# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_24085_a
_database_code_depnum_ccdc_archive 'CCDC 2383107'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2024-09-10 deposited with the CCDC.	2026-06-11 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         'C25 H21 F3 O2'
_chemical_formula_sum            'C25 H21 F3 O2'
_chemical_formula_weight         410.42

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.9675(2)
_cell_length_b                   9.7971(2)
_cell_length_c                   22.7498(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1998.70(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      68.19
_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.873
_shelx_estimated_absorpt_T_min   0.678
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77205
_exptl_absorpt_correction_T_max  0.96554
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18545
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.886
_diffrn_reflns_theta_max         68.190
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3649
_reflns_number_gt                3588
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2014-7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v817 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the unambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.4911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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 
;
 Flack x determined using 1509 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3649
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
F1 F 0.62175(14) 0.38577(14) 0.09214(5) 0.0339(3) Uani 1 1 d . . . . .
C1 C 0.90721(19) 0.26854(18) 0.23433(8) 0.0167(4) Uani 1 1 d . . . . .
H1 H 0.973354 0.339235 0.252372 0.020 Uiso 1 1 calc R U . . .
O1 O 0.94270(15) 0.12866(13) 0.24820(6) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.27033(16) 0.40349(16) 0.37074(7) 0.0345(4) Uani 1 1 d . . . . .
F2 F 0.65511(14) 0.59902(13) 0.11146(5) 0.0340(3) Uani 1 1 d . . . . .
C2 C 0.81217(19) 0.19198(18) 0.27528(8) 0.0171(4) Uani 1 1 d . . . . .
H2 H 0.713822 0.162142 0.259030 0.021 Uiso 1 1 calc R U . . .
C6 C 0.8119(3) 0.2551(2) 0.46085(9) 0.0297(5) Uani 1 1 d . . . . .
H6 H 0.810933 0.268642 0.502200 0.036 Uiso 1 1 calc R U . . .
C5 C 0.9419(2) 0.2764(2) 0.42916(9) 0.0282(4) Uani 1 1 d . . . . .
H5 H 1.029883 0.304773 0.448940 0.034 Uiso 1 1 calc R U . . .
C4 C 0.9445(2) 0.2565(2) 0.36877(8) 0.0220(4) Uani 1 1 d . . . . .
H4 H 1.033767 0.271764 0.347230 0.026 Uiso 1 1 calc R U . . .
F3 F 0.82670(12) 0.48431(12) 0.06839(5) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.8156(2) 0.21414(17) 0.33993(8) 0.0175(4) Uani 1 1 d . . . . .
C7 C 0.6834(2) 0.2141(2) 0.43199(9) 0.0273(4) Uani 1 1 d . . . . .
H7 H 0.594054 0.200079 0.453579 0.033 Uiso 1 1 calc R U . . .
C9 C 0.85687(19) 0.29621(18) 0.17187(8) 0.0159(4) Uani 1 1 d . . . . .
H9 H 0.776845 0.229145 0.161723 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6849(2) 0.19350(19) 0.37163(8) 0.0217(4) Uani 1 1 d . . . . .
H8 H 0.596633 0.165294 0.351972 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7879(2) 0.44206(18) 0.17043(8) 0.0170(4) Uani 1 1 d . . . . .
H10 H 0.870458 0.508133 0.178313 0.020 Uiso 1 1 calc R U . . .
C11 C 0.67320(19) 0.45925(17) 0.21958(7) 0.0157(3) Uani 1 1 d . . . . .
C12 C 0.7120(2) 0.53748(18) 0.26842(8) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.802217 0.588369 0.268098 0.023 Uiso 1 1 calc R U . . .
C13 C 0.6201(2) 0.54177(19) 0.31761(8) 0.0202(4) Uani 1 1 d . . . . .
H13 H 0.648997 0.593922 0.350920 0.024 Uiso 1 1 calc R U . . .
C14 C 0.4859(2) 0.47006(18) 0.31838(8) 0.0188(4) Uani 1 1 d . . . . .
C15 C 0.4443(2) 0.39593(19) 0.26859(8) 0.0211(4) Uani 1 1 d . . . . .
H15 H 0.351728 0.348857 0.268123 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5367(2) 0.39030(19) 0.21992(8) 0.0198(4) Uani 1 1 d . . . . .
