1,4-Bis(1H-benzimidazol-2-yl)benzene methanol monosolvate.

The asymmetric unit of the title compound, C(20)H(14)N(4)·CH(4)O, contains two independent half-mol-ecules, each located on an inversion centre, and a methanol solvent mol-ecule. The benzimidazolyl groups form different dihedral angles [24.0 (1) and 11.6 (1)°] with the plane of the central benzene ring in the two mol-ecules. In the crystal, a two-dimensional network is formed through N-H⋯ N, N-H⋯O and O-H⋯N hydrogen-bonding inter-actions between the benzimidazole units and methanol solvent mol-ecules. π-π stacking inter-actions also occur between the benzimidazole rings of adjacent mol-ecules, with centroid-centroid distances of 3.720 (14) Å and inter-planar distances of 3.53 (1) Å .

Related literature

For the synthesis of the title compound see: Wu et al. (2009 ▶). For the properties and applications of benzimidazoles, see: Tidwell et al. (1993 ▶); Salunke et al. (1994 ▶); Hoorn et al. (1995 ▶); van Berkel et al. (1995 ▶); Dinolfo et al. (2005 ▶); Yang et al. (2008 ▶). For structures of 1,4-bis­(benzimidazol-2-yl)benzene analogues, see: Bei et al. (2000 ▶); Wu et al. (2009 ▶). For bond lengths and angles in similar structures, see: Matthews et al. (1996 ▶); Ozbey et al. (1998 ▶).

Experimental

Crystal data

C20H14N4·CH4O

M = 342.39

Triclinic,

a = 7.1730 (14) Å

b = 10.599 (2) Å

c = 12.260 (3) Å

α = 76.21 (3)°

β = 88.37 (3)°

γ = 77.01 (3)°

V = 881.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.31 × 0.16 × 0.12 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 ▶) T min = 0.432, T max = 1.000

4565 measured reflections

3139 independent reflections

2577 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.04

3139 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049238/bg2370sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049238/bg2370Isup2.hkl

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

C20H14N4·CH4O	Z = 2
Mr = 342.39	F(000) = 360
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1730 (14) Å	Cell parameters from 3188 reflections
b = 10.599 (2) Å	θ = 3.0–27.5°
c = 12.260 (3) Å	µ = 0.08 mm−1
α = 76.21 (3)°	T = 293 K
β = 88.37 (3)°	Prism, yellow
γ = 77.01 (3)°	0.31 × 0.16 × 0.12 mm
V = 881.7 (3) Å3

