2-Chloro-N-(3-chloro-phen-yl)benzamide.

In the structure of the the title compound, C(13)H(9)Cl(2)NO, 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 mol-ecules are linked into infinite chains through inter-molecular 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 = 266.11

Orthorhombic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.139

S = 1.15

1746 reflections

154 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.42 e Å−3

Absolute structure: Flack (1983 ▶), 387 Friedel pairs

Flack parameter: 0.02 (13)

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.

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

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

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

C13H9Cl2NO	F000 = 544
Mr = 266.11	Dx = 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 = 2.4–27.7º
b = 12.209 (2) Å	µ = 0.51 mm−1
c = 8.878 (1) Å	T = 299 (2) K
V = 1238.9 (3) Å3	Plate, colourless
Z = 4	0.48 × 0.18 × 0.04 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1746 independent reflections
Radiation source: fine-focus sealed tube	1248 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.4º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −14→7
Tmin = 0.794, Tmax = 0.980	k = −9→15
4926 measured reflections	l = −11→4

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0797P)2 + 0.0826P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139	(Δ/σ)max = 0.002
S = 1.15	Δρmax = 0.39 e Å−3
1746 reflections	Δρmin = −0.42 e Å−3
154 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 387 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (13)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .