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2‐Ethyl‐1‐[5‐(4‐methylphenyl)pyrazol‐3‐yl]‐3‐(thiophene‐2‐carbonyl)isothiourea: molecular ribbons containing three types of hydrogen‐bonded ring
Author(s) -
Castro Edison,
Insuasty Henry,
Insuasty Braulio,
Cobo Justo,
Glidewell Christopher
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s205322961402244x
Subject(s) - thiophene , hydrogen bond , intramolecular force , chemistry , molecule , pyrazole , crystallography , aromaticity , ring (chemistry) , delocalized electron , solvent , stacking , stereochemistry , organic chemistry
The title compound, C 18 H 18 N 4 OS 2 , was prepared by reaction of S , S ‐diethyl 2‐thenoylimidodithiocarbonate with 5‐amino‐3‐(4‐methylphenyl)‐1 H ‐pyrazole using microwave irradiation under solvent‐free conditions. In the molecule, the thiophene unit is disordered over two sets of atomic sites, with occupancies of 0.814 (4) and 0.186 (4), and the bonded distances provide evidence for polarization in the acylthiourea fragment and for aromatic type delocalization in the pyrazole ring. An intramolecular N—H...O hydrogen bond is present, forming an S (6) motif, and molecules are linked by N—H...O and N—H...N hydrogen bonds to form a ribbon in which centrosymmetric R 2 2 (4) rings, built from N—H...O hydrogen bonds and flanked by inversion‐related pairs of S (6) rings, alternate with centrosymmetric R 2 2 (6) rings built from N—H...N hydrogen bonds.