8-Hydr­oxy-7-phenyl-2,6-dioxabicyclo­[3.3.1]nonan-3-one

Hari Kumar, B.; Varghese, B.; Jaya Kumar, G.; Ajitha Bai, M.D.

doi:10.1107/S1600536806046599

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8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

B. Hari Kumar, B. Varghese, G. Jaya Kumar and M. D. Ajitha Bai

The title compound, C₁₃H₁₄O₄, is isolated from the plant Goniothalamus wightii. There are four independent molecules in the asymmetric unit, having similar conformations. Two molecules are linked via O—H

O hydrogen bonds, forming chains along the a axis in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046599/ob2083sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046599/ob2083Isup2.hkl Contains datablock I

CCDC reference: 630199

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.049
wR factor = 0.147
Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O2D    -   C10D    ..       7.28 su

Alert level C
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...       0.30
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.85
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....         24
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.29 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.66 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.45 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C3B
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C4D
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C3D
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6D
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C7D
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.03
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT751_ALERT_4_C Bond    Calc     1.42083, Rep    1.420(4) ......  Senseless su
              C7A  -O1A     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.53478, Rep    1.534(6) ......  Senseless su
              C7A  -C12A    1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.43740, Rep    1.438(3) ......  Senseless su
              C7B  -O1B     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.52111, Rep    1.521(4) ......  Senseless su
              C7B  -C12B    1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.42451, Rep    1.425(3) ......  Senseless su
              C7C  -O1C     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.52440, Rep    1.524(4) ......  Senseless su
              C7C  -C12C    1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.42796, Rep    1.428(4) ......  Senseless su
              C7D  -O1D     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.50814, Rep    1.508(6) ......  Senseless su
              C7D  -C12D    1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      107.61, Rep  107.62(16) ......  Senseless su
              O1A  -C7A  -C6A     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      110.17, Rep    110.2(3) ......  Senseless su
              O1A  -C7A  -C12A    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      112.89, Rep    112.9(2) ......  Senseless su
              C6A  -C7A  -C12A    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      107.26, Rep    107.3(5) ......  Senseless su
              O3A  -C12A -C7A     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      111.25, Rep    111.3(4) ......  Senseless su
              C11A -C12A -C7A     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      114.17, Rep    114.2(3) ......  Senseless su
              C7A  -O1A  -C8A     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      105.88, Rep  105.87(14) ......  Senseless su
              O1B  -C7B  -C6B     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      110.26, Rep    110.3(2) ......  Senseless su
              O1B  -C7B  -C12B    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      113.04, Rep  113.02(17) ......  Senseless su
              C6B  -C7B  -C12B    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      107.41, Rep    107.4(3) ......  Senseless su
              O3B  -C12B -C7B     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      111.24, Rep    111.2(3) ......  Senseless su
              C11B -C12B -C7B     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      115.13, Rep    115.1(2) ......  Senseless su
              C8B  -O1B  -C7B     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      105.94, Rep  105.91(14) ......  Senseless su
              O1C  -C7C  -C6C     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      111.10, Rep    111.1(2) ......  Senseless su
              O1C  -C7C  -C12C    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      113.68, Rep  113.72(17) ......  Senseless su
              C6C  -C7C  -C12C    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      108.22, Rep    108.2(3) ......  Senseless su
              O3C  -C12C -C7C     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      109.71, Rep    109.7(3) ......  Senseless su
              C11C -C12C -C7C     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      114.51, Rep    114.5(2) ......  Senseless su
              C7C  -O1C  -C8C     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      107.42, Rep  107.41(16) ......  Senseless su
              O1D  -C7D  -C6D     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      111.06, Rep    111.0(3) ......  Senseless su
              O1D  -C7D  -C12D    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      114.35, Rep    114.3(2) ......  Senseless su
              C6D  -C7D  -C12D    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      108.80, Rep    108.8(5) ......  Senseless su
              O3D  -C12D -C7D     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      111.47, Rep    111.5(4) ......  Senseless su
              C11D -C12D -C7D     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      113.50, Rep    113.5(3) ......  Senseless su
              C7D  -O1D  -C8D     1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       53.94, Rep   53.97(18) ......  Senseless su
              C5A -C6A -C7A -O1A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -128.02, Rep -127.99(18) ......  Senseless su
              C1A -C6A -C7A -O1A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -67.85, Rep    -67.9(3) ......  Senseless su
              C5A -C6A -C7A -C12A   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      110.19, Rep    110.2(3) ......  Senseless su
              C1A -C6A -C7A -C12A   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       67.59, Rep     67.6(6) ......  Senseless su
              O2A -C11A-C12A-C7A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -55.09, Rep    -55.0(7) ......  Senseless su
              C13A-C11A-C12A-C7A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      173.56, Rep    173.6(4) ......  Senseless su
              O1A -C7A -C12A-O3A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -66.11, Rep    -66.1(4) ......  Senseless su
              C6A -C7A -C12A-O3A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       51.27, Rep     51.2(6) ......  Senseless su
              O1A -C7A -C12A-C11A   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      171.61, Rep    171.6(4) ......  Senseless su
              C6A -C7A -C12A-C11A   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -178.35, Rep   -178.3(3) ......  Senseless su
              C6A -C7A -O1A -C8A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -54.89, Rep    -54.8(5) ......  Senseless su
              C12A-C7A -O1A -C8A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       61.42, Rep     61.4(5) ......  Senseless su
              C13A-C8A -O1A -C7A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -59.58, Rep    -59.6(5) ......  Senseless su
              C9A -C8A -O1A -C7A    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -114.16, Rep -114.19(15) ......  Senseless su
              C5B -C6B -C7B -O1B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       63.99, Rep   64.00(15) ......  Senseless su
              C1B -C6B -C7B -O1B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      125.03, Rep  125.02(18) ......  Senseless su
              C5B -C6B -C7B -C12B   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -56.82, Rep  -56.79(18) ......  Senseless su
              C1B -C6B -C7B -C12B   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       65.14, Rep     65.1(3) ......  Senseless su
              O2B -C11B-C12B-C7B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -57.23, Rep    -57.3(4) ......  Senseless su
              C13B-C11B-C12B-C7B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      175.17, Rep    175.2(3) ......  Senseless su
              O1B -C7B -C12B-O3B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -66.54, Rep    -66.6(3) ......  Senseless su
              C6B -C7B -C12B-O3B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       51.47, Rep     51.5(3) ......  Senseless su
              O1B -C7B -C12B-C11B   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      169.76, Rep    169.8(2) ......  Senseless su
              C6B -C7B -C12B-C11B   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -62.15, Rep    -62.2(4) ......  Senseless su
              C9B -C8B -O1B -C7B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       59.09, Rep     59.1(4) ......  Senseless su
              C13B-C8B -O1B -C7B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -175.74, Rep   -175.7(2) ......  Senseless su
              C6B -C7B -O1B -C8B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -53.14, Rep    -53.1(4) ......  Senseless su
              C12B-C7B -O1B -C8B    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       63.97, Rep   64.06(15) ......  Senseless su
              C5C -C6C -C7C -O1C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -112.33, Rep -112.31(15) ......  Senseless su
              C1C -C6C -C7C -O1C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -58.30, Rep  -58.27(18) ......  Senseless su
              C5C -C6C -C7C -C12C   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      125.40, Rep  125.37(18) ......  Senseless su
              C1C -C6C -C7C -C12C   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       65.35, Rep     65.4(3) ......  Senseless su
              O2C -C11C-C12C-C7C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -57.91, Rep    -57.9(4) ......  Senseless su
              C13C-C11C-C12C-C7C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      176.75, Rep    176.8(3) ......  Senseless su
              O1C -C7C -C12C-O3C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -63.87, Rep    -63.8(3) ......  Senseless su
              C6C -C7C -C12C-O3C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       52.31, Rep     52.3(3) ......  Senseless su
              O1C -C7C -C12C-C11C   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      171.68, Rep    171.7(2) ......  Senseless su
              C6C -C7C -C12C-C11C   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -177.62, Rep   -177.6(2) ......  Senseless su
              C6C -C7C -O1C -C8C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -53.71, Rep    -53.7(4) ......  Senseless su
              C12C-C7C -O1C -C8C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       58.69, Rep     58.6(4) ......  Senseless su
              C13C-C8C -O1C -C7C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -63.16, Rep    -63.2(4) ......  Senseless su
              C9C -C8C -O1C -C7C    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -109.62, Rep -109.66(19) ......  Senseless su
              C5D -C6D -C7D -O1D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       68.88, Rep   68.87(19) ......  Senseless su
              C1D -C6D -C7D -O1D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      126.64, Rep    126.6(3) ......  Senseless su
              C5D -C6D -C7D -C12D   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -54.86, Rep    -54.8(3) ......  Senseless su
              C1D -C6D -C7D -C12D   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       69.47, Rep     69.5(7) ......  Senseless su
              O2D -C11D-C12D-C7D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -53.24, Rep    -53.2(8) ......  Senseless su
              C13D-C11D-C12D-C7D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      174.37, Rep    174.4(4) ......  Senseless su
              O1D -C7D -C12D-O3D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -63.87, Rep    -63.9(5) ......  Senseless su
              C6D -C7D -C12D-O3D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       49.02, Rep     49.0(6) ......  Senseless su
              O1D -C7D -C12D-C11D   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      170.79, Rep    170.7(4) ......  Senseless su
              C6D -C7D -C12D-C11D   1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -179.71, Rep   -179.7(4) ......  Senseless su
              C6D -C7D -O1D -C8D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -53.99, Rep    -54.0(5) ......  Senseless su
              C12D-C7D -O1D -C8D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       61.39, Rep     61.4(6) ......  Senseless su
              C13D-C8D -O1D -C7D    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -60.81, Rep    -60.8(6) ......  Senseless su
              C9D -C8D -O1D -C7D    1.555   1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C13 H14 O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              C13 H14 O4
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.30

