Methyl (Z,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. Important features of the mol­ecule are the two C=N bonds in a Z,Z configuration, one in the β-­methoxy­acryl­ester system and the other in the oxy­methyl side-chain between the two aromatic rings.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.069
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT241_ALERT_2_A Check High   U(eq) as Compared to Neighbors ....        F3'
PLAT242_ALERT_2_A Check Low    U(eq) as Compared to Neighbors ....        C17

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....        F1'

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        F2'
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         F3
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         F1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.00 Deg.
              F2'  -C17  -F2      1.555   1.555   1.555
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
   2 ALERT level B = Potentially serious problem
   7 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
   7 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO & SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO & SCALEPACK (Otwinowski & Minor, 1997); 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, 2001).

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

Crystal data

C20H19F3N2O4	F(000) = 848
Mr = 408.37	Dx = 1.329 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 3855 reflections
a = 8.0122 (11) Å	θ = 3.0–25.1°
b = 6.9993 (6) Å	µ = 0.11 mm^−1
c = 36.417 (4) Å	T = 291 K
β = 91.945 (5)°	Block, colourless
V = 2041.1 (4) Å^3	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1275 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.1°, θmin = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −9→9
535 frames via ω–rotation (Δω=1°) and two times 50 s per frame (four sets at different κ–angles) scans	k = −8→8
3855 measured reflections	l = −43→43
3538 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H-atom parameters constrained
S = 1.01	[1.0 exp(4.20(sinθ/λ)^2)]/[σ^2(Fo^2)]
3538 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.09 e Å^−3
0 restraints	Δρmin = −0.13 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)
F1	0.3406 (15)	−0.6750 (19)	−0.0049 (3)	0.133 (3)	0.50
F2	0.0816 (15)	−0.705 (3)	−0.0048 (4)	0.159 (6)	0.50
F3	0.228 (3)	−0.8836 (13)	0.0270 (3)	0.191 (6)	0.50
F1'	0.201 (3)	−0.5959 (11)	−0.01664 (18)	0.162 (3)	0.50
F2'	0.096 (2)	−0.807 (3)	0.0115 (3)	0.181 (7)	0.50
F3'	0.3458 (17)	−0.796 (3)	0.0121 (5)	0.219 (8)	0.50
O1	−0.5434 (2)	0.4212 (2)	0.19113 (4)	0.0816 (6)
O2	−0.3203 (2)	0.2627 (2)	0.21423 (4)	0.0694 (5)
O3	−0.62433 (18)	−0.00576 (19)	0.21452 (4)	0.0670 (5)
O4	−0.12953 (19)	−0.3054 (2)	0.13287 (4)	0.0838 (6)
N1	−0.5664 (2)	−0.0342 (2)	0.17892 (5)	0.0577 (5)
N2	−0.1026 (2)	−0.4750 (3)	0.15373 (5)	0.0715 (6)
C1	−0.4063 (3)	0.1056 (3)	0.13232 (6)	0.0492 (6)
C2	−0.3134 (3)	−0.0487 (3)	0.12038 (6)	0.0524 (6)
C3	−0.2494 (3)	−0.0427 (3)	0.08545 (7)	0.0685 (7)
H3A	−0.1883	−0.1459	0.0771	0.082*
C4	−0.2750 (3)	0.1137 (4)	0.06301 (6)	0.0770 (8)
H4A	−0.2326	0.1145	0.0395	0.092*
C5	−0.3625 (3)	0.2681 (4)	0.07513 (7)	0.0765 (8)
H5A	−0.3773	0.3752	0.0603	0.092*
C6	−0.4286 (3)	0.2633 (3)	0.10966 (7)	0.0638 (7)
H6A	−0.4890	0.3675	0.1178	0.077*
C7	−0.4810 (2)	0.1090 (3)	0.16868 (6)	0.0470 (6)
C8	−0.4551 (3)	0.2833 (3)	0.19268 (7)	0.0575 (7)
C9	−0.2770 (3)	0.4259 (3)	0.23721 (6)	0.0981 (9)
