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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_da065

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
(+)-(2R,3R)-tetraphenylbutane-1,2,3,4-tetraol /2-methylcyclohexanone (1:1)
;
_chemical_name_common            ?
_chemical_melting_point          421
_chemical_formula_moiety         'C28 H26 O4, C7 H12 O'
_chemical_formula_sum            'C35 H38 O5'
_chemical_formula_weight         538.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.3843(3)
_cell_length_b                   15.2193(3)
_cell_length_c                   18.2734(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2887.96(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8716
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.702
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.281
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8849
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            15292
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.741
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             6716
_reflns_number_gt                6013
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_max     0.871
_reflns_Friedel_fraction_full    0.941

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.4205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2378 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.31(19)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6716
_refine_ls_number_parameters     440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.18466(12) 0.11511(7) 0.53190(6) 0.0271(2) Uani 1 1 d . . . . .
H1 H -0.1862 0.1640 0.5532 0.041 Uiso 1 1 calc R U . . .
O2 O 0.05372(13) 0.19720(7) 0.54956(6) 0.0301(3) Uani 1 1 d . . . . .
H2A H 0.1099 0.2021 0.5824 0.045 Uiso 1 1 calc R U . . .
O3 O -0.04396(13) 0.15857(9) 0.40911(7) 0.0341(3) Uani 1 1 d . . . . .
H3A H -0.1085 0.1604 0.4368 0.051 Uiso 1 1 calc R U . . .
O4 O 0.20718(13) 0.22439(7) 0.43080(7) 0.0325(3) Uani 1 1 d . . . . .
H4 H 0.1588 0.2382 0.4658 0.049 Uiso 1 1 calc R U . . .
C1 C -0.07581(16) 0.06555(10) 0.55684(8) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.04792(16) 0.10782(9) 0.52555(8) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.1244 0.0756 0.5452 0.027 Uiso 1 1 calc R U . . .
C3 C 0.05221(16) 0.10527(10) 0.44121(8) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.0369 0.0433 0.4253 0.028 Uiso 1 1 calc R U . . .
C4 C 0.18390(17) 0.13470(10) 0.41062(8) 0.0245(3) Uani 1 1 d . . . . .
C11 C -0.07461(18) 0.06331(10) 0.64099(8) 0.0265(3) Uani 1 1 d . . . . .
C12 C 0.0382(2) 0.05286(12) 0.68086(9) 0.0336(4) Uani 1 1 d . . . . .
H12 H 0.1182 0.0493 0.6559 0.040 Uiso 1 1 calc R U . . .
C13 C 0.0358(2) 0.04757(14) 0.75698(10) 0.0445(5) Uani 1 1 d . . . . .
H13 H 0.1138 0.0405 0.7835 0.053 Uiso 1 1 calc R U . . .
C14 C -0.0798(3) 0.05261(15) 0.79378(10) 0.0499(6) Uani 1 1 d . . . . .
H14 H -0.0817 0.0488 0.8457 0.060 Uiso 1 1 calc R U . . .
C15 C -0.1925(3) 0.06316(16) 0.75502(11) 0.0506(5) Uani 1 1 d . . . . .
H15 H -0.2722 0.0669 0.7803 0.061 Uiso 1 1 calc R U . . .
C16 C -0.1903(2) 0.06833(13) 0.67882(10) 0.0389(4) Uani 1 1 d . . . . .
H16 H -0.2686 0.0754 0.6526 0.047 Uiso 1 1 calc R U . . .
C21 C -0.08977(17) -0.02794(10) 0.52668(8) 0.0248(3) Uani 1 1 d . . . . .
C22 C -0.00059(19) -0.09193(11) 0.54584(11) 0.0340(4) Uani 1 1 d . . . . .
H22 H 0.0657 -0.0782 0.5798 0.041 Uiso 1 1 calc R U . . .
C23 C -0.0070(2) -0.17588(12) 0.51601(12) 0.0433(5) Uani 1 1 d . . . . .
H23 H 0.0550 -0.2190 0.5293 0.052 Uiso 1 1 calc R U . . .
C24 C -0.1035(2) -0.19641(12) 0.46702(11) 0.0420(5) Uani 1 1 d . . . . .
H24 H -0.1080 -0.2536 0.4464 0.050 Uiso 1 1 calc R U . . .
C25 C -0.1931(2) -0.13399(12) 0.44815(10) 0.0409(4) Uani 1 1 d . . . . .
H25 H -0.2599 -0.1486 0.4148 0.049 Uiso 1 1 calc R U . . .
C26 C -0.18692(19) -0.04941(11) 0.47739(9) 0.0314(4) Uani 1 1 d . . . . .
H26 H -0.2489 -0.0066 0.4637 0.038 Uiso 1 1 calc R U . . .
C31 C 0.28912(17) 0.07465(11) 0.44184(8) 0.0272(3) Uani 1 1 d . . . . .
C32 C 0.38926(19) 0.10723(14) 0.48372(11) 0.0394(4) Uani 1 1 d . . . . .
H32 H 0.3963 0.1687 0.4920 0.047 Uiso 1 1 calc R U . . .
C33 C 0.4801(2) 0.04997(17) 0.51379(12) 0.0512(6) Uani 1 1 d . . . . .
H33 H 0.5489 0.0729 0.5423 0.061 Uiso 1 1 calc R U . . .
C34 C 0.4713(2) -0.03900(16) 0.50271(12) 0.0488(6) Uani 1 1 d . . . . .
H34 H 0.5327 -0.0775 0.5241 0.059 Uiso 1 1 calc R U . . .
C35 C 0.3732(2) -0.07215(14) 0.46045(11) 0.0439(5) Uani 1 1 d . . . . .
H35 H 0.3671 -0.1337 0.4523 0.053 Uiso 1 1 calc R U . . .
C36 C 0.28309(19) -0.01605(11) 0.42979(9) 0.0336(4) Uani 1 1 d . . . . .
H36 H 0.2162 -0.0395 0.4001 0.040 Uiso 1 1 calc R U . . .
C41 C 0.18808(18) 0.13040(10) 0.32653(9) 0.0282(4) Uani 1 1 d . . . . .
C42 C 0.1150(2) 0.07146(12) 0.28626(10) 0.0371(4) Uani 1 1 d . . . . .
H42 H 0.0577 0.0327 0.3107 0.044 Uiso 1 1 calc R U . . .
C43 C 0.1251(2) 0.06854(14) 0.21011(10) 0.0455(5) Uani 1 1 d . . . . .
H43 H 0.0746 0.0278 0.1831 0.055 Uiso 1 1 calc R U . . .
C44 C 0.2075(2) 0.12420(16) 0.17401(10) 0.0478(6) Uani 1 1 d . . . . .
H44 H 0.2139 0.1222 0.1222 0.057 Uiso 1 1 calc R U . . .
C45 C 0.2804(2) 0.18262(16) 0.21323(12) 0.0501(6) Uani 1 1 d . . . . .
H45 H 0.3376 0.2212 0.1884 0.060 Uiso 1 1 calc R U . . .
C46 C 0.2712(2) 0.18587(13) 0.28931(11) 0.0395(4) Uani 1 1 d . . . . .
H46 H 0.3225 0.2265 0.3159 0.047 Uiso 1 1 calc R U . . .
O5_a O 0.2588(6) 0.1954(6) 0.6418(3) 0.0352(17) Uani 0.645(6) 1 d . . P A 1
C5_a C 0.4779(5) 0.1676(3) 0.7224(3) 0.0590(12) Uani 0.645(6) 1 d . . P A 1
H5A_a H 0.5516 0.1670 0.7559 0.088 Uiso 0.645(6) 1 calc R U P A 1
H5B_a H 0.5087 0.1740 0.6720 0.088 Uiso 0.645(6) 1 calc R U P A 1
H5C_a H 0.4299 0.1125 0.7271 0.088 Uiso 0.645(6) 1 calc R U P A 1
C51_a C 0.2769(11) 0.2493(8) 0.6926(7) 0.034(2) Uani 0.645(6) 1 d . . P A 1
C52_a C 0.3914(4) 0.2432(3) 0.74108(18) 0.0323(8) Uani 0.645(6) 1 d . . P A 1
H52_a H 0.4425 0.2982 0.7337 0.039 Uiso 0.645(6) 1 calc R U P A 1
C53_a C 0.3467(7) 0.2427(5) 0.8206(3) 0.0542(16) Uani 0.645(6) 1 d . . P A 1
H53A_a H 0.2975 0.1882 0.8302 0.065 Uiso 0.645(6) 1 calc R U P A 1
H53B_a H 0.4229 0.2429 0.8532 0.065 Uiso 0.645(6) 1 calc R U P A 1
C54_a C 0.2630(5) 0.3216(4) 0.8380(2) 0.0618(13) Uani 0.645(6) 1 d . . P A 1
H54A_a H 0.2338 0.3182 0.8895 0.074 Uiso 0.645(6) 1 calc R U P A 1
H54B_a H 0.3140 0.3760 0.8321 0.074 Uiso 0.645(6) 1 calc R U P A 1
C55_a C 0.1474(5) 0.3247(3) 0.7880(2) 0.0594(12) Uani 0.645(6) 1 d . . P A 1
H55A_a H 0.0968 0.3784 0.7984 0.071 Uiso 0.645(6) 1 calc R U P A 1
H55B_a H 0.0917 0.2732 0.7976 0.071 Uiso 0.645(6) 1 calc R U P A 1
C56_a C 0.1882(6) 0.3248(3) 0.7072(3) 0.0511(12) Uani 0.645(6) 1 d . . P A 1
H56A_a H 0.1111 0.3200 0.6756 0.061 Uiso 0.645(6) 1 calc R U P A 1
H56B_a H 0.2324 0.3807 0.6955 0.061 Uiso 0.645(6) 1 calc R U P A 1
O6_b O 0.2545(18) 0.1923(14) 0.6438(10) 0.069(5) Uani 0.355(6) 1 d . . P A 2
C6_b C 0.1135(11) 0.3282(7) 0.6902(7) 0.097(4) Uani 0.355(6) 1 d . . P A 2
H6A_b H 0.0603 0.2751 0.6881 0.146 Uiso 0.355(6) 1 calc R U P A 2
H6B_b H 0.1294 0.3497 0.6404 0.146 Uiso 0.355(6) 1 calc R U P A 2
H6C_b H 0.0686 0.3736 0.7184 0.146 Uiso 0.355(6) 1 calc R U P A 2
C61_b C 0.307(2) 0.2323(17) 0.6914(16) 0.039(4) Uani 0.355(6) 1 d . . P A 2
C62_b C 0.2393(9) 0.3073(6) 0.7263(5) 0.0463(19) Uani 0.355(6) 1 d . . P A 2
H62_b H 0.2959 0.3602 0.7218 0.056 Uiso 0.355(6) 1 calc R U P A 2
C63_b C 0.2225(11) 0.2871(7) 0.8089(5) 0.071(3) Uani 0.355(6) 1 d . . P A 2
H63A_b H 0.1871 0.3397 0.8337 0.085 Uiso 0.355(6) 1 calc R U P A 2
H63B_b H 0.1597 0.2387 0.8149 0.085 Uiso 0.355(6) 1 calc R U P A 2
C64_b C 0.3467(18) 0.2618(11) 0.8448(5) 0.068(4) Uani 0.355(6) 1 d . . P A 2
H64A_b H 0.3303 0.2473 0.8968 0.082 Uiso 0.355(6) 1 calc R U P A 2
H64B_b H 0.4066 0.3123 0.8433 0.082 Uiso 0.355(6) 1 calc R U P A 2
C65_b C 0.4096(10) 0.1833(6) 0.8076(4) 0.066(3) Uani 0.355(6) 1 d . . P A 2
H65A_b H 0.4934 0.1701 0.8310 0.079 Uiso 0.355(6) 1 calc R U P A 2
H65B_b H 0.3537 0.1309 0.8122 0.079 Uiso 0.355(6) 1 calc R U P A 2
C66_b C 0.4295(8) 0.2057(6) 0.7276(4) 0.0377(16) Uani 0.355(6) 1 d . . P A 2
H66A_b H 0.4926 0.2542 0.7235 0.045 Uiso 0.355(6) 1 calc R U P A 2
H66B_b H 0.4655 0.1539 0.7019 0.045 Uiso 0.355(6) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4333(19) . ?
O1 H1 0.8400 . ?
O2 C2 1.4306(17) . ?
O2 H2A 0.8400 . ?
O3 C3 1.414(2) . ?
O3 H3A 0.8400 . ?
O4 C4 1.4345(18) . ?
O4 H4 0.8400 . ?
C1 C21 1.533(2) . ?
C1 C11 1.538(2) . ?
C1 C2 1.546(2) . ?
C2 C3 1.542(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.544(2) . ?
C3 H3 1.0000 . ?
C4 C31 1.534(2) . ?
C4 C41 1.539(2) . ?
C11 C16 1.388(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.389(2) . ?
C21 C26 1.391(2) . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.383(3) . ?
C31 C36 1.399(2) . ?
C32 C33 1.397(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.372(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.375(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.386(3) . ?
C41 C46 1.386(3) . ?
C42 C43 1.396(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.373(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.370(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.394(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
O5_a C51_a 1.252(14) . ?
C5_a C52_a 1.499(6) . ?
C5_a H5A_a 0.9800 . ?
C5_a H5B_a 0.9800 . ?
C5_a H5C_a 0.9800 . ?
C51_a C52_a 1.486(13) . ?
C51_a C56_a 1.497(10) . ?
C52_a C53_a 1.525(6) . ?
C52_a H52_a 1.0000 . ?
C53_a C54_a 1.515(9) . ?
C53_a H53A_a 0.9900 . ?
C53_a H53B_a 0.9900 . ?
C54_a C55_a 1.509(7) . ?
C54_a H54A_a 0.9900 . ?
C54_a H54B_a 0.9900 . ?
C55_a C56_a 1.535(6) . ?
C55_a H55A_a 0.9900 . ?
C55_a H55B_a 0.9900 . ?
C56_a H56A_a 0.9900 . ?
C56_a H56B_a 0.9900 . ?
O6_b C61_b 1.19(3) . ?
C6_b C62_b 1.498(13) . ?
C6_b H6A_b 0.9800 . ?
C6_b H6B_b 0.9800 . ?
C6_b H6C_b 0.9800 . ?
C61_b C62_b 1.48(2) . ?
C61_b C66_b 1.49(2) . ?
C62_b C63_b 1.551(12) . ?
C62_b H62_b 1.0000 . ?
C63_b C64_b 1.50(2) . ?
C63_b H63A_b 0.9900 . ?
C63_b H63B_b 0.9900 . ?
C64_b C65_b 1.521(16) . ?
C64_b H64A_b 0.9900 . ?
C64_b H64B_b 0.9900 . ?
C65_b C66_b 1.516(9) . ?
C65_b H65A_b 0.9900 . ?
C65_b H65B_b 0.9900 . ?
C66_b H66A_b 0.9900 . ?
C66_b H66B_b 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C2 O2 H2A 109.5 . . ?
C3 O3 H3A 109.5 . . ?
C4 O4 H4 109.5 . . ?
O1 C1 C21 107.44(13) . . ?
O1 C1 C11 109.63(13) . . ?
C21 C1 C11 109.85(12) . . ?
O1 C1 C2 108.59(12) . . ?
C21 C1 C2 109.38(12) . . ?
C11 C1 C2 111.84(13) . . ?
O2 C2 C3 109.22(12) . . ?
O2 C2 C1 108.50(12) . . ?
C3 C2 C1 112.51(12) . . ?
O2 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
O3 C3 C2 112.31(13) . . ?
O3 C3 C4 108.00(12) . . ?
C2 C3 C4 112.34(13) . . ?
O3 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
O4 C4 C31 110.56(14) . . ?
O4 C4 C41 107.01(12) . . ?
C31 C4 C41 109.02(13) . . ?
O4 C4 C3 109.41(13) . . ?
C31 C4 C3 108.87(12) . . ?
C41 C4 C3 111.98(14) . . ?
C16 C11 C12 118.35(15) . . ?
C16 C11 C1 119.32(16) . . ?
C12 C11 C1 122.27(16) . . ?
C11 C12 C13 121.02(19) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.70(17) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.5(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C22 C21 C26 118.82(15) . . ?
C22 C21 C1 119.82(15) . . ?
C26 C21 C1 121.29(15) . . ?
C21 C22 C23 120.91(18) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 119.80(19) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 119.89(17) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.72(19) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 119.86(17) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C32 C31 C36 118.32(17) . . ?
C32 C31 C4 121.85(16) . . ?
C36 C31 C4 119.81(15) . . ?
C31 C32 C33 120.1(2) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C34 C33 C32 120.8(2) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.64(19) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.1(2) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 120.95(19) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
C42 C41 C46 118.33(16) . . ?
C42 C41 C4 122.84(15) . . ?
C46 C41 C4 118.80(16) . . ?
C41 C42 C43 120.6(2) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 H42 119.7 . . ?
C44 C43 C42 120.4(2) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C45 C44 C43 119.57(18) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C44 C45 C46 120.5(2) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C41 C46 C45 120.7(2) . . ?
C41 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C52_a C5_a H5A_a 109.5 . . ?
C52_a C5_a H5B_a 109.5 . . ?
H5A_a C5_a H5B_a 109.5 . . ?
C52_a C5_a H5C_a 109.5 . . ?
H5A_a C5_a H5C_a 109.5 . . ?
H5B_a C5_a H5C_a 109.5 . . ?
O5_a C51_a C52_a 121.4(7) . . ?
O5_a C51_a C56_a 122.9(10) . . ?
C52_a C51_a C56_a 115.6(9) . . ?
C51_a C52_a C5_a 113.0(5) . . ?
C51_a C52_a C53_a 109.0(6) . . ?
C5_a C52_a C53_a 113.3(4) . . ?
C51_a C52_a H52_a 107.1 . . ?
C5_a C52_a H52_a 107.1 . . ?
C53_a C52_a H52_a 107.1 . . ?
C54_a C53_a C52_a 111.7(5) . . ?
C54_a C53_a H53A_a 109.3 . . ?
C52_a C53_a H53A_a 109.3 . . ?
C54_a C53_a H53B_a 109.3 . . ?
C52_a C53_a H53B_a 109.3 . . ?
