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Two methyl 3‐(1H‐pyrazol‐4‐yl)octahydropyrrolo[3,4‐c]pyrrole‐1‐carboxylates form different hydrogen‐bonded sheets

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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.
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Document Type: Research Article

Publication date: August 15, 2013

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