N-(2,6-Dichloro­phen­yl)benzamide

B Thimme Gowda; Miroslav Tokarčík; Jozef Kožíšek; B P Sowmya; Hartmut Fuess

doi:10.1107/S160053680800305X

. 2008 Jan 30;64(Pt 2):o540. doi: 10.1107/S160053680800305X

N-(2,6-Dichlorophenyl)benzamide

B Thimme Gowda ^a,^*, Miroslav Tokarčík ^b, Jozef Kožíšek ^b, B P Sowmya ^a, Hartmut Fuess ^c

PMCID: PMC2960174 PMID: 21201559

Abstract

The conformation of the N—H and C=O bonds in the structure of the title compound (N26DCPBA), C₁₃H₉Cl₂NO, are anti to each other, similar to that observed in N-phenylbenzamide (NPBA), N-(2-chlorophenyl)benzamide (N2CPBA), N-(2,3-dichlorophenyl)benzamide (N23DCPBA) and other benzanilides. The asymmetric unit of N26DCPBA contains two molecules. The bond parameters in N26DCPBA are similar to those in NPBA, N2CPBA, N23DCPBA and other benzanilides. The amide group, –NHCO–, makes a dihedral angle of 30.8 (1)° with the benzoyl ring in the first molecule and 35.1 (2)° in the second molecule of the asymmetric unit. The dihedral angle between the two benzene rings (benzoyl and aniline) is 56.8 (1)° in the first molecule and 59.1 (1)° in the second molecule. N—H⋯O hydrogen bonds give rise to infinite chains running along the a axis of the crystal structure.

Related literature

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

Experimental

Crystal data

C₁₃H₉Cl₂NO
M _r = 266.11
Monoclinic,
a = 10.0431 (2) Å
b = 13.7150 (3) Å
c = 18.4585 (4) Å
β = 93.623 (2)°
V = 2537.41 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 295 (2) K
0.26 × 0.24 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer
Absorption correction: analytical [(Oxford Diffraction, 2007 ▶); analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995 ▶)] T _min = 0.882, T _max = 0.904
54956 measured reflections
4956 independent reflections
3810 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.127
S = 1.10
4956 reflections
314 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97], PLATON (Spek, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800305X/om2209sup1.cif

e-64-0o540-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800305X/om2209Isup2.hkl

e-64-0o540-Isup2.hkl^{(237.8KB, 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	0.860 (19)	2.09 (2)	2.9035 (18)	158 (2)
N2—H2N⋯O1ⁱ	0.843 (18)	2.060 (19)	2.8831 (18)	165.1 (19)

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Symmetry code: (i) Inline graphic .

Acknowledgments

MT and JK thank the Grant Agency of the Slovak Republic (Grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

supplementary crystallographic information

Comment

In the present work, the structure of N-(2,6-dichlorophenyl)-benzamide (N26DCPBA) has been determined to explore the effect of substituents on the structure of N-aromatic amides (Gowda et al., 2003,2007a,b,c,2008). The conformation of the N—H and C=O bonds in the structure of N26DCPBA (Fig.1) are anti to each other, similar to that observed in N-(phenyl)-benzamide (NPBA)(Gowda et al., 2003), N-(2-chlorophenyl)-benzamide (N2CPBA), N-(2,3-dichlorophenyl)-benzamide (N23DCPBA) and other benzanilides(Gowda et al., 2007a,b,c, 2008). The title compound crystallizes in the space group P21/c, with two molecules in the asymmetric unit. The bond parameters in N26DCPBA are similar to those in NPBA, N2CPBA, N23DCPBA and other benzanilides. The amide group –NHCO– has the dihedral angle of 30.8 (1)° with the benzoyl ring in the first molecule and 35.1 (2)° in the second molecule of the asymmetric unit. The dihedral angle between the two benzene rings (benzoyl and aniline) is 56.8 (1)° in the first molecule and 59.1 (1)° in the second molecule. One-dimensional chains of N26DCPBA along the base vector [1 0 0] formed by hydrogen bonds N1–H1N···O2(i) and N2–H2N···O1 (Table 1) as viewed down the b axis is shown in Fig.2. Symmetry code (i): x + 1,y,z.

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.