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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2870.
Published online 2009 October 28. doi:  10.1107/S1600536809043888
PMCID: PMC2971354

(E)-2-[2-(Penta­fluoro­phen­yl)ethen­yl]-8-quinolyl acetate

Abstract

The title compound, C19H10F5NO2, was synthesized by the 1:1 condensation of 2-methyl-8-hydroxy­quinaldine with penta­fluoro­benzaldehyde. It crystallizes with two almost identical mol­ecules in the asymmetric unit. The penta­fluoro­benzene ring is essentially coplanar with the quinoline ring, forming dihedral angles of 2.49 (17) and 8.72 (16)° in the two mol­ecules.

Related literature

For a recent review on the synthesis of quinoline derivatives, see: Zeng et al. (2006 [triangle]).

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Object name is e-65-o2870-scheme1.jpg

Experimental

Crystal data

  • C19H10F5NO2
  • M r = 379.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2870-efi1.jpg
  • a = 12.3149 (13) Å
  • b = 8.6730 (9) Å
  • c = 15.0491 (16) Å
  • β = 93.786 (2)°
  • V = 1603.8 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 293 K
  • 0.40 × 0.37 × 0.23 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.946, T max = 0.968
  • 9498 measured reflections
  • 3695 independent reflections
  • 2952 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.108
  • S = 0.98
  • 3695 reflections
  • 490 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043888/bt5079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043888/bt5079Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Natural Science Foundation of China (20802010), the Natural Science Foundation of Guangdong Province (No.07300884) and the 211 project of Guangdong University of Technology.

supplementary crystallographic information

Comment

Herein, we report the crystal structure of (E)-2-[2-(pentafluorophenyl)ethenyl]-8-acetoxyquinoline, which was prepared via a reaction of 2-methyl-8-hydroxyquinaldine with pentafluorobenzaldehyde according to the procedure reported by Zeng et al. (2006). The title compound crystallizes with two almost identical molecules in asymmetric unit (Fig. 1.). The pentafluorobenzene ring is essentially coplanar with quinoline ring.

Experimental

To a solution of 8-hydroxyquinaldine(1.19 g, 7.5 mmol) in acetic anhydride (5 mL) was added pentafluorobenzaldehyde (1.47 g, 7.5 mmol). The mixture was heated under reflux for 14 h . After cooling down to room temperature, it was subsequently poured into ice water (50 mL) and stirred overnight. The yellow solid obtained was filtered and washed with water. The solid residue was recrystallized from CH2Cl2 to afford the title compound (2.13 g, 75%) mp 129-131 °C, 1H NMR (CDCl3, 300 MHz): 8.18 (d, J=8.7 Hz, 1H), 7.85 (d, J=16.5 Hz, 1H), 7.70 (dd, J=1.6 Hz, J=7.8 Hz 1H), 7.67 (d, J=16.5 Hz, 1H), 7.55 (t, J=8.4 Hz, 1H), 7.53 (d, J=8.1 Hz, 1H), 7.48 (dd, J=1.6 Hz, J=7.6 Hz, 1H), 2.56(s, 3H); 19F NMR (CDCl3, 282 MHz): -141.35 to 141.41(2F, m), -154.35 to 154.50(1F,m), -162.32 to 162.50 (2F, m); IR (KBr, cm-1): 3056, 1717, 1584, 1512, 1423, 1275, 1128, 987, 878, 765, 710; EI-MS m/z:(%) 379.0 [M+,0.86], 338.0 [(M-61)+, 20], 337.0 [(M-62)+, 100]; Elemental analysis: found C: 59.97, H: 2.30, N: 3.50 calculated for C19H10F5NO2: C, 60.17; H, 2.66; N, 3.69 (%)

Refinement

All H atoms were positioned geometrically and refined using a riding model (including free rotation about the ethanol C-C bond), with C-H = 0.93-0.96 Å and with Uiso(H) = 1.2Ueq(C) or with Uiso(H) = 1.5Ueq(Cmethyl). Due to the absence of anomalous scatterers, the absolute structure could not be determined and was arbitrarily set. Friedel pairs were merged.

Figures

Fig. 1.
View of the two molecules in the asymmetric unit of the title compound.

