2-(2-Chloro-phen-yl)-2-oxo-N-phenyl-acetamide.

In the title compound, C(14)H(10)ClNO(2), the dihedral angle between the two rings is 59.4 (2)°. The two carbonyl groups are oriented almost anti-periplanar to each other, with a torsion angle of -160.43 (2)°. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯O hydrogen bonds.

Related literature

The crystal structure of the title compound was determined within a project on the synthesis of new phenylacetamides, see: Li & Wu (2010 ▶).

Experimental

Crystal data

C14H10ClNO2

M = 259.68

Monoclinic,

a = 11.3513 (11) Å

b = 10.4585 (8) Å

c = 10.2944 (10) Å

β = 100.954 (10)°

V = 1199.86 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.48 × 0.39 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.860, T max = 0.928

5282 measured reflections

2201 independent reflections

1562 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.01

2201 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044886/nc2246sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044886/nc2246Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044886/nc2246Isup3.cml

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

C14H10ClNO2	F(000) = 536
Mr = 259.68	Dx = 1.438 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1968 reflections
a = 11.3513 (11) Å	θ = 3.5–29.2°
b = 10.4585 (8) Å	µ = 0.31 mm−1
c = 10.2944 (10) Å	T = 293 K
β = 100.954 (10)°	Block, yellow
V = 1199.86 (19) Å3	0.48 × 0.39 × 0.25 mm
Z = 4

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	2201 independent reflections
Radiation source: fine-focus sealed tube	1562 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 10.3592 pixels mm-1	θmax = 25.4°, θmin = 3.6°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→12
Tmin = 0.860, Tmax = 0.928	l = −12→7
5282 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0552P)2] where P = (Fo2 + 2Fc2)/3
2201 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 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
Cl	0.39169 (4)	0.11424 (5)	0.07892 (5)	0.0671 (2)
O1	0.12583 (11)	0.05846 (11)	−0.01363 (12)	0.0534 (4)
O2	0.04597 (11)	0.32465 (12)	−0.20894 (12)	0.0556 (4)
N	−0.05486 (12)	0.13663 (13)	−0.20367 (13)	0.0438 (4)
H	−0.0482	0.0637	−0.1643	0.053*
C1	0.13889 (17)	0.38201 (17)	0.07314 (17)	0.0505 (5)
H1	0.0609	0.3986	0.0295	0.061*
C2	0.1960 (2)	0.46949 (19)	0.16282 (18)	0.0627 (5)
H2	0.1563	0.5432	0.1811	0.075*
C3	0.3117 (2)	0.4475 (2)	0.2250 (2)	0.0697 (6)
H3	0.3508	0.5067	0.2856	0.084*
C4	0.37045 (18)	0.3389 (2)	0.19889 (19)	0.0637 (6)
H4	0.4495	0.3254	0.2407	0.076*
C5	0.31215 (15)	0.24881 (17)	0.10994 (18)	0.0483 (5)
C6	0.19425 (14)	0.26908 (16)	0.04560 (16)	0.0409 (4)
C7	0.12143 (13)	0.17184 (16)	−0.03847 (16)	0.0404 (4)
C8	0.03285 (14)	0.22088 (16)	−0.16030 (16)	0.0406 (4)
C9	−0.15676 (14)	0.15162 (15)	−0.30543 (16)	0.0386 (4)
C10	−0.24427 (14)	0.05916 (17)	−0.31498 (16)	0.0449 (4)
H10	−0.2331	−0.0109	−0.2583	0.054*
C11	−0.34801 (16)	0.07007 (19)	−0.40792 (19)	0.0572 (5)
H11	−0.4074	0.0080	−0.4135	0.069*
C12	−0.36407 (17)	0.1729 (2)	−0.49283 (19)	0.0609 (5)
H12	−0.4345	0.1806	−0.5553	0.073*
C13	−0.27627 (18)	0.26376 (18)	−0.48528 (18)	0.0567 (5)
H13	−0.2874	0.3326	−0.5436	0.068*
C14	−0.17155 (16)	0.25492 (16)	−0.39263 (17)	0.0480 (5)
H14	−0.1120	0.3166	−0.3884	0.058*

