organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2,2′-Bis(meth­­oxy­meth­­oxy)-3,3′-di­phenyl-1,1′-bi­naphthalene

aState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, People's Republic of China
*Correspondence e-mail: songling@fjirsm.ac.cn

(Received 3 December 2010; accepted 17 December 2010; online 24 December 2010)

The asymmetric unit of the title compound, C36H30O4, contains two crystallographically independent mol­ecules of similar geometry. In both mol­ecules, the meth­oxy­meth­oxy groups are disordered over two positions with refined site occupancies of 0.613 (3):0.387 (3) and 0.589 (4):0.411 (4). The dihedral angles between the naphthalene planes within the same mol­ecule are 71.72 (7) and 71.73 (8)°. In the crystal, neighbouring mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds, forming double chains parallel to the c axis.

Related literature

For the application of 1,1′-bi-2-naphthol derivatives in asymmetric syntheses, see: Lou et al. (2006[Lou, S., Moquist, P. N. & Schaus, S. E. (2006). J. Am. Chem. Soc. 128, 12660-12661.]); Brunel (2006[Brunel, J. M. (2006). Chem. Rev. 105, 857-897.]). For the synthesis of the title compound, see: Wu et al. (2004[Wu, T. R., Shen, L. X. & Chong, J. M. (2004). Org. Lett, 6, 2701-2704.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C36H30O4

  • Mr = 526.60

  • Monoclinic, P 21

  • a = 11.3166 (3) Å

  • b = 19.4841 (3) Å

  • c = 14.0155 (4) Å

  • β = 110.172 (3)°

  • V = 2900.77 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 K

  • 0.43 × 0.40 × 0.36 mm

Data collection
  • Oxford Xcalibur Eos CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.828, Tmax = 1.000

  • 12553 measured reflections

  • 6211 independent reflections

  • 4315 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.069

  • S = 1.01

  • 6211 reflections

  • 769 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3A⋯O6Ai 0.93 2.59 3.448 (6) 153
C43—H43A⋯O2Bii 0.93 2.57 3.304 (7) 136
C51—H51A⋯O1 0.93 2.38 3.233 (3) 152
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+1]; (ii) x, y, z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England.]); 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: DIAMOND (Brandenburg & Berndt, 1999[Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Chiral compounds especially when used as chiral ligands are particularly important in asymmteric synthesis. 1,1'-Bi-2-naphthol (BINOL) and its derivatives have been widely used in asymmetric synthesis (Lou et al., 2006; Brunel, 2006), and used as effective chiral ligands for various metal complex catalysis. As part of our research in this field, we synthesized the title compound, whose X-ray crystal structure is reported herein.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1). In both molecules, the methoxymethoxy groups are disordered over two positions with refined site occupancies of 0.613 (3):0.387 (3) and 0.589 (4):0.411 (4). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angles between the naphthalene planes belonging to the same molecule are 71.72 (7)° and 71.73 (8)°. In the crystal structure, intramolecular C—H···O hydrogen bonds (Table 1) assemble neighbouring molecule into double chains running parallel to the c axis (Fig. 2).

Related literature top

For the application of 1,1'-bi-2-naphthol derivatives in asymmetric syntheses, see: Lou et al. (2006); Brunel (2006). For the synthesis of the title compound, see: Wu et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of (R,R)-3,3'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene and phenylboronic acid according to the literature method (Wu et al., 2004). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (1.5 g) in ethyl acetate (20 ml) and evaporating the solvent slowly at room temperature for about 28 h.

Refinement top

All methoxymethoxy groups of the two molecules were refined as disordered, with site occupancies of 0.613 (3):0.387 (3) for the major and minor components respectively of O2/C33/C34, and of 0.589 (4):0.411 (4) for the major and minor components respectively of O4/C35/C36. During the refinement, the displacement parameters of the two components of the disordered atoms were set equal to each other. The H atoms were placed at calculated positions (C—H = 0.93 Å for aromatic, 0.97 Å for methylene and 0.96 Å for methyl H atoms), and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. In the absence of significant anomalous scattering effects, 4186 Friedel pairs were merged.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis CCD (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of independent molecules of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Crystal packing of the title compound showing the formation of double chains through intermolecular hydrogen bonds (dashed lines).
2,2'-Bis(methoxymethoxy)-3,3'-diphenyl-1,1'-binaphthalene top
Crystal data top
C36H30O4F(000) = 1112
Mr = 526.60Dx = 1.206 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6318 reflections
a = 11.3166 (3) Åθ = 2.6–28.8°
b = 19.4841 (3) ŵ = 0.08 mm1
c = 14.0155 (4) ÅT = 295 K
β = 110.172 (3)°Block, colourless
V = 2900.77 (12) Å30.43 × 0.40 × 0.36 mm
Z = 4
Data collection top
Oxford Xcalibur Eos CCD
diffractometer
6211 independent reflections
Radiation source: fine-focus sealed tube4315 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 16.2083 pixels mm-1θmax = 26.6°, θmin = 2.6°
ω scansh = 1412
Absorption correction: multi-scan
(CrysAlis CCD; Oxford Diffraction, 2006)
k = 2424
Tmin = 0.828, Tmax = 1.000l = 1017
12553 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.015P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
6211 reflections(Δ/σ)max = 0.009
769 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.20 e Å3
Crystal data top
C36H30O4V = 2900.77 (12) Å3
Mr = 526.60Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.3166 (3) ŵ = 0.08 mm1
b = 19.4841 (3) ÅT = 295 K
c = 14.0155 (4) Å0.43 × 0.40 × 0.36 mm
β = 110.172 (3)°
Data collection top
Oxford Xcalibur Eos CCD
diffractometer
6211 independent reflections
Absorption correction: multi-scan
(CrysAlis CCD; Oxford Diffraction, 2006)
4315 reflections with I > 2σ(I)
Tmin = 0.828, Tmax = 1.000Rint = 0.020
12553 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0361 restraint
wR(F2) = 0.069H-atom parameters constrained
S = 1.01Δρmax = 0.16 e Å3
6211 reflectionsΔρmin = 0.20 e Å3
769 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*/UeqOcc. (<1)
O10.66287 (16)0.31954 (8)0.06996 (12)0.0407 (4)
O30.85866 (16)0.34414 (9)0.28820 (13)0.0488 (5)
C10.8423 (3)0.12956 (14)0.1334 (2)0.0456 (7)
C20.9041 (3)0.06530 (15)0.1496 (2)0.0613 (8)
H2A0.85690.02520.13910.074*
C31.0311 (3)0.06144 (17)0.1803 (3)0.0746 (10)
H3A1.07060.01880.18980.089*
C41.1029 (3)0.12118 (18)0.1977 (3)0.0725 (10)
H4A1.19010.11810.21800.087*
C51.0474 (3)0.18406 (15)0.1854 (2)0.0566 (8)
H5A1.09700.22340.20020.068*
C60.9143 (2)0.19010 (13)0.1501 (2)0.0419 (6)
C70.8511 (2)0.25519 (12)0.12941 (18)0.0375 (6)
C80.7225 (2)0.25634 (12)0.09268 (18)0.0369 (6)
C90.6475 (2)0.19590 (13)0.07966 (18)0.0377 (6)
C100.7102 (3)0.13445 (13)0.1001 (2)0.0439 (6)
H10A0.66350.09420.09150.053*
C110.5089 (2)0.19680 (14)0.05067 (18)0.0404 (6)
C120.4472 (3)0.24327 (15)0.0931 (2)0.0510 (7)
H12A0.49270.27800.13550.061*
C130.3191 (3)0.23809 (18)0.0727 (3)0.0670 (9)
H13A0.27920.26940.10140.080*
C140.2502 (3)0.18733 (19)0.0107 (3)0.0698 (9)
H14A0.16420.18390.00180.084*
C150.3085 (3)0.14150 (17)0.0330 (2)0.0621 (8)
