3-Amino-4-[4-(dimethyl­amino)­phen­yl]-4,5-dihydro-1,2,5-thia­diazole 1,1-dioxide

N Burcu Arslan; Aliye Gediz Ertürk; Canan Kazak; Yunus Bekdemir

doi:10.1107/S1600536811021520

. 2011 Jun 18;67(Pt 7):o1736. doi: 10.1107/S1600536811021520

3-Amino-4-[4-(dimethylamino)phenyl]-4,5-dihydro-1,2,5-thiadiazole 1,1-dioxide

N Burcu Arslan ^a,^*, Aliye Gediz Ertürk ^b, Canan Kazak ^a, Yunus Bekdemir ^c

PMCID: PMC3152090 PMID: 21837124

Abstract

The title compound, C₁₀H₁₄N₄O₂S, exists in the amine tautomeric form. The dihedral angle between the benzene and thiadiazolidine rings is 66.54 (19)°. In the crystal, molecules are linked by N—H⋯O and N—H⋯N hydrogen bonds into a layer parallel to the ac plane. The layers are further linked by C—H⋯O hydrogen bonds.

Related literature

For background to and applications of sulfamides, see: Autrieth et al. (1940 ▶); Bermudez et al. (1997 ▶); Forster et al. (1971 ▶); Gazieva et al. (2000 ▶); Lawson & Tinkler (1970 ▶); Spillane & Benson (1980 ▶). For related structures; see: Gazieva et al. (2000 ▶); Lee et al. (1989 ▶).

Experimental

Crystal data

C₁₀H₁₄N₄O₂S
M _r = 254.32
Monoclinic,
a = 7.2587 (8) Å
b = 9.8187 (8) Å
c = 16.893 (2) Å
β = 101.325 (10)°
V = 1180.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.44 × 0.32 × 0.21 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.955, T _max = 0.985
18500 measured reflections
2615 independent reflections
2294 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.109
S = 1.06
2615 reflections
166 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021520/is2719sup1.cif

e-67-o1736-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021520/is2719Isup2.hkl

e-67-o1736-Isup2.hkl^{(125.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811021520/is2719Isup3.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
N3—H3A⋯O1ⁱ	0.87 (2)	2.16 (2)	2.947 (2)	151.0 (19)
N3—H3B⋯N4ⁱⁱ	0.88 (2)	2.09 (2)	2.930 (2)	160.6 (19)
C2—H2A⋯O2ⁱⁱⁱ	0.959 (18)	2.416 (18)	3.038 (2)	122.3 (13)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

Sulfamides (or sulfonamides) are well known compounds because of belonging to their pharmaceutical applications, especially in the field of antimicrobial chemotherapy. Sulfamides first used in the dye industry, but then come into question as a therapeutic antibacterial drugs for the treatment of infectious diseases. Especially were used for this purpose p-aminophenylsulfonamides (Bermudez et al., 1997; Gazieva et al., 2000). In addition, some studies revealed especially psychiatric effects of cyclic derivatives of sulfamides. They have been as well as use of insecticides and also soothing, relieving depression, pain killers and muscle relaxants (Spillane & Benson, 1980). Apart from being pharmacologically active compounds sulfamides have also been used in the making water-resistant resins (Autrieth et al., 1940; Forster et al., 1971; Lawson & Tinkler, 1970).

Tautomeric forms of 3-imino-1,2,5-thiadiazolidine 1,1-dioxides were studied (Gazieva et al., 2000; Lee et al.. 1989). In solution they ocur as equilibrium mixtures of tautomers A and A^' (Fig. 1). This study verifies the preference of the enamine-imine tautomeric form in the solid state (Fig. 2). In the title compound all bond lenghts are in normal ranges. The benzene and the thiadiazolidine rings are planar with maximum deviations of 0.018 and 0.038 Å at atoms C6 and N2, respectively. S—O bond lenghts are 1.421 and 1.434 Å. The molecules are linked by intermolecular N—H···O, N—H···N and C—H···O hydrogen bonds (Fig. 3).

Experimental

At 25 ml flask, 35 mg (0.72 mmol) sodium cyanide was added into 70% aqueous ethanol solution (1.3 ml) containing 70 mg (0.66 mmol) p-N,N-dimethyl benzaldehyde and 125 mg (1.3 mmol) sulfamide (Lee et al., 1989). Reaction mixtures was heated in microwave oven at 90 W for 3 minutes. 1 N NaOH solution (0.6 ml) was added into the resulting mixture. The aqueous solution was extracted with ethyl acetate (2 × 1.3 ml) and 0.7 ml diethyl ether. The aqueous phase was then acidified with 1 N HCl (pH ~2). The green-colored solids were recrystallized in ethyl alcohol (yield 47%, m.p. 208–210 °C).