3-Meth-oxy-2-[2-({[6-(trifluoro-meth-yl)pyridin-2-yl]-oxy}meth-yl)phen-yl]prop-2-enoic acid.

The title mol-ecule, C(17)H(14)F(3)NO(4), consists of two nearly planar fragments, viz. the 2-benzyl-oxypyridine (r.m.s. deviation 0.016 Å) and (E)-3-meth-oxy-prop2-enoic (r.m.s. deviation 0.004 Å) units, which form a dihedral angle of 84.19 (7)°. In the crystal, pairs of O-H⋯O hydrogen bonds link mol-ecules into dimers that are further connected by C-H⋯O and C-H⋯F inter-actions into (001) layers. In addition, π-π stacking inter-actions are observed within a layer between the pyridine and benzene rings [centroid-centroid distance = 3.768 (2) Å]. The F atoms of the trifluoro-methyl group are disordered over two sets of sites in a 0.53 (4):0.47 (4) ratio.

Related literature

The title compound is the acid metabolite of picoxystrobin [systematic name: methyl (E)-3-meth­oxy-2-{2-[6-(trifluoro­meth­yl)-2-pyridyl­oxymeth­yl]phen­yl}acrylate], a systemic fungicide with broad-spectrum bio-efficacy against various diseases of agricultural crops, see: Balba (2007 ▶); Ammermann et al. (2000 ▶). For a related structure, see: Kant et al. (2012 ▶).

Experimental

Crystal data

C17H14F3NO4

M = 353.29

Triclinic,

a = 7.4701 (4) Å

b = 10.1619 (5) Å

c = 11.8219 (5) Å

α = 94.721 (4)°

β = 100.079 (4)°

γ = 110.685 (5)°

V = 816.42 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.821, T max = 1.000

19533 measured reflections

3214 independent reflections

1988 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.154

S = 1.04

3214 reflections

253 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042316/gk2523sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042316/gk2523Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042316/gk2523Isup3.cml

