2-Propyl-4H-thia-zolo[3,2-a][1,3,5]triazine-4-thione.

In the title compound, C(8)H(9)N(3)S(2), the n-propyl chain is disordered over two orientations (site-occupancy ratio = 0.522:0.478) and is roughly perpendicular to the fused thia-zolotriazine system. The angle between the fused ring and the propyl chain is 83.6 (1)° [ 82.2 (1)° for the disordered chain]. The structure is stabilized by C-H⋯N hydrogen bonds.

Related literature

For related literature, see: Jiang et al. (2007 ▶); Pauling et al. (1960 ▶); Yunus et al. (2007 ▶).

Experimental

Crystal data

C8H9N3S2

M = 211.32

Monoclinic,

a = 9.3240 (7) Å

b = 14.9973 (11) Å

c = 6.8063 (5) Å

β = 95.505 (1)°

V = 947.37 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.52 mm−1

T = 173 (2) K

0.32 × 0.25 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.853, T max = 0.895

5571 measured reflections

2254 independent reflections

2077 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.068

S = 1.05

2254 reflections

161 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006752/pk2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006752/pk2086Isup2.hkl

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

C8H9N3S2	F000 = 440
Mr = 211.32	Dx = 1.481 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5571 reflections
a = 9.3240 (7) Å	θ = 2.6–28.3º
b = 14.9973 (11) Å	µ = 0.52 mm−1
c = 6.8063 (5) Å	T = 173 (2) K
β = 95.505 (1)º	Block, pale yellow
V = 947.37 (12) Å3	0.32 × 0.25 × 0.22 mm
Z = 4

Bruker SMART CCD diffractometer	2254 independent reflections
Radiation source: fine-focus sealed tube	2077 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
T = 173(2) K	θmax = 28.3º
ω and φ scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −12→12
Tmin = 0.853, Tmax = 0.895	k = −19→14
5571 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024	H-atom parameters constrained
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0392P)2 + 0.2601P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2254 reflections	Δρmax = 0.32 e Å−3
161 parameters	Δρmin = −0.28 e Å−3
5 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (12)

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 > 2σ(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	Occ. (<1)
S1	0.20093 (3)	0.710163 (18)	0.27470 (4)	0.02095 (10)
S2	−0.15462 (3)	0.443002 (19)	0.21702 (4)	0.02265 (10)
N1	0.04853 (10)	0.56884 (6)	0.25767 (13)	0.01739 (19)
N2	0.12868 (11)	0.42185 (7)	0.29852 (15)	0.0235 (2)
N3	0.29929 (11)	0.54164 (7)	0.31895 (15)	0.0231 (2)
C1	0.01557 (13)	0.71890 (8)	0.23196 (17)	0.0224 (2)
H1	−0.0344	0.7739	0.2143	0.027*
C2	−0.04951 (12)	0.63902 (8)	0.22664 (17)	0.0211 (2)
H2	−0.1508	0.6311	0.2043	0.025*
C3	0.18861 (12)	0.59613 (7)	0.28536 (15)	0.0185 (2)
C5	0.01588 (12)	0.47711 (7)	0.25939 (15)	0.0187 (2)
C4	0.26174 (14)	0.45502 (8)	0.32834 (18)	0.0259 (3)	0.522 (4)
C6	0.3713 (6)	0.3883 (4)	0.4050 (7)	0.0221 (9)	0.522 (4)
H6A	0.3288	0.3278	0.4003	0.029 (8)*	0.522 (4)
H6B	0.4062	0.4022	0.5436	0.025 (7)*	0.522 (4)
C7	0.4958 (2)	0.39267 (16)	0.2751 (4)	0.0248 (6)	0.522 (4)
H7A	0.5357	0.4539	0.2799	0.021 (7)*	0.522 (4)
H7B	0.5730	0.3517	0.3292	0.036 (8)*	0.522 (4)
C8	0.4516 (9)	0.3679 (6)	0.0614 (6)	0.0357 (13)	0.522 (4)
H8A	0.5357	0.3714	−0.0143	0.030 (8)*	0.522 (4)
H8B	0.3773	0.4093	0.0055	0.045 (10)*	0.522 (4)
H8C	0.4134	0.3070	0.0552	0.061 (12)*	0.522 (4)
C4A	0.26174 (14)	0.45502 (8)	0.32834 (18)	0.0259 (3)	0.478 (4)
C6A	0.3938 (7)	0.3911 (4)	0.3487 (8)	0.0255 (12)	0.478 (4)
H6A1	0.4827	0.4276	0.3621	0.047 (11)*	0.478 (4)
H6A2	0.3913	0.3565	0.4722	0.038 (11)*	0.478 (4)
C7A	0.4034 (3)	0.32554 (16)	0.1781 (4)	0.0247 (7)	0.478 (4)
H7A1	0.4736	0.2781	0.2199	0.036 (9)*	0.478 (4)
H7A2	0.3083	0.2970	0.1461	0.037 (9)*	0.478 (4)
C8A	0.4491 (8)	0.3709 (6)	−0.0056 (8)	0.0320 (11)	0.478 (4)
H8A1	0.4583	0.3263	−0.1087	0.064 (14)*	0.478 (4)
H8A2	0.5420	0.4007	0.0263	0.061 (13)*	0.478 (4)
H8A3	0.3764	0.4152	−0.0528	0.030 (9)*	0.478 (4)

