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

The title compound, C(13)H(9)Cl(2)N, has an intra-molecular C-H⋯O close contact, and presents the NH group syn to the meta-chloro group in the aniline ring and trans to the C=O group. The crystal packing is formed by infinite chains of N-H⋯O hydrogen bonds along the c axis. Cl⋯Cl [3.474 (1) Å] contacts link chains. The crystal used for data collection was a twin, the domains related by the twin law 0.948 (1)/0.052 (1).

Related literature

For halogen inter­actions in the benzanilide series, see: Chopra & Guru Row (2005 ▶, 2008 ▶); Saeed et al. (2008 ▶); Gowda et al. (2008 ▶). For Cl⋯Cl inter­actions, see: Bui et al. (2009 ▶). For the program ROTAX, used to determine the twin law, see: Pearson & Gould (2003 ▶).

Experimental

Crystal data

C13H9Cl2NO

M = 266.11

Monoclinic,

a = 12.8696 (15) Å

b = 9.7485 (10) Å

c = 9.8243 (12) Å

β = 90.265 (11)°

V = 1232.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 292 K

0.42 × 0.28 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Eos (Nova) detector

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.815, T max = 0.910

13416 measured reflections

2407 independent reflections

1678 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.03

2407 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034308/bg2292sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034308/bg2292Isup2.hkl

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

C13H9Cl2NO	F(000) = 544
Mr = 266.11	Dx = 1.434 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 350 reflections
a = 12.8696 (15) Å	θ = 1.0–28.0°
b = 9.7485 (10) Å	µ = 0.51 mm−1
c = 9.8243 (12) Å	T = 292 K
β = 90.265 (11)°	Plate, colorless
V = 1232.5 (2) Å3	0.42 × 0.28 × 0.19 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with an Eos (Nova) detector	2407 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1678 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 16.0839 pixels mm-1	θmax = 26.0°, θmin = 3.2°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.815, Tmax = 0.910	l = −12→12
13416 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0559P)2] where P = (Fo2 + 2Fc2)/3
2407 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
Cl2	−0.01097 (5)	1.07010 (7)	0.17348 (7)	0.0830 (3)
Cl1	0.45841 (6)	0.16654 (6)	0.53117 (7)	0.0811 (3)
O1	0.27955 (14)	0.79207 (16)	0.68009 (14)	0.0682 (5)
N1	0.24298 (14)	0.79496 (18)	0.45618 (16)	0.0512 (4)
H1N	0.2531	0.7516	0.3812	0.061*
C7	0.28063 (16)	0.7347 (2)	0.56910 (19)	0.0485 (5)
C1	0.32291 (15)	0.5931 (2)	0.55447 (18)	0.0459 (5)
C9	0.12551 (16)	0.9361 (2)	0.3325 (2)	0.0513 (5)
H9	0.1205	0.8662	0.2683	0.062*
C8	0.18891 (16)	0.9205 (2)	0.44516 (19)	0.0464 (5)
C6	0.29668 (18)	0.5044 (2)	0.4485 (2)	0.0561 (6)
H6	0.2510	0.5339	0.3810	0.067*
C2	0.39013 (18)	0.5444 (2)	0.6539 (2)	0.0599 (6)
H2	0.4077	0.6010	0.7267	0.072*
C13	0.19596 (19)	1.0256 (2)	0.5399 (2)	0.0602 (6)
H13	0.2385	1.0167	0.6162	0.072*
C3	0.43165 (19)	0.4141 (2)	0.6475 (2)	0.0634 (6)
H3	0.4773	0.3836	0.7147	0.076*
C4	0.40478 (17)	0.3300 (2)	0.5410 (2)	0.0559 (6)
C5	0.33695 (18)	0.3742 (2)	0.4418 (2)	0.0602 (6)
H5	0.3185	0.3162	0.3705	0.072*
C11	0.0749 (2)	1.1604 (2)	0.4082 (3)	0.0699 (7)
H11	0.0364	1.2403	0.3963	0.084*
C10	0.06962 (18)	1.0554 (2)	0.3151 (2)	0.0577 (6)
C12	0.1386 (2)	1.1438 (3)	0.5190 (3)	0.0748 (7)
H12	0.1434	1.2143	0.5825	0.090*

