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The crystal structure of the title compound, C19H17F3N2O4, a metabolite of the fungicide trifloxy­strobin (TFS), contains one mol­ecule in the asymmetric unit. The CF3 group is disordered over two positions. The important characteristics of the mol­ecule are the two C=N bonds in an E,E configuration, one in the β-methoxy system and the other in the oxy­methyl side chain between the two aromatic rings. The mol­ecules are linked via an O—H...N hydrogen bond and an infinite spiral is formed along the b-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012900/bt6649sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012900/bt6649Isup2.hkl
Contains datablock I

CCDC reference: 274337

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.036
  • wR factor = 0.094
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C17
Author Response: The data collection was performed at room temperature and the results are good except the high temperature factor of F1'.

Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
Alert level C PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit P 2ybc PLAT213_ALERT_2_C Atom F3 has ADP max/min Ratio ............. 3.60 prolat PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT220_ALERT_2_C Large Non-Solvent F Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15
Author Response: The data collection was performed at room temperature and the results are good except the high temperature factor of F1'.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O3
Author Response: The data collection was performed at room temperature and the results are good except the high temperature factor of F1'.
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST (Nardelli, 1995) and PLATON (Spek, 2001).

(E,E)-α-(Methoxyimino)-2-[({1-[3-(trifluoromethyl)phenyl]ethyl- idene}amino)oxymethyl]benzeneacetic acid top
Crystal data top
C19H17F3N2O4F(000) = 816
Mr = 394.35Dx = 1.359 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybcCell parameters from 10735 reflections
a = 13.6953 (14) Åθ = 3.1–25.4°
b = 9.0282 (15) ŵ = 0.12 mm1
c = 16.302 (2) ÅT = 291 K
β = 106.983 (7)°Plate, colourless
V = 1927.7 (5) Å30.10 × 0.08 × 0.02 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1216 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 25.4°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 1616
92 frames via ω–rotation (Δω=2°) and two times 150 s per frame (two sets at different κ–angles) scansk = 1010
10735 measured reflectionsl = 1918
3500 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094 w = [exp(4.20(sinθ/λ)2)]/[σ2(Fo2)]
