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

The title compound, C₂₀H₁₉F₃N₂O₄, crystallizes with two mol­ecules in the asymmetric unit. The important characteristics of the mol­ecule are the two C=N bonds in Z,E configuration, one in the β-methoxy-system and the other in the oxy­methyl side chain between the two aromatic rings.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.033
• wR factor = 0.050
• Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C13    -   C17     ..       8.98 su

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.16
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.35
           From the CIF: _reflns_number_total               3790
           Count of symmetry unique reflns         3800
           Completeness (_total/calc)             99.74%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO aand 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, 2001).

Methyl (Z,E)-α-methoxyimino-α-(1-{[3- (trifluoromethyl)phenyl]ethylideneaminooxymethyl}benzene)acetate

Crystal data

C20H19F3N2O4	F(000) = 1696
Mr = 408.37	Dx = 1.414 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 27239 reflections
a = 22.4800 (14) Å	θ = 2.9–25.4°
b = 22.1594 (15) Å	µ = 0.12 mm^−1
c = 7.7029 (6) Å	T = 173 K
V = 3837.1 (5) Å^3	Needle, colourless
Z = 8	0.34 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	2109 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 25.4°, θmin = 2.9°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −27→27
345 frames via ω–rotation (Δω=1°) and two times 100 s per frame (three sets at different κ–angles) scans	k = −26→26
27239 measured reflections	l = −9→9
3790 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.050	H-atom parameters constrained
S = 0.86	w = 1/[σ^2(Fo^2) + (0.005P)^2] where P = (Fo^2 + 2Fc^2)/3
3790 reflections	(Δ/σ)max < 0.001
529 parameters	Δρmax = 0.14 e Å^−3
1 restraint	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
F1	−0.18781 (8)	0.90406 (10)	0.4276 (3)	0.0715 (8)
F2	−0.17031 (9)	0.98851 (10)	0.5498 (3)	0.0642 (7)
F3	−0.21423 (8)	0.98733 (9)	0.3055 (3)	0.0667 (7)
F1'	−0.20367 (8)	0.42721 (9)	0.5017 (3)	0.0516 (6)
F2'	−0.18927 (8)	0.51707 (9)	0.5927 (3)	0.0595 (6)
F3'	−0.23558 (8)	0.50282 (9)	0.3552 (3)	0.0630 (6)
