2-(1H-Benzimidazol-2-yl)-4,6-dichloro-phenol.

The title compound, C(13)H(8)Cl(2)N(2)O, was prepared by the reaction of 3,5-dichloro-2-hy-droxy-benzaldehyde with 1,2-diamino-benzene in methanol at ambient temperature. The title mol-ecule is essentially planar, the mean deviation from the plane of the non-H atoms being 0.037 (2) Å. There is an intra-molecular O-H⋯N hydrogen bond in the mol-ecule. In the crystal, symmetry-related mol-ecules are linked through N-H⋯O hydrogen bonds, forming polymeric chains propagating in [001]. The chains are linked by π-π inter-actions involving the dichloro-phenol ring and the benzoimidazole ring system [centroid-centroid distances = 3.535 (2) and 3.724 (2) Å].

Related literature

For the preparation and crystal structures of some Schiff bases bearing a C=N double bond, see: Jeseentharani et al. (2010 ▶); Hamaker et al. (2010 ▶); Tanaka et al. (2010 ▶); Tunç et al. (2009 ▶); Khalaji et al. (2010 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H8Cl2N2O

M = 279.11

Monoclinic,

a = 11.850 (3) Å

b = 7.446 (3) Å

c = 13.947 (2) Å

β = 104.261 (3)°

V = 1192.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 298 K

0.21 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.897, T max = 0.911

6117 measured reflections

2562 independent reflections

1810 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.03

2562 reflections

167 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027844/su2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027844/su2193Isup2.hkl

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

C13H8Cl2N2O	F(000) = 568
Mr = 279.11	Dx = 1.554 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1560 reflections
a = 11.850 (3) Å	θ = 3.0–26.2°
b = 7.446 (3) Å	µ = 0.53 mm−1
c = 13.947 (2) Å	T = 298 K
β = 104.261 (3)°	Block, yellow
V = 1192.7 (6) Å3	0.21 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2562 independent reflections
Radiation source: fine-focus sealed tube	1810 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 27.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→12
Tmin = 0.897, Tmax = 0.911	k = −9→9
6117 measured reflections	l = −12→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0678P)2] where P = (Fo2 + 2Fc2)/3
2562 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.23 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 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	1.19596 (6)	0.99614 (9)	0.79805 (4)	0.0505 (2)
Cl2	1.37522 (5)	0.87011 (11)	0.48582 (5)	0.0602 (3)
N1	0.91704 (15)	0.6598 (3)	0.37972 (14)	0.0350 (4)
N2	0.85158 (15)	0.7146 (3)	0.51409 (13)	0.0361 (4)
O1	0.98220 (14)	0.8474 (2)	0.67436 (12)	0.0469 (4)
H1	0.9240	0.8028	0.6378	0.070*
C1	1.05692 (18)	0.7881 (3)	0.52982 (15)	0.0312 (5)
C2	1.06961 (18)	0.8491 (3)	0.62790 (16)	0.0337 (5)
C3	1.1788 (2)	0.9158 (3)	0.67846 (15)	0.0345 (5)
C4	1.27187 (19)	0.9217 (3)	0.63599 (16)	0.0389 (5)
H4	1.3434	0.9663	0.6713	0.047*
C5	1.25768 (19)	0.8605 (3)	0.53975 (17)	0.0376 (5)
C6	1.15119 (19)	0.7967 (3)	0.48692 (16)	0.0360 (5)
H6	1.1423	0.7590	0.4219	0.043*
C7	0.94248 (18)	0.7206 (3)	0.47531 (15)	0.0328 (5)
C8	0.79936 (19)	0.6132 (3)	0.35518 (16)	0.0352 (5)
C9	0.75956 (18)	0.6484 (3)	0.44004 (17)	0.0365 (5)
C10	0.6424 (2)	0.6198 (4)	0.43936 (19)	0.0489 (7)
H10	0.6147	0.6440	0.4949	0.059*
C11	0.5702 (2)	0.5549 (4)	0.3542 (2)	0.0584 (8)
H11	0.4922	0.5346	0.3520	0.070*
C12	0.6117 (2)	0.5182 (4)	0.2698 (2)	0.0596 (8)
H12	0.5604	0.4730	0.2135	0.071*
C13	0.7263 (2)	0.5474 (3)	0.26834 (19)	0.0485 (6)
H13	0.7532	0.5244	0.2123	0.058*
H1A	0.968 (2)	0.649 (4)	0.342 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0599 (5)	0.0604 (4)	0.0299 (3)	−0.0096 (3)	0.0084 (3)	−0.0027 (3)
Cl2	0.0373 (4)	0.0907 (6)	0.0589 (4)	−0.0105 (3)	0.0236 (3)	−0.0014 (4)
N1	0.0306 (10)	0.0409 (11)	0.0340 (10)	−0.0020 (8)	0.0090 (8)	−0.0018 (8)
N2	0.0306 (10)	0.0451 (12)	0.0341 (10)	0.0002 (9)	0.0106 (8)	0.0037 (8)
O1	0.0365 (9)	0.0717 (13)	0.0367 (9)	−0.0072 (8)	0.0171 (7)	−0.0077 (8)
C1	0.0297 (11)	0.0315 (12)	0.0326 (11)	0.0013 (9)	0.0085 (9)	0.0032 (9)
C2	0.0327 (12)	0.0374 (13)	0.0326 (11)	0.0040 (9)	0.0112 (9)	0.0065 (9)
C3	0.0384 (13)	0.0367 (13)	0.0283 (11)	0.0003 (10)	0.0077 (9)	0.0038 (9)
C4	0.0318 (13)	0.0438 (14)	0.0384 (12)	−0.0037 (10)	0.0034 (10)	0.0046 (10)
C5	0.0303 (12)	0.0433 (14)	0.0409 (13)	0.0004 (10)	0.0118 (10)	0.0048 (10)
C6	0.0349 (12)	0.0411 (14)	0.0338 (11)	−0.0007 (10)	0.0123 (10)	−0.0020 (10)
C7	0.0331 (12)	0.0339 (12)	0.0320 (11)	0.0028 (10)	0.0088 (9)	0.0043 (9)
C8	0.0299 (12)	0.0370 (13)	0.0382 (12)	0.0004 (9)	0.0073 (9)	0.0048 (10)
C9	0.0281 (12)	0.0399 (13)	0.0402 (12)	0.0007 (10)	0.0058 (10)	0.0074 (10)
C10	0.0343 (13)	0.0657 (18)	0.0486 (15)	−0.0014 (12)	0.0138 (11)	0.0071 (12)
C11	0.0297 (13)	0.082 (2)	0.0626 (18)	−0.0054 (14)	0.0087 (13)	0.0066 (15)
C12	0.0426 (16)	0.075 (2)	0.0530 (16)	−0.0102 (14)	−0.0035 (13)	−0.0045 (14)
C13	0.0425 (15)	0.0583 (17)	0.0435 (14)	−0.0053 (13)	0.0082 (11)	−0.0039 (12)

