2-[2-(Methyl­sulfan­yl)benzimidazol-1-yl]ethanol

Akonan, L.; Molou, K.Y.G.; Adohi-Krou, A.; Abou, A.; Tenon, A.J.

doi:10.1107/S1600536810001960

2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol

L. Akonan, K. Y. G. Molou, A. Adohi-Krou, A. Abou and A. J. Tenon

In the title compound, C₁₀H₁₂N₂OS, the asymmetric unit consists of two independent molecules. In the crystal structure, molecules form R₄⁴(28) centrosymmetric tetramers via O—H

N hydrogen bonds. These tetramers are stacked along the c axis via C—H

O hydrogen bonds. C—H

π and π–π interactions are also present; in the latter, the centroid–centroid distances are 4.075 (1) and 3.719 (1) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810001960/wn2372sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810001960/wn2372Isup2.hkl Contains datablock I

CCDC reference: 765196

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.102
Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) .....         15

Alert level C
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1A    -   H1A    ...       1.01 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         13
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........    <I>CG</
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........    <I>CG</
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........    <I>CG</
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H12 N2 O S
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        202

Alert level G
PLAT960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) ..           6
PLAT808_ALERT_5_G No Parsable SHELXL style Weighting Scheme Found           !
PLAT929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Numerous compounds having benzimidazole ring systems possess versatile pharmacological activities such as antiviral, anthelmintic, spasmolytic, antihypertensive and vasodilator (Akkurt et al., 2006). It has also been reported that many benzimidazole derivatives have antimicrobial and antifungal activities (Küçükbay et al., 2003, 2004, Puratchikody et al., 2008). Therefore, the synthesis of new benzimidazole derivatives is of considerable interest. In order to explore new benzimidazole properties, the title compound has been synthesized and its crystal structure determined.

The two independent molecules in the asymmetric unit of the title compound and the atomic labeling scheme are shown in Fig.1. In this structure, the nine-membered benzimidazole ring systems (N1A/C3A/N2A/C6A/C7A/C8A/C9A/C10A/C5A, N1B/C3B/N2B/C6B/C7B/C8B/C9B/C10B/C5B) of both independent molecules are essentially planar, the maximum deviation from planarity being, respectively, 0.016 (2) Å for atom C8A and 0.078 (16) Å for atom C3B. These two ring systems make a dihedral angle of 73.95 (6)°.

In the crystal structure, we observe the formation of R₄⁴(28) centrosymmetric tetramers (Bernstein et al., 1995) via O—H···N hydrogen bonds. The tetramers are linked by two symmetric C—H···O hydrogen bonds to form a zigzag infinite chain along the c axis. The supramolecular aggregation is completed by the presence of C—H···π interactions (Table 1) and π–π stacking between two parallel imidazole rings. The centroid···centroid distance of those rings, Cg1···Cg1(1 - x,1 - y,1 - z) and Cg4···Cg4(-x,2 - y,-z) are 4.075 (1) Å and 3.719 (1) Å, respectively (Fig.3).

Related literature top

For the biological activity of compounds having benzimidazole ring systems, and a related structure, see: Akkurt et al. (2006). For other studies of the biological activity of benzimidazoles, see: Küçükbay et al. (2003), (2004); Puratchikody et al. (2008). For hydrogen-bond graph sets, see: Bernstein et al. (1995).

Experimental top

2-Chloroethanol (1.6 ml, 24.4 mmol) and potasium carbonate (1.68 g, 12.2 mmol) were added to 2-methylsulfanyl-1H-benzimidazole (1 g, 6.1 mmol) in dimethyl sulfoxide (DMSO) (5 ml). The reaction mixture was successively agitated for 30 min at room temperature and at 323 K for 24 h. 50 ml of water was then added to the reaction mixture, and the products were extracted with dichloromethane (3 × 50 ml). The combined organic extracts were washed with brine (10 g of sodium chloride in 100 ml of water), dried (Na₂SO₄) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (elution: hexane/ethyl acetate (70:30, v/v)) and the title compound resulted as a brown powder (0.77 g, 61%) with a melting point of 409 K. The brown powder was dissolved in ethanol/hexane (3:1, v/v) and, after four days, brown crystals suitable for single-crystal X-ray diffraction analysis were obtained.

