# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 
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data_mo_1095_cg_0m
_database_code_depnum_ccdc_archive 'CCDC 2056406'
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2020-08-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
'cgolz@gwdg.de '
Lutz.Ackermann@chemie.uni-goettingen.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H13 F3 O2'
_chemical_formula_sum            'C22 H13 F3 O2'
_chemical_formula_weight         366.32
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.4761(8)
_cell_length_b                   10.1707(8)
_cell_length_c                   33.232(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.508(3)
_cell_angle_gamma                90
_cell_volume                     3510.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9753
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.660
_cell_measurement_theta_min      2.354
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.8496
_exptl_absorpt_correction_T_min  0.7935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0766 before and 0.0411 after correction.
The Ratio of minimum to maximum transmission is 0.9340.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.226
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            54286
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.706
_diffrn_reflns_theta_min         2.096
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture AgMo Dual Source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7615
_reflns_number_total             9039
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         9039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+1.9986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1300
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35), C37(H37), C38(H38), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.21589(11) 0.40203(10) 0.35573(3) 0.0433(2) Uani 1 1 d . . . . .
F2 F 0.02182(10) 0.44958(10) 0.32909(3) 0.0410(2) Uani 1 1 d . . . . .
F3 F 0.15464(11) 0.60237(9) 0.35012(3) 0.0420(2) Uani 1 1 d . . . . .
O1 O 0.13335(14) 0.26306(11) 0.28552(4) 0.0432(3) Uani 1 1 d . . . . .
O2 O 0.47411(16) 0.90263(14) 0.18575(4) 0.0564(4) Uani 1 1 d . . . . .
C1 C 0.14578(15) 0.48678(15) 0.33108(4) 0.0301(3) Uani 1 1 d . . . . .
C2 C 0.18708(13) 0.48862(14) 0.28891(4) 0.0248(3) Uani 1 1 d . . . . .
C3 C 0.23330(13) 0.59510(13) 0.27177(4) 0.0234(3) Uani 1 1 d . . . . .
C4 C 0.27044(13) 0.59102(14) 0.22839(4) 0.0248(3) Uani 1 1 d . . . . .
C5 C 0.23171(14) 0.46393(15) 0.20544(4) 0.0278(3) Uani 1 1 d . . . . .
C6 C 0.19180(14) 0.35364(14) 0.22509(4) 0.0288(3) Uani 1 1 d . . . . .
C7 C 0.16957(15) 0.35926(14) 0.26802(4) 0.0287(3) Uani 1 1 d . . . . .
C8 C 0.16427(17) 0.23561(16) 0.20377(5) 0.0385(4) Uani 1 1 d . . . . .
H8 H 0.139730 0.159816 0.217606 0.046 Uiso 1 1 calc R U . . .
C9 C 0.17289(19) 0.22978(19) 0.16273(6) 0.0469(5) Uani 1 1 d . . . . .
H9 H 0.153439 0.150342 0.148168 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2100(2) 0.34021(19) 0.14288(5) 0.0467(4) Uani 1 1 d . . . . .
H10 H 0.214478 0.336480 0.114536 0.056 Uiso 1 1 calc R U . . .
C11 C 0.24078(17) 0.45655(18) 0.16388(5) 0.0387(4) Uani 1 1 d . . . . .
H11 H 0.267992 0.531056 0.150004 0.046 Uiso 1 1 calc R U . . .
C12 C 0.20709(15) 0.70520(15) 0.20445(4) 0.0307(3) Uani 1 1 d . . . . .
H12 H 0.115727 0.708063 0.199668 0.037 Uiso 1 1 calc R U . . .
C13 C 0.27304(18) 0.80207(16) 0.18971(5) 0.0374(4) Uani 1 1 d . . . . .
H13 H 0.227258 0.869438 0.174132 0.045 Uiso 1 1 calc R U . . .
C14 C 0.41439(18) 0.80794(16) 0.19679(5) 0.0384(4) Uani 1 1 d . . . . .
C15 C 0.48042(16) 0.69668(17) 0.21798(5) 0.0354(3) Uani 1 1 d . . . . .
H15 H 0.571841 0.694084 0.221242 0.042 Uiso 1 1 calc R U . . .
C16 C 0.41653(14) 0.59851(15) 0.23291(4) 0.0301(3) Uani 1 1 d . . . . .
H16 H 0.464720 0.529813 0.247073 0.036 Uiso 1 1 calc R U . . .
C17 C 0.25794(15) 0.72509(14) 0.29248(4) 0.0276(3) Uani 1 1 d . . . . .
C18 C 0.16463(18) 0.82273(16) 0.28714(5) 0.0381(4) Uani 1 1 d . . . . .
H18 H 0.084922 0.806325 0.270769 0.046 Uiso 1 1 calc R U . . .
C19 C 0.1877(2) 0.94466(18) 0.30575(6) 0.0520(5) Uani 1 1 d . . . . .
H19 H 0.123667 1.011326 0.302141 0.062 Uiso 1 1 calc R U . . .
