# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_JY-740
_database_code_depnum_ccdc_archive 'CCDC 2082935'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
rac-1-((1S,2R,3S)-1-(4-(trifluoromethyl)benzyl)-2-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-benzo[f]chromen-3-yl)naphthalen-2-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H26 F6 O2'
_chemical_formula_sum            'C38 H26 F6 O2'
_chemical_formula_weight         628.59

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'
F F 0.0171 0.0103 '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      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                   10.5131(6)
_cell_length_b                   11.3065(7)
_cell_length_c                   25.1627(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.162(6)
_cell_angle_gamma                90
_cell_volume                     2973.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8252
_cell_measurement_theta_min      2.9620
_cell_measurement_theta_max      26.2860

_exptl_crystal_description       'squared plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.43635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            29061
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.977
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_full        25.028
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5257
_reflns_number_gt                3952
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_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)+(0.0667P)²+1.4216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0060(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5256
_refine_ls_number_parameters     475
_refine_ls_number_restraints     210
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.196
_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
C1 C 0.14214(19) 0.61394(19) 0.28056(8) 0.0423(5) Uani 1 1 d . . . . .
H1 H 0.187382 0.689477 0.285995 0.051 Uiso 1 1 calc R U . . .
C2 C 0.17913(19) 0.53273(19) 0.32911(8) 0.0400(5) Uani 1 1 d . . . . .
H2 H 0.133755 0.457868 0.321598 0.048 Uiso 1 1 calc R U . . .
C3 C 0.13230(19) 0.58264(19) 0.38097(8) 0.0424(5) Uani 1 1 d . . . . .
H3 H 0.204049 0.624355 0.400843 0.051 Uiso 1 1 calc R U . . .
C4 C 0.02257(19) 0.66943(19) 0.37032(9) 0.0442(5) Uani 1 1 d . . . . .
C5 C -0.0381(2) 0.6847(2) 0.32045(9) 0.0481(5) Uani 1 1 d . . . . .
C6 C -0.1517(2) 0.7508(2) 0.30983(11) 0.0607(7) Uani 1 1 d . . . . .
H6 H -0.192244 0.755858 0.275198 0.073 Uiso 1 1 calc R U . . .
C7 C -0.2012(2) 0.8067(2) 0.35040(12) 0.0658(7) Uani 1 1 d . . . . .
H7 H -0.278142 0.847412 0.343820 0.079 Uiso 1 1 calc R U . . .
C8 C -0.1376(2) 0.8041(2) 0.40234(11) 0.0591(7) Uani 1 1 d . . . . .
C9 C -0.0238(2) 0.7361(2) 0.41298(10) 0.0512(6) Uani 1 1 d . . . . .
C10 C 0.0419(3) 0.7427(2) 0.46490(10) 0.0611(7) Uani 1 1 d . . . . .
H10 H 0.116604 0.699241 0.472851 0.073 Uiso 1 1 calc R U . . .
C11 C -0.0020(3) 0.8112(3) 0.50359(12) 0.0768(8) Uani 1 1 d . . . . .
H11 H 0.043819 0.814728 0.537302 0.092 Uiso 1 1 calc R U . . .
C12 C -0.1148(3) 0.8762(3) 0.49319(14) 0.0830(9) Uani 1 1 d . . . . .
H12 H -0.144405 0.922081 0.519977 0.100 Uiso 1 1 calc R U . . .
C13 C -0.1804(3) 0.8724(3) 0.44444(14) 0.0752(8) Uani 1 1 d . . . . .
H13 H -0.255764 0.915505 0.438008 0.090 Uiso 1 1 calc R U . . .
C14 C 0.1734(2) 0.55898(19) 0.22854(8) 0.0423(5) Uani 1 1 d . . . . .
C15 C 0.0921(2) 0.4778(2) 0.20190(9) 0.0490(6) Uani 1 1 d . . . . .
C16 C 0.1251(3) 0.4176(2) 0.15656(10) 0.0583(6) Uani 1 1 d . . . . .
H16 H 0.066798 0.365646 0.138632 0.070 Uiso 1 1 calc R U . . .
C17 C 0.2399(3) 0.4341(2) 0.13867(10) 0.0576(6) Uani 1 1 d . . . . .
H17 H 0.261229 0.391330 0.109331 0.069 Uiso 1 1 calc R U . . .
C18 C 0.3282(2) 0.5155(2) 0.16387(9) 0.0482(5) Uani 1 1 d . . . . .
C19 C 0.2938(2) 0.58159(18) 0.20842(8) 0.0417(5) Uani 1 1 d . . . . .
C20 C 0.3842(2) 0.6655(2) 0.23126(9) 0.0460(5) Uani 1 1 d . . . . .
H20 H 0.363973 0.711826 0.259717 0.055 Uiso 1 1 calc R U . . .
