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The compound 1,c-3-diphenyl­tetran-r-1-ol (systematic name: 1,c-3-diphenyl-1,2,3,4-tetra­hydro-r-1-naphthol), C22H20O, which possesses the tetra­hydro­naphthalene core that is found in a large number of natural products, crystallizes with Z' = 4 and with the four mol­ecules forming a hydrogen-bonded cyclic aggregate. The aliphatic six-membered rings are present with two different conformations in the mol­ecules of the asymmetric unit. A comparison with similar fragments reveals their conformational flexibility. In addition, the structure demonstrates the relative stereochemistries of the chiral centers, which are important since the title compound is used in the stereoselective synthesis of compounds with therapeutic activity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108043655/fa3170sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108043655/fa3170Isup2.hkl
Contains datablock I

CCDC reference: 724198

Comment top

The molecule of the title compound, (I), contains a tetrahydronaphthalene core that is often found in a large number of natural products (Bates et al., 1997), as well as bioactive and pharmaceutically interesting substances (Wang et al. 2006). We have been studying the synthesis and configurational properties of indanic and tetranilic derivatives (Aguirre et al., 1998, 1999; Alesso et al., 2002, 2003; Vega et al., 2006). In particular, we have been seeking alternative routes to stereoselective synthesis of tetranilic derivatives via hydrogenolysis of corresponding tetranols that can be used as intermediates in the synthesis of analogues of bioactive molecules. To progress in stereoselective syntheses, the elucidation of relative configuration at the chiral centers is necessary. The structure of (I) is also of interest for its supramolecular assembly (vide infra), which may be of interest in crystal engineering, as aphorized in Lehn's analogy that `supramolecules are to molecules and the intermolecular bond what molecules are to atoms and the covalent bond' (Desiraju, 1995).

The title compound has two chiral centers, C1 and C3 (Fig. 1); its synthesis has been reported (Hanaya et al., 1981). There have been attempts to assign the configuration by IR spectroscopy (Hanaya et al., 1981) and NMR (Mufato et al., 2007). Nevertheless, these two results have not been confirmed. The aim of the present work is to provide experimental information about the configuration and also about the conformation and supramolecular aggregation of the title compound. There are four molecules (A, B, C and D) in the asymmetric unit, constituting a racemic tetrameric aggregate (Fig. 2). Molecules A and D have an SR configuration, whereas B and C are RS. It is possible to use a different asymmetric unit, with all molecules having an RS or SR configuration, but that asymmetric unit would not have an integral tetramolecular aggregate.

The selected bond distances and angles and torsion angles listed in Table 1 reveal the main differences among the molecules, which are principally conformational. The two benzene rings (C7–C12 and C17–C22) adopt different relative orientations in each molecule, as expected because the rotations around C3—C12 and C1—C17 are free. To perform a better comparison, the reported torsion angles C2—C3—C12—C7 and C6—C1—C17—C22 for molecules B and C in Table 1 are from those molecules equivalent to B and C generated by the center of symmetry, so that we are comparing four molecules with the same SR configuration. In particular the C2—C3—C12—C7 and C6—C1—C17—C22 torsion angles range from -30 to -55° and from -160 to 177° (equivalent to -183°), respectively, which establishes the differences in the relative orientations of the rings in the different molecules.

An extra conformational difference is observed when the puckering of the central six-membered ring C1–C6 is analyzed. This ring can be better described as a half-chair in molecules A and D, but it is twisted in molecules B and C. The puckering parameters (Cremer & Pople, 1975) are Q = 0.506 (4) and 0.494 (4) Å, θ = 132.2 (5) and 133.3 (5)°, and ϕ = 225.3 (7) and 226.4 (6)° for molecules A and D, respectively, and Q = 0.473 (4) and 0.521 (4) Å, θ = 134.6 (6) and 130.9 (4)°, and ϕ = 211.0 (8) and 210.6 (6)° for those molecules equivalent to B and C generated by the center of symmetry.

The conformational differences between the four molecules observed in the non-aromatic six-membered ring merit further analysis. Considering the expected conformational equilibrium shown in the scheme below, case i and case ii can be characterized by the torsion angles C5—C6—C1—O1 or C5—C6—C1—C2. In the cases described in the scheme, the typical values are around 90 and -30° (case i) and around 150 and 30° (case ii) for the C5—C6—C1—O1 and C5—C6—C1—C2 torsion angles, respectively. This is the case if C1 has an S configuration (as shown in the scheme). When C1 has an R configuration, negative values should be obtained for C5—C6—C1—O1. A search of the Cambridge Structural Database (CSD, Version 5.29; Allen, 2002) for fragments such the one described in the scheme below (S and R configuration at atoms C1 and C3), with a benzene ring fused at C6—C5 and a hydroxy group at the O1 position, gave 141 hits with 204 fragments. As expected, the mean value obtained for the C4—C5—C6—C1 torsion angle is low (sample mean value -0.9°, s.u. 5°) because of the aromatic character of the C5—C6 bond. Fig. 3 shows the C5—C6—C1—O1 and C5—C6—C1—C2 torsion angles as a scatter diagram where, as was mentioned, the negative values for the C5—C6—C1—O1 torsion angle mean that C1 has the R configuration. Beyond the obvious correlation between the C5—C6—C1—O1 and C5—C6—C1—C2 torsion angles, Fig. 3 also shows that the C5—C6—C1—C2 torsion angle spans a wide range of values (from -60 to 60°), thus reflecting a quasi-continuous conformational flexibility. In the present work, the flexibility of the central ring becomes evident when inspecting the torsion angles as shown in Table 1. As before, for the purpose of comparison the SR enantiomers of B and C were used. The C5—C6—C1—O1 and C5—C6—C1—C2 torsion angles range from 130 to 146° and 18 to 26°, respectively. The subtle flexibility of this ring becomes evident in the four chemically equivalent molecules.

The four molecules in the asymmetric unit are linked by as many hydrogen bonds (Table 2) to constitute a tetramer (Fig. 2). Each molecule is hydrogen bonded to two neighbours, once as an acceptor and once as a donor. The four hydrogen bonds determine a homodromic ring with a graph set R44(8) (Bürgi & Dunitz, 1994). Searching the CSD for similar rings developed by a molecule with a hydroxy group attached to a six-membered C-atom ring, we found 140 fragments forming R44(8) patterns. We consider two relevant parameters for these rings – the O···O distances and the ring planarity. The O···O distances in the tetramer in (I) have a mean value of 2.712 (6) Å, which seems to be on the low side of the mean found for the 140 fragments (2.79 Å, s.u. 0.09 Å); therefore good cohesion seems to be established in the tetramer. On the other hand, considering the mean plane through the four O atoms, we find that 57 of the 140 fragments have rigorously planar rings, probably owing to the existence of a crystallographic symmetry element to generate the ring. However, for a few fragments, the O atoms in the ring are far from planarity. In particular, there are 14 fragments with distances from the O atoms to the least-squares plane greater than 0.5 Å (the largest value is 0.85 Å). The ring in (I) has a mean distance from the O atom to the least-squares plane of 0.30 (1) Å.

Related literature top

For related literature, see: Aguirre et al. (1998, 1999); Alesso et al. (2002, 2003); Allen (2002); Bürgi & Dunitz (1994); Bates et al. (1997); Cremer & Pople (1975); Desiraju (1995); Hanaya et al. (1981); Mufato et al. (2007); Vega et al. (2006); Wang et al. (2006).

Experimental top

The diasteroisomers 1,3-diphenyltetran-1-ol were synthesized from 3-phenyltetran-1-one and the corresponding Grignard reagent as reported by Hanaya et al. (1981). Crystals of (I) suitable for diffraction were obtained after leaving a methanol solution for several weeks at room temperature.

Refinement top

Crystals of (I) yield poor diffraction data at high 2θ values. Data were corrected for decay. All H atoms were treated as riding atoms, located at idealized positions, with C—H distances of 0.97, (CH2) 0.93 or 0.98 Å (CH), and O—H distances of 0.82 Å. All H atoms were assigned isotropic displacement parameters, with Uiso(H) of 1.2 times Ueq of the parent non-H atoms for CH2 and CH H atoms, and 1.5 times for OH.

Computing details top

Data collection: AFC6S Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: AFC6S Diffractometer Control Software (Molecular Structure Corporation, 1993); data reduction: AFC6S Diffractometer Control Software (Molecular Structure Corporation, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-PC (Sheldrick, 2008) and PARST (Nardelli, 1983).

