# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_210514_zpp_21dj_0m
_database_code_depnum_ccdc_archive 'CCDC 2108044'
loop_
_audit_author_name
_audit_author_address
'Piaopiao Zeng'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-25 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            'C22 H13 F3 O2'
_chemical_formula_weight         366.32

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                   14.1040(6)
_cell_length_b                   15.1682(9)
_cell_length_c                   24.3684(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.661(2)
_cell_angle_gamma                90
_cell_volume                     5086.4(4)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             2256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54654
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         27.117
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11216
_reflns_number_gt                7583
_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)+(0.0354P)²+1.8931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11216
_refine_ls_number_parameters     730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.17583(10) 0.65520(8) 0.73083(6) 0.0409(3) Uani 1 1 d . . . . .
F2 F 0.40286(8) 0.13358(7) 0.73555(5) 0.0291(3) Uani 1 1 d . . . . .
F3 F 0.47064(8) 0.20573(8) 0.67726(5) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.18534(9) 0.20542(9) 0.70026(6) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.18597(9) 0.35056(9) 0.70347(6) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.38311(16) 0.50933(13) 0.75037(9) 0.0280(5) Uani 1 1 d . . . . .
H1 H 0.451843 0.511613 0.762438 0.034 Uiso 1 1 calc R U . . .
C2 C 0.32923(16) 0.58567(14) 0.75025(9) 0.0313(5) Uani 1 1 d . . . . .
H2 H 0.360100 0.640357 0.761710 0.038 Uiso 1 1 calc R U . . .
C3 C 0.22935(16) 0.58013(14) 0.73301(9) 0.0303(5) Uani 1 1 d . . . . .
C4 C 0.18043(16) 0.50282(14) 0.71758(9) 0.0298(5) Uani 1 1 d . . . . .
H4 H 0.111498 0.500932 0.707031 0.036 Uiso 1 1 calc R U . . .
C5 C 0.23624(14) 0.42766(13) 0.71810(8) 0.0251(4) Uani 1 1 d . . . . .
C6 C 0.33768(14) 0.42858(13) 0.73291(8) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.39002(14) 0.34796(13) 0.72566(8) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.33874(13) 0.27430(13) 0.70604(8) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.23340(14) 0.27144(13) 0.70265(8) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.49888(14) 0.35019(12) 0.74283(8) 0.0215(4) Uani 1 1 d . . . . .
C11 C 0.55769(14) 0.37780(14) 0.70727(9) 0.0287(5) Uani 1 1 d . . . . .
H11 H 0.529215 0.396189 0.670040 0.034 Uiso 1 1 calc R U . . .
C12 C 0.65763(15) 0.37856(15) 0.72597(9) 0.0302(5) Uani 1 1 d . . . . .
H12 H 0.697470 0.397415 0.701431 0.036 Uiso 1 1 calc R U . . .
C13 C 0.69994(15) 0.35218(13) 0.77998(9) 0.0276(5) Uani 1 1 d . . . . .
H13 H 0.768678 0.351625 0.792292 0.033 Uiso 1 1 calc R U . . .
C14 C 0.64202(15) 0.32659(13) 0.81603(9) 0.0288(5) Uani 1 1 d . . . . .
H14 H 0.670941 0.310123 0.853586 0.035 Uiso 1 1 calc R U . . .
C15 C 0.54141(15) 0.32480(13) 0.79760(8) 0.0263(4) Uani 1 1 d . . . . .
H15 H 0.501801 0.306284 0.822350 0.032 Uiso 1 1 calc R U . . .
C16 C 0.38139(13) 0.18852(13) 0.68959(8) 0.0226(4) Uani 1 1 d . . . . .
C17 C 0.32010(13) 0.14185(12) 0.63968(8) 0.0206(4) Uani 1 1 d . . . . .
C18 C 0.29119(14) 0.05489(13) 0.64332(9) 0.0245(4) Uani 1 1 d . . . . .
H18 H 0.309251 0.023862 0.677906 0.029 Uiso 1 1 calc R U . . .
C19 C 0.23589(15) 0.01356(13) 0.59632(9) 0.0273(5) Uani 1 1 d . . . . .
H19 H 0.216276 -0.045986 0.598668 0.033 Uiso 1 1 calc R U . . .
C20 C 0.20918(14) 0.05884(13) 0.54597(9) 0.0273(5) Uani 1 1 d . . . . .
