1-[2-(2,6-Dichloro-benz-yloxy)-2-(2-fur-yl)eth-yl]-1H-benzimidazole.

In the mol-ecule of the title compound, C(20)H(16)Cl(2)N(2)O(2), the planar benzimidazole ring system is oriented with respect to the furan and dichloro-benzene rings at dihedral angles of 53.39 (6) and 31.04 (5)°, respectively. In the crystal structure, inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules into centrosymmetric R(2) (2)(8) dimers. These dimers are connected via a C-H⋯π contact between the benzimidazole and the furan rings, and π-π contacts between the benz-imidazole and dichloro-benzene ring systems [centroid-centroid distances = 3.505 (1), 3.567 (1), 3.505 (1) and 3.567 (1) Å].

Related literature

For general background, see: Brammer & Feczko (1988 ▶); Özel Güven et al. (2007 ▶). For related literature, see: Song & Shin (1998 ▶); Freer et al. (1986 ▶); Peeters et al. (1996 ▶); Peeters et al. (1979 ▶); Caira et al. (2004 ▶). For ring motif details, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H16Cl2N2O2

M = 387.25

Orthorhombic,

a = 12.7720 (3) Å

b = 12.9761 (2) Å

c = 21.9732 (5) Å

V = 3641.63 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 120 (2) K

0.50 × 0.40 × 0.20 mm

Data collection

Bruker Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.835, T max = 0.929

27000 measured reflections

4181 independent reflections

3311 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.122

S = 1.10

4181 reflections

300 parameters

All H-atom parameters refined

Δρmax = 0.50 e Å−3

Δρmin = −0.49 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020758/si2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020758/si2098Isup2.hkl

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

C20H16Cl2N2O2	F000 = 1600
Mr = 387.25	Dx = 1.413 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4594 reflections
a = 12.7720 (3) Å	θ = 2.9–27.5º
b = 12.9761 (2) Å	µ = 0.37 mm−1
c = 21.9732 (5) Å	T = 120 (2) K
V = 3641.63 (13) Å3	Block, colorless
Z = 8	0.50 × 0.40 × 0.20 mm

