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Volume 68 
Part 12 
Page o3377  
December 2012  

Received 11 October 2012
Accepted 26 October 2012
Online 17 November 2012

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Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.093
Data-to-parameter ratio = 12.3
Details
Open access

6-Methyl-1,3,5-triazine-2,4-diamine butane-1,4-diol monosolvate

Rajni M. Bhardwaj,a Iain Oswalda and Alastair J. Florencea*

aStrathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, Scotland
Correspondence e-mail: alastair.florence@strath.ac.uk

The title co-crystal, C4H7N5·C4H10O2, crystallizes with one molecule of 6-methyl-1,3,5-triazine-2,4-diamine (DMT) and one molecule of butane-1,4-diol in the asymmetric unit. The DMT molecules form ribbons involving centrosymmetric R22(8) dimer motifs between DMT molecules along the c-axis direction. These ribbons are further hydrogen bonded to each other through butane-1,4-diol, forming sheets parallel to (121).

Related literature

For background to DMT and related structural studies, see: Sebenik et al. (1989[Sebenik, A., Osredkar, U. & Zigon, M. (1989). Polym. Bull. 22, 155-161.]); Kaczmarek et al. (2008[Kaczmarek, M., Radecka-Paryzek, W. & Kubicki, M. (2008). Acta Cryst. E64, o269.]); Portalone (2008[Portalone, G. (2008). Acta Cryst. E64, o1685.]); Xiao (2008[Xiao, Z.-H. (2008). Acta Cryst. E64, o411.]); Fan et al. (2009[Fan, Y., You, W., Qian, H.-F., Liu, J.-L. & Huang, W. (2009). Acta Cryst. E65, o494.]); Qian & Huang (2010[Qian, H.-F. & Huang, W. (2010). Acta Cryst. E66, o759.]); Thanigaimani et al. (2010[Thanigaimani, K., Devi, P., Muthiah, P. T., Lynch, D. E. & Butcher, R. J. (2010). Acta Cryst. C66, o324-o328.]); Perpétuo & Janczak (2007[Perpétuo, G. J. & Janczak, J. (2007). Acta Cryst. C63, o271-o273.]); Portalone & Colapietro (2007[Portalone, G. & Colapietro, M. (2007). Acta Cryst. C63, o655-o658.]); Delori et al. (2008[Delori, A., Suresh, E. & Pedireddi, V. R. (2008). Chem. Eur. J. 14, 6967-6977.]). For details of experimental methods used, see: Florence et al. (2003[Florence, A. J., Baumgartner, B., Weston, C., Shankland, N., Kennedy, A. R., Shankland, K. & David, W. I. F. (2003). J. Pharm. Sci. 92, 1930-1938.]). For ring-motif nomenclature, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data

  • C4H7N5·C4H10O2

  • Mr = 215.27

  • Triclinic, [P \overline 1]

  • a = 5.8755 (3) Å

  • b = 9.0515 (5) Å

  • c = 10.7607 (5) Å

  • [alpha] = 87.911 (3)°

  • [beta] = 74.346 (3)°

  • [gamma] = 83.550 (3)°

  • V = 547.55 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 123 K

  • 0.50 × 0.05 × 0.04 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.637, Tmax = 0.745

  • 7713 measured reflections

  • 1911 independent reflections

  • 1288 reflections with I > 2[sigma](I)

  • Rint = 0.045
Refinement

  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.093

  • S = 1.00

  • 1911 reflections

  • 155 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.84 1.92 2.764 (2) 176
O2-H2...N1ii 0.84 1.94 2.777 (2) 178
N4-H7N...O1iii 0.92 (3) 2.52 (2) 3.173 (2) 128.5 (7)
N4-H8N...N2iv 0.85 (2) 2.19 (2) 3.037 (2) 178 (2)
N5-H9N...O1v 0.88 (2) 2.069 (19) 2.909 (2) 160.1 (18)
N5-H10N...N3v 0.87 (2) 2.14 (2) 3.008 (3) 179 (2)
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z+1; (iii) x+1, y, z-1; (iv) -x+1, -y+1, -z; (v) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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: 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.]) and ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]) and WinGX (Farrugia, 1999)[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.].

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2459 ).

Acknowledgements

RMB thanks the Commonwealth Scholarship Commission for providing a scholarship.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Delori, A., Suresh, E. & Pedireddi, V. R. (2008). Chem. Eur. J. 14, 6967-6977.  [CSD] [CrossRef] [PubMed] [ChemPort]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Fan, Y., You, W., Qian, H.-F., Liu, J.-L. & Huang, W. (2009). Acta Cryst. E65, o494.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Florence, A. J., Baumgartner, B., Weston, C., Shankland, N., Kennedy, A. R., Shankland, K. & David, W. I. F. (2003). J. Pharm. Sci. 92, 1930-1938.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Kaczmarek, M., Radecka-Paryzek, W. & Kubicki, M. (2008). Acta Cryst. E64, o269.  [CSD] [CrossRef] [details]
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]
Perpétuo, G. J. & Janczak, J. (2007). Acta Cryst. C63, o271-o273.  [CSD] [CrossRef] [details]
Portalone, G. (2008). Acta Cryst. E64, o1685.  [CSD] [CrossRef] [details]
Portalone, G. & Colapietro, M. (2007). Acta Cryst. C63, o655-o658.  [CSD] [CrossRef] [details]
Qian, H.-F. & Huang, W. (2010). Acta Cryst. E66, o759.  [CrossRef] [details]
Sebenik, A., Osredkar, U. & Zigon, M. (1989). Polym. Bull. 22, 155-161.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Thanigaimani, K., Devi, P., Muthiah, P. T., Lynch, D. E. & Butcher, R. J. (2010). Acta Cryst. C66, o324-o328.  [CSD] [CrossRef] [details]
Xiao, Z.-H. (2008). Acta Cryst. E64, o411.  [CSD] [CrossRef] [details]

Acta Cryst (2012). E68, o3377  [ doi:10.1107/S1600536812044480 ]

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