3-[4-Amino-3-(4-methyl­phen­yl)-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-3-(2-chloro­phen­yl)-1-phenyl­propan-1-one

Wei Wang; Qing-lei Liu; Xiao-yu Jia; Jing-jing Zhang; Yan Gao

doi:10.1107/S1600536811023993

. 2011 Jun 25;67(Pt 7):o1793. doi: 10.1107/S1600536811023993

3-[4-Amino-3-(4-methylphenyl)-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-3-(2-chlorophenyl)-1-phenylpropan-1-one

Wei Wang ^a,^b, Qing-lei Liu ^a, Xiao-yu Jia ^b, Jing-jing Zhang ^b, Yan Gao ^b,^*

PMCID: PMC3151860 PMID: 21837166

Abstract

In the title molecule, C₂₄H₂₁ClN₄OS, the 1,2,4-triazole ring forms dihedral angles of 37.2 (2), 71.9 (2) and 84.9 (2) ° with the three benzene rings. In the crystal, weak intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers.

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

C₂₄H₂₁ClN₄OS
M _r = 448.96
Monoclinic,
a = 10.9873 (12) Å
b = 11.8220 (14) Å
c = 17.438 (3) Å
β = 94.828 (7)°
V = 2257.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 113 K
0.30 × 0.08 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.919, T _max = 0.978
22007 measured reflections
4989 independent reflections
3972 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.145
S = 1.11
4989 reflections
289 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.93 e Å⁻³
Δρ_min = −0.76 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 datablock(s) global, I. DOI: 10.1107/S1600536811023993/cv5109sup1.cif

e-67-o1793-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023993/cv5109Isup2.hkl

e-67-o1793-Isup2.hkl^{(244.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023993/cv5109Isup3.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
N4—H4B⋯S1ⁱ	0.93 (3)	2.77 (3)	3.526 (3)	139 (2)

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Symmetry code: (i) Inline graphic .

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), all bond lengths and angles are normal and comparable with those observed in related structures (Al-Tamimi et al., 2010; Fun et al., 2009; Tan et al., 2010; Wang et al., 2011). The C1 atom in the triazole ring deviates from the normal C_sp² hybridization state having the bond angles of 102.49 (19)° (N1—C1—N3) and 129.67 (18)° (N1—C1—S1). The three benzene rings in the molecule are inclined with respect to the 1,2,4-triazole ring [dihedral angles of 37.7 (2)° (C18—C23), 71.9 (2)° (C6—C11) and 84.9 (2)% (C12—C17)]. Benzene ring A (C18—C23) attached to the triazole ring makes the dihedral angles of 97.3 (2) and 84.7 (2)° with the benzene rings B (C6—C11) and C (C12—C17), respectively. Rings B and C form a dihedral angle of 60.4 (2)°.

In the crystal structure, intermolecular N—H···S hydrogen bonds (Table 1) link the adjacent molecules into centrosymmetric dimers.

Experimental

The title compound was synthesized by the reaction of the 3-(2-chlorophenyl)-1- (4-methylphenyl)-2-propen-1-one (2.0 mmol) with 4-amino-3-phenyl-4H-1,2,4- triazole-5-thiol (2.0 mmol) in ethanol. 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 colourless solid in 75% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).