H16 H 0.507095 0.339113 0.186436 0.024 Uiso 1 1 calc R U . . .
C17 C 0.3891(2) 0.46309(19) 0.37242(9) 0.0230(4) Uani 1 1 d . . . . .
C18 C 0.4425(2) 0.5298(2) 0.42786(9) 0.0291(4) Uani 1 1 d . . . . .
H18A H 0.540666 0.493153 0.438382 0.044 Uiso 1 1 calc R U . . .
H18B H 0.371726 0.511180 0.459679 0.044 Uiso 1 1 calc R U . . .
H18C H 0.450158 0.628533 0.421751 0.044 Uiso 1 1 calc R U . . .
C19 C 0.7238(2) 0.4770(2) 0.11072(8) 0.0219(4) Uani 1 1 d . . . . .
C20 C 0.9864(2) 0.27549(18) 0.12936(7) 0.0173(4) Uani 1 1 d . . . . .
C21 C 1.1085(2) 0.36303(19) 0.12911(8) 0.0218(4) Uani 1 1 d . . . . .
H21 H 1.113119 0.435947 0.156579 0.026 Uiso 1 1 calc R U . . .
C22 C 1.2241(2) 0.3449(2) 0.08903(8) 0.0237(4) Uani 1 1 d . . . . .
H22 H 1.306305 0.405997 0.088937 0.028 Uiso 1 1 calc R U . . .
C23 C 1.2195(2) 0.2378(2) 0.04926(8) 0.0243(4) Uani 1 1 d . . . . .
H23 H 1.296917 0.226630 0.021181 0.029 Uiso 1 1 calc R U . . .
C24 C 1.1014(2) 0.1476(2) 0.05080(8) 0.0265(4) Uani 1 1 d . . . . .
H24 H 1.099485 0.072284 0.024519 0.032 Uiso 1 1 calc R U . . .
C25 C 0.9850(2) 0.1660(2) 0.09059(8) 0.0224(4) Uani 1 1 d . . . . .
H25 H 0.904141 0.103343 0.091186 0.027 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Thirteen 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.1550
0.00 1.00 0.00 0.0290
0.00 0.00 -1.00 0.0010
0.00 0.00 1.00 0.0370
-1.00 0.00 0.00 0.1740
1.00 0.00 0.00 0.2410

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 C19 1.347(2) . ?
C1 O1 1.442(2) . ?
C1 C2 1.469(2) . ?
C1 C9 1.515(2) . ?
C1 H1 1.0000 . ?
O1 C2 1.461(2) . ?
O2 C17 1.215(2) . ?
F2 C19 1.345(2) . ?
C2 C3 1.487(2) . ?
C2 H2 1.0000 . ?
C6 C7 1.386(3) . ?
C6 C5 1.386(3) . ?
C6 H6 0.9500 . ?
C5 C4 1.388(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.393(3) . ?
C4 H4 0.9500 . ?
F3 C19 1.336(2) . ?
C3 C8 1.391(3) . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C9 C20 1.525(2) . ?
C9 C10 1.558(2) . ?
C9 H9 1.0000 . ?
C8 H8 0.9500 . ?
C10 C19 1.514(2) . ?
C10 C11 1.528(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.394(2) . ?
C11 C16 1.398(3) . ?
C12 C13 1.391(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(3) . ?
C14 C17 1.507(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.499(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C25 1.389(3) . ?
C20 C21 1.391(3) . ?
C21 C22 1.392(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(3) . ?
C24 H24 0.9500 . ?
C25 H25 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
O1 C1 C2 60.25(11) . . ?
O1 C1 C9 116.17(14) . . ?
C2 C1 C9 120.88(15) . . ?
O1 C1 H1 116.0 . . ?
C2 C1 H1 116.0 . . ?
C9 C1 H1 116.0 . . ?
C1 O1 C2 60.78(11) . . ?
O1 C2 C1 58.96(11) . . ?
O1 C2 C3 117.55(15) . . ?
C1 C2 C3 122.74(16) . . ?
O1 C2 H2 115.2 . . ?
C1 C2 H2 115.2 . . ?
C3 C2 H2 115.2 . . ?
