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

Xiao, Y.-H.; Zhu, Y.-Q.; Zou, X.-M.; Hu, F.-Z.; Yang, H.-Z.

doi:10.1107/S1600536808013342

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1044

doi:10.1107/S1600536808013342

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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 and Hua-Zheng Yang ^a

^aState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: zyq8165@nankai.edu.cn

(Received 14 April 2008; accepted 6 May 2008; online 10 May 2008)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.055
wR(F²) = 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

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
Symmetry codes: (i) -x, -y, -z+1; (ii) -x, -y+1, -z+1. Cg1 is the centroid of the C2–C7 ring.

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

For the biological activities of pyridazine derivatives, see: Heinisch & Kopelent (1992); Kolar & Tisler (1999). Cg1 is the centroid of the C2–C7 ring.

Experimental top

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.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Only one disorder component is shown.

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

Crystal data top

C₂₂H₁₉F₃N₂O₃	Z = 2
M_r = 416.39	F(000) = 432
Triclinic, P1	D_x = 1.455 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4916 (19) Å	Cell parameters from 2351 reflections
b = 10.232 (2) Å	θ = 2.0–27.9°
c = 11.022 (2) Å	µ = 0.12 mm⁻¹
α = 81.70 (3)°	T = 113 K
β = 65.12 (3)°	Plate, colourless
γ = 78.92 (3)°	0.20 × 0.16 × 0.06 mm
V = 950.6 (4) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3319 independent reflections
Radiation source: rotating anode	1862 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.054
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ω and ϕ scans	h = −10→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→11
T_min = 0.977, T_max = 0.993	l = −13→11
5529 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0675P)²] where P = (F_o² + 2F_c²)/3
3319 reflections	(Δ/σ)_max = 0.003
301 parameters	Δρ_max = 0.40 e Å⁻³
72 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₂H₁₉F₃N₂O₃	γ = 78.92 (3)°
M_r = 416.39	V = 950.6 (4) Å³
Triclinic, P1	Z = 2
a = 9.4916 (19) Å	Mo Kα radiation
b = 10.232 (2) Å	µ = 0.12 mm⁻¹
c = 11.022 (2) Å	T = 113 K
α = 81.70 (3)°	0.20 × 0.16 × 0.06 mm
β = 65.12 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3319 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1862 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.993	R_int = 0.054
5529 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	72 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
3319 reflections	Δρ_min = −0.39 e Å⁻³
301 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
F1	1.0340 (5)	0.3434 (7)	0.0132 (7)	0.0359 (15)	0.636 (12)
F2	0.8747 (11)	0.3445 (7)	−0.0736 (7)	0.072 (2)	0.636 (12)
F3	0.7991 (6)	0.4176 (6)	0.1223 (8)	0.079 (3)	0.636 (12)
F1'	1.0297 (11)	0.3418 (14)	−0.0418 (14)	0.071 (4)	0.364 (12)
F2'	0.7900 (12)	0.3936 (8)	−0.0042 (15)	0.055 (3)	0.364 (12)
F3'	0.8553 (19)	0.4059 (12)	0.1421 (11)	0.076 (4)	0.364 (12)
O1	0.39298 (18)	0.1498 (2)	0.2418 (2)	0.0286 (6)
O2	−0.5057 (2)	0.5985 (2)	0.6250 (2)	0.0409 (7)
O3	−0.4466 (2)	0.7531 (2)	0.4543 (2)	0.0330 (6)
N1	0.3114 (2)	−0.1545 (3)	0.1899 (3)	0.0246 (7)
N2	0.2934 (2)	−0.0267 (3)	0.2179 (3)	0.0251 (7)
C1	0.8892 (3)	0.3235 (3)	0.0444 (3)	0.0327 (9)
C2	0.8618 (3)	0.1868 (3)	0.1025 (3)	0.0228 (8)
C3	0.9650 (3)	0.1072 (3)	0.1502 (3)	0.0258 (8)
H3	1.0518	0.1399	0.1464	0.031*
C4	0.9393 (3)	−0.0202 (3)	0.2033 (3)	0.0266 (8)
H4	1.0083	−0.0738	0.2361	0.032*
C5	0.8108 (3)	−0.0688 (3)	0.2079 (3)	0.0241 (8)
H5	0.7947	−0.1555	0.2430	0.029*
C6	0.7056 (2)	0.0103 (3)	0.1608 (3)	0.0194 (7)
C7	0.7313 (3)	0.1389 (3)	0.1080 (3)	0.0205 (7)
