N-(2-Chlorophenyl)-N′-(2-methylphenyl)succinamide

B S Saraswathi,B Thimme Gowda,Sabine Foro

doi:10.1107/s1600536811035616

B S Saraswathi, B Thimme Gowda + Show 1 more

Open Access

https://doi.org/10.1107/s1600536811035616

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Abstract

In the title compound, C17H17ClN2O2, the asymmetric unit contains half a molecule with a centre of symmetry at the mid-point of the central C—C bond. The conformations of the amide O atoms are anti to the methylene atoms. Further, the N—H bonds in the amide fragments are anti to the ortho-chloro/methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH—C(O)—CH2 segment in the two halves of the molecule is 62.0 (2)°. In the crystal, a series of N—H⋯O intermolecular hydrogen bonds link the molecules into column-like infinite chains along the a axis. The methyl and Cl groups are disordered with respect to the ortho positions of the benzene ring, with site-occupation factors of 0.5 each.

Highlights

In the title compound, C17H17ClN2O2, the asymmetric unit contains half a molecule with a centre of symmetry at the midpoint of the central C—C bond
The conformations of the amide O atoms are anti to the methylene atoms
A series of N—H O intermolecular hydrogen bonds link the molecules into column-like infinite chains along the a axis

Summary

CCD detector

Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.009 Å; disorder in main residue; R factor = 0.105; wR factor = 0.164; data-to-parameter ratio = 12.4. C17H17ClN2O2, the asymmetric unit contains half a molecule with a centre of symmetry at the midpoint of the central C—C bond. The conformations of the amide O atoms are anti to the methylene atoms. N—H bonds in the amide fragments are anti to the orthochloro/methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH—. A series of N—H O intermolecular hydrogen bonds link the molecules into column-like infinite chains along the a axis. The methyl and Cl groups are disordered with respect to the ortho positions of the benzene ring, with site-occupation factors of 0.5 each

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Crystal data

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