Rigaku Mercury CCD diffractometer	3139 independent reflections
Radiation source: fine-focus sealed tube	2577 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	h = −8→8
Tmin = 0.432, Tmax = 1.000	k = −12→11
4565 measured reflections	l = −12→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.058P)2 + 0.2072P] where P = (Fo2 + 2Fc2)/3
3139 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 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
O1	0.4353 (2)	0.72851 (15)	−0.20907 (11)	0.0655 (4)
H1	0.466 (4)	0.773 (3)	−0.157 (2)	0.099 (9)*
N1	0.5137 (2)	0.81332 (14)	−0.01667 (11)	0.0462 (4)
N2	0.4593 (2)	0.81243 (13)	0.16469 (11)	0.0431 (4)
H2A	0.3999	0.8285	0.2236	0.052*
N3	0.3135 (2)	0.86666 (13)	0.37352 (11)	0.0404 (3)
N4	0.34446 (19)	0.84695 (13)	0.55855 (11)	0.0388 (3)
H4A	0.3731	0.8106	0.6283	0.047*
C1	0.6775 (3)	0.74325 (16)	0.04753 (14)	0.0438 (4)
C2	0.8563 (3)	0.67915 (19)	0.01578 (17)	0.0569 (5)
H2B	0.8818	0.6801	−0.0592	0.068*
C3	0.9931 (3)	0.6147 (2)	0.09908 (19)	0.0624 (6)
H3B	1.1126	0.5717	0.0795	0.075*
C4	0.9576 (3)	0.61209 (19)	0.21223 (18)	0.0584 (5)
H4B	1.0536	0.5670	0.2660	0.070*
C5	0.7826 (3)	0.67513 (18)	0.24601 (16)	0.0502 (5)
H5A	0.7584	0.6733	0.3212	0.060*
C6	0.6448 (2)	0.74142 (16)	0.16162 (14)	0.0412 (4)
C7	0.3870 (3)	0.85267 (16)	0.05676 (13)	0.0403 (4)
C8	0.1892 (2)	0.92809 (15)	0.02858 (13)	0.0394 (4)
C9	0.1321 (3)	0.98685 (17)	−0.08376 (14)	0.0456 (4)
H9A	0.2204	0.9784	−0.1401	0.055*
C10	−0.0540 (3)	1.05739 (17)	−0.11194 (13)	0.0451 (4)
H10A	−0.0896	1.0955	−0.1870	0.068*
C11	0.2500 (2)	0.99128 (16)	0.39671 (14)	0.0394 (4)
C12	0.1739 (3)	1.11565 (18)	0.32434 (16)	0.0541 (5)
H12A	0.1647	1.1252	0.2472	0.065*
C13	0.1133 (3)	1.22324 (18)	0.37161 (18)	0.0590 (5)
H13A	0.0613	1.3065	0.3254	0.071*
C14	0.1282 (3)	1.21002 (18)	0.48749 (18)	0.0551 (5)
H14A	0.0844	1.2846	0.5164	0.066*
C15	0.2059 (3)	1.08975 (17)	0.55992 (16)	0.0484 (4)
H15A	0.2173	1.0816	0.6368	0.058*
C16	0.2667 (2)	0.98057 (16)	0.51249 (13)	0.0379 (4)
C17	0.3672 (2)	0.78377 (15)	0.47268 (13)	0.0358 (4)
C18	0.4362 (2)	0.63846 (15)	0.48859 (13)	0.0356 (4)
C19	0.5493 (2)	0.55926 (16)	0.58125 (13)	0.0421 (4)
H19C	0.5829	0.5982	0.6360	0.063*
C20	0.3879 (3)	0.57685 (16)	0.40750 (14)	0.0426 (4)
H20B	0.3125	0.6281	0.3452	0.064*
C21	0.3492 (5)	0.6260 (3)	−0.1553 (2)	0.0971 (9)
H21A	0.2685	0.6545	−0.0979	0.117*
H21B	0.4481	0.5516	−0.1190	0.117*
H21C	0.2739	0.5965	−0.2043	0.174 (16)*