H53A_a C53_a H53B_a 107.9 . . ?
C55_a C54_a C53_a 110.8(4) . . ?
C55_a C54_a H54A_a 109.5 . . ?
C53_a C54_a H54A_a 109.5 . . ?
C55_a C54_a H54B_a 109.5 . . ?
C53_a C54_a H54B_a 109.5 . . ?
H54A_a C54_a H54B_a 108.1 . . ?
C54_a C55_a C56_a 111.2(4) . . ?
C54_a C55_a H55A_a 109.4 . . ?
C56_a C55_a H55A_a 109.4 . . ?
C54_a C55_a H55B_a 109.4 . . ?
C56_a C55_a H55B_a 109.4 . . ?
H55A_a C55_a H55B_a 108.0 . . ?
C51_a C56_a C55_a 109.9(6) . . ?
C51_a C56_a H56A_a 109.7 . . ?
C55_a C56_a H56A_a 109.7 . . ?
C51_a C56_a H56B_a 109.7 . . ?
C55_a C56_a H56B_a 109.7 . . ?
H56A_a C56_a H56B_a 108.2 . . ?
C62_b C6_b H6A_b 109.5 . . ?
C62_b C6_b H6B_b 109.5 . . ?
H6A_b C6_b H6B_b 109.5 . . ?
C62_b C6_b H6C_b 109.5 . . ?
H6A_b C6_b H6C_b 109.5 . . ?
H6B_b C6_b H6C_b 109.5 . . ?
O6_b C61_b C62_b 119.2(19) . . ?
O6_b C61_b C66_b 125.1(18) . . ?
C62_b C61_b C66_b 115(2) . . ?
C61_b C62_b C6_b 112.8(12) . . ?
C61_b C62_b C63_b 108.6(12) . . ?
C6_b C62_b C63_b 111.9(9) . . ?
C61_b C62_b H62_b 107.8 . . ?
C6_b C62_b H62_b 107.8 . . ?
C63_b C62_b H62_b 107.8 . . ?
C64_b C63_b C62_b 112.3(8) . . ?
C64_b C63_b H63A_b 109.1 . . ?
C62_b C63_b H63A_b 109.1 . . ?
C64_b C63_b H63B_b 109.1 . . ?
C62_b C63_b H63B_b 109.1 . . ?
H63A_b C63_b H63B_b 107.9 . . ?
C63_b C64_b C65_b 112.1(9) . . ?
C63_b C64_b H64A_b 109.2 . . ?
C65_b C64_b H64A_b 109.2 . . ?
C63_b C64_b H64B_b 109.2 . . ?
C65_b C64_b H64B_b 109.2 . . ?
H64A_b C64_b H64B_b 107.9 . . ?
C66_b C65_b C64_b 108.2(8) . . ?
C66_b C65_b H65A_b 110.1 . . ?
C64_b C65_b H65A_b 110.1 . . ?
C66_b C65_b H65B_b 110.1 . . ?
C64_b C65_b H65B_b 110.1 . . ?
H65A_b C65_b H65B_b 108.4 . . ?
C61_b C66_b C65_b 111.9(12) . . ?
C61_b C66_b H66A_b 109.2 . . ?
C65_b C66_b H66A_b 109.2 . . ?
C61_b C66_b H66B_b 109.2 . . ?
C65_b C66_b H66B_b 109.2 . . ?
H66A_b C66_b H66B_b 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 58.41(14) . . . . ?
C21 C1 C2 O2 175.38(12) . . . . ?
C11 C1 C2 O2 -62.69(15) . . . . ?
O1 C1 C2 C3 -62.54(15) . . . . ?
C21 C1 C2 C3 54.42(16) . . . . ?
C11 C1 C2 C3 176.35(13) . . . . ?
O2 C2 C3 O3 -54.00(17) . . . . ?
C1 C2 C3 O3 66.54(16) . . . . ?
O2 C2 C3 C4 67.99(16) . . . . ?
C1 C2 C3 C4 -171.46(12) . . . . ?
O3 C3 C4 O4 61.87(15) . . . . ?
C2 C3 C4 O4 -62.54(16) . . . . ?
O3 C3 C4 C31 -177.21(12) . . . . ?
C2 C3 C4 C31 58.38(16) . . . . ?
O3 C3 C4 C41 -56.59(16) . . . . ?
C2 C3 C4 C41 179.00(13) . . . . ?
O1 C1 C11 C16 29.1(2) . . . . ?
C21 C1 C11 C16 -88.75(19) . . . . ?
C2 C1 C11 C16 149.59(16) . . . . ?
O1 C1 C11 C12 -153.54(15) . . . . ?
C21 C1 C11 C12 88.6(2) . . . . ?
C2 C1 C11 C12 -33.0(2) . . . . ?
C16 C11 C12 C13 0.0(3) . . . . ?
C1 C11 C12 C13 -177.43(17) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C1 C11 C16 C15 177.60(18) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
O1 C1 C21 C22 -176.41(14) . . . . ?
C11 C1 C21 C22 -57.2(2) . . . . ?
C2 C1 C21 C22 65.91(18) . . . . ?
O1 C1 C21 C26 6.7(2) . . . . ?
C11 C1 C21 C26 125.91(16) . . . . ?
C2 C1 C21 C26 -110.97(17) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
C1 C21 C22 C23 -176.37(17) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C22 C21 C26 C25 -0.1(3) . . . . ?
C1 C21 C26 C25 176.78(16) . . . . ?
C24 C25 C26 C21 -0.5(3) . . . . ?
O4 C4 C31 C32 0.4(2) . . . . ?
C41 C4 C31 C32 117.81(17) . . . . ?
C3 C4 C31 C32 -119.77(17) . . . . ?
O4 C4 C31 C36 178.66(14) . . . . ?
C41 C4 C31 C36 -64.0(2) . . . . ?
C3 C4 C31 C36 58.45(18) . . . . ?
C36 C31 C32 C33 -1.0(3) . . . . ?
C4 C31 C32 C33 177.24(18) . . . . ?
C31 C32 C33 C34 -0.3(3) . . . . ?
C32 C33 C34 C35 1.1(3) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C34 C35 C36 C31 -0.8(3) . . . . ?
C32 C31 C36 C35 1.6(3) . . . . ?
C4 C31 C36 C35 -176.70(16) . . . . ?
O4 C4 C41 C42 -148.62(17) . . . . ?
C31 C4 C41 C42 91.8(2) . . . . ?
C3 C4 C41 C42 -28.7(2) . . . . ?
O4 C4 C41 C46 33.4(2) . . . . ?
C31 C4 C41 C46 -86.16(19) . . . . ?
C3 C4 C41 C46 153.31(16) . . . . ?
C46 C41 C42 C43 -0.2(3) . . . . ?
C4 C41 C42 C43 -178.18(18) . . . . ?
C41 C42 C43 C44 -0.1(3) . . . . ?
C42 C43 C44 C45 0.2(3) . . . . ?
C43 C44 C45 C46 -0.1(3) . . . . ?
C42 C41 C46 C45 0.4(3) . . . . ?
C4 C41 C46 C45 178.41(18) . . . . ?
C44 C45 C46 C41 -0.2(3) . . . . ?
O5_a C51_a C52_a C5_a -0.3(14) . . . . ?
C56_a C51_a C52_a C5_a -178.5(7) . . . . ?
O5_a C51_a C52_a C53_a -127.2(11) . . . . ?
C56_a C51_a C52_a C53_a 54.6(10) . . . . ?
C51_a C52_a C53_a C54_a -55.0(8) . . . . ?
C5_a C52_a C53_a C54_a 178.2(5) . . . . ?
C52_a C53_a C54_a C55_a 57.5(6) . . . . ?
C53_a C54_a C55_a C56_a -55.9(6) . . . . ?
O5_a C51_a C56_a C55_a 128.0(11) . . . . ?
C52_a C51_a C56_a C55_a -53.8(11) . . . . ?
C54_a C55_a C56_a C51_a 52.9(8) . . . . ?
O6_b C61_b C62_b C6_b -6(3) . . . . ?
C66_b C61_b C62_b C6_b -177.0(13) . . . . ?
O6_b C61_b C62_b C63_b 119(2) . . . . ?
C66_b C61_b C62_b C63_b -52.3(19) . . . . ?
C61_b C62_b C63_b C64_b 52.0(15) . . . . ?
C6_b C62_b C63_b C64_b 177.2(10) . . . . ?
C62_b C63_b C64_b C65_b -56.7(14) . . . . ?
C63_b C64_b C65_b C66_b 56.9(13) . . . . ?
O6_b C61_b C66_b C65_b -114(2) . . . . ?
C62_b C61_b C66_b C65_b 56.5(19) . . . . ?
C64_b C65_b C66_b C61_b -55.5(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.84 2.05 2.7736(15) 144.1 3_456
O2 H2A O5_a 0.84 1.89 2.716(5) 166.5 .
O3 H3A O1 0.84 2.03 2.7580(18) 144.5 .
O4 H4 O2 0.84 1.98 2.7240(18) 147.0 .
C16 H16 O1 0.95 2.45 2.778(2) 100.2 .
C26 H26 O1 0.95 2.33 2.695(2) 102.1 .
C32 H32 O4 0.95 2.41 2.773(2) 102.1 .

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.032

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 989081'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_n196


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (+)-(2R,3R)-tetraphenylbutane-1,2,3,4-tetraol/3-methylcyclohexanone (1:1) 
;
_chemical_name_common            ?
_chemical_melting_point          421
_chemical_formula_moiety         'C28 H26 O4, C7 H12 O'
_chemical_formula_sum            'C35 H38 O5'
_chemical_formula_weight         538.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.4493(6)
_cell_length_b                   8.2368(4)
_cell_length_c                   13.9466(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.843(2)
_cell_angle_gamma                90.00
_cell_volume                     1422.69(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.469
_exptl_crystal_size_min          0.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9363
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           ?

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         26657
_diffrn_reflns_number            26618
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         28.34
_reflns_number_total             6823
_reflns_number_gt                6031
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0762P)²+0.2746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(8)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6823
_refine_ls_number_parameters     399
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33154(12) 0.23917(19) 0.97478(10) 0.0329(3) Uani 1 1 d . . .
C2 C 0.31395(16) 0.3231(3) 1.05790(13) 0.0508(5) Uani 1 1 d . . .
H2 H 0.2480 0.3797 1.0615 0.061 Uiso 1 1 calc R . .
C3 C 0.3935(2) 0.3245(4) 1.13673(15) 0.0669(7) Uani 1 1 d . . .
H3 H 0.3808 0.3821 1.1935 0.080 Uiso 1 1 calc R . .
C4 C 0.48894(17) 0.2442(3) 1.13290(14) 0.0593(6) Uani 1 1 d . . .
H4 H 0.5419 0.2447 1.1870 0.071 Uiso 1 1 calc R . .
C5 C 0.50809(15) 0.1623(3) 1.04996(14) 0.0496(5) Uani 1 1 d . . .
H5 H 0.5747 0.1075 1.0465 0.060 Uiso 1 1 calc R . .
C6 C 0.42958(13) 0.1601(2) 0.97132(12) 0.0387(3) Uani 1 1 d . . .
H6 H 0.4433 0.1036 0.9145 0.046 Uiso 1 1 calc R . .
C7 C 0.18513(11) 0.06428(17) 0.89260(10) 0.0257(3) Uani 1 1 d . . .
C8 C 0.23802(12) -0.07892(19) 0.87334(12) 0.0339(3) Uani 1 1 d . . .
H8 H 0.3107 -0.0741 0.8582 0.041 Uiso 1 1 calc R . .
C9 C 0.18735(14) -0.2287(2) 0.87561(12) 0.0381(3) Uani 1 1 d . . .
H9 H 0.2249 -0.3248 0.8616 0.046 Uiso 1 1 calc R . .
C10 C 0.08171(15) -0.2376(2) 0.89838(13) 0.0427(4) Uani 1 1 d . . .
H10 H 0.0467 -0.3398 0.9007 0.051 Uiso 1 1 calc R . .
C11 C 0.02806(14) -0.0972(3) 0.91760(14) 0.0483(4) Uani 1 1 d . . .
H11 H -0.0445 -0.1027 0.9328 0.058 Uiso 1 1 calc R . .
C12 C 0.07925(13) 0.0534(2) 0.91501(12) 0.0372(4) Uani 1 1 d . . .
H12 H 0.0412 0.1493 0.9287 0.045 Uiso 1 1 calc R . .
C13 C 0.24156(11) 0.22971(17) 0.89102(10) 0.0262(3) Uani 1 1 d . . .
O14 O 0.16684(9) 0.35617(13) 0.90521(8) 0.0358(3) Uani 1 1 d . . .
H14 H 0.1371 0.3871 0.8516 0.043 Uiso 1 1 calc R . .
C15 C 0.28924(10) 0.25453(18) 0.79337(10) 0.0275(3) Uani 1 1 d . . .
H15 H 0.3437 0.1676 0.7855 0.033 Uiso 1 1 calc R . .
O16 O 0.34115(10) 0.40849(16) 0.79380(9) 0.0446(3) Uani 1 1 d . . .
H16 H 0.4083 0.3957 0.8036 0.054 Uiso 1 1 calc R . .
C17 C 0.20210(11) 0.24951(18) 0.70680(9) 0.0274(3) Uani 1 1 d . . .
H17 H 0.1557 0.1520 0.7141 0.033 Uiso 1 1 calc R . .
O18 O 0.13606(10) 0.39049(16) 0.70984(8) 0.0432(3) Uani 1 1 d . . .
H18 H 0.0910 0.3928 0.6608 0.052 Uiso 1 1 calc R . .
C19 C 0.24859(11) 0.23758(17) 0.60778(10) 0.0273(3) Uani 1 1 d . . .
O20 O 0.31037(10) 0.37971(13) 0.59356(8) 0.0386(3) Uani 1 1 d . . .
H20 H 0.3563 0.3934 0.6413 0.046 Uiso 1 1 calc R . .
C21 C 0.31737(12) 0.08417(18) 0.60443(10) 0.0288(3) Uani 1 1 d . . .
C22 C 0.42479(14) 0.0920(3) 0.58814(13) 0.0448(4) Uani 1 1 d . . .
H22 H 0.4574 0.1940 0.5782 0.054 Uiso 1 1 calc R . .
C23 C 0.48529(18) -0.0504(4) 0.58627(17) 0.0657(7) Uani 1 1 d . . .
H23 H 0.5589 -0.0442 0.5741 0.079 Uiso 1 1 calc R . .
C24 C 0.4405(2) -0.1992(3) 0.60164(15) 0.0609(6) Uani 1 1 d . . .
H24 H 0.4826 -0.2952 0.6010 0.073 Uiso 1 1 calc R . .
C25 C 0.33397(19) -0.2068(2) 0.61783(17) 0.0582(5) Uani 1 1 d . . .
H25 H 0.3020 -0.3091 0.6286 0.070 Uiso 1 1 calc R . .
C26 C 0.27235(15) -0.0671(2) 0.61864(15) 0.0467(4) Uani 1 1 d . . .
H26 H 0.1983 -0.0748 0.6291 0.056 Uiso 1 1 calc R . .
C27 C 0.15802(12) 0.23418(18) 0.52453(10) 0.0307(3) Uani 1 1 d . . .
C28 C 0.17639(15) 0.3048(2) 0.43705(12) 0.0426(4) Uani 1 1 d . . .
H28 H 0.2433 0.3569 0.4305 0.051 Uiso 1 1 calc R . .
C29 C 0.09705(17) 0.2993(3) 0.35900(13) 0.0505(5) Uani 1 1 d . . .
H29 H 0.1109 0.3465 0.2993 0.061 Uiso 1 1 calc R . .
C30 C -0.00053(16) 0.2269(2) 0.36714(13) 0.0470(4) Uani 1 1 d . . .
H30 H -0.0543 0.2244 0.3137 0.056 Uiso 1 1 calc R . .
C31 C -0.01990(15) 0.1576(2) 0.45382(14) 0.0460(4) Uani 1 1 d . . .
H31 H -0.0876 0.1077 0.4602 0.055 Uiso 1 1 calc R . .
C32 C 0.05902(14) 0.1604(2) 0.53175(12) 0.0395(3) Uani 1 1 d . . .
H32 H 0.0450 0.1111 0.5908 0.047 Uiso 1 1 calc R . .
