Pyrimidine-2,4-diamine acetone monosolvate

Draguta, S.; Sandhu, B.; Khrustalev, V.N.; Fonari, M.S.; Timofeeva, T.V.

doi:10.1107/S1600536813001025

Volume 69
Part 2
Page o251
February 2013

Received 1 January 2013
Accepted 11 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.048
wR = 0.139
Data-to-parameter ratio = 17.1
Details

Pyrimidine-2,4-diamine acetone monosolvate

Sergiu Draguta,^a ^* Bhupinder Sandhu,^b Victor N. Khrustalev,^c Marina S. Fonari ^d and Tatiana V. Timofeeva ^b

^aD. Ghitu Institute of Electronic Engineering and Nanotechnologies, 3/3 Academy Street, MD-2028, Chisinau, Republic of Moldova,^bDepartment of Biology & Chemistry, New Mexico Highlands University, 803 University Avenue, Las Vegas, NM 87701, USA,^cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation, and ^dInstitute of Applied Physics Academy of Science of Moldova, 5 Academy Street, MD-2028, Chisinau, Republic of Moldova.
Correspondence e-mail: sergiudraguta@gmail.com

In the title compound, C₄H₆N₄·C₃H₆O, the pyrimidine-2,4-diamine molecule is nearly planar (r.m.s. deviation = 0.005 Å), with the endocyclic angles covering the range 114.36 (10)-126.31 (10)°. In the crystal, N-HN and N-HO hydrogen bonds link the molecules into ribbons along [101], and weak C-H [pi] interactions consolidate further the crystal packing.

Related literature

For the biological activity of pyrimidine derivatives, see: Hall et al. (1993); Gengeliczki et al. (2011). For the crystal structures of related compounds, see: Bertolasi et al. (2002); Draguta et al. (2012). For bond lengths in organic compounds, see: Allen et al. (1987). For hydrogen-bonding graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₄H₆N₄·C₃H₆O
M_r = 168.21
Monoclinic, P 2₁ /c
a = 8.1594 (15) Å
b = 12.728 (2) Å
c = 8.7663 (16) Å
= 99.395 (3)°
V = 898.2 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.974, T_max = 0.982
9693 measured reflections
2170 independent reflections
1752 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.139
S = 1.07
2170 reflections
127 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the pyrimidine ring.

D-HA	D-H	HA	DA	D-HA
N2-H2AN1ⁱ	0.875 (18)	2.191 (18)	3.0608 (18)	177.3 (15)
N2-H2BO1	0.871 (16)	2.247 (19)	3.0990 (17)	164.7 (16)
N4-H4AO1ⁱⁱ	0.879 (17)	2.170 (18)	2.9141 (16)	142.2 (15)
N4-H4BN3ⁱⁱ	0.900 (18)	2.120 (19)	3.0171 (17)	174.9 (15)
C9-H9CCgⁱⁱⁱ	0.96	2.63	3.5484 (17)	159
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5381 ).

Acknowledgements

The authors are grateful for NSF support via DMR grant 0934212 (PREM) and CHE 0832622.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bertolasi, V., Pretto, L., Gilli, P., Ferretti, V. & Gilli, G. (2002). New J. Chem. 26, 1559-1566.
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Draguta, S., Khrustalev, V. N., Fonari, M. S., Antipin, M. Y. & Timofeeva, T. V. (2012). Acta Cryst. E68, o3353.
Gengeliczki, Z., Callahan, M. P., Kabelác, M., Rijs, A. M. & de Vries, M. S. (2011). J. Phys. Chem. A, 115, 11423-11427.
Hall, I. A., Campbell, K. L., Chambers, M. D. & Davis, C. N. (1993). J. Am. Vet. Med. Assoc. 202, 1959-1962.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.