3-Meth­oxy-2-[2-({[6-(trifluoro­meth­yl)pyridin-2-yl]­oxy}meth­yl)phen­yl]prop-2-enoic acid

Kant, R.; Gupta, V.K.; Kapoor, K.; Shripanavar, C.S.; Deshmukh, M.B.; Banerjee, K.

doi:10.1107/S1600536812042316

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3163

doi:10.1107/S1600536812042316

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3-Methoxy-2-[2-({[6-(trifluoromethyl)pyridin-2-yl]oxy}methyl)phenyl]prop-2-enoic acid

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Chetan S. Shripanavar,^b Madhukar B. Deshmukh ^c and Kaushik Banerjee ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^bNational Research Centre for Grapes, Pune 412307, India, and ^cDepartment of Chemistry, Shivaji University, Kolhapur, 416 004, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 24 September 2012; accepted 9 October 2012; online 20 October 2012)

The title molecule, C₁₇H₁₄F₃NO₄, consists of two nearly planar fragments, viz. the 2-benzyloxypyridine (r.m.s. deviation 0.016 Å) and (E)-3-methoxyprop2-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 molecules into dimers that are further connected by C—H⋯O and C—H⋯F interactions into (001) layers. In addition, π–π stacking interactions are observed within a layer between the pyridine and benzene rings [centroid–centroid distance = 3.768 (2) Å]. The F atoms of the trifluoromethyl 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_r = 353.29
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.059
wR(F²) = 0.154
S = 1.04
3214 reflections
253 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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⋯F11Aⁱⁱⁱ	0.96	2.41	3.135 (14)	132
Symmetry codes: (i) -x, -y+2, -z; (ii) -x, -y+1, -z; (iii) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042316/gk2523sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812042316/gk2523Isup3.cml

checkCIF report

Comment top

The above compound is the acid metabolite of picoxystrobin, which is a systemic fungicide of strobilurin group with broad spectrum bio-efficacy against various diseases of economically important agricultural crops (Balba, 2007; Ammermann et al., 2000).

In (I) (Fig.1), all bond lengths and angles are normal and correspond to those observed in the related structure (Kant et al., 2012). The dihedral angle between the two aromatic rings is 1.93 (9)°. The propenoic acid fragment is nearly perpendicular to the attached benzene ring [dihedral angle 82.6 (1)°]. The two nearly planar fragments, 2-(benzyloxy)-3-(trifluoromethyl)pyridine unit (r.m.s. deviation 0.016Å) and (E)-3-methoxyprop2-enoic unit (r.m.s. deviation 0.004Å) form dihedral angle of 84.19 (7)°. The F atoms of the trifluoromethyl group were refined as disordered over two sets of sites with occupancies of 0.53 (4)/0.47 (4). In the crystal, O—H···O hydrogen bonds link molecules to form dimers (Table 1). Dimers are further connected by C—H···O and C—H···F hydrogen bonds into (001) layers (Fig. 2). The crystal structure is further stabilized by π–π interactions between the pyridine ring (C11—C15/N1) of the molecule at (x, y, z) and the benzene ring of an inversion related molecule at(1 - x, 1 - y, - z) [centroid separation = 3.768 (2) Å, interplanar spacing = 3.437 Å and centroid shift = 1.54 Å].

Related literature top

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 of the strobilurin group with broad-spectrum bio-efficacy against various diseases of economically important agricultural crops, see: Balba (2007); Ammermann et al. (2000). For a related structure, see: Kant et al. (2012).

Experimental top

Picoxystrobin (0.353 g, 0.001 mol) was dissolved in 5 ml of acetone and to it 5 ml of 1 N NaOH solution was added. The reaction mixture was refluxed at 343 K for 6 h, and then cooled. The compound was precipitated by neutralizing with 1 N HCl solution. The precipitated compound was dissolved in methanol and crystallized by the process of slow evaporation.(m.p. 415 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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).

Figures top

	Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The thermal ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules viewed down the a axis. The dotted lines show intermolecular C—H···O, O—H···O and C—H···F hydrogen bonds.

3-Methoxy-2-[2-({[6-(trifluoromethyl)pyridin-2-yl]oxy}methyl)phenyl]prop-2-enoic acid top

Crystal data top

C₁₇H₁₄F₃NO₄	Z = 2
M_r = 353.29	F(000) = 364
Triclinic, P1	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3214 independent reflections
Radiation source: fine-focus sealed tube	1988 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
T_min = 0.821, T_max = 1.000	l = −14→14
19533 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)] = 0.059	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(F_o²) + (0.0666P)² + 0.1912P] where P = (F_o² + 2F_c²)/3
3214 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.24 e Å⁻³
6 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₇H₁₄F₃NO₄	γ = 110.685 (5)°
M_r = 353.29	V = 816.42 (7) Å³
Triclinic, P1	Z = 2
a = 7.4701 (4) Å	Mo Kα radiation
b = 10.1619 (5) Å	µ = 0.13 mm⁻¹
c = 11.8219 (5) Å	T = 293 K
α = 94.721 (4)°	0.3 × 0.2 × 0.2 mm
β = 100.079 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3214 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1988 reflections with I > 2σ(I)
T_min = 0.821, T_max = 1.000	R_int = 0.057
19533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	6 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.24 e Å⁻³
3214 reflections	Δρ_min = −0.40 e Å⁻³
253 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y+2, −z; (ii) −x, −y+1, −z; (iii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄F₃NO₄
M_r	353.29
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4701 (4), 10.1619 (5), 11.8219 (5)
α, β, γ (°)	94.721 (4), 100.079 (4), 110.685 (5)
V (Å³)	816.42 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.821, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	19533, 3214, 1988
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.154, 1.04
No. of reflections	3214
No. of parameters	253
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.40

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y+2, −z; (ii) −x, −y+1, −z; (iii) −x+1, −y+2, −z.

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Ammermann, E., Lorenz, G., Schelberger, K., Mueller, B., Kirstgen, R. & Sauter, H. (2000). Proceedings of the BCPC Conference –Pest and Diseases, 2, 541–548. Google Scholar
Balba, H. (2007). J. Environ. Sci. Health Part B, 42, 441–451. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kant, R., Gupta, V. K., Kapoor, K., Shripanavar, C. S. & Banerjee, K. (2012). Acta Cryst. E68, o2425. CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3163

doi:10.1107/S1600536812042316

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

3-Meth­­oxy-2-[2-({[6-(tri­fluoro­meth­yl)pyridin-2-yl]­­oxy}meth­yl)phen­yl]prop-2-enoic acid

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Methoxy-2-[2-({[6-(trifluoromethyl)pyridin-2-yl]oxy}methyl)phenyl]prop-2-enoic acid