# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_F-319
_database_code_depnum_ccdc_archive 'CCDC 1589305'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau' ICSN-CNRS
_audit_update_record             
;
2017-12-05 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 O3, H2 O'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.8748(4)
_cell_length_b                   6.9108(2)
_cell_length_c                   42.592(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.181(6)
_cell_angle_gamma                90
_cell_volume                     3200.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12704
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      71.5

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.756
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_process_details   'Reqab, (Higashi-Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku Rotating Anode'
_diffrn_radiation_monochromator  'Osmic CMF Confocal mirrors'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rapid2 large curved IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku mm007 HF 
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            20575
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         4.152
_diffrn_reflns_theta_max         68.267
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             5711
_reflns_number_gt                3378
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_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)+(0.0642P)²+0.6243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5705
_refine_ls_number_parameters     449
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.092
_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
O1W O 0.1437(2) 0.1216(3) 0.46503(5) 0.0691(6) Uani 1 1 d D . . . .
H1WA H 0.197(3) 0.216(4) 0.4627(8) 0.104 Uiso 1 1 d D U . . .
H1WB H 0.085(3) 0.150(5) 0.4520(7) 0.104 Uiso 1 1 d D U . . .
O2W O 0.6465(2) 0.5466(4) 0.48288(5) 0.0831(7) Uani 1 1 d D . . . .
H2WA H 0.602(4) 0.643(5) 0.4764(9) 0.125 Uiso 1 1 d D U . . .
H2WB H 0.648(4) 0.559(6) 0.5030(4) 0.125 Uiso 1 1 d D U . . .
O1A O 0.26736(17) 0.8166(3) 0.44130(5) 0.0606(5) Uani 1 1 d . . . . .
H1A H 0.232005 0.910864 0.448702 0.091 Uiso 1 1 calc R U . . .
C4A C 0.1795(2) 0.6687(4) 0.43443(5) 0.0443(6) Uani 1 1 d . . . . .
O2A O 0.31417(18) 0.4096(3) 0.44940(4) 0.0618(6) Uani 1 1 d . . . . .
H2OA H 0.378916 0.361398 0.443444 0.093 Uiso 1 1 calc R U . . .
C5A C 0.0798(2) 0.7331(4) 0.41030(5) 0.0415(6) Uani 1 1 d . . . . .
H5A H 0.078107 0.874776 0.411200 0.050 Uiso 1 1 calc R U . . .
O3A O -0.14063(17) 0.6576(3) 0.41259(4) 0.0577(5) Uani 1 1 d . . . . .
C1A C -0.0408(3) 0.6654(4) 0.42528(6) 0.0455(7) Uani 1 1 d . . . . .
C2A C -0.0141(3) 0.6211(4) 0.45814(5) 0.0514(7) Uani 1 1 d . . . . .
H2A H -0.073236 0.594378 0.473262 0.062 Uiso 1 1 calc R U . . .
C3A C 0.1050(3) 0.6241(4) 0.46334(6) 0.0522(7) Uani 1 1 d . . . . .
H3A H 0.139894 0.601049 0.482944 0.063 Uiso 1 1 calc R U . . .
C6A C 0.2512(3) 0.4939(4) 0.42320(6) 0.0528(7) Uani 1 1 d . . . . .
H6AA H 0.195513 0.399934 0.413969 0.063 Uiso 1 1 calc R U . . .
H6AB H 0.310004 0.532618 0.407330 0.063 Uiso 1 1 calc R U . . .
C7A C 0.0968(2) 0.6819(4) 0.37591(5) 0.0429(6) Uani 1 1 d . . . . .
C8A C 0.0461(2) 0.5181(4) 0.36416(5) 0.0486(7) Uani 1 1 d . . . . .
H8A H 0.004308 0.435873 0.377717 0.058 Uiso 1 1 calc R U . . .
C9A C 0.0545(2) 0.4666(4) 0.33179(6) 0.0477(7) Uani 1 1 d . . . . .
C10A C -0.0018(3) 0.2973(5) 0.32067(6) 0.0606(8) Uani 1 1 d . . . . .
H10A H -0.042514 0.216565 0.334676 0.073 Uiso 1 1 calc R U . . .
