3-(4-Chloro-benzo-yl)-6-(4-chloro-phen-yl)-2,4-dimethyl-benzonitrile.

In the title compound, C(22)H(15)Cl(2)NO, the terminal chloro-benzene rings are oriented at 44.51 (15) and 86.06 (17)° with respect to the central polysubstituted benzene ring, and make a dihedral angle of 49.48 (17)°with each other. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯N inter-actions.

Related literature

For background to the title compound, see: Ma (2003 ▶, 2005 ▶, 2007 ▶); Hoffmann-Röder et al. (2004 ▶). For related structures, see: Zhang et al. (2011 ▶); Fun et al. (2012 ▶); Jagadeesan et al. (2011 ▶).

Experimental

Crystal data

C22H15Cl2NO

M = 380.25

Monoclinic,

a = 7.8102 (12) Å

b = 30.032 (5) Å

c = 8.2054 (13) Å

β = 103.739 (2)°

V = 1869.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 296 K

0.39 × 0.33 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.873, T max = 0.922

11684 measured reflections

3442 independent reflections

2013 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.121

S = 1.08

3442 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036409/xu5613sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036409/xu5613Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036409/xu5613Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812036409/xu5613Isup4.cml

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

C22H15Cl2NO	F(000) = 784
Mr = 380.25	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3123 reflections
a = 7.8102 (12) Å	θ = 2.6–22.9°
b = 30.032 (5) Å	µ = 0.36 mm−1
c = 8.2054 (13) Å	T = 296 K
β = 103.739 (2)°	Block, colourless
V = 1869.6 (5) Å3	0.39 × 0.33 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3442 independent reflections
Radiation source: fine-focus sealed tube	2013 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
phi and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
Tmin = 0.873, Tmax = 0.922	k = −36→36
11684 measured reflections	l = −9→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0235P)2 + 1.9216P] where P = (Fo2 + 2Fc2)/3
3442 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.24 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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
C1	0.7995 (4)	0.21705 (10)	0.1502 (4)	0.0402 (7)
C2	0.6497 (4)	0.20687 (10)	0.2063 (4)	0.0452 (8)
H2	0.5945	0.2292	0.2535	0.054*
C3	0.5808 (4)	0.16426 (11)	0.1934 (4)	0.0525 (9)
H3	0.4806	0.1580	0.2318	0.063*
C4	0.6621 (5)	0.13136 (10)	0.1233 (4)	0.0518 (9)
C5	0.8084 (5)	0.14040 (11)	0.0632 (4)	0.0529 (9)
H5	0.8606	0.1181	0.0131	0.063*
C6	0.8767 (4)	0.18288 (10)	0.0779 (4)	0.0483 (8)
H6	0.9767	0.1889	0.0386	0.058*
C7	0.8714 (4)	0.26288 (10)	0.1663 (4)	0.0398 (7)
C8	1.0517 (4)	0.27148 (10)	0.2239 (4)	0.0442 (8)
C9	1.1199 (4)	0.31495 (11)	0.2343 (4)	0.0483 (8)
C10	1.0020 (4)	0.35035 (10)	0.1930 (4)	0.0460 (8)
C11	0.8210 (4)	0.34288 (10)	0.1389 (4)	0.0467 (8)
C12	0.7596 (4)	0.29920 (10)	0.1238 (4)	0.0451 (8)
H12	0.6394	0.2942	0.0838	0.054*
C13	1.1720 (5)	0.23601 (12)	0.2910 (5)	0.0558 (9)
C14	1.3152 (5)	0.32286 (14)	0.2910 (5)	0.0772 (12)
H14A	1.3698	0.3164	0.2005	0.116*
H14B	1.3639	0.3038	0.3845	0.116*
H14C	1.3365	0.3534	0.3241	0.116*
C15	0.6925 (5)	0.38100 (11)	0.0981 (5)	0.0646 (10)
H15A	0.5752	0.3695	0.0592	0.097*
H15B	0.7215	0.3991	0.0122	0.097*
H15C	0.6988	0.3986	0.1969	0.097*
C16	1.0722 (5)	0.39731 (11)	0.2256 (5)	0.0547 (9)
C17	1.1277 (4)	0.42252 (11)	0.0920 (4)	0.0495 (8)
C18	1.2013 (5)	0.46432 (11)	0.1290 (5)	0.0634 (10)
H18	1.2167	0.4758	0.2367	0.076*
C19	1.2517 (5)	0.48886 (12)	0.0070 (5)	0.0693 (11)
H19	1.3029	0.5167	0.0326	0.083*
C20	1.2263 (5)	0.47210 (11)	−0.1532 (5)	0.0589 (10)
C21	1.1562 (5)	0.43075 (11)	−0.1909 (5)	0.0658 (11)
H21	1.1412	0.4194	−0.2988	0.079*
C22	1.1076 (5)	0.40580 (11)	−0.0673 (5)	0.0619 (10)
H22	1.0608	0.3774	−0.0924	0.074*
Cl1	0.57545 (16)	0.07788 (3)	0.10760 (15)	0.0838 (4)
Cl2	1.28408 (16)	0.50406 (3)	−0.30697 (14)	0.0848 (4)
N1	1.2698 (4)	0.20909 (12)	0.3525 (5)	0.0805 (11)
O1	1.0819 (4)	0.41318 (9)	0.3638 (3)	0.0857 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0442 (18)	0.0436 (17)	0.0329 (18)	0.0008 (14)	0.0092 (14)	0.0012 (14)
C2	0.049 (2)	0.0429 (18)	0.045 (2)	0.0041 (15)	0.0140 (16)	−0.0021 (15)
C3	0.055 (2)	0.051 (2)	0.054 (2)	−0.0044 (17)	0.0172 (17)	0.0015 (17)
C4	0.067 (2)	0.0420 (18)	0.045 (2)	−0.0002 (17)	0.0117 (18)	0.0021 (16)
C5	0.069 (2)	0.050 (2)	0.041 (2)	0.0109 (18)	0.0164 (18)	−0.0040 (16)
C6	0.057 (2)	0.0477 (19)	0.044 (2)	0.0038 (17)	0.0204 (17)	0.0003 (16)
C7	0.0453 (19)	0.0439 (18)	0.0323 (18)	−0.0010 (15)	0.0130 (15)	−0.0001 (14)
C8	0.045 (2)	0.0508 (19)	0.040 (2)	0.0009 (16)	0.0165 (15)	−0.0008 (15)
C9	0.046 (2)	0.061 (2)	0.039 (2)	−0.0086 (17)	0.0138 (16)	−0.0054 (16)
C10	0.057 (2)	0.0502 (19)	0.0314 (19)	−0.0099 (17)	0.0125 (16)	−0.0035 (14)
C11	0.058 (2)	0.0470 (19)	0.0354 (19)	−0.0021 (16)	0.0117 (16)	0.0022 (15)
C12	0.0446 (19)	0.0485 (19)	0.042 (2)	−0.0017 (16)	0.0095 (15)	0.0012 (15)
C13	0.050 (2)	0.062 (2)	0.059 (2)	0.0008 (19)	0.0207 (19)	0.0016 (19)
C14	0.054 (2)	0.085 (3)	0.090 (3)	−0.016 (2)	0.013 (2)	−0.010 (2)
C15	0.070 (3)	0.044 (2)	0.076 (3)	0.0014 (18)	0.011 (2)	0.0032 (18)
C16	0.063 (2)	0.055 (2)	0.048 (2)	−0.0154 (18)	0.0178 (18)	−0.0095 (18)
C17	0.059 (2)	0.0467 (18)	0.044 (2)	−0.0116 (17)	0.0144 (17)	−0.0070 (16)
C18	0.083 (3)	0.053 (2)	0.057 (2)	−0.023 (2)	0.021 (2)	−0.0158 (18)
C19	0.092 (3)	0.043 (2)	0.077 (3)	−0.022 (2)	0.030 (2)	−0.010 (2)
C20	0.070 (3)	0.045 (2)	0.066 (3)	−0.0041 (18)	0.026 (2)	0.0057 (18)
C21	0.094 (3)	0.053 (2)	0.056 (2)	−0.020 (2)	0.028 (2)	−0.0097 (18)
C22	0.082 (3)	0.049 (2)	0.058 (3)	−0.0240 (19)	0.022 (2)	−0.0079 (18)
Cl1	0.1082 (9)	0.0465 (5)	0.1010 (9)	−0.0146 (5)	0.0337 (7)	−0.0085 (5)
Cl2	0.1219 (10)	0.0556 (6)	0.0896 (8)	−0.0063 (6)	0.0505 (7)	0.0130 (5)
N1	0.065 (2)	0.083 (2)	0.095 (3)	0.018 (2)	0.023 (2)	0.014 (2)
O1	0.127 (3)	0.0814 (19)	0.0601 (19)	−0.0443 (17)	0.0442 (18)	−0.0276 (15)