C20 C 0.3036(3) 0.9684(2) 0.32942(7) 0.0593(6) Uani 1 1 d . . . . .
H20 H 0.319204 1.051663 0.342088 0.071 Uiso 1 1 calc R U . . .
C21 C 0.3965(2) 0.8727(2) 0.33479(6) 0.0585(6) Uani 1 1 d . . . . .
H21 H 0.476118 0.890084 0.351111 0.070 Uiso 1 1 calc R U . . .
C22 C 0.37483(17) 0.74935(19) 0.31638(5) 0.0406(4) Uani 1 1 d . . . . .
H22 H 0.439163 0.683054 0.320170 0.049 Uiso 1 1 calc R U . . .
F4 F 0.60971(12) 0.82296(12) 0.59286(3) 0.0569(3) Uani 1 1 d . . . . .
F5 F 0.41658(13) 0.85918(15) 0.60040(4) 0.0651(4) Uani 1 1 d . . . . .
F6 F 0.52131(13) 1.00475(11) 0.57111(4) 0.0562(3) Uani 1 1 d . . . . .
O3 O 0.66614(12) 0.87075(15) 0.51670(4) 0.0498(3) Uani 1 1 d . . . . .
O4 O -0.06044(12) 0.60254(16) 0.42532(5) 0.0560(4) Uani 1 1 d . . . . .
C23 C 0.50044(18) 0.87590(18) 0.57422(5) 0.0409(4) Uani 1 1 d . . . . .
C24 C 0.46136(15) 0.81206(14) 0.53319(4) 0.0300(3) Uani 1 1 d . . . . .
C25 C 0.34127(14) 0.77073(13) 0.51995(4) 0.0266(3) Uani 1 1 d . . . . .
C26 C 0.31046(13) 0.69725(13) 0.47939(4) 0.0235(3) Uani 1 1 d . . . . .
C27 C 0.42920(13) 0.66232(14) 0.45932(4) 0.0246(3) Uani 1 1 d . . . . .
C28 C 0.54831(14) 0.72103(14) 0.47155(4) 0.0272(3) Uani 1 1 d . . . . .
C29 C 0.56778(15) 0.80602(15) 0.50771(5) 0.0315(3) Uani 1 1 d . . . . .
C30 C 0.65168(15) 0.69677(16) 0.44970(5) 0.0336(3) Uani 1 1 d . . . . .
H30 H 0.732343 0.738253 0.457540 0.040 Uiso 1 1 calc R U . . .
C31 C 0.63642(16) 0.61280(17) 0.41685(5) 0.0359(4) Uani 1 1 d . . . . .
H31 H 0.706705 0.596684 0.402130 0.043 Uiso 1 1 calc R U . . .
C32 C 0.51852(16) 0.55145(17) 0.40513(5) 0.0363(4) Uani 1 1 d . . . . .
H32 H 0.508951 0.492471 0.382769 0.044 Uiso 1 1 calc R U . . .
C33 C 0.41513(15) 0.57658(16) 0.42615(4) 0.0320(3) Uani 1 1 d . . . . .
H33 H 0.334510 0.535417 0.417974 0.038 Uiso 1 1 calc R U . . .
C34 C 0.24228(14) 0.57097(14) 0.48727(4) 0.0266(3) Uani 1 1 d . . . . .
H34 H 0.285160 0.510726 0.506288 0.032 Uiso 1 1 calc R U . . .
C35 C 0.12514(15) 0.53898(16) 0.46906(4) 0.0312(3) Uani 1 1 d . . . . .
H35 H 0.089326 0.456328 0.474799 0.037 Uiso 1 1 calc R U . . .
C36 C 0.05026(14) 0.62873(17) 0.44031(5) 0.0346(3) Uani 1 1 d . . . . .
C37 C 0.11290(14) 0.75166(15) 0.43083(5) 0.0308(3) Uani 1 1 d . . . . .
H37 H 0.069592 0.808883 0.410955 0.037 Uiso 1 1 calc R U . . .
C38 C 0.22905(14) 0.78555(14) 0.44931(4) 0.0273(3) Uani 1 1 d . . . . .
H38 H 0.262538 0.869104 0.443359 0.033 Uiso 1 1 calc R U . . .
C39 C 0.22587(15) 0.79899(15) 0.54078(4) 0.0312(3) Uani 1 1 d . . . . .
C40 C 0.17439(17) 0.70770(17) 0.56494(5) 0.0371(4) Uani 1 1 d . . . . .
H40 H 0.214132 0.624074 0.569382 0.044 Uiso 1 1 calc R U . . .
C41 C 0.06501(18) 0.7371(2) 0.58281(5) 0.0455(4) Uani 1 1 d . . . . .
H41 H 0.031934 0.674543 0.599986 0.055 Uiso 1 1 calc R U . . .
C42 C 0.0049(2) 0.8557(3) 0.57574(7) 0.0650(7) Uani 1 1 d . . . . .
H42 H -0.071598 0.874690 0.587124 0.078 Uiso 1 1 calc R U . . .
C43 C 0.0567(3) 0.9476(3) 0.55187(9) 0.0861(10) Uani 1 1 d . . . . .
H43 H 0.015998 1.030684 0.547217 0.103 Uiso 1 1 calc R U . . .
C44 C 0.1676(3) 0.9199(2) 0.53455(7) 0.0621(6) Uani 1 1 d . . . . .
H44 H 0.202991 0.984196 0.518485 0.075 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
F1 C1 1.3404(18) . ?
F2 C1 1.3460(18) . ?
F3 C1 1.3325(17) . ?
O1 C7 1.2237(18) . ?
O2 C14 1.230(2) . ?
C1 C2 1.5198(19) . ?
C2 C3 1.3431(19) . ?
C2 C7 1.4877(19) . ?
C3 C4 1.5418(18) . ?
C3 C17 1.4973(19) . ?
C4 C5 1.5285(19) . ?
C4 C12 1.511(2) . ?
C4 C16 1.520(2) . ?
C5 C6 1.389(2) . ?
C5 C11 1.399(2) . ?
C6 C7 1.476(2) . ?
C6 C8 1.404(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.333(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.470(3) . ?
C14 C15 1.459(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.333(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 C22 1.392(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.372(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.401(3) . ?
C22 H22 0.9500 . ?
F4 C23 1.341(2) . ?
F5 C23 1.326(2) . ?
F6 C23 1.335(2) . ?
O3 C29 1.226(2) . ?
O4 C36 1.230(2) . ?
C23 C24 1.517(2) . ?
C24 C25 1.345(2) . ?
C24 C29 1.487(2) . ?
C25 C26 1.5381(19) . ?
C25 C39 1.497(2) . ?
C26 C27 1.5280(18) . ?
C26 C34 1.5091(19) . ?
C26 C38 1.5200(19) . ?
C27 C28 1.395(2) . ?
C27 C33 1.398(2) . ?
C28 C29 1.473(2) . ?
C28 C30 1.402(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.393(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.387(2) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.336(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.472(2) . ?
C36 C37 1.465(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.335(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.382(2) . ?
C39 C44 1.376(2) . ?
C40 H40 0.9500 . ?
C40 C41 1.390(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.366(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.382(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.391(3) . ?
C44 H44 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
F1 C1 F2 107.30(12) . . ?
F1 C1 C2 111.86(13) . . ?
F2 C1 C2 110.32(12) . . ?
F3 C1 F1 106.17(12) . . ?
F3 C1 F2 106.16(13) . . ?
F3 C1 C2 114.61(12) . . ?
C3 C2 C1 124.25(13) . . ?
C3 C2 C7 123.00(12) . . ?
C7 C2 C1 112.75(12) . . ?
C2 C3 C4 121.58(12) . . ?
C2 C3 C17 124.55(12) . . ?
C17 C3 C4 113.84(11) . . ?
C5 C4 C3 113.97(11) . . ?
C12 C4 C3 108.93(11) . . ?
C12 C4 C5 108.51(12) . . ?
C12 C4 C16 112.37(12) . . ?
C16 C4 C3 106.27(11) . . ?
C16 C4 C5 106.85(11) . . ?
C6 C5 C4 121.66(12) . . ?
C6 C5 C11 118.95(14) . . ?
C11 C5 C4 119.35(13) . . ?
C5 C6 C7 121.19(13) . . ?
C5 C6 C8 120.51(14) . . ?
C8 C6 C7 118.20(14) . . ?
O1 C7 C2 120.82(13) . . ?
O1 C7 C6 121.75(13) . . ?
C6 C7 C2 117.37(12) . . ?
C6 C8 H8 120.0 . . ?
C9 C8 C6 119.97(16) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.67(15) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.86(16) . . ?
C11 C10 H10 119.6 . . ?
C5 C11 H11 120.0 . . ?
C10 C11 C5 120.01(16) . . ?
C10 C11 H11 120.0 . . ?
C4 C12 H12 118.4 . . ?
C13 C12 C4 123.26(15) . . ?
C13 C12 H12 118.4 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.06(15) . . ?
C14 C13 H13 119.0 . . ?
O2 C14 C13 121.66(18) . . ?
O2 C14 C15 121.58(18) . . ?
C15 C14 C13 116.75(14) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.08(15) . . ?
C16 C15 H15 119.0 . . ?
C4 C16 H16 118.4 . . ?
C15 C16 C4 123.28(15) . . ?
C15 C16 H16 118.4 . . ?
C18 C17 C3 119.78(14) . . ?
C18 C17 C22 119.89(15) . . ?
C22 C17 C3 120.32(14) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.13(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.44(17) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.45(19) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.24(19) . . ?
C17 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
F4 C23 C24 110.92(14) . . ?
F5 C23 F4 104.13(15) . . ?
F5 C23 F6 107.82(15) . . ?
F5 C23 C24 114.25(15) . . ?
F6 C23 F4 106.94(15) . . ?
F6 C23 C24 112.22(15) . . ?
C25 C24 C23 123.97(14) . . ?
C25 C24 C29 122.68(13) . . ?
C29 C24 C23 113.26(14) . . ?
C24 C25 C26 121.25(12) . . ?
C24 C25 C39 124.47(13) . . ?
C39 C25 C26 114.13(12) . . ?
C27 C26 C25 113.94(11) . . ?
C34 C26 C25 108.14(11) . . ?
C34 C26 C27 107.98(11) . . ?
C34 C26 C38 112.29(12) . . ?
C38 C26 C25 108.95(11) . . ?
C38 C26 C27 105.62(11) . . ?
C28 C27 C26 121.44(12) . . ?
C28 C27 C33 119.64(13) . . ?
C33 C27 C26 118.76(13) . . ?
C27 C28 C29 120.80(13) . . ?
C27 C28 C30 119.72(14) . . ?
C30 C28 C29 119.46(14) . . ?
O3 C29 C24 120.53(15) . . ?
O3 C29 C28 122.42(15) . . ?
C28 C29 C24 117.04(13) . . ?
C28 C30 H30 120.0 . . ?
C31 C30 C28 120.10(15) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.38(14) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 119.91(15) . . ?
C33 C32 H32 120.0 . . ?
C27 C33 H33 119.9 . . ?
C32 C33 C27 120.21(15) . . ?
C32 C33 H33 119.9 . . ?
C26 C34 H34 118.1 . . ?
C35 C34 C26 123.81(13) . . ?
C35 C34 H34 118.1 . . ?
C34 C35 H35 119.2 . . ?
C34 C35 C36 121.56(14) . . ?
C36 C35 H35 119.2 . . ?
O4 C36 C35 121.54(16) . . ?
O4 C36 C37 121.51(16) . . ?
C37 C36 C35 116.94(13) . . ?
C36 C37 H37 119.0 . . ?
C38 C37 C36 121.90(14) . . ?
C38 C37 H37 119.0 . . ?
C26 C38 H38 118.3 . . ?
C37 C38 C26 123.33(13) . . ?
C37 C38 H38 118.3 . . ?
C40 C39 C25 122.65(14) . . ?
C44 C39 C25 118.10(15) . . ?
C44 C39 C40 119.22(16) . . ?
C39 C40 H40 119.7 . . ?
C39 C40 C41 120.63(16) . . ?
C41 C40 H40 119.7 . . ?
C40 C41 H41 119.9 . . ?
C42 C41 C40 120.23(19) . . ?
C42 C41 H41 119.9 . . ?
C41 C42 H42 120.4 . . ?
C41 C42 C43 119.29(18) . . ?
C43 C42 H42 120.4 . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.8(2) . . ?
C44 C43 H43 119.6 . . ?
C39 C44 C43 119.8(2) . . ?
C39 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?

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
F1 C1 C2 C3 -118.77(15) . . . . ?
F1 C1 C2 C7 61.90(16) . . . . ?
F2 C1 C2 C3 121.88(15) . . . . ?
F2 C1 C2 C7 -57.45(16) . . . . ?
F3 C1 C2 C3 2.1(2) . . . . ?
F3 C1 C2 C7 -177.19(13) . . . . ?
O2 C14 C15 C16 174.57(15) . . . . ?
C1 C2 C3 C4 -178.51(13) . . . . ?
C1 C2 C3 C17 3.7(2) . . . . ?
C1 C2 C7 O1 -4.4(2) . . . . ?
C1 C2 C7 C6 172.85(13) . . . . ?
C2 C3 C4 C5 8.43(19) . . . . ?
C2 C3 C4 C12 129.74(14) . . . . ?
C2 C3 C4 C16 -108.98(15) . . . . ?
C2 C3 C17 C18 -95.02(18) . . . . ?
C2 C3 C17 C22 86.26(19) . . . . ?
C3 C2 C7 O1 176.24(15) . . . . ?
C3 C2 C7 C6 -6.5(2) . . . . ?
C3 C4 C5 C6 -12.6(2) . . . . ?
C3 C4 C5 C11 169.61(14) . . . . ?
C3 C4 C12 C13 116.43(15) . . . . ?
C3 C4 C16 C15 -117.79(15) . . . . ?
C3 C17 C18 C19 -178.91(15) . . . . ?
C3 C17 C22 C21 178.75(15) . . . . ?
C4 C3 C17 C18 87.01(16) . . . . ?
C4 C3 C17 C22 -91.71(16) . . . . ?
C4 C5 C6 C7 7.7(2) . . . . ?
C4 C5 C6 C8 -176.09(14) . . . . ?
C4 C5 C11 C10 177.86(16) . . . . ?
C4 C12 C13 C14 -2.1(2) . . . . ?
C5 C4 C12 C13 -118.98(16) . . . . ?
C5 C4 C16 C15 120.16(16) . . . . ?
C5 C6 C7 O1 179.36(15) . . . . ?
C5 C6 C7 C2 2.1(2) . . . . ?
C5 C6 C8 C9 -2.0(3) . . . . ?
C6 C5 C11 C10 0.1(3) . . . . ?
C6 C8 C9 C10 0.7(3) . . . . ?
C7 C2 C3 C4 0.8(2) . . . . ?
C7 C2 C3 C17 -177.07(13) . . . . ?
C7 C6 C8 C9 174.30(16) . . . . ?
C8 C6 C7 O1 3.0(2) . . . . ?
C8 C6 C7 C2 -174.20(14) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C5 -1.4(3) . . . . ?
C11 C5 C6 C7 -174.57(15) . . . . ?
C11 C5 C6 C8 1.7(2) . . . . ?
C12 C4 C5 C6 -134.20(14) . . . . ?
C12 C4 C5 C11 48.06(18) . . . . ?
C12 C4 C16 C15 1.3(2) . . . . ?
C12 C13 C14 O2 -174.37(16) . . . . ?
C12 C13 C14 C15 4.9(2) . . . . ?
C13 C14 C15 C16 -4.7(2) . . . . ?
C14 C15 C16 C4 1.7(2) . . . . ?
C16 C4 C5 C6 104.42(15) . . . . ?
C16 C4 C5 C11 -73.32(17) . . . . ?
C16 C4 C12 C13 -1.1(2) . . . . ?
C17 C3 C4 C5 -173.53(12) . . . . ?
C17 C3 C4 C12 -52.22(16) . . . . ?
C17 C3 C4 C16 69.06(15) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C17 C22 C21 0.0(2) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?
F4 C23 C24 C25 133.34(16) . . . . ?
F4 C23 C24 C29 -49.89(19) . . . . ?
F5 C23 C24 C25 16.0(2) . . . . ?
F5 C23 C24 C29 -167.20(15) . . . . ?
F6 C23 C24 C25 -107.11(19) . . . . ?
F6 C23 C24 C29 69.66(19) . . . . ?
O4 C36 C37 C38 174.72(17) . . . . ?
C23 C24 C25 C26 -175.26(14) . . . . ?
C23 C24 C25 C39 9.3(2) . . . . ?
C23 C24 C29 O3 -13.8(2) . . . . ?
C23 C24 C29 C28 166.97(13) . . . . ?
C24 C25 C26 C27 7.17(19) . . . . ?
C24 C25 C26 C34 127.23(14) . . . . ?
C24 C25 C26 C38 -110.46(15) . . . . ?
C24 C25 C39 C40 -101.1(2) . . . . ?
C24 C25 C39 C44 80.6(2) . . . . ?
C25 C24 C29 O3 163.06(16) . . . . ?
C25 C24 C29 C28 -16.2(2) . . . . ?
C25 C26 C27 C28 -15.31(18) . . . . ?
C25 C26 C27 C33 169.25(12) . . . . ?
C25 C26 C34 C35 121.91(15) . . . . ?
C25 C26 C38 C37 -122.50(15) . . . . ?
C25 C39 C40 C41 -178.25(16) . . . . ?
C25 C39 C44 C43 177.0(2) . . . . ?
C26 C25 C39 C40 83.19(18) . . . . ?
C26 C25 C39 C44 -95.1(2) . . . . ?
C26 C27 C28 C29 8.0(2) . . . . ?
C26 C27 C28 C30 -173.42(12) . . . . ?
C26 C27 C33 C32 174.61(13) . . . . ?
C26 C34 C35 C36 -2.2(2) . . . . ?
C27 C26 C34 C35 -114.36(15) . . . . ?
C27 C26 C38 C37 114.72(15) . . . . ?
C27 C28 C29 O3 -171.59(15) . . . . ?
C27 C28 C29 C24 7.7(2) . . . . ?
C27 C28 C30 C31 -1.5(2) . . . . ?
C28 C27 C33 C32 -0.9(2) . . . . ?
C28 C30 C31 C32 0.0(2) . . . . ?
C29 C24 C25 C26 8.3(2) . . . . ?
C29 C24 C25 C39 -167.13(14) . . . . ?
C29 C28 C30 C31 177.13(13) . . . . ?
C30 C28 C29 O3 9.8(2) . . . . ?
C30 C28 C29 C24 -170.97(13) . . . . ?
C30 C31 C32 C33 1.1(2) . . . . ?
C31 C32 C33 C27 -0.6(2) . . . . ?
C33 C27 C28 C29 -176.64(13) . . . . ?
C33 C27 C28 C30 2.0(2) . . . . ?
C34 C26 C27 C28 -135.46(13) . . . . ?
C34 C26 C27 C33 49.10(16) . . . . ?
C34 C26 C38 C37 -2.73(19) . . . . ?
C34 C35 C36 O4 -175.79(16) . . . . ?
C34 C35 C36 C37 3.3(2) . . . . ?
C35 C36 C37 C38 -4.4(2) . . . . ?
C36 C37 C38 C26 4.3(2) . . . . ?
C38 C26 C27 C28 104.22(14) . . . . ?
C38 C26 C27 C33 -71.22(16) . . . . ?
C38 C26 C34 C35 1.67(19) . . . . ?