C33A C 0.6297(2) 0.4036(4) 0.7559(2) 0.0583(7) Uani 0.778(3) 1 d P A 1
C34A C 0.6950(3) 0.4657(5) 0.6810(3) 0.0773(10) Uani 0.778(3) 1 d P A 1
H34C H 0.7104 0.5823 0.6930 0.093 Uiso 0.778(3) 1 calc PR A 1
H34D H 0.6527 0.4560 0.6172 0.093 Uiso 0.778(3) 1 calc PR A 1
C35A C 0.8013(2) 0.3750(4) 0.6788(2) 0.0613(8) Uani 0.778(3) 1 d PD A 1
H35A H 0.8478 0.4364 0.6369 0.074 Uiso 0.778(3) 1 calc PR A 1
C36A C 0.8608(3) 0.3582(10) 0.7769(4) 0.0986(19) Uani 0.778(3) 1 d P A 1
H36C H 0.9247 0.2879 0.7725 0.118 Uiso 0.778(3) 1 calc PR A 1
H36D H 0.8872 0.4665 0.7994 0.118 Uiso 0.778(3) 1 calc PR A 1
C37A C 0.7943(3) 0.2887(8) 0.8488(2) 0.0990(16) Uani 0.778(3) 1 d P A 1
H37C H 0.8361 0.2941 0.9130 0.119 Uiso 0.778(3) 1 calc PR A 1
H37D H 0.7813 0.1727 0.8332 0.119 Uiso 0.778(3) 1 calc PR A 1
C38A C 0.6874(4) 0.3697(8) 0.8550(3) 0.0809(13) Uani 0.778(3) 1 d P A 1
H38C H 0.6988 0.4732 0.8907 0.097 Uiso 0.778(3) 1 calc PR A 1
H38D H 0.6416 0.2991 0.8914 0.097 Uiso 0.778(3) 1 calc PR A 1
O39A O 0.53423(15) 0.3818(4) 0.73607(17) 0.0825(8) Uani 0.778(3) 1 d P A 1
C40A C 0.7785(4) 0.2141(7) 0.6361(3) 0.1040(15) Uani 0.778(3) 1 d PD A 1
H40D H 0.8438 0.1471 0.6450 0.156 Uiso 0.778(3) 1 calc PR A 1
H40E H 0.7557 0.2259 0.5671 0.156 Uiso 0.778(3) 1 calc PR A 1
H40F H 0.7207 0.1620 0.6678 0.156 Uiso 0.778(3) 1 calc PR A 1
C33B C 0.6657(6) 0.2716(10) 0.8029(6) 0.0474(19) Uiso 0.222(3) 1 d PD A 2
C34B C 0.7553(8) 0.1627(14) 0.7793(9) 0.074(3) Uiso 0.222(3) 1 d PD A 2
H34A H 0.7256 0.0698 0.7401 0.089 Uiso 0.222(3) 1 calc PR A 2
H34B H 0.7942 0.1195 0.8394 0.089 Uiso 0.222(3) 1 calc PR A 2
C35B C 0.8343(7) 0.2605(11) 0.7223(6) 0.052(2) Uiso 0.222(3) 1 d PD A 2
H35B H 0.8978 0.1897 0.7136 0.062 Uiso 0.222(3) 1 calc PR A 2
C36B C 0.8732(10) 0.4019(13) 0.7825(10) 0.042(2) Uiso 0.222(3) 1 d PD A 2
H36A H 0.9231 0.4648 0.7459 0.051 Uiso 0.222(3) 1 calc PR A 2
H36B H 0.9160 0.3595 0.8408 0.051 Uiso 0.222(3) 1 calc PR A 2
C37B C 0.7906(8) 0.5181(13) 0.8149(9) 0.066(3) Uiso 0.222(3) 1 d PD A 2
H37A H 0.8252 0.5925 0.8646 0.079 Uiso 0.222(3) 1 calc PR A 2
H37B H 0.7591 0.5839 0.7597 0.079 Uiso 0.222(3) 1 calc PR A 2
C38B C 0.7043(13) 0.4220(16) 0.8555(12) 0.062(4) Uiso 0.222(3) 1 d PD A 2
H38A H 0.6413 0.4942 0.8593 0.075 Uiso 0.222(3) 1 calc PR A 2
H38B H 0.7310 0.3910 0.9222 0.075 Uiso 0.222(3) 1 calc PR A 2
O39B O 0.5678(6) 0.2495(10) 0.7849(5) 0.0647(19) Uiso 0.222(3) 1 d P A 2
C40B C 0.7921(12) 0.327(2) 0.6255(9) 0.074(3) Uiso 0.222(3) 1 d PD A 2
H40A H 0.7648 0.2372 0.5835 0.111 Uiso 0.222(3) 1 calc PR A 2
H40B H 0.8505 0.3823 0.5966 0.111 Uiso 0.222(3) 1 calc PR A 2
H40C H 0.7336 0.4036 0.6330 0.111 Uiso 0.222(3) 1 calc PR A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.386(2) . ?
C1 C6 1.389(2) . ?
C1 C13 1.5361(18) . ?
C2 C3 1.403(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.365(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.388(2) . ?
C7 C8 1.390(2) . ?
C7 C13 1.5343(19) . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O14 1.4236(16) . ?
C13 C15 1.5535(19) . ?
O14 H14 0.8400 . ?
C15 O16 1.4230(18) . ?
C15 C17 1.5394(19) . ?
C15 H15 1.0000 . ?
O16 H16 0.8400 . ?
C17 O18 1.4259(17) . ?
C17 C19 1.5538(19) . ?
C17 H17 1.0000 . ?
O18 H18 0.8400 . ?
C19 O20 1.4256(16) . ?
C19 C21 1.530(2) . ?
C19 C27 1.5342(19) . ?
O20 H20 0.8400 . ?
C21 C22 1.380(2) . ?
C21 C26 1.389(2) . ?
C22 C23 1.395(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.373(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.369(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.387(2) . ?
C27 C28 1.391(2) . ?
C28 C29 1.394(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.368(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33A O39A 1.206(3) . ?
C33A C34A 1.479(4) . ?
C33A C38A 1.518(6) . ?
C34A C35A 1.522(4) . ?
C34A H34C 0.9900 . ?
C34A H34D 0.9900 . ?
C35A C40A 1.469(5) . ?
C35A C36A 1.494(7) . ?
C35A H35A 1.0000 . ?
C36A C37A 1.479(7) . ?
C36A H36C 0.9900 . ?
C36A H36D 0.9900 . ?
C37A C38A 1.499(6) . ?
C37A H37C 0.9900 . ?
C37A H37D 0.9900 . ?
C38A H38C 0.9900 . ?
C38A H38D 0.9900 . ?
C40A H40D 0.9800 . ?
C40A H40E 0.9800 . ?
C40A H40F 0.9800 . ?
C33B O39B 1.232(11) . ?
C33B C38B 1.494(9) . ?
C33B C34B 1.495(9) . ?
C34B C35B 1.551(9) . ?
C34B H34A 0.9900 . ?
C34B H34B 0.9900 . ?
C35B C36B 1.487(9) . ?
C35B C40B 1.501(9) . ?
C35B H35B 1.0000 . ?
C36B C37B 1.507(9) . ?
C36B H36A 0.9900 . ?
C36B H36B 0.9900 . ?
C37B C38B 1.492(9) . ?
C37B H37A 0.9900 . ?
C37B H37B 0.9900 . ?
C38B H38A 0.9900 . ?
C38B H38B 0.9900 . ?
C40B H40A 0.9800 . ?
C40B H40B 0.9800 . ?
C40B H40C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.52(15) . . ?
C2 C1 C13 119.75(14) . . ?
C6 C1 C13 121.69(13) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.65(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.93(19) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 121.01(17) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C12 C7 C8 117.91(14) . . ?
C12 C7 C13 120.47(13) . . ?
C8 C7 C13 121.61(12) . . ?
C9 C8 C7 121.64(13) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 119.76(15) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 119.43(15) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.65(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 120.61(15) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O14 C13 C7 109.95(11) . . ?
O14 C13 C1 107.06(11) . . ?
C7 C13 C1 109.49(11) . . ?
O14 C13 C15 109.82(11) . . ?
C7 C13 C15 110.23(11) . . ?
C1 C13 C15 110.23(11) . . ?
C13 O14 H14 109.5 . . ?
O16 C15 C17 108.10(11) . . ?
O16 C15 C13 109.11(11) . . ?
C17 C15 C13 112.48(11) . . ?
O16 C15 H15 109.0 . . ?
C17 C15 H15 109.0 . . ?
C13 C15 H15 109.0 . . ?
C15 O16 H16 109.5 . . ?
O18 C17 C15 108.49(11) . . ?
O18 C17 C19 110.24(11) . . ?
C15 C17 C19 113.72(11) . . ?
O18 C17 H17 108.1 . . ?
C15 C17 H17 108.1 . . ?
C19 C17 H17 108.1 . . ?
C17 O18 H18 109.5 . . ?
O20 C19 C21 111.25(11) . . ?
O20 C19 C27 105.96(11) . . ?
C21 C19 C27 109.41(11) . . ?
O20 C19 C17 109.07(11) . . ?
C21 C19 C17 109.86(11) . . ?
C27 C19 C17 111.24(11) . . ?
C19 O20 H20 109.5 . . ?
C22 C21 C26 118.49(16) . . ?
C22 C21 C19 121.41(15) . . ?
C26 C21 C19 120.10(13) . . ?
C21 C22 C23 119.85(19) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 121.24(19) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C25 C24 C23 118.86(18) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 120.7(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 120.85(18) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C32 C27 C28 118.25(14) . . ?
C32 C27 C19 122.89(13) . . ?
C28 C27 C19 118.84(14) . . ?
C27 C28 C29 120.31(17) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 120.90(17) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 119.26(16) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C30 C31 C32 120.38(18) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C27 C32 C31 120.89(16) . . ?
C27 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
O39A C33A C34A 119.3(3) . . ?
O39A C33A C38A 123.1(3) . . ?
C34A C33A C38A 117.6(3) . . ?
C33A C34A C35A 112.7(3) . . ?
C33A C34A H34C 109.0 . . ?
C35A C34A H34C 109.0 . . ?
C33A C34A H34D 109.0 . . ?
C35A C34A H34D 109.0 . . ?
H34C C34A H34D 107.8 . . ?
C40A C35A C36A 110.2(4) . . ?
C40A C35A C34A 108.5(3) . . ?
C36A C35A C34A 112.2(3) . . ?
C40A C35A H35A 108.6 . . ?
C36A C35A H35A 108.6 . . ?
C34A C35A H35A 108.6 . . ?
C37A C36A C35A 113.3(3) . . ?
C37A C36A H36C 108.9 . . ?
C35A C36A H36C 108.9 . . ?
C37A C36A H36D 108.9 . . ?
C35A C36A H36D 108.9 . . ?
H36C C36A H36D 107.7 . . ?
C36A C37A C38A 115.4(5) . . ?
C36A C37A H37C 108.4 . . ?
C38A C37A H37C 108.4 . . ?
C36A C37A H37D 108.4 . . ?
C38A C37A H37D 108.4 . . ?
H37C C37A H37D 107.5 . . ?
