data_publication_text
_publ_requested_journal          'Cryst.Growth Des.'
_publ_contact_author_name        "Braulio Rodríguez-Molina"
_publ_contact_author_email       brodriguez@iquimica.unam.mx
loop_
_publ_author_name
_publ_author_address
"Rodríguez-Molina, Manuel" ''
'Galicia-Badillo, Dazaet' ''
'Enoc, Cetina-Mancilla' ''
"Cárdenas, Jorge" ''
'Olvera, Lilian I.' ''
"Toscano, Rubén A." ''
"Braulio, Rodríguez-Molina" ''
'Zolotukhin, Mikhail G.' ''



data_150CPR17
# start Validation Reply Form
_vrf_PLAT089_150CPR17            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.94 Note
RESPONSE: Poor data/parameter ratio is due to the fact that the structure was refined as a hole structure disordered over two sites, doubling the number of parameters.
;
# Added during the CSD deposition process: Friday 04 February 2022 02:00 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
4,5-dimethyl-9-phenyl-9-(trifluoromethyl)-9H-xanthene-3,6-diol
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H16 F3 O3'
_chemical_formula_sum            'C22 H17 F3 O3'
_exptl_crystal_recrystallization_method 'From DCM evaporation'
_chemical_melting_point          ?

_exptl_crystal_description       flakes
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         385.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_chemical_absolute_configuration ad

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

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

_cell_length_a                   7.7794(3)
_cell_length_b                   19.3621(7)
_cell_length_c                   12.6018(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1898.15(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      77.94
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.926
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4893
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture κ geometry diffractometer'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            30831
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.186
_diffrn_reflns_theta_max         74.445
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3865
_reflns_number_gt                2727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0564P)²+0.3729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1047 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(11)
_refine_ls_number_reflns         3865
_refine_ls_number_parameters     515
_refine_ls_number_restraints     1141
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.388(3) 0.2839(6) 0.4074(10) 0.067(3) Uani 0.579(3) 1 d D U P A 1
