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Volume 68 
Part 11 
Page o3155  
November 2012  

Received 6 October 2012
Accepted 11 October 2012
Online 20 October 2012

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Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.091
Data-to-parameter ratio = 10.0
Details
Open access

Quinolin-3-amine

Arun M. Islor,a B. Chandrakantha,b Prakash Shetty,b Thomas Gerber,c Eric Hostenc and Richard Betzc*

aNational Institute of Technology-Karnataka, Department of Chemistry, Organic Chemistry Laboratory, Surathkal, Mangalore 575 025, India,bManipal Institute of Technology, Department of Chemistry, Manipal 576 104, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the crystal structur of the achiral title compound, C9H8N2, N-H...N hydrogen bonds connect the molecules into zigzag chains in [100]. Weak intermolecular N-H...[pi] interactions further consolidate the crystal packing.

Related literature

For novel applications of quinolin-3-amine and its derivatives, see: Rohmer et al. (2010[Rohmer, M., Meyer, B., Mank, M., Stahl, B., Bahr, U. & Karas, M. (2010). Anal. Chem. 82, 3719-3726.]); Kaneshiro et al. (2011[Kaneshiro, K., Fukuyama, Y., Iwamoto, S., Sekiya, S. & Tanaka, K. (2011). Anal. Chem. 83, 3663-3667.]). For the crystal structure of a rhodium coordination compound featuring the title compound as a ligand, see: Garralda et al. (1999[Garralda, M. A., Hernandez, R., Pinilla, E. & Rosario Torres, M. (1999). J. Organomet. Chem. 586, 150-158.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); 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

  • C9H8N2

  • Mr = 144.17

  • Orthorhombic, P 21 21 21

  • a = 7.6223 (3) Å

  • b = 7.6289 (3) Å

  • c = 12.6967 (4) Å

  • V = 738.31 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 200 K

  • 0.55 × 0.52 × 0.15 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.988

  • 6898 measured reflections

  • 1077 independent reflections

  • 1015 reflections with I > 2[sigma](I)

  • Rint = 0.013
Refinement

  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.091

  • S = 1.03

  • 1077 reflections

  • 108 parameters

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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1/C5-C9 ring.
D-H...A D-H H...A D...A D-H...A
N2-H2B...N1i 0.90 (2) 2.22 (2) 3.0761 (17) 158.2 (18)
N2-H2A...Cgii 0.85 (2) 2.60 (2) 3.3101 (15) 142.3 (19)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5347 ).

Acknowledgements

AMI is thankful to the Director of the National Institute of Technology for providing research facilities and also thanks the Board for Research in Nuclear Sciences, the Department of Atomic Energy and the Government of India for a Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Garralda, M. A., Hernandez, R., Pinilla, E. & Rosario Torres, M. (1999). J. Organomet. Chem. 586, 150-158.  [CSD] [CrossRef] [ChemPort]
Kaneshiro, K., Fukuyama, Y., Iwamoto, S., Sekiya, S. & Tanaka, K. (2011). Anal. Chem. 83, 3663-3667.  [ISI] [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Rohmer, M., Meyer, B., Mank, M., Stahl, B., Bahr, U. & Karas, M. (2010). Anal. Chem. 82, 3719-3726.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2012). E68, o3155  [ doi:10.1107/S1600536812042626 ]

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