Crystal data

C19H10F5NO2F(000) = 768
Mr = 379.28Dx = 1.571 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 12.3149 (13) ÅCell parameters from 3790 reflections
b = 8.6730 (9) Åθ = 2.1–27.0°
c = 15.0491 (16) ŵ = 0.14 mm1
β = 93.786 (2)°T = 293 K
V = 1603.8 (3) Å3Prismatic, colorless
Z = 40.40 × 0.37 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer3695 independent reflections
Radiation source: fine-focus sealed tube2952 reflections with I > 2σ(I)
graphiteRint = 0.041
[var phi] and ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −12→15
Tmin = 0.946, Tmax = 0.968k = −10→11
9498 measured reflectionsl = −18→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.108w = 1/[σ2(Fo2) + (0.0647P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
3695 reflectionsΔρmax = 0.21 e Å3
490 parametersΔρmin = −0.19 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (13)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
F10.33611 (15)−0.0821 (3)0.65824 (12)0.0664 (6)
F20.49061 (15)−0.2657 (3)0.73041 (16)0.0803 (7)
F30.49694 (18)−0.3382 (3)0.90485 (18)0.0946 (8)
F40.3463 (2)−0.2163 (4)1.00830 (16)0.1119 (10)
F50.19062 (18)−0.0336 (3)0.93763 (12)0.0867 (8)
F60.36601 (15)0.4554 (3)0.08205 (11)0.0660 (6)
F70.19161 (18)0.2788 (4)0.07778 (15)0.0931 (8)
F80.06916 (18)0.2615 (4)0.22027 (18)0.1004 (9)
F90.12930 (17)0.4170 (3)0.37066 (14)0.0825 (7)
F100.30608 (16)0.5948 (3)0.37770 (11)0.0660 (6)
O1−0.16350 (15)0.2719 (3)0.84497 (13)0.0506 (5)
O2−0.02488 (19)0.4204 (3)0.89609 (14)0.0641 (6)
O30.61824 (15)1.0012 (3)0.43067 (12)0.0470 (5)
O40.67283 (19)0.7628 (3)0.46897 (16)0.0686 (7)
N1−0.01615 (17)0.2314 (3)0.71999 (14)0.0423 (5)
N20.60340 (17)0.8523 (3)0.27113 (14)0.0394 (5)
C1−0.1009 (2)0.3273 (4)0.70004 (18)0.0412 (6)
C2−0.1761 (2)0.3553 (4)0.76599 (19)0.0458 (7)
C3−0.2632 (2)0.4477 (5)0.7503 (2)0.0578 (8)
H3−0.31160.46350.79440.069*
C4−0.2803 (3)0.5196 (5)0.6673 (3)0.0663 (10)
H4−0.34060.58310.65670.080*
C5−0.2108 (3)0.4990 (4)0.6018 (2)0.0600 (9)
H5−0.22340.54830.54720.072*
C6−0.1195 (2)0.4022 (4)0.61722 (19)0.0487 (7)
C7−0.0439 (3)0.3736 (4)0.55332 (19)0.0532 (8)
H7−0.05290.41850.49720.064*
C80.0428 (3)0.2798 (4)0.57407 (18)0.0514 (7)
H80.09430.26210.53270.062*
C90.0542 (2)0.2100 (4)0.65838 (17)0.0418 (6)
C100.1487 (2)0.1104 (4)0.68194 (19)0.0460 (7)
H100.19910.09410.63960.055*
C110.1649 (2)0.0435 (4)0.76047 (19)0.0460 (7)
H110.11120.06110.79990.055*
C120.2539 (2)−0.0531 (4)0.79412 (19)0.0454 (7)
C130.3347 (2)−0.1141 (4)0.7447 (2)0.0493 (7)
C140.4153 (2)−0.2109 (4)0.7816 (2)0.0560 (8)
C150.4186 (3)−0.2449 (5)0.8695 (3)0.0647 (9)