H7	0.6616	0.1931	0.0763	0.025*
C8	0.5697 (3)	−0.0462 (3)	0.1662 (3)	0.0191 (7)
C9	0.5840 (3)	−0.1748 (3)	0.1379 (3)	0.0227 (7)
H9	0.6818	−0.2278	0.1092	0.027*
C10	0.4511 (3)	−0.2271 (3)	0.1519 (3)	0.0216 (7)
C11	0.4609 (3)	−0.3680 (3)	0.1257 (3)	0.0319 (9)
H11A	0.3575	−0.3868	0.1466	0.048*
H11B	0.5055	−0.4269	0.1806	0.048*
H11C	0.5259	−0.3811	0.0329	0.048*
C12	0.4159 (3)	0.0228 (3)	0.2087 (3)	0.0202 (7)
C13	0.2387 (3)	0.2146 (3)	0.3058 (3)	0.0260 (8)
C14	0.1408 (3)	0.1712 (3)	0.4317 (3)	0.0353 (10)
H14	0.1721	0.0931	0.4743	0.042*
C15	−0.0044 (3)	0.2448 (3)	0.4941 (3)	0.0340 (9)
H15	−0.0710	0.2150	0.5792	0.041*
C16	−0.0543 (3)	0.3619 (3)	0.4340 (3)	0.0215 (7)
C17	0.0473 (3)	0.4015 (3)	0.3070 (3)	0.0311 (9)
H17	0.0168	0.4794	0.2636	0.037*
C18	0.1928 (3)	0.3285 (3)	0.2428 (3)	0.0324 (9)
H18	0.2593	0.3568	0.1570	0.039*
C19	−0.2110 (3)	0.4412 (3)	0.5096 (3)	0.0250 (8)
H19A	−0.2905	0.3833	0.5370	0.030*
H19B	−0.2102	0.4673	0.5905	0.030*
C20	−0.2594 (3)	0.5645 (3)	0.4362 (3)	0.0287 (8)
H20A	−0.1815	0.6240	0.4094	0.034*
H20B	−0.2615	0.5396	0.3554	0.034*
C21	−0.4164 (3)	0.6373 (3)	0.5179 (3)	0.0246 (8)
C22	−0.5929 (3)	0.8355 (3)	0.5257 (4)	0.0392 (9)
H22A	−0.6786	0.7956	0.5298	0.059*
H22B	−0.5942	0.9226	0.4798	0.059*
H22C	−0.6034	0.8431	0.6150	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0233 (17)	0.036 (2)	0.049 (3)	−0.0158 (15)	−0.0157 (19)	0.011 (3)
F2	0.123 (5)	0.063 (4)	0.071 (4)	−0.058 (3)	−0.075 (4)	0.042 (3)
F3	0.041 (3)	0.028 (3)	0.102 (5)	0.003 (2)	0.027 (3)	0.006 (3)
F1'	0.052 (4)	0.035 (4)	0.069 (7)	−0.004 (3)	0.025 (4)	0.012 (5)
F2'	0.057 (4)	0.035 (4)	0.093 (7)	−0.009 (3)	−0.056 (4)	0.019 (4)
F3'	0.129 (8)	0.040 (5)	0.051 (5)	−0.008 (6)	−0.026 (6)	−0.014 (4)
O1	0.0136 (9)	0.0279 (13)	0.0422 (15)	0.0010 (8)	−0.0076 (9)	−0.0135 (11)
O2	0.0284 (11)	0.0378 (15)	0.0377 (16)	0.0032 (10)	−0.0012 (10)	0.0053 (12)
O3	0.0283 (10)	0.0297 (13)	0.0279 (14)	0.0109 (9)	−0.0045 (9)	−0.0039 (11)
N1	0.0212 (11)	0.0294 (15)	0.0253 (16)	−0.0046 (11)	−0.0108 (10)	−0.0031 (12)
N2	0.0198 (11)	0.0284 (16)	0.0286 (16)	−0.0037 (10)	−0.0104 (11)	−0.0046 (12)
C1	0.0232 (15)	0.038 (2)	0.037 (2)	−0.0089 (15)	−0.0131 (15)	0.0076 (19)
C2	0.0160 (12)	0.0280 (18)	0.0207 (18)	−0.0029 (11)	−0.0039 (11)	−0.0019 (14)
C3	0.0154 (12)	0.0360 (19)	0.0261 (19)	−0.0052 (12)	−0.0083 (12)	−0.0008 (15)
C4	0.0179 (13)	0.0323 (19)	0.030 (2)	−0.0012 (12)	−0.0133 (12)	0.0042 (15)
C5	0.0179 (12)	0.0241 (17)	0.0269 (19)	−0.0018 (11)	−0.0070 (12)	0.0003 (14)
C6	0.0124 (12)	0.0271 (17)	0.0154 (16)	−0.0008 (11)	−0.0022 (11)	−0.0053 (13)
C7	0.0146 (12)	0.0280 (18)	0.0161 (17)	0.0013 (11)	−0.0050 (11)	−0.0031 (13)
C8	0.0159 (12)	0.0283 (18)	0.0124 (17)	−0.0022 (12)	−0.0054 (11)	−0.0016 (14)
C9	0.0180 (12)	0.0278 (18)	0.0191 (18)	0.0007 (12)	−0.0059 (12)	−0.0024 (14)
C10	0.0226 (13)	0.0246 (17)	0.0169 (17)	−0.0042 (12)	−0.0069 (12)	−0.0013 (13)
C11	0.0278 (14)	0.0296 (19)	0.035 (2)	−0.0048 (13)	−0.0091 (14)	−0.0047 (16)
C12	0.0156 (12)	0.0246 (17)	0.0194 (18)	0.0002 (12)	−0.0059 (11)	−0.0059 (14)
C13	0.0140 (12)	0.0303 (18)	0.034 (2)	−0.0019 (12)	−0.0080 (12)	−0.0097 (15)
C14	0.0269 (15)	0.040 (2)	0.033 (2)	0.0083 (14)	−0.0122 (14)	0.0010 (17)
C15	0.0232 (14)	0.041 (2)	0.026 (2)	0.0040 (13)	−0.0049 (13)	0.0035 (16)
C16	0.0151 (12)	0.0253 (17)	0.0235 (18)	−0.0003 (11)	−0.0064 (12)	−0.0079 (14)
C17	0.0251 (14)	0.0235 (18)	0.031 (2)	0.0039 (13)	−0.0021 (13)	0.0000 (15)
C18	0.0244 (14)	0.0294 (19)	0.031 (2)	−0.0042 (13)	0.0008 (13)	0.0002 (16)
C19	0.0210 (13)	0.0270 (18)	0.0226 (18)	0.0019 (12)	−0.0057 (12)	−0.0051 (14)
C20	0.0255 (14)	0.0269 (18)	0.029 (2)	−0.0005 (12)	−0.0073 (13)	−0.0027 (15)
C21	0.0216 (13)	0.0245 (18)	0.027 (2)	−0.0018 (12)	−0.0091 (13)	−0.0046 (15)
C22	0.0351 (16)	0.035 (2)	0.039 (2)	0.0139 (14)	−0.0126 (15)	−0.0098 (17)

