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ISSN: 2056-9890
Volume 69| Part 10| October 2013| Pages o1514-o1515

3,3′′-Bis(9-hy­dr­oxy­fluoren-9-yl)-1,1′:3′,1′′-terphen­yl

aDepartment of Chemistry, University of Ioannina, GR-451 10 Ioannina, Greece, and bInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

(Received 18 July 2013; accepted 27 August 2013; online 7 September 2013)

The asymmetric unit of the title compound, C44H30O2, contains two independent mol­ecules in which the terminal rings of the terphenyl element are inclined at angles of 36.3 (1) and 22.5 (1)° with respect to the central ring and the dihedral angles between the fluorenyl units are 72.3 (1) and 62.8 (1)°. In the crystal, pairs of O—H⋯O hydrogen bonds link the mol­ecules into inversion dimers. The hy­droxy H atoms not involved in these hydrogen bonds form O—H⋯π inter­actions in which the central terphenyl rings act as acceptors. Weak C—H⋯O contacts and ππ [centroid–centroid distance = 4.088 (2) Å] stacking inter­actions also occur. Taking into account directed non-covalent bonding between the molecules, the crystal is constructed of supramolecular strands extending along the a-axis direction.

Related literature

For the preparation of the starting material for the synthesis of the title compound, see: Staab & Binnig (1967[Staab, H. A. & Binnig, A. (1967). Chem. Ber. 11, 293-305.]). For background to organic solid-state inclusion chemistry, see: Atwood et al. (1991[Atwood, J. L., Davies, J. E. D. & MacNicol, D. D. (1991). Editors. Inclusion Compounds, Vol. 4. Oxford Universty Press.]). For the design strategy of host compounds, see: Desiraju (1996[Desiraju, G. R. (1996). Comprehensive Supramolecular Chemistry, edited by D. D. MacNicol, F. Toda & R. Bishop, pp. 1-22. Oxford: Elsevier.]). For diol host inclusion complexes, see: Toda (1996[Toda, F. (1996). Comprehensive Supramolecular Chemistry edited by D. D. MacNicol, F. Toda & R. Bishop, pp. 465-516. Oxford: Elsevier.]). For host compound 2,2′-bis­(9-hy­droxy-9-fluoren­yl)biphenyl, see: Weber et al. (1993[Weber, E., Skobridis, K., Wierig, A., Stathi, S., Nassimbeni, L. R. & Niven, M. L. (1993). Angew. Chem. Int. Ed. 32, 606-608.]); Skobridis, Paraskevopoulos et al. (2011[Skobridis, K., Paraskevopoulos, G., Theodorou, V., Seichter, W. & Weber, E. (2011). Cryst. Growth Des. 11, 5275-5288.]); Skobridis, Theodorou et al. (2011[Skobridis, K., Theodorou, V., Seichter, W. & Weber, E. (2011). Cryst. Growth Des. 10, 862-869.]). For weak O—H⋯π and C—H⋯O inter­actions, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. Oxford University Press.]). For ππ stacking inter­actions, see: James (2004[James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.]).

[Scheme 1]

Experimental

Crystal data
  • C44H30O2

  • Mr = 590.68

  • Triclinic, [P \overline 1]

  • a = 11.2292 (3) Å

  • b = 12.4823 (3) Å

  • c = 24.4440 (5) Å

  • α = 76.070 (1)°

  • β = 78.080 (1)°

  • γ = 66.917 (1)°

  • V = 3034.99 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 150 K

  • 0.32 × 0.18 × 0.06 mm

Data collection
  • Bruker X8 APEXII CCD diffractometer

  • 55787 measured reflections

  • 13774 independent reflections

  • 9930 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.109

  • S = 1.03

  • 13774 reflections

  • 845 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C20–C25 and C20A–C25A rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2i 0.86 (1) 2.07 (1) 2.894 (2) 163 (1)
O2—H2⋯Cg1ii 0.84 (1) 3.42 (1) 4.163 (2) 150 (1)
O1A—H1A⋯O2Aiii 0.85 (1) 1.99 (1) 2.807 (2) 160 (1)
O2A—H2ACg2iv 0.85 (2) 3.46 (1) 4.169 (2) 145 (1)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+2; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

In the realm of organic state inclusion chemistry (Atwood et al., 1991), bulkily substituted diols have proven a versatile design strategy for the formation of host compounds (Desiraju, 1996) yielding crystalline host-guest complexes with a variety of guest molecules (Toda, 1996). With regard to that, 2,2'-bis(9-hydroxy-9-fluorenyl)biphenyl is a prototype host structure (Weber et al., 1993; Skobridis, Paraskevopoulos et al., 2010; Skobridis, Theodorou et al., 2011). Following this structural approach, the title compound involving exchange of the central 2,2'-disubstituted biphenyl unit for a 3,3"-disubstituted m-terphenyl moiety was prepared and its crystal structure studied unexpectedly showing a solvent-free crystal species on crystallization from ethanol. The compound was found in the space group P1 with two crystallographically independent molecules in the asymmetric unit (Fig. 1). The twist angles between the aromatic rings of their terpenyl element are 36.3 (1)° (rings A/B), 22.5 (1)° (rings B/C), 33.8 (1)° (rings A'/B') and 17.2° (rings B'/C') while the mean planes of the fluorenyl units are inclined at angles of 72.3 (1)° and 62.8 (1)°, respectively. The crystal structure (Fig. 2 & Fig. 3) is constructed of inversion dimers which are stabilized by classical O–H···O hydrogen bonds. The hydroxy H atoms excluded from strong hydrogen bonding interlink the molecular dimers via O–H···π interactions (Desiraju & Steiner, 1999) with the central rings of the terphenyl units acting as acceptors (O2–H2···C22 = 2.692 (2) Å, 153.3 (1)°; O2A–H2A···C22A = 2.724 (2) Å, 142.5 (1)°). Weak C–H···O contacts (Desiraju & Steiner, 1999) and ππ stacking interactions (James, 2004) (Cg(B)···Cg(B)i, 4.088 (2) Å; symmetry code: (i) 1-x, 2-y, 2-z) complete the pattern of intermolecular interactions.

Related literature top

For the preparation of the starting material for the synthesis of the title compound, see: Staab & Binnig (1967). For background to organic solid-state inclusion chemistry, see: Atwood et al. (1991). For the design strategy of host compounds, see: Desiraju (1996). For diol host inclusion complexes, see: Toda (1996). For host compound 2,2'-bis(9-hydroxy-9-fluorenyl)biphenyl, see: Weber et al. (1993); Skobridis, Paraskevopoulos et al. (2011); ; Skobridis, Theodorou et al. (2011). For weak O—H···π and C—H···O interactions, see: Desiraju & Steiner (1999). For ππ stacking interactions, see: James (2004).

Experimental top

The starting compound 3,3"-dibromo-1,1':2',1"-terphenyl was prepared according to a literature procedure (Staab & Binnig, 1967). To a stirred solution of this dibromide (2.13 g, 5.5 mmol) in dry diethyl ether (25 ml), n-BuLi (1.6 N in n-hexane, 7.0 ml, 12 mmol) was added dropwise at 195 K under argon. Stirring of the mixture was continued at 253 K for 15 min. Then, fluorenone (1.98 g, 11.0 mmol) in 25 ml of dry diethyl ether was added and the mixture kept at reflux. After completion of the reaction (24 h), which was monitored by TLC (hexane/ethyl acetate 2:1, Rf 0.55), the mixture was cooled, quenched with saturated NH4Cl solution and extracted with diethyl ether (2 × 30 ml). The combined organic extracts were dried (Na2SO4) and evaporated. The pale yellow oily residue was precipitated by the addition of hexane and purified by flash chromatography on a SiO2 column (hexane/ethyl acetate 2:1) to yield 3.90 g (65 %) of a colourless solid. M.p. = 485-487 K. IR (KBr) 3446, 3037, 1597, 1467, 1448, 1166, 1120, 769, 738. 1H NMR (500 MHz, CDCl3) δ 2.61 (s, br, 2 H, OH), 7.34-7.62 (m, 21 H, ArH), 7.79-7.92 (m, 7 H, ArH). 13C NMR (125 MHz, CDCl3) δ 83.7 (CO), 120.2, 124.3, 124.7, 124.8, 126.3, 128.5, 128.7, 129.0, 129.2, 139.7, 141.2, 141.8, 143.8. 150.4 (Ar). MS (HR-ESI) m/z: found 613.2126 [M+Na], calc. for C44H30O2 + Na: 613.2138. The melting point (uncorrected) was measured on a hot stage microscope. The IR spectrum was recorded on a Perkin Elmer FT-IR 1600 spectrometer. 1H and 13C NMR spectra were measured on a Bruker Avance AV-500 spectrometer using (CH3)4Si as internal standard. The high resolution ESI mass spectrum was obtained using a ThermoFisher Scientific Orbitrap XL spectrometer. Crystals of the title compound suitable for X-ray structural analysis were grown by slow evaporating a solution of the material in ethanol.

