1-(2,4,6-Trioxo-1,3-diazinan-5-yl-idene)thio-semicarbazide.

The title mol-ecule, C(5)H(5)N(5)O(3)S, is approximately planar, with a maximum deviation from the mean plane through the non-H atoms of 0.182 (3) Å for the amine N atom. In the crystal, mol-ecules are connected via N-H⋯O and N-H⋯S inter-actions, building a three-dimensional hydrogen-bonded network. Additionally, a weak intra-molecular N-H⋯O hydrogen bond is observed.

Related literature

For the synthesis of alloxan-5-thio­semicarbazone, see: Beyer et al. (1956 ▶). For the anti­bacterial activity of alloxan-5-thio­semicarbazone against Staphylococcus aureus and Escherichia coli, see: Douros et al. (1973 ▶).

Experimental

Crystal data

C5H5N5O3S

M = 215.20

Monoclinic,

a = 10.6415 (8) Å

b = 7.3370 (6) Å

c = 11.160 (1) Å

β = 107.380 (5)°

V = 831.55 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 293 K

0.14 × 0.10 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.949, T max = 0.967

15454 measured reflections

1929 independent reflections

955 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.148

S = 1.00

1929 reflections

147 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.39 e Å−3

Data collection: COSMO (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012007/nc2271sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012007/nc2271Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012007/nc2271Isup3.cml

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

C5H5N5O3S	F(000) = 440
Mr = 215.20	Dx = 1.719 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1283 reflections
a = 10.6415 (8) Å	θ = 2.3–19.9°
b = 7.3370 (6) Å	µ = 0.38 mm−1
c = 11.160 (1) Å	T = 293 K
β = 107.380 (5)°	Block, red
V = 831.55 (12) Å3	0.14 × 0.10 × 0.09 mm
Z = 4

Bruker APEXII CCD diffractometer	1929 independent reflections
Radiation source: fine-focus sealed tube	955 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
φ and ω scans	θmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.949, Tmax = 0.967	k = −9→9
15454 measured reflections	l = −14→14

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)] = 0.056	Hydrogen site location: difference Fourier map
wR(F2) = 0.148	All H-atom parameters refined
S = 1.00	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.6101P] where P = (Fo2 + 2Fc2)/3
1929 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.39 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.

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.

	x	y	z	Uiso*/Ueq
S1	0.17866 (11)	0.94933 (14)	1.13122 (11)	0.0487 (4)
O3	0.4802 (2)	0.2077 (3)	1.0689 (2)	0.0426 (8)
O2	0.1726 (2)	−0.0867 (4)	0.7631 (3)	0.0486 (8)
O1	0.0566 (2)	0.4570 (3)	0.8863 (3)	0.0456 (8)
N5	0.4116 (3)	0.7883 (5)	1.1940 (3)	0.0412 (9)
N3	0.3183 (3)	0.4951 (4)	1.0600 (3)	0.0335 (8)
N4	0.2392 (3)	0.6328 (4)	1.0593 (3)	0.0385 (9)
N2	0.3282 (3)	0.0686 (4)	0.9108 (3)	0.0321 (8)
N1	0.1178 (3)	0.1858 (4)	0.8272 (3)	0.0356 (9)
C5	0.2851 (4)	0.7858 (5)	1.1334 (4)	0.0340 (9)
C4	0.3687 (3)	0.2088 (5)	0.9943 (4)	0.0322 (9)
C3	0.2034 (3)	0.0473 (5)	0.8282 (4)	0.0329 (9)
C1	0.2734 (3)	0.3545 (4)	0.9874 (3)	0.0294 (9)
C2	0.1418 (3)	0.3399 (5)	0.8981 (3)	0.0335 (9)
H4	0.465 (4)	0.694 (5)	1.189 (3)	0.043 (12)*
H2	0.382 (4)	−0.019 (5)	0.912 (3)	0.040 (12)*
H5	0.440 (5)	0.887 (7)	1.240 (5)	0.083 (17)*
H3	0.156 (5)	0.639 (6)	1.015 (4)	0.072 (15)*
H1	0.054 (4)	0.175 (5)	0.785 (4)	0.044 (14)*

