Open AccessHydrogen‐bonded chains of rings in methyl 4‐[(5‐methyl‐1 H ‐pyrazol‐3‐yl)amino]‐3‐nitrobenzoate and hydrogen‐bonded sheets in methyl 1‐(5‐methyl‐1 H ‐pyrazol‐3‐yl)‐1 H ‐benzimidazole‐5‐carboxylate
Author(s) -
Portilla Jaime,
Mata Ernesto G.,
Nogueras Manuel,
Cobo Justo,
Low John N.,
Glidewell Christopher
Publication year - 2007
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270106044611
Subject(s) - hydrogen bond , molecule , chemistry , methyl group , ring (chemistry) , benzimidazole , stereochemistry , hydrogen , medicinal chemistry , crystallography , group (periodic table) , organic chemistry
Molecules of methyl 4‐[(5‐methyl‐1 H ‐pyrazol‐3‐yl)amino]‐3‐nitrobenzoate, C 12 H 12 N 4 O 4 , (I), exhibit a polarized (charge‐separated) structure in the nitroaniline portion. The molecules are linked into chains of edge‐fused R 2 2 (16) and R 2 2 (22) rings by a combination of N—H⋯O(carbonyl) and C—H⋯O(nitro) hydrogen bonds. Methyl 1‐(5‐methyl‐1 H ‐pyrazol‐3‐yl)‐1 H ‐benzimidazole‐5‐carboxylate, C 13 H 12 N 4 O 2 , (II), which is readily formed from (I) by reduction followed by ring formation, crystallizes with Z ′ = 2 in the space group P . Each of the two independent molecular types is linked into sheets of R 4 4 (28) rings by a combination of N—H⋯N and C—H⋯O(carbonyl) hydrogen bonds.