H15A0.26190.10720.07580.075*
C160.4369 (3)0.14645 (15)0.0133 (2)0.0519 (7)
H16A0.47560.11540.04350.062*
C170.9245 (2)0.32005 (12)0.14840 (19)0.0390 (6)
C180.9904 (2)0.34052 (13)0.08228 (19)0.0412 (6)
C190.9824 (3)0.30318 (15)0.0060 (2)0.0488 (7)
H19A0.93420.26330.02170.059*
C201.0439 (3)0.32469 (15)0.0684 (2)0.0575 (8)
H20A1.03740.29940.12630.069*
C211.1170 (3)0.38432 (17)0.0467 (3)0.0704 (10)
H21A1.15900.39850.08970.084*
C221.1263 (3)0.42143 (16)0.0378 (2)0.0639 (9)
H22A1.17490.46110.05170.077*
C231.0639 (3)0.40112 (14)0.1047 (2)0.0480 (7)
C241.0673 (3)0.44049 (14)0.1899 (2)0.0512 (7)
H24A1.11730.47970.20520.061*
C251.0005 (2)0.42356 (13)0.2507 (2)0.0446 (7)
C260.9995 (3)0.46893 (14)0.3362 (2)0.0491 (7)
C271.1091 (3)0.48489 (16)0.4141 (2)0.0626 (8)
H27A1.18510.46630.41480.075*
C281.1067 (4)0.52873 (18)0.4919 (3)0.0761 (10)
H28A1.18120.53870.54460.091*
C290.9969 (5)0.55708 (19)0.4917 (3)0.0830 (11)
H29A0.99610.58590.54440.100*
C300.8880 (4)0.5431 (2)0.4138 (3)0.0860 (12)
H30A0.81320.56380.41210.103*
C310.8880 (3)0.49803 (17)0.3367 (3)0.0706 (10)
H31A0.81280.48740.28530.085*
C320.9292 (2)0.36130 (13)0.2287 (2)0.0421 (6)
O2A0.6852 (4)0.3614 (2)0.0778 (3)0.0701 (8)0.613 (3)
C33A0.6000 (19)0.3366 (11)0.0319 (16)0.050 (3)0.613 (3)
H33A0.53730.37150.03600.059*0.613 (3)
H33B0.55690.29650.06840.059*0.613 (3)
C34A0.721 (3)0.4298 (14)0.031 (2)0.092 (3)0.613 (3)
H34A0.78620.44890.05140.137*0.613 (3)
H34B0.75010.42540.04190.137*0.613 (3)
H34C0.64860.45960.05220.137*0.613 (3)
O2B0.5987 (6)0.4032 (3)0.0510 (4)0.0701 (8)0.387 (3)
C33B0.625 (3)0.3315 (18)0.043 (3)0.050 (3)0.387 (3)
H33C0.69250.32010.06750.059*0.387 (3)
H33D0.55060.30500.08010.059*0.387 (3)
C34B0.732 (5)0.438 (3)0.047 (4)0.092 (3)0.387 (3)
H34D0.71840.48600.06380.137*0.387 (3)
H34E0.76150.41580.09570.137*0.387 (3)
H34F0.79270.43310.01970.137*0.387 (3)
O4A0.9249 (5)0.2474 (3)0.3892 (3)0.0944 (11)0.589 (4)
C35A0.919 (3)0.3217 (14)0.387 (2)0.062 (4)0.589 (4)
H35A0.87420.33770.43030.075*0.589 (4)
H35B1.00390.34030.41260.075*0.589 (4)
C36A0.8111 (9)0.2179 (5)0.3762 (9)0.119 (4)0.589 (4)
H36A0.82220.16960.39000.178*0.589 (4)
H36B0.75580.22480.30750.178*0.589 (4)
H36C0.77510.23860.42210.178*0.589 (4)
O4B0.8506 (7)0.2985 (3)0.4337 (5)0.0944 (11)0.411 (4)
C35B0.940 (4)0.306 (2)0.381 (3)0.062 (4)0.411 (4)
H35C0.96740.26230.36380.075*0.411 (4)
H35D1.01280.33310.42020.075*0.411 (4)
C36B0.7513 (14)0.2523 (8)0.3896 (14)0.119 (4)0.411 (4)
H36D0.68610.25990.41760.178*0.411 (4)
H36E0.78180.20610.40350.178*0.411 (4)
H36F0.71810.25950.31740.178*0.411 (4)
O50.67985 (16)0.32761 (9)0.62699 (13)0.0473 (4)
O70.45926 (17)0.34620 (9)0.42540 (13)0.0469 (4)
C370.4630 (2)0.47056 (14)0.41811 (19)0.0424 (6)
C380.4631 (3)0.53195 (14)0.4654 (2)0.0509 (7)
H38A0.46110.57240.42980.061*
C390.4661 (3)0.53555 (15)0.5663 (2)0.0525 (8)
C400.4697 (3)0.59979 (17)0.6154 (3)0.0729 (10)
H40A0.46530.64030.57930.087*
C410.4795 (4)0.6022 (2)0.7146 (3)0.0877 (12)
H41A0.48220.64440.74630.105*
C420.4856 (4)0.5417 (2)0.7692 (3)0.0863 (12)
H42A0.49270.54420.83720.104*
C430.4814 (3)0.47894 (19)0.7251 (2)0.0668 (9)
H43A0.48580.43920.76300.080*
C440.4704 (3)0.47424 (16)0.6209 (2)0.0499 (7)
C450.4664 (2)0.41001 (14)0.57177 (19)0.0430 (6)
C460.4602 (2)0.40943 (13)0.47191 (19)0.0415 (6)
C470.4684 (2)0.47056 (14)0.31353 (19)0.0426 (6)
C480.3975 (3)0.51715 (14)0.2424 (2)0.0481 (7)
H48A0.34250.54630.25910.058*
C490.4071 (3)0.52101 (16)0.1469 (2)0.0579 (8)
H49A0.35800.55220.09960.070*
C500.4888 (3)0.47895 (17)0.1220 (2)0.0623 (8)
H50A0.49520.48160.05770.075*
C510.5615 (3)0.43274 (16)0.1919 (2)0.0620 (8)
H51A0.61700.40420.17480.074*
C520.5525 (3)0.42866 (15)0.2871 (2)0.0533 (7)
H52A0.60280.39770.33430.064*
C530.4726 (2)0.34401 (14)0.62793 (18)0.0443 (7)
