3-[1-(3-Hy-droxy-benz-yl)-1H-benzimid-azol-2-yl]phenol dimethyl sulfoxide monosolvate.

Crystals of the title compound were obtained as a 1:1 dimethyl sulfoxide solvate, C(20)H(16)N(2)O(2)·C(2)H(6)O. The mol-ecular conformation of the organic mol-ecule is similar to that in the previously reported unsolvated structure [Eltayeb et al. (2009 ▶). Acta Cryst. E65, o1374-o1375]. Thus, the dihedral angles formed by the benzimidazole moiety with the two benzene rings are 57.54 (4) and 76.22 (5)°, and the dihedral angle between the benzene rings is 89.23 (5)°. In the crystal, a three-dimensional network features O-H⋯O, O-H⋯N and O-H⋯S hydrogen bonds, as well as C-H⋯O and C-H⋯π inter-actions.

Related literature

For potential applications of benzimidazoles in medicine, see: Narasimhan et al. (2012 ▶); Alper et al. (2003 ▶); Sharma et al. (2011 ▶). For coordination compounds of benzimidazole deriv­atives, see: Tellez et al. (2008 ▶). For the crystal structure of 3-[1-(3-hy­droxy­benz­yl)-1H-benzimidazol-2-yl]phenol, see: Eltayeb et al. (2009 ▶).

Experimental

Crystal data

C20H16N2O2·C2H6OS

M = 394.48

Triclinic,

a = 8.892 (1) Å

b = 9.1951 (10) Å

c = 13.1515 (14) Å

α = 85.399 (2)°

β = 71.947 (2)°

γ = 77.442 (2)°

V = 997.81 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 298 K

0.36 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: analytical (SHELXTL; Sheldrick, 2008 ▶) T min = 0.618, T max = 0.752

8327 measured reflections

3656 independent reflections

2912 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.00

3656 reflections

261 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.32 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/S1600536812040275/tk5153sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040275/tk5153Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812040275/tk5153Isup3.cml

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

C20H16N2O2·C2H6OS	Z = 2
Mr = 394.48	F(000) = 416
Triclinic, P1	Dx = 1.313 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.892 (1) Å	Cell parameters from 4929 reflections
b = 9.1951 (10) Å	θ = 2.5–25.4°
c = 13.1515 (14) Å	µ = 0.19 mm−1
α = 85.399 (2)°	T = 298 K
β = 71.947 (2)°	Prism, colourless
γ = 77.442 (2)°	0.36 × 0.24 × 0.20 mm
V = 997.81 (19) Å3

Bruker SMART APEX CCD area-detector diffractometer	3656 independent reflections
Radiation source: fine-focus sealed tube	2912 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 0.83 pixels mm-1	θmax = 25.4°, θmin = 1.6°
ω scans	h = −10→10
Absorption correction: analytical (SHELXTL; Sheldrick, 2008)	k = −11→11
Tmin = 0.618, Tmax = 0.752	l = −15→15
8327 measured reflections