O1	0.12410 (10)	0.83558 (10)	0.7091 (3)	0.0487 (7)
O2	0.20169 (10)	0.80158 (10)	0.5492 (3)	0.0409 (7)
O3	0.18089 (10)	0.75591 (9)	0.9671 (3)	0.0428 (6)
O4	0.05707 (9)	0.78453 (9)	0.3639 (3)	0.0345 (6)
O1'	0.09532 (10)	0.30972 (10)	0.8162 (3)	0.0485 (7)
O2'	0.16562 (10)	0.23889 (10)	0.8601 (3)	0.0487 (7)
O3'	0.20030 (9)	0.34752 (10)	0.5919 (3)	0.0399 (6)
O4'	0.03553 (9)	0.30183 (9)	0.3520 (3)	0.0341 (6)
N1	0.16091 (11)	0.70979 (12)	0.8582 (4)	0.0350 (7)
N2	0.01372 (11)	0.83046 (12)	0.3573 (4)	0.0316 (7)
N1'	0.17878 (12)	0.30054 (12)	0.4869 (3)	0.0338 (7)
N2'	−0.00869 (11)	0.34702 (12)	0.3618 (4)	0.0329 (7)
C1	0.13219 (14)	0.68363 (14)	0.5719 (4)	0.0272 (9)
C2	0.07979 (14)	0.68811 (14)	0.4757 (4)	0.0285 (9)
C3	0.06578 (14)	0.64182 (15)	0.3611 (4)	0.0338 (9)
H3A	0.0309	0.6440	0.2964	0.041*
C4	0.10272 (16)	0.59270 (15)	0.3418 (5)	0.0385 (9)
H4A	0.0923	0.5618	0.2660	0.046*
C5	0.15467 (15)	0.58919 (15)	0.4337 (4)	0.0369 (10)
H5A	0.1800	0.5565	0.4180	0.044*
C6	0.16950 (14)	0.63431 (14)	0.5497 (4)	0.0342 (9)
H6A	0.2046	0.6316	0.6132	0.041*
C7	0.14879 (14)	0.72980 (15)	0.7044 (5)	0.0288 (9)
C8	0.15537 (17)	0.79495 (17)	0.6573 (5)	0.0368 (10)
C9	0.21402 (16)	0.86298 (14)	0.4952 (5)	0.0575 (11)
H9A	0.2455	0.8629	0.4108	0.086*
H9B	0.2259	0.8864	0.5941	0.086*
H9C	0.1789	0.8803	0.4448	0.086*
C10	0.18715 (15)	0.73239 (14)	1.1403 (4)	0.0451 (10)
H10A	0.2072	0.7615	1.2117	0.068*
H10B	0.2099	0.6958	1.1370	0.068*
H10C	0.1485	0.7242	1.1878	0.068*
C11	−0.01594 (15)	0.92220 (15)	0.2350 (4)	0.0270 (9)
C12	−0.07177 (15)	0.91759 (14)	0.3129 (4)	0.0317 (9)
H12B	−0.0823	0.8824	0.3710	0.038*
C13	−0.11141 (14)	0.96477 (15)	0.3043 (4)	0.0291 (9)
C14	−0.09735 (16)	1.01821 (14)	0.2189 (4)	0.0326 (9)
H14A	−0.1242	1.0501	0.2158	0.039*
C15	−0.04321 (16)	1.02258 (14)	0.1399 (4)	0.0363 (10)
H15A	−0.0332	1.0578	0.0813	0.044*
C16	−0.00283 (15)	0.97523 (15)	0.1455 (4)	0.0351 (10)
H16A	0.0335	0.9789	0.0888	0.042*
C17	−0.17075 (17)	0.96017 (18)	0.3931 (6)	0.0487 (11)
C18	0.02781 (14)	0.87207 (15)	0.2486 (4)	0.0294 (9)
C19	0.08335 (14)	0.87402 (13)	0.1415 (5)	0.0464 (11)
H19A	0.1031	0.8357	0.1476	0.070*
H19B	0.1092	0.9050	0.1851	0.070*
H19C	0.0733	0.8827	0.0229	0.070*
C20	0.03815 (13)	0.74053 (13)	0.4909 (4)	0.0322 (9)