C7 C6 C5 119.75(18) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C4 C3 119.60(19) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C8 C3 C4 119.91(17) . . ?
C8 C3 C2 118.31(17) . . ?
C4 C3 C2 121.77(17) . . ?
C6 C7 C8 120.21(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C1 C9 C20 110.12(14) . . ?
C1 C9 C10 107.60(14) . . ?
C20 C9 C10 114.29(14) . . ?
C1 C9 H9 108.2 . . ?
C20 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C7 C8 C3 119.98(19) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
C19 C10 C11 112.11(14) . . ?
C19 C10 C9 112.15(15) . . ?
C11 C10 C9 110.67(14) . . ?
C19 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C9 C10 H10 107.2 . . ?
C12 C11 C16 118.68(16) . . ?
C12 C11 C10 118.40(15) . . ?
C16 C11 C10 122.67(15) . . ?
C13 C12 C11 120.66(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.46(17) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 118.84(17) . . ?
C13 C14 C17 122.05(17) . . ?
C15 C14 C17 119.00(17) . . ?
C16 C15 C14 120.67(17) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.62(17) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O2 C17 C18 121.08(18) . . ?
O2 C17 C14 120.07(18) . . ?
C18 C17 C14 118.85(17) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F3 C19 F2 106.11(15) . . ?
F3 C19 F1 106.19(15) . . ?
F2 C19 F1 106.41(15) . . ?
F3 C19 C10 113.39(15) . . ?
F2 C19 C10 111.31(15) . . ?
F1 C19 C10 112.91(15) . . ?
C25 C20 C21 118.75(17) . . ?
C25 C20 C9 119.90(16) . . ?
C21 C20 C9 121.35(16) . . ?
C20 C21 C22 120.67(17) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 120.16(18) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.41(17) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.58(18) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 120.36(18) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?

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
C9 C1 O1 C2 -112.21(17) . . . . ?
C1 O1 C2 C3 -113.46(17) . . . . ?
C9 C1 C2 O1 104.48(17) . . . . ?
O1 C1 C2 C3 104.77(18) . . . . ?
C9 C1 C2 C3 -150.75(16) . . . . ?
C7 C6 C5 C4 -0.2(3) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C5 C4 C3 C8 0.7(3) . . . . ?
C5 C4 C3 C2 179.72(18) . . . . ?
O1 C2 C3 C8 -141.71(16) . . . . ?
C1 C2 C3 C8 149.14(17) . . . . ?
O1 C2 C3 C4 39.3(2) . . . . ?
C1 C2 C3 C4 -29.9(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
O1 C1 C9 C20 -68.60(19) . . . . ?
C2 C1 C9 C20 -138.10(17) . . . . ?
O1 C1 C9 C10 166.24(14) . . . . ?
C2 C1 C9 C10 96.75(18) . . . . ?
C6 C7 C8 C3 -0.1(3) . . . . ?
C4 C3 C8 C7 -0.5(3) . . . . ?
C2 C3 C8 C7 -179.54(17) . . . . ?
C1 C9 C10 C19 -176.05(14) . . . . ?
C20 C9 C10 C19 61.3(2) . . . . ?
C1 C9 C10 C11 -50.05(18) . . . . ?
C20 C9 C10 C11 -172.67(14) . . . . ?
C19 C10 C11 C12 -128.44(17) . . . . ?
C9 C10 C11 C12 105.53(18) . . . . ?
C19 C10 C11 C16 57.3(2) . . . . ?
C9 C10 C11 C16 -68.7(2) . . . . ?
C16 C11 C12 C13 3.0(3) . . . . ?
C10 C11 C12 C13 -171.51(16) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C12 C13 C14 C17 175.10(17) . . . . ?
C13 C14 C15 C16 1.9(3) . . . . ?
C17 C14 C15 C16 -174.41(16) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
C12 C11 C16 C15 -2.2(3) . . . . ?
C10 C11 C16 C15 172.07(17) . . . . ?
C13 C14 C17 O2 177.45(18) . . . . ?
C15 C14 C17 O2 -6.4(3) . . . . ?
C13 C14 C17 C18 -3.0(3) . . . . ?
C15 C14 C17 C18 173.17(18) . . . . ?
C11 C10 C19 F3 169.81(15) . . . . ?
