2-(Thio-phen-2-yl)-1-(thio-phen-2-ylmeth-yl)-1H-benzimidazole.

In the title compound, C(16)H(12)N(2)S(2), the thio-phene groups are rotationally disordered over two sets of sites, by approximately 180°, with occupancy ratios of 0.916 (2):0.084 (2) and 0.903 (2):0.097 (2). The major components of the thio-phene and methyl-ene substituted thio-phene rings are canted by 24.06 (12) and 85.07 (10)°, respectively, from the benzimidazole ring system plane and the dihedral angle between the major component thio-phene ring planes is 84.90 (14)°. In the crystal, there is a weak C-H⋯N hydrogen bond which links mol-ecules into chains.

Related literature

For a discussion of the rearrangement of 1,2-diimino­benzene species to form benzimidazoles, see: Smith & Ho (1971 ▶). See Varala et al. (2007 ▶) for examples of proline-catalysed 1,2-disubstituted benzimidazole syntheses. Reich et al. (2004 ▶) provide examples of inter­molecular aldimine coupling. For other syntheses of substituted benzimidazoles, see: Grimmett (1997 ▶); Bahrami et al. (2007 ▶); Du & Wang (2007 ▶). For the biological activity of benzimidazole derivatives, see: López-Rodríguez et al. (1999 ▶); Horton et al. (2003 ▶).

Experimental

Crystal data

C16H12N2S2

M = 296.40

Monoclinic,

a = 8.9859 (13) Å

b = 9.1601 (11) Å

c = 17.476 (3) Å

β = 93.629 (5)°

V = 1435.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 300 K

0.80 × 0.30 × 0.10 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.761, T max = 0.965

8857 measured reflections

2527 independent reflections

1942 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.05

2527 reflections

210 parameters

26 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Bruker, 2004 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055103/lh5359sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811055103/lh5359Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055103/lh5359Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811055103/lh5359Isup4.mol

Supplementary material file. DOI: 10.1107/S1600536811055103/lh5359Isup5.cml

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

C16H12N2S2	F(000) = 616
Mr = 296.40	Dx = 1.371 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2556 reflections
a = 8.9859 (13) Å	θ = 2.3–24.0°
b = 9.1601 (11) Å	µ = 0.36 mm−1
c = 17.476 (3) Å	T = 300 K
β = 93.629 (5)°	Plate, clear yellow
V = 1435.6 (3) Å3	0.80 × 0.30 × 0.10 mm
Z = 4