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.850
            Tmax scaled      0.850 Tmin scaled      0.802
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           67.92
           From the CIF: _reflns_number_total               4350
           Count of symmetry unique reflns         4351
           Completeness (_total/calc)             99.98%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7C    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7D    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8C    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8D    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11A   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11B   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11C   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11D   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12B   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12C   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12D   = .          S

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
 107 ALERT level C = Check and explain
  20 ALERT level G = General alerts; check

  18 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
  94 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and WinGX (Farrugia, 1999).

8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one top

Crystal data top

C₁₃H₁₄O₄	F(000) = 992
M_r = 234.24	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54180 Å
a = 7.1313 (5) Å	Cell parameters from 25 reflections
b = 35.442 (3) Å	θ = 20–30°
c = 9.3061 (16) Å	µ = 0.81 mm⁻¹
β = 90.454 (9)°	T = 293 K
V = 2352.0 (5) Å³	Prism, colourless
Z = 8	0.3 × 0.2 × 0.2 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	3927 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 67.9°, θ_min = 2.5°
ω–2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→42
T_min = 0.943, T_max = 0.999	l = −9→11
4627 measured reflections	2 standard reflections every 60 min
4350 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0822P)² + 0.8943P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.147	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.24 e Å⁻³
4350 reflections	Δρ_min = −0.23 e Å⁻³
542 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0083 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with no Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (3)

