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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o160–o161.
Published online 2008 December 20. doi:  10.1107/S1600536808042566
PMCID: PMC2968073

3-(4-Biphenyl-1-yl)-3-hydr­oxy-1-phenyl­prop-2-en-1-one

Abstract

In the title compound, C21H16O2, the six crystallographically independent mol­ecules (Z′ = 6) all exist in the enolized form. Strong intra­molecular hydrogen bonds are observed: one approximate H-atom-centered O(...)H(...)O hydrogen bond, two tautomeric forms O—H(...)O (three mol­ecules) and O(...)H—O (two mol­ecules). Only one weak inter­molecular C—H(...)O hydrogen bond between two neighboring mol­ecules is observed in the crystal structure. In addition, eight very weak non-conventional inter­molecular C—H(...)π hydrogen-bonding contacts between mol­ecules are observed.

Related literature

For proton transfer in solid 1-phenyl­butane-1,3-dione and related 1,3-diones, see: Vila et al. (1991 [triangle]). For the crystal structures of eight intra­molecular hydrogen-bonded 1,3-diaryl-1,3-propane­dione enols, see: Bertolasi et al. (1991 [triangle]). For a discussion of the covalent versus the electrostatic nature of the strong hydrogen bond, see: Gilli et al. (2004 [triangle]). For electron transfer reactions of aromatic α,β-ep­oxy ketones, see: Hasegawa et al. (1997 [triangle]). For 1,3-diketones used as ligands, see: Jang et al. (2006 [triangle]). For weak hydrogen bonds, see: Desiraju & Steiner (2001 [triangle]).

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Object name is e-65-0o160-scheme1.jpg

Experimental

Crystal data

  • C21H16O2
  • M r = 300.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o160-efi1.jpg
  • a = 10.6087 (13) Å
  • b = 17.814 (2) Å
  • c = 26.394 (3) Å
  • α = 72.170 (2)°
  • β = 86.069 (2)°
  • γ = 89.450 (2)°
  • V = 4736.8 (10) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.980, T max = 0.989
  • 55512 measured reflections
  • 16514 independent reflections
  • 9991 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.078
  • wR(F 2) = 0.154
  • S = 1.07
  • 16514 reflections
  • 1255 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1999 [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 and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042566/si2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042566/si2145Isup2.hkl

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

Acknowledgments

The authors are grateful to Hubei Normal University for financial support.

supplementary crystallographic information

Comment

Both in solution and in the solid state, considerable attention has been focused on the structures of 1,3-diketones due to their enolic tautomeric forms and their ability to form strong intermolecular or intramolecular hydrogen bonds (Vila et al., 1991; Bertolasi et al., 1991; Gilli et al., 2004). These compounds posses sometimes unique chemical properties, which make them extremely attractive as intermediates in syntheses (Hasegawa et al., 1997). They are also used widely in the chemistry of metallocomplexes (Jang et al., 2006).

The crystal structure of the title compound (Fig. 1), has six independent molecules which all exist in the enol form, stabilized by intramolecular hydrogen bonds. The O—H distances of enol six ring and dihedral angles in six independent molecules are different. In molecule 4, the intramolecular O···H···O hydrogen bond can be described as approximately proton-centered, and the others as dynamic or static mixtures (Gilli et al., 2004) of two tautomeric O—H···O and O···H—O forms. Molecules 1, 2, 5 belong to O—H···O, and molecules 3 and 6 to the O···H—H tautomer (Table 1). In addition, there is only one weak intermolecular hydrogen bond between molecules 5 and 6, and other pairs of molecules do not show any C—H···O contacts, but probably C—H···π interactions (Table 1). Details of such non-conventional π contacts are reviewed by Desiraju & Steiner (2001). The following Cgs in Table 1 are the centroids of the π acceptor ring systems: Cg2 = C7 - C12, Cg3 = C16 - C21, Cg8 = C49 - C54, Cg10 = C64 - C69, Cg11 = C70 - C75, Cg14 = C91 - C96, Cg17 = C112 - C117. The central benzene ring in molecule 1 (C7 - C12) makes dihedral angles of 28.04 (8) and 9.01 (7) ° with the benzene rings C1 - C6 and C16 - C21, respectively; in the other five molecules, the corresponding angles are 18.49 (3) and 5.74 (2) °, 30.57 (5) and 12.48 (4) °, 26.58 (4) and 29.54 (3) °, 25.09 (5) and 28.07 (3) °, 27.68 (2) and 13.52 (4) °, respectively.

Experimental

1-(4-bilphenyl)ethanone (7.84 g, 0.04 mol), ethyl benzoate (6.02 g, 0.04 mol), NaNH2 (1.95 g, 0.05 mol) and dry ether (100 ml) were placed into round bottom flask. The mixture was stirred 6 h at room temperature under a blanket of nitrogen, acidified with dilute hydrochloric acid, and stirring was continued until all solids dissolved. The ether layer was separated and washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4 and was removed by evaporation. The residual solid was recrystallized from ethanol solution to give the title compound (yield 4.60 g, 38.3%, m.p. 383 K). Crystals suitable for X-ray diffraction were grown by slow evaporation of the CHCl3—EtOH (1:4) solutions at room temperature.

Refinement

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93 Å, and with Uiso(H) = 1.2 Ueq(C). The H atoms of the hydroxyl groups were located in a difference Fourier map and their positions were refined freely with Uiso(H) = 1.5 Uiso(O).

Figures

Fig. 1.
A view of the molecule 1 out of six independent molecules of the title compound, showing the atom-labeling scheme for non-hydrogen atoms. Displacement ellipsoids are drawn at the 50% probability level. It is difficult to show all molecules with atom labels. ...
Fig. 2.
A view of the six independent molecules, only O atoms were labelled and all H atoms have been omitted for clarity.

Crystal data

C21H16O2Z = 12
Mr = 300.34F(000) = 1896
Triclinic, P1Dx = 1.263 Mg m3
Hall symbol: -P 1Melting point: 383 K
a = 10.6087 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 17.814 (2) ÅCell parameters from 3181 reflections
c = 26.394 (3) Åθ = 2.3–21.5°
α = 72.170 (2)°µ = 0.08 mm1
β = 86.069 (2)°T = 298 K
γ = 89.450 (2)°Block, colorless
V = 4736.8 (10) Å30.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer16514 independent reflections
Radiation source: fine-focus sealed tube9991 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.980, Tmax = 0.989k = −21→19
55512 measured reflectionsl = −30→31

