N-[4-Chloro-2-(2-chlorobenzoyl)phenyl]acetamide.

In the title compound, C(15)H(11)Cl(2)NO(2), the dihedral angle between the two benzene rings is 74.83 (5)°. The N-bound and terminal benzene rings are inclined at dihedral angles of 4.09 (10) and 78.38 (9)°, respectively, to the mean plane through the acetamide group. Intra-molecular C-H⋯O and N-H⋯O hydrogen bonds both generate S(6) rings.

Related literature

For the acetyl­ation reaction, see: Greene et al. (1999 ▶); Gupta et al. (2008 ▶). For solvent-free synthesis, see: Roopan et al. (2008 ▶, 2009 ▶). For reactions of acetic anhydride and acetyl chloride, see: Orita et al. (2000 ▶); Procopiou et al. (1998 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11Cl2NO2

M = 308.15

Monoclinic,

a = 11.1371 (11) Å

b = 5.0661 (6) Å

c = 25.594 (3) Å

β = 100.672 (9)°

V = 1419.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 293 K

0.28 × 0.24 × 0.18 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

14628 measured reflections

2633 independent reflections

1537 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.107

S = 0.98

2633 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018696/tk2672sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018696/tk2672Isup2.hkl

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

C15H11Cl2NO2	F(000) = 632
Mr = 308.15	Dx = 1.442 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1298 reflections
a = 11.1371 (11) Å	θ = 2.0–20.9°
b = 5.0661 (6) Å	µ = 0.46 mm−1
c = 25.594 (3) Å	T = 293 K
β = 100.672 (9)°	Block, colourless
V = 1419.1 (3) Å3	0.28 × 0.24 × 0.18 mm
Z = 4

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	1537 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.080
graphite	θmax = 25.5°, θmin = 2.7°
ω scans	h = −13→13
14628 measured reflections	k = −6→6
2633 independent reflections	l = −30→30

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0469P)2] where P = (Fo2 + 2Fc2)/3
2633 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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	1.01228 (8)	0.21348 (16)	0.05190 (3)	0.0676 (3)
Cl2	0.68968 (8)	0.97146 (17)	0.00452 (3)	0.0706 (3)
O1	0.94298 (18)	0.2513 (5)	0.19297 (8)	0.0777 (9)
O2	0.5030 (2)	0.0779 (5)	0.17216 (10)	0.0936 (11)
N1	0.7034 (2)	0.1634 (5)	0.17250 (9)	0.0533 (9)
C1	0.6927 (2)	0.7372 (6)	0.05413 (10)	0.0477 (10)
C2	0.8029 (2)	0.6603 (5)	0.08384 (10)	0.0429 (9)
C3	0.8082 (2)	0.4689 (5)	0.12330 (10)	0.0396 (9)
C4	0.6978 (2)	0.3551 (5)	0.13289 (10)	0.0431 (10)
C5	0.5876 (3)	0.4396 (6)	0.10239 (12)	0.0580 (11)
C6	0.5855 (3)	0.6267 (6)	0.06384 (12)	0.0566 (11)
C7	0.9300 (2)	0.3982 (6)	0.15419 (11)	0.0459 (10)
C8	1.0428 (2)	0.5175 (5)	0.13994 (10)	0.0399 (9)
C9	1.0892 (2)	0.4451 (5)	0.09588 (10)	0.0435 (10)
C10	1.1978 (3)	0.5487 (6)	0.08559 (12)	0.0565 (11)
C11	1.2597 (3)	0.7314 (7)	0.11949 (14)	0.0661 (13)
C12	1.2151 (3)	0.8101 (7)	0.16279 (13)	0.0686 (12)
C13	1.1075 (3)	0.7045 (6)	0.17374 (11)	0.0586 (11)
C14	0.6092 (3)	0.0330 (6)	0.18928 (13)	0.0607 (12)
C15	0.6499 (3)	−0.1678 (7)	0.23219 (13)	0.0775 (16)
H1	0.77560	0.12130	0.18860	0.0640*
H2	0.87480	0.73680	0.07750	0.0510*
H5	0.51450	0.36760	0.10840	0.0700*
H6	0.51110	0.68050	0.04390	0.0680*
H10	1.22820	0.49410	0.05590	0.0680*
H11	1.33250	0.80190	0.11290	0.0790*
H12	1.25710	0.93660	0.18540	0.0820*
H13	1.07860	0.75900	0.20380	0.0700*
H15A	0.63180	−0.10450	0.26520	0.1160*
H15B	0.73630	−0.19610	0.23590	0.1160*
H15C	0.60750	−0.33100	0.22290	0.1160*