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

	x	y	z	U_iso*/U_eq
C1A	0.0643 (3)	0.05926 (6)	0.2652 (3)	0.0793 (15)
H1A	0.0795	0.0762	0.1898	0.095*
C2A	−0.0732 (3)	0.03152 (6)	0.2569 (3)	0.097 (2)
H2A	−0.1499	0.0299	0.1759	0.116*
C3A	−0.0959 (3)	0.00624 (6)	0.3696 (3)	0.104 (3)
H3A	−0.1878	−0.0123	0.3640	0.125*
C4A	0.0189 (3)	0.00869 (6)	0.4906 (3)	0.0925 (19)
H4A	0.0037	−0.0082	0.5660	0.111*
C5A	0.1564 (3)	0.03642 (6)	0.4990 (3)	0.0772 (14)
H5A	0.2331	0.0381	0.5800	0.093*
C6A	0.1791 (3)	0.06171 (6)	0.3863 (3)	0.0577 (10)
C7A	0.3231 (3)	0.09256 (6)	0.3963 (3)	0.0556 (10)
H7A	0.3321	0.1050	0.3025	0.067*
C8A	0.6495 (6)	0.10154 (16)	0.4463 (6)	0.0690 (14)
H8A	0.7643	0.0873	0.4675	0.083*
C9A	0.6805 (7)	0.12476 (16)	0.3107 (7)	0.0701 (13)
H91A	0.8100	0.1332	0.3102	0.084*
H92A	0.6625	0.1084	0.2282	0.084*
C10A	0.5561 (7)	0.15870 (16)	0.2926 (7)	0.0733 (15)
C11A	0.4361 (8)	0.14961 (16)	0.5321 (7)	0.0785 (15)
H11A	0.4053	0.1664	0.6122	0.094*
C12A	0.2754 (7)	0.12240 (15)	0.5098 (8)	0.0775 (16)
H12A	0.2493	0.1097	0.6009	0.093*
C13A	0.6140 (9)	0.1286 (2)	0.5695 (8)	0.0893 (18)
H13A	0.5993	0.1148	0.6587	0.107*
H14A	0.7180	0.1460	0.5804	0.107*
O1A	0.4984 (4)	0.07545 (9)	0.4293 (4)	0.0625 (8)
O2A	0.4602 (5)	0.17218 (10)	0.4044 (5)	0.0835 (12)
O3A	0.1089 (5)	0.14143 (13)	0.4617 (9)	0.130 (3)
H31A	0.1300	0.1641	0.4546	0.195*
O4A	0.5451 (6)	0.17613 (14)	0.1823 (6)	0.1009 (16)
C1B	0.9585 (3)	0.11424 (6)	0.9156 (2)	0.0873 (18)
H1B	0.8428	0.1263	0.9197	0.105*
C2B	0.9677 (3)	0.07609 (6)	0.8818 (2)	0.125 (3)
H2B	0.8583	0.0626	0.8633	0.149*
C3B	1.1406 (3)	0.05806 (6)	0.8758 (2)	0.141 (4)
H3B	1.1468	0.0325	0.8532	0.169*
C4B	1.3042 (3)	0.07819 (6)	0.9035 (2)	0.122 (3)
H4B	1.4199	0.0661	0.8995	0.146*
C5B	1.2949 (3)	0.11635 (6)	0.9373 (2)	0.0778 (15)
H5B	1.4044	0.1298	0.9559	0.093*
C6B	1.1221 (3)	0.13437 (6)	0.9433 (2)	0.0564 (11)
C7B	1.1107 (3)	0.17539 (6)	0.9841 (2)	0.0430 (8)
H7B	1.2378	0.1854	0.9974	0.052*
C8B	0.9761 (5)	0.21359 (11)	1.1732 (4)	0.0430 (8)
H8B	0.9063	0.2111	1.2630	0.052*
C9B	1.1523 (5)	0.23592 (12)	1.2034 (4)	0.0440 (8)
H91B	1.1249	0.2541	1.2782	0.053*
H92B	1.2462	0.2187	1.2416	0.053*
C10B	1.2367 (5)	0.25668 (11)	1.0795 (4)	0.0441 (8)
C11B	0.9684 (5)	0.23835 (11)	0.9295 (4)	0.0431 (8)
H11B	0.8938	0.2521	0.8578	0.052*
C12B	1.0072 (5)	0.19920 (12)	0.8730 (4)	0.0431 (8)
H12B	0.8871	0.1870	0.8508	0.052*
C13B	0.8569 (5)	0.23565 (12)	1.0670 (4)	0.0462 (9)
H13B	0.8305	0.2606	1.1042	0.055*
H14B	0.7389	0.2228	1.0495	0.055*
O1B	1.0143 (4)	0.17648 (8)	1.1191 (3)	0.0479 (6)
O2B	1.1453 (4)	0.25878 (8)	0.9537 (3)	0.0451 (6)
O3B	1.1172 (4)	0.19953 (9)	0.7467 (3)	0.0535 (7)
H31B	1.0526	0.2065	0.6785	0.080*
O4B	1.3868 (4)	0.27263 (11)	1.0897 (3)	0.0641 (9)
C1C	0.8143 (3)	0.38168 (6)	0.6782 (2)	0.0773 (15)
H1C	0.9187	0.3667	0.6603	0.093*
C2C	0.8365 (3)	0.41991 (6)	0.7069 (2)	0.110 (3)
H2C	0.9558	0.4305	0.7084	0.132*
C3C	0.6805 (3)	0.44227 (6)	0.7336 (2)	0.116 (3)
H3C	0.6953	0.4678	0.7529	0.139*
C4C	0.5022 (3)	0.42640 (6)	0.7315 (2)	0.101 (2)
H4C	0.3978	0.4414	0.7494	0.122*
C5C	0.4800 (3)	0.38817 (6)	0.7027 (2)	0.0784 (15)
H5C	0.3608	0.3775	0.7013	0.094*
C6C	0.6360 (3)	0.36581 (6)	0.6761 (2)	0.0556 (11)
C7C	0.6132 (3)	0.32445 (6)	0.6356 (2)	0.0444 (8)
H7C	0.7378	0.3134	0.6222	0.053*
C8C	0.4740 (5)	0.28716 (11)	0.4468 (4)	0.0443 (8)
H8C	0.4028	0.2900	0.3570	0.053*
C9C	0.6501 (5)	0.26435 (12)	0.4151 (4)	0.0467 (9)