H20A	−0.0024	0.7278	0.4679	0.039*
H20B	0.0399	0.7576	0.6067	0.039*
C1'	0.12275 (15)	0.20897 (15)	0.4869 (4)	0.0291 (9)
C2'	0.06367 (15)	0.20352 (15)	0.4372 (4)	0.0299 (9)
C3'	0.04655 (15)	0.15144 (15)	0.3500 (4)	0.0359 (9)
H3'A	0.0076	0.1478	0.3105	0.043*
C4'	0.08644 (17)	0.10490 (15)	0.3209 (5)	0.0395 (10)
H4'A	0.0738	0.0699	0.2654	0.047*
C5'	0.14457 (16)	0.11018 (15)	0.3735 (4)	0.0396 (10)
H5'A	0.1713	0.0789	0.3546	0.048*
C6'	0.16287 (15)	0.16279 (15)	0.4554 (4)	0.0375 (9)
H6'A	0.2024	0.1671	0.4893	0.045*
C7'	0.14574 (15)	0.26473 (15)	0.5734 (4)	0.0312 (9)
C8'	0.13245 (17)	0.27473 (17)	0.7622 (5)	0.0383 (10)
C9'	0.15676 (16)	0.24265 (16)	1.0492 (4)	0.0605 (12)
H9'A	0.1827	0.2145	1.1062	0.091*
H9'B	0.1162	0.2331	1.0766	0.091*
H9'C	0.1656	0.2828	1.0881	0.091*
C10'	0.23487 (15)	0.38762 (15)	0.4871 (5)	0.0525 (11)
H10D	0.2682	0.3662	0.4395	0.079*
H10E	0.2489	0.4205	0.5572	0.079*
H10F	0.2107	0.4030	0.3944	0.079*
C11'	−0.03794 (15)	0.44339 (15)	0.2684 (4)	0.0285 (9)
C12'	−0.09212 (14)	0.43903 (13)	0.3560 (4)	0.0286 (8)
H12'	−0.1013	0.4038	0.4159	0.034*
C13'	−0.13227 (14)	0.48613 (14)	0.3554 (5)	0.0284 (8)
C14'	−0.11938 (16)	0.53894 (14)	0.2642 (4)	0.0342 (9)
H14'	−0.1463	0.5708	0.2631	0.041*
C15'	−0.06644 (17)	0.54343 (15)	0.1759 (4)	0.0393 (10)
H15'	−0.0576	0.5786	0.1154	0.047*
C16'	−0.02614 (15)	0.49607 (16)	0.1763 (4)	0.0350 (9)
H16'	0.0092	0.4995	0.1143	0.042*
C17'	−0.18901 (16)	0.48230 (16)	0.4482 (5)	0.0401 (10)
C18'	0.00603 (15)	0.39348 (15)	0.2714 (4)	0.0293 (9)
C19'	0.06383 (15)	0.39877 (15)	0.1766 (5)	0.0542 (12)
H19D	0.0899	0.3667	0.2119	0.065*
H19E	0.0819	0.4369	0.2031	0.065*
H19F	0.0568	0.3961	0.0539	0.065*
C20'	0.01912 (13)	0.25281 (14)	0.4670 (4)	0.0356 (9)
H20C	−0.0207	0.2387	0.4408	0.043*
H20D	0.0202	0.2660	0.5870	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0471 (14)	0.0444 (15)	0.123 (2)	−0.0013 (11)	0.0262 (13)	0.0143 (14)
F2	0.0626 (15)	0.0748 (17)	0.0552 (16)	0.0096 (13)	0.0149 (14)	0.0017 (14)
F3	0.0372 (13)	0.0857 (18)	0.0772 (18)	0.0124 (11)	−0.0066 (13)	0.0231 (14)
F1'	0.0457 (13)	0.0367 (13)	0.0726 (16)	−0.0002 (11)	0.0133 (11)	0.0078 (12)
F2'	0.0578 (15)	0.0586 (15)	0.0623 (16)	−0.0075 (11)	0.0172 (13)	−0.0192 (13)
F3'	0.0371 (13)	0.0787 (16)	0.0732 (15)	0.0044 (11)	−0.0075 (14)	0.0281 (14)
