4-Amino-1-(2-benzoyl-1-phenyl­eth­yl)-3-phenyl-1H-1,2,4-triazol-5(4H)-thione

Xiao-qiu Song; Lin Ye; He-wen Wang

doi:10.1107/S1600536810054553

. 2011 Jan 12;67(Pt 2):o347. doi: 10.1107/S1600536810054553

4-Amino-1-(2-benzoyl-1-phenylethyl)-3-phenyl-1H-1,2,4-triazol-5(4H)-thione

Xiao-qiu Song ^a, Lin Ye ^a, He-wen Wang ^b,^*

PMCID: PMC3051625 PMID: 21523028

Abstract

In the title compound, C₂₃H₂₀N₄OS, the two phenyl rings of the diphenylpropanone fragment form a dihedral angle of 86.8 (1)°, and the third phenyl ring attached to the triazole ring is twisted from the latter at 40.1 (1)°. In the crystal, molecules are paired into centrosymmetric dimers via pairs of intermolecular N—H⋯O and N—H⋯S hydrogen bonds.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C₂₃H₂₀N₄OS
M _r = 400.49
Triclinic,
a = 9.4625 (19) Å
b = 11.340 (2) Å
c = 11.655 (2) Å
α = 111.80 (3)°
β = 111.01 (3)°
γ = 98.91 (3)°
V = 1022.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.18 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 = 0.965, T _max = 0.982
9308 measured reflections
3590 independent reflections
2686 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.121
S = 1.04
3590 reflections
271 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054553/cv5022sup1.cif

e-67-0o347-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054553/cv5022Isup2.hkl

e-67-0o347-Isup2.hkl^{(176KB, hkl)}

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
N4—H4A⋯O1ⁱ	0.91 (2)	2.39 (2)	2.873 (3)	114 (2)
N4—H4B⋯S1ⁱ	0.91 (2)	2.66 (2)	3.490 (2)	151 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of structural study of 1,2,4-triazole-5(4H)-thione derivatives in our group (Wang et al., 2011), we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are found to have normal values comparable with those observed in the related 1,2,4-triazole-5(4H)-thione derivatives (Al-Tamimi et al., 2010; Fun et al., 2009; Tan et al., 2010; Wang et al., 2011). There are three phenyl rings in the molecule. Phenyl ring A (C1—C6) attached in the triazole ring makes the dihedral angles of 61.0 (1) and 70.9 (1)° with the phenyl ring B (C10—C15) and C (C18—C23), respectively. Rings B and C form a dihedral angle of 86.8 (1)°.

Intermolecular N—H···S and N—H···O hydrogen bonds (Table 1) link the adjacent molecules into centrosymmetric dimers.

Experimental

The title compound was synthesized by the reaction of the chalcone (2.0 mmol) with 4-amino-3-phenyl-4H-1,2,4-triazole-5-thiol (2.0 mmol) by refluxing in ethanol 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 87% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).