T. Emge, Matthew J. Clements, D. Myers
Apr 1, 2003
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Journal
Acta Crystallographica Section E-structure Reports Online
Abstract
The bromopyrrole moiety of (5-bromopyrrol-3-yl)cyclohexylmethanone, (I), is quite similar to other halopyrroles in the literature (Allen et al., 1983). Notable among these are: oroidin (Walker et al., 1981), pyrrolomycin B (Kaneda et al., 1981), axinohydantoin (Pettit et al., 1990), 2-bromoaldisin (Xu et al., 2001), 2-cyano-4,5-dibromopyrrole (Konig et al., 1998), 5,50-dibromo-3,30-diethyl-4,40-dimethyl-2,20-pyrromethene (Becker et al., 1978), and ethyl 4,7-ethano-3-iodo-5,6-dihydro2H-isoindole-1-carboxylate (Uno et al., 2000). The distances and angles of (I) are as expected (Allen et al., 1983), including the relatively long distance of 1.434 (1) AÊ for the CÐC bond opposite to the NÐH group within the pyrrole ring, and the relatively short NÐC distances of 1.357 (2) and 1.368 (2) AÊ . The latter NÐC distances compare well with those of the substituted pyrroles in 2-bromoaldisin, axinohydantoin, pyrrolomycin B, and ethyl 4,7-ethano-3-iodo-5,6-dihydro-2Hisoindole-1-carboxylate. On the other hand, for the dibromoand bromo-ethyl-methyl-substituted pyrroles of 2-cyano-4,5dibromopyrrole and 5,50-dibromo-3,30-diethyl-4,40-dimethyl2,20-pyrromethene, respectively, the NÐC bond of the HÐ NÐCÐBr moiety is the shortest in the ring by about 0.03 AÊ . These inequalities demonstrate that the magnitude and symmetrical disposition of bonds in the pyrrole ring are expected to be quite sensitive to the electronic and chemical properties of substituents on the ring.