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Acta Cryst. (2011). E67, o1112-o1113    [ doi:10.1107/S1600536811012888 ]

4,4'-Bis[2-(3,5-dimethoxyphenyl)ethenyl]biphenyl

A. Collas, M. Zeller and F. Blockhuys

Abstract top

The title compound, C32H30O4, crystallizes with three different conformers of the same molecule in the asymmetric unit, which explains the unusually large unit cell volume. The supramolecular structure is based on interactions involving the methoxy groups [C...O contacts between 3.090 (2) and 3.204 (2) Å, and C-H...O contacts between (normalized) 2.40 and 2.71 Å], [pi]-[pi] stacking of the electron-rich methoxy-substituted rings [centroid-centroid distances of 3.6454 (9)-3.738 (1) Å] and C-H...[pi] contacts (normalized, 2.62-2.97Å).

Comment top

The title compound was synthesized with its use as the active component in an organic blue-light-emitting diode in mind (Jin et al., 2002). Three conformers of the same molecule are present in the asymmetric unit, displaying different conformations of the methoxy groups and the biphenyl moiety; the molecules have been labeled A, B and C and the numbering scheme is given in Fig. 1. Fig. 2 presents a packing diagram. Molecules A and B have non-planar biphenyl units, with dihedral angles of 30.97 (7)° and 30.51 (7)°, respectively, while the same moiety in molecule C is virtually planar [4.22 (8)°]. In each of the three molecules the methoxy groups are oriented differently: their precise orientations do not have a large influence on the relative stability of the conformer (Vande Velde et al., 2007) but are merely due to the intermolecular contacts they are involved in. The three crystallographically independent molecules are held together by three C–H···π interactions involving aromatic hydrogen atoms. Rings 1 and 2 of molecule A are contacted by H14B and H19B (Table 1, entries 6 and 7) and ring 1 of molecule B is contacted by H10C (Table 1, entry 9). Additionally, molecule A is involved in two methoxy···methoxy contacts (Table 3, entries 1 and 2), two C–H···O contacts involving the methoxy group in the 3-position (Table 3, entries 3 and 4), four C–H···π interactions involving aromatic hydrogen atoms (Table 1, entries 1–4) and two π–π contacts with a symmetry-related A molecule (Table 2, entries 1 and 2). The supramolecular organization of molecule B is based on four methoxy···methoxy contacts (Table 3, entries 5–8), one contact involving the hydrogen atoms of the methoxy group in the 3-position (Table 3, entry 9), two additional C—H···π interactions (Table 1, entries 5 and 8) and two π–π contacts involving the methoxy-substituted rings (1 and 4) of molecules B and C (Table 2, entries 3 and 4). Molecule C participates in five contacts involving the methoxy groups, of which one is a methoxy···methoxy contact (Table 3, entry 10) and four are initiated by hydrogen atoms of the methoxy groups (Table 3, entries 11–14). Two contacts involve the π-systems of the methoxy-substituted rings of molecules B and C (Table 2, entries 5 and 6). Finally, it can be clearly seen from Table 2 that all three molecules are engaged in π–π stacking of the electron-rich methoxy-substituted rings 1 and 4.

Related literature top

For related methoxy-substituted biphenyls with 4,4'-bis(2-phenylethenyl) substitution, see: Vande Velde et al. (2002) [CSD refcode: MODDUE] and Li & Jian (2009) [CSD refcode: POWYUW]. For a study on the blue-light-emitting properties of a related compound, see: Jin et al. (2002). For the conformations of methoxybenzenes, see: Vande Velde et al. (2007). For the preparation, see: Yin et al. (2002).

Experimental top

The title compound was prepared as is outlined in Yin et al. (2002). Crystals suitable for the diffraction experiment were grown by slow evaporation of an acetone solution. M.p. (uncorrected) 452 K. 1H NMR (CDCl3, 400 MHz, TMS): δ 3.83 (s, OCH3), 6.41 (t, 2.2 Hz, H4, H26), 6.69 (d, 2.2 Hz, H2, H6, H24, H28), 7.06 (d, 16.3 Hz, H7/H22 or H8/H21), 7.11 (d, 16.3 Hz, H7/H22 or H8/H21), 7.56 (d, 8.4 Hz, H10, H14, H17, H19), 7.61 (d, 8.4 Hz, H11, H13, H17, H19) p.p.m. 13C NMR (CDCl3, 100 MHz, TMS): δ 55.40 (C29, C30, C31, C32), 100.12 (C4, C26), 104.69 (C2, C6, C24, C28), 127.08 (C10, C14, C17, C19), 127.09 (C11, C13, C16, C20), 128.71 (C7/C22 or C8/C21), 128.81 (C7/C22 or C8/C21), 136.32 (C9, C18), 139.38 (C12, C15), 139.83 (C1, C23), 161.06 (C3, C5, C25, C27) p.p.m.

Refinement top

Hydrogen atoms were placed in calculated positions and refined as riding with C—H distances of 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. : Molecular structure of the title compound showing the numbering scheme of the three crystallographically independent molecules (A, B, C). Displacement ellipsoids are drawn at the 50% probability level; hydrogen atoms are represented by spheres with an arbitrary radius. Hydrogen atoms of methoxy groups are denominated with a lower case suffix: a, b, c for A, d, e, f for B, and g, h, i for C.
[Figure 2] Fig. 2. : Packing scheme of the title compound.
4,4'-Bis[2-(3,5-dimethoxyphenyl)ethenyl]biphenyl top
Crystal data top
C32H30O4F(000) = 3048
Mr = 478.56Dx = 1.283 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9749 reflections
a = 11.8208 (13) Åθ = 2.3–32.8°
b = 27.896 (3) ŵ = 0.08 mm−1
c = 22.875 (3) ÅT = 100 K
β = 99.723 (2)°Plate, colourless
V = 7434.8 (14) Å30.55 × 0.45 × 0.15 mm
Z = 12
Data collection top
Bruker SMART APEX CCD
diffractometer		18422 independent reflections
Radiation source: fine-focus sealed tube13284 reflections with I > 2σ(I)
graphiteRint = 0.034
ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −15→15
Tmin = 0.956, Tmax = 0.988k = −37→37
74405 measured reflectionsl = −30→30
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0954P)2 + 3.3183P]
where P = (Fo2 + 2Fc2)/3
18422 reflections(Δ/σ)max = 0.001
985 parametersΔρmax = 0.68 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C32H30O4V = 7434.8 (14) Å3
Mr = 478.56Z = 12
Monoclinic, P21/cMo Kα radiation
a = 11.8208 (13) ŵ = 0.08 mm−1
b = 27.896 (3) ÅT = 100 K
c = 22.875 (3) Å0.55 × 0.45 × 0.15 mm
β = 99.723 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer		18422 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		13284 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.988Rint = 0.034
74405 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.181Δρmax = 0.68 e Å−3
S = 1.03Δρmin = −0.29 e Å−3
18422 reflectionsAbsolute structure: ?
