N-(5-Sulfanyl­idene-4,5-dihydro-1,3,4-thia­diazol-2-yl)acetamide dimethyl sulfoxide disolvate

Kang, S.K.; Cho, N.S.; Jang, S.

doi:10.1107/S1600536811054298

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o224

doi:10.1107/S1600536811054298

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N-(5-Sulfanylidene-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide dimethyl sulfoxide disolvate

Sung Kwon Kang,^a ^* Nam Sook Cho ^a and Siyoung Jang ^a

^aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

(Received 7 December 2011; accepted 16 December 2011; online 23 December 2011)

In the title compound, C₄H₅N₃OS₂·2C₂H₆OS, the five-membered heterocyclic ring and the N—(C=O)—C plane of the acetamide group are essentially co-planar, with a dihedral angle of 1.25 (3)°. Intermolecular N—H⋯O hydrogen bonds between the acetamide compound and the dimethyl sulfoxide molecules stabilize the crystal structure. The two dimethyl sulfoxide molecules are each disordered over two positions with occupancy ratios of 0.605 (2):0.395 (2) and 0.8629 (18):0.1371 (18).

Related literature

For the synthesis and biological activity of thiadiazole compounds, see: Hildebrandt et al. (2011 ); Cho et al. (1993 ). For the structures of thiadiazole derivatives, see: Zhan et al. (2007 , 2009 ).

Experimental

Crystal data

C₄H₅N₃OS₂·2C₂H₆OS
M_r = 331.49
Triclinic, $[P \overline 1]$
a = 7.090 (2) Å
b = 9.982 (3) Å
c = 11.513 (3) Å
α = 100.872 (6)°
β = 96.827 (4)°
γ = 91.359 (4)°
V = 793.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 296 K
0.28 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.894, T_max = 0.916
24389 measured reflections
3292 independent reflections
2625 reflections with I > 2σ(I)
R_int = 0.180

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.117
S = 1.06
3292 reflections
245 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O16	0.88 (2)	1.91 (2)	2.783 (3)	170 (3)
N7—H7⋯O12	0.86 (2)	1.89 (2)	2.734 (8)	166 (2)

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811054298/is5026sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054298/is5026Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054298/is5026Isup3.cml

checkCIF report

Comment top

Thiadiazole derivatives have recently attracted attention in synthesis and biological activities (Hildebrandt et al., 2011; Zhan et al., 2009; Zhan et al., 2007). Our interest in thiadiazoles have formed systematic efforts to obtain new biologically active pyrimidines, purines and their analogs (Cho et al., 1993). 5-Amino-2H-1,2,4-thiadiazol-3-one is five-membered ring analog of cytosine. 5-Amino-3H-1,3,4-thiadiazole-2-thione is a sulfur analog of 5-amino-3H-1,3,4-thiadizol-2-one which is an isomer of 5-amino-2H-1,2,4-thiadiazol-3-one. Herein, the crystal structure of acetylation of 5-amino-3H-1,3,4-thiadiazole-2-thione, (I), is reported (Fig. 1).

The 1,3,4-thiadiazol-2-yl five-membered ring is planar, with a mean deviation of 0.008 Å from the corresponding least-squares plane defined by the seven constituent atoms. The bond distance of C3—N4 [1.2952 (23) Å] is shorter than that of N4—C1 [1.3365 (22) Å], which is consistent with double bond character. The dihedral angle between the 5-thioxo-1,3,4-thiadiazol-2-yl heterocyclic ring and the acetamide group is 1.25 (3) °, which is essentially planar. The crystal structure is stabilized by the intermolecular N—H···O hydrogen bonds between the compound and the DMSO molecules (Fig. 2 and Table 1).

Related literature top

For the synthesis and biological activity of thiadiazole compounds, see: Hildebrandt et al. (2011); Cho et al. (1993). For the structures of thiadiazole derivatives, see: Zhan et al. (2007, 2009).

Experimental top

5-Amino-3H-1,3,4-thiadiazole-2-thione (1.33 g, 0.011 mol) was dissolved in tetrahydrofuran (50 ml). Triethylamine(1.51 g, 0.015 mol) and a methyl benzoyl chloride (0.01 mol) were added to the solution and the mixture was refluxed with stirring for 4 h. Triethylamine hydrochloride was filtered off, the solution was concentrated to one-third of its original volume, and carefully acidified with concentrated hydrochloric acid. The precipitate was collected by filteration and recrystallized from aqueous ethanol to obtain an analytical product. Colorless crystals of (I) were obtained from its DMSO solution by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids. DMSO molecules show only major parts. Intermolecular N—H···O hydrogen bonds are indicated by dashed lines.
	Fig. 2. Part of the crystal structure of the title compound, showing molecules linked by intermolecular N—H···O hydrogen bonds (dashed lines).

