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

Zhi-jian Wang; Wei-min Jia; Qing-lei Liu; Wei Wang

doi:10.1107/S1600536811025803

. 2011 Jul 6;67(Pt 8):o1922. doi: 10.1107/S1600536811025803

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

Zhi-jian Wang ^a,^*, Wei-min Jia ^a, Qing-lei Liu ^a, Wei Wang ^a,^b

PMCID: PMC3212312 PMID: 22090969

Abstract

In the title molecule, C₁₉H₁₉ClN₄OS, the 1,2,4-triazole ring forms dihedral angles of 86.0 (2) and 65.6 (2)° with the phenyl and chlorophenyl rings, respectively. In the crystal, intermolecular N—H⋯S and N—H⋯O hydrogen bonds link molecules into centrosymmetric dimers, which are further linked into chains in [001] via weak C—H⋯π interactions.

Related literature

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

Experimental

Crystal data

C₁₉H₁₉ClN₄OS
M _r = 386.89
Monoclinic,
a = 29.023 (10) Å
b = 7.561 (2) Å
c = 18.286 (6) Å
β = 109.606 (6)°
V = 3780 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.937, T _max = 0.962
22962 measured reflections
4441 independent reflections
3430 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.088
S = 1.02
4441 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.23 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/S1600536811025803/cv5121sup1.cif

e-67-o1922-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025803/cv5121Isup2.hkl

e-67-o1922-Isup2.hkl^{(217.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811025803/cv5121Isup3.cml

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

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

Cg is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯S1	0.892 (18)	2.763 (16)	3.2239 (16)	113.5 (12)
N4—H4A⋯S1ⁱ	0.914 (18)	2.608 (18)	3.4773 (16)	159.2 (14)
N4—H4A⋯O1ⁱ	0.914 (18)	2.602 (18)	2.9123 (16)	100.6 (14)
N4—H4B⋯O1ⁱ	0.892 (18)	2.466 (15)	2.9123 (16)	111.3 (12)
C10—H10⋯Cgⁱⁱ	0.95	2.62	3.508 (2)	156

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

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; Gao et al., 2011), we present here the crystal structure of the title compound, (I).

The bond lengths and angles in compound (I) are found to have normal values comparable with those reported 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; Gao et al., 2011). The 1,2,4-triazole ring makes the dihedral angles of 94.0 (2) and 65.6 (2)Å with the phenyl ring and the chlorophenyl ring, respectively. The phenyl ring and the chlorophenyl ring form a dihedral angle of 81.8 (2) Å.

In the crystal structure, intermolecular N—H···S and N—H···O (Table 1) hydrogen bonds link molecules into centrosymmetric dimers, which are further linked into chains in [001] via the weak C—H···π interactions (Table 1).

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-ethyl-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 colorless solid in 74% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).