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Volume 69 
Part 12 
Page o1748  
December 2013  

Received 28 October 2013
Accepted 31 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.130
Data-to-parameter ratio = 13.9
Details
Open access

1-(3-Oxo-3-phenyl­prop­yl)piperidinium chloride

aDepartment of Physics, Dr M. G. R. Educational and Research Institute, Maduravoyal, Chennai, India,bDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Chemistry, BET Academy of Higher Education, Bharathi College, Bharthi Nagara, Mandya 571 422, India
Correspondence e-mail: nagendra088@yahoo.co.in

In the title salt, C14H20NO+·Cl-, the piperidine ring adopts a chair conformation. In the crystal, the cations and anions are linked by classical N-H...Cl hydrogen bond and weak C-H...Cl and C-H...O hydrogen bonds; the C-H...O hydrogen bonds exhibit R22(14) ring motifs while the C-H...Cl hydrogen bonds link the mol­ecules into chains along the a-axis direction. [pi]-[pi] stacking is observed between parallel phenyl rings of adjacent cations, the centroid-centroid distance being 3.8164 (15) Å.

Related literature

For the synthesis and biological activity of piperidine derivatives, see: Vartanyan (1984[Vartanyan, R. S. (1984). Pharm. Chem. J. 18, 736-749.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs 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 puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H20NO+·Cl-

  • Mr = 253.76

  • Monoclinic, P 21 /c

  • a = 11.2936 (13) Å

  • b = 12.0531 (15) Å

  • c = 10.9650 (13) Å

  • [beta] = 112.971 (5)°

  • V = 1374.2 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.33 mm-1

  • T = 296 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.558, Tmax = 0.614

  • 7001 measured reflections

  • 2217 independent reflections

  • 1833 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.130

  • S = 1.09

  • 2217 reflections

  • 159 parameters

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H11...Cl1i 0.95 (2) 2.15 (2) 3.0837 (18) 171 (2)
C4-H4...Cl1ii 0.93 2.82 3.745 (3) 172
C14-H14B...O1iii 0.97 2.45 3.249 (3) 139
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). 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: 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 Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5748 ).


Acknowledgements

The authors are thankful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. PN thanks the BET Academy of Higher Education for research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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 (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
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]
Vartanyan, R. S. (1984). Pharm. Chem. J. 18, 736-749.  [CrossRef]


Acta Cryst (2013). E69, o1748  [ doi:10.1107/S1600536813029887 ]

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