C9 C10 C19 F3 -65.0(2) . . . . ?
C11 C10 C19 F2 50.3(2) . . . . ?
C9 C10 C19 F2 175.47(14) . . . . ?
C11 C10 C19 F1 -69.35(19) . . . . ?
C9 C10 C19 F1 55.9(2) . . . . ?
C1 C9 C20 C25 110.78(18) . . . . ?
C10 C9 C20 C25 -127.99(18) . . . . ?
C1 C9 C20 C21 -68.1(2) . . . . ?
C10 C9 C20 C21 53.2(2) . . . . ?
C25 C20 C21 C22 2.8(3) . . . . ?
C9 C20 C21 C22 -178.33(17) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C21 C22 C23 C24 -1.7(3) . . . . ?
C22 C23 C24 C25 2.1(3) . . . . ?
C21 C20 C25 C24 -2.3(3) . . . . ?
C9 C20 C25 C24 178.79(17) . . . . ?
C23 C24 C25 C20 -0.1(3) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_24089_a
_database_code_depnum_ccdc_archive 'CCDC 2383108'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2024-09-10 deposited with the CCDC.	2026-06-11 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         'C23 H17 Cl2 F3'
_chemical_formula_sum            'C23 H17 Cl2 F3'
_chemical_formula_weight         421.26

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'
Cl Cl 0.3639 0.7018 '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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

_cell_length_a                   16.9540(3)
_cell_length_b                   20.1285(3)
_cell_length_c                   5.70930(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1948.35(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      5.11
_cell_measurement_theta_max      68.17
_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    3.296
_shelx_estimated_absorpt_T_min   0.340
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58650
_exptl_absorpt_correction_T_max  0.88818
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17289
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         5.110
_diffrn_reflns_theta_max         68.159
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3462
_reflns_number_gt                3430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.974

_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 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors showed 
little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.9066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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 
;
 Flack x determined using 1410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3462
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Cl1 Cl 0.50718(4) 0.28054(3) 0.20698(12) 0.02173(17) Uani 1 1 d . . . . .
Cl2 Cl 0.69668(4) 0.36917(4) 0.88927(15) 0.0320(2) Uani 1 1 d . . . . .
F1 F 0.29857(10) 0.44403(8) 0.1855(3) 0.0250(4) Uani 1 1 d . . . . .
F2 F 0.32667(10) 0.47851(8) 0.5330(3) 0.0238(4) Uani 1 1 d . . . . .
F3 F 0.41649(10) 0.47616(8) 0.2654(3) 0.0258(4) Uani 1 1 d . . . . .
C1 C 0.37657(15) 0.37193(12) 0.4205(5) 0.0138(5) Uani 1 1 d . . . . .
H1 H 0.379524 0.345381 0.272752 0.017 Uiso 1 1 calc R U . . .
C2 C 0.45803(15) 0.37051(13) 0.5335(5) 0.0155(5) Uani 1 1 d . . . . .
C3 C 0.51997(16) 0.33217(12) 0.4478(5) 0.0160(6) Uani 1 1 d . . . . .
C4 C 0.59432(16) 0.33201(14) 0.5531(6) 0.0203(6) Uani 1 1 d . . . . .
H4 H 0.636009 0.305857 0.490916 0.024 Uiso 1 1 calc R U . . .
C5 C 0.60573(16) 0.37063(14) 0.7489(5) 0.0206(6) Uani 1 1 d . . . . .
C6 C 0.54574(17) 0.40935(14) 0.8421(5) 0.0215(6) Uani 1 1 d . . . . .
H6 H 0.554456 0.435648 0.977810 0.026 Uiso 1 1 calc R U . . .
C7 C 0.47268(16) 0.40874(13) 0.7323(5) 0.0186(6) Uani 1 1 d . . . . .
H7 H 0.431346 0.435243 0.794654 0.022 Uiso 1 1 calc R U . . .
C8 C 0.35441(16) 0.44264(14) 0.3538(5) 0.0181(6) Uani 1 1 d . . . . .
C9 C 0.31490(15) 0.33764(12) 0.5840(5) 0.0135(5) Uani 1 1 d . . . . .
H9 H 0.321681 0.356594 0.744634 0.016 Uiso 1 1 calc R U . . .
