Crystal Structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole

Authors

Narsimha Reddy Penthala, University of Arkansas for Medical Sciences
Jaishankar K. B. Yadlapalli, University of Arkansas for Medical Sciences
Sean Parkin, University of KentuckyFollow
Peter A. Crooks, University of Arkansas for Medical Sciences

Abstract

(Z)-5-[2-(Benzo[b]thio­phen-2-yl)-1-(3,5-di­meth­oxy­phen­yl)ethen­yl]-1H-tetrazole methanol monosolvate, C₁₉H₁₆N₄O₂S·CH₃OH, (I), was prepared by the reaction of (Z)-3-(benzo[b]thio­phen-2-yl)-2-(3,5-di­meth­oxy­phen­yl)acrylo­nitrile with tri­butyl­tin azide via a [3 + 2]cyclo­addition azide condensation reaction. The structurally related compound (Z)-5-[2-(benzo[b]thio­phen-3-yl)-1-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]-1H-tetra­zole, C₂₀H₁₈N₄O₃S, (II), was prepared by the reaction of (Z)-3-(benzo[b]thio­phen-3-yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­nitrile with tri­butyl­tin azide. Crystals of (I) have two mol­ecules in the asymmetric unit (Z′ = 2), whereas crystals of (II) have Z′ = 1. The benzo­thio­phene rings in (I) and (II) are almost planar, with r.m.s deviations from the mean plane of 0.0084 and 0.0037 Å in (I) and 0.0084 Å in (II). The tetra­zole rings of (I) and (II) make dihedral angles with the mean planes of the benzo­thio­phene rings of 88.81 (13) and 88.92 (13)° in (I), and 60.94 (6)° in (II). The di­meth­oxy­phenyl and tri­meth­oxy­phenyl rings make dihedral angles with the benzo­thio­phene rings of 23.91 (8) and 24.99 (8)° in (I) and 84.47 (3)° in (II). In both structures, mol­ecules are linked into hydrogen-bonded chains. In (I), these chains involve both tetra­zole and methanol, and are parallel to the b axis. In (II), mol­ecules are linked into chains parallel to the a axis by N—H⋯N hydrogen bonds between adjacent tetra­zole rings.

Document Type

Article

Publication Date

5-2016

Notes/Citation Information

Published in Acta Crystallographica Section E: Crystallographic Communications, v. 72, part 5, p. 652-655.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Digital Object Identifier (DOI)

https://doi.org/10.1107/S2056989016005600

Funding Information

The authors gratefully acknowledge the Arkansas Research Alliance for financial support, the UAMS sub award to PNR and SA from NIA Claude Pepper Center grant P30-AG028718 (J. Wei, P.I.) and the NIH/National Institute of General Medical Sciences (P20GM109005) for a COBRE award.

Related Content

Supporting information: this article has supporting information at journals.iucr.org/d.

CCDC references: 1472235; 1472234

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S2056989016005600/hg5472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016005600/hg5472Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S2056989016005600/hg5472IIsup3.hkl

checkCIF report

3D view of crystallographic information

Repository Citation

Penthala, Narsimha Reddy; Yadlapalli, Jaishankar K. B.; Parkin, Sean; and Crooks, Peter A., "Crystal Structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole" (2016). Chemistry Faculty Publications. 80.
https://uknowledge.uky.edu/chemistry_facpub/80