Refinement top

The H atoms for hydroxy groups were obtained from the difference electron density map and refined freely. Other aromatic H atoms were positioned geometrically and allowed to ride on their respective parent atoms, with C–H = 0.95Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Asymmetric unit of the title compound, showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing excerpt of the title compound, showing the O—H···O hydrogen-bonded dimers interlinked via O—H···π interactions. O—H···O and O—H···π contacts are presented as broken lines and broken double lines, respectively. Non-relevant hydrogens are omitted for clarity.
[Figure 3] Fig. 3. A view along the a-axis of the title compound. Hydrogen-bond type contacts are presented as broken lines. Non-relevant hydrogens are omitted for clarity.
3,3''-Bis(9-hydroxyfluoren-9-yl)-1,1':3',1''-terphenyl top
Crystal data top
C44H30O2Z = 4
Mr = 590.68F(000) = 1240
Triclinic, P1Dx = 1.293 Mg m3
Hall symbol: -P 1Melting point = 485–487 K
a = 11.2292 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.4823 (3) ÅCell parameters from 9885 reflections
c = 24.4440 (5) Åθ = 2.3–28.4°
α = 76.070 (1)°µ = 0.08 mm1
β = 78.080 (1)°T = 150 K
γ = 66.917 (1)°Irregular, colourless
V = 3034.99 (13) Å30.32 × 0.18 × 0.06 mm
Data collection top
Bruker X8 APEXII CCD
diffractometer
9930 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.4°, θmin = 0.9°
ϕ– and ω–scansh = 1414
55787 measured reflectionsk = 1616
13774 independent reflectionsl = 3131
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.734P]
where P = (Fo2 + 2Fc2)/3
13774 reflections(Δ/σ)max < 0.001
845 parametersΔρmax = 0.24 e Å3
4 restraintsΔρmin = 0.22 e Å3
Crystal data top
C44H30O2γ = 66.917 (1)°
Mr = 590.68V = 3034.99 (13) Å3
Triclinic, P1Z = 4
a = 11.2292 (3) ÅMo Kα radiation
b = 12.4823 (3) ŵ = 0.08 mm1
c = 24.4440 (5) ÅT = 150 K
α = 76.070 (1)°0.32 × 0.18 × 0.06 mm
β = 78.080 (1)°
Data collection top
Bruker X8 APEXII CCD
diffractometer
9930 reflections with I > 2σ(I)
55787 measured reflectionsRint = 0.035
13774 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0444 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.24 e Å3
13774 reflectionsΔρmin = 0.22 e Å3
845 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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. The bond lengths of the hydroxy groups (O1–H1, O2–H2, O1A–H1A, O2A–H2A) were restraint to target values of 0.84 (1)°.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.94347 (11)0.99066 (10)0.89442 (4)0.0298 (2)
H10.9865 (18)1.0357 (15)0.8911 (8)0.058 (6)*
O20.06412 (10)0.85199 (9)1.09227 (4)0.0270 (2)
H20.1445 (10)0.8725 (18)1.0921 (9)0.058 (6)*
C11.12300 (14)0.86200 (13)0.83697 (6)0.0271 (3)
C21.19755 (16)0.77159 (15)0.87461 (8)0.0379 (4)
H2AA1.15940.74620.91140.045*
C31.33026 (18)0.71841 (17)0.85737 (10)0.0499 (5)
H31.38320.65550.88260.060*
C41.38572 (17)0.75594 (18)0.80409 (10)0.0503 (5)
H41.47640.71830.79320.060*
C51.31174 (17)0.84740 (17)0.76627 (8)0.0420 (4)
H51.35080.87310.72970.050*
C61.17897 (15)0.90096 (14)0.78287 (7)0.0299 (3)
C71.07732 (15)0.99960 (14)0.75333 (6)0.0292 (3)
C81.08036 (19)1.06728 (16)0.69911 (7)0.0415 (4)
H81.15941.05300.67390.050*
C90.9664 (2)1.15561 (17)0.68269 (7)0.0459 (5)
H90.96761.20220.64570.055*
C100.85090 (19)1.17759 (15)0.71886 (8)0.0421 (4)
H100.77401.23920.70660.051*
C110.84615 (16)1.11050 (14)0.77289 (7)0.0323 (4)
H110.76661.12480.79770.039*
C120.95974 (15)1.02239 (13)0.78973 (6)0.0255 (3)
C130.97803 (14)0.93475 (13)0.84594 (6)0.0238 (3)
C140.88925 (13)0.86512 (12)0.85287 (6)0.0218 (3)
C150.92373 (14)0.77027 (13)0.82483 (6)0.0247 (3)
H151.00800.74270.80400.030*
C160.83589 (14)0.71609 (13)0.82719 (6)0.0251 (3)
H160.86000.65190.80770.030*
C170.71268 (14)0.75488 (12)0.85783 (6)0.0234 (3)
H170.65250.71790.85880.028*
C180.67726 (13)0.84809 (12)0.88717 (5)0.0210 (3)
C190.76591 (13)0.90268 (12)0.88367 (6)0.0218 (3)
H190.74160.96740.90280.026*
C200.54817 (13)0.88801 (12)0.92254 (6)0.0216 (3)
C210.48126 (14)1.00700 (13)0.92661 (6)0.0243 (3)
H210.51801.06440.90660.029*
C220.36119 (14)1.04162 (13)0.95977 (6)0.0258 (3)
H220.31581.12290.96200.031*
C230.30668 (14)0.95900 (13)0.98970 (6)0.0251 (3)
H230.22400.98421.01200.030*
C240.37232 (13)0.83886 (13)0.98735 (6)0.0223 (3)
C250.49253 (14)0.80609 (13)0.95310 (6)0.0230 (3)
H250.53790.72490.95060.028*
C260.32002 (13)0.74718 (13)1.02154 (6)0.0224 (3)
C270.40254 (14)0.63031 (13)1.03636 (6)0.0252 (3)
