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

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808018102

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1300

doi:10.1107/S1600536808018102

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

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

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 13 June 2008; accepted 14 June 2008; online 19 June 2008)

In the structure of the the title compound, C₁₃H₉Cl₂NO, the N—H and C=O groups are mutually trans. Furthermore, the conformation of the C=O group is syn to the ortho-chloro group in the benzoyl ring, while the N—H bond is anti to the meta-chloro group in the aniline ring. The amide group forms dihedral angles of 89.11 (19) and 22.58 (37)°, respectively, with the benzoyl and aniline rings, while the benzoyl and aniline rings form a dihedral angle of 69.74 (14)°. The molecules are linked into infinite chains through intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ); Gowda, Foro et al. (2008 ); Gowda, Tokarčík et al. (2008 ).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M_r = 266.11
Orthorhombic, P c a 2₁
a = 11.430 (1) Å
b = 12.209 (2) Å
c = 8.878 (1) Å
V = 1238.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 299 (2) K
0.48 × 0.18 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.794, T_max = 0.980
4926 measured reflections
1746 independent reflections
1248 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.139
S = 1.15
1746 reflections
154 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ), 387 Friedel pairs
Flack parameter: 0.02 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.06	2.880 (5)	159
Symmetry code: (i) $[-x+{\script{3\over 2}}, y, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018102/tk2274sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018102/tk2274Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-chloro-N-(3-chlorophenyl)-benzamide (I) has been determined to explore the effect of substituents on the structures of benzanilides (Gowda et al., 2003; Gowda, Foro et al., 2008; Gowda, Tokarčík et al., 2008). The N—H and C=O bonds are trans to each other, Fig. 1, similar to that observed in N-(3-chlorophenyl)-benzamide (N3CPBA) (Gowda, Tokarčík et al., 2008), 2-chloro-N-(phenyl)-benzamide (NP2CBA) (Gowda et al., 2003), 2-methyl-N-(3-chlorophenyl)-benzamide (N3CP2MBA) (Gowda, Foro et al., 2008), and other benzanilides. Further, the conformation of the C=O group is syn to the ortho-chloro group in the benzoyl ring, while the N—H bond is anti to the meta-chloro group in the aniline ring, similar to that observed in N3CP2MBA (Gowda, Foro et al., 2008). The amide group forms dihedral angles of 89.11 (19)° and 22.58 (37)° with the benzoyl and aniline rings, respectively, while the benzoyl and aniline rings form a dihedral angle of 69.74 (14)°. These compare with the corresponding values of 55.8 (7)°, 18.6 (12)° and 37.5 (1)°, respectively, in N3CP2MBA. In the crystal structure of (I), the molecules are linked by N—H···O hydrogen bonds (Table 1) forming chains running along the c axis, Fig. 2.

Related literature top

For related literature, see: Gowda et al. (2003); Gowda, Foro et al. (2008); Gowda, Tokarčík et al. (2008).

Experimental top

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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

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

Crystal data top

C₁₃H₉Cl₂NO	F(000) = 544
M_r = 266.11	D_x = 1.427 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1634 reflections
a = 11.430 (1) Å	θ = 2.4–27.7°
b = 12.209 (2) Å	µ = 0.51 mm⁻¹
c = 8.878 (1) Å	T = 299 K
V = 1238.9 (3) Å³	Plate, colourless
Z = 4	0.48 × 0.18 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1746 independent reflections
Radiation source: fine-focus sealed tube	1248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −14→7
T_min = 0.794, T_max = 0.980	k = −9→15
4926 measured reflections	l = −11→4

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.0797P)² + 0.0826P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.002
1746 reflections	Δρ_max = 0.39 e Å⁻³
154 parameters	Δρ_min = −0.42 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 387 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (13)

Crystal data top

C₁₃H₉Cl₂NO	V = 1238.9 (3) Å³
M_r = 266.11	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 11.430 (1) Å	µ = 0.51 mm⁻¹
b = 12.209 (2) Å	T = 299 K
c = 8.878 (1) Å	0.48 × 0.18 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1746 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1248 reflections with I > 2σ(I)
T_min = 0.794, T_max = 0.980	R_int = 0.022
4926 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.139	Δρ_max = 0.39 e Å⁻³
S = 1.15	Δρ_min = −0.42 e Å⁻³
1746 reflections	Absolute structure: Flack (1983), 387 Friedel pairs
154 parameters	Absolute structure parameter: 0.02 (13)
1 restraint

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.75422 (12)	0.62626 (9)	−0.0970 (2)	0.0776 (5)
Cl2	0.49999 (15)	0.21361 (13)	0.3455 (3)	0.1038 (7)
O1	0.6539 (3)	0.2242 (3)	−0.0041 (3)	0.0597 (8)
N1	0.7788 (3)	0.2603 (3)	0.1873 (4)	0.0499 (9)
H1N	0.8049	0.2334	0.2702	0.060*
C1	0.8275 (3)	0.3614 (3)	0.1443 (5)	0.0437 (9)
C2	0.7719 (3)	0.4339 (3)	0.0469 (5)	0.0433 (9)
H2	0.7012	0.4159	0.0014	0.052*
C3	0.8252 (4)	0.5339 (3)	0.0200 (5)	0.0481 (10)
C4	0.9300 (4)	0.5626 (4)	0.0814 (5)	0.0559 (12)
H4	0.9638	0.6301	0.0602	0.067*
C5	0.9845 (4)	0.4894 (4)	0.1753 (7)	0.0680 (14)
H5	1.0566	0.5072	0.2173	0.082*
C6	0.9340 (4)	0.3903 (4)	0.2082 (6)	0.0577 (11)
H6	0.9713	0.3422	0.2738	0.069*
C7	0.6971 (4)	0.2001 (3)	0.1166 (5)	0.0444 (9)
C8	0.6619 (3)	0.0962 (3)	0.1951 (5)	0.0458 (9)
C9	0.5699 (4)	0.0925 (4)	0.2959 (6)	0.0578 (12)
C10	0.5336 (4)	−0.0053 (4)	0.3608 (7)	0.0766 (16)
H10	0.4709	−0.0067	0.4275	0.092*
C11	0.5915 (6)	−0.0989 (4)	0.3252 (9)	0.0805 (17)
H11	0.5689	−0.1646	0.3696	0.097*
C12	0.6820 (6)	−0.0983 (4)	0.2255 (9)	0.090 (2)
H12	0.7198	−0.1633	0.2007	0.108*
C13	0.7178 (5)	−0.0001 (4)	0.1608 (8)	0.0771 (15)
H13	0.7803	0.0003	0.0937	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0812 (7)	0.0536 (6)	0.0981 (10)	−0.0008 (6)	−0.0181 (7)	0.0268 (7)
Cl2	0.1036 (10)	0.0798 (9)	0.1282 (16)	0.0244 (8)	0.0548 (10)	0.0169 (10)
O1	0.0753 (19)	0.0604 (18)	0.0433 (16)	−0.0176 (15)	−0.0119 (16)	0.0148 (15)
N1	0.059 (2)	0.0434 (17)	0.047 (2)	−0.0080 (15)	−0.0111 (17)	0.0101 (17)
C1	0.043 (2)	0.046 (2)	0.042 (2)	−0.0078 (16)	0.0003 (19)	0.007 (2)
C2	0.044 (2)	0.044 (2)	0.042 (2)	−0.0025 (17)	−0.0062 (19)	0.0029 (18)
C3	0.054 (2)	0.040 (2)	0.051 (3)	0.0010 (18)	0.004 (2)	0.0030 (19)
C4	0.053 (3)	0.060 (3)	0.055 (3)	−0.017 (2)	−0.001 (2)	0.011 (2)
C5	0.051 (2)	0.078 (3)	0.075 (4)	−0.023 (2)	−0.008 (3)	0.018 (3)
C6	0.050 (2)	0.068 (3)	0.056 (3)	−0.005 (2)	−0.011 (2)	0.018 (2)
C7	0.047 (2)	0.046 (2)	0.040 (2)	−0.0003 (18)	0.0013 (19)	0.0077 (19)
C8	0.047 (2)	0.045 (2)	0.046 (2)	−0.0003 (16)	−0.007 (2)	0.0032 (18)
C9	0.050 (2)	0.059 (3)	0.064 (3)	−0.002 (2)	0.001 (2)	0.014 (2)
C10	0.063 (3)	0.078 (3)	0.089 (4)	−0.022 (3)	0.008 (3)	0.029 (4)
C11	0.093 (4)	0.053 (3)	0.096 (4)	−0.020 (3)	−0.016 (4)	0.027 (3)
C12	0.113 (5)	0.042 (3)	0.116 (5)	0.013 (3)	0.003 (5)	0.011 (3)
C13	0.085 (3)	0.056 (3)	0.090 (4)	0.009 (2)	0.013 (4)	0.002 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.735 (4)	C5—H5	0.9300
Cl2—C9	1.737 (5)	C6—H6	0.9300
O1—C7	1.217 (5)	C7—C8	1.502 (6)
N1—C7	1.344 (5)	C8—C13	1.372 (6)
N1—C1	1.406 (5)	C8—C9	1.383 (6)
N1—H1N	0.8600	C9—C10	1.389 (7)
C1—C6	1.389 (6)	C10—C11	1.358 (8)
C1—C2	1.391 (6)	C10—H10	0.9300
C2—C3	1.385 (5)	C11—C12	1.362 (9)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.362 (6)	C12—C13	1.390 (8)
C4—C5	1.372 (7)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.372 (6)

