[Journal logo]

Volume 70 
Part 1 
Pages o25-o26  
January 2014  

Received 28 November 2013
Accepted 3 December 2013
Online 7 December 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.115
Data-to-parameter ratio = 13.1
Details
Open access

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

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hfun.c@ksu.edu.sa

In the title compound, C26H37N5OS, the piperazine ring adopts a chair conformation. The triazole ring forms dihedral angles of 67.85 (9) and 59.41 (9)° with the piperazine and benzene rings, respectively, resulting in an approximate V-shaped conformation for the mol­ecule. An intra­molecular C-H...O hydrogen bond generates an S(6) ring motif. The crystal structure features C-H...[pi] inter­actions, producing a two-dimensional supramolecular architecture.

Related literature

For the pharmacological activity of adamantane derivatives and adamantyl-1,2,4-triazoles, see: Togo et al. (1968[Togo, Y., Hornick, R. B. & Dawkins, A. T. (1968). J. Am. Med. Assoc. 203, 1089-1094.]); El-Emam et al. (2004[El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.], 2013[El-Emam, A. A., Al-Tamimi, A.-S., Al-Omar, A. A., Alrashood, K. A. & Habib, E. E. (2013). Eur. J. Med. Chem. 68, 96-102.]); 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.]); Kadi et al. (2007[Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.], 2010[Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Eur. J. Med. Chem. 45, 5006-5011.]). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2013[Al-Abdullah, E. S., Al-Tuwaijri, H. M., El-Emam, A. A., Chidan Kumar, C. S. & Fun, H.-K. (2013). Acta Cryst. E69, o1813-o1814.]); Al-Tamimi, Alafeefy et al. (2013[Al-Tamimi, A.-M. S., Alafeefy, A. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o683.]); Al-Tamimi, Al-Abdullah et al. (2013[Al-Tamimi, A.-M. S., Al-Abdullah, E. S., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o685-o686.]); El-Emam et al. (2012[El-Emam, A. A., Alrashood, K. A., Al-Tamimi, A.-M. S., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o657-o658.]). For the synthesis of the starting material, see: El-Emam & Ibrahim (1991[El-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch. Drug Res. 41, 1260-1264.]). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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
  • C26H37N5OS

  • Mr = 467.67

  • Monoclinic, C 2/c

  • a = 19.8170 (3) Å

  • b = 11.9384 (3) Å

  • c = 21.7807 (4) Å

  • [beta] = 107.886 (2)°

  • V = 4903.90 (17) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 1.39 mm-1

  • T = 296 K

  • 0.98 × 0.62 × 0.41 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.344, Tmax = 0.599

  • 15455 measured reflections

  • 4029 independent reflections

  • 3606 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.115

  • S = 1.05

  • 4029 reflections

  • 308 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
C11-H11A...O1 0.97 2.26 2.903 (2) 123
C18-H18A...Cgi 0.97 2.81 3.748 (2) 162
Symmetry code: (i) [x-1, -y-1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: RZ5099 ).


Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. CSCK thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

Al-Abdullah, E. S., Al-Tuwaijri, H. M., El-Emam, A. A., Chidan Kumar, C. S. & Fun, H.-K. (2013). Acta Cryst. E69, o1813-o1814.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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-Tamimi, A.-M. S., Al-Abdullah, E. S., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o685-o686.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Al-Tamimi, A.-M. S., Alafeefy, A. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o683.  [CSD] [CrossRef] [IUCr Journals]
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 (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.  [CrossRef] [PubMed] [ChemPort]
El-Emam, A. A., Alrashood, K. A., Al-Tamimi, A.-M. S., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o657-o658.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
El-Emam, A. A., Al-Tamimi, A.-S., Al-Omar, A. A., Alrashood, K. A. & Habib, E. E. (2013). Eur. J. Med. Chem. 68, 96-102.  [ChemPort] [PubMed]
El-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch. Drug Res. 41, 1260-1264.  [ChemPort]
Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Eur. J. Med. Chem. 45, 5006-5011.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Togo, Y., Hornick, R. B. & Dawkins, A. T. (1968). J. Am. Med. Assoc. 203, 1089-1094.  [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o25-o26   [ doi:10.1107/S1600536813032789 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.