985 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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. The data has been truncated at 0.75 Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.15447 (12)0.46499 (5)0.09560 (6)0.0168 (3)
C2A0.06813 (12)0.49166 (5)0.11557 (6)0.0174 (3)
H2A0.08610.51240.14880.021*
C3A−0.04359 (12)0.48741 (5)0.08623 (7)0.0181 (3)
C4A−0.07196 (12)0.45719 (5)0.03724 (7)0.0188 (3)
H4A−0.14900.45490.01720.023*
C5A0.01347 (12)0.43065 (5)0.01832 (7)0.0188 (3)
C6A0.12663 (12)0.43462 (5)0.04730 (7)0.0193 (3)
H6A0.18510.41640.03390.023*
C7A0.27507 (12)0.46747 (5)0.12364 (7)0.0180 (3)
H7A0.32780.45080.10400.022*
C8A0.32024 (12)0.49024 (5)0.17333 (6)0.0155 (3)
H8A0.26920.50690.19410.019*
C9A0.44267 (12)0.49152 (5)0.19832 (6)0.0147 (3)
C10A0.52534 (12)0.46805 (5)0.17172 (7)0.0184 (3)
H10A0.50200.45050.13610.022*
C11A0.63999 (12)0.46991 (5)0.19625 (7)0.0188 (3)
H11A0.69420.45370.17710.023*
C12A0.67846 (12)0.49502 (5)0.24851 (6)0.0145 (3)
C13A0.59664 (12)0.51896 (5)0.27477 (6)0.0179 (3)
H13A0.62020.53690.31010.021*
C14A0.48114 (12)0.51703 (5)0.25009 (6)0.0175 (3)
H14A0.42700.53350.26900.021*
C15A0.80193 (12)0.49572 (5)0.27384 (6)0.0153 (3)
C16A0.87267 (13)0.45705 (6)0.26583 (7)0.0223 (3)
H16A0.83990.42930.24550.027*
C17A0.98942 (13)0.45819 (6)0.28679 (7)0.0236 (3)
H17A1.03540.43150.28010.028*
C18A1.04088 (12)0.49784 (5)0.31748 (6)0.0175 (3)
C19A0.96978 (12)0.53637 (5)0.32649 (6)0.0160 (3)
H19A1.00220.56380.34770.019*
C20A0.85324 (12)0.53519 (5)0.30507 (6)0.0150 (3)
H20A0.80710.56190.31180.018*
C21A1.16440 (12)0.49687 (6)0.34026 (7)0.0197 (3)
H21A1.20780.47220.32580.024*
C22A1.22132 (12)0.52726 (5)0.37928 (6)0.0178 (3)
H22A1.17750.55210.39300.021*
C23A1.34420 (12)0.52665 (5)0.40355 (6)0.0167 (3)
C24A1.41857 (12)0.49137 (6)0.39001 (6)0.0189 (3)
H24A1.39020.46570.36430.023*
C25A1.53484 (12)0.49360 (6)0.41414 (7)0.0187 (3)
C26A1.57761 (12)0.53051 (5)0.45167 (6)0.0184 (3)
H26A1.65710.53200.46780.022*
C27A1.50255 (12)0.56549 (5)0.46552 (6)0.0180 (3)
C28A1.38688 (12)0.56404 (5)0.44188 (6)0.0179 (3)
H28A1.33670.58830.45160.021*
C29A−0.10905 (14)0.54661 (7)0.14674 (7)0.0280 (4)
H29A−0.06780.53180.18300.042*
H29B−0.18070.56080.15480.042*
H29C−0.06120.57160.13340.042*
C30A−0.11888 (14)0.38859 (7)−0.05346 (8)0.0342 (4)
H30A−0.15870.3759−0.02250.051*
H30B−0.11960.3645−0.08470.051*
H30C−0.15790.4177−0.07040.051*
C31A1.72111 (13)0.45930 (7)0.41990 (8)0.0301 (4)
H31A1.75290.48880.40600.045*
H31B1.75820.43150.40500.045*
H31C1.73500.45880.46340.045*
C32A1.47986 (15)0.63504 (6)0.52207 (9)0.0330 (4)
H32A1.43600.65130.48760.050*
H32B1.52620.65860.54740.050*
H32C1.42690.61920.54460.050*
C29B1.22529 (13)0.35012 (7)0.42489 (8)0.0291 (4)
H29D1.24070.35090.46830.044*
H29E1.26800.37590.40930.044*
H29F1.24960.31910.41100.044*
C2B0.91825 (13)0.32978 (6)0.39548 (7)0.0194 (3)
H2B0.89690.35470.36750.023*
C3B1.03183 (13)0.32419 (6)0.42179 (7)0.0199 (3)
C4B1.06591 (13)0.28789 (6)0.46322 (7)0.0202 (3)
H4B1.14410.28440.48100.024*
C5B0.98301 (13)0.25722 (6)0.47757 (7)0.0205 (3)
C6B0.86925 (13)0.26214 (6)0.45118 (7)0.0201 (3)
H6B0.81350.24040.46100.024*
C1B0.83559 (12)0.29863 (5)0.41031 (6)0.0181 (3)
C7B0.71374 (12)0.30156 (6)0.38449 (6)0.0186 (3)
H7B0.66580.27760.39680.022*
C8B0.66159 (12)0.33367 (5)0.34585 (7)0.0192 (3)
H8B0.70800.35800.33300.023*
C9B0.53876 (12)0.33459 (5)0.32160 (6)0.0176 (3)
C10B0.46492 (12)0.29667 (5)0.32902 (6)0.0166 (3)
H10B0.49460.26910.35070.020*
C11B0.34943 (12)0.29875 (5)0.30531 (6)0.0156 (3)
H11B0.30140.27240.31090.019*
C12B0.30172 (12)0.33866 (5)0.27328 (6)0.0161 (3)
C13B0.37525 (13)0.37678 (6)0.26680 (7)0.0212 (3)
H13B0.34520.40470.24600.025*
C14B0.49105 (13)0.37460 (6)0.29016 (7)0.0225 (3)
H14B0.53910.40100.28470.027*
C15B0.17901 (12)0.34021 (5)0.24667 (6)0.0163 (3)
C16B0.09571 (12)0.31668 (5)0.27237 (7)0.0189 (3)
H16B0.11810.29850.30750.023*
C17B−0.01938 (12)0.31947 (6)0.24737 (7)0.0197 (3)
H17B−0.07450.30320.26590.024*
C18B−0.05605 (12)0.34550 (5)0.19575 (7)0.0170 (3)
C19B0.02796 (12)0.36855 (5)0.16970 (7)0.0186 (3)
H19B0.00570.38630.13420.022*
C20B0.14264 (12)0.36598 (5)0.19463 (7)0.0182 (3)
H20B0.19780.38210.17600.022*
C21B−0.17861 (12)0.34744 (5)0.17100 (7)0.0184 (3)
H21B−0.22940.32950.19060.022*
C22B−0.22425 (12)0.37232 (5)0.12328 (7)0.0192 (3)
H22B−0.17210.39030.10470.023*
C23B−0.34536 (12)0.37534 (5)0.09590 (7)0.0173 (3)
C24B−0.43179 (12)0.34840 (5)0.11558 (7)0.0183 (3)
H24B−0.41370.32750.14870.022*
C25B−0.54361 (12)0.35257 (5)0.08623 (7)0.0177 (3)
C26B−0.57203 (12)0.38340 (5)0.03787 (7)0.0174 (3)
H26B−0.64900.38560.01760.021*
C27B−0.48670 (12)0.41062 (5)0.01991 (6)0.0169 (3)
C28B−0.37355 (12)0.40639 (5)0.04856 (7)0.0180 (3)
H28B−0.31520.42500.03550.022*
C30B1.12008 (15)0.20950 (7)0.54112 (8)0.0331 (4)
H30D1.15990.19980.50870.050*
H30E1.12280.18320.56970.050*
H30F1.15770.23780.56090.050*
