Crystal structure of a monoclinic polymorph of 5-amino-1,3,4-thia-diazol-2(3H)-one.

The title compound, C2H3N3OS, is a monoclinic (P21/c) polymorph of the previously reported triclinic structure [Kang et al. (2012 ▶). Acta Cryst. E68, o1198]. The asymmetric unit contains two independent mol-ecules which are essentially planar, with r.m.s. deviations of 0.001 and 0.032 Å from the mean plane defined by the seven non-H atoms. In the crystal, N-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into a sheet parallel to (111).

Related literature

For structures and reactivity of thia­diazole derivatives, see: Parkanyi et al. (1989 ▶); Cho et al. (1996 ▶). For the triclinic polymorph, see; Kang et al. (2012 ▶).

Experimental

Crystal data

C2H3N3OS

M = 117.13

Monoclinic,

a = 3.8182 (3) Å

b = 10.8166 (7) Å

c = 21.8043 (15) Å

β = 91.015 (4)°

V = 900.37 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.58 mm−1

T = 296 K

0.21 × 0.1 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.911, T max = 0.931

5812 measured reflections

1709 independent reflections

1376 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.099

S = 1.08

1709 reflections

151 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016055/tk5326sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016055/tk5326Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016055/tk5326Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016055/tk5326fig1.tif

Mol­ecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids. Inter­molecular N—H⋯N and N—H⋯O hydrogen bonds are indicated by dashed lines.

Click here for additional data file.

. DOI: 10.1107/S1600536814016055/tk5326fig2.tif

Part of the crystal structure of the title compound, showing mol­ecules linked by inter­molecular N—H⋯N and N—H⋯O hydrogen bonds (dashed lines).

CCDC reference: 1013072

Additional supporting information: crystallographic information; 3D view; checkCIF report

C2H3N3OS	F(000) = 480
Mr = 117.13	Dx = 1.728 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1700 reflections
a = 3.8182 (3) Å	θ = 2.7–25.7°
b = 10.8166 (7) Å	µ = 0.58 mm−1
c = 21.8043 (15) Å	T = 296 K
β = 91.015 (4)°	Block, colourless
V = 900.37 (11) Å3	0.21 × 0.1 × 0.09 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	1376 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 25.8°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −4→4
Tmin = 0.911, Tmax = 0.931	k = −12→13
5812 measured reflections	l = −26→26
1709 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	All H-atom parameters refined
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0317P)2 + 0.833P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1709 reflections	Δρmax = 0.37 e Å−3
151 parameters	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.5670 (2)	0.33458 (7)	0.36148 (3)	0.0316 (2)
C2	0.4389 (8)	0.4860 (3)	0.33723 (13)	0.0297 (7)
N3	0.5448 (8)	0.5631 (3)	0.38116 (12)	0.0327 (7)
H3	0.487 (9)	0.631 (3)	0.3829 (14)	0.030 (10)*
N4	0.7091 (7)	0.5177 (2)	0.43328 (11)	0.0301 (6)
C5	0.7362 (8)	0.3992 (3)	0.42932 (13)	0.0259 (7)
O6	0.2779 (7)	0.5107 (2)	0.28964 (10)	0.0454 (6)
N7	0.8708 (8)	0.3270 (3)	0.47486 (13)	0.0349 (7)
H7A	0.968 (9)	0.259 (3)	0.4641 (14)	0.035 (10)*
H7B	0.983 (10)	0.364 (3)	0.5033 (17)	0.049 (11)*
S8	0.0629 (2)	1.02405 (7)	0.34352 (4)	0.0334 (2)
C9	0.2461 (8)	1.0171 (3)	0.41853 (13)	0.0294 (7)
N10	0.3361 (7)	0.9003 (2)	0.42943 (12)	0.0315 (6)
H10	0.438 (8)	0.884 (3)	0.4630 (14)	0.024 (8)*
N11	0.2747 (8)	0.8126 (2)	0.38422 (11)	0.0359 (7)
C12	0.1325 (8)	0.8645 (3)	0.33686 (13)	0.0296 (7)
O13	0.2843 (7)	1.1052 (2)	0.45367 (10)	0.0458 (7)
N14	0.0397 (10)	0.8045 (4)	0.28504 (14)	0.0502 (9)
H14A	−0.052 (11)	0.853 (4)	0.2546 (19)	0.068 (13)*
H14B	0.074 (10)	0.738 (4)	0.2852 (17)	0.043 (12)*