C39 C25 C26 C27 -176.99(12) . . . . ?
C39 C25 C26 C34 -56.93(15) . . . . ?
C39 C25 C26 C38 65.38(15) . . . . ?
C39 C40 C41 C42 1.8(3) . . . . ?
C40 C39 C44 C43 -1.3(4) . . . . ?
C40 C41 C42 C43 -2.3(4) . . . . ?
C41 C42 C43 C44 1.0(5) . . . . ?
C42 C43 C44 C39 0.8(5) . . . . ?
C44 C39 C40 C41 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2075572'
_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 F2 O4'
_chemical_formula_weight         408.38

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'
F F 0.0171 0.0103 '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                   11.1063(6)
_cell_length_b                   11.5675(7)
_cell_length_c                   15.4633(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.479(2)
_cell_angle_gamma                90
_cell_volume                     1946.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5470
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.49

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .968
_exptl_absorpt_correction_T_max  .987
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21337
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4413
_reflns_number_gt                3130
_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       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  "S'Siemens SHELXTL"
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.3080P)²+0.7800P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.32(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.1526
_refine_ls_R_factor_gt           0.1223
_refine_ls_wR_factor_ref         0.4064
_refine_ls_wR_factor_gt          0.3592
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.3840(4) 0.6142(3) 0.3479(3) 0.1024(13) Uani 1 1 d . . . . .
O2 O -0.0733(3) 1.1378(3) 0.1205(2) 0.0885(10) Uani 1 1 d . . . . .
O3 O 0.1363(3) 1.1351(2) 0.05490(18) 0.0719(8) Uani 1 1 d . . . . .
O4 O 0.3086(2) 0.9515(2) 0.12268(17) 0.0627(8) Uani 1 1 d . . . . .
F1 F 0.3977(7) 0.7602(6) 0.4847(3) 0.191(3) Uani 1 1 d . . . . .
F2 F 0.5369(3) 0.8237(6) 0.4146(3) 0.161(2) Uani 1 1 d . . . . .
C1 C 0.3945(4) 1.0812(4) 0.3083(3) 0.0799(12) Uani 1 1 d . . . . .
H1A H 0.4544 1.0410 0.2863 0.096 Uiso 1 1 calc R U . . .
C2 C 0.4115(5) 1.1953(5) 0.3287(4) 0.0902(14) Uani 1 1 d . . . . .
H2A H 0.4837 1.2314 0.3214 0.108 Uiso 1 1 calc R U . . .
C3 C 0.3239(5) 1.2588(4) 0.3602(3) 0.0883(14) Uani 1 1 d . . . . .
H3A H 0.3351 1.3373 0.3718 0.106 Uiso 1 1 calc R U . . .
C4 C 0.2200(5) 1.2032(4) 0.3739(3) 0.0825(13) Uani 1 1 d . . . . .
H4A H 0.1613 1.2442 0.3967 0.099 Uiso 1 1 calc R U . . .
C5 C 0.2012(4) 1.0867(4) 0.3543(2) 0.0680(10) Uani 1 1 d . . . . .
H5A H 0.1305 1.0502 0.3640 0.082 Uiso 1 1 calc R U . . .
C6 C 0.2889(3) 1.0241(3) 0.3198(2) 0.0614(9) Uani 1 1 d . . . . .
C7 C 0.2713(3) 0.8992(3) 0.2927(2) 0.0585(9) Uani 1 1 d . . . . .
C8 C 0.3355(4) 0.8124(4) 0.3375(3) 0.0695(11) Uani 1 1 d . . . . .
C9 C 0.3269(4) 0.6917(4) 0.3043(3) 0.0732(11) Uani 1 1 d . . . . .
C10 C 0.2563(3) 0.6710(3) 0.2141(3) 0.0640(10) Uani 1 1 d . . . . .
C11 C 0.1851(3) 0.7575(3) 0.1674(2) 0.0587(9) Uani 1 1 d . . . . .
C12 C 0.1765(3) 0.8780(3) 0.2085(2) 0.0512(8) Uani 1 1 d . . . . .
C13 C 0.1206(4) 0.7372(3) 0.0823(3) 0.0740(11) Uani 1 1 d . . . . .
H13A H 0.0715 0.7951 0.0518 0.089 Uiso 1 1 calc R U . . .
C14 C 0.1292(6) 0.6310(4) 0.0428(4) 0.0921(15) Uani 1 1 d . . . . .
H14A H 0.0860 0.6174 -0.0142 0.111 Uiso 1 1 calc R U . . .
C15 C 0.2017(6) 0.5459(4) 0.0878(4) 0.0923(15) Uani 1 1 d . . . . .
H15A H 0.2085 0.4753 0.0605 0.111 Uiso 1 1 calc R U . . .
C16 C 0.2638(5) 0.5635(3) 0.1722(4) 0.0852(14) Uani 1 1 d . . . . .
H16A H 0.3114 0.5044 0.2022 0.102 Uiso 1 1 calc R U . . .
C17 C 0.0498(3) 0.8856(3) 0.2311(2) 0.0600(9) Uani 1 1 d . . . . .
H17A H 0.0286 0.8313 0.2698 0.072 Uiso 1 1 calc R U . . .
C18 C -0.0309(3) 0.9646(3) 0.1989(3) 0.0637(9) Uani 1 1 d . . . . .
H18A H -0.1083 0.9622 0.2133 0.076 Uiso 1 1 calc R U . . .
C19 C -0.0034(3) 1.0564(3) 0.1412(2) 0.0605(9) Uani 1 1 d . . . . .
C20 C 0.1141(3) 1.0505(3) 0.1119(2) 0.0555(8) Uani 1 1 d . . . . .
C21 C 0.1973(3) 0.9671(2) 0.1416(2) 0.0497(8) Uani 1 1 d . . . . .
C22 C 0.4227(5) 0.8304(5) 0.4251(3) 0.0916(14) Uani 1 1 d . . . . .
H22A H 0.4098 0.9092 0.4447 0.110 Uiso 1 1 calc R U . . .
C23 C 0.1829(7) 1.2382(4) 0.0984(4) 0.110(2) Uani 1 1 d . . . . .
H23A H 0.1967 1.2941 0.0555 0.165 Uiso 1 1 calc R U . . .
H23B H 0.1247 1.2683 0.1309 0.165 Uiso 1 1 calc R U . . .
H23C H 0.2590 1.2221 0.1382 0.165 Uiso 1 1 calc R U . . .
C24 C 0.3416(5) 0.9958(5) 0.0441(3) 0.0849(13) Uani 1 1 d . . . . .
H24A H 0.4251 0.9752 0.0433 0.127 Uiso 1 1 calc R U . . .
H24B H 0.2882 0.9635 -0.0066 0.127 Uiso 1 1 calc R U . . .
H24C H 0.3336 1.0785 0.0430 0.127 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 C9 1.221(5) . ?
O2 C19 1.221(4) . ?
O3 C20 1.371(4) . ?
O3 C23 1.416(6) . ?
O4 C21 1.338(4) . ?
O4 C24 1.432(5) . ?
F1 C22 1.299(8) . ?
F2 C22 1.314(6) . ?
C1 C2 1.363(7) . ?
C1 C6 1.388(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.382(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.506(5) . ?
C7 C8 1.342(5) . ?
C7 C12 1.523(5) . ?
C8 C9 1.484(6) . ?
C8 C22 1.514(7) . ?
C9 C10 1.478(7) . ?
C10 C11 1.386(5) . ?
C10 C16 1.412(6) . ?
C11 C13 1.387(6) . ?
C11 C12 1.543(4) . ?
C12 C21 1.510(4) . ?
C12 C17 1.518(4) . ?
C13 C14 1.384(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.370(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.364(8) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.308(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.458(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.467(5) . ?
C20 C21 1.351(5) . ?
C22 H22A 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C20 O3 C23 113.0(3) . . ?
C21 O4 C24 122.7(3) . . ?
C2 C1 C6 120.9(4) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 C3 121.4(5) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 118.6(5) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 118.1(4) . . ?
C1 C6 C7 119.1(3) . . ?
C5 C6 C7 122.7(3) . . ?
C8 C7 C6 123.2(4) . . ?
C8 C7 C12 121.9(4) . . ?
C6 C7 C12 114.9(3) . . ?
C7 C8 C9 122.3(4) . . ?
C7 C8 C22 122.6(4) . . ?
C9 C8 C22 115.1(4) . . ?
O1 C9 C10 121.5(4) . . ?
O1 C9 C8 120.6(5) . . ?
C10 C9 C8 117.7(3) . . ?
C11 C10 C16 118.5(4) . . ?
C11 C10 C9 121.0(3) . . ?
C16 C10 C9 120.5(4) . . ?
C10 C11 C13 120.3(3) . . ?
C10 C11 C12 120.9(3) . . ?
C13 C11 C12 118.7(3) . . ?
C21 C12 C17 113.2(3) . . ?
C21 C12 C7 107.6(3) . . ?
C17 C12 C7 108.0(3) . . ?
C21 C12 C11 107.7(2) . . ?
C17 C12 C11 106.5(3) . . ?
C7 C12 C11 114.1(3) . . ?
C14 C13 C11 120.1(4) . . ?
C14 C13 H13A 120.0 . . ?
C11 C13 H13A 120.0 . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C10 120.3(4) . . ?
C15 C16 H16A 119.9 . . ?
C10 C16 H16A 119.9 . . ?
C18 C17 C12 123.3(3) . . ?
C18 C17 H17A 118.3 . . ?
C12 C17 H17A 118.3 . . ?
C17 C18 C19 122.1(3) . . ?
C17 C18 H18A 119.0 . . ?
C19 C18 H18A 119.0 . . ?
O2 C19 C18 121.5(4) . . ?
O2 C19 C20 120.8(4) . . ?
C18 C19 C20 117.6(3) . . ?
C21 C20 O3 122.0(3) . . ?
C21 C20 C19 121.2(3) . . ?
