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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o131.
Published online 2009 December 12. doi:  10.1107/S1600536809052684
PMCID: PMC2980053

10-Benzoyl­phenanthrene-8,9-dicarboxylic anhydride

Abstract

The asymmetric unit of the title compound, C23H12O4, contains two nearly parallel independent mol­ecules; the dihedral angles between the phenanthrene ring systems of the two mol­ecules and between the benzene rings of the two mol­ecules are 4.97 (9) and 8.1 (2)°, respectively. In each mol­ecule, the benzene ring is nearly perpendicular to the phenanthrene ring system, with dihedral angles of 86.42 (19) and 86.68 (18)°. π–π stacking exists between the phenanthrene ring systems of the two independent mol­ecules [centroid–centroid distance = 3.698 (2) Å]. Short intermolec­ular contacts [O(...)O = 2.86 (2) and C(...)O = 2.88 (2) Å] are also present in the crystal structure.

Related literature

The title compound is an important inter­mediate for the synthesis of azonafide [systematic name 2-[2′-(dimethyl-amino)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-dione] derivatives; for the anti­tumor properties of azonafide and its analogues, see: Sami et al. (2000 [triangle]); Hutchings et al. (1988 [triangle]). For the synthesis, see: Zhang et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o131-scheme1.jpg

Experimental

Crystal data

  • C23H12O4
  • M r = 352.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o131-efi1.jpg
  • a = 11.329 (2) Å
  • b = 17.767 (4) Å
  • c = 16.811 (3) Å
  • β = 99.64 (3)°
  • V = 3336.0 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.30 × 0.28 × 0.26 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • 6073 measured reflections
  • 6073 independent reflections
  • 2895 reflections with I > 2σ(I)
  • 3 standard reflections every 3 min
  • intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.160
  • S = 1.01
  • 6073 reflections
  • 487 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052684/xu2667sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052684/xu2667Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of Jiangsu Province, China (BK2007132).

supplementary crystallographic information

Comment

Previous articles have described the preparation and antitumor properties of azonafide and many analogues with structural variations in the side chain and the bent phenanthrene nucleus (Sami, 2000; Hutchings, 1988). In this paper, we present the X-ray crystallographic analysis of the title compound (Fig. 1), which is an important intermediate for the synthesis of azonafide derivatives. The centroids distance between nearly parallel C10-benzene and C40-benzene rings [dihedral angle 4.99°] is 3.698 (2) Å, which suggests the existence of π-π stacking in the crystal structure. Intermolecular sorter contacts [O···O 2.86 Å and C···O 2.88 Å] are present in the crystal structure.

Experimental

A solution of homophthalic anhydride (176 mg, 1 mmol) and diphenyl acetylene (356 mg, 2 mmol) in anhydrous acetonitrile (50 ml) was purged with dry argon for 10 min and then irradiated for 48 h under continuous argon purging. The single crystals of the title compound were obtained from the reaction mixture. The light source was a medium-pressure mercury lamp (500 W) in a cooling water jacket that was further surrounded by a layer of filter solution (1 cm thick, 20% aqueous sodium nitrite) to cut off light of wavelength shorter than 400 nm (Zhang et al., 2000).

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids shown at 30% probability ellipsoids for non-H atoms.

Crystal data

C23H12O4F(000) = 1456
Mr = 352.33Dx = 1.403 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.329 (2) Åθ = 10.8–15.2°
b = 17.767 (4) ŵ = 0.10 mm1
c = 16.811 (3) ÅT = 293 K
β = 99.64 (3)°Block, colourless
V = 3336.0 (11) Å30.30 × 0.28 × 0.26 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.0000
Radiation source: fine-focus sealed tubeθmax = 25.3°, θmin = 1.7°
graphiteh = −13→13
ω/2θ scansk = 0→21
6073 measured reflectionsl = 0→20
6073 independent reflections3 standard reflections every 120 min
2895 reflections with I > 2σ(I) intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0558P)2] where P = (Fo2 + 2Fc2)/3
6073 reflections(Δ/σ)max < 0.001
487 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = −0.17 e Å3