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)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0276P)2 + 3.4135P] where P = (Fo2 + 2Fc2)/3
16514 reflections(Δ/σ)max = 0.001
1255 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.16 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
C10.5878 (3)−0.04592 (19)0.92533 (13)0.0567 (8)
C20.5157 (3)−0.0527 (2)0.88522 (14)0.0655 (9)
H20.4953−0.00750.85840.079*
C30.4738 (3)−0.1249 (2)0.88418 (15)0.0744 (10)
H30.4253−0.12800.85680.089*
C40.5028 (4)−0.1925 (2)0.92335 (17)0.0798 (11)
H40.4742−0.24140.92270.096*
C50.5745 (4)−0.1871 (2)0.96328 (16)0.0826 (11)
H50.5947−0.23260.98990.099*
C60.6170 (3)−0.1146 (2)0.96440 (14)0.0693 (9)
H60.6659−0.11190.99170.083*
C70.6346 (3)0.03222 (18)0.92581 (13)0.0553 (8)
C80.6563 (3)0.09381 (19)0.87890 (13)0.0615 (8)
H80.63890.08640.84670.074*
C90.7029 (3)0.16578 (18)0.87886 (13)0.0600 (8)
H90.71720.20560.84660.072*
C100.7289 (3)0.18012 (19)0.92559 (13)0.0574 (8)
C110.7056 (3)0.1192 (2)0.97302 (13)0.0641 (9)
H110.72110.12721.00520.077*
C120.6600 (3)0.0468 (2)0.97290 (13)0.0642 (9)
H120.64590.00701.00510.077*
C130.7833 (3)0.2558 (2)0.92644 (15)0.0622 (9)
C140.7991 (3)0.32151 (19)0.88152 (14)0.0618 (9)
H140.77130.31930.84940.074*
C150.8558 (3)0.3906 (2)0.88353 (15)0.0655 (9)
C160.8740 (3)0.46205 (19)0.83683 (15)0.0644 (9)
C170.8367 (3)0.4650 (2)0.78706 (16)0.0777 (10)
H170.80130.42050.78200.093*
C180.8517 (4)0.5335 (3)0.74485 (18)0.0937 (13)
H180.82520.53490.71170.112*
C190.9054 (4)0.5995 (2)0.7512 (2)0.0959 (13)
H190.91600.64540.72260.115*
C200.9433 (4)0.5968 (2)0.8004 (2)0.0927 (13)
H200.97960.64130.80510.111*
C210.9280 (3)0.5292 (2)0.84268 (17)0.0804 (11)
H210.95420.52830.87580.097*
C220.2752 (3)−0.08517 (18)0.73658 (12)0.0566 (8)
C230.1476 (3)−0.1027 (2)0.74626 (16)0.0811 (11)
H230.0934−0.06720.75580.097*
C240.0991 (4)−0.1718 (2)0.74203 (19)0.0989 (14)
H240.0128−0.18230.74880.119*
C250.1759 (4)−0.2250 (2)0.72810 (16)0.0860 (12)
H250.1422−0.27140.72510.103*
C260.3026 (4)−0.2099 (2)0.71852 (15)0.0828 (11)
H260.3560−0.24600.70920.099*
C270.3508 (3)−0.1405 (2)0.72289 (14)0.0750 (10)
H270.4373−0.13070.71640.090*
C280.3293 (3)−0.00972 (18)0.73938 (11)0.0530 (8)
C290.2542 (3)0.0553 (2)0.73719 (14)0.0699 (10)
H290.16770.05130.73450.084*
C300.3040 (3)0.1256 (2)0.73883 (14)0.0668 (9)
H300.25100.16820.73680.080*
C310.4318 (3)0.13387 (18)0.74341 (12)0.0533 (8)
C320.5075 (3)0.06965 (19)0.74514 (13)0.0626 (9)
H320.59410.07380.74750.075*
C330.4568 (3)−0.00013 (19)0.74349 (13)0.0628 (9)
H330.5102−0.04240.74520.075*
C340.4883 (3)0.20721 (18)0.74734 (11)0.0537 (8)
C350.4209 (3)0.27266 (19)0.75000 (12)0.0598 (8)
H350.33350.27210.74880.072*
C360.4808 (3)0.34033 (19)0.75456 (12)0.0577 (8)
C370.4095 (3)0.41092 (18)0.75769 (12)0.0549 (8)
C380.2800 (3)0.4143 (2)0.75820 (15)0.0763 (10)
H380.23460.37100.75620.092*
C390.2158 (4)0.4804 (2)0.76161 (17)0.0897 (12)
H390.12800.48110.76250.108*
C400.2813 (4)0.5451 (2)0.76369 (15)0.0813 (11)
H400.23840.59000.76570.098*
C410.4104 (4)0.5433 (2)0.76286 (14)0.0765 (10)
H410.45530.58720.76410.092*
C420.47451 (17)0.47661 (11)0.76022 (7)0.0677 (9)
H420.56220.47580.76010.081*
C430.66144 (17)0.40465 (11)0.57063 (7)0.0542 (8)
C440.61617 (17)0.33663 (11)0.60936 (7)0.0605 (8)
H440.56200.34120.63750.073*
C450.6498 (3)0.2625 (2)0.60731 (14)0.0706 (10)
H450.61760.21800.63370.085*
C460.7308 (3)0.2542 (2)0.56646 (15)0.0715 (10)
H460.75420.20440.56510.086*
C470.7767 (3)0.3206 (2)0.52771 (14)0.0708 (9)
H470.83150.31560.49990.085*
C480.7422 (3)0.3947 (2)0.52958 (13)0.0639 (9)
H480.77380.43890.50270.077*
C490.6198 (3)0.48401 (18)0.57178 (12)0.0546 (8)
C500.5856 (3)0.4987 (2)0.61940 (13)0.0668 (9)
H500.59530.45930.65140.080*
C510.5372 (3)0.5705 (2)0.62040 (13)0.0681 (9)
H510.51350.57840.65300.082*
C520.5238 (3)0.63086 (19)0.57366 (13)0.0580 (8)
C530.5617 (3)0.61754 (19)0.52591 (13)0.0630 (9)
H530.55580.65780.49400.076*
C540.6079 (3)0.54530 (19)0.52530 (13)0.0619 (8)
H540.63190.53750.49270.074*
C550.4654 (3)0.7057 (2)0.57609 (14)0.0631 (9)
C560.4660 (3)0.77418 (19)0.53215 (13)0.0631 (9)
H560.50980.77460.50030.076*
C570.4030 (3)0.8408 (2)0.53510 (14)0.0636 (9)
C580.3959 (3)0.91392 (19)0.48994 (13)0.0582 (8)
C590.3344 (3)0.9786 (2)0.49812 (15)0.0704 (9)
H590.29740.97510.53170.084*
C600.3274 (4)1.0482 (2)0.45687 (18)0.0828 (11)
H600.28621.09120.46290.099*
C610.3807 (4)1.0538 (2)0.40745 (17)0.0867 (12)
H610.37511.10040.37960.104*
C620.4426 (4)0.9904 (2)0.39914 (15)0.0927 (13)
H620.47970.99450.36550.111*
C630.4507 (4)0.9209 (2)0.43984 (14)0.0780 (10)
H630.49340.87840.43350.094*
C64−0.0076 (3)0.64519 (19)0.60137 (13)0.0622 (9)
C650.0684 (4)0.7057 (2)0.60501 (14)0.0751 (10)
H650.15560.69960.60390.090*
