Methyl 3-(4-{6-methyl-4-[3-(trifluoro-meth-yl)phen-yl]pyridazin-3-yl-oxy}phen-yl)propanoate.

In the title compound, C(22)H(19)F(3)N(2)O(3), the benzene rings of the trifluoro-methyl-phenyl and benzoyl-phenyl groups form dihedral angles of 41.89 (10) and 67.44 (10)°, respectively, with the pyridazine ring. The methyl-propanoate group is nearly coplanar with the attached benzene ring [dihedral angle = 3.9 (2)°]. The trifluoro-methyl group is disordered over two positions; the site-occupancy factors are ca 0.64 and 0.36. In the crystal structure, inversion-related mol-ecules are linked through C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C22H19F3N2O3

M = 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

Δρmax = 0.40 e Å−3

Δρmin = −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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H19F3N2O3	Z = 2
Mr = 416.39	F000 = 432
Triclinic, P1	Dx = 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 = 2.0–27.9º
c = 11.022 (2) Å	µ = 0.12 mm−1
α = 81.70 (3)º	T = 113 (2) K
β = 65.12 (3)º	Plate, colourless
γ = 78.92 (3)º	0.20 × 0.16 × 0.06 mm
V = 950.6 (4) Å3

Rigaku Saturn CCD area-detector diffractometer	3319 independent reflections
Radiation source: rotating anode	1862 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.054
Detector resolution: 7.31 pixels mm-1	θmax = 25.0º
T = 113(2) K	θmin = 2.0º
ω and φ scans	h = −10→11
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −12→11
Tmin = 0.977, Tmax = 0.993	l = −13→11
5529 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0675P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
3319 reflections	Δρmax = 0.40 e Å−3
301 parameters	Δρmin = −0.39 e Å−3
72 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) . Cg1 is the centroid of the C2–C7 ring.