H270.49360.60851.02420.030*
C280.35372 (14)0.54571 (13)1.06855 (6)0.0258 (3)
H280.41100.46591.07720.031*
C290.22209 (14)0.57635 (13)1.08829 (6)0.0242 (3)
H290.18930.51781.11050.029*
C300.13789 (13)0.69292 (12)1.07553 (6)0.0215 (3)
C310.18631 (14)0.77647 (13)1.04124 (6)0.0224 (3)
H310.12790.85511.03080.027*
C320.00592 (13)0.72451 (12)1.09871 (6)0.0225 (3)
C330.07417 (13)0.67342 (13)1.06951 (6)0.0241 (3)
C340.08402 (15)0.69123 (14)1.01235 (6)0.0303 (3)
H340.04810.74300.98550.036*
C350.14767 (16)0.63166 (15)0.99506 (7)0.0375 (4)
H350.15490.64230.95590.045*
C360.20056 (17)0.55699 (16)1.03447 (8)0.0424 (4)
H360.24400.51731.02190.051*
C370.19141 (16)0.53890 (15)1.09183 (8)0.0370 (4)
H370.22830.48771.11860.044*
C380.12712 (14)0.59729 (13)1.10932 (6)0.0266 (3)
C390.09714 (14)0.59233 (13)1.16595 (6)0.0259 (3)
C400.12494 (16)0.52828 (14)1.21874 (7)0.0331 (4)
H400.17450.47961.22280.040*
C410.07897 (17)0.53695 (15)1.26528 (7)0.0371 (4)
H410.09650.49311.30150.044*
C420.00772 (17)0.60871 (15)1.25964 (7)0.0360 (4)
H420.02310.61341.29200.043*
C430.01929 (15)0.67407 (14)1.20693 (6)0.0293 (3)
H430.06790.72351.20310.035*
C440.02603 (13)0.66525 (12)1.16066 (6)0.0232 (3)
O1A1.41120 (11)0.32518 (9)0.59705 (5)0.0357 (3)
H1A1.4660 (16)0.3507 (17)0.6037 (8)0.055 (6)*
O2A0.44394 (10)0.54003 (10)0.39659 (5)0.0293 (2)
H2A0.3615 (10)0.5663 (18)0.3979 (9)0.068 (7)*
C1A1.44187 (15)0.15094 (13)0.67427 (6)0.0257 (3)
C2A1.32848 (16)0.17143 (14)0.71175 (7)0.0331 (4)
H2AB1.24720.22450.69970.040*
C3A1.33615 (18)0.11247 (16)0.76755 (7)0.0417 (4)
H3A1.25950.12610.79430.050*
C4A1.45487 (19)0.03382 (17)0.78450 (7)0.0443 (4)
H4A1.45800.00720.82260.053*
C5A1.56883 (17)0.01375 (15)0.74710 (7)0.0369 (4)
H5A1.64990.03960.75930.044*
C6A1.56194 (15)0.07326 (13)0.69149 (6)0.0269 (3)
C7A1.66334 (14)0.07059 (12)0.64249 (6)0.0261 (3)
C8A1.79803 (15)0.01418 (14)0.63803 (7)0.0332 (4)
H8A1.83910.03600.67000.040*
C9A1.87136 (16)0.03244 (15)0.58611 (8)0.0387 (4)
H9A1.96360.00550.58250.046*
C10A1.81221 (17)0.10512 (15)0.53940 (8)0.0379 (4)
H10A1.86420.11630.50410.045*
C11A1.67762 (16)0.16195 (14)0.54350 (7)0.0336 (4)
H11A1.63720.21260.51150.040*
C12A1.60384 (15)0.14348 (13)0.59493 (6)0.0268 (3)
C13A1.45695 (14)0.19901 (12)0.61050 (6)0.0263 (3)
C14A1.37525 (14)0.15922 (13)0.58288 (6)0.0250 (3)
C15A1.41270 (16)0.04087 (14)0.57924 (7)0.0331 (4)
H15A1.49360.01440.59090.040*
C16A1.33264 (16)0.00314 (14)0.55870 (7)0.0358 (4)
H16A1.35900.07790.55620.043*
C17A1.21453 (15)0.08276 (13)0.54183 (6)0.0298 (3)
H17A1.16020.05610.52780.036*
C18A1.17481 (14)0.20167 (13)0.54526 (6)0.0237 (3)
C19A1.25665 (14)0.23819 (13)0.56608 (6)0.0244 (3)
H19A1.23040.31910.56880.029*
C20A1.04741 (14)0.28872 (12)0.52785 (6)0.0229 (3)
C21A0.97615 (14)0.38363 (13)0.55611 (6)0.0250 (3)
H21A1.00910.39340.58670.030*
C22A0.85781 (14)0.46352 (13)0.53978 (6)0.0270 (3)
H22A0.80990.52810.55920.032*
C23A0.80815 (14)0.45033 (13)0.49536 (6)0.0254 (3)
H23A0.72620.50560.48490.030*
C24A0.87711 (14)0.35678 (12)0.46593 (6)0.0228 (3)
C25A0.99691 (14)0.27705 (12)0.48319 (6)0.0231 (3)
H25A1.04540.21270.46370.028*
C26A0.82490 (14)0.34188 (12)0.41805 (6)0.0231 (3)
C27A0.90496 (14)0.27128 (13)0.37860 (6)0.0271 (3)
H27A0.99510.23100.38230.032*
C28A0.85477 (15)0.25912 (14)0.33404 (6)0.0305 (3)
H28A0.91000.20810.30850.037*
C29A0.72513 (15)0.32066 (13)0.32662 (6)0.0286 (3)
H29A0.69200.31380.29540.034*
C30A0.64318 (14)0.39281 (13)0.36500 (6)0.0239 (3)
C31A0.69259 (14)0.40052 (13)0.41083 (6)0.0239 (3)
H31A0.63550.44660.43800.029*
C32A0.50106 (14)0.46201 (13)0.35537 (6)0.0250 (3)
C33A0.42463 (14)0.38268 (13)0.35927 (7)0.0277 (3)
C34A0.40304 (16)0.29852 (14)0.40431 (8)0.0376 (4)
H34A0.43900.28270.43860.045*
C35A0.32739 (18)0.23747 (16)0.39831 (10)0.0502 (5)
H35A0.31070.17990.42900.060*
C36A0.27647 (19)0.25950 (18)0.34843 (11)0.0563 (6)
H36A0.22640.21590.34500.068*
C37A0.29705 (17)0.34435 (17)0.30308 (9)0.0482 (5)
H37A0.26090.35970.26890.058*
C38A0.37171 (15)0.40635 (14)0.30880 (7)0.0317 (4)
C39A0.41085 (15)0.49906 (14)0.26875 (7)0.0309 (4)
C40A0.38515 (18)0.55247 (16)0.21365 (7)0.0427 (4)
H40A0.33260.53110.19560.051*
C41A0.4372 (2)0.63715 (17)0.18554 (7)0.0487 (5)
H41A0.42070.67380.14760.058*
C42A0.51331 (19)0.66985 (15)0.21146 (7)0.0437 (4)
H42A0.54780.72870.19140.052*
C43A0.53934 (16)0.61658 (14)0.26691 (7)0.0330 (4)
H43A0.59180.63820.28490.040*
C44A0.48756 (14)0.53195 (13)0.29503 (6)0.0264 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0302 (6)0.0376 (6)0.0289 (6)0.0191 (5)0.0048 (4)0.0144 (5)