Bruker Nonius KappaCCD diffractometer	4181 independent reflections
Radiation source: fine-focus sealed tube	3311 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
Detector resolution: 9.091 pixels mm-1	θmax = 27.8º
T = 120(2) K	θmin = 3.1º
φ and ω scans	h = −13→16
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −14→16
Tmin = 0.835, Tmax = 0.929	l = −28→22
27000 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.0688P)2 + 0.7891P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.50 e Å−3
4181 reflections	Δρmin = −0.49 e Å−3
300 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: 0.0141 (10)
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	0.52705 (4)	0.15868 (4)	0.27568 (2)	0.03062 (16)
Cl2	0.46363 (3)	0.33374 (4)	0.49707 (2)	0.02746 (16)
O1	0.44665 (9)	−0.10157 (10)	0.42074 (6)	0.0231 (3)
O2	0.36998 (8)	0.13809 (9)	0.42664 (5)	0.0192 (3)
N1	0.24117 (10)	0.14633 (11)	0.53080 (7)	0.0183 (3)
N2	0.22763 (11)	0.31228 (12)	0.56340 (7)	0.0216 (3)
C1	0.21768 (13)	0.24739 (13)	0.51763 (9)	0.0205 (4)
H1	0.1946 (14)	0.2656 (15)	0.4777 (9)	0.018 (5)*
C2	0.26218 (12)	0.24900 (13)	0.61103 (8)	0.0186 (4)
C3	0.28517 (13)	0.27431 (15)	0.67109 (9)	0.0241 (4)
H3	0.2801 (14)	0.3425 (15)	0.6832 (9)	0.018 (5)*
C4	0.31590 (13)	0.19444 (16)	0.70928 (10)	0.0270 (4)
H4	0.3323 (15)	0.2095 (16)	0.7491 (10)	0.026 (5)*
C5	0.32404 (14)	0.09079 (16)	0.68881 (9)	0.0269 (4)
H5	0.3477 (15)	0.0361 (15)	0.7160 (9)	0.026 (5)*
C6	0.30207 (13)	0.06387 (14)	0.62937 (9)	0.0223 (4)
H6	0.3068 (15)	−0.0068 (17)	0.6154 (9)	0.028 (5)*
C7	0.27122 (12)	0.14474 (13)	0.59120 (8)	0.0186 (4)
C8	0.24218 (13)	0.05901 (14)	0.48853 (9)	0.0198 (4)
H81	0.1896 (15)	0.0733 (16)	0.4578 (9)	0.026 (5)*
H82	0.2223 (14)	−0.0048 (16)	0.5104 (8)	0.020 (5)*
C9	0.34849 (12)	0.04456 (13)	0.46028 (8)	0.0178 (4)
H9	0.3996 (14)	0.0367 (14)	0.4940 (8)	0.015 (4)*
C10	0.35358 (12)	−0.05012 (13)	0.42090 (8)	0.0190 (4)
C11	0.28836 (14)	−0.09792 (15)	0.38168 (9)	0.0249 (4)
H11	0.2189 (17)	−0.0773 (17)	0.3727 (10)	0.035 (6)*
C12	0.34340 (15)	−0.18372 (15)	0.35581 (9)	0.0266 (4)
H12	0.3178 (16)	−0.2308 (17)	0.3271 (10)	0.031 (6)*
C13	0.43807 (15)	−0.18196 (15)	0.38007 (9)	0.0252 (4)
H13	0.4966 (17)	−0.2303 (18)	0.3736 (9)	0.032 (6)*
C14	0.47740 (13)	0.14762 (14)	0.41337 (9)	0.0206 (4)
H141	0.5151 (15)	0.1398 (14)	0.4508 (10)	0.019 (5)*
H142	0.4958 (16)	0.0907 (17)	0.3863 (10)	0.030 (5)*
