Methyl (E,Z)-α-(methoxy­imino)-2-[({1-[3-(tri­fluoro­methyl)­phenyl]­ethyl­idene}amino)­oxy­methyl]­benzene­acetate

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.

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

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

Crystal data

C20H19F3N2O4	F(000) = 848
Mr = 408.37	Dx = 1.337 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14739 reflections
a = 8.0256 (12) Å	θ = 3.0–25.3°
b = 33.580 (5) Å	µ = 0.11 mm^−1
c = 8.0957 (11) Å	T = 291 K
β = 111.566 (5)°	Block, colourless
V = 2029.1 (5) Å^3	0.24 × 0.24 × 0.22 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1749 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.3°, θmin = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −9→9
551 frames via ω–rotation (Δω=1°) and two times 30 s per frame (four sets at differnt κ–angles) scans	k = −39→39
14739 measured reflections	l = −9→9
3658 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.021P)^2] where P = (Fo^2 + 2Fc^2)/3
3658 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.11 e Å^−3
30 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C17	−0.0749 (3)	0.21255 (9)	0.0365 (4)	0.0813 (6)
F1	−0.1777 (6)	0.2032 (3)	−0.1234 (10)	0.118 (3)	0.547 (11)
F2	−0.1225 (8)	0.1896 (6)	0.141 (2)	0.219 (7)	0.547 (11)
F3	−0.1331 (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)
O1	0.22879 (18)	0.03251 (4)	−0.19754 (17)	0.0886 (5)
O2	0.38273 (17)	0.02154 (3)	−0.37375 (15)	0.0671 (4)
O3	0.00672 (16)	0.07488 (4)	−0.77416 (16)	0.0803 (4)
O4	0.26611 (15)	0.16329 (3)	−0.31658 (16)	0.0615 (3)
N1	0.1334 (2)	0.05316 (4)	−0.6401 (2)	0.0675 (4)
N2	0.37316 (18)	0.13173 (4)	−0.2145 (2)	0.0616 (4)
C1	−0.0175 (2)	0.08513 (6)	−0.4593 (2)	0.0524 (4)
C2	−0.0079 (2)	0.12630 (6)	−0.4664 (2)	0.0531 (5)
C3	−0.1441 (3)	0.14898 (5)	−0.4459 (2)	0.0671 (5)
H3A	−0.1387	0.1766	−0.4503	0.081*
C4	−0.2872 (3)	0.13120 (7)	−0.4190 (2)	0.0777 (6)
H4A	−0.3777	0.1467	−0.4065	0.093*
C5	−0.2949 (3)	0.09067 (7)	−0.4109 (2)	0.0754 (6)
H5A	−0.3908	0.0786	−0.3924	0.090*
C6	−0.1611 (3)	0.06768 (6)	−0.4302 (2)	0.0675 (5)
H6A	−0.1670	0.0401	−0.4235	0.081*
C7	0.1190 (2)	0.05925 (5)	−0.4892 (2)	0.0538 (5)
C8	0.2474 (3)	0.03660 (5)	−0.3367 (3)	0.0597 (5)
C9	0.5107 (3)	−0.00253 (5)	−0.2366 (2)	0.0884 (6)
H9A	0.5929	−0.0147	−0.2827	0.133*
H9B	0.4482	−0.0229	−0.1992	0.133*
H9C	0.5756	0.0140	−0.1370	0.133*
C10	0.0210 (3)	0.06519 (6)	−0.9415 (2)	0.1083 (8)
H10A	−0.0605	0.0815	−1.0334	0.162*
H10B	−0.0083	0.0376	−0.9683	0.162*
H10C	0.1413	0.0700	−0.9346	0.162*
C11	0.3595 (2)	0.17226 (5)	0.0320 (2)	0.0534 (5)
C12	0.1787 (2)	0.17759 (5)	−0.0038 (2)	0.0549 (5)
H12A	0.0961	0.1604	−0.0817	0.066*
C13	0.1193 (3)	0.20807 (5)	0.0744 (2)	0.0580 (5)
C14	0.2393 (3)	0.23404 (6)	0.1880 (3)	0.0846 (6)
