2-(Methyl­sulfan­yl)-1H-benzimidazole

The benzimidazole ring system in the title mol­ecule, C₈H₈N₂S, is planar The imidazole ring does not exhibit a delocalized aromatic bond system. Mol­ecules are linked by N—H...N hydrogen bonds along the c axis. The crystal structure is further stabilized by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.033
• wR factor = 0.090
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-(Methylsulfanyl)-1H-benzimidazole

Crystal data

C8H8N2S	F(000) = 344
Mr = 164.22	Dx = 1.364 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2320 reflections
a = 6.9279 (4) Å	θ = 2.7–27.8°
b = 11.4613 (7) Å	µ = 0.33 mm^−1
c = 10.1980 (7) Å	T = 273 K
β = 99.052 (1)°	Needle, colourless
V = 799.66 (9) Å^3	0.22 × 0.18 × 0.16 mm
Z = 4

Data collection

Bruker Smart APEX CCD area-detector diffractometer	1298 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
ω scans	h = −8→8
7479 measured reflections	k = −13→13
1405 independent reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0499P)^2 + 0.2519P] where P = (Fo^2 + 2Fc^2)/3
1405 reflections	(Δ/σ)max < 0.001
105 parameters	Δρmax = 0.22 e Å^−3
3 restraints	Δρmin = −0.20 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5030 (3)	0.62613 (14)	0.10178 (17)	0.0464 (4)
H1	0.5094	0.6303	0.0115	0.056*
C2	0.3533 (2)	0.67910 (13)	0.15543 (14)	0.0363 (3)
C3	0.0983 (2)	0.77652 (13)	0.20040 (14)	0.0360 (3)
C4	0.3419 (2)	0.67417 (13)	0.29114 (14)	0.0356 (3)
C5	0.4837 (3)	0.61412 (14)	0.37693 (16)	0.0453 (4)
H5	0.4783	0.6097	0.4673	0.054*
C6	0.6325 (3)	0.56140 (16)	0.32379 (18)	0.0523 (4)
H6	0.7290	0.5210	0.3795	0.063*
C7	0.6415 (3)	0.56717 (15)	0.18836 (19)	0.0523 (4)
H7	0.7437	0.5303	0.1558	0.063*
C8	−0.1792 (3)	0.87225 (18)	0.3269 (2)	0.0639 (6)
H8A	−0.2960	0.9182	0.3220	0.096*
H8B	−0.0773	0.9068	0.3896	0.096*
H8C	−0.2045	0.7945	0.3550	0.096*
N1	0.17943 (18)	0.73652 (11)	0.31710 (12)	0.0372 (3)
N2	0.19456 (19)	0.74460 (12)	0.09984 (13)	0.0400 (3)
S1	−0.10474 (6)	0.86698 (4)	0.16743 (4)	0.0520 (2)
H2N	0.164 (3)	0.7588 (14)	0.018 (2)	0.047 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0557 (10)	0.0493 (9)	0.0383 (9)	−0.0028 (7)	0.0196 (7)	−0.0051 (7)
C2	0.0429 (8)	0.0383 (8)	0.0287 (7)	−0.0054 (6)	0.0089 (6)	−0.0023 (6)
C3	0.0365 (8)	0.0437 (8)	0.0277 (7)	−0.0039 (6)	0.0046 (6)	0.0008 (6)
C4	0.0412 (8)	0.0385 (8)	0.0276 (7)	−0.0023 (6)	0.0073 (6)	−0.0019 (6)
C5	0.0521 (10)	0.0507 (9)	0.0322 (8)	0.0062 (7)	0.0040 (7)	0.0010 (7)
C6	0.0516 (10)	0.0517 (10)	0.0521 (11)	0.0114 (8)	0.0032 (8)	0.0001 (8)
C7	0.0516 (10)	0.0502 (10)	0.0590 (11)	0.0057 (8)	0.0205 (8)	−0.0082 (8)
C8	0.0615 (12)	0.0683 (13)	0.0684 (13)	0.0192 (9)	0.0302 (10)	0.0111 (10)
N1	0.0399 (7)	0.0461 (7)	0.0258 (6)	0.0018 (5)	0.0063 (5)	0.0001 (5)
N2	0.0461 (8)	0.0527 (8)	0.0209 (6)	−0.0010 (6)	0.0049 (5)	0.0022 (5)
S1	0.0425 (3)	0.0682 (3)	0.0443 (3)	0.00987 (19)	0.00372 (19)	0.01144 (19)

Geometric parameters (Å, º)

C1—C7	1.375 (3)	C5—C6	1.377 (2)
C1—C2	1.386 (2)	C5—H5	0.9300
C1—H1	0.9300	C6—C7	1.394 (3)
C2—N2	1.378 (2)	C6—H6	0.9300
C2—C4	1.400 (2)	C7—H7	0.9300
C3—N1	1.3160 (19)	C8—S1	1.783 (2)
C3—N2	1.3584 (19)	C8—H8B	0.9600
C3—S1	1.7374 (16)	C8—H8A	0.9600
C4—C5	1.391 (2)	C8—H8C	0.9600
C4—N1	1.3931 (19)	N2—H2N	0.84 (2)
C7—C1—C2	116.86 (15)	C5—C6—H6	119.3
C7—C1—H1	121.6	C7—C6—H6	119.3
C2—C1—H1	121.6	C1—C7—C6	121.59 (15)
N2—C2—C1	132.41 (14)	C1—C7—H7	119.2
N2—C2—C4	105.27 (13)	C6—C7—H7	119.2
C1—C2—C4	122.32 (15)	S1—C8—H8B	109.5
N1—C3—N2	113.48 (13)	S1—C8—H8A	109.5
N1—C3—S1	126.90 (11)	H8B—C8—H8A	109.5
N2—C3—S1	119.56 (11)	S1—C8—H8C	109.5
C5—C4—N1	130.26 (13)	H8B—C8—H8C	109.5
C5—C4—C2	119.85 (14)	H8A—C8—H8C	109.5
N1—C4—C2	109.89 (13)	C3—N1—C4	104.45 (12)
C6—C5—C4	117.90 (15)	C3—N2—C2	106.91 (12)
C6—C5—H5	121.0	C3—N2—H2N	128.4 (12)
C4—C5—H5	121.0	C2—N2—H2N	124.7 (12)
C5—C6—C7	121.48 (16)	C3—S1—C8	100.69 (8)
C7—C1—C2—N2	179.38 (16)	N2—C3—N1—C4	0.35 (17)
C7—C1—C2—C4	0.3 (2)	S1—C3—N1—C4	−176.85 (12)
N2—C2—C4—C5	−179.55 (14)	C5—C4—N1—C3	179.07 (17)
C1—C2—C4—C5	−0.2 (2)	C2—C4—N1—C3	0.06 (16)
N2—C2—C4—N1	−0.43 (16)	N1—C3—N2—C2	−0.63 (18)
C1—C2—C4—N1	178.88 (14)	S1—C3—N2—C2	176.79 (10)
N1—C4—C5—C6	−178.72 (16)	C1—C2—N2—C3	−178.59 (16)
C2—C4—C5—C6	0.2 (2)	C4—C2—N2—C3	0.61 (16)
C4—C5—C6—C7	−0.2 (3)	N1—C3—S1—C8	−6.48 (16)
C2—C1—C7—C6	−0.3 (3)	N2—C3—S1—C8	176.47 (13)
C5—C6—C7—C1	0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N1^i	0.84 (2)	2.07 (2)	2.8769 (17)	160.3 (16)
C8—H8A···Cg1^ii	0.96	2.71	3.58	150

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+2, y+1/2, −z+1/2.