C31B−0.60962 (15)0.29225 (6)0.14510 (8)0.0283 (4)
H31D−0.56070.26770.13160.042*
H31E−0.68140.27760.15230.042*
H31F−0.56970.30670.18190.042*
C32B−0.62030 (14)0.45357 (7)−0.04972 (8)0.0294 (4)
H32D−0.65920.4247−0.06740.044*
H32E−0.62220.4784−0.08020.044*
H32F−0.65940.4653−0.01800.044*
C6C1.38454 (12)0.22574 (5)0.45759 (6)0.0158 (3)
H6C1.32980.24490.47290.019*
C5C1.49943 (12)0.22673 (5)0.48485 (6)0.0160 (3)
C4C1.57998 (12)0.19932 (5)0.46280 (7)0.0171 (3)
H4C1.65840.20010.48110.021*
C3C1.54444 (12)0.17039 (5)0.41322 (7)0.0168 (3)
C2C1.43104 (12)0.16884 (5)0.38582 (6)0.0165 (3)
H2C1.40830.14900.35210.020*
C1C1.34976 (12)0.19700 (5)0.40838 (6)0.0151 (3)
C7C1.22788 (12)0.19699 (5)0.38199 (6)0.0164 (3)
H7C1.17890.21630.40110.020*
C8C1.17803 (12)0.17304 (5)0.33432 (6)0.0167 (3)
H8C1.22630.15410.31430.020*
C9C1.05527 (12)0.17327 (5)0.31000 (6)0.0151 (3)
C14C1.01218 (13)0.14143 (6)0.26500 (8)0.0264 (4)
H14C1.06350.12040.24990.032*
C13C0.89656 (14)0.13968 (6)0.24167 (8)0.0286 (4)
H13C0.87010.11720.21120.034*
C12C0.81788 (12)0.17009 (5)0.26172 (6)0.0151 (3)
C11C0.86161 (12)0.20175 (6)0.30668 (7)0.0212 (3)
H11C0.81040.22290.32170.025*
C10C0.97666 (13)0.20354 (6)0.33027 (7)0.0212 (3)
H10C1.00290.22590.36090.025*
C15C0.69448 (12)0.16939 (5)0.23627 (6)0.0154 (3)
C20C0.64884 (13)0.13538 (6)0.19423 (7)0.0231 (3)
H20C0.69900.11290.18080.028*
C19C0.53336 (13)0.13335 (6)0.17159 (7)0.0238 (3)
H19C0.50590.10960.14300.029*
C18C0.45600 (12)0.16546 (5)0.18980 (6)0.0162 (3)
C17C0.50090 (14)0.19927 (6)0.23188 (8)0.0291 (4)
H17C0.45050.22140.24590.035*
C16C0.61719 (14)0.20155 (6)0.25398 (8)0.0309 (4)
H16C0.64490.22570.28200.037*
C21C0.33291 (12)0.16459 (5)0.16694 (6)0.0172 (3)
H21C0.28520.18380.18700.021*
C22C0.28167 (12)0.13947 (5)0.12067 (6)0.0168 (3)
H22C0.33010.12050.10090.020*
C23C0.15881 (12)0.13783 (5)0.09682 (6)0.0150 (3)
C28C0.12162 (12)0.10430 (5)0.05276 (6)0.0161 (3)
H28C0.17540.08360.03900.019*
C27C0.00576 (12)0.10107 (5)0.02884 (6)0.0162 (3)
C26C−0.07309 (12)0.13105 (5)0.04851 (6)0.0163 (3)
H26C−0.15230.12870.03220.020*
C25C−0.03562 (12)0.16461 (5)0.09225 (6)0.0162 (3)
C24C0.07974 (12)0.16824 (5)0.11681 (6)0.0170 (3)
H24C0.10460.19120.14690.020*
C30C1.64021 (13)0.26068 (6)0.56038 (8)0.0260 (3)
H30G1.67250.22920.57270.039*
H30H1.64540.28160.59510.039*
H30I1.68340.27490.53170.039*
C29C1.59720 (14)0.10730 (6)0.35327 (7)0.0259 (3)
H29G1.55270.12090.31710.039*
H29H1.55020.08380.37010.039*
H29I1.66600.09160.34380.039*
C32C0.04090 (15)0.04176 (6)−0.04099 (8)0.0279 (4)
H32G0.09070.0634−0.05890.042*
H32H−0.00140.0210−0.07170.042*
H32I0.08780.0220−0.01080.042*
C31C−0.08460 (14)0.23222 (6)0.14598 (8)0.0277 (4)
H31G−0.03840.22090.18310.042*
H31H−0.15260.24910.15470.042*
H31I−0.03870.25410.12600.042*
O1A−0.13450 (9)0.51116 (4)0.10185 (5)0.0246 (3)
O2A−0.00321 (9)0.39978 (4)−0.02838 (5)0.0269 (3)
O3A1.60083 (9)0.45756 (4)0.39861 (5)0.0257 (3)
O4A1.55294 (9)0.60032 (4)0.50278 (5)0.0261 (3)
O1B1.10602 (9)0.35647 (4)0.40456 (5)0.0259 (3)
O2B1.00406 (10)0.22052 (5)0.51787 (5)0.0301 (3)
O3B−0.63448 (9)0.32819 (4)0.10092 (5)0.0261 (3)
O4B−0.50431 (9)0.44240 (4)−0.02580 (5)0.0232 (2)
O2C1.52291 (9)0.25537 (4)0.53358 (5)0.0210 (2)
O1C1.63029 (9)0.14468 (4)0.39530 (5)0.0232 (2)
O4C−0.03835 (9)0.06925 (4)−0.01410 (5)0.0233 (2)
O3C−0.11947 (9)0.19248 (4)0.10853 (5)0.0239 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0112 (6)0.0184 (7)0.0195 (7)−0.0013 (5)−0.0009 (5)0.0008 (5)
C2A0.0129 (7)0.0200 (7)0.0181 (7)−0.0001 (5)−0.0005 (5)−0.0009 (6)
C3A0.0114 (7)0.0224 (7)0.0201 (7)0.0019 (5)0.0014 (5)0.0044 (6)
C4A0.0115 (6)0.0239 (7)0.0199 (7)−0.0029 (5)−0.0005 (5)0.0034 (6)
C5A0.0150 (7)0.0221 (7)0.0184 (7)−0.0056 (6)−0.0001 (5)−0.0013 (6)
C6A0.0124 (7)0.0210 (7)0.0241 (8)−0.0015 (5)0.0019 (6)−0.0038 (6)
C7A0.0108 (6)0.0191 (7)0.0228 (7)0.0006 (5)−0.0008 (5)−0.0028 (6)
C8A0.0105 (6)0.0164 (7)0.0188 (7)0.0002 (5)0.0005 (5)0.0020 (5)
C9A0.0115 (6)0.0144 (6)0.0171 (7)−0.0022 (5)−0.0009 (5)0.0024 (5)
C10A0.0133 (7)0.0202 (7)0.0201 (7)0.0000 (5)−0.0019 (5)−0.0056 (6)
C11A0.0119 (7)0.0214 (7)0.0221 (7)0.0004 (5)−0.0001 (5)−0.0059 (6)
C12A0.0108 (6)0.0150 (6)0.0166 (7)−0.0014 (5)−0.0012 (5)0.0007 (5)
C13A0.0145 (7)0.0212 (7)0.0168 (7)−0.0019 (5)−0.0006 (5)−0.0044 (6)
C14A0.0126 (7)0.0215 (7)0.0181 (7)0.0004 (5)0.0017 (5)−0.0017 (6)
C15A0.0118 (6)0.0178 (7)0.0151 (6)−0.0022 (5)−0.0015 (5)−0.0004 (5)
C16A0.0154 (7)0.0201 (7)0.0285 (8)0.0006 (6)−0.0046 (6)−0.0081 (6)
C17A0.0149 (7)0.0228 (8)0.0301 (8)0.0034 (6)−0.0048 (6)−0.0078 (6)
C18A0.0135 (7)0.0212 (7)0.0163 (7)−0.0018 (5)−0.0019 (5)0.0008 (5)
C19A0.0146 (7)0.0168 (7)0.0150 (6)−0.0033 (5)−0.0020 (5)−0.0005 (5)
C20A0.0131 (7)0.0159 (7)0.0150 (6)−0.0001 (5)−0.0003 (5)−0.0001 (5)
C21A0.0124 (7)0.0235 (8)0.0219 (7)0.0008 (6)−0.0011 (6)−0.0007 (6)
C22A0.0121 (7)0.0214 (7)0.0187 (7)−0.0006 (5)−0.0007 (5)0.0023 (6)