N-(5-Sulfanylidene-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide dimethyl sulfoxide disolvate top

Crystal data top

C₄H₅N₃OS₂·2C₂H₆OS	Z = 2
M_r = 331.49	F(000) = 348
Triclinic, P1	D_x = 1.387 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.090 (2) Å	Cell parameters from 8583 reflections
b = 9.982 (3) Å	θ = 2.5–27.9°
c = 11.513 (3) Å	µ = 0.60 mm⁻¹
α = 100.872 (6)°	T = 296 K
β = 96.827 (4)°	Block, colourless
γ = 91.359 (4)°	0.28 × 0.18 × 0.13 mm
V = 793.6 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2625 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.180
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
T_min = 0.894, T_max = 0.916	k = −12→12
24389 measured reflections	l = −14→14
3292 independent reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0538P)² + 0.016P] where P = (F_o² + 2F_c²)/3
3292 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.22 e Å⁻³
7 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₄H₅N₃OS₂·2C₂H₆OS	γ = 91.359 (4)°
M_r = 331.49	V = 793.6 (4) Å³
Triclinic, P1	Z = 2
a = 7.090 (2) Å	Mo Kα radiation
b = 9.982 (3) Å	µ = 0.60 mm⁻¹
c = 11.513 (3) Å	T = 296 K
α = 100.872 (6)°	0.28 × 0.18 × 0.13 mm
β = 96.827 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3292 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2625 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.916	R_int = 0.180
24389 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	7 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
3292 reflections	Δρ_min = −0.35 e Å⁻³
245 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
C1	0.2794 (2)	0.12725 (17)	0.77693 (18)	0.0551 (4)
S2	0.26666 (7)	0.02071 (4)	0.63771 (4)	0.05621 (17)
C3	0.2555 (2)	0.16373 (16)	0.57197 (17)	0.0504 (4)
N4	0.2592 (2)	0.27936 (14)	0.64572 (16)	0.0618 (4)
N5	0.2732 (2)	0.25591 (15)	0.75980 (16)	0.0604 (4)
H5	0.277 (4)	0.323 (2)	0.822 (2)	0.113 (10)*
S6	0.29892 (10)	0.07416 (6)	0.90641 (5)	0.0767 (2)
N7	0.2429 (2)	0.15853 (15)	0.45173 (15)	0.0566 (4)
H7	0.238 (3)	0.237 (2)	0.432 (2)	0.070 (6)*
C8	0.2374 (3)	0.03883 (18)	0.36972 (18)	0.0577 (5)
C9	0.2250 (3)	0.0526 (2)	0.2426 (2)	0.0721 (6)
H9A	0.2405	0.1472	0.2382	0.108*
H9B	0.103	0.0168	0.2017	0.108*
H9C	0.3234	0.0026	0.2058	0.108*
O10	0.2408 (2)	−0.07095 (13)	0.40190 (14)	0.0768 (4)
S11	0.14717 (14)	0.51941 (8)	0.37275 (8)	0.0627 (4)	0.605 (2)
O12	0.2642 (8)	0.3906 (8)	0.3592 (8)	0.0824 (17)	0.605 (2)
C13	0.265 (2)	0.6272 (13)	0.5029 (11)	0.101 (4)	0.605 (2)
H13A	0.2399	0.5925	0.5721	0.151*	0.605 (2)
H13B	0.2205	0.7179	0.5081	0.151*	0.605 (2)
H13C	0.4	0.6296	0.4989	0.151*	0.605 (2)
C14	0.2160 (13)	0.6060 (7)	0.2625 (7)	0.068 (3)	0.605 (2)
H14A	0.1725	0.5532	0.1848	0.102*	0.605 (2)
H14B	0.352	0.6181	0.2719	0.102*	0.605 (2)
H14C	0.1607	0.6936	0.271	0.102*	0.605 (2)
S11A	0.3122 (2)	0.52142 (13)	0.37732 (12)	0.0645 (5)	0.395 (2)
O12A	0.1799 (11)	0.3913 (11)	0.3575 (12)	0.076 (2)	0.395 (2)
C13A	0.231 (3)	0.6329 (17)	0.4958 (14)	0.080 (4)	0.395 (2)
H13D	0.2722	0.6043	0.5693	0.12*	0.395 (2)
H13E	0.0943	0.6316	0.4838	0.12*	0.395 (2)
H13F	0.2811	0.7239	0.499	0.12*	0.395 (2)