C160.3431 (3)−0.1861 (6)0.9211 (2)0.0691 (10)
C170.2627 (3)−0.0916 (5)0.8837 (2)0.0592 (9)
C18−0.0773 (2)0.3068 (4)0.90196 (19)0.0505 (7)
C19−0.0608 (3)0.1843 (6)0.9706 (3)0.0765 (11)
H19A−0.02310.22671.02290.115*
H19B−0.01850.10220.94770.115*
H19C−0.13020.14510.98560.115*
C200.6904 (2)0.9448 (3)0.28986 (17)0.0372 (6)
C210.7023 (2)1.0169 (4)0.37360 (17)0.0419 (6)
C220.7883 (2)1.1090 (4)0.3970 (2)0.0492 (7)
H220.79451.15490.45290.059*
C230.8684 (2)1.1348 (4)0.3357 (2)0.0542 (8)
H230.92751.19790.35170.065*
C240.8601 (2)1.0690 (4)0.2543 (2)0.0486 (7)
H240.91381.08680.21490.058*
C250.7707 (2)0.9734 (4)0.22833 (18)0.0415 (7)
C260.7552 (2)0.9032 (4)0.14474 (18)0.0468 (7)
H260.80520.91890.10200.056*
C270.6678 (2)0.8130 (4)0.12635 (18)0.0477 (7)
H270.65630.76830.07040.057*
C280.5935 (2)0.7863 (4)0.19247 (17)0.0398 (6)
C290.5021 (2)0.6793 (4)0.17519 (18)0.0446 (7)
H290.48940.63910.11820.053*
C300.4372 (2)0.6379 (4)0.23760 (18)0.0433 (6)
H300.45310.68080.29360.052*
C310.3443 (2)0.5342 (4)0.23035 (18)0.0414 (6)
C320.3102 (2)0.4496 (4)0.15604 (19)0.0483 (7)
C330.2199 (3)0.3571 (5)0.1518 (2)0.0618 (9)
C340.1585 (3)0.3476 (5)0.2244 (3)0.0637 (9)
C350.1887 (2)0.4275 (5)0.2996 (2)0.0576 (8)
C360.2797 (2)0.5173 (4)0.30251 (19)0.0479 (7)
C370.6063 (2)0.8611 (4)0.46929 (18)0.0503 (7)
C380.5006 (3)0.8545 (5)0.5107 (3)0.0732 (11)
H38A0.44260.84870.46500.110*
H38B0.49190.94550.54590.110*
H38C0.49880.76500.54820.110*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0666 (11)0.0732 (15)0.0619 (11)0.0130 (11)0.0232 (9)−0.0028 (11)
F20.0549 (11)0.0711 (15)0.1170 (17)0.0146 (11)0.0214 (11)−0.0119 (13)
F30.0722 (13)0.0779 (17)0.130 (2)0.0198 (13)−0.0197 (13)0.0159 (16)
F40.1202 (19)0.142 (3)0.0729 (14)0.035 (2)−0.0018 (13)0.0403 (17)
F50.0912 (14)0.114 (2)0.0575 (11)0.0362 (15)0.0268 (10)0.0183 (13)
F60.0671 (11)0.0779 (16)0.0541 (10)−0.0180 (10)0.0122 (8)−0.0129 (10)
F70.0866 (15)0.103 (2)0.0887 (15)−0.0428 (15)−0.0011 (12)−0.0268 (16)
F80.0693 (13)0.107 (2)0.1263 (19)−0.0491 (15)0.0166 (13)−0.0048 (18)
F90.0727 (13)0.0947 (19)0.0836 (14)−0.0132 (13)0.0324 (11)0.0185 (14)
F100.0714 (12)0.0817 (16)0.0459 (9)−0.0095 (11)0.0111 (8)−0.0016 (10)
O10.0426 (10)0.0584 (14)0.0512 (11)−0.0076 (10)0.0065 (9)0.0020 (11)
O20.0658 (13)0.0701 (17)0.0568 (13)−0.0208 (13)0.0067 (10)−0.0049 (13)
O30.0470 (10)0.0479 (13)0.0477 (11)0.0005 (10)0.0149 (8)−0.0014 (10)
O40.0649 (13)0.0676 (17)0.0754 (15)0.0162 (14)0.0199 (11)0.0228 (14)
N10.0400 (11)0.0435 (14)0.0433 (12)−0.0035 (11)0.0014 (9)0.0011 (11)
N20.0336 (11)0.0426 (14)0.0427 (12)−0.0016 (10)0.0073 (9)0.0035 (10)