O2 O 0.307(2) 0.6908(5) 0.7930(13) 0.077(3) Uani 0.579(3) 1 d D U P A 1
H2A H 0.222(12) 0.725(5) 0.835(9) 0.116 Uiso 0.579(3) 1 d . U P A 1
C1 C 0.0998(14) 0.3195(4) 0.6267(10) 0.065(2) Uani 0.579(3) 1 d D U P A 1
H1 H 0.030032 0.294396 0.672598 0.078 Uiso 0.579(3) 1 calc R U P A 1
C2 C 0.191(2) 0.2854(5) 0.5499(13) 0.066(2) Uani 0.579(3) 1 d D U P A 1
H2 H 0.178839 0.237876 0.542053 0.079 Uiso 0.579(3) 1 calc R U P A 1
C3 C 0.300(3) 0.3215(5) 0.4841(15) 0.063(2) Uani 0.579(3) 1 d D U P A 1
C4 C 0.3157(16) 0.3924(4) 0.4910(8) 0.066(2) Uani 0.579(3) 1 d D U P A 1
C5 C 0.2733(17) 0.5924(4) 0.6849(11) 0.070(3) Uani 0.579(3) 1 d D U P A 1
C6 C 0.219(4) 0.6302(8) 0.772(2) 0.072(2) Uani 0.579(3) 1 d D U P A 1
C7 C 0.095(3) 0.6054(6) 0.8409(15) 0.077(3) Uani 0.579(3) 1 d D U P A 1
H7 H 0.062113 0.631038 0.899979 0.092 Uiso 0.579(3) 1 calc R U P A 1
C8 C 0.0197(18) 0.5422(5) 0.8209(12) 0.076(3) Uani 0.579(3) 1 d D U P A 1
H8 H -0.067903 0.526497 0.864933 0.091 Uiso 0.579(3) 1 calc R U P A 1
C9 C -0.0026(8) 0.4296(3) 0.7159(5) 0.0699(13) Uani 0.579(3) 1 d D U P A 1
O10 O 0.2479(9) 0.4951(2) 0.5779(4) 0.0728(14) Uani 0.579(3) 1 d D U P A 1
C11 C 0.1097(10) 0.3902(3) 0.6375(6) 0.0648(17) Uani 0.579(3) 1 d D U P A 1
C12 C 0.2219(11) 0.4249(3) 0.5710(6) 0.0655(18) Uani 0.579(3) 1 d D U P A 1
C13 C 0.0724(10) 0.5016(3) 0.7362(6) 0.0700(18) Uani 0.579(3) 1 d D U P A 1
C14 C 0.1951(11) 0.5289(3) 0.6688(6) 0.0683(19) Uani 0.579(3) 1 d D U P A 1
C15 C 0.4586(17) 0.4305(6) 0.4285(9) 0.073(3) Uani 0.579(3) 1 d D U P A 1
H15A H 0.445189 0.421536 0.354024 0.109 Uiso 0.579(3) 1 calc R U P A 1
H15B H 0.569100 0.414218 0.451481 0.109 Uiso 0.579(3) 1 calc R U P A 1
H15C H 0.450141 0.479231 0.441248 0.109 Uiso 0.579(3) 1 calc R U P A 1
C16 C 0.4086(17) 0.6189(7) 0.6106(12) 0.089(5) Uani 0.579(3) 1 d D U P A 1
H16A H 0.358045 0.628138 0.542587 0.134 Uiso 0.579(3) 1 calc R U P A 1
H16B H 0.497509 0.584888 0.602979 0.134 Uiso 0.579(3) 1 calc R U P A 1
H16C H 0.457026 0.660722 0.638689 0.134 Uiso 0.579(3) 1 calc R U P A 1
C17 C -0.1787(11) 0.4396(5) 0.6638(7) 0.087(2) Uani 0.579(3) 1 d D U P A 1
F1 F -0.1649(7) 0.4797(3) 0.5779(4) 0.1055(16) Uani 0.579(3) 1 d D U P A 1
F2 F -0.2514(6) 0.3808(3) 0.6316(6) 0.1115(18) Uani 0.579(3) 1 d D U P A 1
F3 F -0.2911(6) 0.4703(3) 0.7286(5) 0.1077(17) Uani 0.579(3) 1 d D U P A 1
C18 C -0.0130(9) 0.3892(3) 0.8207(5) 0.0794(16) Uani 0.579(3) 1 d D U P A 1
C19 C 0.1279(13) 0.3914(5) 0.8875(7) 0.097(2) Uani 0.579(3) 1 d D U P A 1
H19 H 0.222771 0.417647 0.867692 0.116 Uiso 0.579(3) 1 calc R U P A 1
C20 C 0.1324(14) 0.3560(6) 0.9830(7) 0.121(3) Uani 0.579(3) 1 d D U P A 1