C15	0.49591 (12)	0.25242 (13)	0.38536 (8)	0.0177 (4)
C16	0.51955 (13)	0.26642 (14)	0.32382 (8)	0.0204 (4)
C17	0.53897 (13)	0.36388 (15)	0.29854 (9)	0.0243 (4)
H17	0.5544 (16)	0.3651 (17)	0.2524 (11)	0.037 (6)*
C18	0.53539 (14)	0.45094 (15)	0.33540 (10)	0.0263 (4)
H18	0.5515 (16)	0.5199 (17)	0.3202 (10)	0.031 (6)*
C19	0.51163 (13)	0.44195 (14)	0.39651 (9)	0.0232 (4)
H19	0.5110 (15)	0.5037 (16)	0.4233 (9)	0.025 (5)*
C20	0.49238 (13)	0.34367 (14)	0.42002 (8)	0.0190 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0346 (3)	0.0290 (3)	0.0282 (3)	0.00275 (18)	−0.0013 (2)	−0.0095 (2)
Cl2	0.0261 (2)	0.0342 (3)	0.0221 (3)	−0.00255 (17)	0.00426 (17)	−0.00402 (19)
O1	0.0216 (6)	0.0225 (7)	0.0253 (7)	0.0020 (5)	0.0008 (5)	−0.0037 (5)
O2	0.0150 (5)	0.0167 (6)	0.0258 (7)	−0.0010 (4)	0.0025 (5)	0.0039 (5)
N1	0.0166 (7)	0.0175 (8)	0.0208 (8)	0.0010 (5)	0.0026 (6)	0.0011 (6)
N2	0.0190 (7)	0.0190 (8)	0.0268 (9)	0.0019 (6)	0.0037 (6)	0.0013 (6)
C1	0.0179 (8)	0.0191 (9)	0.0246 (10)	0.0015 (7)	0.0028 (7)	0.0036 (8)
C2	0.0132 (7)	0.0181 (9)	0.0246 (10)	0.0007 (6)	0.0035 (7)	−0.0012 (7)
C3	0.0175 (8)	0.0240 (10)	0.0308 (11)	0.0001 (7)	0.0023 (7)	−0.0072 (8)
C4	0.0187 (8)	0.0375 (11)	0.0249 (11)	0.0014 (7)	−0.0022 (7)	−0.0044 (9)
C5	0.0209 (8)	0.0288 (10)	0.0309 (11)	0.0035 (7)	−0.0013 (8)	0.0042 (9)
C6	0.0189 (8)	0.0202 (9)	0.0279 (10)	0.0018 (7)	0.0008 (7)	0.0019 (8)
C7	0.0125 (7)	0.0208 (9)	0.0224 (9)	0.0002 (6)	0.0021 (7)	−0.0005 (7)
C8	0.0180 (8)	0.0184 (9)	0.0228 (10)	−0.0029 (6)	0.0009 (7)	−0.0012 (7)
C9	0.0175 (8)	0.0162 (8)	0.0198 (9)	−0.0010 (6)	−0.0004 (7)	0.0017 (7)
C10	0.0189 (8)	0.0187 (9)	0.0194 (9)	0.0001 (6)	0.0034 (7)	0.0029 (7)
C11	0.0235 (9)	0.0273 (10)	0.0240 (10)	−0.0006 (7)	−0.0010 (7)	−0.0003 (8)
C12	0.0321 (10)	0.0253 (10)	0.0224 (10)	−0.0033 (8)	0.0019 (8)	−0.0047 (8)
C13	0.0304 (9)	0.0216 (9)	0.0235 (10)	0.0019 (7)	0.0060 (8)	−0.0044 (8)
C14	0.0154 (8)	0.0179 (9)	0.0285 (11)	−0.0003 (6)	0.0027 (7)	0.0026 (8)
C15	0.0118 (7)	0.0182 (9)	0.0233 (9)	0.0002 (6)	0.0006 (7)	0.0012 (7)
C16	0.0166 (8)	0.0214 (9)	0.0232 (10)	0.0002 (6)	−0.0015 (7)	−0.0027 (7)
C17	0.0214 (9)	0.0286 (10)	0.0229 (11)	−0.0012 (7)	−0.0019 (7)	0.0061 (8)
C18	0.0243 (9)	0.0203 (10)	0.0344 (11)	−0.0028 (7)	−0.0040 (8)	0.0076 (8)
C19	0.0198 (8)	0.0188 (9)	0.0311 (11)	−0.0009 (7)	−0.0033 (7)	−0.0026 (8)
C20	0.0144 (7)	0.0225 (9)	0.0200 (9)	0.0006 (6)	−0.0009 (7)	−0.0012 (7)

