N-(3-Chlorophenyl)-2-methylbenzamide

B Thimme Gowda,B P Sowmya,Sabine Foro,Hartmut Fuess

doi:10.1107/s1600536808010143

B Thimme Gowda, B P Sowmya + Show 2 more

Open Access

https://doi.org/10.1107/s1600536808010143

Copy DOI

Abstract

The conformation of the N—H bond in the structure of the title compound, C14H12ClNO, is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring. The conformations of the N—H and C=O bonds are anti to each other, similar to those observed in 2-methyl-N-(3-methylphenyl)benzamide (N3MP2MBA). The –NHC(=O)– group makes a dihedral angle of 55.8 (7)° with the benzoyl ring, while the angle between the benzoyl and aniline rings is 37.5 (1)°; the respective values for N3MP2MBA are 55.2 (7) and 36.2 (1)°. N—H⋯O hydrogen bonds link the molecules into infinite chains running along the c axis.

Highlights

The conformation of the N—H bond in the structure of the title compound, C14H12ClNO, is anti to the meta-chloro substituent in the aniline ring, while the C O bond is syn to the ortho-methyl substituent in the benzoyl ring
The conformations of the N—H and C O bonds are anti to each other, similar to those observed in 2-methyl-N-(3-methylphenyl)benzamide (N3MP2MBA)
N—H O hydrogen bonds link the molecules into infinite chains running along the c axis

Summary

Data collection

P. Sowmyaa and Hartmut Fuessb a Department of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany. The conformation of the N—H bond in the structure of the title compound, C14H12ClNO, is anti to the meta-chloro substituent in the aniline ring, while the C O bond is syn to the ortho-methyl substituent in the benzoyl ring. The conformations of the N—H and C O bonds are anti to each other, similar to those observed in 2-methyl-N-(3-methylphenyl)benzamide (N3MP2MBA). Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Related literature

Cu K radiation

Special details