H91C	0.6206	0.2463	0.3399	0.056*
H92C	0.7446	0.2814	0.3779	0.056*
C10C	0.7333 (5)	0.24330 (12)	0.5404 (4)	0.0447 (8)
C11C	0.4683 (5)	0.26237 (11)	0.6886 (4)	0.0416 (8)
H11C	0.3944	0.2486	0.7597	0.050*
C12C	0.5090 (5)	0.30127 (11)	0.7475 (4)	0.0426 (8)
H12C	0.3894	0.3138	0.7674	0.051*
C13C	0.3548 (5)	0.26489 (12)	0.5514 (4)	0.0466 (9)
H13C	0.2368	0.2777	0.5683	0.056*
H14C	0.3286	0.2399	0.5139	0.056*
O1C	0.5162 (4)	0.32416 (8)	0.5012 (3)	0.0476 (6)
O2C	0.6430 (4)	0.24182 (8)	0.6658 (3)	0.0446 (6)
O3C	0.6170 (4)	0.30096 (9)	0.8748 (3)	0.0516 (7)
H31C	0.5540	0.2925	0.9408	0.077*
O4C	0.8803 (5)	0.22639 (11)	0.5309 (3)	0.0663 (9)
C1D	−0.3835 (3)	0.45678 (6)	0.1017 (3)	0.0847 (17)
H1D	−0.3290	0.4513	0.0137	0.102*
C2D	−0.5171 (3)	0.48520 (6)	0.1115 (3)	0.103 (2)
H2D	−0.5520	0.4988	0.0300	0.124*
C3D	−0.5986 (3)	0.49338 (6)	0.2431 (3)	0.100 (2)
H3D	−0.6879	0.5124	0.2496	0.120*
C4D	−0.5464 (3)	0.47313 (6)	0.3649 (3)	0.132 (4)
H4D	−0.6009	0.4786	0.4529	0.159*
C5D	−0.4128 (3)	0.44470 (6)	0.3552 (3)	0.105 (3)
H5D	−0.3780	0.4312	0.4367	0.127*
C6D	−0.3314 (3)	0.43653 (6)	0.2236 (3)	0.0517 (9)
C7D	−0.1840 (3)	0.40637 (6)	0.2159 (3)	0.0498 (9)
H7D	−0.1762	0.3941	0.3102	0.060*
C8D	0.1465 (7)	0.39881 (18)	0.1794 (8)	0.0804 (18)
H8D	0.2603	0.4135	0.1611	0.096*
C9D	0.1762 (7)	0.37639 (17)	0.3153 (7)	0.0775 (15)
H91D	0.1512	0.3926	0.3970	0.093*
H92D	0.3067	0.3688	0.3211	0.093*
C10D	0.0545 (7)	0.34142 (16)	0.3268 (8)	0.0759 (17)
C11D	−0.0562 (9)	0.3507 (2)	0.0862 (8)	0.0889 (18)
H11D	−0.0814	0.3339	0.0047	0.107*
C12D	−0.2225 (8)	0.37629 (16)	0.1049 (8)	0.0789 (16)
H12D	−0.2463	0.3889	0.0129	0.095*
C13D	0.1161 (10)	0.3724 (2)	0.0560 (8)	0.099 (2)
H13D	0.1017	0.3865	−0.0329	0.119*
H14D	0.2223	0.3555	0.0466	0.119*
O1D	−0.0089 (4)	0.42460 (9)	0.1901 (4)	0.0651 (9)
O2D	−0.0326 (5)	0.32787 (11)	0.2144 (5)	0.0833 (11)
O3D	−0.3864 (6)	0.35684 (14)	0.1428 (9)	0.138 (3)
H31D	−0.4076	0.3402	0.0836	0.207*
O4D	0.0435 (6)	0.32420 (15)	0.4391 (6)	0.1080 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.067 (3)	0.088 (4)	0.082 (4)	−0.015 (3)	0.002 (3)	−0.003 (3)
C2A	0.080 (4)	0.108 (5)	0.102 (5)	−0.024 (4)	−0.004 (3)	−0.016 (4)
C3A	0.088 (4)	0.079 (4)	0.146 (7)	−0.027 (3)	0.036 (4)	−0.037 (4)
C4A	0.111 (5)	0.061 (3)	0.106 (5)	−0.021 (3)	0.034 (4)	0.003 (3)
C5A	0.095 (4)	0.058 (3)	0.078 (3)	−0.014 (3)	0.007 (3)	0.008 (3)
C6A	0.058 (2)	0.050 (2)	0.066 (3)	−0.003 (2)	0.012 (2)	−0.002 (2)
C7A	0.046 (2)	0.052 (2)	0.069 (3)	0.0019 (18)	0.0052 (18)	0.013 (2)
C8A	0.044 (2)	0.076 (3)	0.088 (4)	0.004 (2)	0.000 (2)	0.019 (3)
C9A	0.047 (2)	0.074 (3)	0.090 (4)	−0.002 (2)	0.011 (2)	0.015 (3)
C10A	0.044 (2)	0.065 (3)	0.111 (4)	−0.014 (2)	−0.006 (3)	0.028 (3)
C11A	0.073 (3)	0.063 (3)	0.100 (4)	−0.013 (3)	0.021 (3)	−0.015 (3)
C12A	0.056 (3)	0.052 (3)	0.126 (5)	−0.004 (2)	0.027 (3)	−0.014 (3)
C13A	0.073 (4)	0.099 (5)	0.096 (4)	−0.023 (3)	−0.013 (3)	0.002 (4)
O1A	0.0497 (16)	0.0546 (17)	0.083 (2)	0.0097 (14)	0.0099 (15)	0.0103 (16)
O2A	0.058 (2)	0.0512 (19)	0.141 (4)	−0.0030 (16)	0.012 (2)	0.005 (2)
O3A	0.046 (2)	0.062 (2)	0.282 (8)	0.0100 (18)	0.030 (3)	−0.014 (3)
O4A	0.060 (2)	0.106 (3)	0.137 (4)	−0.013 (2)	−0.005 (2)	0.064 (3)
C1B	0.114 (5)	0.060 (3)	0.087 (4)	−0.010 (3)	−0.029 (3)	−0.008 (3)
C2B	0.217 (11)	0.065 (4)	0.090 (5)	−0.027 (5)	−0.031 (6)	−0.015 (3)
C3B	0.284 (14)	0.052 (4)	0.087 (5)	0.002 (6)	0.050 (7)	−0.013 (3)
C4B	0.187 (9)	0.069 (4)	0.111 (6)	0.050 (5)	0.061 (6)	0.004 (4)
