1-(4-Chloro­phen­yl)-4,4,6-trimethyl-3,4-dihydro­pyrimidine-2(1H)-thione

Saeed, A.; Bolte, M.

doi:10.1107/S1600536810001777

Volume 66
Part 2
Page o440
February 2010

Received 6 January 2010
Accepted 14 January 2010
Online 23 January 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 15.6
Details

1-(4-Chlorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione

Aamer Saeed ^a ^* and Michael Bolte ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: aamersaeed@yahoo.com

The dihydropyrimidine ring of the title compound, C₁₃H₁₅ClN₂S, adopts an envelope conformation with five almost coplanar atoms (r.m.s. deviation = 0.054 Å) and the C atom bearing the two methyl substituents deviating from this plane by 0.441 (2) Å. The best plane through the five almost coplanar atoms forms a dihedral angle of 89.56 (5)° with the benzene ring. The crystal packing is characterized by centrosymmetric dimers connected by pairs of N-HS hydrogen bonds.

Related literature

For details of the biological activity of pyrimidine-2-thiones, see: Alam et al. (2005); Sriram et al. (2006); Leite et al. (2006); Kappe (2000); Rovnyak et al. (1995); Swamy et al. (2005). For a related structure, see: Yamin et al. (2005).

Experimental

Crystal data

C₁₃H₁₅ClN₂S
M_r = 266.78
Monoclinic, C 2/c
a = 20.6710 (18) Å
b = 10.8343 (10) Å
c = 14.8619 (13) Å
= 126.026 (5)°
V = 2691.9 (4) Å³
Z = 8
Mo K radiation
= 0.42 mm^-1
T = 173 K
0.37 × 0.29 × 0.26 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995) T_min = 0.861, T_max = 0.899
7624 measured reflections
2512 independent reflections
2134 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.093
S = 1.02
2512 reflections
161 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1S1ⁱ	0.83 (2)	2.59 (2)	3.4054 (16)	169.1 (17)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2028 ).

Acknowledgements

The authors gratefully acknowledge a research grant from the Higher Education Commission of Pakistan under project No. 20-Miscel/R&D/00/3834.

References

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Sriram, D., Yogeeswari, P. & Devakaram, R. V. (2006). Bioorg. Med. Chem. 14, 3113-3118.
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.
Swamy, S. N., Basappa, Priya, B. S., Prabhuswamy, B., Doreswamy, B. H., Prasad, J. S. & Rangappa K. S. (2005). Eur. J. Med. Chem. 41, 531-538.
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organic compounds