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 (Å2)

xyzUiso*/Ueq
C10.2673 (5)0.1589 (3)−0.0305 (3)0.0998 (16)
H1A0.22950.1738−0.08140.120*
C20.3718 (5)0.1933 (2)0.0036 (3)0.0840 (13)
H2A0.40370.2320−0.02340.101*
C30.4290 (3)0.1700 (2)0.0780 (2)0.0644 (11)
H3A0.50070.19250.10100.077*
C40.3807 (3)0.11345 (19)0.1192 (2)0.0524 (9)
C50.2739 (3)0.0805 (3)0.0847 (3)0.0842 (14)
H5A0.23980.04300.11220.101*
C60.2179 (4)0.1032 (3)0.0093 (3)0.1071 (17)
H6A0.14660.0806−0.01450.129*
C70.4459 (3)0.08948 (18)0.1994 (2)0.0481 (9)
C80.3825 (3)0.03796 (17)0.24980 (19)0.0411 (8)
C90.3994 (3)−0.04183 (18)0.2433 (2)0.0444 (8)
C100.4757 (3)−0.0711 (2)0.1935 (2)0.0604 (10)
H10A0.5160−0.03860.16400.072*
C110.4915 (3)−0.1475 (2)0.1880 (2)0.0717 (12)
H11A0.5429−0.16630.15510.086*
C120.4326 (4)−0.1959 (2)0.2302 (3)0.0743 (12)
H12A0.4444−0.24750.22600.089*
C130.3567 (3)−0.1698 (2)0.2786 (2)0.0667 (11)
H13A0.3158−0.20390.30590.080*
C140.3385 (3)−0.09211 (18)0.2883 (2)0.0485 (9)
C150.2630 (3)−0.06240 (19)0.3414 (2)0.0474 (9)
C160.1970 (3)−0.1080 (2)0.3880 (2)0.0666 (11)
H16A0.2024−0.16010.38490.080*
C170.1263 (4)−0.0769 (3)0.4367 (3)0.0800 (13)
H17A0.0834−0.10800.46590.096*
C180.1174 (4)0.0001 (3)0.4437 (3)0.0812 (13)
H18A0.06640.02490.47540.097*
C190.1796 (3)0.0465 (2)0.4003 (2)0.0540 (9)
C220.3123 (3)0.06531 (17)0.30131 (19)0.0406 (8)
C230.2525 (3)0.01599 (18)0.34878 (19)0.0427 (8)
O60.5567 (3)0.11817 (18)0.44109 (18)0.0940 (10)
O70.7026 (2)0.15182 (13)0.37616 (14)0.0592 (7)
C240.8948 (5)0.2090 (2)0.0165 (3)0.0858 (14)
H24A0.93550.2427−0.01150.103*
C250.9474 (4)0.1832 (2)0.0912 (2)0.0680 (11)
H25A1.02410.19900.11340.082*
C260.8861 (3)0.13347 (19)0.1335 (2)0.0515 (9)
C270.7738 (3)0.1094 (2)0.0989 (2)0.0773 (13)
H27A0.73270.07540.12620.093*
C280.7218 (4)0.1355 (3)0.0239 (3)0.0956 (16)
H28A0.64560.11920.00120.115*
C290.7815 (5)0.1847 (3)−0.0169 (3)0.0898 (15)
H29A0.74590.2021−0.06740.108*
C310.8870 (3)0.04461 (17)0.25475 (19)0.0419 (8)
C320.9170 (3)−0.03219 (18)0.2396 (2)0.0476 (9)
C331.0017 (3)−0.0493 (2)0.1906 (2)0.0663 (11)
H33A1.0385−0.01060.16670.080*
C341.0310 (4)−0.1227 (3)0.1774 (3)0.0824 (14)
H34A1.0885−0.13350.14550.099*
C350.9752 (4)−0.1806 (2)0.2114 (3)0.0856 (15)
H35A0.9952−0.23020.20190.103*
