Open Access11‐Methyl‐2,3‐benzodipyrrin‐1‐one
Author(s) -
Bonnett Raymond,
Motevalli Majid,
Swanson Fiona J.,
Vallés María Asunción
Publication year - 2004
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270104026708
Subject(s) - orthorhombic crystal system , ring (chemistry) , benzene , molecule , intermolecular force , chemistry , hydrogen bond , alkane stereochemistry , stereochemistry , crystallography , condensation , crystal structure , organic chemistry , physics , thermodynamics
The title compound {alternative names: 11‐methyl‐2,3‐benzopyrromethenone and 3‐[(1‐methylpyrrol‐2‐yl)methylidene]‐2,3‐dihydro‐1 H ‐isoindol‐1‐one}, C 14 H 12 N 2 O, was prepared by the base‐catalysed condensation of phthalimidine with 2‐formyl‐1‐methylpyrrole; yellow orthorhombic crystals, space group Pbca , were obtained from ethanol. The molecule is almost planar, having Z (−)antiperiplanar geometry. The molecules are arranged in pairs with intermolecular hydrogen bonding between lactam functions. Comparison with literature values for polyalkyldipyrrin‐1‐ones shows that, apart from the local constraints of the benzene ring, the fused benzo ring has little effect on the molecular dimensions of the dipyrrin‐1‐one skeleton.