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

C17H14F3NO4	Z = 2
Mr = 353.29	F(000) = 364
Triclinic, P1	Dx = 1.437 Mg m−3
Hall symbol: -P 1	Melting point: 415 K
a = 7.4701 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1619 (5) Å	Cell parameters from 7723 reflections
c = 11.8219 (5) Å	θ = 3.5–29.0°
α = 94.721 (4)°	µ = 0.13 mm−1
β = 100.079 (4)°	T = 293 K
γ = 110.685 (5)°	Plate, colourless
V = 816.42 (7) Å3	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3214 independent reflections
Radiation source: fine-focus sealed tube	1988 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
Tmin = 0.821, Tmax = 1.000	l = −14→14
19533 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0666P)2 + 0.1912P] where P = (Fo2 + 2Fc2)/3
3214 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.24 e Å−3
6 restraints	Δρmin = −0.40 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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)
O1	0.3119 (3)	0.52862 (18)	0.05675 (15)	0.0505 (5)
N1	0.5088 (3)	0.6809 (2)	0.22310 (18)	0.0441 (5)
O2	0.5218 (3)	0.88494 (19)	−0.22824 (18)	0.0579 (6)
O3	−0.0083 (3)	0.84278 (19)	−0.05459 (18)	0.0578 (6)
O4	0.2235 (3)	1.05406 (19)	−0.05040 (19)	0.0580 (6)
C1	0.1465 (4)	0.9160 (3)	−0.0804 (2)	0.0403 (6)
C2	0.2512 (4)	0.8515 (2)	−0.1454 (2)	0.0369 (6)
C3	0.4172 (4)	0.9358 (3)	−0.1689 (2)	0.0437 (6)
H3	0.4622	1.0333	−0.1434	0.052*
C4	0.1601 (3)	0.6946 (2)	−0.1883 (2)	0.0358 (6)
C5	0.1822 (3)	0.5959 (2)	−0.1174 (2)	0.0371 (6)
C6	0.0916 (4)	0.4512 (3)	−0.1611 (2)	0.0436 (6)
H6	0.1052	0.3847	−0.1142	0.052*
C7	−0.0180 (4)	0.4060 (3)	−0.2733 (2)	0.0502 (7)
H7	−0.0781	0.3090	−0.3016	0.060*
C8	−0.0393 (4)	0.5030 (3)	−0.3437 (2)	0.0529 (7)
H8	−0.1136	0.4720	−0.4194	0.063*
C9	0.0500 (4)	0.6462 (3)	−0.3013 (2)	0.0477 (7)
H9	0.0363	0.7118	−0.3492	0.057*
C10	0.3053 (4)	0.6487 (3)	0.0043 (2)	0.0434 (6)
H10A	0.4369	0.7114	0.0023	0.052*
H10B	0.2486	0.7015	0.0491	0.052*
C11	0.4141 (4)	0.5507 (3)	0.1669 (2)	0.0402 (6)
C12	0.6087 (4)	0.6917 (3)	0.3322 (2)	0.0492 (7)
C13	0.6148 (4)	0.5784 (3)	0.3857 (2)	0.0521 (7)
H13	0.6848	0.5918	0.4617	0.062*
C14	0.5133 (4)	0.4432 (3)	0.3227 (2)	0.0519 (7)
H14	0.5142	0.3634	0.3558	0.062*
C15	0.4128 (4)	0.4282 (3)	0.2127 (2)	0.0484 (7)
H15	0.3444	0.3384	0.1685	0.058*
C16	0.7204 (6)	0.8399 (4)	0.3923 (3)	0.0835 (12)
C17	0.6970 (5)	0.9862 (3)	−0.2501 (3)	0.0698 (9)
H17A	0.6635	1.0336	−0.3127	0.105*
H17B	0.7790	0.9378	−0.2709	0.105*
H17C	0.7662	1.0551	−0.1813	0.105*
