}\qquad
\oxazolehi{2==CH$_{3}$}
\end{verbatim}
produce the following structures: 
\begin{center}
\pyrrolehi{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad
\pyrazolehi{1==H;3==Ph;5==Ph}\qquad
\imidazolehi{1==H;2==CH$_{3}$}\par
\isoxazolehi{3==CH$_{3}$}\qquad
\oxazolehi{2==CH$_{3}$}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\subsection{Commands for General Use}
The command \verb/\fiveheteroh/ is a general macro used to draw 
five-memered heterocyclic derivatives of horizontal type (hetaromh.sty). 
The format of this command is as follows: 
\begin{verbatim}
   \fiveheteroh[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% ****************************
% * fivehetero derivatives   *
% *  (horizontal type)       *
% ****************************
% The following numbering is adopted in this macro. 
%
%     3  _____  2
%       |       *
%       |         * 1 <===== the original point
%       |       *
%     4  -----  5
%
%  
The locant numbers for designating substitution positions 
are represented by the following diagram: 
\begin{xymspec}
\begin{picture}(800,880)(0,0)
\put(0,0){\fiveheteroh{1==1;2==2;3==3;4==4;5==5}%
{1Sb==1Sb(r);1Sa==1Sa(r);%
2Sb==2Sb(r);2Sa==2Sa(lr);3Sa==\lmoiety{3Sa(lr)};3Sb==3Sb(l);%
4Sb==4Sb(l);4Sa==\lmoiety{4Sa(lr)};5Sb==5Sb(r);5Sa==5Sa(lr)}}
%\put(0,0){\sxloocnth}
\put(0,0){\bdloocnth{{\lower10pt\hbox{c}\kern-.8em}}{b}{a}{e}{d}{}}
\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 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 (Table \ref{tt:b4}). 
The argument ATOMLIST lists a set of atoms placed on the 
edges assigned. 
The argument SUBSLIST for this macro takes a general format, 
in which the modifiers listed in Table \ref{tt:a2} are used. 

\medskip
\noindent
Example:
\begin{verbatim}
\fiveheteroh{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad
\fiveheteroh[b]{1==O}{}\qquad
\fiveheteroh{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad
\fiveheteroh{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}
\end{verbatim}
produce
\begin{center}
\fiveheteroh{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad
\fiveheteroh[b]{1==O}{}\qquad
\fiveheteroh{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad
\fiveheteroh{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}
\end{center}

The command \verb/\fiveheterohi/ is a general macro for drawing 
five-memered heterocyclic derivatives of 
inverse horizontal type (hetaromh.sty). 
The format of this command is as follows: 
\begin{verbatim}
   \fiveheterohi[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% *******************************
% * fivehetero derivatives      *
% *  (horizontal type, inverse) *
% *******************************
% The following numbering is adopted in this macro. 
%
%                       2  -----  3
%                        *       |
% the original point 1 *         |
%                        *       |
%                           _____|
%                        5        4
%
The following diagram shows the numbering 
for designating substitution positions as well as 
the bond specification for writing double bonds:
\begin{xymspec}
\begin{picture}(800,880)(0,0)
\put(0,0){\fiveheterohi{1==1;2==2;3==3;4==4;5==5}%
{4Sb==4Sb(r);4Sa==4Sa(r);%
3Sb==3Sb(r);3Sa==3Sa(r);2Sb==2Sb(l);2Sa==\lmoiety{2Sa(lr)};%
1Sb==1Sb(l);1Sa==1Sa(l);5Sb==5Sb(l);5Sa==\lmoiety{5Sa(lr)}}}%
%\put(0,0){\sxlocnth}
\put(0,0){\bdloocnth{a}{b}{{\kern-.5em\lower10pt\hbox{c}}}{}{d}{e}}
\end{picture}
\qquad\fbox{\parbox{2cm}{$\circ$: (\the\shifti,\the\shiftii) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\end{xymspec}

\noindent
Example:
\begin{verbatim}
\fiveheterohi{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad
\fiveheterohi[b]{1==O}{}\qquad
\fiveheterohi{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad
\fiveheterohi{2==S;5==S}{1Sa==Me$_{3}$Si;1Sb==Li}
\end{verbatim}
produce the following structures: 
\begin{center}
\fiveheterohi{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad
\fiveheterohi[b]{1==O}{}\qquad
\fiveheterohi{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad
\fiveheterohi{2==S;5==S}{1Sa==Me$_{3}$Si;1Sb==Li}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\section{Drawing Four-Membered Heterocycles}

The macro \verb/\fourhetero/ is a command for general use, 
which is capable of giving skeletal atoms as an ATOMLIST. 
This macro is designed for drawing four-membered heterocycles 
by using the following format (hetarom.sty). 
\begin{verbatim}
   \fourhetero[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
% **************************
% * fourhetero derivatives *
% *  (vertical type)       *
% **************************
% The following numbering is adopted in this macro. 
%
%          c
%     4  _____  3
%    d  |     |  b
%       |     |
%     1  -----  2<===== the original point
%          a
%
%  
The locant numbering is common in these commands as 
shown in the following diagram:
\begin{xymspec}
\fourhetero{1==1;2==2;3==3;4==4}{1==1(l);2==2(r);3==3(r);4==4(l)}
\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(1000,1000)(0,0)
\put(0,0){\fourhetero[H]{1==1;2==2;3==3;4==4}{%
1Sb==1Sb(l);1Sa==1Sa(l);2Sb==2Sb(r);2Sa==2Sa(r);%
3Sb==3Sb(r);3Sa==3Sa(r);4Sb==4Sb(l);4Sa==4Sa(l)}}
\put(0,0){\circle{80}}
\put(400,240){\circle{80}}
\put(500,480){c}
\put(500,180){a}
\put(640,320){b}
\put(330,320){d}
\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 for the bond specification 
shown in Table \ref{tt:f4}.
\begin{table}[hpbt]
\caption{Argument BONDLIST for commands {\tt$\backslash$fourhetero} 
and others}
\label{tt:f4}
\begin{center}
\begin{tabular}{ll|ll}
\hline
Character & \multicolumn{1}{c|}{Printed structure} &
Character & \multicolumn{1}{c}{Printed structure} \\
\hline
  none & mother compound (fully saturated) & & \\
     a    &  1,2-double bond     & b    &  2,3-double bond \\
     c    &  3,4-double bond    & d    &  4,1-double bond \\
 $\{n+\}$   &  
    \multicolumn{2}{l}{plus at the $n$-nitrogen atom ($n$ = 1 to 4)} 
            & \\
\hline
\end{tabular}
\end{center}
\end{table}

The argument ATOMLIST takes a usual format with respect to 
heteroatoms attached to $n$ = 1 to 4, {\em e.g.}, 
1==N for a nitrogen atom at 1-position.  

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 4. 

\medskip
\noindent
Example:
\begin{verbatim}
   \fourhetero{1==N}{1==H}
   \fourhetero{1==O}{3Sa==COOH;3Sb==COOH}
   \fourhetero{1==O;2==O}{3Sa==COOH;3Sb==COOH}
\end{verbatim}
produce the following structures: 
\begin{center}
   \fourhetero{1==N}{1==H}
   \fourhetero{1==O}{3Sa==COOH;3Sb==COOH}
   \fourhetero{1==O;2==O}{3Sa==COOH;3Sb==COOH}
\end{center}

%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%%
\section{Drawing Three-Membered Heterocycles}

The macro \verb/\threehetero/ for drawing threee-membered heterocycles 
has the following format (hetarom.sty). 
\begin{verbatim}
   \threehetero[BONDLIST]{ATOMLIST}{SUBSLIST}
\end{verbatim}
%
% ****************************
% * thereehetero derivatives *
% *  (vertical type)         *
% ****************************
% The following numbering is adopted in this macro. 
%
%         b
%     3--------2
%    c `     / a
%        `1/ <===== the original point
%
%
The locant numbering is common as 
shown in the following diagram:
\begin{xymspec}
\threehetero{1==1;2==2;3==3}{1==1(lr);2==2(r);3==3(l)}
\fbox{\parbox{2cm}{$\circ$: (\the\shiftii,\the\shifti) \\
                   $\bullet$: (\the\noshift,\the\noshift)}}
\qquad
\begin{picture}(1000,1000)(0,0)
\put(0,0){\threehetero[H]{1==1;2==2;3==3}{%
1Sb==1Sb(l);1Sa==1Sa(r);2Sb==2Sb(r);2Sa==2Sa(r);%
3Sb==3Sb(l);3Sa==3Sa(l)}}
\put(0,0){\circle{80}}
\put(400,240){\circle{80}}
\put(500,250){a}
\put(300,250){c}
\put(380,460){b}
\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 double bonds 
as shown in Table \ref{tt:f5}.
\begin{table}[hpbt]
\caption{Argument BONDLIST for commands {\tt$\backslash$threehetero} 
and others}
\label{tt:f5}
\begin{center}
\begin{tabular}{ll}
\hline
Character & \multicolumn{1}{c}{Printed structure} \\
\hline
      none       &  saturated \\
      a          &  1,2-double bond\\
      b          &  2,3-double bond\\
      c          &  3,1-double bond\\
      A          &  aromatic circle \\
      $\{n+\}$   &  plus at the n-hetero atom (n = 1 to 3)\\
                 &  $n=4$ -- outer plus at 1 position\\
                 &  $n=5$ -- outer plus at 2 position\\
                 &  $n=6$ -- outer plus at 3 position\\
      $\{0+\}$   &  plus at the center of a cyclopropane ring\\
\hline
\end{tabular}
\end{center}
\end{table}

The argument ATOMLIST takes a usual format with respect to 
heteroatoms attached to $n$ = 1 to 3, {\em e.g.}, 
1==N for a nitrogen atom at 1-position.  

The argument SUBSLIST describes 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 3. 

\medskip
\noindent
Example:
\begin{verbatim}
   \threehetero{1==N}{1==H;2Sa==COOCH$_{3}$;2Sb==COOCH$_{3}$}\qquad
   \threehetero{1==O}{2Sa==COOH;2Sb==COOH}\qquad\qquad
   \threehetero{1==S}{3Sa==H$_{3}$C;3Sb==H$_{3}$C}
\end{verbatim}
produce the following structures: 
\begin{center}
   \threehetero{1==N}{1==H;2Sa==COOCH$_{3}$;2Sb==COOCH$_{3}$}\qquad
   \threehetero{1==O}{2Sa==COOH;2Sb==COOH}\qquad\qquad
   \threehetero{1==S}{3Sa==H$_{3}$C;3Sb==H$_{3}$C}
\end{center}

%