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

In the title compound, C(13)H(9)Cl(2)NO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-Cl atom in the aniline ring is positioned syn to the N-H bond. The two aromatic rings are almost coplanar, making a dihedral angle of 4.73 (5)°. The crystal structure is stabilized by N-H⋯O hydrogen bonds, which link the mol-ecules into chains along the b axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2008 ▶). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶, 2008 ▶); Bowes et al. (2003 ▶); Saeed et al. (2010 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005 ▶) and on N-chloro­aryl­amides, see: Gowda et al. (1996 ▶).

Experimental

Crystal data

C13H9Cl2NO

M = 266.11

Monoclinic,

a = 11.1371 (4) Å

b = 4.85230 (17) Å

c = 21.5198 (8) Å

β = 90.142 (3)°

V = 1162.94 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.54 mm−1

T = 293 K

0.66 × 0.30 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.824, T max = 0.958

22845 measured reflections

3262 independent reflections

2279 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.118

S = 1.07

3262 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051944/ds2157sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051944/ds2157Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051944/ds2157Isup3.cml

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

C13H9Cl2NO	F(000) = 544
Mr = 266.11	Dx = 1.520 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11869 reflections
a = 11.1371 (4) Å	θ = 3.4–29.6°
b = 4.85230 (17) Å	µ = 0.54 mm−1
c = 21.5198 (8) Å	T = 293 K
β = 90.142 (3)°	Rod, colorless
V = 1162.94 (7) Å3	0.66 × 0.30 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3262 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2279 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 10.4340 pixels mm-1	θmax = 29.6°, θmin = 3.4°
ω scans	h = −15→15
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −6→6
Tmin = 0.824, Tmax = 0.958	l = −29→29
22845 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) = 0.118	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0694P)2 + 0.1106P] where P = (Fo2 + 2Fc2)/3
3262 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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
C1	0.28710 (14)	0.3142 (3)	0.01071 (8)	0.0380 (4)
C2	0.34075 (14)	0.4188 (3)	−0.04824 (7)	0.0375 (3)
C3	0.28456 (14)	0.6171 (3)	−0.08504 (7)	0.0376 (3)
H3A	0.2115	0.6930	−0.0731	0.045*
C4	0.33904 (15)	0.6991 (3)	−0.13953 (7)	0.0389 (4)
C5	0.44901 (16)	0.5933 (4)	−0.15784 (8)	0.0454 (4)
H5A	0.4854	0.6537	−0.1942	0.055*
C6	0.50336 (16)	0.3967 (4)	−0.12103 (9)	0.0476 (4)
H6A	0.5772	0.3240	−0.1327	0.057*
C7	0.44943 (15)	0.3067 (3)	−0.06703 (8)	0.0421 (4)
H7A	0.4860	0.1705	−0.0432	0.050*
C8	0.16652 (14)	0.4468 (3)	0.10141 (7)	0.0363 (3)
C9	0.05966 (15)	0.5829 (3)	0.11471 (7)	0.0380 (4)
C10	−0.00095 (17)	0.5387 (4)	0.16973 (9)	0.0498 (4)
H10A	−0.0719	0.6328	0.1778	0.060*
C11	0.04410 (19)	0.3552 (4)	0.21236 (9)	0.0553 (5)
H11A	0.0032	0.3235	0.2493	0.066*
C12	0.15079 (18)	0.2166 (4)	0.20030 (9)	0.0518 (5)
H12A	0.1816	0.0925	0.2292	0.062*
C13	0.21073 (16)	0.2639 (4)	0.14537 (8)	0.0450 (4)
H13A	0.2823	0.1713	0.1376	0.054*
N1	0.22659 (12)	0.5014 (3)	0.04507 (6)	0.0378 (3)
H1A	0.2245	0.6679	0.0314	0.045*
O1	0.29906 (12)	0.0726 (2)	0.02617 (6)	0.0521 (3)
Cl1	−0.00096 (4)	0.81078 (10)	0.06110 (2)	0.05256 (16)
Cl2	0.26902 (4)	0.94011 (10)	−0.18730 (2)	0.05402 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0412 (8)	0.0296 (8)	0.0432 (9)	−0.0022 (6)	0.0019 (7)	0.0005 (6)
C2	0.0435 (8)	0.0289 (7)	0.0400 (8)	−0.0024 (6)	0.0023 (7)	−0.0034 (6)
C3	0.0408 (8)	0.0315 (7)	0.0406 (8)	0.0012 (6)	0.0042 (7)	−0.0026 (6)
C4	0.0462 (9)	0.0320 (8)	0.0384 (8)	−0.0015 (7)	−0.0005 (7)	−0.0016 (6)
C5	0.0499 (9)	0.0456 (9)	0.0409 (9)	−0.0042 (8)	0.0093 (7)	−0.0007 (7)
C6	0.0416 (9)	0.0484 (10)	0.0529 (10)	0.0025 (8)	0.0084 (8)	−0.0044 (8)
C7	0.0432 (9)	0.0381 (9)	0.0448 (9)	0.0036 (7)	0.0002 (7)	−0.0020 (7)
C8	0.0407 (8)	0.0285 (7)	0.0397 (8)	−0.0044 (6)	0.0024 (6)	0.0018 (6)
C9	0.0422 (8)	0.0317 (8)	0.0402 (8)	0.0002 (7)	0.0001 (7)	0.0034 (6)
C10	0.0500 (10)	0.0503 (10)	0.0492 (10)	0.0021 (8)	0.0120 (8)	0.0012 (8)
C11	0.0672 (12)	0.0553 (11)	0.0435 (10)	−0.0023 (10)	0.0150 (9)	0.0090 (8)
C12	0.0654 (12)	0.0467 (10)	0.0433 (10)	−0.0013 (9)	0.0004 (8)	0.0110 (8)
C13	0.0477 (9)	0.0392 (8)	0.0481 (10)	0.0041 (7)	0.0003 (7)	0.0070 (7)
N1	0.0467 (7)	0.0268 (6)	0.0398 (7)	0.0008 (5)	0.0065 (6)	0.0043 (5)
O1	0.0702 (8)	0.0258 (6)	0.0603 (8)	0.0037 (5)	0.0152 (6)	0.0042 (5)
Cl1	0.0524 (3)	0.0506 (3)	0.0547 (3)	0.0111 (2)	0.0019 (2)	0.01349 (19)
Cl2	0.0654 (3)	0.0488 (3)	0.0479 (3)	0.0055 (2)	0.0006 (2)	0.01029 (19)

