2-[(3-Propyl­sulfanyl-5-p-tolyl-4H-1,2,4-triazol-4-yl)imino­meth­yl]phenol

Wei Wang; Qing-lei Liu; Chao Xu; Wen-peng Wu; Yan Gao

doi:10.1107/S1600536811029849

. 2011 Aug 2;67(Pt 9):o2236. doi: 10.1107/S1600536811029849

2-[(3-Propylsulfanyl-5-p-tolyl-4H-1,2,4-triazol-4-yl)iminomethyl]phenol

Wei Wang ^a,^b, Qing-lei Liu ^a, Chao Xu ^b, Wen-peng Wu ^b, Yan Gao ^b,^*

PMCID: PMC3200714 PMID: 22058906

Abstract

In the title molecule, C₁₉H₂₀N₄OS, the two benzene rings form dihedral angles of 16.2 (1) and 12.0 (1)°, respectively, with the central triazole ring. In the crystal, intermolecular O—H⋯N hydrogen bonds link molecules into chains in the [010] direction.

Related literature

For standard values of the bond lengths, see: Allen et al. (1987 ▶). For the crystal structure of a related compound, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C₁₉H₂₀N₄OS
M _r = 352.45
Monoclinic,
a = 22.682 (2) Å
b = 18.1736 (15) Å
c = 9.1557 (8) Å
β = 109.678 (7)°
V = 3553.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.962, T _max = 0.977
16201 measured reflections
3499 independent reflections
3206 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.122
S = 1.14
3499 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 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/S1600536811029849/cv5131sup1.cif

e-67-o2236-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029849/cv5131Isup2.hkl

e-67-o2236-Isup2.hkl^{(171.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029849/cv5131Isup3.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
O1—H1⋯N2ⁱ	0.95 (3)	1.71 (3)	2.658 (2)	175 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

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, (I).

In (I) (Fig.1), all the bond lengths and angles are normal (Allen et al., 1987). The C5 atom in the triazole ring deviates form the normal C_sp² hybridization state having the bond angles of 108.4 (2)° (N2—C5—N3) and 127.6 (2)° (N3—C5—C6), respectively. Rings C6—C11 and C14—C19 are inclined with repect to the 1,2,4-triazole ring at 16.2 (2)° and 12.0 (2)°, respectively. Two benzene rings form a dihedral angle of 18.0 (2)°.

In the crystal structure, intermolecular O—H···N hydrogen bonds (Table 1) link the adjacent molecules into chains in [010].

Experimental

The title compound was synthesized by the reaction of salicylic aldehyde (2.0 mmol) and 4-amino-3-propylthio-5-p-tolyl-1,2,4-triazole (2.0 mmol) by refluxing 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 89% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).