C10.0348 (13)0.0412 (16)0.0473 (14)−0.0060 (12)0.0003 (11)0.0007 (13)
C20.0399 (14)0.0467 (18)0.0509 (16)−0.0044 (13)0.0025 (12)0.0012 (14)
C30.0445 (16)0.062 (2)0.0677 (19)0.0028 (16)0.0081 (14)−0.0006 (19)
C40.0514 (18)0.062 (2)0.084 (2)0.0147 (18)−0.0045 (16)0.006 (2)
C50.0581 (18)0.054 (2)0.0669 (19)0.0023 (17)−0.0064 (16)0.0072 (18)
C60.0465 (16)0.0482 (19)0.0506 (15)−0.0069 (14)−0.0030 (12)0.0034 (14)
C70.0615 (18)0.056 (2)0.0423 (14)−0.0057 (16)0.0010 (13)0.0055 (14)
C80.0571 (16)0.057 (2)0.0411 (14)−0.0033 (16)0.0089 (12)−0.0011 (15)
C90.0426 (14)0.0424 (17)0.0407 (13)−0.0046 (12)0.0043 (11)−0.0037 (13)
C100.0433 (15)0.0485 (19)0.0472 (15)0.0000 (13)0.0103 (12)−0.0032 (13)
C110.0420 (14)0.0492 (18)0.0480 (15)0.0015 (13)0.0112 (11)−0.0010 (14)
C120.0407 (14)0.0419 (17)0.0542 (16)−0.0041 (13)0.0080 (12)−0.0003 (14)
C130.0440 (15)0.0469 (19)0.0577 (17)−0.0060 (14)0.0080 (13)−0.0028 (15)
C140.0415 (16)0.0430 (19)0.084 (2)0.0001 (14)0.0062 (15)−0.0094 (17)
C150.0505 (17)0.050 (2)0.092 (3)0.0023 (16)−0.0093 (17)0.0047 (19)
C160.070 (2)0.073 (3)0.063 (2)0.006 (2)−0.0021 (17)0.015 (2)
C170.0595 (18)0.063 (2)0.0555 (17)0.0064 (17)0.0108 (14)0.0055 (17)
C180.0454 (15)0.060 (2)0.0470 (15)0.0009 (16)0.0123 (12)−0.0009 (15)
C190.074 (2)0.085 (3)0.069 (2)−0.002 (2)−0.0049 (18)0.018 (2)
C200.0337 (12)0.0340 (15)0.0442 (13)0.0044 (11)0.0042 (10)0.0066 (12)
C210.0396 (13)0.0425 (17)0.0446 (14)0.0012 (13)0.0100 (11)0.0041 (13)
C220.0486 (16)0.0466 (18)0.0525 (16)−0.0019 (14)0.0035 (13)−0.0012 (14)
C230.0429 (15)0.051 (2)0.069 (2)−0.0127 (14)0.0024 (14)0.0026 (17)
C240.0390 (15)0.0490 (19)0.0588 (17)−0.0066 (14)0.0099 (12)0.0107 (15)
C250.0372 (13)0.0403 (17)0.0479 (15)0.0009 (12)0.0098 (11)0.0090 (13)
C260.0461 (15)0.0518 (19)0.0442 (14)−0.0007 (14)0.0164 (12)0.0086 (14)
C270.0511 (16)0.054 (2)0.0384 (14)−0.0018 (15)0.0076 (12)0.0011 (14)
C280.0358 (13)0.0426 (16)0.0408 (13)0.0018 (12)0.0025 (10)0.0051 (13)
C290.0404 (14)0.0520 (19)0.0409 (14)0.0007 (13)−0.0005 (11)0.0027 (13)
C300.0374 (13)0.0462 (17)0.0458 (14)0.0020 (12)−0.0013 (11)−0.0013 (13)
C310.0363 (12)0.0411 (17)0.0466 (14)0.0019 (12)0.0015 (11)0.0088 (13)
C320.0415 (14)0.053 (2)0.0508 (15)−0.0039 (14)0.0026 (12)−0.0020 (15)
C330.0545 (18)0.065 (2)0.0650 (19)−0.0119 (17)−0.0017 (15)−0.0051 (18)
C340.0471 (17)0.060 (2)0.084 (2)−0.0156 (17)0.0017 (16)0.0071 (19)
C350.0471 (16)0.062 (2)0.0647 (19)−0.0013 (17)0.0139 (14)0.0155 (18)
C360.0452 (15)0.053 (2)0.0455 (15)0.0037 (14)0.0013 (12)0.0069 (14)
C370.0486 (16)0.060 (2)0.0432 (15)−0.0032 (16)0.0080 (12)0.0048 (14)
C380.066 (2)0.079 (3)0.079 (2)−0.008 (2)0.0320 (17)0.010 (2)