Structure description top

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

	Fig. 1. The structure of the asymmetric unit of the title compound, showing the atomic labeling scheme, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Crystal packing, viewed down the a axis, showing the zigzag infinite chain of cyclic tetramers along the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonds have been omitted for clarity.
	Fig. 3. Crystal packing, showing the π–π and C—H···π stacking interactions. The yellow dots are the centroids of benzene and imidazole rings. H atoms not involved in C—H···π interactions have been omitted for clarity.

2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol top

Crystal data top

C₁₀H₁₂N₂OS	Z = 4
M_r = 208.28	F(000) = 440
Triclinic, P1	D_x = 1.356 Mg m⁻³
Hall symbol: -P 1	Melting point: 409 K
a = 9.3235 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7659 (2) Å	Cell parameters from 13769 reflections
c = 11.4588 (3) Å	θ = 2–29°
α = 78.0849 (9)°	µ = 0.29 mm⁻¹
β = 88.9066 (8)°	T = 223 K
γ = 88.1399 (9)°	Prism, brown
V = 1020.25 (4) Å³	0.20 × 0.20 × 0.15 mm

Data collection top

Nonius KappaCCD diffractometer	3996 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 29.1°, θ_min = 1.8°
φ and ω scans	h = −12→12
13769 measured reflections	k = −12→12
5257 independent reflections	l = −15→15

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Method = Modified Sheldrick w = 1/[σ²(F²) + (0.04P)² + 0.62P], where P = [max(F_o²,0) + 2F_c²]/3
5242 reflections	(Δ/σ)_max = 0.001
261 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³
88 constraints

Crystal data top

C₁₀H₁₂N₂OS	γ = 88.1399 (9)°
M_r = 208.28	V = 1020.25 (4) Å³
Triclinic, P1	Z = 4
a = 9.3235 (2) Å	Mo Kα radiation
b = 9.7659 (2) Å	µ = 0.29 mm⁻¹
c = 11.4588 (3) Å	T = 223 K
α = 78.0849 (9)°	0.20 × 0.20 × 0.15 mm
β = 88.9066 (8)°

Data collection top

Nonius KappaCCD diffractometer	3996 reflections with I > 2σ(I)
13769 measured reflections	R_int = 0.036
5257 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.51 e Å⁻³
5242 reflections	Δρ_min = −0.32 e Å⁻³
261 parameters

Special details top

Experimental. ¹H NMR (DMSO-d₆, 300 MHz, p.p.m.) δ: 2.71 (s, 3H, CH₃); 3.68–3.74 (m 2H, CH₂O, J_CH2—CH2 = 5.7 Hz and J_CH2—OH = 5.4 Hz); 4.17 (t, 2H, CH₂N, J_CH2—CH2 = 5.7 Hz); 5.00 (t, 1H, OH, J_CH2—OH = 5.4 Hz); 7.13–7.17 and 7.46–7.55 (m, 4H, C₆H₄). ¹³C NMR (DMSO-d₆, 300 MHz, p.p.m.) δ: 14.35 (CH₃); 46.25 (CH₂N); 59.14 (CH2O); 109.75, 117.31, 121.14, 121.21, 136.75, 142.92 (C₆H₅); 152.48 (C═N).

Refinement. The 15 reflections 1 0 0; -1 1 0; 0 1 0; 1 1 0; -1 - 1 1; 0 - 1 1; 1 - 1 1; -1 0 1; 0 0 1; 1 0 1; -1 1 1; 0 1 1; 1 1 1; 0 0 2; 0 1 2 have been measured with too low intensities. It might be caused by some systematical error, probably by shielding by a beam stop of these diffractions. They were not used in the refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1A	0.49131 (5)	0.82212 (5)	0.49825 (4)	0.0390
C3A	0.42886 (16)	0.69994 (15)	0.42198 (14)	0.0286
N1A	0.28691 (13)	0.66663 (13)	0.43140 (12)	0.0286
C5A	0.26838 (17)	0.57367 (15)	0.35708 (15)	0.0298
C6A	0.40349 (17)	0.55494 (15)	0.30706 (15)	0.0309
N2A	0.50366 (14)	0.63619 (13)	0.34868 (12)	0.0309
C7A	0.4221 (2)	0.46382 (18)	0.22858 (18)	0.0430
C8A	0.3031 (2)	0.39422 (19)	0.20412 (19)	0.0507
C9A	0.1686 (2)	0.41504 (19)	0.25355 (19)	0.0481
C10A	0.14723 (19)	0.50586 (17)	0.33090 (17)	0.0386
C2A	0.17826 (17)	0.70834 (17)	0.51181 (15)	0.0336
C1A	0.07853 (17)	0.82574 (17)	0.45194 (16)	0.0354
O1A	0.15279 (14)	0.95034 (13)	0.41601 (12)	0.0405
C4A	0.67938 (19)	0.8087 (2)	0.4688 (2)	0.0463
S1B	0.34070 (5)	1.07040 (5)	0.04701 (4)	0.0402
C3B	0.16057 (17)	1.10450 (15)	0.07442 (14)	0.0299
N2B	0.09036 (15)	1.06622 (14)	0.17658 (12)	0.0325
C6B	−0.04765 (17)	1.12427 (16)	0.15371 (14)	0.0307
C5B	−0.05673 (17)	1.19801 (16)	0.03565 (14)	0.0306
N1B	0.07856 (14)	1.18307 (13)	−0.01412 (12)	0.0313
C2B	0.12112 (19)	1.23474 (17)	−0.13814 (14)	0.0357
C1B	0.1892 (2)	1.37598 (19)	−0.15947 (16)	0.0419
O1B	0.21179 (14)	1.42576 (15)	−0.28301 (12)	0.0521
C10B	−0.18151 (19)	1.26805 (18)	−0.01093 (16)	0.0395
C9B	−0.2986 (2)	1.2612 (2)	0.06571 (18)	0.0458
C8B	−0.2918 (2)	1.1879 (2)	0.18335 (18)	0.0449
C7B	−0.16712 (19)	1.11853 (18)	0.22973 (16)	0.0381
C4B	0.3871 (2)	0.9554 (2)	0.18458 (19)	0.0578
H1B	0.305 (3)	1.398 (3)	−0.306 (3)	0.091 (9)*
H1A	0.136 (3)	0.992 (3)	0.329 (3)	0.094 (9)*
H10A	0.0555	0.5211	0.3642	0.0468*
H9A	0.0895	0.3657	0.2337	0.0576*
H8A	0.3134	0.3303	0.1520	0.0612*
H7A	0.5130	0.4501	0.1934	0.0516*
H10B	−0.1862	1.3181	−0.0913	0.0468*
H9B	−0.3860	1.3078	0.0373	0.0552*
H8B	−0.3748	1.1855	0.2331	0.0540*
H7B	−0.1630	1.0688	0.3102	0.0456*
H41A	0.7284	0.8715	0.5062	0.0552*
H42A	0.6966	0.8319	0.3851	0.0552*
H43A	0.7132	0.7157	0.4993	0.0552*
H41B	0.4855	0.9276	0.1822	0.0696*
H42B	0.3707	1.0025	0.2486	0.0681*
H43B	0.3296	0.8751	0.1961	0.0681*
H11A	0.0039	0.8396	0.5063	0.0420*
H12A	0.0383	0.8011	0.3838	0.0420*
H21A	0.2257	0.7382	0.5744	0.0408*
H22A	0.1226	0.6293	0.5442	0.0408*
H21B	0.0383	1.2421	−0.1863	0.0432*
H22B	0.1881	1.1693	−0.1609	0.0432*
H11B	0.1277	1.4401	−0.1289	0.0504*
H12B	0.2787	1.3675	−0.1200	0.0504*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0358 (2)	0.0417 (2)	0.0440 (3)	−0.00593 (17)	−0.00121 (18)	−0.01874 (19)
C3A	0.0264 (7)	0.0263 (7)	0.0320 (8)	−0.0010 (5)	−0.0012 (6)	−0.0030 (6)
N1A	0.0250 (6)	0.0282 (6)	0.0324 (7)	−0.0025 (5)	0.0027 (5)	−0.0059 (5)
C5A	0.0301 (8)	0.0237 (7)	0.0345 (8)	−0.0019 (6)	−0.0017 (6)	−0.0030 (6)
C6A	0.0304 (8)	0.0254 (7)	0.0370 (9)	0.0010 (6)	−0.0024 (6)	−0.0067 (6)
N2A	0.0258 (6)	0.0304 (7)	0.0371 (7)	0.0003 (5)	0.0009 (5)	−0.0085 (5)
C7A	0.0469 (10)	0.0357 (9)	0.0496 (11)	0.0062 (7)	−0.0007 (8)	−0.0174 (8)
C8A	0.0676 (14)	0.0342 (9)	0.0557 (12)	0.0016 (9)	−0.0119 (10)	−0.0213 (8)
C9A	0.0518 (11)	0.0344 (9)	0.0596 (12)	−0.0108 (8)	−0.0156 (10)	−0.0107 (8)
C10A	0.0331 (8)	0.0319 (8)	0.0487 (10)	−0.0086 (6)	−0.0055 (7)	−0.0017 (7)
C2A	0.0312 (8)	0.0368 (8)	0.0311 (8)	−0.0020 (6)	0.0077 (7)	−0.0034 (6)
C1A	0.0288 (8)	0.0419 (9)	0.0362 (9)	0.0013 (6)	0.0049 (7)	−0.0107 (7)
O1A	0.0449 (7)	0.0375 (6)	0.0389 (7)	−0.0012 (5)	−0.0030 (6)	−0.0068 (5)
C4A	0.0330 (9)	0.0471 (10)	0.0608 (13)	−0.0082 (7)	−0.0080 (8)	−0.0140 (9)
S1B	0.0384 (2)	0.0427 (2)	0.0365 (2)	0.00559 (17)	0.00863 (18)	−0.00300 (17)
C3B	0.0355 (8)	0.0259 (7)	0.0286 (8)	−0.0031 (6)	0.0039 (6)	−0.0065 (6)
N2B	0.0381 (7)	0.0304 (7)	0.0284 (7)	−0.0011 (5)	0.0044 (6)	−0.0051 (5)
C6B	0.0365 (8)	0.0270 (7)	0.0296 (8)	−0.0048 (6)	0.0043 (6)	−0.0079 (6)
C5B	0.0341 (8)	0.0292 (7)	0.0292 (8)	−0.0060 (6)	0.0040 (6)	−0.0072 (6)
N1B	0.0349 (7)	0.0315 (7)	0.0263 (7)	−0.0031 (5)	0.0037 (5)	−0.0036 (5)
C2B	0.0414 (9)	0.0400 (9)	0.0245 (8)	−0.0014 (7)	0.0047 (7)	−0.0041 (6)
C1B	0.0409 (10)	0.0404 (9)	0.0397 (10)	−0.0038 (7)	0.0071 (8)	0.0021 (7)
O1B	0.0349 (7)	0.0628 (9)	0.0443 (8)	0.0089 (6)	0.0116 (6)	0.0195 (6)
C10B	0.0398 (9)	0.0407 (9)	0.0367 (9)	−0.0002 (7)	−0.0023 (7)	−0.0052 (7)
C9B	0.0358 (9)	0.0508 (11)	0.0519 (12)	0.0036 (8)	0.0000 (8)	−0.0137 (9)
C8B	0.0390 (10)	0.0491 (10)	0.0491 (11)	−0.0024 (8)	0.0116 (8)	−0.0170 (8)
C7B	0.0433 (10)	0.0378 (9)	0.0336 (9)	−0.0055 (7)	0.0104 (7)	−0.0088 (7)
C4B	0.0442 (11)	0.0745 (14)	0.0448 (12)	0.0157 (10)	0.0037 (9)	0.0072 (10)