	U11	U22	U33	U12	U13	U23
S1	0.02618 (16)	0.01417 (15)	0.02233 (16)	−0.00294 (10)	0.00150 (11)	0.00001 (9)
S2	0.02469 (16)	0.01845 (15)	0.02542 (16)	−0.00432 (10)	0.00559 (11)	−0.00188 (10)
N1	0.0225 (4)	0.0139 (4)	0.0155 (4)	−0.0004 (3)	0.0008 (3)	0.0001 (3)
N2	0.0307 (5)	0.0151 (4)	0.0231 (5)	0.0010 (4)	−0.0059 (4)	−0.0003 (4)
N3	0.0254 (5)	0.0183 (5)	0.0243 (5)	0.0009 (4)	−0.0051 (4)	−0.0020 (4)
C1	0.0273 (6)	0.0166 (5)	0.0236 (6)	0.0020 (4)	0.0037 (4)	−0.0001 (4)
C2	0.0235 (5)	0.0172 (5)	0.0226 (5)	0.0024 (4)	0.0029 (4)	0.0003 (4)
C3	0.0247 (5)	0.0157 (5)	0.0147 (5)	−0.0022 (4)	0.0000 (4)	−0.0010 (4)
C5	0.0280 (5)	0.0148 (5)	0.0130 (5)	−0.0015 (4)	0.0010 (4)	−0.0015 (4)
C4	0.0301 (6)	0.0183 (5)	0.0266 (6)	0.0025 (4)	−0.0106 (5)	−0.0023 (4)
C6	0.0217 (16)	0.0211 (14)	0.023 (2)	0.0022 (11)	−0.0009 (16)	0.0060 (18)
C7	0.0159 (11)	0.0253 (12)	0.0332 (13)	0.0029 (8)	0.0023 (9)	−0.0008 (9)
C8	0.0347 (17)	0.039 (2)	0.034 (3)	0.0051 (15)	0.006 (3)	−0.009 (3)
C4A	0.0301 (6)	0.0183 (5)	0.0266 (6)	0.0025 (4)	−0.0106 (5)	−0.0023 (4)
C6A	0.032 (3)	0.0196 (16)	0.023 (3)	0.0051 (16)	−0.0085 (19)	0.0019 (19)
C7A	0.0224 (11)	0.0180 (12)	0.0337 (15)	0.0042 (9)	0.0030 (10)	0.0003 (10)
C8A	0.0268 (16)	0.0325 (18)	0.038 (3)	−0.0014 (13)	0.009 (3)	0.004 (3)

