3-(Adamantan-1-yl)-1-[(4-benzyl­piperazin-1-yl)meth­yl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione

Ebtehal S Al-Abdullah; Hanadi H Asiri; Ali El-Emam; Seik Weng Ng

doi:10.1107/S160053681105570X

. 2012 Jan 11;68(Pt 2):o344. doi: 10.1107/S160053681105570X

3-(Adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione

Ebtehal S Al-Abdullah ^a, Hanadi H Asiri ^a, Ali El-Emam ^a, Seik Weng Ng ^b,^c,^*

PMCID: PMC3275028 PMID: 22346973

Abstract

The title molecule, C₃₀H₃₇N₅S, displays a chair-shaped piperazine ring, as well as an approximately planar triazole ring [maximum deviation = 0.002 (2) Å] whose phenyl substituent is nearly perpendicular to the mean plane of the five-membered ring [dihedral angle = 80.4 (1)°]. The substituents on the piperazine ring occupy equatorial sites. Weak intermolecular C—H⋯S hydrogen bonding is present in the crystal structure.

Related literature

For background to 3-(1-adamantyl)-4-substituted-5-mercapto-1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991 ▶).

Experimental

Crystal data

C₃₀H₃₇N₅S
M _r = 499.71
Triclinic,
a = 10.1677 (6) Å
b = 11.3287 (7) Å
c = 12.5331 (7) Å
α = 67.037 (6)°
β = 85.768 (5)°
γ = 83.547 (5)°
V = 1320.12 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 100 K
0.15 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.978, T _max = 0.993
9288 measured reflections
6033 independent reflections
4002 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.151
S = 1.01
6033 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105570X/xu5419sup1.cif

e-68-0o344-sup1.cif^{(25.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105570X/xu5419Isup2.hkl

e-68-0o344-Isup2.hkl^{(295.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681105570X/xu5419Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯S1ⁱ	1.00	2.85	3.751 (3)	150
C28—H28⋯S1ⁱⁱ	0.95	2.84	3.673 (4)	146

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We reported the synthesis, anti-inflammatory and analgesic properties of 3-(1-adamantyl)-4-substituted-5-mercapto-1,2,4-triazole derivatives (El-Emam & Ibrahim, 1991). The triazole ring, which possesses a secondary nitrogen site next to a double-bond sulfur, is capable of undergoing a Mannich reaction with an N-substituted piperazine derivative to yield a new class of chemotherapeutic compounds. The C₃₀H₃₇N₅S molecule (Scheme I, Fig. 1) displays a chair-shaped piperazine ring, as well as a planar triazole ring whose phenyl substituent is nearly perpendicular to the mean plane of the five-membered ring (dihedral angle 80.4 (1)°).

Experimental

5-(1-Adamantyl)-4-phenyl-1,2,4-triazole-3-thiol was synthesized according to a reported procedure (El-Emam & Ibrahim, 1991). The compound (2 mmol), 1-benzylpiperazine (2 mmol) and a 37% formaldehyde solution (0.5 ml) in ethanol (8 ml), was heated for 15 minutes. Stirring was continued for 12 h at room temperature. The product was filtered, washed with water, dried, and recrystallized from ethanol to yield (80%) of the title compound as colorless crystals, m.p. 470–472 K.