F111	0.591 (3)	0.888 (3)	0.429 (2)	0.173 (7)	0.47 (4)
F222	0.854 (19)	0.914 (18)	0.334 (12)	0.145 (5)	0.47 (4)
F333	0.848 (3)	0.846 (2)	0.4878 (15)	0.115 (6)	0.47 (4)
F11A	0.6329 (17)	0.9292 (9)	0.3891 (12)	0.105 (4)	0.53 (4)
F22A	0.845 (17)	0.916 (16)	0.331 (11)	0.145 (5)	0.53 (4)
F33A	0.806 (3)	0.847 (2)	0.5018 (9)	0.109 (5)	0.53 (4)
H41	0.160 (6)	1.088 (4)	−0.012 (3)	0.101 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0606 (12)	0.0338 (10)	0.0482 (11)	0.0123 (9)	0.0007 (9)	0.0076 (8)
N1	0.0467 (13)	0.0386 (12)	0.0423 (13)	0.0132 (10)	0.0035 (10)	0.0059 (10)
O2	0.0551 (12)	0.0447 (11)	0.0786 (14)	0.0159 (10)	0.0339 (11)	0.0074 (10)
O3	0.0480 (12)	0.0373 (10)	0.0867 (15)	0.0104 (9)	0.0282 (11)	−0.0015 (10)
O4	0.0540 (13)	0.0321 (10)	0.0882 (16)	0.0125 (9)	0.0301 (11)	−0.0030 (10)
C1	0.0405 (15)	0.0310 (13)	0.0460 (15)	0.0121 (12)	0.0054 (12)	0.0020 (11)
C2	0.0397 (14)	0.0312 (13)	0.0407 (14)	0.0141 (12)	0.0089 (11)	0.0069 (11)
C3	0.0494 (16)	0.0353 (14)	0.0505 (16)	0.0192 (13)	0.0141 (13)	0.0072 (12)
C4	0.0308 (13)	0.0357 (13)	0.0418 (14)	0.0132 (11)	0.0108 (11)	0.0020 (11)
C5	0.0354 (14)	0.0349 (14)	0.0404 (14)	0.0113 (11)	0.0124 (11)	0.0030 (11)
C6	0.0437 (15)	0.0334 (14)	0.0502 (16)	0.0090 (12)	0.0133 (13)	0.0063 (12)
C7	0.0482 (17)	0.0356 (15)	0.0546 (18)	0.0044 (13)	0.0108 (13)	−0.0078 (13)
C8	0.0487 (17)	0.0549 (18)	0.0455 (16)	0.0164 (14)	−0.0004 (13)	−0.0070 (14)
C9	0.0508 (17)	0.0488 (16)	0.0450 (16)	0.0235 (14)	0.0052 (13)	0.0059 (13)
C10	0.0475 (16)	0.0315 (13)	0.0454 (15)	0.0088 (12)	0.0079 (12)	0.0068 (11)
C11	0.0397 (15)	0.0384 (14)	0.0426 (15)	0.0132 (12)	0.0111 (12)	0.0098 (12)
C12	0.0532 (17)	0.0442 (16)	0.0490 (17)	0.0199 (14)	0.0048 (13)	0.0062 (13)
C13	0.0547 (18)	0.0600 (19)	0.0454 (16)	0.0266 (15)	0.0069 (13)	0.0147 (14)
C14	0.0585 (18)	0.0467 (17)	0.0587 (19)	0.0244 (15)	0.0173 (15)	0.0213 (14)
C15	0.0537 (17)	0.0372 (15)	0.0540 (18)	0.0161 (13)	0.0123 (14)	0.0086 (12)
C16	0.104 (3)	0.058 (2)	0.061 (2)	0.014 (2)	−0.017 (2)	0.0047 (18)
C17	0.059 (2)	0.068 (2)	0.086 (2)	0.0171 (17)	0.0335 (18)	0.0197 (18)
F111	0.267 (14)	0.108 (10)	0.142 (12)	0.136 (10)	−0.061 (8)	−0.060 (8)
F222	0.162 (8)	0.077 (4)	0.114 (6)	−0.033 (5)	−0.012 (6)	0.011 (3)
F333	0.121 (8)	0.060 (6)	0.101 (9)	0.002 (5)	−0.067 (8)	0.006 (7)
F11A	0.144 (7)	0.039 (3)	0.111 (6)	0.042 (5)	−0.035 (4)	−0.007 (3)
F22A	0.162 (8)	0.077 (4)	0.114 (6)	−0.033 (5)	−0.012 (6)	0.011 (3)
F33A	0.166 (11)	0.090 (7)	0.046 (4)	0.043 (7)	−0.021 (5)	−0.009 (4)

