2-Chloro-N-(2,3-dichloro­phen­yl)benzamide

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

doi:10.1107/S1600536808018679

. 2008 Jun 25;64(Pt 7):o1342. doi: 10.1107/S1600536808018679

2-Chloro-N-(2,3-dichlorophenyl)benzamide

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

PMCID: PMC2961795 PMID: 21202964

Abstract

Two independent molecules comprise the asymmetric unit in the title compound, C₁₃H₈Cl₃NO, each with the amide N—H and C=O bonds trans to each other. The molecules are linked into chains through intermolecular N—H⋯O and N—H⋯Cl hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₃H₈Cl₃NO
M _r = 300.55
Monoclinic,
a = 12.310 (1) Å
b = 7.8307 (6) Å
c = 14.407 (2) Å
β = 111.52 (1)°
V = 1292.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 299 (2) K
0.75 × 0.75 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.624, T _max = 0.885
5882 measured reflections
3936 independent reflections
3430 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.104
S = 1.14
3936 reflections
326 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: (Flack, 1983 ▶), 365 Friedel pairs
Flack parameter: 0.12 (5)

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/S1600536808018679/tk2277sup1.cif

e-64-o1342-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018679/tk2277Isup2.hkl

e-64-o1342-Isup2.hkl^{(192.9KB, 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⋯O2	0.86	2.16	2.850 (3)	137
N1—H1N⋯Cl3	0.86	2.64	3.114 (3)	116
N2—H2N⋯O1ⁱ	0.86	2.05	2.896 (3)	167

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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-(2,3-dichlorophenyl)- benzamide (I, N23DCP2CBA) has been determined to explore the effect of substituents on the structures of benzanilides (Gowda et al., 2003; 2007; 2008). The amide N—H and C=O bonds in each of the two molecules comprising the crystallographic asymmetric unit are trans to each other (Fig. 1), similar to that observed in 2-chloro-N-(phenyl)-benzamide (NP2CBA) (Gowda et al., 2003), 2-chloro-N-(2-chlorophenyl)-benzamide (N2CP2CBA) (Gowda et al., 2007), and 2-chloro-N-(3-chlorophenyl)-benzamide (N3CP2CBA) (Gowda et al., 2008). In one of the molecules, the conformation of the N—H bond is syn to both the ortho and meta-chloro groups in the aniline ring and of the C=O bond group is also syn to the ortho-chloro group in the benzoyl ring. By contrast, the conformations of these bonds in the second independent molecule are intermediate between syn and anti to the respective groups. The above conformations are in contrast to the syn conformations of both the amide N—H and C=O bonds, with respect to the ortho-chloro groups in the benzoyl and aniline rings, respectively, observed in N2CP2CBA (Gowda et al., 2007). Further, in N3CP2CBA, the conformation of the C=O bond is syn to the ortho-chloro group of the benzoyl ring, while the N—H bond is anti to the meta-chloro group of the aniline ring (Gowda et al., 2008). The –NHCO– group makes the dihedral angles of 42.24 (14)° (molecule 1), 48.89 (12)° (molecule 2), and 35.31 (19)° (molecule 1), 41.88 (13)° (molecule 2) with the benzoyl and aniline rings, respectively. The benzoyl and aniline rings form the dihedral angles of 12.30 (10)° (molecule 1) and 7.25 (9)°) (molecule 2). In the crystal structure of (I), the molecules are linked by intermolecular N—H···O and N—H···Cl hydrogen bonds (Table 1) forming chains running along the a axis, as shown in Fig. 2.

Experimental

Compound (I) was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was confirmed by melting point, and IR and NMR spectra. Single crystals were obtained from an ethanolic solution of (I)