2-(4-Chloro-anilino)-1-(4-chloro-phen-yl)ethanone.

In the title compound, C(14)H(11)Cl(2)NO, the benzene rings form a dihedral angle of 3.14 (6)°. Overall, the mol-ecule is close to being planar (r.m.s. deviation for all the non-H atoms = 0.054 Å). No significant directional inter-molecular inter-actions are observed in the crystal structure.

Related literature

For general background to amine derivatives, see: Sridharan et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C14H11Cl2NO

M = 280.14

Triclinic,

a = 5.7286 (3) Å

b = 7.4225 (5) Å

c = 15.4274 (9) Å

α = 85.337 (1)°

β = 89.772 (1)°

γ = 82.519 (1)°

V = 648.23 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.49 mm−1

T = 296 K

0.55 × 0.26 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.776, T max = 0.931

14634 measured reflections

4406 independent reflections

3279 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.121

S = 1.05

4406 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048276/hb6501sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048276/hb6501Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048276/hb6501Isup3.cml

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

C14H11Cl2NO	Z = 2
Mr = 280.14	F(000) = 288
Triclinic, P1	Dx = 1.435 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7286 (3) Å	Cell parameters from 5676 reflections
b = 7.4225 (5) Å	θ = 2.7–31.5°
c = 15.4274 (9) Å	µ = 0.49 mm−1
α = 85.337 (1)°	T = 296 K
β = 89.772 (1)°	Needle, colorless
γ = 82.519 (1)°	0.55 × 0.26 × 0.15 mm
V = 648.23 (7) Å3

Bruker SMART APEXII DUO CCD diffractometer	4406 independent reflections
Radiation source: fine-focus sealed tube	3279 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 31.9°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.776, Tmax = 0.931	k = −10→10
14634 measured reflections	l = −22→22

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) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.1078P] where P = (Fo2 + 2Fc2)/3
4406 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.31 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 > 2sigma(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
Cl1	0.53272 (7)	0.38195 (5)	0.30213 (2)	0.06177 (13)
Cl2	1.09875 (12)	0.23470 (8)	−0.52931 (3)	0.0986 (2)
O1	1.46099 (17)	0.11247 (15)	−0.11538 (6)	0.0595 (3)
N1	1.1416 (2)	0.20038 (17)	0.00358 (7)	0.0479 (3)
C1	1.0802 (2)	0.20624 (16)	0.15684 (7)	0.0414 (2)
H1A	1.2343	0.1513	0.1664	0.050*
C2	0.9398 (2)	0.24941 (18)	0.22701 (8)	0.0450 (3)
H2A	0.9990	0.2233	0.2833	0.054*
C3	0.7107 (2)	0.33154 (16)	0.21332 (8)	0.0418 (2)
C4	0.6222 (2)	0.37011 (17)	0.13004 (8)	0.0448 (3)
H4A	0.4682	0.4259	0.1213	0.054*
C5	0.7621 (2)	0.32599 (17)	0.05920 (8)	0.0428 (2)
H5A	0.7008	0.3513	0.0032	0.051*
C6	0.99495 (19)	0.24365 (14)	0.07159 (7)	0.0363 (2)
C7	1.0671 (2)	0.23121 (16)	−0.08528 (7)	0.0392 (2)
H7A	1.0121	0.3597	−0.0986	0.047*
H7B	0.9371	0.1631	−0.0946	0.047*
C8	1.2670 (2)	0.17276 (15)	−0.14502 (7)	0.0399 (2)
C9	1.2203 (2)	0.19003 (15)	−0.24018 (7)	0.0392 (2)
C10	1.3956 (2)	0.12290 (19)	−0.29565 (9)	0.0519 (3)
H10A	1.5399	0.0686	−0.2726	0.062*
C11	1.3597 (3)	0.1352 (2)	−0.38450 (9)	0.0623 (4)
H11A	1.4780	0.0889	−0.4212	0.075*
C12	1.1463 (3)	0.2168 (2)	−0.41788 (9)	0.0583 (4)
C13	0.9689 (3)	0.2858 (2)	−0.36467 (9)	0.0592 (4)
H13A	0.8257	0.3412	−0.3883	0.071*
C14	1.0057 (2)	0.27170 (19)	−0.27579 (8)	0.0497 (3)
H14A	0.8861	0.3172	−0.2394	0.060*
H1N1	1.266 (3)	0.146 (2)	0.0124 (11)	0.058 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0600 (2)	0.0724 (2)	0.0522 (2)	−0.00031 (16)	0.01890 (15)	−0.01462 (16)
Cl2	0.1357 (5)	0.1203 (4)	0.03485 (19)	0.0016 (4)	−0.0021 (2)	−0.0062 (2)
O1	0.0450 (5)	0.0820 (7)	0.0464 (5)	0.0127 (5)	−0.0019 (4)	−0.0088 (5)
N1	0.0406 (5)	0.0649 (7)	0.0342 (5)	0.0077 (5)	0.0009 (4)	−0.0032 (4)
C1	0.0368 (5)	0.0484 (6)	0.0370 (5)	0.0015 (4)	−0.0030 (4)	−0.0028 (4)
C2	0.0460 (6)	0.0537 (7)	0.0343 (5)	−0.0022 (5)	−0.0024 (4)	−0.0050 (5)
C3	0.0422 (6)	0.0426 (6)	0.0409 (5)	−0.0038 (4)	0.0072 (4)	−0.0075 (4)
C4	0.0354 (5)	0.0496 (6)	0.0472 (6)	0.0009 (5)	0.0017 (4)	−0.0003 (5)
C5	0.0382 (5)	0.0511 (6)	0.0370 (5)	−0.0008 (5)	−0.0029 (4)	0.0007 (4)
C6	0.0370 (5)	0.0370 (5)	0.0346 (5)	−0.0034 (4)	0.0006 (4)	−0.0028 (4)
C7	0.0390 (5)	0.0440 (6)	0.0342 (5)	−0.0033 (4)	0.0020 (4)	−0.0044 (4)
C8	0.0402 (5)	0.0407 (5)	0.0382 (5)	−0.0017 (4)	0.0028 (4)	−0.0051 (4)
C9	0.0424 (5)	0.0389 (5)	0.0360 (5)	−0.0036 (4)	0.0041 (4)	−0.0042 (4)
C10	0.0497 (7)	0.0587 (7)	0.0442 (6)	0.0056 (6)	0.0078 (5)	−0.0063 (5)
C11	0.0715 (9)	0.0697 (9)	0.0429 (7)	0.0045 (7)	0.0163 (6)	−0.0099 (6)
C12	0.0788 (10)	0.0608 (8)	0.0348 (6)	−0.0071 (7)	0.0034 (6)	−0.0044 (5)
C13	0.0592 (8)	0.0745 (9)	0.0408 (6)	0.0020 (7)	−0.0048 (6)	−0.0024 (6)
C14	0.0463 (6)	0.0611 (8)	0.0393 (6)	0.0028 (5)	0.0028 (5)	−0.0056 (5)