	U11	U22	U33	U12	U13	U23
O1	0.1004 (12)	0.0687 (9)	0.0363 (7)	−0.0341 (8)	0.0012 (7)	−0.0157 (7)
N1	0.0571 (9)	0.0468 (8)	0.0349 (8)	−0.0070 (7)	−0.0014 (7)	−0.0143 (6)
N2	0.0505 (9)	0.0457 (8)	0.0305 (7)	−0.0023 (7)	−0.0035 (6)	−0.0115 (6)
N3	0.0500 (8)	0.0365 (7)	0.0327 (7)	−0.0029 (6)	−0.0045 (6)	−0.0097 (6)
N4	0.0495 (8)	0.0389 (8)	0.0280 (7)	−0.0082 (6)	−0.0005 (6)	−0.0093 (6)
C1	0.0525 (11)	0.0401 (9)	0.0406 (9)	−0.0095 (8)	0.0004 (8)	−0.0138 (7)
C2	0.0608 (13)	0.0566 (12)	0.0539 (12)	−0.0086 (10)	0.0084 (10)	−0.0195 (9)
C3	0.0517 (12)	0.0574 (12)	0.0775 (15)	−0.0048 (10)	0.0052 (11)	−0.0226 (11)
C4	0.0532 (12)	0.0514 (11)	0.0690 (14)	−0.0085 (9)	−0.0142 (10)	−0.0125 (10)
C5	0.0556 (12)	0.0501 (11)	0.0451 (10)	−0.0100 (9)	−0.0089 (8)	−0.0126 (8)
C6	0.0481 (10)	0.0373 (9)	0.0392 (9)	−0.0085 (7)	−0.0028 (7)	−0.0117 (7)
C7	0.0546 (10)	0.0354 (8)	0.0315 (8)	−0.0086 (7)	−0.0031 (7)	−0.0100 (7)
C8	0.0524 (10)	0.0336 (8)	0.0320 (9)	−0.0073 (7)	−0.0060 (7)	−0.0087 (7)
C9	0.0550 (11)	0.0481 (10)	0.0310 (9)	−0.0064 (8)	0.0005 (7)	−0.0090 (7)
C10	0.0585 (11)	0.0451 (10)	0.0281 (8)	−0.0057 (8)	−0.0069 (8)	−0.0063 (7)
C11	0.0417 (9)	0.0366 (9)	0.0400 (9)	−0.0066 (7)	−0.0033 (7)	−0.0108 (7)
C12	0.0682 (13)	0.0429 (10)	0.0471 (11)	−0.0068 (9)	−0.0139 (9)	−0.0063 (8)
C13	0.0660 (13)	0.0350 (10)	0.0711 (14)	−0.0029 (9)	−0.0159 (10)	−0.0092 (9)
C14	0.0553 (12)	0.0420 (10)	0.0718 (14)	−0.0055 (9)	−0.0010 (10)	−0.0254 (9)
C15	0.0542 (11)	0.0471 (10)	0.0491 (10)	−0.0115 (8)	0.0049 (8)	−0.0222 (8)
C16	0.0392 (9)	0.0377 (9)	0.0386 (9)	−0.0096 (7)	0.0021 (7)	−0.0118 (7)
C17	0.0380 (9)	0.0388 (9)	0.0313 (8)	−0.0075 (7)	−0.0006 (6)	−0.0109 (7)
C18	0.0380 (9)	0.0366 (8)	0.0313 (8)	−0.0063 (7)	−0.0011 (7)	−0.0082 (7)
C19	0.0541 (11)	0.0405 (9)	0.0332 (9)	−0.0089 (8)	−0.0084 (7)	−0.0122 (7)
C20	0.0526 (10)	0.0392 (9)	0.0337 (9)	−0.0063 (8)	−0.0122 (7)	−0.0064 (7)
C21	0.141 (3)	0.107 (2)	0.0643 (16)	−0.072 (2)	0.0164 (16)	−0.0224 (15)

