2-Propyl-4H-thia­zolo[3,2-a][1,3,5]triazine-4-thione

Uzma Yunus; Muhammad Kalim Tahir; Moazzam Hussain Bhatti; Wai-Yeung Wong

doi:10.1107/S1600536808006752

. 2008 Mar 20;64(Pt 4):o722. doi: 10.1107/S1600536808006752

2-Propyl-4H-thiazolo[3,2-a][1,3,5]triazine-4-thione

Uzma Yunus ^a,^*, Muhammad Kalim Tahir ^a, Moazzam Hussain Bhatti ^a, Wai-Yeung Wong ^b

PMCID: PMC2961019 PMID: 21202112

Abstract

In the title compound, C₈H₉N₃S₂, the n-propyl chain is disordered over two orientations (site-occupancy ratio = 0.522:0.478) and is roughly perpendicular to the fused thiazolotriazine 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 _r = 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
Δρ_max = 0.32 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-64-0o722-sup1.cif^{(17KB, cif)}

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

e-64-0o722-Isup2.hkl^{(110.8KB, hkl)}

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
C1—H1⋯N2ⁱ	0.95	2.38	3.3261 (16)	171

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge Allama Iqbal Open University, Islamabad, Pakistan, for providing research facilities.

supplementary crystallographic information

Comment

We have previously reported the crystal structure of 2-phenyl-4H-thiazolo[3,2,-a]- [1,3,5]triazine-4-thione with a phenyl group attached to the 1,3,5-triazine ring (Yunus et al., 2007). The molecule was essentially planar. In contrast, in the title compound the pendant n-propyl group is almost perpendicular to the fused thiazolo[3,2,-a][1,3,5]triazine ring, which are themselves co-planar (maximum deviation from mean plane is 0.0437 (1) Å from atom C4). The n-propyl chain is disordered over two orientations with a site occupancy ratio of 0.522:0.478 (Jiang et al., 2007). The CN bond distances of the 1,3,5-triazine ring are in the range 1.3191 (15) to 1.4093 (14) Å, in which N1—C5 bond length is slightly longer than that of N2—C5. These values are intermediate between those expected for single and double C—N bonds (1.47 and 1.27 Å, respectively). The C=S bond length of 1.6686 (12) Å is similar to that of the phenyl analog (Yunus et al., 2007) but is slightly longer then the pure double bond distance (1.61 Å) (Pauling 1960). The bond angles and bond lengths in the thiazole ring are within the normal ranges. The crystal structure is stabilized by weak C—H···N hydrogen bonding interactions.

Experimental

A mixture of ammonium thiocyanate (26 mmol) and butyryl chloride (26 mmol) in dry acetone (60 ml) was stirred for 30 min. Then 2-aminothiazole (26 mmol) was added and the reaction mixture was refluxed for 2 h. After cooling, the reaction mixture was poured into acidified cold water. The resulting yellow solid was filtered and washed with cold acetone. Single crystals of the title compound suitable for single-crystal x-ray analysis were obtained by recrystallization of the yellow solid from acetonitrile.