where P = 0.33333Fo2 + 0.66667Fc2
S = 1.05(Δ/σ)max < 0.001
3500 reflectionsΔρmax = 0.12 e Å3
288 parametersΔρmin = 0.11 e Å3
33 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (5)
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
xyzUiso*/UeqOcc. (<1)
C170.9526 (3)0.5666 (6)0.2122 (3)0.0932 (14)
F10.9111 (7)0.4445 (11)0.2340 (7)0.089 (4)0.44 (2)
F20.9547 (14)0.6602 (15)0.2711 (9)0.210 (10)0.44 (2)
F31.0445 (7)0.529 (2)0.2164 (10)0.207 (8)0.44 (2)
F1'0.9391 (14)0.4306 (10)0.2235 (8)0.239 (8)0.56 (2)
F2'0.9338 (6)0.6413 (10)0.2748 (4)0.093 (3)0.56 (2)
F3'1.0510 (5)0.5860 (19)0.2253 (6)0.179 (5)0.56 (2)
O10.32229 (17)1.0672 (3)0.22413 (12)0.0808 (7)
O20.38587 (15)0.9345 (3)0.34255 (13)0.0611 (6)
H20.401 (3)1.033 (4)0.367 (2)0.130 (15)*
O30.31048 (17)0.5601 (3)0.21431 (12)0.0822 (7)
O40.47856 (14)0.7508 (2)0.04261 (12)0.0642 (6)
N10.33628 (17)0.6911 (3)0.26012 (14)0.0616 (7)
N20.57742 (16)0.6904 (3)0.06055 (13)0.0524 (6)
C10.2685 (2)0.8080 (3)0.11721 (16)0.0498 (7)
C20.31563 (19)0.7461 (3)0.06103 (17)0.0514 (8)
C30.2680 (2)0.7527 (4)0.02663 (18)0.0680 (10)
H3A0.29940.71100.06460.082*
C40.1745 (2)0.8209 (4)0.05745 (19)0.0833 (11)
H4A0.14300.82530.11630.100*
C50.1276 (2)0.8822 (4)0.0021 (2)0.0851 (12)
H5A0.06430.92750.02330.102*
C60.1742 (2)0.8768 (4)0.08491 (19)0.0692 (10)
H6A0.14240.91930.12230.083*
C70.3161 (2)0.8058 (4)0.21186 (17)0.0497 (7)
C80.3413 (2)0.9489 (4)0.25920 (19)0.0533 (8)
C100.3324 (3)0.4370 (4)0.2734 (2)0.1358 (18)
H10D0.31970.34570.24180.204*
H10E0.28940.44250.31040.204*
H10F0.40270.44080.30720.204*
C110.7341 (2)0.7043 (3)0.02873 (18)0.0534 (8)
C120.7927 (2)0.6592 (3)0.10947 (17)0.0590 (9)
H12A0.76360.65640.15440.071*
C130.8931 (2)0.6186 (4)0.1240 (2)0.0672 (10)
C140.9378 (2)0.6263 (4)0.0594 (3)0.0874 (12)
H14A1.00600.60040.06960.105*
C150.8812 (3)0.6729 (5)0.0213 (2)0.0986 (13)
H15A0.91130.67800.06550.118*
C160.7806 (3)0.7116 (4)0.0360 (2)0.0779 (11)
H16A0.74300.74310.09040.093*
C180.6265 (2)0.7509 (3)0.01302 (17)0.0523 (8)
C190.5795 (2)0.8618 (4)0.05471 (19)0.0828 (11)
H19A0.51480.82550.08960.124*
H19B0.62380.87800.08990.124*
H19D0.56960.95340.02830.124*
C200.42022 (19)0.6758 (4)0.09013 (16)0.0575 (8)
H20A0.45080.68940.15130.069*
H20C0.41610.57060.07750.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C170.069 (3)0.095 (4)0.101 (4)0.005 (3)0.001 (3)0.004 (4)
F10.085 (6)0.116 (10)0.067 (4)0.001 (4)0.022 (4)0.027 (5)
F20.244 (16)0.152 (12)0.159 (13)0.011 (10)0.058 (11)0.055 (10)
F30.084 (8)0.365 (19)0.183 (12)0.123 (10)0.059 (8)0.159 (13)
F1'0.369 (19)0.106 (9)0.157 (10)0.051 (11)0.059 (11)0.012 (7)