Geometric parameters (Å, º) top

F1—C1	1.319 (5)	C8—C12	1.405 (3)
F2—C1	1.347 (5)	C9—C10	1.405 (4)
F3—C1	1.304 (7)	C9—H9	0.93
F1'—C1	1.302 (8)	C10—C11	1.489 (4)
F2'—C1	1.320 (6)	C11—H11A	0.96
F3'—C1	1.357 (9)	C11—H11B	0.96
O1—C12	1.353 (4)	C11—H11C	0.96
O1—C13	1.405 (3)	C13—C18	1.363 (4)
O2—C21	1.192 (3)	C13—C14	1.372 (4)
O3—C21	1.333 (3)	C14—C15	1.375 (4)
O3—C22	1.442 (3)	C14—H14	0.93
N1—C10	1.316 (3)	C15—C16	1.384 (4)
N1—N2	1.348 (4)	C15—H15	0.93
N2—C12	1.317 (3)	C16—C17	1.380 (4)
C1—C2	1.475 (4)	C16—C19	1.502 (4)
C2—C3	1.379 (3)	C17—C18	1.379 (4)
C2—C7	1.393 (4)	C17—H17	0.93
C3—C4	1.372 (4)	C18—H18	0.93
C3—H3	0.93	C19—C20	1.501 (4)
C4—C5	1.382 (4)	C19—H19A	0.97
C4—H4	0.93	C19—H19B	0.97
C5—C6	1.388 (3)	C20—C21	1.491 (4)
C5—H5	0.93	C20—H20A	0.97
C6—C7	1.382 (4)	C20—H20B	0.97
C6—C8	1.488 (4)	C22—H22A	0.96
C7—H7	0.93	C22—H22B	0.96
C8—C9	1.364 (4)	C22—H22C	0.96

