# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_WM0189_1_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1875124'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H16 F10 O4 S2'
_chemical_formula_weight         814.65

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'
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'
S S 0.1246 0.1234 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   17.738(18)
_cell_length_b                   5.738(6)
_cell_length_c                   16.944(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.92(2)
_cell_angle_gamma                90
_cell_volume                     1720(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6646
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.18

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13709
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.151
_diffrn_reflns_theta_max         23.726
_diffrn_reflns_theta_full        23.726
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measured_fraction_theta_full 0.830
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_Laue_measured_fraction_full 0.830
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_point_group_measured_fraction_full 0.830
_reflns_number_total             2174
_reflns_number_gt                1760
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1614P)²+1.3482P] 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_number_reflns         2174
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2683
_refine_ls_wR_factor_gt          0.2434
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.216
_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
S0 S 0.93314(9) 0.2771(2) 0.43977(7) 0.0592(6) Uani 1 1 d . . . . .
C1 C 0.8129(3) 0.6647(9) 0.1890(3) 0.0465(11) Uani 1 1 d . . . . .
O1 O 0.7570(4) 0.7424(8) 0.3465(2) 0.0877(17) Uani 1 1 d . . . . .
O2 O 0.7168(3) 1.0950(6) 0.3067(2) 0.0646(11) Uani 1 1 d . . . . .
C2 C 0.7686(3) 0.8572(8) 0.2114(3) 0.0465(11) Uani 1 1 d . . . . .
C3 C 0.7426(4) 1.0172(10) 0.1543(3) 0.0625(14) Uani 1 1 d . . . . .
H3 H 0.7142 1.1446 0.1688 0.075 Uiso 1 1 calc R U . . .
C4 C 0.7585(4) 0.9887(11) 0.0759(3) 0.0749(18) Uani 1 1 d . . . . .
H4 H 0.7415 1.0986 0.0385 0.090 Uiso 1 1 calc R U . . .
C5 C 0.7993(4) 0.7993(12) 0.0529(3) 0.0733(18) Uani 1 1 d . . . . .
H5 H 0.8083 0.7795 -0.0001 0.088 Uiso 1 1 calc R U . . .
C6 C 0.8272(3) 0.6372(11) 0.1087(3) 0.0625(14) Uani 1 1 d . . . . .
H6 H 0.8553 0.5106 0.0929 0.075 Uiso 1 1 calc R U . . .
C12 C 0.8475(3) 0.5010(9) 0.2444(3) 0.0503(12) Uani 1 1 d . . . . .
C13 C 0.8811(3) 0.3623(9) 0.2861(3) 0.0534(13) Uani 1 1 d . . . . .
C14 C 0.9209(3) 0.2080(8) 0.3402(3) 0.0498(12) Uani 1 1 d . . . . .
C15 C 0.9541(3) -0.0017(9) 0.3248(3) 0.0573(13) Uani 1 1 d . . . . .
H15 H 0.9534 -0.0673 0.2745 0.069 Uiso 1 1 calc R U . . .
C16 C 0.9892(3) -0.1067(9) 0.3921(3) 0.0560(13) Uani 1 1 d . . . . .
H16 H 1.0135 -0.2502 0.3910 0.067 Uiso 1 1 calc R U . . .
C17 C 0.9845(3) 0.0222(8) 0.4604(3) 0.0488(12) Uani 1 1 d . . . . .
C21 C 0.7483(3) 0.8856(9) 0.2953(3) 0.0512(12) Uani 1 1 d . . . . .
C22 C 0.6905(4) 1.1454(11) 0.3844(3) 0.0663(15) Uani 1 1 d . . . . .
H22A H 0.7019 1.3060 0.3986 0.080 Uiso 1 1 calc R U . . .
H22B H 0.7161 1.0451 0.4238 0.080 Uiso 1 1 calc R U . . .
C23 C 0.6064(3) 1.1049(9) 0.3824(2) 0.0541(13) Uani 1 1 d . . . . .
C24 C 0.5733(4) 0.9117(9) 0.4167(3) 0.0593(15) Uani 1 1 d . . . . .
F24 F 0.6164(3) 0.7529(6) 0.4564(2) 0.0859(13) Uani 1 1 d . . . . .
C25 C 0.4963(4) 0.8759(9) 0.4124(3) 0.0622(15) Uani 1 1 d . . . . .
F25 F 0.4663(3) 0.6879(6) 0.4471(2) 0.0899(14) Uani 1 1 d . . . . .
C26 C 0.4484(4) 1.0355(10) 0.3733(3) 0.0628(15) Uani 1 1 d . . . . .
F26 F 0.3736(2) 1.0035(7) 0.3703(2) 0.0888(12) Uani 1 1 d . . . . .
C27 C 0.4793(4) 1.2300(9) 0.3394(3) 0.0572(14) Uani 1 1 d . . . . .
F27 F 0.4334(2) 1.3856(6) 0.3005(2) 0.0822(11) Uani 1 1 d . . . . .
C28 C 0.5564(4) 1.2606(8) 0.3442(3) 0.0549(14) Uani 1 1 d . . . . .
F28 F 0.5844(2) 1.4515(6) 0.30906(18) 0.0744(10) 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
S0 C14 1.732(5) . ?
S0 C17 1.746(5) . ?
C1 C6 1.410(7) . ?
C1 C2 1.423(7) . ?
C1 C12 1.436(7) . ?
O1 C21 1.197(6) . ?
O2 C21 1.344(7) . ?
O2 C22 1.455(6) . ?
C2 C3 1.390(7) . ?
C2 C21 1.499(6) . ?
C3 C4 1.386(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C12 C13 1.196(7) . ?
C13 C14 1.426(7) . ?
C14 C15 1.373(7) . ?
C15 C16 1.398(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(7) . ?
C16 H16 0.9300 . ?
C17 C17 1.437(10) 3_756 ?
C22 C23 1.509(9) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C28 1.388(8) . ?
C23 C24 1.399(8) . ?
C24 F24 1.341(7) . ?
C24 C25 1.379(10) . ?
C25 F25 1.355(7) . ?
C25 C26 1.386(9) . ?
C26 F26 1.338(8) . ?
C26 C27 1.385(8) . ?
C27 F27 1.349(7) . ?
C27 C28 1.376(9) . ?
C28 F28 1.357(6) . ?

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
C14 S0 C17 91.9(2) . . ?
C6 C1 C2 118.9(4) . . ?
C6 C1 C12 117.5(5) . . ?
C2 C1 C12 123.6(4) . . ?
C21 O2 C22 118.0(4) . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 C21 119.9(5) . . ?
C1 C2 C21 120.7(4) . . ?
C4 C3 C2 120.6(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.1(6) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C13 C12 C1 174.3(5) . . ?
C12 C13 C14 176.0(6) . . ?
C15 C14 C13 128.4(5) . . ?
C15 C14 S0 111.1(4) . . ?
C13 C14 S0 120.5(4) . . ?
C14 C15 C16 113.3(5) . . ?
C14 C15 H15 123.4 . . ?
C16 C15 H15 123.4 . . ?
C17 C16 C15 113.8(5) . . ?
C17 C16 H16 123.1 . . ?
C15 C16 H16 123.1 . . ?
C16 C17 C17 130.2(6) . 3_756 ?
C16 C17 S0 110.0(4) . . ?
C17 C17 S0 119.8(5) 3_756 . ?
O1 C21 O2 122.9(4) . . ?
O1 C21 C2 125.8(5) . . ?
O2 C21 C2 111.3(4) . . ?
O2 C22 C23 109.1(5) . . ?
O2 C22 H22A 109.9 . . ?
C23 C22 H22A 109.9 . . ?
O2 C22 H22B 109.9 . . ?
C23 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C28 C23 C24 115.6(6) . . ?
C28 C23 C22 120.7(5) . . ?
C24 C23 C22 123.7(5) . . ?
F24 C24 C25 117.0(5) . . ?
F24 C24 C23 120.4(6) . . ?
C25 C24 C23 122.5(5) . . ?
F25 C25 C24 120.8(6) . . ?
F25 C25 C26 119.2(6) . . ?
C24 C25 C26 120.0(5) . . ?
F26 C26 C27 121.0(6) . . ?
F26 C26 C25 120.1(5) . . ?
C27 C26 C25 118.9(6) . . ?
F27 C27 C28 120.5(5) . . ?
F27 C27 C26 119.5(6) . . ?
C28 C27 C26 119.9(5) . . ?
F28 C28 C27 118.1(5) . . ?
F28 C28 C23 118.8(6) . . ?
C27 C28 C23 123.1(5) . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.112



####################################################################### 
# 
# 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_WM0195_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1875127'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H20 F10 O4'
_chemical_formula_weight         826.62

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.507(2)
_cell_length_b                   7.869(2)
_cell_length_c                   16.680(5)
_cell_angle_alpha                98.558(6)
_cell_angle_beta                 99.414(6)
_cell_angle_gamma                106.779(6)
_cell_volume                     910.4(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6765
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.85

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             418
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18585
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.265
_diffrn_reflns_theta_max         28.954
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4805
_reflns_number_gt                3182
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0966P)²+0.1422P] 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_number_reflns         4805
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1849
_refine_ls_wR_factor_gt          0.1584
_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 1.1231(2) 0.2050(2) 0.36423(13) 0.0940(6) Uani 1 1 d . . . . .
C1 C 1.0145(2) 0.6292(2) 0.39171(10) 0.0469(4) Uani 1 1 d . . . . .
O2 O 0.85574(17) 0.25722(17) 0.31422(9) 0.0645(4) Uani 1 1 d . . . . .
C2 C 1.1006(2) 0.4984(2) 0.40746(10) 0.0477(4) Uani 1 1 d . . . . .
C3 C 1.2653(2) 0.5482(3) 0.47025(12) 0.0609(5) Uani 1 1 d . . . . .
H3 H 1.3222 0.4612 0.4811 0.073 Uiso 1 1 calc R U . . .
C4 C 1.3451(3) 0.7214(3) 0.51612(13) 0.0709(6) Uani 1 1 d . . . . .
H4 H 1.4544 0.7512 0.5578 0.085 Uiso 1 1 calc R U . . .
C5 C 1.2625(3) 0.8508(3) 0.50021(13) 0.0704(6) Uani 1 1 d . . . . .
H5 H 1.3164 0.9689 0.5311 0.084 Uiso 1 1 calc R U . . .
C6 C 1.0996(3) 0.8065(3) 0.43857(12) 0.0619(5) Uani 1 1 d . . . . .
H6 H 1.0456 0.8957 0.4281 0.074 Uiso 1 1 calc R U . . .
C11 C 0.8445(2) 0.5952(2) 0.32902(11) 0.0502(4) Uani 1 1 d . . . . .
C12 C 0.7076(2) 0.5788(2) 0.27795(11) 0.0529(4) Uani 1 1 d . . . . .
C13 C 0.5432(2) 0.5566(2) 0.21377(10) 0.0496(4) Uani 1 1 d . . . . .
C14 C 0.3597(3) 0.4824(3) 0.22533(12) 0.0634(5) Uani 1 1 d . . . . .
H14 H 0.3427 0.4445 0.2746 0.076 Uiso 1 1 calc R U . . .
C15 C 0.2020(3) 0.4640(3) 0.16463(13) 0.0658(5) Uani 1 1 d . . . . .
H15 H 0.0801 0.4138 0.1731 0.079 Uiso 1 1 calc R U . . .
C16 C 0.2261(2) 0.5208(2) 0.09086(11) 0.0536(4) Uani 1 1 d . . . . .
C17 C 0.4092(3) 0.5947(3) 0.07943(11) 0.0567(4) Uani 1 1 d . . . . .
H17 H 0.4263 0.6329 0.0303 0.068 Uiso 1 1 calc R U . . .
C18 C 0.5667(3) 0.6124(3) 0.14006(11) 0.0553(4) Uani 1 1 d . . . . .
H18 H 0.6887 0.6618 0.1314 0.066 Uiso 1 1 calc R U . . .
C19 C 0.0648(3) 0.5052(3) 0.02702(12) 0.0613(5) Uani 1 1 d . . . . .
C21 C 1.0310(2) 0.3066(2) 0.36103(12) 0.0544(4) Uani 1 1 d . . . . .
C22 C 0.7823(3) 0.0749(3) 0.26517(16) 0.0738(6) Uani 1 1 d . . . . .
H22A H 0.7803 -0.0122 0.3008 0.089 Uiso 1 1 calc R U . . .
H22B H 0.8618 0.0579 0.2263 0.089 Uiso 1 1 calc R U . . .
C23 C 0.5838(3) 0.0487(2) 0.21916(13) 0.0587(5) Uani 1 1 d . . . . .
C24 C 0.4255(3) -0.0340(2) 0.24762(12) 0.0585(5) Uani 1 1 d . . . . .
F24 F 0.4460(2) -0.09060(19) 0.31942(8) 0.0848(4) Uani 1 1 d . . . . .
C25 C 0.2431(3) -0.0654(3) 0.20365(13) 0.0601(5) Uani 1 1 d . . . . .
F25 F 0.09241(18) -0.1512(2) 0.23150(9) 0.0870(4) Uani 1 1 d . . . . .
C26 C 0.2158(3) -0.0108(3) 0.13018(13) 0.0639(5) Uani 1 1 d . . . . .
F26 F 0.03901(18) -0.0388(2) 0.08797(10) 0.0937(5) Uani 1 1 d . . . . .
C27 C 0.3699(3) 0.0742(3) 0.10000(13) 0.0652(5) Uani 1 1 d . . . . .
F27 F 0.3426(2) 0.1288(2) 0.02799(9) 0.0986(5) Uani 1 1 d . . . . .
C28 C 0.5505(3) 0.1033(3) 0.14489(14) 0.0649(5) Uani 1 1 d . . . . .
F28 F 0.6987(2) 0.1879(2) 0.11393(11) 0.0965(5) 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
O1 C21 1.200(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.401(3) . ?
C1 C11 1.441(2) . ?
O2 C21 1.331(2) . ?
O2 C22 1.442(2) . ?
C2 C3 1.398(2) . ?
C2 C21 1.488(3) . ?
C3 C4 1.367(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C11 C12 1.185(2) . ?
C12 C13 1.445(2) . ?
C13 C18 1.387(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(3) . ?
C16 C19 1.439(2) . ?
C17 C18 1.383(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C19 1.188(3) 2_565 ?
C22 C23 1.501(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.375(3) . ?
C23 C28 1.379(3) . ?
C24 F24 1.340(2) . ?
C24 C25 1.377(3) . ?
C25 F25 1.333(2) . ?
C25 C26 1.362(3) . ?
C26 F26 1.336(2) . ?
C26 C27 1.372(3) . ?
C27 F27 1.339(3) . ?
C27 C28 1.374(3) . ?
C28 F28 1.345(3) . ?

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 118.43(15) . . ?
C2 C1 C11 124.37(15) . . ?
C6 C1 C11 117.18(15) . . ?
C21 O2 C22 116.44(14) . . ?
C3 C2 C1 118.96(16) . . ?
C3 C2 C21 116.38(15) . . ?
C1 C2 C21 124.66(14) . . ?
C4 C3 C2 121.82(18) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.44(17) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.35(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.97(18) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C12 C11 C1 175.82(18) . . ?
C11 C12 C13 178.3(2) . . ?
C18 C13 C14 119.03(15) . . ?
C18 C13 C12 120.16(17) . . ?
C14 C13 C12 120.81(16) . . ?
C15 C14 C13 120.93(18) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.92(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.06(15) . . ?
C17 C16 C19 119.81(17) . . ?
C15 C16 C19 121.13(18) . . ?
C18 C17 C16 120.97(17) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 120.10(17) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C19 C19 C16 178.1(3) 2_565 . ?
O1 C21 O2 122.47(17) . . ?
O1 C21 C2 123.93(16) . . ?
O2 C21 C2 113.60(14) . . ?
O2 C22 C23 107.11(14) . . ?
O2 C22 H22A 110.3 . . ?
C23 C22 H22A 110.3 . . ?
O2 C22 H22B 110.3 . . ?
C23 C22 H22B 110.3 . . ?
H22A C22 H22B 108.5 . . ?
C24 C23 C28 116.34(17) . . ?
C24 C23 C22 122.1(2) . . ?
C28 C23 C22 121.6(2) . . ?
F24 C24 C23 119.97(18) . . ?
F24 C24 C25 117.84(19) . . ?
C23 C24 C25 122.17(19) . . ?
F25 C25 C26 119.44(18) . . ?
F25 C25 C24 120.78(19) . . ?
C26 C25 C24 119.77(19) . . ?
F26 C26 C25 119.89(19) . . ?
F26 C26 C27 120.2(2) . . ?
C25 C26 C27 119.94(18) . . ?
F27 C27 C26 119.80(19) . . ?
F27 C27 C28 121.0(2) . . ?
C26 C27 C28 119.2(2) . . ?
F28 C28 C27 117.8(2) . . ?
F28 C28 C23 119.63(19) . . ?
C27 C28 C23 122.58(19) . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_WM0173_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1875125'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H22 Cl6 F10 O4'
_chemical_formula_weight         1041.10

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.224(4)
_cell_length_b                   10.029(5)
_cell_length_c                   13.383(7)
_cell_angle_alpha                79.95(4)
_cell_angle_beta                 77.865(19)
_cell_angle_gamma                88.186(19)
_cell_volume                     1062.5(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.77

