# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ssspiro
_database_code_depnum_ccdc_archive 'CCDC 1986058'
loop_
_audit_author_name
_audit_author_address
'Jeff W. Kampf'
;University of Michigan
United States of America
;
_audit_update_record             
;
2020-02-24 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(1S,3S,3'S)-3,3'-diethyl-3H,3'H-1,1'-spirobi[isobenzofuran]-7,7'-diol
_chemical_name_common            (S,S,S)-SPIROL
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 O4'
_chemical_formula_sum            'C19 H20 O4'
_chemical_formula_weight         312.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   12.81980(10)
_cell_length_b                   12.81980(10)
_cell_length_c                   27.9907(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3983.88(9)
_cell_formula_units_Z            9
_cell_measurement_temperature    85(2)
_cell_measurement_reflns_used    33076
_cell_measurement_theta_min      3.1490
_cell_measurement_theta_max      69.0340

_exptl_crystal_description       hexagonal
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             1494
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.664
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      85(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61312
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.982
_diffrn_reflns_theta_max         69.164
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4949
_reflns_number_gt                4874
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Two reflections were deemed to be affected by secondary extinction effects
 and/or beam stop truncation and were excluded from the refinement.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0880P)²+0.4027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2032 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 

 Bayesian Statistics                       
 Student_T Nu       13                                  
 Select Pairs     2123                              
 Theta_Min ..     6.91                                    
 Theta_Max ..    69.01                        
 P2(true)....    1.000                
 P3(true)....    1.000                               
 P3(rac-twin)  0.8E-40                        
 P3(false) ..  0.2-129                            
 G ..........   1.2271                         
 G (su) .....   0.0876                                       
 Hooft y .... -0.11(4)                         
 
;
_refine_ls_abs_structure_Flack   -0.11(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4949
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.95670(16) 0.44900(15) 0.49894(6) 0.0509(4) Uani 1 1 d . . . . .
H1 H 0.998(4) 0.517(4) 0.4932(13) 0.096(13) Uiso 1 1 d . . . . .
O2 O 0.69009(12) 0.07793(12) 0.48428(5) 0.0361(3) Uani 1 1 d . . . . .
O3 O 0.87803(12) 0.17763(13) 0.52194(5) 0.0367(3) Uani 1 1 d . . . . .
O4 O 0.59920(16) 0.26321(18) 0.50186(6) 0.0498(4) Uani 1 1 d . . . . .
H4 H 0.560(4) 0.294(4) 0.5066(14) 0.100(14) Uiso 1 1 d . . . . .
O5 O 0.11565(14) 0.29326(18) 0.49935(5) 0.0476(4) Uani 1 1 d . . . . .
H5 H 0.045(4) 0.262(4) 0.4955(12) 0.075(10) Uiso 1 1 d . . . . .
O6 O 0.38750(13) 0.48178(12) 0.51903(5) 0.0342(3) Uani 1 1 d . . . . .
C1 C 0.90909(18) 0.39271(18) 0.45710(8) 0.0362(4) Uani 1 1 d . . . . .
C2 C 0.9385(2) 0.4476(2) 0.41231(8) 0.0464(5) Uani 1 1 d . . . . .
H2 H 0.995804 0.530965 0.409627 0.056 Uiso 1 1 calc R U . . .
C3 C 0.8839(2) 0.3804(2) 0.37170(9) 0.0517(6) Uani 1 1 d . . . . .
H3 H 0.903754 0.419503 0.341508 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8014(2) 0.2582(2) 0.37359(8) 0.0512(6) Uani 1 1 d . . . . .
H4A H 0.765571 0.213124 0.345396 0.061 Uiso 1 1 calc R U . . .
C5 C 0.77285(18) 0.20401(19) 0.41858(7) 0.0390(4) Uani 1 1 d . . . . .
C6 C 0.82592(16) 0.27042(17) 0.45906(7) 0.0320(4) Uani 1 1 d . . . . .
C7 C 0.78273(15) 0.19150(17) 0.50236(6) 0.0312(4) Uani 1 1 d . . . . .
C8 C 0.6891(2) 0.0757(2) 0.43232(8) 0.0459(5) Uani 1 1 d . . . . .
H8 H 0.606202 0.050548 0.420574 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7267(4) -0.0128(3) 0.41427(11) 0.0762(10) Uani 1 1 d . . . . .
H9A H 0.809041 0.012759 0.425840 0.091 Uiso 1 1 calc R U . . .
H9B H 0.729003 -0.010637 0.378914 0.091 Uiso 1 1 calc R U . . .
C10 C 0.6416(5) -0.1415(3) 0.43070(16) 0.1104(16) Uani 1 1 d . . . . .
H10A H 0.649673 -0.147173 0.465281 0.166 Uiso 1 1 calc R U . . .