O1	0.0631 (18)	0.0327 (17)	0.0504 (18)	0.0048 (14)	0.0069 (15)	−0.0050 (14)
O2	0.0522 (17)	0.0330 (16)	0.0374 (16)	−0.0074 (13)	0.0125 (14)	0.0039 (13)
O3	0.0556 (17)	0.0367 (15)	0.0360 (15)	−0.0103 (13)	−0.0032 (14)	−0.0021 (14)
O4	0.0401 (15)	0.0283 (14)	0.0349 (14)	0.0086 (12)	0.0036 (13)	0.0065 (13)
O1'	0.0561 (18)	0.0464 (18)	0.0429 (17)	0.0058 (13)	0.0121 (15)	−0.0073 (14)
O2'	0.0654 (18)	0.0512 (18)	0.0295 (16)	0.0157 (14)	0.0038 (15)	0.0068 (16)
O3'	0.0516 (16)	0.0320 (15)	0.0361 (16)	−0.0130 (13)	0.0098 (14)	−0.0037 (13)
O4'	0.0327 (14)	0.0302 (15)	0.0395 (14)	0.0037 (11)	0.0054 (13)	0.0070 (13)
N1	0.0336 (18)	0.0353 (19)	0.0361 (19)	−0.0046 (14)	0.0030 (16)	−0.0082 (18)
N2	0.0381 (18)	0.0244 (18)	0.0322 (19)	0.0041 (15)	−0.0011 (16)	0.0043 (17)
N1'	0.042 (2)	0.0254 (18)	0.0334 (18)	−0.0032 (15)	0.0021 (16)	−0.0045 (17)
N2'	0.0334 (18)	0.0320 (19)	0.0334 (18)	0.0039 (15)	−0.0043 (16)	−0.0010 (18)
C1	0.030 (2)	0.021 (2)	0.030 (2)	−0.0018 (18)	0.0053 (19)	−0.0035 (19)
C2	0.033 (2)	0.027 (2)	0.026 (2)	0.0011 (18)	0.0035 (19)	0.003 (2)
C3	0.036 (2)	0.037 (2)	0.029 (2)	−0.0022 (19)	−0.002 (2)	0.003 (2)
C4	0.051 (3)	0.030 (2)	0.035 (2)	−0.009 (2)	0.005 (2)	−0.004 (2)
C5	0.042 (3)	0.032 (2)	0.037 (2)	0.005 (2)	0.008 (2)	−0.003 (2)
C6	0.035 (2)	0.030 (2)	0.037 (2)	0.0000 (19)	0.0004 (19)	−0.002 (2)
C7	0.030 (2)	0.028 (2)	0.028 (2)	0.0027 (18)	0.0063 (18)	0.000 (2)
C8	0.045 (3)	0.034 (3)	0.031 (2)	0.000 (2)	−0.007 (2)	−0.005 (2)
C9	0.079 (3)	0.040 (3)	0.053 (3)	−0.013 (2)	0.009 (2)	0.006 (2)
C10	0.052 (3)	0.053 (3)	0.030 (2)	−0.002 (2)	0.001 (2)	0.006 (2)
C11	0.032 (2)	0.027 (2)	0.021 (2)	−0.0030 (18)	−0.0036 (18)	−0.0042 (18)
C12	0.036 (2)	0.028 (2)	0.031 (2)	−0.0002 (18)	−0.002 (2)	0.0014 (19)
C13	0.025 (2)	0.031 (2)	0.032 (2)	−0.0007 (18)	−0.0014 (19)	−0.0051 (19)
C14	0.043 (3)	0.022 (2)	0.033 (2)	0.0014 (19)	−0.008 (2)	0.0026 (19)
C15	0.049 (3)	0.025 (2)	0.035 (2)	−0.003 (2)	−0.002 (2)	0.007 (2)
C16	0.043 (2)	0.036 (2)	0.026 (2)	−0.005 (2)	0.0038 (19)	−0.002 (2)
C17	0.048 (3)	0.035 (3)	0.063 (3)	0.005 (2)	−0.011 (3)	0.006 (2)
C18	0.028 (2)	0.026 (2)	0.034 (2)	0.0017 (18)	−0.0049 (19)	−0.0053 (19)
C19	0.042 (3)	0.043 (3)	0.055 (3)	0.0021 (19)	0.006 (2)	0.013 (2)
