5-[(4-Meth-oxy-benz-yl)sulfan-yl]-2-methyl-1,3,4-thia-diazole.

The title mol-ecule, C(11)H(12)N(2)OS(2), is twisted with a dihedral angle of 83.63 (12)° between the 1,3,4-thia-diazole and benzene rings. The meth-oxy group deviates slightly from the attached benzene ring, with a C-C-O-C torsion angle of 4.2 (4)°. In the crystal, mol-ecules are linked by weak C-H⋯N inter-actions and stacked along the c axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Wang et al. (2010 ▶). For background to and applications of thia­diazole derivatives, see: Bernard et al. (1985 ▶); Chandrakantha et al. (2010 ▶); El-Sabbagh et al. (2009) ▶; Isloor et al. (2010 ▶); Kalluraya et al. (2004 ▶). For the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H12N2OS2

M = 252.35

Monoclinic,

a = 14.7765 (4) Å

b = 8.6916 (3) Å

c = 9.7339 (3) Å

β = 96.477 (1)°

V = 1242.16 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 296 K

0.25 × 0.19 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.907, T max = 0.987

11429 measured reflections

2828 independent reflections

1660 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.118

S = 1.02

2828 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051858/is2640sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051858/is2640Isup2.hkl

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

C11H12N2OS2	F(000) = 528
Mr = 252.35	Dx = 1.349 Mg m−3
Monoclinic, P21/c	Melting point = 413–415 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.7765 (4) Å	Cell parameters from 2828 reflections
b = 8.6916 (3) Å	θ = 2.7–27.5°
c = 9.7339 (3) Å	µ = 0.41 mm−1
β = 96.477 (1)°	T = 296 K
V = 1242.16 (7) Å3	Plate, yellow
Z = 4	0.25 × 0.19 × 0.03 mm

Bruker APEXII CCD area-detector diffractometer	2828 independent reflections
Radiation source: sealed tube	1660 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
Tmin = 0.907, Tmax = 0.987	k = −11→11
11429 measured reflections	l = −12→12

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2899P] where P = (Fo2 + 2Fc2)/3
2828 reflections	(Δ/σ)max = 0.001
147 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.19 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
S1	0.43447 (5)	0.19481 (8)	0.95596 (7)	0.0631 (2)
S2	0.56474 (5)	0.40517 (9)	0.81756 (8)	0.0805 (3)
O1	0.99330 (14)	0.4254 (2)	0.7932 (2)	0.0899 (7)
N1	0.30610 (16)	0.3239 (3)	0.8041 (2)	0.0770 (7)
N2	0.38487 (18)	0.3952 (3)	0.7726 (2)	0.0795 (7)
C1	0.24763 (19)	0.1218 (4)	0.9455 (3)	0.0849 (9)
H1A	0.1893	0.1624	0.9098	0.127*
H1B	0.2534	0.1234	1.0447	0.127*
H1C	0.2529	0.0178	0.9141	0.127*
C2	0.32087 (18)	0.2174 (3)	0.8958 (2)	0.0616 (7)
C3	0.45726 (18)	0.3383 (3)	0.8427 (2)	0.0609 (7)
C4	0.63995 (18)	0.2718 (3)	0.9180 (3)	0.0672 (7)
H4A	0.6353	0.2848	1.0159	0.081*
H4B	0.6239	0.1665	0.8925	0.081*
C5	0.73488 (17)	0.3071 (3)	0.8867 (2)	0.0581 (7)
C6	0.7820 (2)	0.4335 (3)	0.9444 (3)	0.0697 (8)
H6A	0.7551	0.4956	1.0062	0.084*
C7	0.8673 (2)	0.4688 (3)	0.9122 (3)	0.0738 (8)
H7A	0.8977	0.5539	0.9528	0.089*
C8	0.90874 (18)	0.3794 (3)	0.8200 (3)	0.0624 (7)
C9	0.86360 (19)	0.2522 (3)	0.7635 (3)	0.0678 (7)
H9A	0.8909	0.1892	0.7029	0.081*
C10	0.77752 (18)	0.2183 (3)	0.7970 (3)	0.0653 (7)
H10A	0.7475	0.1324	0.7573	0.078*
C11	1.0358 (2)	0.3427 (5)	0.6936 (4)	0.1167 (14)
H11A	1.0964	0.3813	0.6905	0.175*
H11B	1.0014	0.3548	0.6046	0.175*
H11C	1.0385	0.2356	0.7180	0.175*