C14A	0.220 (3)	0.6115 (17)	0.2720 (14)	0.114 (7)	0.395 (2)
H14D	0.2269	0.5592	0.1938	0.171*	0.395 (2)
H14E	0.2912	0.6967	0.2821	0.171*	0.395 (2)
H14F	0.0893	0.6289	0.2815	0.171*	0.395 (2)
S15	0.30211 (9)	0.63050 (5)	0.96900 (5)	0.0570 (2)	0.8629 (18)
O16	0.2521 (8)	0.4816 (3)	0.9404 (3)	0.0775 (9)	0.8629 (18)
C17	0.0886 (7)	0.7112 (4)	0.9385 (3)	0.0873 (8)	0.8629 (18)
H17A	0.0047	0.6992	0.9957	0.131*	0.8629 (18)
H17B	0.029	0.6716	0.8598	0.131*	0.8629 (18)
H17C	0.1156	0.807	0.9433	0.131*	0.8629 (18)
C18	0.4168 (7)	0.6718 (6)	0.8504 (5)	0.096 (2)	0.8629 (18)
H18A	0.5394	0.6329	0.8514	0.144*	0.8629 (18)
H18B	0.432	0.7692	0.8598	0.144*	0.8629 (18)
H18C	0.341	0.6355	0.7758	0.144*	0.8629 (18)
S15A	0.2077 (7)	0.6133 (4)	0.8695 (4)	0.0785 (16)	0.1371 (18)
O16A	0.235 (6)	0.4742 (18)	0.8952 (17)	0.085 (7)	0.1371 (18)
C17A	0.136 (4)	0.735 (3)	0.9939 (13)	0.084 (9)	0.1371 (18)
H17D	0.0093	0.7106	1.0059	0.126*	0.1371 (18)
H17E	0.141	0.8248	0.9765	0.126*	0.1371 (18)
H17F	0.2215	0.732	1.0647	0.126*	0.1371 (18)
C18A	0.444 (3)	0.679 (2)	0.876 (3)	0.074 (9)	0.1371 (18)
H18D	0.5276	0.6042	0.8642	0.111*	0.1371 (18)
H18E	0.4821	0.7358	0.9524	0.111*	0.1371 (18)
H18F	0.4509	0.7311	0.8146	0.111*	0.1371 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0548 (10)	0.0387 (8)	0.0736 (12)	0.0039 (7)	0.0097 (8)	0.0141 (8)
S2	0.0670 (3)	0.0319 (2)	0.0721 (3)	0.00558 (19)	0.0085 (2)	0.0157 (2)
C3	0.0503 (9)	0.0337 (8)	0.0705 (12)	0.0047 (7)	0.0102 (8)	0.0162 (7)
N4	0.0803 (11)	0.0341 (7)	0.0735 (11)	0.0070 (7)	0.0120 (8)	0.0148 (7)
N5	0.0752 (10)	0.0376 (8)	0.0700 (11)	0.0056 (7)	0.0123 (8)	0.0125 (7)
S6	0.1065 (5)	0.0548 (3)	0.0725 (4)	0.0054 (3)	0.0090 (3)	0.0227 (3)
N7	0.0644 (9)	0.0363 (7)	0.0729 (11)	0.0053 (6)	0.0091 (7)	0.0196 (7)
C8	0.0561 (10)	0.0457 (9)	0.0719 (12)	0.0033 (8)	0.0072 (9)	0.0132 (8)
C9	0.0815 (14)	0.0619 (12)	0.0734 (14)	0.0056 (10)	0.0078 (11)	0.0155 (10)
O10	0.1132 (12)	0.0372 (7)	0.0806 (10)	0.0058 (7)	0.0118 (9)	0.0129 (6)
S11	0.0750 (8)	0.0494 (5)	0.0673 (6)	−0.0013 (4)	0.0127 (4)	0.0184 (4)
O12	0.120 (4)	0.0437 (17)	0.093 (3)	0.019 (3)	0.030 (4)	0.0259 (16)
C13	0.151 (8)	0.073 (6)	0.066 (5)	0.012 (4)	−0.019 (4)	0.000 (4)
C14	0.116 (6)	0.040 (3)	0.057 (4)	−0.003 (3)	0.007 (3)	0.032 (3)
S11A	0.0768 (12)	0.0559 (8)	0.0666 (8)	0.0172 (6)	0.0152 (6)	0.0216 (6)
O12A	0.115 (6)	0.036 (2)	0.079 (4)	0.008 (4)	0.003 (5)	0.020 (2)
C13A	0.123 (9)	0.061 (7)	0.064 (8)	0.008 (5)	0.031 (7)	0.020 (5)
C14A	0.151 (16)	0.097 (9)	0.089 (10)	0.037 (8)	0.025 (9)	−0.004 (7)
S15	0.0831 (4)	0.0407 (3)	0.0477 (4)	0.0060 (2)	0.0121 (3)	0.0067 (2)
O16	0.117 (2)	0.0372 (13)	0.080 (2)	0.0071 (13)	0.026 (2)	0.0065 (14)
C17	0.096 (2)	0.0585 (18)	0.11	0.0158 (16)	0.019 (3)	0.019 (2)
C18	0.126 (4)	0.093 (3)	0.073 (3)	−0.013 (3)	0.045 (3)	0.012 (2)
S15A	0.106 (3)	0.056 (2)	0.068 (3)	0.000 (2)	−0.002 (2)	0.0071 (18)
O16A	0.159 (16)	0.023 (6)	0.064 (13)	−0.004 (7)	0.029 (14)	−0.021 (7)
C17A	0.15 (3)	0.077 (14)	0.039 (8)	0.048 (15)	0.054 (13)	0.010 (10)
C18A	0.103 (16)	0.034 (9)	0.067 (15)	0.016 (9)	−0.030 (12)	−0.013 (8)

