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The crystal structure of the title compound, C20H19F3N2O4, 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,Z-configuration, viz. E in the β-methoxy system and Z in the oxymethyl chain between the two aromatic rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014972/bt6668sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014972/bt6668Isup2.hkl
Contains datablock I

CCDC reference: 274346

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.073
  • Data-to-parameter ratio = 12.5

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 factors of the disordered F atoms.
PLAT431_ALERT_2_A Short Inter HL..A Contact  F1'    ..  F3'     ..       2.40 Ang.
Author Response: The data collection was performed at room temperature and F atoms are disordered.

Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
Author Response: The data collection was performed at room temperature and the results are good except the high temperature factors of the disordered F atoms.
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C20 H19 F3 N2 O4

2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 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, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).

Methyl (E,Z)-α-(methoxyimino)-2-[({1-[3- (trifluoromethyl)phenyl]ethylidene}amino)oxymethyl]benzeneacetate top
Crystal data top
C20H19F3N2O4F(000) = 848
Mr = 408.37Dx = 1.337 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14739 reflections
a = 8.0256 (12) Åθ = 3.0–25.3°
b = 33.580 (5) ŵ = 0.11 mm1
c = 8.0957 (11) ÅT = 291 K
β = 111.566 (5)°Block, colourless
V = 2029.1 (5) Å30.24 × 0.24 × 0.22 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1749 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 25.3°, θmin = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 99
551 frames via ω–rotation (Δω=1°) and two times 30 s per frame (four sets at differnt κ–angles) scansk = 3939
14739 measured reflectionsl = 99
3658 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.021P)2]
where P = (Fo2 + 2Fc2)/3
3658 reflections(Δ/σ)max = 0.001
293 parametersΔρmax = 0.11 e Å3
30 restraintsΔρmin = 0.15 e Å3
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)
C170.0749 (3)0.21255 (9)0.0365 (4)0.0813 (6)
F10.1777 (6)0.2032 (3)0.1234 (10)0.118 (3)0.547 (11)
F20.1225 (8)0.1896 (6)0.141 (2)0.219 (7)0.547 (11)
F30.1331 (6)0.24801 (18)0.049 (2)0.148 (4)0.547 (11)
F1'0.1473 (14)0.2357 (7)0.094 (2)0.220 (7)0.453 (11)
F2'0.1657 (9)0.1793 (2)0.004 (2)0.127 (4)0.453 (11)