	U11	U22	U33	U12	U13	U23
S1	0.0756 (5)	0.0557 (4)	0.0557 (4)	0.0085 (3)	−0.0024 (3)	0.0090 (3)
S2	0.0880 (6)	0.0761 (6)	0.0793 (5)	0.0158 (4)	0.0181 (4)	0.0313 (4)
O1	0.0779 (14)	0.0861 (16)	0.1076 (16)	−0.0229 (11)	0.0186 (12)	−0.0254 (12)
N1	0.0787 (17)	0.0942 (19)	0.0594 (14)	0.0339 (14)	0.0139 (12)	0.0159 (14)
N2	0.0849 (17)	0.0896 (18)	0.0665 (15)	0.0385 (15)	0.0200 (13)	0.0277 (14)
C1	0.079 (2)	0.094 (2)	0.079 (2)	−0.0025 (18)	−0.0034 (16)	0.0020 (18)
C2	0.0744 (18)	0.0651 (18)	0.0449 (14)	0.0152 (14)	0.0056 (13)	−0.0067 (13)
C3	0.0806 (18)	0.0570 (17)	0.0466 (14)	0.0229 (14)	0.0137 (13)	0.0045 (12)
C4	0.0779 (19)	0.0640 (18)	0.0595 (16)	0.0065 (14)	0.0061 (14)	0.0151 (14)
C5	0.0708 (17)	0.0520 (16)	0.0507 (14)	0.0007 (13)	0.0035 (13)	0.0073 (13)
C6	0.099 (2)	0.0566 (18)	0.0563 (16)	−0.0032 (16)	0.0208 (15)	−0.0093 (14)
C7	0.099 (2)	0.0593 (18)	0.0631 (17)	−0.0209 (16)	0.0091 (16)	−0.0141 (15)
C8	0.0659 (17)	0.0571 (17)	0.0626 (17)	−0.0049 (14)	0.0002 (13)	−0.0044 (14)
C9	0.0701 (18)	0.0569 (17)	0.0758 (18)	0.0007 (14)	0.0062 (14)	−0.0168 (15)
C10	0.0701 (18)	0.0512 (17)	0.0726 (18)	−0.0057 (13)	−0.0011 (14)	−0.0122 (14)
C11	0.092 (2)	0.105 (3)	0.162 (4)	−0.014 (2)	0.051 (3)	−0.037 (3)

S1—C3	1.723 (3)	C4—H4B	0.9700
S1—C2	1.725 (3)	C5—C10	1.371 (3)
S2—C3	1.734 (3)	C5—C6	1.386 (4)
S2—C4	1.814 (3)	C6—C7	1.367 (4)
O1—C8	1.365 (3)	C6—H6A	0.9300
O1—C11	1.410 (3)	C7—C8	1.382 (4)
N1—C2	1.288 (3)	C7—H7A	0.9300
N1—N2	1.383 (3)	C8—C9	1.373 (4)
N2—C3	1.300 (3)	C9—C10	1.380 (3)
C1—C2	1.488 (4)	C9—H9A	0.9300
C1—H1A	0.9600	C10—H10A	0.9300
C1—H1B	0.9600	C11—H11A	0.9600
C1—H1C	0.9600	C11—H11B	0.9600
C4—C5	1.500 (3)	C11—H11C	0.9600
C4—H4A	0.9700
C3—S1—C2	87.33 (13)	C10—C5—C4	121.5 (2)
C3—S2—C4	102.99 (12)	C6—C5—C4	121.2 (2)
C8—O1—C11	118.1 (2)	C7—C6—C5	121.3 (2)
C2—N1—N2	113.2 (2)	C7—C6—H6A	119.4
C3—N2—N1	112.1 (2)	C5—C6—H6A	119.4
C2—C1—H1A	109.5	C6—C7—C8	120.7 (3)
C2—C1—H1B	109.5	C6—C7—H7A	119.7
H1A—C1—H1B	109.5	C8—C7—H7A	119.7
C2—C1—H1C	109.5	O1—C8—C9	125.0 (2)
H1A—C1—H1C	109.5	O1—C8—C7	116.2 (2)
H1B—C1—H1C	109.5	C9—C8—C7	118.8 (3)
N1—C2—C1	123.7 (3)	C8—C9—C10	119.8 (3)
N1—C2—S1	113.5 (2)	C8—C9—H9A	120.1
C1—C2—S1	122.8 (2)	C10—C9—H9A	120.1
N2—C3—S1	113.7 (2)	C5—C10—C9	122.2 (2)
N2—C3—S2	120.7 (2)	C5—C10—H10A	118.9
S1—C3—S2	125.53 (16)	C9—C10—H10A	118.9
C5—C4—S2	106.83 (17)	O1—C11—H11A	109.5
C5—C4—H4A	110.4	O1—C11—H11B	109.5
S2—C4—H4A	110.4	H11A—C11—H11B	109.5
C5—C4—H4B	110.4	O1—C11—H11C	109.5
S2—C4—H4B	110.4	H11A—C11—H11C	109.5
H4A—C4—H4B	108.6	H11B—C11—H11C	109.5
C10—C5—C6	117.3 (2)
C2—N1—N2—C3	0.2 (3)	S2—C4—C5—C6	76.6 (3)
N2—N1—C2—C1	−178.9 (2)	C10—C5—C6—C7	0.5 (4)
N2—N1—C2—S1	0.9 (3)	C4—C5—C6—C7	−177.7 (2)
C3—S1—C2—N1	−1.3 (2)	C5—C6—C7—C8	0.4 (4)
C3—S1—C2—C1	178.5 (2)	C11—O1—C8—C9	4.2 (4)
N1—N2—C3—S1	−1.3 (3)	C11—O1—C8—C7	−176.3 (3)
N1—N2—C3—S2	178.12 (18)	C6—C7—C8—O1	179.1 (2)
C2—S1—C3—N2	1.5 (2)	C6—C7—C8—C9	−1.4 (4)
C2—S1—C3—S2	−177.88 (18)	O1—C8—C9—C10	−179.1 (3)
C4—S2—C3—N2	−171.8 (2)	C7—C8—C9—C10	1.5 (4)
C4—S2—C3—S1	7.5 (2)	C6—C5—C10—C9	−0.4 (4)
C3—S2—C4—C5	172.25 (18)	C4—C5—C10—C9	177.8 (2)
S2—C4—C5—C10	−101.5 (3)	C8—C9—C10—C5	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N1i	0.96	2.59	3.532 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯N1i	0.96	2.59	3.532 (4)	164

Symmetry code: (i) .