Geometric parameters (Å, º) top

S1A—C3A	1.7383 (16)	S1B—C3B	1.7369 (16)
S1A—C4A	1.7851 (19)	S1B—C4B	1.788 (2)
C3A—N1A	1.3700 (19)	C3B—N2B	1.321 (2)
C3A—N2A	1.321 (2)	C3B—N1B	1.368 (2)
N1A—C5A	1.384 (2)	N2B—C6B	1.396 (2)
N1A—C2A	1.461 (2)	C6B—C5B	1.398 (2)
C5A—C6A	1.396 (2)	C6B—C7B	1.396 (2)
C5A—C10A	1.396 (2)	C5B—N1B	1.390 (2)
C6A—N2A	1.397 (2)	C5B—C10B	1.388 (2)
C6A—C7A	1.395 (2)	N1B—C2B	1.458 (2)
C7A—C8A	1.382 (3)	C2B—C1B	1.509 (2)
C7A—H7A	0.950	C2B—H21B	0.950
C8A—C9A	1.392 (3)	C2B—H22B	0.950
C8A—H8A	0.950	C1B—O1B	1.413 (2)
C9A—C10A	1.385 (3)	C1B—H11B	0.950
C9A—H9A	0.950	C1B—H12B	0.950
C10A—H10A	0.950	O1B—H1B	0.95 (3)
C2A—C1A	1.510 (2)	C10B—C9B	1.382 (3)
C2A—H21A	0.950	C10B—H10B	0.950
C2A—H22A	0.950	C9B—C8B	1.391 (3)
C1A—O1A	1.402 (2)	C9B—H9B	0.950
C1A—H11A	0.950	C8B—C7B	1.385 (3)
C1A—H12A	0.950	C8B—H8B	0.950
O1A—H1A	1.01 (3)	C7B—H7B	0.950
C4A—H41A	0.950	C4B—H41B	0.950
C4A—H42A	0.950	C4B—H42B	0.950
C4A—H43A	0.950	C4B—H43B	0.950