C1—C2	1.389 (4)	C12—H12	0.9300
C1—C6	1.393 (4)	C13—N1	1.144 (4)
C1—C7	1.481 (4)	C14—H14A	0.9600
C2—C3	1.382 (4)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.373 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.374 (5)	C15—H15C	0.9600
C4—Cl1	1.736 (3)	C16—O1	1.216 (4)
C5—C6	1.377 (4)	C16—C17	1.479 (4)
C5—H5	0.9300	C17—C22	1.374 (4)
C6—H6	0.9300	C17—C18	1.384 (4)
C7—C12	1.389 (4)	C18—C19	1.373 (5)
C7—C8	1.398 (4)	C18—H18	0.9300
C8—C9	1.405 (4)	C19—C20	1.377 (5)
C8—C13	1.440 (5)	C19—H19	0.9300
C9—C10	1.395 (4)	C20—C21	1.363 (5)
C9—C14	1.504 (5)	C20—Cl2	1.729 (3)
C10—C11	1.396 (4)	C21—C22	1.384 (5)
C10—C16	1.514 (4)	C21—H21	0.9300
C11—C12	1.392 (4)	C22—H22	0.9300
C11—C15	1.507 (4)
C2—C1—C6	117.6 (3)	C11—C12—H12	118.8
C2—C1—C7	120.4 (3)	N1—C13—C8	176.2 (4)
C6—C1—C7	122.0 (3)	C9—C14—H14A	109.5
C3—C2—C1	121.4 (3)	C9—C14—H14B	109.5
C3—C2—H2	119.3	H14A—C14—H14B	109.5
C1—C2—H2	119.3	C9—C14—H14C	109.5
C4—C3—C2	119.2 (3)	H14A—C14—H14C	109.5
C4—C3—H3	120.4	H14B—C14—H14C	109.5
C2—C3—H3	120.4	C11—C15—H15A	109.5
C3—C4—C5	121.0 (3)	C11—C15—H15B	109.5
C3—C4—Cl1	119.1 (3)	H15A—C15—H15B	109.5
C5—C4—Cl1	119.9 (3)	C11—C15—H15C	109.5
C4—C5—C6	119.3 (3)	H15A—C15—H15C	109.5
C4—C5—H5	120.3	H15B—C15—H15C	109.5
C6—C5—H5	120.3	O1—C16—C17	121.8 (3)
C5—C6—C1	121.5 (3)	O1—C16—C10	118.0 (3)
C5—C6—H6	119.3	C17—C16—C10	120.2 (3)
C1—C6—H6	119.3	C22—C17—C18	119.2 (3)
C12—C7—C8	117.5 (3)	C22—C17—C16	122.0 (3)
C12—C7—C1	120.3 (3)	C18—C17—C16	118.8 (3)
C8—C7—C1	122.2 (3)	C19—C18—C17	120.2 (3)
C7—C8—C9	121.9 (3)	C19—C18—H18	119.9
C7—C8—C13	120.4 (3)	C17—C18—H18	119.9
C9—C8—C13	117.4 (3)	C18—C19—C20	119.9 (3)
C10—C9—C8	118.4 (3)	C18—C19—H19	120.1
C10—C9—C14	121.1 (3)	C20—C19—H19	120.1
C8—C9—C14	120.5 (3)	C21—C20—C19	120.6 (3)
C9—C10—C11	121.0 (3)	C21—C20—Cl2	120.0 (3)