	U11	U22	U33	U12	U13	U23
Cl1	0.0736 (6)	0.0686 (6)	0.0632 (5)	−0.0187 (5)	0.0197 (4)	−0.0213 (4)
Cl2	0.0681 (6)	0.0796 (6)	0.0622 (5)	0.0248 (5)	0.0069 (4)	0.0221 (5)
O1	0.0495 (13)	0.117 (2)	0.0670 (14)	0.0078 (13)	0.0115 (11)	0.0456 (14)
O2	0.0531 (15)	0.121 (2)	0.109 (2)	−0.0246 (16)	0.0209 (14)	0.0138 (17)
N1	0.0417 (14)	0.0620 (17)	0.0590 (16)	−0.0031 (13)	0.0164 (12)	0.0079 (14)
C1	0.0450 (18)	0.054 (2)	0.0428 (16)	0.0096 (15)	0.0050 (14)	−0.0018 (14)
C2	0.0343 (15)	0.0506 (18)	0.0446 (16)	0.0030 (13)	0.0098 (13)	−0.0003 (15)
C3	0.0334 (15)	0.0486 (18)	0.0367 (15)	0.0029 (13)	0.0061 (12)	0.0003 (14)
C4	0.0394 (16)	0.0466 (18)	0.0446 (16)	0.0048 (14)	0.0110 (13)	−0.0019 (15)
C5	0.0325 (16)	0.077 (2)	0.064 (2)	0.0005 (16)	0.0074 (15)	−0.0017 (19)
C6	0.0357 (17)	0.075 (2)	0.0552 (19)	0.0166 (16)	−0.0017 (14)	−0.0033 (18)
C7	0.0460 (17)	0.056 (2)	0.0368 (16)	0.0067 (15)	0.0108 (13)	0.0062 (15)
C8	0.0304 (14)	0.0515 (19)	0.0357 (15)	0.0058 (14)	0.0004 (12)	0.0049 (14)
C9	0.0392 (16)	0.0481 (18)	0.0427 (16)	−0.0041 (14)	0.0066 (13)	−0.0055 (14)
C10	0.0502 (19)	0.064 (2)	0.060 (2)	−0.0023 (17)	0.0223 (16)	−0.0031 (17)
C11	0.0431 (18)	0.081 (3)	0.072 (2)	−0.0194 (19)	0.0052 (17)	0.001 (2)
C12	0.066 (2)	0.071 (2)	0.061 (2)	−0.022 (2)	−0.0085 (18)	−0.0118 (19)
C13	0.060 (2)	0.071 (2)	0.0425 (17)	−0.0004 (18)	0.0032 (15)	−0.0111 (17)
C14	0.062 (2)	0.066 (2)	0.059 (2)	−0.0170 (19)	0.0242 (18)	−0.0106 (18)
C15	0.098 (3)	0.071 (3)	0.071 (2)	−0.026 (2)	0.035 (2)	0.003 (2)