C660.0184 (4)0.7749 (2)0.61019 (16)0.0867 (12)
H660.07180.81490.61210.104*
C67−0.1092 (5)0.7849 (2)0.61256 (18)0.0971 (13)
H67−0.14320.83090.61710.116*
C68−0.1863 (4)0.7270 (2)0.60815 (19)0.1032 (14)
H68−0.27330.73400.60900.124*
C69−0.1368 (4)0.6580 (2)0.60241 (16)0.0827 (11)
H69−0.19110.61920.59920.099*
C700.0463 (3)0.56919 (18)0.59860 (12)0.0575 (8)
C710.1609 (3)0.5435 (2)0.61956 (14)0.0711 (10)
H710.20450.57480.63510.085*
C720.2118 (3)0.4727 (2)0.61792 (14)0.0685 (9)
H720.28930.45760.63200.082*
C730.1497 (3)0.42378 (18)0.59562 (12)0.0564 (8)
C740.0361 (3)0.44957 (19)0.57408 (13)0.0638 (9)
H74−0.00690.41850.55820.077*
C75−0.0149 (3)0.52034 (19)0.57562 (13)0.0636 (9)
H75−0.09180.53580.56100.076*
C760.2072 (3)0.34779 (19)0.59541 (13)0.0599 (8)
C770.1470 (3)0.29011 (19)0.58078 (14)0.0666 (9)
H770.06690.29960.56810.080*
C780.2039 (3)0.2175 (2)0.58464 (14)0.0679 (9)
C790.1364 (3)0.1508 (2)0.57565 (14)0.0655 (9)
C800.1699 (4)0.0748 (2)0.60239 (15)0.0791 (11)
H800.23770.06640.62390.095*
C810.1048 (5)0.0114 (2)0.59783 (17)0.0919 (13)
H810.1273−0.03950.61680.110*
C820.0065 (4)0.0232 (3)0.5654 (2)0.0965 (14)
H82−0.0381−0.01980.56230.116*
C83−0.0265 (4)0.0987 (3)0.5371 (2)0.1031 (14)
H83−0.09220.10680.51450.124*
C840.0386 (4)0.1624 (2)0.54246 (17)0.0881 (12)
H840.01620.21340.52350.106*
C850.7565 (3)−0.22780 (17)0.09724 (12)0.0546 (8)
C860.8340 (3)−0.2897 (2)0.09348 (15)0.0724 (10)
H860.9211−0.28210.08890.087*
C870.7834 (4)−0.3621 (2)0.09647 (16)0.0827 (11)
H870.8365−0.40290.09410.099*
C880.6558 (4)−0.3740 (2)0.10284 (15)0.0753 (10)
H880.6220−0.42280.10470.090*
C890.5777 (3)−0.3141 (2)0.10649 (14)0.0710 (10)
H890.4907−0.32230.11090.085*
C900.6274 (3)−0.24147 (19)0.10365 (13)0.0631 (9)
H900.5733−0.20110.10610.076*
C910.8121 (3)−0.15018 (17)0.09457 (12)0.0541 (8)
C920.9297 (3)−0.12523 (18)0.06898 (13)0.0599 (8)
H920.9749−0.15790.05300.072*
C930.9814 (3)−0.05386 (18)0.06658 (13)0.0619 (9)
H931.0613−0.03960.04970.074*
C940.9167 (3)−0.00299 (17)0.08885 (12)0.0525 (8)
C950.7998 (3)−0.02704 (18)0.11531 (13)0.0630 (9)
H950.75540.00580.13140.076*
C960.7484 (3)−0.09917 (18)0.11802 (13)0.0632 (9)
H960.6697−0.11400.13590.076*
C970.9728 (3)0.07476 (19)0.08389 (13)0.0590 (8)
C980.9081 (3)0.13606 (18)0.09470 (13)0.0625 (9)
H980.82480.12790.10880.075*
C990.9644 (4)0.2103 (2)0.08496 (14)0.0668 (9)
C1000.8937 (3)0.27851 (19)0.09247 (14)0.0662 (9)
C1010.7873 (4)0.2697 (2)0.12713 (16)0.0782 (11)
H1010.75950.21940.14730.094*
C1020.7220 (4)0.3343 (2)0.13221 (18)0.0944 (13)
H1020.65100.32770.15590.113*
C1030.7623 (5)0.4089 (3)0.1020 (2)0.1068 (15)
H1030.71780.45270.10510.128*
C1040.8675 (5)0.4189 (2)0.0675 (2)0.1082 (15)
H1040.89440.46940.04720.130*
C1050.9333 (4)0.3543 (2)0.06286 (16)0.0860 (12)
H1051.00530.36130.03960.103*
C1060.0752 (3)−0.15222 (19)0.25599 (13)0.0562 (8)
C1070.0131 (3)−0.1710 (2)0.21710 (14)0.0693 (9)
H107−0.0088−0.13080.18720.083*
C108−0.0173 (4)−0.2479 (2)0.22154 (16)0.0811 (11)
H108−0.0593−0.25890.19480.097*
C1090.0138 (4)−0.3083 (2)0.26497 (19)0.0856 (12)
H109−0.0065−0.36020.26790.103*
C1100.0754 (4)−0.2910 (2)0.30415 (18)0.0918 (13)
H1100.0975−0.33160.33380.110*
C1110.1046 (3)−0.2143 (2)0.29990 (15)0.0800 (11)
H1110.1451−0.20370.32720.096*
C1120.1156 (3)−0.07058 (19)0.25050 (13)0.0556 (8)
C1130.1400 (3)−0.01567 (19)0.20068 (14)0.0616 (8)
H1130.1245−0.02960.17050.074*
C1140.1862 (3)0.0587 (2)0.19444 (14)0.0631 (9)
H1140.20220.09350.16030.076*
C1150.2094 (3)0.0824 (2)0.23827 (14)0.0592 (8)
C1160.1825 (3)0.0292 (2)0.28834 (15)0.0737 (10)
H1160.19620.04390.31840.088*
C1170.1356 (3)−0.0453 (2)0.29452 (14)0.0684 (9)
H1170.1169−0.07940.32870.082*
C1180.2652 (3)0.1608 (2)0.23286 (16)0.0690 (9)
C1190.2692 (3)0.2225 (2)0.18547 (15)0.0685 (9)
H1190.23100.21550.15650.082*
C1200.3283 (3)0.2946 (2)0.17956 (17)0.0730 (10)
C1210.3364 (3)0.3613 (2)0.12977 (16)0.0679 (9)
C1220.2953 (4)0.3548 (2)0.08281 (17)0.0834 (11)
H1220.26270.30700.08190.100*
C1230.3021 (4)0.4183 (3)0.03741 (18)0.1027 (14)
H1230.27420.41280.00610.123*
C1240.3493 (4)0.4896 (3)0.0375 (2)0.0992 (13)
H1240.35340.53240.00650.119*
C1250.3899 (4)0.4970 (2)0.0834 (2)0.0974 (14)
H1250.42180.54520.08380.117*
C1260.3846 (3)0.4337 (2)0.12953 (19)0.0884 (12)
H1260.41340.43960.16060.106*
O10.8195 (3)0.25799 (15)0.97179 (10)0.0871 (8)
H1A0.857 (4)0.325 (3)0.9602 (17)0.131*
O20.8954 (2)0.39522 (15)0.92758 (11)0.0836 (7)
O30.6110 (2)0.20682 (14)0.74853 (9)0.0714 (6)
H3A0.631 (3)0.272 (2)0.7511 (14)0.107*
O40.6002 (2)0.34201 (14)0.75623 (10)0.0741 (7)
O50.4111 (3)0.70518 (15)0.62114 (10)0.0903 (8)
H5A0.363 (4)0.777 (3)0.6100 (17)0.135*
O60.3433 (3)0.84226 (15)0.57949 (10)0.0863 (8)
O70.3205 (2)0.33673 (15)0.61127 (11)0.0833 (7)