H20 H 0.229000 0.358031 1.026416 0.145 Uiso 0.579(3) 1 calc R U P A 1
C21 C -0.0093(14) 0.3175(6) 1.0125(8) 0.130(3) Uani 0.579(3) 1 d D U P A 1
H21 H -0.008891 0.293936 1.076792 0.156 Uiso 0.579(3) 1 calc R U P A 1
C22 C -0.1512(14) 0.3139(6) 0.9474(8) 0.127(3) Uani 0.579(3) 1 d D U P A 1
H22 H -0.243723 0.285895 0.965693 0.152 Uiso 0.579(3) 1 calc R U P A 1
C23 C -0.1554(14) 0.3521(7) 0.8542(9) 0.107(3) Uani 0.579(3) 1 d D U P A 1
H23 H -0.255258 0.352868 0.813705 0.128 Uiso 0.579(3) 1 calc R U P A 1
O1B O 0.383(4) 0.2920(8) 0.3793(15) 0.079(5) Uani 0.421(3) 1 d D U P A 2
H1C H 0.483(19) 0.309(6) 0.363(7) 0.119 Uiso 0.421(3) 1 calc R U P A 2
O2B O 0.290(3) 0.7011(7) 0.770(2) 0.085(6) Uani 0.421(3) 1 d D U P A 2
C1B C 0.148(2) 0.3156(5) 0.6254(13) 0.070(3) Uani 0.421(3) 1 d D U P A 2
H1B H 0.070619 0.290453 0.666514 0.083 Uiso 0.421(3) 1 calc R U P A 2
C2B C 0.225(4) 0.2848(7) 0.5395(19) 0.070(3) Uani 0.421(3) 1 d D U P A 2
H2B H 0.210972 0.237668 0.527713 0.084 Uiso 0.421(3) 1 calc R U P A 2
C3B C 0.322(5) 0.3236(8) 0.471(2) 0.066(3) Uani 0.421(3) 1 d D U P A 2
C4B C 0.363(2) 0.3915(6) 0.4936(11) 0.063(3) Uani 0.421(3) 1 d D U P A 2
C5B C 0.316(2) 0.5921(6) 0.6886(15) 0.067(3) Uani 0.421(3) 1 d D U P A 2
C6B C 0.231(5) 0.6339(11) 0.760(3) 0.072(3) Uani 0.421(3) 1 d D U P A 2
C7B C 0.097(4) 0.6093(8) 0.822(2) 0.076(3) Uani 0.421(3) 1 d D U P A 2
H7B H 0.032698 0.639467 0.863726 0.091 Uiso 0.421(3) 1 calc R U P A 2
C8B C 0.060(3) 0.5395(7) 0.8216(16) 0.075(3) Uani 0.421(3) 1 d D U P A 2
H8C H -0.019056 0.521764 0.869740 0.090 Uiso 0.421(3) 1 calc R U P A 2
C9B C 0.1102(10) 0.4171(4) 0.7517(6) 0.0696(16) Uani 0.421(3) 1 d D U P A 2
O10B O 0.3485(11) 0.4850(3) 0.6078(6) 0.0707(17) Uani 0.421(3) 1 d D U P A 2
C11B C 0.1827(13) 0.3835(4) 0.6517(7) 0.067(2) Uani 0.421(3) 1 d D U P A 2
C12B C 0.2948(14) 0.4190(4) 0.5871(7) 0.065(2) Uani 0.421(3) 1 d D U P A 2
C13B C 0.1400(13) 0.4954(4) 0.7495(8) 0.071(2) Uani 0.421(3) 1 d D U P A 2
C14B C 0.2630(15) 0.5236(4) 0.6838(9) 0.069(2) Uani 0.421(3) 1 d D U P A 2
C15B C 0.425(3) 0.4397(9) 0.4029(13) 0.084(5) Uani 0.421(3) 1 d D U P A 2
H15D H 0.548256 0.440722 0.401672 0.126 Uiso 0.421(3) 1 calc R U P A 2
H15E H 0.381718 0.485509 0.414737 0.126 Uiso 0.421(3) 1 calc R U P A 2
H15F H 0.382858 0.422712 0.336215 0.126 Uiso 0.421(3) 1 calc R U P A 2
C16B C 0.467(2) 0.6170(9) 0.6254(16) 0.073(4) Uani 0.421(3) 1 d D U P A 2
H16D H 0.462212 0.597813 0.555188 0.110 Uiso 0.421(3) 1 calc R U P A 2
H16E H 0.571536 0.602654 0.659426 0.110 Uiso 0.421(3) 1 calc R U P A 2
H16F H 0.464303 0.666494 0.621054 0.110 Uiso 0.421(3) 1 calc R U P A 2