C21 C 0.4999(2) 0.6796(2) 0.21235(10) 0.0581(6) Uani 1 1 d . . . . .
H21 H 0.557223 0.735166 0.228139 0.070 Uiso 1 1 calc R U . . .
C22 C 0.5338(3) 0.6117(3) 0.16958(11) 0.0681(7) Uani 1 1 d . . . . .
H22 H 0.613916 0.620552 0.157584 0.082 Uiso 1 1 calc R U . . .
C23 C 0.4485(3) 0.5329(2) 0.14576(10) 0.0617(7) Uani 1 1 d . . . . .
H23 H 0.470285 0.489325 0.116730 0.074 Uiso 1 1 calc R U . . .
C24 C 0.32070(19) 0.50420(18) 0.33378(8) 0.0385(5) Uani 1 1 d . . . . .
C25 C 0.3626(2) 0.4022(2) 0.31087(9) 0.0498(6) Uani 1 1 d . . . . .
H25 H 0.302812 0.351032 0.293339 0.060 Uiso 1 1 calc R U . . .
C26 C 0.4904(2) 0.3745(2) 0.31335(11) 0.0584(6) Uani 1 1 d . . . . .
H26 H 0.516286 0.305359 0.297584 0.070 Uiso 1 1 calc R U . . .
C27 C 0.5798(2) 0.4491(2) 0.33914(10) 0.0538(6) Uani 1 1 d . . . . .
C28 C 0.5409(2) 0.5526(2) 0.36144(10) 0.0538(6) Uani 1 1 d . . . . .
H28 H 0.601254 0.604352 0.378171 0.065 Uiso 1 1 calc R U . . .
C29 C 0.4127(2) 0.5792(2) 0.35891(9) 0.0457(5) Uani 1 1 d . . . . .
H29 H 0.387250 0.648790 0.374370 0.055 Uiso 1 1 calc R U . . .
C30 C 0.7181(3) 0.4189(3) 0.34253(15) 0.0839(9) Uani 1 1 d D . . . .
C31 C 0.0938(2) 0.4780(2) 0.41618(9) 0.0508(6) Uani 1 1 d . . . . .
H31A H 0.055721 0.509368 0.446680 0.061 Uiso 1 1 calc R U . . .
H31B H 0.029806 0.430120 0.395530 0.061 Uiso 1 1 calc R U . . .
C32 C 0.2060(2) 0.4011(2) 0.43579(8) 0.0459(5) Uani 1 1 d . . . . .
C33 C 0.2308(2) 0.2966(2) 0.41049(9) 0.0531(6) Uani 1 1 d . . . . .
H33 H 0.172461 0.269404 0.382782 0.064 Uiso 1 1 calc R U . . .
C34 C 0.3400(2) 0.2314(2) 0.42527(10) 0.0592(6) Uani 1 1 d . . . . .
H34 H 0.355339 0.161860 0.407299 0.071 Uiso 1 1 calc R U . . .
C35 C 0.4256(2) 0.2699(2) 0.46658(10) 0.0577(6) Uani 1 1 d . . . . .
C36 C 0.4006(3) 0.3713(2) 0.49359(11) 0.0691(8) Uani 1 1 d . . . . .
H36 H 0.457448 0.396445 0.522246 0.083 Uiso 1 1 calc R U . . .
C37 C 0.2919(3) 0.4361(2) 0.47845(9) 0.0620(7) Uani 1 1 d . . . . .
H37 H 0.275855 0.504393 0.497196 0.074 Uiso 1 1 calc R U . . .
C38 C 0.5452(3) 0.2033(3) 0.48206(15) 0.0881(9) Uani 1 1 d D . . . .
O39 O 0.00627(13) 0.63492(14) 0.27563(6) 0.0507(4) Uani 1 1 d . . . . .
O40 O -0.02430(17) 0.44644(17) 0.21725(8) 0.0674(5) Uani 1 1 d . . . . .
H40O H -0.041(3) 0.506(3) 0.2450(14) 0.101 Uiso 1 1 d . U . . .