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.495
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16511
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0230
_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       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.062
_diffrn_reflns_theta_max         25.841
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4063
_reflns_number_gt                3760
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0331P)²+1.2990P] 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_number_reflns         4063
_refine_ls_number_parameters     653
_refine_ls_number_restraints     1763
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.001
_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 0.244(2) 0.2140(18) 0.7213(15) 0.0214(18) Uani 0.5 1 d D U P A -1
H1 H 0.304445 0.179395 0.662637 0.026 Uiso 0.5 1 calc R U P A -1
C2 C 0.3032(16) 0.3283(15) 0.7486(12) 0.0205(16) Uani 0.5 1 d D U P A -1
C3 C 0.214(2) 0.3807(19) 0.8351(15) 0.0188(19) Uani 0.5 1 d D U P A -1
C4 C 0.0692(16) 0.3138(17) 0.8914(12) 0.021(2) Uani 0.5 1 d D U P A -1
H4 H 0.008605 0.346601 0.950799 0.025 Uiso 0.5 1 calc R U P A -1
C5 C 0.0108(18) 0.2014(16) 0.8632(12) 0.024(2) Uani 0.5 1 d D U P A -1
H5 H -0.090022 0.158986 0.902110 0.029 Uiso 0.5 1 calc R U P A -1
C6 C 0.099(2) 0.1505(16) 0.7783(12) 0.022(2) Uani 0.5 1 d D U P A -1
H6 H 0.060709 0.072147 0.759289 0.026 Uiso 0.5 1 calc R U P A -1
C21 C 0.462(2) 0.386(2) 0.6799(14) 0.0258(19) Uani 0.5 1 d D U P A -1
O21 O 0.514(2) 0.3625(14) 0.5943(9) 0.0370(17) Uani 0.5 1 d D U P A -1
C22 C 0.6948(9) 0.5257(7) 0.6767(6) 0.0406(15) Uani 0.5 1 d D U P A -1
H22A H 0.763978 0.462228 0.715224 0.049 Uiso 0.5 1 calc R U P A -1
H22B H 0.732212 0.525243 0.601468 0.049 Uiso 0.5 1 calc R U P A -1
O22 O 0.5114(10) 0.4904(8) 0.7134(8) 0.0302(15) Uani 0.5 1 d D U P A -1
C23 C 0.7004(9) 0.6661(7) 0.7011(6) 0.0277(13) Uani 0.5 1 d D U P A -1
C24 C 0.6309(15) 0.7732(8) 0.6459(8) 0.0312(15) Uani 0.5 1 d D U P A -1
F24 F 0.5589(12) 0.7528(6) 0.5689(6) 0.0578(18) Uani 0.5 1 d D U P A -1
C25 C 0.632(2) 0.9022(9) 0.6643(10) 0.0331(15) Uani 0.5 1 d D U P A -1
F25 F 0.5621(14) 1.0058(7) 0.6118(8) 0.058(2) Uani 0.5 1 d D U P A -1
C26 C 0.7085(18) 0.9278(8) 0.7417(10) 0.0277(14) Uani 0.5 1 d D U P A -1
F26 F 0.7152(16) 1.0522(6) 0.7621(9) 0.0514(16) Uani 0.5 1 d D U P A -1
C27 C 0.7796(19) 0.8243(7) 0.7986(10) 0.0265(13) Uani 0.5 1 d D U P A -1
F27 F 0.8563(16) 0.8465(8) 0.8727(8) 0.0487(13) Uani 0.5 1 d D U P A -1
C28 C 0.7740(19) 0.6949(8) 0.7789(10) 0.0273(13) Uani 0.5 1 d D U P A -1
F28 F 0.8400(13) 0.5938(6) 0.8366(7) 0.0489(14) Uani 0.5 1 d D U P A -1
C31 C 0.263(3) 0.500(2) 0.869(2) 0.022(2) Uani 0.5 1 d D U P A -1
C32 C 0.292(3) 0.6011(14) 0.8970(16) 0.0216(19) Uani 0.5 1 d D U P A -1
C33 C 0.3449(17) 0.7195(10) 0.9276(10) 0.0232(16) Uani 0.5 1 d D U P A -1
C34 C 0.2860(12) 0.8492(9) 0.8970(7) 0.0223(15) Uani 0.5 1 d D U P A -1
H34 H 0.203356 0.861020 0.856179 0.027 Uiso 0.5 1 calc R U P A -1
C35 C 0.3468(11) 0.9597(9) 0.9255(7) 0.0202(15) Uani 0.5 1 d D U P A -1
H35 H 0.304179 1.046775 0.904302 0.024 Uiso 0.5 1 calc R U P A -1
C36 C 0.469(3) 0.9480(9) 0.9848(17) 0.0193(14) Uani 0.5 1 d D U P A -1
C37 C 0.5210(9) 0.8182(8) 1.0193(5) 0.0227(14) Uani 0.5 1 d D U P A -1
H37 H 0.600642 0.806317 1.062230 0.027 Uiso 0.5 1 calc R U P A -1
C38 C 0.4592(10) 0.7058(8) 0.9928(6) 0.0234(15) Uani 0.5 1 d D U P A -1
H38 H 0.494691 0.618114 1.019140 0.028 Uiso 0.5 1 calc R U P A -1
C51 C 0.770(2) 1.7801(19) 1.2876(15) 0.024(2) Uani 0.5 1 d D U P A -1
H51 H 0.707664 1.813363 1.346258 0.029 Uiso 0.5 1 calc R U P A -1
C52 C 0.7090(17) 1.6707(16) 1.2555(12) 0.0212(16) Uani 0.5 1 d D U P A -1
C53 C 0.807(2) 1.6207(19) 1.1702(15) 0.018(2) Uani 0.5 1 d D U P A -1
C54 C 0.9579(16) 1.6823(17) 1.1197(12) 0.021(2) Uani 0.5 1 d D U P A -1
H54 H 1.023909 1.648023 1.062598 0.025 Uiso 0.5 1 calc R U P A -1
C55 C 1.0125(18) 1.7931(17) 1.1521(12) 0.026(2) Uani 0.5 1 d D U P A -1
H55 H 1.114549 1.836094 1.116145 0.031 Uiso 0.5 1 calc R U P A -1
C56 C 0.919(2) 1.8416(16) 1.2369(13) 0.025(2) Uani 0.5 1 d D U P A -1
H56 H 0.957931 1.916917 1.259842 0.030 Uiso 0.5 1 calc R U P A -1
C71 C 0.545(2) 1.615(2) 1.3150(16) 0.030(2) Uani 0.5 1 d D U P A -1
O71 O 0.465(2) 1.6630(13) 1.3873(9) 0.051(3) Uani 0.5 1 d D U P A -1
C72 C 0.3389(8) 1.4497(6) 1.3551(5) 0.0339(14) Uani 0.5 1 d D U P A -1
H72A H 0.380805 1.429640 1.420215 0.041 Uiso 0.5 1 calc R U P A -1
H72B H 0.231587 1.497693 1.368662 0.041 Uiso 0.5 1 calc R U P A -1
O72 O 0.4652(10) 1.5366(8) 1.2697(8) 0.0365(19) Uani 0.5 1 d D U P A -1
C73 C 0.3172(9) 1.3221(8) 1.3165(5) 0.0246(12) Uani 0.5 1 d D U P A -1
C74 C 0.3738(14) 1.1992(7) 1.3610(8) 0.0243(13) Uani 0.5 1 d D U P A -1
F74 F 0.4487(11) 1.1956(5) 1.4403(6) 0.0396(11) Uani 0.5 1 d D U P A -1
C75 C 0.3539(19) 1.0812(8) 1.3263(10) 0.0336(15) Uani 0.5 1 d D U P A -1
F75 F 0.4162(14) 0.9661(6) 1.3710(8) 0.0583(18) Uani 0.5 1 d D U P A -1
C76 C 0.274(2) 1.0841(10) 1.2458(10) 0.0450(18) Uani 0.5 1 d D U P A -1
F76 F 0.2584(16) 0.9660(8) 1.2154(9) 0.075(3) Uani 0.5 1 d D U P A -1
C77 C 0.216(2) 1.2022(10) 1.2008(12) 0.0483(18) Uani 0.5 1 d D U P A -1
F77 F 0.1372(18) 1.1987(10) 1.1239(9) 0.088(3) Uani 0.5 1 d D U P A -1
C78 C 0.242(2) 1.3198(9) 1.2344(10) 0.0362(15) Uani 0.5 1 d D U P A -1
F78 F 0.1850(13) 1.4334(8) 1.1867(7) 0.0649(19) Uani 0.5 1 d D U P A -1
C81 C 0.758(2) 1.506(2) 1.1335(19) 0.0179(18) Uani 0.5 1 d D U P A -1
C82 C 0.722(3) 1.4134(14) 1.0982(16) 0.023(2) Uani 0.5 1 d D U P A -1
C83 C 0.6623(16) 1.2972(10) 1.0658(9) 0.0191(14) Uani 0.5 1 d D U P A -1
C84 C 0.6817(11) 1.1683(9) 1.1212(7) 0.0209(15) Uani 0.5 1 d D U P A -1
H84 H 0.737541 1.157930 1.177350 0.025 Uiso 0.5 1 calc R U P A -1
C85 C 0.6201(11) 1.0556(9) 1.0948(7) 0.0201(15) Uani 0.5 1 d D U P A -1
H85 H 0.632689 0.968545 1.133683 0.024 Uiso 0.5 1 calc R U P A -1
C86 C 0.539(3) 1.0684(9) 1.0110(17) 0.0189(13) Uani 0.5 1 d D U P A -1
C87 C 0.5231(8) 1.1983(8) 0.9561(5) 0.0188(12) Uani 0.5 1 d D U P A -1
H87 H 0.469698 1.209370 0.898751 0.023 Uiso 0.5 1 calc R U P A -1
C88 C 0.5828(9) 1.3105(8) 0.9830(6) 0.0193(12) Uani 0.5 1 d D U P A -1
H88 H 0.569478 1.397712 0.944605 0.023 Uiso 0.5 1 calc R U P A -1
C29 C 0.8255(12) 0.2483(5) 0.4660(5) 0.0303(5) Uani 0.693(3) 1 d D U P B 1
H29 H 0.708367 0.243349 0.506624 0.036 Uiso 0.693(3) 1 calc R U P B 1
Cl1 Cl 0.8519(2) 0.40108(19) 0.37776(15) 0.0417(5) Uani 0.693(3) 1 d D U P B 1
Cl2 Cl 0.8606(5) 0.1094(3) 0.4010(2) 0.0546(8) Uani 0.693(3) 1 d D U P B 1
Cl3 Cl 0.9596(5) 0.2432(3) 0.5522(2) 0.0400(6) Uani 0.693(3) 1 d D U P B 1
C29A C 0.824(4) 0.2392(16) 0.4655(17) 0.0303(5) Uani 0.167(3) 1 d D U P C 2
H29A H 0.710090 0.238120 0.510828 0.036 Uiso 0.167(3) 1 calc R U P C 2
Cl1A Cl 0.8278(12) 0.3591(10) 0.3532(7) 0.048(2) Uani 0.167(3) 1 d D U P C 2
Cl2A Cl 0.863(2) 0.0795(9) 0.4283(10) 0.044(2) Uani 0.167(3) 1 d D U P C 2
Cl3A Cl 0.9693(18) 0.2767(13) 0.5346(9) 0.042(2) Uani 0.167(3) 1 d D U P C 2
C29B C 0.821(4) 0.251(2) 0.454(2) 0.0303(5) Uani 0.054(2) 1 d D U P D 3
H29B H 0.709317 0.244578 0.501158 0.036 Uiso 0.054(2) 1 calc R U P D 3
Cl1B Cl 0.9685(15) 0.1687(19) 0.5202(11) 0.049(3) Uani 0.054(2) 1 d D U P D 3
Cl2B Cl 0.820(2) 0.1624(18) 0.3515(13) 0.048(3) Uani 0.054(2) 1 d D U P D 3
Cl3B Cl 0.879(3) 0.4217(18) 0.4106(16) 0.046(3) Uani 0.054(2) 1 d D U P D 3
C29C C 0.835(4) 0.2495(15) 0.4643(19) 0.0303(5) Uani 0.085(2) 1 d D U P E 4
H29C H 0.723198 0.243327 0.512036 0.036 Uiso 0.085(2) 1 calc R U P E 4
Cl1C Cl 0.8119(19) 0.3106(11) 0.3365(9) 0.040(2) Uani 0.085(2) 1 d D U P E 4
Cl2C Cl 0.9266(12) 0.0880(8) 0.4716(8) 0.0450(18) Uani 0.085(2) 1 d D U P E 4
Cl3C Cl 0.9636(11) 0.3591(12) 0.5033(8) 0.050(2) Uani 0.085(2) 1 d D U P E 4


_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 C6 1.379(10) . ?
C1 C2 1.393(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(9) . ?
C2 C21 1.496(9) . ?
C3 C4 1.393(9) . ?
C3 C31 1.447(8) . ?
C4 C5 1.379(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C21 O21 1.198(10) . ?
C21 O22 1.317(11) . ?
C22 C23 1.504(8) . ?
C22 O22 1.517(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.374(8) . ?
C23 C28 1.384(7) . ?
C24 F24 1.339(7) . ?
C24 C25 1.359(8) . ?
C25 F25 1.334(7) . ?
C25 C26 1.384(8) . ?
C26 F26 1.329(7) . ?
C26 C27 1.368(7) . ?
C27 F27 1.334(7) . ?
C27 C28 1.373(7) . ?
C28 F28 1.337(7) . ?
C31 C32 1.188(9) . ?
C32 C33 1.429(8) . ?
C33 C34 1.397(9) . ?
C33 C38 1.400(9) . ?
C34 C35 1.374(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.399(9) . ?
C35 H35 0.9500 . ?
C36 C37 1.388(8) . ?
C36 C86 1.478(5) . ?
C37 C38 1.380(8) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C51 C56 1.377(10) . ?
C51 C52 1.391(10) . ?
C51 H51 0.9500 . ?
C52 C53 1.411(9) . ?
C52 C71 1.481(9) . ?
C53 C54 1.391(9) . ?
C53 C81 1.425(8) . ?
C54 C55 1.381(9) . ?
C54 H54 0.9500 . ?
C55 C56 1.383(10) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C71 O71 1.215(11) . ?
C71 O72 1.339(11) . ?
C72 C73 1.490(7) . ?
C72 O72 1.535(10) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C73 C78 1.373(7) . ?
C73 C74 1.384(7) . ?
C74 F74 1.329(7) . ?
C74 C75 1.372(7) . ?
C75 F75 1.343(8) . ?
C75 C76 1.372(9) . ?
C76 F76 1.335(8) . ?
C76 C77 1.351(10) . ?
C77 F77 1.332(8) . ?
C77 C78 1.371(9) . ?
C78 F78 1.329(8) . ?
C81 C82 1.187(8) . ?
C82 C83 1.443(8) . ?
C83 C88 1.385(9) . ?
C83 C84 1.396(8) . ?
C84 C85 1.381(8) . ?
C84 H84 0.9500 . ?
C85 C86 1.405(9) . ?
C85 H85 0.9500 . ?
C86 C87 1.397(8) . ?
C87 C88 1.373(7) . ?
C87 H87 0.9500 . ?
C88 H88 0.9500 . ?
C29 Cl3 1.750(5) . ?
C29 Cl1 1.752(6) . ?
C29 Cl2 1.753(6) . ?
C29 H29 1.0000 . ?
C29A Cl3A 1.746(16) . ?
C29A Cl1A 1.747(15) . ?
C29A Cl2A 1.759(15) . ?
C29A H29A 1.0000 . ?
C29B Cl1B 1.751(16) . ?
C29B Cl3B 1.754(16) . ?
C29B Cl2B 1.759(16) . ?
C29B H29B 1.0000 . ?
C29C Cl1C 1.760(16) . ?
C29C Cl2C 1.761(16) . ?
C29C Cl3C 1.762(16) . ?
C29C H29C 1.0000 . ?
Cl2C Cl2C 2.222(15) 2_756 ?

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
C6 C1 C2 120.8(10) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 120.0(9) . . ?
C1 C2 C21 114.8(9) . . ?
C3 C2 C21 125.2(9) . . ?
C4 C3 C2 117.8(8) . . ?
C4 C3 C31 117.6(9) . . ?
C2 C3 C31 124.6(9) . . ?
C5 C4 C3 121.8(8) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 119.9(9) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.7(10) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O21 C21 O22 122.9(13) . . ?
O21 C21 C2 124.2(11) . . ?
O22 C21 C2 110.7(9) . . ?
C23 C22 O22 102.0(5) . . ?
C23 C22 H22A 111.4 . . ?
O22 C22 H22A 111.4 . . ?
C23 C22 H22B 111.4 . . ?
O22 C22 H22B 111.4 . . ?
H22A C22 H22B 109.2 . . ?
C21 O22 C22 115.5(10) . . ?
C24 C23 C28 116.5(6) . . ?
C24 C23 C22 120.7(6) . . ?
C28 C23 C22 122.7(6) . . ?
F24 C24 C25 116.8(6) . . ?
F24 C24 C23 119.7(6) . . ?
C25 C24 C23 123.5(7) . . ?
F25 C25 C24 123.5(6) . . ?
F25 C25 C26 118.1(6) . . ?
C24 C25 C26 118.4(6) . . ?
F26 C26 C27 118.7(6) . . ?
F26 C26 C25 121.1(6) . . ?
C27 C26 C25 120.2(6) . . ?
F27 C27 C26 121.4(6) . . ?
F27 C27 C28 118.9(6) . . ?
C26 C27 C28 119.7(6) . . ?
F28 C28 C27 119.4(5) . . ?
F28 C28 C23 119.0(6) . . ?
C27 C28 C23 121.6(6) . . ?
C32 C31 C3 176(2) . . ?
C31 C32 C33 174.1(17) . . ?
C34 C33 C38 117.8(7) . . ?
C34 C33 C32 123.3(9) . . ?
C38 C33 C32 118.9(9) . . ?
C35 C34 C33 120.4(7) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 122.1(7) . . ?
C34 C35 H35 118.9 . . ?
C36 C35 H35 118.9 . . ?
C37 C36 C35 117.0(7) . . ?
C37 C36 C86 121.4(5) . . ?
C35 C36 C86 121.6(5) . . ?
C38 C37 C36 121.5(7) . . ?
C38 C37 H37 119.2 . . ?
C36 C37 H37 119.2 . . ?
C37 C38 C33 120.9(7) . . ?
C37 C38 H38 119.6 . . ?
C33 C38 H38 119.6 . . ?
C56 C51 C52 121.8(10) . . ?
C56 C51 H51 119.1 . . ?
C52 C51 H51 119.1 . . ?
C51 C52 C53 118.0(9) . . ?
C51 C52 C71 116.8(9) . . ?
C53 C52 C71 125.2(9) . . ?
C54 C53 C52 119.9(8) . . ?
C54 C53 C81 117.6(8) . . ?
C52 C53 C81 122.4(9) . . ?
C55 C54 C53 120.4(9) . . ?
C55 C54 H54 119.8 . . ?
C53 C54 H54 119.8 . . ?
C54 C55 C56 120.3(9) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C51 C56 C55 119.6(10) . . ?
C51 C56 H56 120.2 . . ?
C55 C56 H56 120.2 . . ?
O71 C71 O72 117.7(13) . . ?
O71 C71 C52 122.7(11) . . ?
O72 C71 C52 117.0(9) . . ?
C73 C72 O72 106.5(6) . . ?
C73 C72 H72A 110.4 . . ?
O72 C72 H72A 110.4 . . ?
C73 C72 H72B 110.4 . . ?
O72 C72 H72B 110.4 . . ?
H72A C72 H72B 108.6 . . ?
C71 O72 C72 108.0(10) . . ?
C78 C73 C74 116.3(6) . . ?
C78 C73 C72 122.2(6) . . ?
C74 C73 C72 121.5(5) . . ?
F74 C74 C75 119.1(6) . . ?
F74 C74 C73 118.9(5) . . ?
C75 C74 C73 122.0(7) . . ?
F75 C75 C74 118.9(7) . . ?
F75 C75 C76 121.8(7) . . ?
C74 C75 C76 119.3(7) . . ?
F76 C76 C77 123.2(7) . . ?
F76 C76 C75 116.4(8) . . ?
C77 C76 C75 120.4(7) . . ?
F77 C77 C76 117.7(8) . . ?
F77 C77 C78 122.9(8) . . ?
C76 C77 C78 119.4(7) . . ?
F78 C78 C77 117.1(7) . . ?
F78 C78 C73 120.2(6) . . ?
C77 C78 C73 122.6(7) . . ?
C82 C81 C53 177(2) . . ?
C81 C82 C83 173.4(18) . . ?
C88 C83 C84 119.1(7) . . ?
C88 C83 C82 121.8(8) . . ?
C84 C83 C82 119.0(9) . . ?
C85 C84 C83 120.4(7) . . ?
C85 C84 H84 119.8 . . ?
C83 C84 H84 119.8 . . ?
C84 C85 C86 120.7(7) . . ?
C84 C85 H85 119.6 . . ?
C86 C85 H85 119.6 . . ?
C87 C86 C85 117.7(6) . . ?
C87 C86 C36 121.7(5) . . ?
C85 C86 C36 120.6(5) . . ?
C88 C87 C86 121.5(7) . . ?
C88 C87 H87 119.2 . . ?
C86 C87 H87 119.2 . . ?
C87 C88 C83 120.5(7) . . ?
C87 C88 H88 119.8 . . ?
C83 C88 H88 119.8 . . ?
Cl3 C29 Cl1 110.0(4) . . ?
Cl3 C29 Cl2 110.4(4) . . ?
Cl1 C29 Cl2 111.0(4) . . ?
Cl3 C29 H29 108.5 . . ?
Cl1 C29 H29 108.5 . . ?
Cl2 C29 H29 108.5 . . ?
Cl3A C29A Cl1A 111.7(12) . . ?
Cl3A C29A Cl2A 110.7(13) . . ?
Cl1A C29A Cl2A 107.9(11) . . ?
Cl3A C29A H29A 108.8 . . ?
Cl1A C29A H29A 108.8 . . ?
Cl2A C29A H29A 108.8 . . ?
Cl1B C29B Cl3B 109.3(17) . . ?
Cl1B C29B Cl2B 105.5(16) . . ?
Cl3B C29B Cl2B 112.9(18) . . ?
Cl1B C29B H29B 109.7 . . ?
Cl3B C29B H29B 109.7 . . ?
Cl2B C29B H29B 109.7 . . ?
Cl1C C29C Cl2C 110.0(12) . . ?
Cl1C C29C Cl3C 110.4(13) . . ?
Cl2C C29C Cl3C 108.5(12) . . ?
Cl1C C29C H29C 109.3 . . ?
Cl2C C29C H29C 109.3 . . ?
Cl3C C29C H29C 109.3 . . ?
C29C Cl2C Cl2C 158.5(11) . 2_756 ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_WM104_1_0m_a_a_a
_database_code_depnum_ccdc_archive 'CCDC 1875126'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H24 F10 O4'
_chemical_formula_weight         842.66