C5B	0.097 (4)	0.059 (3)	0.077 (3)	0.020 (3)	0.020 (3)	0.000 (2)
C6B	0.085 (3)	0.048 (2)	0.0359 (19)	0.005 (2)	0.0032 (19)	−0.0013 (17)
C7B	0.0481 (19)	0.045 (2)	0.0356 (17)	0.0030 (16)	0.0083 (14)	−0.0023 (15)
C8B	0.0434 (19)	0.049 (2)	0.0367 (17)	0.0037 (16)	0.0119 (14)	0.0008 (15)
C9B	0.048 (2)	0.050 (2)	0.0334 (17)	0.0040 (17)	0.0021 (14)	0.0012 (15)
C10B	0.045 (2)	0.052 (2)	0.0360 (17)	0.0008 (17)	0.0052 (14)	−0.0041 (16)
C11B	0.0405 (18)	0.053 (2)	0.0357 (17)	0.0037 (16)	−0.0004 (14)	−0.0016 (16)
C12B	0.0411 (18)	0.053 (2)	0.0353 (17)	0.0011 (17)	0.0020 (14)	−0.0023 (16)
C13B	0.0390 (18)	0.056 (2)	0.0441 (19)	0.0055 (16)	0.0066 (15)	−0.0004 (17)
O1B	0.0575 (15)	0.0472 (15)	0.0393 (13)	−0.0008 (12)	0.0116 (11)	0.0031 (11)
O2B	0.0463 (14)	0.0531 (15)	0.0361 (12)	−0.0055 (12)	0.0039 (10)	0.0030 (11)
O3B	0.0589 (16)	0.0682 (18)	0.0335 (12)	0.0092 (14)	0.0069 (11)	−0.0009 (12)
O4B	0.0579 (17)	0.090 (2)	0.0444 (15)	−0.0286 (17)	0.0033 (13)	−0.0002 (15)
C1C	0.101 (4)	0.066 (3)	0.065 (3)	−0.029 (3)	−0.002 (3)	0.007 (2)
C2C	0.176 (8)	0.069 (4)	0.085 (4)	−0.053 (5)	−0.008 (5)	0.009 (3)
C3C	0.238 (11)	0.056 (3)	0.053 (3)	−0.024 (5)	−0.005 (5)	0.000 (3)
C4C	0.166 (7)	0.066 (4)	0.072 (4)	0.034 (4)	0.007 (4)	−0.003 (3)
C5C	0.106 (4)	0.060 (3)	0.069 (3)	0.017 (3)	0.011 (3)	0.000 (2)
C6C	0.083 (3)	0.046 (2)	0.038 (2)	−0.007 (2)	−0.0004 (19)	0.0007 (16)
C7C	0.047 (2)	0.051 (2)	0.0349 (17)	−0.0001 (17)	−0.0010 (14)	0.0007 (16)
C8C	0.046 (2)	0.052 (2)	0.0350 (17)	−0.0030 (16)	−0.0065 (14)	0.0010 (15)
C9C	0.048 (2)	0.056 (2)	0.0360 (18)	−0.0028 (17)	0.0017 (15)	−0.0006 (17)
C10C	0.0436 (19)	0.056 (2)	0.0347 (17)	0.0036 (17)	−0.0001 (14)	−0.0025 (16)
C11C	0.0393 (17)	0.051 (2)	0.0348 (17)	−0.0021 (16)	0.0061 (14)	0.0042 (15)
C12C	0.0405 (18)	0.052 (2)	0.0352 (17)	0.0015 (16)	0.0021 (13)	0.0010 (16)
C13C	0.0397 (18)	0.058 (2)	0.0424 (19)	−0.0035 (17)	−0.0010 (15)	−0.0018 (17)
O1C	0.0559 (15)	0.0488 (14)	0.0382 (13)	0.0019 (13)	−0.0036 (11)	0.0031 (11)
O2C	0.0478 (14)	0.0511 (15)	0.0348 (12)	0.0051 (12)	−0.0001 (10)	0.0022 (11)
O3C	0.0622 (16)	0.0602 (16)	0.0325 (12)	−0.0035 (14)	−0.0003 (11)	−0.0006 (12)
O4C	0.0598 (18)	0.092 (2)	0.0476 (15)	0.0272 (18)	0.0032 (13)	−0.0038 (15)
C1D	0.121 (5)	0.068 (3)	0.065 (3)	0.024 (3)	0.005 (3)	0.010 (3)
C2D	0.127 (6)	0.062 (3)	0.121 (6)	0.020 (4)	−0.016 (5)	0.030 (4)
C3D	0.088 (4)	0.069 (4)	0.143 (7)	0.027 (3)	0.011 (4)	0.006 (4)
C4D	0.136 (7)	0.161 (8)	0.099 (5)	0.077 (7)	0.026 (5)	−0.006 (5)
C5D	0.106 (5)	0.146 (7)	0.065 (3)	0.064 (5)	0.018 (3)	0.015 (4)
C6D	0.053 (2)	0.047 (2)	0.055 (2)	−0.0012 (18)	0.0003 (18)	−0.0010 (18)
C7D	0.046 (2)	0.047 (2)	0.056 (2)	−0.0028 (17)	0.0008 (17)	0.0048 (18)
C8D	0.039 (2)	0.080 (4)	0.123 (5)	−0.011 (2)	0.006 (3)	0.037 (4)
C9D	0.051 (3)	0.075 (3)	0.106 (4)	−0.005 (2)	−0.015 (3)	0.015 (3)
C10D	0.047 (2)	0.067 (3)	0.114 (5)	0.020 (2)	0.013 (3)	0.035 (3)
C11D	0.086 (4)	0.085 (4)	0.096 (4)	0.030 (3)	−0.011 (3)	−0.024 (3)
C12D	0.065 (3)	0.064 (3)	0.108 (4)	0.011 (3)	−0.018 (3)	−0.026 (3)
C13D	0.088 (4)	0.113 (5)	0.097 (5)	0.036 (4)	0.032 (4)	0.009 (4)
O1D	0.0488 (16)	0.0527 (17)	0.094 (2)	−0.0091 (13)	−0.0045 (15)	0.0137 (16)
O2D	0.060 (2)	0.063 (2)	0.127 (3)	0.0033 (17)	−0.005 (2)	−0.001 (2)
O3D	0.054 (2)	0.071 (3)	0.288 (8)	−0.004 (2)	−0.032 (3)	−0.054 (4)
O4D	0.075 (3)	0.111 (3)	0.138 (4)	0.029 (2)	0.018 (2)	0.064 (3)

