2-Chloro-N-[4-chloro-2-(2-chloro-benzo-yl)phen-yl]acetamide.

In the title compound, C(15)H(10)Cl(3)NO(2), an intra-molecular N-H⋯O hydrogen bond forms a six-membered ring and enforces an almost coplanar conformation for the acetamido group, the central benzene ring and the bridging carbonyl C-C(=O)-C group: the dihedral angles between the benzene ring and the acetamide and carbonyl C-C(=O)-C planes are 7.06 (11) and 7.17 (12)°, respectively. The dihedral angle between the two benzene rings is 67.43 (9)°. Because a strong hydrogen-bond donor is involved in the intra-molecular inter-action, the crystal packing is determined by weak C-H⋯O and C-H⋯Cl inter-actions.

Related literature

The title compound is isostructural with 2-chloro­acetamido-5-chloro-2′-fluoro­benzophenone (Prasanna & Guru Row, 2000 ▶). For the isostructurality index, see: Kálmán et al. (1991 ▶); Kubicki & Szafrański (1998 ▶). For a related structure, see: Malathy Sony et al. (2005 ▶). For the biological activity of benzophenone derivatives, see: Evans et al. (1987 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C15H10Cl3NO2

M = 342.59

Triclinic,

a = 7.5776 (9) Å

b = 10.1565 (10) Å

c = 10.7862 (12) Å

α = 70.069 (8)°

β = 77.604 (9)°

γ = 70.388 (8)°

V = 730.47 (14) Å3

Z = 2

Cu Kα radiation

μ = 5.71 mm−1

T = 295 K

0.35 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.117, T max = 0.319

5245 measured reflections

2917 independent reflections

2610 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.05

2917 reflections

230 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003375/is2519sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003375/is2519Isup2.hkl

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

C15H10Cl3NO2	Z = 2
Mr = 342.59	F(000) = 348
Triclinic, P1	Dx = 1.558 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.5776 (9) Å	Cell parameters from 3832 reflections
b = 10.1565 (10) Å	θ = 4.4–75.1°
c = 10.7862 (12) Å	µ = 5.71 mm−1
α = 70.069 (8)°	T = 295 K
β = 77.604 (9)°	Prism, pink
γ = 70.388 (8)°	0.35 × 0.2 × 0.2 mm
V = 730.47 (14) Å3

