2-Chloro-N-(3,5-dimethyl­phen­yl)benzamide

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

doi:10.1107/S1600536809001706

. 2009 Feb 4;65(Pt 3):o444. doi: 10.1107/S1600536809001706

2-Chloro-N-(3,5-dimethylphenyl)benzamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, B P Sowmya ^a, Hartmut Fuess ^b

PMCID: PMC2968629 PMID: 21582117

Abstract

In the structure of the the title compound, C₁₅H₁₄ClNO, the N—H and C=O bonds are trans to each other and the amide O atom is anti to the ortho-Cl atom in the benzoyl ring. The amide group makes dihedral angles of 61.2 (6) and 42.2 (8)° with the benzoyl and aniline rings, respectively. In the crystal, the molecules are linked into infinite chains by N—H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Gowda et al. (2003 ▶). For structure of the 3,5-dichlorophenyl analog and other benzanilides, see: Gowda et al. (2008a ▶,b ▶).

Experimental

Crystal data

C₁₅H₁₄ClNO
M _r = 259.72
Orthorhombic,
a = 9.1867 (6) Å
b = 13.9710 (8) Å
c = 10.2711 (7) Å
V = 1318.27 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 100 (2) K
0.48 × 0.28 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.879, T _max = 0.965
6034 measured reflections
2136 independent reflections
1977 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.083
S = 1.03
2136 reflections
187 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ▶), 712 Friedel pairs
Flack parameter: 0.01 (7)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001706/ng2536sup1.cif

e-65-0o444-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001706/ng2536Isup2.hkl

e-65-0o444-Isup2.hkl^{(105.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.831 (17)	2.120 (18)	2.918 (2)	161 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

In the present work, the structure of 2-chloro-N-(3,5-dimethylphenyl)- benzamide (N35DMP2CBA) has been determined to explore the substituent effects on the solid state structures of benzanilides (Gowda et al., 2003, 2008a,b). The conformations of N—H and C=O bonds in the amide group of N35DMP2CBA are trans to each other (Fig.1), similar to that observed in 2-chloro-N-(3,5-dichlorophenyl)-benzamide(N35DCP2CBA) (Gowda et al., 2008a), 2-chloro-N-(phenyl)-benzamide (NP2CBA) (Gowda et al., 2003) and other benzanilides (Gowda et al., 2008b). Further, the conformation of the amide oxygen in N35DMP2CBA is anti to the ortho-chloro group in the benzoyl ring similar to that observed in N35DCP2CBA but in contrast to the syn conformation observed in NP2CBA. The amide group –NHCO– makes the dihedral angles of 61.2 (6)° and 42.2 (8)° with the benzoyl and aniline rings, respectively, while the benzoyl and aniline rings form the dihedral angle of 76.7 (1)°), compared to the corresponding values of 63.1 (12)°, 31.1 (17)° and 32.1 (2)°) in N35DCP2CBA. Part of the crystal structure of the title compound with infinite molecular chains running along the a axis is shown in Fig. 2. The chains are generated by N—H···O hydrogen bonds (Table 1)

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.