5-(3,4,5-Trimeth-oxy-phen-yl)-1,3,4-oxadiazole-2(3H)-thione.

The two rings in the title compound, C(11)H(12)N(2)O(4)S, are roughly coplanar [dihedral angle = 6.77 (8)°]. Whereas the two outer methyl groups of the three meth-oxy groups are almost coplanar with the aromatic ring to which they are attached [C-C-O-C torsion angles = 8.5 (3) and -8.3 (3)°], the methyl group of the central meth-oxy substituent is not [C-C-C-C = -78.4 (3)°]. The crystal packing is stabilized by N-H⋯O hydrogen bonding.

Related literature

For background to the use of 1,3,4-oxadiazo­les, see: Erden et al. (2005 ▶); Smicius et al. (2002 ▶); Dutta & Kataky (1992 ▶). For details of the biological activity of 1,3,4-oxadiazo­les, see: Chen, et al. (2000 ▶); Mehuskiene, et al. (2003 ▶); El-Emam et al. (2004 ▶); Krasovshii et al. (2000 ▶).

Experimental

Crystal data

C11H12N2O4S

M = 268.29

Monoclinic,

a = 12.506 (2) Å

b = 7.1577 (7) Å

c = 13.451 (2) Å

β = 96.558 (12)°

V = 1196.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 173 K

0.37 × 0.33 × 0.32 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.904, T max = 0.916

7121 measured reflections

2235 independent reflections

1679 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.112

S = 0.94

2235 reflections

171 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024967/tk2682sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024967/tk2682Isup2.hkl

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

C11H12N2O4S	F(000) = 560
Mr = 268.29	Dx = 1.490 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5950 reflections
a = 12.506 (2) Å	θ = 3.6–25.9°
b = 7.1577 (7) Å	µ = 0.28 mm−1
c = 13.451 (2) Å	T = 173 K
β = 96.558 (12)°	Block, colourless
V = 1196.2 (3) Å3	0.37 × 0.33 × 0.32 mm
Z = 4

Stoe IPDS II two-circle diffractometer	2235 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
graphite	Rint = 0.075
ω scans	θmax = 25.7°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −12→15
Tmin = 0.904, Tmax = 0.916	k = −7→8
7121 measured reflections	l = −16→16

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0699P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
2235 reflections	Δρmax = 0.45 e Å−3
171 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (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	0.40007 (5)	0.10396 (10)	0.11859 (4)	0.0358 (2)
O1	0.40507 (12)	0.1537 (2)	0.31509 (9)	0.0258 (4)
C1	0.45909 (18)	0.1504 (3)	0.23147 (14)	0.0260 (5)
N1	0.56078 (16)	0.1912 (3)	0.26552 (13)	0.0278 (4)
H1	0.619 (2)	0.211 (4)	0.233 (2)	0.040 (7)*
N2	0.57512 (15)	0.2258 (3)	0.36818 (12)	0.0273 (4)
C2	0.48040 (17)	0.2018 (3)	0.39406 (14)	0.0234 (5)
C11	0.44138 (17)	0.2288 (3)	0.49170 (14)	0.0232 (5)
C12	0.33315 (17)	0.2074 (3)	0.49941 (14)	0.0248 (5)
H12	0.2854	0.1702	0.4428	0.030*
C13	0.29410 (17)	0.2409 (3)	0.59106 (14)	0.0234 (5)
C14	0.36466 (18)	0.3006 (3)	0.67290 (14)	0.0238 (5)
C15	0.47369 (17)	0.3228 (3)	0.66338 (14)	0.0239 (5)
C16	0.51427 (18)	0.2840 (3)	0.57291 (14)	0.0246 (5)
H16	0.5890	0.2948	0.5669	0.030*
O17	0.18925 (12)	0.2223 (2)	0.60687 (10)	0.0289 (4)
O18	0.32183 (13)	0.3468 (2)	0.75958 (10)	0.0288 (4)
O19	0.53524 (12)	0.3899 (2)	0.74645 (10)	0.0307 (4)
C17	0.11725 (18)	0.1399 (4)	0.52800 (16)	0.0336 (6)
H17A	0.1079	0.2252	0.4707	0.050*
H17B	0.0473	0.1169	0.5520	0.050*
H17C	0.1474	0.0215	0.5075	0.050*
C18	0.34058 (19)	0.2114 (4)	0.83861 (15)	0.0328 (6)
H18A	0.3103	0.0907	0.8153	0.049*
H18B	0.3061	0.2531	0.8966	0.049*
H18C	0.4182	0.1980	0.8578	0.049*
C19	0.64872 (18)	0.3968 (4)	0.74341 (16)	0.0335 (6)
H19A	0.6768	0.2696	0.7393	0.050*
H19B	0.6830	0.4575	0.8042	0.050*
H19C	0.6644	0.4682	0.6846	0.050*