	U11	U22	U33	U12	U13	U23
Cl	0.0447 (3)	0.0726 (4)	0.0818 (4)	0.0070 (2)	0.0062 (2)	0.0104 (3)
O1	0.0500 (7)	0.0414 (7)	0.0634 (8)	−0.0033 (6)	−0.0028 (6)	0.0056 (6)
O2	0.0601 (8)	0.0440 (8)	0.0578 (8)	−0.0130 (6)	−0.0017 (6)	0.0081 (6)
N	0.0394 (8)	0.0385 (8)	0.0499 (9)	−0.0037 (6)	−0.0002 (7)	0.0092 (6)
C1	0.0499 (11)	0.0514 (11)	0.0501 (11)	−0.0042 (9)	0.0089 (9)	−0.0006 (9)
C2	0.0786 (15)	0.0572 (12)	0.0541 (12)	−0.0067 (11)	0.0174 (11)	−0.0115 (10)
C3	0.0906 (17)	0.0681 (15)	0.0469 (11)	−0.0216 (13)	0.0042 (11)	−0.0083 (10)
C4	0.0551 (12)	0.0788 (15)	0.0501 (11)	−0.0204 (11)	−0.0075 (9)	0.0080 (11)
C5	0.0444 (10)	0.0534 (11)	0.0467 (10)	−0.0062 (8)	0.0077 (8)	0.0080 (8)
C6	0.0405 (9)	0.0438 (10)	0.0384 (9)	−0.0047 (8)	0.0074 (7)	0.0050 (7)
C7	0.0352 (9)	0.0402 (10)	0.0466 (10)	−0.0006 (7)	0.0100 (7)	0.0030 (8)
C8	0.0385 (9)	0.0397 (10)	0.0441 (10)	−0.0034 (8)	0.0087 (7)	0.0006 (8)
C9	0.0367 (9)	0.0397 (9)	0.0390 (9)	0.0038 (7)	0.0063 (7)	−0.0013 (7)
C10	0.0412 (10)	0.0442 (10)	0.0485 (10)	−0.0028 (8)	0.0070 (8)	0.0030 (8)
C11	0.0412 (10)	0.0627 (13)	0.0632 (12)	−0.0080 (9)	−0.0013 (9)	−0.0011 (10)
C12	0.0484 (11)	0.0669 (13)	0.0597 (12)	0.0075 (10)	−0.0091 (9)	−0.0009 (10)
C13	0.0666 (13)	0.0495 (11)	0.0496 (11)	0.0108 (10)	−0.0002 (10)	0.0076 (8)
C14	0.0524 (11)	0.0401 (10)	0.0497 (11)	−0.0034 (8)	0.0053 (9)	0.0023 (8)

Cl—C5	1.7342 (19)	C5—C6	1.392 (2)
O1—C7	1.2120 (19)	C6—C7	1.481 (2)
O2—C8	1.2161 (19)	C7—C8	1.539 (2)
N—C8	1.341 (2)	C9—C10	1.376 (2)
N—C9	1.414 (2)	C9—C14	1.394 (2)
N—H	0.8600	C10—C11	1.374 (2)
C1—C2	1.372 (3)	C10—H10	0.9300
C1—C6	1.392 (2)	C11—C12	1.376 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.366 (3)	C12—C13	1.369 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.370 (3)	C13—C14	1.378 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.391 (3)	C14—H14	0.9300
C4—H4	0.9300
C8—N—C9	128.68 (14)	C6—C7—C8	116.93 (14)
C8—N—H	115.7	O2—C8—N	126.20 (15)
C9—N—H	115.7	O2—C8—C7	121.39 (14)
C2—C1—C6	121.93 (18)	N—C8—C7	112.41 (14)
C2—C1—H1	119.0	C10—C9—C14	120.10 (15)
C6—C1—H1	119.0	C10—C9—N	116.92 (14)
C3—C2—C1	119.5 (2)	C14—C9—N	122.98 (15)
C3—C2—H2	120.3	C11—C10—C9	120.19 (17)
C1—C2—H2	120.3	C11—C10—H10	119.9
C2—C3—C4	120.56 (18)	C9—C10—H10	119.9
C2—C3—H3	119.7	C10—C11—C12	119.99 (18)
C4—C3—H3	119.7	C10—C11—H11	120.0
C3—C4—C5	120.16 (19)	C12—C11—H11	120.0
C3—C4—H4	119.9	C13—C12—C11	119.97 (17)
C5—C4—H4	119.9	C13—C12—H12	120.0
C4—C5—C6	120.28 (18)	C11—C12—H12	120.0
C4—C5—Cl	118.15 (15)	C12—C13—C14	121.04 (17)
C6—C5—Cl	121.54 (14)	C12—C13—H13	119.5
C5—C6—C1	117.56 (15)	C14—C13—H13	119.5
C5—C6—C7	123.55 (16)	C13—C14—C9	118.68 (16)
C1—C6—C7	118.56 (14)	C13—C14—H14	120.7
O1—C7—C6	123.52 (14)	C9—C14—H14	120.7
O1—C7—C8	119.50 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N—H···O1i	0.86	2.52	3.241 (4)	141.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H⋯O1i	0.86	2.52	3.241 (4)	141

Symmetry code: (i) .