C11A C 0.0023(3) 0.2490(5) 0.28957(7) 0.0710(9) Uani 1 1 d . . . . .
H11A H -0.035447 0.136342 0.282480 0.085 Uiso 1 1 calc R U . . .
C12A C 0.0631(3) 0.3694(6) 0.26866(7) 0.0760(10) Uani 1 1 d . . . . .
H12A H 0.065528 0.337055 0.247472 0.091 Uiso 1 1 calc R U . . .
C13A C 0.1193(3) 0.5346(5) 0.27882(6) 0.0668(9) Uani 1 1 d . . . . .
H13A H 0.160134 0.612413 0.264408 0.080 Uiso 1 1 calc R U . . .
C14A C 0.1169(2) 0.5902(4) 0.31075(5) 0.0499(7) Uani 1 1 d . . . . .
C15A C 0.1731(2) 0.7655(4) 0.32296(6) 0.0495(7) Uani 1 1 d . . . . .
C16A C 0.2374(3) 0.8950(5) 0.30341(6) 0.0630(9) Uani 1 1 d . . . . .
H16A H 0.240749 0.870865 0.281954 0.076 Uiso 1 1 calc R U . . .
C17A C 0.2947(3) 1.0548(5) 0.31517(7) 0.0722(10) Uani 1 1 d . . . . .
H17A H 0.337025 1.137086 0.301725 0.087 Uiso 1 1 calc R U . . .
C18A C 0.2906(3) 1.0954(5) 0.34689(7) 0.0687(9) Uani 1 1 d . . . . .
H18A H 0.331211 1.203167 0.354909 0.082 Uiso 1 1 calc R U . . .
C19A C 0.2259(3) 0.9751(4) 0.36648(6) 0.0575(8) Uani 1 1 d . . . . .
H19A H 0.222009 1.004798 0.387746 0.069 Uiso 1 1 calc R U . . .
C20A C 0.1655(2) 0.8091(4) 0.35551(5) 0.0457(7) Uani 1 1 d . . . . .
C4B C 0.6301(2) 0.1248(4) 0.44227(5) 0.0455(7) Uani 1 1 d . . . . .
O1B O 0.53517(17) 0.2533(3) 0.45160(4) 0.0649(6) Uani 1 1 d . . . . .
H1B H 0.565582 0.348911 0.459967 0.097 Uiso 1 1 calc R U . . .
C5B C 0.7250(2) 0.2194(4) 0.41963(5) 0.0421(6) Uani 1 1 d . . . . .
H5B H 0.717587 0.359477 0.422712 0.051 Uiso 1 1 calc R U . . .
O2B O 0.51253(19) -0.1671(4) 0.45258(5) 0.0796(7) Uani 1 1 d . . . . .
H2OB H 0.438936 -0.178486 0.448766 0.119 Uiso 1 1 calc R U . . .
C1B C 0.8484(3) 0.1626(4) 0.43366(5) 0.0455(6) Uani 1 1 d . . . . .
O3B O 0.94925(17) 0.1831(3) 0.42148(4) 0.0553(5) Uani 1 1 d . . . . .
C2B C 0.8273(3) 0.0862(4) 0.46530(6) 0.0510(7) Uani 1 1 d . . . . .
H2B H 0.888405 0.054367 0.479714 0.061 Uiso 1 1 calc R U . . .
C3B C 0.7077(3) 0.0696(4) 0.47013(6) 0.0538(8) Uani 1 1 d . . . . .
H3B H 0.674648 0.027637 0.489056 0.065 Uiso 1 1 calc R U . . .
C6B C 0.5692(3) -0.0544(4) 0.42852(6) 0.0596(8) Uani 1 1 d . . . . .
H6BA H 0.507679 -0.015760 0.413223 0.072 Uiso 1 1 calc R U . . .
H6BB H 0.630433 -0.132083 0.417824 0.072 Uiso 1 1 calc R U . . .
C7B C 0.7088(2) 0.1851(4) 0.38460(5) 0.0409(6) Uani 1 1 d . . . . .
C8B C 0.7618(2) 0.0282(4) 0.37118(5) 0.0473(7) Uani 1 1 d . . . . .