C37A C38A C33A 111.7(3) . . ?
C37A C38A H38C 109.3 . . ?
C33A C38A H38C 109.3 . . ?
C37A C38A H38D 109.3 . . ?
C33A C38A H38D 109.3 . . ?
H38C C38A H38D 107.9 . . ?
O39B C33B C38B 119.0(9) . . ?
O39B C33B C34B 127.7(9) . . ?
C38B C33B C34B 113.3(10) . . ?
C33B C34B C35B 109.1(8) . . ?
C33B C34B H34A 109.9 . . ?
C35B C34B H34A 109.9 . . ?
C33B C34B H34B 109.9 . . ?
C35B C34B H34B 109.9 . . ?
H34A C34B H34B 108.3 . . ?
C36B C35B C40B 106.7(10) . . ?
C36B C35B C34B 107.8(9) . . ?
C40B C35B C34B 117.9(10) . . ?
C36B C35B H35B 108.0 . . ?
C40B C35B H35B 108.0 . . ?
C34B C35B H35B 108.0 . . ?
C35B C36B C37B 118.3(11) . . ?
C35B C36B H36A 107.7 . . ?
C37B C36B H36A 107.7 . . ?
C35B C36B H36B 107.7 . . ?
C37B C36B H36B 107.7 . . ?
H36A C36B H36B 107.1 . . ?
C38B C37B C36B 108.5(11) . . ?
C38B C37B H37A 110.0 . . ?
C36B C37B H37A 110.0 . . ?
C38B C37B H37B 110.0 . . ?
C36B C37B H37B 110.0 . . ?
H37A C37B H37B 108.4 . . ?
C37B C38B C33B 117.5(11) . . ?
C37B C38B H38A 107.9 . . ?
C33B C38B H38A 107.9 . . ?
C37B C38B H38B 107.9 . . ?
C33B C38B H38B 107.9 . . ?
H38A C38B H38B 107.2 . . ?
C35B C40B H40A 109.5 . . ?
C35B C40B H40B 109.5 . . ?
H40A C40B H40B 109.5 . . ?
C35B C40B H40C 109.5 . . ?
H40A C40B H40C 109.5 . . ?
H40B C40B H40C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(3) . . . . ?
C13 C1 C2 C3 176.39(19) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C13 C1 C6 C5 -176.38(14) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
C13 C7 C8 C9 179.41(14) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C8 C7 C12 C11 -0.2(2) . . . . ?
C13 C7 C12 C11 -179.26(14) . . . . ?
C10 C11 C12 C7 0.3(3) . . . . ?
C12 C7 C13 O14 -5.81(18) . . . . ?
C8 C7 C13 O14 175.20(12) . . . . ?
C12 C7 C13 C1 111.56(15) . . . . ?
C8 C7 C13 C1 -67.44(16) . . . . ?
C12 C7 C13 C15 -127.01(14) . . . . ?
C8 C7 C13 C15 53.99(16) . . . . ?
C2 C1 C13 O14 18.32(19) . . . . ?
C6 C1 C13 O14 -164.26(14) . . . . ?
C2 C1 C13 C7 -100.84(17) . . . . ?
C6 C1 C13 C7 76.57(17) . . . . ?
C2 C1 C13 C15 137.73(16) . . . . ?
C6 C1 C13 C15 -44.85(19) . . . . ?
O14 C13 C15 O16 58.78(14) . . . . ?
C7 C13 C15 O16 -179.93(11) . . . . ?
C1 C13 C15 O16 -58.94(15) . . . . ?
O14 C13 C15 C17 -61.17(14) . . . . ?
C7 C13 C15 C17 60.12(14) . . . . ?
C1 C13 C15 C17 -178.89(11) . . . . ?
O16 C15 C17 O18 -51.47(15) . . . . ?
C13 C15 C17 O18 69.06(14) . . . . ?
O16 C15 C17 C19 71.58(14) . . . . ?
C13 C15 C17 C19 -167.88(12) . . . . ?
O18 C17 C19 O20 58.99(15) . . . . ?
C15 C17 C19 O20 -63.10(14) . . . . ?
O18 C17 C19 C21 -178.82(12) . . . . ?
C15 C17 C19 C21 59.08(14) . . . . ?
O18 C17 C19 C27 -57.53(15) . . . . ?
C15 C17 C19 C27 -179.62(11) . . . . ?
O20 C19 C21 C22 -0.74(19) . . . . ?
C27 C19 C21 C22 115.99(15) . . . . ?
C17 C19 C21 C22 -121.62(15) . . . . ?
O20 C19 C21 C26 178.75(14) . . . . ?
C27 C19 C21 C26 -64.51(18) . . . . ?
C17 C19 C21 C26 57.87(18) . . . . ?
C26 C21 C22 C23 0.0(3) . . . . ?
C19 C21 C22 C23 179.53(16) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C21 -0.9(3) . . . . ?
C22 C21 C26 C25 0.9(3) . . . . ?
C19 C21 C26 C25 -178.65(17) . . . . ?
O20 C19 C27 C32 -152.56(15) . . . . ?
C21 C19 C27 C32 87.40(17) . . . . ?
C17 C19 C27 C32 -34.16(19) . . . . ?
O20 C19 C27 C28 28.95(18) . . . . ?
C21 C19 C27 C28 -91.08(16) . . . . ?
C17 C19 C27 C28 147.36(15) . . . . ?
C32 C27 C28 C29 -0.6(3) . . . . ?
C19 C27 C28 C29 177.98(16) . . . . ?
C27 C28 C29 C30 0.9(3) . . . . ?
C28 C29 C30 C31 -0.4(3) . . . . ?
C29 C30 C31 C32 -0.4(3) . . . . ?
C28 C27 C32 C31 -0.3(3) . . . . ?
C19 C27 C32 C31 -178.75(15) . . . . ?
C30 C31 C32 C27 0.8(3) . . . . ?
O39A C33A C34A C35A -135.3(3) . . . . ?
C38A C33A C34A C35A 44.5(5) . . . . ?
C33A C34A C35A C40A 73.6(4) . . . . ?
C33A C34A C35A C36A -48.4(5) . . . . ?
C40A C35A C36A C37A -68.9(6) . . . . ?
C34A C35A C36A C37A 52.1(6) . . . . ?
C35A C36A C37A C38A -51.3(7) . . . . ?
C36A C37A C38A C33A 44.3(7) . . . . ?
O39A C33A C38A C37A 138.0(4) . . . . ?
C34A C33A C38A C37A -41.8(6) . . . . ?
O39B C33B C34B C35B 125.8(11) . . . . ?
C38B C33B C34B C35B -54.9(13) . . . . ?
C33B C34B C35B C36B 57.2(12) . . . . ?
C33B C34B C35B C40B -63.5(14) . . . . ?
C40B C35B C36B C37B 70.4(14) . . . . ?
C34B C35B C36B C37B -57.1(14) . . . . ?
C35B C36B C37B C38B 48.2(16) . . . . ?
C36B C37B C38B C33B -42.0(18) . . . . ?
O39B C33B C38B C37B -131.4(13) . . . . ?
C34B C33B C38B C37B 49.3(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.037

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 3-methylcyclohexanone'
_database_code_depnum_ccdc_archive 'CCDC 989004'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c:\ntwin5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol/
4-methylcyclohexanone (1:1)
;
_chemical_name_common            none
_chemical_melting_point          421
_chemical_formula_moiety         'C28 H26 O4, C7 H12 O1'
_chemical_formula_sum            'C35 H38 O5'
_chemical_formula_weight         538.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   8.181(2)
_cell_length_b                   9.952(3)
_cell_length_c                   10.163(3)
_cell_angle_alpha                79.296(6)
_cell_angle_beta                 68.813(5)
_cell_angle_gamma                65.825(5)
_cell_volume                     703.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      26.0
_chemical_absolute_configuration syn

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6189
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 All crystal specimens tested displayed non-merohedral twinning.
For the best specimen selected for analysis, the correct unit cell 
and orientation matrix were determined using the program CELL_NOW 
(GM Sheldrick, http:/shelx.uni-ac.gwdg.de/SHELX/), the second twin 
domain being located and indexed by appropriate rotation 
of the cell.In the final refinement, the SHELXL-97 instructions HKLF 5, 
MERG 0 and BASF 0.45 were employed, the latter refining to 0.422(2).
This recommended treatment of the non-merohedral twinning was succesful; 
the ALERT B warning in the checkCIF file is a known consequence of the 
necessary employment of the HKLF 5 refinement mode in SHELXL-97.       
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Duo diffractometer'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean n/a
_diffrn_standards_number         n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            9415
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0925
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.14
_reflns_number_total             9403
_reflns_number_gt                5729
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury (Macrae at al., 2006) and POV-RAY (Cason, 2003)
;
_computing_publication_material  'PLATON (Spek, 1990)'


_refine_special_details          
; 
 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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.1(13)
_refine_ls_number_reflns         9403
_refine_ls_number_parameters     366
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3761(6) 0.2637(5) 0.2123(4) 0.0273(11) Uani 1 1 d . . .
C2 C 0.3822(6) 0.1931(5) 0.1044(4) 0.0326(12) Uani 1 1 d . . .
H2 H 0.3349 0.2502 0.0308 0.039 Uiso 1 1 calc R . .