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   11.3978(11)
_cell_length_b                   13.2721(12)
_cell_length_c                   14.4774(14)
_cell_angle_alpha                108.224(2)
_cell_angle_beta                 95.725(2)
_cell_angle_gamma                115.411(2)
_cell_volume                     1807.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      29.43

_exptl_crystal_description       Prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .6954
_exptl_absorpt_correction_T_max  .7459
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39050
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.539
_diffrn_reflns_theta_max         29.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10037
_reflns_number_gt                7224
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0748P)²+0.5207P] 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_number_reflns         10037
_refine_ls_number_parameters     562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
F001 F 0.14016(11) 0.55036(10) 0.77097(8) 0.0345(3) Uani 1 1 d . . . . .
F002 F 0.12077(12) 0.54339(9) 0.95366(8) 0.0364(3) Uani 1 1 d . . . . .
F003 F 0.03116(12) 0.33059(10) 0.97638(8) 0.0349(3) Uani 1 1 d . . . . .
F004 F 0.81154(11) 1.30513(11) 0.35765(10) 0.0383(3) Uani 1 1 d . . . . .
F005 F 0.92083(12) 1.02303(9) 0.41617(8) 0.0350(3) Uani 1 1 d . . . . .
F006 F 1.17067(11) 1.14609(11) 0.39902(9) 0.0402(3) Uani 1 1 d . . . . .
O007 O 0.05053(11) 0.08355(10) 0.84150(10) 0.0264(3) Uani 1 1 d . . . . .
F008 F 0.06434(15) 0.34321(12) 0.60910(8) 0.0486(3) Uani 1 1 d . . . . .
F009 F 1.24259(11) 1.35041(12) 0.36239(11) 0.0485(3) Uani 1 1 d . . . . .
O00A O 0.71153(14) 1.16874(11) 0.48983(9) 0.0305(3) Uani 1 1 d . . . . .
F00B F 1.06402(13) 1.43031(13) 0.34352(12) 0.0549(4) Uani 1 1 d . . . . .
F00C F -0.03085(17) 0.13006(11) 0.63013(9) 0.0564(4) Uani 1 1 d . . . . .
O00D O -0.09413(13) -0.07672(13) 0.86674(12) 0.0399(4) Uani 1 1 d . . . . .
C00E C 0.45810(15) 0.50402(13) 0.79963(11) 0.0152(3) Uani 1 1 d . . . . .
C00F C 0.25613(15) 0.01853(13) 0.85878(11) 0.0160(3) Uani 1 1 d . . . . .
C00G C 0.57482(15) 0.81218(13) 0.80221(12) 0.0170(3) Uani 1 1 d . . . . .
H00G H 0.614171 0.873882 0.868621 0.020 Uiso 1 1 calc R U . . .
C00H C 0.43002(15) 0.48334(13) 0.69696(11) 0.0160(3) Uani 1 1 d . . . . .
C00I C 0.52968(15) 0.63912(13) 0.86601(11) 0.0152(3) Uani 1 1 d . . . . .
C00J C 0.32439(15) 0.19004(13) 0.78781(11) 0.0176(3) Uani 1 1 d . . . . .
C00K C 0.29052(15) 0.11195(13) 0.82000(11) 0.0165(3) Uani 1 1 d . . . . .
C00L C 0.47205(15) 0.60072(13) 0.68891(11) 0.0162(3) Uani 1 1 d . . . . .
C00M C 0.42267(15) 0.40802(13) 0.82937(11) 0.0167(3) Uani 1 1 d . . . . .
H00M H 0.439724 0.422372 0.899123 0.020 Uiso 1 1 calc R U . . .
C00N C 0.13096(15) -0.04022(13) 0.87875(11) 0.0174(3) Uani 1 1 d . . . . .
C00O C 0.56215(15) 0.84163(14) 0.71805(12) 0.0177(3) Uani 1 1 d . . . . .
C00P C 0.46168(16) 0.62991(14) 0.60530(12) 0.0193(3) Uani 1 1 d . . . . .
H00P H 0.424251 0.568226 0.538896 0.023 Uiso 1 1 calc R U . . .
C00Q C 0.01721(16) -0.01477(14) 0.86248(12) 0.0211(3) Uani 1 1 d . . . . .
C00R C 0.52911(15) 0.69191(13) 0.78687(11) 0.0153(3) Uani 1 1 d . . . . .
C00S C 0.66290(15) 1.18070(13) 0.73585(12) 0.0178(3) Uani 1 1 d . . . . .
C00T C 0.36121(15) 0.28896(13) 0.75556(11) 0.0175(3) Uani 1 1 d . . . . .
C00U C 0.60245(15) 0.96415(14) 0.73074(12) 0.0193(3) Uani 1 1 d . . . . .
C00V C 0.67574(15) 0.68270(14) 0.92199(12) 0.0194(3) Uani 1 1 d . . . . .
H00A H 0.722898 0.660559 0.872958 0.029 Uiso 1 1 calc R U . . .
H00B H 0.674607 0.644135 0.969863 0.029 Uiso 1 1 calc R U . . .
H00C H 0.722610 0.771117 0.958762 0.029 Uiso 1 1 calc R U . . .
C00W C 0.37113(16) 0.36599(14) 0.62338(12) 0.0201(3) Uani 1 1 d . . . . .
H00W H 0.354146 0.352187 0.553739 0.024 Uiso 1 1 calc R U . . .
C00X C 0.45341(16) 0.67137(14) 0.94103(11) 0.0188(3) Uani 1 1 d . . . . .
H00D H 0.363178 0.648822 0.903988 0.028 Uiso 1 1 calc R U . . .
H00E H 0.502918 0.758909 0.982142 0.028 Uiso 1 1 calc R U . . .
H00F H 0.445237 0.627051 0.985065 0.028 Uiso 1 1 calc R U . . .
C00Y C 0.35191(16) -0.01789(14) 0.87537(12) 0.0198(3) Uani 1 1 d . . . . .
H00Y H 0.436756 0.020939 0.862604 0.024 Uiso 1 1 calc R U . . .
C00Z C 0.85850(16) 1.16015(15) 0.38607(12) 0.0217(3) Uani 1 1 d . . . . .
C010 C 0.50673(16) 0.75022(14) 0.62022(12) 0.0200(3) Uani 1 1 d . . . . .
H010 H 0.500005 0.771025 0.563555 0.024 Uiso 1 1 calc R U . . .
C011 C 0.68201(16) 1.21052(14) 0.65110(12) 0.0206(3) Uani 1 1 d . . . . .
C012 C 0.67640(16) 1.27007(14) 0.82537(12) 0.0212(3) Uani 1 1 d . . . . .
H012 H 0.665474 1.252086 0.883526 0.025 Uiso 1 1 calc R U . . .
C013 C 0.63115(15) 1.06319(14) 0.73322(12) 0.0190(3) Uani 1 1 d . . . . .
C014 C 0.33729(17) 0.26891(14) 0.65277(12) 0.0208(3) Uani 1 1 d . . . . .
H014 H 0.297741 0.188572 0.602890 0.025 Uiso 1 1 calc R U . . .
C015 C 0.70546(17) 1.38440(15) 0.83033(13) 0.0238(3) Uani 1 1 d . . . . .
H015 H 0.714354 1.444163 0.891781 0.029 Uiso 1 1 calc R U . . .
C016 C 0.72163(17) 1.41226(15) 0.74675(14) 0.0248(3) Uani 1 1 d . . . . .
H016 H 0.740370 1.490600 0.750365 0.030 Uiso 1 1 calc R U . . .
C017 C 0.95269(17) 1.12238(15) 0.39661(12) 0.0235(3) Uani 1 1 d . . . . .
C018 C 0.32545(18) -0.10928(15) 0.90998(13) 0.0253(3) Uani 1 1 d . . . . .
H018 H 0.391959 -0.132603 0.920695 0.030 Uiso 1 1 calc R U . . .
C019 C 0.71051(18) 1.32598(15) 0.65773(13) 0.0246(3) Uani 1 1 d . . . . .
H019 H 0.722434 1.345644 0.600423 0.030 Uiso 1 1 calc R U . . .
C01A C 0.08428(17) 0.44038(15) 0.87399(13) 0.0240(3) Uani 1 1 d . . . . .
C01B C 0.03756(17) 0.33117(15) 0.88436(13) 0.0232(3) Uani 1 1 d . . . . .
C01C C 0.10647(18) -0.13243(14) 0.91355(13) 0.0237(3) Uani 1 1 d . . . . .
H01C H 0.022156 -0.172065 0.926750 0.028 Uiso 1 1 calc R U . . .
C01D C 0.20233(19) -0.16707(15) 0.92913(14) 0.0275(4) Uani 1 1 d . . . . .
H01D H 0.184118 -0.230008 0.952792 0.033 Uiso 1 1 calc R U . . .
C01E C -0.00339(16) 0.22309(15) 0.80357(13) 0.0233(3) Uani 1 1 d . . . . .
C01F C 1.08149(18) 1.18462(17) 0.38820(13) 0.0284(4) Uani 1 1 d . . . . .
C01G C 0.89876(17) 1.26446(16) 0.36772(13) 0.0261(4) Uani 1 1 d . . . . .
C01H C 0.09386(17) 0.44467(15) 0.78126(13) 0.0252(3) Uani 1 1 d . . . . .
C01I C -0.06076(17) 0.10424(15) 0.81552(15) 0.0270(4) Uani 1 1 d . . . . .
H01A H -0.107510 0.107378 0.869586 0.032 Uiso 1 1 calc R U . . .
H01B H -0.126633 0.037656 0.751684 0.032 Uiso 1 1 calc R U . . .
C01J C 0.71920(18) 1.09438(16) 0.39619(13) 0.0272(4) Uani 1 1 d . . . . .
H01E H 0.651363 1.080435 0.338564 0.033 Uiso 1 1 calc R U . . .
H01F H 0.700986 1.014657 0.396779 0.033 Uiso 1 1 calc R U . . .
C01K C 1.11809(18) 1.28781(18) 0.36992(15) 0.0320(4) Uani 1 1 d . . . . .
C01L C 0.0560(2) 0.33921(18) 0.69929(13) 0.0307(4) Uani 1 1 d . . . . .
C01M C 1.02714(19) 1.32872(18) 0.36022(15) 0.0327(4) Uani 1 1 d . . . . .
C01N C 0.0082(2) 0.23085(16) 0.71167(14) 0.0314(4) Uani 1 1 d . . . . .
C01O C 0.6751(2) 1.11981(16) 0.55577(14) 0.0309(4) Uani 1 1 d . . . . .
O01P O 0.6901(17) 1.0316(9) 0.5507(5) 0.050(3) Uani 0.48(2) 1 d . . P A 1
O01Q O 0.6064(12) 1.0087(3) 0.5292(4) 0.043(2) Uani 0.52(2) 1 d . . 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
F001 C01H 1.3340(19) . ?
F002 C01A 1.3426(19) . ?
F003 C01B 1.344(2) . ?
F004 C01G 1.335(2) . ?
F005 C017 1.339(2) . ?
F006 C01F 1.336(2) . ?
O007 C00Q 1.3361(19) . ?
O007 C01I 1.4472(19) . ?
F008 C01L 1.334(2) . ?
F009 C01K 1.338(2) . ?
O00A C01O 1.319(2) . ?
O00A C01J 1.442(2) . ?
F00B C01M 1.338(2) . ?
F00C C01N 1.333(2) . ?
O00D C00Q 1.201(2) . ?
C00E C00M 1.381(2) . ?
C00E C00H 1.401(2) . ?
C00E C00I 1.521(2) . ?
C00F C00Y 1.399(2) . ?
C00F C00N 1.413(2) . ?
C00F C00K 1.438(2) . ?
C00G C00R 1.382(2) . ?
C00G C00O 1.403(2) . ?
C00G H00G 0.9500 . ?
C00H C00W 1.390(2) . ?
C00H C00L 1.4678(19) . ?
C00I C00R 1.5193(19) . ?
C00I C00X 1.528(2) . ?
C00I C00V 1.541(2) . ?
C00J C00K 1.198(2) . ?
C00J C00T 1.438(2) . ?
C00L C00P 1.390(2) . ?
C00L C00R 1.402(2) . ?
C00M C00T 1.405(2) . ?
C00M H00M 0.9500 . ?
C00N C01C 1.396(2) . ?
C00N C00Q 1.488(2) . ?
C00O C010 1.402(2) . ?
C00O C00U 1.430(2) . ?
C00P C010 1.385(2) . ?
C00P H00P 0.9500 . ?
C00S C012 1.397(2) . ?
C00S C011 1.412(2) . ?
C00S C013 1.428(2) . ?
C00T C014 1.403(2) . ?
C00U C013 1.198(2) . ?
C00V H00A 0.9800 . ?
C00V H00B 0.9800 . ?
C00V H00C 0.9800 . ?
C00W C014 1.393(2) . ?
C00W H00W 0.9500 . ?
C00X H00D 0.9800 . ?
C00X H00E 0.9800 . ?
C00X H00F 0.9800 . ?
C00Y C018 1.382(2) . ?
C00Y H00Y 0.9500 . ?
C00Z C017 1.380(2) . ?
C00Z C01G 1.381(2) . ?
C00Z C01J 1.497(2) . ?
C010 H010 0.9500 . ?
C011 C019 1.392(2) . ?
C011 C01O 1.489(2) . ?
C012 C015 1.383(2) . ?
C012 H012 0.9500 . ?
C014 H014 0.9500 . ?
C015 C016 1.379(2) . ?
C015 H015 0.9500 . ?
C016 C019 1.381(2) . ?
C016 H016 0.9500 . ?
C017 C01F 1.382(3) . ?
C018 C01D 1.386(2) . ?
C018 H018 0.9500 . ?
C019 H019 0.9500 . ?
C01A C01H 1.374(2) . ?
C01A C01B 1.377(2) . ?
C01B C01E 1.382(2) . ?
C01C C01D 1.379(2) . ?
C01C H01C 0.9500 . ?
C01D H01D 0.9500 . ?
C01E C01N 1.381(3) . ?
C01E C01I 1.501(2) . ?
C01F C01K 1.370(3) . ?
C01G C01M 1.378(2) . ?
C01H C01L 1.376(3) . ?
C01I H01A 0.9900 . ?
C01I H01B 0.9900 . ?
C01J H01E 0.9900 . ?
C01J H01F 0.9900 . ?
C01K C01M 1.375(3) . ?
C01L C01N 1.380(3) . ?
C01O O01P 1.235(4) . ?
C01O O01Q 1.237(3) . ?

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
C00Q O007 C01I 114.83(12) . . ?
C01O O00A C01J 117.75(14) . . ?
C00M C00E C00H 120.61(13) . . ?
C00M C00E C00I 128.15(13) . . ?
C00H C00E C00I 111.23(12) . . ?
C00Y C00F C00N 118.30(13) . . ?
C00Y C00F C00K 117.60(13) . . ?
C00N C00F C00K 124.08(14) . . ?
C00R C00G C00O 118.89(14) . . ?
C00R C00G H00G 120.6 . . ?
C00O C00G H00G 120.6 . . ?
C00W C00H C00E 120.34(13) . . ?
C00W C00H C00L 131.39(14) . . ?
C00E C00H C00L 108.27(13) . . ?
C00R C00I C00E 100.86(12) . . ?
C00R C00I C00X 111.73(12) . . ?
C00E C00I C00X 112.19(12) . . ?
C00R C00I C00V 110.31(12) . . ?
C00E C00I C00V 110.92(12) . . ?
C00X C00I C00V 110.49(12) . . ?
C00K C00J C00T 175.18(17) . . ?
C00J C00K C00F 177.23(16) . . ?
C00P C00L C00R 120.52(13) . . ?
C00P C00L C00H 131.33(14) . . ?
C00R C00L C00H 108.15(12) . . ?
C00E C00M C00T 119.42(13) . . ?
C00E C00M H00M 120.3 . . ?
C00T C00M H00M 120.3 . . ?
C01C C00N C00F 119.42(14) . . ?
C01C C00N C00Q 115.51(14) . . ?
C00F C00N C00Q 125.03(13) . . ?
C010 C00O C00G 120.11(14) . . ?
C010 C00O C00U 119.16(14) . . ?
C00G C00O C00U 120.71(14) . . ?
C010 C00P C00L 119.04(14) . . ?
C010 C00P H00P 120.5 . . ?
C00L C00P H00P 120.5 . . ?
O00D C00Q O007 122.96(15) . . ?
O00D C00Q C00N 123.67(15) . . ?
O007 C00Q C00N 113.37(13) . . ?
C00G C00R C00L 120.70(13) . . ?
C00G C00R C00I 127.95(14) . . ?
C00L C00R C00I 111.34(12) . . ?
C012 C00S C011 118.42(14) . . ?
C012 C00S C013 119.22(14) . . ?
C011 C00S C013 122.36(14) . . ?
C014 C00T C00M 119.79(13) . . ?
C014 C00T C00J 121.50(14) . . ?
C00M C00T C00J 118.71(13) . . ?
C013 C00U C00O 174.70(17) . . ?
C00I C00V H00A 109.5 . . ?
C00I C00V H00B 109.5 . . ?
H00A C00V H00B 109.5 . . ?
C00I C00V H00C 109.5 . . ?
H00A C00V H00C 109.5 . . ?
H00B C00V H00C 109.5 . . ?
C00H C00W C014 119.35(14) . . ?
C00H C00W H00W 120.3 . . ?
C014 C00W H00W 120.3 . . ?
C00I C00X H00D 109.5 . . ?
C00I C00X H00E 109.5 . . ?
H00D C00X H00E 109.5 . . ?
C00I C00X H00F 109.5 . . ?
H00D C00X H00F 109.5 . . ?
H00E C00X H00F 109.5 . . ?
C018 C00Y C00F 121.25(14) . . ?
C018 C00Y H00Y 119.4 . . ?
C00F C00Y H00Y 119.4 . . ?
C017 C00Z C01G 117.07(15) . . ?
C017 C00Z C01J 122.53(16) . . ?
C01G C00Z C01J 120.39(16) . . ?
C00P C010 C00O 120.72(14) . . ?
C00P C010 H010 119.6 . . ?
C00O C010 H010 119.6 . . ?
C019 C011 C00S 119.75(15) . . ?
C019 C011 C01O 120.12(14) . . ?
C00S C011 C01O 120.11(14) . . ?
C015 C012 C00S 120.80(15) . . ?
C015 C012 H012 119.6 . . ?
C00S C012 H012 119.6 . . ?
C00U C013 C00S 178.99(16) . . ?
C00W C014 C00T 120.44(14) . . ?
C00W C014 H014 119.8 . . ?
C00T C014 H014 119.8 . . ?
C016 C015 C012 120.48(15) . . ?
C016 C015 H015 119.8 . . ?
C012 C015 H015 119.8 . . ?
C015 C016 C019 119.83(15) . . ?
C015 C016 H016 120.1 . . ?
C019 C016 H016 120.1 . . ?
F005 C017 C00Z 120.08(15) . . ?
F005 C017 C01F 117.92(16) . . ?
C00Z C017 C01F 122.00(16) . . ?
C00Y C018 C01D 120.31(15) . . ?
C00Y C018 H018 119.8 . . ?
C01D C018 H018 119.8 . . ?
C016 C019 C011 120.71(15) . . ?
C016 C019 H019 119.6 . . ?
C011 C019 H019 119.6 . . ?
F002 C01A C01H 119.29(15) . . ?
F002 C01A C01B 120.74(15) . . ?
C01H C01A C01B 119.96(16) . . ?
F003 C01B C01A 118.36(15) . . ?
F003 C01B C01E 119.38(15) . . ?
C01A C01B C01E 122.26(16) . . ?
C01D C01C C00N 121.28(15) . . ?
C01D C01C H01C 119.4 . . ?
C00N C01C H01C 119.4 . . ?
C01C C01D C018 119.44(15) . . ?
C01C C01D H01D 120.3 . . ?
C018 C01D H01D 120.3 . . ?
C01N C01E C01B 116.21(16) . . ?
C01N C01E C01I 122.43(16) . . ?
C01B C01E C01I 121.34(16) . . ?
F006 C01F C01K 119.91(16) . . ?
F006 C01F C017 120.68(17) . . ?
C01K C01F C017 119.40(17) . . ?
F004 C01G C01M 118.79(16) . . ?
F004 C01G C00Z 119.31(15) . . ?
C01M C01G C00Z 121.90(16) . . ?
F001 C01H C01A 120.22(16) . . ?
F001 C01H C01L 120.30(16) . . ?
C01A C01H C01L 119.49(16) . . ?
O007 C01I C01E 107.50(13) . . ?
O007 C01I H01A 110.2 . . ?
C01E C01I H01A 110.2 . . ?
O007 C01I H01B 110.2 . . ?
C01E C01I H01B 110.2 . . ?
H01A C01I H01B 108.5 . . ?
O00A C01J C00Z 107.70(13) . . ?
O00A C01J H01E 110.2 . . ?
C00Z C01J H01E 110.2 . . ?
O00A C01J H01F 110.2 . . ?
C00Z C01J H01F 110.2 . . ?
H01E C01J H01F 108.5 . . ?
F009 C01K C01F 120.59(17) . . ?
F009 C01K C01M 119.35(18) . . ?
C01F C01K C01M 120.06(16) . . ?
F008 C01L C01H 119.50(17) . . ?
F008 C01L C01N 121.20(17) . . ?
C01H C01L C01N 119.29(17) . . ?
F00B C01M C01K 119.75(16) . . ?
F00B C01M C01G 120.68(17) . . ?
C01K C01M C01G 119.56(17) . . ?
F00C C01N C01L 117.69(17) . . ?
F00C C01N C01E 119.52(17) . . ?
C01L C01N C01E 122.77(16) . . ?
O01P C01O O00A 118.4(3) . . ?
O01Q C01O O00A 121.6(2) . . ?
O01P C01O C011 124.3(3) . . ?
O01Q C01O C011 123.7(3) . . ?
O00A C01O C011 111.18(14) . . ?