H10B H 0.662063 -0.196485 0.414307 0.166 Uiso 1 1 calc R U . . .
H10C H 0.558477 -0.163603 0.423068 0.166 Uiso 1 1 calc R U . . .
C11 C 0.8843(2) 0.1886(2) 0.57366(8) 0.0445(5) Uani 1 1 d . . . . .
H11 H 0.965862 0.255535 0.582951 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8640(3) 0.0734(4) 0.59645(12) 0.0794(10) Uani 1 1 d . . . . .
H12A H 0.783088 0.007238 0.587350 0.095 Uiso 1 1 calc R U . . .
H12B H 0.865352 0.082226 0.631618 0.095 Uiso 1 1 calc R U . . .
C13 C 0.9577(5) 0.0393(5) 0.58204(19) 0.129(2) Uani 1 1 d . . . . .
H13A H 0.944519 0.012207 0.548724 0.194 Uiso 1 1 calc R U . . .
H13B H 0.950270 -0.025748 0.602705 0.194 Uiso 1 1 calc R U . . .
H13C H 1.038463 0.109599 0.585428 0.194 Uiso 1 1 calc R U . . .
C14 C 0.79200(19) 0.22388(19) 0.58570(7) 0.0394(5) Uani 1 1 d . . . . .
C15 C 0.7603(2) 0.2508(2) 0.62967(8) 0.0516(6) Uani 1 1 d . . . . .
H15 H 0.798052 0.247699 0.658414 0.062 Uiso 1 1 calc R U . . .
C16 C 0.6711(3) 0.2824(2) 0.62981(9) 0.0533(6) Uani 1 1 d . . . . .
H16 H 0.647388 0.300447 0.659403 0.064 Uiso 1 1 calc R U . . .
C17 C 0.6157(2) 0.2884(2) 0.58826(8) 0.0461(5) Uani 1 1 d . . . . .
H17 H 0.555509 0.310881 0.589620 0.055 Uiso 1 1 calc R U . . .
C18 C 0.64822(18) 0.26161(18) 0.54465(8) 0.0372(4) Uani 1 1 d . . . . .
C19 C 0.73590(17) 0.22806(17) 0.54433(7) 0.0326(4) Uani 1 1 d . . . . .
C20 C 0.16823(18) 0.30209(18) 0.45670(7) 0.0356(4) Uani 1 1 d . . . . .
C21 C 0.1120(2) 0.2818(2) 0.41233(8) 0.0422(5) Uani 1 1 d . . . . .
H21 H 0.028996 0.257802 0.410524 0.051 Uiso 1 1 calc R U . . .
C22 C 0.1771(2) 0.2964(2) 0.37068(8) 0.0466(5) Uani 1 1 d . . . . .
H22 H 0.137576 0.283342 0.340739 0.056 Uiso 1 1 calc R U . . .
C23 C 0.2982(2) 0.3297(2) 0.37152(7) 0.0428(5) Uani 1 1 d . . . . .
H23 H 0.341524 0.338739 0.342832 0.051 Uiso 1 1 calc R U . . .
C24 C 0.35366(17) 0.34919(17) 0.41608(7) 0.0346(4) Uani 1 1 d . . . . .
C25 C 0.28947(16) 0.33611(16) 0.45739(7) 0.0308(4) Uani 1 1 d . . . . .
C26 C 0.3706(2) 0.3706(2) 0.500000 0.0300(5) Uani 1 2 d S T P . .
C27 C 0.3853(2) 0.48118(18) 0.57094(7) 0.0380(4) Uani 1 1 d . . . . .
H27 H 0.321550 0.498726 0.582100 0.046 Uiso 1 1 calc R U . . .
C28 C 0.5063(3) 0.5770(2) 0.59017(9) 0.0578(7) Uani 1 1 d . . . . .
H28A H 0.568731 0.557350 0.580428 0.069 Uiso 1 1 calc R U . . .
H28B H 0.503123 0.576046 0.625519 0.069 Uiso 1 1 calc R U . . .
C29 C 0.5419(4) 0.7020(3) 0.57264(14) 0.0917(13) Uani 1 1 d . . . . .
H29A H 0.547254 0.704151 0.537695 0.138 Uiso 1 1 calc R U . . .
H29B H 0.620327 0.760249 0.586157 0.138 Uiso 1 1 calc R U . . .
H29C H 0.481262 0.722693 0.582712 0.138 Uiso 1 1 calc R U . . .


_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 1.351(3) . ?
O1 H1 0.78(5) . ?
O2 C7 1.434(2) . ?
O2 C8 1.455(2) . ?
O3 C7 1.429(2) . ?
O3 C11 1.453(2) . ?
O4 C18 1.358(3) . ?