	U11	U22	U33	U12	U13	U23
Cl2	0.0831 (5)	0.0747 (5)	0.0911 (5)	0.0067 (3)	−0.0221 (4)	0.0229 (3)
Cl1	0.0923 (5)	0.0617 (4)	0.0892 (5)	0.0194 (3)	−0.0156 (4)	0.0071 (3)
O1	0.1067 (13)	0.0635 (9)	0.0343 (8)	0.0055 (9)	0.0007 (8)	−0.0038 (7)
N1	0.0644 (11)	0.0550 (10)	0.0343 (9)	0.0082 (9)	−0.0023 (8)	−0.0031 (7)
C7	0.0550 (13)	0.0561 (13)	0.0344 (11)	−0.0050 (10)	0.0026 (9)	0.0013 (10)
C1	0.0491 (12)	0.0533 (13)	0.0351 (10)	−0.0028 (10)	−0.0013 (9)	0.0045 (9)
C9	0.0556 (13)	0.0462 (12)	0.0520 (13)	−0.0034 (10)	0.0010 (10)	0.0026 (9)
C8	0.0492 (12)	0.0462 (12)	0.0439 (11)	−0.0008 (9)	0.0080 (9)	0.0015 (9)
C6	0.0640 (14)	0.0567 (14)	0.0475 (12)	0.0033 (11)	−0.0149 (11)	0.0039 (10)
C2	0.0721 (15)	0.0671 (15)	0.0402 (12)	0.0010 (12)	−0.0125 (11)	0.0003 (10)
C13	0.0698 (15)	0.0545 (14)	0.0562 (13)	−0.0013 (12)	−0.0024 (12)	−0.0046 (11)
C3	0.0696 (15)	0.0708 (16)	0.0497 (13)	0.0078 (12)	−0.0142 (12)	0.0146 (11)
C4	0.0595 (14)	0.0525 (13)	0.0557 (13)	0.0053 (10)	−0.0036 (11)	0.0106 (10)
C5	0.0723 (15)	0.0546 (14)	0.0536 (13)	0.0021 (12)	−0.0141 (11)	−0.0016 (11)
C11	0.0802 (17)	0.0479 (14)	0.0816 (18)	0.0108 (12)	0.0045 (15)	0.0070 (12)
C10	0.0582 (14)	0.0512 (13)	0.0638 (14)	0.0002 (11)	0.0019 (11)	0.0132 (11)
C12	0.096 (2)	0.0515 (15)	0.0774 (17)	0.0021 (14)	0.0097 (16)	−0.0137 (13)

Cl2—C10	1.738 (2)	C6—H6	0.9300
Cl1—C4	1.740 (2)	C2—C3	1.380 (3)
O1—C7	1.226 (2)	C2—H2	0.9300
N1—C7	1.344 (2)	C13—C12	1.384 (3)
N1—C8	1.412 (3)	C13—H13	0.9300
N1—H1N	0.8600	C3—C4	1.373 (3)
C7—C1	1.491 (3)	C3—H3	0.9300
C1—C2	1.385 (3)	C4—C5	1.375 (3)
C1—C6	1.394 (3)	C5—H5	0.9300
C9—C10	1.378 (3)	C11—C12	1.369 (4)
C9—C8	1.381 (3)	C11—C10	1.374 (3)
C9—H9	0.9300	C11—H11	0.9300
C8—C13	1.386 (3)	C12—H12	0.9300
C6—C5	1.372 (3)
C7—N1—C8	128.18 (17)	C12—C13—C8	118.8 (2)
C7—N1—H1N	115.9	C12—C13—H13	120.6
C8—N1—H1N	115.9	C8—C13—H13	120.6
O1—C7—N1	121.9 (2)	C4—C3—C2	119.22 (19)
O1—C7—C1	120.94 (18)	C4—C3—H3	120.4
N1—C7—C1	117.11 (17)	C2—C3—H3	120.4
C2—C1—C6	117.5 (2)	C3—C4—C5	120.7 (2)
C2—C1—C7	118.44 (18)	C3—C4—Cl1	119.41 (17)
C6—C1—C7	124.01 (17)	C5—C4—Cl1	119.90 (18)
C10—C9—C8	119.9 (2)	C6—C5—C4	119.6 (2)
C10—C9—H9	120.1	C6—C5—H5	120.2
C8—C9—H9	120.1	C4—C5—H5	120.2
C9—C8—C13	119.6 (2)	C12—C11—C10	117.9 (2)
C9—C8—N1	116.49 (18)	C12—C11—H11	121.0
C13—C8—N1	123.91 (19)	C10—C11—H11	121.0
C5—C6—C1	121.30 (19)	C11—C10—C9	121.5 (2)
C5—C6—H6	119.4	C11—C10—Cl2	119.93 (18)
C1—C6—H6	119.4	C9—C10—Cl2	118.53 (18)
C3—C2—C1	121.6 (2)	C11—C12—C13	122.3 (2)
C3—C2—H2	119.2	C11—C12—H12	118.9
C1—C2—H2	119.2	C13—C12—H12	118.9
C8—N1—C7—O1	−6.8 (3)	C9—C8—C13—C12	0.2 (3)
C8—N1—C7—C1	172.39 (18)	N1—C8—C13—C12	−179.4 (2)
O1—C7—C1—C2	−20.6 (3)	C1—C2—C3—C4	−0.8 (4)
N1—C7—C1—C2	160.2 (2)	C2—C3—C4—C5	−0.3 (4)
O1—C7—C1—C6	157.4 (2)	C2—C3—C4—Cl1	179.05 (18)
N1—C7—C1—C6	−21.8 (3)	C1—C6—C5—C4	−0.2 (3)
C10—C9—C8—C13	−0.2 (3)	C3—C4—C5—C6	0.8 (4)
C10—C9—C8—N1	179.50 (18)	Cl1—C4—C5—C6	−178.57 (18)
C7—N1—C8—C9	−156.2 (2)	C12—C11—C10—C9	0.6 (4)
C7—N1—C8—C13	23.4 (3)	C12—C11—C10—Cl2	179.3 (2)
C2—C1—C6—C5	−0.8 (3)	C8—C9—C10—C11	−0.3 (3)
C7—C1—C6—C5	−178.9 (2)	C8—C9—C10—Cl2	−178.96 (16)
C6—C1—C2—C3	1.3 (3)	C10—C11—C12—C13	−0.6 (4)
C7—C1—C2—C3	179.5 (2)	C8—C13—C12—C11	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.05	2.883 (2)	163
C13—H13···O1	0.93	2.34	2.868 (3)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.05	2.883 (2)	163
C13—H13⋯O1	0.93	2.34	2.868 (3)	116

Symmetry code: (i) .