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Volume 68 
Part 12 
Page o3353  
December 2012  

Received 6 November 2012
Accepted 8 November 2012
Online 17 November 2012

[cv5359sup1]
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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.109
Data-to-parameter ratio = 18.8
Details
Open access

Pyridine-2,5-diamine

Sergiu Draguta,a* Victor N. Khrustalev,b Marina S. Fonari,c Mikhail Yu. Antipind and Tatiana V. Timofeevad

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

In the title molecule, C5H7N3, intracyclic angles cover the range 117.15 (10)-124.03 (11)°. The N atoms of the amino groups have trigonal-pyramidal configurations deviating slightly from the pyridine plane by 0.106 (2) and -0.042 (2) Å. In the crystal, the pyridine N atom serves as an acceptor of an N-H...N hydrogen bond which links two molecules into a centrosymmetric dimer. Intermolecular N-H...N hydrogen bonds between the amino groups further consolidate the crystal packing, forming a three-dimensional network.

Related literature

For general background, see: Domenicano et al. (1975[Domenicano, A., Vaciago, A. & Coulson, C. A. (1975). Acta Cryst. B31, 221-234.]); Domenicano & Vaciago (1979[Domenicano, A. & Vaciago, A. (1979). Acta Cryst. B35, 1382-1388.]); Mootz & Wussow (1981[Mootz, D. & Wussow, H.-G. (1981). J. Chem. Phys. 75, 1517-1522.]); Crawford et al. (2009[Crawford, S., Kirchner, M. T., Blaser, D., Boese, R., David, W. I. F., Dawson, A., Gehrke, A., Ibberson, R. M., Marshall, W. G., Parsons, S. & Yamamuro, O. (2009). Angew. Chem. Int. Ed. 48, 755-757.]). For the crystal structures of isomeric diaminopyridines, see: Schwalbe et al. (1987[Schwalbe, C. H., Williams, G. J. B. & Koetzle, T. F. (1987). Acta Cryst. C43, 2191-2195.]); Rubin-Preminger & Englert (2007[Rubin-Preminger, J. M. & Englert, U. (2007). Acta Cryst. E63, o757-o758.]); Al-Dajani et al. (2009[Al-Dajani, M. T. M., Salhin, A., Mohamed, N., Loh, W.-S. & Fun, H.-K. (2009). Acta Cryst. E65, o2931-o2932.]); Betz et al. (2011[Betz, R., Gerber, T., Hosten, E. & Schalekamp, H. (2011). Acta Cryst. E67, o2154.]).

[Scheme 1]

Experimental

Crystal data

  • C5H7N3

  • Mr = 109.14

  • Orthorhombic, P b c a

  • a = 11.4447 (11) Å

  • b = 7.1447 (7) Å

  • c = 12.8030 (12) Å

  • V = 1046.89 (17) Å3

  • Z = 8

  • 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. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.982

  • 13022 measured reflections

  • 1595 independent reflections

  • 1240 reflections with I > 2[sigma](I)

  • Rint = 0.049
Refinement

  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.109

  • S = 1.01

  • 1595 reflections

  • 85 parameters

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

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...N1i 0.874 (17) 2.183 (17) 3.0541 (15) 175.1 (10)
N2-H2B...N3ii 0.879 (17) 2.309 (17) 3.1457 (16) 159.3 (10)
N3-H3A...N2iii 0.894 (16) 2.397 (17) 3.2150 (16) 152.2 (10)
N3-H3B...N2iv 0.898 (17) 2.593 (17) 3.4803 (16) 170.0 (10)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+1, 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: CV5359 ).

Acknowledgements

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

References

Al-Dajani, M. T. M., Salhin, A., Mohamed, N., Loh, W.-S. & Fun, H.-K. (2009). Acta Cryst. E65, o2931-o2932.  [CSD] [CrossRef] [details]
Betz, R., Gerber, T., Hosten, E. & Schalekamp, H. (2011). Acta Cryst. E67, o2154.  [CSD] [CrossRef] [details]
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Crawford, S., Kirchner, M. T., Blaser, D., Boese, R., David, W. I. F., Dawson, A., Gehrke, A., Ibberson, R. M., Marshall, W. G., Parsons, S. & Yamamuro, O. (2009). Angew. Chem. Int. Ed. 48, 755-757.  [CSD] [CrossRef] [ChemPort]
Domenicano, A. & Vaciago, A. (1979). Acta Cryst. B35, 1382-1388.  [CrossRef] [details] [ISI]
Domenicano, A., Vaciago, A. & Coulson, C. A. (1975). Acta Cryst. B31, 221-234.  [CrossRef] [details] [ISI]
Mootz, D. & Wussow, H.-G. (1981). J. Chem. Phys. 75, 1517-1522.  [CrossRef] [ChemPort]
Rubin-Preminger, J. M. & Englert, U. (2007). Acta Cryst. E63, o757-o758.  [CSD] [CrossRef] [details]
Schwalbe, C. H., Williams, G. J. B. & Koetzle, T. F. (1987). Acta Cryst. C43, 2191-2195.  [CrossRef] [details]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2012). E68, o3353  [ doi:10.1107/S1600536812046260 ]

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