H8B H 0.810100 -0.052384 0.383630 0.057 Uiso 1 1 calc R U . . .
C9B C 0.7467(2) -0.0186(4) 0.33872(5) 0.0445(6) Uani 1 1 d . . . . .
C10B C 0.8029(3) -0.1856(4) 0.32628(6) 0.0566(8) Uani 1 1 d . . . . .
H10B H 0.849166 -0.265521 0.339335 0.068 Uiso 1 1 calc R U . . .
C11B C 0.7900(3) -0.2312(5) 0.29518(6) 0.0651(9) Uani 1 1 d . . . . .
H11B H 0.828270 -0.340501 0.287026 0.078 Uiso 1 1 calc R U . . .
C12B C 0.7193(3) -0.1132(5) 0.27589(6) 0.0677(9) Uani 1 1 d . . . . .
H12B H 0.709761 -0.145101 0.254817 0.081 Uiso 1 1 calc R U . . .
C13B C 0.6635(3) 0.0496(5) 0.28740(6) 0.0587(8) Uani 1 1 d . . . . .
H13B H 0.616468 0.126136 0.274008 0.070 Uiso 1 1 calc R U . . .
C14B C 0.6761(2) 0.1032(4) 0.31921(5) 0.0448(6) Uani 1 1 d . . . . .
C15B C 0.6207(2) 0.2748(4) 0.33276(5) 0.0446(6) Uani 1 1 d . . . . .
C16B C 0.5520(3) 0.4052(5) 0.31452(6) 0.0593(8) Uani 1 1 d . . . . .
H16B H 0.542820 0.382127 0.293132 0.071 Uiso 1 1 calc R U . . .
C17B C 0.4979(3) 0.5657(5) 0.32744(7) 0.0674(9) Uani 1 1 d . . . . .
H17B H 0.452873 0.649998 0.314859 0.081 Uiso 1 1 calc R U . . .
C18B C 0.5106(3) 0.6020(5) 0.35925(7) 0.0632(8) Uani 1 1 d . . . . .
H18B H 0.473713 0.710598 0.368039 0.076 Uiso 1 1 calc R U . . .
C19B C 0.5771(3) 0.4790(4) 0.37774(6) 0.0546(7) Uani 1 1 d . . . . .
H19B H 0.584019 0.505135 0.399097 0.066 Uiso 1 1 calc R U . . .
C20B C 0.6354(2) 0.3139(4) 0.36549(5) 0.0427(6) Uani 1 1 d . . . . .


_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
O1W H1WA 0.876(18) . ?
O1W H1WB 0.870(18) . ?
O2W H2WA 0.870(19) . ?
O2W H2WB 0.863(18) . ?
O1A C4A 1.429(3) . ?
O1A H1A 0.8200 . ?
C4A C3A 1.508(3) . ?
C4A C6A 1.516(4) . ?
C4A C5A 1.557(3) . ?
O2A C6A 1.431(3) . ?
O2A H2OA 0.8200 . ?
C5A C7A 1.519(3) . ?
C5A C1A 1.533(3) . ?
C5A H5A 0.9800 . ?
O3A C1A 1.213(3) . ?
C1A C2A 1.461(3) . ?
C2A C3A 1.313(3) . ?
C2A H2A 0.9300 . ?
C3A H3A 0.9300 . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C7A C8A 1.354(4) . ?
C7A C20A 1.446(3) . ?
C8A C9A 1.427(3) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.402(4) . ?
C9A C14A 1.414(3) . ?
C10A C11A 1.367(4) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.388(4) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.365(4) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.413(3) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.453(4) . ?
C15A C16A 1.409(4) . ?
C15A C20A 1.421(3) . ?
C16A C17A 1.363(4) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.381(4) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.373(4) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.401(4) . ?
C19A H19A 0.9300 . ?
C4B O1B 1.419(3) . ?
C4B C3B 1.504(3) . ?
C4B C6B 1.520(4) . ?
C4B C5B 1.559(3) . ?
O1B H1B 0.8200 . ?
C5B C1B 1.519(3) . ?
C5B C7B 1.521(3) . ?
C5B H5B 0.9800 . ?
O2B C6B 1.429(3) . ?
O2B H2OB 0.8200 . ?
C1B O3B 1.223(3) . ?
C1B C2B 1.466(3) . ?
C2B C3B 1.322(4) . ?
C2B H2B 0.9300 . ?
C3B H3B 0.9300 . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C7B C8B 1.355(3) . ?
C7B C20B 1.445(3) . ?
C8B C9B 1.429(3) . ?
C8B H8B 0.9300 . ?
C9B C14B 1.409(3) . ?
C9B C10B 1.410(4) . ?
C10B C11B 1.368(3) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.388(4) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.370(4) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.411(3) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.451(4) . ?
C15B C16B 1.404(3) . ?
C15B C20B 1.428(3) . ?
C16B C17B 1.371(4) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.384(4) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.365(4) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.407(3) . ?
C19B H19B 0.9300 . ?

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
H1WA O1W H1WB 104(3) . . ?
H2WA O2W H2WB 104(4) . . ?
C4A O1A H1A 109.5 . . ?
O1A C4A C3A 109.9(2) . . ?
O1A C4A C6A 106.9(2) . . ?
C3A C4A C6A 111.9(2) . . ?
O1A C4A C5A 113.2(2) . . ?
C3A C4A C5A 102.8(2) . . ?
C6A C4A C5A 112.2(2) . . ?
C6A O2A H2OA 109.5 . . ?
C7A C5A C1A 115.9(2) . . ?
C7A C5A C4A 118.9(2) . . ?
C1A C5A C4A 103.47(19) . . ?
C7A C5A H5A 105.8 . . ?
C1A C5A H5A 105.8 . . ?
C4A C5A H5A 105.8 . . ?
O3A C1A C2A 126.3(2) . . ?
O3A C1A C5A 126.5(2) . . ?
C2A C1A C5A 107.2(2) . . ?
C3A C2A C1A 110.5(2) . . ?
C3A C2A H2A 124.7 . . ?
C1A C2A H2A 124.7 . . ?
C2A C3A C4A 113.5(2) . . ?
C2A C3A H3A 123.3 . . ?
C4A C3A H3A 123.3 . . ?
O2A C6A C4A 108.9(2) . . ?
O2A C6A H6AA 109.9 . . ?
C4A C6A H6AA 109.9 . . ?
O2A C6A H6AB 109.9 . . ?
C4A C6A H6AB 109.9 . . ?
H6AA C6A H6AB 108.3 . . ?
C8A C7A C20A 119.8(2) . . ?
C8A C7A C5A 120.0(2) . . ?
C20A C7A C5A 120.2(2) . . ?
C7A C8A C9A 122.6(2) . . ?
C7A C8A H8A 118.7 . . ?
C9A C8A H8A 118.7 . . ?
C10A C9A C14A 120.0(2) . . ?
C10A C9A C8A 120.4(2) . . ?
C14A C9A C8A 119.6(3) . . ?
C11A C10A C9A 121.0(3) . . ?
C11A C10A H10A 119.5 . . ?
C9A C10A H10A 119.5 . . ?
C10A C11A C12A 119.5(3) . . ?
C10A C11A H11A 120.2 . . ?
C12A C11A H11A 120.2 . . ?
C13A C12A C11A 120.8(3) . . ?
C13A C12A H12A 119.6 . . ?
C11A C12A H12A 119.6 . . ?
C12A C13A C14A 121.5(3) . . ?
C12A C13A H13A 119.2 . . ?
C14A C13A H13A 119.2 . . ?
C13A C14A C9A 117.1(3) . . ?
C13A C14A C15A 124.2(3) . . ?
C9A C14A C15A 118.7(2) . . ?
C16A C15A C20A 118.2(3) . . ?
C16A C15A C14A 121.8(2) . . ?
C20A C15A C14A 120.0(2) . . ?
C17A C16A C15A 121.7(3) . . ?
C17A C16A H16A 119.2 . . ?
C15A C16A H16A 119.2 . . ?
C16A C17A C18A 120.6(3) . . ?
C16A C17A H17A 119.7 . . ?
C18A C17A H17A 119.7 . . ?
C19A C18A C17A 119.3(3) . . ?