C17B C 0.2106(12) 0.3881(5) 0.8464(8) 0.088(2) Uani 0.421(3) 1 d D U P A 2
F1B F 0.3760(8) 0.4065(4) 0.8407(6) 0.108(2) Uani 0.421(3) 1 d D U P A 2
F2B F 0.2080(11) 0.3196(3) 0.8532(6) 0.112(2) Uani 0.421(3) 1 d D U P A 2
F3B F 0.1518(12) 0.4125(4) 0.9396(6) 0.110(2) Uani 0.421(3) 1 d D U P A 2
C18B C -0.0829(10) 0.4015(5) 0.7571(8) 0.0779(19) Uani 0.421(3) 1 d D U P A 2
C19B C -0.1866(13) 0.4351(8) 0.6838(12) 0.087(3) Uani 0.421(3) 1 d D U P A 2
H19B H -0.136867 0.466961 0.637884 0.104 Uiso 0.421(3) 1 calc R U P A 2
C20B C -0.3619(12) 0.4228(6) 0.6768(10) 0.102(3) Uani 0.421(3) 1 d D U P A 2
H20B H -0.429651 0.447458 0.629223 0.122 Uiso 0.421(3) 1 calc R U P A 2
C21B C -0.4338(15) 0.3732(7) 0.7420(11) 0.115(3) Uani 0.421(3) 1 d D U P A 2
H21B H -0.549617 0.362242 0.735273 0.138 Uiso 0.421(3) 1 calc R U P A 2
C22B C -0.3345(13) 0.3399(7) 0.8170(11) 0.112(3) Uani 0.421(3) 1 d D U P A 2
H22B H -0.385506 0.309879 0.865197 0.134 Uiso 0.421(3) 1 calc R U P A 2
C23B C -0.1581(15) 0.3513(10) 0.8203(14) 0.100(3) Uani 0.421(3) 1 d D U P A 2
H23B H -0.089830 0.324995 0.865441 0.120 Uiso 0.421(3) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.392(9) . ?
O2 C6 1.383(10) . ?
O2 H2A 1.07(11) . ?
C1 C2 1.369(9) . ?
C1 C11 1.379(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(8) . ?
C4 C12 1.394(8) . ?
C4 C15 1.548(10) . ?
C5 C6 1.384(9) . ?
C5 C14 1.387(8) . ?
C5 C16 1.500(9) . ?
C6 C7 1.388(9) . ?
C7 C8 1.378(10) . ?
C7 H7 0.9300 . ?
C8 C13 1.387(9) . ?
C8 H8 0.9300 . ?
C9 C11 1.524(8) . ?
C9 C17 1.531(11) . ?
C9 C13 1.533(8) . ?
C9 C18 1.538(8) . ?
O10 C12 1.377(7) . ?
O10 C14 1.382(7) . ?
C11 C12 1.384(8) . ?
C13 C14 1.383(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 F2 1.334(9) . ?
C17 F3 1.336(9) . ?
C17 F1 1.338(8) . ?
C18 C19 1.382(6) . ?
C18 C23 1.386(6) . ?
C19 C20 1.386(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
O1B C3B 1.393(11) . ?
O1B H1C 0.87(15) . ?
O2B C6B 1.383(10) . ?
C1B C2B 1.375(11) . ?
C1B C11B 1.382(9) . ?
C1B H1B 0.9300 . ?
C2B C3B 1.371(11) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.382(10) . ?
C4B C12B 1.398(10) . ?
C4B C15B 1.552(12) . ?
C5B C6B 1.381(11) . ?
C5B C14B 1.388(9) . ?
C5B C16B 1.502(11) . ?
C6B C7B 1.387(10) . ?
C7B C8B 1.382(11) . ?
C7B H7B 0.9300 . ?
C8B C13B 1.393(10) . ?
C8B H8C 0.9300 . ?
C9B C11B 1.527(10) . ?
C9B C13B 1.532(9) . ?
C9B C17B 1.534(12) . ?
C9B C18B 1.534(9) . ?
O10B C12B 1.370(8) . ?
O10B C14B 1.385(9) . ?
C11B C12B 1.376(10) . ?
C13B C14B 1.379(10) . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17B F2B 1.329(9) . ?
C17B F1B 1.337(9) . ?
C17B F3B 1.345(9) . ?
C18B C23B 1.386(6) . ?
C18B C19B 1.389(7) . ?
