1-[2-(3,4-Dichloro-benz-yloxy)-2-phenyl-ethyl]-1H-benzimidazole.

In the mol-ecule of the title compound, C(22)H(18)Cl(2)N(2)O, the planar benzimidazole ring system is oriented with respect to the phenyl and dichloro-benzene rings at dihedral angles of 12.73 (3) and 36.57 (4)°, respectively. The dihedral angle between the dichloro-benzene and phenyl rings is 29.95 (6)°. There are C-H⋯π contacts between the benzimidazole and dichloro-benzene rings, between the benzimidazole and phenyl rings, and between a methylene group and the dichlorobenzene ring.

Related literature

For general background, see: Brammer & Feczko (1988 ▶); Özel Güven et al. (2007a ▶,b ▶). For related literature, see: Song & Shin (1998 ▶); Freer et al. (1986 ▶); Peeters et al. (1996 ▶, 1979a ▶,b ▶); Caira et al. (2004 ▶); Özel Güven et al. (2008a ▶,b ▶).

Experimental

Crystal data

C22H18Cl2N2O

M = 397.28

Monoclinic,

a = 14.4664 (3) Å

b = 7.3995 (2) Å

c = 19.1030 (3) Å

β = 111.653 (1)°

V = 1900.57 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 120 (2) K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker–Nonius Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.871, T max = 0.901

23210 measured reflections

4358 independent reflections

3480 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.137

S = 1.09

4358 reflections

245 parameters

H-atom parameters constrained

Δρmax = 1.00 e Å−3

Δρmin = −0.45 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; 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, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022629/dn2369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022629/dn2369Isup2.hkl

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

C22H18Cl2N2O	F000 = 824
Mr = 397.28	Dx = 1.388 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4593 reflections
a = 14.4664 (3) Å	θ = 2.9–27.5º
b = 7.3995 (2) Å	µ = 0.36 mm−1
c = 19.1030 (3) Å	T = 120 (2) K
β = 111.6530 (10)º	Block, colorless
V = 1900.57 (7) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Bruker–Nonius Kappa CCD diffractometer	4358 independent reflections
Radiation source: fine-focus sealed tube	3480 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
Detector resolution: 9.091 pixels mm-1	θmax = 27.5º
T = 120(2) K	θmin = 3.0º
φ and ω scans	h = −18→18
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −9→9
Tmin = 0.871, Tmax = 0.901	l = −24→24
23210 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0784P)2 + 0.7143P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.137	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 1.00 e Å−3
4358 reflections	Δρmin = −0.45 e Å−3
245 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (2)
Secondary atom site location: difference Fourier map