Cl1—C9	1.738 (3)	C8—C9	1.374 (3)
Cl2—C1	1.734 (3)	C9—C10	1.388 (4)
O1—C7	1.228 (4)	C10—C11	1.365 (5)
O2—C14	1.205 (4)	C11—C12	1.356 (5)
N1—C4	1.397 (3)	C12—C13	1.388 (5)
N1—C14	1.374 (4)	C14—C15	1.504 (5)
N1—H1	0.8600	C2—H2	0.9300
C1—C6	1.382 (4)	C5—H5	0.9300
C1—C2	1.375 (3)	C6—H6	0.9300
C2—C3	1.393 (4)	C10—H10	0.9300
C3—C4	1.420 (3)	C11—H11	0.9300
C3—C7	1.482 (3)	C12—H12	0.9300
C4—C5	1.394 (4)	C13—H13	0.9300
C5—C6	1.365 (4)	C15—H15A	0.9600
C7—C8	1.499 (3)	C15—H15B	0.9600
C8—C13	1.391 (4)	C15—H15C	0.9600
Cl1···C2	3.455 (3)	C13···O1x	3.407 (4)
Cl1···C3	3.423 (3)	C7···H1	2.5000
Cl1···Cl1i	3.3974 (12)	C8···H2	2.4900
Cl2···C11ii	3.650 (4)	C9···H2	2.7700
Cl1···H2iii	3.0000	C12···H15Axi	3.0900
Cl2···H6iv	2.9400	C14···H5	2.7300
Cl2···H10v	3.0500	C15···H12xii	2.9500
O1···N1	2.660 (3)	H1···O1	1.9600
O1···C13iii	3.407 (4)	H1···C7	2.5000
O2···C5	2.839 (4)	H1···H15B	2.1100
O2···C11vi	3.300 (4)	H2···Cl1x	3.0000
O1···H13vii	2.7000	H2···C8	2.4900
O1···H1	1.9600	H2···C9	2.7700
O1···H13iii	2.9000	H5···O2	2.2200
O2···H5	2.2200	H5···C14	2.7300
O2···H11vi	2.6100	H6···Cl2iv	2.9400
O2···H12vi	2.9100	H10···Cl2v	3.0500
O2···H15Aviii	2.8800	H11···O2ix	2.6100
N1···O1	2.660 (3)	H12···O2ix	2.9100
C2···Cl1	3.455 (3)	H12···C15xiii	2.9500
C2···C9	3.330 (3)	H13···O1x	2.9000
C3···Cl1	3.423 (3)	H13···O1xi	2.7000
C5···O2	2.839 (4)	H15A···O2xiv	2.8800
C9···C2	3.330 (3)	H15A···C12vii	3.0900
C11···O2ix	3.300 (4)	H15B···H1	2.1100
C11···Cl2ii	3.650 (4)
C4—N1—C14	128.8 (2)	C11—C12—C13	120.8 (3)
C14—N1—H1	116.00	C8—C13—C12	120.3 (3)
C4—N1—H1	116.00	N1—C14—C15	114.2 (3)
Cl2—C1—C6	120.6 (2)	O2—C14—N1	123.4 (3)
C2—C1—C6	119.9 (3)	O2—C14—C15	122.4 (3)
Cl2—C1—C2	119.55 (19)	C1—C2—H2	120.00
C1—C2—C3	120.8 (2)	C3—C2—H2	120.00
C2—C3—C7	117.8 (2)	C4—C5—H5	120.00
C2—C3—C4	119.1 (2)	C6—C5—H5	120.00
C4—C3—C7	123.1 (2)	C1—C6—H6	120.00
N1—C4—C5	122.4 (2)	C5—C6—H6	120.00
C3—C4—C5	118.6 (2)	C9—C10—H10	120.00
N1—C4—C3	119.0 (2)	C11—C10—H10	120.00
C4—C5—C6	120.9 (3)	C10—C11—H11	120.00
C1—C6—C5	120.8 (3)	C12—C11—H11	120.00
O1—C7—C3	122.5 (2)	C11—C12—H12	120.00
C3—C7—C8	119.9 (2)	C13—C12—H12	120.00
O1—C7—C8	117.6 (2)	C8—C13—H13	120.00
C7—C8—C13	119.0 (2)	C12—C13—H13	120.00
C9—C8—C13	117.5 (2)	C14—C15—H15A	109.00
C7—C8—C9	123.5 (2)	C14—C15—H15B	110.00
C8—C9—C10	121.9 (2)	C14—C15—H15C	109.00
Cl1—C9—C8	119.76 (18)	H15A—C15—H15B	109.00
Cl1—C9—C10	118.4 (2)	H15A—C15—H15C	109.00
C9—C10—C11	119.4 (3)	H15B—C15—H15C	110.00
C10—C11—C12	120.0 (3)
C14—N1—C4—C3	178.3 (3)	N1—C4—C5—C6	−179.7 (3)
C14—N1—C4—C5	−1.6 (4)	C3—C4—C5—C6	0.4 (4)
C4—N1—C14—O2	−3.1 (5)	C4—C5—C6—C1	−0.1 (5)
C4—N1—C14—C15	178.4 (3)	O1—C7—C8—C9	109.0 (3)
Cl2—C1—C2—C3	−178.8 (2)	O1—C7—C8—C13	−68.5 (4)
C6—C1—C2—C3	0.9 (4)	C3—C7—C8—C9	−73.8 (4)
Cl2—C1—C6—C5	179.1 (2)	C3—C7—C8—C13	108.7 (3)
C2—C1—C6—C5	−0.6 (4)	C7—C8—C9—Cl1	2.8 (4)
C1—C2—C3—C4	−0.6 (4)	C7—C8—C9—C10	−176.2 (3)
C1—C2—C3—C7	−179.3 (2)	C13—C8—C9—Cl1	−179.7 (2)
C2—C3—C4—N1	−180.0 (2)	C13—C8—C9—C10	1.4 (4)
C2—C3—C4—C5	−0.1 (4)	C7—C8—C13—C12	177.2 (3)
C7—C3—C4—N1	−1.3 (4)	C9—C8—C13—C12	−0.4 (4)
C7—C3—C4—C5	178.5 (3)	Cl1—C9—C10—C11	179.8 (2)
C2—C3—C7—O1	172.8 (3)	C8—C9—C10—C11	−1.2 (4)
C2—C3—C7—C8	−4.3 (4)	C9—C10—C11—C12	0.0 (5)
C4—C3—C7—O1	−5.8 (4)	C10—C11—C12—C13	0.9 (5)
C4—C3—C7—C8	177.1 (2)	C11—C12—C13—C8	−0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.96	2.660 (3)	138
C5—H5···O2	0.93	2.22	2.839 (4)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.96	2.660 (3)	138
C5—H5⋯O2	0.93	2.22	2.839 (4)	124