F1 F 0.7737(2) 0.4555(3) 0.30064(12) 0.1200(11) Uani 0.899(4) 1 d D . P A 1
F2 F 0.7387(2) 0.3037(2) 0.34339(15) 0.1342(13) Uani 0.899(4) 1 d D . P A 1
F3 F 0.78543(19) 0.4690(3) 0.38407(12) 0.1307(13) Uani 0.899(4) 1 d D . P A 1
F1B F 0.749(3) 0.3559(11) 0.3042(6) 0.136(7) Uani 0.101(4) 1 d D . P A 1
F2B F 0.752(2) 0.3617(12) 0.3869(6) 0.136(5) Uani 0.101(4) 1 d D U P A 1
F3B F 0.800(2) 0.5009(19) 0.3416(5) 0.129(6) Uani 0.101(4) 1 d D . P A 1
F4 F 0.6482(3) 0.2657(4) 0.4693(3) 0.1361(17) Uani 0.684(5) 1 d D U P B 1
F5 F 0.5580(4) 0.1061(4) 0.4554(2) 0.1240(17) Uani 0.684(5) 1 d D . P B 1
F6 F 0.5626(6) 0.1780(7) 0.53164(17) 0.170(2) Uani 0.684(5) 1 d D U P B 1
F4B F 0.6126(10) 0.1848(11) 0.4431(4) 0.156(3) Uani 0.316(5) 1 d D . P B 1
F5B F 0.5209(11) 0.1015(7) 0.5036(5) 0.164(4) Uani 0.316(5) 1 d D . P B 1
F6B F 0.6250(7) 0.2567(8) 0.5189(4) 0.120(3) Uani 0.316(5) 1 d D U P B 1


_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 O39 1.440(2) . ?
C1 C14 1.517(3) . ?
C1 C2 1.544(3) . ?
C2 C24 1.515(3) . ?
C2 C3 1.550(3) . ?
C3 C4 1.516(3) . ?
C3 C31 1.557(3) . ?
C4 C5 1.356(3) . ?
C4 C9 1.439(3) . ?
C5 O39 1.385(3) . ?
C5 C6 1.410(3) . ?
C6 C7 1.352(4) . ?
C7 C8 1.403(4) . ?
C8 C13 1.422(4) . ?
C8 C9 1.423(3) . ?
C9 C10 1.412(4) . ?
C10 C11 1.363(4) . ?
C11 C12 1.396(5) . ?
C12 C13 1.342(4) . ?
C14 C15 1.379(3) . ?
C14 C19 1.435(3) . ?
C15 O40 1.368(3) . ?
C15 C16 1.403(3) . ?
C16 C17 1.346(4) . ?
C17 C18 1.408(3) . ?
C18 C23 1.403(3) . ?
C18 C19 1.425(3) . ?
C19 C20 1.420(3) . ?
C20 C21 1.362(3) . ?
C21 C22 1.399(4) . ?
C22 C23 1.358(4) . ?
C24 C25 1.382(3) . ?
C24 C29 1.387(3) . ?
C25 C26 1.375(3) . ?
C26 C27 1.373(3) . ?
C27 C28 1.379(3) . ?
C27 C30 1.486(4) . ?
C28 C29 1.376(3) . ?
C30 F3B 1.267(13) . ?
C30 F1B 1.268(14) . ?
C30 F2B 1.306(14) . ?
C30 F2 1.321(4) . ?
C30 F3 1.325(4) . ?
C30 F1 1.325(4) . ?
C31 C32 1.506(3) . ?
C32 C33 1.380(3) . ?
C32 C37 1.384(3) . ?
C33 C34 1.381(3) . ?
C34 C35 1.370(3) . ?
C35 C36 1.373(4) . ?
C35 C38 1.482(4) . ?
C36 C37 1.376(4) . ?
C38 F6 1.274(5) . ?
C38 F4B 1.286(9) . ?
C38 F5 1.302(5) . ?
C38 F5B 1.308(8) . ?
C38 F6B 1.327(7) . ?
C38 F4 1.360(5) . ?
F1 F3B 1.157(12) . ?
F1 F1B 1.161(12) . ?
F2 F1B 1.164(12) . ?
F2 F2B 1.270(13) . ?
F3 F3B 1.155(12) . ?
F3 F2B 1.266(13) . ?
F4 F4B 1.165(10) . ?
F4 F6B 1.302(9) . ?
F5 F4B 1.120(10) . ?
F5 F5B 1.314(11) . ?
F6 F6B 1.171(8) . ?
F6 F5B 1.171(10) . ?

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
O39 C1 C14 107.36(16) . . ?
O39 C1 C2 109.22(16) . . ?
C14 C1 C2 112.31(17) . . ?
C24 C2 C1 110.47(17) . . ?
C24 C2 C3 114.24(16) . . ?
C1 C2 C3 111.95(17) . . ?
C4 C3 C2 113.03(17) . . ?
C4 C3 C31 110.66(17) . . ?
C2 C3 C31 109.14(18) . . ?
C5 C4 C9 117.4(2) . . ?
C5 C4 C3 121.29(19) . . ?
C9 C4 C3 121.29(19) . . ?
C4 C5 O39 122.37(19) . . ?
C4 C5 C6 123.2(2) . . ?
O39 C5 C6 114.4(2) . . ?
C7 C6 C5 119.5(2) . . ?
C6 C7 C8 120.7(2) . . ?
C7 C8 C13 121.7(3) . . ?
C7 C8 C9 119.6(2) . . ?