C1—O1	1.2257 (19)	C8—C13	1.387 (2)
C1—N1	1.352 (2)	C8—C9	1.391 (2)
C1—C2	1.493 (2)	C8—N1	1.411 (2)
C2—C7	1.388 (2)	C9—C10	1.381 (2)
C2—C3	1.393 (2)	C9—Cl1	1.7337 (16)
C3—C4	1.380 (2)	C10—C11	1.373 (3)
C3—H3A	0.9300	C10—H10A	0.9300
C4—C5	1.386 (2)	C11—C12	1.390 (3)
C4—Cl2	1.7404 (16)	C11—H11A	0.9300
C5—C6	1.379 (3)	C12—C13	1.378 (3)
C5—H5A	0.9300	C12—H12A	0.9300
C6—C7	1.380 (3)	C13—H13A	0.9300
C6—H6A	0.9300	N1—H1A	0.8600
C7—H7A	0.9300
O1—C1—N1	123.23 (15)	C13—C8—C9	117.77 (15)
O1—C1—C2	120.84 (15)	C13—C8—N1	122.54 (15)
N1—C1—C2	115.93 (13)	C9—C8—N1	119.69 (14)
C7—C2—C3	119.73 (15)	C10—C9—C8	121.52 (15)
C7—C2—C1	117.73 (14)	C10—C9—Cl1	118.63 (13)
C3—C2—C1	122.53 (14)	C8—C9—Cl1	119.84 (12)
C4—C3—C2	118.95 (15)	C11—C10—C9	119.68 (17)
C4—C3—H3A	120.5	C11—C10—H10A	120.2
C2—C3—H3A	120.5	C9—C10—H10A	120.2
C3—C4—C5	121.70 (15)	C10—C11—C12	120.00 (17)
C3—C4—Cl2	119.88 (13)	C10—C11—H11A	120.0
C5—C4—Cl2	118.41 (13)	C12—C11—H11A	120.0
C6—C5—C4	118.66 (16)	C13—C12—C11	119.71 (17)
C6—C5—H5A	120.7	C13—C12—H12A	120.1
C4—C5—H5A	120.7	C11—C12—H12A	120.1
C5—C6—C7	120.75 (16)	C12—C13—C8	121.31 (17)
C5—C6—H6A	119.6	C12—C13—H13A	119.3
C7—C6—H6A	119.6	C8—C13—H13A	119.3
C6—C7—C2	120.17 (16)	C1—N1—C8	125.58 (13)
C6—C7—H7A	119.9	C1—N1—H1A	117.2
C2—C7—H7A	119.9	C8—N1—H1A	117.2
O1—C1—C2—C7	−34.2 (2)	N1—C8—C9—C10	−178.97 (16)
N1—C1—C2—C7	145.40 (15)	C13—C8—C9—Cl1	−179.20 (13)
O1—C1—C2—C3	144.21 (17)	N1—C8—C9—Cl1	1.8 (2)
N1—C1—C2—C3	−36.2 (2)	C8—C9—C10—C11	−0.5 (3)
C7—C2—C3—C4	−0.4 (2)	Cl1—C9—C10—C11	178.75 (15)
C1—C2—C3—C4	−178.75 (14)	C9—C10—C11—C12	0.6 (3)
C2—C3—C4—C5	−1.3 (2)	C10—C11—C12—C13	−0.2 (3)
C2—C3—C4—Cl2	178.43 (11)	C11—C12—C13—C8	−0.3 (3)
C3—C4—C5—C6	1.5 (3)	C9—C8—C13—C12	0.4 (3)
Cl2—C4—C5—C6	−178.26 (14)	N1—C8—C13—C12	179.35 (16)
C4—C5—C6—C7	0.0 (3)	O1—C1—N1—C8	−2.0 (3)
C5—C6—C7—C2	−1.7 (3)	C2—C1—N1—C8	178.39 (14)
C3—C2—C7—C6	1.8 (2)	C13—C8—N1—C1	37.2 (2)
C1—C2—C7—C6	−179.71 (15)	C9—C8—N1—C1	−143.89 (16)
C13—C8—C9—C10	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.14	2.9157 (17)	151.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.14	2.9157 (17)	151

Symmetry code: (i) .