5-[1-(3,4-Dichloro-phen-oxy)eth-yl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate.

In the title compound, C(10)H(8)Cl(2)N(2)O(2)S·0.5H(2)O, the atoms in the oxadiazole ring are essentially coplanar (r.m.s. deviation 0.010 Å). The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds involving the water mol-ecule, which is situated on an a twofold rotation axis, and two organic mol-ecules, leading to a thione tautomer in the solid state. The C atom attached to the oxadiazole ring adopts a typical sp(3) hybridization. The dihedral angle between the mean plane of the benzene ring of the dichloro-phenyl group and the mean plane of the oxadiazole ring is 74.18 (4)°. The crystal structure is stabilized by intermolecular N-H⋯O and O-H⋯S hydrogen bonds.

Related literature

For the structures and properties of oxadiazoles, see: Almasirad et al., (2004 ▶); Aboraia et al. (2006 ▶); Akhtar, Hameed, Al-Masoudi et al. (2008 ▶); Khan et al. (2005 ▶); Akhtar, Hameed et al. (2007 ▶); Akhtar, Hameed, Khan et al. (2008 ▶); Akhtar, Rauf et al. (2007 ▶); Aydogan et al., 2002 ▶). For a related structure, see: Thamotharan et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H8Cl2N2O2S·0.5H2O

M = 300.15

Monoclinic,

a = 11.8725 (2) Å

b = 7.89320 (10) Å

c = 26.6092 (4) Å

β = 92.9130 (10)°

V = 2490.38 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.68 mm−1

T = 123 K

0.40 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

10568 measured reflections

3088 independent reflections

2490 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.078

S = 1.09

3088 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029894/su2129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029894/su2129Isup2.hkl

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

C10H8Cl2N2O2S·0.5H2O	F(000) = 1224
Mr = 300.15	Dx = 1.601 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4427 reflections
a = 11.8725 (2) Å	θ = 3.1–28.3°
b = 7.8932 (1) Å	µ = 0.68 mm−1
c = 26.6092 (4) Å	T = 123 K
β = 92.913 (1)°	Block, colorless
V = 2490.38 (6) Å3	0.40 × 0.30 × 0.25 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2490 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 28.3°, θmin = 3.1°
φ and ω scans	h = −15→15
10568 measured reflections	k = −10→10
3088 independent reflections	l = −35→35

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.7008P] where P = (Fo2 + 2Fc2)/3
3088 reflections	(Δ/σ)max = 0.001
162 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 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
O1	0.25873 (7)	0.32348 (12)	0.33123 (4)	0.0347 (2)
C1	0.26630 (11)	0.47444 (17)	0.30643 (5)	0.0321 (3)
S1	0.15653 (3)	0.59419 (5)	0.290316 (15)	0.04313 (11)
N1	0.37606 (9)	0.49544 (15)	0.30057 (4)	0.0373 (3)
H1	0.4040	0.5814	0.2857	0.045*
N2	0.44029 (9)	0.36407 (16)	0.32095 (5)	0.0379 (3)
C2	0.36727 (11)	0.26539 (17)	0.33892 (5)	0.0330 (3)
C3	0.38524 (12)	0.09920 (18)	0.36521 (5)	0.0381 (3)
H3	0.4630	0.0612	0.3616	0.046*
C4	0.30442 (15)	−0.0347 (2)	0.34486 (6)	0.0495 (4)
H4A	0.3187	−0.1393	0.3625	0.074*
H4B	0.3148	−0.0510	0.3096	0.074*
H4C	0.2284	0.0010	0.3495	0.074*
O2	0.36403 (8)	0.11531 (14)	0.41765 (4)	0.0417 (2)
C5	0.44340 (11)	0.18810 (17)	0.45029 (5)	0.0351 (3)
C6	0.54468 (11)	0.25923 (18)	0.43709 (5)	0.0374 (3)
H6	0.5649	0.2584	0.4038	0.045*
C7	0.61526 (11)	0.33147 (19)	0.47429 (5)	0.0379 (3)
H7	0.6830	0.3797	0.4656	0.046*
C8	0.58683 (11)	0.33307 (17)	0.52386 (5)	0.0354 (3)
Cl1	0.67766 (3)	0.42681 (5)	0.568937 (14)	0.04480 (11)
C9	0.48523 (12)	0.26045 (17)	0.53664 (5)	0.0360 (3)
Cl2	0.44427 (3)	0.26092 (6)	0.598122 (14)	0.05328 (13)
C10	0.41405 (11)	0.18835 (18)	0.50013 (5)	0.0380 (3)
H10	0.3464	0.1399	0.5089	0.046*
O1W	0.5000	0.75760 (19)	0.2500	0.0457 (4)
H1W	0.5445 (15)	0.817 (2)	0.2687 (7)	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.0320 (4)	0.0336 (5)	0.0389 (5)	0.0003 (4)	0.0056 (4)	0.0056 (4)
C1	0.0360 (6)	0.0313 (7)	0.0291 (6)	0.0000 (5)	0.0026 (5)	−0.0009 (5)
S1	0.03808 (18)	0.0406 (2)	0.0504 (2)	0.00707 (14)	−0.00080 (15)	0.00403 (16)
N1	0.0354 (5)	0.0342 (6)	0.0425 (6)	0.0001 (5)	0.0062 (5)	0.0078 (5)
N2	0.0337 (5)	0.0384 (6)	0.0419 (6)	0.0037 (5)	0.0046 (5)	0.0045 (5)
C2	0.0349 (6)	0.0327 (7)	0.0315 (6)	0.0034 (5)	0.0032 (5)	−0.0013 (5)
C3	0.0434 (7)	0.0358 (7)	0.0355 (7)	0.0051 (6)	0.0045 (6)	0.0038 (6)
C4	0.0664 (10)	0.0345 (8)	0.0473 (9)	−0.0019 (7)	−0.0005 (7)	0.0028 (7)
O2	0.0414 (5)	0.0494 (6)	0.0344 (5)	−0.0037 (4)	0.0027 (4)	0.0062 (4)
C5	0.0356 (6)	0.0341 (7)	0.0356 (7)	0.0075 (5)	0.0025 (5)	0.0065 (6)
C6	0.0361 (7)	0.0437 (8)	0.0328 (7)	0.0066 (6)	0.0058 (5)	0.0059 (6)
C7	0.0335 (6)	0.0409 (8)	0.0400 (7)	0.0065 (6)	0.0065 (5)	0.0052 (6)
C8	0.0361 (6)	0.0332 (7)	0.0371 (7)	0.0098 (5)	0.0019 (5)	0.0023 (6)
Cl1	0.04519 (19)	0.0466 (2)	0.0423 (2)	0.00724 (15)	−0.00057 (14)	−0.00463 (16)
C9	0.0402 (7)	0.0363 (7)	0.0321 (7)	0.0119 (6)	0.0074 (5)	0.0071 (6)
Cl2	0.0564 (2)	0.0696 (3)	0.03508 (19)	0.00834 (19)	0.01402 (16)	0.00641 (18)
C10	0.0364 (7)	0.0380 (8)	0.0401 (7)	0.0051 (6)	0.0078 (6)	0.0096 (6)
O1W	0.0431 (8)	0.0329 (8)	0.0612 (10)	0.000	0.0048 (7)	0.000

O1—C1	1.3672 (16)	O2—C5	1.3745 (17)
O1—C2	1.3733 (15)	C5—C10	1.3882 (19)
C1—N1	1.3306 (16)	C5—C6	1.3884 (19)
C1—S1	1.6489 (13)	C6—C7	1.387 (2)
N1—N2	1.3817 (16)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.3783 (19)
N2—C2	1.2763 (18)	C7—H7	0.9300
C2—C3	1.4967 (19)	C8—C9	1.3931 (19)
C3—O2	1.4363 (17)	C8—Cl1	1.7371 (15)
C3—C4	1.509 (2)	C9—C10	1.378 (2)
C3—H3	0.9800	C9—Cl2	1.7302 (14)
C4—H4A	0.9600	C10—H10	0.9300
C4—H4B	0.9600	O1W—H1W	0.846 (17)
C4—H4C	0.9600
C1—O1—C2	106.18 (10)	H4A—C4—H4C	109.5
N1—C1—O1	104.71 (11)	H4B—C4—H4C	109.5
N1—C1—S1	131.59 (11)	C5—O2—C3	120.17 (10)
O1—C1—S1	123.69 (9)	O2—C5—C10	114.02 (12)
C1—N1—N2	112.63 (11)	O2—C5—C6	125.73 (12)
C1—N1—H1	123.7	C10—C5—C6	120.25 (14)
N2—N1—H1	123.7	C7—C6—C5	119.04 (13)
C2—N2—N1	103.48 (10)	C7—C6—H6	120.5
N2—C2—O1	112.99 (12)	C5—C6—H6	120.5
N2—C2—C3	128.79 (12)	C8—C7—C6	121.23 (13)
O1—C2—C3	118.20 (11)	C8—C7—H7	119.4
O2—C3—C2	110.40 (11)	C6—C7—H7	119.4
O2—C3—C4	105.72 (12)	C7—C8—C9	119.15 (13)
C2—C3—C4	111.92 (12)	C7—C8—Cl1	119.41 (11)
O2—C3—H3	109.6	C9—C8—Cl1	121.44 (10)
C2—C3—H3	109.6	C10—C9—C8	120.36 (12)
C4—C3—H3	109.6	C10—C9—Cl2	118.41 (11)
C3—C4—H4A	109.5	C8—C9—Cl2	121.22 (11)
C3—C4—H4B	109.5	C9—C10—C5	119.97 (13)
H4A—C4—H4B	109.5	C9—C10—H10	120.0
C3—C4—H4C	109.5	C5—C10—H10	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.86	2.06	2.9084 (16)	168
O1W—H1W···S1i	0.846 (17)	2.612 (18)	3.3854 (13)	152.5 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1W	0.86	2.06	2.9084 (16)	168
O1W—H1W⋯S1i	0.846 (17)	2.612 (18)	3.3854 (13)	152.5 (17)

Symmetry code: (i) .