C23A0.0128 (7)0.0213 (7)0.0150 (7)−0.0025 (5)−0.0005 (5)0.0049 (5)
C24A0.0150 (7)0.0230 (7)0.0172 (7)−0.0023 (6)−0.0014 (5)0.0012 (6)
C25A0.0152 (7)0.0224 (7)0.0182 (7)0.0007 (6)0.0018 (5)0.0044 (6)
C26A0.0122 (7)0.0233 (7)0.0183 (7)−0.0035 (5)−0.0015 (5)0.0069 (6)
C27A0.0166 (7)0.0186 (7)0.0173 (7)−0.0044 (5)−0.0015 (5)0.0055 (5)
C28A0.0156 (7)0.0182 (7)0.0187 (7)−0.0008 (5)−0.0005 (5)0.0042 (6)
C29A0.0231 (8)0.0379 (10)0.0228 (8)0.0110 (7)0.0036 (6)−0.0032 (7)
C30A0.0205 (8)0.0429 (11)0.0360 (10)−0.0110 (7)−0.0046 (7)−0.0150 (8)
C31A0.0162 (8)0.0386 (10)0.0345 (9)0.0034 (7)0.0014 (7)−0.0026 (8)
C32A0.0286 (9)0.0219 (8)0.0447 (11)−0.0001 (7)−0.0052 (8)−0.0094 (7)
C29B0.0162 (8)0.0372 (10)0.0333 (9)−0.0027 (7)0.0027 (7)−0.0052 (7)
C2B0.0172 (7)0.0223 (7)0.0175 (7)0.0014 (6)−0.0007 (6)−0.0021 (6)
C3B0.0161 (7)0.0232 (7)0.0203 (7)−0.0014 (6)0.0028 (6)−0.0080 (6)
C4B0.0135 (7)0.0273 (8)0.0186 (7)0.0036 (6)−0.0006 (5)−0.0069 (6)
C5B0.0172 (7)0.0248 (8)0.0183 (7)0.0049 (6)−0.0001 (6)−0.0024 (6)
C6B0.0156 (7)0.0238 (8)0.0205 (7)0.0011 (6)0.0016 (6)−0.0021 (6)
C1B0.0131 (7)0.0225 (7)0.0172 (7)0.0027 (5)−0.0015 (5)−0.0045 (6)
C7B0.0126 (7)0.0231 (7)0.0191 (7)0.0008 (5)−0.0004 (5)−0.0023 (6)
C8B0.0146 (7)0.0204 (7)0.0212 (7)−0.0009 (5)−0.0013 (6)−0.0020 (6)
C9B0.0148 (7)0.0192 (7)0.0174 (7)0.0009 (5)−0.0017 (5)−0.0017 (5)
C10B0.0137 (7)0.0167 (7)0.0176 (7)0.0027 (5)−0.0023 (5)0.0004 (5)
C11B0.0145 (7)0.0153 (7)0.0167 (7)0.0000 (5)0.0014 (5)0.0008 (5)
C12B0.0135 (7)0.0184 (7)0.0150 (6)0.0016 (5)−0.0016 (5)−0.0007 (5)
C13B0.0175 (7)0.0182 (7)0.0251 (8)0.0008 (6)−0.0043 (6)0.0042 (6)
C14B0.0175 (7)0.0201 (7)0.0274 (8)−0.0034 (6)−0.0032 (6)0.0032 (6)
C15B0.0140 (7)0.0156 (7)0.0178 (7)0.0017 (5)−0.0016 (5)−0.0006 (5)
C16B0.0156 (7)0.0220 (7)0.0179 (7)0.0016 (6)−0.0007 (5)0.0022 (6)
C17B0.0147 (7)0.0229 (8)0.0210 (7)−0.0005 (6)0.0017 (6)−0.0001 (6)
C18B0.0123 (7)0.0166 (7)0.0207 (7)0.0018 (5)−0.0012 (5)−0.0022 (5)
C19B0.0145 (7)0.0189 (7)0.0206 (7)0.0025 (5)−0.0026 (5)0.0040 (6)
C20B0.0129 (7)0.0189 (7)0.0216 (7)0.0010 (5)−0.0005 (5)0.0047 (6)
C21B0.0122 (7)0.0181 (7)0.0234 (7)0.0003 (5)−0.0012 (5)−0.0022 (6)
C22B0.0136 (7)0.0190 (7)0.0237 (8)−0.0017 (5)−0.0006 (6)0.0004 (6)
C23B0.0135 (7)0.0173 (7)0.0199 (7)0.0007 (5)−0.0011 (5)−0.0032 (6)
C24B0.0166 (7)0.0173 (7)0.0198 (7)0.0002 (5)−0.0004 (6)−0.0005 (6)
C25B0.0145 (7)0.0173 (7)0.0208 (7)−0.0012 (5)0.0017 (5)−0.0033 (6)
C26B0.0113 (6)0.0193 (7)0.0203 (7)0.0014 (5)−0.0008 (5)−0.0048 (6)
C27B0.0146 (7)0.0178 (7)0.0174 (7)0.0038 (5)0.0001 (5)−0.0009 (5)
C28B0.0123 (7)0.0177 (7)0.0233 (7)−0.0007 (5)0.0009 (6)−0.0008 (6)
C30B0.0234 (9)0.0391 (10)0.0352 (10)0.0069 (7)−0.0002 (7)0.0114 (8)
C31B0.0262 (9)0.0316 (9)0.0275 (8)−0.0060 (7)0.0061 (7)0.0034 (7)
C32B0.0197 (8)0.0351 (9)0.0308 (9)0.0056 (7)−0.0029 (7)0.0111 (7)
C6C0.0117 (6)0.0150 (6)0.0200 (7)0.0003 (5)0.0005 (5)−0.0012 (5)
C5C0.0158 (7)0.0133 (6)0.0179 (7)−0.0030 (5)−0.0004 (5)0.0002 (5)
C4C0.0097 (6)0.0181 (7)0.0222 (7)−0.0017 (5)−0.0010 (5)0.0015 (6)
C3C0.0126 (7)0.0165 (7)0.0215 (7)0.0018 (5)0.0032 (5)0.0014 (5)
C2C0.0132 (7)0.0173 (7)0.0181 (7)−0.0002 (5)−0.0001 (5)−0.0012 (5)
C1C0.0114 (6)0.0145 (6)0.0184 (7)−0.0008 (5)−0.0001 (5)0.0009 (5)
C7C0.0101 (6)0.0190 (7)0.0192 (7)0.0013 (5)−0.0001 (5)−0.0014 (5)
C8C0.0118 (6)0.0170 (7)0.0204 (7)0.0011 (5)−0.0002 (5)−0.0014 (5)
C9C0.0122 (6)0.0164 (7)0.0152 (6)−0.0005 (5)−0.0019 (5)0.0002 (5)
C14C0.0171 (7)0.0277 (8)0.0306 (9)0.0085 (6)−0.0072 (6)−0.0138 (7)
C13C0.0189 (8)0.0279 (9)0.0336 (9)0.0064 (6)−0.0112 (7)−0.0177 (7)
C12C0.0135 (7)0.0162 (7)0.0141 (6)−0.0011 (5)−0.0022 (5)−0.0005 (5)
C11C0.0112 (7)0.0285 (8)0.0233 (8)0.0004 (6)0.0012 (6)−0.0118 (6)
C10C0.0136 (7)0.0261 (8)0.0224 (7)−0.0021 (6)−0.0012 (6)−0.0121 (6)
C15C0.0124 (7)0.0170 (7)0.0152 (7)−0.0008 (5)−0.0025 (5)0.0002 (5)
C20C0.0131 (7)0.0304 (8)0.0254 (8)0.0002 (6)0.0023 (6)−0.0146 (6)
C19C0.0131 (7)0.0305 (8)0.0260 (8)−0.0014 (6)−0.0014 (6)−0.0157 (7)
C18C0.0139 (7)0.0166 (7)0.0167 (7)−0.0010 (5)−0.0012 (5)−0.0009 (5)
C17C0.0162 (8)0.0297 (9)0.0366 (9)0.0094 (6)−0.0095 (7)−0.0164 (7)
C16C0.0201 (8)0.0278 (9)0.0386 (10)0.0064 (6)−0.0128 (7)−0.0198 (7)
C21C0.0123 (7)0.0190 (7)0.0190 (7)0.0016 (5)−0.0011 (5)−0.0018 (5)
C22C0.0123 (7)0.0183 (7)0.0191 (7)0.0003 (5)0.0005 (5)−0.0027 (5)
C23C0.0116 (6)0.0167 (7)0.0156 (7)−0.0004 (5)−0.0006 (5)0.0003 (5)
C28C0.0144 (7)0.0148 (7)0.0185 (7)0.0010 (5)0.0009 (5)−0.0014 (5)
C27C0.0158 (7)0.0144 (6)0.0172 (7)−0.0026 (5)−0.0010 (5)0.0000 (5)
C26C0.0122 (6)0.0165 (7)0.0186 (7)−0.0010 (5)−0.0019 (5)0.0015 (5)
C25C0.0126 (7)0.0180 (7)0.0177 (7)0.0026 (5)0.0015 (5)0.0007 (5)
C24C0.0157 (7)0.0175 (7)0.0163 (7)0.0003 (5)−0.0013 (5)−0.0039 (5)
C30C0.0208 (8)0.0255 (8)0.0283 (8)−0.0050 (6)−0.0059 (6)−0.0035 (7)
C29C0.0222 (8)0.0270 (8)0.0283 (8)0.0052 (6)0.0037 (6)−0.0075 (7)
