Ethyl 2-(5-phenyl-1,3,4-oxadiazol-2-ylsulfan-yl)acetate.

The title mol-ecule, C(12)H(12)N(2)O(3)S, is composed of two individually planar units, viz. 5-phenyl-1,3,4-oxadiazol-2-yl-sulfanyl and ethyl acetate, which are oriented at almost right angles [80.07 (8)°] with respect to each other. The structure is stabilized by weak inter-molecular C-H⋯O and C-H⋯N hydrogen bonds. The phenyl and oxadiazole rings show π-π stacking inter-actions [centroid-centroid distance = 3.846 (2) Å] and there is also a short π-inter-action between the carbonyl O atom and the oxadiazole ring [the distance from this O atom to the centroid of the oxadiazole ring is 3.156 (2) Å].

Related literature

For related literature, see: Cao et al. (2002 ▶); Iqbal et al. (2007 ▶); Kadi et al. (2007 ▶); Mir & Siddiqui (1970 ▶); Zareef et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C12H12N2O3S

M = 264.30

Monoclinic,

a = 8.777 (3) Å

b = 11.008 (5) Å

c = 13.177 (6) Å

β = 103.59 (3)°

V = 1237.5 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 173 (2) K

0.16 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.959, T max = 0.979

5263 measured reflections

2820 independent reflections

1943 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.02

2820 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SAPI91 (Fan, 1991 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007125/fb2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007125/fb2092Isup2.hkl

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

C12H12N2O3S	F000 = 552
Mr = 264.30	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Melting point = 344–345 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 8.777 (3) Å	Cell parameters from 5263 reflections
b = 11.008 (5) Å	θ = 3.7–27.5º
c = 13.177 (6) Å	µ = 0.26 mm−1
β = 103.59 (3)º	T = 173 (2) K
V = 1237.5 (9) Å3	Prism, colourless
Z = 4	0.16 × 0.10 × 0.08 mm

Nonius KappaCCD diffractometer	2820 independent reflections
Radiation source: fine-focus sealed tube	1943 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.046
T = 173(2) K	θmax = 27.5º
ω and φ scans	θmin = 3.7º
Absorption correction: multi-scan(SORTAV; Blessing, 1997)	h = −11→11
Tmin = 0.959, Tmax = 0.979	k = −13→14
5263 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.058P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2820 reflections	Δρmax = 0.25 e Å−3
165 parameters	Δρmin = −0.27 e Å−3
47 constraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (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.

	x	y	z	Uiso*/Ueq
S1	0.76489 (6)	0.36024 (5)	0.69782 (4)	0.0336 (2)
O1	0.67313 (14)	0.20172 (11)	0.54296 (10)	0.0264 (3)
O2	0.86894 (16)	0.19182 (14)	0.88791 (12)	0.0412 (4)
O3	1.12555 (15)	0.22664 (13)	0.90282 (11)	0.0354 (4)
N1	0.87361 (18)	0.07562 (15)	0.55872 (13)	0.0307 (4)
N2	0.91309 (18)	0.16477 (15)	0.63754 (13)	0.0319 (4)
C1	0.6404 (2)	0.03494 (16)	0.41660 (14)	0.0245 (4)
C2	0.7088 (2)	−0.06503 (17)	0.37915 (15)	0.0283 (5)
H2	0.8131	−0.0882	0.4116	0.034*
C3	0.6246 (2)	−0.13002 (18)	0.29499 (16)	0.0339 (5)
H3	0.6717	−0.1972	0.2690	0.041*
C4	0.4712 (2)	−0.09762 (19)	0.24806 (16)	0.0335 (5)
H4	0.4130	−0.1429	0.1905	0.040*
C5	0.4040 (2)	0.0005 (2)	0.28557 (16)	0.0342 (5)
H5	0.2991	0.0225	0.2534	0.041*
C6	0.4870 (2)	0.06791 (19)	0.36949 (15)	0.0291 (5)
H6	0.4397	0.1357	0.3945	0.035*
C7	0.7333 (2)	0.10069 (16)	0.50595 (15)	0.0245 (4)
C8	0.7925 (2)	0.23515 (17)	0.62486 (15)	0.0266 (4)
C9	0.9529 (2)	0.35400 (18)	0.78938 (17)	0.0337 (5)
H9A	1.0358	0.3499	0.7498	0.040*
H9B	0.9684	0.4302	0.8304	0.040*
C10	0.9730 (2)	0.24772 (19)	0.86414 (16)	0.0311 (5)
C11	1.1623 (2)	0.1290 (2)	0.97896 (17)	0.0392 (6)
H11A	1.1105	0.0528	0.9492	0.047*
H11B	1.1252	0.1498	1.0422	0.047*
C12	1.3366 (2)	0.1135 (2)	1.00597 (17)	0.0421 (6)
H12A	1.3655	0.0466	1.0558	0.051*
H12B	1.3864	0.1887	1.0373	0.051*
H12C	1.3722	0.0952	0.9425	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0300 (3)	0.0316 (3)	0.0369 (3)	0.0048 (2)	0.0031 (2)	−0.0069 (2)
O1	0.0232 (7)	0.0275 (7)	0.0273 (7)	0.0048 (6)	0.0037 (5)	−0.0008 (6)
O2	0.0280 (7)	0.0554 (10)	0.0392 (9)	−0.0054 (7)	0.0056 (7)	−0.0009 (8)
O3	0.0235 (7)	0.0397 (8)	0.0407 (9)	0.0003 (6)	0.0026 (6)	0.0013 (7)
N1	0.0292 (8)	0.0333 (10)	0.0278 (9)	0.0061 (7)	0.0031 (7)	−0.0055 (8)
N2	0.0279 (9)	0.0354 (10)	0.0308 (10)	0.0070 (8)	0.0038 (7)	−0.0050 (8)
C1	0.0265 (9)	0.0261 (10)	0.0219 (10)	−0.0015 (8)	0.0074 (8)	0.0045 (8)
C2	0.0275 (10)	0.0286 (10)	0.0288 (11)	0.0000 (9)	0.0066 (8)	0.0020 (9)
C3	0.0403 (12)	0.0296 (11)	0.0327 (12)	−0.0022 (10)	0.0103 (9)	−0.0023 (9)
C4	0.0349 (11)	0.0373 (12)	0.0278 (11)	−0.0128 (10)	0.0061 (9)	−0.0010 (9)
C5	0.0250 (10)	0.0473 (13)	0.0286 (11)	−0.0036 (10)	0.0031 (9)	0.0057 (10)
C6	0.0265 (10)	0.0354 (11)	0.0264 (11)	0.0028 (9)	0.0085 (8)	0.0044 (9)
C7	0.0241 (9)	0.0235 (10)	0.0278 (10)	0.0056 (8)	0.0101 (8)	0.0034 (8)
C8	0.0243 (9)	0.0283 (10)	0.0267 (10)	0.0011 (9)	0.0050 (8)	0.0005 (8)
C9	0.0269 (10)	0.0336 (11)	0.0382 (12)	−0.0033 (9)	0.0027 (9)	−0.0088 (9)
C10	0.0241 (10)	0.0381 (12)	0.0300 (11)	−0.0027 (9)	0.0040 (8)	−0.0111 (9)
C11	0.0353 (11)	0.0437 (14)	0.0387 (13)	0.0012 (10)	0.0089 (10)	0.0031 (10)
C12	0.0356 (12)	0.0534 (15)	0.0360 (13)	0.0066 (11)	0.0056 (10)	0.0033 (11)