C19A C18A H18A 120.4 . . ?
C17A C18A H18A 120.4 . . ?
C18A C19A C20A 122.3(3) . . ?
C18A C19A H19A 118.9 . . ?
C20A C19A H19A 118.9 . . ?
C19A C20A C15A 118.0(2) . . ?
C19A C20A C7A 122.7(2) . . ?
C15A C20A C7A 119.3(2) . . ?
O1B C4B C3B 110.2(2) . . ?
O1B C4B C6B 107.5(2) . . ?
C3B C4B C6B 109.9(2) . . ?
O1B C4B C5B 113.2(2) . . ?
C3B C4B C5B 102.9(2) . . ?
C6B C4B C5B 113.1(2) . . ?
C4B O1B H1B 109.5 . . ?
C1B C5B C7B 116.5(2) . . ?
C1B C5B C4B 103.54(19) . . ?
C7B C5B C4B 117.8(2) . . ?
C1B C5B H5B 106.0 . . ?
C7B C5B H5B 106.0 . . ?
C4B C5B H5B 106.0 . . ?
C6B O2B H2OB 109.5 . . ?
O3B C1B C2B 125.1(3) . . ?
O3B C1B C5B 126.5(2) . . ?
C2B C1B C5B 108.3(2) . . ?
C3B C2B C1B 109.4(2) . . ?
C3B C2B H2B 125.3 . . ?
C1B C2B H2B 125.3 . . ?
C2B C3B C4B 113.9(2) . . ?
C2B C3B H3B 123.1 . . ?
C4B C3B H3B 123.1 . . ?
O2B C6B C4B 110.9(2) . . ?
O2B C6B H6BA 109.5 . . ?
C4B C6B H6BA 109.5 . . ?
O2B C6B H6BB 109.5 . . ?
C4B C6B H6BB 109.5 . . ?
H6BA C6B H6BB 108.1 . . ?
C8B C7B C20B 119.4(2) . . ?
C8B C7B C5B 119.4(2) . . ?
C20B C7B C5B 121.2(2) . . ?
C7B C8B C9B 122.8(2) . . ?
C7B C8B H8B 118.6 . . ?
C9B C8B H8B 118.6 . . ?
C14B C9B C10B 120.2(2) . . ?
C14B C9B C8B 119.8(2) . . ?
C10B C9B C8B 120.0(2) . . ?
C11B C10B C9B 120.6(3) . . ?
C11B C10B H10B 119.7 . . ?
C9B C10B H10B 119.7 . . ?
C10B C11B C12B 119.5(3) . . ?
C10B C11B H11B 120.3 . . ?
C12B C11B H11B 120.3 . . ?
C13B C12B C11B 121.1(3) . . ?
C13B C12B H12B 119.5 . . ?
C11B C12B H12B 119.5 . . ?
C12B C13B C14B 121.2(3) . . ?
C12B C13B H13B 119.4 . . ?
C14B C13B H13B 119.4 . . ?
C9B C14B C13B 117.4(2) . . ?
C9B C14B C15B 118.7(2) . . ?
C13B C14B C15B 123.9(2) . . ?
C16B C15B C20B 118.4(3) . . ?
C16B C15B C14B 121.7(2) . . ?
C20B C15B C14B 119.9(2) . . ?
C17B C16B C15B 121.7(3) . . ?
C17B C16B H16B 119.2 . . ?
C15B C16B H16B 119.2 . . ?
C16B C17B C18B 119.9(3) . . ?
C16B C17B H17B 120.1 . . ?
C18B C17B H17B 120.1 . . ?
C19B C18B C17B 120.2(3) . . ?
C19B C18B H18B 119.9 . . ?
C17B C18B H18B 119.9 . . ?
C18B C19B C20B 122.0(3) . . ?
C18B C19B H19B 119.0 . . ?
C20B C19B H19B 119.0 . . ?
C19B C20B C15B 117.8(2) . . ?
C19B C20B C7B 122.7(2) . . ?
C15B C20B C7B 119.5(2) . . ?

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
O1A C4A C5A C7A 96.4(3) . . . . ?
C3A C4A C5A C7A -145.1(2) . . . . ?
C6A C4A C5A C7A -24.7(3) . . . . ?
O1A C4A C5A C1A -133.3(2) . . . . ?
C3A C4A C5A C1A -14.9(3) . . . . ?
C6A C4A C5A C1A 105.5(2) . . . . ?
C7A C5A C1A O3A -35.6(4) . . . . ?
C4A C5A C1A O3A -167.6(3) . . . . ?
C7A C5A C1A C2A 147.1(2) . . . . ?
C4A C5A C1A C2A 15.1(3) . . . . ?
O3A C1A C2A C3A 173.2(3) . . . . ?
C5A C1A C2A C3A -9.5(3) . . . . ?
C1A C2A C3A C4A -0.9(3) . . . . ?
O1A C4A C3A C2A 131.3(3) . . . . ?
C6A C4A C3A C2A -110.1(3) . . . . ?
C5A C4A C3A C2A 10.4(3) . . . . ?
O1A C4A C6A O2A 71.9(3) . . . . ?
C3A C4A C6A O2A -48.4(3) . . . . ?
C5A C4A C6A O2A -163.4(2) . . . . ?
C1A C5A C7A C8A -31.0(4) . . . . ?
C4A C5A C7A C8A 93.4(3) . . . . ?
C1A C5A C7A C20A 148.2(2) . . . . ?
C4A C5A C7A C20A -87.5(3) . . . . ?
C20A C7A C8A C9A -1.9(4) . . . . ?
C5A C7A C8A C9A 177.2(2) . . . . ?
C7A C8A C9A C10A -178.6(3) . . . . ?
C7A C8A C9A C14A -0.4(4) . . . . ?
C14A C9A C10A C11A -0.2(4) . . . . ?
C8A C9A C10A C11A 178.0(3) . . . . ?
C9A C10A C11A C12A 0.0(5) . . . . ?
C10A C11A C12A C13A 0.3(5) . . . . ?
C11A C12A C13A C14A -0.6(5) . . . . ?
C12A C13A C14A C9A 0.4(4) . . . . ?
C12A C13A C14A C15A -179.0(3) . . . . ?
C10A C9A C14A C13A -0.1(4) . . . . ?
C8A C9A C14A C13A -178.3(3) . . . . ?
C10A C9A C14A C15A 179.4(3) . . . . ?
C8A C9A C14A C15A 1.2(4) . . . . ?
C13A C14A C15A C16A -0.9(4) . . . . ?
C9A C14A C15A C16A 179.7(2) . . . . ?
C13A C14A C15A C20A 179.9(3) . . . . ?
C9A C14A C15A C20A 0.5(4) . . . . ?
C20A C15A C16A C17A 2.2(4) . . . . ?
C14A C15A C16A C17A -177.0(3) . . . . ?
C15A C16A C17A C18A -0.5(5) . . . . ?
C16A C17A C18A C19A -1.3(5) . . . . ?
C17A C18A C19A C20A 1.4(5) . . . . ?
C18A C19A C20A C15A 0.4(4) . . . . ?
C18A C19A C20A C7A -179.7(3) . . . . ?
C16A C15A C20A C19A -2.1(4) . . . . ?
C14A C15A C20A C19A 177.1(3) . . . . ?
C16A C15A C20A C7A 178.0(2) . . . . ?
C14A C15A C20A C7A -2.8(4) . . . . ?
C8A C7A C20A C19A -176.4(3) . . . . ?
C5A C7A C20A C19A 4.4(4) . . . . ?
C8A C7A C20A C15A 3.5(4) . . . . ?
C5A C7A C20A C15A -175.7(2) . . . . ?
O1B C4B C5B C1B 132.3(2) . . . . ?
C3B C4B C5B C1B 13.5(3) . . . . ?
C6B C4B C5B C1B -105.0(2) . . . . ?
O1B C4B C5B C7B -97.5(3) . . . . ?
C3B C4B C5B C7B 143.6(2) . . . . ?
C6B C4B C5B C7B 25.1(3) . . . . ?
C7B C5B C1B O3B 38.6(4) . . . . ?
C4B C5B C1B O3B 169.6(3) . . . . ?
C7B C5B C1B C2B -144.0(2) . . . . ?