C3 C 0.4569(7) 0.0385(6) 0.1016(5) 0.0422(13) Uani 1 1 d . . .
H3 H 0.4601 -0.0089 0.0272 0.051 Uiso 1 1 calc R . .
C4 C 0.5265(7) -0.0446(6) 0.2103(5) 0.0372(12) Uani 1 1 d . . .
H4 H 0.5790 -0.1491 0.2090 0.045 Uiso 1 1 calc R . .
C5 C 0.5197(7) 0.0231(5) 0.3175(5) 0.0355(12) Uani 1 1 d . . .
H5 H 0.5659 -0.0345 0.3914 0.043 Uiso 1 1 calc R . .
C6 C 0.4451(7) 0.1770(5) 0.3201(4) 0.0299(11) Uani 1 1 d . . .
H6 H 0.4412 0.2230 0.3956 0.036 Uiso 1 1 calc R . .
C7 C 0.4660(6) 0.4887(5) 0.1531(4) 0.0224(10) Uani 1 1 d . . .
C8 C 0.6014(6) 0.4462(5) 0.2190(4) 0.0276(11) Uani 1 1 d . . .
H8 H 0.5904 0.3847 0.3027 0.033 Uiso 1 1 calc R . .
C9 C 0.7546(7) 0.4917(5) 0.1652(5) 0.0345(12) Uani 1 1 d . . .
H9 H 0.8451 0.4624 0.2133 0.041 Uiso 1 1 calc R . .
C10 C 0.7748(7) 0.5789(5) 0.0431(4) 0.0317(11) Uani 1 1 d . . .
H10 H 0.8810 0.6073 0.0045 0.038 Uiso 1 1 calc R . .
C11 C 0.6388(7) 0.6244(5) -0.0225(4) 0.0369(12) Uani 1 1 d . . .
H11 H 0.6501 0.6870 -0.1053 0.044 Uiso 1 1 calc R . .
C12 C 0.4839(6) 0.5800(5) 0.0307(4) 0.0266(10) Uani 1 1 d . . .
H12 H 0.3918 0.6118 -0.0161 0.032 Uiso 1 1 calc R . .
C13 C 0.3003(6) 0.4344(4) 0.2087(4) 0.0207(10) Uani 1 1 d . . .
O14 O 0.1884(4) 0.4848(3) 0.1164(2) 0.0278(7) Uani 1 1 d . . .
H14 H 0.1423 0.5774 0.1124 0.033 Uiso 1 1 calc R . .
C15 C 0.1751(6) 0.4899(5) 0.3582(4) 0.0245(10) Uani 1 1 d . . .
H15 H 0.2528 0.4506 0.4234 0.029 Uiso 1 1 calc R . .
O16 O 0.0234(4) 0.4376(3) 0.4076(3) 0.0325(8) Uani 1 1 d . . .
H16 H 0.0359 0.3773 0.4764 0.039 Uiso 1 1 calc R . .
C17 C 0.0890(7) 0.6586(5) 0.3594(4) 0.0239(10) Uani 1 1 d . . .
H17 H 0.1911 0.6955 0.3002 0.029 Uiso 1 1 calc R . .
O18 O -0.0559(5) 0.7141(3) 0.2945(3) 0.0369(8) Uani 1 1 d . . .
H18 H -0.1332 0.6720 0.3326 0.044 Uiso 1 1 calc R . .
C19 C 0.0113(6) 0.7214(5) 0.5090(4) 0.0223(10) Uani 1 1 d . . .
O20 O -0.1443(4) 0.6756(3) 0.5947(3) 0.0309(7) Uani 1 1 d . . .
H20 H -0.1174 0.5879 0.5788 0.037 Uiso 1 1 calc R . .
C21 C 0.1696(6) 0.6645(5) 0.5759(4) 0.0248(10) Uani 1 1 d . . .
C22 C 0.1702(7) 0.5651(5) 0.6905(4) 0.0342(12) Uani 1 1 d . . .
H22 H 0.0658 0.5349 0.7335 0.041 Uiso 1 1 calc R . .
C23 C 0.3220(8) 0.5077(5) 0.7446(4) 0.0436(14) Uani 1 1 d . . .
H23 H 0.3205 0.4390 0.8231 0.052 Uiso 1 1 calc R . .
C24 C 0.4738(8) 0.5517(6) 0.6832(5) 0.0472(14) Uani 1 1 d . . .
H24 H 0.5768 0.5134 0.7197 0.057 Uiso 1 1 calc R . .
C25 C 0.4758(8) 0.6514(7) 0.5688(5) 0.0490(14) Uani 1 1 d . . .
H25 H 0.5804 0.6814 0.5259 0.059 Uiso 1 1 calc R . .
C26 C 0.3252(7) 0.7069(5) 0.5172(4) 0.0389(13) Uani 1 1 d . . .
H26 H 0.3272 0.7763 0.4392 0.047 Uiso 1 1 calc R . .
C27 C -0.0755(6) 0.8901(5) 0.5042(4) 0.0245(10) Uani 1 1 d . . .
C28 C -0.2283(7) 0.9633(5) 0.6157(4) 0.0329(11) Uani 1 1 d . . .
H28 H -0.2828 0.9072 0.6918 0.039 Uiso 1 1 calc R . .
C29 C -0.3047(7) 1.1164(6) 0.6200(5) 0.0401(12) Uani 1 1 d . . .
H29 H -0.4116 1.1644 0.6966 0.048 Uiso 1 1 calc R . .
C30 C -0.2209(7) 1.1982(5) 0.5091(4) 0.0395(12) Uani 1 1 d . . .
H30 H -0.2692 1.3026 0.5112 0.047 Uiso 1 1 calc R . .
C31 C -0.0690(7) 1.1279(6) 0.3973(5) 0.0384(12) Uani 1 1 d . . .
H31 H -0.0137 1.1837 0.3214 0.046 Uiso 1 1 calc R . .
C32 C 0.0036(7) 0.9747(5) 0.3955(4) 0.0329(12) Uani 1 1 d . . .
H32 H 0.1095 0.9269 0.3183 0.039 Uiso 1 1 calc R . .
C33 C -0.0017(7) 0.2120(5) 0.7520(4) 0.0350(11) Uani 1 1 d . . .
C34 C -0.1349(7) 0.2076(5) 0.8961(4) 0.0381(11) Uani 1 1 d . . .
H34A H -0.2240 0.1656 0.8928 0.046 Uiso 1 1 calc R . .
H34B H -0.2095 0.3096 0.9280 0.046 Uiso 1 1 calc R . .
C35 C -0.0358(7) 0.1165(5) 1.0034(4) 0.0406(13) Uani 1 1 d . . .
H35A H 0.0288 0.1711 1.0244 0.049 Uiso 1 1 calc R . .
H35B H -0.1316 0.1028 1.0924 0.049 Uiso 1 1 calc R . .
C36 C 0.1087(7) -0.0343(5) 0.9501(4) 0.0369(11) Uani 1 1 d . . .
H36 H 0.1801 -0.0813 1.0190 0.044 Uiso 1 1 calc R . .
C37 C 0.2479(7) -0.0160(5) 0.8099(5) 0.0457(12) Uani 1 1 d . . .
H37A H 0.3398 -0.1146 0.7761 0.055 Uiso 1 1 calc R . .
H37B H 0.3188 0.0382 0.8225 0.055 Uiso 1 1 calc R . .
C38 C 0.1534(7) 0.0666(6) 0.6986(4) 0.0437(14) Uani 1 1 d . . .
H38A H 0.2489 0.0848 0.6118 0.052 Uiso 1 1 calc R . .
H38B H 0.0993 0.0055 0.6745 0.052 Uiso 1 1 calc R . .
O39 O -0.0201(5) 0.3268(3) 0.6775(3) 0.0485(9) Uani 1 1 d . . .
C40 C 0.0125(7) -0.1360(5) 0.9429(5) 0.0450(12) Uani 1 1 d . . .
H40A H -0.0573 -0.0931 0.8750 0.067 Uiso 1 1 calc R . .
H40B H -0.0752 -0.1465 1.0364 0.067 Uiso 1 1 calc R . .
H40C H 0.1088 -0.2331 0.9127 0.067 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.385(6) . ?
C1 C6 1.400(6) . ?
C1 C13 1.550(6) . ?
C2 C3 1.405(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.357(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.379(6) . ?
C7 C12 1.397(5) . ?
C7 C13 1.544(6) . ?
C8 C9 1.397(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.403(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O14 1.428(5) . ?
C13 C15 1.545(5) . ?
O14 H14 0.8400 . ?
C15 O16 1.430(5) . ?
C15 C17 1.533(4) . ?
C15 H15 1.0000 . ?
O16 H16 0.8400 . ?
C17 O18 1.428(5) . ?
C17 C19 1.560(5) . ?
C17 H17 1.0000 . ?
O18 H18 0.8400 . ?
C19 O20 1.454(5) . ?
C19 C21 1.534(6) . ?
C19 C27 1.530(6) . ?
O20 H20 0.8400 . ?
C21 C22 1.381(6) . ?
C21 C26 1.397(6) . ?
C22 C23 1.402(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.383(6) . ?
C27 C32 1.390(5) . ?
