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

Arslan, N.B.; Ertürk, A.G.; Kazak, C.; Bekdemir, Y.

doi:10.1107/S1600536811021520

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1736

doi:10.1107/S1600536811021520

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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 and Yunus Bekdemir ^c

^aDepartment of Physics, Arts and Sciences Faculty, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, ^bDepartment of Chemistry, Arts and Sciences Faculty, Ordu University, TR-52200 Ordu, Turkey, and ^cDepartment of Chemistry, Arts and Sciences Faculty, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
^*Correspondence e-mail: barslan@omu.edu.tr

(Received 22 May 2011; accepted 3 June 2011; online 18 June 2011)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.038
wR(F²) = 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

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)
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021520/is2719sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811021520/is2719Isup3.cml

checkCIF report

Comment top

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).

Related literature top

For background 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 top

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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. The tautomeric forms of 3-imino-1,2,5-thiadiazolidine 1,1-dioxides.
	Fig. 2. An ORTEP view of the title compound, with the atom-numbering scheme and 30% probability of displacement ellipsoids.
	Fig. 3. A packing diagram of the title compound, viewed down the a axis.

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

Crystal data top

C₁₀H₁₄N₄O₂S	F(000) = 536
M_r = 254.32	D_x = 1.431 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 24497 reflections
a = 7.2587 (8) Å	θ = 2.1–27.7°
b = 9.8187 (8) Å	µ = 0.27 mm⁻¹
c = 16.893 (2) Å	T = 293 K
β = 101.325 (10)°	Prism, light green
V = 1180.6 (2) Å³	0.44 × 0.32 × 0.21 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	2615 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2294 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.042
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.2°, θ_min = 2.4°
ω scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.955, T_max = 0.985	l = −21→21
18500 measured 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0564P)² + 0.4122P] where P = (F_o² + 2F_c²)/3
2615 reflections	(Δ/σ)_max = 0.008
166 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₀H₁₄N₄O₂S	V = 1180.6 (2) Å³
M_r = 254.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2587 (8) Å	µ = 0.27 mm⁻¹
b = 9.8187 (8) Å	T = 293 K
c = 16.893 (2) Å	0.44 × 0.32 × 0.21 mm
β = 101.325 (10)°