C10 C 0.22888(15) 0.34748(12) 0.5135(5) 0.0145(5) Uani 1 1 d . . . . .
C11 C 0.17811(16) 0.37953(13) 0.6682(5) 0.0182(5) Uani 1 1 d . . . . .
H11 H 0.198162 0.396960 0.810942 0.022 Uiso 1 1 calc R U . . .
C12 C 0.09833(17) 0.38633(14) 0.6163(6) 0.0235(6) Uani 1 1 d . . . . .
H12 H 0.064300 0.408251 0.723576 0.028 Uiso 1 1 calc R U . . .
C13 C 0.06848(17) 0.36129(15) 0.4093(6) 0.0260(7) Uani 1 1 d . . . . .
H13 H 0.013988 0.365871 0.374165 0.031 Uiso 1 1 calc R U . . .
C14 C 0.11876(18) 0.32917(15) 0.2517(5) 0.0236(7) Uani 1 1 d . . . . .
H14 H 0.098482 0.312056 0.108794 0.028 Uiso 1 1 calc R U . . .
C15 C 0.19845(18) 0.32226(13) 0.3041(5) 0.0198(6) Uani 1 1 d . . . . .
H15 H 0.232414 0.300258 0.196878 0.024 Uiso 1 1 calc R U . . .
C16 C 0.33192(15) 0.26397(12) 0.5984(5) 0.0156(5) Uani 1 1 d . . . . .
H16 H 0.329126 0.238919 0.457612 0.019 Uiso 1 1 calc R U . . .
C17 C 0.35053(14) 0.23181(13) 0.7943(5) 0.0147(5) Uani 1 1 d . . . . .
H17 H 0.356663 0.257813 0.932014 0.018 Uiso 1 1 calc R U . . .
C18 C 0.36254(14) 0.15939(13) 0.8177(5) 0.0135(5) Uani 1 1 d . . . . .
C19 C 0.39721(15) 0.13416(14) 1.0207(5) 0.0165(5) Uani 1 1 d . . . . .
H19 H 0.412581 0.163620 1.142421 0.020 Uiso 1 1 calc R U . . .
C20 C 0.40951(16) 0.06587(14) 1.0463(5) 0.0182(6) Uani 1 1 d . . . . .
H20 H 0.433392 0.049174 1.184873 0.022 Uiso 1 1 calc R U . . .
C21 C 0.38702(17) 0.02254(14) 0.8706(6) 0.0219(6) Uani 1 1 d . . . . .
H21 H 0.395810 -0.023824 0.887564 0.026 Uiso 1 1 calc R U . . .
C22 C 0.35160(18) 0.04708(14) 0.6698(6) 0.0227(6) Uani 1 1 d . . . . .
H22 H 0.336093 0.017391 0.548886 0.027 Uiso 1 1 calc R U . . .
C23 C 0.33870(16) 0.11454(14) 0.6442(5) 0.0178(6) Uani 1 1 d . . . . .
H23 H 0.313327 0.130648 0.507152 0.021 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Twelve frame 
series were integrated and filtered for statistical outliers using SAINT 
(Bruker, 2016) then corrected for absorption by integration using 
SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale the combined 
data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.1800
0.00 0.00 1.00 0.2090
0.00 1.00 0.00 0.0170
0.00 -1.00 0.00 0.0220
1.00 -1.00 0.00 0.0340
-1.00 1.00 0.00 0.0320
1.00 1.00 0.00 0.0270

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
Cl1 C3 1.737(3) . ?
Cl2 C5 1.738(3) . ?
F1 C8 1.349(3) . ?
F2 C8 1.338(3) . ?
F3 C8 1.348(3) . ?
C1 C8 1.520(3) . ?
C1 C2 1.525(3) . ?
C1 C9 1.562(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.392(4) . ?
C2 C7 1.394(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.375(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C16 1.513(3) . ?
C9 C10 1.526(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.392(4) . ?
C10 C15 1.397(4) . ?
C11 C12 1.391(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.398(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.331(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.478(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(4) . ?
C18 C23 1.400(4) . ?
C19 C20 1.398(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(4) . ?
C22 H22 0.9500 . ?
C23 H23 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
C8 C1 C2 110.3(2) . . ?