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_WM0133_0M_P1bar_a
_database_code_depnum_ccdc_archive 'CCDC 1875129'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 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         ?
_chemical_formula_sum            'C38 H26 O4'
_chemical_formula_weight         546.59

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.7395(8)
_cell_length_b                   9.8000(9)
_cell_length_c                   32.564(3)
_cell_angle_alpha                89.928(2)
_cell_angle_beta                 86.471(2)
_cell_angle_gamma                89.982(2)
_cell_volume                     2783.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      38.16

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48402
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         0.626
_diffrn_reflns_theta_max         26.874
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11837
_reflns_number_gt                9021
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0598P)²+0.7950P] 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_number_reflns         11837
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_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
C1A C 0.35571(15) 1.00159(13) 0.06244(4) 0.0182(3) Uani 1 1 d . . . . .
C1B C 0.85433(15) 0.49879(13) 0.56157(4) 0.0175(3) Uani 1 1 d . . . . .
C2A C 0.27862(17) 1.00006(15) 0.02618(4) 0.0232(3) Uani 1 1 d . . . . .
H2A H 0.302551 0.931629 0.006162 0.028 Uiso 1 1 calc R U . . .
C2B C 0.78444(16) 0.49781(14) 0.52419(4) 0.0211(3) Uani 1 1 d . . . . .
H2B H 0.815995 0.432376 0.503894 0.025 Uiso 1 1 calc R U . . .
C3A C 0.16772(17) 1.09674(15) 0.01887(4) 0.0255(3) Uani 1 1 d . . . . .
H3A H 0.115895 1.094499 -0.005925 0.031 Uiso 1 1 calc R U . . .
C4A C 0.13306(17) 1.19679(15) 0.04806(4) 0.0247(3) Uani 1 1 d . . . . .
H4A H 0.058504 1.264337 0.043007 0.030 Uiso 1 1 calc R U . . .
C3B C 0.67015(17) 0.59003(15) 0.51599(4) 0.0240(3) Uani 1 1 d . . . . .
H3B H 0.624557 0.588498 0.490249 0.029 Uiso 1 1 calc R U . . .
C5A C 0.20675(16) 1.19879(14) 0.08466(4) 0.0225(3) Uani 1 1 d . . . . .
H5A H 0.181560 1.267622 0.104455 0.027 Uiso 1 1 calc R U . . .
C4B C 0.62291(16) 0.68482(14) 0.54583(4) 0.0228(3) Uani 1 1 d . . . . .
H4B H 0.544877 0.748752 0.540450 0.027 Uiso 1 1 calc R U . . .
C6A C 0.31798(15) 1.10050(14) 0.09282(4) 0.0182(3) Uani 1 1 d . . . . .
C5B C 0.68907(16) 0.68653(14) 0.58339(4) 0.0208(3) Uani 1 1 d . . . . .
H5B H 0.655442 0.751842 0.603512 0.025 Uiso 1 1 calc R U . . .
C7A C 0.38097(15) 1.10317(13) 0.13274(4) 0.0191(3) Uani 1 1 d . . . . .
C6B C 0.80518(15) 0.59340(13) 0.59237(4) 0.0177(3) Uani 1 1 d . . . . .
C8A C 0.42428(15) 1.10615(14) 0.16711(4) 0.0197(3) Uani 1 1 d . . . . .
C7B C 0.86015(15) 0.59681(13) 0.63303(4) 0.0182(3) Uani 1 1 d . . . . .
C9A C 0.47327(16) 1.10462(13) 0.20843(4) 0.0187(3) Uani 1 1 d . . . . .
C8B C 0.89397(16) 0.60234(13) 0.66827(4) 0.0194(3) Uani 1 1 d . . . . .
C10A C 0.39094(16) 1.02895(14) 0.23886(4) 0.0216(3) Uani 1 1 d . . . . .
H10A H 0.304517 0.977171 0.231811 0.026 Uiso 1 1 calc R U . . .
C9B C 0.93859(16) 0.60321(13) 0.70999(4) 0.0187(3) Uani 1 1 d . . . . .
C11A C 0.43369(16) 1.02861(14) 0.27898(4) 0.0210(3) Uani 1 1 d . . . . .
H11A H 0.375832 0.977411 0.299275 0.025 Uiso 1 1 calc R U . . .
C10B C 1.06652(16) 0.52837(14) 0.72109(4) 0.0213(3) Uani 1 1 d . . . . .
H10B H 1.124238 0.476860 0.700875 0.026 Uiso 1 1 calc R U . . .
C12A C 0.56169(16) 1.10313(13) 0.29003(4) 0.0189(3) Uani 1 1 d . . . . .
C11B C 1.10909(16) 0.52912(14) 0.76124(4) 0.0214(3) Uani 1 1 d . . . . .
H11B H 1.195743 0.477649 0.768344 0.026 Uiso 1 1 calc R U . . .
C13A C 0.64518(17) 1.17768(15) 0.25959(4) 0.0248(3) Uani 1 1 d . . . . .
H13A H 0.732319 1.228587 0.266583 0.030 Uiso 1 1 calc R U . . .
C12B C 1.02657(15) 0.60452(13) 0.79162(4) 0.0187(3) Uani 1 1 d . . . . .
C14A C 0.60199(17) 1.17796(15) 0.21936(4) 0.0241(3) Uani 1 1 d . . . . .
H14A H 0.660331 1.228439 0.198990 0.029 Uiso 1 1 calc R U . . .
C13B C 0.89812(17) 0.67803(15) 0.78068(4) 0.0240(3) Uani 1 1 d . . . . .
H13B H 0.839948 0.728724 0.801008 0.029 Uiso 1 1 calc R U . . .
C15A C 0.60607(16) 1.10235(13) 0.33180(4) 0.0195(3) Uani 1 1 d . . . . .
C14B C 0.85492(17) 0.67758(14) 0.74044(4) 0.0242(3) Uani 1 1 d . . . . .
H14B H 0.767583 0.728292 0.733426 0.029 Uiso 1 1 calc R U . . .
C16A C 0.63989(15) 1.09693(13) 0.36706(4) 0.0182(3) Uani 1 1 d . . . . .
C15B C 1.07586(16) 0.60631(14) 0.83299(4) 0.0203(3) Uani 1 1 d . . . . .
C17A C 0.69495(15) 1.09360(13) 0.40772(4) 0.0176(3) Uani 1 1 d . . . . .
C16B C 1.11897(15) 0.60336(13) 0.86733(4) 0.0191(3) Uani 1 1 d . . . . .
C18A C 0.64584(15) 0.99871(13) 0.43844(4) 0.0177(3) Uani 1 1 d . . . . .
C17B C 1.18202(15) 0.60078(13) 0.90722(4) 0.0180(3) Uani 1 1 d . . . . .
C19A C 0.71561(16) 0.99777(14) 0.47590(4) 0.0213(3) Uani 1 1 d . . . . .
H19A H 0.683754 0.932483 0.496256 0.026 Uiso 1 1 calc R U . . .
C18B C 1.14433(15) 0.50168(13) 0.93759(4) 0.0185(3) Uani 1 1 d . . . . .
C20A C 0.83025(17) 1.08985(15) 0.48409(4) 0.0237(3) Uani 1 1 d . . . . .
H20A H 0.876111 1.087978 0.509790 0.028 Uiso 1 1 calc R U . . .
C19B C 1.22160(17) 0.50022(15) 0.97384(4) 0.0230(3) Uani 1 1 d . . . . .
H19B H 1.197630 0.431788 0.993900 0.028 Uiso 1 1 calc R U . . .
C21A C 0.87717(16) 1.18497(14) 0.45419(4) 0.0227(3) Uani 1 1 d . . . . .
H21A H 0.955021 1.249014 0.459557 0.027 Uiso 1 1 calc R U . . .
C20B C 1.33265(17) 0.59668(15) 0.98115(4) 0.0257(3) Uani 1 1 d . . . . .
H20B H 1.384646 0.594189 1.005911 0.031 Uiso 1 1 calc R U . . .
C22A C 0.81096(16) 1.18679(14) 0.41663(4) 0.0206(3) Uani 1 1 d . . . . .
H22A H 0.844460 1.252191 0.396476 0.025 Uiso 1 1 calc R U . . .
C21B C 1.36698(17) 0.69678(15) 0.95193(4) 0.0247(3) Uani 1 1 d . . . . .
H21B H 1.441402 0.764381 0.956971 0.030 Uiso 1 1 calc R U . . .
C31A C 0.47693(15) 0.89508(13) 0.06577(4) 0.0191(3) Uani 1 1 d . . . . .
O31A O 0.49070(12) 0.79735(10) 0.04322(3) 0.0273(2) Uani 1 1 d . . . . .
C22B C 1.29348(16) 0.69898(14) 0.91539(4) 0.0224(3) Uani 1 1 d . . . . .
H22B H 1.318788 0.767860 0.895573 0.027 Uiso 1 1 calc R U . . .
C32A C 0.68748(17) 0.81724(15) 0.10109(5) 0.0268(3) Uani 1 1 d . . . . .
H32A H 0.753217 0.806803 0.075420 0.032 Uiso 1 1 calc R U . . .
H32B H 0.639862 0.727969 0.108206 0.032 Uiso 1 1 calc R U . . .
O32A O 0.56989(12) 0.92005(10) 0.09579(3) 0.0257(2) Uani 1 1 d . . . . .
C31B C 0.97626(15) 0.39328(13) 0.56584(4) 0.0179(3) Uani 1 1 d . . . . .
O31B O 0.99120(12) 0.29565(10) 0.54327(3) 0.0248(2) Uani 1 1 d . . . . .
C33A C 0.78061(16) 0.86639(14) 0.13543(5) 0.0229(3) Uani 1 1 d . . . . .
C32B C 1.18289(16) 0.31171(14) 0.60135(4) 0.0230(3) Uani 1 1 d . . . . .
H32C H 1.240813 0.294670 0.574759 0.028 Uiso 1 1 calc R U . . .
H32D H 1.132598 0.225578 0.610618 0.028 Uiso 1 1 calc R U . . .
O32B O 1.06801(11) 0.41738(10) 0.59643(3) 0.0215(2) Uani 1 1 d . . . . .
C34A C 0.75557(19) 0.81561(17) 0.17510(5) 0.0324(4) Uani 1 1 d . . . . .
H34A H 0.680549 0.746753 0.180558 0.039 Uiso 1 1 calc R U . . .
C33B C 1.28977(15) 0.35973(14) 0.63277(4) 0.0196(3) Uani 1 1 d . . . . .
C35A C 0.8394(2) 0.86464(17) 0.20693(5) 0.0350(4) Uani 1 1 d . . . . .
H35A H 0.821989 0.828760 0.233932 0.042 Uiso 1 1 calc R U . . .
C34B C 1.32534(16) 0.27504(14) 0.66519(4) 0.0220(3) Uani 1 1 d . . . . .
H34B H 1.280376 0.186947 0.667712 0.026 Uiso 1 1 calc R U . . .
C36A C 0.94763(17) 0.96537(16) 0.19927(5) 0.0278(3) Uani 1 1 d . . . . .
H36A H 1.004524 0.999352 0.220991 0.033 Uiso 1 1 calc R U . . .
C35B C 1.42612(17) 0.31830(15) 0.69392(4) 0.0246(3) Uani 1 1 d . . . . .
H35B H 1.450333 0.259496 0.715814 0.030 Uiso 1 1 calc R U . . .
C37A C 0.97315(18) 1.01683(16) 0.15978(5) 0.0286(3) Uani 1 1 d . . . . .
H37A H 1.047380 1.086445 0.154448 0.034 Uiso 1 1 calc R U . . .
C36B C 1.49126(16) 0.44697(15) 0.69068(4) 0.0248(3) Uani 1 1 d . . . . .
H36B H 1.559596 0.476844 0.710397 0.030 Uiso 1 1 calc R U . . .
C38A C 0.89068(18) 0.96697(15) 0.12808(5) 0.0276(3) Uani 1 1 d . . . . .
H38A H 0.909632 1.001968 0.101023 0.033 Uiso 1 1 calc R U . . .
C37B C 1.45620(17) 0.53201(15) 0.65849(5) 0.0243(3) Uani 1 1 d . . . . .
H37B H 1.500231 0.620531 0.656252 0.029 Uiso 1 1 calc R U . . .
C41A C 0.52402(15) 0.89332(13) 0.43424(4) 0.0174(3) Uani 1 1 d . . . . .
O41A O 0.50908(12) 0.79573(10) 0.45679(3) 0.0250(2) Uani 1 1 d . . . . .
C38B C 1.35719(16) 0.48830(14) 0.62958(4) 0.0228(3) Uani 1 1 d . . . . .
H38B H 1.335112 0.546595 0.607373 0.027 Uiso 1 1 calc R U . . .
C42A C 0.31730(16) 0.81158(14) 0.39863(4) 0.0228(3) Uani 1 1 d . . . . .
H42A H 0.259504 0.793997 0.425215 0.027 Uiso 1 1 calc R U . . .
H42B H 0.367754 0.725664 0.389269 0.027 Uiso 1 1 calc R U . . .
O42A O 0.43205(11) 0.91731(10) 0.40363(3) 0.0218(2) Uani 1 1 d . . . . .
C41B C 1.02340(15) 0.39500(13) 0.93430(4) 0.0190(3) Uani 1 1 d . . . . .
O41B O 1.00971(12) 0.29735(10) 0.95682(3) 0.0273(2) Uani 1 1 d . . . . .
C43A C 0.21038(15) 0.85996(14) 0.36733(4) 0.0197(3) Uani 1 1 d . . . . .
C42B C 0.81260(17) 0.31699(15) 0.89898(5) 0.0267(3) Uani 1 1 d . . . . .
H42C H 0.746967 0.306153 0.924650 0.032 Uiso 1 1 calc R U . . .
H42D H 0.860464 0.227893 0.891813 0.032 Uiso 1 1 calc R U . . .
O42B O 0.93010(11) 0.42013(10) 0.90429(3) 0.0257(2) Uani 1 1 d . . . . .
C44A C 0.14283(16) 0.98828(14) 0.37053(4) 0.0226(3) Uani 1 1 d . . . . .
H44A H 0.164587 1.046378 0.392758 0.027 Uiso 1 1 calc R U . . .
C43B C 0.71928(16) 0.36643(14) 0.86468(4) 0.0227(3) Uani 1 1 d . . . . .
C45A C 0.04390(17) 1.03214(15) 0.34151(5) 0.0249(3) Uani 1 1 d . . . . .
H45A H 0.000075 1.120764 0.343638 0.030 Uiso 1 1 calc R U . . .
C44B C 0.60954(18) 0.46703(15) 0.87201(5) 0.0273(3) Uani 1 1 d . . . . .
H44B H 0.590796 0.502120 0.899032 0.033 Uiso 1 1 calc R U . . .
C46A C 0.00867(16) 0.94699(15) 0.30936(4) 0.0245(3) Uani 1 1 d . . . . .
H46A H -0.059925 0.976816 0.289678 0.029 Uiso 1 1 calc R U . . .
C45B C 0.52693(18) 0.51686(16) 0.84024(5) 0.0289(3) Uani 1 1 d . . . . .
H45B H 0.452502 0.586331 0.845530 0.035 Uiso 1 1 calc R U . . .
C47A C 0.07401(17) 0.81842(15) 0.30614(4) 0.0247(3) Uani 1 1 d . . . . .
H47A H 0.049982 0.759728 0.284257 0.030 Uiso 1 1 calc R U . . .
C46B C 0.55263(17) 0.46560(16) 0.80077(5) 0.0279(3) Uani 1 1 d . . . . .
H46B H 0.495808 0.499787 0.779029 0.033 Uiso 1 1 calc R U . . .
C48A C 0.17468(16) 0.77515(14) 0.33489(4) 0.0222(3) Uani 1 1 d . . . . .
H48A H 0.219619 0.687026 0.332437 0.027 Uiso 1 1 calc R U . . .
C48B C 0.74434(19) 0.31548(16) 0.82502(5) 0.0320(4) Uani 1 1 d . . . . .
H48B H 0.819099 0.246351 0.819634 0.038 Uiso 1 1 calc R U . . .
C47B C 0.6608(2) 0.36493(17) 0.79311(5) 0.0350(4) Uani 1 1 d . . . . .
H47B H 0.678293 0.329319 0.766108 0.042 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
C1A C2A 1.3954(19) . ?
C1A C6A 1.4104(19) . ?
C1A C31A 1.4956(19) . ?
C1B C2B 1.3952(19) . ?
C1B C6B 1.4141(19) . ?
C1B C31B 1.4970(18) . ?
C2A C3A 1.386(2) . ?
C2A H2A 0.9500 . ?
C2B C3B 1.385(2) . ?
C2B H2B 0.9500 . ?
C3A C4A 1.387(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.389(2) . ?
C4A H4A 0.9500 . ?
C3B C4B 1.390(2) . ?
C3B H3B 0.9500 . ?
C5A C6A 1.4050(19) . ?
C5A H5A 0.9500 . ?
C4B C5B 1.385(2) . ?
C4B H4B 0.9500 . ?
C6A C7A 1.4428(19) . ?
C5B C6B 1.4084(19) . ?
C5B H5B 0.9500 . ?
C7A C8A 1.2038(19) . ?
C6B C7B 1.4363(19) . ?
C8A C9A 1.4369(19) . ?
C7B C8B 1.2039(19) . ?
C9A C14A 1.3998(19) . ?
C9A C10A 1.4001(19) . ?
C8B C9B 1.4363(19) . ?
C10A C11A 1.3808(19) . ?
C10A H10A 0.9500 . ?
C9B C14B 1.4005(19) . ?
C9B C10B 1.4025(19) . ?
C11A C12A 1.4018(19) . ?
C11A H11A 0.9500 . ?
C10B C11B 1.3812(19) . ?
C10B H10B 0.9500 . ?
C12A C13A 1.3992(19) . ?
C12A C15A 1.4371(19) . ?
C11B C12B 1.3994(19) . ?
C11B H11B 0.9500 . ?
C13A C14A 1.386(2) . ?
C13A H13A 0.9500 . ?
C12B C13B 1.3979(19) . ?
C12B C15B 1.4396(19) . ?
C14A H14A 0.9500 . ?
C13B C14B 1.386(2) . ?
C13B H13B 0.9500 . ?
C15A C16A 1.2044(19) . ?
C14B H14B 0.9500 . ?
C16A C17A 1.4367(19) . ?
C15B C16B 1.2022(19) . ?
C17A C22A 1.4084(19) . ?
C17A C18A 1.4123(19) . ?
C16B C17B 1.4422(19) . ?
C18A C19A 1.3970(19) . ?
C18A C41A 1.4959(18) . ?
C17B C22B 1.4068(19) . ?
C17B C18B 1.4098(19) . ?
C19A C20A 1.387(2) . ?
C19A H19A 0.9500 . ?
C18B C19B 1.3955(19) . ?
C18B C41B 1.4955(19) . ?
C20A C21A 1.391(2) . ?
C20A H20A 0.9500 . ?
C19B C20B 1.386(2) . ?
C19B H19B 0.9500 . ?
C21A C22A 1.385(2) . ?
C21A H21A 0.9500 . ?
C20B C21B 1.386(2) . ?
C20B H20B 0.9500 . ?
C22A H22A 0.9500 . ?
C21B C22B 1.387(2) . ?
C21B H21B 0.9500 . ?
C31A O31A 1.2090(16) . ?
C31A O32A 1.3320(16) . ?
C22B H22B 0.9500 . ?
C32A O32A 1.4567(16) . ?
C32A C33A 1.503(2) . ?
C32A H32A 0.9900 . ?
C32A H32B 0.9900 . ?
C31B O31B 1.2093(16) . ?
C31B O32B 1.3380(16) . ?
C33A C38A 1.388(2) . ?
C33A C34A 1.389(2) . ?
C32B O32B 1.4577(16) . ?
C32B C33B 1.5034(19) . ?
C32B H32C 0.9900 . ?
C32B H32D 0.9900 . ?
C34A C35A 1.392(2) . ?
C34A H34A 0.9500 . ?
C33B C38B 1.392(2) . ?
C33B C34B 1.3922(19) . ?
C35A C36A 1.380(2) . ?
C35A H35A 0.9500 . ?
C34B C35B 1.390(2) . ?
C34B H34B 0.9500 . ?
C36A C37A 1.386(2) . ?
C36A H36A 0.9500 . ?
C35B C36B 1.385(2) . ?
C35B H35B 0.9500 . ?
C37A C38A 1.385(2) . ?
C37A H37A 0.9500 . ?
C36B C37B 1.387(2) . ?
C36B H36B 0.9500 . ?
C38A H38A 0.9500 . ?
C37B C38B 1.386(2) . ?
C37B H37B 0.9500 . ?
C41A O41A 1.2074(16) . ?
C41A O42A 1.3390(16) . ?
C38B H38B 0.9500 . ?
C42A O42A 1.4584(16) . ?
C42A C43A 1.5009(19) . ?
C42A H42A 0.9900 . ?
C42A H42B 0.9900 . ?
C41B O41B 1.2064(17) . ?
C41B O42B 1.3334(16) . ?
C43A C44A 1.390(2) . ?
C43A C48A 1.3954(19) . ?
C42B O42B 1.4590(17) . ?
C42B C43B 1.503(2) . ?
C42B H42C 0.9900 . ?
C42B H42D 0.9900 . ?
C44A C45A 1.387(2) . ?
C44A H44A 0.9500 . ?
C43B C44B 1.386(2) . ?
C43B C48B 1.390(2) . ?
C45A C46A 1.389(2) . ?
C45A H45A 0.9500 . ?
C44B C45B 1.386(2) . ?
C44B H44B 0.9500 . ?
C46A C47A 1.385(2) . ?
C46A H46A 0.9500 . ?
C45B C46B 1.386(2) . ?
C45B H45B 0.9500 . ?
C47A C48A 1.389(2) . ?
C47A H47A 0.9500 . ?
C46B C47B 1.378(2) . ?
C46B H46B 0.9500 . ?
C48A H48A 0.9500 . ?
C48B C47B 1.393(2) . ?
C48B H48B 0.9500 . ?
C47B H47B 0.9500 . ?