C13 C8 C9 118.7(3) . . ?
C10 C9 C8 117.6(2) . . ?
C10 C9 C4 123.1(2) . . ?
C8 C9 C4 119.2(2) . . ?
C11 C10 C9 121.4(3) . . ?
C10 C11 C12 120.7(3) . . ?
C13 C12 C11 119.8(3) . . ?
C12 C13 C8 121.7(3) . . ?
C15 C14 C19 118.1(2) . . ?
C15 C14 C1 120.77(19) . . ?
C19 C14 C1 120.84(18) . . ?
O40 C15 C14 124.2(2) . . ?
O40 C15 C16 114.3(2) . . ?
C14 C15 C16 121.5(2) . . ?
C17 C16 C15 120.9(2) . . ?
C16 C17 C18 120.7(2) . . ?
C23 C18 C17 121.2(2) . . ?
C23 C18 C19 119.7(2) . . ?
C17 C18 C19 119.1(2) . . ?
C20 C19 C18 116.9(2) . . ?
C20 C19 C14 123.59(19) . . ?
C18 C19 C14 119.44(19) . . ?
C21 C20 C19 121.4(2) . . ?
C20 C21 C22 121.0(2) . . ?
C23 C22 C21 119.3(2) . . ?
C22 C23 C18 121.6(2) . . ?
C25 C24 C29 117.53(19) . . ?
C25 C24 C2 119.98(18) . . ?
C29 C24 C2 122.45(18) . . ?
C26 C25 C24 121.7(2) . . ?
C27 C26 C25 119.8(2) . . ?
C26 C27 C28 119.7(2) . . ?
C26 C27 C30 120.1(2) . . ?
C28 C27 C30 120.2(2) . . ?
C29 C28 C27 119.9(2) . . ?
C28 C29 C24 121.3(2) . . ?
F3B C30 F1B 99.6(12) . . ?
F3B C30 F2B 104.7(12) . . ?
F1B C30 F2B 107.5(12) . . ?
F3B C30 F2 127.7(12) . . ?
F1B C30 F2 53.4(6) . . ?
F2B C30 F2 57.8(6) . . ?
F3B C30 F3 52.9(5) . . ?
F1B C30 F3 132.9(13) . . ?
F2B C30 F3 57.5(6) . . ?
F2 C30 F3 109.6(3) . . ?
F3B C30 F1 52.9(6) . . ?
F1B C30 F1 53.1(6) . . ?
F2B C30 F1 136.8(11) . . ?
F2 C30 F1 103.6(3) . . ?
F3 C30 F1 104.5(3) . . ?
F3B C30 C27 119.5(13) . . ?
F1B C30 C27 114.4(13) . . ?
F2B C30 C27 109.9(12) . . ?
F2 C30 C27 112.6(3) . . ?
F3 C30 C27 112.6(3) . . ?
F1 C30 C27 113.3(3) . . ?
C32 C31 C3 112.51(17) . . ?
C33 C32 C37 117.6(2) . . ?
C33 C32 C31 121.5(2) . . ?
C37 C32 C31 120.8(2) . . ?
C32 C33 C34 121.7(2) . . ?
C35 C34 C33 119.6(2) . . ?
C34 C35 C36 119.7(2) . . ?
C34 C35 C38 120.5(3) . . ?
C36 C35 C38 119.8(2) . . ?
C35 C36 C37 120.3(2) . . ?
C36 C37 C32 121.1(2) . . ?
F6 C38 F4B 132.6(6) . . ?
F6 C38 F5 107.7(4) . . ?
F4B C38 F5 51.3(5) . . ?
F6 C38 F5B 53.9(5) . . ?
F4B C38 F5B 108.7(7) . . ?
F5 C38 F5B 60.5(5) . . ?
F6 C38 F6B 53.5(4) . . ?
F4B C38 F6B 104.3(7) . . ?
F5 C38 F6B 130.7(4) . . ?
F5B C38 F6B 104.4(6) . . ?
F6 C38 F4 108.3(4) . . ?
F4B C38 F4 52.2(5) . . ?
F5 C38 F4 100.8(4) . . ?
F5B C38 F4 138.6(6) . . ?
F6B C38 F4 57.9(5) . . ?
F6 C38 C35 113.6(4) . . ?
F4B C38 C35 113.8(6) . . ?
F5 C38 C35 115.1(3) . . ?
F5B C38 C35 110.9(6) . . ?
F6B C38 C35 114.0(4) . . ?
F4 C38 C35 110.4(3) . . ?
C5 O39 C1 114.48(16) . . ?
F3B F1 F1B 113.3(14) . . ?
F3B F1 C30 60.9(7) . . ?
F1B F1 C30 60.9(7) . . ?
F1B F2 F2B 117.0(12) . . ?
F1B F2 C30 61.0(7) . . ?
