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Volume 69 
Part 8 
Page o1235  
August 2013  

Received 25 June 2013
Accepted 1 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.069
wR = 0.210
Data-to-parameter ratio = 13.5
Details
Open access

2-Amino-4,6-dimethylpyrimidine-sorbic acid (1/1)

aSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India
Correspondence e-mail: tommtrichy@yahoo.co.in

In the crystal of the title compound, C6H9N3·C6H8O2, the 2-amino-4,6-dimethylpyrimidine and sorbic acid molecules are linked through N-H...O and O-H...N hydrogen bonds, which generate a cyclic bimolecular heterosynthon with an R22(8) graph-set motif. Further, two inversion-related pyrimidine molecules are base-paired via a pair of N-H...N hydrogen bonds, forming a cyclic bimolecular homosynthon with a graph-set of R22(8). A discrete hetero tetrameric supramolecular unit along the b axis is formed by the fusion of two heterosynthons and one homosynthon. An aromatic [pi]-[pi] interaction [centroid-centroid distance = 3.7945 (16) Å] is observed between these tetrameric units.

Related literature

For aminopyrimidine-carboxylic acid interactions, see: Hunt et al. (1980[Hunt, W. E., Schwalbe, C. H., Bird, K. & Mallinson, P. D. (1980). J. Biochem. 187, 533-536.]). For related structures, see: Thanigaimani et al. (2007[Thanigaimani, K., Muthiah, P. T. & Lynch, D. E. (2007). Acta Cryst. E63, o4450-o4451.]); Ebenezer & Muthiah (2010[Ebenezer, S. & Muthiah, P. T. (2010). Acta Cryst. E66, o2634-o2635.], 2012[Ebenezer, S. & Muthiah, P. T. (2012). Cryst. Growth Des. 12, 3766-3785.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N3·C6H8O2

  • Mr = 235.29

  • Triclinic, [P \overline 1]

  • a = 7.8441 (6) Å

  • b = 9.9413 (8) Å

  • c = 10.2846 (13) Å

  • [alpha] = 112.058 (7)°

  • [beta] = 98.333 (8)°

  • [gamma] = 111.306 (5)°

  • V = 654.69 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.12 × 0.11 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.990, Tmax = 0.993

  • 9667 measured reflections

  • 2280 independent reflections

  • 1585 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.210

  • S = 1.03

  • 2280 reflections

  • 169 parameters

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...N1 0.99 (4) 1.70 (4) 2.674 (3) 167 (4)
N2-H2A...N3i 0.89 (3) 2.19 (3) 3.076 (4) 176 (2)
N2-H2B...O1 0.86 (4) 2.10 (4) 2.946 (4) 171 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), 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 POV-RAY (Cason, 2004[Cason, C. J. (2004). POV-RAY. Persistence of Vision Raytracer Pty. Ltd, Victoria, Australia.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5286 ).


Acknowledgements

SG thanks the UGC-SAP, India, for the award of an RFSMS. The authors thank the DST India (FIST programme) for the use of Bruker SMART APEXII diffractometer at the School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamilnadu, India.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cason, C. J. (2004). POV-RAY. Persistence of Vision Raytracer Pty. Ltd, Victoria, Australia.
Ebenezer, S. & Muthiah, P. T. (2010). Acta Cryst. E66, o2634-o2635.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Ebenezer, S. & Muthiah, P. T. (2012). Cryst. Growth Des. 12, 3766-3785.  [CSD] [CrossRef] [ChemPort]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [Web of Science]
Hunt, W. E., Schwalbe, C. H., Bird, K. & Mallinson, P. D. (1980). J. Biochem. 187, 533-536.  [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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Thanigaimani, K., Muthiah, P. T. & Lynch, D. E. (2007). Acta Cryst. E63, o4450-o4451.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1235  [ doi:10.1107/S1600536813018175 ]

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