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
Cl1	0.08238 (4)	1.15550 (8)	0.12348 (3)	0.03377 (18)
Cl2	0.27151 (4)	1.15173 (8)	0.27688 (3)	0.03349 (17)
O	−0.00599 (9)	0.69157 (18)	0.39047 (7)	0.0198 (3)
N1	−0.11880 (11)	0.5111 (2)	0.25401 (8)	0.0181 (3)
N2	−0.25862 (12)	0.6632 (2)	0.18736 (9)	0.0248 (4)
C1	−0.20915 (13)	0.5751 (3)	0.24963 (11)	0.0226 (4)
H1	−0.2338	0.5577	0.2877	0.027*
C2	−0.19558 (13)	0.6596 (2)	0.14714 (10)	0.0201 (4)
C3	−0.20642 (15)	0.7361 (3)	0.07797 (10)	0.0256 (4)
H3	−0.2636	0.7999	0.0502	0.031*
C4	−0.13019 (16)	0.7146 (3)	0.05170 (10)	0.0292 (5)
H4	−0.1367	0.7643	0.0054	0.035*
C5	−0.04303 (16)	0.6198 (3)	0.09293 (11)	0.0268 (4)
H5	0.0069	0.6079	0.0735	0.032*
C6	−0.03008 (14)	0.5433 (3)	0.16255 (10)	0.0207 (4)
H6	0.0276	0.4807	0.1904	0.025*
C7	−0.10738 (13)	0.5649 (2)	0.18831 (9)	0.0177 (4)
C8	−0.04415 (13)	0.4222 (3)	0.31792 (9)	0.0189 (4)
H8A	−0.0160	0.3212	0.3002	0.023*
H8B	−0.0753	0.3751	0.3512	0.023*
C9	0.03905 (13)	0.5531 (2)	0.36165 (9)	0.0167 (4)
H9	0.0662	0.6079	0.3266	0.020*
C10	0.12201 (13)	0.4534 (2)	0.42245 (9)	0.0165 (4)
C11	0.21552 (13)	0.4418 (3)	0.41786 (10)	0.0194 (4)
H11	0.2275	0.4995	0.3788	0.023*
C12	0.29134 (14)	0.3446 (3)	0.47127 (11)	0.0231 (4)
H12	0.3537	0.3378	0.4678	0.028*
C13	0.27398 (14)	0.2579 (3)	0.52970 (10)	0.0237 (4)
H13	0.3246	0.1924	0.5653	0.028*
C14	0.18091 (15)	0.2691 (3)	0.53482 (10)	0.0246 (4)
H14	0.1692	0.2119	0.5741	0.029*
C15	0.10499 (14)	0.3660 (3)	0.48123 (10)	0.0207 (4)
H15	0.0426	0.3724	0.4846	0.025*
C16	0.04829 (15)	0.8583 (3)	0.40680 (10)	0.0225 (4)
H16A	0.1144	0.8364	0.4438	0.027*
H16B	0.0150	0.9426	0.4286	0.027*
C17	0.05701 (13)	0.9422 (2)	0.33712 (10)	0.0193 (4)
C18	−0.02613 (14)	0.9540 (2)	0.27082 (10)	0.0202 (4)
H18	−0.0877	0.9163	0.2702	0.024*
C19	−0.01811 (14)	1.0213 (3)	0.20569 (10)	0.0221 (4)
H19	−0.0739	1.0270	0.1614	0.027*
C20	0.07358 (15)	1.0803 (3)	0.20677 (10)	0.0237 (4)
C21	0.15655 (14)	1.0755 (3)	0.27335 (11)	0.0229 (4)
C22	0.14856 (14)	1.0041 (3)	0.33816 (10)	0.0216 (4)
H22	0.2044	0.9977	0.3824	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.0443 (3)	0.0369 (3)	0.0292 (3)	0.0115 (2)	0.0242 (2)	0.0078 (2)
Cl2	0.0271 (3)	0.0344 (3)	0.0450 (3)	−0.0047 (2)	0.0204 (2)	−0.0018 (2)
O	0.0211 (6)	0.0179 (7)	0.0222 (6)	−0.0002 (5)	0.0103 (5)	0.0002 (5)
N1	0.0156 (7)	0.0187 (8)	0.0181 (7)	−0.0008 (6)	0.0042 (6)	0.0008 (6)
N2	0.0180 (8)	0.0252 (9)	0.0280 (8)	0.0022 (6)	0.0050 (7)	−0.0017 (7)
C1	0.0163 (9)	0.0259 (10)	0.0250 (9)	−0.0021 (7)	0.0067 (7)	−0.0020 (8)
C2	0.0170 (9)	0.0175 (9)	0.0208 (9)	0.0003 (7)	0.0012 (7)	−0.0028 (7)
C3	0.0264 (10)	0.0206 (10)	0.0209 (9)	0.0028 (8)	−0.0017 (7)	0.0006 (7)
C4	0.0390 (12)	0.0280 (11)	0.0175 (9)	−0.0024 (9)	0.0069 (8)	0.0020 (8)
C5	0.0321 (11)	0.0271 (11)	0.0241 (10)	−0.0015 (8)	0.0138 (8)	−0.0030 (8)
C6	0.0188 (9)	0.0189 (9)	0.0220 (9)	0.0016 (7)	0.0048 (7)	−0.0032 (7)
C7	0.0170 (8)	0.0163 (9)	0.0161 (8)	−0.0018 (7)	0.0018 (6)	−0.0018 (6)
C8	0.0191 (9)	0.0180 (9)	0.0165 (8)	−0.0013 (7)	0.0030 (7)	0.0022 (7)
C9	0.0188 (8)	0.0160 (9)	0.0151 (8)	0.0017 (7)	0.0062 (6)	0.0007 (6)
C10	0.0174 (8)	0.0161 (9)	0.0138 (8)	−0.0010 (7)	0.0031 (6)	−0.0017 (6)
C11	0.0194 (9)	0.0211 (10)	0.0160 (8)	−0.0012 (7)	0.0045 (7)	0.0005 (7)
C12	0.0182 (9)	0.0247 (10)	0.0241 (9)	0.0010 (7)	0.0050 (7)	−0.0018 (7)
C13	0.0240 (9)	0.0201 (10)	0.0207 (9)	0.0026 (8)	0.0009 (7)	0.0004 (7)
C14	0.0305 (10)	0.0237 (10)	0.0190 (9)	0.0008 (8)	0.0084 (7)	0.0045 (7)
C15	0.0201 (9)	0.0221 (10)	0.0208 (9)	0.0007 (7)	0.0086 (7)	0.0017 (7)
C16	0.0277 (10)	0.0180 (10)	0.0204 (9)	−0.0024 (7)	0.0071 (7)	−0.0016 (7)
C17	0.0223 (9)	0.0121 (9)	0.0212 (9)	−0.0007 (7)	0.0055 (7)	−0.0018 (7)
C18	0.0200 (9)	0.0151 (9)	0.0246 (9)	−0.0006 (7)	0.0073 (7)	−0.0025 (7)
C19	0.0234 (9)	0.0183 (9)	0.0221 (9)	0.0041 (7)	0.0055 (7)	−0.0012 (7)
C20	0.0337 (11)	0.0185 (10)	0.0245 (9)	0.0062 (8)	0.0172 (8)	0.0002 (7)
C21	0.0221 (9)	0.0183 (10)	0.0310 (10)	0.0010 (7)	0.0128 (8)	−0.0031 (8)
C22	0.0219 (9)	0.0167 (9)	0.0232 (9)	0.0005 (7)	0.0046 (7)	−0.0023 (7)