C360.8920 (4)−0.1663 (2)0.2583 (3)0.0731 (12)
H36A0.8549−0.20630.28000.088*
C370.8601 (3)−0.09157 (18)0.2752 (2)0.0557 (10)
C380.7729 (3)−0.0747 (2)0.3260 (2)0.0539 (9)
C390.7101 (4)−0.1307 (2)0.3626 (2)0.0723 (12)
H39A0.7264−0.18130.35510.087*
C400.6263 (4)−0.1115 (3)0.4086 (3)0.0822 (13)
H40A0.5859−0.14910.43170.099*
C410.6012 (4)−0.0382 (3)0.4211 (2)0.0766 (12)
H41A0.5427−0.02610.45180.092*
C420.6612 (3)0.0183 (2)0.3890 (2)0.0555 (9)
C430.6329 (4)0.0960 (3)0.4042 (2)0.0675 (11)
C450.8067 (3)0.05975 (17)0.30482 (19)0.0408 (8)
C460.7477 (3)0.00066 (18)0.34088 (19)0.0447 (8)
O80.8217 (2)0.19227 (13)0.29575 (16)0.0649 (7)
O10.54992 (19)0.10725 (13)0.22378 (14)0.0591 (7)
C440.7792 (3)0.1380 (2)0.3224 (2)0.0483 (9)
O30.2359 (2)0.17298 (12)0.36796 (15)0.0591 (7)
O40.3390 (2)0.19411 (13)0.27183 (17)0.0680 (8)
O51.0484 (2)0.12609 (14)0.24210 (15)0.0681 (7)
O20.1008 (3)0.15884 (17)0.44693 (18)0.0973 (10)
C210.2981 (3)0.14706 (19)0.3096 (2)0.0476 (9)
C300.9469 (3)0.10541 (19)0.2136 (2)0.0509 (9)
C200.1671 (4)0.1276 (2)0.4076 (2)0.0634 (10)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.117 (4)0.113 (4)0.059 (3)0.017 (4)−0.016 (3)0.021 (3)
C20.123 (4)0.065 (3)0.061 (3)0.003 (3)0.009 (3)0.016 (2)
C30.077 (3)0.059 (3)0.057 (3)0.002 (2)0.010 (2)0.006 (2)
C40.052 (2)0.056 (2)0.047 (2)0.0066 (19)0.0024 (18)0.0072 (18)
C50.057 (3)0.117 (4)0.072 (3)−0.018 (3)−0.005 (2)0.027 (3)
C60.070 (3)0.162 (5)0.078 (4)−0.008 (3)−0.021 (3)0.034 (4)
C70.049 (2)0.041 (2)0.055 (2)0.0016 (17)0.0100 (19)−0.0010 (17)
C80.0389 (18)0.0389 (19)0.043 (2)0.0027 (15)−0.0009 (16)0.0013 (16)
C90.0410 (19)0.042 (2)0.048 (2)0.0076 (16)−0.0002 (17)−0.0055 (17)
C100.055 (2)0.056 (2)0.068 (3)0.0075 (19)0.005 (2)−0.008 (2)
C110.065 (3)0.068 (3)0.080 (3)0.018 (2)0.006 (2)−0.020 (2)
C120.065 (3)0.046 (2)0.105 (4)0.005 (2)−0.007 (3)−0.018 (2)
C130.056 (2)0.044 (2)0.095 (3)−0.0048 (19)−0.003 (2)0.000 (2)
C140.045 (2)0.0349 (19)0.060 (2)0.0001 (16)−0.0083 (18)0.0005 (17)
C150.042 (2)0.047 (2)0.049 (2)−0.0037 (17)−0.0030 (17)0.0033 (17)
C160.060 (3)0.059 (3)0.077 (3)−0.010 (2)−0.001 (2)0.019 (2)
C170.065 (3)0.090 (4)0.091 (3)−0.008 (3)0.030 (3)0.029 (3)
C180.076 (3)0.084 (3)0.091 (3)0.006 (3)0.034 (3)0.018 (3)
C190.049 (2)0.061 (3)0.053 (2)−0.0024 (19)0.0113 (18)0.0062 (19)
