1-(4-Bromo­phen­yl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)meth­yl]-4-phenyl-4H-1,2,4-triazol-3-ylsulfan­yl}ethanone

Shan-Mei Xiao

doi:10.1107/S1600536809000403

. 2009 Jan 10;65(Pt 2):o273. doi: 10.1107/S1600536809000403

1-(4-Bromophenyl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-phenyl-4H-1,2,4-triazol-3-ylsulfanyl}ethanone

Shan-Mei Xiao ^a,^*

PMCID: PMC2968199 PMID: 21581887

Abstract

The title compound, C₂₂H₂₀BrN₅OS, is a potent new fungicide. The planes of the phenyl and pyrozole rings are almost perpendicular, making a dihedral angle of 86.5 (4)°. There are two non-classical intermolecular C—H⋯O and C—H⋯N hydrogen bonds in the crystal structure.

Related literature

For background to heterocyclic compounds, see: Gong et al. (2008 ▶); Liu et al. (2007 ▶). For the synthesis, see: He et al. (2008 ▶). graphic file with name e-65-0o273-scheme1.jpg

Experimental

Crystal data

C₂₂H₂₀BrN₅OS
M _r = 482.40
Triclinic,
a = 8.705 (2) Å
b = 9.173 (2) Å
c = 14.564 (4) Å
α = 94.561 (4)°
β = 97.659 (4)°
γ = 103.086 (4)°
V = 1115.3 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 294 (2) K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.592, T _max = 0.674
5704 measured reflections
3914 independent reflections
2419 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.101
S = 1.02
3914 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536809000403/bq2115sup1.cif

e-65-0o273-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000403/bq2115Isup2.hkl

e-65-0o273-Isup2.hkl^{(191.8KB, hkl)}

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
C6—H6B⋯O1ⁱ	0.97	2.45	3.365 (3)	157
C15—H15B⋯N4ⁱⁱ	0.97	2.50	3.429 (3)	161

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

supplementary crystallographic information

Comment

A variety of pyrazole and triazole heterocyclics could exhibit many activities. Meanwhile, heterocyclic compounds is an important developmental direction in medical (Gong et al., 2008) and pesticidal (Liu et al., 2007) chemistry.

In view of these facts and in continuation of our interest in the agriculture, we attempted to synthesize a series of amide derivatives, some of which have comparatively high fungicidal activity.

The molecular structure of title compound is showing in Fig.1. The x-ray analysis reveals that acetyl group is a planar with thio-ether group. The pyrozole ring is vertical with the benzene ring [dihedral angle 93.5 (4)°]. The packing of the structure is due to the weak intermolecular C-H..O and C-H..N H-bonds (Table 1. and Fig 2.).

Experimental

The compound 5-((3,5-Dimethyl-1H-pyrazol-1-yl)methyl)-4-phenyl-4H-1,2,4 -triazole-3-thiol was synthesized according to the reference (He et al., 2008). Then added p-bromo-phenacyl bromide, potassium carbonate anhydrous and N,N-Dimethyl formamide was stirred at room temperature for 5 h, giving the title compound. Colorless single crystals suitable for x-ray diffraction were obtained by recrystallization from a mixture of ethyl acetate and petroleum ether.