F2B F2 C30 60.5(6) . . ?
F3B F3 F2B 114.6(13) . . ?
F3B F3 C30 61.0(7) . . ?
F2B F3 C30 60.5(6) . . ?
F1 F1B F2 126.9(15) . . ?
F1 F1B C30 66.0(7) . . ?
F2 F1B C30 65.6(7) . . ?
F3 F2B F2 117.0(13) . . ?
F3 F2B C30 62.0(7) . . ?
F2 F2B C30 61.6(6) . . ?
F3 F3B F1 130.0(14) . . ?
F3 F3B C30 66.1(7) . . ?
F1 F3B C30 66.1(7) . . ?
F4B F4 F6B 113.4(8) . . ?
F4B F4 C38 60.7(5) . . ?
F6B F4 C38 59.7(4) . . ?
F4B F5 C38 63.7(5) . . ?
F4B F5 F5B 119.8(8) . . ?
C38 F5 F5B 60.0(4) . . ?
F6B F6 F5B 125.5(9) . . ?
F6B F6 C38 65.6(5) . . ?
F5B F6 C38 64.5(5) . . ?
F5 F4B F4 127.7(10) . . ?
F5 F4B C38 65.1(6) . . ?
F4 F4B C38 67.2(6) . . ?
F6 F5B C38 61.5(5) . . ?
F6 F5B F5 113.5(9) . . ?
C38 F5B F5 59.5(5) . . ?
F6 F6B F4 119.4(7) . . ?
F6 F6B C38 61.0(4) . . ?
F4 F6B C38 62.3(4) . . ?

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
O39 C1 C2 C24 177.28(16) . . . . ?
C14 C1 C2 C24 58.3(2) . . . . ?
O39 C1 C2 C3 -54.2(2) . . . . ?
C14 C1 C2 C3 -173.18(16) . . . . ?
C24 C2 C3 C4 148.21(18) . . . . ?
C1 C2 C3 C4 21.7(2) . . . . ?
C24 C2 C3 C31 -88.2(2) . . . . ?
C1 C2 C3 C31 145.30(17) . . . . ?
C2 C3 C4 C5 9.6(3) . . . . ?
C31 C3 C4 C5 -113.2(2) . . . . ?
C2 C3 C4 C9 -172.34(19) . . . . ?
C31 C3 C4 C9 64.9(3) . . . . ?
C9 C4 C5 O39 173.10(19) . . . . ?
C3 C4 C5 O39 -8.7(3) . . . . ?
C9 C4 C5 C6 -7.8(3) . . . . ?
C3 C4 C5 C6 170.4(2) . . . . ?
C4 C5 C6 C7 3.1(4) . . . . ?
O39 C5 C6 C7 -177.7(2) . . . . ?
C5 C6 C7 C8 2.9(4) . . . . ?
C6 C7 C8 C13 173.2(3) . . . . ?
C6 C7 C8 C9 -3.7(4) . . . . ?
C7 C8 C9 C10 175.6(2) . . . . ?
C13 C8 C9 C10 -1.3(3) . . . . ?
C7 C8 C9 C4 -1.2(3) . . . . ?
C13 C8 C9 C4 -178.2(2) . . . . ?
C5 C4 C9 C10 -170.0(2) . . . . ?
C3 C4 C9 C10 11.9(3) . . . . ?
C5 C4 C9 C8 6.7(3) . . . . ?
C3 C4 C9 C8 -171.5(2) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C4 C9 C10 C11 176.9(2) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C8 -0.5(5) . . . . ?
C7 C8 C13 C12 -175.4(3) . . . . ?
C9 C8 C13 C12 1.6(4) . . . . ?
O39 C1 C14 C15 -38.4(3) . . . . ?
C2 C1 C14 C15 81.7(2) . . . . ?
O39 C1 C14 C19 147.49(19) . . . . ?
C2 C1 C14 C19 -92.4(2) . . . . ?
C19 C14 C15 O40 178.9(2) . . . . ?
C1 C14 C15 O40 4.6(3) . . . . ?
C19 C14 C15 C16 0.4(3) . . . . ?
C1 C14 C15 C16 -173.8(2) . . . . ?
O40 C15 C16 C17 -176.1(2) . . . . ?
C14 C15 C16 C17 2.5(4) . . . . ?
C15 C16 C17 C18 -2.3(4) . . . . ?
C16 C17 C18 C23 179.6(2) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C23 C18 C19 C20 1.9(3) . . . . ?
C17 C18 C19 C20 -177.82(19) . . . . ?
C23 C18 C19 C14 -176.7(2) . . . . ?
C17 C18 C19 C14 3.6(3) . . . . ?
C15 C14 C19 C20 178.1(2) . . . . ?
C1 C14 C19 C20 -7.6(3) . . . . ?
C15 C14 C19 C18 -3.4(3) . . . . ?
C1 C14 C19 C18 170.84(19) . . . . ?
C18 C19 C20 C21 -1.9(3) . . . . ?
C14 C19 C20 C21 176.7(2) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 1.7(4) . . . . ?
C21 C22 C23 C18 -1.7(4) . . . . ?
C17 C18 C23 C22 179.5(2) . . . . ?
C19 C18 C23 C22 -0.2(4) . . . . ?
C1 C2 C24 C25 -93.9(2) . . . . ?
C3 C2 C24 C25 138.8(2) . . . . ?
C1 C2 C24 C29 83.7(2) . . . . ?
C3 C2 C24 C29 -43.5(3) . . . . ?
C29 C24 C25 C26 0.9(3) . . . . ?
C2 C24 C25 C26 178.7(2) . . . . ?
C24 C25 C26 C27 0.1(4) . . . . ?
C25 C26 C27 C28 -1.3(4) . . . . ?
C25 C26 C27 C30 179.3(3) . . . . ?
C26 C27 C28 C29 1.6(4) . . . . ?
C30 C27 C28 C29 -179.0(3) . . . . ?
C27 C28 C29 C24 -0.6(4) . . . . ?
C25 C24 C29 C28 -0.6(3) . . . . ?
C2 C24 C29 C28 -178.4(2) . . . . ?
C26 C27 C30 F3B 146.1(7) . . . . ?
C28 C27 C30 F3B -33.3(8) . . . . ?
C26 C27 C30 F1B 28.3(7) . . . . ?
C28 C27 C30 F1B -151.1(7) . . . . ?
C26 C27 C30 F2B -92.8(7) . . . . ?
C28 C27 C30 F2B 87.8(7) . . . . ?
C26 C27 C30 F2 -30.4(4) . . . . ?
C28 C27 C30 F2 150.2(3) . . . . ?
C26 C27 C30 F3 -154.9(3) . . . . ?
C28 C27 C30 F3 25.7(4) . . . . ?
C26 C27 C30 F1 86.8(4) . . . . ?
C28 C27 C30 F1 -92.6(3) . . . . ?
C4 C3 C31 C32 -169.98(18) . . . . ?
C2 C3 C31 C32 65.0(2) . . . . ?
C3 C31 C32 C33 -98.3(3) . . . . ?
C3 C31 C32 C37 78.4(3) . . . . ?
C37 C32 C33 C34 -2.9(4) . . . . ?
C31 C32 C33 C34 173.9(2) . . . . ?
C32 C33 C34 C35 1.0(4) . . . . ?
C33 C34 C35 C36 1.4(4) . . . . ?
C33 C34 C35 C38 -178.2(3) . . . . ?
C34 C35 C36 C37 -1.7(4) . . . . ?
C38 C35 C36 C37 177.9(3) . . . . ?
C35 C36 C37 C32 -0.3(4) . . . . ?
C33 C32 C37 C36 2.6(4) . . . . ?
C31 C32 C37 C36 -174.2(2) . . . . ?
C34 C35 C38 F6 -127.6(5) . . . . ?
C36 C35 C38 F6 52.8(6) . . . . ?
C34 C35 C38 F4B 53.9(7) . . . . ?
C36 C35 C38 F4B -125.6(7) . . . . ?
C34 C35 C38 F5 -2.8(5) . . . . ?
C36 C35 C38 F5 177.6(4) . . . . ?
C34 C35 C38 F5B -69.0(7) . . . . ?
C36 C35 C38 F5B 111.4(7) . . . . ?
C34 C35 C38 F6B 173.5(6) . . . . ?
C36 C35 C38 F6B -6.1(7) . . . . ?
C34 C35 C38 F4 110.5(4) . . . . ?
C36 C35 C38 F4 -69.1(5) . . . . ?
C4 C5 O39 C1 -26.8(3) . . . . ?
C6 C5 O39 C1 154.0(2) . . . . ?
C14 C1 O39 C5 179.61(17) . . . . ?
C2 C1 O39 C5 57.6(2) . . . . ?
F1B C30 F1 F3B -146(2) . . . . ?
F2B C30 F1 F3B -70.1(18) . . . . ?
F2 C30 F1 F3B -127.3(15) . . . . ?
F3 C30 F1 F3B -12.5(16) . . . . ?
C27 C30 F1 F3B 110.4(16) . . . . ?
F3B C30 F1 F1B 146(2) . . . . ?
F2B C30 F1 F1B 75.6(18) . . . . ?
F2 C30 F1 F1B 18.4(16) . . . . ?
F3 C30 F1 F1B 133.2(16) . . . . ?
C27 C30 F1 F1B -103.9(16) . . . . ?
F3B C30 F2 F1B -71.8(17) . . . . ?