H14A	0.1992	0.2548	0.2400	0.102*
C15	0.4175 (3)	0.22918 (7)	0.2240 (3)	0.1057 (8)
H15A	0.4993	0.2469	0.2995	0.127*
C16	0.4777 (3)	0.19805 (6)	0.1490 (3)	0.0854 (6)
H16A	0.6001	0.1945	0.1782	0.102*
C18	0.4217 (2)	0.13849 (5)	−0.0482 (3)	0.0568 (5)
C19	0.5494 (3)	0.10889 (6)	0.0722 (3)	0.0926 (7)
H19A	0.5704	0.0877	0.0024	0.139*
H19B	0.4987	0.0981	0.1532	0.139*
H19C	0.6606	0.1219	0.1379	0.139*
C20	0.1504 (2)	0.14761 (5)	−0.4841 (2)	0.0645 (5)
H20A	0.2171	0.1292	−0.5288	0.077*
H20B	0.1080	0.1692	−0.5690	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C17	0.081 (2)	0.091 (2)	0.080 (2)	0.0138 (17)	0.0381 (18)	−0.0024 (19)
F1	0.060 (2)	0.156 (6)	0.124 (5)	0.023 (3)	0.016 (3)	−0.049 (5)
F2	0.074 (3)	0.356 (16)	0.237 (10)	0.033 (6)	0.069 (5)	0.196 (10)
F3	0.112 (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)
O1	0.1004 (11)	0.1148 (11)	0.0593 (9)	0.0330 (8)	0.0395 (9)	0.0221 (8)
O2	0.0692 (9)	0.0750 (8)	0.0571 (8)	0.0247 (7)	0.0234 (8)	0.0127 (6)
O3	0.0895 (10)	0.1028 (10)	0.0415 (8)	0.0377 (8)	0.0158 (8)	0.0033 (7)
O4	0.0657 (8)	0.0561 (7)	0.0582 (8)	0.0012 (7)	0.0175 (7)	−0.0008 (7)
N1	0.0752 (11)	0.0769 (11)	0.0456 (10)	0.0205 (9)	0.0167 (10)	0.0004 (9)
N2	0.0495 (9)	0.0607 (10)	0.0715 (12)	0.0089 (8)	0.0186 (10)	−0.0007 (9)
C1	0.0523 (12)	0.0620 (13)	0.0411 (11)	0.0015 (10)	0.0152 (10)	−0.0040 (9)
C2	0.0530 (12)	0.0630 (13)	0.0419 (11)	0.0037 (11)	0.0157 (10)	−0.0031 (9)
C3	0.0669 (14)	0.0689 (13)	0.0615 (13)	0.0126 (12)	0.0188 (11)	−0.0045 (10)
C4	0.0602 (15)	0.1034 (18)	0.0685 (15)	0.0171 (14)	0.0224 (12)	−0.0100 (13)
C5	0.0546 (14)	0.1059 (18)	0.0682 (14)	−0.0075 (13)	0.0254 (11)	−0.0075 (12)
C6	0.0698 (14)	0.0702 (13)	0.0638 (14)	−0.0046 (12)	0.0262 (12)	−0.0054 (10)
C7	0.0602 (12)	0.0553 (11)	0.0440 (12)	0.0046 (10)	0.0170 (11)	−0.0026 (10)
C8	0.0646 (14)	0.0594 (12)	0.0543 (14)	0.0071 (10)	0.0210 (12)	0.0002 (11)
C9	0.0968 (16)	0.0926 (15)	0.0691 (15)	0.0440 (13)	0.0227 (13)	0.0205 (12)
C10	0.134 (2)	0.148 (2)	0.0393 (13)	0.0458 (16)	0.0275 (14)	−0.0004 (12)
C11	0.0481 (12)	0.0575 (12)	0.0544 (12)	−0.0032 (10)	0.0187 (11)	−0.0018 (9)
C12	0.0507 (13)	0.0556 (11)	0.0561 (12)	−0.0012 (9)	0.0167 (10)	−0.0008 (9)
C13	0.0563 (13)	0.0601 (12)	0.0632 (13)	−0.0004 (11)	0.0287 (11)	−0.0018 (10)
C14	0.0921 (18)	0.0780 (14)	0.0987 (18)	−0.0097 (14)	0.0528 (16)	−0.0288 (13)
C15	0.0782 (17)	0.1183 (19)	0.129 (2)	−0.0365 (15)	0.0479 (16)	−0.0668 (16)
C16	0.0516 (13)	0.1095 (17)	0.0968 (17)	−0.0151 (13)	0.0293 (13)	−0.0316 (14)
C18	0.0454 (12)	0.0619 (13)	0.0585 (13)	0.0036 (9)	0.0136 (12)	−0.0003 (11)
C19	0.0776 (14)	0.0940 (15)	0.0886 (16)	0.0298 (12)	0.0098 (13)	0.0028 (12)
C20	0.0709 (14)	0.0692 (12)	0.0517 (13)	0.0040 (11)	0.0207 (12)	0.0014 (10)

