3-{4-[(2-Hy­droxy­benzyl­idene)amino]-3-methyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenyl­propan-1-one

Wei Wang; Yan Gao; Jing-jing Zhang; Xiao-yu Jia; Wen-peng Wu

doi:10.1107/S1600536811034878

. 2011 Aug 31;67(Pt 9):o2533. doi: 10.1107/S1600536811034878

3-{4-[(2-Hydroxybenzylidene)amino]-3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenylpropan-1-one

Wei Wang ^a,^b,^*, Yan Gao ^b, Jing-jing Zhang ^b, Xiao-yu Jia ^b, Wen-peng Wu ^b

PMCID: PMC3200874 PMID: 22059065

Abstract

There are two crystallographically independent molecules (A and B) in the asymmetric unit of the title compound, C₂₅H₂₂N₄O₂S, with almost identical molecular conformations. The hydroxyphenyl ring plane and the 1,2,4-triazole ring form dihedral angles of 17.1 (2) and 7.4 (2)° in A and B, respectively. The dihedral angles between 1,2,4-triazole ring and the other two phenyl rings are 89.6 (3) and 83.3 (2)° in molecule A, and 89.2 (3) and 82.2 (2)° in molecule B. One intramolecular O—H⋯N hydrogen bond is present in each molecule. Weak intermolecular 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 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C₂₅H₂₂N₄O₂S
M _r = 442.53
Triclinic,
a = 12.1053 (12) Å
b = 12.4682 (12) Å
c = 15.5480 (16) Å
α = 95.056 (11)°
β = 103.342 (12)°
γ = 100.212 (15)°
V = 2226.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.18 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 = 0.966, T _max = 0.979
27078 measured reflections
9643 independent reflections
6461 reflections with I > 2σ(I)
R _int = 0.073

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.145
S = 1.00
9643 reflections
585 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.33 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/S1600536811034878/bh2375sup1.cif

e-67-o2533-sup1.cif^{(33.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034878/bh2375Isup2.hkl

e-67-o2533-Isup2.hkl^{(471.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034878/bh2375Isup3.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
O2—H2⋯N4	0.85 (3)	1.92 (3)	2.653 (3)	144 (3)
O4—H4⋯N8	0.95 (3)	1.80 (3)	2.658 (3)	149 (3)
C29—H29B⋯O1ⁱ	0.99	2.52	3.331 (3)	139 (2)
C38—H38⋯O1ⁱ	0.95	2.56	3.440 (3)	154 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of structural study of Mannich bases derivatives synthesized by reactions of the amino heterocycles and aromatic aldehydes in our group (Wang et al., 2011), we present here the crystal structure of the title compound.

There are two independent molecules (A and B) in the asymmetric unit (Fig. 1). The two molecules have slightly different bond lengths and the bond lengths and angles in the compound are found to have normal values, compared to 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). The two independent molecular conformations are similar, the hydroxyphenyl ring plane and 1,2,4-triazole ring forming dihedral angles of 17.1 (2) and 7.4 (2)°, in A and B, respectively. The dihedral angles between 1,2,4-triazole ring and the other two phenyl rings are 89.6 (3) and 83.3 (2)°, respectively in molecule A, and 89.2 (3) and 82.2 (2)° in molecule B. Two C atoms in the 1,2,4-triazole ring show distorted Csp² hybridization states with the bond angles of 101.2 (2)° (N1—C1—N3), 130.68 (19)° (N3—C1—S1), 110.8 (2)° (N2—C2—N3) and 125.7 (2)° (N2—C2—C25) in molecule A [the corresponding values are 101.8 (2), 131.0 (2), 111.2 (2) and 125.1 (2)° in molecule B], which are similar to the reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011).

An intramolecular O—H···N hydrogen bond is present in each molecule. The crystal structure is consolidated by weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

The title compound was synthesized by the reaction of 2-hydroxybenzaldehyde (2.0 mmol) and 3-(4-amino-3-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one (2.0 mmol) in refluxing 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 a colorless solid in 73% yield. Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).