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) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0674P)2] where P = (Fo2 + 2Fc2)/3
3656 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.23 e Å−3
2 restraints	Δρmin = −0.32 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
S1	0.19023 (5)	0.03592 (5)	0.01994 (4)	0.05482 (17)
O1	0.06161 (15)	0.77881 (14)	0.21845 (10)	0.0553 (3)
H1	−0.002 (2)	0.8399 (19)	0.2668 (13)	0.066*
O2	0.15779 (16)	0.67344 (14)	0.95005 (9)	0.0580 (3)
H2	0.201 (2)	0.7438 (18)	0.9583 (16)	0.070*
O3	0.29883 (16)	−0.10268 (15)	−0.03524 (10)	0.0635 (4)
N1	0.31522 (15)	0.88121 (14)	0.49775 (10)	0.0394 (3)
C2	0.21131 (18)	0.90591 (18)	0.59903 (12)	0.0393 (4)
N3	0.15587 (16)	1.04883 (15)	0.61919 (10)	0.0431 (3)
C4	0.2058 (2)	1.27426 (19)	0.50197 (15)	0.0524 (4)
H4	0.1374	1.3442	0.5519	0.063*
C5	0.2900 (2)	1.3174 (2)	0.40181 (16)	0.0585 (5)
H5	0.2778	1.4182	0.3837	0.070*
C6	0.3932 (2)	1.2133 (2)	0.32689 (15)	0.0590 (5)
H6	0.4492	1.2463	0.2600	0.071*
C7	0.4145 (2)	1.0629 (2)	0.34927 (14)	0.0526 (4)
H7	0.4840	0.9934	0.2994	0.063*
C8	0.32694 (19)	1.01973 (18)	0.45009 (13)	0.0417 (4)
C9	0.22605 (19)	1.12258 (18)	0.52616 (13)	0.0428 (4)
C10	0.4119 (2)	0.74040 (19)	0.45014 (13)	0.0455 (4)
H10A	0.3916	0.6610	0.5026	0.055*
H10B	0.5254	0.7442	0.4324	0.055*
C11	0.37785 (18)	0.70334 (17)	0.35053 (12)	0.0389 (4)
C12	0.23086 (19)	0.75994 (17)	0.33238 (12)	0.0400 (4)
H12	0.1509	0.8236	0.3818	0.048*
C13	0.2017 (2)	0.72253 (17)	0.24104 (12)	0.0421 (4)
C14	0.3202 (2)	0.62518 (19)	0.16856 (13)	0.0506 (4)
H14	0.3013	0.5981	0.1077	0.061*
C15	0.4652 (2)	0.5692 (2)	0.18709 (14)	0.0537 (5)
H15	0.5444	0.5039	0.1383	0.064*
C16	0.4962 (2)	0.60800 (19)	0.27712 (13)	0.0482 (4)
H16	0.5959	0.5702	0.2881	0.058*
C17	0.16366 (18)	0.78669 (18)	0.67598 (12)	0.0404 (4)
C18	0.18420 (18)	0.78701 (17)	0.77632 (12)	0.0410 (4)
H18	0.2303	0.8601	0.7927	0.049*
C19	0.13664 (19)	0.67954 (18)	0.85205 (12)	0.0429 (4)
C20	0.0629 (2)	0.57380 (19)	0.82858 (14)	0.0498 (4)
H20	0.0278	0.5028	0.8798	0.060*
C21	0.0419 (2)	0.5743 (2)	0.72924 (15)	0.0554 (5)
H21	−0.0072	0.5029	0.7136	0.066*
C22	0.0925 (2)	0.6792 (2)	0.65240 (14)	0.0524 (4)
H22	0.0788	0.6777	0.5852	0.063*
C23	0.2768 (3)	0.0778 (2)	0.11599 (16)	0.0656 (5)
H23A	0.2826	−0.0043	0.1655	0.098*
H23B	0.2112	0.1656	0.1540	0.098*
H23C	0.3835	0.0949	0.0804	0.098*
C24	0.2345 (3)	0.1831 (3)	−0.07215 (18)	0.0875 (7)
H24A	0.3493	0.1756	−0.0984	0.131*
H24B	0.1844	0.2768	−0.0372	0.131*
H24C	0.1936	0.1767	−0.1309	0.131*