H20 H 0.170576 0.030590 0.513951 0.033 Uiso 1 1 calc R U . . .
C21 C 0.23863(14) 0.14506(13) 0.54226(9) 0.0262(4) Uani 1 1 d . . . . .
H21 H 0.220775 0.175781 0.507550 0.031 Uiso 1 1 calc R U . . .
C22 C 0.29423(14) 0.18705(13) 0.58905(8) 0.0232(4) Uani 1 1 d . . . . .
H22 H 0.314440 0.246350 0.586433 0.028 Uiso 1 1 calc R U . . .
F4 F 0.48759(9) -0.15074(8) 0.57370(5) 0.0334(3) Uani 1 1 d . . . . .
F5 F 0.65534(10) 0.38208(8) 0.59764(5) 0.0378(3) Uani 1 1 d . . . . .
F6 F 0.78119(8) 0.33004(8) 0.57152(5) 0.0364(3) Uani 1 1 d . . . . .
O3 O 0.48392(10) 0.29953(9) 0.54657(7) 0.0339(4) Uani 1 1 d . . . . .
O4 O 0.49204(9) 0.15587(9) 0.55653(6) 0.0250(3) Uani 1 1 d . . . . .
C23 C 0.69192(14) -0.00356(13) 0.58482(9) 0.0246(4) Uani 1 1 d . . . . .
H23 H 0.760799 -0.006046 0.591458 0.030 Uiso 1 1 calc R U . . .
C24 C 0.63961(15) -0.08050(14) 0.58484(9) 0.0284(5) Uani 1 1 d . . . . .
H24 H 0.671556 -0.135925 0.590940 0.034 Uiso 1 1 calc R U . . .
C25 C 0.53962(14) -0.07481(13) 0.57577(8) 0.0255(4) Uani 1 1 d . . . . .
C26 C 0.48925(14) 0.00299(13) 0.56743(8) 0.0245(4) Uani 1 1 d . . . . .
H26 H 0.420541 0.004861 0.562346 0.029 Uiso 1 1 calc R U . . .
C27 C 0.54392(14) 0.07909(12) 0.56681(8) 0.0211(4) Uani 1 1 d . . . . .
C28 C 0.64467(13) 0.07846(12) 0.57512(8) 0.0211(4) Uani 1 1 d . . . . .
C29 C 0.69512(14) 0.16188(13) 0.57251(8) 0.0208(4) Uani 1 1 d . . . . .
C30 C 0.64223(14) 0.23736(13) 0.56264(8) 0.0223(4) Uani 1 1 d . . . . .
C31 C 0.53617(15) 0.23584(13) 0.55476(8) 0.0246(4) Uani 1 1 d . . . . .
C32 C 0.80348(13) 0.15874(12) 0.58101(8) 0.0218(4) Uani 1 1 d . . . . .
C33 C 0.84739(14) 0.14820(13) 0.53574(8) 0.0250(4) Uani 1 1 d . . . . .
H33 H 0.808614 0.141260 0.498857 0.030 Uiso 1 1 calc R U . . .
C34 C 0.94823(15) 0.14781(14) 0.54440(9) 0.0288(5) Uani 1 1 d . . . . .
H34 H 0.978235 0.140631 0.513379 0.035 Uiso 1 1 calc R U . . .
C35 C 1.00483(15) 0.15783(13) 0.59798(9) 0.0277(5) Uani 1 1 d . . . . .
H35 H 1.073664 0.158500 0.603736 0.033 Uiso 1 1 calc R U . . .
C36 C 0.96124(14) 0.16684(13) 0.64309(9) 0.0282(5) Uani 1 1 d . . . . .
H36 H 1.000281 0.172894 0.679973 0.034 Uiso 1 1 calc R U . . .
C37 C 0.86104(14) 0.16714(13) 0.63500(8) 0.0257(4) Uani 1 1 d . . . . .
H37 H 0.831510 0.173088 0.666294 0.031 Uiso 1 1 calc R U . . .
C38 C 0.68154(15) 0.32965(13) 0.55736(9) 0.0261(4) Uani 1 1 d . . . . .
C39 C 0.65016(13) 0.37260(12) 0.50030(8) 0.0224(4) Uani 1 1 d . . . . .
C40 C 0.66022(15) 0.32729(14) 0.45264(9) 0.0298(5) Uani 1 1 d . . . . .