	U11	U22	U33	U12	U13	U23
S1	0.0504 (7)	0.0356 (6)	0.0614 (8)	0.0045 (5)	0.0185 (5)	−0.0041 (6)
O3	0.0296 (14)	0.0404 (15)	0.0424 (17)	0.0099 (12)	−0.0126 (13)	−0.0101 (13)
O2	0.0382 (15)	0.0385 (17)	0.057 (2)	0.0004 (12)	−0.0034 (14)	−0.0207 (14)
O1	0.0344 (15)	0.0366 (16)	0.0530 (19)	0.0122 (13)	−0.0066 (13)	−0.0042 (14)
N5	0.034 (2)	0.031 (2)	0.052 (2)	−0.0026 (16)	0.0027 (17)	−0.0090 (18)
N3	0.0344 (18)	0.0289 (17)	0.0325 (19)	0.0029 (14)	0.0027 (14)	−0.0003 (14)
N4	0.0332 (19)	0.0305 (18)	0.044 (2)	0.0037 (15)	0.0001 (17)	−0.0064 (16)
N2	0.0257 (17)	0.0281 (17)	0.034 (2)	0.0058 (14)	−0.0034 (14)	−0.0037 (14)
N1	0.0248 (18)	0.0354 (19)	0.037 (2)	0.0010 (15)	−0.0055 (16)	−0.0062 (16)
C5	0.039 (2)	0.0248 (19)	0.037 (2)	−0.0024 (17)	0.0101 (18)	0.0021 (17)
C4	0.0299 (19)	0.030 (2)	0.033 (2)	0.0011 (16)	0.0035 (17)	−0.0035 (17)
C3	0.027 (2)	0.033 (2)	0.036 (2)	0.0024 (17)	0.0047 (17)	0.0017 (19)
C1	0.0280 (19)	0.0268 (19)	0.029 (2)	0.0048 (15)	0.0015 (16)	0.0018 (16)
C2	0.029 (2)	0.032 (2)	0.033 (2)	0.0023 (17)	0.0000 (17)	−0.0010 (17)

S1—C5	1.645 (4)	N4—H3	0.88 (4)
O3—C4	1.229 (4)	N2—C4	1.368 (4)
O2—C3	1.208 (4)	N2—C3	1.380 (4)
O1—C2	1.227 (4)	N2—H2	0.86 (4)
N5—C5	1.314 (4)	N1—C2	1.360 (5)
N5—H4	0.91 (4)	N1—C3	1.362 (5)
N5—H5	0.89 (5)	N1—H1	0.70 (4)
N3—C1	1.311 (4)	C4—C1	1.460 (5)
N3—N4	1.313 (4)	C1—C2	1.460 (5)
N4—C5	1.394 (4)
C5—N5—H4	121 (2)	N5—C5—S1	126.3 (3)
C5—N5—H5	115 (3)	N4—C5—S1	117.5 (3)
H4—N5—H5	123 (4)	O3—C4—N2	120.1 (3)
C1—N3—N4	119.1 (3)	O3—C4—C1	123.7 (3)
N3—N4—C5	120.4 (3)	N2—C4—C1	116.2 (3)
N3—N4—H3	126 (3)	O2—C3—N1	122.8 (3)
C5—N4—H3	114 (3)	O2—C3—N2	121.8 (3)
C4—N2—C3	125.8 (3)	N1—C3—N2	115.4 (3)
C4—N2—H2	119 (2)	N3—C1—C2	125.4 (3)
C3—N2—H2	115 (2)	N3—C1—C4	115.1 (3)
C2—N1—C3	127.3 (3)	C2—C1—C4	119.5 (3)
C2—N1—H1	117 (3)	O1—C2—N1	121.0 (3)
C3—N1—H1	116 (3)	O1—C2—C1	123.3 (3)
N5—C5—N4	116.1 (3)	N1—C2—C1	115.7 (3)
C1—N3—N4—C5	−178.6 (4)	O3—C4—C1—N3	5.6 (6)
N3—N4—C5—N5	5.3 (5)	N2—C4—C1—N3	−174.0 (3)
N3—N4—C5—S1	−177.8 (3)	O3—C4—C1—C2	−178.0 (4)
C3—N2—C4—O3	175.4 (4)	N2—C4—C1—C2	2.5 (5)
C3—N2—C4—C1	−5.1 (6)	C3—N1—C2—O1	178.4 (4)
C2—N1—C3—O2	178.7 (4)	C3—N1—C2—C1	−1.7 (6)
C2—N1—C3—N2	−0.4 (6)	N3—C1—C2—O1	−3.5 (6)
C4—N2—C3—O2	−175.0 (4)	C4—C1—C2—O1	−179.6 (4)
C4—N2—C3—N1	4.1 (6)	N3—C1—C2—N1	176.6 (4)
N4—N3—C1—C2	3.5 (6)	C4—C1—C2—N1	0.6 (5)
N4—N3—C1—C4	179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H4···O2i	0.91 (4)	2.26 (4)	3.036 (4)	143 (3)
N2—H2···O3ii	0.86 (4)	1.98 (4)	2.837 (4)	173 (4)
N5—H5···O1iii	0.89 (5)	2.08 (5)	2.916 (4)	158 (4)
N4—H3···O1	0.88 (4)	2.01 (4)	2.631 (4)	126 (4)
N1—H1···O3iv	0.70 (4)	2.46 (4)	2.923 (4)	125 (4)
N1—H1···S1v	0.70 (4)	3.03 (4)	3.468 (4)	123 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H4⋯O2i	0.91 (4)	2.26 (4)	3.036 (4)	143 (3)
N2—H2⋯O3ii	0.86 (4)	1.98 (4)	2.837 (4)	173 (4)
N5—H5⋯O1iii	0.89 (5)	2.08 (5)	2.916 (4)	158 (4)
N4—H3⋯O1	0.88 (4)	2.01 (4)	2.631 (4)	126 (4)
N1—H1⋯O3iv	0.70 (4)	2.46 (4)	2.923 (4)	125 (4)
N1—H1⋯S1v	0.70 (4)	3.03 (4)	3.468 (4)	123 (4)

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