# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_CMC-01
_database_code_depnum_ccdc_archive 'CCDC 1988572'
loop_
_audit_author_name
_audit_author_address
'R. Sidick Basha'
;National University of Kaohsiung
Taiwan
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 O2'
_chemical_formula_weight         320.41

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.8570(6)
_cell_length_b                   10.6978(9)
_cell_length_c                   11.0526(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.428(5)
_cell_angle_gamma                90
_cell_volume                     895.52(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4172
_cell_measurement_theta_min      2.6893
_cell_measurement_theta_max      26.2718

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8079
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_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 8.3333
_diffrn_reflns_number            8878
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.911
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3288
_reflns_number_gt                3031
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.976

_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.1834P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.7(15)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         3288
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.52426(18) 0.72597(15) 0.07669(14) 0.0223(4) Uani 1 1 d . . . . .
O2 O 0.6726(2) 0.62411(17) -0.03885(16) 0.0279(4) Uani 1 1 d . . . . .
C1 C 0.3693(3) 0.7941(3) 0.4794(2) 0.0342(7) Uani 1 1 d . . . . .
H1 H 0.3304 0.7831 0.5530 0.041 Uiso 1 1 calc R U . . .
C2 C 0.4553(3) 0.6983(3) 0.4364(2) 0.0337(6) Uani 1 1 d . . . . .
H3 H 0.4750 0.6210 0.4803 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5132(3) 0.7143(3) 0.3294(2) 0.0275(5) Uani 1 1 d . . . . .
H4 H 0.5744 0.6486 0.3012 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4819(3) 0.8267(2) 0.2629(2) 0.0202(5) Uani 1 1 d . . . . .
C5 C 0.5360(3) 0.8452(2) 0.1434(2) 0.0203(5) Uani 1 1 d . . . . .
H22 H 0.4539 0.9065 0.0891 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7280(3) 0.8880(2) 0.1581(2) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.8059 0.8423 0.2309 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7548(3) 1.0249(2) 0.1814(2) 0.0205(5) Uani 1 1 d . . . . .
H11 H 0.6753 1.0806 0.1275 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8824(3) 1.0738(2) 0.2726(2) 0.0202(5) Uani 1 1 d . . . . .
H10 H 0.9609 1.0164 0.3250 0.024 Uiso 1 1 calc R U . . .
C9 C 0.9158(3) 1.2077(2) 0.3017(2) 0.0203(5) Uani 1 1 d . . . . .
C10 C 0.8180(3) 1.3029(2) 0.2281(2) 0.0230(5) Uani 1 1 d . . . . .
H6 H 0.7275 1.2822 0.1550 0.028 Uiso 1 1 calc R U . . .
C11 C 0.8521(3) 1.4277(2) 0.2610(2) 0.0285(6) Uani 1 1 d . . . . .
H9 H 0.7836 1.4914 0.2108 0.034 Uiso 1 1 calc R U . . .
C12 C 0.9849(3) 1.4602(3) 0.3664(3) 0.0306(6) Uani 1 1 d . . . . .
H2 H 1.0076 1.5456 0.3883 0.037 Uiso 1 1 calc R U . . .
C13 C 0.3400(3) 0.9064(3) 0.4149(2) 0.0315(6) Uani 1 1 d . . . . .
H24 H 0.2819 0.9727 0.4450 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3949(3) 0.9227(3) 0.3064(2) 0.0269(5) Uani 1 1 d . . . . .
H23 H 0.3730 0.9996 0.2620 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6563(3) 0.7170(2) 0.0182(2) 0.0203(5) Uani 1 1 d . . . . .
C16 C 0.7645(3) 0.8367(2) 0.0361(2) 0.0210(5) Uani 1 1 d . . . . .
C17 C 1.0842(3) 1.3672(3) 0.4394(2) 0.0295(6) Uani 1 1 d . . . . .
H8 H 1.1758 1.3886 0.5117 0.035 Uiso 1 1 calc R U . . .