F2'0.075 (4)0.150 (8)0.050 (4)0.017 (4)0.014 (3)0.002 (5)
F3'0.059 (5)0.375 (13)0.089 (5)0.001 (6)0.004 (4)0.059 (7)
O10.140 (2)0.0459 (17)0.0537 (14)0.0015 (14)0.0240 (13)0.0039 (12)
O20.0844 (15)0.0489 (16)0.0451 (14)0.0051 (11)0.0113 (11)0.0038 (11)
O30.141 (2)0.0417 (16)0.0605 (14)0.0133 (14)0.0250 (13)0.0067 (13)
O40.0583 (13)0.0684 (15)0.0693 (14)0.0160 (11)0.0240 (11)0.0210 (11)
N10.0918 (18)0.0419 (18)0.0520 (15)0.0078 (15)0.0222 (13)0.0067 (15)
N20.0555 (14)0.0526 (17)0.0492 (14)0.0122 (13)0.0153 (12)0.0050 (14)
C10.0567 (17)0.050 (2)0.0432 (17)0.0021 (16)0.0158 (15)0.0035 (16)
C20.0494 (17)0.054 (2)0.0483 (18)0.0057 (15)0.0109 (15)0.0037 (15)
C30.067 (2)0.086 (3)0.0457 (19)0.0136 (19)0.0088 (16)0.0093 (17)
C40.074 (2)0.116 (3)0.049 (2)0.020 (2)0.0011 (18)0.008 (2)
C50.064 (2)0.121 (4)0.063 (2)0.028 (2)0.0061 (19)0.004 (2)
C60.0612 (19)0.085 (3)0.064 (2)0.0182 (19)0.0210 (17)0.0017 (18)
C70.0625 (18)0.042 (2)0.0484 (17)0.0041 (17)0.0217 (14)0.0009 (17)
C80.071 (2)0.050 (2)0.042 (2)0.0073 (17)0.0207 (17)0.0007 (18)
C100.265 (5)0.042 (3)0.087 (3)0.015 (3)0.031 (3)0.021 (2)
C110.0614 (19)0.052 (2)0.0495 (18)0.0022 (16)0.0212 (16)0.0018 (16)
C120.0622 (19)0.061 (2)0.056 (2)0.0010 (17)0.0208 (16)0.0023 (17)
C130.059 (2)0.077 (3)0.066 (2)0.0038 (18)0.0189 (19)0.0001 (19)
C140.064 (2)0.104 (3)0.097 (3)0.013 (2)0.029 (2)0.004 (2)
C150.086 (3)0.138 (4)0.084 (3)0.029 (3)0.045 (2)0.019 (3)
C160.081 (2)0.098 (3)0.060 (2)0.021 (2)0.0292 (19)0.014 (2)
C180.067 (2)0.047 (2)0.0457 (19)0.0047 (16)0.0208 (16)0.0048 (15)
C190.089 (2)0.080 (3)0.087 (2)0.024 (2)0.0377 (19)0.039 (2)
C200.0640 (19)0.060 (2)0.0515 (17)0.0063 (17)0.0219 (15)0.0024 (17)
Geometric parameters (Å, º) top
C17—F1'1.263 (9)C5—C61.376 (3)
C17—F21.272 (11)C5—H5A0.9300
C17—F31.287 (9)C6—H6A0.9300
C17—F2'1.309 (7)C7—C81.492 (4)
C17—F3'1.313 (8)C10—H10D0.9600
C17—F11.335 (9)C10—H10E0.9600
C17—C131.506 (5)C10—H10F0.9600
O1—C81.204 (3)C11—C161.384 (4)
O2—C81.323 (3)C11—C121.387 (3)
O2—H20.97 (4)C11—C181.481 (4)
O3—N11.388 (3)C12—C131.376 (3)
O3—C101.444 (4)C12—H12A0.9300
O4—N21.409 (2)C13—C141.366 (4)
O4—C201.435 (3)C14—C151.383 (4)
N1—C71.281 (3)C14—H14A0.9300
N2—C181.286 (3)C15—C161.373 (4)
C1—C21.383 (3)C15—H15A0.9300
C1—C61.391 (3)C16—H16A0.9300
C1—C71.490 (3)C18—C191.491 (4)
C2—C31.388 (3)C19—H19A0.9600
C2—C201.511 (3)C19—H19B0.9600
C3—C41.377 (4)C19—H19D0.9600
C3—H3A0.9300C20—H20A0.9700
C4—C51.367 (4)C20—H20C0.9700
C4—H4A0.9300
F2—C17—F3109.3 (9)O2—C8—C7114.4 (3)
F1'—C17—F2'108.5 (8)O3—C10—H10D109.5
F1'—C17—F3'107.0 (8)O3—C10—H10E109.5
F2'—C17—F3'103.3 (6)H10D—C10—H10E109.5
F2—C17—F1105.4 (9)O3—C10—H10F109.5