	U11	U22	U33	U12	U13	U23
S1	0.0410 (5)	0.0227 (4)	0.0307 (4)	0.0018 (4)	−0.0078 (3)	−0.0059 (3)
C2	0.0324 (18)	0.0272 (17)	0.0295 (16)	0.0007 (14)	−0.0021 (13)	−0.0011 (13)
N3	0.0497 (19)	0.0174 (14)	0.0307 (15)	0.0063 (13)	−0.0095 (12)	−0.0019 (11)
N4	0.0401 (16)	0.0220 (14)	0.0278 (13)	0.0087 (12)	−0.0088 (11)	−0.0033 (11)
C5	0.0287 (17)	0.0221 (16)	0.0269 (15)	0.0020 (13)	0.0001 (12)	−0.0042 (12)
O6	0.0609 (17)	0.0390 (14)	0.0355 (13)	0.0025 (12)	−0.0201 (12)	0.0028 (11)
N7	0.0482 (19)	0.0240 (16)	0.0319 (15)	0.0073 (14)	−0.0118 (13)	−0.0026 (13)
S8	0.0422 (5)	0.0250 (4)	0.0326 (4)	0.0077 (4)	−0.0091 (3)	0.0031 (3)
C9	0.0343 (18)	0.0242 (16)	0.0296 (16)	0.0068 (14)	−0.0037 (13)	0.0004 (13)
N10	0.0479 (18)	0.0233 (14)	0.0229 (13)	0.0116 (12)	−0.0093 (12)	−0.0023 (11)
N11	0.0550 (19)	0.0239 (14)	0.0284 (14)	0.0093 (13)	−0.0091 (12)	−0.0033 (11)
C12	0.0358 (19)	0.0242 (16)	0.0288 (16)	0.0051 (14)	−0.0027 (13)	−0.0019 (13)
O13	0.0714 (18)	0.0255 (13)	0.0400 (13)	0.0124 (12)	−0.0154 (12)	−0.0079 (11)
N14	0.079 (3)	0.036 (2)	0.0346 (18)	0.0114 (18)	−0.0230 (16)	−0.0056 (15)

S1—C5	1.749 (3)	S8—C12	1.753 (3)
S1—C2	1.786 (3)	S8—C9	1.769 (3)
C2—O6	1.226 (4)	C9—O13	1.230 (3)
C2—N3	1.328 (4)	C9—N10	1.329 (4)
N3—N4	1.379 (3)	N10—N11	1.385 (3)
N3—H3	0.77 (3)	N10—H10	0.84 (3)
N4—C5	1.289 (4)	N11—C12	1.287 (4)
C5—N7	1.357 (4)	C12—N14	1.345 (4)
N7—H7A	0.86 (3)	N14—H14A	0.91 (4)
N7—H7B	0.85 (4)	N14—H14B	0.73 (4)
C5—S1—C2	88.81 (14)	C12—S8—C9	88.66 (14)
O6—C2—N3	127.9 (3)	O13—C9—N10	126.7 (3)
O6—C2—S1	125.5 (2)	O13—C9—S8	125.7 (2)
N3—C2—S1	106.5 (2)	N10—C9—S8	107.6 (2)
C2—N3—N4	120.0 (3)	C9—N10—N11	118.9 (3)
C2—N3—H3	123 (2)	C9—N10—H10	118 (2)
N4—N3—H3	115 (2)	N11—N10—H10	123 (2)
C5—N4—N3	109.5 (2)	C12—N11—N10	109.6 (2)
N4—C5—N7	123.6 (3)	N11—C12—N14	124.4 (3)
N4—C5—S1	115.1 (2)	N11—C12—S8	115.2 (2)
N7—C5—S1	121.2 (2)	N14—C12—S8	120.4 (3)
C5—N7—H7A	117 (2)	C12—N14—H14A	115 (3)
C5—N7—H7B	116 (2)	C12—N14—H14B	115 (3)
H7A—N7—H7B	113 (3)	H14A—N14—H14B	130 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N11	0.77 (3)	2.12 (3)	2.891 (4)	174 (3)
N7—H7A···O13i	0.86 (3)	2.07 (4)	2.913 (4)	167 (3)
N7—H7B···N4ii	0.85 (4)	2.21 (4)	3.048 (4)	171 (3)
N10—H10···O13iii	0.84 (3)	2.09 (3)	2.910 (3)	165 (3)
N14—H14A···O6iv	0.91 (4)	2.14 (4)	3.005 (4)	159 (4)
N14—H14B···O6	0.73 (4)	2.58 (4)	3.306 (5)	173 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N11	0.77 (3)	2.12 (3)	2.891 (4)	174 (3)
N7—H7A⋯O13i	0.86 (3)	2.07 (4)	2.913 (4)	167 (3)
N7—H7B⋯N4ii	0.85 (4)	2.21 (4)	3.048 (4)	171 (3)
N10—H10⋯O13iii	0.84 (3)	2.09 (3)	2.910 (3)	165 (3)
N14—H14A⋯O6iv	0.91 (4)	2.14 (4)	3.005 (4)	159 (4)
N14—H14B⋯O6	0.73 (4)	2.58 (4)	3.306 (5)	173 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .