1-(2-Benzoyl-1-phenyl­eth­yl)-4-[(2-hy­droxy-1-naphth­yl)methyl­idene­amino]-3-phenyl-1H-1,2,4-triazole-5(4H)-thione

Wei Wang; Hong-guo Yao; Yan Gao; Jing-jing Zhang; Xiao-yu Jia

doi:10.1107/S1600536811005721

. 2011 Feb 19;67(Pt 3):o675. doi: 10.1107/S1600536811005721

1-(2-Benzoyl-1-phenylethyl)-4-[(2-hydroxy-1-naphthyl)methylideneamino]-3-phenyl-1H-1,2,4-triazole-5(4H)-thione

Wei Wang ^a,^b,^*, Hong-guo Yao ^b, Yan Gao ^b, Jing-jing Zhang ^b, Xiao-yu Jia ^b

PMCID: PMC3051956 PMID: 21522423

Abstract

In the title molecule, C₃₄H₂₆N₄O₂S, the hydroxy group is involved in an intramolecular O—H⋯N hydrogen bond. The naphthyl ring system and the central triazole ring form a dihedral angle of 37.8 (1)°. The crystal packing exhibits weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the pharmacological properties and applications of Mannich bases, see: Joshi et al. (2004 ▶); Holla et al. (2003 ▶); Negm et al. (2005 ▶). For a related structure, see: Wang et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₃₄H₂₆N₄O₂S
M _r = 554.65
Monoclinic,
a = 13.142 (3) Å
b = 21.563 (4) Å
c = 10.097 (2) Å
β = 99.22 (3)°
V = 2824.4 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.970, T _max = 0.985
23204 measured reflections
4960 independent reflections
4082 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.142
S = 1.11
4960 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005721/cv5051sup1.cif

e-67-0o675-sup1.cif^{(26.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005721/cv5051Isup2.hkl

e-67-0o675-Isup2.hkl^{(243KB, hkl)}

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

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

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N4	0.84	1.85	2.582 (2)	145
C32—H32⋯O1ⁱ	0.95	2.53	3.196 (2)	127
C14—H14⋯Cg1ⁱⁱ	0.95	2.60	3.465 (2)	151

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

Acknowledgments

We gratefully acknowledge support from the Key Laboratory Project of Liaoning Province (grant No. 2008S127) and the Doctoral Starting Foundation of Liaoning Province (grant No. 20071103).

supplementary crystallographic information

Comment

We are paying attention to the synthesis and applications of Mannich base due to their comprehensive biological activities (Joshi et al., 2004; Holla et al., 2003; Negm et al., 2005). Recently, we have reported a crystal structure of Mannich base modified by the triazole thione (Wang et al., 2011). Herewith we present the crystal structure of the title compound (I), which is a new Mannich base.

In (I) (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987). An intramolecular O—H···N hydrogen bond (Table 1) results in the formation of a planar (r.m.s. deviation = 0.0094 (2) Å) six-membered ring. This six-membered ring forms a dihedral angle of 36.3 (3)° with the triazole ring. The naphthyl system and central triazole ring form a dihedral angle of 37.8 (1)°.

The weak intermolecular C—H···O and C—H···π interactions (Table 1) contribute to the crystal packing stabilisation.

Experimental

The title compound was synthesized by the reaction of the chalcone (2.0 mmol) with its corresponding Schiff base, which was inturn obtained by refluxing 4-amino-1-methyl-4H-1,2,4-triazole-5-thiol (2.0 mmol), 2-hydroxynaphthalene-1 -carbaldehyde (2.0 mmol) in ethanol. A mixture of Schiff base and chalcone in ethanol was stirring for 24 h.The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as colorless solid in 84% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).