S1—C8	1.729 (2)	C3—H3	0.9500
S1—C9	1.802 (2)	C4—C5	1.377 (3)
O1—C8	1.366 (2)	C4—H4	0.9500
O1—C7	1.369 (2)	C5—C6	1.387 (3)
O2—C10	1.202 (2)	C5—H5	0.9500
O3—C10	1.336 (2)	C6—H6	0.9500
O3—C11	1.454 (3)	C9—C10	1.513 (3)
N1—C7	1.294 (2)	C9—H9A	0.9900
N1—N2	1.412 (2)	C9—H9B	0.9900
N2—C8	1.291 (2)	C11—C12	1.497 (3)
C1—C6	1.392 (2)	C11—H11A	0.9900
C1—C2	1.398 (3)	C11—H11B	0.9900
C1—C7	1.457 (3)	C12—H12A	0.9800
C2—C3	1.379 (3)	C12—H12B	0.9800
C2—H2	0.9500	C12—H12C	0.9800
C3—C4	1.390 (3)
C8—S1—C9	96.66 (9)	O1—C7—C1	120.13 (15)
C8—O1—C7	102.24 (13)	N2—C8—O1	113.20 (17)
C10—O3—C11	115.56 (16)	N2—C8—S1	128.61 (15)
C7—N1—N2	106.58 (15)	O1—C8—S1	118.18 (13)
C8—N2—N1	105.66 (15)	C10—C9—S1	114.43 (14)
C6—C1—C2	119.91 (17)	C10—C9—H9A	108.7
C6—C1—C7	121.99 (18)	S1—C9—H9A	108.7
C2—C1—C7	118.10 (16)	C10—C9—H9B	108.7
C3—C2—C1	119.90 (18)	S1—C9—H9B	108.7
C3—C2—H2	120.0	H9A—C9—H9B	107.6
C1—C2—H2	120.0	O2—C10—O3	124.49 (19)
C2—C3—C4	120.3 (2)	O2—C10—C9	125.87 (18)
C2—C3—H3	119.8	O3—C10—C9	109.62 (17)
C4—C3—H3	119.8	O3—C11—C12	107.26 (18)
C5—C4—C3	119.56 (18)	O3—C11—H11A	110.3
C5—C4—H4	120.2	C12—C11—H11A	110.3
C3—C4—H4	120.2	O3—C11—H11B	110.3
C4—C5—C6	121.14 (18)	C12—C11—H11B	110.3
C4—C5—H5	119.4	H11A—C11—H11B	108.5
C6—C5—H5	119.4	C11—C12—H12A	109.5
C5—C6—C1	119.2 (2)	C11—C12—H12B	109.5
C5—C6—H6	120.4	H12A—C12—H12B	109.5
C1—C6—H6	120.4	C11—C12—H12C	109.5
N1—C7—O1	112.32 (16)	H12A—C12—H12C	109.5
N1—C7—C1	127.55 (18)	H12B—C12—H12C	109.5
C7—N1—N2—C8	0.1 (2)	C6—C1—C7—O1	−3.2 (3)
C6—C1—C2—C3	0.6 (3)	C2—C1—C7—O1	177.68 (16)
C7—C1—C2—C3	179.73 (18)	N1—N2—C8—O1	−0.3 (2)
C1—C2—C3—C4	−0.9 (3)	N1—N2—C8—S1	178.66 (15)
C2—C3—C4—C5	0.5 (3)	C7—O1—C8—N2	0.4 (2)
C3—C4—C5—C6	0.1 (3)	C7—O1—C8—S1	−178.68 (14)
C4—C5—C6—C1	−0.3 (3)	C9—S1—C8—N2	0.1 (2)
C2—C1—C6—C5	0.0 (3)	C9—S1—C8—O1	179.01 (15)
C7—C1—C6—C5	−179.09 (18)	C8—S1—C9—C10	−69.82 (17)
N2—N1—C7—O1	0.2 (2)	C11—O3—C10—O2	−0.3 (3)
N2—N1—C7—C1	−179.84 (18)	C11—O3—C10—C9	177.96 (16)
C8—O1—C7—N1	−0.4 (2)	S1—C9—C10—O2	−22.7 (3)
C8—O1—C7—C1	179.66 (16)	S1—C9—C10—O3	159.06 (14)
C6—C1—C7—N1	176.80 (19)	C10—O3—C11—C12	175.61 (18)
C2—C1—C7—N1	−2.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.95	2.51	3.268 (3)	137
C9—H9B···N1ii	0.99	2.38	3.293 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.95	2.51	3.268 (3)	137
C9—H9B⋯N1ii	0.99	2.38	3.293 (3)	153

Symmetry codes: (i) ; (ii) .