Geometric parameters (Å, º)

C17—F1'	1.265 (6)	C5—H5A	0.9300
C17—F1	1.292 (5)	C6—H6A	0.9300
C17—F3	1.296 (4)	C7—C8	1.493 (2)
C17—F3'	1.301 (5)	C9—H9A	0.9600
C17—F2	1.304 (5)	C9—H9B	0.9600
C17—F2'	1.305 (6)	C9—H9C	0.9600
C17—C13	1.481 (3)	C10—H10A	0.9600
O1—C8	1.1980 (17)	C10—H10B	0.9600
O2—C8	1.3282 (18)	C10—H10C	0.9600
O2—C9	1.4500 (18)	C11—C16	1.374 (2)
O3—N1	1.3903 (16)	C11—C12	1.383 (2)
O3—C10	1.4384 (17)	C11—C18	1.482 (2)
O4—N2	1.4219 (16)	C12—C13	1.377 (2)
O4—C20	1.4328 (18)	C12—H12A	0.9300
N1—C7	1.2853 (17)	C13—C14	1.372 (2)
N2—C18	1.2769 (19)	C14—C15	1.360 (3)
C1—C2	1.387 (2)	C14—H14A	0.9300
C1—C6	1.388 (2)	C15—C16	1.382 (2)
C1—C7	1.486 (2)	C15—H15A	0.9300
C2—C3	1.392 (2)	C16—H16A	0.9300
C2—C20	1.510 (2)	C18—C19	1.501 (2)
C3—C4	1.380 (2)	C19—H19A	0.9600
C3—H3A	0.9300	C19—H19B	0.9600
C4—C5	1.365 (2)	C19—H19C	0.9600
C4—H4A	0.9300	C20—H20A	0.9700
C5—C6	1.377 (2)	C20—H20B	0.9700
F1—C17—F3	100.6 (4)	H9A—C9—H9B	109.5
F1'—C17—F3'	107.6 (5)	O2—C9—H9C	109.5
F1—C17—F2	106.1 (5)	H9A—C9—H9C	109.5
F3—C17—F2	107.1 (5)	H9B—C9—H9C	109.5
F1'—C17—F2'	107.8 (7)	O3—C10—H10A	109.5
F3'—C17—F2'	103.4 (5)	O3—C10—H10B	109.5
F1'—C17—C13	111.1 (4)	H10A—C10—H10B	109.5
F1—C17—C13	114.7 (3)	O3—C10—H10C	109.5
F3—C17—C13	117.3 (3)	H10A—C10—H10C	109.5
F3'—C17—C13	111.5 (4)	H10B—C10—H10C	109.5
F2—C17—C13	110.1 (3)	C16—C11—C12	117.93 (16)
F2'—C17—C13	114.9 (3)	C16—C11—C18	121.74 (17)
C8—O2—C9	116.56 (13)	C12—C11—C18	120.27 (16)
N1—O3—C10	109.15 (13)	C13—C12—C11	120.93 (16)
N2—O4—C20	108.60 (12)	C13—C12—H12A	119.5
C7—N1—O3	111.29 (13)	C11—C12—H12A	119.5
C18—N2—O4	111.40 (14)	C14—C13—C12	120.25 (17)
C2—C1—C6	119.35 (16)	C14—C13—C17	120.0 (2)
C2—C1—C7	121.36 (16)	C12—C13—C17	119.7 (2)
C6—C1—C7	119.25 (17)	C15—C14—C13	119.40 (18)
C1—C2—C3	118.84 (16)	C15—C14—H14A	120.3
C1—C2—C20	122.54 (16)	C13—C14—H14A	120.3
C3—C2—C20	118.51 (17)	C14—C15—C16	120.44 (19)
C4—C3—C2	121.18 (17)	C14—C15—H15A	119.8
C4—C3—H3A	119.4	C16—C15—H15A	119.8
C2—C3—H3A	119.4	C11—C16—C15	121.01 (18)
C5—C4—C3	119.59 (18)	C11—C16—H16A	119.5