C12—O1—C13	119.0 (2)	C10—C11—H11A	109.5
C21—O3—C22	116.2 (2)	C10—C11—H11B	109.5
C10—N1—N2	119.7 (2)	H11A—C11—H11B	109.5
C12—N2—N1	119.3 (2)	C10—C11—H11C	109.5
F1'—C1—F3	119.9 (8)	H11A—C11—H11C	109.5
F3—C1—F1	105.4 (5)	H11B—C11—H11C	109.5
F1'—C1—F2'	106.9 (7)	N2—C12—O1	117.9 (2)
F3—C1—F2'	69.2 (6)	N2—C12—C8	124.8 (3)
F1—C1—F2'	126.6 (5)	O1—C12—C8	117.2 (2)
F1'—C1—F2	76.7 (7)	C18—C13—C14	120.7 (3)
F3—C1—F2	109.6 (4)	C18—C13—O1	117.6 (2)
F1—C1—F2	103.9 (4)	C14—C13—O1	121.6 (2)
F1'—C1—F3'	104.6 (9)	C13—C14—C15	119.1 (3)
F1—C1—F3'	82.7 (7)	C13—C14—H14	120.5
F2'—C1—F3'	95.6 (7)	C15—C14—H14	120.5
F2—C1—F3'	132.0 (6)	C14—C15—C16	122.0 (3)
F1'—C1—C2	118.4 (6)	C14—C15—H15	119.0
F3—C1—C2	114.6 (4)	C16—C15—H15	119.0
F1—C1—C2	112.6 (4)	C17—C16—C15	117.1 (3)
F2'—C1—C2	117.7 (4)	C17—C16—C19	123.3 (2)
F2—C1—C2	110.1 (4)	C15—C16—C19	119.5 (2)
F3'—C1—C2	110.7 (6)	C18—C17—C16	121.6 (3)
C3—C2—C7	120.5 (3)	C18—C17—H17	119.2
C3—C2—C1	120.2 (2)	C16—C17—H17	119.2
C7—C2—C1	119.4 (2)	C13—C18—C17	119.6 (3)
C4—C3—C2	119.8 (2)	C13—C18—H18	120.2
C4—C3—H3	120.1	C17—C18—H18	120.2
C2—C3—H3	120.1	C20—C19—C16	116.4 (2)
C3—C4—C5	120.0 (2)	C20—C19—H19A	108.2
C3—C4—H4	120.0	C16—C19—H19A	108.2
C5—C4—H4	120.0	C20—C19—H19B	108.2
C4—C5—C6	120.8 (3)	C16—C19—H19B	108.2
C4—C5—H5	119.6	H19A—C19—H19B	107.3
C6—C5—H5	119.6	C21—C20—C19	113.1 (2)
C7—C6—C5	119.1 (2)	C21—C20—H20A	109.0
C7—C6—C8	121.7 (2)	C19—C20—H20A	109.0
C5—C6—C8	119.2 (2)	C21—C20—H20B	109.0
C6—C7—C2	119.8 (2)	C19—C20—H20B	109.0
C6—C7—H7	120.1	H20A—C20—H20B	107.8
C2—C7—H7	120.1	O2—C21—O3	123.5 (3)
C9—C8—C12	114.3 (2)	O2—C21—C20	125.7 (2)
C9—C8—C6	121.7 (2)	O3—C21—C20	110.9 (2)
C12—C8—C6	123.9 (3)	O3—C22—H22A	109.5
C8—C9—C10	120.0 (2)	O3—C22—H22B	109.5
C8—C9—H9	120.0	H22A—C22—H22B	109.5
C10—C9—H9	120.0	O3—C22—H22C	109.5
N1—C10—C9	121.7 (3)	H22A—C22—H22C	109.5
N1—C10—C11	116.6 (2)	H22B—C22—H22C	109.5
C9—C10—C11	121.7 (2)