H7A0.347 (4)0.269 (3)0.6064 (16)0.125*
O80.3175 (2)0.20547 (15)0.59834 (11)0.0851 (7)
O91.0918 (2)0.08344 (15)0.06661 (10)0.0750 (7)
H9A1.109 (3)0.152 (3)0.0606 (14)0.112*
O101.0808 (3)0.22160 (15)0.06791 (11)0.0878 (8)
O110.3126 (3)0.16920 (17)0.27458 (11)0.0952 (8)
H11A0.345 (4)0.245 (3)0.2566 (18)0.143*
O120.3820 (3)0.30490 (17)0.21993 (13)0.1007 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0436 (18)0.061 (2)0.065 (2)0.0014 (15)0.0072 (16)−0.0211 (18)
C20.056 (2)0.061 (2)0.081 (2)0.0003 (17)−0.0077 (18)−0.0231 (19)
C30.068 (2)0.071 (3)0.089 (3)−0.0040 (19)−0.011 (2)−0.031 (2)
C40.081 (3)0.064 (3)0.098 (3)−0.006 (2)0.000 (2)−0.031 (2)
C50.099 (3)0.060 (2)0.083 (3)−0.002 (2)−0.007 (2)−0.014 (2)
C60.075 (2)0.065 (2)0.066 (2)−0.0018 (19)−0.0002 (18)−0.0169 (19)
C70.0460 (18)0.062 (2)0.059 (2)0.0012 (15)0.0059 (15)−0.0215 (18)
C80.064 (2)0.065 (2)0.059 (2)−0.0029 (17)−0.0030 (17)−0.0237 (18)
C90.061 (2)0.054 (2)0.061 (2)0.0006 (16)−0.0005 (16)−0.0128 (17)
C100.0492 (19)0.061 (2)0.064 (2)0.0019 (15)0.0015 (16)−0.0241 (18)
C110.066 (2)0.069 (2)0.060 (2)0.0010 (18)0.0013 (17)−0.0249 (19)
C120.067 (2)0.064 (2)0.057 (2)−0.0033 (17)0.0066 (17)−0.0139 (17)
C130.053 (2)0.067 (2)0.072 (2)0.0048 (17)−0.0052 (17)−0.029 (2)
C140.055 (2)0.062 (2)0.071 (2)−0.0022 (16)−0.0109 (17)−0.0220 (19)
C150.053 (2)0.064 (2)0.085 (3)0.0037 (17)−0.0056 (18)−0.030 (2)
C160.0484 (19)0.058 (2)0.089 (3)0.0004 (16)−0.0038 (18)−0.026 (2)
C170.065 (2)0.067 (2)0.096 (3)−0.0107 (19)−0.005 (2)−0.017 (2)
C180.082 (3)0.087 (3)0.099 (3)−0.019 (2)−0.012 (2)−0.009 (3)
C190.077 (3)0.069 (3)0.122 (4)−0.010 (2)0.002 (3)−0.001 (3)
C200.082 (3)0.062 (3)0.131 (4)−0.008 (2)0.007 (3)−0.027 (3)
C210.070 (2)0.068 (3)0.109 (3)−0.004 (2)−0.003 (2)−0.036 (2)
C220.062 (2)0.056 (2)0.0523 (19)0.0034 (16)−0.0018 (16)−0.0172 (16)
C230.065 (2)0.061 (2)0.119 (3)0.0034 (19)−0.010 (2)−0.029 (2)
C240.069 (3)0.067 (3)0.165 (4)0.001 (2)−0.023 (3)−0.037 (3)
C250.098 (3)0.061 (2)0.099 (3)−0.009 (2)−0.023 (3)−0.022 (2)
C260.104 (3)0.063 (2)0.089 (3)−0.003 (2)0.009 (2)−0.037 (2)
C270.072 (2)0.073 (2)0.085 (3)−0.004 (2)0.012 (2)−0.036 (2)
C280.053 (2)0.058 (2)0.0500 (19)0.0029 (16)−0.0018 (15)−0.0201 (15)
C290.048 (2)0.073 (2)0.097 (3)0.0004 (18)−0.0002 (18)−0.040 (2)
C300.053 (2)0.063 (2)0.093 (3)0.0052 (17)−0.0014 (18)−0.038 (2)
C310.052 (2)0.060 (2)0.0499 (18)0.0031 (16)−0.0031 (15)−0.0199 (15)
C320.0468 (19)0.070 (2)0.077 (2)0.0050 (17)−0.0113 (16)−0.0301 (19)
C330.059 (2)0.060 (2)0.076 (2)0.0110 (17)−0.0099 (17)−0.0301 (18)
C340.053 (2)0.064 (2)0.0447 (18)−0.0018 (16)−0.0005 (15)−0.0172 (15)
C350.0499 (19)0.065 (2)0.068 (2)−0.0016 (17)−0.0031 (16)−0.0264 (18)
C360.058 (2)0.062 (2)0.054 (2)−0.0115 (17)0.0001 (16)−0.0197 (16)
C370.059 (2)0.057 (2)0.0504 (19)−0.0034 (16)−0.0026 (15)−0.0195 (15)
C380.067 (2)0.063 (2)0.107 (3)−0.0023 (19)−0.012 (2)−0.037 (2)
C390.072 (3)0.082 (3)0.127 (4)0.008 (2)−0.015 (2)−0.048 (3)
C400.094 (3)0.062 (2)0.095 (3)0.008 (2)−0.020 (2)−0.031 (2)
C410.101 (3)0.056 (2)0.078 (3)−0.010 (2)−0.016 (2)−0.0263 (19)
C420.073 (2)0.064 (2)0.070 (2)−0.0131 (19)−0.0098 (18)−0.0245 (18)
C430.0445 (18)0.061 (2)0.055 (2)−0.0007 (15)−0.0094 (15)−0.0135 (16)
C440.056 (2)0.062 (2)0.062 (2)0.0019 (16)−0.0042 (16)−0.0159 (18)
C450.072 (2)0.065 (2)0.068 (2)−0.0041 (18)−0.0132 (19)−0.0089 (19)
C460.077 (3)0.061 (2)0.077 (3)0.0049 (19)−0.013 (2)−0.021 (2)
C470.071 (2)0.074 (3)0.070 (2)0.0074 (19)−0.0018 (19)−0.026 (2)
C480.063 (2)0.064 (2)0.061 (2)0.0007 (17)−0.0015 (17)−0.0134 (17)
C490.0493 (19)0.060 (2)0.052 (2)−0.0041 (15)−0.0074 (15)−0.0123 (17)
C500.080 (2)0.062 (2)0.051 (2)−0.0015 (18)−0.0052 (17)−0.0062 (17)
C510.083 (3)0.066 (2)0.052 (2)0.0007 (19)0.0033 (18)−0.0166 (18)
C520.059 (2)0.060 (2)0.053 (2)−0.0043 (16)−0.0029 (16)−0.0140 (17)
C530.071 (2)0.061 (2)0.052 (2)0.0008 (17)−0.0098 (17)−0.0084 (17)
C540.065 (2)0.066 (2)0.055 (2)0.0013 (17)−0.0022 (16)−0.0189 (18)
C550.064 (2)0.065 (2)0.063 (2)−0.0021 (17)−0.0045 (18)−0.0221 (19)
C560.066 (2)0.064 (2)0.058 (2)0.0040 (17)−0.0005 (17)−0.0168 (18)
C570.061 (2)0.070 (2)0.065 (2)−0.0046 (18)0.0021 (18)−0.0292 (19)
C580.0531 (19)0.060 (2)0.064 (2)−0.0036 (16)−0.0092 (16)−0.0210 (18)
C590.069 (2)0.069 (2)0.076 (2)0.0100 (19)−0.0080 (19)−0.027 (2)
C600.088 (3)0.068 (3)0.098 (3)0.016 (2)−0.023 (2)−0.030 (2)
C610.100 (3)0.075 (3)0.080 (3)0.014 (2)−0.024 (2)−0.014 (2)
C620.125 (4)0.083 (3)0.062 (3)0.016 (3)−0.004 (2)−0.012 (2)
C630.098 (3)0.065 (2)0.069 (3)0.009 (2)0.000 (2)−0.020 (2)
C640.068 (2)0.056 (2)0.062 (2)−0.0013 (17)−0.0076 (17)−0.0170 (17)
C650.073 (2)0.068 (2)0.091 (3)0.002 (2)−0.018 (2)−0.033 (2)
C660.093 (3)0.063 (3)0.112 (3)0.001 (2)−0.023 (3)−0.036 (2)