C540.3679 (2)0.32041 (16)0.65318 (19)0.0501 (7)
C550.2527 (3)0.3570 (2)0.6262 (2)0.0683 (9)
H55A0.24440.39870.59200.082*
C560.1539 (3)0.3316 (2)0.6498 (3)0.0872 (12)
H56A0.07900.35630.63210.105*
C570.1641 (4)0.2690 (3)0.7004 (3)0.0953 (13)
H57A0.09590.25220.71590.114*
C580.2717 (3)0.2326 (2)0.7270 (3)0.0789 (11)
H58A0.27680.19100.76070.095*
C590.3778 (3)0.25672 (17)0.7046 (2)0.0546 (7)
C600.4909 (3)0.21998 (16)0.7319 (2)0.0532 (8)
H60A0.49740.17890.76710.064*
C610.5926 (3)0.24246 (14)0.70861 (19)0.0442 (6)
C620.5801 (2)0.30555 (14)0.65524 (18)0.0416 (6)
C630.7117 (3)0.20217 (13)0.7404 (2)0.0449 (7)
C640.7621 (3)0.17739 (13)0.8390 (2)0.0498 (7)
H64A0.72150.18640.88510.060*
C650.8718 (3)0.13948 (15)0.8696 (3)0.0614 (8)
H65A0.90420.12300.93580.074*
C660.9327 (3)0.12617 (16)0.8033 (3)0.0704 (10)
H66A1.00710.10100.82450.084*
C670.8848 (3)0.14971 (17)0.7052 (3)0.0715 (10)
H67A0.92650.14030.66010.086*
C680.7742 (3)0.18753 (16)0.6731 (2)0.0596 (8)
H68A0.74170.20310.60640.072*
O6A0.7764 (4)0.4266 (2)0.7012 (3)0.0740 (9)0.545 (3)
C69A0.785 (3)0.3544 (13)0.699 (3)0.060 (4)0.545 (3)
H69A0.85900.34120.68430.071*0.545 (3)
H69B0.79220.33590.76540.071*0.545 (3)
C70A0.792 (5)0.457 (3)0.609 (4)0.120 (8)0.545 (3)
H70A0.81070.50480.61990.181*0.545 (3)
H70B0.71520.45110.55210.181*0.545 (3)
H70C0.85940.43400.59510.181*0.545 (3)
O6B0.8608 (5)0.3931 (3)0.6772 (4)0.0740 (9)0.455 (3)
C69B0.767 (3)0.3710 (17)0.711 (3)0.060 (4)0.455 (3)
H69C0.72140.40990.72480.071*0.455 (3)
H69D0.80130.34430.77260.071*0.455 (3)
C70B0.816 (6)0.441 (3)0.601 (5)0.120 (8)0.455 (3)
H70D0.88490.46920.59770.181*0.455 (3)
H70E0.75520.47010.61480.181*0.455 (3)
H70F0.77760.41860.53690.181*0.455 (3)
O8A0.2554 (2)0.30346 (14)0.3860 (2)0.0771 (9)0.883 (4)
C71A0.3449 (8)0.3271 (3)0.3501 (6)0.0604 (13)0.883 (4)
H71A0.31140.36650.30700.072*0.883 (4)
H71B0.36210.29180.30790.072*0.883 (4)
C72A0.2872 (8)0.2372 (3)0.4296 (6)0.0946 (18)0.883 (4)
H72A0.22210.22120.45340.142*0.883 (4)
H72B0.36540.23960.48550.142*0.883 (4)
H72C0.29560.20600.37920.142*0.883 (4)
O8B0.3269 (18)0.2599 (11)0.3404 (16)0.0771 (9)0.117 (4)
C71B0.332 (8)0.345 (3)0.337 (5)0.0604 (13)0.117 (4)
H71C0.33770.36220.27340.072*0.117 (4)
H71D0.26460.36690.35230.072*0.117 (4)
C72B0.264 (8)0.220 (3)0.411 (5)0.0946 (18)0.117 (4)
H72D0.27970.17160.40910.142*0.117 (4)
H72E0.17490.22810.38630.142*0.117 (4)
H72F0.29980.23630.47950.142*0.117 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0491 (10)0.0326 (9)0.0388 (10)0.0060 (8)0.0132 (8)0.0004 (8)
O30.0545 (11)0.0461 (11)0.0469 (11)0.0033 (9)0.0190 (9)0.0004 (9)
C10.0488 (17)0.0370 (15)0.0515 (17)0.0037 (13)0.0182 (14)0.0014 (13)
C20.062 (2)0.0340 (16)0.085 (2)0.0034 (15)0.0225 (19)0.0010 (16)
C30.069 (2)0.0446 (19)0.103 (3)0.0176 (17)0.021 (2)0.0040 (19)
C40.0449 (18)0.065 (2)0.098 (3)0.0163 (17)0.0120 (18)0.002 (2)
C50.0467 (18)0.0438 (17)0.074 (2)0.0011 (14)0.0138 (16)0.0018 (16)
C60.0410 (15)0.0356 (14)0.0482 (16)0.0025 (12)0.0142 (13)0.0000 (13)
C70.0405 (15)0.0315 (13)0.0408 (15)0.0013 (12)0.0143 (12)0.0028 (12)
C80.0472 (16)0.0290 (13)0.0367 (14)0.0048 (12)0.0174 (12)0.0017 (12)
C90.0417 (15)0.0368 (14)0.0379 (14)0.0004 (12)0.0178 (12)0.0009 (12)
C100.0479 (17)0.0344 (14)0.0514 (17)0.0070 (13)0.0198 (14)0.0047 (13)
C110.0433 (15)0.0403 (14)0.0401 (15)0.0014 (13)0.0174 (13)0.0047 (13)
C120.0508 (18)0.0549 (19)0.0480 (17)0.0036 (15)0.0178 (14)0.0034 (15)
C130.052 (2)0.079 (2)0.077 (2)0.0111 (18)0.0317 (18)0.002 (2)
C140.0424 (18)0.081 (2)0.085 (2)0.0039 (18)0.0213 (18)0.002 (2)
C150.0499 (19)0.061 (2)0.070 (2)0.0108 (16)0.0135 (17)0.0062 (17)
C160.0536 (18)0.0476 (17)0.0575 (19)0.0024 (14)0.0228 (16)0.0028 (15)
C170.0376 (14)0.0326 (14)0.0427 (14)0.0004 (11)0.0087 (12)0.0001 (12)