Figures top
[Figure 1] Fig. 1. Molecule A of (I) (SR configuration), with displacement ellipsoids shown at the 30% probability level.
[Figure 2] Fig. 2. A view of the tetramer, showing the numbering scheme. The benzene rings attached to atoms C1 and C3 have been omitted. The benzene rings fused to the central rings (at C5 and C6) are depicted with open dashed lines. The hydrogen bonds that determine the tetramer are drawn as solid dashed lines.
[Figure 3] Fig. 3. A scatter diagram of the C5—C6—C1—O1 versus C5—C6—C1—C2 torsion angles. Positive and negative values are obtained for the C5—C6—C1—O1 torsion angles when C1 has S and R configuration, respectively.
1,c-3-diphenyl-1,2,3,4-tetrahydro-r-1-naphthol top
Crystal data top
C22H20OF(000) = 2560
Mr = 300.38Dx = 1.171 Mg m3
Monoclinic, P21/cMelting point: 382(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 16.546 (3) ÅCell parameters from 25 reflections
b = 13.124 (3) Åθ = 14–25°
c = 31.942 (6) ŵ = 0.07 mm1
β = 100.62 (3)°T = 293 K
V = 6817 (2) Å3Plate, colourless
Z = 160.4 × 0.2 × 0.05 mm
Data collection top
Rigaku AFC6 DiffractometerRint = 0.112
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.6°
Graphite monochromatorh = 120
ω scansk = 116
16186 measured reflectionsl = 3938
13368 independent reflections3 standard reflections every 147 reflections
3121 reflections with I > 2σ(I) intensity decay: 13%
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202H-atom parameters constrained
S = 0.85 w = 1/[σ2(Fo2) + (0.0682P)2]
where P = (Fo2 + 2Fc2)/3
13368 reflections(Δ/σ)max < 0.001
835 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C22H20OV = 6817 (2) Å3
Mr = 300.38Z = 16
Monoclinic, P21/cMo Kα radiation
a = 16.546 (3) ŵ = 0.07 mm1
b = 13.124 (3) ÅT = 293 K
c = 31.942 (6) Å0.4 × 0.2 × 0.05 mm
β = 100.62 (3)°
Data collection top
Rigaku AFC6 DiffractometerRint = 0.112
16186 measured reflections3 standard reflections every 147 reflections
13368 independent reflections intensity decay: 13%
3121 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.202H-atom parameters constrained
S = 0.85Δρmax = 0.21 e Å3
13368 reflectionsΔρmin = 0.17 e Å3
835 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.2205 (2)0.3103 (3)0.30439 (9)0.0803 (11)
H1A0.22340.25910.31930.121*
C3A0.1840 (3)0.1514 (5)0.20362 (15)0.0785 (17)
H3A10.12430.16120.19630.094*
C2A0.2110 (3)0.1805 (4)0.25074 (13)0.0699 (15)
H2A10.18960.13060.26830.084*
H2A20.27050.17880.25800.084*
C1A0.1814 (3)0.2844 (5)0.26040 (14)0.0707 (16)
C6A0.2098 (3)0.3656 (5)0.23238 (17)0.0696 (15)
C5A0.2272 (3)0.3368 (6)0.19206 (19)0.0822 (17)
C4A0.2238 (3)0.2279 (6)0.17740 (16)0.0940 (19)
H4A10.27950.20540.17710.113*
H4A20.19390.22570.14830.113*
C7A0.2738 (4)0.0032 (6)0.2121 (2)0.104 (2)
H7A0.31210.03360.23120.125*
C8A0.2905 (4)0.1030 (7)0.2034 (2)0.111 (2)
H8A0.33850.13370.21750.133*
C9A0.2372 (6)0.1568 (6)0.1743 (3)0.123 (3)
H9A0.24920.22350.16780.147*
C10A0.1655 (6)0.1118 (8)0.1546 (2)0.128 (3)
H10A0.12820.14830.13480.153*
C11A0.1485 (4)0.0123 (7)0.16407 (18)0.106 (2)
H11A0.09980.01760.15040.127*
C12A0.2017 (4)0.0431 (5)0.19315 (18)0.0760 (16)
C13A0.2520 (4)0.4149 (7)0.1675 (2)0.104 (2)
H13A0.26330.39800.14090.124*
C14A0.2606 (4)0.5131 (7)0.1798 (3)0.118 (3)
H14A0.27730.56180.16200.142*
C15A0.2440 (4)0.5407 (5)0.2197 (3)0.109 (2)
H15A0.25040.60770.22910.131*
C16A0.2180 (4)0.4662 (6)0.2447 (2)0.0938 (19)
H16A0.20550.48470.27090.113*
C17A0.0872 (3)0.2885 (5)0.25882 (16)0.0719 (16)
C18A0.0377 (4)0.3595 (6)0.23636 (19)0.113 (2)
H18A0.06100.40770.22080.136*
C19A0.0473 (5)0.3629 (6)0.2357 (2)0.128 (3)
H19A0.07950.41290.22010.153*
C20A0.0814 (4)0.2937 (7)0.2577 (2)0.119 (3)
H20A0.13770.29550.25750.143*
C21A0.0348 (5)0.2220 (7)0.2798 (2)0.142 (3)
H21A0.05880.17380.29510.170*
C22A0.0495 (4)0.2188 (6)0.2804 (2)0.120 (3)
H22A0.08090.16790.29580.144*
O1B0.1896 (2)0.1608 (3)0.36679 (9)0.0759 (10)
H1B0.19450.21280.38130.114*
C3B0.2805 (3)0.0317 (4)0.47041 (16)0.0801 (16)
H3B10.30170.03060.45940.096*
C2B0.2678 (3)0.1103 (4)0.43527 (14)0.0769 (16)
H2B10.32090.12860.42870.092*
H2B20.24440.17120.44550.092*
C1B0.2110 (3)0.0739 (4)0.39387 (16)0.0670 (14)
C6B0.1338 (3)0.0253 (4)0.40493 (17)0.0673 (15)
C5B0.1291 (4)0.0106 (4)0.44544 (18)0.0830 (16)
C4B0.1976 (4)0.0074 (5)0.48220 (17)0.110 (2)
H4B10.20370.05280.50010.132*
H4B20.18230.06340.49900.132*
C7B0.3333 (4)0.1582 (6)0.5292 (2)0.122 (2)
H7B0.28750.19870.51960.146*
C8B0.3923 (5)0.1896 (6)0.5637 (2)0.134 (3)
H8B0.38580.25200.57650.161*
C9B0.4591 (5)0.1317 (7)0.5791 (2)0.122 (2)
H9B0.49840.15410.60190.146*
C10B0.4667 (5)0.0424 (7)0.5608 (3)0.136 (3)
H10B0.51130.00100.57170.163*
C11B0.4095 (4)0.0082 (5)0.5255 (2)0.111 (2)
H11B0.41690.05440.51310.134*
C12B0.3428 (4)0.0674 (5)0.50928 (18)0.0871 (18)
C13B0.0566 (4)0.0580 (5)0.4511 (2)0.101 (2)
H13B0.05250.08110.47820.121*
C14B0.0094 (4)0.0721 (5)0.4184 (3)0.103 (2)
H14B0.05630.10550.42330.123*
C15B0.0052 (4)0.0369 (5)0.3788 (2)0.101 (2)
H15B0.04950.04550.35650.121*