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer	2917 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2610 reflections with I > 2σ(I)
mirror	Rint = 0.017
Detector resolution: 10.5357 pixels mm-1	θmax = 75.2°, θmin = 4.4°
ω–scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.117, Tmax = 0.319	l = −13→13
5245 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0551P)2 + 0.3949P] where P = (Fo2 + 2Fc2)/3
2917 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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	0.2330 (3)	0.4690 (2)	0.74281 (19)	0.0407 (4)
O1	0.1250 (3)	0.58486 (19)	0.68930 (16)	0.0679 (5)
C2	0.2780 (3)	0.4324 (2)	0.87982 (17)	0.0347 (4)
C3	0.3816 (3)	0.2896 (2)	0.94118 (19)	0.0391 (4)
H3	0.422 (3)	0.219 (2)	0.889 (2)	0.043 (6)*
C4	0.4253 (3)	0.2515 (2)	1.06806 (19)	0.0419 (4)
Cl4	0.55643 (9)	0.07373 (6)	1.14246 (6)	0.05951 (19)
C5	0.3676 (3)	0.3534 (2)	1.1378 (2)	0.0482 (5)
H5	0.393 (4)	0.325 (3)	1.228 (3)	0.074 (9)*
C6	0.2645 (3)	0.4939 (2)	1.0804 (2)	0.0454 (5)
H6	0.230 (4)	0.562 (3)	1.129 (3)	0.059 (7)*
C7	0.2178 (3)	0.5364 (2)	0.95170 (18)	0.0358 (4)
N8	0.1173 (3)	0.67993 (18)	0.88973 (17)	0.0415 (4)
H8	0.094 (4)	0.696 (3)	0.812 (3)	0.067 (8)*
C9	0.0393 (3)	0.7935 (2)	0.9426 (2)	0.0448 (5)
O10	0.0375 (3)	0.78715 (18)	1.05679 (17)	0.0650 (5)
C11	−0.0562 (4)	0.9388 (3)	0.8497 (3)	0.0545 (6)
H11B	−0.006 (4)	1.010 (3)	0.851 (3)	0.066 (8)*
H11A	−0.189 (5)	0.970 (4)	0.878 (3)	0.083 (10)*
Cl12	−0.03818 (13)	0.94573 (7)	0.68136 (7)	0.0826 (3)
C13	0.3127 (3)	0.3605 (2)	0.66429 (18)	0.0403 (4)
C14	0.5017 (3)	0.3148 (2)	0.61956 (19)	0.0465 (5)
Cl14	0.66554 (9)	0.37077 (10)	0.66357 (7)	0.0759 (2)
C15	0.5645 (5)	0.2289 (3)	0.5339 (2)	0.0701 (9)
H15	0.693 (6)	0.200 (4)	0.509 (4)	0.102 (12)*
C16	0.4381 (7)	0.1877 (3)	0.4935 (3)	0.0855 (12)
H16	0.478 (5)	0.129 (4)	0.433 (4)	0.109 (12)*
C17	0.2507 (8)	0.2312 (4)	0.5360 (3)	0.0885 (12)
H17	0.162 (6)	0.198 (4)	0.511 (4)	0.110 (13)*
C18	0.1858 (5)	0.3185 (3)	0.6211 (3)	0.0646 (7)
H18	0.054 (4)	0.345 (3)	0.647 (3)	0.064 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0457 (11)	0.0416 (10)	0.0345 (9)	−0.0059 (8)	−0.0076 (8)	−0.0154 (8)
O1	0.0874 (13)	0.0584 (10)	0.0450 (9)	0.0187 (9)	−0.0284 (8)	−0.0254 (8)
C2	0.0395 (9)	0.0372 (9)	0.0292 (8)	−0.0102 (8)	−0.0037 (7)	−0.0129 (7)
C3	0.0472 (11)	0.0362 (9)	0.0353 (9)	−0.0107 (8)	−0.0050 (8)	−0.0129 (8)
C4	0.0495 (11)	0.0382 (10)	0.0356 (9)	−0.0121 (8)	−0.0076 (8)	−0.0065 (8)
Cl4	0.0745 (4)	0.0419 (3)	0.0526 (3)	−0.0059 (3)	−0.0225 (3)	−0.0034 (2)
C5	0.0644 (14)	0.0501 (12)	0.0308 (9)	−0.0150 (10)	−0.0110 (9)	−0.0105 (9)
C6	0.0595 (13)	0.0464 (11)	0.0339 (10)	−0.0124 (9)	−0.0062 (9)	−0.0185 (9)
C7	0.0415 (10)	0.0362 (9)	0.0319 (9)	−0.0112 (8)	−0.0031 (7)	−0.0132 (7)
N8	0.0518 (10)	0.0364 (8)	0.0364 (9)	−0.0057 (7)	−0.0076 (7)	−0.0161 (7)
C9	0.0521 (12)	0.0401 (10)	0.0465 (11)	−0.0124 (9)	−0.0024 (9)	−0.0205 (9)
O10	0.0977 (14)	0.0495 (9)	0.0508 (9)	−0.0098 (9)	−0.0101 (9)	−0.0283 (8)
C11	0.0611 (15)	0.0390 (11)	0.0633 (14)	−0.0044 (10)	−0.0096 (12)	−0.0231 (10)
Cl12	0.1198 (6)	0.0491 (3)	0.0563 (4)	0.0106 (4)	−0.0247 (4)	−0.0128 (3)
C13	0.0556 (12)	0.0394 (10)	0.0296 (9)	−0.0123 (9)	−0.0095 (8)	−0.0129 (7)
C14	0.0579 (12)	0.0412 (10)	0.0317 (9)	0.0000 (9)	−0.0095 (9)	−0.0111 (8)
Cl14	0.0489 (3)	0.1181 (6)	0.0624 (4)	−0.0212 (4)	−0.0057 (3)	−0.0312 (4)
C15	0.101 (2)	0.0478 (13)	0.0343 (11)	0.0192 (14)	−0.0117 (13)	−0.0156 (10)
C16	0.172 (4)	0.0390 (12)	0.0384 (13)	−0.0081 (17)	−0.0247 (18)	−0.0161 (10)
C17	0.171 (4)	0.074 (2)	0.0541 (16)	−0.064 (2)	−0.033 (2)	−0.0190 (15)
C18	0.0825 (19)	0.0759 (17)	0.0535 (14)	−0.0381 (15)	−0.0126 (13)	−0.0231 (13)