C180.0408 (14)0.0336 (14)0.0454 (15)0.0016 (12)0.0100 (12)0.0005 (12)
C190.0487 (16)0.0444 (16)0.0520 (16)0.0000 (14)0.0157 (14)0.0039 (14)
C200.069 (2)0.0539 (19)0.0529 (17)0.0046 (17)0.0245 (16)0.0044 (16)
C210.084 (3)0.068 (2)0.074 (2)0.0061 (19)0.046 (2)0.0056 (19)
C220.073 (2)0.0508 (19)0.078 (2)0.0146 (16)0.0398 (19)0.0001 (18)
C230.0492 (16)0.0378 (15)0.0565 (18)0.0030 (13)0.0176 (14)0.0005 (14)
C240.0504 (17)0.0344 (15)0.068 (2)0.0091 (13)0.0196 (16)0.0038 (14)
C250.0456 (16)0.0347 (15)0.0486 (16)0.0011 (12)0.0099 (13)0.0006 (13)
C260.0592 (19)0.0358 (15)0.0539 (17)0.0024 (14)0.0214 (15)0.0009 (14)
C270.068 (2)0.0546 (19)0.060 (2)0.0007 (16)0.0141 (17)0.0113 (17)
C280.091 (3)0.070 (2)0.063 (2)0.011 (2)0.020 (2)0.0181 (19)
C290.118 (3)0.067 (2)0.077 (2)0.015 (2)0.050 (2)0.023 (2)
C300.086 (3)0.078 (3)0.109 (3)0.004 (2)0.052 (3)0.021 (2)
C310.064 (2)0.066 (2)0.084 (3)0.0064 (18)0.0285 (19)0.0211 (19)
C320.0412 (15)0.0368 (14)0.0469 (16)0.0014 (12)0.0133 (13)0.0027 (13)
O2A0.095 (2)0.061 (2)0.0567 (18)0.0074 (17)0.0295 (17)0.0117 (16)
C33A0.062 (9)0.043 (4)0.045 (5)0.014 (4)0.021 (4)0.000 (3)
C34A0.099 (6)0.073 (6)0.099 (9)0.017 (5)0.030 (5)0.048 (5)
O2B0.095 (2)0.061 (2)0.0567 (18)0.0074 (17)0.0295 (17)0.0117 (16)
C33B0.062 (9)0.043 (4)0.045 (5)0.014 (4)0.021 (4)0.000 (3)
C34B0.099 (6)0.073 (6)0.099 (9)0.017 (5)0.030 (5)0.048 (5)
O4A0.109 (3)0.086 (3)0.082 (3)0.005 (2)0.024 (2)0.023 (2)
C35A0.066 (10)0.064 (12)0.058 (4)0.004 (7)0.023 (4)0.009 (7)
C36A0.108 (9)0.109 (9)0.136 (6)0.022 (5)0.037 (6)0.050 (7)
O4B0.109 (3)0.086 (3)0.082 (3)0.005 (2)0.024 (2)0.023 (2)
C35B0.066 (10)0.064 (12)0.058 (4)0.004 (7)0.023 (4)0.009 (7)
C36B0.108 (9)0.109 (9)0.136 (6)0.022 (5)0.037 (6)0.050 (7)
O50.0445 (10)0.0479 (11)0.0513 (11)0.0031 (9)0.0188 (9)0.0023 (9)
O70.0583 (12)0.0385 (10)0.0408 (10)0.0047 (9)0.0133 (9)0.0031 (9)
C370.0453 (15)0.0426 (15)0.0398 (15)0.0075 (13)0.0155 (13)0.0024 (14)
C380.064 (2)0.0406 (16)0.0491 (17)0.0101 (14)0.0212 (15)0.0013 (14)
C390.0585 (19)0.0513 (18)0.0466 (18)0.0085 (15)0.0169 (15)0.0112 (15)
C400.092 (3)0.056 (2)0.069 (2)0.0125 (19)0.027 (2)0.0140 (18)
C410.114 (3)0.074 (3)0.069 (3)0.017 (2)0.025 (2)0.033 (2)
C420.112 (3)0.098 (3)0.048 (2)0.033 (3)0.027 (2)0.012 (2)
C430.079 (2)0.078 (2)0.0417 (18)0.0182 (19)0.0183 (16)0.0058 (18)
C440.0524 (17)0.0575 (18)0.0390 (15)0.0119 (15)0.0148 (14)0.0047 (15)
C450.0421 (15)0.0488 (16)0.0373 (15)0.0071 (13)0.0125 (12)0.0011 (13)
C460.0434 (16)0.0405 (15)0.0390 (15)0.0072 (13)0.0119 (12)0.0030 (13)
C470.0497 (16)0.0384 (14)0.0418 (15)0.0030 (13)0.0183 (13)0.0000 (13)
C480.0550 (17)0.0435 (16)0.0507 (17)0.0067 (13)0.0243 (15)0.0079 (14)
C490.072 (2)0.0544 (19)0.0509 (18)0.0031 (16)0.0259 (17)0.0111 (15)
C500.087 (2)0.0595 (19)0.0494 (18)0.0061 (19)0.0357 (18)0.0024 (17)
C510.074 (2)0.0569 (19)0.068 (2)0.0051 (17)0.0414 (18)0.0101 (18)
C520.0621 (19)0.0483 (17)0.0528 (18)0.0087 (15)0.0238 (15)0.0004 (15)
C530.0481 (17)0.0504 (17)0.0334 (14)0.0022 (14)0.0127 (13)0.0002 (13)
C540.0425 (16)0.071 (2)0.0355 (14)0.0030 (15)0.0118 (12)0.0021 (15)
C550.0529 (19)0.097 (3)0.0548 (19)0.0117 (19)0.0186 (16)0.0119 (19)
C560.050 (2)0.137 (4)0.079 (2)0.012 (2)0.0276 (19)0.006 (3)
C570.062 (2)0.145 (4)0.090 (3)0.006 (3)0.041 (2)0.019 (3)
C580.063 (2)0.104 (3)0.076 (2)0.006 (2)0.031 (2)0.023 (2)
C590.0485 (17)0.071 (2)0.0449 (16)0.0041 (16)0.0165 (14)0.0073 (16)
C600.059 (2)0.0559 (18)0.0451 (17)0.0067 (15)0.0185 (15)0.0058 (14)
C610.0492 (16)0.0456 (16)0.0360 (15)0.0040 (13)0.0125 (13)0.0013 (13)
C620.0418 (15)0.0489 (16)0.0346 (14)0.0018 (13)0.0141 (12)0.0014 (13)
C630.0525 (17)0.0324 (14)0.0494 (17)0.0055 (13)0.0172 (14)0.0061 (13)