	U11	U22	U33	U12	U13	U23
S1	0.0502 (3)	0.0617 (3)	0.0535 (3)	−0.0095 (2)	−0.0182 (2)	−0.0014 (2)
O1	0.0558 (8)	0.0622 (8)	0.0513 (7)	−0.0008 (6)	−0.0261 (6)	−0.0111 (6)
O2	0.0754 (9)	0.0598 (8)	0.0412 (7)	−0.0147 (7)	−0.0218 (6)	0.0059 (6)
O3	0.0678 (8)	0.0618 (8)	0.0617 (8)	−0.0089 (7)	−0.0206 (7)	−0.0126 (6)
N1	0.0410 (7)	0.0417 (8)	0.0385 (7)	−0.0093 (6)	−0.0155 (6)	−0.0009 (6)
C2	0.0398 (8)	0.0451 (9)	0.0378 (8)	−0.0094 (7)	−0.0176 (7)	−0.0025 (7)
N3	0.0457 (8)	0.0430 (8)	0.0430 (7)	−0.0095 (6)	−0.0160 (6)	−0.0011 (6)
C4	0.0572 (11)	0.0447 (10)	0.0618 (11)	−0.0121 (8)	−0.0259 (9)	−0.0007 (8)
C5	0.0646 (12)	0.0502 (11)	0.0734 (13)	−0.0230 (10)	−0.0350 (11)	0.0155 (10)
C6	0.0592 (11)	0.0679 (13)	0.0573 (11)	−0.0285 (10)	−0.0220 (10)	0.0174 (10)
C7	0.0501 (10)	0.0625 (12)	0.0474 (10)	−0.0175 (9)	−0.0145 (8)	0.0022 (9)
C8	0.0422 (9)	0.0468 (9)	0.0429 (9)	−0.0135 (7)	−0.0198 (7)	0.0019 (7)
C9	0.0442 (9)	0.0454 (9)	0.0465 (9)	−0.0134 (7)	−0.0218 (8)	0.0006 (7)
C10	0.0413 (9)	0.0474 (9)	0.0479 (9)	−0.0035 (7)	−0.0168 (8)	−0.0021 (8)
C11	0.0409 (8)	0.0348 (8)	0.0392 (8)	−0.0087 (7)	−0.0098 (7)	0.0028 (7)
C12	0.0398 (8)	0.0372 (8)	0.0406 (9)	−0.0054 (7)	−0.0093 (7)	−0.0046 (7)
C13	0.0478 (9)	0.0380 (9)	0.0420 (9)	−0.0103 (7)	−0.0154 (7)	0.0023 (7)
C14	0.0649 (12)	0.0473 (10)	0.0381 (9)	−0.0087 (9)	−0.0138 (8)	−0.0057 (8)
C15	0.0560 (11)	0.0495 (10)	0.0446 (10)	0.0003 (9)	−0.0052 (8)	−0.0069 (8)
C16	0.0414 (9)	0.0478 (10)	0.0490 (10)	−0.0033 (8)	−0.0086 (8)	0.0003 (8)
C17	0.0382 (8)	0.0424 (9)	0.0413 (9)	−0.0068 (7)	−0.0136 (7)	−0.0012 (7)
C18	0.0394 (8)	0.0409 (9)	0.0427 (9)	−0.0065 (7)	−0.0126 (7)	−0.0035 (7)
C19	0.0416 (9)	0.0419 (9)	0.0412 (9)	−0.0003 (7)	−0.0120 (7)	−0.0013 (7)
C20	0.0529 (10)	0.0400 (9)	0.0506 (10)	−0.0088 (8)	−0.0085 (8)	0.0042 (8)
C21	0.0616 (11)	0.0486 (10)	0.0621 (11)	−0.0227 (9)	−0.0190 (9)	−0.0030 (9)
C22	0.0604 (11)	0.0569 (11)	0.0483 (10)	−0.0207 (9)	−0.0222 (9)	−0.0011 (8)
C23	0.0727 (13)	0.0642 (13)	0.0660 (13)	−0.0122 (10)	−0.0292 (11)	−0.0068 (10)
C24	0.0954 (18)	0.0770 (16)	0.0777 (16)	−0.0072 (14)	−0.0207 (14)	0.0205 (13)