C9—C10—C16	118.5 (3)	C19—C20—Cl2	119.4 (3)
C11—C10—C16	120.2 (3)	C20—C21—C22	119.5 (3)
C12—C11—C10	118.8 (3)	C20—C21—H21	120.3
C12—C11—C15	119.9 (3)	C22—C21—H21	120.3
C10—C11—C15	121.3 (3)	C17—C22—C21	120.6 (3)
C7—C12—C11	122.3 (3)	C17—C22—H22	119.7
C7—C12—H12	118.8	C21—C22—H22	119.7
C6—C1—C2—C3	1.0 (5)	C16—C10—C11—C12	−174.6 (3)
C7—C1—C2—C3	−179.6 (3)	C9—C10—C11—C15	178.5 (3)
C1—C2—C3—C4	−0.2 (5)	C16—C10—C11—C15	5.1 (5)
C2—C3—C4—C5	−1.2 (5)	C8—C7—C12—C11	−0.9 (4)
C2—C3—C4—Cl1	179.9 (3)	C1—C7—C12—C11	179.2 (3)
C3—C4—C5—C6	1.8 (5)	C10—C11—C12—C7	2.4 (5)
Cl1—C4—C5—C6	−179.4 (3)	C15—C11—C12—C7	−177.3 (3)
C4—C5—C6—C1	−0.9 (5)	C7—C8—C13—N1	−119 (6)
C2—C1—C6—C5	−0.4 (5)	C9—C8—C13—N1	55 (6)
C7—C1—C6—C5	−179.9 (3)	C9—C10—C16—O1	−86.8 (4)
C2—C1—C7—C12	−44.8 (4)	C11—C10—C16—O1	86.8 (4)
C6—C1—C7—C12	134.6 (3)	C9—C10—C16—C17	92.8 (4)
C2—C1—C7—C8	135.3 (3)	C11—C10—C16—C17	−93.6 (4)
C6—C1—C7—C8	−45.3 (4)	O1—C16—C17—C22	−176.1 (4)
C12—C7—C8—C9	−1.9 (4)	C10—C16—C17—C22	4.3 (5)
C1—C7—C8—C9	178.1 (3)	O1—C16—C17—C18	3.5 (6)
C12—C7—C8—C13	171.8 (3)	C10—C16—C17—C18	−176.1 (3)
C1—C7—C8—C13	−8.3 (4)	C22—C17—C18—C19	0.7 (6)
C7—C8—C9—C10	3.0 (5)	C16—C17—C18—C19	−179.0 (4)
C13—C8—C9—C10	−170.8 (3)	C17—C18—C19—C20	1.0 (6)
C7—C8—C9—C14	−177.8 (3)	C18—C19—C20—C21	−1.9 (6)
C13—C8—C9—C14	8.4 (5)	C18—C19—C20—Cl2	178.0 (3)
C8—C9—C10—C11	−1.4 (4)	C19—C20—C21—C22	1.1 (6)
C14—C9—C10—C11	179.4 (3)	Cl2—C20—C21—C22	−178.9 (3)
C8—C9—C10—C16	172.1 (3)	C18—C17—C22—C21	−1.5 (6)
C14—C9—C10—C16	−7.1 (5)	C16—C17—C22—C21	178.1 (4)
C9—C10—C11—C12	−1.2 (5)	C20—C21—C22—C17	0.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1i	0.93	2.61	3.305 (5)	132
C5—H5···O1ii	0.93	2.53	3.390 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.93	2.61	3.305 (5)	132
C5—H5⋯O1ii	0.93	2.53	3.390 (5)	155

Symmetry codes: (i) ; (ii) .