O3 C20 C19 116.8(3) . . ?
O4 C21 C20 128.4(3) . . ?
O4 C21 C12 109.4(3) . . ?
C20 C21 C12 122.2(3) . . ?
F1 C22 F2 113.5(5) . . ?
F1 C22 C8 111.1(5) . . ?
F2 C22 C8 110.0(4) . . ?
F1 C22 H22A 107.3 . . ?
F2 C22 H22A 107.3 . . ?
C8 C22 H22A 107.3 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 -1.1(8) . . . . ?
C1 C2 C3 C4 2.5(8) . . . . ?
C2 C3 C4 C5 -1.9(7) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
C2 C1 C6 C7 177.4(4) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C4 C5 C6 C7 -176.8(3) . . . . ?
C1 C6 C7 C8 72.5(5) . . . . ?
C5 C6 C7 C8 -109.3(4) . . . . ?
C1 C6 C7 C12 -106.1(4) . . . . ?
C5 C6 C7 C12 72.2(4) . . . . ?
C6 C7 C8 C9 -172.9(3) . . . . ?
C12 C7 C8 C9 5.5(5) . . . . ?
C6 C7 C8 C22 6.6(6) . . . . ?
C12 C7 C8 C22 -175.0(4) . . . . ?
C7 C8 C9 O1 -177.9(4) . . . . ?
C22 C8 C9 O1 2.6(6) . . . . ?
C7 C8 C9 C10 7.3(6) . . . . ?
C22 C8 C9 C10 -172.2(4) . . . . ?
O1 C9 C10 C11 175.6(4) . . . . ?
C8 C9 C10 C11 -9.7(5) . . . . ?
O1 C9 C10 C16 -7.0(6) . . . . ?
C8 C9 C10 C16 167.8(3) . . . . ?
C16 C10 C11 C13 1.6(5) . . . . ?
C9 C10 C11 C13 179.1(3) . . . . ?
C16 C10 C11 C12 -178.1(3) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C8 C7 C12 C21 -134.4(3) . . . . ?
C6 C7 C12 C21 44.1(3) . . . . ?
C8 C7 C12 C17 103.1(4) . . . . ?
C6 C7 C12 C17 -78.3(3) . . . . ?
C8 C7 C12 C11 -15.0(4) . . . . ?
C6 C7 C12 C11 163.6(3) . . . . ?
C10 C11 C12 C21 131.8(3) . . . . ?
C13 C11 C12 C21 -48.0(4) . . . . ?
C10 C11 C12 C17 -106.6(3) . . . . ?
C13 C11 C12 C17 73.7(4) . . . . ?
C10 C11 C12 C7 12.4(4) . . . . ?
C13 C11 C12 C7 -167.3(3) . . . . ?
C10 C11 C13 C14 -1.5(6) . . . . ?
C12 C11 C13 C14 178.2(4) . . . . ?
C11 C13 C14 C15 0.0(7) . . . . ?
C13 C14 C15 C16 1.4(8) . . . . ?
C14 C15 C16 C10 -1.2(8) . . . . ?
C11 C10 C16 C15 -0.3(6) . . . . ?
C9 C10 C16 C15 -177.8(4) . . . . ?
C21 C12 C17 C18 -2.9(5) . . . . ?
C7 C12 C17 C18 116.0(4) . . . . ?
C11 C12 C17 C18 -121.1(4) . . . . ?
C12 C17 C18 C19 -3.0(6) . . . . ?
C17 C18 C19 O2 -170.7(4) . . . . ?
C17 C18 C19 C20 6.6(6) . . . . ?
C23 O3 C20 C21 -95.3(5) . . . . ?
C23 O3 C20 C19 83.1(5) . . . . ?
O2 C19 C20 C21 173.3(4) . . . . ?
C18 C19 C20 C21 -4.0(5) . . . . ?
O2 C19 C20 O3 -5.2(5) . . . . ?
C18 C19 C20 O3 177.5(3) . . . . ?
C24 O4 C21 C20 -23.1(6) . . . . ?
C24 O4 C21 C12 160.0(4) . . . . ?
O3 C20 C21 O4 -0.2(6) . . . . ?
C19 C20 C21 O4 -178.6(3) . . . . ?
O3 C20 C21 C12 176.3(3) . . . . ?
C19 C20 C21 C12 -2.1(5) . . . . ?
C17 C12 C21 O4 -177.5(3) . . . . ?
C7 C12 C21 O4 63.4(3) . . . . ?
C11 C12 C21 O4 -60.0(3) . . . . ?
C17 C12 C21 C20 5.5(5) . . . . ?
C7 C12 C21 C20 -113.7(3) . . . . ?
C11 C12 C21 C20 122.9(3) . . . . ?
C7 C8 C22 F1 127.0(5) . . . . ?
C9 C8 C22 F1 -53.4(6) . . . . ?
C7 C8 C22 F2 -106.4(5) . . . . ?
C9 C8 C22 F2 73.1(6) . . . . ?

_refine_diff_density_max         2.174
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.179