Geometric parameters (Å, º) top

C1A—C2A	1.3900	C1C—C2C	1.3900
C1A—C6A	1.3900	C1C—C6C	1.3900
C1A—H1A	0.9300	C1C—H1C	0.9300
C2A—C3A	1.3900	C2C—C3C	1.3900
C2A—H2A	0.9300	C2C—H2C	0.9300
C3A—C4A	1.3900	C3C—C4C	1.3900
C3A—H3A	0.9300	C3C—H3C	0.9300
C4A—C5A	1.3900	C4C—C5C	1.3900
C4A—H4A	0.9300	C4C—H4C	0.9300
C5A—C6A	1.3900	C5C—C6C	1.3900
C5A—H5A	0.9300	C5C—H5C	0.9300
C6A—C7A	1.5027	C6C—C7C	1.5219
C7A—O1A	1.420 (4)	C7C—O1C	1.425 (3)
C7A—C12A	1.534 (6)	C7C—C12C	1.524 (4)
C7A—H7A	0.9800	C7C—H7C	0.9800
C8A—O1A	1.428 (6)	C8C—O1C	1.437 (5)
C8A—C13A	1.516 (9)	C8C—C13C	1.518 (5)
C8A—C9A	1.524 (7)	C8C—C9C	1.525 (6)
C8A—H8A	0.9800	C8C—H8C	0.9800
C9A—C10A	1.504 (8)	C9C—C10C	1.502 (5)
C9A—H91A	0.9700	C9C—H91C	0.9700
C9A—H92A	0.9700	C9C—H92C	0.9700
C10A—O4A	1.200 (7)	C10C—O4C	1.212 (5)
C10A—O2A	1.338 (8)	C10C—O2C	1.338 (4)
C11A—O2A	1.444 (8)	C11C—O2C	1.460 (4)
C11A—C13A	1.510 (9)	C11C—C13C	1.508 (5)
C11A—C12A	1.511 (7)	C11C—C12C	1.511 (5)
C11A—H11A	0.9800	C11C—H11C	0.9800
C12A—O3A	1.434 (8)	C12C—O3C	1.408 (4)
C12A—H12A	0.9800	C12C—H12C	0.9800
C13A—H13A	0.9700	C13C—H13C	0.9700
C13A—H14A	0.9700	C13C—H14C	0.9700
O3A—H31A	0.8200	O3C—H31C	0.8200
C1B—C2B	1.3900	C1D—C2D	1.3900
C1B—C6B	1.3900	C1D—C6D	1.3900
C1B—H1B	0.9300	C1D—H1D	0.9300
C2B—C3B	1.3900	C2D—C3D	1.3900
C2B—H2B	0.9300	C2D—H2D	0.9300
C3B—C4B	1.3900	C3D—C4D	1.3900
C3B—H3B	0.9300	C3D—H3D	0.9300
C4B—C5B	1.3900	C4D—C5D	1.3900
C4B—H4B	0.9300	C4D—H4D	0.9300
C5B—C6B	1.3900	C5D—C6D	1.3900
C5B—H5B	0.9300	C5D—H5D	0.9300
C6B—C7B	1.5050	C6D—C7D	1.5012
C7B—O1B	1.438 (3)	C7D—O1D	1.428 (4)
C7B—C12B	1.521 (4)	C7D—C12D	1.508 (6)
C7B—H7B	0.9800	C7D—H7D	0.9800
C8B—O1B	1.435 (5)	C8D—O1D	1.440 (7)
C8B—C9B	1.510 (5)	C8D—C13D	1.496 (10)
C8B—C13B	1.515 (5)	C8D—C9D	1.508 (8)
C8B—H8B	0.9800	C8D—H8D	0.9800
C9B—C10B	1.499 (5)	C9D—C10D	1.517 (8)
C9B—H91B	0.9700	C9D—H91D	0.9700
C9B—H92B	0.9700	C9D—H92D	0.9700
C10B—O4B	1.214 (5)	C10D—O4D	1.213 (7)
C10B—O2B	1.337 (5)	C10D—O2D	1.304 (8)
C11B—O2B	1.470 (5)	C11D—O2D	1.451 (9)
C11B—C12B	1.510 (6)	C11D—C13D	1.478 (10)
C11B—C13B	1.516 (5)	C11D—C12D	1.504 (8)
C11B—H11B	0.9800	C11D—H11D	0.9800
C12B—O3B	1.418 (4)	C12D—O3D	1.404 (8)
C12B—H12B	0.9800	C12D—H12D	0.9800
C13B—H13B	0.9700	C13D—H13D	0.9700
C13B—H14B	0.9700	C13D—H14D	0.9700
O3B—H31B	0.8200	O3D—H31D	0.8200