C18 C 1.0497(3) 1.2426(2) 0.4071(2) 0.0242(5) Uani 1 1 d . . . . .
H7 H 1.1188 1.1796 0.4579 0.029 Uiso 1 1 calc R U . . .
C19 C 0.9596(3) 0.8111(2) 0.0464(2) 0.0276(6) Uani 1 1 d . . . . .
H16 H 0.9702 0.7825 -0.0365 0.033 Uiso 1 1 calc R U . . .
H12 H 1.0252 0.8909 0.0657 0.033 Uiso 1 1 calc R U . . .
C20 C 1.0485(3) 0.7149(3) 0.1447(3) 0.0334(6) Uani 1 1 d . . . . .
H15 H 0.9826 0.6361 0.1288 0.050 Uiso 1 1 calc R U . . .
H13 H 1.0501 0.7458 0.2285 0.050 Uiso 1 1 calc R U . . .
H14 H 1.1698 0.7008 0.1401 0.050 Uiso 1 1 calc R U . . .
C21 C 0.6831(3) 0.9236(3) -0.0767(2) 0.0275(6) Uani 1 1 d . . . . .
H17 H 0.5629 0.9474 -0.0729 0.033 Uiso 1 1 calc R U . . .
H18 H 0.7545 1.0010 -0.0671 0.033 Uiso 1 1 calc R U . . .
C22 C 0.6706(4) 0.8693(3) -0.2055(2) 0.0381(7) Uani 1 1 d . . . . .
H20 H 0.5970 0.7939 -0.2178 0.057 Uiso 1 1 calc R U . . .
H21 H 0.7891 0.8478 -0.2120 0.057 Uiso 1 1 calc R U . . .
H19 H 0.6175 0.9311 -0.2700 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.364(3) . ?
O1 C5 1.464(3) . ?
O2 C15 1.202(3) . ?
C1 C2 1.380(4) . ?
C1 C13 1.384(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(4) . ?
C2 H3 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H4 0.9500 . ?
C4 C14 1.389(3) . ?
C4 C5 1.504(3) . ?
C5 C6 1.543(3) . ?
C5 H22 1.0000 . ?
C6 C7 1.493(3) . ?
C6 C16 1.551(3) . ?
C6 H5 1.0000 . ?
C7 C8 1.325(3) . ?
C7 H11 0.9500 . ?
C8 C9 1.477(3) . ?
C8 H10 0.9500 . ?
C9 C18 1.397(3) . ?
C9 C10 1.399(3) . ?
C10 C11 1.391(4) . ?
C10 H6 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H9 0.9500 . ?
C12 C17 1.384(4) . ?
C12 H2 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H24 0.9500 . ?
C14 H23 0.9500 . ?
C15 C16 1.520(3) . ?
C16 C19 1.532(3) . ?
C16 C21 1.550(3) . ?
C17 C18 1.387(4) . ?
C17 H8 0.9500 . ?
C18 H7 0.9500 . ?
C19 C20 1.525(4) . ?
C19 H16 0.9900 . ?
C19 H12 0.9900 . ?
C20 H15 0.9800 . ?
C20 H13 0.9800 . ?
C20 H14 0.9800 . ?
C21 C22 1.516(4) . ?
C21 H17 0.9900 . ?
C21 H18 0.9900 . ?
C22 H20 0.9800 . ?
C22 H21 0.9800 . ?
C22 H19 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C5 110.26(16) . . ?
C2 C1 C13 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C13 C1 H1 120.1 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H3 119.9 . . ?
C3 C2 H3 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H4 119.9 . . ?
C4 C3 H4 119.9 . . ?
C14 C4 C3 119.2(2) . . ?
C14 C4 C5 119.1(2) . . ?
C3 C4 C5 121.6(2) . . ?
O1 C5 C4 109.41(18) . . ?
O1 C5 C6 103.89(17) . . ?