C19B C20B 1.387(7) . ?
C19B H19B 0.9300 . ?
C20B C21B 1.382(7) . ?
C20B H20B 0.9300 . ?
C21B C22B 1.381(7) . ?
C21B H21B 0.9300 . ?
C22B C23B 1.391(7) . ?
C22B H22B 0.9300 . ?
C23B H23B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 H2A 108(5) . . ?
C2 C1 C11 121.3(7) . . ?
C2 C1 H1 119.3 . . ?
C11 C1 H1 119.3 . . ?
C1 C2 C3 120.0(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 121.5(7) . . ?
C2 C3 O1 117.2(6) . . ?
C4 C3 O1 121.3(7) . . ?
C3 C4 C12 116.5(6) . . ?
C3 C4 C15 120.4(8) . . ?
C12 C4 C15 121.9(6) . . ?
C6 C5 C14 116.9(6) . . ?
C6 C5 C16 121.8(7) . . ?
C14 C5 C16 121.3(7) . . ?
O2 C6 C5 116.7(7) . . ?
O2 C6 C7 121.3(9) . . ?
C5 C6 C7 121.7(6) . . ?
C8 C7 C6 119.2(7) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C13 121.2(7) . . ?
C7 C8 H8 119.4 . . ?
C13 C8 H8 119.4 . . ?
C11 C9 C17 107.3(6) . . ?
C11 C9 C13 110.2(5) . . ?
C17 C9 C13 107.3(6) . . ?
C11 C9 C18 109.4(5) . . ?
C17 C9 C18 112.7(6) . . ?
C13 C9 C18 109.9(5) . . ?
C12 O10 C14 118.4(5) . . ?
C1 C11 C12 117.2(6) . . ?
C1 C11 C9 122.0(6) . . ?
C12 C11 C9 120.8(5) . . ?
O10 C12 C11 122.2(5) . . ?
O10 C12 C4 114.4(6) . . ?
C11 C12 C4 123.3(5) . . ?
C14 C13 C8 117.4(6) . . ?
C14 C13 C9 120.5(6) . . ?
C8 C13 C9 122.1(6) . . ?
O10 C14 C13 122.2(5) . . ?
O10 C14 C5 114.3(6) . . ?
C13 C14 C5 123.4(6) . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F2 C17 F3 106.7(7) . . ?
F2 C17 F1 106.4(8) . . ?
F3 C17 F1 106.8(7) . . ?
F2 C17 C9 113.8(7) . . ?
F3 C17 C9 112.3(7) . . ?
F1 C17 C9 110.4(6) . . ?
C19 C18 C23 117.7(8) . . ?
C19 C18 C9 117.7(6) . . ?
C23 C18 C9 124.6(7) . . ?
C18 C19 C20 122.2(8) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 118.7(9) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C20 120.5(9) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.7(9) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 121.0(9) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C3B O1B H1C 109.5 . . ?
C2B C1B C11B 121.0(8) . . ?
C2B C1B H1B 119.5 . . ?
C11B C1B H1B 119.5 . . ?
C3B C2B C1B 119.8(8) . . ?
C3B C2B H2B 120.1 . . ?
C1B C2B H2B 120.1 . . ?
C2B C3B C4B 121.5(8) . . ?
C2B C3B O1B 117.9(8) . . ?
C4B C3B O1B 120.6(9) . . ?
C3B C4B C12B 116.5(7) . . ?
C3B C4B C15B 119.6(11) . . ?
C12B C4B C15B 120.6(8) . . ?
C6B C5B C14B 116.6(7) . . ?
C6B C5B C16B 122.1(8) . . ?
C14B C5B C16B 121.0(8) . . ?
C5B C6B O2B 116.9(9) . . ?
C5B C6B C7B 121.6(8) . . ?
O2B C6B C7B 121.4(9) . . ?
C8B C7B C6B 119.3(10) . . ?
C8B C7B H7B 120.4 . . ?
C6B C7B H7B 120.4 . . ?
