1,4-Bis(benzimidazol-2-yl)benzene dimethyl-formamide disolvate.

The aromatic mol-ecule of the title compound, C(20)H(14)N(4)·2C(3)H(7)NO, occupies a special position on an inversion center. The benzimidazole unit (planar to within 0.008 Å) forms a dihedral angle of 9.1 (2)° with the central benzene ring. The benzimidazole H atom participates in a hydrogen bond with the dimethyl-formamide solvent molecule, thus giving rise to the title 1:2 aggregate. These aggregates are further linked in the crystal structure by aromatic π-π stacking inter-actions [centroid-centroid distance = 6.356 (2) Å].

Related literature

For background literature concerning benzimidazole compounds, see: Zarrinmayeh et al. (1998 ▶); Gallagher et al. (2001 ▶); Howarth & Hanlon (2001 ▶). For the unsolvated structure, see: Bei et al. (2000 ▶); Dudd et al. (2003 ▶).

Experimental

Crystal data

C20H14N4·2C3H7NO

M = 456.54

Monoclinic,

a = 6.3556 (13) Å

b = 20.931 (2) Å

c = 9.0097 (18) Å

β = 98.26 (2)°

V = 1186.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.32 × 0.26 × 0.24 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.970, T max = 0.990

12310 measured reflections

2723 independent reflections

1718 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.158

S = 1.00

2723 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004759/ya2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004759/ya2086Isup2.hkl

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

C20H14N4·2C3H7NO	F(000) = 484
Mr = 456.54	Dx = 1.278 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9216 reflections
a = 6.3556 (13) Å	θ = 3.0–27.7°
b = 20.931 (2) Å	µ = 0.08 mm−1
c = 9.0097 (18) Å	T = 291 K
β = 98.26 (2)°	Block, yellow
V = 1186.1 (4) Å3	0.32 × 0.26 × 0.24 mm
Z = 2

Rigaku Mercury2 diffractometer	2723 independent reflections
Radiation source: fine-focus sealed tube	1718 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD profile fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −27→27
Tmin = 0.970, Tmax = 0.990	l = −11→11
12310 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0615P)2 + 0.4757P] where P = (Fo2 + 2Fc2)/3
2723 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.4424 (3)	0.03145 (10)	0.6222 (2)	0.0442 (5)
H1A	0.4027	0.0527	0.7045	0.053*
C2	0.6334 (3)	0.04722 (9)	0.5722 (2)	0.0394 (5)
C3	0.6877 (3)	0.01491 (10)	0.4482 (2)	0.0454 (5)
H3A	0.8140	0.0249	0.4126	0.054*
C4	0.7705 (3)	0.09548 (9)	0.6530 (2)	0.0396 (5)
C5	0.9076 (3)	0.16201 (10)	0.8206 (2)	0.0431 (5)
C6	1.0397 (3)	0.16157 (9)	0.7099 (2)	0.0425 (5)
C7	1.2235 (4)	0.19770 (11)	0.7212 (3)	0.0563 (6)
H7A	1.3119	0.1966	0.6474	0.068*
C8	1.2694 (4)	0.23526 (12)	0.8464 (3)	0.0655 (7)
H8A	1.3914	0.2604	0.8575	0.079*
C9	1.1379 (4)	0.23673 (12)	0.9574 (3)	0.0638 (7)
H9A	1.1734	0.2630	1.0404	0.077*
C10	0.9577 (4)	0.20035 (11)	0.9471 (3)	0.0578 (6)
H10A	0.8713	0.2012	1.0221	0.069*
C11	0.7511 (4)	0.87860 (14)	0.7174 (3)	0.0663 (7)
H11A	0.6668	0.8486	0.6607	0.080*
C12	0.7988 (5)	0.95068 (16)	0.9240 (3)	0.0905 (10)
H12A	0.9305	0.9584	0.8865	0.136*
H12B	0.8277	0.9357	1.0255	0.136*
H12C	0.7187	0.9897	0.9210	0.136*
C13	0.4746 (5)	0.88579 (18)	0.8728 (4)	0.0984 (11)
H13A	0.4093	0.8540	0.8042	0.148*
H13B	0.3850	0.9229	0.8681	0.148*
H13C	0.4937	0.8689	0.9728	0.148*
N1	0.7398 (3)	0.12012 (9)	0.78322 (19)	0.0470 (5)
N2	0.9489 (3)	0.11884 (8)	0.60413 (19)	0.0442 (4)
H2A	0.9957	0.1087	0.5223	0.053*
N3	0.6781 (3)	0.90317 (9)	0.8324 (2)	0.0526 (5)
O1	0.9230 (3)	0.89199 (11)	0.6780 (2)	0.0845 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0431 (11)	0.0534 (13)	0.0382 (11)	0.0016 (10)	0.0135 (9)	−0.0061 (9)
C2	0.0390 (11)	0.0442 (11)	0.0355 (10)	0.0044 (9)	0.0071 (8)	0.0028 (8)
C3	0.0397 (11)	0.0537 (12)	0.0451 (12)	−0.0003 (10)	0.0144 (9)	−0.0011 (10)
C4	0.0386 (11)	0.0425 (11)	0.0385 (10)	0.0033 (9)	0.0088 (9)	0.0043 (9)
C5	0.0431 (11)	0.0414 (11)	0.0457 (12)	0.0015 (9)	0.0088 (9)	0.0011 (9)
C6	0.0441 (11)	0.0398 (11)	0.0440 (11)	0.0015 (9)	0.0080 (9)	0.0061 (9)
C7	0.0494 (13)	0.0570 (14)	0.0655 (15)	−0.0081 (11)	0.0183 (11)	0.0020 (12)
C8	0.0543 (15)	0.0584 (15)	0.0827 (19)	−0.0146 (12)	0.0066 (13)	−0.0018 (13)
C9	0.0672 (16)	0.0582 (15)	0.0649 (16)	−0.0106 (13)	0.0052 (13)	−0.0125 (12)
C10	0.0635 (15)	0.0580 (14)	0.0537 (14)	−0.0070 (12)	0.0146 (12)	−0.0107 (11)
C11	0.0706 (17)	0.0797 (18)	0.0501 (14)	0.0029 (14)	0.0129 (13)	−0.0001 (13)
C12	0.112 (3)	0.085 (2)	0.0701 (19)	0.0047 (19)	−0.0020 (18)	−0.0122 (16)
C13	0.078 (2)	0.126 (3)	0.101 (2)	−0.001 (2)	0.0443 (19)	0.023 (2)
N1	0.0467 (10)	0.0530 (10)	0.0439 (10)	−0.0042 (8)	0.0158 (8)	−0.0052 (8)
N2	0.0454 (10)	0.0488 (10)	0.0414 (9)	−0.0018 (8)	0.0166 (8)	−0.0012 (8)
N3	0.0540 (11)	0.0625 (12)	0.0438 (10)	0.0004 (9)	0.0153 (9)	0.0007 (9)
O1	0.0695 (12)	0.1293 (18)	0.0613 (12)	0.0077 (12)	0.0318 (10)	0.0092 (11)