Cl1—C20	1.7340 (19)	C9—H9	0.9800
Cl2—C21	1.7339 (19)	C11—C10	1.390 (2)
O—C9	1.429 (2)	C11—C12	1.391 (3)
O—C16	1.434 (2)	C11—H11	0.9300
N1—C1	1.363 (2)	C12—C13	1.388 (3)
N1—C7	1.383 (2)	C12—H12	0.9300
N1—C8	1.455 (2)	C13—H13	0.9300
N2—C1	1.313 (3)	C14—C13	1.388 (3)
N2—C2	1.393 (2)	C14—H14	0.9300
C1—H1	0.9300	C15—C10	1.394 (2)
C2—C3	1.392 (3)	C15—C14	1.392 (3)
C2—C7	1.413 (2)	C15—H15	0.9300
C3—C4	1.379 (3)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—H4	0.9300	C17—C16	1.516 (2)
C5—C4	1.403 (3)	C18—C17	1.391 (2)
C5—H5	0.9300	C18—H18	0.9300
C6—C5	1.393 (3)	C19—C18	1.384 (3)
C6—H6	0.9300	C19—C20	1.389 (3)
C7—C6	1.387 (3)	C19—H19	0.9300
C8—H8A	0.9700	C21—C20	1.390 (3)
C8—H8B	0.9700	C22—C17	1.395 (3)
C9—C8	1.531 (2)	C22—C21	1.389 (3)
C9—C10	1.518 (2)	C22—H22	0.9300
C9—O—C16	114.20 (14)	C15—C10—C9	121.13 (15)
C1—N1—C7	106.09 (15)	C10—C11—C12	120.52 (17)
C1—N1—C8	127.33 (15)	C10—C11—H11	119.7
C7—N1—C8	126.25 (15)	C12—C11—H11	119.7
C1—N2—C2	103.97 (15)	C13—C12—C11	120.07 (18)
N2—C1—N1	114.69 (17)	C13—C12—H12	120.0
N2—C1—H1	122.7	C11—C12—H12	120.0
N1—C1—H1	122.7	C14—C13—C12	119.79 (17)
C3—C2—N2	130.43 (17)	C14—C13—H13	120.1
C3—C2—C7	119.48 (18)	C12—C13—H13	120.1
N2—C2—C7	110.06 (16)	C13—C14—C15	120.10 (17)
C4—C3—C2	118.26 (18)	C13—C14—H14	119.9
C4—C3—H3	120.9	C15—C14—H14	119.9
C2—C3—H3	120.9	C14—C15—C10	120.35 (17)
C3—C4—C5	121.79 (18)	C14—C15—H15	119.8
C3—C4—H4	119.1	C10—C15—H15	119.8
C5—C4—H4	119.1	O—C16—C17	112.19 (14)
C6—C5—C4	121.03 (19)	O—C16—H16A	109.2
C6—C5—H5	119.5	C17—C16—H16A	109.2
C4—C5—H5	119.5	O—C16—H16B	109.2
C7—C6—C5	116.73 (17)	C17—C16—H16B	109.2
C7—C6—H6	121.6	H16A—C16—H16B	107.9
C5—C6—H6	121.6	C18—C17—C22	119.34 (17)
N1—C7—C6	132.09 (16)	C18—C17—C16	120.09 (16)
N1—C7—C2	105.19 (15)	C22—C17—C16	120.56 (16)
C6—C7—C2	122.71 (17)	C19—C18—C17	120.66 (17)
N1—C8—C9	111.26 (15)	C19—C18—H18	119.7
N1—C8—H8A	109.4	C17—C18—H18	119.7
C9—C8—H8A	109.4	C18—C19—C20	119.73 (17)
N1—C8—H8B	109.4	C18—C19—H19	120.1
C9—C8—H8B	109.4	C20—C19—H19	120.1
H8A—C8—H8B	108.0	C19—C20—C21	120.17 (17)