F3'0.1041 (9)0.2272 (4)0.1722 (13)0.120 (3)0.453 (11)
O10.22879 (18)0.03251 (4)0.19754 (17)0.0886 (5)
O20.38273 (17)0.02154 (3)0.37375 (15)0.0671 (4)
O30.00672 (16)0.07488 (4)0.77416 (16)0.0803 (4)
O40.26611 (15)0.16329 (3)0.31658 (16)0.0615 (3)
N10.1334 (2)0.05316 (4)0.6401 (2)0.0675 (4)
N20.37316 (18)0.13173 (4)0.2145 (2)0.0616 (4)
C10.0175 (2)0.08513 (6)0.4593 (2)0.0524 (4)
C20.0079 (2)0.12630 (6)0.4664 (2)0.0531 (5)
C30.1441 (3)0.14898 (5)0.4459 (2)0.0671 (5)
H3A0.13870.17660.45030.081*
C40.2872 (3)0.13120 (7)0.4190 (2)0.0777 (6)
H4A0.37770.14670.40650.093*
C50.2949 (3)0.09067 (7)0.4109 (2)0.0754 (6)
H5A0.39080.07860.39240.090*
C60.1611 (3)0.06768 (6)0.4302 (2)0.0675 (5)
H6A0.16700.04010.42350.081*
C70.1190 (2)0.05925 (5)0.4892 (2)0.0538 (5)
C80.2474 (3)0.03660 (5)0.3367 (3)0.0597 (5)
C90.5107 (3)0.00253 (5)0.2366 (2)0.0884 (6)
H9A0.59290.01470.28270.133*
H9B0.44820.02290.19920.133*
H9C0.57560.01400.13700.133*
C100.0210 (3)0.06519 (6)0.9415 (2)0.1083 (8)
H10A0.06050.08151.03340.162*
H10B0.00830.03760.96830.162*
H10C0.14130.07000.93460.162*
C110.3595 (2)0.17226 (5)0.0320 (2)0.0534 (5)
C120.1787 (2)0.17759 (5)0.0038 (2)0.0549 (5)
H12A0.09610.16040.08170.066*
C130.1193 (3)0.20807 (5)0.0744 (2)0.0580 (5)
C140.2393 (3)0.23404 (6)0.1880 (3)0.0846 (6)
H14A0.19920.25480.24000.102*
C150.4175 (3)0.22918 (7)0.2240 (3)0.1057 (8)
H15A0.49930.24690.29950.127*
C160.4777 (3)0.19805 (6)0.1490 (3)0.0854 (6)
H16A0.60010.19450.17820.102*
C180.4217 (2)0.13849 (5)0.0482 (3)0.0568 (5)
C190.5494 (3)0.10889 (6)0.0722 (3)0.0926 (7)
H19A0.57040.08770.00240.139*
H19B0.49870.09810.15320.139*
H19C0.66060.12190.13790.139*
C200.1504 (2)0.14761 (5)0.4841 (2)0.0645 (5)
H20A0.21710.12920.52880.077*
H20B0.10800.16920.56900.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C170.081 (2)0.091 (2)0.080 (2)0.0138 (17)0.0381 (18)0.0024 (19)
F10.060 (2)0.156 (6)0.124 (5)0.023 (3)0.016 (3)0.049 (5)
F20.074 (3)0.356 (16)0.237 (10)0.033 (6)0.069 (5)0.196 (10)
F30.112 (2)0.107 (4)0.216 (9)0.047 (2)0.049 (4)0.045 (5)
F1'0.161 (6)0.320 (17)0.200 (12)0.158 (9)0.093 (7)0.152 (11)
F2'0.063 (3)0.107 (5)0.210 (10)0.016 (3)0.050 (6)0.040 (6)
F3'0.089 (3)0.172 (7)0.124 (5)0.006 (4)0.071 (4)0.048 (5)
O10.1004 (11)0.1148 (11)0.0593 (9)0.0330 (8)0.0395 (9)0.0221 (8)
O20.0692 (9)0.0750 (8)0.0571 (8)0.0247 (7)0.0234 (8)0.0127 (6)
O30.0895 (10)0.1028 (10)0.0415 (8)0.0377 (8)0.0158 (8)0.0033 (7)
O40.0657 (8)0.0561 (7)0.0582 (8)0.0012 (7)0.0175 (7)0.0008 (7)
N10.0752 (11)0.0769 (11)0.0456 (10)0.0205 (9)0.0167 (10)0.0004 (9)