C1—C3i	1.370 (3)	C8—H8A	0.9300
C1—C2	1.394 (3)	C9—C10	1.367 (3)
C1—H1A	0.9300	C9—H9A	0.9300
C2—C3	1.391 (3)	C10—H10A	0.9300
C2—C4	1.459 (3)	C11—O1	1.229 (3)
C3—C1i	1.370 (3)	C11—N3	1.300 (3)
C3—H3A	0.9300	C11—H11A	0.9300
C4—N1	1.322 (2)	C12—N3	1.441 (3)
C4—N2	1.364 (2)	C12—H12A	0.9600
C5—N1	1.384 (3)	C12—H12B	0.9600
C5—C10	1.393 (3)	C12—H12C	0.9600
C5—C6	1.393 (3)	C13—N3	1.440 (3)
C6—N2	1.372 (3)	C13—H13A	0.9600
C6—C7	1.383 (3)	C13—H13B	0.9600
C7—C8	1.372 (4)	C13—H13C	0.9600
C7—H7A	0.9300	N2—H2A	0.8600
C8—C9	1.393 (4)
C3i—C1—C2	120.91 (18)	C8—C9—H9A	119.3
C3i—C1—H1A	119.5	C9—C10—C5	117.9 (2)
C2—C1—H1A	119.5	C9—C10—H10A	121.1
C3—C2—C1	118.20 (19)	C5—C10—H10A	121.1
C3—C2—C4	122.55 (18)	O1—C11—N3	125.0 (3)
C1—C2—C4	119.23 (17)	O1—C11—H11A	117.5
C1i—C3—C2	120.89 (19)	N3—C11—H11A	117.5
C1i—C3—H3A	119.6	N3—C12—H12A	109.5
C2—C3—H3A	119.6	N3—C12—H12B	109.5
N1—C4—N2	112.48 (18)	H12A—C12—H12B	109.5
N1—C4—C2	124.01 (18)	N3—C12—H12C	109.5
N2—C4—C2	123.48 (17)	H12A—C12—H12C	109.5
N1—C5—C10	129.9 (2)	H12B—C12—H12C	109.5
N1—C5—C6	110.11 (18)	N3—C13—H13A	109.5
C10—C5—C6	120.0 (2)	N3—C13—H13B	109.5
N2—C6—C7	132.4 (2)	H13A—C13—H13B	109.5
N2—C6—C5	105.38 (17)	N3—C13—H13C	109.5
C7—C6—C5	122.2 (2)	H13A—C13—H13C	109.5
C8—C7—C6	116.9 (2)	H13B—C13—H13C	109.5
C8—C7—H7A	121.6	C4—N1—C5	104.84 (16)
C6—C7—H7A	121.6	C4—N2—C6	107.19 (16)
C7—C8—C9	121.6 (2)	C4—N2—H2A	126.4
C7—C8—H8A	119.2	C6—N2—H2A	126.4
C9—C8—H8A	119.2	C11—N3—C13	122.5 (3)
C10—C9—C8	121.5 (2)	C11—N3—C12	120.5 (2)
C10—C9—H9A	119.3	C13—N3—C12	117.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ii	0.86	1.95	2.787 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	1.95	2.787 (3)	165

Symmetry code: (i) .