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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 [sigma](C-C) = 0.002 Å
R = 0.048
wR = 0.139
Data-to-parameter ratio = 17.1
Details
Open access

Pyrimidine-2,4-diamine acetone monosolvate

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-H...N and N-H...O 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[Hall, I. A., Campbell, K. L., Chambers, M. D. & Davis, C. N. (1993). J. Am. Vet. Med. Assoc. 202, 1959-1962.]); Gengeliczki et al. (2011[Gengeliczki, Z., Callahan, M. P., Kabelác, M., Rijs, A. M. & de Vries, M. S. (2011). J. Phys. Chem. A, 115, 11423-11427.]). For the crystal structures of related compounds, see: Bertolasi et al. (2002[Bertolasi, V., Pretto, L., Gilli, P., Ferretti, V. & Gilli, G. (2002). New J. Chem. 26, 1559-1566.]); Draguta et al. (2012[Draguta, S., Khrustalev, V. N., Fonari, M. S., Antipin, M. Y. & Timofeeva, T. V. (2012). Acta Cryst. E68, o3353.]). For bond lengths in organic compounds, see: Allen et al. (1987[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.]). For hydrogen-bonding graph-set notation, see: 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
  • C4H6N4·C3H6O

  • Mr = 168.21

  • Monoclinic, P 21 /c

  • a = 8.1594 (15) Å

  • b = 12.728 (2) Å

  • c = 8.7663 (16) Å

  • [beta] = 99.395 (3)°

  • V = 898.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.982

  • 9693 measured reflections

  • 2170 independent reflections

  • 1752 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the pyrimidine ring.

D-H...A D-H H...A D...A D-H...A
N2-H2A...N1i 0.875 (18) 2.191 (18) 3.0608 (18) 177.3 (15)
N2-H2B...O1 0.871 (16) 2.247 (19) 3.0990 (17) 164.7 (16)
N4-H4A...O1ii 0.879 (17) 2.170 (18) 2.9141 (16) 142.2 (15)
N4-H4B...N3ii 0.900 (18) 2.120 (19) 3.0171 (17) 174.9 (15)
C9-H9C...Cgiii 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[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [ChemPort] [ISI]
Bertolasi, V., Pretto, L., Gilli, P., Ferretti, V. & Gilli, G. (2002). New J. Chem. 26, 1559-1566.  [ISI] [CSD] [CrossRef] [ChemPort]
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.  [CSD] [CrossRef] [details]
Gengeliczki, Z., Callahan, M. P., Kabelác, M., Rijs, A. M. & de Vries, M. S. (2011). J. Phys. Chem. A, 115, 11423-11427.  [ISI] [CrossRef] [ChemPort] [PubMed]
Hall, I. A., Campbell, K. L., Chambers, M. D. & Davis, C. N. (1993). J. Am. Vet. Med. Assoc. 202, 1959-1962.  [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o251  [ doi:10.1107/S1600536813001025 ]

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