C7B C8B C13B 120.7(8) . . ?
C7B C8B H8C 119.6 . . ?
C13B C8B H8C 119.6 . . ?
C11B C9B C13B 110.6(6) . . ?
C11B C9B C17B 107.4(7) . . ?
C13B C9B C17B 107.4(7) . . ?
C11B C9B C18B 108.4(7) . . ?
C13B C9B C18B 110.1(7) . . ?
C17B C9B C18B 113.1(6) . . ?
C12B O10B C14B 119.3(7) . . ?
C12B C11B C1B 117.3(7) . . ?
C12B C11B C9B 120.6(6) . . ?
C1B C11B C9B 122.0(7) . . ?
O10B C12B C11B 123.1(6) . . ?
O10B C12B C4B 113.6(7) . . ?
C11B C12B C4B 123.3(7) . . ?
C14B C13B C8B 117.2(7) . . ?
C14B C13B C9B 120.5(7) . . ?
C8B C13B C9B 121.8(8) . . ?
C13B C14B O10B 122.3(7) . . ?
C13B C14B C5B 123.9(7) . . ?
O10B C14B C5B 113.8(7) . . ?
C4B C15B H15D 109.5 . . ?
C4B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C4B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C5B C16B H16D 109.5 . . ?
C5B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C5B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
F2B C17B F1B 106.5(8) . . ?
F2B C17B F3B 106.7(8) . . ?
F1B C17B F3B 106.3(8) . . ?
F2B C17B C9B 114.1(7) . . ?
F1B C17B C9B 110.5(7) . . ?
F3B C17B C9B 112.2(8) . . ?
C23B C18B C19B 117.8(9) . . ?
C23B C18B C9B 125.3(8) . . ?
C19B C18B C9B 116.5(7) . . ?
C20B C19B C18B 122.2(9) . . ?
C20B C19B H19B 118.9 . . ?
C18B C19B H19B 118.9 . . ?
C21B C20B C19B 118.6(10) . . ?
C21B C20B H20B 120.7 . . ?
C19B C20B H20B 120.7 . . ?
C22B C21B C20B 120.4(10) . . ?
C22B C21B H21B 119.8 . . ?
C20B C21B H21B 119.8 . . ?
C21B C22B C23B 119.9(10) . . ?
C21B C22B H22B 120.1 . . ?
C23B C22B H22B 120.1 . . ?
C18B C23B C22B 120.7(10) . . ?
C18B C23B H23B 119.7 . . ?
C22B C23B H23B 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 3(2) . . . . ?
C1 C2 C3 C4 -2(3) . . . . ?
C1 C2 C3 O1 -180(2) . . . . ?
C2 C3 C4 C12 3(3) . . . . ?
O1 C3 C4 C12 -180(2) . . . . ?
C2 C3 C4 C15 170.6(18) . . . . ?
O1 C3 C4 C15 -12(3) . . . . ?
C14 C5 C6 O2 175(2) . . . . ?
C16 C5 C6 O2 -6(4) . . . . ?
C14 C5 C6 C7 1(4) . . . . ?
C16 C5 C6 C7 -180(2) . . . . ?
O2 C6 C7 C8 -175(3) . . . . ?
C5 C6 C7 C8 -2(4) . . . . ?
C6 C7 C8 C13 3(3) . . . . ?
C2 C1 C11 C12 -3.2(16) . . . . ?
C2 C1 C11 C9 174.4(12) . . . . ?
C17 C9 C11 C1 -81.1(10) . . . . ?
C13 C9 C11 C1 162.3(9) . . . . ?
C18 C9 C11 C1 41.4(10) . . . . ?
C17 C9 C11 C12 96.4(8) . . . . ?
C13 C9 C11 C12 -20.2(10) . . . . ?
C18 C9 C11 C12 -141.1(7) . . . . ?
C14 O10 C12 C11 16.4(12) . . . . ?
C14 O10 C12 C4 -164.5(9) . . . . ?
C1 C11 C12 O10 -177.1(9) . . . . ?
