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

Sung Kwon Kang; Nam Sook Cho; Siyoung Jang

doi:10.1107/S1600536811054298

. 2011 Dec 23;68(Pt 1):o224. doi: 10.1107/S1600536811054298

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

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

PMCID: PMC3254557 PMID: 22259506

Abstract

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,
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[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 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

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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054298/is5026sup1.cif

e-68-0o224-sup1.cif^{(24.9KB, cif)}

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

e-68-0o224-Isup2.hkl^{(158.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811054298/is5026Isup3.cml

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

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)

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supplementary crystallographic information

Comment

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).

Experimental

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.