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
C2A C1A C6A 119.85(13) . . ?
C2A C1A C31A 115.72(12) . . ?
C6A C1A C31A 124.43(12) . . ?
C2B C1B C6B 119.61(12) . . ?
C2B C1B C31B 115.32(12) . . ?
C6B C1B C31B 125.05(12) . . ?
C3A C2A C1A 121.09(14) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C3B C2B C1B 121.52(13) . . ?
C3B C2B H2B 119.2 . . ?
C1B C2B H2B 119.2 . . ?
C2A C3A C4A 119.42(13) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
C3A C4A C5A 120.38(13) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C2B C3B C4B 119.23(13) . . ?
C2B C3B H3B 120.4 . . ?
C4B C3B H3B 120.4 . . ?
C4A C5A C6A 120.96(13) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A H5A 119.5 . . ?
C5B C4B C3B 120.30(13) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C5A C6A C1A 118.25(12) . . ?
C5A C6A C7A 117.65(12) . . ?
C1A C6A C7A 124.03(12) . . ?
C4B C5B C6B 121.34(13) . . ?
C4B C5B H5B 119.3 . . ?
C6B C5B H5B 119.3 . . ?
C8A C7A C6A 175.89(14) . . ?
C5B C6B C1B 117.97(12) . . ?
C5B C6B C7B 117.50(12) . . ?
C1B C6B C7B 124.45(12) . . ?
C7A C8A C9A 177.78(15) . . ?
C8B C7B C6B 174.55(14) . . ?
C14A C9A C10A 118.55(12) . . ?
C14A C9A C8A 121.59(12) . . ?
C10A C9A C8A 119.86(12) . . ?
C7B C8B C9B 177.28(14) . . ?
C11A C10A C9A 120.87(13) . . ?
C11A C10A H10A 119.6 . . ?
C9A C10A H10A 119.6 . . ?
C14B C9B C10B 118.65(12) . . ?
C14B C9B C8B 120.86(12) . . ?
C10B C9B C8B 120.48(12) . . ?
C10A C11A C12A 120.60(13) . . ?
C10A C11A H11A 119.7 . . ?
C12A C11A H11A 119.7 . . ?
C11B C10B C9B 120.40(13) . . ?
C11B C10B H10B 119.8 . . ?
C9B C10B H10B 119.8 . . ?
C13A C12A C11A 118.67(12) . . ?
C13A C12A C15A 120.87(13) . . ?
C11A C12A C15A 120.46(12) . . ?
C10B C11B C12B 121.03(13) . . ?
C10B C11B H11B 119.5 . . ?
C12B C11B H11B 119.5 . . ?
C14A C13A C12A 120.64(13) . . ?
C14A C13A H13A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C13B C12B C11B 118.63(12) . . ?
C13B C12B C15B 121.51(12) . . ?
C11B C12B C15B 119.85(12) . . ?
C13A C14A C9A 120.67(13) . . ?
C13A C14A H14A 119.7 . . ?
C9A C14A H14A 119.7 . . ?
C14B C13B C12B 120.55(13) . . ?
C14B C13B H13B 119.7 . . ?
C12B C13B H13B 119.7 . . ?
C16A C15A C12A 177.35(14) . . ?
C13B C14B C9B 120.73(13) . . ?
C13B C14B H14B 119.6 . . ?
C9B C14B H14B 119.6 . . ?
C15A C16A C17A 174.52(14) . . ?
C16B C15B C12B 177.76(15) . . ?
C22A C17A C18A 118.18(12) . . ?
C22A C17A C16A 117.52(12) . . ?
C18A C17A C16A 124.22(12) . . ?
C15B C16B C17B 175.80(14) . . ?
C19A C18A C17A 119.48(12) . . ?
C19A C18A C41A 115.31(12) . . ?
C17A C18A C41A 125.20(12) . . ?
C22B C17B C18B 118.23(12) . . ?
C22B C17B C16B 117.81(12) . . ?
C18B C17B C16B 123.88(12) . . ?
C20A C19A C18A 121.59(13) . . ?
C20A C19A H19A 119.2 . . ?
C18A C19A H19A 119.2 . . ?
C19B C18B C17B 119.68(13) . . ?
C19B C18B C41B 115.81(12) . . ?
C17B C18B C41B 124.51(12) . . ?
C19A C20A C21A 119.12(13) . . ?
C19A C20A H20A 120.4 . . ?
C21A C20A H20A 120.4 . . ?
C20B C19B C18B 121.29(14) . . ?
C20B C19B H19B 119.4 . . ?
C18B C19B H19B 119.4 . . ?
C22A C21A C20A 120.33(13) . . ?
C22A C21A H21A 119.8 . . ?
C20A C21A H21A 119.8 . . ?
C21B C20B C19B 119.27(13) . . ?
C21B C20B H20B 120.4 . . ?
C19B C20B H20B 120.4 . . ?
C21A C22A C17A 121.30(13) . . ?
C21A C22A H22A 119.4 . . ?
C17A C22A H22A 119.4 . . ?
C20B C21B C22B 120.47(13) . . ?
C20B C21B H21B 119.8 . . ?
C22B C21B H21B 119.8 . . ?
O31A C31A O32A 123.36(13) . . ?
O31A C31A C1A 123.62(13) . . ?
O32A C31A C1A 113.01(11) . . ?
C21B C22B C17B 121.01(13) . . ?
C21B C22B H22B 119.5 . . ?
C17B C22B H22B 119.5 . . ?
O32A C32A C33A 106.50(11) . . ?
O32A C32A H32A 110.4 . . ?
C33A C32A H32A 110.4 . . ?
O32A C32A H32B 110.4 . . ?
C33A C32A H32B 110.4 . . ?
H32A C32A H32B 108.6 . . ?
C31A O32A C32A 115.20(10) . . ?
O31B C31B O32B 123.09(12) . . ?
O31B C31B C1B 122.76(12) . . ?
O32B C31B C1B 114.15(11) . . ?
C38A C33A C34A 118.82(14) . . ?
C38A C33A C32A 120.10(14) . . ?
C34A C33A C32A 121.05(14) . . ?
O32B C32B C33B 108.23(11) . . ?
O32B C32B H32C 110.1 . . ?
C33B C32B H32C 110.1 . . ?
O32B C32B H32D 110.1 . . ?
C33B C32B H32D 110.1 . . ?
H32C C32B H32D 108.4 . . ?
C31B O32B C32B 113.83(10) . . ?
C33A C34A C35A 120.62(15) . . ?
C33A C34A H34A 119.7 . . ?
C35A C34A H34A 119.7 . . ?
C38B C33B C34B 118.82(13) . . ?
C38B C33B C32B 120.75(13) . . ?
C34B C33B C32B 120.42(13) . . ?
C36A C35A C34A 119.97(15) . . ?
C36A C35A H35A 120.0 . . ?
C34A C35A H35A 120.0 . . ?
C35B C34B C33B 120.56(13) . . ?
C35B C34B H34B 119.7 . . ?
C33B C34B H34B 119.7 . . ?
C35A C36A C37A 119.79(14) . . ?
C35A C36A H36A 120.1 . . ?
C37A C36A H36A 120.1 . . ?
C36B C35B C34B 120.11(13) . . ?
C36B C35B H35B 119.9 . . ?
C34B C35B H35B 119.9 . . ?
C38A C37A C36A 120.13(14) . . ?
C38A C37A H37A 119.9 . . ?
C36A C37A H37A 119.9 . . ?
C35B C36B C37B 119.66(13) . . ?
C35B C36B H36B 120.2 . . ?
C37B C36B H36B 120.2 . . ?
C37A C38A C33A 120.66(14) . . ?
C37A C38A H38A 119.7 . . ?
C33A C38A H38A 119.7 . . ?
C38B C37B C36B 120.23(14) . . ?
C38B C37B H37B 119.9 . . ?
C36B C37B H37B 119.9 . . ?
O41A C41A O42A 122.93(12) . . ?
O41A C41A C18A 122.82(12) . . ?
O42A C41A C18A 114.25(11) . . ?
C37B C38B C33B 120.61(13) . . ?
C37B C38B H38B 119.7 . . ?
C33B C38B H38B 119.7 . . ?
O42A C42A C43A 108.24(11) . . ?
O42A C42A H42A 110.0 . . ?
C43A C42A H42A 110.0 . . ?
O42A C42A H42B 110.0 . . ?
C43A C42A H42B 110.0 . . ?
H42A C42A H42B 108.4 . . ?
C41A O42A C42A 114.04(10) . . ?
O41B C41B O42B 123.28(13) . . ?
O41B C41B C18B 123.69(13) . . ?
O42B C41B C18B 113.01(11) . . ?
C44A C43A C48A 118.86(13) . . ?
C44A C43A C42A 120.88(13) . . ?
C48A C43A C42A 120.25(13) . . ?
O42B C42B C43B 106.47(11) . . ?
O42B C42B H42C 110.4 . . ?
C43B C42B H42C 110.4 . . ?
O42B C42B H42D 110.4 . . ?
C43B C42B H42D 110.4 . . ?
H42C C42B H42D 108.6 . . ?
C41B O42B C42B 115.23(11) . . ?
C45A C44A C43A 120.52(13) . . ?
C45A C44A H44A 119.7 . . ?
C43A C44A H44A 119.7 . . ?
C44B C43B C48B 118.96(13) . . ?
C44B C43B C42B 120.14(14) . . ?
C48B C43B C42B 120.87(14) . . ?
C44A C45A C46A 120.26(13) . . ?
C44A C45A H45A 119.9 . . ?
C46A C45A H45A 119.9 . . ?
C45B C44B C43B 120.54(14) . . ?
C45B C44B H44B 119.7 . . ?
C43B C44B H44B 119.7 . . ?
C47A C46A C45A 119.68(13) . . ?
C47A C46A H46A 120.2 . . ?
C45A C46A H46A 120.2 . . ?
C44B C45B C46B 120.16(14) . . ?
C44B C45B H45B 119.9 . . ?
C46B C45B H45B 119.9 . . ?
C46A C47A C48A 120.07(13) . . ?
C46A C47A H47A 120.0 . . ?
C48A C47A H47A 120.0 . . ?
C47B C46B C45B 119.88(14) . . ?
C47B C46B H46B 120.1 . . ?
C45B C46B H46B 120.1 . . ?
C47A C48A C43A 120.59(13) . . ?
C47A C48A H48A 119.7 . . ?
C43A C48A H48A 119.7 . . ?
C43B C48B C47B 120.55(14) . . ?
C43B C48B H48B 119.7 . . ?
C47B C48B H48B 119.7 . . ?
C46B C47B C48B 119.90(15) . . ?
C46B C47B H47B 120.1 . . ?
C48B C47B H47B 120.1 . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_WM01105_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1875128'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H16 F10 O4'
_chemical_formula_weight         726.51

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.8623(4)
_cell_length_b                   10.4103(6)
_cell_length_c                   19.6258(11)
_cell_angle_alpha                77.8230(10)
_cell_angle_beta                 80.4870(10)
_cell_angle_gamma                78.4090(10)
_cell_volume                     1525.47(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9147
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      40.27