N20.0495 (9)0.0607 (10)0.0715 (12)0.0089 (8)0.0186 (10)0.0007 (9)
C10.0523 (12)0.0620 (13)0.0411 (11)0.0015 (10)0.0152 (10)0.0040 (9)
C20.0530 (12)0.0630 (13)0.0419 (11)0.0037 (11)0.0157 (10)0.0031 (9)
C30.0669 (14)0.0689 (13)0.0615 (13)0.0126 (12)0.0188 (11)0.0045 (10)
C40.0602 (15)0.1034 (18)0.0685 (15)0.0171 (14)0.0224 (12)0.0100 (13)
C50.0546 (14)0.1059 (18)0.0682 (14)0.0075 (13)0.0254 (11)0.0075 (12)
C60.0698 (14)0.0702 (13)0.0638 (14)0.0046 (12)0.0262 (12)0.0054 (10)
C70.0602 (12)0.0553 (11)0.0440 (12)0.0046 (10)0.0170 (11)0.0026 (10)
C80.0646 (14)0.0594 (12)0.0543 (14)0.0071 (10)0.0210 (12)0.0002 (11)
C90.0968 (16)0.0926 (15)0.0691 (15)0.0440 (13)0.0227 (13)0.0205 (12)
C100.134 (2)0.148 (2)0.0393 (13)0.0458 (16)0.0275 (14)0.0004 (12)
C110.0481 (12)0.0575 (12)0.0544 (12)0.0032 (10)0.0187 (11)0.0018 (9)
C120.0507 (13)0.0556 (11)0.0561 (12)0.0012 (9)0.0167 (10)0.0008 (9)
C130.0563 (13)0.0601 (12)0.0632 (13)0.0004 (11)0.0287 (11)0.0018 (10)
C140.0921 (18)0.0780 (14)0.0987 (18)0.0097 (14)0.0528 (16)0.0288 (13)
C150.0782 (17)0.1183 (19)0.129 (2)0.0365 (15)0.0479 (16)0.0668 (16)
C160.0516 (13)0.1095 (17)0.0968 (17)0.0151 (13)0.0293 (13)0.0316 (14)
C180.0454 (12)0.0619 (13)0.0585 (13)0.0036 (9)0.0136 (12)0.0003 (11)
C190.0776 (14)0.0940 (15)0.0886 (16)0.0298 (12)0.0098 (13)0.0028 (12)
C200.0709 (14)0.0692 (12)0.0517 (13)0.0040 (11)0.0207 (12)0.0014 (10)
Geometric parameters (Å, º) top
C17—F1'1.265 (6)C5—H5A0.9300
C17—F11.292 (5)C6—H6A0.9300
C17—F31.296 (4)C7—C81.493 (2)
C17—F3'1.301 (5)C9—H9A0.9600
C17—F21.304 (5)C9—H9B0.9600
C17—F2'1.305 (6)C9—H9C0.9600
C17—C131.481 (3)C10—H10A0.9600
O1—C81.1980 (17)C10—H10B0.9600
O2—C81.3282 (18)C10—H10C0.9600
O2—C91.4500 (18)C11—C161.374 (2)
O3—N11.3903 (16)C11—C121.383 (2)
O3—C101.4384 (17)C11—C181.482 (2)
O4—N21.4219 (16)C12—C131.377 (2)
O4—C201.4328 (18)C12—H12A0.9300
N1—C71.2853 (17)C13—C141.372 (2)
N2—C181.2769 (19)C14—C151.360 (3)
C1—C21.387 (2)C14—H14A0.9300
C1—C61.388 (2)C15—C161.382 (2)
C1—C71.486 (2)C15—H15A0.9300
C2—C31.392 (2)C16—H16A0.9300
C2—C201.510 (2)C18—C191.501 (2)
C3—C41.380 (2)C19—H19A0.9600
C3—H3A0.9300C19—H19B0.9600
C4—C51.365 (2)C19—H19C0.9600
C4—H4A0.9300C20—H20A0.9700
C5—C61.377 (2)C20—H20B0.9700
F1—C17—F3100.6 (4)H9A—C9—H9B109.5
F1'—C17—F3'107.6 (5)O2—C9—H9C109.5
F1—C17—F2106.1 (5)H9A—C9—H9C109.5
F3—C17—F2107.1 (5)H9B—C9—H9C109.5
F1'—C17—F2'107.8 (7)O3—C10—H10A109.5
F3'—C17—F2'103.4 (5)O3—C10—H10B109.5
F1'—C17—C13111.1 (4)H10A—C10—H10B109.5
F1—C17—C13114.7 (3)O3—C10—H10C109.5
F3—C17—C13117.3 (3)H10A—C10—H10C109.5
F3'—C17—C13111.5 (4)H10B—C10—H10C109.5