C1—O1	1.217 (3)	C9—O10	1.209 (3)
C1—C2	1.482 (2)	C9—C11	1.514 (3)
C1—C13	1.506 (3)	C11—Cl12	1.770 (3)
C2—C3	1.401 (3)	C11—H11B	0.93 (3)
C2—C7	1.417 (2)	C11—H11A	0.96 (3)
C3—C4	1.371 (3)	C13—C14	1.381 (3)
C3—H3	0.99 (2)	C13—C18	1.388 (3)
C4—C5	1.383 (3)	C14—C15	1.387 (3)
C4—Cl4	1.744 (2)	C14—Cl14	1.732 (2)
C5—C6	1.374 (3)	C15—C16	1.363 (5)
C5—H5	0.96 (3)	C15—H15	0.92 (4)
C6—C7	1.392 (3)	C16—C17	1.363 (6)
C6—H6	0.94 (3)	C16—H16	0.97 (4)
C7—N8	1.401 (3)	C17—C18	1.392 (4)
N8—C9	1.361 (3)	C17—H17	0.96 (4)
N8—H8	0.84 (3)	C18—H18	0.95 (3)
O1—C1—C2	122.49 (17)	N8—C9—C11	116.46 (19)
O1—C1—C13	116.25 (17)	C9—C11—Cl12	116.35 (15)
C2—C1—C13	121.21 (17)	C9—C11—H11B	109.2 (18)
C3—C2—C7	118.78 (17)	Cl12—C11—H11B	106.8 (18)
C3—C2—C1	118.91 (16)	C9—C11—H11A	111 (2)
C7—C2—C1	122.30 (17)	Cl12—C11—H11A	106 (2)
C4—C3—C2	120.57 (18)	H11B—C11—H11A	107 (3)
C4—C3—H3	122.2 (13)	C14—C13—C18	118.3 (2)
C2—C3—H3	117.3 (13)	C14—C13—C1	123.67 (19)
C3—C4—C5	120.60 (19)	C18—C13—C1	117.5 (2)
C3—C4—Cl4	120.01 (16)	C13—C14—C15	121.3 (3)
C5—C4—Cl4	119.38 (16)	C13—C14—Cl14	120.50 (15)
C6—C5—C4	120.02 (19)	C15—C14—Cl14	118.2 (2)
C6—C5—H5	119.4 (18)	C16—C15—C14	119.6 (3)
C4—C5—H5	120.5 (18)	C16—C15—H15	123 (2)
C5—C6—C7	120.93 (19)	C14—C15—H15	117 (2)
C5—C6—H6	118.3 (16)	C15—C16—C17	120.4 (2)
C7—C6—H6	120.8 (16)	C15—C16—H16	121 (2)
C6—C7—N8	121.99 (17)	C17—C16—H16	118 (2)
C6—C7—C2	119.09 (18)	C16—C17—C18	120.6 (3)
N8—C7—C2	118.90 (16)	C16—C17—H17	121 (2)
C9—N8—C7	128.23 (18)	C18—C17—H17	119 (3)
C9—N8—H8	116 (2)	C13—C18—C17	119.9 (3)
C7—N8—H8	116 (2)	C13—C18—H18	123.9 (17)
O10—C9—N8	125.6 (2)	C17—C18—H18	116.2 (17)
O10—C9—C11	117.95 (19)
O1—C1—C2—C3	170.9 (2)	C7—N8—C9—O10	−3.3 (4)
C13—C1—C2—C3	−6.2 (3)	C7—N8—C9—C11	178.0 (2)
O1—C1—C2—C7	−8.3 (3)	O10—C9—C11—Cl12	176.4 (2)
C13—C1—C2—C7	174.60 (18)	N8—C9—C11—Cl12	−4.8 (3)
C7—C2—C3—C4	−0.6 (3)	O1—C1—C13—C14	114.9 (2)
C1—C2—C3—C4	−179.76 (19)	C2—C1—C13—C14	−67.8 (3)
C2—C3—C4—C5	0.1 (3)	O1—C1—C13—C18	−56.9 (3)
C2—C3—C4—Cl4	−179.37 (15)	C2—C1—C13—C18	120.4 (2)
C3—C4—C5—C6	0.4 (4)	C18—C13—C14—C15	−0.2 (3)
Cl4—C4—C5—C6	179.89 (18)	C1—C13—C14—C15	−171.9 (2)
C4—C5—C6—C7	−0.5 (4)	C18—C13—C14—Cl14	176.90 (18)
C5—C6—C7—N8	−178.2 (2)	C1—C13—C14—Cl14	5.2 (3)
C5—C6—C7—C2	0.1 (3)	C13—C14—C15—C16	−0.4 (3)
C3—C2—C7—C6	0.4 (3)	Cl14—C14—C15—C16	−177.56 (19)
C1—C2—C7—C6	179.63 (19)	C14—C15—C16—C17	0.5 (4)
C3—C2—C7—N8	178.80 (18)	C15—C16—C17—C18	0.1 (5)
C1—C2—C7—N8	−2.0 (3)	C14—C13—C18—C17	0.7 (4)
C6—C7—N8—C9	−5.3 (3)	C1—C13—C18—C17	172.9 (2)
C2—C7—N8—C9	176.4 (2)	C16—C17—C18—C13	−0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1	0.84 (3)	1.95 (3)	2.634 (2)	138 (3)
C6—H6···Cl14i	0.94 (3)	2.87 (3)	3.675 (2)	143 (2)
C11—H11B···O10ii	0.93 (3)	2.50 (3)	3.320 (3)	147 (2)
C18—H18···Cl14iii	0.95 (3)	2.84 (3)	3.745 (3)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O1	0.84 (3)	1.95 (3)	2.634 (2)	138 (3)
C6—H6⋯Cl14i	0.94 (3)	2.87 (3)	3.675 (2)	143 (2)
C11—H11B⋯O10ii	0.93 (3)	2.50 (3)	3.320 (3)	147 (2)
C18—H18⋯Cl14iii	0.95 (3)	2.84 (3)	3.745 (3)	161 (2)

Symmetry codes: (i) ; (ii) ; (iii) .