(E)-2-[2-(2-Thien-yl)vin-yl]-1H-1,3-benzimidazole.

In the title compound, C(13)H(10)N(2)S, the dihedral angle between the imidazole and thio-phene rings is 16.89 (19)°, and the double bond adopts an E configuration. In the crystal structure, N-H⋯N hydrogen bonds link the mol-ecules into rows along b. There is also evidence of weak C-H⋯S inter-actions.

Related literature

For general background, see: Huang et al. (2003 ▶); Wang et al. (2005 ▶); Ye et al. (2006 ▶, 2007 ▶). For the crystal structures of related compounds, see: Ozbey et al. (1998 ▶); Li & Clarkson (2007 ▶).

Experimental

Crystal data

C13H10N2S

M = 226.06

Orthorhombic,

a = 12.239 (2) Å

b = 16.389 (3) Å

c = 11.487 (2) Å

V = 2304.1 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 293 (2) K

0.15 × 0.10 × 0.07 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.796, T max = 1.000 (expected range = 0.782–0.983)

21849 measured reflections

2637 independent reflections

1360 reflections with I > 2σ(I)

R int = 0.145

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.214

S = 1.07

2637 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.28 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/S1600536808006405/sj2460sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006405/sj2460Isup2.hkl

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

C13H10N2S	F000 = 944
Mr = 226.06	Dx = 1.305 Mg m−3
Orthorhombic, Pnna	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2a 2bc	Cell parameters from 14820 reflections
a = 12.239 (2) Å	θ = 3.0–29.2º
b = 16.389 (3) Å	µ = 0.25 mm−1
c = 11.487 (2) Å	T = 293 (2) K
V = 2304.1 (7) Å3	Block, colorless
Z = 8	0.15 × 0.10 × 0.07 mm

Mercury2 (2x2 bin mode) diffractometer	2637 independent reflections
Radiation source: fine-focus sealed tube	1360 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.145
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.3º
CCD profile fitting scans	h = −15→15
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −21→21
Tmin = 0.796, Tmax = 1.000	l = −14→14
21849 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.084	H-atom parameters constrained
wR(F2) = 0.214	w = 1/[σ2(Fo2) + (0.081P)2 + 0.7151P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2637 reflections	Δρmax = 0.22 e Å−3
145 parameters	Δρmin = −0.28 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.88515 (10)	0.06908 (7)	0.51647 (11)	0.0801 (5)
N1	0.6821 (2)	0.07121 (18)	0.1000 (3)	0.0577 (9)
H1B	0.7264	0.0309	0.0924	0.069*	0.50
N2	0.5945 (2)	0.17665 (16)	0.1790 (2)	0.0452 (7)
H2B	0.5751	0.2134	0.2283	0.054*	0.50
C1	0.5111 (4)	0.1178 (3)	−0.1555 (4)	0.0824 (14)
H1A	0.4956	0.1028	−0.2319	0.099*
C2	0.8179 (4)	0.1317 (3)	0.7051 (4)	0.0898 (15)
H2A	0.8136	0.1453	0.7836	0.108*
C3	0.8987 (5)	0.0855 (3)	0.6610 (4)	0.0890 (16)
H3A	0.9559	0.0647	0.7053	0.107*
C4	0.7391 (3)	0.1583 (3)	0.6209 (3)	0.0653 (11)
H4A	0.6790	0.1913	0.6364	0.078*
C5	0.5901 (4)	0.0750 (3)	−0.0942 (4)	0.0753 (13)
H5A	0.6278	0.0316	−0.1277	0.090*
C6	0.4751 (3)	0.2076 (2)	0.0054 (3)	0.0604 (11)
H6A	0.4376	0.2514	0.0381	0.073*
C7	0.4546 (4)	0.1825 (3)	−0.1057 (4)	0.0720 (12)
H7A	0.4015	0.2094	−0.1492	0.086*
C8	0.7672 (3)	0.1264 (2)	0.5105 (3)	0.0581 (10)
C9	0.7079 (3)	0.1380 (2)	0.4039 (3)	0.0532 (10)
H9A	0.6461	0.1709	0.4074	0.064*
C10	0.6101 (3)	0.0995 (2)	0.0186 (3)	0.0515 (9)
C11	0.7328 (3)	0.1064 (2)	0.3007 (3)	0.0526 (10)
H11A	0.7950	0.0740	0.2961	0.063*
C12	0.6700 (3)	0.1188 (2)	0.1941 (3)	0.0479 (9)
C13	0.5538 (3)	0.1655 (2)	0.0678 (3)	0.0461 (9)

	U11	U22	U33	U12	U13	U23
S1	0.0830 (9)	0.0654 (8)	0.0918 (10)	−0.0012 (6)	−0.0304 (7)	0.0032 (6)
N1	0.0607 (19)	0.0583 (19)	0.054 (2)	0.0158 (16)	−0.0072 (15)	−0.0140 (16)
N2	0.0532 (17)	0.0401 (16)	0.0422 (17)	0.0063 (13)	0.0015 (13)	−0.0027 (13)
C1	0.097 (3)	0.096 (4)	0.054 (3)	0.004 (3)	−0.017 (3)	−0.015 (3)
C2	0.113 (4)	0.106 (4)	0.050 (3)	−0.026 (3)	−0.023 (2)	0.013 (3)
C3	0.112 (4)	0.076 (3)	0.079 (4)	−0.023 (3)	−0.043 (3)	0.023 (3)
C4	0.070 (3)	0.081 (3)	0.045 (2)	−0.018 (2)	−0.0037 (18)	0.001 (2)
C5	0.083 (3)	0.079 (3)	0.064 (3)	0.018 (2)	−0.011 (2)	−0.028 (2)
C6	0.072 (3)	0.054 (2)	0.055 (2)	0.009 (2)	−0.009 (2)	0.001 (2)
C7	0.081 (3)	0.071 (3)	0.064 (3)	0.009 (2)	−0.021 (2)	0.007 (2)
C8	0.063 (2)	0.051 (2)	0.061 (3)	−0.0153 (19)	−0.014 (2)	0.0087 (19)
C9	0.055 (2)	0.049 (2)	0.056 (3)	−0.0009 (18)	−0.0023 (18)	0.0054 (18)
C10	0.053 (2)	0.051 (2)	0.051 (2)	0.0034 (18)	−0.0051 (18)	−0.0070 (18)
C11	0.051 (2)	0.048 (2)	0.059 (3)	0.0005 (17)	−0.0004 (19)	−0.0009 (18)
C12	0.048 (2)	0.049 (2)	0.047 (2)	−0.0011 (17)	0.0016 (17)	0.0022 (17)
C13	0.052 (2)	0.0418 (19)	0.044 (2)	−0.0023 (17)	0.0020 (17)	0.0001 (16)

S1—C3	1.690 (5)	C4—C8	1.415 (5)
S1—C8	1.723 (4)	C4—H4A	0.9300
N1—C12	1.341 (4)	C5—C10	1.379 (5)
N1—C10	1.366 (4)	C5—H5A	0.9300
N1—H1B	0.8600	C6—C7	1.365 (5)
N2—C12	1.335 (4)	C6—C13	1.385 (5)
N2—C13	1.383 (4)	C6—H6A	0.9300
N2—H2B	0.8600	C7—H7A	0.9300
C1—C5	1.386 (6)	C8—C9	1.436 (5)
C1—C7	1.390 (6)	C9—C11	1.329 (5)
C1—H1A	0.9300	C9—H9A	0.9300
C2—C3	1.344 (6)	C10—C13	1.401 (5)
C2—C4	1.435 (6)	C11—C12	1.461 (4)
C2—H2A	0.9300	C11—H11A	0.9300
C3—H3A	0.9300
C3—S1—C8	92.0 (3)	C7—C6—H6A	121.3
C12—N1—C10	106.4 (3)	C13—C6—H6A	121.3
C12—N1—H1B	126.8	C6—C7—C1	121.6 (4)
C10—N1—H1B	126.8	C6—C7—H7A	119.2
C12—N2—C13	106.0 (3)	C1—C7—H7A	119.2
C12—N2—H2B	127.0	C4—C8—C9	126.3 (4)
C13—N2—H2B	127.0	C4—C8—S1	111.7 (3)
C5—C1—C7	121.6 (4)	C9—C8—S1	122.0 (3)
C5—C1—H1A	119.2	C11—C9—C8	126.3 (4)
C7—C1—H1A	119.2	C11—C9—H9A	116.8
C3—C2—C4	114.3 (4)	C8—C9—H9A	116.8
C3—C2—H2A	122.8	N1—C10—C5	131.2 (4)
C4—C2—H2A	122.8	N1—C10—C13	107.7 (3)
C2—C3—S1	112.8 (4)	C5—C10—C13	121.1 (4)
C2—C3—H3A	123.6	C9—C11—C12	125.0 (3)
S1—C3—H3A	123.6	C9—C11—H11A	117.5
C8—C4—C2	109.2 (4)	C12—C11—H11A	117.5
C8—C4—H4A	125.4	N1—C12—N2	112.7 (3)
C2—C4—H4A	125.4	N1—C12—C11	122.5 (3)
C1—C5—C10	117.0 (4)	N2—C12—C11	124.9 (3)
C1—C5—H5A	121.5	N2—C13—C6	131.5 (3)
C10—C5—H5A	121.5	N2—C13—C10	107.3 (3)
C7—C6—C13	117.5 (4)	C6—C13—C10	121.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···S1	0.93	2.76	3.161 (4)	107
N1—H1B···N1i	0.86	2.01	2.865 (6)	170
N2—H2B···N2ii	0.86	2.11	2.906 (5)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯S1	0.93	2.76	3.161 (4)	107
N1—H1B⋯N1i	0.86	2.01	2.865 (6)	170
N2—H2B⋯N2ii	0.86	2.11	2.906 (5)	154

Symmetry codes: (i) ; (ii) .