4-Meth­oxy-4-methyl-6-phenyl-1,3-diazinane-2-thione

Samshuddin, S.; Narayana, B.; Yathirajan, H.S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812044662

Volume 68
Part 12
Page o3271
December 2012

Received 13 October 2012
Accepted 29 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.089
Data-to-parameter ratio = 20.5
Details

4-Methoxy-4-methyl-6-phenyl-1,3-diazinane-2-thione

Seranthimata Samshuddin,^a Badiadka Narayana,^a Hemmige S. Yathirajan,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India,^bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title pyrimidine derivative, C₁₂H₁₆N₂OS, the tetrahydropyrimidine ring adopts an envelope conformation with the C atom of the methylene -CH₂- group as the flap. In the crystal, N-HO and N-HS hydrogen bonds connect molecules into undulating sheets perpendicular to the a axis.

Related literature

For the pharmacological importance of pyrimidines, see: Selvam et al. (2012); Gupta et al. (2010); Lagoja (2005). For the crystal structures of related compounds, see: Kant et al. (2012); Fun et al. (2012); Betz et al. (2012). For puckering analysis of six-membered rings, see: Cremer & Pople (1975); Boeyens (1978). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₂H₁₆N₂OS
M_r = 236.33
Monoclinic, P 2₁ /c
a = 10.1894 (3) Å
b = 14.6889 (4) Å
c = 9.2026 (2) Å
= 111.719 (1)°
V = 1279.58 (6) Å³
Z = 4
Mo K radiation
= 0.24 mm^-1
T = 200 K
0.47 × 0.41 × 0.33 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.898, T_max = 0.926
12126 measured reflections
3173 independent reflections
2876 reflections with I > 2(I)
R_int = 0.011

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.089
S = 1.07
3173 reflections
155 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.33 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1S1ⁱ	0.862 (15)	2.503 (16)	3.3527 (9)	168.8 (12)
N2-H2O1ⁱⁱ	0.841 (15)	2.076 (16)	2.8863 (12)	161.7 (13)
Symmetry codes: (i) -x+2, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5545 ).

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. HSY thanks Mysore University for the research facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o476-o477.
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o807-o808.
Gupta, J. K., Chaudhary, A., Dudhe, R., Varuna, K., Sharma, P. K. & Verma, P. K. (2010). Int. J. Pharm. Sci. Res. 1, 34-49.
Kant, R., Gupta, V. K., Kapoor, K., Samshuddin, S. & Narayana, B. (2012). Acta Cryst. E68, o2398.
Lagoja, I. M. (2005). Chem. Biodivers. 2, 1-50.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Selvam, T. P., James, C. R., Dniandev, P. V. & Valzita, S. K. (2012). Res. Pharm. 2, 1-9.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds