Three closely related 4,5,6,7-tetra\-hydro-1\it H-pyrazolo\-4,3-{\it c}pyridines: synthesis, mol{\-}ecular conformations and hydrogen bonding in zero, one and two dimensions

Sagar, B. K. and Harsha, K. B. and Yathirajan, H. S. and Rangappa, K. S. and Rathore, Ravindranath S. and Glidewell, Christopher (2017) Three closely related 4,5,6,7-tetra\-hydro-1\it H-pyrazolo\-4,3-{\it c}pyridines: synthesis, mol{\-}ecular conformations and hydrogen bonding in zero, one and two dimensions. Acta Crystallographica Section C, 73 (3). pp. 298-304. ISSN 2053-2296

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Abstract

In each of 1-(4-fluoro\-phen\-yl)-5-methyl\-sulfonyl-3-4-(tri{\-}fluoro{\-}meth{\-}yl)phen{\-}yl-4,5,6,7-tetra{\-}hydro-1{\it H}-pyrazolo{\-}4,3-{\it c}pyridine, C${\sb 21}$H${\sb 19}$F${\sb 4}$N${\sb 3}$O${\sb 2}$S, (I), 1-(4-chloro{\-}phen{\-}yl)-5-methyl{\-}sulfonyl-3-4-(tri{\-}fluoro{\-}meth{\-}yl)phen{\-}yl-4,5,6,7-tetra{\-}hydro-1{\it H}-pyrazolo{\-}4,3-{\it c}pyridine, C${\sb 21}$H${\sb 19}$ClF${\sb 3}$N${\sb 3}$O${\sb 2}$S, (II), and 1-(3-methyl{\-}phen{\-}yl)-5-methyl{\-}sulfonyl-3-4-(tri{\-}fluoro{\-}meth{\-}yl)phen{\-}yl-4,5,6,7-tetra{\-}hydro-1{\it H}-pyrazolo4,3-{\it c}pyridine, C${\sb 22}$H${\sb 22}$F${\sb 3}$N${\sb 3}$O${\sb 2}$S, (III), the reduced pyridine ring adopts a half-chair conformation with the methyl{\-}sulfonyl substituent occupying an equatorial site. Although compounds (I) and (II) are not isostructural, having the space groups {\it Pbca} and {\it P}2${\sb 1}$2${\sb 1}$2${\sb 1}$, respectively, their mol{\-}ecular conformations are very similar, but the conformation of compound (III) differs from those of (I) and (II) in the relative orientation of the {\it N}-benzyl and methyl{\-}sulfonyl substituents. In compounds (II) and (III), but not in (I), the tri{\-}fluoro{\-}methyl groups are disordered over two sets of atomic sites. Mol{\-}ecules of (I) are linked into centrosymmetric dimers by C{---}H{$\cdots$}{$\pi$}(arene) hydrogen bonds, molecules of (II) are linked by two C{---}H{$\cdots$}O hydrogen bonds to form ribbons of {\it R}${\sb 3}$${\sp 3}$(18) rings, which are themselves further linked by a C{---}Cl{$\cdots$}{$\pi$}(arene) inter{\-}action, and a combination of C{---}H{$\cdots$}O and C{---}H{$\cdots$}{$\pi$}(arene) hydrogen bonds links the mol{\-}ecules of (III) into sheets. Comparisons are made with the structures of some related compounds.

Item Type:	Article
Uncontrolled Keywords:	synthesis, heterocyclic compounds, crystal structure, molecular structure, molecular conformation, pyrazolo4,3-cpyridine, hydrogen bonding, C-H...pi(arene) interactions, C-Cl...pi(arene) interactions
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	C Swapna Library Assistant
Date Deposited:	13 Jun 2019 10:53
Last Modified:	13 Jun 2019 10:53
URI:	http://eprints.uni-mysore.ac.in/id/eprint/3017

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