F2B C30 F2 F1B -156(2) . . . . ?
F3 C30 F2 F1B -129.4(16) . . . . ?
F1 C30 F2 F1B -18.4(16) . . . . ?
C27 C30 F2 F1B 104.4(16) . . . . ?
F3B C30 F2 F2B 83.8(15) . . . . ?
F1B C30 F2 F2B 156(2) . . . . ?
F3 C30 F2 F2B 26.1(13) . . . . ?
F1 C30 F2 F2B 137.2(13) . . . . ?
C27 C30 F2 F2B -100.0(13) . . . . ?
F1B C30 F3 F3B 65.2(17) . . . . ?
F2B C30 F3 F3B 149(2) . . . . ?
F2 C30 F3 F3B 123.0(16) . . . . ?
F1 C30 F3 F3B 12.5(16) . . . . ?
C27 C30 F3 F3B -110.8(16) . . . . ?
F3B C30 F3 F2B -149(2) . . . . ?
F1B C30 F3 F2B -84.0(15) . . . . ?
F2 C30 F3 F2B -26.2(13) . . . . ?
F1 C30 F3 F2B -136.7(13) . . . . ?
C27 C30 F3 F2B 100.0(13) . . . . ?
F3B F1 F1B F2 7(4) . . . . ?
C30 F1 F1B F2 -26(2) . . . . ?
F3B F1 F1B C30 32.4(19) . . . . ?
F2B F2 F1B F1 2(4) . . . . ?
C30 F2 F1B F1 26(2) . . . . ?
F2B F2 F1B C30 -24(2) . . . . ?
F3B C30 F1B F1 -27.1(16) . . . . ?
F2B C30 F1B F1 -135.9(12) . . . . ?
F2 C30 F1B F1 -157.5(19) . . . . ?
F3 C30 F1B F1 -74.3(13) . . . . ?
C27 C30 F1B F1 101.6(10) . . . . ?
F3B C30 F1B F2 130.4(13) . . . . ?
F2B C30 F1B F2 21.5(17) . . . . ?
F3 C30 F1B F2 83.2(11) . . . . ?
F1 C30 F1B F2 157.5(19) . . . . ?
C27 C30 F1B F2 -100.9(10) . . . . ?
F3B F3 F2B F2 0(3) . . . . ?
C30 F3 F2B F2 29.0(12) . . . . ?
F3B F3 F2B C30 -29.5(18) . . . . ?
F1B F2 F2B F3 -5(3) . . . . ?
C30 F2 F2B F3 -29.1(12) . . . . ?
F1B F2 F2B C30 24(2) . . . . ?
F3B C30 F2B F3 24.9(15) . . . . ?
F1B C30 F2B F3 130.2(13) . . . . ?
F2 C30 F2B F3 150.5(14) . . . . ?
F1 C30 F2B F3 75.8(11) . . . . ?
C27 C30 F2B F3 -104.7(8) . . . . ?
F3B C30 F2B F2 -125.6(12) . . . . ?
F1B C30 F2B F2 -20.4(16) . . . . ?
F3 C30 F2B F2 -150.5(14) . . . . ?
F1 C30 F2B F2 -74.7(11) . . . . ?
C27 C30 F2B F2 104.8(8) . . . . ?
F2B F3 F3B F1 11(4) . . . . ?
C30 F3 F3B F1 -18(2) . . . . ?
F2B F3 F3B C30 29.3(18) . . . . ?
F1B F1 F3B F3 -14(4) . . . . ?
C30 F1 F3B F3 18(2) . . . . ?
F1B F1 F3B C30 -32.4(19) . . . . ?
F1B C30 F3B F3 -137.6(14) . . . . ?
F2B C30 F3B F3 -26.5(16) . . . . ?
F2 C30 F3B F3 -86.9(11) . . . . ?
F1 C30 F3B F3 -164.8(19) . . . . ?
C27 C30 F3B F3 97.1(10) . . . . ?
F1B C30 F3B F1 27.2(16) . . . . ?
F2B C30 F3B F1 138.3(12) . . . . ?
F2 C30 F3B F1 77.8(12) . . . . ?
F3 C30 F3B F1 164.8(19) . . . . ?
C27 C30 F3B F1 -98.1(10) . . . . ?
F6 C38 F4 F4B 130.2(8) . . . . ?
F5 C38 F4 F4B 17.3(7) . . . . ?
F5B C38 F4 F4B 74.4(12) . . . . ?
F6B C38 F4 F4B 148.9(9) . . . . ?
C35 C38 F4 F4B -104.8(7) . . . . ?
F6 C38 F4 F6B -18.7(6) . . . . ?
F4B C38 F4 F6B -148.9(9) . . . . ?
F5 C38 F4 F6B -131.6(5) . . . . ?