Cl1—C16	1.7557 (19)	C8—H82	0.99 (2)
Cl2—C20	1.7373 (19)	C9—C8	1.505 (2)
O1—C10	1.363 (2)	C9—C10	1.504 (2)
O1—C13	1.378 (2)	C9—H9	0.992 (18)
O2—C9	1.4474 (19)	C10—C11	1.350 (2)
O2—C14	1.4081 (19)	C11—C12	1.434 (3)
N1—C1	1.376 (2)	C11—H11	0.95 (2)
N1—C7	1.382 (2)	C12—H12	0.94 (2)
N1—C8	1.465 (2)	C13—C12	1.322 (3)
N2—C1	1.318 (2)	C13—H13	0.99 (2)
C1—H1	0.95 (2)	C14—H141	0.96 (2)
C2—N2	1.401 (2)	C14—H142	0.98 (2)
C2—C3	1.391 (3)	C15—C14	1.511 (2)
C2—C7	1.426 (2)	C15—C16	1.397 (3)
C3—H3	0.926 (19)	C15—C20	1.409 (2)
C4—C3	1.390 (3)	C17—C16	1.403 (3)
C4—C5	1.422 (3)	C17—C18	1.391 (3)
C4—H4	0.92 (2)	C17—H17	1.03 (2)
C5—H5	0.98 (2)	C18—H18	0.98 (2)
C6—C5	1.381 (3)	C19—C18	1.382 (3)
C6—C7	1.400 (2)	C19—H19	0.99 (2)
C6—H6	0.97 (2)	C20—C19	1.398 (2)
C8—H81	0.97 (2)
C10—O1—C13	107.64 (14)	C10—C9—H9	108.5 (10)
C14—O2—C9	111.36 (12)	O1—C10—C9	116.05 (14)
C1—N1—C7	106.07 (15)	C11—C10—O1	108.15 (15)
C1—N1—C8	127.26 (16)	C11—C10—C9	135.73 (15)
C7—N1—C8	126.52 (15)	C10—C11—C12	107.90 (16)
C1—N2—C2	103.05 (15)	C10—C11—H11	125.6 (14)
N1—C1—H1	119.8 (12)	C12—C11—H11	126.5 (14)
N2—C1—N1	115.30 (17)	C11—C12—H12	127.0 (13)
N2—C1—H1	124.9 (12)	C13—C12—C11	105.97 (18)
N2—C2—C7	110.68 (15)	C13—C12—H12	127.0 (13)
C3—C2—N2	129.52 (17)	O1—C13—H13	121.0 (12)
C3—C2—C7	119.78 (16)	C12—C13—O1	110.33 (17)
C4—C3—C2	117.14 (18)	C12—C13—H13	128.6 (12)
C4—C3—H3	123.9 (12)	O2—C14—C15	108.41 (13)
C2—C3—H3	118.9 (12)	O2—C14—H141	107.6 (12)
C3—C4—C5	122.33 (19)	O2—C14—H142	107.1 (12)
C3—C4—H4	118.7 (13)	C15—C14—H141	111.5 (12)
C5—C4—H4	119.0 (13)	C15—C14—H142	113.3 (13)
C4—C5—H5	121.1 (12)	H141—C14—H142	108.7 (17)
C6—C5—C4	121.58 (18)	C16—C15—C20	114.88 (15)
C6—C5—H5	117.3 (12)	C16—C15—C14	123.02 (16)
C5—C6—C7	115.74 (17)	C20—C15—C14	122.09 (16)
C5—C6—H6	121.8 (12)	C15—C16—C17	122.57 (16)
C7—C6—H6	122.5 (12)	C15—C16—Cl1	119.42 (13)
N1—C7—C6	131.67 (17)	C17—C16—Cl1	118.00 (14)
N1—C7—C2	104.89 (14)	C16—C17—H17	115.9 (12)
C6—C7—C2	123.42 (17)	C18—C17—C16	119.71 (18)
N1—C8—C9	111.46 (14)	C18—C17—H17	124.4 (12)
N1—C8—H81	106.7 (12)	C17—C18—H18	122.6 (13)
N1—C8—H82	109.6 (11)	C19—C18—C17	120.31 (18)
C9—C8—H81	111.2 (12)	C19—C18—H18	117.1 (13)
C9—C8—H82	109.1 (11)	C18—C19—C20	118.35 (18)
H81—C8—H82	108.7 (16)	C18—C19—H19	120.6 (12)
O2—C9—C10	112.52 (14)	C20—C19—H19	121.0 (12)
O2—C9—C8	106.10 (13)	C15—C20—Cl2	118.12 (13)
O2—C9—H9	110.0 (10)	C19—C20—C15	124.17 (17)
C8—C9—H9	107.4 (10)	C19—C20—Cl2	117.71 (14)
C10—C9—C8	112.22 (14)
C13—O1—C10—C11	0.53 (19)	C5—C6—C7—C2	−0.1 (2)
C13—O1—C10—C9	−176.90 (14)	O2—C9—C8—N1	−61.67 (18)
C10—O1—C13—C12	−1.1 (2)	O2—C9—C10—C11	−81.3 (2)
C14—O2—C9—C10	−74.57 (17)	O2—C9—C10—O1	95.24 (17)
C14—O2—C9—C8	162.36 (15)	C8—C9—C10—C11	38.3 (3)
C9—O2—C14—C15	−173.07 (14)	C8—C9—C10—O1	−145.19 (15)
C7—N1—C1—N2	−0.99 (19)	C10—C9—C8—N1	175.07 (14)
C8—N1—C1—N2	−176.72 (15)	O1—C10—C11—C12	0.1 (2)
C1—N1—C7—C2	0.65 (16)	C9—C10—C11—C12	176.83 (18)
C1—N1—C7—C6	178.95 (17)	C10—C11—C12—C13	−0.8 (2)
C8—N1—C7—C2	176.41 (14)	O1—C13—C12—C11	1.1 (2)
C8—N1—C7—C6	−5.3 (3)	C16—C15—C14—O2	−108.33 (18)
C1—N1—C8—C9	90.6 (2)	C20—C15—C14—O2	72.8 (2)
C7—N1—C8—C9	−84.3 (2)	C14—C15—C16—Cl1	0.8 (2)
C2—N2—C1—N1	0.85 (18)	C14—C15—C16—C17	−178.50 (15)
C3—C2—N2—C1	−179.27 (17)	C20—C15—C16—Cl1	179.66 (11)
C7—C2—N2—C1	−0.38 (17)	C20—C15—C16—C17	0.4 (2)
N2—C2—C3—C4	178.50 (16)	C14—C15—C20—Cl2	−1.0 (2)
C7—C2—C3—C4	−0.3 (2)	C14—C15—C20—C19	178.26 (15)
N2—C2—C7—N1	−0.18 (17)	C16—C15—C20—Cl2	−179.96 (12)
N2—C2—C7—C6	−178.66 (15)	C16—C15—C20—C19	−0.7 (2)
C3—C2—C7—N1	178.83 (14)	C18—C17—C16—Cl1	−178.99 (13)
C3—C2—C7—C6	0.3 (2)	C18—C17—C16—C15	0.3 (3)
C5—C4—C3—C2	0.0 (3)	C16—C17—C18—C19	−0.8 (3)
C3—C4—C5—C6	0.3 (3)	C20—C19—C18—C17	0.5 (3)
C7—C6—C5—C4	−0.2 (2)	Cl2—C20—C19—C18	179.51 (13)
C5—C6—C7—N1	−178.12 (16)	C15—C20—C19—C18	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Cl2i	1.00 (2)	2.76 (2)	3.7470 (19)	172.0 (15)
C1—H1···Cg1ii	0.95 (2)	2.533 (19)	3.441 (2)	158.8 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯Cl2i	1.00 (2)	2.76 (2)	3.7470 (19)	172.0 (15)
C1—H1⋯Cg1ii	0.95 (2)	2.533 (19)	3.441 (2)	158.8 (16)

Symmetry codes: (i) ; (ii) .