Geometric parameters (Å, °)

F1—C131.332 (4)C12—C171.386 (4)
F2—C141.332 (4)C12—C131.387 (4)
F3—C151.341 (4)C13—C141.387 (5)
F4—C161.336 (4)C14—C151.354 (5)
F5—C171.339 (4)C15—C161.350 (5)
F6—C321.348 (3)C16—C171.378 (5)
F7—C331.331 (4)C18—C191.486 (5)
F8—C341.328 (4)C19—H19A0.9600
F9—C351.338 (3)C19—H19B0.9600
F10—C361.338 (4)C19—H19C0.9600
O1—C181.354 (3)C20—C211.406 (4)
O1—C21.391 (4)C20—C251.421 (3)
O2—C181.184 (4)C21—C221.354 (4)
O3—C371.359 (4)C22—C231.411 (4)
O3—C211.395 (3)C22—H220.9300
O4—C371.182 (4)C23—C241.349 (5)
N1—C91.323 (3)C23—H230.9300
N1—C11.352 (4)C24—C251.412 (4)
N2—C281.313 (4)C24—H240.9300
N2—C201.354 (3)C25—C261.399 (4)
C1—C61.411 (4)C26—C271.344 (4)
C1—C21.423 (4)C26—H260.9300
C2—C31.347 (4)C27—C281.415 (4)
C3—C41.400 (5)C27—H270.9300
C3—H30.9300C28—C291.469 (4)
C4—C51.359 (5)C29—C301.323 (4)
C4—H40.9300C29—H290.9300
C5—C61.411 (5)C30—C311.454 (4)
C5—H50.9300C30—H300.9300
C6—C71.404 (4)C31—C321.380 (4)
C7—C81.362 (5)C31—C361.395 (4)
C7—H70.9300C32—C331.370 (4)
C8—C91.405 (4)C33—C341.371 (5)
C8—H80.9300C34—C351.357 (5)
C9—C101.473 (4)C35—C361.363 (5)
C10—C111.320 (4)C37—C381.482 (4)
C10—H100.9300C38—H38A0.9600
C11—C121.443 (4)C38—H38B0.9600
C11—H110.9300C38—H38C0.9600
C18—O1—C2117.6 (2)H19A—C19—H19C109.5
C37—O3—C21117.1 (2)H19B—C19—H19C109.5
C9—N1—C1117.5 (2)N2—C20—C21119.0 (2)
C28—N2—C20118.1 (2)N2—C20—C25122.9 (2)
N1—C1—C6123.8 (3)C21—C20—C25118.1 (2)
N1—C1—C2118.6 (2)C22—C21—O3119.8 (2)
C6—C1—C2117.6 (3)C22—C21—C20121.9 (2)
C3—C2—O1120.1 (3)O3—C21—C20118.1 (2)
C3—C2—C1121.8 (3)C21—C22—C23119.5 (3)
O1—C2—C1117.8 (3)C21—C22—H22120.3
C2—C3—C4119.5 (3)C23—C22—H22120.3
C2—C3—H3120.3C24—C23—C22120.8 (3)
C4—C3—H3120.3C24—C23—H23119.6
C5—C4—C3121.6 (3)C22—C23—H23119.6
C5—C4—H4119.2C23—C24—C25120.7 (3)
C3—C4—H4119.2C23—C24—H24119.6
C4—C5—C6119.5 (3)C25—C24—H24119.6
C4—C5—H5120.3C26—C25—C24124.2 (2)
C6—C5—H5120.3C26—C25—C20116.7 (3)
C7—C6—C5123.4 (3)C24—C25—C20119.0 (3)
C7—C6—C1116.6 (3)C27—C26—C25119.9 (2)
C5—C6—C1120.0 (3)C27—C26—H26120.0
C8—C7—C6119.6 (3)C25—C26—H26120.0
C8—C7—H7120.2C26—C27—C28119.8 (3)
C6—C7—H7120.2C26—C27—H27120.1
C7—C8—C9119.6 (3)C28—C27—H27120.1
