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

Al-Tamimi, A.-M.S.; Bari, A.; Al-Omar, M.A.; Alrashood, K.A.; El-Emam, A.A.

doi:10.1107/S1600536810022695

Volume 66
Part 7
Page o1756
July 2010

Received 24 May 2010
Accepted 13 June 2010
Online 23 June 2010

Key indicators
Single-crystal X-ray study
T = 220 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.110
Data-to-parameter ratio = 19.3
Details

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

Abdul-Malek S. Al-Tamimi,^a Ahmed Bari,^a Mohamed A. Al-Omar,^a Khalid A. Alrashood ^a and Ali A. El-Emam ^a ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
Correspondence e-mail: elemam5@hotmail.com

The title compound, C₂₅H₃₅N₅OS, is a functionalized triazoline-3-thione with substituted piperazine and adamantyl substituents attached at the 2- and 5-positions, respectively, of a triazole spacer with an approximately C-shaped conformation of the molecule. The piperazine ring adopts a chair conformation.

Related literature

For the antiviral activity of adamantane derviatives, see: Vernier et al. (1969); Balzarini et al. (2007); El-Emam et al. (2004). For our study of the chemical and pharmacological properties of adamantane derivatives, see: Al-Omar et al. (2010); Al-Abdullah et al. (2007); Al-Deeb et al. (2006); El-Emam et al. (2004). For related structures, see: Hayden et al. (1981); Kadi et al. (2007); Khan et al. (2009); Smith (1969).

Experimental

Crystal data

C₂₅H₃₅N₅OS
M_r = 453.64
Monoclinic, P 2₁ /n
a = 11.0203 (2) Å
b = 12.1148 (2) Å
c = 18.7624 (4) Å
= 103.473 (1)°
V = 2436.01 (8) Å³
Z = 4
Mo K radiation
= 0.16 mm^-1
T = 220 K
0.49 × 0.45 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.657, T_max = 0.746
24895 measured reflections
5620 independent reflections
3796 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.110
S = 1.03
5620 reflections
291 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.28 e Å^-3

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2263 ).

Acknowledgements

The authors thank Dr Frank W. Heinemann, University of Erlangen-Nurnberg, Germany, for providing technical assistance.

References

Al-Abdullah, E. S., Shehata, I. A., Al-Deeb, O. A. & El-Emam, A. A. (2007). Heterocycles, 71, 379-388.
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, M. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, I. M. & El-Emam, A. A. (2010). Molecules, 15, 2526-2550.
Balzarini, J., Orzeszko, B., Mauri, J. K. & Orzeszko, A. (2007). Eur. J. Med. Chem. 42, 993-1003.
Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.
Hayden, F. G., Gwaltney, J. M. I., Van, C. R. L., Adam, K. F. & Giordani, B. (1981). Antimicrob. Agents Chemother. 19, 226-233.
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.
Khan, M.-H., Hameed, S., Tahir, M. N., Bokhari, T. H. & Khan, I. U. (2009). Acta Cryst. E65, o1437.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, D. H. (1969). Toxicol. Appl. Pharmacol. 15, 642-665.
Vernier, V. G., Harmon, J. B., Stump, J. M., Lynes, T. L., Marvel, M. P. & Smith, D. H. (1969). Toxicol. Appl. Pharmacol. 15, 642-665.

organic compounds