F3—C17—F1104.6 (9)H10D—C10—H10F109.5
F1'—C17—C13112.4 (7)H10E—C10—H10F109.5
F2—C17—C13113.6 (8)C16—C11—C12118.1 (3)
F3—C17—C13112.4 (8)C16—C11—C18120.7 (3)
F2'—C17—C13114.1 (5)C12—C11—C18121.2 (3)
F3'—C17—C13110.9 (6)C13—C12—C11120.9 (3)
F1—C17—C13111.0 (5)C13—C12—H12A119.6
C8—O2—H2108 (2)C11—C12—H12A119.6
N1—O3—C10109.0 (2)C14—C13—C12120.3 (3)
N2—O4—C20111.0 (2)C14—C13—C17120.9 (4)
C7—N1—O3112.5 (2)C12—C13—C17118.8 (4)
C18—N2—O4110.5 (2)C13—C14—C15119.7 (3)
C2—C1—C6119.4 (2)C13—C14—H14A120.1
C2—C1—C7122.2 (2)C15—C14—H14A120.1
C6—C1—C7118.4 (3)C16—C15—C14119.9 (3)
C1—C2—C3119.6 (3)C16—C15—H15A120.0
C1—C2—C20123.0 (2)C14—C15—H15A120.0
C3—C2—C20117.3 (3)C15—C16—C11121.1 (3)
C4—C3—C2120.1 (3)C15—C16—H16A119.5
C4—C3—H3A119.9C11—C16—H16A119.5
C2—C3—H3A119.9N2—C18—C11116.4 (3)
C5—C4—C3120.4 (3)N2—C18—C19122.8 (3)
C5—C4—H4A119.8C11—C18—C19120.8 (3)
C3—C4—H4A119.8C18—C19—H19A109.5
C4—C5—C6120.0 (3)C18—C19—H19B109.5
C4—C5—H5A120.0H19A—C19—H19B109.5
C6—C5—H5A120.0C18—C19—H19D109.5
C5—C6—C1120.4 (3)H19A—C19—H19D109.5
C5—C6—H6A119.8H19B—C19—H19D109.5
C1—C6—H6A119.8O4—C20—C2105.0 (2)
N1—C7—C1126.7 (3)O4—C20—H20A110.7
N1—C7—C8114.0 (3)C2—C20—H20A110.8
C1—C7—C8119.3 (3)O4—C20—H20C110.8
O1—C8—O2123.1 (3)C2—C20—H20C110.7
O1—C8—C7122.5 (3)H20A—C20—H20C108.8
C10—O3—N1—C7178.1 (3)F1'—C17—C13—C1496.1 (11)
C20—O4—N2—C18175.2 (2)F2—C17—C13—C14122.8 (12)
C6—C1—C2—C30.3 (4)F3—C17—C13—C141.9 (13)
C7—C1—C2—C3179.4 (3)F2'—C17—C13—C14139.9 (6)
C6—C1—C2—C20177.0 (3)F3'—C17—C13—C1423.7 (10)
C7—C1—C2—C202.1 (5)F1—C17—C13—C14118.7 (7)
C1—C2—C3—C40.1 (5)F1'—C17—C13—C1284.2 (11)
C20—C2—C3—C4177.3 (3)F2—C17—C13—C1256.9 (12)
C2—C3—C4—C50.2 (6)F3—C17—C13—C12178.4 (11)
C3—C4—C5—C60.4 (6)F2'—C17—C13—C1239.8 (7)
C4—C5—C6—C10.6 (6)F3'—C17—C13—C12156.0 (8)
C2—C1—C6—C50.5 (5)F1—C17—C13—C1261.6 (7)
C7—C1—C6—C5179.7 (3)C12—C13—C14—C151.1 (5)
O3—N1—C7—C11.2 (4)C17—C13—C14—C15179.3 (4)
O3—N1—C7—C8179.1 (2)C13—C14—C15—C160.2 (6)
C2—C1—C7—N164.0 (4)C14—C15—C16—C110.2 (6)
C6—C1—C7—N1116.9 (3)C12—C11—C16—C151.1 (5)
C2—C1—C7—C8118.3 (3)C18—C11—C16—C15178.0 (3)
C6—C1—C7—C860.8 (4)O4—N2—C18—C11176.4 (2)
N1—C7—C8—O1176.1 (3)O4—N2—C18—C193.6 (4)
C1—C7—C8—O11.9 (4)C16—C11—C18—N2153.6 (3)
N1—C7—C8—O23.8 (4)C12—C11—C18—N229.5 (4)
C1—C7—C8—O2178.2 (2)C16—C11—C18—C1926.3 (4)
C16—C11—C12—C131.9 (5)C12—C11—C18—C19150.6 (3)
C18—C11—C12—C13178.8 (3)N2—O4—C20—C2177.0 (2)
C11—C12—C13—C141.9 (5)C1—C2—C20—O4125.2 (3)
C11—C12—C13—C17178.4 (4)C3—C2—C20—O452.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N2i0.97 (4)1.81 (4)2.761 (3)164 (3)
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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