C7—C8—H8120.2N2—C28—C27122.5 (3)
C9—C8—H8120.2N2—C28—C29117.3 (2)
N1—C9—C8122.8 (3)C27—C28—C29120.2 (3)
N1—C9—C10117.2 (2)C30—C29—C28122.5 (3)
C8—C9—C10120.0 (3)C30—C29—H29118.7
C11—C10—C9122.9 (3)C28—C29—H29118.7
C11—C10—H10118.5C29—C30—C31128.6 (3)
C9—C10—H10118.5C29—C30—H30115.7
C10—C11—C12129.5 (3)C31—C30—H30115.7
C10—C11—H11115.2C32—C31—C36114.6 (3)
C12—C11—H11115.2C32—C31—C30125.8 (2)
C17—C12—C13114.6 (3)C36—C31—C30119.5 (3)
C17—C12—C11119.3 (3)F6—C32—C33116.1 (3)
C13—C12—C11126.1 (3)F6—C32—C31120.4 (3)
F1—C13—C14117.5 (3)C33—C32—C31123.5 (3)
F1—C13—C12120.0 (3)F7—C33—C32120.3 (3)
C14—C13—C12122.5 (3)F7—C33—C34120.6 (3)
F2—C14—C15120.7 (3)C32—C33—C34119.1 (3)
F2—C14—C13119.5 (3)F8—C34—C35120.4 (3)
C15—C14—C13119.8 (3)F8—C34—C33119.6 (3)
F3—C15—C16120.3 (4)C35—C34—C33119.9 (3)
F3—C15—C14119.6 (3)F9—C35—C34119.8 (3)
C16—C15—C14120.2 (3)F9—C35—C36120.3 (3)
F4—C16—C15121.0 (3)C34—C35—C36119.8 (3)
F4—C16—C17119.4 (3)F10—C36—C35117.9 (3)
C15—C16—C17119.6 (3)F10—C36—C31119.1 (3)
F5—C17—C16117.6 (3)C35—C36—C31123.0 (3)
F5—C17—C12119.1 (3)O4—C37—O3123.2 (3)
C16—C17—C12123.3 (3)O4—C37—C38127.0 (3)
O2—C18—O1123.1 (3)O3—C37—C38109.7 (3)
O2—C18—C19126.6 (3)C37—C38—H38A109.5
O1—C18—C19110.3 (3)C37—C38—H38B109.5
C18—C19—H19A109.5H38A—C38—H38B109.5
C18—C19—H19B109.5C37—C38—H38C109.5
H19A—C19—H19B109.5H38A—C38—H38C109.5
C18—C19—H19C109.5H38B—C38—H38C109.5
C9—N1—C1—C61.4 (4)C28—N2—C20—C21179.8 (3)
C9—N1—C1—C2−178.4 (3)C28—N2—C20—C250.1 (4)
C18—O1—C2—C3−115.3 (3)C37—O3—C21—C22−112.4 (3)
C18—O1—C2—C171.0 (4)C37—O3—C21—C2072.5 (3)
N1—C1—C2—C3−179.1 (3)N2—C20—C21—C22179.0 (3)
C6—C1—C2—C31.1 (5)C25—C20—C21—C22−1.2 (4)
N1—C1—C2—O1−5.4 (4)N2—C20—C21—O3−6.0 (4)
C6—C1—C2—O1174.7 (3)C25—C20—C21—O3173.8 (2)
O1—C2—C3—C4−174.1 (3)O3—C21—C22—C23−174.5 (3)
C1—C2—C3—C4−0.6 (5)C20—C21—C22—C230.4 (5)
C2—C3—C4—C5−0.2 (6)C21—C22—C23—C240.1 (5)
C3—C4—C5—C60.4 (6)C22—C23—C24—C250.4 (5)
C4—C5—C6—C7179.7 (3)C23—C24—C25—C26178.8 (3)
C4—C5—C6—C10.2 (5)C23—C24—C25—C20−1.2 (5)
N1—C1—C6—C7−0.3 (5)N2—C20—C25—C261.3 (4)
C2—C1—C6—C7179.6 (3)C21—C20—C25—C26−178.4 (3)
N1—C1—C6—C5179.3 (3)N2—C20—C25—C24−178.6 (3)
C2—C1—C6—C5−0.9 (5)C21—C20—C25—C241.6 (4)
C5—C6—C7—C8179.3 (3)C24—C25—C26—C27179.5 (3)
C1—C6—C7—C8−1.2 (5)C20—C25—C26—C27−0.5 (4)
C6—C7—C8—C91.5 (5)C25—C26—C27—C28−1.6 (5)
C1—N1—C9—C8−1.2 (4)C20—N2—C28—C27−2.4 (4)
C1—N1—C9—C10177.6 (3)C20—N2—C28—C29176.5 (2)
C7—C8—C9—N1−0.3 (5)C26—C27—C28—N23.2 (5)
C7—C8—C9—C10−179.0 (3)C26—C27—C28—C29−175.7 (3)
N1—C9—C10—C110.1 (5)N2—C28—C29—C30−6.2 (5)
C8—C9—C10—C11178.9 (3)C27—C28—C29—C30172.7 (3)
C9—C10—C11—C12−178.3 (3)C28—C29—C30—C31179.9 (3)
C10—C11—C12—C17170.0 (3)C29—C30—C31—C324.7 (5)
C10—C11—C12—C13−10.0 (6)C29—C30—C31—C36−173.8 (3)
C17—C12—C13—F1−178.5 (3)C36—C31—C32—F6−179.7 (3)
C11—C12—C13—F11.5 (5)C30—C31—C32—F61.8 (5)
C17—C12—C13—C142.4 (5)C36—C31—C32—C330.7 (5)
C11—C12—C13—C14−177.5 (3)C30—C31—C32—C33−177.9 (3)
F1—C13—C14—F20.9 (5)F6—C32—C33—F70.2 (5)
C12—C13—C14—F2180.0 (3)C31—C32—C33—F7179.9 (3)
F1—C13—C14—C15178.9 (3)F6—C32—C33—C34−179.1 (3)
C12—C13—C14—C15−2.0 (5)C31—C32—C33—C340.5 (6)
F2—C14—C15—F3−1.8 (6)F7—C33—C34—F8−1.1 (6)
C13—C14—C15—F3−179.8 (3)C32—C33—C34—F8178.2 (3)
F2—C14—C15—C16178.6 (4)F7—C33—C34—C35179.7 (4)
C13—C14—C15—C160.6 (6)C32—C33—C34—C35−1.0 (6)
F3—C15—C16—F41.6 (7)F8—C34—C35—F91.5 (6)
C14—C15—C16—F4−178.8 (4)C33—C34—C35—F9−179.4 (4)
F3—C15—C16—C17−179.5 (4)F8—C34—C35—C36−179.0 (3)
C14—C15—C16—C170.1 (7)C33—C34—C35—C360.1 (6)
F4—C16—C17—F50.1 (6)F9—C35—C36—F10−0.9 (5)
C15—C16—C17—F5−178.9 (4)C34—C35—C36—F10179.6 (3)
F4—C16—C17—C12179.4 (4)F9—C35—C36—C31−179.3 (3)
C15—C16—C17—C120.5 (7)C34—C35—C36—C311.2 (5)
C13—C12—C17—F5177.6 (3)C32—C31—C36—F10−180.0 (3)
C11—C12—C17—F5−2.4 (5)C30—C31—C36—F10−1.3 (4)
C13—C12—C17—C16−1.7 (6)C32—C31—C36—C35−1.6 (5)
C11—C12—C17—C16178.3 (4)C30—C31—C36—C35177.1 (3)
C2—O1—C18—O214.2 (4)C21—O3—C37—O413.1 (4)
C2—O1—C18—C19−166.2 (3)C21—O3—C37—C38−167.5 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5079).

References

  • Bruker (2001). SAINT, SMART and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zeng, H., OuYang, X., Wang, T., Yuan, G., Zhang, G. & Zhang, X. (2006). Cryst. Growth Des.6, 1697–1702.

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