C20	0.035 (2)	0.029 (2)	0.032 (2)	0.0002 (18)	0.0016 (18)	0.007 (2)
C1'	0.033 (2)	0.030 (2)	0.024 (2)	0.0005 (19)	0.0020 (18)	−0.0025 (19)
C2'	0.039 (3)	0.028 (2)	0.022 (2)	−0.0021 (19)	0.0056 (18)	0.0020 (18)
C3'	0.032 (2)	0.043 (3)	0.033 (2)	−0.003 (2)	0.002 (2)	0.001 (2)
C4'	0.050 (3)	0.034 (2)	0.034 (2)	−0.007 (2)	0.004 (2)	−0.0105 (19)
C5'	0.048 (3)	0.032 (2)	0.038 (2)	0.0080 (19)	0.003 (2)	−0.012 (2)
C6'	0.034 (2)	0.037 (2)	0.041 (2)	0.001 (2)	−0.001 (2)	−0.003 (2)
C7'	0.033 (2)	0.032 (2)	0.029 (2)	0.0065 (19)	0.0022 (19)	−0.005 (2)
C8'	0.042 (3)	0.033 (3)	0.040 (3)	−0.006 (2)	0.008 (2)	−0.001 (2)
C9'	0.076 (3)	0.078 (3)	0.027 (2)	0.007 (3)	0.008 (2)	0.007 (2)
C10'	0.062 (3)	0.041 (3)	0.054 (3)	−0.015 (2)	0.015 (2)	−0.002 (2)
C11'	0.032 (2)	0.028 (2)	0.025 (2)	−0.0033 (19)	−0.0044 (19)	−0.0022 (19)
C12'	0.038 (2)	0.025 (2)	0.022 (2)	−0.0036 (18)	−0.006 (2)	0.0006 (19)
C13'	0.034 (2)	0.022 (2)	0.029 (2)	−0.0017 (18)	−0.005 (2)	0.000 (2)
C14'	0.044 (3)	0.026 (2)	0.033 (2)	−0.0015 (19)	−0.005 (2)	−0.0001 (19)
C15'	0.055 (3)	0.029 (2)	0.034 (2)	−0.009 (2)	0.001 (2)	0.0047 (19)
C16'	0.041 (2)	0.034 (2)	0.030 (2)	−0.004 (2)	0.0013 (18)	0.000 (2)
C17'	0.039 (3)	0.027 (2)	0.054 (3)	0.001 (2)	−0.006 (2)	0.002 (2)
C18'	0.033 (2)	0.031 (2)	0.024 (2)	−0.0054 (19)	−0.0022 (18)	−0.004 (2)
C19'	0.053 (3)	0.039 (2)	0.071 (3)	0.005 (2)	0.020 (2)	0.006 (2)
C20'	0.035 (2)	0.037 (2)	0.036 (2)	0.0008 (19)	0.002 (2)	0.004 (2)

Geometric parameters (Å, º)

F1—C17	1.328 (4)	C13—C17	1.502 (5)
F2—C17	1.361 (4)	C14—C15	1.364 (4)
F3—C17	1.331 (4)	C14—H14A	0.9300
F1'—C17'	1.330 (3)	C15—C16	1.388 (4)
F2'—C17'	1.354 (4)	C15—H15A	0.9300
F3'—C17'	1.347 (4)	C16—H16A	0.9300
O1—C8	1.210 (4)	C18—C19	1.497 (4)
O2—C8	1.341 (4)	C19—H19A	0.9600
O2—C9	1.450 (3)	C19—H19B	0.9600
O3—N1	1.396 (3)	C19—H19C	0.9600
O3—C10	1.439 (3)	C20—H20A	0.9700
O4—N2	1.410 (3)	C20—H20B	0.9700
O4—C20	1.445 (3)	C1'—C6'	1.386 (4)
O1'—C8'	1.213 (4)	C1'—C2'	1.387 (4)
O2'—C8'	1.325 (4)	C1'—C7'	1.496 (4)
O2'—C9'	1.473 (3)	C2'—C3'	1.390 (4)
O3'—N1'	1.404 (3)	C2'—C20'	1.500 (4)
O3'—C10'	1.430 (3)	C3'—C4'	1.385 (4)
O4'—N2'	1.413 (3)	C3'—H3'A	0.9300
O4'—C20'	1.449 (3)	C4'—C5'	1.373 (4)
N1—C7	1.294 (4)	C4'—H4'A	0.9300
N2—C18	1.285 (3)	C5'—C6'	1.388 (4)
N1'—C7'	1.275 (3)	C5'—H5'A	0.9300