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.143
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58188
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.070
_diffrn_reflns_theta_max         40.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             19157
_reflns_number_gt                12209
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0788P)²+0.3703P] 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_number_reflns         19157
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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 0.21461(14) 0.77954(8) 0.36011(5) 0.02710(19) Uani 1 1 d . . . . .
O1 O 1.68872(10) -0.11276(10) 0.07436(5) 0.02268(17) Uani 1 1 d . . . . .
C1' C 0.34685(12) 0.44251(9) 0.45428(5) 0.01303(15) Uani 1 1 d . . . . .
C1 C 1.21947(12) -0.10536(9) 0.07932(5) 0.01186(14) Uani 1 1 d . . . . .
O2' O 0.29218(11) 0.58907(7) 0.31667(4) 0.01745(14) Uani 1 1 d . . . . .
O2 O 1.46671(9) -0.06137(8) 0.15724(4) 0.01595(13) Uani 1 1 d . . . . .
C2' C 0.24902(12) 0.57212(9) 0.44011(5) 0.01287(15) Uani 1 1 d . . . . .
C2 C 1.40205(12) -0.14228(9) 0.06280(5) 0.01253(15) Uani 1 1 d . . . . .
C3' C 0.14290(13) 0.62745(10) 0.49490(6) 0.01701(17) Uani 1 1 d . . . . .
H3' H 0.0793 0.7157 0.4853 0.020 Uiso 1 1 calc R U . . .
C3 C 1.46790(13) -0.21815(11) 0.01034(5) 0.01691(17) Uani 1 1 d . . . . .
H3 H 1.5909 -0.2414 -0.0013 0.020 Uiso 1 1 calc R U . . .
C4' C 0.12926(15) 0.55536(12) 0.56297(6) 0.02007(19) Uani 1 1 d . . . . .
H4' H 0.0553 0.5934 0.5997 0.024 Uiso 1 1 calc R U . . .
C4 C 1.35627(14) -0.26007(12) -0.02510(6) 0.01940(19) Uani 1 1 d . . . . .
H4 H 1.4023 -0.3134 -0.0599 0.023 Uiso 1 1 calc R U . . .
C5' C 0.22464(15) 0.42691(12) 0.57717(6) 0.0208(2) Uani 1 1 d . . . . .
H5' H 0.2157 0.3771 0.6237 0.025 Uiso 1 1 calc R U . . .
C5 C 1.17596(14) -0.22300(11) -0.00914(5) 0.01758(17) Uani 1 1 d . . . . .
H5 H 1.0989 -0.2507 -0.0335 0.021 Uiso 1 1 calc R U . . .
C6' C 0.33273(14) 0.37124(11) 0.52362(5) 0.01770(18) Uani 1 1 d . . . . .
H6' H 0.3980 0.2838 0.5340 0.021 Uiso 1 1 calc R U . . .
C6 C 1.10811(12) -0.14614(10) 0.04193(5) 0.01429(16) Uani 1 1 d . . . . .
H6 H 0.9849 -0.1207 0.0518 0.017 Uiso 1 1 calc R U . . .
C14 C 0.93612(12) 0.10449(10) 0.22571(5) 0.01389(16) Uani 1 1 d . . . . .
C14' C 0.70324(12) 0.24629(10) 0.32004(5) 0.01378(15) Uani 1 1 d . . . . .
C13 C 1.04578(13) 0.03107(10) 0.17589(6) 0.01573(17) Uani 1 1 d . . . . .
C13' C 0.57760(13) 0.31623(10) 0.36675(5) 0.01545(16) Uani 1 1 d . . . . .
C12 C 1.13476(12) -0.02902(10) 0.13229(5) 0.01369(15) Uani 1 1 d . . . . .
C12' C 0.46734(13) 0.37900(10) 0.40350(5) 0.01417(16) Uani 1 1 d . . . . .
C15 C 0.83784(13) 0.22958(10) 0.20145(5) 0.01596(17) Uani 1 1 d . . . . .
H15 H 0.8501 0.2665 0.1527 0.019 Uiso 1 1 calc R U . . .
C15' C 0.72330(13) 0.29946(10) 0.24789(5) 0.01577(17) Uani 1 1 d . . . . .
H15' H 0.6579 0.3840 0.2308 0.019 Uiso 1 1 calc R U . . .
C16 C 0.91979(13) 0.05250(10) 0.29800(5) 0.01648(17) Uani 1 1 d . . . . .
H16 H 0.9873 -0.0311 0.3152 0.020 Uiso 1 1 calc R U . . .
C16' C 0.80488(13) 0.12301(10) 0.34472(5) 0.01641(17) Uani 1 1 d . . . . .
H16' H 0.7951 0.0875 0.3937 0.020 Uiso 1 1 calc R U . . .
C21 C 1.53487(12) -0.10456(10) 0.09723(5) 0.01335(15) Uani 1 1 d . . . . .
C21' C 0.25067(13) 0.65915(10) 0.36938(5) 0.01530(16) Uani 1 1 d . . . . .
C22 C 1.58604(13) -0.01365(10) 0.19106(5) 0.01547(16) Uani 1 1 d . . . . .
H22A H 1.6382 0.0589 0.1585 0.019 Uiso 1 1 calc R U . . .
H22B H 1.6815 -0.0869 0.2061 0.019 Uiso 1 1 calc R U . . .
C22' C 0.30554(14) 0.66536(11) 0.24581(5) 0.01811(18) Uani 1 1 d . . . . .
H22C H 0.4289 0.6526 0.2237 0.022 Uiso 1 1 calc R U . . .
H22D H 0.2658 0.7615 0.2468 0.022 Uiso 1 1 calc R U . . .
C23 C 1.47821(12) 0.03677(10) 0.25340(5) 0.01415(16) Uani 1 1 d . . . . .
C23' C 0.19372(13) 0.61911(10) 0.20405(5) 0.01467(16) Uani 1 1 d . . . . .
C24 C 1.48520(14) -0.03406(10) 0.32125(6) 0.01791(18) Uani 1 1 d . . . . .
C24' C 0.01243(13) 0.65263(10) 0.21522(6) 0.01705(17) Uani 1 1 d . . . . .
F24 F 1.59304(11) -0.15153(8) 0.33273(4) 0.02881(17) Uani 1 1 d . . . . .
F24' F -0.06181(9) 0.72647(7) 0.26423(4) 0.02446(15) Uani 1 1 d . . . . .
C25 C 1.38333(15) 0.01210(11) 0.37877(6) 0.02026(19) Uani 1 1 d . . . . .
C25' C -0.09497(14) 0.61336(11) 0.17758(6) 0.0210(2) Uani 1 1 d . . . . .
F25 F 1.39420(12) -0.05832(9) 0.44371(4) 0.0341(2) Uani 1 1 d . . . . .
F25' F -0.26922(10) 0.64601(9) 0.19080(5) 0.03302(19) Uani 1 1 d . . . . .
C26 C 1.26946(14) 0.13220(11) 0.36865(6) 0.01835(18) Uani 1 1 d . . . . .
F26 F 1.16976(11) 0.17692(8) 0.42364(4) 0.02743(16) Uani 1 1 d . . . . .
F26' F -0.12392(13) 0.50512(9) 0.08721(5) 0.0366(2) Uani 1 1 d . . . . .
C26' C -0.02116(17) 0.54039(12) 0.12544(7) 0.0233(2) Uani 1 1 d . . . . .
C27 C 1.25861(13) 0.20557(10) 0.30149(6) 0.01712(17) Uani 1 1 d . . . . .
F27 F 1.14776(10) 0.32176(7) 0.29165(4) 0.02628(16) Uani 1 1 d . . . . .
F27' F 0.23019(13) 0.43504(8) 0.06234(4) 0.0347(2) Uani 1 1 d . . . . .
C27' C 0.15879(17) 0.50497(11) 0.11291(6) 0.0218(2) Uani 1 1 d . . . . .
C28 C 1.36242(13) 0.15746(10) 0.24515(5) 0.01528(16) Uani 1 1 d . . . . .
F28 F 1.35004(10) 0.23032(7) 0.18053(4) 0.02399(15) Uani 1 1 d . . . . .
F28' F 0.43750(9) 0.50847(8) 0.13834(4) 0.02564(16) Uani 1 1 d . . . . .
C28' C 0.26299(14) 0.54436(10) 0.15223(5) 0.01747(18) 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
O1' C21' 1.2093(13) . ?
O1 C21 1.2112(12) . ?
C1' C6' 1.4043(14) . ?
C1' C2' 1.4089(13) . ?
C1' C12' 1.4290(12) . ?
C1 C6 1.4066(14) . ?
C1 C2 1.4109(12) . ?
C1 C12 1.4363(12) . ?
O2' C21' 1.3490(12) . ?
O2' C22' 1.4474(13) . ?
O2 C21 1.3396(12) . ?
O2 C22 1.4490(12) . ?
C2' C3' 1.3985(13) . ?
C2' C21' 1.4888(14) . ?
C2 C3 1.3981(13) . ?
C2 C21 1.4871(14) . ?
C3' C4' 1.3862(16) . ?
C3' H3' 0.9500 . ?
C3 C4 1.3886(16) . ?
C3 H3 0.9500 . ?
C4' C5' 1.3917(16) . ?
C4' H4' 0.9500 . ?
C4 C5 1.3933(15) . ?
C4 H4 0.9500 . ?
C5' C6' 1.3880(14) . ?
C5' H5' 0.9500 . ?
C5 C6 1.3854(14) . ?
C5 H5 0.9500 . ?
C6' H6' 0.9500 . ?
C6 H6 0.9500 . ?
C14 C16 1.4022(14) . ?
C14 C15 1.4054(14) . ?
C14 C13 1.4336(13) . ?
C14' C15' 1.4024(14) . ?
C14' C16' 1.4049(14) . ?
C14' C13' 1.4282(13) . ?
C13 C12 1.2104(13) . ?
C13' C12' 1.2096(13) . ?
C15 C15' 1.3842(13) . ?
C15 H15 0.9500 . ?
C15' H15' 0.9500 . ?
C16 C16' 1.3925(13) . ?
C16 H16 0.9500 . ?
C16' H16' 0.9500 . ?
C22 C23 1.4968(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22' C23' 1.5004(15) . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?
C23 C24 1.3834(15) . ?
C23 C28 1.3917(13) . ?
C23' C28' 1.3845(14) . ?
C23' C24' 1.3895(14) . ?
C24 F24 1.3399(12) . ?
C24 C25 1.3863(14) . ?
C24' F24' 1.3427(12) . ?
C24' C25' 1.3777(17) . ?
C25 F25 1.3364(13) . ?
C25 C26 1.3814(15) . ?
C25' F25' 1.3388(13) . ?
C25' C26' 1.3840(18) . ?
C26 F26 1.3348(12) . ?
C26 C27 1.3835(16) . ?
F26' C26' 1.3366(14) . ?
C26' C27' 1.3827(18) . ?
C27 F27 1.3392(12) . ?
C27 C28 1.3824(14) . ?
F27' C27' 1.3366(13) . ?
C27' C28' 1.3829(17) . ?
C28 F28 1.3410(12) . ?
F28' C28' 1.3452(12) . ?

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
C6' C1' C2' 118.59(8) . . ?
C6' C1' C12' 116.64(8) . . ?
C2' C1' C12' 124.71(9) . . ?
C6 C1 C2 118.57(8) . . ?
C6 C1 C12 116.01(8) . . ?
C2 C1 C12 125.41(9) . . ?
C21' O2' C22' 116.72(8) . . ?
C21 O2 C22 115.76(7) . . ?
C3' C2' C1' 119.78(9) . . ?
C3' C2' C21' 115.66(8) . . ?
C1' C2' C21' 124.55(8) . . ?
C3 C2 C1 119.73(9) . . ?
C3 C2 C21 115.89(8) . . ?
C1 C2 C21 124.37(8) . . ?
C4' C3' C2' 120.91(9) . . ?
C4' C3' H3' 119.5 . . ?
C2' C3' H3' 119.5 . . ?
C4 C3 C2 121.03(9) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3' C4' C5' 119.53(9) . . ?
C3' C4' H4' 120.2 . . ?
C5' C4' H4' 120.2 . . ?
C3 C4 C5 119.28(9) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6' C5' C4' 120.32(10) . . ?
C6' C5' H5' 119.8 . . ?
C4' C5' H5' 119.8 . . ?
C6 C5 C4 120.57(10) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5' C6' C1' 120.86(9) . . ?
C5' C6' H6' 119.6 . . ?
C1' C6' H6' 119.6 . . ?
C5 C6 C1 120.78(9) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C16 C14 C15 119.07(8) . . ?
C16 C14 C13 121.57(9) . . ?
C15 C14 C13 119.32(9) . . ?
C15' C14' C16' 119.05(8) . . ?
C15' C14' C13' 119.72(9) . . ?
C16' C14' C13' 121.21(9) . . ?
C12 C13 C14 177.93(11) . . ?
C12' C13' C14' 176.79(11) . . ?
C13 C12 C1 172.47(10) . . ?
C13' C12' C1' 172.76(11) . . ?
C15' C15 C14 120.67(9) . . ?
C15' C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C15' C14' 120.43(9) . . ?
C15 C15' H15' 119.8 . . ?
C14' C15' H15' 119.8 . . ?
C16' C16 C14 120.21(9) . . ?
C16' C16 H16 119.9 . . ?
C14 C16 H16 119.9 . . ?
C16 C16' C14' 120.52(9) . . ?
C16 C16' H16' 119.7 . . ?
C14' C16' H16' 119.7 . . ?
O1 C21 O2 123.07(9) . . ?
O1 C21 C2 124.19(9) . . ?
O2 C21 C2 112.74(8) . . ?
O1' C21' O2' 123.56(10) . . ?
O1' C21' C2' 123.69(9) . . ?
O2' C21' C2' 112.72(8) . . ?
O2 C22 C23 105.79(8) . . ?
O2 C22 H22A 110.6 . . ?
C23 C22 H22A 110.6 . . ?
O2 C22 H22B 110.6 . . ?
C23 C22 H22B 110.6 . . ?
H22A C22 H22B 108.7 . . ?
O2' C22' C23' 108.98(9) . . ?
O2' C22' H22C 109.9 . . ?
C23' C22' H22C 109.9 . . ?
O2' C22' H22D 109.9 . . ?
C23' C22' H22D 109.9 . . ?
H22C C22' H22D 108.3 . . ?
C24 C23 C28 116.77(9) . . ?
C24 C23 C22 122.38(9) . . ?
C28 C23 C22 120.84(9) . . ?
C28' C23' C24' 116.60(10) . . ?
C28' C23' C22' 122.82(9) . . ?
C24' C23' C22' 120.57(9) . . ?
F24 C24 C23 119.73(9) . . ?
F24 C24 C25 118.07(9) . . ?
C23 C24 C25 122.21(9) . . ?
F24' C24' C25' 118.41(9) . . ?
F24' C24' C23' 119.15(10) . . ?
C25' C24' C23' 122.45(10) . . ?
F25 C25 C26 119.80(9) . . ?
F25 C25 C24 120.71(9) . . ?
C26 C25 C24 119.49(10) . . ?
F25' C25' C24' 120.52(11) . . ?
F25' C25' C26' 120.07(11) . . ?
C24' C25' C26' 119.40(10) . . ?
F26 C26 C25 119.93(10) . . ?
F26 C26 C27 120.17(9) . . ?
C25 C26 C27 119.90(9) . . ?
F26' C26' C27' 120.32(12) . . ?
F26' C26' C25' 119.92(11) . . ?
C27' C26' C25' 119.76(11) . . ?
F27 C27 C28 120.73(10) . . ?
F27 C27 C26 119.90(9) . . ?
C28 C27 C26 119.37(9) . . ?
F27' C27' C26' 119.80(11) . . ?
F27' C27' C28' 120.75(11) . . ?
C26' C27' C28' 119.44(10) . . ?
F28 C28 C27 118.38(9) . . ?
F28 C28 C23 119.36(9) . . ?
C27 C28 C23 122.26(9) . . ?
F28' C28' C27' 117.74(9) . . ?
F28' C28' C23' 119.94(10) . . ?
C27' C28' C23' 122.32(10) . . ?

_refine_diff_density_max         0.916
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.103



####################################################################### 
# 
# 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_X18062
_database_code_depnum_ccdc_archive 'CCDC 1875131'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/2
_shelx_SHELXL_version_number     2017/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H30 O4, 0.84(C H Cl3)'
_chemical_formula_sum            'C46.84 H30.84 Cl2.52 O4'
_chemical_formula_weight         746.97

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.1455(7)
_cell_length_b                   9.8705(8)
_cell_length_c                   23.767(2)
_cell_angle_alpha                80.595(2)
_cell_angle_beta                 84.255(2)
_cell_angle_gamma                88.725(3)
_cell_volume                     1875.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9503
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      29.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             773
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7036
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            59772
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.132
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11450
_reflns_number_gt                7572
_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       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/2 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 The asymmetric unit contains ca. 85% of a chloroform molecule that 
 is disordered over three positions.  Two of those positions are 
 near crystalographic inversion centers, however their occupancies
 are 39% and 31%, respectively, so there is no clash.

 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.8968P] 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_number_reflns         11450
_refine_ls_number_parameters     562
_refine_ls_number_restraints     291
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1523
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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 0.35267(14) 1.01139(12) 0.15443(5) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.44411(15) 1.16802(12) 0.07923(5) 0.0288(3) Uani 1 1 d . . . . .
O3 O 0.09983(15) 0.64442(13) 0.86463(5) 0.0261(3) Uani 1 1 d . . . . .
O4 O -0.00174(16) 0.71156(13) 0.94663(5) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.4599(2) 1.05827(17) 0.10932(7) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.59837(19) 0.96112(16) 0.09903(7) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.6844(2) 0.98553(17) 0.04454(7) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.654778 1.062357 0.017795 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8115(2) 0.90058(19) 0.02868(7) 0.0264(4) Uani 1 1 d . . . . .
H4 H 0.866641 0.917589 -0.008927 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8586(2) 0.78967(18) 0.06813(7) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.946387 0.731067 0.057554 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7770(2) 0.76501(17) 0.12285(7) 0.0224(3) Uani 1 1 d . . . . .
H6 H 0.810848 0.689938 0.149657 0.027 Uiso 1 1 calc R U . . .
C7 C 0.64549(19) 0.84880(16) 0.13940(6) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.57114(19) 0.81630(16) 0.19712(7) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.5215(2) 0.78236(16) 0.24656(7) 0.0207(3) Uani 1 1 d . . . . .
C10 C 0.4596(2) 0.74937(16) 0.30574(6) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.3262(2) 0.82332(17) 0.32774(7) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.277017 0.895448 0.303337 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2657(2) 0.79192(17) 0.38477(7) 0.0226(3) Uani 1 1 d . . . . .
H12 H 0.175151 0.842642 0.399300 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3369(2) 0.68584(16) 0.42126(7) 0.0206(3) Uani 1 1 d . . . . .
C14 C 0.4699(2) 0.61172(18) 0.39932(7) 0.0260(4) Uani 1 1 d . . . . .
H14 H 0.518979 0.539510 0.423722 0.031 Uiso 1 1 calc R U . . .
C15 C 0.5303(2) 0.64310(18) 0.34228(7) 0.0254(3) Uani 1 1 d . . . . .
H15 H 0.620592 0.592124 0.327740 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2722(2) 0.65369(17) 0.48041(7) 0.0226(3) Uani 1 1 d . . . . .
C17 C 0.2154(2) 0.62888(17) 0.52941(7) 0.0225(3) Uani 1 1 d . . . . .
C18 C 0.1487(2) 0.59911(16) 0.58844(7) 0.0208(3) Uani 1 1 d . . . . .
C19 C 0.0144(2) 0.51131(19) 0.60494(7) 0.0270(4) Uani 1 1 d . . . . .
H19 H -0.034413 0.471298 0.576940 0.032 Uiso 1 1 calc R U . . .
C20 C -0.0483(2) 0.48219(18) 0.66195(7) 0.0267(4) Uani 1 1 d . . . . .
H20 H -0.139719 0.422252 0.672759 0.032 Uiso 1 1 calc R U . . .
C21 C 0.02210(19) 0.54037(16) 0.70379(7) 0.0196(3) Uani 1 1 d . . . . .
C22 C 0.1565(2) 0.62858(16) 0.68709(7) 0.0209(3) Uani 1 1 d . . . . .
H22 H 0.205388 0.668583 0.715066 0.025 Uiso 1 1 calc R U . . .
C23 C 0.2187(2) 0.65801(17) 0.63012(7) 0.0220(3) Uani 1 1 d . . . . .
H23 H 0.309566 0.718572 0.619217 0.026 Uiso 1 1 calc R U . . .
C24 C -0.04083(19) 0.51017(16) 0.76293(7) 0.0208(3) Uani 1 1 d . . . . .
C25 C -0.09215(19) 0.49000(16) 0.81265(7) 0.0193(3) Uani 1 1 d . . . . .
C26 C -0.16961(19) 0.46007(16) 0.87027(7) 0.0194(3) Uani 1 1 d . . . . .
C27 C -0.2923(2) 0.35868(17) 0.88136(7) 0.0226(3) Uani 1 1 d . . . . .
H27 H -0.316560 0.311046 0.851569 0.027 Uiso 1 1 calc R U . . .
C28 C -0.3784(2) 0.32713(18) 0.93509(7) 0.0252(3) Uani 1 1 d . . . . .
H28 H -0.460052 0.257587 0.941875 0.030 Uiso 1 1 calc R U . . .
C29 C -0.3462(2) 0.39621(18) 0.97889(7) 0.0257(3) Uani 1 1 d . . . . .
H29 H -0.405698 0.374664 1.015643 0.031 Uiso 1 1 calc R U . . .
C30 C -0.2263(2) 0.49716(18) 0.96874(7) 0.0238(3) Uani 1 1 d . . . . .
H30 H -0.205209 0.545102 0.998804 0.029 Uiso 1 1 calc R U . . .
C31 C -0.13599(19) 0.52982(16) 0.91539(7) 0.0198(3) Uani 1 1 d . . . . .
C32 C -0.0085(2) 0.63755(17) 0.91123(7) 0.0207(3) Uani 1 1 d . . . . .
C33 C 0.2166(2) 1.10475(18) 0.16521(8) 0.0269(4) Uani 1 1 d . . . . .
H33A H 0.155827 1.127863 0.130811 0.032 Uiso 1 1 calc R U . . .
H33B H 0.258777 1.190801 0.174611 0.032 Uiso 1 1 calc R U . . .
C34 C 0.10475(19) 1.03360(17) 0.21461(7) 0.0223(3) Uani 1 1 d . . . . .
C35 C 0.0634(2) 1.09571(18) 0.26259(7) 0.0254(3) Uani 1 1 d . . . . .
H35 H 0.105911 1.183808 0.264043 0.030 Uiso 1 1 calc R U . . .
C36 C -0.0402(2) 1.02911(19) 0.30864(8) 0.0283(4) Uani 1 1 d . . . . .
H36 H -0.068410 1.072062 0.341299 0.034 Uiso 1 1 calc R U . . .
C37 C -0.1018(2) 0.90068(19) 0.30681(8) 0.0296(4) Uani 1 1 d . . . . .
H37 H -0.171107 0.854814 0.338403 0.035 Uiso 1 1 calc R U . . .
C38 C -0.0624(2) 0.83902(18) 0.25882(8) 0.0285(4) Uani 1 1 d . . . . .
H38 H -0.105874 0.751277 0.257344 0.034 Uiso 1 1 calc R U . . .
C39 C 0.0400(2) 0.90489(18) 0.21304(7) 0.0250(3) Uani 1 1 d . . . . .
H39 H 0.066407 0.862047 0.180247 0.030 Uiso 1 1 calc R U . . .
C40 C 0.2282(2) 0.74699(19) 0.86056(7) 0.0266(4) Uani 1 1 d . . . . .
H40A H 0.284757 0.733514 0.896049 0.032 Uiso 1 1 calc R U . . .
H40B H 0.179379 0.840429 0.855260 0.032 Uiso 1 1 calc R U . . .
C41 C 0.3482(2) 0.73001(17) 0.81013(7) 0.0227(3) Uani 1 1 d . . . . .
C42 C 0.4259(2) 0.60420(18) 0.80681(8) 0.0277(4) Uani 1 1 d . . . . .
H42 H 0.403649 0.528909 0.836885 0.033 Uiso 1 1 calc R U . . .
C43 C 0.5355(2) 0.5882(2) 0.76000(9) 0.0322(4) Uani 1 1 d . . . . .
H43 H 0.587577 0.501884 0.757855 0.039 Uiso 1 1 calc R U . . .
C44 C 0.5694(2) 0.6983(2) 0.71606(8) 0.0332(4) Uani 1 1 d . . . . .
H44 H 0.643953 0.687080 0.683748 0.040 Uiso 1 1 calc R U . . .
C45 C 0.4948(2) 0.8237(2) 0.71944(8) 0.0313(4) Uani 1 1 d . . . . .
H45 H 0.519317 0.899276 0.689700 0.038 Uiso 1 1 calc R U . . .
C46 C 0.3837(2) 0.83984(17) 0.76626(7) 0.0250(3) Uani 1 1 d . . . . .
H46 H 0.331903 0.926337 0.768270 0.030 Uiso 1 1 calc R U . . .
C1S C 0.1323(8) 1.1474(5) 0.4864(2) 0.0454(14) Uani 0.393(2) 1 d D U P A -1
H1S H 0.015080 1.178035 0.483757 0.055 Uiso 0.393(2) 1 calc R U P A -1
Cl1 Cl 0.2116(6) 1.2573(5) 0.5205(3) 0.0702(11) Uani 0.393(2) 1 d D U P A -1
Cl2 Cl 0.1188(3) 0.98047(16) 0.52340(7) 0.0645(6) Uani 0.393(2) 1 d D U P A -1
Cl3 Cl 0.2120(4) 1.14995(19) 0.41648(8) 0.0682(7) Uani 0.393(2) 1 d D U P A -1
C1T C 0.3896(15) 1.1350(8) 0.5032(3) 0.062(2) Uani 0.308(3) 1 d D U P B -2
H1T H 0.504447 1.163548 0.507053 0.075 Uiso 0.308(3) 1 calc R U P B -2
Cl1A Cl 0.2857(6) 1.2815(3) 0.4911(2) 0.0896(13) Uani 0.308(3) 1 d D U P B -2
Cl2A Cl 0.3385(6) 1.0241(4) 0.56318(13) 0.0865(13) Uani 0.308(3) 1 d D U P B -2
Cl3A Cl 0.4096(4) 1.0519(4) 0.44286(11) 0.0809(13) Uani 0.308(3) 1 d D U P B -2
C1U C 0.375(3) 1.1323(16) 0.5007(6) 0.075(3) Uani 0.140(3) 1 d D U P C 3
H1U H 0.495084 1.141617 0.505090 0.089 Uiso 0.140(3) 1 calc R U P C 3
Cl1B Cl 0.2563(18) 1.2499(13) 0.5281(6) 0.076(3) Uani 0.140(3) 1 d D U P C 3
Cl2B Cl 0.2898(13) 0.9865(8) 0.5392(5) 0.102(3) Uani 0.140(3) 1 d D U P C 3
Cl3B Cl 0.3322(14) 1.1516(11) 0.4305(3) 0.092(3) Uani 0.140(3) 1 d D U P C 3