C670.102 (4)0.068 (3)0.132 (4)0.020 (2)−0.028 (3)−0.043 (3)
C680.082 (3)0.081 (3)0.157 (4)0.023 (2)−0.031 (3)−0.047 (3)
C690.072 (3)0.067 (3)0.115 (3)0.003 (2)−0.022 (2)−0.034 (2)
C700.054 (2)0.059 (2)0.058 (2)−0.0075 (16)−0.0053 (16)−0.0165 (16)
C710.067 (2)0.073 (2)0.084 (3)−0.0020 (19)−0.018 (2)−0.037 (2)
C720.060 (2)0.072 (2)0.080 (2)0.0055 (18)−0.0227 (18)−0.029 (2)
C730.0509 (19)0.059 (2)0.060 (2)−0.0048 (16)−0.0032 (16)−0.0178 (16)
C740.060 (2)0.059 (2)0.075 (2)−0.0080 (17)−0.0123 (18)−0.0219 (18)
C750.052 (2)0.060 (2)0.082 (2)0.0000 (16)−0.0160 (17)−0.0236 (18)
C760.053 (2)0.064 (2)0.061 (2)−0.0011 (17)−0.0046 (16)−0.0171 (17)
C770.053 (2)0.066 (2)0.086 (3)0.0055 (17)−0.0087 (18)−0.031 (2)
C780.058 (2)0.076 (3)0.072 (2)0.0034 (19)−0.0022 (18)−0.0269 (19)
C790.067 (2)0.058 (2)0.074 (2)0.0038 (18)0.0044 (19)−0.0260 (19)
C800.097 (3)0.065 (3)0.078 (3)0.004 (2)−0.001 (2)−0.027 (2)
C810.123 (4)0.066 (3)0.087 (3)−0.003 (3)0.009 (3)−0.029 (2)
C820.101 (3)0.077 (3)0.126 (4)−0.016 (3)0.022 (3)−0.057 (3)
C830.088 (3)0.088 (3)0.153 (4)0.004 (3)−0.023 (3)−0.063 (3)
C840.081 (3)0.072 (3)0.122 (4)0.011 (2)−0.021 (3)−0.043 (2)
C850.059 (2)0.0496 (19)0.059 (2)0.0033 (15)−0.0113 (16)−0.0195 (15)
C860.055 (2)0.064 (2)0.108 (3)0.0037 (17)−0.0126 (19)−0.039 (2)
C870.075 (3)0.057 (2)0.128 (3)0.0077 (19)−0.013 (2)−0.045 (2)
C880.075 (3)0.057 (2)0.098 (3)−0.0052 (19)−0.013 (2)−0.029 (2)
C890.061 (2)0.066 (2)0.087 (3)−0.0089 (19)−0.0056 (19)−0.024 (2)
C900.059 (2)0.058 (2)0.075 (2)0.0031 (17)−0.0055 (17)−0.0244 (18)
C910.053 (2)0.0501 (19)0.059 (2)0.0047 (15)−0.0077 (16)−0.0164 (16)
C920.061 (2)0.056 (2)0.069 (2)0.0076 (16)−0.0012 (17)−0.0282 (17)
C930.057 (2)0.059 (2)0.072 (2)−0.0007 (16)0.0008 (17)−0.0253 (18)
C940.0493 (19)0.0483 (18)0.062 (2)0.0015 (15)−0.0066 (15)−0.0184 (16)
C950.064 (2)0.053 (2)0.077 (2)0.0032 (17)0.0024 (18)−0.0292 (18)
C960.053 (2)0.061 (2)0.079 (2)−0.0011 (16)0.0064 (17)−0.0284 (18)
C970.056 (2)0.061 (2)0.064 (2)0.0019 (17)−0.0113 (17)−0.0227 (17)
C980.056 (2)0.055 (2)0.079 (2)0.0007 (16)−0.0056 (17)−0.0253 (18)
C990.069 (2)0.059 (2)0.080 (2)−0.0040 (19)−0.015 (2)−0.0297 (19)
C1000.075 (2)0.054 (2)0.076 (2)−0.0007 (18)−0.026 (2)−0.0258 (19)
C1010.087 (3)0.060 (2)0.094 (3)−0.001 (2)−0.014 (2)−0.030 (2)
C1020.103 (3)0.077 (3)0.117 (4)0.018 (3)−0.016 (3)−0.048 (3)
C1030.135 (4)0.066 (3)0.133 (4)0.027 (3)−0.037 (3)−0.045 (3)
C1040.144 (5)0.056 (3)0.127 (4)0.008 (3)−0.034 (4)−0.027 (3)
C1050.106 (3)0.058 (2)0.096 (3)−0.003 (2)−0.022 (2)−0.022 (2)
C1060.0381 (17)0.066 (2)0.062 (2)0.0002 (15)0.0003 (15)−0.0163 (18)
C1070.065 (2)0.066 (2)0.075 (2)0.0034 (18)−0.0113 (19)−0.0184 (19)
C1080.082 (3)0.071 (3)0.090 (3)−0.008 (2)−0.011 (2)−0.023 (2)
C1090.070 (3)0.067 (3)0.115 (4)−0.010 (2)0.006 (2)−0.024 (3)
C1100.080 (3)0.073 (3)0.101 (3)−0.012 (2)−0.014 (2)0.007 (2)
C1110.069 (2)0.084 (3)0.074 (3)−0.012 (2)−0.007 (2)−0.004 (2)
C1120.0372 (17)0.067 (2)0.062 (2)0.0049 (15)−0.0038 (15)−0.0192 (18)
C1130.056 (2)0.066 (2)0.066 (2)0.0043 (17)−0.0096 (17)−0.0254 (19)
C1140.060 (2)0.065 (2)0.065 (2)0.0043 (17)−0.0064 (17)−0.0217 (18)
C1150.0479 (19)0.067 (2)0.069 (2)0.0093 (16)−0.0071 (16)−0.0292 (19)
C1160.071 (2)0.090 (3)0.070 (3)0.000 (2)−0.0104 (19)−0.038 (2)
C1170.063 (2)0.081 (3)0.060 (2)−0.0004 (19)−0.0060 (17)−0.0192 (19)
C1180.053 (2)0.080 (3)0.085 (3)0.0089 (18)−0.0155 (19)−0.039 (2)
C1190.061 (2)0.070 (2)0.084 (3)−0.0013 (18)−0.0140 (19)−0.034 (2)
C1200.057 (2)0.078 (3)0.100 (3)0.0080 (19)−0.021 (2)−0.048 (2)
C1210.053 (2)0.062 (2)0.096 (3)0.0003 (17)−0.0075 (19)−0.034 (2)
C1220.096 (3)0.070 (3)0.095 (3)−0.007 (2)−0.004 (2)−0.041 (2)
C1230.133 (4)0.085 (3)0.092 (3)−0.017 (3)−0.005 (3)−0.028 (3)
C1240.085 (3)0.090 (3)0.120 (4)−0.015 (2)−0.003 (3)−0.028 (3)
C1250.074 (3)0.067 (3)0.151 (4)−0.011 (2)−0.022 (3)−0.029 (3)
C1260.073 (3)0.079 (3)0.126 (4)−0.002 (2)−0.030 (2)−0.043 (3)
O10.115 (2)0.0733 (17)0.0788 (18)−0.0072 (15)−0.0237 (16)−0.0285 (14)
O20.0937 (19)0.0717 (17)0.094 (2)−0.0030 (14)−0.0219 (16)−0.0346 (15)
O30.0497 (14)0.0723 (16)0.0941 (18)−0.0024 (12)−0.0069 (12)−0.0277 (14)
O40.0568 (15)0.0720 (16)0.0970 (18)−0.0068 (12)−0.0079 (13)−0.0301 (14)
O50.127 (2)0.0739 (17)0.0641 (16)0.0133 (16)0.0173 (15)−0.0177 (13)
O60.106 (2)0.0730 (17)0.0753 (17)0.0084 (15)0.0215 (15)−0.0215 (14)
O70.0647 (16)0.0781 (17)0.115 (2)0.0099 (13)−0.0272 (15)−0.0376 (16)
O80.0710 (18)0.0760 (18)0.114 (2)0.0137 (14)−0.0186 (15)−0.0355 (16)
O90.0578 (15)0.0729 (16)0.0995 (19)−0.0068 (12)0.0041 (13)−0.0359 (14)
O100.0745 (18)0.0729 (17)0.122 (2)−0.0160 (14)0.0023 (16)−0.0406 (16)
O110.113 (2)0.090 (2)0.093 (2)−0.0050 (16)−0.0384 (17)−0.0355 (16)
O120.111 (2)0.086 (2)0.117 (2)−0.0121 (16)−0.0431 (19)−0.0391 (18)