C4 C5 C6 116.31(17) . . ?
O1 C5 H22 109.0 . . ?
C4 C5 H22 109.0 . . ?
C6 C5 H22 109.0 . . ?
C7 C6 C5 113.47(18) . . ?
C7 C6 C16 116.58(19) . . ?
C5 C6 C16 101.84(17) . . ?
C7 C6 H5 108.2 . . ?
C5 C6 H5 108.2 . . ?
C16 C6 H5 108.2 . . ?
C8 C7 C6 124.2(2) . . ?
C8 C7 H11 117.9 . . ?
C6 C7 H11 117.9 . . ?
C7 C8 C9 127.1(2) . . ?
C7 C8 H10 116.5 . . ?
C9 C8 H10 116.5 . . ?
C18 C9 C10 117.8(2) . . ?
C18 C9 C8 119.4(2) . . ?
C10 C9 C8 122.8(2) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H6 119.7 . . ?
C9 C10 H6 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H9 119.7 . . ?
C10 C11 H9 119.7 . . ?
C17 C12 C11 119.5(2) . . ?
C17 C12 H2 120.3 . . ?
C11 C12 H2 120.3 . . ?
C1 C13 C14 120.4(2) . . ?
C1 C13 H24 119.8 . . ?
C14 C13 H24 119.8 . . ?
C4 C14 C13 120.0(2) . . ?
C4 C14 H23 120.0 . . ?
C13 C14 H23 120.0 . . ?
O2 C15 O1 120.5(2) . . ?
O2 C15 C16 129.1(2) . . ?
O1 C15 C16 110.36(19) . . ?
C15 C16 C19 111.9(2) . . ?
C15 C16 C21 107.66(17) . . ?
C19 C16 C21 110.91(19) . . ?
C15 C16 C6 100.68(17) . . ?
C19 C16 C6 114.32(17) . . ?
C21 C16 C6 110.8(2) . . ?
C12 C17 C18 119.9(2) . . ?
C12 C17 H8 120.0 . . ?
C18 C17 H8 120.0 . . ?
C17 C18 C9 121.5(2) . . ?
C17 C18 H7 119.2 . . ?
C9 C18 H7 119.2 . . ?
C20 C19 C16 115.6(2) . . ?
C20 C19 H16 108.4 . . ?
C16 C19 H16 108.4 . . ?
C20 C19 H12 108.4 . . ?
C16 C19 H12 108.4 . . ?
H16 C19 H12 107.4 . . ?
C19 C20 H15 109.5 . . ?
C19 C20 H13 109.5 . . ?
H15 C20 H13 109.5 . . ?
C19 C20 H14 109.5 . . ?
H15 C20 H14 109.5 . . ?
H13 C20 H14 109.5 . . ?
C22 C21 C16 115.8(2) . . ?
C22 C21 H17 108.3 . . ?
C16 C21 H17 108.3 . . ?
C22 C21 H18 108.3 . . ?
C16 C21 H18 108.3 . . ?
H17 C21 H18 107.4 . . ?
C21 C22 H20 109.5 . . ?
C21 C22 H21 109.5 . . ?
H20 C22 H21 109.5 . . ?
C21 C22 H19 109.5 . . ?
H20 C22 H19 109.5 . . ?
H21 C22 H19 109.5 . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_21JUL08_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2096072'
loop_
_audit_author_name
_audit_author_address
'Chih-Ming Chou'
;National University of Kaohsiung
Taiwan
;
_audit_update_record             
;
2021-07-13 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 F3 O2'
_chemical_formula_weight         388.41

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/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                   11.4578(9)
_cell_length_b                   22.1975(18)
_cell_length_c                   8.4627(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.640(2)
_cell_angle_gamma                90
_cell_volume                     2027.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      28.38

_exptl_crystal_description       cuboid
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.699
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker D8 Venture PHOTON III diff'
_diffrn_measurement_device_type  'φ and ω scans'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31882
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         28.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5072
_reflns_number_gt                4497
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0376P)²+1.0782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5072
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.54227(10) 0.50419(4) -0.15916(15) 0.0563(3) Uani 1 1 d . . . . .