O4 H4 0.79(5) . ?
O5 C20 1.348(3) . ?
O5 H5 0.80(4) . ?
O6 C26 1.4329(19) . ?
O6 C27 1.453(2) . ?
C1 C6 1.388(3) . ?
C1 C2 1.394(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.376(3) . ?
C5 C8 1.497(3) . ?
C6 C7 1.496(3) . ?
C7 C19 1.497(3) . ?
C8 C9 1.523(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.525(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C14 1.502(3) . ?
C11 C12 1.506(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.523(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.378(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(3) . ?
C20 C25 1.389(3) . ?
C20 C21 1.394(3) . ?
C21 C22 1.391(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(3) . ?
C24 C27 1.504(3) 4_556 ?
C25 C26 1.497(2) . ?
C27 C28 1.516(3) . ?
C27 H27 1.0000 . ?
C28 C29 1.512(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
C1 O1 H1 107(3) . . ?
C7 O2 C8 111.55(14) . . ?
C7 O3 C11 112.33(14) . . ?
C18 O4 H4 106(3) . . ?
C20 O5 H5 109(3) . . ?
C26 O6 C27 111.94(12) . . ?
O1 C1 C6 117.13(18) . . ?
O1 C1 C2 125.0(2) . . ?
C6 C1 C2 117.82(19) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 122.3(2) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 117.4(2) . . ?
C3 C4 H4A 121.3 . . ?
C5 C4 H4A 121.3 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 C8 109.24(18) . . ?
C4 C5 C8 130.1(2) . . ?
C5 C6 C1 121.97(18) . . ?
C5 C6 C7 110.33(17) . . ?
C1 C6 C7 127.69(17) . . ?
O3 C7 O2 109.55(16) . . ?
O3 C7 C6 110.15(14) . . ?
O2 C7 C6 103.85(14) . . ?
O3 C7 C19 103.87(14) . . ?
O2 C7 C19 109.66(14) . . ?
C6 C7 C19 119.64(17) . . ?
O2 C8 C5 103.94(16) . . ?
O2 C8 C9 110.1(2) . . ?
C5 C8 C9 114.4(2) . . ?
O2 C8 H8 109.4 . . ?
C5 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
C8 C9 C10 112.6(3) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C14 103.80(15) . . ?
O3 C11 C12 110.7(2) . . ?
C14 C11 C12 115.1(2) . . ?
O3 C11 H11 109.0 . . ?
C14 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
C11 C12 C13 113.2(3) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 120.7(2) . . ?
C19 C14 C11 109.17(17) . . ?
C15 C14 C11 130.1(2) . . ?
C16 C15 C14 117.3(2) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C17 C16 C15 122.2(2) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O4 C18 C17 125.0(2) . . ?
O4 C18 C19 116.81(19) . . ?
C17 C18 C19 118.1(2) . . ?
C14 C19 C18 121.67(19) . . ?
C14 C19 C7 110.39(17) . . ?
C18 C19 C7 127.94(18) . . ?
O5 C20 C25 116.63(18) . . ?
O5 C20 C21 125.70(19) . . ?
C25 C20 C21 117.66(19) . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 122.0(2) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C22 C23 C24 117.47(19) . . ?
C22 C23 H23 121.3 . . ?
C24 C23 H23 121.3 . . ?
C25 C24 C23 120.51(18) . . ?
C25 C24 C27 109.00(16) . 4_556 ?
C23 C24 C27 130.50(18) . 4_556 ?
C24 C25 C20 122.16(18) . . ?
C24 C25 C26 110.34(15) . . ?
C20 C25 C26 127.40(17) . . ?
O6 C26 O6 110.1(2) . 4_556 ?
O6 C26 C25 109.10(8) . . ?
O6 C26 C25 103.90(9) 4_556 . ?
O6 C26 C25 103.89(9) . 4_556 ?
O6 C26 C25 109.10(8) 4_556 4_556 ?
C25 C26 C25 120.6(2) . 4_556 ?
O6 C27 C24 104.00(15) . 4_556 ?
O6 C27 C28 109.97(19) . . ?
C24 C27 C28 115.40(18) 4_556 . ?
O6 C27 H27 109.1 . . ?
C24 C27 H27 109.1 4_556 . ?
C28 C27 H27 109.1 . . ?
C27 C28 C29 112.8(2) . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C29 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
O1 C1 C2 C3 179.8(2) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 C8 -179.5(2) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C8 C5 C6 C1 179.31(19) . . . . ?
C4 C5 C6 C7 -178.71(19) . . . . ?
C8 C5 C6 C7 0.6(2) . . . . ?
O1 C1 C6 C5 -179.29(19) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
O1 C1 C6 C7 -0.8(3) . . . . ?
C2 C1 C6 C7 178.26(19) . . . . ?