C9 C11 C12 O10 5.3(12) . . . . ?
C1 C11 C12 C4 3.9(14) . . . . ?
C9 C11 C12 C4 -173.7(9) . . . . ?
C3 C4 C12 O10 177.2(15) . . . . ?
C15 C4 C12 O10 9.7(17) . . . . ?
C3 C4 C12 C11 -4(2) . . . . ?
C15 C4 C12 C11 -171.3(11) . . . . ?
C7 C8 C13 C14 -4(2) . . . . ?
C7 C8 C13 C9 176.7(18) . . . . ?
C11 C9 C13 C14 15.7(10) . . . . ?
C17 C9 C13 C14 -100.9(9) . . . . ?
C18 C9 C13 C14 136.3(8) . . . . ?
C11 C9 C13 C8 -165.1(11) . . . . ?
C17 C9 C13 C8 78.3(12) . . . . ?
C18 C9 C13 C8 -44.5(12) . . . . ?
C12 O10 C14 C13 -21.1(12) . . . . ?
C12 O10 C14 C5 160.0(10) . . . . ?
C8 C13 C14 O10 -175.3(11) . . . . ?
C9 C13 C14 O10 3.9(13) . . . . ?
C8 C13 C14 C5 3.5(16) . . . . ?
C9 C13 C14 C5 -177.3(10) . . . . ?
C6 C5 C14 O10 177(2) . . . . ?
C16 C5 C14 O10 -2.5(18) . . . . ?
C6 C5 C14 C13 -2(3) . . . . ?
C16 C5 C14 C13 178.6(12) . . . . ?
C11 C9 C17 F2 55.0(8) . . . . ?
C13 C9 C17 F2 173.4(7) . . . . ?
C18 C9 C17 F2 -65.5(9) . . . . ?
C11 C9 C17 F3 176.4(6) . . . . ?
C13 C9 C17 F3 -65.2(8) . . . . ?
C18 C9 C17 F3 55.9(8) . . . . ?
C11 C9 C17 F1 -64.6(8) . . . . ?
C13 C9 C17 F1 53.8(8) . . . . ?
C18 C9 C17 F1 174.9(6) . . . . ?
C11 C9 C18 C19 76.3(9) . . . . ?
C17 C9 C18 C19 -164.4(8) . . . . ?
C13 C9 C18 C19 -44.8(9) . . . . ?
C11 C9 C18 C23 -105.6(11) . . . . ?
C17 C9 C18 C23 13.7(12) . . . . ?
C13 C9 C18 C23 133.3(10) . . . . ?
C23 C18 C19 C20 2.7(16) . . . . ?
C9 C18 C19 C20 -179.0(10) . . . . ?
C18 C19 C20 C21 -0.5(18) . . . . ?
C19 C20 C21 C22 0.9(19) . . . . ?
C20 C21 C22 C23 -4(2) . . . . ?
C19 C18 C23 C22 -5.4(18) . . . . ?
C9 C18 C23 C22 176.5(10) . . . . ?
C21 C22 C23 C18 6(2) . . . . ?
C11B C1B C2B C3B -8(3) . . . . ?
C1B C2B C3B C4B 8(4) . . . . ?
C1B C2B C3B O1B -173(3) . . . . ?
C2B C3B C4B C12B -2(4) . . . . ?
O1B C3B C4B C12B 179(3) . . . . ?
C2B C3B C4B C15B -162(3) . . . . ?
O1B C3B C4B C15B 20(4) . . . . ?
C14B C5B C6B O2B 176(3) . . . . ?
C16B C5B C6B O2B 2(6) . . . . ?
C14B C5B C6B C7B -2(5) . . . . ?
C16B C5B C6B C7B -177(3) . . . . ?
C5B C6B C7B C8B 8(6) . . . . ?
O2B C6B C7B C8B -170(4) . . . . ?
C6B C7B C8B C13B -9(5) . . . . ?
C2B C1B C11B C12B 1(2) . . . . ?
C2B C1B C11B C9B -174.9(17) . . . . ?
C13B C9B C11B C12B 14.9(13) . . . . ?
C17B C9B C11B C12B -101.9(11) . . . . ?
C18B C9B C11B C12B 135.7(10) . . . . ?
C13B C9B C11B C1B -168.9(13) . . . . ?
C17B C9B C11B C1B 74.3(14) . . . . ?
C18B C9B C11B C1B -48.1(14) . . . . ?
C14B O10B C12B C11B -13.5(17) . . . . ?
C14B O10B C12B C4B 165.9(12) . . . . ?
C1B C11B C12B O10B -175.8(13) . . . . ?
C9B C11B C12B O10B 0.5(17) . . . . ?
C1B C11B C12B C4B 5(2) . . . . ?
C9B C11B C12B C4B -178.9(12) . . . . ?
C3B C4B C12B O10B 176(2) . . . . ?
C15B C4B C12B O10B -24(2) . . . . ?
C3B C4B C12B C11B -4(3) . . . . ?
C15B C4B C12B C11B 155.0(16) . . . . ?
C7B C8B C13B C14B 3(3) . . . . ?
C7B C8B C13B C9B 176(2) . . . . ?
C11B C9B C13B C14B -19.2(14) . . . . ?
C17B C9B C13B C14B 97.6(11) . . . . ?
C18B C9B C13B C14B -139.0(11) . . . . ?
C11B C9B C13B C8B 168.4(15) . . . . ?
C17B C9B C13B C8B -74.8(16) . . . . ?
C18B C9B C13B C8B 48.7(17) . . . . ?
C8B C13B C14B O10B -178.8(15) . . . . ?
C9B C13B C14B O10B 8.5(18) . . . . ?
C8B C13B C14B C5B 3(2) . . . . ?
C9B C13B C14B C5B -169.9(15) . . . . ?
C12B O10B C14B C13B 8.8(17) . . . . ?
C12B O10B C14B C5B -172.6(14) . . . . ?
C6B C5B C14B C13B -4(4) . . . . ?
C16B C5B C14B C13B 171.3(16) . . . . ?
C6B C5B C14B O10B 178(3) . . . . ?
C16B C5B C14B O10B -7(2) . . . . ?
C11B C9B C17B F2B -55.9(9) . . . . ?
C13B C9B C17B F2B -174.8(8) . . . . ?
C18B C9B C17B F2B 63.5(10) . . . . ?
C11B C9B C17B F1B 64.1(9) . . . . ?
C13B C9B C17B F1B -54.8(9) . . . . ?
C18B C9B C17B F1B -176.5(8) . . . . ?
C11B C9B C17B F3B -177.4(8) . . . . ?
C13B C9B C17B F3B 63.7(9) . . . . ?
C18B C9B C17B F3B -58.0(10) . . . . ?
C11B C9B C18B C23B 101.1(15) . . . . ?
C13B C9B C18B C23B -137.8(15) . . . . ?
C17B C9B C18B C23B -17.8(17) . . . . ?
C11B C9B C18B C19B -71.1(13) . . . . ?
C13B C9B C18B C19B 50.0(13) . . . . ?
C17B C9B C18B C19B 170.0(11) . . . . ?
C23B C18B C19B C20B 4(2) . . . . ?
C9B C18B C19B C20B 176.6(13) . . . . ?
C18B C19B C20B C21B -3(2) . . . . ?
C19B C20B C21B C22B 4(2) . . . . ?
C20B C21B C22B C23B -6(2) . . . . ?
C19B C18B C23B C22B -6(3) . . . . ?
C9B C18B C23B C22B -178.0(14) . . . . ?
C21B C22B C23B C18B 7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A O1 1.07(11) 1.70(11) 2.77(2) 172(8) 4 yes
C2 H2 F2 0.93 2.62 3.409(14) 143.4 3 yes
O1B H1C O2B 0.87 2.14 2.90(4) 147.1 2_664 yes

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035