N2'—C18'	1.286 (3)	C6'—H6'A	0.9300
C1—C6	1.388 (4)	C7'—C8'	1.501 (5)
C1—C2	1.395 (4)	C9'—H9'A	0.9600
C1—C7	1.493 (4)	C9'—H9'B	0.9600
C2—C3	1.389 (4)	C9'—H9'C	0.9600
C2—C20	1.496 (4)	C10'—H10D	0.9600
C3—C4	1.377 (4)	C10'—H10E	0.9600
C3—H3A	0.9300	C10'—H10F	0.9600
C4—C5	1.368 (4)	C11'—C16'	1.391 (4)
C4—H4A	0.9300	C11'—C12'	1.396 (4)
C5—C6	1.382 (4)	C11'—C18'	1.484 (4)
C5—H5A	0.9300	C12'—C13'	1.380 (4)
C6—H6A	0.9300	C12'—H12'	0.9300
C7—C8	1.496 (4)	C13'—C14'	1.395 (4)
C9—H9A	0.9600	C13'—C17'	1.465 (4)
C9—H9B	0.9600	C14'—C15'	1.374 (4)
C9—H9C	0.9600	C14'—H14'	0.9300
C10—H10A	0.9600	C15'—C16'	1.386 (4)
C10—H10B	0.9600	C15'—H15'	0.9300
C10—H10C	0.9600	C16'—H16'	0.9300
C11—C16	1.394 (4)	C18'—C19'	1.495 (4)
C11—C12	1.395 (4)	C19'—H19D	0.9600
C11—C18	1.487 (4)	C19'—H19E	0.9600
C12—C13	1.375 (4)	C19'—H19F	0.9600
C12—H12B	0.9300	C20'—H20C	0.9700
C13—C14	1.391 (4)	C20'—H20D	0.9700
C8—O2—C9	115.4 (3)	O4—C20—H20A	110.4
N1—O3—C10	108.8 (2)	C2—C20—H20A	110.4
N2—O4—C20	107.9 (2)	O4—C20—H20B	110.4
C8'—O2'—C9'	116.9 (3)	C2—C20—H20B	110.4
N1'—O3'—C10'	108.9 (2)	H20A—C20—H20B	108.6
N2'—O4'—C20'	108.6 (2)	C6'—C1'—C2'	120.7 (3)
C7—N1—O3	111.5 (3)	C6'—C1'—C7'	117.6 (3)
C18—N2—O4	111.8 (3)	C2'—C1'—C7'	121.7 (3)
C7'—N1'—O3'	111.2 (3)	C3'—C2'—C1'	118.1 (3)
C18'—N2'—O4'	110.9 (3)	C3'—C2'—C20'	119.6 (3)
C6—C1—C2	120.1 (3)	C1'—C2'—C20'	122.2 (3)
C6—C1—C7	118.2 (3)	C4'—C3'—C2'	121.1 (3)
C2—C1—C7	121.7 (3)	C4'—C3'—H3'A	119.4
C3—C2—C1	118.4 (3)	C2'—C3'—H3'A	119.4
C3—C2—C20	118.7 (3)	C5'—C4'—C3'	120.3 (3)
C1—C2—C20	122.8 (3)	C5'—C4'—H4'A	119.8
C4—C3—C2	121.0 (3)	C3'—C4'—H4'A	119.8
C4—C3—H3A	119.5	C4'—C5'—C6'	119.2 (3)
C2—C3—H3A	119.5	C4'—C5'—H5'A	120.4
C5—C4—C3	120.3 (3)	C6'—C5'—H5'A	120.4
C5—C4—H4A	119.9	C1'—C6'—C5'	120.5 (3)
C3—C4—H4A	119.9	C1'—C6'—H6'A	119.8
C4—C5—C6	120.0 (3)	C5'—C6'—H6'A	119.8
C4—C5—H5A	120.0	N1'—C7'—C1'	118.8 (3)
C6—C5—H5A	120.0	N1'—C7'—C8'	122.0 (3)
C5—C6—C1	120.2 (3)	C1'—C7'—C8'	119.0 (3)
C5—C6—H6A	119.9	O1'—C8'—O2'	125.1 (4)
C1—C6—H6A	119.9	O1'—C8'—C7'	124.3 (4)
N1—C7—C1	116.4 (3)	O2'—C8'—C7'	110.5 (3)
N1—C7—C8	122.2 (3)	O2'—C9'—H9'A	109.5
C1—C7—C8	121.3 (3)	O2'—C9'—H9'B	109.5
O1—C8—O2	125.1 (4)	H9'A—C9'—H9'B	109.5
O1—C8—C7	125.5 (4)	O2'—C9'—H9'C	109.5
O2—C8—C7	109.5 (3)	H9'A—C9'—H9'C	109.5
O2—C9—H9A	109.5	H9'B—C9'—H9'C	109.5
O2—C9—H9B	109.5	O3'—C10'—H10D	109.5
H9A—C9—H9B	109.5	O3'—C10'—H10E	109.5
O2—C9—H9C	109.5	H10D—C10'—H10E	109.5
H9A—C9—H9C	109.5	O3'—C10'—H10F	109.5
H9B—C9—H9C	109.5	H10D—C10'—H10F	109.5
O3—C10—H10A	109.5	H10E—C10'—H10F	109.5
O3—C10—H10B	109.5	C16'—C11'—C12'	118.1 (3)
H10A—C10—H10B	109.5	C16'—C11'—C18'	120.4 (3)
O3—C10—H10C	109.5	C12'—C11'—C18'	121.5 (3)
H10A—C10—H10C	109.5	C13'—C12'—C11'	121.1 (3)
H10B—C10—H10C	109.5	C13'—C12'—H12'	119.4
C16—C11—C12	117.7 (3)	C11'—C12'—H12'	119.4
C16—C11—C18	121.7 (3)	C12'—C13'—C14'	120.0 (3)
C12—C11—C18	120.7 (3)	C12'—C13'—C17'	121.6 (3)
C13—C12—C11	120.5 (3)	C14'—C13'—C17'	118.4 (3)
C13—C12—H12B	119.8	C15'—C14'—C13'	119.3 (3)
C11—C12—H12B	119.8	C15'—C14'—H14'	120.3
C12—C13—C14	121.5 (3)	C13'—C14'—H14'	120.3
C12—C13—C17	120.1 (3)	C14'—C15'—C16'	120.7 (3)
C14—C13—C17	118.3 (3)	C14'—C15'—H15'	119.7
C15—C14—C13	118.3 (3)	C16'—C15'—H15'	119.7
C15—C14—H14A	120.8	C15'—C16'—C11'	120.8 (3)
C13—C14—H14A	120.8	C15'—C16'—H16'	119.6
C14—C15—C16	121.1 (3)	C11'—C16'—H16'	119.6
C14—C15—H15A	119.5	F1'—C17'—F3'	106.4 (3)
C16—C15—H15A	119.5	F1'—C17'—F2'	105.5 (3)
C15—C16—C11	121.0 (3)	F3'—C17'—F2'	104.0 (3)
C15—C16—H16A	119.5	F1'—C17'—C13'	114.8 (3)
C11—C16—H16A	119.5	F3'—C17'—C13'	113.4 (3)
F1—C17—F3	108.2 (3)	F2'—C17'—C13'	111.9 (3)
F1—C17—F2	104.9 (3)	N2'—C18'—C11'	115.7 (3)
F3—C17—F2	104.3 (3)	N2'—C18'—C19'	123.4 (3)
F1—C17—C13	114.3 (3)	C11'—C18'—C19'	120.9 (3)
F3—C17—C13	113.0 (3)	C18'—C19'—H19D	109.5
F2—C17—C13	111.5 (3)	C18'—C19'—H19E	109.5
N2—C18—C11	114.8 (3)	H19D—C19'—H19E	109.5
N2—C18—C19	125.8 (3)	C18'—C19'—H19F	109.5
C11—C18—C19	119.4 (3)	H19D—C19'—H19F	109.5
C18—C19—H19A	109.5	H19E—C19'—H19F	109.5
C18—C19—H19B	109.5	O4'—C20'—C2'	106.4 (3)
H19A—C19—H19B	109.5	O4'—C20'—H20C	110.5
C18—C19—H19C	109.5	C2'—C20'—H20C	110.5
H19A—C19—H19C	109.5	O4'—C20'—H20D	110.5
H19B—C19—H19C	109.5	C2'—C20'—H20D	110.5
O4—C20—C2	106.7 (3)	H20C—C20'—H20D	108.6
C10—O3—N1—C7	173.6 (3)	C3—C2—C20—O4	−89.8 (3)
C20—O4—N2—C18	179.0 (2)	C1—C2—C20—O4	90.3 (4)
C10'—O3'—N1'—C7'	−177.6 (3)	C6'—C1'—C2'—C3'	−2.1 (5)
C20'—O4'—N2'—C18'	175.3 (2)	C7'—C1'—C2'—C3'	176.9 (3)
C6—C1—C2—C3	1.2 (5)	C6'—C1'—C2'—C20'	−179.2 (3)
C7—C1—C2—C3	−176.7 (3)	C7'—C1'—C2'—C20'	−0.1 (5)