Bruker SMART X2S benchtop diffractometer	2527 independent reflections
Radiation source: fine-focus sealed tube	1942 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.761, Tmax = 0.965	k = −10→10
8857 measured reflections	l = −20→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.2347P] where P = (Fo2 + 2Fc2)/3
2527 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.18 e Å−3
26 restraints	Δρmin = −0.25 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	Occ. (<1)
S1	0.21859 (8)	0.28769 (8)	0.08330 (3)	0.0467 (2)	0.916 (2)
C9	0.0913 (5)	0.3386 (5)	0.2054 (2)	0.0620 (12)	0.916 (2)
H9	0.0724	0.3488	0.2568	0.074*	0.916 (2)
C10	−0.0188 (4)	0.3558 (5)	0.1464 (2)	0.0648 (10)	0.916 (2)
H10	−0.1168	0.3819	0.1540	0.078*	0.916 (2)
C11	0.0332 (3)	0.3301 (5)	0.07718 (18)	0.0585 (9)	0.916 (2)
H11	−0.0251	0.3349	0.0313	0.070*	0.916 (2)
S1'	0.0789 (14)	0.3656 (15)	0.2202 (7)	0.0467 (2)	0.084 (2)
C9'	0.208 (3)	0.300 (4)	0.1075 (11)	0.0620 (12)	0.084 (2)
H9'	0.2835	0.2677	0.0773	0.074*	0.084 (2)
C11'	−0.017 (3)	0.384 (6)	0.1320 (15)	0.0585 (9)	0.084 (2)
H11'	−0.1150	0.4159	0.1246	0.070*	0.084 (2)
C10'	0.071 (3)	0.344 (6)	0.0747 (16)	0.0648 (10)	0.084 (2)
H10'	0.0434	0.3457	0.0225	0.078*	0.084 (2)
S2	0.18792 (12)	0.42615 (9)	0.47929 (5)	0.0647 (3)	0.903 (2)
C14	0.2441 (4)	0.1896 (4)	0.41297 (19)	0.0411 (8)	0.903 (2)
H14	0.2767	0.1211	0.3785	0.049*	0.903 (2)
C15	0.1692 (5)	0.1519 (4)	0.4778 (3)	0.0510 (8)	0.903 (2)
H15	0.1469	0.0563	0.4907	0.061*	0.903 (2)
C16	0.1329 (4)	0.2674 (5)	0.51922 (17)	0.0549 (10)	0.903 (2)
H16	0.0835	0.2618	0.5643	0.066*	0.903 (2)
S2'	0.2508 (19)	0.1572 (12)	0.3994 (8)	0.0647 (3)	0.097 (2)
C14'	0.187 (3)	0.394 (3)	0.4642 (13)	0.0411 (8)	0.097 (2)
H14'	0.1810	0.4923	0.4762	0.049*	0.097 (2)
C16'	0.146 (5)	0.146 (3)	0.478 (2)	0.0549 (10)	0.097 (2)
H16'	0.1140	0.0590	0.4989	0.066*	0.097 (2)
C15'	0.117 (5)	0.280 (4)	0.5038 (19)	0.0510 (8)	0.097 (2)
H15'	0.0564	0.2969	0.5442	0.061*	0.097 (2)
N1	0.41824 (18)	0.32345 (17)	0.29374 (9)	0.0385 (4)
N2	0.47184 (19)	0.18925 (19)	0.19147 (9)	0.0453 (4)
C1	0.5604 (2)	0.2661 (2)	0.31017 (12)	0.0405 (5)
C2	0.5918 (2)	0.1839 (2)	0.24593 (12)	0.0450 (5)
C3	0.7282 (3)	0.1124 (3)	0.24430 (15)	0.0606 (7)
H3	0.749 (3)	0.062 (3)	0.2051 (14)	0.073*
C4	0.8285 (3)	0.1262 (3)	0.30724 (16)	0.0731 (8)
H4	0.9203	0.0793	0.3071	0.088*
C5	0.7950 (3)	0.2087 (3)	0.37082 (16)	0.0671 (7)
H5	0.8650	0.2161	0.4122	0.081*
C6	0.6600 (2)	0.2799 (3)	0.37371 (13)	0.0536 (6)
H6	0.6369	0.3345	0.4162	0.064*
C7	0.3719 (2)	0.2722 (2)	0.22212 (11)	0.0380 (5)
C8	0.2290 (2)	0.3058 (2)	0.18189 (11)	0.0398 (5)
C12	0.3420 (2)	0.4205 (2)	0.34473 (11)	0.0422 (5)
H12A	0.2690	0.4782	0.3148	0.051*
H12B	0.4139	0.4870	0.3695	0.051*
C13	0.2649 (2)	0.3368 (2)	0.40501 (10)	0.0374 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0584 (4)	0.0489 (4)	0.0324 (4)	0.0037 (3)	0.0007 (3)	−0.0022 (3)
C9	0.0552 (18)	0.079 (3)	0.053 (2)	0.0069 (17)	0.0129 (16)	−0.0182 (18)
C10	0.0447 (14)	0.078 (3)	0.071 (2)	0.0102 (15)	−0.0007 (15)	−0.0031 (18)
C11	0.0576 (19)	0.0612 (18)	0.0542 (16)	0.0000 (18)	−0.0167 (15)	−0.0041 (14)
S1'	0.0584 (4)	0.0489 (4)	0.0324 (4)	0.0037 (3)	0.0007 (3)	−0.0022 (3)
C9'	0.0552 (18)	0.079 (3)	0.053 (2)	0.0069 (17)	0.0129 (16)	−0.0182 (18)
C11'	0.0576 (19)	0.0612 (18)	0.0542 (16)	0.0000 (18)	−0.0167 (15)	−0.0041 (14)
C10'	0.0447 (14)	0.078 (3)	0.071 (2)	0.0102 (15)	−0.0007 (15)	−0.0031 (18)
S2	0.0900 (6)	0.0564 (6)	0.0515 (5)	−0.0007 (4)	0.0340 (4)	−0.0160 (3)
C14	0.0445 (14)	0.044 (2)	0.0355 (19)	0.0040 (14)	0.0106 (13)	−0.0070 (13)
C15	0.045 (2)	0.0523 (16)	0.0560 (16)	−0.0033 (12)	0.0097 (14)	0.0101 (13)
C16	0.0478 (17)	0.083 (2)	0.0345 (17)	0.0014 (15)	0.0113 (15)	0.0023 (15)
S2'	0.0900 (6)	0.0564 (6)	0.0515 (5)	−0.0007 (4)	0.0340 (4)	−0.0160 (3)
C14'	0.0445 (14)	0.044 (2)	0.0355 (19)	0.0040 (14)	0.0106 (13)	−0.0070 (13)
C16'	0.0478 (17)	0.083 (2)	0.0345 (17)	0.0014 (15)	0.0113 (15)	0.0023 (15)
C15'	0.045 (2)	0.0523 (16)	0.0560 (16)	−0.0033 (12)	0.0097 (14)	0.0101 (13)
N1	0.0465 (9)	0.0396 (9)	0.0300 (9)	−0.0002 (8)	0.0080 (7)	−0.0035 (7)
N2	0.0478 (10)	0.0536 (11)	0.0354 (10)	0.0049 (8)	0.0092 (8)	−0.0070 (8)
C1	0.0421 (11)	0.0424 (12)	0.0375 (12)	−0.0069 (9)	0.0068 (9)	0.0027 (9)
C2	0.0428 (11)	0.0526 (13)	0.0405 (12)	0.0011 (10)	0.0106 (10)	0.0035 (10)
C3	0.0491 (14)	0.0785 (18)	0.0558 (16)	0.0117 (13)	0.0157 (12)	−0.0021 (13)
C4	0.0437 (13)	0.100 (2)	0.076 (2)	0.0125 (14)	0.0076 (14)	0.0171 (17)
C5	0.0483 (14)	0.090 (2)	0.0617 (17)	−0.0087 (13)	−0.0084 (12)	0.0143 (15)
C6	0.0548 (14)	0.0645 (15)	0.0411 (13)	−0.0096 (11)	−0.0009 (11)	0.0010 (11)
C7	0.0458 (11)	0.0380 (11)	0.0309 (11)	−0.0025 (9)	0.0088 (9)	0.0011 (9)
C8	0.0463 (11)	0.0373 (11)	0.0360 (11)	−0.0022 (9)	0.0036 (9)	0.0019 (9)
C12	0.0575 (12)	0.0360 (11)	0.0341 (11)	0.0022 (9)	0.0108 (10)	−0.0061 (9)
C13	0.0398 (10)	0.0423 (12)	0.0303 (10)	0.0048 (9)	0.0046 (9)	−0.0055 (9)

S1—C11	1.708 (3)	C14'—C13	1.388 (17)
S1—C8	1.728 (2)	C14'—C15'	1.42 (2)
C9—C8	1.362 (4)	C14'—H14'	0.9300
C9—C10	1.392 (5)	C16'—C15'	1.345 (19)
C9—H9	0.9300	C16'—H16'	0.9300
C10—C11	1.345 (4)	C15'—H15'	0.9300
C10—H10	0.9300	N1—C7	1.377 (2)
C11—H11	0.9300	N1—C1	1.394 (3)
S1'—C8	1.638 (10)	N1—C12	1.460 (2)
S1'—C11'	1.726 (14)	N2—C7	1.316 (2)
C9'—C8	1.303 (19)	N2—C2	1.393 (3)
C9'—C10'	1.39 (2)	C1—C6	1.387 (3)
C9'—H9'	0.9300	C1—C2	1.395 (3)
C11'—C10'	1.366 (19)	C2—C3	1.392 (3)
C11'—H11'	0.9300	C3—C4	1.383 (4)
C10'—H10'	0.9300	C3—H3	0.86 (2)
S2—C16	1.700 (4)	C4—C5	1.393 (4)
S2—C13	1.7166 (18)	C4—H4	0.9300
C14—C13	1.370 (4)	C5—C6	1.381 (3)
C14—C15	1.397 (4)	C5—H5	0.9300
C14—H14	0.9300	C6—H6	0.9300
C15—C16	1.334 (4)	C7—C8	1.457 (3)
C15—H15	0.9300	C12—C13	1.507 (3)
C16—H16	0.9300	C12—H12A	0.9700
S2'—C13	1.653 (10)	C12—H12B	0.9700
S2'—C16'	1.711 (15)
C11—S1—C8	91.82 (13)	N1—C1—C2	105.49 (18)
C8—C9—C10	114.7 (3)	C3—C2—N2	130.3 (2)
C8—C9—H9	122.6	C3—C2—C1	119.6 (2)
C10—C9—H9	122.6	N2—C2—C1	110.09 (17)
C11—C10—C9	112.0 (3)	C4—C3—C2	118.1 (2)
C11—C10—H10	124.0	C4—C3—H3	121.3 (18)
C9—C10—H10	124.0	C2—C3—H3	120.6 (18)
C10—C11—S1	112.1 (2)	C3—C4—C5	121.4 (2)
C10—C11—H11	123.9	C3—C4—H4	119.3
S1—C11—H11	123.9	C5—C4—H4	119.3
C8—S1'—C11'	92.6 (11)	C6—C5—C4	121.3 (2)
C8—C9'—C10'	118 (2)	C6—C5—H5	119.3
C8—C9'—H9'	121.1	C4—C5—H5	119.3
C10'—C9'—H9'	121.1	C5—C6—C1	116.8 (2)
C10'—C11'—S1'	110.5 (16)	C5—C6—H6	121.6
C10'—C11'—H11'	124.7	C1—C6—H6	121.6
S1'—C11'—H11'	124.7	N2—C7—N1	113.07 (18)
C11'—C10'—C9'	108 (2)	N2—C7—C8	121.92 (18)
C11'—C10'—H10'	125.8	N1—C7—C8	125.00 (17)
C9'—C10'—H10'	125.8	C9'—C8—C9	103.6 (14)
C16—S2—C13	92.54 (14)	C9'—C8—C7	122.6 (13)
C13—C14—C15	113.6 (3)	C9—C8—C7	133.7 (2)
C13—C14—H14	123.2	C9'—C8—S1'	110.7 (13)
C15—C14—H14	123.2	C9—C8—S1'	10.0 (6)
C16—C15—C14	113.1 (3)	C7—C8—S1'	126.6 (5)
C16—C15—H15	123.5	C9'—C8—S1	6.0 (13)
C14—C15—H15	123.5	C9—C8—S1	109.2 (2)
C15—C16—S2	111.6 (2)	C7—C8—S1	116.84 (14)
C15—C16—H16	124.2	S1'—C8—S1	116.5 (5)
S2—C16—H16	124.2	N1—C12—C13	111.81 (16)
C13—S2'—C16'	93.3 (11)	N1—C12—H12A	109.3
C13—C14'—C15'	110.4 (19)	C13—C12—H12A	109.3
C13—C14'—H14'	124.8	N1—C12—H12B	109.3
C15'—C14'—H14'	124.8	C13—C12—H12B	109.3
C15'—C16'—S2'	110.1 (16)	H12A—C12—H12B	107.9
C15'—C16'—H16'	124.9	C14—C13—C14'	102.4 (12)
S2'—C16'—H16'	124.9	C14—C13—C12	130.06 (19)
C16'—C15'—C14'	114 (2)	C14'—C13—C12	127.4 (11)
C16'—C15'—H15'	123.1	C14—C13—S2'	10.1 (5)
C14'—C15'—H15'	123.1	C14'—C13—S2'	112.2 (12)
C7—N1—C1	106.23 (16)	C12—C13—S2'	120.1 (4)
C7—N1—C12	129.49 (17)	C14—C13—S2	109.18 (17)
C1—N1—C12	124.27 (17)	C14'—C13—S2	8.3 (11)
C7—N2—C2	105.12 (16)	C12—C13—S2	120.76 (15)
C6—C1—N1	131.82 (19)	S2'—C13—S2	119.1 (4)
C6—C1—C2	122.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N2i	0.93	2.54	3.445 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯N2i	0.93	2.54	3.445 (4)	166

Symmetry code: (i) .