2-Chloro-N,N-diphenyl-acetamide.

In the title compound, C(14)H(12)ClNO, the central acetamide plane forms dihedral angles of 76.0 (2) and 64.0 (2)° with the phenyl rings and the phenyl rings form a dihedral angle of 71.8 (2)° with each other.

Related literature

The title compound is an important inter­mediate in the synthesis of N-phenyl-indolin-2-one, which can be further transformed to l-aryl-3-(amino­alkyl­idene)oxindoles, a new class of ‘GABAergic’ agents (Shindikar et al., 2006 ▶; Sarges et al., 1989 ▶) using a new variant of the Friedel–Crafts cyclization (Hennessy & Buchwald, 2003 ▶; Trost & Frederiksen, 2005 ▶; Trost & Yong, 2006 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.70

Orthorhombic,

a = 6.4350 (13) Å

b = 12.799 (3) Å

c = 14.944 (3) Å

V = 1230.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.917, T max = 0.971

2519 measured reflections

2231 independent reflections

1842 reflections with I > 2σ(I)

R int = 0.064

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.112

S = 1.00

2231 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 912 Friedel pairs

Flack parameter: −0.14 (9)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024052/ya2097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024052/ya2097Isup2.hkl

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

C14H12ClNO	Dx = 1.326 Mg m−3
Mr = 245.70	Melting point: 393 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.4350 (13) Å	θ = 9.0–13.0°
b = 12.799 (3) Å	µ = 0.29 mm−1
c = 14.944 (3) Å	T = 293 K
V = 1230.8 (5) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 512

Enraf–Nonius CAD-4 diffractometer	1842 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
graphite	θmax = 25.3°, θmin = 2.1°
ω/2θ scans	h = −7→0
Absorption correction: ψ scan (North et al., 1968)	k = −15→15
Tmin = 0.917, Tmax = 0.971	l = −17→0
2519 measured reflections	3 standard reflections every 200 reflections
2231 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2231 reflections	Δρmax = 0.18 e Å−3
154 parameters	Δρmin = −0.21 e Å−3
0 restraints	Absolute structure: Flack (1983), 912 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.14 (9)

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	0.97222 (13)	0.79305 (6)	0.11836 (6)	0.0621 (3)
O	1.0050 (3)	0.63002 (15)	−0.01779 (12)	0.0490 (5)
N	1.2460 (3)	0.52988 (16)	0.05137 (14)	0.0354 (5)
C1	1.6477 (5)	0.4811 (2)	0.2686 (2)	0.0543 (8)
H1A	1.7359	0.4711	0.3172	0.065*
C2	1.4544 (5)	0.4359 (2)	0.26845 (19)	0.0514 (8)
H2A	1.4111	0.3956	0.3167	0.062*
C3	1.3243 (5)	0.4509 (2)	0.19570 (17)	0.0410 (7)
H3A	1.1943	0.4193	0.1943	0.049*
C4	1.3879 (4)	0.51270 (19)	0.12568 (16)	0.0343 (6)
C5	1.5827 (5)	0.5572 (2)	0.1258 (2)	0.0485 (7)
H5A	1.6263	0.5978	0.0777	0.058*
C6	1.7120 (5)	0.5409 (3)	0.1976 (2)	0.0596 (9)
H6A	1.8439	0.5706	0.1981	0.072*
C7	1.1939 (8)	0.2816 (3)	−0.1312 (2)	0.0726 (12)
H7A	1.1834	0.2270	−0.1719	0.087*
C8	1.0262 (7)	0.3081 (3)	−0.0781 (3)	0.0695 (11)
H8A	0.9034	0.2702	−0.0825	0.083*
C9	1.0392 (5)	0.3908 (2)	−0.0181 (2)	0.0527 (8)
H9A	0.9261	0.4090	0.0174	0.063*
C10	1.2238 (5)	0.4453 (2)	−0.01240 (17)	0.0381 (7)
C11	1.3920 (5)	0.4182 (2)	−0.06415 (18)	0.0500 (8)
H11A	1.5165	0.4546	−0.0594	0.060*
C12	1.3728 (7)	0.3355 (3)	−0.1236 (2)	0.0626 (9)
H12A	1.4858	0.3170	−0.1590	0.075*
C13	1.1327 (4)	0.6186 (2)	0.04201 (16)	0.0341 (6)
C14	1.1818 (4)	0.7040 (2)	0.10923 (18)	0.0410 (6)
H14A	1.3058	0.7412	0.0905	0.049*
H14B	1.2092	0.6729	0.1672	0.049*