O20.0185 (5)0.0238 (6)0.0369 (6)0.0063 (5)0.0019 (4)0.0056 (4)
C10.0208 (7)0.0281 (8)0.0360 (8)0.0108 (6)0.0019 (6)0.0102 (6)
C20.0293 (9)0.0366 (9)0.0495 (10)0.0126 (8)0.0115 (8)0.0043 (8)
C30.0309 (10)0.0397 (11)0.0808 (15)0.0065 (8)0.0203 (10)0.0131 (10)
C40.0204 (9)0.0529 (12)0.0846 (15)0.0093 (9)0.0009 (9)0.0382 (11)
C50.0292 (9)0.0527 (11)0.0533 (11)0.0201 (9)0.0110 (8)0.0305 (9)
C60.0240 (8)0.0346 (9)0.0387 (9)0.0160 (7)0.0050 (6)0.0184 (7)
C70.0325 (9)0.0355 (9)0.0278 (8)0.0216 (7)0.0033 (6)0.0102 (6)
C80.0532 (12)0.0542 (11)0.0298 (9)0.0374 (10)0.0058 (8)0.0089 (8)
C90.0715 (14)0.0488 (11)0.0296 (9)0.0393 (11)0.0130 (9)0.0066 (8)
C100.0546 (12)0.0328 (9)0.0449 (10)0.0204 (9)0.0213 (9)0.0028 (8)
C110.0318 (9)0.0283 (8)0.0389 (9)0.0133 (7)0.0058 (7)0.0041 (7)
C120.0279 (8)0.0254 (8)0.0273 (7)0.0146 (7)0.0010 (6)0.0056 (6)
C130.0205 (7)0.0258 (8)0.0254 (7)0.0088 (6)0.0002 (6)0.0070 (6)
C140.0202 (7)0.0225 (7)0.0216 (7)0.0082 (6)0.0021 (5)0.0014 (5)
C150.0194 (7)0.0283 (8)0.0239 (7)0.0075 (6)0.0018 (6)0.0059 (6)
C160.0263 (8)0.0244 (8)0.0250 (7)0.0086 (6)0.0011 (6)0.0075 (6)
C170.0228 (7)0.0256 (8)0.0229 (7)0.0110 (6)0.0029 (6)0.0023 (6)
C180.0191 (7)0.0223 (7)0.0187 (6)0.0061 (6)0.0028 (5)0.0001 (5)
C190.0223 (7)0.0207 (7)0.0220 (7)0.0081 (6)0.0021 (5)0.0032 (5)
C200.0184 (7)0.0259 (8)0.0204 (7)0.0077 (6)0.0023 (5)0.0045 (6)
C210.0224 (7)0.0268 (8)0.0249 (7)0.0113 (6)0.0027 (6)0.0026 (6)
C220.0218 (7)0.0235 (8)0.0294 (8)0.0047 (6)0.0040 (6)0.0053 (6)
C230.0183 (7)0.0304 (8)0.0246 (7)0.0067 (6)0.0004 (6)0.0069 (6)
C240.0183 (7)0.0275 (8)0.0212 (7)0.0084 (6)0.0026 (5)0.0044 (6)
C250.0204 (7)0.0241 (7)0.0239 (7)0.0074 (6)0.0017 (6)0.0055 (6)
C260.0206 (7)0.0270 (8)0.0198 (7)0.0084 (6)0.0016 (5)0.0057 (6)
C270.0170 (7)0.0306 (8)0.0253 (7)0.0064 (6)0.0005 (6)0.0058 (6)
C280.0224 (7)0.0239 (8)0.0268 (7)0.0037 (6)0.0034 (6)0.0042 (6)
C290.0236 (7)0.0253 (8)0.0237 (7)0.0103 (6)0.0018 (6)0.0028 (6)
C300.0187 (7)0.0267 (8)0.0203 (7)0.0089 (6)0.0019 (5)0.0057 (6)
C310.0199 (7)0.0229 (7)0.0228 (7)0.0057 (6)0.0022 (5)0.0050 (6)
C320.0189 (7)0.0212 (7)0.0260 (7)0.0061 (6)0.0021 (6)0.0042 (6)
C330.0162 (7)0.0239 (8)0.0299 (8)0.0034 (6)0.0032 (6)0.0070 (6)
C340.0233 (8)0.0306 (8)0.0317 (8)0.0020 (7)0.0064 (6)0.0067 (6)
C350.0307 (9)0.0405 (10)0.0401 (9)0.0013 (8)0.0155 (7)0.0154 (8)
C360.0305 (9)0.0443 (10)0.0606 (12)0.0096 (8)0.0159 (8)0.0223 (9)
C370.0285 (9)0.0357 (9)0.0513 (10)0.0148 (7)0.0034 (7)0.0117 (8)
C380.0183 (7)0.0271 (8)0.0344 (8)0.0071 (6)0.0011 (6)0.0092 (6)
C390.0181 (7)0.0242 (8)0.0325 (8)0.0058 (6)0.0026 (6)0.0078 (6)
C400.0288 (8)0.0286 (8)0.0372 (9)0.0119 (7)0.0080 (7)0.0050 (7)
C410.0394 (10)0.0331 (9)0.0283 (8)0.0093 (8)0.0058 (7)0.0017 (7)
C420.0389 (10)0.0383 (9)0.0256 (8)0.0078 (8)0.0032 (7)0.0075 (7)
C430.0268 (8)0.0318 (8)0.0295 (8)0.0100 (7)0.0019 (6)0.0080 (6)
C440.0172 (7)0.0235 (7)0.0261 (7)0.0052 (6)0.0005 (6)0.0054 (6)
O1A0.0337 (6)0.0204 (6)0.0557 (7)0.0077 (5)0.0239 (6)0.0004 (5)
O2A0.0193 (6)0.0333 (6)0.0350 (6)0.0042 (5)0.0057 (5)0.0129 (5)
C1A0.0265 (8)0.0222 (7)0.0322 (8)0.0086 (6)0.0100 (6)0.0068 (6)
C2A0.0287 (8)0.0328 (9)0.0410 (9)0.0098 (7)0.0058 (7)0.0135 (7)
C3A0.0424 (10)0.0525 (11)0.0367 (9)0.0228 (9)0.0034 (8)0.0174 (8)
C4A0.0566 (12)0.0546 (12)0.0278 (9)0.0275 (10)0.0092 (8)0.0022 (8)
C5A0.0402 (10)0.0379 (10)0.0345 (9)0.0141 (8)0.0168 (7)0.0004 (7)
C6A0.0282 (8)0.0253 (8)0.0313 (8)0.0096 (7)0.0124 (6)0.0047 (6)
C7A0.0253 (8)0.0209 (7)0.0352 (8)0.0083 (6)0.0105 (6)0.0046 (6)
C8A0.0269 (8)0.0263 (8)0.0477 (10)0.0070 (7)0.0141 (7)0.0052 (7)
C9A0.0253 (8)0.0328 (9)0.0621 (12)0.0123 (7)0.0021 (8)0.0159 (8)
C10A0.0374 (10)0.0377 (10)0.0445 (10)0.0211 (8)0.0060 (8)0.0145 (8)
C11A0.0388 (10)0.0325 (9)0.0339 (8)0.0176 (8)0.0076 (7)0.0033 (7)
C12A0.0269 (8)0.0246 (8)0.0325 (8)0.0103 (6)0.0094 (6)0.0053 (6)
C13A0.0249 (8)0.0204 (7)0.0338 (8)0.0058 (6)0.0121 (6)0.0023 (6)
C14A0.0231 (7)0.0259 (8)0.0249 (7)0.0063 (6)0.0086 (6)0.0018 (6)
C15A0.0278 (8)0.0262 (8)0.0434 (9)0.0007 (7)0.0185 (7)0.0061 (7)
C16A0.0342 (9)0.0250 (8)0.0504 (10)0.0034 (7)0.0186 (8)0.0118 (7)
C17A0.0278 (8)0.0308 (9)0.0348 (8)0.0087 (7)0.0120 (7)0.0092 (7)
C18A0.0221 (7)0.0273 (8)0.0206 (7)0.0072 (6)0.0058 (6)0.0027 (6)
C19A0.0255 (8)0.0231 (7)0.0243 (7)0.0071 (6)0.0075 (6)0.0025 (6)
C20A0.0204 (7)0.0246 (8)0.0228 (7)0.0084 (6)0.0051 (6)0.0000 (6)
C21A0.0252 (8)0.0283 (8)0.0231 (7)0.0107 (6)0.0053 (6)0.0040 (6)
C22A0.0251 (8)0.0254 (8)0.0275 (8)0.0063 (6)0.0012 (6)0.0062 (6)