S1—O3	1.5040 (14)	C11—C12	1.383 (2)
S1—C24	1.768 (2)	C11—C16	1.383 (2)
S1—C23	1.7739 (18)	C12—C13	1.388 (2)
O1—C13	1.353 (2)	C12—H12	0.9300
O1—H1	0.857 (9)	C13—C14	1.387 (2)
O2—C19	1.3541 (19)	C14—C15	1.368 (3)
O2—H2	0.848 (9)	C14—H14	0.9300
N1—C2	1.3689 (19)	C15—C16	1.385 (2)
N1—C8	1.384 (2)	C15—H15	0.9300
N1—C10	1.456 (2)	C16—H16	0.9300
C2—N3	1.317 (2)	C17—C22	1.385 (2)
C2—C17	1.471 (2)	C17—C18	1.388 (2)
N3—C9	1.387 (2)	C18—C19	1.382 (2)
C4—C5	1.374 (3)	C18—H18	0.9300
C4—C9	1.391 (2)	C19—C20	1.386 (2)
C4—H4	0.9300	C20—C21	1.375 (2)
C5—C6	1.392 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.380 (2)
C6—C7	1.375 (3)	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.390 (2)	C23—H23A	0.9600
C7—H7	0.9300	C23—H23B	0.9600
C8—C9	1.388 (2)	C23—H23C	0.9600
C10—C11	1.512 (2)	C24—H24A	0.9600
C10—H10A	0.9700	C24—H24B	0.9600
C10—H10B	0.9700	C24—H24C	0.9600
O3—S1—C24	105.19 (10)	O1—C13—C14	117.93 (14)
O3—S1—C23	106.18 (9)	O1—C13—C12	122.59 (14)
C24—S1—C23	98.83 (11)	C14—C13—C12	119.47 (15)
C13—O1—H1	110.5 (14)	C15—C14—C13	119.66 (15)
C19—O2—H2	111.5 (14)	C15—C14—H14	120.2
C2—N1—C8	106.73 (13)	C13—C14—H14	120.2
C2—N1—C10	128.31 (13)	C14—C15—C16	121.20 (16)
C8—N1—C10	124.60 (13)	C14—C15—H15	119.4
N3—C2—N1	112.33 (14)	C16—C15—H15	119.4
N3—C2—C17	123.64 (14)	C11—C16—C15	119.50 (16)
N1—C2—C17	124.01 (14)	C11—C16—H16	120.3
C2—N3—C9	105.51 (13)	C15—C16—H16	120.3
C5—C4—C9	117.81 (18)	C22—C17—C18	119.58 (15)
C5—C4—H4	121.1	C22—C17—C2	121.67 (14)
C9—C4—H4	121.1	C18—C17—C2	118.67 (14)
C4—C5—C6	121.35 (17)	C19—C18—C17	120.52 (15)
C4—C5—H5	119.3	C19—C18—H18	119.7
C6—C5—H5	119.3	C17—C18—H18	119.7
C7—C6—C5	121.67 (17)	O2—C19—C18	122.55 (15)
C7—C6—H6	119.2	O2—C19—C20	117.87 (15)
C5—C6—H6	119.2	C18—C19—C20	119.58 (15)
C6—C7—C8	116.73 (18)	C21—C20—C19	119.72 (16)
C6—C7—H7	121.6	C21—C20—H20	120.1
C8—C7—H7	121.6	C19—C20—H20	120.1
N1—C8—C9	105.65 (14)	C20—C21—C22	120.98 (16)
N1—C8—C7	132.22 (16)	C20—C21—H21	119.5
C9—C8—C7	122.13 (16)	C22—C21—H21	119.5
N3—C9—C8	109.77 (14)	C21—C22—C17	119.58 (16)
N3—C9—C4	129.92 (16)	C21—C22—H22	120.2
C8—C9—C4	120.29 (16)	C17—C22—H22	120.2
N1—C10—C11	113.71 (13)	S1—C23—H23A	109.5
N1—C10—H10A	108.8	S1—C23—H23B	109.5
C11—C10—H10A	108.8	H23A—C23—H23B	109.5
N1—C10—H10B	108.8	S1—C23—H23C	109.5
C11—C10—H10B	108.8	H23A—C23—H23C	109.5
H10A—C10—H10B	107.7	H23B—C23—H23C	109.5
C12—C11—C16	119.56 (15)	S1—C24—H24A	109.5
