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Volume 68 
Part 12 
Page o3452  
December 2012  

Received 26 October 2012
Accepted 21 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 19.2
Details
Open access

N1-(4-Methylphenyl)piperidine-1,4-dicarboxamide

aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India,bGM Institute of Technology, Department of Physics, Davangere 577 006, India,cSiddaganga Institute of Technololgy, Department of Physics, Tumkur 572 103, India,dSree Siddaganga College for Women, Tumkur 572 103, India, and eNelson 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 title compound, C14H19N3O2, the heterocycle adopts a 1C4 conformation with the N atom being one of the flap atoms. In the crystal, classical N-H...O hydrogen bonds and C-H...O contacts connect the molecules into a three-dimensional network.

Related literature

For the pharmacological importance of piperidine and its derivatives, see: Chen et al. (2012[Chen, X., Zhan, P., Pannecouque, C., Balzarini, J., Clercq, E. D. & Liu, X. (2012). Eur. J. Med. Chem. 51, 60-66.]); Boja et al. (2011[Boja, P., Won, S., Suh, D. H., Chu, J., Park, W. K. & Lim, H. (2011). Bull. Korean Chem. Soc. 32, 1249-1252.]); Jakubowska et al. (2012[Jakubowska, A., Kulig, K., Guzior, N. & Malawska, B. (2012). Acta Pol. Pharm. Drug Res. 69, 449-455.]). For puckering analysis of six-membered rings, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Boeyens (1978[Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.]). 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
  • C14H19N3O2

  • Mr = 261.32

  • Monoclinic, P 21 /c

  • a = 5.0102 (1) Å

  • b = 28.6642 (7) Å

  • c = 10.1131 (2) Å

  • [beta] = 103.113 (1)°

  • V = 1414.50 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 200 K

  • 0.42 × 0.25 × 0.11 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.991

  • 27256 measured reflections

  • 3556 independent reflections

  • 3014 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.124

  • S = 1.06

  • 3556 reflections

  • 185 parameters

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.834 (17) 2.128 (17) 2.9481 (13) 167.9 (15)
N3-H3A...O2ii 0.886 (18) 2.071 (18) 2.9451 (14) 168.9 (15)
N3-H3B...O2iii 0.890 (17) 2.034 (17) 2.8875 (13) 160.3 (15)
C3-H3C...O1i 0.99 2.41 3.2987 (17) 149
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+1; (iii) x+1, y, z.

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: ORTEP-3 (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: BG2489 ).


Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a Young scientist award. JMR thanks the Principal of GMIT Davavangere for providing research facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.  [CrossRef]
Boja, P., Won, S., Suh, D. H., Chu, J., Park, W. K. & Lim, H. (2011). Bull. Korean Chem. Soc. 32, 1249-1252.  [ChemPort]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Chen, X., Zhan, P., Pannecouque, C., Balzarini, J., Clercq, E. D. & Liu, X. (2012). Eur. J. Med. Chem. 51, 60-66.  [ISI] [CrossRef] [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jakubowska, A., Kulig, K., Guzior, N. & Malawska, B. (2012). Acta Pol. Pharm. Drug Res. 69, 449-455.  [ChemPort]
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]
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, o3452  [ doi:10.1107/S1600536812047836 ]

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