_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 1.3399(19) . ?
O1 C33 1.456(2) . ?
O2 C1 1.2085(19) . ?
O3 C32 1.3387(19) . ?
O3 C40 1.4567(19) . ?
O4 C32 1.2069(19) . ?
C1 C2 1.491(2) . ?
C2 C3 1.397(2) . ?
C2 C7 1.416(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.403(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.432(2) . ?
C8 C9 1.199(2) . ?
C9 C10 1.433(2) . ?
C10 C15 1.401(2) . ?
C10 C11 1.401(2) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(2) . ?
C13 C16 1.438(2) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.198(2) . ?
C17 C18 1.438(2) . ?
C18 C19 1.396(2) . ?
C18 C23 1.400(2) . ?
C19 C20 1.385(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.401(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.399(2) . ?
C21 C24 1.433(2) . ?
C22 C23 1.384(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.200(2) . ?
C25 C26 1.436(2) . ?
C26 C27 1.405(2) . ?
C26 C31 1.417(2) . ?
C27 C28 1.385(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.394(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.488(2) . ?
C33 C34 1.499(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.390(2) . ?
C34 C39 1.394(2) . ?
C35 C36 1.395(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.383(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.385(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.383(2) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.498(2) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C46 1.389(2) . ?
C41 C42 1.392(2) . ?
C42 C43 1.382(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.390(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.377(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.390(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C1S Cl1 1.634(7) . ?
C1S Cl3 1.719(5) . ?
C1S Cl2 1.737(5) . ?
C1S H1S 1.0000 . ?
C1T Cl1A 1.658(9) . ?
C1T Cl2A 1.672(8) . ?
C1T Cl3A 1.757(8) . ?
C1T H1T 1.0000 . ?
C1U Cl1B 1.668(15) . ?
C1U Cl2B 1.698(14) . ?
C1U Cl3B 1.718(14) . ?
C1U H1U 1.0000 . ?

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 C33 114.58(12) . . ?
C32 O3 C40 114.57(13) . . ?
O2 C1 O1 123.03(15) . . ?
O2 C1 C2 123.24(15) . . ?
O1 C1 C2 113.71(13) . . ?
C3 C2 C7 119.24(15) . . ?
C3 C2 C1 115.51(14) . . ?
C7 C2 C1 125.25(14) . . ?
C4 C3 C2 121.49(15) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.62(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.89(16) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.26(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 118.47(14) . . ?
C6 C7 C8 117.04(14) . . ?
C2 C7 C8 124.47(14) . . ?
C9 C8 C7 174.08(17) . . ?
C8 C9 C10 176.90(17) . . ?
C15 C10 C11 119.06(14) . . ?
C15 C10 C9 120.88(15) . . ?
C11 C10 C9 120.06(14) . . ?
C12 C11 C10 120.38(15) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.45(15) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.23(14) . . ?
C14 C13 C16 120.85(15) . . ?
C12 C13 C16 119.91(15) . . ?
C15 C14 C13 120.29(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.59(15) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C13 178.51(18) . . ?
C16 C17 C18 179.43(18) . . ?
C19 C18 C23 119.22(14) . . ?
C19 C18 C17 120.68(15) . . ?
C23 C18 C17 120.10(15) . . ?
C20 C19 C18 120.35(15) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.57(15) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 118.95(14) . . ?
C22 C21 C24 120.00(14) . . ?
C20 C21 C24 121.05(14) . . ?
C23 C22 C21 120.49(15) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 120.43(15) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
C25 C24 C21 177.46(17) . . ?
C24 C25 C26 173.72(16) . . ?
C27 C26 C31 118.40(14) . . ?
C27 C26 C25 117.04(14) . . ?
C31 C26 C25 124.50(14) . . ?
C28 C27 C26 121.01(15) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C29 C28 C27 120.43(16) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 119.47(15) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C29 C30 C31 121.43(16) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C30 C31 C26 119.25(15) . . ?
C30 C31 C32 115.49(14) . . ?
C26 C31 C32 125.25(14) . . ?
O4 C32 O3 122.74(15) . . ?
O4 C32 C31 123.47(15) . . ?
O3 C32 C31 113.79(13) . . ?
O1 C33 C34 107.50(13) . . ?
O1 C33 H33A 110.2 . . ?
C34 C33 H33A 110.2 . . ?
O1 C33 H33B 110.2 . . ?
C34 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
C35 C34 C39 119.07(16) . . ?
C35 C34 C33 120.30(16) . . ?
C39 C34 C33 120.63(16) . . ?
C34 C35 C36 120.22(16) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C37 C36 C35 120.10(17) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 119.88(17) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C39 C38 C37 120.17(17) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C38 C39 C34 120.55(16) . . ?
C38 C39 H39 119.7 . . ?
C34 C39 H39 119.7 . . ?
O3 C40 C41 107.49(13) . . ?
O3 C40 H40A 110.2 . . ?
C41 C40 H40A 110.2 . . ?
O3 C40 H40B 110.2 . . ?
C41 C40 H40B 110.2 . . ?
H40A C40 H40B 108.5 . . ?
C46 C41 C42 119.24(16) . . ?
C46 C41 C40 120.39(16) . . ?
C42 C41 C40 120.37(16) . . ?
C43 C42 C41 120.35(17) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C42 C43 C44 120.06(18) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C45 C44 C43 119.92(18) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.16(17) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C41 C46 C45 120.25(17) . . ?
C41 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
Cl1 C1S Cl3 115.9(4) . . ?
Cl1 C1S Cl2 114.7(4) . . ?
Cl3 C1S Cl2 111.0(3) . . ?
Cl1 C1S H1S 104.6 . . ?
Cl3 C1S H1S 104.6 . . ?
Cl2 C1S H1S 104.6 . . ?
Cl1A C1T Cl2A 119.2(6) . . ?
Cl1A C1T Cl3A 111.7(5) . . ?
Cl2A C1T Cl3A 111.2(5) . . ?
Cl1A C1T H1T 104.4 . . ?
Cl2A C1T H1T 104.4 . . ?
Cl3A C1T H1T 104.4 . . ?
Cl1B C1U Cl2B 100.2(11) . . ?
Cl1B C1U Cl3B 104.1(12) . . ?
Cl2B C1U Cl3B 111.0(12) . . ?
Cl1B C1U H1U 113.5 . . ?
Cl2B C1U H1U 113.5 . . ?
Cl3B C1U H1U 113.5 . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_WM0210_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1875132'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 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         ?
_chemical_formula_sum            'C48 H28 F10 O4'
_chemical_formula_weight         858.70

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   12.0511(11)
_cell_length_b                   12.6535(11)
_cell_length_c                   14.0972(12)
_cell_angle_alpha                68.452(2)
_cell_angle_beta                 76.554(2)
_cell_angle_gamma                74.515(2)
_cell_volume                     1905.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      36.48

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7186
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61842
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.571
_diffrn_reflns_theta_max         36.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             18728
_reflns_number_gt                12962
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0791P)²+0.3143P] 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_number_reflns         18728
_refine_ls_number_parameters     563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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 0.23587(8) 1.31980(8) 0.19321(7) 0.01322(15) Uani 1 1 d . . . . .
C1' C 0.10023(8) 0.08410(7) 0.83441(7) 0.01306(15) Uani 1 1 d . . . . .
O1 O 0.53444(7) 1.32543(8) 0.06609(7) 0.02826(19) Uani 1 1 d . . . . .
O1' O 0.28541(8) -0.03232(7) 1.03816(7) 0.02539(17) Uani 1 1 d . . . . .
C2 C 0.33680(8) 1.36524(8) 0.14232(7) 0.01391(15) Uani 1 1 d . . . . .
O2 O 0.47120(7) 1.19325(6) 0.21065(6) 0.01948(14) Uani 1 1 d . . . . .
O2' O 0.24749(7) 0.14805(6) 0.92772(6) 0.01889(14) Uani 1 1 d . . . . .
C2' C 0.15597(8) 0.00789(7) 0.91918(7) 0.01294(15) Uani 1 1 d . . . . .
C3' C 0.13524(9) -0.10507(8) 0.96531(8) 0.01686(17) Uani 1 1 d . . . . .
H3' H 0.172734 -0.156125 1.022504 0.020 Uiso 1 1 calc R U . . .
C3 C 0.32733(10) 1.48440(8) 0.09321(8) 0.01804(18) Uani 1 1 d . . . . .
H3 H 0.395429 1.514493 0.058198 0.022 Uiso 1 1 calc R U . . .
C4' C 0.06123(10) -0.14418(8) 0.92945(8) 0.01873(18) Uani 1 1 d . . . . .
H4' H 0.048561 -0.221264 0.961443 0.022 Uiso 1 1 calc R U . . .
C4 C 0.22021(10) 1.55960(9) 0.09467(8) 0.02107(19) Uani 1 1 d . . . . .
H4 H 0.215205 1.640722 0.061798 0.025 Uiso 1 1 calc R U . . .
C5 C 0.12032(10) 1.51603(9) 0.14430(9) 0.02108(19) Uani 1 1 d . . . . .
H5 H 0.046643 1.567263 0.145475 0.025 Uiso 1 1 calc R U . . .
C5' C 0.00589(9) -0.06931(9) 0.84624(8) 0.01791(17) Uani 1 1 d . . . . .
H5' H -0.045505 -0.095032 0.821512 0.021 Uiso 1 1 calc R U . . .
C6' C 0.02533(9) 0.04287(8) 0.79908(8) 0.01690(17) Uani 1 1 d . . . . .
H6' H -0.012584 0.092900 0.741842 0.020 Uiso 1 1 calc R U . . .
C6 C 0.12813(9) 1.39716(9) 0.19237(8) 0.01810(17) Uani 1 1 d . . . . .
H6 H 0.059133 1.367889 0.225251 0.022 Uiso 1 1 calc R U . . .
C11 C 0.23527(8) 1.19860(8) 0.24364(7) 0.01428(16) Uani 1 1 d . . . . .
C11' C 0.11289(9) 0.20179(8) 0.78046(7) 0.01562(16) Uani 1 1 d . . . . .
C12 C 0.22430(8) 1.09936(8) 0.28860(7) 0.01499(16) Uani 1 1 d . . . . .
C12' C 0.11554(9) 0.30114(8) 0.72731(8) 0.01604(16) Uani 1 1 d . . . . .
C13 C 0.20745(8) 0.98401(8) 0.34908(7) 0.01358(15) Uani 1 1 d . . . . .
C13' C 0.12582(9) 0.41743(8) 0.66448(7) 0.01439(16) Uani 1 1 d . . . . .
C18 C 0.16306(8) 0.96041(8) 0.45395(7) 0.01405(15) Uani 1 1 d . . . . .
H18 H 0.145667 1.020406 0.483599 0.017 Uiso 1 1 calc R U . . .
C18' C 0.23203(9) 0.45178(8) 0.64668(7) 0.01545(16) Uani 1 1 d . . . . .
H18' H 0.295407 0.398630 0.678710 0.019 Uiso 1 1 calc R U . . .
C17 C 0.14395(8) 0.85037(8) 0.51555(7) 0.01315(15) Uani 1 1 d . . . . .
C17' C 0.24622(8) 0.56256(8) 0.58278(7) 0.01472(16) Uani 1 1 d . . . . .
C16 C 0.16774(8) 0.76203(7) 0.47104(7) 0.01274(15) Uani 1 1 d . . . . .
C16' C 0.15151(8) 0.64265(7) 0.53788(7) 0.01281(15) Uani 1 1 d . . . . .
C15 C 0.21104(8) 0.78504(8) 0.36550(7) 0.01372(15) Uani 1 1 d . . . . .
C15' C 0.04336(8) 0.61040(7) 0.55763(7) 0.01281(15) Uani 1 1 d . . . . .
C14 C 0.23181(8) 0.89563(8) 0.30533(7) 0.01431(16) Uani 1 1 d . . . . .
H14 H 0.262671 0.910959 0.234250 0.017 Uiso 1 1 calc R U . . .
C14' C 0.03243(9) 0.49759(8) 0.61921(7) 0.01452(16) Uani 1 1 d . . . . .
H14' H -0.039860 0.474854 0.630590 0.017 Uiso 1 1 calc R U . . .
C19 C 0.09927(10) 0.82766(9) 0.62871(8) 0.01791(17) Uani 1 1 d . . . . .
H19A H 0.151429 0.761017 0.669029 0.027 Uiso 1 1 calc R U . . .
H19B H 0.020935 0.811003 0.643965 0.027 Uiso 1 1 calc R U . . .
H19C H 0.096336 0.896183 0.646833 0.027 Uiso 1 1 calc R U . . .
C19' C 0.36294(9) 0.59560(9) 0.56164(9) 0.0216(2) Uani 1 1 d . . . . .
H19D H 0.393236 0.613268 0.487899 0.032 Uiso 1 1 calc R U . . .
H19E H 0.417289 0.530978 0.601454 0.032 Uiso 1 1 calc R U . . .
H19F H 0.354219 0.664031 0.581831 0.032 Uiso 1 1 calc R U . . .
C21 C 0.45637(9) 1.29479(8) 0.13438(8) 0.01621(17) Uani 1 1 d . . . . .
C21' C 0.23563(9) 0.03706(8) 0.96822(7) 0.01525(16) Uani 1 1 d . . . . .
C20 C 0.23375(10) 0.69272(9) 0.31543(8) 0.02093(19) Uani 1 1 d . . . . .
H20A H 0.272508 0.721101 0.244271 0.031 Uiso 1 1 calc R U . . .
H20B H 0.159661 0.674531 0.315345 0.031 Uiso 1 1 calc R U . . .
H20C H 0.283794 0.622637 0.354183 0.031 Uiso 1 1 calc R U . . .
C20' C -0.06114(9) 0.69643(8) 0.51507(8) 0.01747(17) Uani 1 1 d . . . . .
H20D H -0.124840 0.656116 0.527623 0.026 Uiso 1 1 calc R U . . .
H20E H -0.040620 0.733491 0.440706 0.026 Uiso 1 1 calc R U . . .
H20F H -0.085926 0.755620 0.549217 0.026 Uiso 1 1 calc R U . . .
C22 C 0.58655(9) 1.12255(9) 0.20023(9) 0.0212(2) Uani 1 1 d . . . . .
H22A H 0.645131 1.160449 0.206746 0.025 Uiso 1 1 calc R U . . .
H22B H 0.606441 1.111126 0.131989 0.025 Uiso 1 1 calc R U . . .
C22' C 0.31865(10) 0.17956(9) 0.97929(8) 0.01997(19) Uani 1 1 d . . . . .
H22C H 0.399083 0.133605 0.974234 0.024 Uiso 1 1 calc R U . . .
H22D H 0.285779 0.164872 1.053121 0.024 Uiso 1 1 calc R U . . .
C23 C 0.58492(9) 1.00858(9) 0.28460(9) 0.01866(18) Uani 1 1 d . . . . .
C23' C 0.31828(9) 0.30579(9) 0.92597(8) 0.01730(17) Uani 1 1 d . . . . .
C24 C 0.62140(10) 0.98542(10) 0.37748(10) 0.0234(2) Uani 1 1 d . . . . .
F24 F 0.65713(8) 1.06810(7) 0.39429(7) 0.0379(2) Uani 1 1 d . . . . .
F24' F 0.52042(6) 0.27197(7) 0.86867(6) 0.02774(15) Uani 1 1 d . . . . .
C24' C 0.41885(9) 0.34671(10) 0.87331(8) 0.01964(18) Uani 1 1 d . . . . .
C25 C 0.62223(11) 0.87928(11) 0.45486(9) 0.0253(2) Uani 1 1 d . . . . .
F25 F 0.65827(8) 0.85966(8) 0.54342(7) 0.0401(2) Uani 1 1 d . . . . .
F25' F 0.51582(7) 0.50064(8) 0.77313(6) 0.03460(18) Uani 1 1 d . . . . .
C25' C 0.41804(10) 0.46394(10) 0.82499(9) 0.0233(2) Uani 1 1 d . . . . .
C26 C 0.58508(9) 0.79307(9) 0.43959(9) 0.0217(2) Uani 1 1 d . . . . .
F26 F 0.58756(7) 0.68977(6) 0.51298(6) 0.03155(17) Uani 1 1 d . . . . .
F26' F 0.31308(8) 0.65657(7) 0.78344(7) 0.0377(2) Uani 1 1 d . . . . .
C26' C 0.31476(11) 0.54309(9) 0.82949(9) 0.0243(2) Uani 1 1 d . . . . .
C27 C 0.54580(9) 0.81419(8) 0.34852(8) 0.01825(18) Uani 1 1 d . . . . .
F27 F 0.50938(6) 0.73119(6) 0.33316(6) 0.02444(14) Uani 1 1 d . . . . .
F27' F 0.11288(7) 0.58319(7) 0.88467(7) 0.03390(18) Uani 1 1 d . . . . .
C27' C 0.21271(10) 0.50557(10) 0.88111(9) 0.0230(2) Uani 1 1 d . . . . .
C28 C 0.54583(9) 0.92094(9) 0.27283(8) 0.01725(17) Uani 1 1 d . . . . .
F28 F 0.50786(6) 0.93912(6) 0.18484(5) 0.02417(14) Uani 1 1 d . . . . .
F28' F 0.11643(6) 0.35333(7) 0.97954(6) 0.02730(15) Uani 1 1 d . . . . .
C28' C 0.21567(9) 0.38861(9) 0.92850(8) 0.01953(18) 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
C1 C6 1.4015(14) . ?
C1 C2 1.4104(13) . ?
C1 C11 1.4353(12) . ?
C1' C6' 1.4093(14) . ?
C1' C2' 1.4107(13) . ?
C1' C11' 1.4335(12) . ?
O1 C21 1.2090(12) . ?
O1' C21' 1.2086(12) . ?
C2 C3 1.3942(13) . ?
C2 C21 1.4819(14) . ?
O2 C21 1.3382(12) . ?
O2 C22 1.4463(13) . ?
O2' C21' 1.3413(12) . ?
O2' C22' 1.4520(12) . ?
C2' C3' 1.4002(13) . ?
C2' C21' 1.4902(14) . ?
C3' C4' 1.3876(15) . ?
C3' H3' 0.9500 . ?
C3 C4 1.3852(16) . ?
C3 H3 0.9500 . ?
C4' C5' 1.3887(15) . ?
C4' H4' 0.9500 . ?
C4 C5 1.3863(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3913(14) . ?
C5 H5 0.9500 . ?
C5' C6' 1.3869(13) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C6 H6 0.9500 . ?
C11 C12 1.2087(12) . ?
C11' C12' 1.2088(13) . ?
C12 C13 1.4360(12) . ?
C12' C13' 1.4331(12) . ?
C13 C18 1.3978(13) . ?
C13 C14 1.4015(13) . ?
C13' C14' 1.3970(13) . ?
C13' C18' 1.3992(14) . ?
C18 C17 1.3913(12) . ?
C18 H18 0.9500 . ?
C18' C17' 1.3909(13) . ?
C18' H18' 0.9500 . ?
C17 C16 1.4092(13) . ?
C17 C19 1.5045(13) . ?
C17' C16' 1.4063(13) . ?
C17' C19' 1.5065(14) . ?
C16 C15 1.4044(13) . ?
C16 C16' 1.4949(12) . ?
C16' C15' 1.4051(13) . ?
C15 C14 1.3989(12) . ?
C15 C20 1.5110(14) . ?
C15' C14' 1.3948(12) . ?
C15' C20' 1.5068(13) . ?
C14 H14 0.9500 . ?
C14' H14' 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C22 C23 1.4964(15) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22' C23' 1.4941(14) . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?
C23 C24 1.3823(16) . ?
C23 C28 1.3891(14) . ?
C23' C24' 1.3865(15) . ?
C23' C28' 1.3941(15) . ?
C24 F24 1.3439(13) . ?
C24 C25 1.3841(17) . ?
F24' C24' 1.3369(13) . ?
C24' C25' 1.3847(16) . ?
C25 F25 1.3325(14) . ?
C25 C26 1.3838(17) . ?
F25' C25' 1.3345(13) . ?
C25' C26' 1.3786(18) . ?
C26 F26 1.3342(12) . ?
C26 C27 1.3808(16) . ?
F26' C26' 1.3378(13) . ?
C26' C27' 1.3818(17) . ?
C27 F27 1.3417(12) . ?
C27 C28 1.3800(14) . ?
F27' C27' 1.3385(14) . ?
C27' C28' 1.3764(16) . ?
C28 F28 1.3412(12) . ?
F28' C28' 1.3402(13) . ?

