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

In the mol-ecular structure of the title compound, C(13)H(9)Cl(2)NO, the amide N-C=O plane makes dihedral angles of 31.53 (8) and 36.23 (8)°, respectively, with the 4-chloro- and 2-chloro-phenyl rings. The dihedral angle between the two benzene rings is 6.25 (8)°. The mol-ecules are stacked in columns along the b axis through inter-molecular N-H⋯O hydrogen bonds. The columns are further connected by weak C-H⋯O hydrogen bonds. The compound is not isomorphous with the fluoro analogue.

Related literature

For general background, see: Capdeville et al. (2002 ▶); Chopra & Row (2005 ▶); Ho et al. (2002 ▶); Igawa et al. (1999 ▶); Jackson et al. (1994 ▶); Makino et al. (2003 ▶); Zhichkin et al. (2007 ▶). For related structures, see: Chopra & Row (2005 ▶).

Experimental

Crystal data

C13H9Cl2NO

M = 266.13

Monoclinic,

a = 10.7913 (14) Å

b = 4.8078 (6) Å

c = 23.570 (3) Å

β = 97.718 (3)°

V = 1211.8 (3) Å3

Z = 4

Mo- Kα radiation

μ = 0.52 mm−1

T = 223 (1) K

0.35 × 0.31 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.884, T max = 0.975

14924 measured reflections

3527 independent reflections

1847 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.154

S = 1.00

3527 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.39 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028882/bh2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028882/bh2189Isup2.hkl

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

C13H9Cl2NO	F(000) = 544.00
Mr = 266.13	Dx = 1.459 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 8924 reflections
a = 10.7913 (14) Å	θ = 3.0–30.0°
b = 4.8078 (6) Å	µ = 0.52 mm−1
c = 23.570 (3) Å	T = 223 K
β = 97.718 (3)°	Plate, colourless
V = 1211.8 (3) Å3	0.35 × 0.31 × 0.05 mm
Z = 4

Rigaku R-AXIS RAPID II diffractometer	1847 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.042
ω scans	θmax = 30.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→15
Tmin = 0.884, Tmax = 0.975	k = −6→6
14924 measured reflections	l = −31→33
3527 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	0 constraints
R[F2 > 2σ(F2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.079P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3527 reflections	Δρmax = 0.23 e Å−3
158 parameters	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.01681 (5)	0.18996 (11)	0.55784 (3)	0.0701 (2)
Cl2	0.40856 (8)	0.29994 (18)	0.27592 (3)	0.1044 (3)
O1	0.31900 (14)	0.9176 (3)	0.52035 (6)	0.0704 (4)
N1	0.24949 (15)	0.4883 (3)	0.54060 (7)	0.0533 (4)
H1	0.246 (2)	0.321 (5)	0.5293 (10)	0.074 (7)*
C1	0.32607 (17)	0.5666 (4)	0.45021 (8)	0.0523 (4)
C2	0.4236 (2)	0.6900 (4)	0.42566 (10)	0.0650 (6)
H2	0.4721	0.8303	0.4456	0.078*
C3	0.4487 (2)	0.6070 (5)	0.37257 (11)	0.0725 (6)
H3	0.5152	0.6882	0.3565	0.087*
C4	0.3765 (2)	0.4053 (5)	0.34303 (10)	0.0695 (6)
C5	0.2787 (2)	0.2815 (5)	0.36606 (10)	0.0680 (6)
H5	0.2295	0.1444	0.3454	0.082*
C6	0.25440 (19)	0.3623 (4)	0.41982 (9)	0.0599 (5)
H6	0.1887	0.2780	0.4359	0.072*
C7	0.29897 (17)	0.6734 (3)	0.50645 (9)	0.0528 (5)
C8	0.20311 (18)	0.5546 (4)	0.59237 (8)	0.0531 (4)
C9	0.09424 (19)	0.4263 (4)	0.60525 (8)	0.0554 (5)
C10	0.0457 (2)	0.4875 (5)	0.65537 (9)	0.0727 (6)
H10	−0.0267	0.3965	0.6639	0.087*
C11	0.1041 (3)	0.6823 (6)	0.69252 (11)	0.0870 (8)
H11	0.0701	0.7295	0.7259	0.104*
C12	0.2115 (3)	0.8069 (5)	0.68088 (11)	0.0833 (8)
H12	0.2517	0.9368	0.7069	0.100*
C13	0.2623 (2)	0.7451 (4)	0.63118 (10)	0.0694 (6)
H13	0.3366	0.8322	0.6239	0.083*