C3A—S1A—C4A	100.28 (8)	C3B—S1B—C4B	100.22 (9)
S1A—C3A—N1A	119.56 (12)	S1B—C3B—N2B	126.69 (13)
S1A—C3A—N2A	126.71 (12)	S1B—C3B—N1B	119.73 (12)
N1A—C3A—N2A	113.67 (14)	N2B—C3B—N1B	113.53 (14)
C3A—N1A—C5A	106.27 (13)	C3B—N2B—C6B	104.41 (13)
C3A—N1A—C2A	127.66 (14)	N2B—C6B—C5B	110.28 (14)
C5A—N1A—C2A	125.82 (13)	N2B—C6B—C7B	129.65 (15)
N1A—C5A—C6A	105.66 (13)	C5B—C6B—C7B	120.07 (16)
N1A—C5A—C10A	131.55 (15)	C6B—C5B—N1B	105.33 (14)
C6A—C5A—C10A	122.79 (15)	C6B—C5B—C10B	122.56 (15)
C5A—C6A—N2A	110.23 (13)	N1B—C5B—C10B	132.10 (15)
C5A—C6A—C7A	120.05 (15)	C5B—N1B—C3B	106.45 (13)
N2A—C6A—C7A	129.72 (15)	C5B—N1B—C2B	126.32 (14)
C6A—N2A—C3A	104.17 (13)	C3B—N1B—C2B	127.15 (14)
C6A—C7A—C8A	117.44 (17)	N1B—C2B—C1B	113.41 (14)
C6A—C7A—H7A	120.6	N1B—C2B—H21B	108.5
C8A—C7A—H7A	122.0	C1B—C2B—H21B	108.4
C7A—C8A—C9A	121.94 (17)	N1B—C2B—H22B	108.5
C7A—C8A—H8A	119.0	C1B—C2B—H22B	108.5
C9A—C8A—H8A	119.0	H21B—C2B—H22B	109.5
C8A—C9A—C10A	121.66 (17)	C2B—C1B—O1B	109.85 (15)
C8A—C9A—H9A	119.2	C2B—C1B—H11B	109.4
C10A—C9A—H9A	119.2	O1B—C1B—H11B	109.5
C5A—C10A—C9A	116.10 (17)	C2B—C1B—H12B	109.4
C5A—C10A—H10A	122.0	O1B—C1B—H12B	109.3
C9A—C10A—H10A	121.9	H11B—C1B—H12B	109.5
N1A—C2A—C1A	113.63 (13)	C1B—O1B—H1B	110.3 (18)
N1A—C2A—H21A	108.4	C5B—C10B—C9B	116.51 (17)
C1A—C2A—H21A	108.3	C5B—C10B—H10B	121.8
N1A—C2A—H22A	108.5	C9B—C10B—H10B	121.7
C1A—C2A—H22A	108.5	C10B—C9B—C8B	121.79 (18)
H21A—C2A—H22A	109.5	C10B—C9B—H9B	119.1
C2A—C1A—O1A	110.78 (13)	C8B—C9B—H9B	119.1
C2A—C1A—H11A	109.2	C9B—C8B—C7B	121.60 (17)
O1A—C1A—H11A	109.2	C9B—C8B—H8B	119.2
C2A—C1A—H12A	109.1	C7B—C8B—H8B	119.2
O1A—C1A—H12A	109.0	C6B—C7B—C8B	117.47 (17)
H11A—C1A—H12A	109.5	C6B—C7B—H7B	121.3
C1A—O1A—H1A	110.8 (16)	C8B—C7B—H7B	121.3
S1A—C4A—H41A	109.5	S1B—C4B—H41B	109.5
S1A—C4A—H42A	109.5	S1B—C4B—H42B	109.5
H41A—C4A—H42A	109.5	H41B—C4B—H42B	109.5
S1A—C4A—H43A	109.5	S1B—C4B—H43B	109.4
H41A—C4A—H43A	109.5	H41B—C4B—H43B	109.5
H42A—C4A—H43A	109.5	H42B—C4B—H43B	109.5

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1A-C3A-N2A-C6A-C5A and C5A—C10A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···N2Aⁱ	0.95 (3)	1.88 (3)	2.825 (3)	174 (3)
O1A—H1A···N2B	1.01 (3)	1.80 (3)	2.808 (3)	175 (3)
C4A—H41A···O1Aⁱⁱ	0.95	2.42	3.366 (3)	174
C4A—H43A···Cg2ⁱⁱⁱ	0.95	2.86	3.627 (2)	139
C4B—H43B···Cg1	0.95	2.86	3.486 (2)	125
C10B—H10B···Cg2^iv	0.95	2.74	3.631 (2)	157

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂OS
M_r	208.28
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	9.3235 (2), 9.7659 (2), 11.4588 (3)
α, β, γ (°)	78.0849 (9), 88.9066 (8), 88.1399 (9)
V (Å³)	1020.25 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13769, 5257, 3996
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.102, 0.96
No. of reflections	5242
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.32

Computer programs: COLLECT (Nonius, 2001), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).