C10—N1—N2—C12	−1.1 (4)	N2—N1—C10—C11	178.8 (3)
F1'—C1—C2—C3	46.6 (11)	C8—C9—C10—N1	1.2 (4)
F3—C1—C2—C3	−104.0 (6)	C8—C9—C10—C11	−178.3 (3)
F1—C1—C2—C3	16.5 (6)	N1—N2—C12—O1	−177.8 (2)
F2'—C1—C2—C3	177.6 (8)	N1—N2—C12—C8	2.6 (4)
F2—C1—C2—C3	131.9 (6)	C13—O1—C12—N2	11.0 (4)
F3'—C1—C2—C3	−74.0 (8)	C13—O1—C12—C8	−169.4 (2)
F1'—C1—C2—C7	−133.2 (10)	C9—C8—C12—N2	−2.1 (4)
F3—C1—C2—C7	76.3 (6)	C6—C8—C12—N2	−178.0 (3)
F1—C1—C2—C7	−163.2 (5)	C9—C8—C12—O1	178.3 (3)
F2'—C1—C2—C7	−2.2 (9)	C6—C8—C12—O1	2.5 (4)
F2—C1—C2—C7	−47.8 (6)	C12—O1—C13—C18	−119.9 (3)
F3'—C1—C2—C7	106.2 (8)	C12—O1—C13—C14	64.9 (4)
C7—C2—C3—C4	0.2 (5)	C18—C13—C14—C15	−0.4 (5)
C1—C2—C3—C4	−179.6 (3)	O1—C13—C14—C15	174.6 (3)
C2—C3—C4—C5	0.5 (5)	C13—C14—C15—C16	−0.4 (5)
C3—C4—C5—C6	−0.8 (5)	C14—C15—C16—C17	0.9 (5)
C4—C5—C6—C7	0.5 (5)	C14—C15—C16—C19	−177.2 (3)
C4—C5—C6—C8	179.4 (3)	C15—C16—C17—C18	−0.5 (5)
C5—C6—C7—C2	0.2 (5)	C19—C16—C17—C18	177.4 (3)
C8—C6—C7—C2	−178.7 (3)	C14—C13—C18—C17	0.7 (5)
C3—C2—C7—C6	−0.5 (5)	O1—C13—C18—C17	−174.5 (3)
C1—C2—C7—C6	179.3 (3)	C16—C17—C18—C13	−0.3 (5)
C7—C6—C8—C9	139.4 (3)	C17—C16—C19—C20	4.1 (5)
C5—C6—C8—C9	−39.5 (4)	C15—C16—C19—C20	−178.0 (3)
C7—C6—C8—C12	−45.0 (4)	C16—C19—C20—C21	179.8 (3)
C5—C6—C8—C12	136.1 (3)	C22—O3—C21—O2	3.2 (5)
C12—C8—C9—C10	0.1 (4)	C22—O3—C21—C20	−177.6 (3)
C6—C8—C9—C10	176.1 (2)	C19—C20—C21—O2	−7.7 (5)
N2—N1—C10—C9	−0.8 (4)	C19—C20—C21—O3	173.1 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉F₃N₂O₃
M_r	416.39
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.4916 (19), 10.232 (2), 11.022 (2)
α, β, γ (°)	81.70 (3), 65.12 (3), 78.92 (3)
V (Å³)	950.6 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.16 × 0.06

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.977, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5529, 3319, 1862
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.147, 1.06
No. of reflections	3319
No. of parameters	301
No. of restraints	72
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.39

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+1.

Acknowledgements

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

References

Heinisch, G. & Kopelent, H. (1992). Prog. Med. Chem. 29, 141–183. CrossRef PubMed CAS Google Scholar
Kolar, P. & Tisler, M. (1999). Adv. Heterocycl. Chem. 75, 167–241. CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 6| June 2008| Page o1044

doi:10.1107/S1600536808013342

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

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organic compounds

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