C32C0.0295 (9)0.0237 (8)0.0303 (9)−0.0030 (7)0.0044 (7)−0.0103 (7)
C31C0.0238 (8)0.0255 (8)0.0331 (9)0.0055 (6)0.0028 (7)−0.0094 (7)
O1A0.0116 (5)0.0341 (6)0.0274 (6)0.0058 (4)0.0015 (4)−0.0023 (5)
O2A0.0170 (5)0.0343 (7)0.0279 (6)−0.0068 (5)−0.0009 (5)−0.0123 (5)
O3A0.0144 (5)0.0316 (6)0.0292 (6)0.0032 (4)−0.0014 (4)−0.0045 (5)
O4A0.0190 (6)0.0215 (6)0.0348 (6)−0.0035 (4)−0.0040 (5)−0.0049 (5)
O1B0.0161 (5)0.0285 (6)0.0319 (6)−0.0047 (4)0.0011 (5)−0.0021 (5)
O2B0.0210 (6)0.0373 (7)0.0302 (6)0.0082 (5)−0.0005 (5)0.0110 (5)
O3B0.0167 (5)0.0303 (6)0.0311 (6)−0.0063 (5)0.0032 (5)0.0036 (5)
O4B0.0161 (5)0.0275 (6)0.0251 (6)0.0033 (4)0.0003 (4)0.0079 (5)
O2C0.0163 (5)0.0216 (5)0.0223 (5)−0.0026 (4)−0.0044 (4)−0.0054 (4)
O1C0.0131 (5)0.0258 (6)0.0298 (6)0.0046 (4)0.0013 (4)−0.0067 (5)
O4C0.0198 (5)0.0200 (5)0.0271 (6)−0.0010 (4)−0.0044 (4)−0.0089 (4)
O3C0.0152 (5)0.0270 (6)0.0279 (6)0.0066 (4)−0.0012 (4)−0.0083 (5)
Geometric parameters (Å, °) top
C1A—C6A1.387 (2)C17B—C18B1.392 (2)
C1A—C2A1.401 (2)C17B—H17B0.9500
C1A—C7A1.4627 (19)C18B—C19B1.398 (2)
C2A—C3A1.3817 (19)C18B—C21B1.4647 (19)
C2A—H2A0.9500C19B—C20B1.3809 (19)
C3A—O1A1.3607 (18)C19B—H19B0.9500
C3A—C4A1.397 (2)C20B—H20B0.9500
C4A—C5A1.379 (2)C21B—C22B1.329 (2)
C4A—H4A0.9500C21B—H21B0.9500
C5A—O2A1.3603 (18)C22B—C23B1.4650 (19)
C5A—C6A1.3933 (19)C22B—H22B0.9500
C6A—H6A0.9500C23B—C28B1.383 (2)
C7A—C8A1.333 (2)C23B—C24B1.402 (2)
C7A—H7A0.9500C24B—C25B1.383 (2)
C8A—C9A1.4638 (18)C24B—H24B0.9500
C8A—H8A0.9500C25B—O3B1.3605 (18)
C9A—C14A1.391 (2)C25B—C26B1.397 (2)
C9A—C10A1.398 (2)C26B—C27B1.379 (2)
C10A—C11A1.3774 (19)C26B—H26B0.9500
C10A—H10A0.9500C27B—O4B1.3597 (18)
C11A—C12A1.3940 (19)C27B—C28B1.3915 (19)
C11A—H11A0.9500C28B—H28B0.9500
C12A—C13A1.392 (2)C30B—O2B1.4184 (19)
C12A—C15A1.4768 (18)C30B—H30D0.9800
C13A—C14A1.3876 (19)C30B—H30E0.9800
C13A—H13A0.9500C30B—H30F0.9800
C14A—H14A0.9500C31B—O3B1.419 (2)
C15A—C20A1.3943 (19)C31B—H31D0.9800
C15A—C16A1.396 (2)C31B—H31E0.9800
C16A—C17A1.383 (2)C31B—H31F0.9800
C16A—H16A0.9500C32B—O4B1.4224 (18)
C17A—C18A1.394 (2)C32B—H32D0.9800
C17A—H17A0.9500C32B—H32E0.9800
C18A—C19A1.401 (2)C32B—H32F0.9800
C18A—C21A1.4654 (19)C6C—C1C1.3866 (19)
C19A—C20A1.3824 (19)C6C—C5C1.3957 (19)
C19A—H19A0.9500C6C—H6C0.9500
C20A—H20A0.9500C5C—O2C1.3614 (17)
C21A—C22A1.329 (2)C5C—C4C1.381 (2)
C21A—H21A0.9500C4C—C3C1.397 (2)
C22A—C23A1.4649 (19)C4C—H4C0.9500
C22A—H22A0.9500C3C—O1C1.3613 (17)
C23A—C24A1.389 (2)C3C—C2C1.3813 (19)
C23A—C28A1.400 (2)C2C—C1C1.405 (2)
C24A—C25A1.393 (2)C2C—H2C0.9500
C24A—H24A0.9500C1C—C7C1.4651 (18)
C25A—O3A1.3559 (18)C7C—C8C1.329 (2)
C25A—C26A1.381 (2)C7C—H7C0.9500
C26A—C27A1.391 (2)C8C—C9C1.4637 (19)
C26A—H26A0.9500C8C—H8C0.9500
C27A—O4A1.3615 (18)C9C—C14C1.390 (2)
C27A—C28A1.3835 (19)C9C—C10C1.392 (2)
C28A—H28A0.9500C14C—C13C1.382 (2)
C29A—O1A1.421 (2)C14C—H14C0.9500
C29A—H29A0.9800C13C—C12C1.392 (2)
C29A—H29B0.9800C13C—H13C0.9500
C29A—H29C0.9800C12C—C11C1.3877 (19)
C30A—O2A1.4251 (18)C12C—C15C1.4766 (19)
C30A—H30A0.9800C11C—C10C1.377 (2)
C30A—H30B0.9800C11C—H11C0.9500
C30A—H30C0.9800C10C—H10C0.9500
C31A—O3A1.4239 (18)C15C—C16C1.389 (2)
C31A—H31A0.9800C15C—C20C1.393 (2)
C31A—H31B0.9800C20C—C19C1.377 (2)
C31A—H31C0.9800C20C—H20C0.9500
C32A—O4A1.417 (2)C19C—C18C1.393 (2)
C32A—H32A0.9800C19C—H19C0.9500
C32A—H32B0.9800C18C—C17C1.388 (2)
C32A—H32C0.9800C18C—C21C1.4609 (19)
C29B—O1B1.4191 (18)C17C—C16C1.384 (2)
C29B—H29D0.9800C17C—H17C0.9500
C29B—H29E0.9800C16C—H16C0.9500
C29B—H29F0.9800C21C—C22C1.327 (2)
C2B—C3B1.384 (2)C21C—H21C0.9500
C2B—C1B1.392 (2)C22C—C23C1.4634 (19)
C2B—H2B0.9500C22C—H22C0.9500
C3B—O1B1.3608 (19)C23C—C28C1.3906 (19)
C3B—C4B1.399 (2)C23C—C24C1.395 (2)
C4B—C5B1.382 (2)C28C—C27C1.3892 (19)
C4B—H4B0.9500C28C—H28C0.9500
C5B—O2B1.3719 (19)C27C—O4C1.3607 (17)
C5B—C6B1.385 (2)C27C—C26C1.383 (2)
C6B—C1B1.394 (2)C26C—C25C1.387 (2)
C6B—H6B0.9500C26C—H26C0.9500
C1B—C7B1.4638 (19)C25C—O3C1.3602 (17)
C7B—C8B1.334 (2)C25C—C24C1.3880 (19)
C7B—H7B0.9500C24C—H24C0.9500
C8B—C9B1.464 (2)C30C—O2C1.4259 (17)
C8B—H8B0.9500C30C—H30G0.9800
C9B—C14B1.394 (2)C30C—H30H0.9800
C9B—C10B1.400 (2)C30C—H30I0.9800
C10B—C11B1.3825 (19)C29C—O1C1.4274 (19)
C10B—H10B0.9500C29C—H29G0.9800
C11B—C12B1.3980 (19)C29C—H29H0.9800
C11B—H11B0.9500C29C—H29I0.9800
C12B—C13B1.397 (2)C32C—O4C1.4278 (19)
C12B—C15B1.4760 (19)C32C—H32G0.9800
C13B—C14B1.384 (2)C32C—H32H0.9800
C13B—H13B0.9500C32C—H32I0.9800
C14B—H14B0.9500C31C—O3C1.4191 (19)
C15B—C16B1.393 (2)C31C—H31G0.9800
C15B—C20B1.395 (2)C31C—H31H0.9800
C16B—C17B1.3861 (19)C31C—H31I0.9800
C16B—H16B0.9500
C6A—C1A—C2A119.76 (13)C20B—C19B—C18B121.23 (14)
C6A—C1A—C7A117.44 (13)C20B—C19B—H19B119.4
C2A—C1A—C7A122.80 (13)C18B—C19B—H19B119.4
C3A—C2A—C1A119.03 (13)C19B—C20B—C15B121.26 (14)
C3A—C2A—H2A120.5C19B—C20B—H20B119.4
C1A—C2A—H2A120.5C15B—C20B—H20B119.4
O1A—C3A—C2A124.27 (14)C22B—C21B—C18B125.08 (14)
