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

Ebenezer, S.; Muthiah, P.T.

doi:10.1107/S1600536810003661

Volume 66
Part 3
Page o516
March 2010

Received 21 January 2010
Accepted 29 January 2010
Online 3 February 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.053
wR = 0.174
Data-to-parameter ratio = 23.5
Details

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

Samuel Ebenezer ^a and Packianathan Thomas Muthiah ^a ^*

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

In the title 1:1 adduct, C₆H₉N₃·C₇H₇NO₂, the crystal structure is stabilized by hydrogen bonds involving two different R₂²(8) motifs. One of them is formed by the interaction of 2-amino-4,6-dimethylpyrimidine (AMPY) with the carboxyl group of anthranilic acid (AA) through N-HO and O-HN hydrogen bonds, whereas the other is formed through the interaction of two centrosymmetrically related pyrimidines involving N-HN hydrogen bonds. These two combined motifs form a heterotetramer. The heterotetramer sheets are stacked into three-dimensional network.

Related literature

For the importance the reaction of aminopyrimidine derivatives and carboxylic acids in protein-nucleic acid recognition and drug binding, see: Hunt et al. (1980); Baker & Santi (1965). For pyrimidine-carboxylic acid interactions, see: Allen et al. (1999). For co-crystals of AMPY, see: Balasubramani et al. (2005, 2006); Devi & Muthiah (2007). For hydrogen-bonded synthons, see: Thakur & Desiraju (2008). For packing patterns in 2-amino-4,6-dimethylpyrimidine-salicylate, see: Muthiah et al. (2006). For typical geometric parameters in aromatic stacking, see: Hunter (1994).

Experimental

Crystal data

C₆H₉N₃·C₇H₇NO₂
M_r = 260.30
Triclinic, $[P \overline 1]$
a = 7.1922 (2) Å
b = 7.4269 (2) Å
c = 13.0675 (3) Å
= 77.583 (1)°
= 78.990 (1)°
= 82.473 (1)°
V = 666.19 (3) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.975, T_max = 0.982
16171 measured reflections
4279 independent reflections
3021 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.174
S = 1.04
4279 reflections
182 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.81	1.90	2.7014 (13)	168
N2-H2AN3ⁱ	0.86	2.26	3.0745 (14)	159
N2-H2BO2	0.86	1.98	2.8303 (15)	169
N4-H4AO2	0.94 (2)	1.91 (2)	2.6571 (17)	135.5 (17)
N4-H4BN4ⁱⁱ	0.89 (2)	2.62 (2)	3.1409 (18)	118.7 (17)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2248 ).

Acknowledgements

The authors thank the DST-India (FIST programme) for the use of diffractometer at the School of Chemistry, Bharathidasan University.

References

Allen, F. H., Motherwell, W. D. S., Raithby, P. R., Shields, G. P. & Taylor, R. (1999). New J. Chem. pp. 25-34.
Baker, B. R. & Santi, D. V. (1965). J. Pharm. Sci. 54, 1252-1257.
Balasubramani, K., Muthiah, P. T. & Lynch, D. E. (2006). Acta Cryst. E62, o2907-o2909.
Balasubramani, K., Muthiah, P. T., RajaRam, R. K. & Sridhar, B. (2005). Acta Cryst. E61, o4203-o4205.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Devi, P. & Muthiah, P. T. (2007). Acta Cryst. E63, o4822-o4823.
Hunt, W. E., Schwalbe, C. H., Bird, K. & Mallinson, P. D. (1980). J. Biochem. 187, 533-536.
Hunter, C. A. (1994). Chem. Soc. Rev. 23, 101-109.
Muthiah, P. T., Balasubramani, K., Rychlewska, U. & Plutecka, A. (2006). Acta Cryst. C62, o605-o607.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Thakur, T. S. & Desiraju, G. R. (2008). Cryst. Growth Des. 8, 4031-4044.

organic compounds