C7—N1—C1	128.9 (3)	O1—C7—N1	124.1 (4)
C7—N1—H1N	115.5	O1—C7—C8	120.3 (4)
C1—N1—H1N	115.5	N1—C7—C8	115.6 (3)
C6—C1—C2	119.5 (3)	C13—C8—C9	118.0 (4)
C6—C1—N1	117.3 (3)	C13—C8—C7	119.8 (4)
C2—C1—N1	123.1 (3)	C9—C8—C7	122.1 (4)
C3—C2—C1	117.9 (4)	C8—C9—C10	121.6 (5)
C3—C2—H2	121.1	C8—C9—Cl2	119.1 (3)
C1—C2—H2	121.1	C10—C9—Cl2	119.3 (4)
C4—C3—C2	123.0 (4)	C11—C10—C9	118.8 (5)
C4—C3—Cl1	118.9 (3)	C11—C10—H10	120.6
C2—C3—Cl1	118.1 (3)	C9—C10—H10	120.6
C3—C4—C5	118.4 (4)	C10—C11—C12	121.1 (5)
C3—C4—H4	120.8	C10—C11—H11	119.4
C5—C4—H4	120.8	C12—C11—H11	119.4
C4—C5—C6	120.8 (4)	C11—C12—C13	119.8 (5)
C4—C5—H5	119.6	C11—C12—H12	120.1
C6—C5—H5	119.6	C13—C12—H12	120.1
C5—C6—C1	120.4 (4)	C8—C13—C12	120.7 (5)
C5—C6—H6	119.8	C8—C13—H13	119.7
C1—C6—H6	119.8	C12—C13—H13	119.7

C7—N1—C1—C6	−160.3 (4)	N1—C7—C8—C13	−92.5 (5)
C7—N1—C1—C2	22.4 (7)	O1—C7—C8—C9	−90.1 (5)
C6—C1—C2—C3	−1.1 (6)	N1—C7—C8—C9	91.1 (5)
N1—C1—C2—C3	176.2 (4)	C13—C8—C9—C10	−0.4 (7)
C1—C2—C3—C4	1.6 (6)	C7—C8—C9—C10	176.0 (5)
C1—C2—C3—Cl1	−178.2 (3)	C13—C8—C9—Cl2	178.2 (4)
C2—C3—C4—C5	−0.7 (7)	C7—C8—C9—Cl2	−5.3 (6)
Cl1—C3—C4—C5	179.2 (4)	C8—C9—C10—C11	0.9 (8)
C3—C4—C5—C6	−0.8 (8)	Cl2—C9—C10—C11	−177.8 (5)
C4—C5—C6—C1	1.3 (8)	C9—C10—C11—C12	−1.3 (9)
C2—C1—C6—C5	−0.3 (7)	C10—C11—C12—C13	1.2 (10)
N1—C1—C6—C5	−177.7 (5)	C9—C8—C13—C12	0.3 (9)
C1—N1—C7—O1	2.6 (7)	C7—C8—C13—C12	−176.2 (5)
C1—N1—C7—C8	−178.6 (4)	C11—C12—C13—C8	−0.8 (10)
O1—C7—C8—C13	86.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.06	2.880 (5)	159

Symmetry code: (i) −x+3/2, y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉Cl₂NO
M_r	266.11
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	299
a, b, c (Å)	11.430 (1), 12.209 (2), 8.878 (1)
V (Å³)	1238.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.48 × 0.18 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.794, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	4926, 1746, 1248
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.139, 1.15
No. of reflections	1746
No. of parameters	154
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.42
Absolute structure	Flack (1983), 387 Friedel pairs
Absolute structure parameter	0.02 (13)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.06	2.880 (5)	159

Symmetry code: (i) −x+3/2, y, z+1/2.

Acknowledgements

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

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o861. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o462. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar