1,3-Bis(ethoxy-meth-yl)-1H-benzimidazole-2(3H)-thione.

In the structure of the title compound, C(13)H(18)N(2)O(2)S, mol-ecules are linked together by inter-molecular C-H⋯S inter-actions into one-dimensional extended chains along the a axis. The crystal packing is further influenced by weak C-H⋯O inter-actions.

Related literature

For related structures, see: Odabaşoğlu et al. (2007 ▶). For applications and uses of benzimidazole-2-thio­nes, see: Zhang et al. (2001 ▶, 2007 ▶); Monforte et al. (2008 ▶); Mazloum et al. (2000 ▶); Perrin & Pagetti (1998 ▶). For chemical background on the synthesis of the title compound, see: Wang & Liu (1996 ▶, 2007 ▶); Rivera & Maldonado (2006 ▶); Rivera et al. (2008 ▶).

Experimental

Crystal data

C13H18N2O2S

M = 266.4

Monoclinic,

a = 4.7176 (2) Å

b = 16.0664 (6) Å

c = 17.5128 (6) Å

β = 96.524 (3)°

V = 1318.78 (9) Å3

Z = 4

Cu Kα radiation

μ = 2.14 mm−1

T = 120 K

0.36 × 0.09 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.239, T max = 1.000

11526 measured reflections

2096 independent reflections

1718 reflections with I > 3σ(I)

R int = 0.035

θmax = 62.3°

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 2.09

2096 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013036/bt5233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013036/bt5233Isup2.hkl

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

C13H18N2O2S	F(000) = 568
Mr = 266.4	Dx = 1.341 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 7933 reflections
a = 4.7176 (2) Å	θ = 3.7–62.4°
b = 16.0664 (6) Å	µ = 2.14 mm−1
c = 17.5128 (6) Å	T = 120 K
β = 96.524 (3)°	Needle, colorless
V = 1318.78 (9) Å3	0.36 × 0.09 × 0.07 mm
Z = 4

Oxford diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	2096 independent reflections
Radiation source: X-ray tube	1718 reflections with I > 3σ(I)
mirror	Rint = 0.035
Detector resolution: 10.3784 pixels mm-1	θmax = 62.3°, θmin = 3.7°
Rotation method data acquisition using ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −17→18
Tmin = 0.239, Tmax = 1.000	l = −19→19
11526 measured reflections

Refinement on F2	72 constraints
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.110	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 2.09	(Δ/σ)max = 0.001
2096 reflections	Δρmax = 0.40 e Å−3
163 parameters	Δρmin = −0.20 e Å−3
0 restraints

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.51 (release 27-10-2009 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
S1	0.66272 (9)	0.13029 (3)	0.10850 (3)	0.01931 (18)
O1	0.2405 (3)	−0.07593 (7)	0.17048 (7)	0.0188 (4)
O2	0.2199 (3)	0.33197 (7)	0.16433 (7)	0.0195 (4)
N1	0.3657 (3)	0.06085 (9)	0.21698 (8)	0.0149 (5)
N2	0.3556 (3)	0.19758 (9)	0.21569 (8)	0.0145 (5)
C1	0.4612 (4)	0.12960 (10)	0.18039 (10)	0.0155 (5)
C2	0.1990 (4)	0.08518 (11)	0.27371 (10)	0.0146 (5)
C3	0.1912 (4)	0.17210 (11)	0.27292 (10)	0.0139 (5)
C4	0.0581 (4)	0.03918 (11)	0.32458 (10)	0.0177 (6)
C5	−0.0933 (4)	0.08446 (12)	0.37497 (11)	0.0208 (6)
C6	−0.0995 (4)	0.17090 (12)	0.37354 (11)	0.0206 (6)
C7	0.0434 (4)	0.21684 (11)	0.32276 (10)	0.0175 (6)
C8	0.4585 (4)	−0.02431 (11)	0.20549 (11)	0.0176 (6)
C9	0.1567 (4)	−0.05799 (11)	0.09047 (10)	0.0184 (6)
C10	−0.0375 (4)	−0.12746 (11)	0.05950 (11)	0.0226 (6)
C11	0.4382 (4)	0.28343 (10)	0.20354 (11)	0.0175 (6)
C12	0.1586 (4)	0.31173 (12)	0.08429 (10)	0.0202 (6)
C13	−0.0308 (4)	0.37927 (12)	0.04732 (12)	0.0271 (7)
H4	0.063937	−0.020541	0.325288	0.0212*
H5	−0.194831	0.055195	0.411191	0.0249*
H6	−0.206135	0.199806	0.408844	0.0247*
H7	0.039587	0.276581	0.322332	0.021*
H8a	0.615369	−0.023937	0.175068	0.0211*
H8b	0.53383	−0.047767	0.254005	0.0211*
H9a	0.322743	−0.056905	0.063475	0.0221*
H9b	0.054516	−0.006229	0.085929	0.0221*
H10a	−0.113617	−0.114992	0.007583	0.0271*
H10b	0.068439	−0.178548	0.060477	0.0271*
H10c	−0.191054	−0.133156	0.090688	0.0271*
H11a	0.50122	0.308783	0.252159	0.021*
H11b	0.602547	0.284351	0.17585	0.021*
H12a	0.060143	0.259395	0.079039	0.0242*
H12b	0.333216	0.31009	0.061016	0.0242*
H13a	−0.091255	0.364675	−0.005165	0.0325*
H13b	−0.194805	0.385461	0.07462	0.0325*
H13c	0.07297	0.430762	0.048906	0.0325*