H9A	−0.1735	0.4013	0.2504	0.147*
H9B	−0.3636	0.4472	0.2543	0.147*
H9C	−0.2653	0.5371	0.2221	0.147*
C10	−0.7284 (3)	−0.1627 (3)	0.22408 (7)	0.0997 (10)
H10A	−0.7684	−0.1437	0.2484	0.150*
H10B	−0.6652	−0.2791	0.2234	0.150*
H10C	−0.8216	−0.1707	0.2069	0.150*
C11	0.1175 (3)	−0.5121 (3)	0.10884 (7)	0.0592 (7)
C12	0.1234 (3)	−0.6287 (3)	0.07833 (7)	0.0657 (7)
H12A	0.0680	−0.7455	0.0780	0.079*
C13	0.2115 (3)	−0.5719 (4)	0.04830 (7)	0.0702 (7)
C14	0.2953 (3)	−0.4015 (4)	0.04828 (8)	0.0829 (8)
H14A	0.3532	−0.3643	0.0278	0.099*
C15	0.2933 (3)	−0.2859 (4)	0.07868 (9)	0.0842 (9)
H15A	0.3513	−0.1709	0.0790	0.101*
C16	0.2048 (3)	−0.3407 (3)	0.10890 (7)	0.0748 (8)
H16A	0.2038	−0.2619	0.1295	0.090*
C17	0.2142 (8)	−0.7002 (8)	0.01544 (13)	0.1008 (11)
C18	0.0182 (3)	−0.5702 (3)	0.14086 (6)	0.0596 (7)
C19	0.0574 (3)	−0.7568 (3)	0.15948 (6)	0.0838 (8)
H19A	−0.0203	−0.7785	0.1785	0.126*
H19B	0.1689	−0.7529	0.1700	0.126*
H19C	0.0488	−0.8585	0.1418	0.126*
C20	−0.2780 (3)	−0.2182 (3)	0.14481 (6)	0.0689 (7)
H20A	−0.2637	−0.1774	0.1702	0.083*
H20B	−0.3701	−0.3080	0.1431	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.101 (6)	0.202 (9)	0.099 (6)	−0.017 (6)	0.044 (5)	−0.032 (5)
F2	0.107 (7)	0.263 (14)	0.104 (9)	0.047 (9)	−0.033 (6)	−0.071 (8)
F3	0.395 (19)	0.095 (4)	0.086 (5)	0.053 (7)	0.031 (8)	−0.030 (4)
F1'	0.231 (10)	0.190 (6)	0.068 (4)	−0.032 (8)	0.024 (5)	−0.007 (3)
F2'	0.232 (14)	0.239 (14)	0.073 (7)	−0.131 (11)	0.046 (7)	−0.063 (7)
F3'	0.195 (11)	0.317 (19)	0.141 (13)	0.143 (11)	−0.047 (7)	−0.131 (12)
O1	0.0922 (14)	0.0560 (11)	0.0971 (14)	0.0199 (10)	0.0107 (11)	−0.0128 (10)
O2	0.0827 (13)	0.0658 (11)	0.0591 (12)	−0.0057 (9)	−0.0081 (10)	−0.0045 (9)
O3	0.0795 (11)	0.0562 (11)	0.0671 (11)	0.0034 (9)	0.0306 (9)	0.0018 (9)
O4	0.0846 (13)	0.0749 (12)	0.0948 (14)	0.0362 (10)	0.0436 (10)	0.0204 (11)
N1	0.0614 (13)	0.0555 (13)	0.0572 (14)	0.0067 (10)	0.0184 (10)	−0.0027 (11)
N2	0.0800 (15)	0.0663 (14)	0.0692 (15)	0.0229 (12)	0.0167 (12)	0.0074 (12)
C1	0.0518 (15)	0.0482 (15)	0.0478 (16)	−0.0001 (12)	0.0052 (12)	−0.0012 (14)
C2	0.0551 (15)	0.0542 (16)	0.0485 (16)	0.0035 (13)	0.0093 (12)	−0.0001 (13)
C3	0.0717 (19)	0.0724 (19)	0.0621 (19)	0.0135 (14)	0.0138 (15)	−0.0059 (15)
C4	0.083 (2)	0.096 (2)	0.0528 (18)	0.0095 (17)	0.0163 (15)	0.0038 (17)
C5	0.086 (2)	0.082 (2)	0.062 (2)	0.0080 (16)	0.0113 (16)	0.0224 (16)
C6	0.0659 (17)	0.0623 (17)	0.0636 (19)	0.0096 (13)	0.0088 (14)	0.0008 (15)
C7	0.0463 (15)	0.0418 (15)	0.0531 (16)	0.0101 (12)	0.0057 (12)	−0.0007 (13)
C8	0.068 (2)	0.0528 (18)	0.0531 (18)	−0.0030 (15)	0.0168 (15)	−0.0013 (15)
C9	0.135 (2)	0.089 (2)	0.069 (2)	−0.0376 (18)	−0.0094 (17)	−0.0201 (17)
C10	0.117 (2)	0.0674 (18)	0.119 (2)	−0.0090 (17)	0.0643 (19)	0.0118 (17)
C11	0.0483 (16)	0.0594 (17)	0.070 (2)	0.0101 (14)	0.0043 (13)	0.0008 (16)
C12	0.0580 (17)	0.0691 (18)	0.0703 (19)	0.0027 (13)	0.0081 (14)	−0.0066 (16)
C13	0.0631 (19)	0.086 (2)	0.062 (2)	0.0037 (16)	0.0075 (15)	−0.0077 (18)
C14	0.072 (2)	0.097 (2)	0.081 (2)	0.0041 (18)	0.0177 (17)	0.0149 (19)
C15	0.073 (2)	0.072 (2)	0.108 (3)	−0.0079 (16)	0.0132 (19)	0.007 (2)
C16	0.0677 (19)	0.071 (2)	0.085 (2)	0.0080 (15)	0.0045 (16)	−0.0096 (17)
C17	0.081 (4)	0.132 (4)	0.090 (4)	−0.005 (3)	0.017 (3)	−0.013 (3)
C18	0.0561 (17)	0.0618 (17)	0.0609 (18)	0.0098 (14)	0.0048 (13)	−0.0023 (14)
C19	0.0782 (19)	0.0797 (18)	0.094 (2)	0.0228 (15)	0.0098 (15)	0.0182 (16)
C20	0.0746 (18)	0.0609 (16)	0.0730 (19)	0.0168 (14)	0.0256 (14)	0.0020 (15)