	U11	U22	U33	U12	U13	U23
Cl1	0.0638 (4)	0.0686 (4)	0.0792 (4)	−0.0099 (2)	0.0140 (3)	−0.0038 (3)
Cl2	0.1190 (6)	0.1252 (6)	0.0763 (5)	0.0111 (5)	0.0399 (4)	−0.0089 (4)
O1	0.0844 (10)	0.0411 (7)	0.0895 (11)	−0.0058 (7)	0.0258 (8)	−0.0078 (7)
N1	0.0588 (10)	0.0416 (8)	0.0610 (10)	−0.0015 (7)	0.0138 (7)	−0.0073 (7)
C1	0.0492 (11)	0.0427 (9)	0.0664 (12)	0.0048 (8)	0.0125 (9)	0.0010 (8)
C2	0.0556 (12)	0.0544 (11)	0.0883 (16)	−0.0030 (9)	0.0215 (11)	−0.0019 (10)
C3	0.0654 (14)	0.0695 (13)	0.0890 (16)	0.0007 (11)	0.0333 (12)	0.0051 (12)
C4	0.0710 (14)	0.0737 (14)	0.0667 (13)	0.0155 (11)	0.0193 (11)	0.0037 (11)
C5	0.0673 (14)	0.0718 (13)	0.0649 (14)	−0.0011 (11)	0.0085 (10)	−0.0083 (10)
C6	0.0560 (12)	0.0605 (11)	0.0647 (12)	−0.0051 (9)	0.0137 (9)	−0.0010 (9)
C7	0.0468 (10)	0.0411 (9)	0.0714 (12)	0.0028 (7)	0.0114 (9)	−0.0016 (8)
C8	0.0581 (11)	0.0459 (9)	0.0546 (11)	0.0081 (8)	0.0050 (8)	−0.0026 (8)
C9	0.0584 (12)	0.0542 (10)	0.0536 (10)	0.0086 (9)	0.0078 (9)	0.0019 (9)
C10	0.0785 (15)	0.0826 (14)	0.0596 (12)	0.0170 (12)	0.0185 (11)	0.0073 (12)
C11	0.111 (2)	0.0959 (19)	0.0554 (14)	0.0370 (17)	0.0142 (14)	−0.0010 (13)
C12	0.105 (2)	0.0804 (16)	0.0593 (14)	0.0151 (15)	−0.0073 (13)	−0.0202 (11)
C13	0.0756 (15)	0.0632 (12)	0.0665 (14)	0.0028 (11)	−0.0010 (11)	−0.0106 (10)

Cl1—C9	1.729 (2)	C5—C6	1.384 (3)
Cl2—C4	1.739 (2)	C5—H5	0.9400
O1—C7	1.230 (2)	C6—H6	0.9400
N1—C7	1.357 (2)	C8—C13	1.388 (3)
N1—C8	1.416 (2)	C8—C9	1.396 (3)
N1—H1	0.84 (2)	C9—C10	1.387 (3)
C1—C6	1.388 (3)	C10—C11	1.376 (4)
C1—C2	1.399 (3)	C10—H10	0.9400
C1—C7	1.487 (3)	C11—C12	1.364 (4)
C2—C3	1.375 (3)	C11—H11	0.9400
C2—H2	0.9400	C12—C13	1.391 (3)
C3—C4	1.373 (3)	C12—H12	0.9400
C3—H3	0.9400	C13—H13	0.9400
C4—C5	1.384 (3)
C7—N1—C8	125.20 (16)	O1—C7—N1	122.49 (18)
C7—N1—H1	116.3 (16)	O1—C7—C1	121.24 (16)
C8—N1—H1	118.4 (16)	N1—C7—C1	116.26 (16)
C6—C1—C2	118.98 (18)	C13—C8—C9	118.34 (19)
C6—C1—C7	122.80 (16)	C13—C8—N1	122.11 (19)
C2—C1—C7	118.10 (18)	C9—C8—N1	119.55 (17)
C3—C2—C1	120.3 (2)	C10—C9—C8	121.1 (2)
C3—C2—H2	119.8	C10—C9—Cl1	119.00 (17)
C1—C2—H2	119.8	C8—C9—Cl1	119.86 (15)
C4—C3—C2	119.9 (2)	C11—C10—C9	119.5 (2)
C4—C3—H3	120.0	C11—C10—H10	120.2
C2—C3—H3	120.0	C9—C10—H10	120.2
C3—C4—C5	121.0 (2)	C12—C11—C10	120.0 (2)
C3—C4—Cl2	119.89 (18)	C12—C11—H11	120.0
C5—C4—Cl2	119.1 (2)	C10—C11—H11	120.0
C6—C5—C4	119.1 (2)	C11—C12—C13	121.2 (2)
C6—C5—H5	120.4	C11—C12—H12	119.4
C4—C5—H5	120.4	C13—C12—H12	119.4
C5—C6—C1	120.66 (19)	C8—C13—C12	119.8 (2)
C5—C6—H6	119.7	C8—C13—H13	120.1
C1—C6—H6	119.7	C12—C13—H13	120.1
C6—C1—C2—C3	−0.8 (3)	C2—C1—C7—N1	−151.15 (18)
C7—C1—C2—C3	−177.11 (19)	C7—N1—C8—C13	−39.9 (3)
C1—C2—C3—C4	1.1 (3)	C7—N1—C8—C9	140.0 (2)
C2—C3—C4—C5	−0.5 (3)	C13—C8—C9—C10	0.3 (3)
C2—C3—C4—Cl2	−179.88 (18)	N1—C8—C9—C10	−179.58 (17)
C3—C4—C5—C6	−0.4 (3)	C13—C8—C9—Cl1	179.47 (15)
Cl2—C4—C5—C6	179.04 (17)	N1—C8—C9—Cl1	−0.4 (2)
C4—C5—C6—C1	0.6 (3)	C8—C9—C10—C11	1.4 (3)
C2—C1—C6—C5	0.0 (3)	Cl1—C9—C10—C11	−177.82 (17)
C7—C1—C6—C5	176.07 (19)	C9—C10—C11—C12	−2.2 (4)
C8—N1—C7—O1	7.0 (3)	C10—C11—C12—C13	1.4 (4)
C8—N1—C7—C1	−171.95 (16)	C9—C8—C13—C12	−1.1 (3)
C6—C1—C7—O1	−146.2 (2)	N1—C8—C13—C12	178.72 (19)
C2—C1—C7—O1	29.9 (3)	C11—C12—C13—C8	0.3 (4)
C6—C1—C7—N1	32.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.85 (2)	2.12 (2)	2.901 (2)	154 (2)
C2—H2···O1ii	0.94	2.59	3.456 (3)	153
C13—H13···O1	0.94	2.46	2.884 (3)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.85 (2)	2.12 (2)	2.901 (2)	154 (2)
C2—H2⋯O1ii	0.94	2.59	3.456 (3)	153

Symmetry codes: (i) ; (ii) .