C23A0.0202 (7)0.0250 (8)0.0283 (7)0.0060 (6)0.0057 (6)0.0014 (6)
C24A0.0200 (7)0.0237 (7)0.0221 (7)0.0070 (6)0.0033 (5)0.0002 (6)
C25A0.0209 (7)0.0230 (7)0.0248 (7)0.0063 (6)0.0037 (6)0.0049 (6)
C26A0.0213 (7)0.0223 (7)0.0235 (7)0.0069 (6)0.0055 (6)0.0007 (6)
C27A0.0199 (7)0.0291 (8)0.0277 (8)0.0042 (6)0.0059 (6)0.0024 (6)
C28A0.0254 (8)0.0342 (9)0.0280 (8)0.0035 (7)0.0036 (6)0.0106 (6)
C29A0.0247 (8)0.0334 (9)0.0272 (8)0.0062 (7)0.0081 (6)0.0077 (6)
C30A0.0208 (7)0.0246 (8)0.0257 (7)0.0077 (6)0.0058 (6)0.0017 (6)
C31A0.0204 (7)0.0235 (7)0.0251 (7)0.0045 (6)0.0046 (6)0.0036 (6)
C32A0.0203 (7)0.0250 (8)0.0289 (8)0.0048 (6)0.0059 (6)0.0068 (6)
C33A0.0165 (7)0.0232 (8)0.0397 (9)0.0023 (6)0.0015 (6)0.0092 (6)
C34A0.0249 (8)0.0270 (9)0.0502 (10)0.0030 (7)0.0047 (7)0.0061 (7)
C35A0.0304 (10)0.0282 (9)0.0819 (15)0.0098 (8)0.0161 (10)0.0128 (9)
C36A0.0318 (10)0.0431 (11)0.1030 (18)0.0191 (9)0.0077 (11)0.0333 (12)
C37A0.0290 (9)0.0500 (12)0.0758 (14)0.0127 (9)0.0101 (9)0.0295 (10)
C38A0.0195 (8)0.0298 (8)0.0478 (10)0.0044 (7)0.0079 (7)0.0151 (7)
C39A0.0239 (8)0.0311 (8)0.0364 (8)0.0012 (7)0.0123 (7)0.0114 (7)
C40A0.0402 (10)0.0451 (11)0.0404 (10)0.0017 (9)0.0201 (8)0.0140 (8)
C41A0.0581 (12)0.0435 (11)0.0295 (9)0.0004 (10)0.0147 (8)0.0036 (8)
C42A0.0510 (11)0.0330 (10)0.0365 (9)0.0087 (9)0.0020 (8)0.0008 (7)
C43A0.0337 (9)0.0296 (9)0.0355 (9)0.0099 (7)0.0052 (7)0.0073 (7)
C44A0.0215 (7)0.0246 (8)0.0311 (8)0.0031 (6)0.0082 (6)0.0059 (6)
Geometric parameters (Å, º) top
O1—C131.4276 (17)O1A—C13A1.4276 (18)
O1—H10.855 (9)O1A—H1A0.852 (9)
O2—C321.4458 (17)O2A—C32A1.4459 (17)
O2—H20.837 (9)O2A—H2A0.849 (9)
C1—C21.378 (2)C1A—C2A1.379 (2)
C1—C61.402 (2)C1A—C6A1.396 (2)
C1—C131.520 (2)C1A—C13A1.529 (2)
C2—C31.392 (2)C2A—C3A1.387 (2)
C2—H2AA0.9500C2A—H2AB0.9500
C3—C41.380 (3)C3A—C4A1.385 (3)
C3—H30.9500C3A—H3A0.9500
C4—C51.383 (3)C4A—C5A1.383 (2)
C4—H40.9500C4A—H4A0.9500
C5—C61.391 (2)C5A—C6A1.385 (2)
C5—H50.9500C5A—H5A0.9500
C6—C71.467 (2)C6A—C7A1.469 (2)
C7—C81.392 (2)C7A—C8A1.389 (2)
C7—C121.399 (2)C7A—C12A1.400 (2)
C8—C91.381 (3)C8A—C9A1.384 (2)
C8—H80.9500C8A—H8A0.9500
C9—C101.380 (3)C9A—C10A1.382 (2)
C9—H90.9500C9A—H9A0.9500
C10—C111.386 (2)C10A—C11A1.389 (2)
C10—H100.9500C10A—H10A0.9500
C11—C121.380 (2)C11A—C12A1.378 (2)
C11—H110.9500C11A—H11A0.9500
C12—C131.531 (2)C12A—C13A1.522 (2)
C13—C141.522 (2)C13A—C14A1.523 (2)
C14—C191.3910 (19)C14A—C19A1.384 (2)
C14—C151.394 (2)C14A—C15A1.388 (2)
C15—C161.384 (2)C15A—C16A1.384 (2)
C15—H150.9500C15A—H15A0.9500
C16—C171.390 (2)C16A—C17A1.383 (2)
C16—H160.9500C16A—H16A0.9500
C17—C181.396 (2)C17A—C18A1.391 (2)
C17—H170.9500C17A—H17A0.9500
C18—C191.390 (2)C18A—C19A1.395 (2)
C18—C201.4900 (18)C18A—C20A1.4894 (19)
C19—H190.9500C19A—H19A0.9500
C20—C251.391 (2)C20A—C25A1.390 (2)
C20—C211.395 (2)C20A—C21A1.394 (2)
C21—C221.3864 (19)C21A—C22A1.381 (2)
C21—H210.9500C21A—H21A0.9500
C22—C231.386 (2)C22A—C23A1.388 (2)
C22—H220.9500C22A—H22A0.9500
C23—C241.397 (2)C23A—C24A1.395 (2)
C23—H230.9500C23A—H23A0.9500
C24—C251.3984 (19)C24A—C25A1.4002 (19)
C24—C261.489 (2)C24A—C26A1.491 (2)
C25—H250.9500C25A—H25A0.9500
C26—C271.394 (2)C26A—C27A1.394 (2)
C26—C311.4056 (19)C26A—C31A1.4027 (19)
C27—C281.382 (2)C27A—C28A1.388 (2)
C27—H270.9500C27A—H27A0.9500
C28—C291.384 (2)C28A—C29A1.381 (2)
C28—H280.9500C28A—H28A0.9500
C29—C301.390 (2)C29A—C30A1.392 (2)
C29—H290.9500C29A—H29A0.9500
C30—C311.3861 (19)C30A—C31A1.387 (2)
C30—C321.5214 (19)C30A—C32A1.5248 (19)
C31—H310.9500C31A—H31A0.9500
C32—C331.527 (2)C32A—C33A1.521 (2)
C32—C441.5304 (19)C32A—C44A1.526 (2)
C33—C341.382 (2)C33A—C34A1.381 (2)
C33—C381.401 (2)C33A—C38A1.397 (2)
C34—C351.391 (2)C34A—C35A1.392 (3)
C34—H340.9500C34A—H34A0.9500
C35—C361.384 (3)C35A—C36A1.376 (3)
C35—H350.9500C35A—H35A0.9500
C36—C371.384 (2)C36A—C37A1.387 (3)
C36—H360.9500C36A—H36A0.9500
C37—C381.388 (2)C37A—C38A1.389 (2)
C37—H370.9500C37A—H37A0.9500
C38—C391.472 (2)C38A—C39A1.472 (2)
C39—C401.391 (2)C39A—C40A1.385 (2)
C39—C441.398 (2)C39A—C44A1.399 (2)
C40—C411.385 (2)C40A—C41A1.379 (3)
C40—H400.9500C40A—H40A0.9500
C41—C421.385 (2)C41A—C42A1.385 (3)
C41—H410.9500C41A—H41A0.9500
C42—C431.394 (2)C42A—C43A1.393 (2)
C42—H420.9500C42A—H42A0.9500
C43—C441.375 (2)C43A—C44A1.376 (2)
C43—H430.9500C43A—H43A0.9500
C13—O1—H1110.5 (14)C13A—O1A—H1A110.5 (13)
C32—O2—H2108.7 (14)C32A—O2A—H2A109.0 (15)
C2—C1—C6121.17 (15)C2A—C1A—C6A121.42 (14)
C2—C1—C13128.26 (14)C2A—C1A—C13A127.86 (14)
C6—C1—C13110.55 (13)C6A—C1A—C13A110.61 (13)
