3-Chloro-N-(3-chloro­phen­yl)benzamide

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

doi:10.1107/S1600536808012099

. 2008 Apr 30;64(Pt 5):o949. doi: 10.1107/S1600536808012099

3-Chloro-N-(3-chlorophenyl)benzamide

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

PMCID: PMC2961234 PMID: 21202429

Abstract

In the crystal structure of the title compound, C₁₃H₉Cl₂NO, the N—H and C=O bonds are anti to each other in the two independent molecules. In one molecule, the N—H bond is syn to the meta-chloro group of the attached ring; it is anti in the other molecule. This relationship is also observed between the C=O bond and the meta-chloro substituent of its attached ring. The amide –NHCO– group makes dihedral angles of 31.5 (4) and 34.7 (3)° with the aniline rings; it makes dihedral angles of 37.4 (3) and 37.2 (3)° with the benzoyl rings. The two rings are nearly coplanar, with dihedral angles of 9.1 (2) and 7.3 (3)° in the two independent molecules. Adjacent molecules are linked into infinite chains through N—H⋯O hydrogen bonds.

Related literature

For background literature, see: Gowda et al. (2003 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M _r = 266.11
Monoclinic,
a = 8.577 (1) Å
b = 13.551 (1) Å
c = 10.357 (1) Å
β = 93.04 (1)°
V = 1202.1 (2) Å³
Z = 4
Cu Kα radiation
μ = 4.70 mm⁻¹
T = 296 (2) K
0.60 × 0.28 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.265, T _max = 0.341
3088 measured reflections
2249 independent reflections
2165 reflections with I > 2˘I)
R _int = 0.022
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.131
S = 1.10
2249 reflections
308 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.49 e Å⁻³
Absolute structure: Flack (1983 ▶), no Friedel pairs
Flack parameter: 0.07 (2)

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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012099/ng2449sup1.cif

e-64-0o949-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012099/ng2449Isup2.hkl

e-64-0o949-Isup2.hkl^{(110.5KB, 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⋯O2ⁱ	0.86	2.05	2.877 (4)	162
N2—H2n⋯O1	0.86	2.06	2.884 (5)	161

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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

As part of a study of the substituent effects on the structures of N-aromatic amides,in the present work, the structure of 3-Chloro-N-(3-chlorophenyl)- benzamide(N3CP3CBA) has been determined(Gowda et al., 2003; 2007, 2008). In the structure of N3CP3CBA (Fig. 1),the conformations of the N—H and C=O bonds are anti to each other. The asymmetric unit of the structure contains two molecules. In one of the molecules, the conformation of the N—H bond is syn to the meta-chloro group in the aniline ring and anti to each other in the other molecule. Similar conformations were observed between the C=O bond and meta-chloro substituent in the benzoyl ring. This is in contrast to the single molecule observed in the asymmetric unit of 2-chloro-N-(2-Chlorophenyl)-benzamide (N2CP2CBA) and syn conformation of the N—H bond to the ortho-chloro substituent in the aniline ring and the C=O bond to the ortho-chloro substituent in the benzoyl ring (Gowda et al., 2007). The bond parameters in N3CP3CBA are similar to those in N-(3-chlorophenyl)-benzamide, N2CP2CBA and other benzanilides (Gowda et al., 2003; 2008). The amide group,-NHCO– makes the dihedral angles of 31.5 (4), 37.4 (3)° (molecule 1) and 34.7 (3), 37.2 (3)° (molecule 2) with the aniline and benzoyl rings, respectively, while those between the benzoyl and aniline rings are 9.1 (2)° and 7.3 (3)° in the molecules 1 and 2, respectively. The packing diagram of N3CP3CBA molecules showing the hydrogen bonds N1—H1N···O2 and N2—H2N···O1 (Table 1) involved in the formation of molecular chains is given 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.