Cl1—C3	1.7406 (12)	C5—H5A	0.9300
Cl2—C12	1.7332 (14)	C7—C8	1.5091 (15)
O1—C8	1.2187 (14)	C7—H7A	0.9700
N1—C6	1.3738 (15)	C7—H7B	0.9700
N1—C7	1.4290 (15)	C8—C9	1.4855 (16)
N1—H1N1	0.780 (17)	C9—C10	1.3860 (16)
C1—C2	1.3798 (16)	C9—C14	1.3921 (17)
C1—C6	1.3985 (15)	C10—C11	1.3808 (19)
C1—H1A	0.9300	C10—H10A	0.9300
C2—C3	1.3823 (17)	C11—C12	1.374 (2)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.3774 (17)	C12—C13	1.377 (2)
C4—C5	1.3881 (17)	C13—C14	1.3817 (18)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.4000 (16)	C14—H14A	0.9300
C6—N1—C7	122.77 (10)	N1—C7—H7B	109.5
C6—N1—H1N1	120.3 (13)	C8—C7—H7B	109.5
C7—N1—H1N1	116.5 (13)	H7A—C7—H7B	108.1
C2—C1—C6	121.18 (10)	O1—C8—C9	121.31 (11)
C2—C1—H1A	119.4	O1—C8—C7	120.43 (10)
C6—C1—H1A	119.4	C9—C8—C7	118.26 (10)
C1—C2—C3	119.77 (11)	C10—C9—C14	118.66 (11)
C1—C2—H2A	120.1	C10—C9—C8	119.16 (11)
C3—C2—H2A	120.1	C14—C9—C8	122.18 (10)
C4—C3—C2	120.29 (11)	C11—C10—C9	121.18 (13)
C4—C3—Cl1	120.13 (9)	C11—C10—H10A	119.4
C2—C3—Cl1	119.56 (9)	C9—C10—H10A	119.4
C3—C4—C5	120.22 (11)	C12—C11—C10	118.92 (13)
C3—C4—H4A	119.9	C12—C11—H11A	120.5
C5—C4—H4A	119.9	C10—C11—H11A	120.5
C4—C5—C6	120.41 (10)	C11—C12—C13	121.39 (13)
C4—C5—H5A	119.8	C11—C12—Cl2	119.56 (12)
C6—C5—H5A	119.8	C13—C12—Cl2	119.05 (12)
N1—C6—C1	119.28 (10)	C12—C13—C14	119.30 (13)
N1—C6—C5	122.59 (10)	C12—C13—H13A	120.4
C1—C6—C5	118.13 (10)	C14—C13—H13A	120.4
N1—C7—C8	110.63 (10)	C13—C14—C9	120.55 (12)
N1—C7—H7A	109.5	C13—C14—H14A	119.7
C8—C7—H7A	109.5	C9—C14—H14A	119.7
C6—C1—C2—C3	−0.17 (19)	O1—C8—C9—C10	5.16 (19)
C1—C2—C3—C4	0.11 (19)	C7—C8—C9—C10	−174.56 (11)
C1—C2—C3—Cl1	178.85 (10)	O1—C8—C9—C14	−174.82 (13)
C2—C3—C4—C5	0.29 (19)	C7—C8—C9—C14	5.46 (17)
Cl1—C3—C4—C5	−178.44 (10)	C14—C9—C10—C11	−0.3 (2)
C3—C4—C5—C6	−0.64 (19)	C8—C9—C10—C11	179.70 (13)
C7—N1—C6—C1	178.89 (11)	C9—C10—C11—C12	0.5 (2)
C7—N1—C6—C5	−1.74 (19)	C10—C11—C12—C13	−0.1 (3)
C2—C1—C6—N1	179.23 (12)	C10—C11—C12—Cl2	179.61 (12)
C2—C1—C6—C5	−0.16 (18)	C11—C12—C13—C14	−0.3 (3)
C4—C5—C6—N1	−178.81 (12)	Cl2—C12—C13—C14	179.92 (12)
C4—C5—C6—C1	0.57 (18)	C12—C13—C14—C9	0.5 (2)
C6—N1—C7—C8	179.16 (11)	C10—C9—C14—C13	−0.2 (2)
N1—C7—C8—O1	−1.37 (17)	C8—C9—C14—C13	179.82 (13)
N1—C7—C8—C9	178.35 (10)