organic compounds
3-Methoxy-2-[2-({[6-(trifluoromethyl)pyridin-2-yl]oxy}methyl)phenyl]prop-2-enoic acid
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
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
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell 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
10.1107/S1600536812042316/gk2523sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042316/gk2523Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042316/gk2523Isup3.cml
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).
H atom bonded to O atom was located in a difference map and refined freely. Other H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). In the
process restraints were imposed on C-F distances of the disordered molecular fragments.Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
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).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 |
C17H14F3NO4 | γ = 110.685 (5)° |
Mr = 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)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 3214 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 1988 reflections with I > 2σ(I) |
Tmin = 0.821, Tmax = 1.000 | Rint = 0.057 |
19533 measured reflections |
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 | Δρmax = 0.24 e Å−3 |
3214 reflections | Δρmin = −0.40 e Å−3 |
253 parameters |
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 |
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 |
Mr | 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) |
Tmin, Tmax | 0.821, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19533, 3214, 1988 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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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].