C2A—C1A—C6A	120.0	C2C—C1C—C6C	120.0
C2A—C1A—H1A	120.0	C2C—C1C—H1C	120.0
C6A—C1A—H1A	120.0	C6C—C1C—H1C	120.0
C1A—C2A—C3A	120.0	C3C—C2C—C1C	120.0
C1A—C2A—H2A	120.0	C3C—C2C—H2C	120.0
C3A—C2A—H2A	120.0	C1C—C2C—H2C	120.0
C4A—C3A—C2A	120.0	C4C—C3C—C2C	120.0
C4A—C3A—H3A	120.0	C4C—C3C—H3C	120.0
C2A—C3A—H3A	120.0	C2C—C3C—H3C	120.0
C5A—C4A—C3A	120.0	C3C—C4C—C5C	120.0
C5A—C4A—H4A	120.0	C3C—C4C—H4C	120.0
C3A—C4A—H4A	120.0	C5C—C4C—H4C	120.0
C4A—C5A—C6A	120.0	C6C—C5C—C4C	120.0
C4A—C5A—H5A	120.0	C6C—C5C—H5C	120.0
C6A—C5A—H5A	120.0	C4C—C5C—H5C	120.0
C5A—C6A—C1A	120.0	C5C—C6C—C1C	120.0
C5A—C6A—C7A	120.4	C5C—C6C—C7C	120.6
C1A—C6A—C7A	119.6	C1C—C6C—C7C	119.3
O1A—C7A—C6A	107.62 (16)	O1C—C7C—C6C	105.91 (14)
O1A—C7A—C12A	110.2 (3)	O1C—C7C—C12C	111.1 (2)
C6A—C7A—C12A	112.9 (2)	C6C—C7C—C12C	113.72 (17)
O1A—C7A—H7A	108.7	O1C—C7C—H7C	108.6
C6A—C7A—H7A	108.7	C6C—C7C—H7C	108.6
C12A—C7A—H7A	108.7	C12C—C7C—H7C	108.6
O1A—C8A—C13A	111.2 (4)	O1C—C8C—C13C	111.5 (3)
O1A—C8A—C9A	111.8 (4)	O1C—C8C—C9C	112.4 (3)
C13A—C8A—C9A	108.1 (5)	C13C—C8C—C9C	108.3 (3)
O1A—C8A—H8A	108.5	O1C—C8C—H8C	108.2
C13A—C8A—H8A	108.5	C13C—C8C—H8C	108.2
C9A—C8A—H8A	108.5	C9C—C8C—H8C	108.2
C10A—C9A—C8A	115.8 (5)	C10C—C9C—C8C	115.7 (3)
C10A—C9A—H91A	108.3	C10C—C9C—H91C	108.4
C8A—C9A—H91A	108.3	C8C—C9C—H91C	108.4
C10A—C9A—H92A	108.3	C10C—C9C—H92C	108.4
C8A—C9A—H92A	108.3	C8C—C9C—H92C	108.4
H91A—C9A—H92A	107.4	H91C—C9C—H92C	107.4
O4A—C10A—O2A	116.8 (5)	O4C—C10C—O2C	117.9 (3)
O4A—C10A—C9A	122.9 (6)	O4C—C10C—C9C	121.7 (3)
O2A—C10A—C9A	120.2 (5)	O2C—C10C—C9C	120.4 (3)
O2A—C11A—C13A	111.0 (5)	O2C—C11C—C13C	111.1 (3)
O2A—C11A—C12A	109.6 (5)	O2C—C11C—C12C	110.2 (3)
C13A—C11A—C12A	110.6 (5)	C13C—C11C—C12C	110.7 (3)
O2A—C11A—H11A	108.6	O2C—C11C—H11C	108.3
C13A—C11A—H11A	108.6	C13C—C11C—H11C	108.3
C12A—C11A—H11A	108.6	C12C—C11C—H11C	108.3
O3A—C12A—C11A	111.6 (5)	O3C—C12C—C11C	113.6 (3)
O3A—C12A—C7A	107.3 (5)	O3C—C12C—C7C	108.2 (3)
C11A—C12A—C7A	111.3 (4)	C11C—C12C—C7C	109.7 (3)
O3A—C12A—H12A	108.9	O3C—C12C—H12C	108.4
C11A—C12A—H12A	108.9	C11C—C12C—H12C	108.4
C7A—C12A—H12A	108.9	C7C—C12C—H12C	108.4
C11A—C13A—C8A	106.4 (5)	C11C—C13C—C8C	105.9 (3)
C11A—C13A—H13A	110.4	C11C—C13C—H13C	110.6
C8A—C13A—H13A	110.4	C8C—C13C—H13C	110.6
C11A—C13A—H14A	110.4	C11C—C13C—H14C	110.6
C8A—C13A—H14A	110.4	C8C—C13C—H14C	110.6
H13A—C13A—H14A	108.6	H13C—C13C—H14C	108.7
C7A—O1A—C8A	114.2 (3)	C7C—O1C—C8C	114.5 (2)
C10A—O2A—C11A	120.5 (4)	C10C—O2C—C11C	121.6 (3)
C12A—O3A—H31A	109.5	C12C—O3C—H31C	109.5
C2B—C1B—C6B	120.0	C2D—C1D—C6D	120.0
C2B—C1B—H1B	120.0	C2D—C1D—H1D	120.0
C6B—C1B—H1B	120.0	C6D—C1D—H1D	120.0
C1B—C2B—C3B	120.0	C3D—C2D—C1D	120.0
C1B—C2B—H2B	120.0	C3D—C2D—H2D	120.0
C3B—C2B—H2B	120.0	C1D—C2D—H2D	120.0
C2B—C3B—C4B	120.0	C2D—C3D—C4D	120.0
C2B—C3B—H3B	120.0	C2D—C3D—H3D	120.0
C4B—C3B—H3B	120.0	C4D—C3D—H3D	120.0
C5B—C4B—C3B	120.0	C5D—C4D—C3D	120.0
C5B—C4B—H4B	120.0	C5D—C4D—H4D	120.0
C3B—C4B—H4B	120.0	C3D—C4D—H4D	120.0
C6B—C5B—C4B	120.0	C4D—C5D—C6D	120.0
C6B—C5B—H5B	120.0	C4D—C5D—H5D	120.0
C4B—C5B—H5B	120.0	C6D—C5D—H5D	120.0
C5B—C6B—C1B	120.0	C5D—C6D—C1D	120.0
C5B—C6B—C7B	120.2	C5D—C6D—C7D	119.2
C1B—C6B—C7B	119.7	C1D—C6D—C7D	120.8
O1B—C7B—C6B	105.87 (14)	O1D—C7D—C6D	107.41 (16)
O1B—C7B—C12B	110.3 (2)	O1D—C7D—C12D	111.0 (3)
C6B—C7B—C12B	113.02 (17)	C6D—C7D—C12D	114.3 (2)
O1B—C7B—H7B	109.2	O1D—C7D—H7D	107.9
C6B—C7B—H7B	109.2	C6D—C7D—H7D	107.9
C12B—C7B—H7B	109.2	C12D—C7D—H7D	107.9
O1B—C8B—C9B	112.7 (3)	O1D—C8D—C13D	110.1 (5)
O1B—C8B—C13B	110.6 (3)	O1D—C8D—C9D	112.3 (5)
C9B—C8B—C13B	108.2 (3)	C13D—C8D—C9D	109.5 (6)
O1B—C8B—H8B	108.4	O1D—C8D—H8D	108.3
C9B—C8B—H8B	108.4	C13D—C8D—H8D	108.3
C13B—C8B—H8B	108.4	C9D—C8D—H8D	108.3
C10B—C9B—C8B	116.9 (3)	C8D—C9D—C10D	114.4 (5)
C10B—C9B—H91B	108.1	C8D—C9D—H91D	108.7
C8B—C9B—H91B	108.1	C10D—C9D—H91D	108.7
C10B—C9B—H92B	108.1	C8D—C9D—H92D	108.7
C8B—C9B—H92B	108.1	C10D—C9D—H92D	108.7
H91B—C9B—H92B	107.3	H91D—C9D—H92D	107.6
O4B—C10B—O2B	117.8 (3)	O4D—C10D—O2D	118.1 (6)
O4B—C10B—C9B	121.8 (3)	O4D—C10D—C9D	120.8 (7)
O2B—C10B—C9B	120.3 (3)	O2D—C10D—C9D	120.9 (5)
O2B—C11B—C12B	110.3 (3)	O2D—C11D—C13D	110.8 (5)
O2B—C11B—C13B	110.9 (3)	O2D—C11D—C12D	109.1 (6)
C12B—C11B—C13B	109.5 (3)	C13D—C11D—C12D	111.4 (6)
O2B—C11B—H11B	108.7	O2D—C11D—H11D	108.5
C12B—C11B—H11B	108.7	C13D—C11D—H11D	108.5
C13B—C11B—H11B	108.7	C12D—C11D—H11D	108.5
O3B—C12B—C11B	112.6 (3)	O3D—C12D—C11D	113.1 (5)
O3B—C12B—C7B	107.4 (3)	O3D—C12D—C7D	108.8 (5)
C11B—C12B—C7B	111.2 (3)	C11D—C12D—C7D	111.5 (4)
O3B—C12B—H12B	108.5	O3D—C12D—H12D	107.8
C11B—C12B—H12B	108.5	C11D—C12D—H12D	107.8
C7B—C12B—H12B	108.5	C7D—C12D—H12D	107.8
C8B—C13B—C11B	106.7 (3)	C11D—C13D—C8D	107.2 (5)
C8B—C13B—H13B	110.4	C11D—C13D—H13D	110.3
C11B—C13B—H13B	110.4	C8D—C13D—H13D	110.3
C8B—C13B—H14B	110.4	C11D—C13D—H14D	110.3
C11B—C13B—H14B	110.4	C8D—C13D—H14D	110.3
H13B—C13B—H14B	108.6	H13D—C13D—H14D	108.5
C8B—O1B—C7B	115.1 (2)	C7D—O1D—C8D	113.5 (3)
C10B—O2B—C11B	121.3 (3)	C10D—O2D—C11D	120.4 (5)
C12B—O3B—H31B	109.5	C12D—O3D—H31D	109.5

