Diethyl {3-[β-(2,4-dichlorophenyl)vinyl]-N-(phenylsulfonyl)indol-2-ylmethyl}phosphonate and diethyl {3-[β-(4-bromophenyl)vinyl]-N-(phenylsulfonyl)indol-2-ylmethyl}phosphonate

Abstract

The title compounds, C(27)H(26)Cl(2)NO(5)PS, (I), and C(27)H(27)BrNO(5)PS, (II), respectively, crystallize in the centrosymmetric space group P2(1)/n with one molecule in the asymmetric unit in each case. The dihedral angle between the benzene and pyrrole rings is 2.1 (1) degrees in (I) and 0.9 (2) degrees in (II). The phenylsulfonyl group is orthogonal to the halophenyl moiety, with a dihedral angle of 82.0 (1) degrees in (I) and 78.7 (2) degrees in (II). In both compounds, the molecular structures and packing are stabilized by C-H...O and C-H...halogen interactions. The intermolecular hydrogen bonds in (I) form cyclic dimers with graph-set descriptors R(2)(1)(10) and R(2)(2)(8) about a 2(1) axis, and those in (II) form a C(2)(2)(20) chain.

Diethyl [(3-cyano-1-phenylsulfonyl-1H-indol-2-yl)methyl]phosphonate

“…This would appear to be a real effect caused by the fusion of the smaller pyrrole ring to the six-membered benzene ring and the strain is taken up by the angular distortion rather than by bond-length distortions (Allen, 1981;Sethu Sankar et al, 2002).…”

“…For comparison of molecular dimensions, see: Bassindale (1984); Sethu Sankar et al (2002); Allen (1981). For graph-set motif notations, see: Bernstein et al (1995).…”