Geometric parameters (Å, º)

F1—C17	1.288 (9)	C6—H6A	0.9300
F2—C17	1.274 (10)	C7—C8	1.511 (3)
F3—C17	1.354 (11)	C9—H9A	0.9600
F1'—C17	1.379 (9)	C9—H9B	0.9600
F2'—C17	1.212 (10)	C9—H9C	0.9600
F3'—C17	1.259 (10)	C10—H10A	0.9600
O1—C8	1.197 (2)	C10—H10B	0.9600
O2—C8	1.321 (3)	C10—H10C	0.9600
O2—C9	1.451 (2)	C11—C12	1.381 (3)
O3—N1	1.4063 (19)	C11—C16	1.389 (3)
O3—C10	1.429 (2)	C11—C18	1.490 (3)
O4—C20	1.419 (2)	C12—C13	1.380 (3)
O4—N2	1.4220 (19)	C12—H12A	0.9300
N1—C7	1.276 (2)	C13—C14	1.369 (3)
N2—C18	1.277 (2)	C13—C17	1.497 (4)
C1—C6	1.386 (3)	C14—C15	1.372 (3)
C1—C2	1.390 (2)	C14—H14A	0.9300
C1—C7	1.472 (2)	C15—C16	1.383 (3)
C2—C3	1.388 (3)	C15—H15A	0.9300
C2—C20	1.504 (2)	C16—H16A	0.9300
C3—C4	1.377 (3)	C18—C19	1.500 (3)
C3—H3A	0.9300	C19—H19A	0.9600
C4—C5	1.369 (3)	C19—H19B	0.9600
C4—H4A	0.9300	C19—H19C	0.9600
C5—C6	1.381 (2)	C20—H20A	0.9700
C5—H5A	0.9300	C20—H20B	0.9700
C8—O2—C9	115.55 (19)	C14—C13—C17	120.1 (3)
N1—O3—C10	109.23 (16)	C12—C13—C17	118.9 (3)
C20—O4—N2	108.02 (16)	C13—C14—C15	119.6 (3)
C7—N1—O3	110.79 (17)	C13—C14—H14A	120.2
C18—N2—O4	110.04 (18)	C15—C14—H14A	120.2
C6—C1—C2	119.5 (2)	C14—C15—C16	119.9 (2)
C6—C1—C7	118.3 (2)	C14—C15—H15A	120.0
C2—C1—C7	122.2 (2)	C16—C15—H15A	120.0
C3—C2—C1	118.8 (2)	C15—C16—C11	120.7 (2)
C3—C2—C20	119.9 (2)	C15—C16—H16A	119.7
C1—C2—C20	121.4 (2)	C11—C16—H16A	119.7
C4—C3—C2	121.1 (2)	F2'—C17—F3'	108.3 (11)
C4—C3—H3A	119.5	F2'—C17—F2	44.0 (7)
C2—C3—H3A	119.5	F3'—C17—F2	127.9 (7)
C5—C4—C3	120.2 (2)	F2'—C17—F1	130.1 (7)
C5—C4—H4A	119.9	F3'—C17—F1	48.8 (8)
C3—C4—H4A	119.9	F2—C17—F1	109.0 (7)
C4—C5—C6	119.4 (2)	F2'—C17—F3	60.6 (8)
C4—C5—H5A	120.3	F3'—C17—F3	57.6 (9)
C6—C5—H5A	120.3	F2—C17—F3	102.3 (10)
C5—C6—C1	121.1 (2)	F1—C17—F3	104.6 (9)
C5—C6—H6A	119.5	F2'—C17—F1'	100.8 (9)
C1—C6—H6A	119.5	F3'—C17—F1'	104.1 (8)
N1—C7—C1	119.2 (2)	F2—C17—F1'	58.8 (7)
N1—C7—C8	121.99 (19)	F1—C17—F1'	58.7 (5)
C1—C7—C8	118.8 (2)	F3—C17—F1'	140.2 (6)
O1—C8—O2	125.9 (2)	F2'—C17—C13	115.5 (6)
O1—C8—C7	123.7 (3)	F3'—C17—C13	115.6 (6)
O2—C8—C7	110.4 (2)	F2—C17—C13	116.4 (5)
O2—C9—H9A	109.5	F1—C17—C13	114.3 (5)
O2—C9—H9B	109.5	F3—C17—C13	108.9 (6)
H9A—C9—H9B	109.5	F1'—C17—C13	110.9 (5)
O2—C9—H9C	109.5	N2—C18—C11	125.2 (2)
H9A—C9—H9C	109.5	N2—C18—C19	116.0 (2)
H9B—C9—H9C	109.5	C11—C18—C19	118.8 (2)
O3—C10—H10A	109.5	C18—C19—H19A	109.5
O3—C10—H10B	109.5	C18—C19—H19B	109.5
H10A—C10—H10B	109.5	H19A—C19—H19B	109.5
O3—C10—H10C	109.5	C18—C19—H19C	109.5
H10A—C10—H10C	109.5	H19A—C19—H19C	109.5
H10B—C10—H10C	109.5	H19B—C19—H19C	109.5
C12—C11—C16	118.7 (2)	O4—C20—C2	107.55 (17)
C12—C11—C18	120.1 (2)	O4—C20—H20A	110.2
C16—C11—C18	121.1 (2)	C2—C20—H20A	110.2
C13—C12—C11	120.0 (2)	O4—C20—H20B	110.2
C13—C12—H12A	120.0	C2—C20—H20B	110.2
C11—C12—H12A	120.0	H20A—C20—H20B	108.5
C14—C13—C12	121.0 (3)
C10—O3—N1—C7	176.13 (18)	C11—C12—C13—C17	−179.3 (3)
C20—O4—N2—C18	172.09 (19)	C12—C13—C14—C15	0.7 (4)
C6—C1—C2—C3	−1.9 (3)	C17—C13—C14—C15	−179.4 (4)
C7—C1—C2—C3	178.9 (2)	C13—C14—C15—C16	−1.0 (4)
C6—C1—C2—C20	176.6 (2)	C14—C15—C16—C11	0.0 (4)
C7—C1—C2—C20	−2.6 (3)	C12—C11—C16—C15	1.3 (3)
C1—C2—C3—C4	0.8 (3)	C18—C11—C16—C15	−178.4 (2)
C20—C2—C3—C4	−177.7 (2)	C14—C13—C17—F2'	−154.1 (15)
C2—C3—C4—C5	1.0 (4)	C12—C13—C17—F2'	25.8 (16)
C3—C4—C5—C6	−1.7 (4)	C14—C13—C17—F3'	77.9 (17)
C4—C5—C6—C1	0.6 (4)	C12—C13—C17—F3'	−102.1 (16)
C2—C1—C6—C5	1.2 (3)	C14—C13—C17—F2	−104.9 (14)
C7—C1—C6—C5	−179.5 (2)	C12—C13—C17—F2	75.1 (14)
O3—N1—C7—C1	178.86 (16)	C14—C13—C17—F1	23.7 (12)
O3—N1—C7—C8	−1.6 (3)	C12—C13—C17—F1	−156.3 (10)
C6—C1—C7—N1	131.4 (2)	C14—C13—C17—F3	140.2 (12)
C2—C1—C7—N1	−49.3 (3)	C12—C13—C17—F3	−39.8 (13)
C6—C1—C7—C8	−48.2 (3)	C14—C13—C17—F1'	−40.3 (13)
C2—C1—C7—C8	131.1 (2)	C12—C13—C17—F1'	139.6 (12)
C9—O2—C8—O1	−1.3 (3)	O4—N2—C18—C11	0.4 (3)
C9—O2—C8—C7	176.72 (17)	O4—N2—C18—C19	−178.07 (18)
N1—C7—C8—O1	−92.6 (3)	C12—C11—C18—N2	−120.8 (3)
C1—C7—C8—O1	87.0 (3)	C16—C11—C18—N2	58.9 (3)
N1—C7—C8—O2	89.4 (3)	C12—C11—C18—C19	57.7 (3)
C1—C7—C8—O2	−91.1 (2)	C16—C11—C18—C19	−122.6 (2)
C16—C11—C12—C13	−1.6 (3)	N2—O4—C20—C2	−175.14 (17)
C18—C11—C12—C13	178.1 (2)	C3—C2—C20—O4	23.6 (3)
C11—C12—C13—C14	0.6 (4)	C1—C2—C20—O4	−154.84 (19)