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

Yan Gao; Li-hua Zhang; He-wen Wang

doi:10.1107/S1600536811023750

. 2011 Jun 25;67(Pt 7):o1794. doi: 10.1107/S1600536811023750

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

Yan Gao ^a, Li-hua Zhang ^a, He-wen Wang ^b,^*

PMCID: PMC3152103 PMID: 21837167

Abstract

In the title molecule, C₂₃H₁₉ClN₄OS, the 1,2,4-triazole ring forms dihedral angles of 46.5 (2), 87.4 (2) and 80.9 (2) Å with the three six-membered rings. Weak intermolecular N—H⋯S and C—H⋯O hydrogen bonds consolidate the crystal packing.

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

C₂₃H₁₉ClN₄OS
M _r = 434.93
Triclinic,
a = 10.559 (3) Å
b = 10.787 (4) Å
c = 10.835 (3) Å
α = 99.582 (2)°
β = 96.638 (4)°
γ = 115.267 (3)°
V = 1076.2 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 113 K
0.20 × 0.20 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.943, T _max = 0.960
13931 measured reflections
5111 independent reflections
3433 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.079
S = 0.95
5111 reflections
279 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023750/cv5107sup1.cif

e-67-o1794-sup1.cif^{(22KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023750/cv5107Isup2.hkl

e-67-o1794-Isup2.hkl^{(250.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023750/cv5107Isup3.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	0.945 (18)	2.714 (17)	3.4928 (17)	140.2 (12)
C7—H7⋯O1ⁱⁱ	0.95	2.52	3.436 (2)	161
C21—H21⋯O1ⁱⁱⁱ	0.95	2.53	3.415 (2)	156

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

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 1,2,4-triazole ring is planar with an r.m.s. deviation of 0.002 (2) Å. The C1 atom in the triazole ring deviates from the normal C_sp² hybridization state having the bond angles of 102.56 (10)° (N1—C1—N3) and 129.94 (10)° (N1—C1—S1). There are three benzene rings in the molecule. The three benzene rings are inclined with respect to the 1,2,4-triazole ring [dihedral angles of 46.5 (2)° (C18—C23), 87.4 (2)° (C6—C11) and 80.9 (2)% (C12—C17)]. Benzene ring A (C18—C23) attached to the triazole ring makes the dihedral angle of 90.6 (2) and 126.9 (2)° with the benzene rings B (C6—C11) and C (C12—C17), respectively. Ring B and ring C form a dihedral angle 93.6 (2)°.

In the crystal structure, weak intermolecular N—H···S and C—H···O hydrogen bonds (Table 1) consolidate the crystal packing.

Experimental

The title compound was synthesized by the reaction of the 3-(2-chlorophenyl)-1- phenyl-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).