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Volume 69 
Part 6 
Page o845  
June 2013  

Received 22 April 2013
Accepted 2 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.040
wR = 0.098
Data-to-parameter ratio = 14.4
Details
Open access

3,5-Dimethyl-1-{2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetyl}-2,6-diphenylpiperidin-4-one

aResearch Development Centre, Orchid Chemicals and Pharmaceuticals Ltd, Sozhinganallur, Chennai 600 119, India,bDepartment of Chemistry, Presidency College (Autonomous), Chennai 600 005, India, and cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C24H25N3O2S2, the piperidine ring adopts a distorted boat conformation. The phenyl rings subtend angles of 75.6 (1)° and 86.3 (1)° with the mean plane of the piperidine ring. In the crystal, molecules are linked through a network C-H...N hydrogen bonds, forming zigzag chains along [100]. The thiadiazol ring methyl group is disordered over two positions with an occupancy ratio of 0.69 (4):0.31 (4).

Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009[Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S. & Jeong, Y. T. (2009). Eur. J. Med. Chem. 44, 577-592.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) and for asymmetry parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C24H25N3O2S2

  • Mr = 451.59

  • Orthorhombic, P 21 21 21

  • a = 9.1342 (6) Å

  • b = 9.2874 (6) Å

  • c = 27.0454 (14) Å

  • V = 2294.3 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.927, Tmax = 0.938

  • 10655 measured reflections

  • 4215 independent reflections

  • 3623 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.098

  • S = 1.06

  • 4215 reflections

  • 293 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1461 Friedel pairs

  • Flack parameter: 0.26 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...N3i 0.98 2.48 3.460 (4) 175
C22-H22B...N2i 0.97 2.47 3.403 (4) 161
C22-H22B...N3i 0.97 2.57 3.505 (4) 161
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. 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.]); 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: NG5326 ).


Acknowledgements

SG thanks Orchid Chemicals and Pharmaceuticals Ltd (www.orchidpharma.com), Chennai, India, for consent to perform this research and PS is thankful to the UGC, New Delhi, for financial support in the form of a Research Fellowship in Science for Meritorious Students.

References

Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S. & Jeong, Y. T. (2009). Eur. J. Med. Chem. 44, 577-592.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o845  [ doi:10.1107/S1600536813012014 ]

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