F2 F 0.37783(9) 0.45111(5) -0.22771(15) 0.0515(3) Uani 1 1 d . . . . .
F3 F 0.48379(10) 0.45535(5) -0.39031(12) 0.0478(3) Uani 1 1 d . . . . .
O1 O 1.11450(9) 0.03627(4) 0.45819(13) 0.0279(2) Uani 1 1 d . . . . .
O2 O 0.97193(9) 0.07602(4) 0.55331(12) 0.0261(2) Uani 1 1 d . . . . .
H2A H 0.949064 0.040054 0.549292 0.039 Uiso 1 1 d R U . . .
C1 C 0.56720(12) 0.39857(6) -0.14376(17) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.54626(12) 0.34351(6) -0.22583(17) 0.0266(3) Uani 1 1 d . . . . .
H2 H 0.484226 0.339872 -0.333136 0.032 Uiso 1 1 calc R U . . .
C3 C 0.61594(12) 0.29396(6) -0.15101(16) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.601281 0.256321 -0.207735 0.029 Uiso 1 1 calc R U . . .
C4 C 0.70772(11) 0.29831(6) 0.00691(16) 0.0213(2) Uani 1 1 d . . . . .
C5 C 0.72508(13) 0.35388(6) 0.08838(17) 0.0286(3) Uani 1 1 d . . . . .
H5 H 0.785573 0.357546 0.196901 0.034 Uiso 1 1 calc R U . . .
C6 C 0.65597(13) 0.40376(6) 0.01431(18) 0.0290(3) Uani 1 1 d . . . . .
H6 H 0.669218 0.441337 0.071349 0.035 Uiso 1 1 calc R U . . .
C7 C 0.49403(13) 0.45219(6) -0.22837(18) 0.0304(3) Uani 1 1 d . . . . .
C8 C 0.78346(11) 0.24522(5) 0.07643(16) 0.0213(2) Uani 1 1 d . . . . .
H8 H 0.764345 0.209411 0.011285 0.026 Uiso 1 1 calc R U . . .
C9 C 0.87684(11) 0.24213(5) 0.22248(16) 0.0208(2) Uani 1 1 d . . . . .
H9 H 0.895852 0.277435 0.289789 0.025 Uiso 1 1 calc R U . . .
C10 C 0.95198(11) 0.18837(5) 0.28638(15) 0.0198(2) Uani 1 1 d . . . . .
C11 C 0.92295(11) 0.13471(5) 0.17386(15) 0.0195(2) Uani 1 1 d . . . . .
C12 C 0.81988(12) 0.09933(6) 0.16048(17) 0.0249(3) Uani 1 1 d . . . . .
H12 H 0.772677 0.106979 0.231619 0.030 Uiso 1 1 calc R U . . .
C13 C 0.78545(13) 0.05295(6) 0.04401(18) 0.0301(3) Uani 1 1 d . . . . .
H13 H 0.714550 0.029200 0.035093 0.036 Uiso 1 1 calc R U . . .
C14 C 0.85423(14) 0.04128(6) -0.05907(18) 0.0306(3) Uani 1 1 d . . . . .
H14 H 0.830640 0.009482 -0.138653 0.037 Uiso 1 1 calc R U . . .
C15 C 0.95721(13) 0.07582(6) -0.04638(17) 0.0286(3) Uani 1 1 d . . . . .
H15 H 1.004816 0.067589 -0.116636 0.034 Uiso 1 1 calc R U . . .
C16 C 0.99125(12) 0.12266(6) 0.06920(16) 0.0230(3) Uani 1 1 d . . . . .
H16 H 1.061644 0.146606 0.076725 0.028 Uiso 1 1 calc R U . . .