C5—C4—H4A	120.2	C15—C16—H16A	119.5
C3—C4—H4A	120.2	N2—C18—C11	125.24 (17)
C4—C5—C6	120.15 (18)	N2—C18—C19	115.96 (16)
C4—C5—H5A	119.9	C11—C18—C19	118.80 (17)
C6—C5—H5A	119.9	C18—C19—H19A	109.5
C5—C6—C1	120.88 (17)	C18—C19—H19B	109.5
C5—C6—H6A	119.6	H19A—C19—H19B	109.5
C1—C6—H6A	119.6	C18—C19—H19C	109.5
N1—C7—C1	125.25 (15)	H19A—C19—H19C	109.5
N1—C7—C8	115.38 (16)	H19B—C19—H19C	109.5
C1—C7—C8	119.32 (15)	O4—C20—C2	111.08 (13)
O1—C8—O2	124.31 (17)	O4—C20—H20A	109.4
O1—C8—C7	123.30 (18)	C2—C20—H20A	109.4
O2—C8—C7	112.39 (16)	O4—C20—H20B	109.4
O2—C9—H9A	109.5	C2—C20—H20B	109.4
O2—C9—H9B	109.5	H20A—C20—H20B	108.0
C10—O3—N1—C7	−176.45 (15)	C11—C12—C13—C17	−178.72 (19)
C20—O4—N2—C18	−153.17 (14)	F1'—C17—C13—C14	88.8 (14)
C6—C1—C2—C3	−0.7 (2)	F1—C17—C13—C14	145.5 (7)
C7—C1—C2—C3	176.95 (14)	F3—C17—C13—C14	27.8 (9)
C6—C1—C2—C20	175.39 (15)	F3'—C17—C13—C14	−31.3 (8)
C7—C1—C2—C20	−7.0 (2)	F2—C17—C13—C14	−94.9 (12)
C1—C2—C3—C4	−0.1 (2)	F2'—C17—C13—C14	−148.5 (9)
C20—C2—C3—C4	−176.28 (16)	F1'—C17—C13—C12	−91.7 (14)
C2—C3—C4—C5	0.5 (3)	F1—C17—C13—C12	−34.9 (8)
C3—C4—C5—C6	−0.2 (3)	F3—C17—C13—C12	−152.7 (8)
C4—C5—C6—C1	−0.5 (3)	F3'—C17—C13—C12	148.3 (8)
C2—C1—C6—C5	1.0 (2)	F2—C17—C13—C12	84.6 (12)
C7—C1—C6—C5	−176.69 (16)	F2'—C17—C13—C12	31.0 (10)
O3—N1—C7—C1	1.6 (2)	C12—C13—C14—C15	−0.6 (3)
O3—N1—C7—C8	178.93 (13)	C17—C13—C14—C15	178.9 (2)
C2—C1—C7—N1	−72.7 (2)	C13—C14—C15—C16	−0.9 (3)
C6—C1—C7—N1	104.9 (2)	C12—C11—C16—C15	−2.1 (3)
C2—C1—C7—C8	110.05 (18)	C18—C11—C16—C15	−179.36 (18)
C6—C1—C7—C8	−72.4 (2)	C14—C15—C16—C11	2.4 (3)
C9—O2—C8—O1	2.3 (3)	O4—N2—C18—C11	6.6 (2)
C9—O2—C8—C7	−177.32 (14)	O4—N2—C18—C19	−174.58 (13)
N1—C7—C8—O1	−164.21 (17)	C16—C11—C18—N2	−125.3 (2)
C1—C7—C8—O1	13.3 (3)	C12—C11—C18—N2	57.5 (2)
N1—C7—C8—O2	15.5 (2)	C16—C11—C18—C19	55.9 (2)
C1—C7—C8—O2	−167.04 (14)	C12—C11—C18—C19	−121.21 (18)
C16—C11—C12—C13	0.6 (2)	N2—O4—C20—C2	78.71 (15)
C18—C11—C12—C13	177.84 (15)	C1—C2—C20—O4	−101.74 (18)
C11—C12—C13—C14	0.8 (2)	C3—C2—C20—O4	74.31 (18)