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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 [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.089
Data-to-parameter ratio = 20.5
Details
Open access

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

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-H...O and N-H...S 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[Selvam, T. P., James, C. R., Dniandev, P. V. & Valzita, S. K. (2012). Res. Pharm. 2, 1-9.]); Gupta et al. (2010[Gupta, J. K., Chaudhary, A., Dudhe, R., Varuna, K., Sharma, P. K. & Verma, P. K. (2010). Int. J. Pharm. Sci. Res. 1, 34-49.]); Lagoja (2005[Lagoja, I. M. (2005). Chem. Biodivers. 2, 1-50.]). For the crystal structures of related compounds, see: Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Samshuddin, S. & Narayana, B. (2012). Acta Cryst. E68, o2398.]); Fun et al. (2012[Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o807-o808.]); Betz et al. (2012[Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o476-o477.]). For puckering analysis of six-membered rings, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Boeyens (1978[Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C12H16N2OS

  • Mr = 236.33

  • Monoclinic, P 21 /c

  • a = 10.1894 (3) Å

  • b = 14.6889 (4) Å

  • c = 9.2026 (2) Å

  • [beta] = 111.719 (1)°

  • V = 1279.58 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.898, Tmax = 0.926

  • 12126 measured reflections

  • 3173 independent reflections

  • 2876 reflections with I > 2[sigma](I)

  • Rint = 0.011

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...S1i 0.862 (15) 2.503 (16) 3.3527 (9) 168.8 (12)
N2-H2...O1ii 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[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o476-o477.  [CSD] [CrossRef] [details]
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.  [CrossRef]
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.  [CrossRef] [ChemPort] [ISI]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o807-o808.  [CSD] [CrossRef] [details]
Gupta, J. K., Chaudhary, A., Dudhe, R., Varuna, K., Sharma, P. K. & Verma, P. K. (2010). Int. J. Pharm. Sci. Res. 1, 34-49.  [ChemPort]
Kant, R., Gupta, V. K., Kapoor, K., Samshuddin, S. & Narayana, B. (2012). Acta Cryst. E68, o2398.  [CSD] [CrossRef] [details]
Lagoja, I. M. (2005). Chem. Biodivers. 2, 1-50.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3271  [ doi:10.1107/S1600536812044662 ]

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