	U11	U22	U33	U12	U13	U23
S1	0.0358 (4)	0.0522 (4)	0.0195 (3)	−0.0034 (3)	0.0042 (2)	−0.0050 (2)
O1	0.0240 (8)	0.0374 (10)	0.0168 (7)	−0.0006 (7)	0.0050 (5)	−0.0010 (6)
C1	0.0267 (12)	0.0313 (13)	0.0212 (10)	0.0023 (10)	0.0076 (8)	0.0022 (8)
N1	0.0250 (10)	0.0401 (12)	0.0196 (8)	0.0001 (9)	0.0086 (7)	−0.0011 (8)
N2	0.0262 (10)	0.0376 (12)	0.0186 (8)	0.0003 (8)	0.0050 (7)	0.0000 (7)
C2	0.0231 (11)	0.0263 (12)	0.0208 (9)	0.0004 (9)	0.0018 (8)	0.0015 (8)
C11	0.0273 (11)	0.0243 (12)	0.0186 (9)	0.0029 (9)	0.0051 (8)	0.0017 (8)
C12	0.0249 (11)	0.0317 (13)	0.0179 (9)	−0.0018 (10)	0.0021 (8)	−0.0004 (8)
C13	0.0218 (11)	0.0284 (12)	0.0203 (10)	0.0009 (9)	0.0037 (8)	0.0013 (8)
C14	0.0281 (12)	0.0278 (12)	0.0161 (9)	0.0046 (9)	0.0046 (8)	−0.0004 (8)
C15	0.0252 (11)	0.0265 (11)	0.0190 (9)	0.0027 (9)	−0.0012 (8)	0.0010 (8)
C16	0.0213 (11)	0.0289 (13)	0.0239 (10)	0.0018 (9)	0.0038 (8)	0.0021 (8)
O17	0.0209 (8)	0.0453 (10)	0.0212 (7)	−0.0042 (7)	0.0053 (6)	−0.0041 (6)
O18	0.0321 (9)	0.0370 (10)	0.0183 (7)	0.0087 (7)	0.0064 (6)	−0.0004 (6)
O19	0.0245 (8)	0.0438 (10)	0.0228 (7)	0.0001 (7)	−0.0020 (6)	−0.0049 (6)
C17	0.0250 (12)	0.0430 (16)	0.0332 (12)	−0.0056 (11)	0.0043 (9)	−0.0109 (10)
C18	0.0358 (13)	0.0436 (15)	0.0197 (10)	0.0028 (11)	0.0060 (9)	0.0018 (9)
C19	0.0249 (12)	0.0435 (15)	0.0306 (11)	−0.0001 (11)	−0.0034 (9)	−0.0019 (10)

S1—C1	1.645 (2)	C15—O19	1.369 (2)
O1—C1	1.377 (2)	C15—C16	1.399 (3)
O1—C2	1.381 (2)	C16—H16	0.9500
C1—N1	1.334 (3)	O17—C17	1.437 (3)
N1—N2	1.394 (2)	O18—C18	1.438 (3)
N1—H1	0.90 (3)	O19—C19	1.425 (3)
N2—C2	1.284 (3)	C17—H17A	0.9800
C2—C11	1.465 (3)	C17—H17B	0.9800
C11—C12	1.378 (3)	C17—H17C	0.9800
C11—C16	1.398 (3)	C18—H18A	0.9800
C12—C13	1.398 (3)	C18—H18B	0.9800
C12—H12	0.9500	C18—H18C	0.9800
C13—O17	1.359 (3)	C19—H19A	0.9800
C13—C14	1.397 (3)	C19—H19B	0.9800
C14—O18	1.378 (2)	C19—H19C	0.9800
C14—C15	1.393 (3)
C1—O1—C2	106.11 (16)	C14—C15—C16	120.90 (18)
N1—C1—O1	104.66 (17)	C11—C16—C15	117.8 (2)
N1—C1—S1	132.15 (17)	C11—C16—H16	121.1
O1—C1—S1	123.19 (17)	C15—C16—H16	121.1
C1—N1—N2	112.87 (18)	C13—O17—C17	117.32 (16)
C1—N1—H1	131.5 (16)	C14—O18—C18	114.68 (17)
N2—N1—H1	115.3 (16)	C15—O19—C19	117.23 (17)
C2—N2—N1	103.10 (17)	O17—C17—H17A	109.5
N2—C2—O1	113.23 (17)	O17—C17—H17B	109.5
N2—C2—C11	129.62 (18)	H17A—C17—H17B	109.5
O1—C2—C11	117.04 (18)	O17—C17—H17C	109.5
C12—C11—C16	122.09 (18)	H17A—C17—H17C	109.5
C12—C11—C2	118.92 (18)	H17B—C17—H17C	109.5
C16—C11—C2	118.92 (19)	O18—C18—H18A	109.5
C11—C12—C13	119.51 (18)	O18—C18—H18B	109.5
C11—C12—H12	120.2	H18A—C18—H18B	109.5
C13—C12—H12	120.2	O18—C18—H18C	109.5
O17—C13—C14	116.15 (18)	H18A—C18—H18C	109.5
O17—C13—C12	124.19 (18)	H18B—C18—H18C	109.5
C14—C13—C12	119.6 (2)	O19—C19—H19A	109.5
O18—C14—C15	121.99 (18)	O19—C19—H19B	109.5
O18—C14—C13	117.95 (19)	H19A—C19—H19B	109.5
C15—C14—C13	119.95 (18)	O19—C19—H19C	109.5
O19—C15—C14	115.45 (18)	H19A—C19—H19C	109.5
O19—C15—C16	123.6 (2)	H19B—C19—H19C	109.5
C2—O1—C1—N1	1.4 (2)	C12—C13—C14—O18	174.8 (2)
C2—O1—C1—S1	−178.55 (17)	O17—C13—C14—C15	179.80 (19)
O1—C1—N1—N2	−1.4 (3)	C12—C13—C14—C15	−1.3 (3)
S1—C1—N1—N2	178.49 (19)	O18—C14—C15—O19	1.2 (3)
C1—N1—N2—C2	0.9 (3)	C13—C14—C15—O19	177.2 (2)
N1—N2—C2—O1	0.1 (2)	O18—C14—C15—C16	−176.7 (2)
N1—N2—C2—C11	−175.9 (2)	C13—C14—C15—C16	−0.7 (3)
C1—O1—C2—N2	−0.9 (2)	C12—C11—C16—C15	−1.8 (3)
C1—O1—C2—C11	175.60 (19)	C2—C11—C16—C15	175.1 (2)
N2—C2—C11—C12	175.1 (2)	O19—C15—C16—C11	−175.5 (2)
O1—C2—C11—C12	−0.8 (3)	C14—C15—C16—C11	2.2 (3)
N2—C2—C11—C16	−1.9 (4)	C14—C13—O17—C17	−172.7 (2)
O1—C2—C11—C16	−177.8 (2)	C12—C13—O17—C17	8.5 (3)
C16—C11—C12—C13	−0.2 (3)	C15—C14—O18—C18	−78.4 (3)
C2—C11—C12—C13	−177.1 (2)	C13—C14—O18—C18	105.6 (2)
C11—C12—C13—O17	−179.4 (2)	C14—C15—O19—C19	173.8 (2)
C11—C12—C13—C14	1.8 (3)	C16—C15—O19—C19	−8.3 (3)
O17—C13—C14—O18	−4.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O17i	0.90 (3)	2.06 (3)	2.881 (2)	151 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O17i	0.90 (3)	2.06 (3)	2.881 (2)	151 (2)

Symmetry code: (i) .