Methyl 3-(4-{6-methyl-4-[3-(trifluoro­meth­yl)phen­yl]pyridazin-3-yl­oxy}phen­yl)propanoate

Yu-Hong Xiao; You-Quan Zhu; Xiao-Mao Zou; Fang-Zhong Hu; Hua-Zheng Yang

doi:10.1107/S1600536808013342

. 2008 May 10;64(Pt 6):o1044. doi: 10.1107/S1600536808013342

Methyl 3-(4-{6-methyl-4-[3-(trifluoromethyl)phenyl]pyridazin-3-yloxy}phenyl)propanoate

Yu-Hong Xiao ^a, You-Quan Zhu ^a, Xiao-Mao Zou ^a,^*, Fang-Zhong Hu ^a, Hua-Zheng Yang ^a

PMCID: PMC2961364 PMID: 21202564

Abstract

In the title compound, C₂₂H₁₉F₃N₂O₃, the benzene rings of the trifluoromethylphenyl and benzoylphenyl groups form dihedral angles of 41.89 (10) and 67.44 (10)°, respectively, with the pyridazine ring. The methylpropanoate group is nearly coplanar with the attached benzene ring [dihedral angle = 3.9 (2)°]. The trifluoromethyl group is disordered over two positions; the site-occupancy factors are ca 0.64 and 0.36. In the crystal structure, inversion-related molecules are linked through C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activities of pyridazine derivatives, see: Heinisch & Kopelent (1992 ▶); Kolar & Tisler (1999 ▶).

Experimental

Crystal data

C₂₂H₁₉F₃N₂O₃
M _r = 416.39
Triclinic,
a = 9.4916 (19) Å
b = 10.232 (2) Å
c = 11.022 (2) Å
α = 81.70 (3)°
β = 65.12 (3)°
γ = 78.92 (3)°
V = 950.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 113 (2) K
0.20 × 0.16 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.977, T _max = 0.993
5529 measured reflections
3319 independent reflections
1862 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.147
S = 1.06
3319 reflections
301 parameters
72 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.39 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013342/ci2581sup1.cif

e-64-o1044-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013342/ci2581Isup2.hkl

e-64-o1044-Isup2.hkl^{(162.8KB, 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
C11—H11B⋯O2ⁱ	0.96	2.57	3.467 (4)	156
C22—H22C⋯Cg1ⁱⁱ	0.96	2.73	3.486 (4)	136

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C2–C7 ring.

Acknowledgments

This work was supported by the National Key Project for Basic Research (No. 20772067).

supplementary crystallographic information

Comment

Many pyridazine derivatives have been found to exhibit biological activities such as insecticidal, fungicidal, herbicidal, plant-growth regulatory activity, etc (Heinisch & Kopelent, 1992). For example, pyridate, credazine and maleic hydrazide (Kolar & Tisler, 1999) have been commercialized as herbicides. In order to discover new biologically active pyridazine compounds, the title compound was synthesized and its structure is reported here.

In the title molecule (Fig. 1), the C2—C7 and C13—C18 benzene rings form dihedral angles of 41.89 (10)° and 67.44 (10)°, respectively, with the central pyridazine ring (C2—C4/C12/N1/N2). The methylpropanoate group is nearly coplanar with the C13—C18 benzene ring (dihedral angle 3.9 (2)°).

The crystal packing is stabilized by C—H···O hydrogen bonds and C—H···π interactions (Table 1) involving the C2—C7 ring (centroid Cg1).

Experimental

A mixture of methyl 3-(4-hydroxyphenyl)propanoate (2.3 mmol), 3-chloro-4- (3-(trifluoromethyl)phenyl)-6-methylpyridazine (2.3 mmol) and K₂CO₃ (5 mmol) was stirred at 313 K for 2 h. The crude product was recrystallized from ethanol and single crystals of the title compound suitable for X-ray analysis were grown from ethyl acetate-petroleum ether (3:1 v/v) at room temperature.