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

Yan Gao; Lu Wang; He-wen Wang

doi:10.1107/S1600536811020988

. 2011 Jun 11;67(Pt 7):o1609. doi: 10.1107/S1600536811020988

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

Yan Gao ^a, Lu Wang ^b, He-wen Wang ^c,^*

PMCID: PMC3151869 PMID: 21837017

Abstract

In the title molecule, C₁₆H₁₆N₄O₂S, the plane of the 1,2,4-triazole ring forms dihedral angles of 77.9 (2) and 30.0 (2)° with the planes of the furyl and phenyl rings, respectively. 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 derivates, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₆N₄O₂S
M _r = 328.39
Monoclinic,
a = 7.3702 (8) Å
b = 24.131 (2) Å
c = 9.240 (1) Å
β = 106.745 (5)°
V = 1573.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.22 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 = 0.957, T _max = 0.974
15993 measured reflections
3746 independent reflections
2835 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.119
S = 1.06
3746 reflections
217 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/S1600536811020988/cv5087sup1.cif

e-67-o1609-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020988/cv5087Isup2.hkl

e-67-o1609-Isup2.hkl^{(183.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020988/cv5087Isup3.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—H4A⋯S1ⁱ	0.95 (3)	2.64 (3)	3.475 (2)	148 (2)
C4—H4D⋯O1ⁱⁱ	0.99	2.45	3.346 (2)	151
C14—H14⋯O1ⁱⁱⁱ	0.95	2.55	3.490 (2)	169

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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), the bond lengths and angles are normal and comparable with those reported for 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). The 1,2,4-triazole ring makes the dihedral angles of 30.2 (2) and 77.9 (2)° with the phenyl ring and the furanyl ring, respectively. The phenyl and furanyl rings form a dihedral angle of 71.1 (2) °.

Intermolecular N—H···S hydrogen bond (Table 1) links the adjacent molecule into centrosymmetric dimers, which are further linked by the weak C—H···O interactions (Table 1) into three-dimensional structure.

Experimental

The title compound was synthesized by the reaction of the 3-(furan-2-yl)-1- phenyl-2-propen-1-one (2.0 mmol) with 4-amino-3-methyl-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 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).