F5B C38 F4 F6B -74.5(10) . . . . ?
C35 C38 F4 F6B 106.3(5) . . . . ?
F6 C38 F5 F4B -130.9(8) . . . . ?
F5B C38 F5 F4B -157.9(10) . . . . ?
F6B C38 F5 F4B -74.3(10) . . . . ?
F4 C38 F5 F4B -17.6(7) . . . . ?
C35 C38 F5 F4B 101.2(8) . . . . ?
F6 C38 F5 F5B 27.0(7) . . . . ?
F4B C38 F5 F5B 157.9(10) . . . . ?
F6B C38 F5 F5B 83.6(9) . . . . ?
F4 C38 F5 F5B 140.4(6) . . . . ?
C35 C38 F5 F5B -100.8(7) . . . . ?
F4B C38 F6 F6B 74.8(10) . . . . ?
F5 C38 F6 F6B 128.0(6) . . . . ?
F5B C38 F6 F6B 157.3(9) . . . . ?
F4 C38 F6 F6B 19.8(6) . . . . ?
C35 C38 F6 F6B -103.3(6) . . . . ?
F4B C38 F6 F5B -82.5(10) . . . . ?
F5 C38 F6 F5B -29.3(8) . . . . ?
F6B C38 F6 F5B -157.3(9) . . . . ?
F4 C38 F6 F5B -137.5(7) . . . . ?
C35 C38 F6 F5B 99.4(7) . . . . ?
C38 F5 F4B F4 25.9(9) . . . . ?
F5B F5 F4B F4 3.9(17) . . . . ?
F5B F5 F4B C38 -22.0(9) . . . . ?
F6B F4 F4B F5 3.6(15) . . . . ?
C38 F4 F4B F5 -25.5(9) . . . . ?
F6B F4 F4B C38 29.1(7) . . . . ?
F6 C38 F4B F5 77.9(9) . . . . ?
F5B C38 F4B F5 20.2(9) . . . . ?
F6B C38 F4B F5 131.1(6) . . . . ?
F4 C38 F4B F5 158.0(9) . . . . ?
C35 C38 F4B F5 -104.0(6) . . . . ?
F6 C38 F4B F4 -80.0(9) . . . . ?
F5 C38 F4B F4 -158.0(9) . . . . ?
F5B C38 F4B F4 -137.8(7) . . . . ?
F6B C38 F4B F4 -26.9(7) . . . . ?
C35 C38 F4B F4 98.1(6) . . . . ?
F6B F6 F5B C38 -25.6(9) . . . . ?
F6B F6 F5B F5 4.6(14) . . . . ?
C38 F6 F5B F5 30.2(6) . . . . ?
F4B C38 F5B F6 129.6(7) . . . . ?
F5 C38 F5B F6 147.6(8) . . . . ?
F6B C38 F5B F6 18.7(8) . . . . ?
F4 C38 F5B F6 76.2(11) . . . . ?
C35 C38 F5B F6 -104.6(6) . . . . ?
F6 C38 F5B F5 -147.6(8) . . . . ?
F4B C38 F5B F5 -18.0(8) . . . . ?
F6B C38 F5B F5 -128.9(5) . . . . ?
F4 C38 F5B F5 -71.5(10) . . . . ?
C35 C38 F5B F5 107.8(5) . . . . ?
F4B F5 F5B F6 -8.0(13) . . . . ?
C38 F5 F5B F6 -30.9(6) . . . . ?
F4B F5 F5B C38 22.8(9) . . . . ?
F5B F6 F6B F4 2.7(13) . . . . ?
C38 F6 F6B F4 -22.7(6) . . . . ?
F5B F6 F6B C38 25.4(9) . . . . ?
F4B F4 F6B F6 -7.0(11) . . . . ?
C38 F4 F6B F6 22.4(6) . . . . ?
F4B F4 F6B C38 -29.4(7) . . . . ?
F4B C38 F6B F6 -132.8(7) . . . . ?
F5 C38 F6B F6 -82.0(8) . . . . ?
F5B C38 F6B F6 -18.8(8) . . . . ?
F4 C38 F6B F6 -157.7(7) . . . . ?
C35 C38 F6B F6 102.4(5) . . . . ?
F6 C38 F6B F4 157.7(7) . . . . ?
F4B C38 F6B F4 24.9(7) . . . . ?
F5 C38 F6B F4 75.7(8) . . . . ?
F5B C38 F6B F4 138.9(6) . . . . ?
C35 C38 F6B F4 -99.9(4) . . . . ?

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
C6 H6 F1B 0.93 2.32 3.173(19) 152.6 2 yes
O40 H40O O39 1.00(4) 1.70(4) 2.589(3) 146(3) . yes
O40 H40O F1 1.00(4) 2.58(3) 3.143(3) 116(2) 1_455 yes

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044

