title: Two methyl 3-(1H-pyrazol-4-yl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylates form different hydrogen-bonded sheets.
abstract: In the molecules of both methyl (1RS,3SR,3aRS,6aSR)-1-methyl-3-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate, C₂₅H₂₄N₄O₄, (I), and methyl (1RS,3SR,3aRS,6aSR)-5-(4-chlorophenyl)-1-methyl-3-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate, C₂₅H₂₃ClN₄O₄, (II), the two rings of the pyrrolopyrrole fragment are both nonplanar, with conformations close to half-chair forms. The overall conformations of the molecules of (I) and (II) are very similar, apart from the orientation of the ester function. The molecules of (I) are linked into sheets by a combination of an N-H∙∙∙π(pyrrole) hydrogen bond and three independent C-H∙∙∙O hydrogen bonds. The molecules of (II) are also linked into sheets, which are generated by a combination of an N-H∙∙∙N hydrogen bond and two independent C-H∙∙∙O hydrogen bonds, weakly augmented by a C-H∙∙∙π(arene) hydrogen bond.
authors.affiliation: Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.
authors.forename: Jairo
authors.initials: J
authors.lastname: Quiroga
authors.forename: Jaime
authors.initials: J
authors.lastname: Gálvez
authors.forename: Justo
authors.initials: J
authors.lastname: Cobo
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D013058:Mass Spectrometry; D008958:Models, Molecular; D008968:Molecular Conformation; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D011720:Pyrazoles; D011758:Pyrroles
keywords: crystal structure; hydrogen bonding; pyrazole derivatives; pyrrolopyrrole derivatives; supramolecular assemblies