C1—C2—C3118.30 (17)C1A—C2A—C3A118.30 (15)
C1—C2—H2AA120.8C1A—C2A—H2AB120.9
C3—C2—H2AA120.8C3A—C2A—H2AB120.9
C4—C3—C2120.78 (18)C4A—C3A—C2A120.38 (16)
C4—C3—H3119.6C4A—C3A—H3A119.8
C2—C3—H3119.6C2A—C3A—H3A119.8
C3—C4—C5121.25 (17)C5A—C4A—C3A121.42 (16)
C3—C4—H4119.4C5A—C4A—H4A119.3
C5—C4—H4119.4C3A—C4A—H4A119.3
C4—C5—C6118.55 (17)C4A—C5A—C6A118.44 (16)
C4—C5—H5120.7C4A—C5A—H5A120.8
C6—C5—H5120.7C6A—C5A—H5A120.8
C5—C6—C1119.95 (16)C5A—C6A—C1A120.03 (15)
C5—C6—C7131.22 (15)C5A—C6A—C7A131.35 (14)
C1—C6—C7108.82 (13)C1A—C6A—C7A108.61 (13)
C8—C7—C12119.53 (16)C8A—C7A—C12A120.10 (14)
C8—C7—C6131.96 (15)C8A—C7A—C6A131.28 (14)
C12—C7—C6108.52 (13)C12A—C7A—C6A108.57 (13)
C9—C8—C7118.76 (16)C9A—C8A—C7A118.76 (15)
C9—C8—H8120.6C9A—C8A—H8A120.6
C7—C8—H8120.6C7A—C8A—H8A120.6
C10—C9—C8121.35 (16)C10A—C9A—C8A120.90 (16)
C10—C9—H9119.3C10A—C9A—H9A119.6
C8—C9—H9119.3C8A—C9A—H9A119.6
C9—C10—C11120.57 (17)C9A—C10A—C11A120.72 (16)
C9—C10—H10119.7C9A—C10A—H10A119.6
C11—C10—H10119.7C11A—C10A—H10A119.6
C12—C11—C10118.45 (16)C12A—C11A—C10A118.74 (15)
C12—C11—H11120.8C12A—C11A—H11A120.6
C10—C11—H11120.8C10A—C11A—H11A120.6
C11—C12—C7121.34 (14)C11A—C12A—C7A120.77 (15)
C11—C12—C13128.05 (13)C11A—C12A—C13A128.44 (14)
C7—C12—C13110.56 (13)C7A—C12A—C13A110.69 (13)
O1—C13—C1112.25 (12)O1A—C13A—C12A112.08 (12)
O1—C13—C14107.04 (11)O1A—C13A—C14A107.06 (11)
C1—C13—C14114.50 (12)C12A—C13A—C14A115.11 (12)
O1—C13—C12113.36 (12)O1A—C13A—C1A113.48 (12)
C1—C13—C12101.52 (11)C12A—C13A—C1A101.39 (11)
C14—C13—C12108.22 (12)C14A—C13A—C1A107.77 (12)
C19—C14—C15118.63 (13)C19A—C14A—C15A119.01 (14)
C19—C14—C13119.65 (12)C19A—C14A—C13A120.41 (13)
C15—C14—C13121.47 (12)C15A—C14A—C13A120.29 (13)
C16—C15—C14120.32 (13)C16A—C15A—C14A120.22 (14)
C16—C15—H15119.8C16A—C15A—H15A119.9
C14—C15—H15119.8C14A—C15A—H15A119.9
C15—C16—C17120.51 (14)C17A—C16A—C15A120.35 (15)
C15—C16—H16119.7C17A—C16A—H16A119.8
C17—C16—H16119.7C15A—C16A—H16A119.8
C16—C17—C18120.05 (14)C16A—C17A—C18A120.43 (14)
C16—C17—H17120.0C16A—C17A—H17A119.8
C18—C17—H17120.0C18A—C17A—H17A119.8
C19—C18—C17118.71 (13)C17A—C18A—C19A118.47 (13)
C19—C18—C20119.99 (13)C17A—C18A—C20A121.33 (13)
C17—C18—C20121.29 (13)C19A—C18A—C20A120.20 (13)
C18—C19—C14121.76 (13)C14A—C19A—C18A121.51 (14)
C18—C19—H19119.1C14A—C19A—H19A119.2
C14—C19—H19119.1C18A—C19A—H19A119.2
C25—C20—C21118.43 (12)C25A—C20A—C21A118.57 (13)
C25—C20—C18120.20 (12)C25A—C20A—C18A120.79 (13)
C21—C20—C18121.36 (12)C21A—C20A—C18A120.64 (13)
C22—C21—C20120.10 (13)C22A—C21A—C20A120.16 (14)
C22—C21—H21120.0C22A—C21A—H21A119.9
C20—C21—H21120.0C20A—C21A—H21A119.9
C23—C22—C21120.77 (14)C21A—C22A—C23A120.65 (14)
C23—C22—H22119.6C21A—C22A—H22A119.7
C21—C22—H22119.6C23A—C22A—H22A119.7
C22—C23—C24120.54 (13)C22A—C23A—C24A120.75 (13)
C22—C23—H23119.7C22A—C23A—H23A119.6
C24—C23—H23119.7C24A—C23A—H23A119.6
C23—C24—C25117.72 (13)C23A—C24A—C25A117.56 (13)
C23—C24—C26121.86 (12)C23A—C24A—C26A121.23 (12)
C25—C24—C26120.38 (13)C25A—C24A—C26A121.21 (13)
C20—C25—C24122.42 (13)C20A—C25A—C24A122.31 (13)
C20—C25—H25118.8C20A—C25A—H25A118.8
C24—C25—H25118.8C24A—C25A—H25A118.8
C27—C26—C31117.89 (13)C27A—C26A—C31A117.68 (13)
C27—C26—C24121.07 (12)C27A—C26A—C24A121.73 (13)
C31—C26—C24121.02 (12)C31A—C26A—C24A120.58 (13)
C28—C27—C26120.87 (13)C28A—C27A—C26A120.92 (13)
C28—C27—H27119.6C28A—C27A—H27A119.5
C26—C27—H27119.6C26A—C27A—H27A119.5
C27—C28—C29120.51 (13)C29A—C28A—C27A120.46 (14)
C27—C28—H28119.7C29A—C28A—H28A119.8
C29—C28—H28119.7C27A—C28A—H28A119.8
C28—C29—C30119.92 (13)C28A—C29A—C30A119.84 (14)
C28—C29—H29120.0C28A—C29A—H29A120.1
C30—C29—H29120.0C30A—C29A—H29A120.1
C31—C30—C29119.37 (13)C31A—C30A—C29A119.39 (13)
C31—C30—C32121.83 (12)C31A—C30A—C32A121.58 (13)
C29—C30—C32118.79 (12)C29A—C30A—C32A119.03 (13)
C30—C31—C26121.34 (13)C30A—C31A—C26A121.59 (13)
C30—C31—H31119.3C30A—C31A—H31A119.2
C26—C31—H31119.3C26A—C31A—H31A119.2
O2—C32—C30107.55 (11)O2A—C32A—C33A111.49 (12)
O2—C32—C33112.49 (11)O2A—C32A—C30A107.26 (11)
C30—C32—C33111.75 (11)C33A—C32A—C30A113.03 (12)
O2—C32—C44111.42 (11)O2A—C32A—C44A110.87 (11)
C30—C32—C44112.09 (11)C33A—C32A—C44A101.93 (12)
C33—C32—C44101.58 (11)C30A—C32A—C44A112.30 (12)
C34—C33—C38120.92 (14)C34A—C33A—C38A120.90 (16)
C34—C33—C32128.55 (14)C34A—C33A—C32A128.75 (15)
C38—C33—C32110.50 (12)C38A—C33A—C32A110.35 (13)
C33—C34—C35118.52 (15)C33A—C34A—C35A118.49 (18)
C33—C34—H34120.7C33A—C34A—H34A120.8
C35—C34—H34120.7C35A—C34A—H34A120.8
C36—C35—C34120.49 (16)C36A—C35A—C34A120.77 (18)
C36—C35—H35119.8C36A—C35A—H35A119.6
C34—C35—H35119.8C34A—C35A—H35A119.6
C35—C36—C37121.35 (16)C35A—C36A—C37A121.13 (18)
C35—C36—H36119.3C35A—C36A—H36A119.4
C37—C36—H36119.3C37A—C36A—H36A119.4
C36—C37—C38118.46 (16)C36A—C37A—C38A118.52 (19)
C36—C37—H37120.8C36A—C37A—H37A120.7
C38—C37—H37120.8C38A—C37A—H37A120.7
C37—C38—C33120.26 (15)C37A—C38A—C33A120.18 (17)
C37—C38—C39131.01 (14)C37A—C38A—C39A130.96 (16)
C33—C38—C39108.69 (13)C33A—C38A—C39A108.86 (14)
C40—C39—C44120.15 (15)C40A—C39A—C44A120.02 (16)
C40—C39—C38131.16 (15)C40A—C39A—C38A131.49 (16)
C44—C39—C38108.67 (12)C44A—C39A—C38A108.48 (13)
C41—C40—C39118.68 (15)C41A—C40A—C39A118.79 (17)
C41—C40—H40120.7C41A—C40A—H40A120.6
C39—C40—H40120.7C39A—C40A—H40A120.6
C40—C41—C42120.83 (15)C40A—C41A—C42A121.30 (16)
C40—C41—H41119.6C40A—C41A—H41A119.3
C42—C41—H41119.6C42A—C41A—H41A119.3
C41—C42—C43120.74 (16)C41A—C42A—C43A120.18 (17)
C41—C42—H42119.6C41A—C42A—H42A119.9
C43—C42—H42119.6C43A—C42A—H42A119.9
C44—C43—C42118.45 (15)C44A—C43A—C42A118.63 (16)
C44—C43—H43120.8C44A—C43A—H43A120.7
C42—C43—H43120.8C42A—C43A—H43A120.7
C43—C44—C39121.13 (14)C43A—C44A—C39A121.08 (14)
C43—C44—C32128.29 (13)C43A—C44A—C32A128.56 (14)
C39—C44—C32110.54 (13)C39A—C44A—C32A110.36 (13)
C6—C1—C2—C30.8 (2)C6A—C1A—C2A—C3A0.1 (2)
C13—C1—C2—C3178.89 (16)C13A—C1A—C2A—C3A175.92 (15)
C1—C2—C3—C40.4 (3)C1A—C2A—C3A—C4A1.0 (3)
C2—C3—C4—C50.2 (3)C2A—C3A—C4A—C5A1.5 (3)
C3—C4—C5—C60.4 (3)C3A—C4A—C5A—C6A0.8 (3)
C4—C5—C6—C10.1 (2)C4A—C5A—C6A—C1A0.3 (2)
C4—C5—C6—C7178.64 (16)C4A—C5A—C6A—C7A179.59 (16)
C2—C1—C6—C50.6 (2)C2A—C1A—C6A—C5A0.7 (2)
C13—C1—C6—C5178.96 (14)C13A—C1A—C6A—C5A175.89 (14)
C2—C1—C6—C7178.32 (15)C2A—C1A—C6A—C7A179.80 (14)
C13—C1—C6—C70.08 (17)C13A—C1A—C6A—C7A3.56 (17)
C5—C6—C7—C82.8 (3)C5A—C6A—C7A—C8A5.3 (3)
C1—C6—C7—C8178.51 (17)C1A—C6A—C7A—C8A175.30 (16)
C5—C6—C7—C12177.63 (16)C5A—C6A—C7A—C12A177.18 (16)
C1—C6—C7—C121.08 (17)C1A—C6A—C7A—C12A2.18 (17)
C12—C7—C8—C90.0 (2)C12A—C7A—C8A—C9A0.6 (2)
C6—C7—C8—C9179.56 (17)C6A—C7A—C8A—C9A176.65 (15)
C7—C8—C9—C100.1 (3)C7A—C8A—C9A—C10A0.1 (2)
C8—C9—C10—C110.4 (3)C8A—C9A—C10A—C11A0.2 (3)
C9—C10—C11—C120.7 (3)C9A—C10A—C11A—C12A0.7 (2)
C10—C11—C12—C70.6 (2)C10A—C11A—C12A—C7A1.2 (2)
C10—C11—C12—C13177.73 (15)C10A—C11A—C12A—C13A177.29 (15)
C8—C7—C12—C110.3 (2)C8A—C7A—C12A—C11A1.1 (2)
C6—C7—C12—C11179.35 (14)C6A—C7A—C12A—C11A176.70 (14)
C8—C7—C12—C13177.85 (14)C8A—C7A—C12A—C13A177.87 (13)
C6—C7—C12—C131.80 (17)C6A—C7A—C12A—C13A0.06 (17)
C2—C1—C13—O155.8 (2)C11A—C12A—C13A—O1A53.1 (2)
C6—C1—C13—O1122.45 (13)C7A—C12A—C13A—O1A123.37 (14)
C2—C1—C13—C1466.5 (2)C11A—C12A—C13A—C14A69.6 (2)
C6—C1—C13—C14115.25 (14)C7A—C12A—C13A—C14A113.97 (14)
C2—C1—C13—C12177.18 (16)C11A—C12A—C13A—C1A174.42 (15)
C6—C1—C13—C121.08 (16)C7A—C12A—C13A—C1A2.02 (16)
C11—C12—C13—O160.3 (2)C2A—C1A—C13A—O1A59.9 (2)
C7—C12—C13—O1122.35 (13)C6A—C1A—C13A—O1A123.76 (14)
C11—C12—C13—C1179.10 (15)C2A—C1A—C13A—C12A179.77 (15)
C7—C12—C13—C11.75 (16)C6A—C1A—C13A—C12A3.40 (16)
C11—C12—C13—C1458.26 (19)C2A—C1A—C13A—C14A58.50 (19)
C7—C12—C13—C14119.08 (13)C6A—C1A—C13A—C14A117.87 (13)
O1—C13—C14—C1928.10 (17)O1A—C13A—C14A—C19A18.55 (18)
C1—C13—C14—C19153.19 (13)C12A—C13A—C14A—C19A143.86 (14)
C12—C13—C14—C1994.41 (15)C1A—C13A—C14A—C19A103.86 (15)
O1—C13—C14—C15157.72 (13)O1A—C13A—C14A—C15A167.68 (14)
C1—C13—C14—C1532.64 (19)C12A—C13A—C14A—C15A42.36 (19)
C12—C13—C14—C1579.77 (16)C1A—C13A—C14A—C15A69.92 (17)
C19—C14—C15—C160.8 (2)C19A—C14A—C15A—C16A0.5 (2)
C13—C14—C15—C16173.41 (13)C13A—C14A—C15A—C16A174.32 (15)
C14—C15—C16—C170.5 (2)C14A—C15A—C16A—C17A0.2 (3)
C15—C16—C17—C180.9 (2)C15A—C16A—C17A—C18A0.0 (3)
C16—C17—C18—C191.8 (2)C16A—C17A—C18A—C19A0.1 (2)
C16—C17—C18—C20177.17 (12)C16A—C17A—C18A—C20A179.40 (14)
C17—C18—C19—C141.5 (2)C15A—C14A—C19A—C18A0.5 (2)
C20—C18—C19—C14177.53 (12)C13A—C14A—C19A—C18A174.35 (13)
C15—C14—C19—C180.1 (2)C17A—C18A—C19A—C14A0.3 (2)
C13—C14—C19—C18174.49 (12)C20A—C18A—C19A—C14A179.63 (13)
C19—C18—C20—C25142.93 (14)C17A—C18A—C20A—C25A34.0 (2)
C17—C18—C20—C2536.04 (19)C19A—C18A—C20A—C25A146.67 (14)
C19—C18—C20—C2136.10 (19)C17A—C18A—C20A—C21A145.90 (14)
C17—C18—C20—C21144.94 (14)C19A—C18A—C20A—C21A33.4 (2)
C25—C20—C21—C221.1 (2)C25A—C20A—C21A—C22A0.2 (2)
C18—C20—C21—C22179.90 (13)C18A—C20A—C21A—C22A179.69 (13)
C20—C21—C22—C230.7 (2)C20A—C21A—C22A—C23A0.2 (2)
C21—C22—C23—C240.5 (2)C21A—C22A—C23A—C24A0.6 (2)
C22—C23—C24—C251.2 (2)C22A—C23A—C24A—C25A0.5 (2)
C22—C23—C24—C26176.48 (13)C22A—C23A—C24A—C26A179.85 (13)
C21—C20—C25—C240.3 (2)C21A—C20A—C25A—C24A0.3 (2)
C18—C20—C25—C24179.33 (13)C18A—C20A—C25A—C24A179.59 (13)
C23—C24—C25—C200.9 (2)C23A—C24A—C25A—C20A0.0 (2)
C26—C24—C25—C20176.89 (13)C26A—C24A—C25A—C20A179.71 (13)
C23—C24—C26—C27155.25 (14)C23A—C24A—C26A—C27A161.96 (14)
C25—C24—C26—C2722.4 (2)C25A—C24A—C26A—C27A18.4 (2)
C23—C24—C26—C3123.0 (2)C23A—C24A—C26A—C31A17.1 (2)
C25—C24—C26—C31159.38 (13)C25A—C24A—C26A—C31A162.58 (13)
C31—C26—C27—C281.1 (2)C31A—C26A—C27A—C28A0.4 (2)
C24—C26—C27—C28179.40 (13)C24A—C26A—C27A—C28A179.53 (14)
C26—C27—C28—C292.1 (2)C26A—C27A—C28A—C29A2.6 (2)
C27—C28—C29—C300.3 (2)C27A—C28A—C29A—C30A1.9 (2)
C28—C29—C30—C312.4 (2)C28A—C29A—C30A—C31A1.0 (2)
C28—C29—C30—C32178.89 (13)C28A—C29A—C30A—C32A178.74 (14)
C29—C30—C31—C263.4 (2)C29A—C30A—C31A—C26A3.2 (2)
C32—C30—C31—C26177.94 (13)C32A—C30A—C31A—C26A176.55 (13)
C27—C26—C31—C301.6 (2)C27A—C26A—C31A—C30A2.4 (2)
C24—C26—C31—C30176.63 (13)C24A—C26A—C31A—C30A176.67 (13)
C31—C30—C32—O215.88 (18)C31A—C30A—C32A—O2A6.98 (18)
C29—C30—C32—O2165.48 (12)C29A—C30A—C32A—O2A172.73 (13)
C31—C30—C32—C33108.04 (15)C31A—C30A—C32A—C33A116.31 (15)
C29—C30—C32—C3370.61 (16)C29A—C30A—C32A—C33A63.98 (17)
C31—C30—C32—C44138.68 (14)C31A—C30A—C32A—C44A129.03 (14)
C29—C30—C32—C4442.67 (18)C29A—C30A—C32A—C44A50.67 (18)
O2—C32—C33—C3463.47 (18)O2A—C32A—C33A—C34A62.11 (19)
C30—C32—C33—C3457.62 (19)C30A—C32A—C33A—C34A58.8 (2)
C44—C32—C33—C34177.30 (14)C44A—C32A—C33A—C34A179.56 (14)
O2—C32—C33—C38118.49 (13)O2A—C32A—C33A—C38A116.84 (13)
C30—C32—C33—C38120.42 (13)C30A—C32A—C33A—C38A122.23 (13)
C44—C32—C33—C380.74 (15)C44A—C32A—C33A—C38A1.49 (15)
C38—C33—C34—C350.1 (2)C38A—C33A—C34A—C35A0.1 (2)
C32—C33—C34—C35177.76 (14)C32A—C33A—C34A—C35A178.95 (14)
C33—C34—C35—C360.5 (2)C33A—C34A—C35A—C36A0.7 (2)
C34—C35—C36—C370.3 (3)C34A—C35A—C36A—C37A1.1 (3)
C35—C36—C37—C380.2 (2)C35A—C36A—C37A—C38A0.6 (3)
C36—C37—C38—C330.6 (2)C36A—C37A—C38A—C33A0.2 (2)
C36—C37—C38—C39177.10 (15)C36A—C37A—C38A—C39A179.37 (16)
C34—C33—C38—C370.4 (2)C34A—C33A—C38A—C37A0.5 (2)
C32—C33—C38—C37178.64 (13)C32A—C33A—C38A—C37A179.59 (14)
C34—C33—C38—C39177.73 (13)C34A—C33A—C38A—C39A179.89 (13)
C32—C33—C38—C390.48 (16)C32A—C33A—C38A—C39A1.06 (17)
C37—C38—C39—C400.4 (3)C37A—C38A—C39A—C40A0.2 (3)
C33—C38—C39—C40178.32 (15)C33A—C38A—C39A—C40A179.42 (16)
C37—C38—C39—C44177.87 (16)C37A—C38A—C39A—C44A179.38 (16)
C33—C38—C39—C440.02 (16)C33A—C38A—C39A—C44A0.12 (17)
C44—C39—C40—C411.1 (2)C44A—C39A—C40A—C41A0.5 (2)
C38—C39—C40—C41177.07 (15)C38A—C39A—C40A—C41A179.00 (16)
C39—C40—C41—C420.6 (2)C39A—C40A—C41A—C42A0.5 (3)
C40—C41—C42—C430.1 (2)C40A—C41A—C42A—C43A0.4 (3)
C41—C42—C43—C440.3 (2)C41A—C42A—C43A—C44A0.3 (2)
C42—C43—C44—C390.2 (2)C42A—C43A—C44A—C39A0.3 (2)
C42—C43—C44—C32178.00 (14)C42A—C43A—C44A—C32A179.63 (15)
C40—C39—C44—C430.9 (2)C40A—C39A—C44A—C43A0.4 (2)
C38—C39—C44—C43177.61 (13)C38A—C39A—C44A—C43A179.16 (14)
C40—C39—C44—C32179.03 (13)C40A—C39A—C44A—C32A179.53 (14)
C38—C39—C44—C320.51 (16)C38A—C39A—C44A—C32A0.87 (17)
O2—C32—C44—C4362.81 (19)O2A—C32A—C44A—C43A62.61 (19)
C30—C32—C44—C4357.77 (19)C33A—C32A—C44A—C43A178.62 (15)
C33—C32—C44—C43177.20 (14)C30A—C32A—C44A—C43A57.4 (2)
O2—C32—C44—C39119.23 (13)O2A—C32A—C44A—C39A117.36 (14)
C30—C32—C44—C39120.18 (13)C33A—C32A—C44A—C39A1.41 (15)
C33—C32—C44—C390.75 (15)C30A—C32A—C44A—C39A122.66 (14)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C20–C25 and C20A–C25A rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.86 (1)2.07 (1)2.894 (2)163 (1)
O2—H2···Cg1ii0.84 (1)3.42 (1)4.163 (2)150 (1)
O1A—H1A···O2Aiii0.85 (1)1.99 (1)2.807 (2)160 (1)
O2A—H2A···Cg2iv0.85 (2)3.46 (1)4.169 (2)145 (1)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x, y+2, z+2; (iii) x+2, y+1, z+1; (iv) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C20–C25 and C20A–C25A rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.86 (1)2.066 (2)2.894 (2)162.8 (1)
O2—H2···Cg1ii0.84 (1)3.418 (2)4.163 (2)149.5 (1)
O1A—H1A···O2Aiii0.85 (1)1.989 (2)2.807 (2)160.4 (1)
O2A—H2A···Cg2iv0.85 (2)3.455 (2)4.169 (2)144.6 (1)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x, y+2, z+2; (iii) x+2, y+1, z+1; (iv) x+1, y+1, z+1.
 

Acknowledgements

We thank the NMR Center and Mass Spectrometry Unit of the University of Ioannina for measuring the 1H NMR and HRMS spectra. KS thanks the State Scholarships Foundation (IKY) for supporting this work.

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Volume 69| Part 10| October 2013| Pages o1514-o1515
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