Geometric parameters (Å, º) top

C1—N5	1.337 (2)	S11A—C13A	1.754 (15)
C1—S6	1.666 (2)	C13A—H13D	0.96
C1—S2	1.740 (2)	C13A—H13E	0.96
S2—C3	1.7367 (17)	C13A—H13F	0.96
C3—N4	1.295 (2)	C14A—H14D	0.96
C3—N7	1.368 (2)	C14A—H14E	0.96
N4—N5	1.370 (2)	C14A—H14F	0.96
N5—H5	0.878 (17)	S15—O16	1.486 (4)
N7—C8	1.373 (2)	S15—C17	1.762 (4)
N7—H7	0.86 (2)	S15—C18	1.777 (5)
C8—O10	1.221 (2)	C17—H17A	0.96
C8—C9	1.488 (3)	C17—H17B	0.96
C9—H9A	0.96	C17—H17C	0.96
C9—H9B	0.96	C18—H18A	0.96
C9—H9C	0.96	C18—H18B	0.96
S11—O12	1.540 (7)	C18—H18C	0.96
S11—C14	1.772 (5)	S15A—O16A	1.485 (18)
S11—C13	1.777 (12)	S15A—C18A	1.772 (19)
C13—H13A	0.96	S15A—C17A	1.822 (14)
C13—H13B	0.96	C17A—H17D	0.96
C13—H13C	0.96	C17A—H17E	0.96
C14—H14A	0.96	C17A—H17F	0.96
C14—H14B	0.96	C18A—H18D	0.96
C14—H14C	0.96	C18A—H18E	0.96
S11A—O12A	1.548 (11)	C18A—H18F	0.96
S11A—C14A	1.720 (12)

N5—C1—S6	127.50 (16)	S11A—C13A—H13E	109.5
N5—C1—S2	107.67 (15)	H13D—C13A—H13E	109.5
S6—C1—S2	124.82 (10)	S11A—C13A—H13F	109.5
C3—S2—C1	89.24 (9)	H13D—C13A—H13F	109.5
N4—C3—N7	121.00 (16)	H13E—C13A—H13F	109.5
N4—C3—S2	115.01 (15)	S11A—C14A—H14D	109.5
N7—C3—S2	124.00 (13)	S11A—C14A—H14E	109.5
C3—N4—N5	109.17 (14)	H14D—C14A—H14E	109.5
C1—N5—N4	118.91 (17)	S11A—C14A—H14F	109.5
C1—N5—H5	119 (2)	H14D—C14A—H14F	109.5
N4—N5—H5	121.9 (19)	H14E—C14A—H14F	109.5
C3—N7—C8	123.36 (16)	O16—S15—C17	105.9 (3)
C3—N7—H7	113.9 (15)	O16—S15—C18	107.7 (3)
C8—N7—H7	122.7 (15)	C17—S15—C18	97.3 (3)
O10—C8—N7	120.52 (19)	S15—C17—H17A	109.5
O10—C8—C9	123.44 (18)	S15—C17—H17B	109.5
N7—C8—C9	116.04 (17)	H17A—C17—H17B	109.5
C8—C9—H9A	109.5	S15—C17—H17C	109.5
C8—C9—H9B	109.5	H17A—C17—H17C	109.5
H9A—C9—H9B	109.5	H17B—C17—H17C	109.5
C8—C9—H9C	109.5	S15—C18—H18A	109.5
H9A—C9—H9C	109.5	S15—C18—H18B	109.5
H9B—C9—H9C	109.5	H18A—C18—H18B	109.5
O12—S11—C14	104.0 (4)	S15—C18—H18C	109.5
O12—S11—C13	103.8 (6)	H18A—C18—H18C	109.5
C14—S11—C13	99.9 (5)	H18B—C18—H18C	109.5
S11—C13—H13A	109.5	O16A—S15A—C18A	102.8 (19)
S11—C13—H13B	109.5	O16A—S15A—C17A	113.6 (12)
H13A—C13—H13B	109.5	C18A—S15A—C17A	98.3 (14)
S11—C13—H13C	109.5	S15A—C17A—H17D	109.5
H13A—C13—H13C	109.5	S15A—C17A—H17E	109.5
H13B—C13—H13C	109.5	H17D—C17A—H17E	109.5
S11—C14—H14A	109.5	S15A—C17A—H17F	109.5
S11—C14—H14B	109.5	H17D—C17A—H17F	109.5
H14A—C14—H14B	109.5	H17E—C17A—H17F	109.5
S11—C14—H14C	109.5	S15A—C18A—H18D	109.5
H14A—C14—H14C	109.5	S15A—C18A—H18E	109.5
H14B—C14—H14C	109.5	H18D—C18A—H18E	109.5
O12A—S11A—C14A	104.9 (8)	S15A—C18A—H18F	109.5
O12A—S11A—C13A	104.7 (7)	H18D—C18A—H18F	109.5
C14A—S11A—C13A	93.7 (9)	H18E—C18A—H18F	109.5
S11A—C13A—H13D	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O16	0.88 (2)	1.91 (2)	2.783 (3)	170 (3)
N7—H7···O12	0.86 (2)	1.89 (2)	2.734 (8)	166 (2)

Experimental details

Crystal data
Chemical formula	C₄H₅N₃OS₂·2C₂H₆OS
M_r	331.49
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.090 (2), 9.982 (3), 11.513 (3)
α, β, γ (°)	100.872 (6), 96.827 (4), 91.359 (4)
V (Å³)	793.6 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.28 × 0.18 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.894, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections	24389, 3292, 2625
R_int	0.180
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.06
No. of reflections	3292
No. of parameters	245
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.35

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O16	0.878 (17)	1.913 (18)	2.783 (3)	170 (3)
N7—H7···O12	0.86 (2)	1.89 (2)	2.734 (8)	166 (2)

References

Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cho, N. S., Kim, G. N. & Parkanyi, C. (1993). J. Heterocycl. Chem. 30, 397–401. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hildebrandt, A., Schaarschmidt, D., van As, L., Swarts, J. C. & Lang, H. (2011). Inorg. Chim. Acta, 374, 112–118. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhan, P., Liu, X., Fang, Z., Li, Z., Pannecouque, C. & De Clercq, E. (2009). Eur. J. Med. Chem. 44, 4648–4653. Web of Science CrossRef PubMed CAS Google Scholar
Zhan, J.-Y., Xiong, D.-J., Wang, Y.-G. & Li, H.-B. (2007). Acta Cryst. E63, o2184–o2185. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 1| January 2012| Page o224

doi:10.1107/S1600536811054298

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(5-Sulfanyl­­idene-4,5-di­hydro-1,3,4-thia­diazol-2-yl)acetamide di­methyl sulfoxide disolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N-(5-Sulfanylidene-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide dimethyl sulfoxide disolvate