O—C9—C10	113.44 (13)	C19—C20—Cl1	118.70 (15)
O—C9—C8	106.58 (14)	C21—C20—Cl1	121.12 (15)
C10—C9—C8	110.51 (15)	C22—C21—C20	119.83 (17)
O—C9—H9	108.7	C22—C21—Cl2	118.88 (14)
C10—C9—H9	108.7	C20—C21—Cl2	121.27 (15)
C8—C9—H9	108.7	C21—C22—C17	120.19 (17)
C11—C10—C15	119.17 (16)	C21—C22—H22	119.9
C11—C10—C9	119.64 (15)	C17—C22—H22	119.9
C16—O—C9—C10	81.33 (18)	O—C9—C10—C11	−125.62 (17)
C16—O—C9—C8	−156.82 (14)	C8—C9—C10—C11	114.75 (18)
C9—O—C16—C17	61.95 (19)	O—C9—C10—C15	57.3 (2)
C2—N2—C1—N1	−0.7 (2)	C8—C9—C10—C15	−62.3 (2)
C1—N2—C2—C3	−177.7 (2)	C10—C11—C12—C13	0.1 (3)
C1—N2—C2—C7	0.3 (2)	C12—C11—C10—C15	−0.1 (3)
C7—N1—C1—N2	0.9 (2)	C12—C11—C10—C9	−177.28 (17)
C8—N1—C1—N2	174.54 (17)	C11—C12—C13—C14	−0.3 (3)
C1—N1—C7—C6	178.1 (2)	C15—C14—C13—C12	0.5 (3)
C8—N1—C7—C6	4.3 (3)	C14—C15—C10—C11	0.3 (3)
C1—N1—C7—C2	−0.58 (19)	C14—C15—C10—C9	177.43 (17)
C8—N1—C7—C2	−174.36 (16)	C10—C15—C14—C13	−0.5 (3)
C1—N1—C8—C9	−100.7 (2)	C18—C17—C16—O	46.3 (2)
C7—N1—C8—C9	71.8 (2)	C22—C17—C16—O	−132.13 (18)
N2—C2—C3—C4	178.49 (19)	C19—C18—C17—C22	2.0 (3)
C7—C2—C3—C4	0.6 (3)	C19—C18—C17—C16	−176.48 (17)
C3—C2—C7—N1	178.44 (16)	C20—C19—C18—C17	−1.0 (3)
N2—C2—C7—N1	0.2 (2)	C18—C19—C20—C21	−1.4 (3)
C3—C2—C7—C6	−0.4 (3)	C18—C19—C20—Cl1	177.45 (14)
N2—C2—C7—C6	−178.63 (17)	C22—C21—C20—C19	2.8 (3)
C2—C3—C4—C5	−0.5 (3)	Cl2—C21—C20—C19	−178.87 (15)
C6—C5—C4—C3	0.0 (3)	C22—C21—C20—Cl1	−176.03 (15)
C7—C6—C5—C4	0.3 (3)	Cl2—C21—C20—Cl1	2.3 (2)
N1—C7—C6—C5	−178.58 (19)	C21—C22—C17—C18	−0.5 (3)
C2—C7—C6—C5	−0.1 (3)	C21—C22—C17—C16	177.89 (17)
O—C9—C8—N1	62.89 (17)	C17—C22—C21—C20	−1.8 (3)
C10—C9—C8—N1	−173.43 (14)	C17—C22—C21—Cl2	179.81 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg3i	0.93	2.87	3.583 (2)	135
C8—H8A···Cg4ii	0.97	2.71	3.670 (2)	171
C13—H13···Cg2iii	0.93	2.68	3.474 (2)	144
C18—H18···Cg1	0.93	2.78	3.380 (2)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg3i	0.93	2.87	3.583 (2)	135
C8—H8A⋯Cg4ii	0.97	2.71	3.670 (2)	171
C13—H13⋯Cg2iii	0.93	2.68	3.474 (2)	144
C18—H18⋯Cg1	0.93	2.78	3.380 (2)	124

Symmetry codes: (i) ; (ii) ; (iii) .