4′-Phenyl-3,4-di­hydro-2H-spiro­[naph­tha­lene-1,3′-[1,2,4]triazole]-5′-thione

Joel T Mague; Mehmet Akkurt; Shaaban K Mohamed; Alaa A Hassan; Mustafa R Albayati

doi:10.1107/S1600536814012409

. 2014 May 31;70(Pt 6):o740–o741. doi: 10.1107/S1600536814012409

4′-Phenyl-3,4-dihydro-2H-spiro[naphthalene-1,3′-[1,2,4]triazole]-5′-thione

Joel T Mague ^a, Mehmet Akkurt ^b, Shaaban K Mohamed ^c,^d, Alaa A Hassan ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4051013 PMID: 24940303

Abstract

In the title molecule, C₁₇H₁₅N₃S, the phenyl group makes a dihedral angle of 57.29 (11)° with the mean plane of the triazole ring, which in turn makes an angle of 86.83 (12)° with the plane of the aromatic portion of the tetrahydronaphthalene moiety. In the crystal, molecules are linked by weak C—H⋯S hydrogen bonds into supramolecular chains propagating along the a-axis direction. Weak C—H⋯π interactions are also observed.

Related literature

For the synthesis of different triazole thione compounds, see: Wujec et al. (2004 ▶); Zamani et al. (2004 ▶); Pitucha et al. (2007 ▶); Farghaly & El-Kashef (2006 ▶); Guelerman et al. (1998 ▶); Salgin-Gökşen et al. (2007 ▶). For the biological activity of triazole thiones, see: Amir & Kumar (2007 ▶); Gokce et al. (2001 ▶); Ezabadi et al. (2008 ▶); Mazzone et al. (1981 ▶); Küçükgüzel et al. (2008 ▶); Dogan et al. (2005 ▶); Kane et al. (1994 ▶); Kane et al. (1988 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₇H₁₅N₃S
M _r = 293.39
Orthorhombic,
a = 6.2091 (9) Å
b = 13.1804 (19) Å
c = 17.391 (3) Å
V = 1423.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 150 K
0.25 × 0.15 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.80, T _max = 0.98
25736 measured reflections
3564 independent reflections
3274 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.085
S = 1.04
3564 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack x determined using 1312 quotients [(I ⁺)−(I ⁻)]/[(I ⁺)+(I ⁻)] (Parsons et al., 2013 ▶)
Absolute structure parameter: −0.02 (3)

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814012409/xu5795sup1.cif

e-70-0o740-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012409/xu5795Isup2.hkl

e-70-0o740-Isup2.hkl^{(195.7KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814012409/xu5795Isup3.cml

CCDC reference: 1005633

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg3 is the centroid of the benzene ring of the 1,2,3,4-tetrahydronaphthalene group.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯S1ⁱ	0.95	2.86	3.568 (3)	132
C6—H6⋯Cg3ⁱⁱ	0.95	2.84	3.602 (2)	138
C16—H16⋯Cg3ⁱⁱⁱ	0.95	2.90	3.676 (3)	139

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

Acknowledgments

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

supplementary crystallographic information

1. Comment

Triazole thiones have been prepared by different methods based mostly on cyclodehydration of thiosemicarbazides with a variety of basic reagents such as sodium hydroxide (Wujec et al., 2004; Zamani et al., 2004; Pitucha et al., 2007), potassium hydroxide (Farghaly & El-Kashef, 2006), sodium carbonate (Guelerman et al., 1998) and triethylamine (Salgin-Gökşen et al., 2007). On other hand the pharmacological properties such as anti-inflammatory, analgesic (Amir & Kumar, 2007; Gokce et al., 2001), anti-bacterial, anti-fungal (Ezabadi et al., 2008; Mazzone et al., 1981), anti-tubercular, anti-viral (Küçükgüzel et al., 2008), anti-tumoral (Dogan et al., 2005), anti-convulsant (Kane et al., 1994) and anti-depressant (Kane et al., 1988) activities have been reported for mercapto-and thione-substituted 1,2,4-triazole systems. Based on above findings, we herein report the use of chloranil as a dehydrogenating agent of (1E)-3,4,4a,5,8,8a-hexahydronaphthalen-1(2H)-one N-phenylthiosemicarbazone to give the corresponding triazole thione compound.

In the title compound, the phenyl group (C3–C8) attached to N3 makes a dihedral angle of 57.29 (11)° with the mean plane of the triazole ring (N1–N3/C1/C2) which in turn makes an angle of 86.83 (12)° with the plane of the aromatic portion (C12–C17) of the tetrahydronaphthalene moiety (Fig. 1). A Cremer-Pople analysis of the conformation of the ring C2/C9–C12/C17 gave puckering parameters Q(2) = 0.356 (3) Å, Q(3) = -0.332 (3) Å and φ(2) = 275.4 (4)° (Cremer & Pople, 1975). In the solid there are no unusual intermolecular contacts. Only weak C—H···S and C—H···π interactions are observed (Table 1, Fig. 2).

2. Experimental

A mixture of 1 mmol (299 mg) of (1E)-3,4,4a,5,8,8a-hexahydronaphthalen-1(2H)-one N-phenylthiosemicarbazone and 1 mmol (246 mg) of 2,3,5,6-tetrachloro-1,4-benzoquinone in 30 ml dry ethyl acetate was stirred for 96 h at room temperature. The precipitate was filtered off, dried under vacuum and recrytallized from ethanol to give pure orange crystals.