O1—C21	1.391 (3)	C9—C10	1.384 (3)
O1—H1	0.93 (3)	C9—H9A	0.9300
N1—C7	1.331 (2)	C10—C8i	1.400 (2)
N1—C1	1.391 (2)	C10—H10A	0.9300
N2—C7	1.368 (2)	C11—C16	1.403 (2)
N2—C6	1.378 (2)	C11—C12	1.403 (2)
N2—H2A	0.8600	C12—C13	1.380 (3)
N3—C17	1.328 (2)	C12—H12A	0.9300
N3—C11	1.391 (2)	C13—C14	1.399 (3)
N4—C17	1.3640 (19)	C13—H13A	0.9300
N4—C16	1.385 (2)	C14—C15	1.376 (3)
N4—H4A	0.8600	C14—H14A	0.9300
C1—C2	1.401 (3)	C15—C16	1.395 (2)
C1—C6	1.408 (2)	C15—H15A	0.9300
C2—C3	1.377 (3)	C17—C18	1.475 (2)
C2—H2B	0.9300	C18—C19	1.395 (2)
C3—C4	1.398 (3)	C18—C20	1.402 (2)
C3—H3B	0.9300	C19—C20ii	1.386 (2)
C4—C5	1.385 (3)	C19—H19C	0.9300
C4—H4B	0.9300	C20—C19ii	1.386 (2)
C5—C6	1.393 (2)	C20—H20B	0.9300
C5—H5A	0.9300	C21—H21A	0.9600
C7—C8	1.469 (2)	C21—H21B	0.9600
C8—C10i	1.400 (2)	C21—H21C	0.9600
C8—C9	1.400 (2)
C21—O1—H1	109.8 (16)	C8i—C10—H10A	119.7
C7—N1—C1	104.98 (14)	N3—C11—C16	110.02 (14)
C7—N2—C6	107.32 (14)	N3—C11—C12	130.11 (16)
C7—N2—H2A	126.3	C16—C11—C12	119.85 (16)
C6—N2—H2A	126.3	C13—C12—C11	117.72 (18)
C17—N3—C11	104.91 (13)	C13—C12—H12A	121.1
C17—N4—C16	107.26 (13)	C11—C12—H12A	121.1
C17—N4—H4A	126.4	C12—C13—C14	121.53 (18)
C16—N4—H4A	126.4	C12—C13—H13A	119.2
N1—C1—C2	130.63 (17)	C14—C13—H13A	119.2
N1—C1—C6	109.80 (15)	C15—C14—C13	121.84 (17)
C2—C1—C6	119.57 (17)	C15—C14—H14A	119.1
C3—C2—C1	117.88 (19)	C13—C14—H14A	119.1
C3—C2—H2B	121.1	C14—C15—C16	116.80 (17)
C1—C2—H2B	121.1	C14—C15—H15A	121.6
C2—C3—C4	121.92 (19)	C16—C15—H15A	121.6
C2—C3—H3B	119.0	N4—C16—C15	132.62 (16)
C4—C3—H3B	119.0	N4—C16—C11	105.12 (14)
C5—C4—C3	121.46 (19)	C15—C16—C11	122.22 (16)
C5—C4—H4B	119.3	N3—C17—N4	112.68 (14)
C3—C4—H4B	119.3	N3—C17—C18	123.53 (14)
C4—C5—C6	116.64 (18)	N4—C17—C18	123.74 (14)
C4—C5—H5A	121.7	C19—C18—C20	118.34 (15)
C6—C5—H5A	121.7	C19—C18—C17	122.54 (14)
N2—C6—C5	132.09 (16)	C20—C18—C17	119.12 (14)
N2—C6—C1	105.38 (15)	C20ii—C19—C18	120.63 (15)
C5—C6—C1	122.52 (17)	C20ii—C19—H19C	119.7
N1—C7—N2	112.51 (15)	C18—C19—H19C	119.7
N1—C7—C8	125.12 (15)	C19ii—C20—C18	121.03 (15)
N2—C7—C8	122.36 (15)	C19ii—C20—H20B	119.5
C10i—C8—C9	118.54 (16)	C18—C20—H20B	119.5
C10i—C8—C7	121.45 (15)	O1—C21—H21A	109.0
C9—C8—C7	120.00 (16)	O1—C21—H21B	108.1
C10—C9—C8	120.80 (16)	H21A—C21—H21B	107.6
C10—C9—H9A	119.6	O1—C21—H21C	114.6
C8—C9—H9A	119.6	H21A—C21—H21C	108.7
C9—C10—C8i	120.66 (15)	H21B—C21—H21C	108.7
C9—C10—H10A	119.7

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.93 (3)	1.93 (3)	2.829 (2)	162 (2)
N2—H2A···N3	0.86	2.03	2.873 (2)	168.
N4—H4A···O1iii	0.86	1.99	2.855 (2)	179.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.93 (3)	1.93 (3)	2.829 (2)	162 (2)
N2—H2A⋯N3	0.86	2.03	2.873 (2)	168
N4—H4A⋯O1i	0.86	1.99	2.855 (2)	179

Symmetry code: (i) .