title: Hydrogen-bonded chains of rings in methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate and hydrogen-bonded sheets in methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate.
abstract: Molecules of methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate, C12H12N4O4, (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-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate, C13H12N4O2, (II), which is readily formed from (I) by reduction followed by ring formation, crystallizes with Z' = 2 in the space group P-1. 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.
authors.affiliation: Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.
authors.forename: Jaime
authors.initials: J
authors.lastname: Portilla
authors.forename: Ernesto G
authors.initials: EG
authors.lastname: Mata
authors.forename: Manuel
authors.initials: M
authors.lastname: Nogueras
authors.forename: Justo
authors.initials: J
authors.lastname: Cobo
authors.forename: John N
authors.initials: JN
authors.lastname: Low
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D001562:Benzimidazoles / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D009579:Nitrobenzoates / Q000737:chemistry*; D011720:Pyrazoles / Q000737:chemistry*
chemical_list: D001562:Benzimidazoles; D002264:Carboxylic Acids; D009579:Nitrobenzoates; D011720:Pyrazoles; C518423:methyl 1-(5-methyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate; C518422:methyl 4-((5-methyl-1H-pyrazol-3-yl)amino)-3-nitrobenzoate