Cl1—C3	1.736 (2)	C4—C5	1.388 (3)
Cl2—C5	1.740 (2)	C4—H4	0.9300
N1—C7	1.370 (3)	C5—C6	1.379 (3)
N1—C8	1.395 (3)	C6—H6	0.9300
N1—H1A	0.90 (3)	C8—C13	1.393 (3)
N2—C7	1.320 (3)	C8—C9	1.403 (3)
N2—C9	1.394 (3)	C9—C10	1.402 (3)
O1—C2	1.350 (2)	C10—C11	1.369 (4)
O1—H1	0.8200	C10—H10	0.9300
C1—C6	1.393 (3)	C11—C12	1.409 (4)
C1—C2	1.414 (3)	C11—H11	0.9300
C1—C7	1.470 (3)	C12—C13	1.380 (4)
C2—C3	1.403 (3)	C12—H12	0.9300
C3—C4	1.375 (3)	C13—H13	0.9300
C7—N1—C8	106.74 (18)	C1—C6—H6	119.6
C7—N1—H1A	125 (2)	N2—C7—N1	112.43 (19)
C8—N1—H1A	128 (2)	N2—C7—C1	122.80 (19)
C7—N2—C9	106.08 (18)	N1—C7—C1	124.77 (19)
C2—O1—H1	109.5	C13—C8—N1	132.1 (2)
C6—C1—C2	119.70 (19)	C13—C8—C9	122.2 (2)
C6—C1—C7	121.93 (19)	N1—C8—C9	105.67 (19)
C2—C1—C7	118.35 (19)	N2—C9—C10	130.6 (2)
O1—C2—C3	118.9 (2)	N2—C9—C8	109.08 (19)
O1—C2—C1	123.35 (19)	C10—C9—C8	120.3 (2)
C3—C2—C1	117.71 (19)	C11—C10—C9	117.7 (2)
C4—C3—C2	122.2 (2)	C11—C10—H10	121.1
C4—C3—Cl1	119.11 (17)	C9—C10—H10	121.1
C2—C3—Cl1	118.67 (17)	C10—C11—C12	121.4 (2)
C3—C4—C5	119.1 (2)	C10—C11—H11	119.3
C3—C4—H4	120.4	C12—C11—H11	119.3
C5—C4—H4	120.4	C13—C12—C11	121.9 (2)
C6—C5—C4	120.4 (2)	C13—C12—H12	119.0
C6—C5—Cl2	120.51 (18)	C11—C12—H12	119.0
C4—C5—Cl2	119.04 (17)	C12—C13—C8	116.5 (2)
C5—C6—C1	120.8 (2)	C12—C13—H13	121.8
C5—C6—H6	119.6	C8—C13—H13	121.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.85	2.582 (2)	148
N1—H1A···O1i	0.90 (3)	2.39 (2)	3.145 (2)	143 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.85	2.582 (2)	148
N1—H1A⋯O1i	0.90 (3)	2.39 (2)	3.145 (2)	143 (3)

Symmetry code: (i) .