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Volume 69 
Part 12 
Page o1807  
December 2013  

Received 9 October 2013
Accepted 10 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.060
wR = 0.148
Data-to-parameter ratio = 17.0
Details
Open access

2-Amino-6-(piperidin-1-yl)-4-p-tolyl­pyridine-3,5-dicarbo­nitrile

aSri Ram Engineering College, Chennai 602 024, India,bDepartment of Chemistry, Pondichery University, Pondichery 605 014, India, and cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C19H19N5, the piperidine ring adopts a chair conformation. The pyridine ring is essentially planar, with a maximum deviation of 0.039 (2) Å for a C atom substituted with a carbonitrile group. The mean plane of the central pyridine ring makes the dihedral angles of 37.90 (14) and 56.10 (12)° with the piperidine and benzene rings, respectively. In the crystal, mol­ecules are linked via N-H...N and C-H...N hydrogen bonds, forming chains along [101], and enclosing R22(17) ring motifs. The chains are linked by further C-H...N hydrogen bonds, forming two-dimensional networks lying parallel to (10-1), and enclosing inversion dimers with R22(20) ring motifs.

Related literature

For background to pyridine derivatives and their biological activity, see: Chaubey & Pandeya (2011[Chaubey, A. & Pandeya, S. N. (2011). Asian J. Pharm. Clin. Res. 4, 5-8.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For 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.]). For a related structure, see: Inglebert et al. (2011[Inglebert, S. A., Kamalraja, J., Vasuki, G. & Sethusankar, K. (2011). Acta Cryst. E67, o1972.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19N5

  • Mr = 317.39

  • Monoclinic, P 21 /n

  • a = 14.8695 (12) Å

  • b = 7.7350 (6) Å

  • c = 15.2791 (13) Å

  • [beta] = 107.196 (8)°

  • V = 1678.8 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.37 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.981

  • 7726 measured reflections

  • 3705 independent reflections

  • 1346 reflections with I > 2[sigma](I)

  • Rint = 0.056

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.148

  • S = 0.77

  • 3705 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5-H5C...N3i 0.86 2.18 2.999 (4) 160
C2-H2B...N4ii 0.97 2.62 3.509 (4) 153
C19-H19A...N4iii 0.96 2.61 3.509 (4) 156
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) -x, -y+2, -z; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: RK2416 ).


Acknowledgements

The authors gratefully acknowledge Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chaubey, A. & Pandeya, S. N. (2011). Asian J. Pharm. Clin. Res. 4, 5-8.  [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Inglebert, S. A., Kamalraja, J., Vasuki, G. & Sethusankar, K. (2011). Acta Cryst. E67, o1972.  [CSD] [CrossRef] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1807  [ doi:10.1107/S1600536813030845 ]

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