5-[1-(3,4-Dichloro­phen­oxy)eth­yl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate

Akhtar, T.; Khawar Rauf, M.; Hameed, S.; Lu, X.

doi:10.1107/S1600536809029894

organic compounds

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Volume 65| Part 9| September 2009| Pages o2075-o2076

doi:10.1107/S1600536809029894

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5-[1-(3,4-Dichlorophenoxy)ethyl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate

Tashfeen Akhtar,^a M. Khawar Rauf,^a Shahid Hameed ^a ^* and Xiaoming Lu ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Capital Normal University, Beijing Taiyuan 100037, People's Republic of China
^*Correspondence e-mail: shameed@qau.edu.pk

(Received 11 July 2009; accepted 28 July 2009; online 8 August 2009)

In the title compound, C₁₀H₈Cl₂N₂O₂S·0.5H₂O, the atoms in the oxadiazole ring are essentially coplanar (r.m.s. deviation 0.010 Å). The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds involving the water molecule, which is situated on an a twofold rotation axis, and two organic molecules, leading to a thione tautomer in the solid state. The C atom attached to the oxadiazole ring adopts a typical sp³ hybridization. The dihedral angle between the mean plane of the benzene ring of the dichlorophenyl 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_r = 300.15
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.078
S = 1.09
3088 reflections
162 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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).

Supporting information

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

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

checkCIF report

Comment top

1,3,4-Oxadiazoles are an important class of five-membered heterocycles. They show diverse biological activities, for example, antifungal, antibacterial (Almasirad et al., 2004), anti-convulsant (Aboraia et al. 2006), antitumour (Akhtar, Hameed, Khan et al., 2008) and enzyme inhibitory activities (Khan et al., 2005). In continuation to our work on five membered heterocycles (Akhtar & Hameed et al., 2007), the title compound was synthesized and evaluated for its biological activities (Akhtar et al., 2008a). Herein, we report on the crystal structure of 5-[1-(3,4-dichlorophenoxy) ethyl]-1,3,4-oxadiazole-2(3H)-thione, derived from 3,4-dichlorophenoxy propionic acid (Akhtar & Rauf et al., 2007).

The molecular structure of the title compound is illustrated in Fig. 1. The dihedral angle between the mean planes of the benzene and 1,3,4-oxadiazole rings is 74.18 (4)°. The bond lengths and angles are in good agreement with the expected values (Allen et al., 1987; Thamotharan et al., 2005). The N1—N2 [1.3817 (16) A°] and C1=S1 [1.6489 (13) A°] bond lengths correspond to the usual single bond N—N distance and C=S distance.

1,3,4-Oxadizole-2-thiones/thiols can exist in two tautomeric forms (Aydogan et al., 2002). In the title compound the thione form is observed. The H-atom of the thiol group has been transferred to the adjacent N atom of the oxadiazole ring (Fig. 1).

The title compound crystallized as a hemihydrate, with the water molecule lieing on a crystallographic two-fold axis. The water molecule O-atom hydrogen bonds to the NH group, while the water H-atom hydrogen bonds to the S-atom of the S=C moiety (see Table 1 and Fig. 2).

Related literature top

For related literature on oxadiazoles, their structures and properties, 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 related structures, see: Allen et al. (1987); Thamotharan et al. (2005).

Experimental top

3,4-dichlorophenoxy acid hydrazide (10.30 mmol) was stirred with KOH (12.37 mmol) dissolved in methanol (30 ml). Carbon disulfide (0.75 mL, 12.37 mmol) was added slowly with stirring. The yellow solution obtained was refluxed until the evolution of hydrogen sulfide had ceased (18h). The reaction mixture was then cooled to rt and filtered. The filtrate was then poured into ice cooled water and acidified with 6M HCl until the colour turned congo red. The precipitate that formed was filtered off and dried. Recrystallization from ethanol/water (1:1) afforded colorless block-like crystals, suitable for X-ray diffraction analysis.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Partial crystal packing diagram of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed pale-blue lines.

5-[1-(3,4-Dichlorophenoxy)ethyl]-1,3,4-oxadiazole-2(3H)- thione hemihydrate top

Crystal data top

C₁₀H₈Cl₂N₂O₂S·0.5H₂O	F(000) = 1224
M_r = 300.15	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0399P)² + 0.7008P] where P = (F_o² + 2F_c²)/3
3088 reflections	(Δ/σ)_max = 0.001
162 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₀H₈Cl₂N₂O₂S·0.5H₂O	V = 2490.38 (6) Å³
M_r = 300.15	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 11.8725 (2) Å	µ = 0.68 mm⁻¹
b = 7.8932 (1) Å	T = 123 K
c = 26.6092 (4) Å	0.40 × 0.30 × 0.25 mm
β = 92.913 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2490 reflections with I > 2σ(I)
10568 measured reflections	R_int = 0.019
3088 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.22 e Å⁻³
3088 reflections	Δρ_min = −0.21 e Å⁻³
162 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₈Cl₂N₂O₂S·0.5H₂O
M_r	300.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	11.8725 (2), 7.8932 (1), 26.6092 (4)
β (°)	92.913 (1)
V (Å³)	2490.38 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.40 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10568, 3088, 2490
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.078, 1.09
No. of reflections	3088
No. of parameters	162
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y+1/2, z.

Acknowledgements

The authors are grateful to Professor G. B. Jameson, Institute of Fundamental Sciences, Private Bag 11 222, Massey University, Palmerston North, New Zealand, for fruitful discussions.

References

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5-[1-(3,4-Di­chloro­phen­­oxy)eth­yl]-1,3,4-oxa­diazole-2(3H)-thione hemihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-[1-(3,4-Dichlorophenoxy)ethyl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate