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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3309.
Published online 2010 November 27. doi:  10.1107/S1600536810048610
PMCID: PMC3011608

(2E,6E)-2,6-Bis(2-fluoro-5-meth­oxy­benzyl­idene)cyclo­hexan-1-one

Abstract

The title compound, C22H20F2O3, a derivative of curcumin, crystallized with two independent mol­ecules in the asymmetric unit. The mean planes of the two 2-fluoro-5-meth­oxy­phenyl groups are aligned at 24.88 (11)° in one mol­ecule and 24.19 (15)° in the other. The dihedral angles between the mean plane of the penta-1,4-dien-3-one group and those of the two 2-fluoro-5-meth­oxy­phenyl rings are 51.16 (11) and 49.16 (10)° in the first mol­ecule, and 45.69 (15) and 54.00 (14)° in the second. The mol­ecules adopt E configurations about the central olefinic bonds.

Related literature

For related structures, see: Liang et al. (2007 [triangle]); Zhao et al. (2009 [triangle]); Zhao, Yang, Liang et al. (2010 [triangle]). For background to and applications of related compounds, see: Aggarwal et al. (2003 [triangle]); Began et al. (1999 [triangle]); Ganesh & Aggarwal (2007) [triangle]; Liang et al.(2009 [triangle]); Zhao, Yang, Wang et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3309-scheme1.jpg

Experimental

Crystal data

  • C22H20F2O3
  • M r = 370.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3309-efi1.jpg
  • a = 9.2334 (10) Å
  • b = 9.7601 (11) Å
  • c = 21.433 (2) Å
  • α = 90.195 (2)°
  • β = 100.568 (2)°
  • γ = 92.934 (2)°
  • V = 1896.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 273 K
  • 0.10 × 0.10 × 0.10 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.990, T max = 0.990
  • 10069 measured reflections
  • 6634 independent reflections
  • 3949 reflections with I > 2σ(I)
  • R int = 0.101

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.147
  • S = 1.00
  • 6634 reflections
  • 492 parameters
  • H-atom parameters not refined
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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/S1600536810048610/ng5065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048610/ng5065Isup2.hkl

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

Acknowledgments

This work was supported by the Xinmiao Talent Project of Zhejiang Province (CLF). The use of the X-ray crystallographic service at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, and the valuable assistance of the staff is gratefully acknowledged.

supplementary crystallographic information

Comment

The title compound, (2E,6E)-2,6-bis(2-fluoro-5-hydroxybenzylidene)cyclohexanone (I), is one of mono-carbonyl analogues of curcumin designed and synthesized by our group.Curcumin reportedly possesses several pharmacological properties including anti-inflammatory, antimicrobial,antiviral, antifungal, antioxidant, chemosensitizing, radiosensitizing,and wound healing activities.Curcumin can suppress tumor initiation, promotion, and metastasis in experimental models. (Began, et al.1999;Ganesh et al.2007).Unlike most chemotherapeutic agents, curcumin has been reported to show almost nontoxicity. These compound have attracted more and more attention. (Aggarwal et al.2003). The need for curcumin-like compounds with improved bioavailability characteristics has led to the chemical synthesis of a series of analogues, using curcumin as the primary structure. In our previous study, a series of fluorine-containing, mono-carbonyl analogues of curcumin were designed and synthesized by the deletion of β-diketone moiety, and their bioactivities were evaluated (Liang et al., 2009; Zhao et al., 2010). Among those compounds, the cyclohexanone-containing analogues exhibited better anti-tumor properties and a wider anti-tumor spectrum than acetone- and cyclopentanone-containing analogues. As a continuation of our broad program of work on the synthesis and structural study of chalcones, the title chalcone derivative has been obtained and an X-ray diffraction study was carried out. Therefore, the structure of one of cyclohexanone-containing compounds (I), was further determined and analyzed using single-crystal X-ray diffraction. Accumulation of detailed structural and pharmacological data facilitated the explanation of the observed structure–activity relationships and modeling of new compounds with potential biological activity.

In this paper, we report the molecular and crystal structures of fluorine-containing, mono-carbonyl analogues of curcumin, (I). The molecule (I), consists of three ring systems, i.e., one cyclohexanone ring and two aryl rings. The central cyclohexanone ring has a distorted chair conformation, and molecular structures have an E-configuration towards the central olefinic bonds, exhibiting a butterfly-shaped geometry. The dihedral angle between the two terminal phenyl rings is 27.19 (13)°, and the two phenyl rings are twisted out of the plane of the central cyclohexanone on the two sides, respectively. Among these derivatives, some of them were reported of their crystal structures ( Liang et al., 2007; Zhao et al., 2009; Zhao et al., 2010).

Experimental

Cyclohexanone (7.5 mmol) was dissolved in ethanol (5 ml) and crushed KOH (15 mmol) was added. The flask was immersed in a bath of crushed ice and a solution of 2-fluoro-5-hydroxybenzaldehyde (15 mmol) in ethanol (5 mmol) was added. The reaction mixture was stirred at 300 K and completion of the reaction was monitored by thin-layer chromatography. Ice-cold water was added to the reaction mixture after 48 h and the yellow solid that separated was filtered off, washed with water and cold ethanol, dried and purified by column chromatography on silica gel (yield: 58.3%). Single crystals of the title compound were grown in a CH2Cl2/CH3OH mixture (5:2 v/v) by slow evaporation (mp 91.3-93.4 °C).

Yellow powder, 58.3% yield, mp 91.3-93.4°C. 1H-NMR (CDCl3) δ: 7.77 (2H, s, Ar-CH=C×2), 7.03 (2H, t, J=9.0Hz, Ar-H3×2), 6.83-6.87 (4H, m, Ar-H4,6×2), 3.80 (6H, s, Ar-OCH3×2), 2.81 (4H, t, J=5.4Hz, CH2-C-CH2), 1.78 (2H, m, >CH2). ESI-MS m/z: 371.0 (M+H)+, calcd for C22H20F2O3: 370.39.

Refinement

The H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% displacement ellipsoids for the non-hydrogen atoms. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C22H20F2O3Z = 4
Mr = 370.38F(000) = 776
Triclinic, P1Dx = 1.297 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2334 (10) ÅCell parameters from 3025 reflections
b = 9.7601 (11) Åθ = 2.3–23.1°
c = 21.433 (2) ŵ = 0.10 mm1
α = 90.195 (2)°T = 273 K
β = 100.568 (2)°Block, colorless
γ = 92.934 (2)°0.10 × 0.10 × 0.10 mm
V = 1896.1 (4) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer6634 independent reflections
Radiation source: fine-focus sealed tube3949 reflections with I > 2σ(I)
graphiteRint = 0.101
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −10→10
Tmin = 0.990, Tmax = 0.990k = −11→11
10069 measured reflectionsl = −18→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters not refined
wR(F2) = 0.147w = 1/[σ2(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.015
6634 reflectionsΔρmax = 0.26 e Å3
492 parametersΔρmin = −0.27 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0102 (12)

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
F10.64586 (15)−0.51316 (13)0.03944 (7)0.0840 (4)
O10.59989 (17)−0.11281 (16)−0.08404 (7)0.0687 (4)
O40.94423 (17)0.60048 (16)−0.09902 (8)0.0769 (5)
F20.94845 (17)0.08313 (16)−0.19582 (7)0.0938 (5)
C50.7533 (2)0.0813 (2)−0.04416 (10)0.0525 (5)
C60.6674 (2)−0.0492 (2)−0.03706 (10)0.0521 (5)
C70.9400 (2)0.4676 (2)−0.12065 (11)0.0602 (6)
C80.5428 (2)−0.2508 (2)0.13952 (10)0.0577 (6)
H80.5357−0.15620.14120.069*
C90.6657 (2)−0.1030 (2)0.02818 (10)0.0513 (5)
C100.8601 (2)0.3605 (2)−0.09952 (10)0.0585 (6)
H100.80330.3770−0.06890.070*
O30.4590 (2)−0.25806 (18)0.23530 (8)0.0859 (5)
C120.9460 (3)0.2116 (2)−0.17015 (11)0.0666 (6)
C130.6103 (2)−0.2322 (2)0.03145 (10)0.0561 (5)
H130.5820−0.2785−0.00720.067*
C140.5881 (2)−0.3100 (2)0.08760 (10)0.0541 (5)
C150.7815 (2)0.1087 (2)−0.10238 (11)0.0593 (6)
H150.74410.0433−0.13360.071*
C160.6001 (2)−0.4513 (2)0.08892 (11)0.0631 (6)
C170.8626 (2)0.2266 (2)−0.12325 (10)0.0576 (6)
C180.7318 (2)−0.0142 (2)0.08455 (10)0.0603 (6)
H18A0.7671−0.07220.12020.072*
H18B0.65610.04090.09610.072*
C190.5085 (2)−0.3297 (2)0.18834 (11)0.0633 (6)
C200.5209 (3)−0.4707 (3)0.18760 (12)0.0742 (7)
H200.4980−0.52380.22080.089*
C210.8076 (3)0.1678 (2)0.01397 (10)0.0664 (6)
H21A0.72920.22370.02220.080*
H21B0.88910.22880.00680.080*
C220.5255 (3)0.7126 (3)0.62792 (12)0.0742 (7)
H220.53770.61860.62680.089*
C230.3185 (3)0.5673 (3)0.51074 (11)0.0715 (7)
C240.5675 (3)−0.5308 (3)0.13702 (13)0.0727 (7)
H240.5766−0.62520.13580.087*
C251.0243 (3)0.4454 (3)−0.16668 (12)0.0723 (7)
H251.07920.5179−0.18050.087*
O50.6789 (2)0.7139 (2)0.72684 (9)0.1000 (6)
C271.0266 (3)0.3162 (3)−0.19182 (12)0.0780 (7)
H271.08200.3002−0.22300.094*
O20.2913 (2)0.5903 (2)0.39992 (8)0.1026 (6)
C290.8584 (2)0.0796 (2)0.07149 (11)0.0682 (6)
H29A0.93840.02510.06380.082*
H29B0.89480.13820.10830.082*
C300.5948 (3)0.7889 (3)0.68033 (13)0.0799 (7)
C310.2607 (3)0.5211 (3)0.44426 (12)0.0769 (7)
F4−0.1739 (2)0.4179 (2)0.28990 (8)0.1210 (6)
C330.1666 (3)0.3919 (3)0.43095 (12)0.0733 (7)
C340.3691 (3)0.6978 (3)0.51894 (12)0.0803 (7)
H340.35880.74920.48210.096*
C35−0.0142 (3)0.2610 (3)0.34497 (12)0.0787 (8)
C360.0179 (3)0.1235 (3)0.35708 (12)0.0826 (8)
H360.10250.10300.38560.099*
C370.8455 (3)0.6307 (3)−0.05740 (13)0.0797 (7)
H37A0.74620.6047−0.07750.120*
H37B0.85340.7272−0.04780.120*
H37C0.87060.5804−0.01880.120*
C380.4382 (3)0.7727 (3)0.57692 (13)0.0776 (7)
C390.3083 (3)0.4666 (3)0.56284 (12)0.0808 (7)
H39A0.30550.51660.60180.097*
H39B0.39590.41390.56990.097*
C40−0.1396 (4)0.2852 (4)0.30224 (14)0.0935 (9)
C410.0852 (3)0.3759 (3)0.37287 (13)0.0840 (8)
H410.09280.44930.34590.101*
O6−0.0522 (3)−0.1187 (2)0.33634 (11)0.1141 (7)
F30.3415 (3)0.97700 (19)0.53269 (11)0.1524 (9)
C440.1740 (3)0.3700 (3)0.54768 (12)0.0921 (9)
H44A0.08630.42170.54570.111*
H44B0.17570.30420.58160.111*
C450.1653 (3)0.2928 (3)0.48495 (12)0.0846 (8)
H45A0.24850.23490.48790.102*
H45B0.07560.23430.47660.102*
C460.5792 (4)0.9275 (3)0.68372 (16)0.0975 (9)
H460.62640.97860.71900.117*
C47−0.0755 (3)0.0179 (4)0.32694 (15)0.0913 (9)
C480.3954 (4)−0.3343 (3)0.28049 (13)0.1087 (10)
H48A0.3209−0.39890.25890.163*
H48B0.3517−0.27300.30600.163*
H48C0.4704−0.38260.30720.163*
C490.4926 (4)0.9889 (3)0.6342 (2)0.1229 (12)
H490.47921.08250.63580.147*
C50−0.2011 (4)0.0478 (4)0.28457 (16)0.1095 (11)
H50−0.2637−0.02290.26430.131*
C51−0.2339 (4)0.1829 (5)0.27229 (16)0.1145 (11)
H51−0.31890.20370.24410.137*
C520.4259 (4)0.9131 (3)0.58215 (17)0.1020 (9)
C540.0799 (4)−0.1549 (4)0.3739 (2)0.1360 (14)
H54A0.1614−0.11180.35810.204*
H54B0.0861−0.25270.37260.204*
H54C0.0830−0.12520.41690.204*
C550.7647 (4)0.7839 (3)0.77809 (15)0.1175 (11)
H55A0.82650.85350.76300.176*
H55B0.82520.72080.80390.176*
H55C0.70190.82580.80290.176*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.1075 (10)0.0526 (8)0.1018 (11)0.0057 (7)0.0447 (9)−0.0015 (7)
O10.0905 (11)0.0540 (10)0.0632 (10)−0.0054 (8)0.0210 (9)−0.0035 (8)
O40.0902 (11)0.0533 (10)0.0936 (12)−0.0070 (8)0.0364 (10)0.0036 (8)
F20.1283 (12)0.0732 (10)0.0938 (11)0.0039 (9)0.0572 (9)−0.0062 (8)
C50.0541 (12)0.0410 (12)0.0645 (14)0.0075 (9)0.0151 (10)0.0029 (10)
C60.0572 (12)0.0434 (12)0.0591 (14)0.0080 (10)0.0183 (11)−0.0030 (10)
C70.0629 (13)0.0544 (15)0.0648 (14)0.0012 (11)0.0163 (11)0.0092 (11)
C80.0638 (13)0.0511 (13)0.0594 (14)−0.0038 (10)0.0160 (11)0.0065 (11)
C90.0541 (11)0.0437 (12)0.0594 (13)0.0057 (9)0.0180 (10)0.0009 (10)
C100.0642 (13)0.0559 (14)0.0602 (14)0.0032 (11)0.0237 (11)0.0092 (11)
O30.1237 (14)0.0769 (12)0.0651 (11)−0.0099 (10)0.0422 (10)0.0060 (9)
C120.0820 (15)0.0563 (15)0.0671 (15)0.0027 (12)0.0283 (13)0.0022 (12)
C130.0669 (13)0.0447 (13)0.0606 (13)0.0033 (10)0.0222 (11)−0.0028 (10)
C140.0573 (12)0.0472 (13)0.0603 (14)0.0004 (10)0.0178 (10)0.0058 (10)
C150.0664 (13)0.0504 (13)0.0651 (15)0.0049 (10)0.0222 (11)0.0045 (11)
C160.0705 (14)0.0533 (14)0.0684 (15)0.0007 (11)0.0213 (12)0.0024 (12)
C170.0617 (13)0.0541 (14)0.0598 (14)0.0024 (10)0.0189 (11)0.0093 (11)
C180.0670 (13)0.0535 (13)0.0616 (14)0.0004 (11)0.0158 (11)0.0040 (11)
C190.0717 (14)0.0625 (16)0.0565 (14)−0.0056 (12)0.0162 (11)0.0068 (12)
C200.0850 (16)0.0688 (18)0.0674 (16)−0.0083 (13)0.0134 (13)0.0227 (13)
C210.0795 (15)0.0544 (14)0.0632 (15)−0.0096 (11)0.0108 (12)0.0057 (11)
C220.0987 (18)0.0635 (16)0.0681 (17)0.0113 (14)0.0334 (14)0.0018 (13)
C230.0922 (17)0.0703 (18)0.0614 (16)0.0245 (14)0.0337 (13)0.0114 (12)
C240.0839 (16)0.0494 (14)0.0856 (18)0.0006 (12)0.0185 (14)0.0153 (13)
C250.0761 (15)0.0691 (17)0.0772 (17)−0.0067 (13)0.0311 (13)0.0148 (13)
O50.1470 (17)0.0775 (13)0.0736 (13)−0.0049 (12)0.0182 (12)0.0008 (11)
C270.0853 (17)0.084 (2)0.0748 (17)0.0039 (14)0.0420 (14)0.0101 (14)
O20.1667 (18)0.0881 (14)0.0632 (11)0.0080 (13)0.0474 (12)0.0147 (10)
C290.0729 (14)0.0639 (15)0.0650 (15)−0.0100 (12)0.0087 (12)0.0079 (12)
C300.0995 (19)0.0662 (18)0.0807 (19)0.0013 (15)0.0351 (16)0.0068 (15)
C310.1073 (19)0.0776 (18)0.0566 (15)0.0314 (15)0.0355 (14)0.0123 (13)
F40.1282 (13)0.1394 (17)0.1007 (12)0.0539 (12)0.0215 (10)0.0341 (11)
C330.0932 (17)0.0785 (19)0.0570 (16)0.0277 (15)0.0305 (14)0.0111 (13)
C340.1038 (19)0.080 (2)0.0666 (17)0.0287 (16)0.0325 (14)0.0184 (14)
C350.0879 (18)0.098 (2)0.0588 (15)0.0259 (17)0.0311 (14)0.0082 (15)
C360.0878 (18)0.099 (2)0.0680 (17)0.0251 (17)0.0271 (14)0.0042 (16)
C370.0767 (15)0.0667 (17)0.101 (2)0.0059 (13)0.0291 (15)−0.0043 (14)
C380.0963 (18)0.0647 (17)0.0798 (19)0.0160 (14)0.0339 (15)0.0086 (14)
C390.0998 (18)0.089 (2)0.0597 (15)0.0095 (16)0.0302 (14)0.0125 (13)
C400.097 (2)0.122 (3)0.0701 (19)0.041 (2)0.0291 (17)0.0216 (19)
C410.107 (2)0.088 (2)0.0671 (18)0.0394 (17)0.0333 (16)0.0119 (15)
O60.1315 (18)0.0947 (18)0.1233 (18)0.0054 (14)0.0425 (15)−0.0041 (13)
F30.196 (2)0.0803 (13)0.1656 (19)0.0409 (13)−0.0178 (16)0.0237 (12)
C440.113 (2)0.104 (2)0.0666 (17)0.0101 (18)0.0360 (15)0.0221 (15)
C450.1054 (19)0.088 (2)0.0659 (17)0.0096 (15)0.0288 (14)0.0173 (14)
C460.123 (2)0.071 (2)0.099 (2)−0.0025 (18)0.0245 (19)−0.0082 (17)
C470.091 (2)0.110 (3)0.081 (2)0.011 (2)0.0364 (17)−0.0005 (19)
C480.162 (3)0.104 (2)0.0699 (18)−0.014 (2)0.0522 (19)0.0138 (16)
C490.146 (3)0.058 (2)0.162 (4)0.013 (2)0.020 (3)−0.005 (2)
C500.101 (2)0.137 (3)0.093 (2)0.001 (2)0.026 (2)−0.006 (2)
C510.098 (2)0.158 (4)0.088 (2)0.019 (3)0.0149 (19)0.012 (2)
C520.125 (2)0.070 (2)0.111 (2)0.0194 (19)0.016 (2)0.0157 (19)
C540.109 (3)0.091 (3)0.218 (4)0.025 (2)0.049 (3)0.038 (3)
C550.166 (3)0.104 (3)0.076 (2)−0.010 (2)0.009 (2)−0.0054 (18)

Geometric parameters (Å, °)

F1—C161.362 (3)O2—C311.234 (3)
O1—C61.231 (2)C29—H29A0.9700
O4—C71.372 (3)C29—H29B0.9700
O4—C371.427 (3)C30—C461.371 (4)
F2—C121.371 (3)C31—C331.490 (4)
C5—C151.346 (3)F4—C401.364 (4)
C5—C61.489 (3)C33—C411.335 (3)
C5—C211.495 (3)C33—C451.512 (3)
C6—C91.498 (3)C34—C381.464 (4)
C7—C101.375 (3)C34—H340.9300
C7—C251.387 (3)C35—C401.370 (4)
C8—C191.375 (3)C35—C361.404 (4)
C8—C141.392 (3)C35—C411.465 (4)
C8—H80.9300C36—C471.387 (4)
C9—C131.343 (3)C36—H360.9300
C9—C181.501 (3)C37—H37A0.9600
C10—C171.404 (3)C37—H37B0.9600
C10—H100.9300C37—H37C0.9600
O3—C191.381 (3)C38—C521.386 (4)
O3—C481.416 (3)C39—C441.504 (4)
C12—C271.366 (3)C39—H39A0.9700
C12—C171.385 (3)C39—H39B0.9700
C13—C141.465 (3)C40—C511.368 (5)
C13—H130.9300C41—H410.9300
C14—C161.389 (3)O6—C471.370 (4)
C15—C171.457 (3)O6—C541.395 (4)
C15—H150.9300F3—C521.368 (3)
C16—C241.361 (3)C44—C451.526 (4)
C18—C291.515 (3)C44—H44A0.9700
C18—H18A0.9700C44—H44B0.9700
C18—H18B0.9700C45—H45A0.9700
C19—C201.387 (3)C45—H45B0.9700
C20—C241.378 (3)C46—C491.367 (4)
C20—H200.9300C46—H460.9300
C21—C291.522 (3)C47—C501.381 (4)
C21—H21A0.9700C48—H48A0.9600
C21—H21B0.9700C48—H48B0.9600
C22—C301.381 (3)C48—H48C0.9600
C22—C381.385 (3)C49—C521.366 (5)
C22—H220.9300C49—H490.9300
C23—C341.334 (4)C50—C511.383 (5)
C23—C311.486 (4)C50—H500.9300
C23—C391.502 (3)C51—H510.9300
C24—H240.9300C54—H54A0.9600
C25—C271.372 (3)C54—H54B0.9600
C25—H250.9300C54—H54C0.9600
O5—C301.383 (3)C55—H55A0.9600
O5—C551.386 (3)C55—H55B0.9600
C27—H270.9300C55—H55C0.9600
C7—O4—C37116.94 (17)C23—C31—C33120.4 (2)
C15—C5—C6116.80 (19)C41—C33—C31117.1 (2)
C15—C5—C21125.17 (19)C41—C33—C45125.2 (3)
C6—C5—C21117.96 (19)C31—C33—C45117.6 (2)
O1—C6—C5120.62 (19)C23—C34—C38130.1 (2)
O1—C6—C9120.33 (18)C23—C34—H34115.0
C5—C6—C9119.04 (19)C38—C34—H34115.0
O4—C7—C10124.4 (2)C40—C35—C36117.3 (3)
O4—C7—C25115.3 (2)C40—C35—C41120.1 (3)
C10—C7—C25120.3 (2)C36—C35—C41122.6 (3)
C19—C8—C14121.1 (2)C47—C36—C35120.6 (3)
C19—C8—H8119.4C47—C36—H36119.7
C14—C8—H8119.4C35—C36—H36119.7
C13—C9—C6116.31 (19)O4—C37—H37A109.5
C13—C9—C18124.71 (19)O4—C37—H37B109.5
C6—C9—C18118.90 (18)H37A—C37—H37B109.5
C7—C10—C17121.2 (2)O4—C37—H37C109.5
C7—C10—H10119.4H37A—C37—H37C109.5
C17—C10—H10119.4H37B—C37—H37C109.5
C19—O3—C48118.0 (2)C52—C38—C22115.7 (3)
C27—C12—F2118.2 (2)C52—C38—C34120.7 (3)
C27—C12—C17124.2 (2)C22—C38—C34123.5 (2)
F2—C12—C17117.6 (2)C23—C39—C44112.5 (2)
C9—C13—C14128.9 (2)C23—C39—H39A109.1
C9—C13—H13115.6C44—C39—H39A109.1
C14—C13—H13115.6C23—C39—H39B109.1
C16—C14—C8116.4 (2)C44—C39—H39B109.1
C16—C14—C13120.4 (2)H39A—C39—H39B107.8
C8—C14—C13122.94 (19)F4—C40—C51118.3 (3)
C5—C15—C17129.0 (2)F4—C40—C35118.5 (3)
C5—C15—H15115.5C51—C40—C35123.2 (3)
C17—C15—H15115.5C33—C41—C35130.2 (3)
C24—C16—F1118.5 (2)C33—C41—H41114.9
C24—C16—C14123.2 (2)C35—C41—H41114.9
F1—C16—C14118.3 (2)C47—O6—C54118.4 (3)
C12—C17—C10115.72 (19)C39—C44—C45112.5 (2)
C12—C17—C15120.5 (2)C39—C44—H44A109.1
C10—C17—C15123.8 (2)C45—C44—H44A109.1
C9—C18—C29112.16 (18)C39—C44—H44B109.1
C9—C18—H18A109.2C45—C44—H44B109.1
C29—C18—H18A109.2H44A—C44—H44B107.8
C9—C18—H18B109.2C33—C45—C44110.8 (2)
C29—C18—H18B109.2C33—C45—H45A109.5
H18A—C18—H18B107.9C44—C45—H45A109.5
C8—C19—O3114.9 (2)C33—C45—H45B109.5
C8—C19—C20120.6 (2)C44—C45—H45B109.5
O3—C19—C20124.4 (2)H45A—C45—H45B108.1
C24—C20—C19119.0 (2)C49—C46—C30118.6 (3)
C24—C20—H20120.5C49—C46—H46120.7
C19—C20—H20120.5C30—C46—H46120.7
C5—C21—C29111.31 (19)O6—C47—C50116.0 (3)
C5—C21—H21A109.4O6—C47—C36124.1 (3)
C29—C21—H21A109.4C50—C47—C36119.9 (3)
C5—C21—H21B109.4O3—C48—H48A109.5
C29—C21—H21B109.4O3—C48—H48B109.5
H21A—C21—H21B108.0H48A—C48—H48B109.5
C30—C22—C38121.5 (3)O3—C48—H48C109.5
C30—C22—H22119.3H48A—C48—H48C109.5
C38—C22—H22119.3H48B—C48—H48C109.5
C34—C23—C31116.4 (2)C46—C49—C52120.1 (3)
C34—C23—C39125.6 (2)C46—C49—H49119.9
C31—C23—C39117.9 (2)C52—C49—H49119.9
C16—C24—C20119.6 (2)C47—C50—C51120.1 (4)
C16—C24—H24120.2C47—C50—H50120.0
C20—C24—H24120.2C51—C50—H50120.0
C27—C25—C7119.9 (2)C40—C51—C50119.0 (3)
C27—C25—H25120.1C40—C51—H51120.5
C7—C25—H25120.1C50—C51—H51120.5
C30—O5—C55118.4 (2)C49—C52—F3119.2 (3)
C12—C27—C25118.7 (2)C49—C52—C38123.1 (3)
C12—C27—H27120.7F3—C52—C38117.7 (3)
C25—C27—H27120.7O6—C54—H54A109.5
C18—C29—C21110.31 (18)O6—C54—H54B109.5
C18—C29—H29A109.6H54A—C54—H54B109.5
C21—C29—H29A109.6O6—C54—H54C109.5
C18—C29—H29B109.6H54A—C54—H54C109.5
C21—C29—H29B109.6H54B—C54—H54C109.5
H29A—C29—H29B108.1O5—C55—H55A109.5
C46—C30—O5124.6 (3)O5—C55—H55B109.5
C46—C30—C22121.0 (3)H55A—C55—H55B109.5
O5—C30—C22114.4 (2)O5—C55—H55C109.5
O2—C31—C23119.6 (3)H55A—C55—H55C109.5
O2—C31—C33119.9 (2)H55B—C55—H55C109.5

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5065).

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