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Volume 69 
Part 5 
Pages o695-o696  
May 2013  

Received 8 April 2013
Accepted 8 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.006 Å
R = 0.058
wR = 0.151
Data-to-parameter ratio = 15.2
Details
Open access

3-(Adamantan-1-yl)-4-methyl-1-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}methyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, Salman bin Abdulaziz University, Alkharj 11942, Saudi Arabia,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C25H32F3N5S, two independent molecules comprise the asymmetric unit and are related across a pseudo-centre of inversion. The piperazine rings have chair conformations with each N-bound substituent occupying an equatorial position so that the dihedral angles between the planes of the triazole and benzene ring are 78.20 (19) and 79.10 (19)° for the two independent molecules, indicating that the molecules have an L-shape. In the crystal, a three-dimensional architecture is stabilized by C-H...[pi] interactions. The crystal studied was an inversion twin with the fractional contribution of the minor component being 0.27 (9).

Related literature

For the diverse biological activities of adamantane derivatives, see: Al-Deeb et al. (2006[Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug. Res. 56, 40-47.]); Al-Omar et al. (2010[Al-Omar, M. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Molecules, 15, 2526-2550.]). For a related adamantanyl structure, see: El-Emam et al. (2012[El-Emam, A. A., Al-Omar, M. A., Al-Tamimi, A.-M. S., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1772-o1773.]).

[Scheme 1]

Experimental

Crystal data
  • C25H32F3N5S

  • Mr = 491.62

  • Orthorhombic, P n a 21

  • a = 28.8100 (15) Å

  • b = 6.6052 (4) Å

  • c = 25.7717 (14) Å

  • V = 4904.2 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 295 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.878, Tmax = 1.000

  • 19420 measured reflections

  • 9351 independent reflections

  • 6701 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.151

  • S = 1.03

  • 9351 reflections

  • 616 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3730 Friedel pairs

  • Flack parameter: 0.27 (9)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1-Cg4 are the centroids of the N1-N3,C2,C3, C19-C24, N6-N8,C27,C28 and C44-C49 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C6-H6...Cg2i 0.98 2.95 3.817 (4) 148
C13-H13B...Cg3ii 0.97 2.86 3.782 (4) 158
C31-H31...Cg4iii 0.98 2.94 3.873 (5) 159
C38-H38B...Cg1iv 0.97 2.97 3.723 (5) 135
C45-H45...Cg2v 0.93 2.97 3.708 (5) 137
Symmetry codes: (i) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (iii) [-x+1, -y, z-{\script{1\over 2}}]; (iv) [-x+1, -y+1, z-{\script{1\over 2}}]; (v) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]), QMol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5307 ).


Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug. Res. 56, 40-47.  [ChemPort]
Al-Omar, M. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Molecules, 15, 2526-2550.  [ChemPort] [PubMed]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
El-Emam, A. A., Al-Omar, M. A., Al-Tamimi, A.-M. S., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1772-o1773.  [CSD] [CrossRef] [ChemPort] [details]
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]
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o695-o696   [ doi:10.1107/S1600536813009495 ]

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