C17 C 1.04029(11) 0.19052(5) 0.43810(16) 0.0217(2) Uani 1 1 d . . . . .
H17 H 1.047917 0.228143 0.494212 0.026 Uiso 1 1 calc R U . . .
C18 C 1.12983(11) 0.14217(5) 0.53387(15) 0.0214(2) Uani 1 1 d . . . . .
C19 C 1.16089(13) 0.15707(6) 0.72299(16) 0.0272(3) Uani 1 1 d . . . . .
H19A H 1.196137 0.198211 0.743704 0.033 Uiso 1 1 calc R U . . .
H19B H 1.082773 0.157330 0.748787 0.033 Uiso 1 1 calc R U . . .
C20 C 1.25106(15) 0.11393(8) 0.84322(18) 0.0375(3) Uani 1 1 d . . . . .
H20A H 1.261078 0.125186 0.959022 0.056 Uiso 1 1 calc R U . . .
H20B H 1.331518 0.116047 0.826402 0.056 Uiso 1 1 calc R U . . .
H20C H 1.218703 0.072761 0.821705 0.056 Uiso 1 1 calc R U . . .
C21 C 1.24743(12) 0.14091(6) 0.48367(18) 0.0277(3) Uani 1 1 d . . . . .
H21A H 1.300725 0.107176 0.543095 0.033 Uiso 1 1 calc R U . . .
H21B H 1.222792 0.132786 0.361810 0.033 Uiso 1 1 calc R U . . .
C22 C 1.32305(15) 0.19889(7) 0.5224(2) 0.0389(4) Uani 1 1 d . . . . .
H22A H 1.269774 0.233048 0.470466 0.058 Uiso 1 1 calc R U . . .
H22B H 1.391364 0.196094 0.477568 0.058 Uiso 1 1 calc R U . . .
H22C H 1.356636 0.204812 0.644183 0.058 Uiso 1 1 calc R U . . .
C23 C 1.07055(11) 0.07951(5) 0.50795(15) 0.0211(2) 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 C7 1.3280(17) . ?
F2 C7 1.3335(17) . ?
F3 C7 1.3374(18) . ?
O1 C23 1.2226(15) . ?
O2 C23 1.3122(16) . ?
O2 H2A 0.8375 . ?
C1 C2 1.3862(19) . ?
C1 C6 1.3866(18) . ?
C1 C7 1.4929(18) . ?
C2 C3 1.3814(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3988(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3945(18) . ?
C4 C8 1.4644(16) . ?
C5 C6 1.3828(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.3373(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.4646(16) . ?
C9 H9 0.9500 . ?
C10 C17 1.3422(17) . ?
C10 C11 1.4910(17) . ?
C11 C16 1.3908(17) . ?
C11 C12 1.3908(18) . ?
C12 C13 1.3877(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3905(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.5175(16) . ?
C17 H17 0.9500 . ?
C18 C23 1.5309(17) . ?
C18 C21 1.5432(19) . ?
C18 C19 1.5540(18) . ?
C19 C20 1.5209(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.524(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O2 H2A 109.4 . . ?
C2 C1 C6 120.26(12) . . ?
C2 C1 C7 119.20(12) . . ?
C6 C1 C7 120.54(12) . . ?
C3 C2 C1 119.76(12) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.07(12) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.03(11) . . ?
C5 C4 C8 123.12(11) . . ?
C3 C4 C8 118.82(11) . . ?
C6 C5 C4 121.29(12) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.56(12) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
F1 C7 F2 106.37(13) . . ?
F1 C7 F3 106.65(12) . . ?
F2 C7 F3 105.15(12) . . ?
F1 C7 C1 113.46(12) . . ?
F2 C7 C1 112.60(12) . . ?
F3 C7 C1 112.02(12) . . ?
C9 C8 C4 126.48(12) . . ?
C9 C8 H8 116.8 . . ?
C4 C8 H8 116.8 . . ?
C8 C9 C10 124.85(11) . . ?