C640.0574 (18)0.0394 (16)0.0494 (17)0.0036 (14)0.0142 (15)0.0040 (14)
C650.065 (2)0.0397 (17)0.066 (2)0.0017 (16)0.0052 (18)0.0009 (16)
C660.054 (2)0.0440 (18)0.105 (3)0.0012 (15)0.018 (2)0.011 (2)
C670.081 (3)0.052 (2)0.096 (3)0.0046 (18)0.050 (2)0.009 (2)
C680.075 (2)0.0517 (18)0.0574 (19)0.0024 (17)0.0289 (18)0.0020 (16)
O6A0.070 (2)0.070 (2)0.079 (2)0.0185 (18)0.0209 (19)0.0046 (19)
C69A0.048 (7)0.065 (12)0.060 (7)0.005 (6)0.012 (4)0.009 (8)
C70A0.118 (14)0.114 (18)0.107 (8)0.045 (12)0.010 (8)0.050 (10)
O6B0.070 (2)0.070 (2)0.079 (2)0.0185 (18)0.0209 (19)0.0046 (19)
C69B0.048 (7)0.065 (12)0.060 (7)0.005 (6)0.012 (4)0.009 (8)
C70B0.118 (14)0.114 (18)0.107 (8)0.045 (12)0.010 (8)0.050 (10)
O8A0.0642 (17)0.0719 (19)0.0846 (19)0.0076 (14)0.0122 (14)0.0010 (15)
C71A0.078 (3)0.043 (4)0.045 (3)0.002 (3)0.002 (2)0.003 (3)
C72A0.125 (5)0.064 (5)0.081 (4)0.041 (3)0.018 (4)0.003 (3)
O8B0.0642 (17)0.0719 (19)0.0846 (19)0.0076 (14)0.0122 (14)0.0010 (15)
C71B0.078 (3)0.043 (4)0.045 (3)0.002 (3)0.002 (2)0.003 (3)
C72B0.125 (5)0.064 (5)0.081 (4)0.041 (3)0.018 (4)0.003 (3)
Geometric parameters (Å, º) top
O1—C81.387 (3)O5—C69A1.37 (3)
O1—C33A1.40 (2)O5—C621.387 (3)
O1—C33B1.51 (4)O5—C69B1.50 (4)
O3—C321.380 (3)O7—C461.392 (3)
O3—C35A1.39 (3)O7—C71A1.409 (8)
O3—C35B1.50 (4)O7—C71B1.54 (7)
C1—C61.407 (4)C37—C381.367 (4)
C1—C101.406 (4)C37—C461.416 (4)
C1—C21.414 (4)C37—C471.488 (3)
C2—C31.353 (4)C38—C391.405 (4)
C2—H2A0.9300C38—H38A0.9300
C3—C41.392 (5)C39—C441.410 (4)
C3—H3A0.9300C39—C401.422 (4)
C4—C51.360 (4)C40—C411.357 (5)
C4—H4A0.9300C40—H40A0.9300
C5—C61.418 (4)C41—C421.394 (5)
C5—H5A0.9300C41—H41A0.9300
C6—C71.436 (3)C42—C431.364 (5)
C7—C81.367 (3)C42—H42A0.9300
C7—C171.485 (3)C43—C441.425 (4)
C8—C91.426 (3)C43—H43A0.9300
C9—C101.371 (4)C44—C451.422 (4)
C9—C111.478 (3)C45—C461.377 (3)
C10—H10A0.9300C45—C531.497 (4)
C11—C161.388 (4)C47—C481.382 (4)
C11—C121.396 (4)C47—C521.397 (4)
C12—C131.381 (4)C48—C491.382 (4)
C12—H12A0.9300C48—H48A0.9300
C13—C141.369 (4)C49—C501.368 (4)
C13—H13A0.9300C49—H49A0.9300
C14—C151.374 (4)C50—C511.376 (4)
C14—H14A0.9300C50—H50A0.9300
C15—C161.386 (4)C51—C521.375 (4)
C15—H15A0.9300C51—H51A0.9300
C16—H16A0.9300C52—H52A0.9300
C17—C321.369 (3)C53—C621.367 (4)
C17—C181.433 (3)C53—C541.424 (4)
C18—C191.411 (4)C54—C551.419 (4)
C18—C231.416 (4)C54—C591.420 (4)
C19—C201.359 (4)C55—C561.364 (4)
C19—H19A0.9300C55—H55A0.9300
C20—C211.397 (4)C56—C571.397 (6)
C20—H20A0.9300C56—H56A0.9300
C21—C221.360 (4)C57—C581.346 (5)
C21—H21A0.9300C57—H57A0.9300
C22—C231.411 (4)C58—C591.422 (4)
C22—H22A0.9300C58—H58A0.9300
C23—C241.408 (4)C59—C601.400 (4)
C24—C251.360 (4)C60—C611.372 (4)
C24—H24A0.9300C60—H60A0.9300
C25—C321.430 (4)C61—C621.420 (4)
C25—C261.493 (4)C61—C631.489 (4)
C26—C271.375 (4)C63—C641.387 (4)
C26—C311.385 (4)C63—C681.389 (4)
C27—C281.392 (4)C64—C651.379 (4)
C27—H27A0.9300C64—H64A0.9300
C28—C291.359 (5)C65—C661.360 (4)
C28—H28A0.9300C65—H65A0.9300
C29—C301.363 (5)C66—C671.370 (5)
C29—H29A0.9300C66—H66A0.9300
C30—C311.392 (5)C67—C681.387 (4)
C30—H30A0.9300C67—H67A0.9300
C31—H31A0.9300C68—H68A0.9300
O2A—C33A1.416 (19)O6A—C69A1.41 (3)
O2A—C34A1.48 (3)O6A—C70A1.49 (5)
C33A—H33A0.9700C69A—H69A0.9700
C33A—H33B0.9700C69A—H69B0.9700
C34A—H34A0.9600C70A—H70A0.9600
C34A—H34B0.9600C70A—H70B0.9600
C34A—H34C0.9600C70A—H70C0.9600
O2B—C33B1.42 (3)O6B—C69B1.37 (4)
O2B—C34B1.63 (4)O6B—C70B1.38 (7)
C33B—H33C0.9700C69B—H69C0.9700
C33B—H33D0.9700C69B—H69D0.9700
C34B—H34D0.9600C70B—H70D0.9600
C34B—H34E0.9600C70B—H70E0.9600
C34B—H34F0.9600C70B—H70F0.9600
O4A—C36A1.364 (10)O8A—C71A1.357 (9)
O4A—C35A1.45 (3)O8A—C72A1.421 (8)
C35A—H35A0.9700C71A—H71A0.9700
C35A—H35B0.9700C71A—H71B0.9700
C36A—H36A0.9600C72A—H72A0.9600
C36A—H36B0.9600C72A—H72B0.9600
C36A—H36C0.9600C72A—H72C0.9600
O4B—C36B1.406 (17)O8B—C72B1.60 (7)
O4B—C35B1.45 (4)O8B—C71B1.66 (5)
C35B—H35C0.9700C71B—H71C0.9700
C35B—H35D0.9700C71B—H71D0.9700
C36B—H36D0.9600C72B—H72D0.9600
C36B—H36E0.9600C72B—H72E0.9600
C36B—H36F0.9600C72B—H72F0.9600
C8—O1—C33A118.8 (7)C69A—O5—C62119.3 (13)
C8—O1—C33B108.6 (11)C62—O5—C69B109.1 (13)
C32—O3—C35A119.3 (11)C46—O7—C71A116.2 (3)
C32—O3—C35B109.4 (15)C46—O7—C71B104 (2)
C6—C1—C10119.1 (2)C38—C37—C46118.3 (2)
C6—C1—C2119.3 (2)C38—C37—C47119.0 (2)
C10—C1—C2121.6 (3)C46—C37—C47122.7 (2)
C3—C2—C1120.9 (3)C37—C38—C39121.8 (3)
C3—C2—H2A119.6C37—C38—H38A119.1
C1—C2—H2A119.6C39—C38—H38A119.1
C2—C3—C4120.1 (3)C38—C39—C44119.2 (2)
C2—C3—H3A120.0C38—C39—C40121.2 (3)
C4—C3—H3A120.0C44—C39—C40119.5 (3)
C5—C4—C3121.0 (3)C41—C40—C39120.3 (3)
C5—C4—H4A119.5C41—C40—H40A119.8
C3—C4—H4A119.5C39—C40—H40A119.8
C4—C5—C6120.5 (3)C40—C41—C42120.3 (3)
C4—C5—H5A119.8C40—C41—H41A119.9
C6—C5—H5A119.8C42—C41—H41A119.9
C1—C6—C5118.2 (2)C43—C42—C41121.4 (3)
C1—C6—C7119.1 (2)C43—C42—H42A119.3
C5—C6—C7122.6 (2)C41—C42—H42A119.3
C8—C7—C6118.9 (2)C42—C43—C44120.0 (3)
C8—C7—C17120.7 (2)C42—C43—H43A120.0
C6—C7—C17120.4 (2)C44—C43—H43A120.0
C7—C8—O1118.1 (2)C39—C44—C45119.6 (2)
C7—C8—C9123.0 (2)C39—C44—C43118.4 (3)
O1—C8—C9118.9 (2)C45—C44—C43122.0 (3)
C10—C9—C8116.9 (2)C46—C45—C44118.8 (2)
C10—C9—C11119.5 (2)C46—C45—C53120.3 (2)
C8—C9—C11123.6 (2)C44—C45—C53120.9 (2)
C9—C10—C1122.9 (2)C45—C46—O7118.2 (2)
C9—C10—H10A118.6C45—C46—C37122.1 (2)
C1—C10—H10A118.6O7—C46—C37119.5 (2)
C16—C11—C12117.7 (3)C48—C47—C52118.2 (2)
C16—C11—C9120.0 (2)C48—C47—C37120.0 (2)
C12—C11—C9122.0 (2)C52—C47—C37121.6 (2)
C13—C12—C11120.5 (3)C49—C48—C47120.9 (3)
C13—C12—H12A119.7C49—C48—H48A119.5
C11—C12—H12A119.7C47—C48—H48A119.5
C14—C13—C12120.8 (3)C50—C49—C48120.1 (3)
C14—C13—H13A119.6C50—C49—H49A120.0
C12—C13—H13A119.6C48—C49—H49A120.0
C13—C14—C15119.8 (3)C49—C50—C51120.1 (3)
C13—C14—H14A120.1C49—C50—H50A120.0
C15—C14—H14A120.1C51—C50—H50A120.0
C14—C15—C16119.9 (3)C52—C51—C50120.2 (3)
C14—C15—H15A120.1C52—C51—H51A119.9
C16—C15—H15A120.1C50—C51—H51A119.9
C15—C16—C11121.3 (3)C51—C52—C47120.6 (3)
C15—C16—H16A119.3C51—C52—H52A119.7
C11—C16—H16A119.3C47—C52—H52A119.7
C32—C17—C18119.1 (2)C62—C53—C54119.3 (3)
C32—C17—C7120.5 (2)C62—C53—C45119.6 (2)
C18—C17—C7120.3 (2)C54—C53—C45121.1 (2)
C19—C18—C23118.7 (2)C55—C54—C59118.6 (3)
C19—C18—C17122.2 (2)C55—C54—C53122.5 (3)
C23—C18—C17119.0 (2)C59—C54—C53118.8 (3)
C20—C19—C18120.9 (3)C56—C55—C54120.5 (3)
C20—C19—H19A119.6C56—C55—H55A119.7
C18—C19—H19A119.6C54—C55—H55A119.7
C19—C20—C21120.8 (3)C55—C56—C57120.6 (4)
C19—C20—H20A119.6C55—C56—H56A119.7
C21—C20—H20A119.6C57—C56—H56A119.7
C22—C21—C20119.6 (3)C58—C57—C56120.6 (3)
C22—C21—H21A120.2C58—C57—H57A119.7
C20—C21—H21A120.2C56—C57—H57A119.7
C21—C22—C23121.6 (3)C57—C58—C59121.2 (4)
C21—C22—H22A119.2C57—C58—H58A119.4
C23—C22—H22A119.2C59—C58—H58A119.4
C24—C23—C22122.5 (3)C60—C59—C54119.4 (3)
C24—C23—C18119.0 (2)C60—C59—C58122.2 (3)
C22—C23—C18118.4 (3)C54—C59—C58118.4 (3)
C25—C24—C23122.7 (3)C61—C60—C59122.3 (3)
C25—C24—H24A118.7C61—C60—H60A118.8
C23—C24—H24A118.7C59—C60—H60A118.8
C24—C25—C32117.7 (2)C60—C61—C62117.6 (3)
C24—C25—C26121.3 (2)C60—C61—C63120.5 (3)
C32—C25—C26121.0 (2)C62—C61—C63121.9 (2)
C27—C26—C31118.5 (3)C53—C62—O5118.9 (2)
C27—C26—C25121.1 (3)C53—C62—C61122.6 (2)
C31—C26—C25120.3 (3)O5—C62—C61118.4 (2)
C26—C27—C28120.3 (3)C64—C63—C68118.3 (3)
C26—C27—H27A119.8C64—C63—C61120.0 (2)
C28—C27—H27A119.8C68—C63—C61121.7 (3)
C29—C28—C27120.8 (3)C65—C64—C63120.8 (3)
C29—C28—H28A119.6C65—C64—H64A119.6
C27—C28—H28A119.6C63—C64—H64A119.6
C28—C29—C30119.6 (3)C66—C65—C64120.3 (3)
C28—C29—H29A120.2C66—C65—H65A119.9
C30—C29—H29A120.2C64—C65—H65A119.9
