Abstract

The title compound, C19H17N3O3S (I), was prepared by a [3 + 2]cyclo­addition azide condensation reaction using sodium azide and l-proline as a Lewis base catalyst. N-Methyl­ation of compound (I) using CH3I gave compound (II), C20H19N3O3S. The benzo­thio­phene ring systems in (I) and (II) are almost planar, with r.m.s deviations from the mean plane = 0.0205 (14) in (I) and 0.016 (2) Å in (II). In (I) and (II), the triazole rings make dihedral angles of 32.68 (5) and 10.43 (8)°, respectively, with the mean planes of the benzo­thio­phene ring systems. The trimeth­oxy phenyl rings make dihedral angles with the benzo­thio­phene rings of 38.48 (4) in (I) and 60.43 (5)° in (II). In the crystal of (I), the mol­ecules are linked into chains by N—H⋯O hydrogen bonds with R 2 1(5) ring motifs. After the N-methyl­ation of structure (I), no hydrogen-bonding inter­actions were observed for structure (II). The crystal structure of (II) has a minor component of disorder that corresponds to a 180° flip of the benzo­thio­phene ring system [occupancy ratio 0.9363 (14):0.0637 (14)].

Document Type

Article

Publication Date

11-2014

Notes/Citation Information

Published in Acta Crystallographica Section E Structure Reports Online, v. 70, no. 11, p. 392-395.

Copyright © Penthala et al. 2014

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

Digital Object Identifier (DOI)

http://dx.doi.org/10.1107/S1600536814023095

Funding Information

This investigation was supported by NIH/National Cancer Institute grant R01 CA140409.

Related Content

CCDC references: 1030172, 1030173

Additional supporting information: crystallographic information; 3D view; checkCIF report

e-70-00392-sup1.cif (1928 kB)
Crystal structure: contains datablock(s) global I, II. DOI: 10.1107/S1600536814023095/hg5414sup1.cif

e-70-00392-Isup2.hkl (218 kB)
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023095/hg5414Isup2.hkl

e-70-00392-IIsup3.hkl (224 kB)
Structure factors: contains datablock(s) II. DOI: 10.1107/S1600536814023095/hg5414IIsup3.hkl

e-70-00392-Isup4.cml (7 kB)
Supporting information file. DOI: 10.1107/S1600536814023095/hg5414Isup4.cml

e-70-00392-IIsup5.cml (7 kB)
Supporting information file. DOI: 10.1107/S1600536814023095/hg5414IIsup5.cml

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