C8 C1 C9 113.4(2) . . ?
C2 C1 C9 110.2(2) . . ?
C8 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
C9 C1 H1 107.5 . . ?
C3 C2 C7 117.2(2) . . ?
C3 C2 C1 123.1(3) . . ?
C7 C2 C1 119.7(2) . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 Cl1 121.0(2) . . ?
C4 C3 Cl1 116.9(2) . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 Cl2 119.3(2) . . ?
C6 C5 Cl2 118.9(2) . . ?
C5 C6 C7 118.4(3) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C2 122.1(3) . . ?
C6 C7 H7 118.9 . . ?
C2 C7 H7 118.9 . . ?
F2 C8 F3 106.9(2) . . ?
F2 C8 F1 106.7(2) . . ?
F3 C8 F1 105.7(2) . . ?
F2 C8 C1 113.6(2) . . ?
F3 C8 C1 111.7(2) . . ?
F1 C8 C1 111.8(2) . . ?
C16 C9 C10 108.9(2) . . ?
C16 C9 C1 109.7(2) . . ?
C10 C9 C1 115.1(2) . . ?
C16 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
C1 C9 H9 107.6 . . ?
C11 C10 C15 118.9(3) . . ?
C11 C10 C9 118.9(3) . . ?
C15 C10 C9 122.1(2) . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C17 C16 C9 124.6(2) . . ?
C17 C16 H16 117.7 . . ?
C9 C16 H16 117.7 . . ?
C16 C17 C18 126.1(3) . . ?
C16 C17 H17 117.0 . . ?
C18 C17 H17 117.0 . . ?
C19 C18 C23 118.3(2) . . ?
C19 C18 C17 119.5(2) . . ?
C23 C18 C17 122.2(2) . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 120.9(3) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?

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
C8 C1 C2 C3 -123.0(3) . . . . ?
C9 C1 C2 C3 111.0(3) . . . . ?
C8 C1 C2 C7 57.2(3) . . . . ?
C9 C1 C2 C7 -68.8(3) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 179.5(2) . . . . ?
C7 C2 C3 Cl1 177.8(2) . . . . ?
C1 C2 C3 Cl1 -2.0(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
Cl1 C3 C4 C5 -177.9(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 Cl2 177.8(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
Cl2 C5 C6 C7 -178.3(2) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C3 C2 C7 C6 0.2(4) . . . . ?
C1 C2 C7 C6 -180.0(3) . . . . ?
C2 C1 C8 F2 -81.0(3) . . . . ?
C9 C1 C8 F2 43.2(3) . . . . ?
C2 C1 C8 F3 40.0(3) . . . . ?
C9 C1 C8 F3 164.2(2) . . . . ?
C2 C1 C8 F1 158.2(2) . . . . ?
C9 C1 C8 F1 -77.6(3) . . . . ?
C8 C1 C9 C16 167.7(2) . . . . ?
C2 C1 C9 C16 -68.0(3) . . . . ?
C8 C1 C9 C10 44.5(3) . . . . ?
C2 C1 C9 C10 168.7(2) . . . . ?
C16 C9 C10 C11 117.4(3) . . . . ?
C1 C9 C10 C11 -118.9(3) . . . . ?
C16 C9 C10 C15 -59.1(3) . . . . ?
C1 C9 C10 C15 64.6(3) . . . . ?
C15 C10 C11 C12 0.1(4) . . . . ?
C9 C10 C11 C12 -176.5(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C10 -0.2(4) . . . . ?
C11 C10 C15 C14 0.0(4) . . . . ?
C9 C10 C15 C14 176.5(2) . . . . ?
C10 C9 C16 C17 -114.9(3) . . . . ?
C1 C9 C16 C17 118.3(3) . . . . ?
C9 C16 C17 C18 175.8(2) . . . . ?
C16 C17 C18 C19 167.0(3) . . . . ?
C16 C17 C18 C23 -14.3(4) . . . . ?
C23 C18 C19 C20 1.6(4) . . . . ?
C17 C18 C19 C20 -179.7(2) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C18 1.4(4) . . . . ?
C19 C18 C23 C22 -2.2(4) . . . . ?
C17 C18 C23 C22 179.2(3) . . . . ?

_refine_diff_density_max         0.539
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.052