S1—C3	1.7161 (11)	C6—H6B	0.9900
S1—C1	1.7299 (13)	C7—C8	1.519 (5)
S2—C5	1.6686 (12)	C7—H7A	0.9900
N1—C3	1.3644 (14)	C7—H7B	0.9900
N1—C2	1.3967 (14)	C8—H8A	0.9800
N1—C5	1.4093 (14)	C8—H8B	0.9800
N2—C4	1.3340 (16)	C8—H8C	0.9800
N2—C5	1.3455 (15)	C6A—C7A	1.531 (6)
N3—C3	1.3191 (15)	C6A—H6A1	0.9900
N3—C4	1.3485 (15)	C6A—H6A2	0.9900
C1—C2	1.3418 (17)	C7A—C8A	1.520 (6)
C1—H1	0.9500	C7A—H7A1	0.9900
C2—H2	0.9500	C7A—H7A2	0.9900
C4—C6	1.488 (6)	C8A—H8A1	0.9800
C6—C7	1.526 (5)	C8A—H8A2	0.9800
C6—H6A	0.9900	C8A—H8A3	0.9800
C3—S1—C1	90.73 (6)	C8—C7—C6	113.1 (4)
C3—N1—C2	113.50 (9)	C8—C7—H7A	109.0
C3—N1—C5	119.76 (9)	C6—C7—H7A	109.0
C2—N1—C5	126.73 (10)	C8—C7—H7B	109.0
C4—N2—C5	119.89 (10)	C6—C7—H7B	109.0
C3—N3—C4	113.74 (10)	H7A—C7—H7B	107.8
C2—C1—S1	112.26 (9)	C7—C8—H8A	109.5
C2—C1—H1	123.9	C7—C8—H8B	109.5
S1—C1—H1	123.9	H8A—C8—H8B	109.5
C1—C2—N1	112.39 (10)	C7—C8—H8C	109.5
C1—C2—H2	123.8	H8A—C8—H8C	109.5
N1—C2—H2	123.8	H8B—C8—H8C	109.5
N3—C3—N1	124.11 (10)	C7A—C6A—H6A1	108.4
N3—C3—S1	124.77 (9)	C7A—C6A—H6A2	108.4
N1—C3—S1	111.11 (8)	H6A1—C6A—H6A2	107.5
N2—C5—N1	115.95 (10)	C8A—C7A—C6A	112.2 (4)
N2—C5—S2	123.99 (9)	C8A—C7A—H7A1	109.2
N1—C5—S2	120.05 (8)	C6A—C7A—H7A1	109.2
N2—C4—N3	126.44 (11)	C8A—C7A—H7A2	109.2
N2—C4—C6	113.6 (3)	C6A—C7A—H7A2	109.2
N3—C4—C6	119.4 (3)	H7A1—C7A—H7A2	107.9
C4—C6—C7	107.7 (3)	C7A—C8A—H8A1	109.5
C4—C6—H6A	110.2	C7A—C8A—H8A2	109.5
C7—C6—H6A	110.2	H8A1—C8A—H8A2	109.5
C4—C6—H6B	110.2	C7A—C8A—H8A3	109.5
C7—C6—H6B	110.2	H8A1—C8A—H8A3	109.5
H6A—C6—H6B	108.5	H8A2—C8A—H8A3	109.5
C3—S1—C1—C2	−0.03 (9)	C4—N2—C5—S2	179.23 (9)
S1—C1—C2—N1	0.23 (13)	C3—N1—C5—N2	3.03 (15)
C3—N1—C2—C1	−0.38 (14)	C2—N1—C5—N2	−178.04 (10)
C5—N1—C2—C1	−179.36 (10)	C3—N1—C5—S2	−177.64 (8)
C4—N3—C3—N1	−1.45 (16)	C2—N1—C5—S2	1.28 (15)
C4—N3—C3—S1	177.43 (9)	C5—N2—C4—N3	−1.78 (19)
C2—N1—C3—N3	179.37 (10)	C5—N2—C4—C6	169.6 (2)
C5—N1—C3—N3	−1.58 (16)	C3—N3—C4—N2	3.24 (19)
C2—N1—C3—S1	0.35 (11)	C3—N3—C4—C6	−167.7 (2)
C5—N1—C3—S1	179.41 (7)	N2—C4—C6—C7	129.4 (3)
C1—S1—C3—N3	−179.19 (10)	N3—C4—C6—C7	−58.6 (4)
C1—S1—C3—N1	−0.19 (8)	C4—C6—C7—C8	−62.5 (5)
C4—N2—C5—N1	−1.48 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2i	0.95	2.38	3.3261 (16)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N2i	0.95	2.38	3.3261 (16)	171

Symmetry code: (i) .