Data collection top

Stoe IPDS 2 diffractometer	2615 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2294 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.985	R_int = 0.042
18500 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.40 e Å⁻³
2615 reflections	Δρ_min = −0.47 e Å⁻³
166 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
C1	0.8325 (2)	0.14751 (15)	0.83505 (9)	0.0338 (3)
C2	0.7810 (2)	0.06451 (16)	0.75795 (9)	0.0349 (3)
C3	0.8875 (2)	0.10603 (16)	0.69385 (9)	0.0342 (3)
C4	0.8616 (2)	0.23280 (17)	0.65646 (10)	0.0409 (4)
H4	0.7726	0.2926	0.6694	0.049*
C5	0.9665 (2)	0.27045 (18)	0.60042 (10)	0.0436 (4)
H5	0.9465	0.3552	0.5757	0.052*
C6	1.1026 (2)	0.18340 (17)	0.57999 (9)	0.0360 (3)
C7	1.1227 (2)	0.05506 (17)	0.61548 (10)	0.0410 (4)
H7	1.2082	−0.0064	0.6014	0.049*
C8	1.0168 (2)	0.01820 (17)	0.67143 (10)	0.0401 (4)
H8	1.0328	−0.0679	0.6946	0.048*
C9	1.3411 (3)	0.1279 (3)	0.50170 (13)	0.0593 (5)
H9A	1.4068	0.1674	0.4633	0.089*
H9B	1.2723	0.0494	0.4783	0.089*
H9C	1.4297	0.1013	0.5491	0.089*
C10	1.3040 (3)	0.3598 (2)	0.54390 (13)	0.0623 (6)
H10A	1.3742	0.3836	0.5033	0.093*
H10B	1.3876	0.3534	0.5954	0.093*
H10C	1.2112	0.4286	0.5462	0.093*
N1	0.69481 (19)	0.20064 (15)	0.86387 (9)	0.0431 (3)
N2	0.57725 (19)	0.08209 (17)	0.73433 (9)	0.0458 (4)
H2	0.5095	0.0530	0.6900	0.055*
N3	1.0099 (2)	0.16048 (16)	0.86985 (9)	0.0421 (3)
N4	1.21057 (19)	0.22794 (16)	0.52365 (8)	0.0420 (3)
O1	0.38231 (17)	0.07726 (15)	0.84236 (9)	0.0557 (4)
O2	0.4074 (2)	0.28818 (16)	0.77361 (12)	0.0796 (5)
S1	0.49704 (6)	0.16529 (4)	0.80460 (3)	0.04255 (15)
H2A	0.810 (2)	−0.0288 (19)	0.7719 (10)	0.034 (4)*
H3A	1.094 (3)	0.128 (2)	0.8452 (13)	0.057 (6)*
H3B	1.046 (3)	0.206 (2)	0.9150 (13)	0.047 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0345 (7)	0.0316 (7)	0.0359 (7)	−0.0033 (6)	0.0085 (6)	0.0016 (6)
C2	0.0330 (7)	0.0332 (7)	0.0384 (7)	−0.0033 (6)	0.0069 (6)	−0.0003 (6)
C3	0.0329 (7)	0.0347 (8)	0.0348 (7)	−0.0023 (6)	0.0062 (6)	−0.0034 (6)
C4	0.0415 (8)	0.0378 (8)	0.0462 (9)	0.0087 (7)	0.0152 (7)	0.0021 (7)
C5	0.0494 (9)	0.0375 (8)	0.0463 (9)	0.0075 (7)	0.0154 (7)	0.0076 (7)
C6	0.0341 (7)	0.0422 (8)	0.0313 (7)	−0.0004 (6)	0.0056 (6)	−0.0021 (6)
C7	0.0411 (8)	0.0408 (9)	0.0425 (8)	0.0083 (7)	0.0118 (7)	−0.0026 (7)
C8	0.0469 (9)	0.0316 (7)	0.0425 (8)	0.0043 (6)	0.0105 (7)	−0.0002 (6)
C9	0.0528 (11)	0.0781 (14)	0.0528 (10)	0.0145 (10)	0.0248 (9)	0.0044 (10)
C10	0.0648 (12)	0.0711 (14)	0.0544 (11)	−0.0258 (11)	0.0199 (10)	−0.0071 (10)
N1	0.0368 (7)	0.0461 (8)	0.0481 (8)	−0.0002 (6)	0.0125 (6)	−0.0084 (6)
N2	0.0305 (7)	0.0643 (10)	0.0417 (7)	−0.0074 (6)	0.0053 (6)	−0.0045 (7)
N3	0.0324 (7)	0.0532 (9)	0.0405 (7)	−0.0038 (6)	0.0066 (6)	−0.0087 (6)
N4	0.0400 (7)	0.0512 (8)	0.0369 (7)	−0.0002 (6)	0.0126 (6)	−0.0002 (6)
O1	0.0367 (6)	0.0680 (9)	0.0675 (8)	−0.0022 (6)	0.0228 (6)	0.0048 (7)
O2	0.0696 (10)	0.0509 (9)	0.1102 (14)	0.0219 (8)	−0.0019 (9)	0.0156 (9)
S1	0.0325 (2)	0.0407 (2)	0.0549 (3)	0.00558 (15)	0.00952 (17)	0.00524 (18)

Geometric parameters (Å, º) top

C1—N1	1.304 (2)	C8—H8	0.9300
C1—N3	1.313 (2)	C9—N4	1.462 (2)
C1—C2	1.520 (2)	C9—H9A	0.9600
C2—N2	1.465 (2)	C9—H9B	0.9600
C2—C3	1.505 (2)	C9—H9C	0.9600
C2—H2A	0.959 (18)	C10—N4	1.471 (3)
C3—C8	1.381 (2)	C10—H10A	0.9600
C3—C4	1.392 (2)	C10—H10B	0.9600
C4—C5	1.377 (2)	C10—H10C	0.9600
C4—H4	0.9300	N1—S1	1.6184 (15)
C5—C6	1.400 (2)	N2—S1	1.6393 (15)
C5—H5	0.9300	N2—H2	0.8600
C6—C7	1.391 (2)	N3—H3A	0.87 (2)
C6—N4	1.415 (2)	N3—H3B	0.88 (2)
C7—C8	1.379 (2)	O1—S1	1.4339 (13)
C7—H7	0.9300	O2—S1	1.4210 (15)

