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( E )‐1‐[(5‐Chloro‐3‐methyl‐1‐phenyl‐1 H ‐pyrazol‐4‐yl)methylidene]‐2‐phenylhydrazine: sheets built from π‐stacked hydrogen‐bonded chains
Author(s) -
Trilleras Jorge,
Utria Michael,
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/s2053229614000680
Subject(s) - phenylhydrazine , ring (chemistry) , pyrazole , stacking , hydrogen bond , chemistry , molecule , nucleophilic substitution , medicinal chemistry , stereochemistry , crystallography , organic chemistry
The reaction between 5‐chloro‐3‐methyl‐1‐phenyl‐1 H ‐pyrazole‐4‐carbaldehyde and phenylhydrazine proceeds via condensation to provide the title compound, C 17 H 15 ClN 4 , (I), rather than via the alternative routes of simple nucleophilic substitution or cyclocondensation. With the exception of the phenyl group bonded directly to the pyrazole ring, the non‐H atoms of (I) are nearly coplanar, with an r.m.s. deviation of 0.058 Å. The molecules are linked into C (7) chains by a single N—H...N hydrogen bond, and the chains are linked by π–π stacking interactions to form sheets.