C6A—C1A—C2A—C3A	0.0	C6C—C1C—C2C—C3C	0.0
C1A—C2A—C3A—C4A	0.0	C1C—C2C—C3C—C4C	0.0
C2A—C3A—C4A—C5A	0.0	C2C—C3C—C4C—C5C	0.0
C3A—C4A—C5A—C6A	0.0	C3C—C4C—C5C—C6C	0.0
C4A—C5A—C6A—C1A	0.0	C4C—C5C—C6C—C1C	0.0
C4A—C5A—C6A—C7A	178.0	C4C—C5C—C6C—C7C	−176.3
C2A—C1A—C6A—C5A	0.0	C2C—C1C—C6C—C5C	0.0
C2A—C1A—C6A—C7A	−178.0	C2C—C1C—C6C—C7C	176.4
C5A—C6A—C7A—O1A	53.97 (18)	C5C—C6C—C7C—O1C	64.06 (15)
C1A—C6A—C7A—O1A	−127.99 (18)	C1C—C6C—C7C—O1C	−112.31 (15)
C5A—C6A—C7A—C12A	−67.9 (3)	C5C—C6C—C7C—C12C	−58.27 (18)
C1A—C6A—C7A—C12A	110.2 (3)	C1C—C6C—C7C—C12C	125.37 (18)
O1A—C8A—C9A—C10A	83.1 (6)	O1C—C8C—C9C—C10C	85.5 (4)
C13A—C8A—C9A—C10A	−39.7 (6)	C13C—C8C—C9C—C10C	−38.2 (4)
C8A—C9A—C10A—O4A	−168.4 (5)	C8C—C9C—C10C—O4C	−174.7 (4)
C8A—C9A—C10A—O2A	15.7 (7)	C8C—C9C—C10C—O2C	7.3 (5)
O2A—C11A—C12A—O3A	−52.2 (7)	O2C—C11C—C12C—O3C	−55.9 (4)
C13A—C11A—C12A—O3A	−174.8 (6)	C13C—C11C—C12C—O3C	−179.2 (3)
O2A—C11A—C12A—C7A	67.6 (6)	O2C—C11C—C12C—C7C	65.4 (3)
C13A—C11A—C12A—C7A	−55.0 (7)	C13C—C11C—C12C—C7C	−57.9 (4)
O1A—C7A—C12A—O3A	173.6 (4)	O1C—C7C—C12C—O3C	176.8 (3)
C6A—C7A—C12A—O3A	−66.1 (4)	C6C—C7C—C12C—O3C	−63.8 (3)
O1A—C7A—C12A—C11A	51.2 (6)	O1C—C7C—C12C—C11C	52.3 (3)
C6A—C7A—C12A—C11A	171.6 (4)	C6C—C7C—C12C—C11C	171.7 (2)
O2A—C11A—C13A—C8A	−63.8 (6)	O2C—C11C—C13C—C8C	−62.5 (4)
C12A—C11A—C13A—C8A	58.0 (7)	C12C—C11C—C13C—C8C	60.3 (4)
O1A—C8A—C13A—C11A	−60.5 (6)	O1C—C8C—C13C—C11C	−59.5 (4)
C9A—C8A—C13A—C11A	62.7 (5)	C9C—C8C—C13C—C11C	64.7 (4)
C6A—C7A—O1A—C8A	−178.3 (3)	C6C—C7C—O1C—C8C	−177.6 (2)
C12A—C7A—O1A—C8A	−54.8 (5)	C12C—C7C—O1C—C8C	−53.7 (4)
C13A—C8A—O1A—C7A	61.4 (5)	C13C—C8C—O1C—C7C	58.6 (4)
C9A—C8A—O1A—C7A	−59.6 (5)	C9C—C8C—O1C—C7C	−63.2 (4)
O4A—C10A—O2A—C11A	168.2 (5)	O4C—C10C—O2C—C11C	177.9 (4)
C9A—C10A—O2A—C11A	−15.7 (7)	C9C—C10C—O2C—C11C	−4.0 (5)
C13A—C11A—O2A—C10A	40.4 (7)	C13C—C11C—O2C—C10C	32.5 (5)
C12A—C11A—O2A—C10A	−82.0 (6)	C12C—C11C—O2C—C10C	−90.5 (4)
C6B—C1B—C2B—C3B	0.0	C6D—C1D—C2D—C3D	0.0
C1B—C2B—C3B—C4B	0.0	C1D—C2D—C3D—C4D	0.0
C2B—C3B—C4B—C5B	0.0	C2D—C3D—C4D—C5D	0.0
C3B—C4B—C5B—C6B	0.0	C3D—C4D—C5D—C6D	0.0
C4B—C5B—C6B—C1B	0.0	C4D—C5D—C6D—C1D	0.0
C4B—C5B—C6B—C7B	178.2	C4D—C5D—C6D—C7D	178.5
C2B—C1B—C6B—C5B	0.0	C2D—C1D—C6D—C5D	0.0
C2B—C1B—C6B—C7B	−178.2	C2D—C1D—C6D—C7D	−178.5
C5B—C6B—C7B—O1B	−114.19 (15)	C5D—C6D—C7D—O1D	−109.66 (19)
C1B—C6B—C7B—O1B	64.00 (15)	C1D—C6D—C7D—O1D	68.87 (19)
C5B—C6B—C7B—C12B	125.02 (18)	C5D—C6D—C7D—C12D	126.6 (3)
C1B—C6B—C7B—C12B	−56.79 (18)	C1D—C6D—C7D—C12D	−54.8 (3)
O1B—C8B—C9B—C10B	84.9 (4)	O1D—C8D—C9D—C10D	84.3 (7)
C13B—C8B—C9B—C10B	−37.7 (4)	C13D—C8D—C9D—C10D	−38.3 (7)
C8B—C9B—C10B—O4B	−173.4 (4)	C8D—C9D—C10D—O4D	−168.7 (5)
C8B—C9B—C10B—O2B	8.1 (5)	C8D—C9D—C10D—O2D	15.2 (8)
O2B—C11B—C12B—O3B	−55.5 (4)	O2D—C11D—C12D—O3D	−53.5 (7)
C13B—C11B—C12B—O3B	−177.9 (3)	C13D—C11D—C12D—O3D	−176.2 (6)
O2B—C11B—C12B—C7B	65.1 (3)	O2D—C11D—C12D—C7D	69.5 (7)
C13B—C11B—C12B—C7B	−57.3 (4)	C13D—C11D—C12D—C7D	−53.2 (8)
O1B—C7B—C12B—O3B	175.2 (3)	O1D—C7D—C12D—O3D	174.4 (4)
C6B—C7B—C12B—O3B	−66.6 (3)	C6D—C7D—C12D—O3D	−63.9 (5)
O1B—C7B—C12B—C11B	51.5 (3)	O1D—C7D—C12D—C11D	49.0 (6)
C6B—C7B—C12B—C11B	169.8 (2)	C6D—C7D—C12D—C11D	170.7 (4)
O1B—C8B—C13B—C11B	−60.5 (4)	O2D—C11D—C13D—C8D	−63.2 (6)
C9B—C8B—C13B—C11B	63.4 (4)	C12D—C11D—C13D—C8D	58.5 (7)
O2B—C11B—C13B—C8B	−61.7 (4)	O1D—C8D—C13D—C11D	−61.7 (6)
C12B—C11B—C13B—C8B	60.3 (4)	C9D—C8D—C13D—C11D	62.2 (6)
C9B—C8B—O1B—C7B	−62.2 (4)	C6D—C7D—O1D—C8D	−179.7 (4)
C13B—C8B—O1B—C7B	59.1 (4)	C12D—C7D—O1D—C8D	−54.0 (5)
C6B—C7B—O1B—C8B	−175.7 (2)	C13D—C8D—O1D—C7D	61.4 (6)
C12B—C7B—O1B—C8B	−53.1 (4)	C9D—C8D—O1D—C7D	−60.8 (6)
O4B—C10B—O2B—C11B	176.2 (4)	O4D—C10D—O2D—C11D	167.5 (5)
C9B—C10B—O2B—C11B	−5.2 (5)	C9D—C10D—O2D—C11D	−16.2 (7)
C12B—C11B—O2B—C10B	−88.9 (4)	C13D—C11D—O2D—C10D	40.8 (7)
C13B—C11B—O2B—C10B	32.7 (5)	C12D—C11D—O2D—C10D	−82.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3B—H31B···O4C	0.82	1.97	2.783 (4)	173
O3C—H31C···O4Bⁱ	0.82	1.97	2.784 (4)	176
O3D—H31D···O3Cⁱⁱ	0.82	2.40	3.185 (7)	161

Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z−1.

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