O1—C11	1.346 (3)	C8—H8	0.9300
O1—C10	1.425 (3)	C9—H9	0.9300
N1—C11	1.313 (3)	C10—H10A	0.9700
N1—C12	1.347 (3)	C10—H10B	0.9700
O2—C3	1.336 (3)	C11—C15	1.396 (3)
O2—C17	1.432 (3)	C12—C13	1.370 (4)
O3—C1	1.240 (3)	C12—C16	1.482 (4)
O4—C1	1.304 (3)	C13—C14	1.384 (4)
O4—H41	0.85 (4)	C13—H13	0.9300
C1—C2	1.457 (3)	C14—C15	1.350 (4)
C2—C3	1.326 (3)	C14—H14	0.9300
C2—C4	1.497 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—F11A	1.291 (7)
C4—C9	1.387 (3)	C16—F33A	1.324 (8)
C4—C5	1.394 (3)	C16—F333	1.326 (9)
C5—C6	1.392 (3)	C16—F111	1.346 (10)
C5—C10	1.505 (3)	C16—F222	1.350 (10)
C6—C7	1.376 (4)	C16—F22A	1.350 (9)
C6—H6	0.9300	C17—H17A	0.9600
C7—C8	1.375 (4)	C17—H17B	0.9600
C7—H7	0.9300	C17—H17C	0.9600
C8—C9	1.375 (4)
C11—O1—C10	118.71 (19)	O1—C10—H10A	110.0
C11—N1—C12	115.5 (2)	C5—C10—H10A	110.0
C3—O2—C17	117.1 (2)	O1—C10—H10B	110.0
C1—O4—H41	115 (3)	C5—C10—H10B	110.0
O3—C1—O4	121.7 (2)	H10A—C10—H10B	108.4
O3—C1—C2	121.4 (2)	N1—C11—O1	120.1 (2)
O4—C1—C2	116.9 (2)	N1—C11—C15	124.4 (2)
C3—C2—C1	118.3 (2)	O1—C11—C15	115.5 (2)
C3—C2—C4	123.2 (2)	N1—C12—C13	124.6 (3)
C1—C2—C4	118.4 (2)	N1—C12—C16	114.5 (2)
C2—C3—O2	122.0 (2)	C13—C12—C16	120.9 (3)
C2—C3—H3	119.0	C12—C13—C14	117.7 (3)
O2—C3—H3	119.0	C12—C13—H13	121.1
C9—C4—C5	119.2 (2)	C14—C13—H13	121.1
C9—C4—C2	119.2 (2)	C15—C14—C13	119.3 (3)
C5—C4—C2	121.6 (2)	C15—C14—H14	120.3
C6—C5—C4	119.3 (2)	C13—C14—H14	120.3
C6—C5—C10	121.6 (2)	C14—C15—C11	118.4 (3)
C4—C5—C10	119.1 (2)	C14—C15—H15	120.8
C7—C6—C5	120.4 (2)	C11—C15—H15	120.8
C7—C6—H6	119.8	F11A—C16—C12	118.5 (5)
C5—C6—H6	119.8	F33A—C16—C12	113.2 (9)
C8—C7—C6	120.5 (2)	F333—C16—C12	112.1 (9)
C8—C7—H7	119.8	F111—C16—C12	106.9 (10)
C6—C7—H7	119.8	F222—C16—C12	112 (8)
C7—C8—C9	119.5 (3)	F22A—C16—C12	112 (7)
C7—C8—H8	120.2	O2—C17—H17A	109.5
C9—C8—H8	120.2	O2—C17—H17B	109.5
C8—C9—C4	121.1 (3)	H17A—C17—H17B	109.5
C8—C9—H9	119.4	O2—C17—H17C	109.5
C4—C9—H9	119.4	H17A—C17—H17C	109.5
O1—C10—C5	108.36 (19)	H17B—C17—H17C	109.5
O3—C1—C2—C3	−179.2 (2)	C12—N1—C11—O1	−179.1 (2)
O4—C1—C2—C3	0.5 (4)	C12—N1—C11—C15	−0.2 (4)
O3—C1—C2—C4	4.4 (4)	C10—O1—C11—N1	−1.5 (3)
O4—C1—C2—C4	−175.9 (2)	C10—O1—C11—C15	179.5 (2)
C1—C2—C3—O2	−179.9 (2)	C11—N1—C12—C13	−0.6 (4)
C4—C2—C3—O2	−3.7 (4)	C11—N1—C12—C16	177.8 (3)
C17—O2—C3—C2	179.1 (2)	N1—C12—C13—C14	0.9 (4)
C3—C2—C4—C9	−80.6 (3)	C16—C12—C13—C14	−177.4 (3)
C1—C2—C4—C9	95.6 (3)	C12—C13—C14—C15	−0.3 (4)
C3—C2—C4—C5	99.8 (3)	C13—C14—C15—C11	−0.5 (4)
C1—C2—C4—C5	−84.0 (3)	N1—C11—C15—C14	0.8 (4)
C9—C4—C5—C6	−0.7 (3)	O1—C11—C15—C14	179.7 (2)
C2—C4—C5—C6	178.9 (2)	N1—C12—C16—F11A	47.7 (9)
C9—C4—C5—C10	178.7 (2)	C13—C12—C16—F11A	−133.9 (8)
C2—C4—C5—C10	−1.7 (3)	N1—C12—C16—F33A	175.8 (12)
C4—C5—C6—C7	0.3 (4)	C13—C12—C16—F33A	−5.8 (13)
C10—C5—C6—C7	−179.1 (2)	N1—C12—C16—F333	−166.4 (15)
C5—C6—C7—C8	0.1 (4)	C13—C12—C16—F333	12.1 (16)
C6—C7—C8—C9	0.1 (4)	N1—C12—C16—F111	78.5 (15)
C7—C8—C9—C4	−0.5 (4)	C13—C12—C16—F111	−103.0 (16)
C5—C4—C9—C8	0.8 (4)	N1—C12—C16—F222	−60 (8)
C2—C4—C9—C8	−178.8 (2)	C13—C12—C16—F222	119 (9)
C11—O1—C10—C5	−179.7 (2)	N1—C12—C16—F22A	−56 (8)
C6—C5—C10—O1	1.9 (3)	C13—C12—C16—F22A	123 (8)
C4—C5—C10—O1	−177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O3i	0.85 (4)	1.78 (4)	2.626 (3)	174 (4)
C15—H15···O3ii	0.93	2.58	3.392 (3)	146
C17—H17A···F11Aiii	0.96	2.41	3.135 (14)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O3i	0.85 (4)	1.78 (4)	2.626 (3)	174 (4)
C15—H15⋯O3ii	0.93	2.58	3.392 (3)	146
C17—H17A⋯F11A iii	0.96	2.41	3.135 (14)	132

Symmetry codes: (i) ; (ii) ; (iii) .