N1—C1—N3	123.42 (15)	N4—C9—H9B	109.5
N1—C1—C2	117.21 (14)	H9A—C9—H9B	109.5
N3—C1—C2	119.36 (14)	N4—C9—H9C	109.5
N2—C2—C3	113.96 (13)	H9A—C9—H9C	109.5
N2—C2—C1	103.62 (13)	H9B—C9—H9C	109.5
C3—C2—C1	113.38 (13)	N4—C10—H10A	109.5
N2—C2—H2A	109.9 (10)	N4—C10—H10B	109.5
C3—C2—H2A	108.5 (10)	H10A—C10—H10B	109.5
C1—C2—H2A	107.3 (10)	N4—C10—H10C	109.5
C8—C3—C4	118.22 (15)	H10A—C10—H10C	109.5
C8—C3—C2	120.05 (14)	H10B—C10—H10C	109.5
C4—C3—C2	121.72 (14)	C1—N1—S1	109.59 (12)
C5—C4—C3	120.54 (15)	C2—N2—S1	110.17 (11)
C5—C4—H4	119.7	C2—N2—H2	124.9
C3—C4—H4	119.7	S1—N2—H2	124.9
C4—C5—C6	121.20 (15)	C1—N3—H3A	118.3 (15)
C4—C5—H5	119.4	C1—N3—H3B	122.7 (13)
C6—C5—H5	119.4	H3A—N3—H3B	119 (2)
C7—C6—C5	117.77 (15)	C6—N4—C9	115.77 (15)
C7—C6—N4	123.02 (15)	C6—N4—C10	113.99 (14)
C5—C6—N4	119.19 (15)	C9—N4—C10	110.99 (16)
C8—C7—C6	120.55 (15)	O2—S1—O1	114.33 (10)
C8—C7—H7	119.7	O2—S1—N1	109.39 (10)
C6—C7—H7	119.7	O1—S1—N1	112.09 (8)
C7—C8—C3	121.63 (15)	O2—S1—N2	111.00 (10)
C7—C8—H8	119.2	O1—S1—N2	109.98 (9)
C3—C8—H8	119.2	N1—S1—N2	99.02 (7)
N4—C9—H9A	109.5

N1—C1—C2—N2	5.40 (19)	C4—C3—C8—C7	2.0 (2)
N3—C1—C2—N2	−175.73 (14)	C2—C3—C8—C7	−177.17 (15)
N1—C1—C2—C3	129.45 (15)	N3—C1—N1—S1	179.30 (13)
N3—C1—C2—C3	−51.7 (2)	C2—C1—N1—S1	−1.88 (18)
N2—C2—C3—C8	−129.18 (16)	C3—C2—N2—S1	−130.03 (12)
C1—C2—C3—C8	112.61 (16)	C1—C2—N2—S1	−6.35 (15)
N2—C2—C3—C4	51.7 (2)	C7—C6—N4—C9	2.6 (2)
C1—C2—C3—C4	−66.6 (2)	C5—C6—N4—C9	−176.21 (16)
C8—C3—C4—C5	−1.9 (2)	C7—C6—N4—C10	−127.99 (19)
C2—C3—C4—C5	177.27 (15)	C5—C6—N4—C10	53.2 (2)
C3—C4—C5—C6	−0.5 (3)	C1—N1—S1—O2	−118.20 (14)
C4—C5—C6—C7	2.8 (2)	C1—N1—S1—O1	113.90 (13)
C4—C5—C6—N4	−178.32 (16)	C1—N1—S1—N2	−2.06 (14)
C5—C6—C7—C8	−2.7 (2)	C2—N2—S1—O2	120.26 (13)
N4—C6—C7—C8	178.48 (15)	C2—N2—S1—O1	−112.22 (12)
C6—C7—C8—C3	0.3 (3)	C2—N2—S1—N1	5.36 (13)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₄N₄O₂S
M_r	254.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.2587 (8), 9.8187 (8), 16.893 (2)
β (°)	101.325 (10)
V (Å³)	1180.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.44 × 0.32 × 0.21

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.955, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	18500, 2615, 2294
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 1.06
No. of reflections	2615
No. of parameters	166
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.47

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2.

References

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Volume 67| Part 7| July 2011| Page o1736

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

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

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Experimental

Crystal data

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organic compounds

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