Geometric parameters (Å, °)

C1—C21.382 (4)C65—H650.9300
C1—C61.386 (4)C66—C671.363 (5)
C1—C71.486 (4)C66—H660.9300
C2—C31.374 (4)C67—C681.360 (5)
C2—H20.9300C67—H670.9300
C3—C41.375 (5)C68—C691.379 (5)
C3—H30.9300C68—H680.9300
C4—C51.368 (5)C69—H690.9300
C4—H40.9300C70—C711.385 (4)
C5—C61.382 (5)C70—C751.391 (4)
C5—H50.9300C71—C721.379 (4)
C6—H60.9300C71—H710.9300
C7—C81.387 (4)C72—C731.385 (4)
C7—C121.389 (4)C72—H720.9300
C8—C91.378 (4)C73—C741.382 (4)
C8—H80.9300C73—C761.481 (4)
C9—C101.380 (4)C74—C751.378 (4)
C9—H90.9300C74—H740.9300
C10—C111.392 (4)C75—H750.9300
C10—C131.479 (4)C76—O71.293 (4)
C11—C121.382 (4)C76—C771.379 (4)
C11—H110.9300C77—C781.399 (4)
C12—H120.9300C77—H770.9300
C13—O11.294 (4)C78—O81.280 (4)
C13—C141.390 (4)C78—C791.481 (5)
C14—C151.393 (4)C79—C841.377 (5)
C14—H140.9300C79—C801.378 (5)
C15—O21.288 (4)C80—C811.369 (5)
C15—C161.479 (5)C80—H800.9300
C16—C171.383 (5)C81—C821.369 (6)
C16—C211.386 (4)C81—H810.9300
C17—C181.379 (5)C82—C831.379 (6)
C17—H170.9300C82—H820.9300
C18—C191.372 (5)C83—C841.383 (5)
C18—H180.9300C83—H830.9300
C19—C201.373 (6)C84—H840.9300
C19—H190.9300C85—C901.383 (4)
C20—C211.371 (5)C85—C861.392 (4)
C20—H200.9300C85—C911.488 (4)
C21—H210.9300C86—C871.379 (4)
C22—C231.381 (4)C86—H860.9300
C22—C271.381 (4)C87—C881.362 (5)
C22—C281.491 (4)C87—H870.9300
C23—C241.377 (5)C88—C891.368 (4)
C23—H230.9300C88—H880.9300
C24—C251.362 (5)C89—C901.380 (4)
C24—H240.9300C89—H890.9300
C25—C261.365 (5)C90—H900.9300
C25—H250.9300C91—C921.387 (4)
C26—C271.383 (5)C91—C961.393 (4)
C26—H260.9300C92—C931.372 (4)
C27—H270.9300C92—H920.9300
C28—C331.381 (4)C93—C941.377 (4)
C28—C291.388 (4)C93—H930.9300
C29—C301.379 (4)C94—C951.385 (4)
C29—H290.9300C94—C971.478 (4)
C30—C311.382 (4)C95—C961.380 (4)
C30—H300.9300C95—H950.9300
C31—C321.382 (4)C96—H960.9300
C31—C341.477 (4)C97—O91.307 (4)
C32—C331.374 (4)C97—C981.376 (4)
C32—H320.9300C98—C991.400 (4)
C33—H330.9300C98—H980.9300
C34—O31.304 (3)C99—O101.281 (4)
C34—C351.379 (4)C99—C1001.479 (5)
C35—C361.409 (4)C100—C1011.382 (5)
C35—H350.9300C100—C1051.388 (5)
C36—O41.271 (4)C101—C1021.374 (5)
C36—C371.482 (4)C101—H1010.9300
C37—C381.374 (4)C102—C1031.379 (6)
C37—C421.385 (3)C102—H1020.9300
C38—C391.379 (5)C103—C1041.368 (6)
C38—H380.9300C103—H1030.9300
C39—C401.368 (5)C104—C1051.374 (5)
C39—H390.9300C104—H1040.9300
C40—C411.369 (5)C105—H1050.9300
C40—H400.9300C106—C1071.381 (4)
C41—C421.380 (4)C106—C1111.386 (4)
C41—H410.9300C106—C1121.481 (4)
C42—H420.9300C107—C1081.379 (5)
C43—C481.388C107—H1070.9300
C43—C441.3890C108—C1091.367 (5)
C43—C491.486C108—H1080.9300
C44—C451.381C109—C1101.372 (5)
C44—H440.9300C109—H1090.9300
C45—C461.375 (5)C110—C1111.374 (5)
C45—H450.9300C110—H1100.9300
C46—C471.373 (5)C111—H1110.9300
C46—H460.9300C112—C1131.387 (4)
C47—C481.381 (4)C112—C1171.398 (4)
C47—H470.9300C113—C1141.375 (4)
C48—H480.9300C113—H1130.9300
C49—C541.383 (4)C114—C1151.385 (4)
C49—C501.384 (4)C114—H1140.9300
C50—C511.381 (4)C115—C1161.383 (5)
C50—H500.9300C115—C1181.484 (5)
C51—C521.381 (4)C116—C1171.379 (4)
C51—H510.9300C116—H1160.9300
C52—C531.385 (4)C117—H1170.9300
C52—C551.482 (4)C118—O111.291 (4)
C53—C541.377 (4)C118—C1191.388 (5)
C53—H530.9300C119—C1201.396 (5)
C54—H540.9300C119—H1190.9300
C55—O51.283 (4)C120—O121.303 (4)
C55—C561.402 (4)C120—C1211.475 (5)
C56—C571.377 (4)C121—C1221.379 (5)
C56—H560.9300C121—C1261.390 (5)
C57—O61.300 (4)C122—C1231.371 (5)
C57—C581.477 (4)C122—H1220.9300
C58—C631.378 (4)C123—C1241.371 (5)
C58—C591.384 (4)C123—H1230.9300
C59—C601.382 (5)C124—C1251.358 (6)
C59—H590.9300C124—H1240.9300
C60—C611.360 (5)C125—C1261.381 (5)
C60—H600.9300C125—H1250.9300
C61—C621.368 (5)C126—H1260.9300
C61—H610.9300O1—H1A1.21 (5)
C62—C631.376 (5)O3—H3A1.20 (4)
C62—H620.9300O6—H5A1.22 (5)
C63—H630.9300O7—H7A1.27 (5)
C64—C651.383 (4)O8—H7A1.26 (4)
C64—C691.387 (5)O9—H9A1.19 (4)
C64—C701.485 (4)O12—H11A1.24 (5)
C65—C661.378 (5)
C2—C1—C6117.7 (3)C67—C66—C65120.2 (4)
C2—C1—C7121.1 (3)C67—C66—H66119.9
C6—C1—C7121.2 (3)C65—C66—H66119.9
C3—C2—C1121.3 (3)C68—C67—C66119.4 (4)
C3—C2—H2119.4C68—C67—H67120.3
C1—C2—H2119.4C66—C67—H67120.3
C2—C3—C4120.4 (4)C67—C68—C69120.7 (4)
C2—C3—H3119.8C67—C68—H68119.6
C4—C3—H3119.8C69—C68—H68119.6
C5—C4—C3119.2 (4)C68—C69—C64121.2 (4)
C5—C4—H4120.4C68—C69—H69119.4
C3—C4—H4120.4C64—C69—H69119.4
C4—C5—C6120.5 (4)C71—C70—C75116.9 (3)
C4—C5—H5119.7C71—C70—C64120.8 (3)
C6—C5—H5119.7C75—C70—C64122.4 (3)
C5—C6—C1120.9 (3)C72—C71—C70121.6 (3)
C5—C6—H6119.6C72—C71—H71119.2
C1—C6—H6119.6C70—C71—H71119.2
C8—C7—C12116.9 (3)C71—C72—C73121.3 (3)
C8—C7—C1121.2 (3)C71—C72—H72119.4
C12—C7—C1121.9 (3)C73—C72—H72119.4
C9—C8—C7121.6 (3)C74—C73—C72117.3 (3)
C9—C8—H8119.2C74—C73—C76123.3 (3)
C7—C8—H8119.2C72—C73—C76119.4 (3)
C8—C9—C10121.5 (3)C75—C74—C73121.5 (3)
C8—C9—H9119.3C75—C74—H74119.3
C10—C9—H9119.3C73—C74—H74119.3
C9—C10—C11117.5 (3)C74—C75—C70121.4 (3)
C9—C10—C13122.5 (3)C74—C75—H75119.3
C11—C10—C13120.0 (3)C70—C75—H75119.3
C12—C11—C10120.9 (3)O7—C76—C77120.2 (3)
C12—C11—H11119.5O7—C76—C73115.5 (3)
C10—C11—H11119.5C77—C76—C73124.3 (3)
C11—C12—C7121.6 (3)C76—C77—C78121.4 (3)
C11—C12—H12119.2C76—C77—H77119.3
C7—C12—H12119.2C78—C77—H77119.3
O1—C13—C14120.3 (3)O8—C78—C77120.2 (3)
O1—C13—C10116.4 (3)O8—C78—C79116.9 (3)
C14—C13—C10123.3 (3)C77—C78—C79122.9 (3)
C13—C14—C15121.5 (3)C84—C79—C80118.8 (3)
C13—C14—H14119.2C84—C79—C78121.9 (3)
C15—C14—H14119.2C80—C79—C78119.2 (4)
O2—C15—C14120.4 (3)C81—C80—C79121.1 (4)
O2—C15—C16116.2 (3)C81—C80—H80119.4
C14—C15—C16123.4 (3)C79—C80—H80119.4
C17—C16—C21118.2 (4)C82—C81—C80119.9 (4)
C17—C16—C15122.2 (3)C82—C81—H81120.1
C21—C16—C15119.6 (4)C80—C81—H81120.1
C18—C17—C16120.4 (4)C81—C82—C83120.0 (4)
C18—C17—H17119.8C81—C82—H82120.0
C16—C17—H17119.8C83—C82—H82120.0
C19—C18—C17120.7 (4)C82—C83—C84119.8 (4)
C19—C18—H18119.6C82—C83—H83120.1
C17—C18—H18119.6C84—C83—H83120.1
C18—C19—C20119.1 (4)C79—C84—C83120.4 (4)
C18—C19—H19120.5C79—C84—H84119.8
C20—C19—H19120.5C83—C84—H84119.8
C21—C20—C19120.6 (4)C90—C85—C86117.6 (3)
C21—C20—H20119.7C90—C85—C91121.8 (3)
C19—C20—H20119.7C86—C85—C91120.6 (3)
C20—C21—C16120.9 (4)C87—C86—C85121.0 (3)
C20—C21—H21119.5C87—C86—H86119.5
C16—C21—H21119.5C85—C86—H86119.5
C23—C22—C27116.6 (3)C88—C87—C86120.3 (3)
C23—C22—C28122.2 (3)C88—C87—H87119.9
C27—C22—C28121.2 (3)C86—C87—H87119.9
C24—C23—C22121.3 (4)C87—C88—C89119.8 (3)
C24—C23—H23119.4C87—C88—H88120.1
C22—C23—H23119.4C89—C88—H88120.1
C25—C24—C23120.8 (4)C88—C89—C90120.4 (3)
C25—C24—H24119.6C88—C89—H89119.8
C23—C24—H24119.6C90—C89—H89119.8
C24—C25—C26119.6 (4)C89—C90—C85121.0 (3)
C24—C25—H25120.2C89—C90—H90119.5
C26—C25—H25120.2C85—C90—H90119.5
C25—C26—C27119.3 (4)C92—C91—C96116.7 (3)
C25—C26—H26120.3C92—C91—C85121.8 (3)
C27—C26—H26120.3C96—C91—C85121.5 (3)
C22—C27—C26122.4 (4)C93—C92—C91122.0 (3)
C22—C27—H27118.8C93—C92—H92119.0
C26—C27—H27118.8C91—C92—H92119.0
C33—C28—C29116.3 (3)C92—C93—C94120.9 (3)
C33—C28—C22122.0 (3)C92—C93—H93119.5
C29—C28—C22121.7 (3)C94—C93—H93119.5
C30—C29—C28122.0 (3)C93—C94—C95118.1 (3)
C30—C29—H29119.0C93—C94—C97119.7 (3)
C28—C29—H29119.0C95—C94—C97122.1 (3)
C29—C30—C31120.9 (3)C96—C95—C94120.8 (3)
C29—C30—H30119.5C96—C95—H95119.6
C31—C30—H30119.5C94—C95—H95119.6
C32—C31—C30117.5 (3)C95—C96—C91121.4 (3)
C32—C31—C34119.8 (3)C95—C96—H96119.3
C30—C31—C34122.6 (3)C91—C96—H96119.3
C33—C32—C31121.0 (3)O9—C97—C98120.3 (3)
C33—C32—H32119.5O9—C97—C94114.9 (3)
C31—C32—H32119.5C98—C97—C94124.7 (3)
C32—C33—C28122.3 (3)C97—C98—C99121.7 (3)
C32—C33—H33118.8C97—C98—H98119.2
C28—C33—H33118.8C99—C98—H98119.2
O3—C34—C35120.2 (3)O10—C99—C98120.1 (3)
O3—C34—C31115.0 (3)O10—C99—C100117.5 (3)
C35—C34—C31124.8 (3)C98—C99—C100122.5 (3)
C34—C35—C36121.8 (3)C101—C100—C105118.4 (3)
C34—C35—H35119.1C101—C100—C99122.4 (3)
C36—C35—H35119.1C105—C100—C99119.2 (4)
O4—C36—C35119.8 (3)C102—C101—C100120.9 (4)
O4—C36—C37117.8 (3)C102—C101—H101119.6
C35—C36—C37122.3 (3)C100—C101—H101119.6
C38—C37—C42117.9 (3)C101—C102—C103119.7 (4)
C38—C37—C36122.6 (3)C101—C102—H102120.2
C42—C37—C36119.5 (3)C103—C102—H102120.2
C37—C38—C39121.5 (3)C104—C103—C102120.3 (4)
C37—C38—H38119.2C104—C103—H103119.8
C39—C38—H38119.2C102—C103—H103119.8
C40—C39—C38119.9 (4)C103—C104—C105119.9 (4)
C40—C39—H39120.0C103—C104—H104120.1
C38—C39—H39120.0C105—C104—H104120.1
C39—C40—C41119.6 (4)C104—C105—C100120.8 (4)
C39—C40—H40120.2C104—C105—H105119.6
C41—C40—H40120.2C100—C105—H105119.6
C40—C41—C42120.4 (3)C107—C106—C111116.9 (3)
C40—C41—H41119.8C107—C106—C112122.4 (3)
C42—C41—H41119.8C111—C106—C112120.7 (3)
C41—C42—C37120.7 (3)C108—C107—C106121.5 (3)
C41—C42—H42119.7C108—C107—H107119.2
C37—C42—H42119.7C106—C107—H107119.2
C48—C43—C44116.86C109—C108—C107120.6 (4)
C48—C43—C49121.8C109—C108—H108119.7
C44—C43—C49121.30C107—C108—H108119.7
C45—C44—C43121.73C108—C109—C110118.9 (4)
C45—C44—H44119.2C108—C109—H109120.5
C43—C44—H44119.1C110—C109—H109120.5
C46—C45—C44120.3C109—C110—C111120.5 (4)
C46—C45—H45119.9C109—C110—H110119.8
C44—C45—H45119.9C111—C110—H110119.8
C47—C46—C45119.0 (3)C110—C111—C106121.6 (4)
C47—C46—H46120.5C110—C111—H111119.2
C45—C46—H46120.5C106—C111—H111119.2
C46—C47—C48120.7 (3)C113—C112—C117116.4 (3)
C46—C47—H47119.7C113—C112—C106121.1 (3)
C48—C47—H47119.7C117—C112—C106122.5 (3)
C47—C48—C43121.4C114—C113—C112122.2 (3)
C47—C48—H48119.3C114—C113—H113118.9
C43—C48—H48119.3C112—C113—H113118.9
C54—C49—C50117.2 (3)C113—C114—C115121.0 (3)
C54—C49—C43121.4C113—C114—H114119.5
C50—C49—C43121.3C115—C114—H114119.5
C51—C50—C49121.4 (3)C116—C115—C114117.6 (3)
C51—C50—H50119.3C116—C115—C118120.1 (3)
C49—C50—H50119.3C114—C115—C118122.2 (3)
C52—C51—C50120.9 (3)C117—C116—C115121.3 (3)
C52—C51—H51119.6C117—C116—H116119.3
C50—C51—H51119.6C115—C116—H116119.3
C51—C52—C53118.1 (3)C116—C117—C112121.4 (3)
C51—C52—C55119.4 (3)C116—C117—H117119.3
C53—C52—C55122.5 (3)C112—C117—H117119.3
C54—C53—C52120.6 (3)O11—C118—C119120.6 (3)
C54—C53—H53119.7O11—C118—C115116.7 (4)
C52—C53—H53119.7C119—C118—C115122.7 (3)
C53—C54—C49121.8 (3)C118—C119—C120122.6 (3)
C53—C54—H54119.1C118—C119—H119118.7
C49—C54—H54119.1C120—C119—H119118.7
O5—C55—C56120.3 (3)O12—C120—C119119.1 (4)
O5—C55—C52116.4 (3)O12—C120—C121116.6 (3)
C56—C55—C52123.3 (3)C119—C120—C121124.3 (3)
C57—C56—C55121.4 (3)C122—C121—C126118.1 (4)
C57—C56—H56119.3C122—C121—C120122.0 (3)
C55—C56—H56119.3C126—C121—C120119.9 (4)
O6—C57—C56120.4 (3)C123—C122—C121120.6 (4)
O6—C57—C58115.3 (3)C123—C122—H122119.7
C56—C57—C58124.3 (3)C121—C122—H122119.7
C63—C58—C59118.4 (3)C122—C123—C124121.1 (4)
C63—C58—C57122.3 (3)C122—C123—H123119.5
C59—C58—C57119.3 (3)C124—C123—H123119.5
C60—C59—C58120.7 (4)C125—C124—C123119.0 (5)
C60—C59—H59119.6C125—C124—H124120.5
C58—C59—H59119.6C123—C124—H124120.5
C61—C60—C59120.2 (4)C124—C125—C126120.8 (4)
C61—C60—H60119.9C124—C125—H125119.6
C59—C60—H60119.9C126—C125—H125119.6
C60—C61—C62119.4 (4)C125—C126—C121120.4 (4)
C60—C61—H61120.3C125—C126—H126119.8
C62—C61—H61120.3C121—C126—H126119.8
C61—C62—C63121.0 (4)C13—O1—H1A101 (2)
C61—C62—H62119.5C15—O2—H1A99.8 (18)
C63—C62—H62119.5C34—O3—H3A101.3 (17)
C62—C63—C58120.2 (4)C36—O4—H3A101.2 (16)
C62—C63—H63119.9C55—O5—H5A102.3 (18)
C58—C63—H63119.9C57—O6—H5A103 (2)
C65—C64—C69116.7 (3)C76—O7—H7A102.5 (18)
C65—C64—C70121.5 (3)C78—O8—H7A102.8 (18)
C69—C64—C70121.7 (3)C97—O9—H9A101.3 (18)
C66—C65—C64121.7 (4)C99—O10—H9A100.7 (16)
C66—C65—H65119.1C118—O11—H11A100.3 (19)
C64—C65—H65119.1C120—O12—H11A102 (2)
C6—C1—C2—C30.4 (5)C69—C64—C65—C660.9 (5)
C7—C1—C2—C3179.1 (3)C70—C64—C65—C66−176.8 (3)
C1—C2—C3—C4−0.1 (5)C64—C65—C66—C670.9 (6)
C2—C3—C4—C5−0.2 (6)C65—C66—C67—C68−2.0 (7)
C3—C4—C5—C60.2 (6)C66—C67—C68—C691.3 (7)
C4—C5—C6—C10.2 (6)C67—C68—C69—C640.5 (7)
C2—C1—C6—C5−0.5 (5)C65—C64—C69—C68−1.6 (6)
C7—C1—C6—C5−179.1 (3)C70—C64—C69—C68176.1 (4)
C2—C1—C7—C8−27.5 (4)C65—C64—C70—C7125.2 (5)
C6—C1—C7—C8151.1 (3)C69—C64—C70—C71−152.4 (4)
C2—C1—C7—C12153.2 (3)C65—C64—C70—C75−155.3 (3)
C6—C1—C7—C12−28.1 (4)C69—C64—C70—C7527.1 (5)
C12—C7—C8—C91.1 (5)C75—C70—C71—C72−0.2 (5)
C1—C7—C8—C9−178.2 (3)C64—C70—C71—C72179.3 (3)
C7—C8—C9—C10−0.7 (5)C70—C71—C72—C73−0.6 (6)
C8—C9—C10—C11−0.3 (5)C71—C72—C73—C741.4 (5)
C8—C9—C10—C13177.7 (3)C71—C72—C73—C76−179.2 (3)
C9—C10—C11—C120.9 (5)C72—C73—C74—C75−1.3 (5)
C13—C10—C11—C12−177.1 (3)C76—C73—C74—C75179.3 (3)
C10—C11—C12—C7−0.5 (5)C73—C74—C75—C700.5 (5)
C8—C7—C12—C11−0.4 (5)C71—C70—C75—C740.3 (5)
C1—C7—C12—C11178.8 (3)C64—C70—C75—C74−179.2 (3)
C9—C10—C13—O1−170.7 (3)C74—C73—C76—O7172.0 (3)
C11—C10—C13—O17.3 (4)C72—C73—C76—O7−7.4 (5)
C9—C10—C13—C147.8 (5)C74—C73—C76—C77−9.4 (5)
C11—C10—C13—C14−174.3 (3)C72—C73—C76—C77171.2 (3)
O1—C13—C14—C151.1 (5)O7—C76—C77—C782.6 (5)
C10—C13—C14—C15−177.2 (3)C73—C76—C77—C78−176.0 (3)
C13—C14—C15—O20.1 (5)C76—C77—C78—O8−5.1 (5)
C13—C14—C15—C16−179.7 (3)C76—C77—C78—C79172.3 (3)
O2—C15—C16—C17179.5 (3)O8—C78—C79—C84−154.5 (4)
C14—C15—C16—C17−0.7 (5)C77—C78—C79—C8428.1 (5)
O2—C15—C16—C21−1.7 (5)O8—C78—C79—C8027.5 (5)
C14—C15—C16—C21178.1 (3)C77—C78—C79—C80−150.0 (3)
C21—C16—C17—C18−0.8 (5)C84—C79—C80—C81−2.3 (5)
C15—C16—C17—C18177.9 (3)C78—C79—C80—C81175.9 (3)
C16—C17—C18—C190.9 (6)C79—C80—C81—C821.4 (6)
C17—C18—C19—C20−0.5 (6)C80—C81—C82—C830.3 (6)
C18—C19—C20—C210.1 (6)C81—C82—C83—C84−1.2 (7)
C19—C20—C21—C160.0 (6)C80—C79—C84—C831.4 (6)
C17—C16—C21—C200.4 (5)C78—C79—C84—C83−176.7 (4)
C15—C16—C21—C20−178.4 (3)C82—C83—C84—C790.3 (6)
C27—C22—C23—C24−0.4 (6)C90—C85—C86—C87−0.5 (5)
C28—C22—C23—C24178.2 (4)C91—C85—C86—C87179.3 (3)
C22—C23—C24—C250.0 (7)C85—C86—C87—C880.4 (6)
C23—C24—C25—C260.4 (7)C86—C87—C88—C89−0.2 (6)
C24—C25—C26—C27−0.3 (6)C87—C88—C89—C900.1 (6)
C23—C22—C27—C260.5 (5)C88—C89—C90—C85−0.2 (5)
C28—C22—C27—C26−178.1 (3)C86—C85—C90—C890.4 (5)
C25—C26—C27—C22−0.1 (6)C91—C85—C90—C89−179.4 (3)
C23—C22—C28—C33162.9 (3)C90—C85—C91—C92−155.1 (3)
C27—C22—C28—C33−18.6 (5)C86—C85—C91—C9225.1 (5)
C23—C22—C28—C29−18.1 (5)C90—C85—C91—C9625.3 (5)
C27—C22—C28—C29160.4 (3)C86—C85—C91—C96−154.5 (3)
C33—C28—C29—C300.2 (5)C96—C91—C92—C93−0.2 (5)
C22—C28—C29—C30−178.9 (3)C85—C91—C92—C93−179.8 (3)
C28—C29—C30—C31−0.8 (5)C91—C92—C93—C94−1.3 (5)
C29—C30—C31—C321.3 (5)C92—C93—C94—C952.2 (5)
C29—C30—C31—C34−177.7 (3)C92—C93—C94—C97−177.7 (3)
C30—C31—C32—C33−1.3 (5)C93—C94—C95—C96−1.6 (5)
C34—C31—C32—C33177.7 (3)C97—C94—C95—C96178.2 (3)
C31—C32—C33—C280.8 (5)C94—C95—C96—C910.2 (5)
C29—C28—C33—C32−0.2 (5)C92—C91—C96—C950.7 (5)
C22—C28—C33—C32178.8 (3)C85—C91—C96—C95−179.7 (3)
C32—C31—C34—O34.6 (4)C93—C94—C97—O9−12.0 (4)
C30—C31—C34—O3−176.5 (3)C95—C94—C97—O9168.1 (3)
C32—C31—C34—C35−175.0 (3)C93—C94—C97—C98166.3 (3)
C30—C31—C34—C353.9 (5)C95—C94—C97—C98−13.6 (5)
O3—C34—C35—C36−0.6 (5)O9—C97—C98—C993.5 (5)
C31—C34—C35—C36179.0 (3)C94—C97—C98—C99−174.7 (3)
C34—C35—C36—O40.1 (5)C97—C98—C99—O10−3.3 (5)
C34—C35—C36—C37−179.7 (3)C97—C98—C99—C100175.3 (3)
O4—C36—C37—C38−177.6 (3)O10—C99—C100—C101−156.2 (3)
C35—C36—C37—C382.3 (5)C98—C99—C100—C10125.1 (5)
O4—C36—C37—C422.5 (4)O10—C99—C100—C10525.3 (5)
C35—C36—C37—C42−177.7 (3)C98—C99—C100—C105−153.3 (3)
C42—C37—C38—C39−0.6 (5)C105—C100—C101—C1020.0 (5)
C36—C37—C38—C39179.4 (3)C99—C100—C101—C102−178.4 (3)
C37—C38—C39—C401.1 (6)C100—C101—C102—C1030.7 (6)
C38—C39—C40—C41−0.6 (6)C101—C102—C103—C104−0.7 (7)
C39—C40—C41—C42−0.3 (6)C102—C103—C104—C1050.0 (7)
C40—C41—C42—C370.8 (5)C103—C104—C105—C1000.7 (7)
C38—C37—C42—C41−0.4 (4)C101—C100—C105—C104−0.7 (5)
C36—C37—C42—C41179.6 (3)C99—C100—C105—C104177.8 (3)
C48—C43—C44—C450.1C111—C106—C107—C108−0.6 (5)
C49—C43—C44—C45177.0C112—C106—C107—C108176.2 (3)
C43—C44—C45—C460.4C106—C107—C108—C109−0.1 (6)
C44—C45—C46—C47−0.5C107—C108—C109—C1100.2 (6)
C45—C46—C47—C480.0 (5)C108—C109—C110—C1110.4 (6)
C46—C47—C48—C430.5C109—C110—C111—C106−1.1 (6)
C44—C43—C48—C47−0.6C107—C106—C111—C1101.1 (5)
C49—C43—C48—C47−177.5C112—C106—C111—C110−175.7 (3)
C48—C43—C49—C5430.0C107—C106—C112—C113−26.1 (4)
C44—C43—C49—C54−146.8C111—C106—C112—C113150.6 (3)
C48—C43—C49—C50−153.1C107—C106—C112—C117156.3 (3)
C44—C43—C49—C5030.1C111—C106—C112—C117−27.0 (5)
C54—C49—C50—C512.3 (5)C117—C112—C113—C1142.6 (5)
C43—C49—C50—C51−174.7C106—C112—C113—C114−175.2 (3)
C49—C50—C51—C52−1.2 (5)C112—C113—C114—C115−0.7 (5)
C50—C51—C52—C53−0.9 (5)C113—C114—C115—C116−1.0 (5)
C50—C51—C52—C55176.8 (3)C113—C114—C115—C118176.9 (3)
C51—C52—C53—C541.9 (5)C114—C115—C116—C1170.8 (5)
C55—C52—C53—C54−175.7 (3)C118—C115—C116—C117−177.2 (3)
C52—C53—C54—C49−0.8 (5)C115—C116—C117—C1121.2 (5)
C50—C49—C54—C53−1.3 (5)C113—C112—C117—C116−2.8 (5)
C43—C49—C54—C53175.7C106—C112—C117—C116174.9 (3)
C51—C52—C55—O5−11.5 (5)C116—C115—C118—O1115.4 (5)
C53—C52—C55—O5166.1 (3)C114—C115—C118—O11−162.5 (3)
C51—C52—C55—C56169.5 (3)C116—C115—C118—C119−165.7 (3)
C53—C52—C55—C56−13.0 (5)C114—C115—C118—C11916.4 (5)
O5—C55—C56—C57−3.6 (5)O11—C118—C119—C1202.8 (5)
C52—C55—C56—C57175.4 (3)C115—C118—C119—C120−176.1 (3)
C55—C56—C57—O61.5 (5)C118—C119—C120—O120.0 (5)
C55—C56—C57—C58−177.7 (3)C118—C119—C120—C121179.1 (3)
O6—C57—C58—C63−177.9 (3)O12—C120—C121—C122173.0 (3)
C56—C57—C58—C631.3 (5)C119—C120—C121—C122−6.2 (5)
O6—C57—C58—C593.5 (4)O12—C120—C121—C126−8.2 (5)
C56—C57—C58—C59−177.2 (3)C119—C120—C121—C126172.7 (3)
C63—C58—C59—C600.5 (5)C126—C121—C122—C1230.0 (6)
C57—C58—C59—C60179.1 (3)C120—C121—C122—C123178.9 (4)
C58—C59—C60—C610.3 (6)C121—C122—C123—C124−0.2 (7)
C59—C60—C61—C62−0.9 (6)C122—C123—C124—C1250.1 (7)
C60—C61—C62—C630.6 (7)C123—C124—C125—C1260.2 (7)
C61—C62—C63—C580.2 (6)C124—C125—C126—C121−0.5 (6)
C59—C58—C63—C62−0.8 (5)C122—C121—C126—C1250.4 (6)
C57—C58—C63—C62−179.3 (3)C120—C121—C126—C125−178.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···O21.20 (5)1.33 (5)2.480 (4)156 (4)
O3—H3A···O41.21 (4)1.33 (4)2.479 (4)156 (3)
O5—H5A···O61.33 (5)1.22 (5)2.474 (4)152 (4)
O7—H7A···O81.28 (5)1.26 (5)2.465 (4)152 (4)
O9—H9A···O101.20 (5)1.34 (5)2.473 (4)154 (3)
O11—H11A···O121.33 (5)1.25 (5)2.494 (4)152 (4)
C122—H122···O10i0.932.583.429 (5)152
C19—H19···Cg10ii0.932.933.739 (5)147
C23—H23···Cg17iii0.932.903.714 (4)146
C32—H32···Cg17iv0.932.943.749 (4)147
C39—H39···Cg3i0.932.823.674 (5)152
C48—H48···Cg11v0.932.793.618 (4)149
C69—H69···Cg8i0.932.953.820 (4)155
C93—H93···Cg2vi0.933.003.692 (3)133
C107—H107···Cg14i0.932.833.670 (4)151

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x, −y, −z+1; (iv) −x+1, −y, −z+1; (v) −x+1, −y+1, −z+1; (vi) −x+2, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2145).

References

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