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

Islor, A.M.; Jagadeesh, M.R.; Suresh Kumar, H.M.; Ananda Kumari, R.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812047836

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 (C-C) = 0.002 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 19.2
Details

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

Arun M. Islor,^a M. R. Jagadeesh,^b H. M. Suresh Kumar,^c R. Ananda Kumari,^d Thomas Gerber,^e Eric Hosten ^e and Richard Betz ^e ^*

^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-HO hydrogen bonds and C-HO 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); Boja et al. (2011); Jakubowska et al. (2012). For puckering analysis of six-membered rings, see: Cremer & Pople (1975); Boeyens (1978). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₉N₃O₂
M_r = 261.32
Monoclinic, P 2₁ /c
a = 5.0102 (1) Å
b = 28.6642 (7) Å
c = 10.1131 (2) Å
= 103.113 (1)°
V = 1414.50 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.966, T_max = 0.991
27256 measured reflections
3556 independent reflections
3014 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(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
_max = 0.31 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.834 (17)	2.128 (17)	2.9481 (13)	167.9 (15)
N3-H3AO2ⁱⁱ	0.886 (18)	2.071 (18)	2.9451 (14)	168.9 (15)
N3-H3BO2ⁱⁱⁱ	0.890 (17)	2.034 (17)	2.8875 (13)	160.3 (15)
C3-H3CO1ⁱ	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.
Boja, P., Won, S., Suh, D. H., Chu, J., Park, W. K. & Lim, H. (2011). Bull. Korean Chem. Soc. 32, 1249-1252.
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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Jakubowska, A., Kulig, K., Guzior, N. & Malawska, B. (2012). Acta Pol. Pharm. Drug Res. 69, 449-455.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.