	U11	U22	U33	U12	U13	U23
Cl	0.0602 (5)	0.0518 (5)	0.0743 (6)	0.0188 (4)	−0.0070 (4)	−0.0153 (4)
O	0.0505 (12)	0.0557 (12)	0.0409 (10)	0.0128 (10)	−0.0121 (10)	−0.0018 (9)
N	0.0378 (12)	0.0378 (12)	0.0306 (11)	0.0016 (11)	−0.0061 (10)	−0.0002 (10)
C1	0.055 (2)	0.063 (2)	0.0450 (17)	0.0191 (17)	−0.0191 (17)	−0.0039 (16)
C2	0.066 (2)	0.0570 (18)	0.0315 (15)	0.0058 (16)	−0.0011 (15)	0.0079 (13)
C3	0.0404 (16)	0.0448 (15)	0.0377 (15)	−0.0018 (13)	0.0028 (13)	0.0058 (13)
C4	0.0360 (14)	0.0374 (13)	0.0295 (13)	0.0037 (11)	−0.0034 (12)	−0.0008 (11)
C5	0.0403 (16)	0.0593 (18)	0.0459 (17)	−0.0076 (13)	−0.0032 (14)	0.0137 (15)
C6	0.0380 (18)	0.078 (2)	0.063 (2)	−0.0050 (16)	−0.0138 (17)	−0.0025 (19)
C7	0.122 (4)	0.0484 (19)	0.047 (2)	0.006 (2)	−0.023 (2)	−0.0115 (16)
C8	0.086 (3)	0.0488 (19)	0.073 (2)	−0.020 (2)	−0.029 (2)	0.0012 (17)
C9	0.057 (2)	0.0487 (17)	0.0525 (17)	−0.0111 (16)	−0.0092 (16)	0.0001 (15)
C10	0.0508 (17)	0.0327 (14)	0.0307 (14)	0.0016 (13)	−0.0058 (13)	0.0035 (11)
C11	0.060 (2)	0.0472 (17)	0.0429 (16)	0.0021 (15)	0.0058 (16)	−0.0007 (14)
C12	0.086 (3)	0.0569 (19)	0.0447 (18)	0.012 (2)	0.000 (2)	−0.0085 (16)
C13	0.0329 (14)	0.0406 (14)	0.0288 (13)	0.0003 (12)	0.0009 (12)	0.0045 (11)
C14	0.0385 (14)	0.0403 (15)	0.0443 (15)	0.0026 (12)	0.0001 (13)	−0.0028 (13)

Cl—C14	1.771 (3)	C6—H6A	0.9300
O—C13	1.223 (3)	C7—C12	1.347 (6)
N—C13	1.357 (3)	C7—C8	1.382 (6)
N—C10	1.449 (3)	C7—H7A	0.9300
N—C4	1.454 (3)	C8—C9	1.390 (5)
C1—C2	1.372 (5)	C8—H8A	0.9300
C1—C6	1.372 (5)	C9—C10	1.380 (4)
C1—H1A	0.9300	C9—H9A	0.9300
C2—C3	1.386 (4)	C10—C11	1.375 (4)
C2—H2A	0.9300	C11—C12	1.386 (4)
C3—C4	1.374 (4)	C11—H11A	0.9300
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.377 (4)	C13—C14	1.518 (4)
C5—C6	1.374 (4)	C14—H14A	0.9700
C5—H5A	0.9300	C14—H14B	0.9700
C13—N—C10	120.3 (2)	C7—C8—C9	120.7 (3)
C13—N—C4	122.9 (2)	C7—C8—H8A	119.7
C10—N—C4	116.8 (2)	C9—C8—H8A	119.7
C2—C1—C6	120.5 (3)	C10—C9—C8	118.5 (3)
C2—C1—H1A	119.8	C10—C9—H9A	120.8
C6—C1—H1A	119.8	C8—C9—H9A	120.8
C1—C2—C3	119.4 (3)	C11—C10—C9	121.0 (3)
C1—C2—H2A	120.3	C11—C10—N	118.7 (3)
C3—C2—H2A	120.3	C9—C10—N	120.2 (3)
C4—C3—C2	119.8 (3)	C10—C11—C12	118.9 (3)
C4—C3—H3A	120.1	C10—C11—H11A	120.6
C2—C3—H3A	120.1	C12—C11—H11A	120.6
C3—C4—C5	120.6 (3)	C7—C12—C11	121.4 (4)
C3—C4—N	118.8 (2)	C7—C12—H12A	119.3
C5—C4—N	120.7 (2)	C11—C12—H12A	119.3
C6—C5—C4	119.3 (3)	O—C13—N	122.4 (2)
C6—C5—H5A	120.3	O—C13—C14	122.5 (2)
C4—C5—H5A	120.3	N—C13—C14	115.0 (2)
C1—C6—C5	120.4 (3)	C13—C14—Cl	110.84 (19)
C1—C6—H6A	119.8	C13—C14—H14A	109.5
C5—C6—H6A	119.8	Cl—C14—H14A	109.5
C12—C7—C8	119.6 (3)	C13—C14—H14B	109.5
C12—C7—H7A	120.2	Cl—C14—H14B	109.5
C8—C7—H7A	120.2	H14A—C14—H14B	108.1
C6—C1—C2—C3	0.2 (5)	C8—C9—C10—N	−178.0 (3)
C1—C2—C3—C4	−1.6 (4)	C13—N—C10—C11	116.2 (3)
C2—C3—C4—C5	2.1 (4)	C4—N—C10—C11	−65.9 (3)
C2—C3—C4—N	−178.1 (2)	C13—N—C10—C9	−66.3 (3)
C13—N—C4—C3	100.9 (3)	C4—N—C10—C9	111.6 (3)
C10—N—C4—C3	−77.0 (3)	C9—C10—C11—C12	0.9 (4)
C13—N—C4—C5	−79.4 (3)	N—C10—C11—C12	178.4 (2)
C10—N—C4—C5	102.8 (3)	C8—C7—C12—C11	−0.7 (5)
C3—C4—C5—C6	−1.3 (4)	C10—C11—C12—C7	−0.2 (5)
N—C4—C5—C6	179.0 (3)	C10—N—C13—O	2.1 (4)
C2—C1—C6—C5	0.7 (5)	C4—N—C13—O	−175.7 (2)
C4—C5—C6—C1	−0.1 (5)	C10—N—C13—C14	−175.8 (2)
C12—C7—C8—C9	1.1 (5)	C4—N—C13—C14	6.4 (4)
C7—C8—C9—C10	−0.4 (5)	O—C13—C14—Cl	23.3 (3)
C8—C9—C10—C11	−0.6 (4)	N—C13—C14—Cl	−158.8 (2)