O1A—C3A—C4A114.28 (13)C22B—C21B—H21B117.5
C2A—C3A—C4A121.45 (14)C18B—C21B—H21B117.5
C5A—C4A—C3A119.08 (13)C21B—C22B—C23B127.82 (14)
C5A—C4A—H4A120.5C21B—C22B—H22B116.1
C3A—C4A—H4A120.5C23B—C22B—H22B116.1
O2A—C5A—C4A124.70 (13)C28B—C23B—C24B119.66 (13)
O2A—C5A—C6A115.09 (13)C28B—C23B—C22B117.36 (13)
C4A—C5A—C6A120.21 (14)C24B—C23B—C22B122.98 (13)
C1A—C6A—C5A120.46 (14)C25B—C24B—C23B119.19 (14)
C1A—C6A—H6A119.8C25B—C24B—H24B120.4
C5A—C6A—H6A119.8C23B—C24B—H24B120.4
C8A—C7A—C1A128.11 (14)O3B—C25B—C24B124.61 (14)
C8A—C7A—H7A115.9O3B—C25B—C26B114.15 (13)
C1A—C7A—H7A115.9C24B—C25B—C26B121.24 (13)
C7A—C8A—C9A124.89 (13)C27B—C26B—C25B118.99 (13)
C7A—C8A—H8A117.6C27B—C26B—H26B120.5
C9A—C8A—H8A117.6C25B—C26B—H26B120.5
C14A—C9A—C10A117.26 (13)O4B—C27B—C26B124.28 (13)
C14A—C9A—C8A120.30 (13)O4B—C27B—C28B115.31 (13)
C10A—C9A—C8A122.44 (13)C26B—C27B—C28B120.41 (13)
C11A—C10A—C9A121.14 (13)C23B—C28B—C27B120.48 (14)
C11A—C10A—H10A119.4C23B—C28B—H28B119.8
C9A—C10A—H10A119.4C27B—C28B—H28B119.8
C10A—C11A—C12A121.61 (14)O2B—C30B—H30D109.5
C10A—C11A—H11A119.2O2B—C30B—H30E109.5
C12A—C11A—H11A119.2H30D—C30B—H30E109.5
C13A—C12A—C11A117.47 (13)O2B—C30B—H30F109.5
C13A—C12A—C15A122.48 (13)H30D—C30B—H30F109.5
C11A—C12A—C15A120.05 (13)H30E—C30B—H30F109.5
C14A—C13A—C12A120.88 (13)O3B—C31B—H31D109.5
C14A—C13A—H13A119.6O3B—C31B—H31E109.5
C12A—C13A—H13A119.6H31D—C31B—H31E109.5
C13A—C14A—C9A121.62 (13)O3B—C31B—H31F109.5
C13A—C14A—H14A119.2H31D—C31B—H31F109.5
C9A—C14A—H14A119.2H31E—C31B—H31F109.5
C20A—C15A—C16A117.33 (13)O4B—C32B—H32D109.5
C20A—C15A—C12A121.80 (13)O4B—C32B—H32E109.5
C16A—C15A—C12A120.84 (13)H32D—C32B—H32E109.5
C17A—C16A—C15A121.45 (14)O4B—C32B—H32F109.5
C17A—C16A—H16A119.3H32D—C32B—H32F109.5
C15A—C16A—H16A119.3H32E—C32B—H32F109.5
C16A—C17A—C18A121.20 (14)C1C—C6C—C5C120.45 (13)
C16A—C17A—H17A119.4C1C—C6C—H6C119.8
C18A—C17A—H17A119.4C5C—C6C—H6C119.8
C17A—C18A—C19A117.48 (13)O2C—C5C—C4C124.48 (13)
C17A—C18A—C21A119.24 (14)O2C—C5C—C6C115.20 (13)
C19A—C18A—C21A123.25 (13)C4C—C5C—C6C120.31 (13)
C20A—C19A—C18A121.08 (13)C5C—C4C—C3C118.99 (13)
C20A—C19A—H19A119.5C5C—C4C—H4C120.5
C18A—C19A—H19A119.5C3C—C4C—H4C120.5
C19A—C20A—C15A121.44 (13)O1C—C3C—C2C124.23 (13)
C19A—C20A—H20A119.3O1C—C3C—C4C114.29 (12)
C15A—C20A—H20A119.3C2C—C3C—C4C121.47 (13)
C22A—C21A—C18A126.04 (14)C3C—C2C—C1C119.16 (13)
C22A—C21A—H21A117.0C3C—C2C—H2C120.4
C18A—C21A—H21A117.0C1C—C2C—H2C120.4
C21A—C22A—C23A127.20 (14)C6C—C1C—C2C119.61 (13)
C21A—C22A—H22A116.4C6C—C1C—C7C118.07 (13)
C23A—C22A—H22A116.4C2C—C1C—C7C122.31 (13)
C24A—C23A—C28A119.52 (13)C8C—C7C—C1C127.38 (13)
C24A—C23A—C22A123.22 (13)C8C—C7C—H7C116.3
C28A—C23A—C22A117.26 (13)C1C—C7C—H7C116.3
C23A—C24A—C25A119.94 (14)C7C—C8C—C9C125.69 (13)
C23A—C24A—H24A120.0C7C—C8C—H8C117.2
C25A—C24A—H24A120.0C9C—C8C—H8C117.2
O3A—C25A—C26A123.32 (13)C14C—C9C—C10C116.93 (13)
O3A—C25A—C24A115.83 (13)C14C—C9C—C8C119.64 (13)
C26A—C25A—C24A120.84 (14)C10C—C9C—C8C123.42 (13)
C25A—C26A—C27A118.96 (13)C13C—C14C—C9C121.58 (14)
C25A—C26A—H26A120.5C13C—C14C—H14C119.2
C27A—C26A—H26A120.5C9C—C14C—H14C119.2
O4A—C27A—C28A124.38 (14)C14C—C13C—C12C121.57 (14)
O4A—C27A—C26A114.51 (13)C14C—C13C—H13C119.2
C28A—C27A—C26A121.11 (14)C12C—C13C—H13C119.2
C27A—C28A—C23A119.63 (14)C11C—C12C—C13C116.48 (13)
C27A—C28A—H28A120.2C11C—C12C—C15C121.35 (13)
C23A—C28A—H28A120.2C13C—C12C—C15C122.17 (13)
O1A—C29A—H29A109.5C10C—C11C—C12C122.23 (14)
O1A—C29A—H29B109.5C10C—C11C—H11C118.9
H29A—C29A—H29B109.5C12C—C11C—H11C118.9
O1A—C29A—H29C109.5C11C—C10C—C9C121.22 (13)
H29A—C29A—H29C109.5C11C—C10C—H10C119.4
H29B—C29A—H29C109.5C9C—C10C—H10C119.4
O2A—C30A—H30A109.5C16C—C15C—C20C116.37 (13)
O2A—C30A—H30B109.5C16C—C15C—C12C122.08 (13)
H30A—C30A—H30B109.5C20C—C15C—C12C121.52 (13)
O2A—C30A—H30C109.5C19C—C20C—C15C122.10 (14)
H30A—C30A—H30C109.5C19C—C20C—H20C118.9
H30B—C30A—H30C109.5C15C—C20C—H20C118.9
O3A—C31A—H31A109.5C20C—C19C—C18C121.35 (14)
O3A—C31A—H31B109.5C20C—C19C—H19C119.3
H31A—C31A—H31B109.5C18C—C19C—H19C119.3
O3A—C31A—H31C109.5C17C—C18C—C19C116.81 (13)
H31A—C31A—H31C109.5C17C—C18C—C21C120.05 (13)
H31B—C31A—H31C109.5C19C—C18C—C21C123.15 (13)
O4A—C32A—H32A109.5C16C—C17C—C18C121.65 (15)
O4A—C32A—H32B109.5C16C—C17C—H17C119.2
H32A—C32A—H32B109.5C18C—C17C—H17C119.2
O4A—C32A—H32C109.5C17C—C16C—C15C121.70 (14)
H32A—C32A—H32C109.5C17C—C16C—H16C119.1
H32B—C32A—H32C109.5C15C—C16C—H16C119.1
O1B—C29B—H29D109.5C22C—C21C—C18C125.94 (14)
O1B—C29B—H29E109.5C22C—C21C—H21C117.0
H29D—C29B—H29E109.5C18C—C21C—H21C117.0
O1B—C29B—H29F109.5C21C—C22C—C23C127.19 (14)
H29D—C29B—H29F109.5C21C—C22C—H22C116.4
H29E—C29B—H29F109.5C23C—C22C—H22C116.4
C3B—C2B—C1B119.53 (14)C28C—C23C—C24C119.95 (13)
C3B—C2B—H2B120.2C28C—C23C—C22C117.63 (13)
C1B—C2B—H2B120.2C24C—C23C—C22C122.43 (13)
O1B—C3B—C2B115.13 (14)C27C—C28C—C23C119.94 (13)
O1B—C3B—C4B123.32 (13)C27C—C28C—H28C120.0
C2B—C3B—C4B121.56 (14)C23C—C28C—H28C120.0
C5B—C4B—C3B118.33 (13)O4C—C27C—C26C115.61 (12)
C5B—C4B—H4B120.8O4C—C27C—C28C123.97 (13)
C3B—C4B—H4B120.8C26C—C27C—C28C120.41 (13)
O2B—C5B—C4B124.50 (14)C27C—C26C—C25C119.49 (13)
O2B—C5B—C6B114.80 (14)C27C—C26C—H26C120.3
C4B—C5B—C6B120.71 (14)C25C—C26C—H26C120.3
C5B—C6B—C1B120.73 (14)O3C—C25C—C26C115.12 (12)
C5B—C6B—H6B119.6O3C—C25C—C24C123.99 (13)
C1B—C6B—H6B119.6C26C—C25C—C24C120.89 (13)
C2B—C1B—C6B119.13 (13)C25C—C24C—C23C119.31 (13)
C2B—C1B—C7B123.39 (14)C25C—C24C—H24C120.3
C6B—C1B—C7B117.48 (14)C23C—C24C—H24C120.3
C8B—C7B—C1B128.17 (14)O2C—C30C—H30G109.5
C8B—C7B—H7B115.9O2C—C30C—H30H109.5
C1B—C7B—H7B115.9H30G—C30C—H30H109.5
C7B—C8B—C9B125.49 (14)O2C—C30C—H30I109.5
C7B—C8B—H8B117.3H30G—C30C—H30I109.5
C9B—C8B—H8B117.3H30H—C30C—H30I109.5
C14B—C9B—C10B117.48 (13)O1C—C29C—H29G109.5
C14B—C9B—C8B119.89 (13)O1C—C29C—H29H109.5
C10B—C9B—C8B122.63 (13)H29G—C29C—H29H109.5
C11B—C10B—C9B121.01 (13)O1C—C29C—H29I109.5
C11B—C10B—H10B119.5H29G—C29C—H29I109.5
C9B—C10B—H10B119.5H29H—C29C—H29I109.5
C10B—C11B—C12B121.56 (13)O4C—C32C—H32G109.5
C10B—C11B—H11B119.2O4C—C32C—H32H109.5
C12B—C11B—H11B119.2H32G—C32C—H32H109.5
C13B—C12B—C11B117.30 (13)O4C—C32C—H32I109.5
C13B—C12B—C15B121.30 (13)H32G—C32C—H32I109.5
C11B—C12B—C15B121.40 (13)H32H—C32C—H32I109.5
C14B—C13B—C12B121.20 (14)O3C—C31C—H31G109.5
C14B—C13B—H13B119.4O3C—C31C—H31H109.5
C12B—C13B—H13B119.4H31G—C31C—H31H109.5
C13B—C14B—C9B121.44 (14)O3C—C31C—H31I109.5
C13B—C14B—H14B119.3H31G—C31C—H31I109.5
C9B—C14B—H14B119.3H31H—C31C—H31I109.5
C16B—C15B—C20B117.71 (13)C3A—O1A—C29A116.65 (12)
C16B—C15B—C12B121.83 (13)C5A—O2A—C30A117.18 (13)
C20B—C15B—C12B120.47 (13)C25A—O3A—C31A118.07 (12)
C17B—C16B—C15B120.92 (14)C27A—O4A—C32A117.23 (12)
C17B—C16B—H16B119.5C3B—O1B—C29B118.41 (13)
C15B—C16B—H16B119.5C5B—O2B—C30B117.89 (13)
C16B—C17B—C18B121.51 (14)C25B—O3B—C31B116.87 (12)
C16B—C17B—H17B119.2C27B—O4B—C32B116.82 (12)
C18B—C17B—H17B119.2C5C—O2C—C30C117.52 (12)
C17B—C18B—C19B117.37 (13)C3C—O1C—C29C117.02 (12)
C17B—C18B—C21B119.56 (13)C27C—O4C—C32C117.52 (12)
C19B—C18B—C21B123.07 (13)C25C—O3C—C31C117.45 (12)
C6A—C1A—C2A—C3A−0.5 (2)C17B—C18B—C21B—C22B177.60 (15)
C7A—C1A—C2A—C3A179.58 (14)C19B—C18B—C21B—C22B−2.8 (2)
C1A—C2A—C3A—O1A179.44 (14)C18B—C21B—C22B—C23B179.20 (14)
C1A—C2A—C3A—C4A0.0 (2)C21B—C22B—C23B—C28B175.56 (15)
O1A—C3A—C4A—C5A−178.75 (13)C21B—C22B—C23B—C24B−4.5 (2)
C2A—C3A—C4A—C5A0.8 (2)C28B—C23B—C24B—C25B1.6 (2)
C3A—C4A—C5A—O2A179.50 (14)C22B—C23B—C24B—C25B−178.41 (13)
C3A—C4A—C5A—C6A−0.9 (2)C23B—C24B—C25B—O3B179.65 (14)
C2A—C1A—C6A—C5A0.4 (2)C23B—C24B—C25B—C26B−0.7 (2)
C7A—C1A—C6A—C5A−179.74 (13)O3B—C25B—C26B—C27B178.71 (13)
O2A—C5A—C6A—C1A179.98 (14)C24B—C25B—C26B—C27B−1.0 (2)
C4A—C5A—C6A—C1A0.4 (2)C25B—C26B—C27B—O4B−178.84 (13)
C6A—C1A—C7A—C8A−173.06 (16)C25B—C26B—C27B—C28B1.8 (2)
C2A—C1A—C7A—C8A6.8 (2)C24B—C23B—C28B—C27B−0.8 (2)
C1A—C7A—C8A—C9A−179.23 (14)C22B—C23B—C28B—C27B179.17 (13)
C7A—C8A—C9A—C14A179.00 (15)O4B—C27B—C28B—C23B179.68 (13)
C7A—C8A—C9A—C10A−0.4 (2)C26B—C27B—C28B—C23B−0.9 (2)
C14A—C9A—C10A—C11A0.5 (2)C1C—C6C—C5C—O2C−178.51 (13)
C8A—C9A—C10A—C11A179.95 (14)C1C—C6C—C5C—C4C0.5 (2)
C9A—C10A—C11A—C12A0.2 (2)O2C—C5C—C4C—C3C178.37 (13)
C10A—C11A—C12A—C13A−1.0 (2)C6C—C5C—C4C—C3C−0.5 (2)
C10A—C11A—C12A—C15A179.27 (14)C5C—C4C—C3C—O1C−179.65 (13)
C11A—C12A—C13A—C14A1.1 (2)C5C—C4C—C3C—C2C0.3 (2)
C15A—C12A—C13A—C14A−179.21 (13)O1C—C3C—C2C—C1C179.92 (14)
C12A—C13A—C14A—C9A−0.4 (2)C4C—C3C—C2C—C1C0.0 (2)
C10A—C9A—C14A—C13A−0.4 (2)C5C—C6C—C1C—C2C−0.2 (2)
C8A—C9A—C14A—C13A−179.89 (13)C5C—C6C—C1C—C7C179.33 (13)
C13A—C12A—C15A—C20A−31.9 (2)C3C—C2C—C1C—C6C0.0 (2)
C11A—C12A—C15A—C20A147.87 (15)C3C—C2C—C1C—C7C−179.55 (13)
C13A—C12A—C15A—C16A150.00 (15)C6C—C1C—C7C—C8C178.32 (15)
C11A—C12A—C15A—C16A−30.3 (2)C2C—C1C—C7C—C8C−2.2 (2)
C20A—C15A—C16A—C17A−1.5 (2)C1C—C7C—C8C—C9C178.72 (14)
C12A—C15A—C16A—C17A176.78 (15)C7C—C8C—C9C—C14C−170.93 (16)
C15A—C16A—C17A—C18A0.9 (3)C7C—C8C—C9C—C10C7.9 (2)
C16A—C17A—C18A—C19A0.3 (2)C10C—C9C—C14C—C13C−0.4 (3)
C16A—C17A—C18A—C21A178.35 (15)C8C—C9C—C14C—C13C178.54 (16)
C17A—C18A—C19A—C20A−0.7 (2)C9C—C14C—C13C—C12C0.7 (3)
C21A—C18A—C19A—C20A−178.74 (14)C14C—C13C—C12C—C11C−0.7 (3)
C18A—C19A—C20A—C15A0.1 (2)C14C—C13C—C12C—C15C178.57 (16)
C16A—C15A—C20A—C19A1.0 (2)C13C—C12C—C11C—C10C0.4 (2)
C12A—C15A—C20A—C19A−177.24 (13)C15C—C12C—C11C—C10C−178.83 (15)
C17A—C18A—C21A—C22A−166.43 (16)C12C—C11C—C10C—C9C−0.2 (3)
C19A—C18A—C21A—C22A11.5 (2)C14C—C9C—C10C—C11C0.1 (2)
C18A—C21A—C22A—C23A178.86 (14)C8C—C9C—C10C—C11C−178.75 (15)
C21A—C22A—C23A—C24A−3.0 (2)C11C—C12C—C15C—C16C2.9 (2)
C21A—C22A—C23A—C28A176.53 (15)C13C—C12C—C15C—C16C−176.30 (16)
C28A—C23A—C24A—C25A−0.5 (2)C11C—C12C—C15C—C20C−175.23 (15)
C22A—C23A—C24A—C25A179.02 (13)C13C—C12C—C15C—C20C5.5 (2)
C23A—C24A—C25A—O3A179.81 (13)C16C—C15C—C20C—C19C−0.4 (2)
C23A—C24A—C25A—C26A0.2 (2)C12C—C15C—C20C—C19C177.83 (15)
O3A—C25A—C26A—C27A−179.18 (13)C15C—C20C—C19C—C18C0.0 (3)
C24A—C25A—C26A—C27A0.5 (2)C20C—C19C—C18C—C17C−0.3 (3)
C25A—C26A—C27A—O4A−179.96 (13)C20C—C19C—C18C—C21C179.99 (15)
C25A—C26A—C27A—C28A−0.7 (2)C19C—C18C—C17C—C16C1.1 (3)
O4A—C27A—C28A—C23A179.51 (13)C21C—C18C—C17C—C16C−179.18 (16)
C26A—C27A—C28A—C23A0.3 (2)C18C—C17C—C16C—C15C−1.6 (3)
C24A—C23A—C28A—C27A0.3 (2)C20C—C15C—C16C—C17C1.2 (3)
C22A—C23A—C28A—C27A−179.27 (13)C12C—C15C—C16C—C17C−177.03 (16)
C1B—C2B—C3B—O1B−179.80 (13)C17C—C18C—C21C—C22C168.93 (16)
C1B—C2B—C3B—C4B−0.1 (2)C19C—C18C—C21C—C22C−11.3 (2)
O1B—C3B—C4B—C5B179.74 (14)C18C—C21C—C22C—C23C179.92 (14)
C2B—C3B—C4B—C5B0.1 (2)C21C—C22C—C23C—C28C−171.75 (15)
C3B—C4B—C5B—O2B−179.20 (14)C21C—C22C—C23C—C24C8.0 (2)
C3B—C4B—C5B—C6B0.5 (2)C24C—C23C—C28C—C27C−0.2 (2)
O2B—C5B—C6B—C1B178.66 (14)C22C—C23C—C28C—C27C179.64 (13)
C4B—C5B—C6B—C1B−1.1 (2)C23C—C28C—C27C—O4C−179.64 (13)
C3B—C2B—C1B—C6B−0.4 (2)C23C—C28C—C27C—C26C0.1 (2)
C3B—C2B—C1B—C7B−179.55 (13)O4C—C27C—C26C—C25C179.99 (13)
C5B—C6B—C1B—C2B1.0 (2)C28C—C27C—C26C—C25C0.3 (2)
C5B—C6B—C1B—C7B−179.80 (13)C27C—C26C—C25C—O3C179.86 (13)
C2B—C1B—C7B—C8B−2.4 (2)C27C—C26C—C25C—C24C−0.5 (2)
C6B—C1B—C7B—C8B178.46 (15)O3C—C25C—C24C—C23C−179.99 (14)
C1B—C7B—C8B—C9B179.96 (14)C26C—C25C—C24C—C23C0.4 (2)
C7B—C8B—C9B—C14B168.33 (16)C28C—C23C—C24C—C25C−0.1 (2)
C7B—C8B—C9B—C10B−11.0 (2)C22C—C23C—C24C—C25C−179.86 (13)
C14B—C9B—C10B—C11B0.8 (2)C2A—C3A—O1A—C29A7.8 (2)
C8B—C9B—C10B—C11B−179.79 (14)C4A—C3A—O1A—C29A−172.69 (14)
C9B—C10B—C11B—C12B−0.2 (2)C4A—C5A—O2A—C30A−10.2 (2)
C10B—C11B—C12B—C13B−0.8 (2)C6A—C5A—O2A—C30A170.20 (15)
C10B—C11B—C12B—C15B178.33 (13)C26A—C25A—O3A—C31A−3.1 (2)
C11B—C12B—C13B—C14B1.3 (2)C24A—C25A—O3A—C31A177.21 (14)
C15B—C12B—C13B—C14B−177.88 (14)C28A—C27A—O4A—C32A5.3 (2)
C12B—C13B—C14B—C9B−0.7 (2)C26A—C27A—O4A—C32A−175.46 (14)
C10B—C9B—C14B—C13B−0.4 (2)C2B—C3B—O1B—C29B−173.65 (13)
C8B—C9B—C14B—C13B−179.78 (15)C4B—C3B—O1B—C29B6.7 (2)
C13B—C12B—C15B—C16B−149.58 (15)C4B—C5B—O2B—C30B−8.0 (2)
C11B—C12B—C15B—C16B31.3 (2)C6B—C5B—O2B—C30B172.27 (15)
C13B—C12B—C15B—C20B29.9 (2)C24B—C25B—O3B—C31B−7.4 (2)
C11B—C12B—C15B—C20B−149.26 (14)C26B—C25B—O3B—C31B172.87 (13)
C20B—C15B—C16B—C17B−0.9 (2)C26B—C27B—O4B—C32B10.7 (2)
C12B—C15B—C16B—C17B178.55 (13)C28B—C27B—O4B—C32B−169.93 (14)
C15B—C16B—C17B—C18B0.4 (2)C4C—C5C—O2C—C30C5.9 (2)
C16B—C17B—C18B—C19B0.4 (2)C6C—C5C—O2C—C30C−175.15 (13)
C16B—C17B—C18B—C21B−179.96 (14)C2C—C3C—O1C—C29C−12.6 (2)
C17B—C18B—C19B—C20B−0.7 (2)C4C—C3C—O1C—C29C167.30 (13)
C21B—C18B—C19B—C20B179.72 (14)C26C—C27C—O4C—C32C172.34 (14)
C18B—C19B—C20B—C15B0.1 (2)C28C—C27C—O4C—C32C−7.9 (2)
C16B—C15B—C20B—C19B0.7 (2)C26C—C25C—O3C—C31C−170.26 (14)
C12B—C15B—C20B—C19B−178.81 (14)C24C—C25C—O3C—C31C10.1 (2)
Table 1
Relevant C—H···π contacts in the crystal packing of the title compound (Å, °). top
EntryDHAH···AD—H···A
1C10AH10ACg(B4)i2.62148
2C17AH17ACg(B3)i2.86150
3C19AH19ACg(C4)ii2.80143
4C29AH29aCg(A3)iii2.79147
5C10BH10BCg(C1)iii2.84148
6C14BH14BCg(A2)iv2.97147
7C19BH19BCg(A1)iv2.67149
8C31BH31FCg(B2)iii2.80148
9C10CH10CCg(B1)iv2.70148
10C19CH19CCg(A4)v2.85152
11C29CH29GCg(C3)i2.76143
12C31CH31GCg(C2)iii2.78140
Symmetry codes: (i) x+1, y, z; (ii) -x+1, y+1/2, -z+1/2; (iii) x-1, y, z; (iv) x, y, z; (v) -x+2, y-1/2, -z+1/2.
Table 2
Relevant π–π contacts in the crystal packing of the title compound (Å, °). top
The angle related to a pair of centroids is defined as the angle between the Cg(I)···Cg(J) vector and the normal to plane I. Centroids as in Table 1.
EntryCg(I)Cg(J)Cg···CgAngle
1Cg(A1)Cg(A1)vi3.738 (1)26.65
2Cg(A4)Cg(A4)vii3.6454 (9)25.18
3Cg(B1)Cg(C4)viii3.713 (1)25.39
4Cg(B4)Cg(C1)ix3.697 (1)26.83
5Cg(C1)Cg(B4)x3.697 (1)25.86
6Cg(C4)Cg(B1)xi3.713 (1)25.72
Symmetry codes: (vi) -x, -y+1, -z; (vii) -x+3, -y+1, -z+1; (viii) x+1, -y+1/2, z+1/2; (ix) x-2, -y+1/2, z-1/2; (x) x+2, -y+1/2, z+1/2; (xi) x-1, -y+1/2, z-1/2.
Table 3
Relevant short contacts involving the methoxy groups in the crystal packing of the title compound (Å, °). top
EntryDXAX···AD–X···A
1O2AC30AO1Cix3.139 (2)175.28 (12)
2O3AC31AO4Cx3.090 (2)160.33 (12)
3C32AH32AO2Cvii2.71120
4C32AH32cO3Avii2.55142
5C15BC16BO1Biii3.204 (2)108.54 (9)
6O1BC29BO4Avii3.171 (2)143.57 (12)
7O2BC30BO3Bx3.171 (2)171.88 (12)
8O4BC32BO1Axii3.102 (2)174.13 (12)
9C31BH31DO2Cix2.68139
10O2CC30CO3Cx3.152 (2)161.25 (11)
11C29CH29HO4Bx2.67141
12C31CH31IO2Bxi2.70143
13C32CH32GO1Bxi2.40144
14C32CH32IO4Cxiii2.69124
Symmetry codes: (xii) -x-1, -y+1, -z; (xiii) -x, -y, -z.
Acknowledgements top

AC wishes to thank the Institute for the Promotion of Innovation by Science and Technology in Flanders (IWT) for a predoctoral grant. The X-ray diffractometer was funded by NSF Grant 0087210, Ohio Board of Regents Grant CAP-491, and by Youngstown State University.

references
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