H40 H 0.682950 0.268149 0.455647 0.036 Uiso 1 1 calc R U . . .
C41 C 0.63718(16) 0.36807(14) 0.40049(9) 0.0307(5) Uani 1 1 d . . . . .
H41 H 0.644613 0.337012 0.367844 0.037 Uiso 1 1 calc R U . . .
C42 C 0.60353(16) 0.45354(14) 0.39599(9) 0.0317(5) Uani 1 1 d . . . . .
H42 H 0.587684 0.481490 0.360259 0.038 Uiso 1 1 calc R U . . .
C43 C 0.5929(2) 0.49843(15) 0.44340(10) 0.0440(6) Uani 1 1 d . . . . .
H43 H 0.569420 0.557328 0.440307 0.053 Uiso 1 1 calc R U . . .
C44 C 0.61626(18) 0.45811(14) 0.49541(10) 0.0378(6) Uani 1 1 d . . . . .
H44 H 0.608932 0.489439 0.527979 0.045 Uiso 1 1 calc R U . . .
F7 F 1.12624(10) 0.35868(8) 0.55456(6) 0.0417(3) Uani 1 1 d . . . . .
F8 F 0.95100(8) 0.88546(7) 0.57124(5) 0.0294(3) Uani 1 1 d . . . . .
F9 F 0.85060(8) 0.82637(7) 0.61639(5) 0.0289(3) Uani 1 1 d . . . . .
O5 O 1.13534(10) 0.80638(9) 0.59817(6) 0.0272(3) Uani 1 1 d . . . . .
O6 O 1.12485(10) 0.66366(9) 0.58261(6) 0.0274(3) Uani 1 1 d . . . . .
C45 C 0.93553(15) 0.49781(13) 0.58324(8) 0.0248(4) Uani 1 1 d . . . . .
H45 H 0.870684 0.492928 0.588048 0.030 Uiso 1 1 calc R U . . .
C46 C 0.98435(15) 0.42313(14) 0.57271(9) 0.0284(5) Uani 1 1 d . . . . .
H46 H 0.954238 0.366842 0.570608 0.034 Uiso 1 1 calc R U . . .
C47 C 1.07834(16) 0.43227(14) 0.56527(9) 0.0296(5) Uani 1 1 d . . . . .
C48 C 1.12610(15) 0.51153(14) 0.56800(9) 0.0287(5) Uani 1 1 d . . . . .
H48 H 1.190502 0.515632 0.562362 0.034 Uiso 1 1 calc R U . . .
C49 C 1.07568(14) 0.58525(13) 0.57939(8) 0.0238(4) Uani 1 1 d . . . . .
C50 C 0.98039(14) 0.58128(12) 0.58699(8) 0.0215(4) Uani 1 1 d . . . . .
C51 C 0.93345(13) 0.66263(12) 0.59886(8) 0.0203(4) Uani 1 1 d . . . . .
C52 C 0.98404(14) 0.73996(12) 0.60238(8) 0.0209(4) Uani 1 1 d . . . . .
C53 C 1.08458(14) 0.74168(13) 0.59479(8) 0.0234(4) Uani 1 1 d . . . . .
C54 C 0.83248(13) 0.65497(12) 0.60844(8) 0.0209(4) Uani 1 1 d . . . . .
C55 C 0.75128(15) 0.66048(13) 0.56429(9) 0.0289(5) Uani 1 1 d . . . . .
H55 H 0.758950 0.668617 0.526846 0.035 Uiso 1 1 calc R U . . .
C56 C 0.65885(16) 0.65400(14) 0.57527(11) 0.0377(6) Uani 1 1 d . . . . .
H56 H 0.603269 0.659230 0.545327 0.045 Uiso 1 1 calc R U . . .
C57 C 0.64741(16) 0.64008(15) 0.62922(11) 0.0384(6) Uani 1 1 d . . . . .
H57 H 0.584037 0.635957 0.636434 0.046 Uiso 1 1 calc R U . . .
C58 C 0.72785(16) 0.63208(14) 0.67290(10) 0.0344(5) Uani 1 1 d . . . . .
H58 H 0.719847 0.620930 0.709976 0.041 Uiso 1 1 calc R U . . .
C59 C 0.82036(14) 0.64033(13) 0.66264(9) 0.0252(4) Uani 1 1 d . . . . .
H59 H 0.875608 0.635929 0.692865 0.030 Uiso 1 1 calc R U . . .