C6—C1—C2—C20	−178.9 (3)	C1'—C2'—C3'—C4'	3.2 (5)
C7—C1—C2—C20	3.2 (5)	C20'—C2'—C3'—C4'	−179.7 (3)
C1—C2—C3—C4	−0.3 (5)	C2'—C3'—C4'—C5'	−2.0 (5)
C20—C2—C3—C4	179.8 (3)	C3'—C4'—C5'—C6'	−0.3 (5)
C2—C3—C4—C5	−1.1 (5)	C2'—C1'—C6'—C5'	−0.1 (5)
C3—C4—C5—C6	1.7 (5)	C7'—C1'—C6'—C5'	−179.2 (3)
C4—C5—C6—C1	−0.8 (5)	C4'—C5'—C6'—C1'	1.3 (5)
C2—C1—C6—C5	−0.6 (5)	O3'—N1'—C7'—C1'	−175.0 (3)
C7—C1—C6—C5	177.3 (3)	O3'—N1'—C7'—C8'	1.0 (4)
O3—N1—C7—C1	174.7 (2)	C6'—C1'—C7'—N1'	72.4 (4)
O3—N1—C7—C8	−0.8 (4)	C2'—C1'—C7'—N1'	−106.7 (4)
C6—C1—C7—N1	−51.3 (4)	C6'—C1'—C7'—C8'	−103.7 (4)
C2—C1—C7—N1	126.7 (3)	C2'—C1'—C7'—C8'	77.2 (4)
C6—C1—C7—C8	124.3 (3)	C9'—O2'—C8'—O1'	−0.7 (5)
C2—C1—C7—C8	−57.8 (4)	C9'—O2'—C8'—C7'	−178.8 (3)
C9—O2—C8—O1	0.7 (5)	N1'—C7'—C8'—O1'	80.4 (5)
C9—O2—C8—C7	−178.9 (3)	C1'—C7'—C8'—O1'	−103.6 (4)
N1—C7—C8—O1	−70.2 (5)	N1'—C7'—C8'—O2'	−101.4 (4)
C1—C7—C8—O1	114.5 (4)	C1'—C7'—C8'—O2'	74.6 (4)
N1—C7—C8—O2	109.4 (3)	C16'—C11'—C12'—C13'	−1.6 (5)
C1—C7—C8—O2	−65.9 (4)	C18'—C11'—C12'—C13'	178.7 (3)
C16—C11—C12—C13	−1.7 (4)	C11'—C12'—C13'—C14'	0.9 (5)
C18—C11—C12—C13	178.1 (3)	C11'—C12'—C13'—C17'	−179.4 (3)
C11—C12—C13—C14	−0.1 (5)	C12'—C13'—C14'—C15'	−0.2 (5)
C11—C12—C13—C17	−178.2 (3)	C17'—C13'—C14'—C15'	−179.9 (3)
C12—C13—C14—C15	1.3 (5)	C13'—C14'—C15'—C16'	0.3 (5)
C17—C13—C14—C15	179.3 (3)	C14'—C15'—C16'—C11'	−1.1 (5)
C13—C14—C15—C16	−0.6 (5)	C12'—C11'—C16'—C15'	1.8 (5)
C14—C15—C16—C11	−1.3 (5)	C18'—C11'—C16'—C15'	−178.6 (3)
C12—C11—C16—C15	2.3 (4)	C12'—C13'—C17'—F1'	−12.8 (5)
C18—C11—C16—C15	−177.4 (3)	C14'—C13'—C17'—F1'	166.9 (3)
C12—C13—C17—F1	−20.1 (5)	C12'—C13'—C17'—F3'	−135.5 (3)
C14—C13—C17—F1	161.8 (3)	C14'—C13'—C17'—F3'	44.3 (5)
C12—C13—C17—F3	−144.4 (3)	C12'—C13'—C17'—F2'	107.3 (4)
C14—C13—C17—F3	37.5 (5)	C14'—C13'—C17'—F2'	−73.0 (4)
C12—C13—C17—F2	98.6 (4)	O4'—N2'—C18'—C11'	178.5 (3)
C14—C13—C17—F2	−79.5 (4)	O4'—N2'—C18'—C19'	−2.6 (4)
O4—N2—C18—C11	−179.9 (2)	C16'—C11'—C18'—N2'	179.2 (3)
O4—N2—C18—C19	−0.9 (4)	C12'—C11'—C18'—N2'	−1.2 (5)
C16—C11—C18—N2	169.2 (3)	C16'—C11'—C18'—C19'	0.3 (5)
C12—C11—C18—N2	−10.5 (4)	C12'—C11'—C18'—C19'	179.9 (3)
C16—C11—C18—C19	−9.8 (4)	N2'—O4'—C20'—C2'	173.9 (2)
C12—C11—C18—C19	170.5 (3)	C3'—C2'—C20'—O4'	−108.0 (3)
N2—O4—C20—C2	171.6 (2)	C1'—C2'—C20'—O4'	69.0 (4)