C4B C5B C1B C2B -13.1(3) . . . . ?
O3B C1B C2B C3B -175.3(3) . . . . ?
C5B C1B C2B C3B 7.3(3) . . . . ?
C1B C2B C3B C4B 2.2(3) . . . . ?
O1B C4B C3B C2B -131.3(3) . . . . ?
C6B C4B C3B C2B 110.4(3) . . . . ?
C5B C4B C3B C2B -10.3(3) . . . . ?
O1B C4B C6B O2B -71.5(3) . . . . ?
C3B C4B C6B O2B 48.4(3) . . . . ?
C5B C4B C6B O2B 162.8(2) . . . . ?
C1B C5B C7B C8B 35.4(3) . . . . ?
C4B C5B C7B C8B -88.5(3) . . . . ?
C1B C5B C7B C20B -146.2(2) . . . . ?
C4B C5B C7B C20B 89.9(3) . . . . ?
C20B C7B C8B C9B -1.1(4) . . . . ?
C5B C7B C8B C9B 177.3(2) . . . . ?
C7B C8B C9B C14B 1.3(4) . . . . ?
C7B C8B C9B C10B -179.1(3) . . . . ?
C14B C9B C10B C11B 0.2(4) . . . . ?
C8B C9B C10B C11B -179.5(3) . . . . ?
C9B C10B C11B C12B -1.0(5) . . . . ?
C10B C11B C12B C13B 0.8(5) . . . . ?
C11B C12B C13B C14B 0.2(5) . . . . ?
C10B C9B C14B C13B 0.7(4) . . . . ?
C8B C9B C14B C13B -179.6(2) . . . . ?
C10B C9B C14B C15B -179.4(2) . . . . ?
C8B C9B C14B C15B 0.3(4) . . . . ?
C12B C13B C14B C9B -0.9(4) . . . . ?
C12B C13B C14B C15B 179.2(3) . . . . ?
C9B C14B C15B C16B 178.3(2) . . . . ?
C13B C14B C15B C16B -1.8(4) . . . . ?
C9B C14B C15B C20B -1.9(4) . . . . ?
C13B C14B C15B C20B 178.0(2) . . . . ?
C20B C15B C16B C17B -0.9(4) . . . . ?
C14B C15B C16B C17B 178.9(3) . . . . ?
C15B C16B C17B C18B -0.1(5) . . . . ?
C16B C17B C18B C19B 0.3(5) . . . . ?
C17B C18B C19B C20B 0.5(5) . . . . ?
C18B C19B C20B C15B -1.5(4) . . . . ?
C18B C19B C20B C7B 178.3(3) . . . . ?
C16B C15B C20B C19B 1.6(4) . . . . ?
C14B C15B C20B C19B -178.2(2) . . . . ?
C16B C15B C20B C7B -178.2(2) . . . . ?
C14B C15B C20B C7B 2.0(4) . . . . ?
C8B C7B C20B C19B 179.7(3) . . . . ?
C5B C7B C20B C19B 1.3(4) . . . . ?
C8B C7B C20B C15B -0.5(4) . . . . ?
C5B C7B C20B C15B -179.0(2) . . . . ?

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
O1W H1WA O2A 0.876(18) 1.936(19) 2.802(3) 169(3) . yes
O1W H1WB O3B 0.870(18) 1.975(19) 2.841(3) 174(4) 1_455 yes
O2W H2WA O2B 0.870(19) 1.92(2) 2.773(3) 167(4) 1_565 yes
O2W H2WB O2A 0.863(18) 2.08(2) 2.930(3) 170(4) 3_666 yes
O1A H1A O1W 0.82 1.88 2.698(3) 177.2 1_565 yes
O2A H2OA O1B 0.82 1.89 2.636(3) 151.3 . yes
C5A H5A O3B 0.98 2.59 3.452(3) 147.0 1_465 yes
O1B H1B O2W 0.82 1.89 2.709(3) 172.4 . yes
C5B H5B O3A 0.98 2.61 3.376(3) 135.1 1_655 yes
O2B H2OB O1A 0.82 1.89 2.710(3) 175.2 1_545 yes

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.046






_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Water and methanol'