C11 O3 C7 O2 -110.14(17) . . . . ?
C11 O3 C7 C6 136.23(17) . . . . ?
C11 O3 C7 C19 6.9(2) . . . . ?
C8 O2 C7 O3 -107.07(18) . . . . ?
C8 O2 C7 C6 10.6(2) . . . . ?
C8 O2 C7 C19 139.54(17) . . . . ?
C5 C6 C7 O3 110.50(18) . . . . ?
C1 C6 C7 O3 -68.1(2) . . . . ?
C5 C6 C7 O2 -6.7(2) . . . . ?
C1 C6 C7 O2 174.64(18) . . . . ?
C5 C6 C7 C19 -129.33(18) . . . . ?
C1 C6 C7 C19 52.0(3) . . . . ?
C7 O2 C8 C5 -10.3(2) . . . . ?
C7 O2 C8 C9 112.7(2) . . . . ?
C6 C5 C8 O2 5.7(2) . . . . ?
C4 C5 C8 O2 -175.1(2) . . . . ?
C6 C5 C8 C9 -114.4(2) . . . . ?
C4 C5 C8 C9 64.8(3) . . . . ?
O2 C8 C9 C10 61.2(4) . . . . ?
C5 C8 C9 C10 177.8(3) . . . . ?
C7 O3 C11 C14 -5.7(2) . . . . ?
C7 O3 C11 C12 118.3(2) . . . . ?
O3 C11 C12 C13 61.0(4) . . . . ?
C14 C11 C12 C13 178.3(4) . . . . ?
O3 C11 C14 C19 2.0(2) . . . . ?
C12 C11 C14 C19 -119.1(3) . . . . ?
O3 C11 C14 C15 -177.7(2) . . . . ?
C12 C11 C14 C15 61.2(4) . . . . ?
C19 C14 C15 C16 -0.4(4) . . . . ?
C11 C14 C15 C16 179.3(2) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 O4 179.2(2) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C15 C14 C19 C18 1.5(3) . . . . ?
C11 C14 C19 C18 -178.25(19) . . . . ?
C15 C14 C19 C7 -178.1(2) . . . . ?
C11 C14 C19 C7 2.2(2) . . . . ?
O4 C18 C19 C14 179.70(19) . . . . ?
C17 C18 C19 C14 -1.6(3) . . . . ?
O4 C18 C19 C7 -0.8(3) . . . . ?
C17 C18 C19 C7 177.90(19) . . . . ?
O3 C7 C19 C14 -5.5(2) . . . . ?
O2 C7 C19 C14 111.47(18) . . . . ?
C6 C7 C19 C14 -128.82(18) . . . . ?
O3 C7 C19 C18 174.96(18) . . . . ?
O2 C7 C19 C18 -68.0(2) . . . . ?
C6 C7 C19 C18 51.7(3) . . . . ?
O5 C20 C21 C22 178.6(2) . . . . ?
C25 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C23 0.9(4) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C22 C23 C24 C27 180.0(2) . . . 4_556 ?
C23 C24 C25 C20 0.7(3) . . . . ?
C27 C24 C25 C20 -179.44(17) 4_556 . . . ?
C23 C24 C25 C26 -175.82(17) . . . . ?
C27 C24 C25 C26 4.0(2) 4_556 . . . ?
O5 C20 C25 C24 -179.50(18) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
O5 C20 C25 C26 -3.5(3) . . . . ?
C21 C20 C25 C26 175.59(19) . . . . ?
C27 O6 C26 O6 -107.32(14) . . . 4_556 ?
C27 O6 C26 C25 139.27(15) . . . . ?
C27 O6 C26 C25 9.4(2) . . . 4_556 ?
C24 C25 C26 O6 109.28(16) . . . . ?
C20 C25 C26 O6 -67.1(3) . . . . ?
C24 C25 C26 O6 -8.1(2) . . . 4_556 ?
C20 C25 C26 O6 175.51(18) . . . 4_556 ?
C24 C25 C26 C25 -130.70(16) . . . 4_556 ?
C20 C25 C26 C25 52.95(17) . . . 4_556 ?
C26 O6 C27 C24 -7.2(2) . . . 4_556 ?
C26 O6 C27 C28 116.92(19) . . . . ?
O6 C27 C28 C29 58.1(3) . . . . ?
C24 C27 C28 C29 175.4(3) 4_556 . . . ?

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
_geom_hbond_publ_flag
O1 H1 O2 0.78(5) 2.02(4) 2.717(2) 148(4) 4_656 yes
O4 H4 O6 0.79(5) 2.04(5) 2.747(2) 149(4) 4_556 yes
O5 H5 O3 0.80(4) 1.99(4) 2.713(2) 150(3) 1_455 yes

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.066