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
C6 C1 C2 118.28(8) . . ?
C6 C1 C11 117.31(8) . . ?
C2 C1 C11 124.38(9) . . ?
C6' C1' C2' 118.24(8) . . ?
C6' C1' C11' 116.48(8) . . ?
C2' C1' C11' 125.28(9) . . ?
C3 C2 C1 119.78(9) . . ?
C3 C2 C21 115.46(8) . . ?
C1 C2 C21 124.75(8) . . ?
C21 O2 C22 113.70(8) . . ?
C21' O2' C22' 114.45(8) . . ?
C3' C2' C1' 119.41(9) . . ?
C3' C2' C21' 114.89(8) . . ?
C1' C2' C21' 125.68(8) . . ?
C4' C3' C2' 121.55(9) . . ?
C4' C3' H3' 119.2 . . ?
C2' C3' H3' 119.2 . . ?
C4 C3 C2 121.04(9) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3' C4' C5' 119.22(9) . . ?
C3' C4' H4' 120.4 . . ?
C5' C4' H4' 120.4 . . ?
C3 C4 C5 119.74(9) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.90(10) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6' C5' C4' 120.28(9) . . ?
C6' C5' H5' 119.9 . . ?
C4' C5' H5' 119.9 . . ?
C5' C6' C1' 121.30(9) . . ?
C5' C6' H6' 119.4 . . ?
C1' C6' H6' 119.4 . . ?
C5 C6 C1 121.24(9) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C12 C11 C1 174.22(10) . . ?
C12' C11' C1' 172.39(10) . . ?
C11 C12 C13 175.53(11) . . ?
C11' C12' C13' 176.66(11) . . ?
C18 C13 C14 119.35(8) . . ?
C18 C13 C12 118.83(8) . . ?
C14 C13 C12 121.81(9) . . ?
C14' C13' C18' 118.84(8) . . ?
C14' C13' C12' 121.58(9) . . ?
C18' C13' C12' 119.58(9) . . ?
C17 C18 C13 121.00(8) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C17' C18' C13' 120.99(9) . . ?
C17' C18' H18' 119.5 . . ?
C13' C18' H18' 119.5 . . ?
C18 C17 C16 119.43(8) . . ?
C18 C17 C19 119.34(8) . . ?
C16 C17 C19 121.23(8) . . ?
C18' C17' C16' 119.64(9) . . ?
C18' C17' C19' 119.83(9) . . ?
C16' C17' C19' 120.53(8) . . ?
C15 C16 C17 120.10(8) . . ?
C15 C16 C16' 120.37(8) . . ?
C17 C16 C16' 119.48(8) . . ?
C15' C16' C17' 119.93(8) . . ?
C15' C16' C16 121.16(8) . . ?
C17' C16' C16 118.90(8) . . ?
C14 C15 C16 119.57(8) . . ?
C14 C15 C20 119.39(8) . . ?
C16 C15 C20 121.03(8) . . ?
C14' C15' C16' 119.30(8) . . ?
C14' C15' C20' 119.70(8) . . ?
C16' C15' C20' 120.99(8) . . ?
C15 C14 C13 120.53(8) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C15' C14' C13' 121.22(9) . . ?
C15' C14' H14' 119.4 . . ?
C13' C14' H14' 119.4 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17' C19' H19D 109.5 . . ?
C17' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C17' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
O1 C21 O2 122.39(10) . . ?
O1 C21 C2 123.75(9) . . ?
O2 C21 C2 113.86(8) . . ?
O1' C21' O2' 122.58(9) . . ?
O1' C21' C2' 123.53(9) . . ?
O2' C21' C2' 113.89(8) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15' C20' H20D 109.5 . . ?
C15' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C15' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
O2 C22 C23 106.92(8) . . ?
O2 C22 H22A 110.3 . . ?
C23 C22 H22A 110.3 . . ?
O2 C22 H22B 110.3 . . ?
C23 C22 H22B 110.3 . . ?
H22A C22 H22B 108.6 . . ?
O2' C22' C23' 106.54(8) . . ?
O2' C22' H22C 110.4 . . ?
C23' C22' H22C 110.4 . . ?
O2' C22' H22D 110.4 . . ?
C23' C22' H22D 110.4 . . ?
H22C C22' H22D 108.6 . . ?
C24 C23 C28 116.89(10) . . ?
C24 C23 C22 122.05(10) . . ?
C28 C23 C22 121.06(10) . . ?
C24' C23' C28' 116.74(10) . . ?
C24' C23' C22' 122.28(10) . . ?
C28' C23' C22' 120.97(10) . . ?
F24 C24 C23 119.51(10) . . ?
F24 C24 C25 118.30(11) . . ?
C23 C24 C25 122.19(10) . . ?
F24' C24' C25' 118.23(10) . . ?
F24' C24' C23' 119.80(10) . . ?
C25' C24' C23' 121.96(10) . . ?
F25 C25 C26 119.98(11) . . ?
F25 C25 C24 120.68(11) . . ?
C26 C25 C24 119.34(11) . . ?
F25' C25' C26' 119.87(11) . . ?
F25' C25' C24' 120.63(11) . . ?
C26' C25' C24' 119.49(10) . . ?
F26 C26 C27 120.29(10) . . ?
F26 C26 C25 119.78(10) . . ?
C27 C26 C25 119.93(10) . . ?
F26' C26' C25' 119.99(11) . . ?
F26' C26' C27' 119.81(11) . . ?
C25' C26' C27' 120.20(10) . . ?
F27 C27 C28 120.26(10) . . ?
F27 C27 C26 120.33(9) . . ?
C28 C27 C26 119.41(10) . . ?
F27' C27' C28' 121.08(11) . . ?
F27' C27' C26' 119.67(10) . . ?
C28' C27' C26' 119.25(10) . . ?
F28 C28 C27 118.29(9) . . ?
F28 C28 C23 119.50(9) . . ?
C27 C28 C23 122.21(10) . . ?
F28' C28' C27' 118.73(10) . . ?
F28' C28' C23' 118.92(10) . . ?
C27' C28' C23' 122.35(10) . . ?

_refine_diff_density_max         0.692
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.087



####################################################################### 
# 
# 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_WM02113_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1875130'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H32 F10 O6'
_chemical_formula_weight         870.71

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                   13.2155(10)
_cell_length_b                   9.1259(7)
_cell_length_c                   15.7624(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.357(3)
_cell_angle_gamma                90
_cell_volume                     1901.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9692
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      30.57

_exptl_crystal_description       Prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7231
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            86329
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.017
_diffrn_reflns_theta_max         30.586
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5823
_reflns_number_gt                5023
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0672P)²+0.7491P] 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_number_reflns         5823
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_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
F1 F 0.37235(5) 0.39078(8) 0.85657(5) 0.02297(16) Uani 1 1 d . . . . .
O1 O 0.34440(5) 0.66342(8) 0.42897(5) 0.01519(15) Uani 1 1 d . . . . .
C1 C 0.10599(7) 0.41684(10) 0.59129(6) 0.01066(17) Uani 1 1 d . . . . .
O2 O 0.08355(6) 0.65676(9) 0.77611(5) 0.01912(17) Uani 1 1 d . . . . .
F2 F 0.56914(5) 0.31799(8) 0.83962(5) 0.02282(15) Uani 1 1 d . . . . .
C2 C 0.04261(7) 0.33414(11) 0.53772(6) 0.01346(18) Uani 1 1 d . . . . .
H2 H 0.070541 0.286399 0.489705 0.016 Uiso 1 1 calc R U . . .
F3 F 0.69369(5) 0.48699(9) 0.74425(5) 0.02383(16) Uani 1 1 d . . . . .
O3 O 0.22162(6) 0.54844(9) 0.72314(5) 0.01630(16) Uani 1 1 d . . . . .
C3 C -0.06019(8) 0.32108(12) 0.55384(7) 0.01581(19) Uani 1 1 d . . . . .
H3 H -0.101768 0.264209 0.517107 0.019 Uiso 1 1 calc R U . . .
F4 F 0.61811(6) 0.72308(9) 0.65998(5) 0.02661(17) Uani 1 1 d . . . . .
C4 C -0.10250(7) 0.39098(12) 0.62357(7) 0.0164(2) Uani 1 1 d . . . . .
H4 H -0.173049 0.383730 0.633990 0.020 Uiso 1 1 calc R U . . .
C5 C -0.04081(7) 0.47131(12) 0.67770(7) 0.01449(19) Uani 1 1 d . . . . .
H5 H -0.069641 0.518272 0.725606 0.017 Uiso 1 1 calc R U . . .
F5 F 0.42031(6) 0.79202(8) 0.67272(4) 0.02359(16) Uani 1 1 d . . . . .
C6 C 0.06323(7) 0.48453(11) 0.66311(6) 0.01119(17) Uani 1 1 d . . . . .
C15 C 0.42394(7) 0.58749(11) 0.46297(6) 0.01164(18) Uani 1 1 d . . . . .
C16 C 0.52526(7) 0.61087(11) 0.44287(6) 0.01201(18) Uani 1 1 d . . . . .
H16 H 0.542861 0.686237 0.404096 0.014 Uiso 1 1 calc R U . . .
C17 C 0.36585(8) 0.79559(11) 0.38269(7) 0.01446(19) Uani 1 1 d . . . . .
H17A H 0.304489 0.826112 0.350964 0.017 Uiso 1 1 calc R U . . .
H17B H 0.419831 0.775767 0.340966 0.017 Uiso 1 1 calc R U . . .
C18 C 0.39912(8) 0.91918(12) 0.44057(7) 0.0181(2) Uani 1 1 d . . . . .
H18A H 0.415550 1.005797 0.405438 0.022 Uiso 1 1 calc R U . . .
H18B H 0.461740 0.889188 0.470674 0.022 Uiso 1 1 calc R U . . .
C19 C 0.32004(9) 0.96327(14) 0.50617(7) 0.0210(2) Uani 1 1 d . . . . .
H19A H 0.298025 0.874672 0.537248 0.025 Uiso 1 1 calc R U . . .
H19B H 0.351664 1.030754 0.547753 0.025 Uiso 1 1 calc R U . . .
C20 C 0.22739(9) 1.03754(14) 0.46731(8) 0.0220(2) Uani 1 1 d . . . . .
H20A H 0.248497 1.125392 0.436350 0.033 Uiso 1 1 calc R U . . .
H20B H 0.180477 1.065310 0.512452 0.033 Uiso 1 1 calc R U . . .
H20C H 0.193634 0.969659 0.428143 0.033 Uiso 1 1 calc R U . . .
C61 C 0.12145(7) 0.57307(11) 0.72614(6) 0.01269(18) Uani 1 1 d . . . . .
C62 C 0.28216(8) 0.63888(13) 0.77948(7) 0.0178(2) Uani 1 1 d . . . . .
H62A H 0.262262 0.622518 0.839178 0.021 Uiso 1 1 calc R U . . .
H62B H 0.272503 0.743850 0.765787 0.021 Uiso 1 1 calc R U . . .
C63 C 0.39054(8) 0.59556(11) 0.76668(6) 0.01459(19) Uani 1 1 d . . . . .
C64 C 0.43162(8) 0.47410(11) 0.80720(7) 0.01529(19) Uani 1 1 d . . . . .
C65 C 0.53241(8) 0.43552(12) 0.79957(7) 0.01582(19) Uani 1 1 d . . . . .
C66 C 0.59558(8) 0.52080(12) 0.75021(7) 0.0159(2) Uani 1 1 d . . . . .
C67 C 0.55713(8) 0.64099(12) 0.70768(7) 0.0167(2) Uani 1 1 d . . . . .
C68 C 0.45550(8) 0.67568(12) 0.71542(7) 0.01569(19) Uani 1 1 d . . . . .
C14 C 0.39862(7) 0.47609(11) 0.52052(6) 0.01116(17) Uani 1 1 d . . . . .
C13 C 0.29514(7) 0.45222(11) 0.54303(6) 0.01223(18) Uani 1 1 d . . . . .
C12 C 0.20967(7) 0.43455(11) 0.56686(6) 0.01213(18) 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
F1 C64 1.3434(12) . ?
O1 C15 1.3657(12) . ?
O1 C17 1.4387(12) . ?
C1 C2 1.4055(13) . ?
C1 C6 1.4108(13) . ?
C1 C12 1.4347(13) . ?
O2 C61 1.2082(12) . ?
F2 C65 1.3345(12) . ?
C2 C3 1.3887(14) . ?
C2 H2 0.9500 . ?
F3 C66 1.3367(12) . ?
O3 C61 1.3438(12) . ?
O3 C62 1.4495(12) . ?
C3 C4 1.3912(15) . ?
C3 H3 0.9500 . ?
F4 C67 1.3355(12) . ?
C4 C5 1.3862(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4007(13) . ?
C5 H5 0.9500 . ?
F5 C68 1.3390(12) . ?
C6 C61 1.4907(14) . ?
C15 C16 1.3943(12) . ?
C15 C14 1.4044(13) . ?
C16 C14 1.4027(13) 3_666 ?
C16 H16 0.9500 . ?
C17 C18 1.5142(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5286(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5247(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C62 C63 1.5007(14) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.3882(15) . ?
C63 C68 1.3903(15) . ?
C64 C65 1.3837(14) . ?
C65 C66 1.3842(15) . ?
C66 C67 1.3807(16) . ?
C67 C68 1.3860(15) . ?
C14 C13 1.4316(13) . ?
C13 C12 1.2035(14) . ?

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
C15 O1 C17 118.08(8) . . ?
C2 C1 C6 118.49(9) . . ?
C2 C1 C12 117.76(9) . . ?
C6 C1 C12 123.65(9) . . ?
C3 C2 C1 121.08(9) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C61 O3 C62 115.05(8) . . ?
C2 C3 C4 120.24(9) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.41(9) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.24(9) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.51(9) . . ?
C5 C6 C61 116.12(9) . . ?
C1 C6 C61 124.36(8) . . ?
O1 C15 C16 124.82(9) . . ?
O1 C15 C14 115.78(8) . . ?
C16 C15 C14 119.38(9) . . ?
C15 C16 C14 120.48(9) . 3_666 ?
C15 C16 H16 119.8 . . ?
C14 C16 H16 119.8 3_666 . ?
O1 C17 C18 112.11(9) . . ?
O1 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
O1 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 113.98(9) . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 113.32(10) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C61 O3 122.76(9) . . ?
O2 C61 C6 124.25(9) . . ?
O3 C61 C6 112.98(8) . . ?
O3 C62 C63 106.94(8) . . ?
O3 C62 H62A 110.3 . . ?
C63 C62 H62A 110.3 . . ?
O3 C62 H62B 110.3 . . ?
C63 C62 H62B 110.3 . . ?
H62A C62 H62B 108.6 . . ?
C64 C63 C68 116.50(9) . . ?
C64 C63 C62 121.28(10) . . ?
C68 C63 C62 122.20(10) . . ?
F1 C64 C65 118.13(10) . . ?
F1 C64 C63 119.39(9) . . ?
C65 C64 C63 122.48(10) . . ?
F2 C65 C64 120.72(10) . . ?
F2 C65 C66 119.93(9) . . ?
C64 C65 C66 119.35(10) . . ?
F3 C66 C67 120.23(10) . . ?
F3 C66 C65 119.89(10) . . ?
C67 C66 C65 119.88(10) . . ?
F4 C67 C66 119.83(10) . . ?
F4 C67 C68 120.66(10) . . ?
C66 C67 C68 119.51(10) . . ?
F5 C68 C67 118.07(10) . . ?
F5 C68 C63 119.69(10) . . ?
C67 C68 C63 122.23(10) . . ?
C16 C14 C15 120.14(8) 3_666 . ?
C16 C14 C13 119.72(9) 3_666 . ?
C15 C14 C13 120.13(9) . . ?
C12 C13 C14 176.06(10) . . ?
C13 C12 C1 177.07(10) . . ?

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.078