C220.0341 (17)0.0364 (19)0.047 (2)−0.0009 (15)−0.0045 (16)0.0022 (16)
C230.0345 (18)0.043 (2)0.049 (2)−0.0022 (16)0.0005 (16)−0.0013 (17)
O60.092 (2)0.113 (3)0.087 (2)0.0019 (19)0.0443 (19)−0.0154 (18)
O70.0616 (16)0.0548 (15)0.0624 (16)0.0000 (13)0.0142 (13)−0.0130 (13)
C240.131 (4)0.061 (3)0.069 (3)−0.013 (3)0.026 (3)0.007 (2)
C250.075 (3)0.066 (3)0.064 (3)−0.016 (2)0.013 (2)0.002 (2)
C260.048 (2)0.053 (2)0.054 (2)0.0040 (18)0.0093 (19)0.0022 (18)
C270.052 (2)0.114 (4)0.065 (3)−0.005 (2)0.005 (2)0.028 (3)
C280.053 (3)0.168 (5)0.064 (3)0.011 (3)0.005 (2)0.042 (3)
C290.117 (4)0.094 (4)0.056 (3)0.032 (3)0.006 (3)0.016 (3)
C310.0362 (18)0.042 (2)0.045 (2)−0.0027 (15)−0.0015 (16)0.0017 (16)
C320.0402 (19)0.044 (2)0.052 (2)0.0089 (16)−0.0090 (17)−0.0114 (18)
C330.053 (2)0.068 (3)0.074 (3)0.014 (2)−0.001 (2)−0.020 (2)
C340.055 (3)0.097 (4)0.090 (3)0.023 (3)−0.003 (2)−0.036 (3)
C350.065 (3)0.064 (3)0.118 (4)0.019 (3)−0.014 (3)−0.031 (3)
C360.072 (3)0.041 (2)0.092 (3)0.010 (2)−0.026 (2)−0.003 (2)
C370.059 (2)0.034 (2)0.063 (2)0.0024 (18)−0.021 (2)0.0012 (19)
C380.052 (2)0.049 (2)0.054 (2)−0.0086 (19)−0.0105 (19)0.0079 (19)
C390.080 (3)0.052 (2)0.073 (3)−0.014 (2)−0.020 (2)0.014 (2)
C400.087 (3)0.084 (4)0.077 (3)−0.027 (3)0.016 (3)0.022 (3)
C410.089 (3)0.084 (3)0.057 (3)−0.024 (3)0.014 (2)0.011 (2)
C420.058 (2)0.060 (3)0.046 (2)−0.010 (2)0.0021 (19)0.0021 (19)
C430.067 (3)0.084 (3)0.049 (2)−0.006 (3)0.004 (2)−0.006 (2)
C450.0432 (19)0.0332 (19)0.041 (2)0.0001 (16)−0.0059 (16)0.0038 (15)
C460.049 (2)0.042 (2)0.038 (2)−0.0033 (17)−0.0086 (16)0.0032 (16)
O80.0635 (16)0.0380 (14)0.095 (2)−0.0049 (13)0.0196 (15)0.0039 (14)
O10.0393 (14)0.0691 (17)0.0689 (17)−0.0031 (12)0.0090 (12)0.0105 (13)
C440.039 (2)0.051 (2)0.051 (2)0.0000 (18)−0.0030 (17)−0.0033 (18)
O30.0591 (15)0.0508 (15)0.0677 (17)0.0008 (13)0.0113 (14)−0.0130 (13)
O40.0642 (17)0.0409 (14)0.104 (2)−0.0070 (13)0.0282 (16)0.0030 (14)
O50.0396 (14)0.0793 (18)0.0827 (19)−0.0116 (13)0.0027 (13)0.0030 (15)
O20.108 (2)0.100 (2)0.097 (2)0.0240 (19)0.056 (2)−0.0096 (19)
C210.0404 (19)0.045 (2)0.055 (2)−0.0018 (17)−0.0005 (17)−0.0070 (19)
C300.037 (2)0.051 (2)0.063 (2)0.0050 (17)0.0063 (18)−0.0063 (19)
C200.064 (3)0.069 (3)0.057 (3)0.009 (2)0.007 (2)−0.007 (2)

Geometric parameters (Å, °)

C1—C61.367 (6)C24—C291.381 (6)
C1—C21.370 (6)C24—H24A0.9303
C1—H1A0.9289C25—C261.390 (5)
C2—C31.371 (5)C25—H25A0.9298
C2—H2A0.9297C26—C271.376 (5)
C3—C41.384 (4)C26—C301.492 (5)
C3—H3A0.9303C27—C281.379 (5)
C4—C51.382 (5)C27—H27A0.9293
C4—C71.486 (4)C28—C291.360 (6)
C5—C61.379 (5)C28—H28A0.9297
C5—H5A0.9310C29—H29A0.9294
C6—H6A0.9303C31—C451.366 (4)
C7—O11.223 (3)C31—C321.439 (4)
C7—C81.509 (4)C31—C301.504 (4)
C8—C221.360 (4)C32—C331.399 (4)
C8—C91.437 (4)C32—C371.419 (5)
C9—C101.399 (4)C33—C341.372 (5)
C9—C141.422 (4)C33—H33A0.9308
C10—C111.375 (5)C34—C351.381 (6)
C10—H10A0.9293C34—H34A0.9305
C11—C121.360 (5)C35—C361.351 (6)
C11—H11A0.9298C35—H35A0.9303
C12—C131.361 (5)C36—C371.417 (5)
C12—H12A0.9309C36—H36A0.9308
C13—C141.408 (4)C37—C381.442 (5)
C13—H13A0.9293C38—C461.400 (5)
C14—C151.436 (4)C38—C391.422 (5)
C15—C231.405 (4)C39—C401.364 (5)
C15—C161.423 (4)C39—H39A0.9308
C16—C171.354 (5)C40—C411.358 (5)
C16—H16A0.9299C40—H40A0.9306
C17—C181.378 (5)C41—C421.372 (5)
C17—H17A0.9292C41—H41A0.9312
C18—C191.371 (5)C42—C461.406 (4)
C18—H18A0.9556C42—C431.450 (5)
C19—C231.402 (4)C45—C461.433 (4)
C19—C201.455 (5)C45—C441.466 (4)
C22—C231.430 (4)O8—C441.197 (4)
C22—C211.471 (4)O3—C201.370 (4)
O6—C431.210 (4)O3—C211.380 (4)
O7—C441.376 (4)O4—C211.189 (4)
O7—C431.397 (4)O5—C301.226 (3)
C24—C251.376 (5)O2—C201.214 (4)
C6—C1—C2120.9 (4)C27—C26—C25119.2 (3)
C6—C1—H1A119.6C27—C26—C30122.1 (3)
C2—C1—H1A119.5C25—C26—C30118.7 (3)
C1—C2—C3119.4 (4)C26—C27—C28120.3 (4)
C1—C2—H2A120.3C26—C27—H27A119.9
C3—C2—H2A120.3C28—C27—H27A119.8
C2—C3—C4120.6 (4)C29—C28—C27120.3 (4)
C2—C3—H3A119.7C29—C28—H28A119.9
C4—C3—H3A119.6C27—C28—H28A119.7
C5—C4—C3119.3 (3)C28—C29—C24120.2 (4)
C5—C4—C7121.8 (3)C28—C29—H29A119.9
C3—C4—C7119.0 (3)C24—C29—H29A119.9
C6—C5—C4119.8 (4)C45—C31—C32119.8 (3)
C6—C5—H5A120.1C45—C31—C30122.7 (3)
C4—C5—H5A120.1C32—C31—C30117.5 (3)
C1—C6—C5120.0 (4)C33—C32—C37119.4 (3)
C1—C6—H6A120.0C33—C32—C31121.1 (3)
C5—C6—H6A120.1C37—C32—C31119.5 (3)
O1—C7—C4122.3 (3)C34—C33—C32120.7 (4)
O1—C7—C8119.4 (3)C34—C33—H33A119.7
C4—C7—C8118.2 (3)C32—C33—H33A119.6
C22—C8—C9120.1 (3)C33—C34—C35120.0 (4)
C22—C8—C7121.7 (3)C33—C34—H34A120.1
C9—C8—C7118.3 (3)C35—C34—H34A119.9
C10—C9—C14119.2 (3)C36—C35—C34121.0 (4)
C10—C9—C8121.0 (3)C36—C35—H35A119.5
C14—C9—C8119.7 (3)C34—C35—H35A119.5
C11—C10—C9120.5 (4)C35—C36—C37121.3 (4)
C11—C10—H10A119.8C35—C36—H36A119.4
C9—C10—H10A119.7C37—C36—H36A119.4
C12—C11—C10120.6 (4)C36—C37—C32117.6 (4)
C12—C11—H11A119.6C36—C37—C38122.4 (4)
C10—C11—H11A119.8C32—C37—C38120.0 (3)
C11—C12—C13120.7 (4)C46—C38—C39117.4 (4)
C11—C12—H12A119.6C46—C38—C37119.0 (3)
C13—C12—H12A119.7C39—C38—C37123.6 (4)
C12—C13—C14121.6 (4)C40—C39—C38121.1 (4)
C12—C13—H13A119.3C40—C39—H39A119.4
C14—C13—H13A119.1C38—C39—H39A119.5
C13—C14—C9117.4 (3)C41—C40—C39120.8 (4)
C13—C14—C15123.1 (3)C41—C40—H40A119.6
C9—C14—C15119.5 (3)C39—C40—H40A119.6
C23—C15—C16117.1 (3)C40—C41—C42120.7 (4)
C23—C15—C14119.2 (3)C40—C41—H41A119.6
C16—C15—C14123.7 (3)C42—C41—H41A119.7
C17—C16—C15121.3 (4)C41—C42—C46120.1 (4)
C17—C16—H16A119.4C41—C42—C43119.2 (4)
C15—C16—H16A119.3C46—C42—C43120.6 (3)
C16—C17—C18121.1 (4)O6—C43—O7115.7 (4)
C16—C17—H17A119.5O6—C43—C42126.7 (4)
C18—C17—H17A119.5O7—C43—C42117.5 (3)
C19—C18—C17119.9 (4)C31—C45—C46121.5 (3)
C19—C18—H18A115.6C31—C45—C44119.8 (3)
C17—C18—H18A124.4C46—C45—C44118.7 (3)
C18—C19—C23120.3 (4)C38—C46—C42119.9 (3)
C18—C19—C20119.0 (4)C38—C46—C45120.1 (3)
C23—C19—C20120.7 (3)C42—C46—C45120.0 (3)
C8—C22—C23121.2 (3)O8—C44—O7116.1 (3)
C8—C22—C21119.9 (3)O8—C44—C45125.1 (3)
C23—C22—C21118.9 (3)O7—C44—C45118.7 (3)
C19—C23—C15120.3 (3)C20—O3—C21123.4 (3)
C19—C23—C22119.4 (3)O4—C21—O3115.9 (3)
C15—C23—C22120.2 (3)O4—C21—C22125.8 (3)
C44—O7—C43123.3 (3)O3—C21—C22118.3 (3)
C25—C24—C29119.8 (4)O5—C30—C26120.9 (3)
C25—C24—H24A120.1O5—C30—C31120.1 (3)
C29—C24—H24A120.1C26—C30—C31118.7 (3)
C24—C25—C26120.1 (4)O2—C20—O3116.7 (4)
C24—C25—H25A119.9O2—C20—C19125.2 (4)
C26—C25—H25A120.0O3—C20—C19118.1 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2667).

References

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