C8 C9 H9 117.6 . . ?
C10 C9 H9 117.6 . . ?
C17 C10 C9 118.99(11) . . ?
C17 C10 C11 125.03(11) . . ?
C9 C10 C11 115.97(10) . . ?
C16 C11 C12 118.93(12) . . ?
C16 C11 C10 120.52(11) . . ?
C12 C11 C10 120.27(11) . . ?
C13 C12 C11 120.50(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.07(13) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.02(13) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.02(13) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.45(12) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C10 C17 C18 129.99(11) . . ?
C10 C17 H17 115.0 . . ?
C18 C17 H17 115.0 . . ?
C17 C18 C23 112.23(10) . . ?
C17 C18 C21 111.22(10) . . ?
C23 C18 C21 109.30(10) . . ?
C17 C18 C19 106.21(10) . . ?
C23 C18 C19 106.14(10) . . ?
C21 C18 C19 111.62(11) . . ?
C20 C19 C18 115.08(12) . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
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 . . ?
C22 C21 C18 114.28(12) . . ?
C22 C21 H21A 108.7 . . ?
C18 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C18 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C23 O2 123.32(12) . . ?
O1 C23 C18 123.25(12) . . ?
O2 C23 C18 113.32(10) . . ?

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
C6 C1 C2 C3 -1.3(2) . . . . ?
C7 C1 C2 C3 178.07(12) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C2 C3 C4 C8 -176.69(12) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
C8 C4 C5 C6 176.45(13) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C7 C1 C6 C5 -178.21(13) . . . . ?
C2 C1 C7 F1 -163.92(13) . . . . ?
C6 C1 C7 F1 15.4(2) . . . . ?
C2 C1 C7 F2 75.18(17) . . . . ?
C6 C1 C7 F2 -105.45(16) . . . . ?
C2 C1 C7 F3 -43.09(18) . . . . ?
C6 C1 C7 F3 136.27(14) . . . . ?
C5 C4 C8 C9 0.0(2) . . . . ?
C3 C4 C8 C9 177.94(13) . . . . ?
C4 C8 C9 C10 -178.84(12) . . . . ?
C8 C9 C10 C17 -177.56(13) . . . . ?
C8 C9 C10 C11 2.59(18) . . . . ?
C17 C10 C11 C16 -83.49(16) . . . . ?
C9 C10 C11 C16 96.36(14) . . . . ?
C17 C10 C11 C12 102.68(15) . . . . ?
C9 C10 C11 C12 -77.47(15) . . . . ?
C16 C11 C12 C13 -0.29(18) . . . . ?
C10 C11 C12 C13 173.64(12) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C15 C16 C11 0.67(19) . . . . ?
C12 C11 C16 C15 -0.28(18) . . . . ?
C10 C11 C16 C15 -174.20(11) . . . . ?
C9 C10 C17 C18 179.66(12) . . . . ?
C11 C10 C17 C18 -0.5(2) . . . . ?
C10 C17 C18 C23 -36.76(19) . . . . ?
C10 C17 C18 C21 86.04(16) . . . . ?
C10 C17 C18 C19 -152.32(14) . . . . ?
C17 C18 C19 C20 -179.62(12) . . . . ?
C23 C18 C19 C20 60.75(15) . . . . ?
C21 C18 C19 C20 -58.25(15) . . . . ?
C17 C18 C21 C22 62.09(15) . . . . ?
C23 C18 C21 C22 -173.44(11) . . . . ?
C19 C18 C21 C22 -56.33(15) . . . . ?
C17 C18 C23 O1 125.25(13) . . . . ?
C21 C18 C23 O1 1.37(16) . . . . ?
C19 C18 C23 O1 -119.15(13) . . . . ?
C17 C18 C23 O2 -58.36(14) . . . . ?
C21 C18 C23 O2 177.77(10) . . . . ?
C19 C18 C23 O2 57.25(13) . . . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.042