C29—C30—C31120.3 (3)C65—C66—C67120.2 (3)
C29—C30—H30A119.8C65—C66—H66A119.9
C31—C30—H30A119.8C67—C66—H66A119.9
C26—C31—C30120.4 (3)C66—C67—C68120.3 (3)
C26—C31—H31A119.8C66—C67—H67A119.9
C30—C31—H31A119.8C68—C67—H67A119.9
C17—C32—O3119.2 (2)C67—C68—C63120.1 (3)
C17—C32—C25122.3 (2)C67—C68—H68A119.9
O3—C32—C25118.4 (2)C63—C68—H68A119.9
C33A—O2A—C34A103.1 (12)C69A—O6A—C70A111 (2)
O1—C33A—O2A111.0 (14)O5—C69A—O6A110 (2)
O1—C33A—H33A109.4O5—C69A—H69A109.6
O2A—C33A—H33A109.4O6A—C69A—H69A109.6
O1—C33A—H33B109.4O5—C69A—H69B109.6
O2A—C33A—H33B109.4O6A—C69A—H69B109.6
H33A—C33A—H33B108.0H69A—C69A—H69B108.1
C33B—O2B—C34B104 (2)C69B—O6B—C70B111 (3)
O2B—C33B—O1102 (2)O6B—C69B—O5106 (2)
O2B—C33B—H33C111.3O6B—C69B—H69C110.5
O1—C33B—H33C111.3O5—C69B—H69C110.5
O2B—C33B—H33D111.3O6B—C69B—H69D110.5
O1—C33B—H33D111.3O5—C69B—H69D110.5
H33C—C33B—H33D109.2H69C—C69B—H69D108.6
O2B—C34B—H34D109.5O6B—C70B—H70D109.5
O2B—C34B—H34E109.5O6B—C70B—H70E109.5
H34D—C34B—H34E109.5H70D—C70B—H70E109.5
O2B—C34B—H34F109.5O6B—C70B—H70F109.5
H34D—C34B—H34F109.5H70D—C70B—H70F109.5
H34E—C34B—H34F109.5H70E—C70B—H70F109.5
C36A—O4A—C35A112.7 (13)C71A—O8A—C72A110.9 (5)
O3—C35A—O4A109.9 (19)O8A—C71A—O7115.0 (5)
O3—C35A—H35A109.7O8A—C71A—H71A108.5
O4A—C35A—H35A109.7O7—C71A—H71A108.5
O3—C35A—H35B109.7O8A—C71A—H71B108.5
O4A—C35A—H35B109.7O7—C71A—H71B108.5
H35A—C35A—H35B108.2H71A—C71A—H71B107.5
C36B—O4B—C35B116 (2)C72B—O8B—C71B122 (4)
O4B—C35B—O399 (2)O7—C71B—O8B92 (3)
O4B—C35B—H35C111.9O7—C71B—H71C113.4
O3—C35B—H35C111.9O8B—C71B—H71C113.4
O4B—C35B—H35D111.9O7—C71B—H71D113.4
O3—C35B—H35D111.9O8B—C71B—H71D113.4
H35C—C35B—H35D109.6H71C—C71B—H71D110.7
O4B—C36B—H36D109.5O8B—C72B—H72D109.5
O4B—C36B—H36E109.5O8B—C72B—H72E109.5
H36D—C36B—H36E109.5H72D—C72B—H72E109.5
O4B—C36B—H36F109.5O8B—C72B—H72F109.5
H36D—C36B—H36F109.5H72D—C72B—H72F109.5
H36E—C36B—H36F109.5H72E—C72B—H72F109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O6Ai0.932.593.448 (6)153
C43—H43A···O2Bii0.932.573.304 (7)136
C51—H51A···O10.932.383.233 (3)152
Symmetry codes: (i) x+2, y1/2, z+1; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC36H30O4
Mr526.60
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)11.3166 (3), 19.4841 (3), 14.0155 (4)
β (°) 110.172 (3)
V3)2900.77 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.43 × 0.40 × 0.36
Data collection
DiffractometerOxford Xcalibur Eos CCD
diffractometer
Absorption correctionMulti-scan
(CrysAlis CCD; Oxford Diffraction, 2006)
Tmin, Tmax0.828, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
12553, 6211, 4315
Rint0.020
(sin θ/λ)max1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.069, 1.01
No. of reflections6211
No. of parameters769
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.20

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Berndt, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O6Ai0.932.593.448 (6)153
C43—H43A···O2Bii0.932.573.304 (7)136
C51—H51A···O10.932.383.233 (3)152
Symmetry codes: (i) x+2, y1/2, z+1; (ii) x, y, z+1.
 

Acknowledgements

The authors are grateful to the Natural Science Foundation of Fujian province (No. 2010 J01055) for financial support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationBrandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBrunel, J. M. (2006). Chem. Rev. 105, 857–897.  Web of Science CrossRef
First citationLou, S., Moquist, P. N. & Schaus, S. E. (2006). J. Am. Chem. Soc. 128, 12660–12661.  Web of Science CrossRef PubMed CAS
First citationOxford Diffraction (2006). CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWu, T. R., Shen, L. X. & Chong, J. M. (2004). Org. Lett, 6, 2701–2704.  Web of Science CrossRef PubMed CAS

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