C16B0.0651 (4)0.0115 (4)0.37195 (18)0.0848 (17)
H16B0.06740.03580.34480.102*
C17B0.2563 (4)0.0017 (5)0.36872 (15)0.0692 (15)
C18B0.2373 (4)0.0985 (6)0.36161 (18)0.0913 (19)
H18B0.19400.12580.37280.110*
C19B0.2800 (5)0.1618 (5)0.3382 (2)0.112 (2)
H19B0.26460.22960.33330.134*
C20B0.3464 (5)0.1217 (8)0.3221 (2)0.118 (3)
H20B0.37640.16220.30660.142*
C21B0.3662 (4)0.0222 (8)0.3297 (2)0.109 (2)
H21B0.41040.00480.31910.131*
C22B0.3233 (4)0.0405 (5)0.35250 (18)0.0944 (19)
H22B0.33870.10840.35710.113*
O1C0.19744 (19)0.3428 (2)0.40912 (10)0.0676 (9)
H1C0.22330.38600.39850.101*
C3C0.0047 (3)0.3405 (4)0.45429 (13)0.0612 (14)
H3C10.00920.41290.45090.073*
C2C0.0653 (3)0.3162 (4)0.42511 (13)0.0601 (14)
H2C10.03630.31560.39580.072*
H2C20.08790.24870.43180.072*
C1C0.1356 (3)0.3930 (4)0.42941 (15)0.0587 (14)
C6C0.1742 (3)0.4049 (4)0.47697 (15)0.0627 (14)
C5C0.1335 (3)0.3748 (4)0.50934 (16)0.0700 (15)
C4C0.0498 (3)0.3241 (4)0.50009 (14)0.0820 (17)
H4C10.01640.35090.51950.098*
H4C20.05660.25160.50540.098*
C7C0.0796 (3)0.1855 (5)0.42851 (16)0.0735 (15)
H7C0.03220.15530.42250.088*
C8C0.1532 (4)0.1310 (5)0.42014 (16)0.0845 (17)
H8C0.15500.06620.40820.101*
C9C0.2232 (3)0.1748 (6)0.42992 (17)0.0827 (18)
H9C0.27280.13970.42450.099*
C10C0.2193 (3)0.2685 (6)0.44729 (16)0.0826 (18)
H10C0.26650.29750.45410.099*
C11C0.1455 (3)0.3231 (4)0.45524 (14)0.0723 (15)
H11C0.14380.38770.46730.087*
C12C0.0746 (3)0.2807 (5)0.44511 (14)0.0569 (13)
C13C0.1718 (4)0.3879 (5)0.55212 (16)0.0904 (19)
H13C0.14450.36730.57360.108*
C14C0.2492 (4)0.4309 (5)0.56289 (18)0.099 (2)
H14C0.27380.43970.59130.118*
C15C0.2887 (3)0.4602 (4)0.53061 (19)0.0881 (18)
H15C0.34100.48830.53730.106*
C16C0.2515 (3)0.4484 (4)0.48765 (17)0.0747 (16)
H16C0.27880.47000.46630.090*
C17C0.1101 (3)0.4908 (4)0.40705 (16)0.0545 (13)
C18C0.1039 (3)0.5809 (5)0.42687 (18)0.0725 (15)
H18C0.11610.58210.45650.087*
C19C0.0809 (3)0.6702 (5)0.4061 (2)0.0918 (18)
H19C0.07650.72970.42130.110*
C20C0.0642 (3)0.6706 (6)0.3614 (3)0.096 (2)
H20C0.04860.73020.34630.115*
C21C0.0714 (4)0.5824 (6)0.3411 (2)0.094 (2)
H21C0.06240.58250.31150.112*
C22C0.0915 (3)0.4923 (5)0.36200 (16)0.0712 (15)
H22C0.09290.43230.34670.085*
O1D0.29327 (17)0.4547 (3)0.36375 (9)0.0673 (10)
H1D0.28810.41090.34510.101*
C3D0.4795 (3)0.5857 (4)0.33546 (15)0.0654 (14)
H3D10.49210.62850.36100.079*
C2D0.3907 (3)0.5490 (4)0.33128 (13)0.0671 (15)
H2D10.37760.50380.30690.081*
H2D20.35390.60700.32630.081*
C1D0.3768 (3)0.4926 (4)0.37150 (14)0.0541 (13)
C6D0.4366 (3)0.4072 (4)0.38254 (15)0.0578 (13)
C5D0.5139 (3)0.4098 (5)0.37007 (15)0.0655 (14)
C4D0.5365 (3)0.4932 (5)0.34233 (16)0.0889 (19)
H4D10.53920.46420.31470.107*
H4D20.59130.51670.35460.107*
C7D0.4683 (4)0.6146 (5)0.25692 (19)0.102 (2)
H7D0.43680.55560.25220.123*
C8D0.4869 (5)0.6678 (7)0.2226 (2)0.120 (2)
H8D0.46930.64290.19520.143*
C9D0.5308 (4)0.7569 (7)0.2284 (2)0.117 (3)
H9D0.54130.79400.20520.141*
C10D0.5587 (3)0.7899 (5)0.2689 (3)0.106 (2)
H10D0.59040.84870.27360.127*
C11D0.5399 (3)0.7356 (5)0.30328 (19)0.0906 (18)
H11D0.55810.76060.33060.109*
C12D0.4959 (3)0.6476 (5)0.29838 (17)0.0716 (15)
C13D0.5680 (3)0.3290 (6)0.38185 (17)0.0843 (18)
H13D0.61860.33020.37320.101*
C14D0.5501 (3)0.2487 (5)0.40536 (18)0.0853 (18)
H14D0.58810.19640.41260.102*
C15D0.4739 (4)0.2451 (5)0.41872 (16)0.0815 (17)
H15D0.46010.19090.43490.098*
C16D0.4202 (3)0.3247 (4)0.40704 (15)0.0676 (14)
H16D0.36990.32320.41610.081*
C17D0.3805 (3)0.5663 (4)0.40946 (15)0.0627 (14)
C18D0.4486 (3)0.5737 (5)0.44295 (17)0.0835 (18)
H18D0.49380.53130.44350.100*
C19D0.4480 (4)0.6441 (5)0.47494 (18)0.100 (2)
H19D0.49360.64890.49680.119*
C20D0.3830 (5)0.7064 (5)0.47551 (19)0.099 (2)
H20D0.38390.75310.49750.118*
C21D0.3151 (4)0.7000 (4)0.44307 (19)0.0858 (17)
H21D0.27000.74230.44320.103*
C22D0.3146 (3)0.6308 (4)0.41061 (15)0.0686 (15)
H22D0.26880.62720.38890.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.086 (2)0.106 (3)0.0437 (19)0.005 (2)0.0019 (19)0.0029 (19)
C3A0.059 (3)0.127 (6)0.049 (3)0.018 (4)0.009 (3)0.017 (4)
C2A0.057 (3)0.101 (5)0.049 (3)0.010 (3)0.002 (2)0.010 (3)
C1A0.065 (4)0.103 (5)0.036 (3)0.003 (4)0.012 (3)0.005 (3)
C6A0.062 (3)0.081 (5)0.060 (4)0.005 (3)0.004 (3)0.010 (4)
C5A0.061 (4)0.117 (6)0.065 (4)0.003 (4)0.002 (3)0.013 (5)
C4A0.091 (4)0.135 (6)0.053 (4)0.001 (4)0.007 (3)0.010 (4)
C7A0.074 (5)0.119 (7)0.118 (5)0.005 (5)0.019 (4)0.053 (5)
C8A0.097 (5)0.140 (8)0.105 (6)0.002 (5)0.041 (5)0.030 (5)
C9A0.158 (8)0.129 (7)0.101 (6)0.026 (7)0.077 (6)0.033 (6)
C10A0.154 (8)0.157 (9)0.073 (5)0.062 (7)0.021 (5)0.047 (6)
C11A0.107 (5)0.145 (7)0.064 (4)0.048 (5)0.014 (4)0.040 (5)
C12A0.066 (4)0.103 (5)0.065 (4)0.011 (4)0.028 (3)0.026 (4)
C13A0.102 (5)0.133 (7)0.075 (4)0.011 (5)0.013 (4)0.030 (5)
C14A0.119 (6)0.144 (8)0.087 (6)0.026 (6)0.007 (4)0.032 (6)
C15A0.110 (5)0.094 (6)0.102 (6)0.014 (4)0.034 (4)0.025 (5)
C16A0.100 (5)0.089 (5)0.085 (4)0.008 (4)0.005 (4)0.011 (5)
C17A0.055 (4)0.110 (5)0.047 (3)0.009 (4)0.000 (3)0.001 (3)
C18A0.071 (5)0.170 (7)0.102 (5)0.016 (5)0.028 (4)0.030 (5)
C19A0.097 (6)0.174 (8)0.111 (6)0.029 (5)0.014 (5)0.038 (5)
C20A0.081 (5)0.202 (9)0.075 (5)0.012 (6)0.018 (4)0.003 (5)
C21A0.078 (5)0.222 (10)0.128 (6)0.012 (6)0.024 (4)0.061 (6)
C22A0.060 (5)0.172 (8)0.127 (6)0.000 (5)0.012 (4)0.048 (5)
O1B0.093 (2)0.080 (3)0.056 (2)0.005 (2)0.0171 (19)0.004 (2)
C3B0.091 (4)0.090 (5)0.057 (3)0.005 (4)0.006 (3)0.003 (3)
C2B0.084 (4)0.092 (4)0.054 (3)0.001 (3)0.013 (3)0.006 (3)
C1B0.078 (4)0.062 (4)0.059 (3)0.001 (3)0.005 (3)0.008 (3)
C6B0.061 (4)0.079 (4)0.059 (3)0.004 (3)0.005 (3)0.003 (3)
C5B0.080 (4)0.102 (5)0.067 (4)0.001 (4)0.013 (3)0.009 (4)
C4B0.089 (4)0.163 (7)0.073 (4)0.016 (4)0.002 (4)0.047 (4)
C7B0.111 (5)0.151 (7)0.089 (5)0.046 (5)0.023 (4)0.035 (5)
C8B0.156 (7)0.129 (6)0.097 (5)0.037 (6)0.030 (5)0.029 (5)
C9B0.117 (6)0.137 (8)0.093 (5)0.005 (6)0.029 (4)0.019 (5)
C10B0.125 (6)0.125 (7)0.134 (7)0.026 (6)0.040 (5)0.027 (6)
C11B0.113 (5)0.093 (5)0.117 (5)0.020 (5)0.007 (5)0.016 (4)
C12B0.096 (5)0.095 (5)0.072 (4)0.026 (4)0.018 (4)0.003 (4)
C13B0.092 (5)0.118 (6)0.103 (5)0.006 (5)0.044 (5)0.017 (4)
C14B0.072 (5)0.108 (6)0.129 (6)0.008 (4)0.021 (5)0.003 (5)
C15B0.085 (5)0.123 (6)0.095 (5)0.005 (4)0.016 (4)0.010 (5)
C16B0.089 (4)0.094 (5)0.076 (4)0.002 (4)0.024 (4)0.009 (3)
C17B0.076 (4)0.079 (5)0.053 (3)0.019 (4)0.014 (3)0.002 (3)
C18B0.111 (5)0.082 (5)0.085 (4)0.016 (4)0.026 (4)0.010 (4)
C19B0.140 (6)0.098 (6)0.097 (5)0.035 (5)0.022 (5)0.012 (5)
C20B0.116 (6)0.153 (9)0.092 (5)0.055 (6)0.034 (5)0.006 (6)
C21B0.091 (5)0.145 (7)0.091 (5)0.026 (6)0.015 (4)0.008 (5)
C22B0.099 (5)0.099 (5)0.087 (4)0.019 (4)0.022 (4)0.010 (4)
O1C0.063 (2)0.077 (2)0.071 (2)0.008 (2)0.0334 (17)0.002 (2)
C3C0.047 (3)0.081 (4)0.056 (3)0.009 (3)0.014 (3)0.004 (3)
C2C0.069 (3)0.071 (4)0.043 (3)0.002 (3)0.019 (3)0.002 (3)
C1C0.053 (3)0.068 (4)0.060 (3)0.006 (3)0.025 (3)0.003 (3)
C6C0.044 (3)0.085 (4)0.060 (3)0.003 (3)0.013 (3)0.005 (3)
C5C0.059 (3)0.104 (5)0.050 (3)0.003 (3)0.018 (3)0.001 (3)
C4C0.067 (4)0.125 (5)0.056 (3)0.006 (4)0.017 (3)0.000 (3)
C7C0.056 (4)0.081 (5)0.085 (4)0.004 (4)0.018 (3)0.003 (4)
C8C0.067 (4)0.096 (5)0.091 (4)0.012 (4)0.014 (3)0.003 (3)
C9C0.048 (4)0.116 (6)0.085 (4)0.008 (4)0.014 (3)0.008 (4)
C10C0.049 (4)0.132 (6)0.068 (4)0.001 (4)0.012 (3)0.006 (4)
C11C0.060 (4)0.104 (5)0.055 (3)0.004 (4)0.015 (3)0.015 (3)
C12C0.043 (3)0.080 (4)0.046 (3)0.005 (3)0.003 (2)0.002 (3)
C13C0.083 (4)0.137 (6)0.051 (4)0.008 (4)0.011 (3)0.001 (3)
C14C0.084 (4)0.143 (6)0.065 (4)0.014 (4)0.003 (4)0.002 (4)
C15C0.062 (4)0.114 (5)0.087 (4)0.001 (4)0.011 (4)0.001 (4)
C16C0.068 (4)0.095 (5)0.061 (4)0.008 (4)0.013 (3)0.005 (3)
C17C0.055 (3)0.048 (4)0.064 (4)0.007 (3)0.020 (3)0.001 (3)
C18C0.079 (4)0.052 (4)0.092 (4)0.012 (3)0.030 (3)0.021 (4)
C19C0.097 (5)0.078 (5)0.105 (5)0.018 (4)0.031 (4)0.006 (4)
C20C0.072 (4)0.087 (6)0.127 (7)0.024 (4)0.017 (4)0.040 (5)
C21C0.097 (5)0.099 (6)0.089 (5)0.020 (4)0.026 (4)0.035 (5)
C22C0.067 (4)0.090 (5)0.058 (4)0.002 (3)0.017 (3)0.004 (3)
O1D0.047 (2)0.100 (3)0.056 (2)0.0036 (19)0.0119 (16)0.0076 (19)
C3D0.053 (3)0.086 (4)0.055 (3)0.006 (3)0.005 (3)0.001 (3)
C2D0.051 (3)0.109 (5)0.043 (3)0.003 (3)0.013 (2)0.003 (3)
C1D0.050 (3)0.061 (3)0.054 (3)0.001 (3)0.017 (2)0.008 (3)
C6D0.048 (3)0.074 (4)0.050 (3)0.001 (3)0.005 (2)0.004 (3)
C5D0.056 (4)0.086 (4)0.056 (3)0.014 (3)0.013 (3)0.007 (3)
C4D0.060 (4)0.143 (6)0.063 (3)0.001 (4)0.009 (3)0.016 (4)
C7D0.126 (5)0.124 (6)0.064 (4)0.024 (4)0.037 (4)0.010 (4)
C8D0.127 (6)0.158 (8)0.077 (5)0.007 (6)0.028 (4)0.008 (5)
C9D0.076 (5)0.185 (9)0.088 (6)0.007 (5)0.009 (4)0.058 (6)
C10D0.071 (4)0.110 (6)0.131 (6)0.021 (4)0.002 (4)0.051 (5)
C11D0.083 (4)0.095 (5)0.095 (5)0.014 (4)0.021 (4)0.024 (4)
C12D0.070 (4)0.089 (5)0.063 (4)0.002 (3)0.031 (3)0.010 (4)
C13D0.072 (4)0.121 (6)0.065 (4)0.010 (4)0.027 (3)0.008 (4)
C14D0.051 (4)0.122 (6)0.076 (4)0.023 (4)0.007 (3)0.004 (4)
C15D0.075 (4)0.086 (5)0.082 (4)0.007 (4)0.008 (3)0.015 (3)
C16D0.060 (3)0.074 (4)0.069 (3)0.007 (4)0.013 (3)0.005 (3)
C17D0.070 (4)0.066 (4)0.060 (3)0.007 (3)0.032 (3)0.000 (3)
C18D0.059 (3)0.119 (5)0.067 (4)0.007 (4)0.002 (3)0.017 (4)
C19D0.115 (5)0.116 (6)0.065 (4)0.010 (5)0.010 (4)0.036 (4)
C20D0.126 (6)0.101 (5)0.075 (5)0.007 (5)0.035 (5)0.032 (4)
C21D0.094 (5)0.092 (5)0.076 (4)0.017 (4)0.027 (4)0.012 (4)
C22D0.077 (4)0.072 (4)0.057 (3)0.001 (3)0.012 (3)0.014 (3)
Geometric parameters (Å, º) top
O1A—C1A1.474 (5)O1C—C1C1.464 (5)
O1A—H1A0.8200O1C—H1C0.8200
C3A—C12A1.502 (7)C3C—C12C1.511 (6)
C3A—C4A1.531 (7)C3C—C2C1.523 (5)
C3A—C2A1.537 (6)C3C—C4C1.530 (6)
C3A—H3A10.9800C3C—H3C10.9800
C2A—C1A1.500 (6)C2C—C1C1.526 (6)
C2A—H2A10.9700C2C—H2C10.9700
C2A—H2A20.9700C2C—H2C20.9700
C1A—C6A1.520 (7)C1C—C17C1.491 (6)
C1A—C17A1.551 (7)C1C—C6C1.543 (6)
C6A—C16A1.377 (7)C6C—C16C1.384 (6)
C6A—C5A1.422 (7)C6C—C5C1.390 (6)
C5A—C13A1.399 (8)C5C—C13C1.407 (6)
C5A—C4A1.502 (7)C5C—C4C1.516 (6)
C4A—H4A10.9700C4C—H4C10.9700
C4A—H4A20.9700C4C—H4C20.9700
C7A—C12A1.376 (7)C7C—C12C1.354 (6)
C7A—C8A1.377 (8)C7C—C8C1.395 (7)
C7A—H7A0.9300C7C—H7C0.9300
C8A—C9A1.355 (8)C8C—C9C1.379 (7)
C8A—H8A0.9300C8C—H8C0.9300
C9A—C10A1.370 (9)C9C—C10C1.346 (7)
C9A—H9A0.9300C9C—H9C0.9300
C10A—C11A1.382 (9)C10C—C11C1.398 (7)
C10A—H10A0.9300C10C—H10C0.9300
C11A—C12A1.365 (7)C11C—C12C1.389 (6)
C11A—H11A0.9300C11C—H11C0.9300
C13A—C14A1.346 (8)C13C—C14C1.382 (7)
C13A—H13A0.9300C13C—H13C0.9300
C14A—C15A1.400 (8)C14C—C15C1.374 (7)
C14A—H14A0.9300C14C—H14C0.9300
C15A—C16A1.381 (7)C15C—C16C1.405 (6)
C15A—H15A0.9300C15C—H15C0.9300
C16A—H16A0.9300C16C—H16C0.9300
C17A—C18A1.355 (7)C17C—C18C1.354 (6)
C17A—C22A1.362 (7)C17C—C22C1.415 (6)
C18A—C19A1.403 (8)C18C—C19C1.365 (7)
C18A—H18A0.9300C18C—H18C0.9300
C19A—C20A1.336 (8)C19C—C20C1.403 (7)
C19A—H19A0.9300C19C—H19C0.9300
C20A—C21A1.334 (8)C20C—C21C1.343 (8)
C20A—H20A0.9300C20C—H20C0.9300
C21A—C22A1.393 (8)C21C—C22C1.368 (7)
C21A—H21A0.9300C21C—H21C0.9300
C22A—H22A0.9300C22C—H22C0.9300
O1B—C1B1.436 (5)O1D—C1D1.446 (5)
O1B—H1B0.8200O1D—H1D0.8200
C3B—C2B1.511 (6)C3D—C12D1.501 (6)
C3B—C4B1.521 (7)C3D—C4D1.528 (7)
C3B—C12B1.534 (7)C3D—C2D1.530 (6)
C3B—H3B10.9800C3D—H3D10.9800
C2B—C1B1.551 (6)C2D—C1D1.536 (6)
C2B—H2B10.9700C2D—H2D10.9700
C2B—H2B20.9700C2D—H2D20.9700
C1B—C17B1.526 (7)C1D—C6D1.494 (6)
C1B—C6B1.527 (7)C1D—C17D1.543 (6)
C6B—C5B1.392 (6)C6D—C16D1.392 (6)
C6B—C16B1.411 (7)C6D—C5D1.407 (6)
C5B—C13B1.393 (7)C5D—C13D1.394 (7)
C5B—C4B1.493 (7)C5D—C4D1.498 (7)
C4B—H4B10.9700C4D—H4D10.9700
C4B—H4B20.9700C4D—H4D20.9700
C7B—C12B1.374 (7)C7D—C8D1.382 (7)
C7B—C8B1.394 (8)C7D—C12D1.388 (7)
C7B—H7B0.9300C7D—H7D0.9300
C8B—C9B1.357 (8)C8D—C9D1.372 (8)
C8B—H8B0.9300C8D—H8D0.9300
C9B—C10B1.327 (8)C9D—C10D1.362 (8)
C9B—H9B0.9300C9D—H9D0.9300
C10B—C11B1.407 (8)C10D—C11D1.391 (7)
C10B—H10B0.9300C10D—H10D0.9300
C11B—C12B1.371 (7)C11D—C12D1.360 (7)
C11B—H11B0.9300C11D—H11D0.9300
C13B—C14B1.378 (7)C13D—C14D1.358 (7)
C13B—H13B0.9300C13D—H13D0.9300
C14B—C15B1.358 (7)C14D—C15D1.405 (7)
C14B—H14B0.9300C14D—H14D0.9300
C15B—C16B1.378 (7)C15D—C16D1.377 (6)
C15B—H15B0.9300C15D—H15D0.9300
C16B—H16B0.9300C16D—H16D0.9300
C17B—C18B1.361 (7)C17D—C22D1.387 (6)
C17B—C22B1.403 (7)C17D—C18D1.406 (6)
C18B—C19B1.395 (7)C18D—C19D1.379 (7)
C18B—H18B0.9300C18D—H18D0.9300
C19B—C20B1.400 (9)C19D—C20D1.354 (7)
C19B—H19B0.9300C19D—H19D0.9300
C20B—C21B1.357 (8)C20D—C21D1.383 (7)
C20B—H20B0.9300C20D—H20D0.9300
C21B—C22B1.380 (8)C21D—C22D1.377 (6)
C21B—H21B0.9300C21D—H21D0.9300
C22B—H22B0.9300C22D—H22D0.9300
C1A—O1A—H1A109.5C1C—O1C—H1C109.5
C12A—C3A—C4A112.2 (5)C12C—C3C—C2C114.8 (4)
C12A—C3A—C2A114.8 (5)C12C—C3C—C4C111.5 (4)
C4A—C3A—C2A107.2 (4)C2C—C3C—C4C107.2 (4)
C12A—C3A—H3A1107.4C12C—C3C—H3C1107.7
C4A—C3A—H3A1107.4C2C—C3C—H3C1107.7
C2A—C3A—H3A1107.4C4C—C3C—H3C1107.7
C1A—C2A—C3A112.4 (4)C3C—C2C—C1C112.6 (4)
C1A—C2A—H2A1109.1C3C—C2C—H2C1109.1
C3A—C2A—H2A1109.1C1C—C2C—H2C1109.1
C1A—C2A—H2A2109.1C3C—C2C—H2C2109.1
C3A—C2A—H2A2109.1C1C—C2C—H2C2109.1
H2A1—C2A—H2A2107.9H2C1—C2C—H2C2107.8
O1A—C1A—C2A107.7 (4)O1C—C1C—C17C109.5 (4)
O1A—C1A—C6A105.7 (4)O1C—C1C—C2C104.2 (4)
C2A—C1A—C6A111.6 (4)C17C—C1C—C2C112.4 (4)
O1A—C1A—C17A106.5 (4)O1C—C1C—C6C106.6 (4)
C2A—C1A—C17A112.8 (5)C17C—C1C—C6C114.5 (4)
C6A—C1A—C17A112.0 (5)C2C—C1C—C6C109.0 (4)
C16A—C6A—C5A119.2 (6)C16C—C6C—C5C119.0 (5)
C16A—C6A—C1A121.9 (6)C16C—C6C—C1C118.7 (5)
C5A—C6A—C1A118.9 (6)C5C—C6C—C1C122.3 (5)
C13A—C5A—C6A116.3 (7)C6C—C5C—C13C119.6 (5)
C13A—C5A—C4A121.4 (7)C6C—C5C—C4C122.0 (4)
C6A—C5A—C4A122.2 (6)C13C—C5C—C4C118.4 (5)
C5A—C4A—C3A116.6 (5)C5C—C4C—C3C113.1 (4)
C5A—C4A—H4A1108.1C5C—C4C—H4C1109.0
C3A—C4A—H4A1108.1C3C—C4C—H4C1109.0
C5A—C4A—H4A2108.1C5C—C4C—H4C2109.0
C3A—C4A—H4A2108.1C3C—C4C—H4C2109.0
H4A1—C4A—H4A2107.3H4C1—C4C—H4C2107.8
C12A—C7A—C8A121.4 (6)C12C—C7C—C8C122.5 (5)
C12A—C7A—H7A119.3C12C—C7C—H7C118.8
C8A—C7A—H7A119.3C8C—C7C—H7C118.8
C9A—C8A—C7A120.3 (7)C9C—C8C—C7C118.8 (6)
C9A—C8A—H8A119.9C9C—C8C—H8C120.6
C7A—C8A—H8A119.9C7C—C8C—H8C120.6
C8A—C9A—C10A119.3 (8)C10C—C9C—C8C119.7 (6)
C8A—C9A—H9A120.4C10C—C9C—H9C120.1
C10A—C9A—H9A120.4C8C—C9C—H9C120.1
C9A—C10A—C11A120.1 (8)C9C—C10C—C11C121.1 (6)
C9A—C10A—H10A120.0C9C—C10C—H10C119.4
C11A—C10A—H10A120.0C11C—C10C—H10C119.4
C12A—C11A—C10A121.3 (7)C12C—C11C—C10C119.9 (5)
C12A—C11A—H11A119.3C12C—C11C—H11C120.0
C10A—C11A—H11A119.3C10C—C11C—H11C120.0
C11A—C12A—C7A117.6 (6)C7C—C12C—C11C117.9 (5)
C11A—C12A—C3A121.8 (7)C7C—C12C—C3C122.9 (5)
C7A—C12A—C3A120.6 (6)C11C—C12C—C3C119.2 (5)
C14A—C13A—C5A124.3 (7)C14C—C13C—C5C121.5 (5)
C14A—C13A—H13A117.9C14C—C13C—H13C119.3
C5A—C13A—H13A117.9C5C—C13C—H13C119.3
C13A—C14A—C15A119.1 (7)C15C—C14C—C13C118.3 (5)
C13A—C14A—H14A120.5C15C—C14C—H14C120.9
C15A—C14A—H14A120.5C13C—C14C—H14C120.9
C16A—C15A—C14A118.6 (7)C14C—C15C—C16C121.3 (5)
C16A—C15A—H15A120.7C14C—C15C—H15C119.4
C14A—C15A—H15A120.7C16C—C15C—H15C119.4
C6A—C16A—C15A122.5 (6)C6C—C16C—C15C120.3 (5)
C6A—C16A—H16A118.7C6C—C16C—H16C119.8
C15A—C16A—H16A118.7C15C—C16C—H16C119.8
C18A—C17A—C22A116.2 (5)C18C—C17C—C22C116.2 (5)
C18A—C17A—C1A123.1 (6)C18C—C17C—C1C124.5 (5)
C22A—C17A—C1A120.8 (6)C22C—C17C—C1C119.3 (5)
C17A—C18A—C19A122.4 (6)C17C—C18C—C19C124.1 (5)
C17A—C18A—H18A118.8C17C—C18C—H18C118.0
C19A—C18A—H18A118.8C19C—C18C—H18C118.0
C20A—C19A—C18A119.3 (7)C18C—C19C—C20C118.9 (6)
C20A—C19A—H19A120.3C18C—C19C—H19C120.5
C18A—C19A—H19A120.3C20C—C19C—H19C120.5
C21A—C20A—C19A120.0 (7)C21C—C20C—C19C118.0 (6)
C21A—C20A—H20A120.0C21C—C20C—H20C121.0
C19A—C20A—H20A120.0C19C—C20C—H20C121.0
C20A—C21A—C22A120.4 (7)C20C—C21C—C22C122.9 (6)
C20A—C21A—H21A119.8C20C—C21C—H21C118.5
C22A—C21A—H21A119.8C22C—C21C—H21C118.5
C17A—C22A—C21A121.6 (6)C21C—C22C—C17C119.8 (5)
C17A—C22A—H22A119.2C21C—C22C—H22C120.1
C21A—C22A—H22A119.2C17C—C22C—H22C120.1
C1B—O1B—H1B109.5C1D—O1D—H1D109.5
C2B—C3B—C4B108.6 (5)C12D—C3D—C4D110.3 (4)
C2B—C3B—C12B111.9 (5)C12D—C3D—C2D114.3 (4)
C4B—C3B—C12B111.5 (5)C4D—C3D—C2D108.6 (4)
C2B—C3B—H3B1108.2C12D—C3D—H3D1107.8
C4B—C3B—H3B1108.2C4D—C3D—H3D1107.8
C12B—C3B—H3B1108.2C2D—C3D—H3D1107.8
C3B—C2B—C1B113.7 (4)C3D—C2D—C1D111.6 (4)
C3B—C2B—H2B1108.8C3D—C2D—H2D1109.3
C1B—C2B—H2B1108.8C1D—C2D—H2D1109.3
C3B—C2B—H2B2108.8C3D—C2D—H2D2109.3
C1B—C2B—H2B2108.8C1D—C2D—H2D2109.3
H2B1—C2B—H2B2107.7H2D1—C2D—H2D2108.0
O1B—C1B—C17B105.5 (4)O1D—C1D—C6D110.7 (4)
O1B—C1B—C6B110.3 (4)O1D—C1D—C2D107.9 (4)
C17B—C1B—C6B112.1 (5)C6D—C1D—C2D111.3 (4)
O1B—C1B—C2B108.2 (4)O1D—C1D—C17D104.4 (3)
C17B—C1B—C2B111.1 (4)C6D—C1D—C17D110.8 (4)
C6B—C1B—C2B109.5 (4)C2D—C1D—C17D111.4 (4)
C5B—C6B—C16B118.4 (5)C16D—C6D—C5D117.4 (5)
C5B—C6B—C1B123.2 (5)C16D—C6D—C1D121.8 (4)
C16B—C6B—C1B118.2 (5)C5D—C6D—C1D120.8 (5)
C6B—C5B—C13B117.9 (5)C13D—C5D—C6D118.4 (5)
C6B—C5B—C4B120.9 (5)C13D—C5D—C4D119.8 (5)
C13B—C5B—C4B121.0 (6)C6D—C5D—C4D121.6 (5)
C5B—C4B—C3B115.3 (5)C5D—C4D—C3D116.8 (4)
C5B—C4B—H4B1108.5C5D—C4D—H4D1108.1
C3B—C4B—H4B1108.5C3D—C4D—H4D1108.1
C5B—C4B—H4B2108.5C5D—C4D—H4D2108.1
C3B—C4B—H4B2108.5C3D—C4D—H4D2108.1
H4B1—C4B—H4B2107.5H4D1—C4D—H4D2107.3
C12B—C7B—C8B119.9 (6)C8D—C7D—C12D121.2 (6)
C12B—C7B—H7B120.0C8D—C7D—H7D119.4
C8B—C7B—H7B120.0C12D—C7D—H7D119.4
C9B—C8B—C7B121.8 (7)C9D—C8D—C7D120.9 (7)
C9B—C8B—H8B119.1C9D—C8D—H8D119.5
C7B—C8B—H8B119.1C7D—C8D—H8D119.5
C10B—C9B—C8B118.2 (7)C10D—C9D—C8D118.5 (7)
C10B—C9B—H9B120.9C10D—C9D—H9D120.7
C8B—C9B—H9B120.9C8D—C9D—H9D120.7
C9B—C10B—C11B122.1 (7)C9D—C10D—C11D120.1 (6)
C9B—C10B—H10B119.0C9D—C10D—H10D119.9
C11B—C10B—H10B119.0C11D—C10D—H10D119.9
C12B—C11B—C10B119.9 (7)C12D—C11D—C10D122.5 (6)
C12B—C11B—H11B120.1C12D—C11D—H11D118.8
C10B—C11B—H11B120.1C10D—C11D—H11D118.8
C11B—C12B—C7B118.1 (6)C11D—C12D—C7D116.7 (5)
C11B—C12B—C3B120.4 (6)C11D—C12D—C3D122.6 (5)
C7B—C12B—C3B121.5 (6)C7D—C12D—C3D120.6 (6)
C14B—C13B—C5B122.8 (6)C14D—C13D—C5D123.1 (5)
C14B—C13B—H13B118.6C14D—C13D—H13D118.5
C5B—C13B—H13B118.6C5D—C13D—H13D118.5
C15B—C14B—C13B119.4 (6)C13D—C14D—C15D119.5 (5)
C15B—C14B—H14B120.3C13D—C14D—H14D120.2
C13B—C14B—H14B120.3C15D—C14D—H14D120.2
C14B—C15B—C16B119.6 (6)C16D—C15D—C14D117.5 (5)
C14B—C15B—H15B120.2C16D—C15D—H15D121.2
C16B—C15B—H15B120.2C14D—C15D—H15D121.2
C15B—C16B—C6B121.8 (5)C15D—C16D—C6D124.1 (5)
C15B—C16B—H16B119.1C15D—C16D—H16D118.0
C6B—C16B—H16B119.1C6D—C16D—H16D118.0
C18B—C17B—C22B117.7 (6)C22D—C17D—C18D117.5 (5)
C18B—C17B—C1B124.5 (6)C22D—C17D—C1D119.0 (5)
C22B—C17B—C1B117.8 (6)C18D—C17D—C1D123.5 (5)
C17B—C18B—C19B122.7 (6)C19D—C18D—C17D119.7 (5)
C17B—C18B—H18B118.7C19D—C18D—H18D120.1
C19B—C18B—H18B118.7C17D—C18D—H18D120.1
C18B—C19B—C20B118.8 (7)C20D—C19D—C18D121.9 (6)
C18B—C19B—H19B120.6C20D—C19D—H19D119.0
C20B—C19B—H19B120.6C18D—C19D—H19D119.0
C21B—C20B—C19B118.5 (8)C19D—C20D—C21D119.4 (6)
C21B—C20B—H20B120.8C19D—C20D—H20D120.3
C19B—C20B—H20B120.8C21D—C20D—H20D120.3
C20B—C21B—C22B122.5 (8)C22D—C21D—C20D119.7 (5)
C20B—C21B—H21B118.8C22D—C21D—H21D120.1
C22B—C21B—H21B118.8C20D—C21D—H21D120.1
C21B—C22B—C17B119.8 (6)C21D—C22D—C17D121.8 (5)
C21B—C22B—H22B120.1C21D—C22D—H22D119.1
C17B—C22B—H22B120.1C17D—C22D—H22D119.1
C12A—C3A—C2A—C1A172.0 (4)C1C—C6C—C5C—C13C179.8 (5)
C4A—C3A—C2A—C1A62.6 (6)C16C—C6C—C5C—C4C178.4 (5)
C3A—C2A—C1A—O1A171.9 (4)C1C—C6C—C5C—C4C2.7 (8)
C3A—C2A—C1A—C6A56.3 (5)C6C—C5C—C4C—C3C18.3 (7)
C3A—C2A—C1A—C17A70.8 (5)C13C—C5C—C4C—C3C164.1 (5)
O1A—C1A—C6A—C16A38.5 (6)C12C—C3C—C4C—C5C174.6 (4)
C2A—C1A—C6A—C16A155.3 (5)C2C—C3C—C4C—C5C48.2 (6)
C17A—C1A—C6A—C16A77.1 (6)C12C—C7C—C8C—C9C1.3 (8)
O1A—C1A—C6A—C5A142.4 (4)C7C—C8C—C9C—C10C0.1 (8)
C2A—C1A—C6A—C5A25.6 (6)C8C—C9C—C10C—C11C0.7 (8)
C17A—C1A—C6A—C5A102.0 (5)C9C—C10C—C11C—C12C0.1 (8)
C16A—C6A—C5A—C13A0.0 (7)C8C—C7C—C12C—C11C2.1 (8)
C1A—C6A—C5A—C13A179.2 (5)C8C—C7C—C12C—C3C180.0 (4)
C16A—C6A—C5A—C4A176.9 (5)C10C—C11C—C12C—C7C1.5 (7)
C1A—C6A—C5A—C4A4.0 (7)C10C—C11C—C12C—C3C179.5 (4)
C13A—C5A—C4A—C3A171.4 (5)C2C—C3C—C12C—C7C29.9 (7)
C6A—C5A—C4A—C3A12.0 (7)C4C—C3C—C12C—C7C92.2 (5)
C12A—C3A—C4A—C5A166.1 (5)C2C—C3C—C12C—C11C152.2 (4)
C2A—C3A—C4A—C5A39.1 (6)C4C—C3C—C12C—C11C85.7 (5)
C12A—C7A—C8A—C9A2.9 (10)C6C—C5C—C13C—C14C0.4 (9)
C7A—C8A—C9A—C10A1.9 (10)C4C—C5C—C13C—C14C178.1 (5)
C8A—C9A—C10A—C11A0.7 (11)C5C—C13C—C14C—C15C0.5 (9)
C9A—C10A—C11A—C12A0.4 (10)C13C—C14C—C15C—C16C0.9 (9)
C10A—C11A—C12A—C7A1.3 (9)C5C—C6C—C16C—C15C1.2 (8)
C10A—C11A—C12A—C3A179.8 (6)C1C—C6C—C16C—C15C179.8 (5)
C8A—C7A—C12A—C11A2.5 (9)C14C—C15C—C16C—C6C1.3 (9)
C8A—C7A—C12A—C3A179.0 (6)O1C—C1C—C17C—C18C133.0 (5)
C4A—C3A—C12A—C11A94.8 (6)C2C—C1C—C17C—C18C111.7 (5)
C2A—C3A—C12A—C11A142.4 (5)C6C—C1C—C17C—C18C13.4 (7)
C4A—C3A—C12A—C7A83.7 (6)O1C—C1C—C17C—C22C46.3 (6)
C2A—C3A—C12A—C7A39.1 (7)C2C—C1C—C17C—C22C69.1 (5)
C6A—C5A—C13A—C14A0.5 (9)C6C—C1C—C17C—C22C165.9 (4)
C4A—C5A—C13A—C14A176.3 (6)C22C—C17C—C18C—C19C0.3 (7)
C5A—C13A—C14A—C15A0.0 (11)C1C—C17C—C18C—C19C179.6 (5)
C13A—C14A—C15A—C16A1.1 (10)C17C—C18C—C19C—C20C1.5 (8)
C5A—C6A—C16A—C15A1.2 (8)C18C—C19C—C20C—C21C0.2 (9)
C1A—C6A—C16A—C15A179.7 (5)C19C—C20C—C21C—C22C2.3 (9)
C14A—C15A—C16A—C6A1.7 (9)C20C—C21C—C22C—C17C3.5 (9)
O1A—C1A—C17A—C18A112.4 (6)C18C—C17C—C22C—C21C2.1 (7)
C2A—C1A—C17A—C18A129.6 (6)C1C—C17C—C22C—C21C177.2 (5)
C6A—C1A—C17A—C18A2.7 (7)C12D—C3D—C2D—C1D176.1 (4)
O1A—C1A—C17A—C22A67.8 (7)C4D—C3D—C2D—C1D60.2 (5)
C2A—C1A—C17A—C22A50.1 (7)C3D—C2D—C1D—O1D176.1 (4)
C6A—C1A—C17A—C22A177.1 (5)C3D—C2D—C1D—C6D54.5 (5)
C22A—C17A—C18A—C19A1.1 (10)C3D—C2D—C1D—C17D69.8 (5)
C1A—C17A—C18A—C19A179.2 (6)O1D—C1D—C6D—C16D36.8 (6)
C17A—C18A—C19A—C20A0.4 (11)C2D—C1D—C6D—C16D156.9 (4)
C18A—C19A—C20A—C21A0.2 (12)C17D—C1D—C6D—C16D78.6 (5)
C19A—C20A—C21A—C22A0.2 (12)O1D—C1D—C6D—C5D146.2 (4)
C18A—C17A—C22A—C21A1.1 (10)C2D—C1D—C6D—C5D26.1 (6)
C1A—C17A—C22A—C21A179.1 (6)C17D—C1D—C6D—C5D98.4 (5)
C20A—C21A—C22A—C17A0.6 (12)C16D—C6D—C5D—C13D1.8 (7)
C4B—C3B—C2B—C1B61.4 (6)C1D—C6D—C5D—C13D178.9 (4)
C12B—C3B—C2B—C1B175.1 (5)C16D—C6D—C5D—C4D177.7 (5)
C3B—C2B—C1B—O1B167.7 (4)C1D—C6D—C5D—C4D5.2 (7)
C3B—C2B—C1B—C17B77.0 (6)C13D—C5D—C4D—C3D172.4 (5)
C3B—C2B—C1B—C6B47.4 (6)C6D—C5D—C4D—C3D11.8 (7)
O1B—C1B—C6B—C5B138.6 (5)C12D—C3D—C4D—C5D164.4 (4)
C17B—C1B—C6B—C5B104.1 (6)C2D—C3D—C4D—C5D38.3 (6)
C2B—C1B—C6B—C5B19.7 (7)C12D—C7D—C8D—C9D2.2 (10)
O1B—C1B—C6B—C16B44.6 (6)C7D—C8D—C9D—C10D2.6 (11)
C17B—C1B—C6B—C16B72.6 (6)C8D—C9D—C10D—C11D2.4 (10)
C2B—C1B—C6B—C16B163.6 (5)C9D—C10D—C11D—C12D2.0 (9)
C16B—C6B—C5B—C13B0.2 (8)C10D—C11D—C12D—C7D1.5 (8)
C1B—C6B—C5B—C13B176.9 (5)C10D—C11D—C12D—C3D176.4 (5)
C16B—C6B—C5B—C4B176.2 (5)C8D—C7D—C12D—C11D1.6 (9)
C1B—C6B—C5B—C4B7.1 (8)C8D—C7D—C12D—C3D176.3 (5)
C6B—C5B—C4B—C3B20.5 (8)C4D—C3D—C12D—C11D102.3 (6)
C13B—C5B—C4B—C3B163.6 (6)C2D—C3D—C12D—C11D134.9 (5)
C2B—C3B—C4B—C5B46.1 (7)C4D—C3D—C12D—C7D75.5 (6)
C12B—C3B—C4B—C5B169.9 (5)C2D—C3D—C12D—C7D47.3 (7)
C12B—C7B—C8B—C9B1.4 (11)C6D—C5D—C13D—C14D1.1 (8)
C7B—C8B—C9B—C10B1.0 (12)C4D—C5D—C13D—C14D177.1 (5)
C8B—C9B—C10B—C11B2.1 (13)C5D—C13D—C14D—C15D0.2 (9)
C9B—C10B—C11B—C12B0.9 (12)C13D—C14D—C15D—C16D0.0 (8)
C10B—C11B—C12B—C7B1.5 (10)C14D—C15D—C16D—C6D0.8 (8)
C10B—C11B—C12B—C3B179.3 (6)C5D—C6D—C16D—C15D1.7 (7)
C8B—C7B—C12B—C11B2.6 (10)C1D—C6D—C16D—C15D178.8 (4)
C8B—C7B—C12B—C3B178.2 (6)O1D—C1D—C17D—C22D41.1 (6)
C2B—C3B—C12B—C11B126.0 (6)C6D—C1D—C17D—C22D160.3 (4)
C4B—C3B—C12B—C11B112.1 (7)C2D—C1D—C17D—C22D75.1 (5)
C2B—C3B—C12B—C7B54.8 (7)O1D—C1D—C17D—C18D140.4 (5)
C4B—C3B—C12B—C7B67.0 (8)C6D—C1D—C17D—C18D21.2 (6)
C6B—C5B—C13B—C14B1.2 (9)C2D—C1D—C17D—C18D103.4 (5)
C4B—C5B—C13B—C14B177.2 (6)C22D—C17D—C18D—C19D0.7 (7)
C5B—C13B—C14B—C15B1.4 (10)C1D—C17D—C18D—C19D177.8 (5)
C13B—C14B—C15B—C16B0.6 (10)C17D—C18D—C19D—C20D0.8 (9)
C14B—C15B—C16B—C6B0.4 (9)C18D—C19D—C20D—C21D0.3 (9)
C5B—C6B—C16B—C15B0.6 (8)C19D—C20D—C21D—C22D0.2 (9)
C1B—C6B—C16B—C15B176.3 (5)C20D—C21D—C22D—C17D0.2 (8)
O1B—C1B—C17B—C18B128.2 (5)C18D—C17D—C22D—C21D0.2 (7)
C6B—C1B—C17B—C18B8.2 (7)C1D—C17D—C22D—C21D178.3 (4)
C2B—C1B—C17B—C18B114.7 (6)C2A—C3A—C12A—C7A39.1 (7)
O1B—C1B—C17B—C22B53.1 (6)C2Bi—C3Bi—C12Bi—C7Bi54.8 (7)
C6B—C1B—C17B—C22B173.2 (5)C2Ci—C3Ci—C12Ci—C7Ci29.9 (7)
C2B—C1B—C17B—C22B64.0 (6)C2D—C3D—C12D—C7D47.3 (7)
C22B—C17B—C18B—C19B1.7 (9)C6A—C1A—C17A—C22A177.1 (5)
C1B—C17B—C18B—C19B179.6 (5)C6Bi—C1Bi—C17Bi—C22Bi173.2 (5)
C17B—C18B—C19B—C20B1.5 (9)C6Ci—C1Ci—C17Ci—C22Ci165.9 (4)
C18B—C19B—C20B—C21B0.5 (10)C6D—C1D—C17D—C22D160.3 (4)
C19B—C20B—C21B—C22B0.1 (11)C11A—C12A—C3A—C2A142.4 (5)
C20B—C21B—C22B—C17B0.1 (10)C11Bi—C12Bi—C3Bi—C2Bi126.0 (6)
C18B—C17B—C22B—C21B1.0 (8)C11Ci—C12Ci—C3Ci—C2Ci152.2 (4)
C1B—C17B—C22B—C21B179.8 (5)C11D—C12D—C3D—C2D134.9 (5)
C12C—C3C—C2C—C1C168.0 (4)C6A—C1A—C17A—C18A2.7 (7)
C4C—C3C—C2C—C1C67.6 (5)C6Bi—C1Bi—C17Bi—C18Bi8.2 (7)
C3C—C2C—C1C—O1C164.6 (3)C6Ci—C1Ci—C17Ci—C18Ci13.4 (7)
C3C—C2C—C1C—C17C76.9 (5)C6D—C1D—C17D—C18D21.2 (6)
C3C—C2C—C1C—C6C51.1 (5)C5A—C6A—C1A—O1A142.4 (4)
O1C—C1C—C6C—C16C50.9 (6)C5Bi—C6Bi—C1Bi—O1Bi138.6 (5)
C17C—C1C—C6C—C16C70.3 (6)C5Ci—C6Ci—C1Ci—O1Ci130.1 (5)
C2C—C1C—C6C—C16C162.8 (4)C5D—C6D—C1D—O1D146.2 (4)
O1C—C1C—C6C—C5C130.1 (5)C5A—C6A—C1A—C2A25.6 (6)
C17C—C1C—C6C—C5C108.6 (6)C5Bi—C6Bi—C1Bi—C2Bi19.7 (7)
C2C—C1C—C6C—C5C18.2 (6)C5Ci—C6Ci—C1Ci—C2Ci18.2 (6)
C16C—C6C—C5C—C13C0.8 (8)C5D—C6D—C1D—C2D26.1 (6)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1B0.822.142.909 (5)155
O1B—H1B···O1C0.821.922.737 (5)173
O1C—H1C···O1D0.821.962.759 (5)163
O1D—H1D···O1A0.822.042.792 (5)153

Experimental details

Crystal data
Chemical formulaC22H20O
Mr300.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)16.546 (3), 13.124 (3), 31.942 (6)
β (°) 100.62 (3)
V3)6817 (2)
Z16
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.4 × 0.2 × 0.05
Data collection
DiffractometerRigaku AFC6 Diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16186, 13368, 3121
Rint0.112
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.202, 0.85
No. of reflections13368
No. of parameters835
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.17

Computer programs: AFC6S Diffractometer Control Software (Molecular Structure Corporation, 1993), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-PC (Sheldrick, 2008) and PARST (Nardelli, 1983).

Selected geometric parameters (Å, º) top
O1A—C1A1.474 (5)O1C—C1C1.464 (5)
O1B—C1B1.436 (5)O1D—C1D1.446 (5)
O1A—C1A—C2A107.7 (4)O1C—C1C—C2C104.2 (4)
O1B—C1B—C2B108.2 (4)O1D—C1D—C2D107.9 (4)
C2A—C3A—C12A—C7A39.1 (7)C5A—C6A—C1A—O1A142.4 (4)
C2Bi—C3Bi—C12Bi—C7Bi54.8 (7)C5Bi—C6Bi—C1Bi—O1Bi138.6 (5)
C2Ci—C3Ci—C12Ci—C7Ci29.9 (7)C5Ci—C6Ci—C1Ci—O1Ci130.1 (5)
C2D—C3D—C12D—C7D47.3 (7)C5D—C6D—C1D—O1D146.2 (4)
C6A—C1A—C17A—C22A177.1 (5)C5A—C6A—C1A—C2A25.6 (6)
C6Bi—C1Bi—C17Bi—C22Bi173.2 (5)C5Bi—C6Bi—C1Bi—C2Bi19.7 (7)
C6Ci—C1Ci—C17Ci—C22Ci165.9 (4)C5Ci—C6Ci—C1Ci—C2Ci18.2 (6)
C6D—C1D—C17D—C22D160.3 (4)C5D—C6D—C1D—C2D26.1 (6)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1B0.8202.1432.909 (5)155.43
O1B—H1B···O1C0.8201.9222.737 (5)172.73
O1C—H1C···O1D0.8201.9642.759 (5)163.26
O1D—H1D···O1A0.8202.0382.792 (5)152.67
 

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