C28 C29 1.393(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.400(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.374(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(6) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 O39 1.233(5) . ?
C33 C34 1.481(5) . ?
C33 C38 1.513(7) . ?
C34 C35 1.530(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.525(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.504(6) . ?
C36 C40 1.540(6) . ?
C36 H36 1.0000 . ?
C37 C38 1.523(6) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.2(4) . . ?
C2 C1 C13 119.8(4) . . ?
C6 C1 C13 121.9(4) . . ?
C1 C2 C3 121.3(4) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.6(4) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C12 118.5(4) . . ?
C8 C7 C13 121.8(3) . . ?
C12 C7 C13 119.7(4) . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 121.3(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 119.5(4) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
O14 C13 C15 109.6(3) . . ?
O14 C13 C7 110.8(3) . . ?
C15 C13 C7 110.1(3) . . ?
O14 C13 C1 106.1(3) . . ?
C15 C13 C1 109.9(3) . . ?
C7 C13 C1 110.3(3) . . ?
C13 O14 H14 109.5 . . ?
O16 C15 C17 107.9(4) . . ?
O16 C15 C13 109.0(3) . . ?
C17 C15 C13 112.0(3) . . ?
O16 C15 H15 109.3 . . ?
C17 C15 H15 109.3 . . ?
C13 C15 H15 109.3 . . ?
C15 O16 H16 109.5 . . ?
O18 C17 C15 109.7(4) . . ?
O18 C17 C19 110.3(4) . . ?
C15 C17 C19 114.3(3) . . ?
O18 C17 H17 107.4 . . ?
C15 C17 H17 107.4 . . ?
C19 C17 H17 107.4 . . ?
C17 O18 H18 109.5 . . ?
O20 C19 C21 110.9(3) . . ?
O20 C19 C27 104.9(3) . . ?
C21 C19 C27 110.7(3) . . ?
O20 C19 C17 108.4(3) . . ?
C21 C19 C17 109.8(3) . . ?
C27 C19 C17 112.1(3) . . ?
C19 O20 H20 109.5 . . ?
C22 C21 C26 117.3(4) . . ?
C22 C21 C19 122.3(4) . . ?
C26 C21 C19 120.3(4) . . ?
C21 C22 C23 121.3(5) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 119.7(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 119.5(5) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C21 122.2(4) . . ?
C25 C26 H26 118.9 . . ?
C21 C26 H26 118.9 . . ?
C28 C27 C32 117.7(4) . . ?
C28 C27 C19 120.1(4) . . ?
C32 C27 C19 122.0(4) . . ?
C27 C28 C29 122.2(4) . . ?
C27 C28 H28 118.9 . . ?
C29 C28 H28 118.9 . . ?
C28 C29 C30 118.7(4) . . ?
C28 C29 H29 120.7 . . ?
C30 C29 H29 120.7 . . ?
C31 C30 C29 120.2(5) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 119.8(4) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C27 121.5(4) . . ?
C31 C32 H32 119.3 . . ?
C27 C32 H32 119.3 . . ?
O39 C33 C34 121.9(4) . . ?
O39 C33 C38 121.7(4) . . ?
C34 C33 C38 116.3(4) . . ?
C33 C34 C35 113.1(4) . . ?
C33 C34 H34A 109.0 . . ?
C35 C34 H34A 109.0 . . ?
C33 C34 H34B 109.0 . . ?
C35 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C36 C35 C34 112.3(3) . . ?
C36 C35 H35A 109.1 . . ?
C34 C35 H35A 109.1 . . ?
C36 C35 H35B 109.1 . . ?
C34 C35 H35B 109.1 . . ?
H35A C35 H35B 107.9 . . ?
C37 C36 C35 109.9(4) . . ?
C37 C36 C40 111.9(4) . . ?
C35 C36 C40 111.6(4) . . ?
C37 C36 H36 107.7 . . ?
C35 C36 H36 107.7 . . ?
C40 C36 H36 107.7 . . ?
C36 C37 C38 112.7(4) . . ?
C36 C37 H37A 109.1 . . ?
C38 C37 H37A 109.1 . . ?
C36 C37 H37B 109.1 . . ?
C38 C37 H37B 109.1 . . ?
H37A C37 H37B 107.8 . . ?
C33 C38 C37 110.8(4) . . ?
C33 C38 H38A 109.5 . . ?
C37 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 108.1 . . ?
C36 C40 H40A 109.5 . . ?
C36 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C36 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(6) . . . . ?
C13 C1 C2 C3 177.5(4) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C3 C4 C5 C6 -0.8(7) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C13 C1 C6 C5 -177.4(4) . . . . ?
C4 C5 C6 C1 0.1(7) . . . . ?
C12 C7 C8 C9 -0.4(6) . . . . ?
C13 C7 C8 C9 177.7(4) . . . . ?
C7 C8 C9 C10 -1.0(7) . . . . ?
C8 C9 C10 C11 2.1(7) . . . . ?
C9 C10 C11 C12 -1.9(7) . . . . ?
C8 C7 C12 C11 0.7(6) . . . . ?
C13 C7 C12 C11 -177.5(4) . . . . ?
C10 C11 C12 C7 0.4(6) . . . . ?
C8 C7 C13 O14 -175.6(4) . . . . ?
C12 C7 C13 O14 2.6(5) . . . . ?
C8 C7 C13 C15 63.0(5) . . . . ?
C12 C7 C13 C15 -118.8(4) . . . . ?
C8 C7 C13 C1 -58.4(5) . . . . ?
C12 C7 C13 C1 119.8(4) . . . . ?
C2 C1 C13 O14 20.5(5) . . . . ?
C6 C1 C13 O14 -161.4(4) . . . . ?
C2 C1 C13 C15 138.9(4) . . . . ?
C6 C1 C13 C15 -43.0(6) . . . . ?
C2 C1 C13 C7 -99.6(4) . . . . ?
C6 C1 C13 C7 78.5(5) . . . . ?
O14 C13 C15 O16 58.2(4) . . . . ?
C7 C13 C15 O16 -179.7(3) . . . . ?
C1 C13 C15 O16 -58.1(4) . . . . ?
O14 C13 C15 C17 -61.2(5) . . . . ?
C7 C13 C15 C17 60.9(5) . . . . ?
C1 C13 C15 C17 -177.5(4) . . . . ?
O16 C15 C17 O18 -47.6(3) . . . . ?
C13 C15 C17 O18 72.4(5) . . . . ?
O16 C15 C17 C19 76.8(5) . . . . ?
C13 C15 C17 C19 -163.1(3) . . . . ?
O18 C17 C19 O20 60.2(4) . . . . ?
C15 C17 C19 O20 -63.9(5) . . . . ?
O18 C17 C19 C21 -178.5(3) . . . . ?
C15 C17 C19 C21 57.4(5) . . . . ?
O18 C17 C19 C27 -55.0(4) . . . . ?
C15 C17 C19 C27 -179.2(4) . . . . ?
O20 C19 C21 C22 9.0(5) . . . . ?
C27 C19 C21 C22 125.0(4) . . . . ?
C17 C19 C21 C22 -110.8(4) . . . . ?
O20 C19 C21 C26 -174.3(4) . . . . ?
C27 C19 C21 C26 -58.3(5) . . . . ?
C17 C19 C21 C26 65.9(5) . . . . ?
C26 C21 C22 C23 -0.7(6) . . . . ?
C19 C21 C22 C23 176.1(4) . . . . ?
C21 C22 C23 C24 0.4(7) . . . . ?
C22 C23 C24 C25 -0.2(7) . . . . ?
C23 C24 C25 C26 0.4(7) . . . . ?
C24 C25 C26 C21 -0.7(8) . . . . ?
C22 C21 C26 C25 0.9(7) . . . . ?
C19 C21 C26 C25 -176.0(5) . . . . ?
O20 C19 C27 C28 29.3(5) . . . . ?
C21 C19 C27 C28 -90.4(5) . . . . ?
C17 C19 C27 C28 146.7(4) . . . . ?
O20 C19 C27 C32 -156.0(4) . . . . ?
C21 C19 C27 C32 84.3(5) . . . . ?
C17 C19 C27 C32 -38.6(6) . . . . ?
C32 C27 C28 C29 1.1(7) . . . . ?
C19 C27 C28 C29 176.0(5) . . . . ?
C27 C28 C29 C30 -1.5(7) . . . . ?
C28 C29 C30 C31 1.5(7) . . . . ?
C29 C30 C31 C32 -1.1(7) . . . . ?
C30 C31 C32 C27 0.7(7) . . . . ?
C28 C27 C32 C31 -0.7(6) . . . . ?
C19 C27 C32 C31 -175.5(4) . . . . ?
O39 C33 C34 C35 -137.2(5) . . . . ?
C38 C33 C34 C35 45.4(6) . . . . ?
C33 C34 C35 C36 -48.8(5) . . . . ?
C34 C35 C36 C37 55.0(5) . . . . ?
C34 C35 C36 C40 -69.8(5) . . . . ?
C35 C36 C37 C38 -58.1(5) . . . . ?
C40 C36 C37 C38 66.6(5) . . . . ?
O39 C33 C38 C37 135.5(5) . . . . ?
C34 C33 C38 C37 -47.0(6) . . . . ?
C36 C37 C38 C33 53.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        27.14
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 1007403'