C12—C11—C10	121.69 (14)	S1—C24—H24B	109.5
C16—C11—C10	118.74 (14)	H24A—C24—H24B	109.5
C11—C12—C13	120.60 (15)	S1—C24—H24C	109.5
C11—C12—H12	119.7	H24A—C24—H24C	109.5
C13—C12—H12	119.7	H24B—C24—H24C	109.5
C8—N1—C2—N3	0.23 (17)	N1—C10—C11—C16	156.07 (14)
C10—N1—C2—N3	173.56 (13)	C16—C11—C12—C13	−0.3 (2)
C8—N1—C2—C17	178.88 (13)	C10—C11—C12—C13	−179.05 (14)
C10—N1—C2—C17	−7.8 (2)	C11—C12—C13—O1	−177.93 (14)
N1—C2—N3—C9	0.35 (17)	C11—C12—C13—C14	1.2 (2)
C17—C2—N3—C9	−178.30 (13)	O1—C13—C14—C15	178.17 (16)
C9—C4—C5—C6	−0.4 (3)	C12—C13—C14—C15	−1.0 (2)
C4—C5—C6—C7	0.6 (3)	C13—C14—C15—C16	0.0 (3)
C5—C6—C7—C8	0.5 (3)	C12—C11—C16—C15	−0.7 (2)
C2—N1—C8—C9	−0.70 (16)	C10—C11—C16—C15	178.00 (15)
C10—N1—C8—C9	−174.35 (12)	C14—C15—C16—C11	1.0 (3)
C2—N1—C8—C7	179.60 (16)	N3—C2—C17—C22	121.37 (18)
C10—N1—C8—C7	6.0 (3)	N1—C2—C17—C22	−57.1 (2)
C6—C7—C8—N1	177.93 (16)	N3—C2—C17—C18	−55.6 (2)
C6—C7—C8—C9	−1.7 (2)	N1—C2—C17—C18	125.91 (16)
C2—N3—C9—C8	−0.81 (17)	C22—C17—C18—C19	1.1 (2)
C2—N3—C9—C4	177.74 (16)	C2—C17—C18—C19	178.10 (14)
N1—C8—C9—N3	0.94 (16)	C17—C18—C19—O2	178.41 (14)
C7—C8—C9—N3	−179.32 (14)	C17—C18—C19—C20	−2.2 (2)
N1—C8—C9—C4	−177.77 (14)	O2—C19—C20—C21	−178.78 (15)
C7—C8—C9—C4	2.0 (2)	C18—C19—C20—C21	1.8 (2)
C5—C4—C9—N3	−179.26 (16)	C19—C20—C21—C22	−0.3 (3)
C5—C4—C9—C8	−0.8 (2)	C20—C21—C22—C17	−0.8 (3)
C2—N1—C10—C11	121.77 (16)	C18—C17—C22—C21	0.4 (2)
C8—N1—C10—C11	−66.00 (19)	C2—C17—C22—C21	−176.51 (16)
N1—C10—C11—C12	−25.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.85 (1)	1.83 (1)	2.6804 (19)	176 (2)
O2—H2···S1i	0.85 (1)	2.84 (1)	3.6209 (14)	154 (2)
O1—H1···N3ii	0.86 (1)	1.88 (2)	2.7316 (19)	172 (2)
C18—H18···O3i	0.93	2.58	3.260 (2)	130
C23—H23C···O3iii	0.96	2.72	3.643 (3)	162
C10—H10B···Cg1iv	0.97	2.95	3.622 (2)	127
C5—H5···Cg2v	0.93	2.76	3.624 (2)	156
C23—H23B···Cg3vi	0.96	2.86	3.679 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C4–C9, C11–C16 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.85 (1)	1.83 (1)	2.6804 (19)	176 (2)
O2—H2⋯S1i	0.85 (1)	2.84 (1)	3.6209 (14)	154 (2)
O1—H1⋯N3ii	0.86 (1)	1.88 (2)	2.7316 (19)	172 (2)
C18—H18⋯O3i	0.93	2.58	3.260 (2)	130
C23—H23C⋯O3iii	0.96	2.72	3.643 (3)	162
C10—H10B⋯Cg1iv	0.97	2.95	3.622 (2)	127
C5—H5⋯Cg2v	0.93	2.76	3.624 (2)	156
C23—H23B⋯Cg3vi	0.96	2.86	3.679 (2)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .