N-(3-Chlorophenyl)benzamide

The conformation of the N—H bond in the structure of the title compound (N3CPBA), C13H10ClNO, is anti to the meta chloro substituent in the aniline benzene ring, similar to that observed with respect to the ortho chloro substituent in N-(2-chlorophenyl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichlorophenyl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to both the ortho and the meta chloro substituents in N-(2,3-dichlorophenyl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenylbenzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group –NHCO– makes a dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings is 61.0 (1)°. The molecules are linked into chains along the b axis by N—H⋯O hydrogen bonds.

The conformation of the N-H bond in the structure of the title compound (N3CPBA), C 13 H 10 ClNO, is anti to the meta chloro substituent in the aniline benzene ring, similar to that observed with respect to the ortho chloro substituent in N-(2chlorophenyl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichlorophenyl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to both the ortho and the meta chloro substituents in N-(2,3dichlorophenyl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenylbenzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group -NHCO-makes a dihedral angle of 18.2 (2) with the benzoyl ring, while the dihedral angle between the two benzene rings is 61.0 (1) . The molecules are linked into chains along the b axis by N-HÁ Á ÁO hydrogen bonds.

Comment
In the present work, the structure of N-(3-chlorophenyl)-benzamide (N3CPBA) has been determined to explore the effect of substituents on the structure of N-aromatic amides (Gowda et al., 2003;. The conformation of the N-H bond in the structure of N3CPBA( Fig.1) is anti to the meta chloro substituent in the aniline phenyl ring, similar to that observed with respect to the ortho-chloro sub-  and meta-chloro substituent in N-(3,4-dichlorophenyl)-benzamide (N34DCPBA) , but in contrast to the syn conformation observed with respect to both the ortho & meta-Chloro substituents in N-(2,3-dichlorophenyl)-benzamide (N23DCPBA) . The bond parameters in N3CPBA are similar to those in N-(phenyl)benzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group -NHCO-has the dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 61.0 (1)°.
One-dimensional chains of the title compound along the base vector [0 1 0] formed by hydrogen bonds N1-H1N···O1 (Table   1) as viewed down the a axis is shown in Fig.2.

Experimental
The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Refinement
H atoms bonded to C atoms were placed in geometrically calculated positions and subsequently treated as riding with C-H bond distance 0.93 Å. H(N) atom was visible in the difference map. In refinement the N-H distance was restrained to 0.86 (4) Å. The U iso (H) values were set at 1.2 U eq (C,N).  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.  (9) 0.0005 (7) 0.0040 (7) −0.0044 (7)  C9 0.0392 (9) 0.0500 (9) 0.0520 (9)