F2—C17—C13110.1 (3)C16—C11—C12117.93 (16)
F2'—C17—C13114.9 (3)C16—C11—C18121.74 (17)
C8—O2—C9116.56 (13)C12—C11—C18120.27 (16)
N1—O3—C10109.15 (13)C13—C12—C11120.93 (16)
N2—O4—C20108.60 (12)C13—C12—H12A119.5
C7—N1—O3111.29 (13)C11—C12—H12A119.5
C18—N2—O4111.40 (14)C14—C13—C12120.25 (17)
C2—C1—C6119.35 (16)C14—C13—C17120.0 (2)
C2—C1—C7121.36 (16)C12—C13—C17119.7 (2)
C6—C1—C7119.25 (17)C15—C14—C13119.40 (18)
C1—C2—C3118.84 (16)C15—C14—H14A120.3
C1—C2—C20122.54 (16)C13—C14—H14A120.3
C3—C2—C20118.51 (17)C14—C15—C16120.44 (19)
C4—C3—C2121.18 (17)C14—C15—H15A119.8
C4—C3—H3A119.4C16—C15—H15A119.8
C2—C3—H3A119.4C11—C16—C15121.01 (18)
C5—C4—C3119.59 (18)C11—C16—H16A119.5
C5—C4—H4A120.2C15—C16—H16A119.5
C3—C4—H4A120.2N2—C18—C11125.24 (17)
C4—C5—C6120.15 (18)N2—C18—C19115.96 (16)
C4—C5—H5A119.9C11—C18—C19118.80 (17)
C6—C5—H5A119.9C18—C19—H19A109.5
C5—C6—C1120.88 (17)C18—C19—H19B109.5
C5—C6—H6A119.6H19A—C19—H19B109.5
C1—C6—H6A119.6C18—C19—H19C109.5
N1—C7—C1125.25 (15)H19A—C19—H19C109.5
N1—C7—C8115.38 (16)H19B—C19—H19C109.5
C1—C7—C8119.32 (15)O4—C20—C2111.08 (13)
O1—C8—O2124.31 (17)O4—C20—H20A109.4
O1—C8—C7123.30 (18)C2—C20—H20A109.4
O2—C8—C7112.39 (16)O4—C20—H20B109.4
O2—C9—H9A109.5C2—C20—H20B109.4
O2—C9—H9B109.5H20A—C20—H20B108.0
C10—O3—N1—C7176.45 (15)C11—C12—C13—C17178.72 (19)
C20—O4—N2—C18153.17 (14)F1'—C17—C13—C1488.8 (14)
C6—C1—C2—C30.7 (2)F1—C17—C13—C14145.5 (7)
C7—C1—C2—C3176.95 (14)F3—C17—C13—C1427.8 (9)
C6—C1—C2—C20175.39 (15)F3'—C17—C13—C1431.3 (8)
C7—C1—C2—C207.0 (2)F2—C17—C13—C1494.9 (12)
C1—C2—C3—C40.1 (2)F2'—C17—C13—C14148.5 (9)
C20—C2—C3—C4176.28 (16)F1'—C17—C13—C1291.7 (14)
C2—C3—C4—C50.5 (3)F1—C17—C13—C1234.9 (8)
C3—C4—C5—C60.2 (3)F3—C17—C13—C12152.7 (8)
C4—C5—C6—C10.5 (3)F3'—C17—C13—C12148.3 (8)
C2—C1—C6—C51.0 (2)F2—C17—C13—C1284.6 (12)
C7—C1—C6—C5176.69 (16)F2'—C17—C13—C1231.0 (10)
O3—N1—C7—C11.6 (2)C12—C13—C14—C150.6 (3)
O3—N1—C7—C8178.93 (13)C17—C13—C14—C15178.9 (2)
C2—C1—C7—N172.7 (2)C13—C14—C15—C160.9 (3)
C6—C1—C7—N1104.9 (2)C12—C11—C16—C152.1 (3)
C2—C1—C7—C8110.05 (18)C18—C11—C16—C15179.36 (18)
C6—C1—C7—C872.4 (2)C14—C15—C16—C112.4 (3)
C9—O2—C8—O12.3 (3)O4—N2—C18—C116.6 (2)
C9—O2—C8—C7177.32 (14)O4—N2—C18—C19174.58 (13)
N1—C7—C8—O1164.21 (17)C16—C11—C18—N2125.3 (2)
C1—C7—C8—O113.3 (3)C12—C11—C18—N257.5 (2)
N1—C7—C8—O215.5 (2)C16—C11—C18—C1955.9 (2)
C1—C7—C8—O2167.04 (14)C12—C11—C18—C19121.21 (18)
C16—C11—C12—C130.6 (2)N2—O4—C20—C278.71 (15)
C18—C11—C12—C13177.84 (15)C1—C2—C20—O4101.74 (18)
C11—C12—C13—C140.8 (2)C3—C2—C20—O474.31 (18)
 

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