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Volume 68 
Part 12 
Page o3466  
December 2012  

Received 16 November 2012
Accepted 21 November 2012
Online 28 November 2012

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.130
Data-to-parameter ratio = 17.3
Details
Open access

6-Methylpyridin-2-amine

Sergiu Draguta,a* Victor N. Khrustalev,b Bhupinder Sandhu,c Mikhail Yu. Antipind and Tatiana V. Timofeevac

aD. Ghitu Institute of Electronic Engineering and Nanotechnologies, 3/3 Academy str., MD-2028, Chisinau, Republic of 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,cDepartment of Chemistry & Biology, New Mexico Highlands University, 803 University Avenue, Las Vegas, NM 87701, USA, and dDepartment of Chemistry & Biology, New Mexico Highlands University, 803 University Avenue, Las mVegas, NM 87701, USA
Correspondence e-mail: sergiudraguta@gmail.com

In the title molecule, C6H8N2, the endocyclic angles are in the range 118.43 (9)-122.65 (10)°. The molecular skeleton is planar (r.m.s. deviation = 0.007 Å). One of the two amino H atoms is involved in an N-H...N hydrogen bond, forming an inversion dimer, while the other amino H atom participates in N-H...[pi] interactions between the dimers, forming layers parallel to (100).

Related literature

For general background to the design of chiral or acentric co-crystals, see: Jacques et al. (1981[Jacques, J., Collet, A. & Wilen, S. H. (1981). In Enantiomers, Racemates, and Resolutions. New York: John Wiley & Sons.]); Miyata (1991[Miyata, S. (1991). In Organic Molecules for Nonlinear Optics and Photonics, edited by J. Messier, F. Kajzar & P. Prasad, P. Dordrecht: Kluwer Academic Publishers.]); Scheiner (1997[Scheiner, S. (1997). In Molecular Interactions. Chichester: John Wiley & Sons.]). For related compounds, see: Büyükgüngör & Odabasoglu (2006[Büyükgüngör, O. & Odabasoglu, M. (2006). Acta Cryst. E62, o2749-o2750.]); Chtioui & Jouini (2006[Chtioui, A. & Jouini, A. (2006). Mater. Res. Bull. 41, 569-575.]); Ni et al. (2007[Ni, S.-F., Feng, W.-J., Guo, H. & Jin, Z.-M. (2007). Acta Cryst. E63, o3866.]); Dai et al. (2011[Dai, W.-M., Zhou, H. & Hu, Y.-Q. (2011). Acta Cryst. E67, o578.]); Waddell et al. (2011[Waddell, P. G., Hulse, J. O. S. & Cole, J. M. (2011). Acta Cryst. C67, o255-o258.]).

[Scheme 1]

Experimental

Crystal data

  • C6H8N2

  • Mr = 108.14

  • Monoclinic, P 21 /c

  • a = 9.1006 (11) Å

  • b = 6.2458 (8) Å

  • c = 10.5598 (13) Å

  • [beta] = 100.952 (2)°

  • V = 589.29 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 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 = 0.977, Tmax = 0.985

  • 5852 measured reflections

  • 1420 independent reflections

  • 1196 reflections with I > 2[sigma](I)

  • Rint = 0.030
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.130

  • S = 1.00

  • 1420 reflections

  • 82 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C2-C6 ring.
D-H...A D-H H...A D...A D-H...A
N2-H2A...N1i 0.896 (17) 2.211 (17) 3.1062 (14) 177.5 (11)
N2-H2B...Cgii 0.867 (17) 2.674 (16) 3.4875 (12) 163.5 (11)
Symmetry codes: (i) -x, -y+1, -z+2; (ii) [-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: CV5366 ).

Acknowledgements

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

References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Büyükgüngör, O. & Odabasoglu, M. (2006). Acta Cryst. E62, o2749-o2750.  [CrossRef] [details]
Chtioui, A. & Jouini, A. (2006). Mater. Res. Bull. 41, 569-575.  [ISI] [CSD] [CrossRef] [ChemPort]
Dai, W.-M., Zhou, H. & Hu, Y.-Q. (2011). Acta Cryst. E67, o578.  [CSD] [CrossRef] [details]
Jacques, J., Collet, A. & Wilen, S. H. (1981). In Enantiomers, Racemates, and Resolutions. New York: John Wiley & Sons.
Miyata, S. (1991). In Organic Molecules for Nonlinear Optics and Photonics, edited by J. Messier, F. Kajzar & P. Prasad, P. Dordrecht: Kluwer Academic Publishers.
Ni, S.-F., Feng, W.-J., Guo, H. & Jin, Z.-M. (2007). Acta Cryst. E63, o3866.  [CSD] [CrossRef] [details]
Scheiner, S. (1997). In Molecular Interactions. Chichester: John Wiley & Sons.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Waddell, P. G., Hulse, J. O. S. & Cole, J. M. (2011). Acta Cryst. C67, o255-o258.  [CSD] [CrossRef] [details]

Acta Cryst (2012). E68, o3466  [ doi:10.1107/S1600536812047800 ]

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