	U11	U22	U33	U12	U13	U23
S1	0.0197 (3)	0.0185 (3)	0.0207 (3)	−0.00013 (18)	0.0067 (2)	−0.00118 (18)
O1	0.0274 (7)	0.0112 (6)	0.0176 (7)	−0.0036 (5)	0.0012 (5)	−0.0003 (5)
O2	0.0273 (8)	0.0129 (7)	0.0181 (7)	0.0033 (5)	0.0022 (6)	0.0001 (5)
N1	0.0165 (8)	0.0109 (8)	0.0174 (8)	−0.0002 (6)	0.0020 (6)	−0.0006 (6)
N2	0.0164 (8)	0.0103 (7)	0.0169 (8)	0.0000 (6)	0.0025 (6)	−0.0016 (6)
C1	0.0147 (9)	0.0146 (10)	0.0164 (9)	−0.0007 (7)	−0.0020 (7)	−0.0016 (7)
C2	0.0136 (9)	0.0145 (9)	0.0155 (9)	0.0008 (7)	0.0003 (7)	−0.0027 (7)
C3	0.0128 (9)	0.0140 (9)	0.0141 (9)	−0.0018 (7)	−0.0013 (7)	0.0009 (7)
C4	0.0194 (10)	0.0124 (10)	0.0205 (10)	−0.0012 (7)	−0.0008 (8)	0.0005 (7)
C5	0.0210 (10)	0.0232 (10)	0.0179 (10)	−0.0055 (8)	0.0015 (8)	0.0052 (8)
C6	0.0211 (10)	0.0212 (10)	0.0201 (10)	0.0027 (8)	0.0051 (8)	−0.0025 (8)
C7	0.0191 (10)	0.0124 (10)	0.0205 (10)	0.0017 (7)	−0.0003 (8)	−0.0009 (7)
C8	0.0203 (10)	0.0106 (9)	0.0215 (10)	0.0029 (7)	0.0006 (8)	−0.0028 (7)
C9	0.0219 (10)	0.0148 (9)	0.0185 (9)	0.0028 (7)	0.0029 (7)	0.0016 (7)
C10	0.0255 (11)	0.0201 (11)	0.0216 (10)	0.0000 (8)	0.0003 (8)	−0.0013 (8)
C11	0.0220 (11)	0.0115 (9)	0.0186 (10)	−0.0033 (7)	0.0007 (7)	0.0005 (7)
C12	0.0244 (11)	0.0182 (10)	0.0181 (10)	−0.0043 (8)	0.0026 (8)	−0.0014 (7)
C13	0.0275 (11)	0.0282 (12)	0.0246 (11)	0.0005 (8)	−0.0011 (9)	0.0036 (8)

S1—C1	1.6618 (19)	C6—H6	0.96
O1—C8	1.406 (2)	C7—H7	0.96
O1—C9	1.441 (2)	C8—H8a	0.96
O2—C11	1.407 (2)	C8—H8b	0.96
O2—C12	1.436 (2)	C9—C10	1.505 (3)
N1—C1	1.378 (2)	C9—H9a	0.96
N1—C2	1.392 (2)	C9—H9b	0.96
N1—C8	1.457 (2)	C10—H10a	0.96
N2—C1	1.376 (2)	C10—H10b	0.96
N2—C3	1.397 (2)	C10—H10c	0.96
N2—C11	1.456 (2)	C11—H11a	0.96
C2—C3	1.397 (2)	C11—H11b	0.96
C2—C4	1.384 (3)	C12—C13	1.504 (3)
C3—C7	1.379 (3)	C12—H12a	0.96
C4—C5	1.401 (3)	C12—H12b	0.96
C4—H4	0.96	C13—H13a	0.96
C5—C6	1.389 (3)	C13—H13b	0.96
C5—H5	0.96	C13—H13c	0.96
C6—C7	1.388 (3)
C8—O1—C9	114.35 (13)	N1—C8—H8b	109.4708
C11—O2—C12	113.95 (13)	H8a—C8—H8b	105.1992
C1—N1—C2	110.36 (14)	O1—C9—C10	106.89 (14)
C1—N1—C8	124.70 (15)	O1—C9—H9a	109.4714
C2—N1—C8	124.42 (15)	O1—C9—H9b	109.4714
C1—N2—C3	110.40 (14)	C10—C9—H9a	109.4711
C1—N2—C11	124.75 (15)	C10—C9—H9b	109.4713
C3—N2—C11	124.23 (15)	H9a—C9—H9b	111.9358
S1—C1—N1	127.08 (13)	C9—C10—H10a	109.4709
S1—C1—N2	127.05 (13)	C9—C10—H10b	109.4709
N1—C1—N2	105.86 (15)	C9—C10—H10c	109.4713
N1—C2—C3	106.86 (15)	H10a—C10—H10b	109.4713
N1—C2—C4	131.39 (16)	H10a—C10—H10c	109.4718
C3—C2—C4	121.75 (16)	H10b—C10—H10c	109.4711
N2—C3—C2	106.50 (15)	O2—C11—N2	113.78 (14)
N2—C3—C7	131.54 (16)	O2—C11—H11a	109.4713
C2—C3—C7	121.95 (17)	O2—C11—H11b	109.4723
C2—C4—C5	116.41 (16)	N2—C11—H11a	109.4702
C2—C4—H4	121.7924	N2—C11—H11b	109.4712
C5—C4—H4	121.793	H11a—C11—H11b	104.7886
C4—C5—C6	121.26 (18)	O2—C12—C13	107.50 (15)
C4—C5—H5	119.3691	O2—C12—H12a	109.4709
C6—C5—H5	119.369	O2—C12—H12b	109.4714
C5—C6—C7	122.17 (18)	C13—C12—H12a	109.4711
C5—C6—H6	118.9156	C13—C12—H12b	109.4711
C7—C6—H6	118.916	H12a—C12—H12b	111.3742
C3—C7—C6	116.46 (17)	C12—C13—H13a	109.4719
C3—C7—H7	121.7704	C12—C13—H13b	109.4712
C6—C7—H7	121.771	C12—C13—H13c	109.471
O1—C8—N1	113.43 (14)	H13a—C13—H13b	109.471
O1—C8—H8a	109.4721	H13a—C13—H13c	109.4706
O1—C8—H8b	109.4715	H13b—C13—H13c	109.4717
N1—C8—H8a	109.4706

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.95	2.57	3.489 (2)	158.46
C7—H7···O1ii	0.95	2.58	3.480 (2)	155.41
C8—H8a···S1	0.95	2.75	3.2180 (19)	110.16
C11—H11b···S1	0.95	2.77	3.2166 (19)	109.21
C12—H12a···S1iii	0.96	2.88	3.7915 (19)	158.58

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.95	2.57	3.489 (2)	158.46
C7—H7⋯O1ii	0.95	2.58	3.480 (2)	155.41
C12—H12a⋯S1iii	0.96	2.88	3.7915 (19)	158.58

Symmetry codes: (i) ; (ii) ; (iii) .