C60 C 0.94774(14) 0.83026(13) 0.61559(8) 0.0230(4) Uani 1 1 d . . . . .
C61 C 1.00114(13) 0.87087(12) 0.67005(8) 0.0210(4) Uani 1 1 d . . . . .
C62 C 1.04819(14) 0.95108(13) 0.67105(9) 0.0244(4) Uani 1 1 d . . . . .
H62 H 1.048448 0.981060 0.636856 0.029 Uiso 1 1 calc R U . . .
C63 C 1.09479(15) 0.98762(13) 0.72172(9) 0.0273(5) Uani 1 1 d . . . . .
H63 H 1.127131 1.042666 0.722297 0.033 Uiso 1 1 calc R U . . .
C64 C 1.09450(15) 0.94429(13) 0.77161(9) 0.0273(5) Uani 1 1 d . . . . .
H64 H 1.127059 0.969281 0.806393 0.033 Uiso 1 1 calc R U . . .
C65 C 1.04677(17) 0.86456(14) 0.77078(9) 0.0330(5) Uani 1 1 d . . . . .
H65 H 1.046013 0.835052 0.805071 0.040 Uiso 1 1 calc R U . . .
C66 C 1.00013(16) 0.82765(14) 0.72018(9) 0.0318(5) Uani 1 1 d . . . . .
H66 H 0.967430 0.772809 0.719692 0.038 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 C3 1.361(2) . ?
F2 C16 1.375(2) . ?
F3 C16 1.382(2) . ?
O1 C9 1.204(2) . ?
O2 C5 1.373(2) . ?
O2 C9 1.376(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.404(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.371(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C6 C7 1.459(3) . ?
C7 C8 1.360(3) . ?
C7 C10 1.501(3) . ?
C8 C9 1.471(3) . ?
C8 C16 1.524(3) . ?
C10 C11 1.389(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.506(3) . ?
C17 C22 1.389(3) . ?
C17 C18 1.389(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
F4 C25 1.361(2) . ?
F5 C38 1.375(2) . ?
F6 C38 1.372(2) . ?
O3 C31 1.205(2) . ?
O4 C31 1.368(2) . ?
O4 C27 1.369(2) . ?
C23 C24 1.381(3) . ?
C23 C28 1.407(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.370(3) . ?
C26 C27 1.390(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(3) . ?
C28 C29 1.460(3) . ?
C29 C30 1.359(3) . ?
C29 C32 1.497(3) . ?
C30 C31 1.466(3) . ?
C30 C38 1.522(3) . ?
C32 C33 1.388(3) . ?
C32 C37 1.392(3) . ?
C33 C34 1.391(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.383(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C39 1.511(3) . ?
C39 C44 1.378(3) . ?
C39 C40 1.383(3) . ?
C40 C41 1.386(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.377(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.377(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.380(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
F7 C47 1.359(2) . ?
F8 C60 1.376(2) . ?
F9 C60 1.376(2) . ?
O5 C53 1.207(2) . ?
O6 C49 1.370(2) . ?
O6 C53 1.373(2) . ?
C45 C46 1.379(3) . ?
C45 C50 1.409(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.384(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.372(3) . ?
C48 C49 1.385(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.398(3) . ?
C50 C51 1.459(3) . ?
C51 C52 1.366(3) . ?
C51 C54 1.497(3) . ?
C52 C53 1.470(3) . ?
C52 C60 1.521(3) . ?
C54 C59 1.386(3) . ?
C54 C55 1.391(3) . ?
C55 C56 1.391(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.376(3) . ?
C56 H56 0.9500 . ?
C57 C58 1.380(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.387(3) . ?
C58 H58 0.9500 . ?
C59 H59 0.9500 . ?
C60 C61 1.506(3) . ?
C61 C62 1.384(3) . ?
C61 C66 1.389(3) . ?
C62 C63 1.381(3) . ?
C62 H62 0.9500 . ?
C63 C64 1.383(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.382(3) . ?
C64 H64 0.9500 . ?
C65 C66 1.382(3) . ?
C65 H65 0.9500 . ?
C66 H66 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
C5 O2 C9 121.43(15) . . ?
C2 C1 C6 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
F1 C3 C4 117.62(19) . . ?
F1 C3 C2 118.74(19) . . ?
C4 C3 C2 123.64(19) . . ?
C3 C4 C5 116.8(2) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
O2 C5 C4 116.04(18) . . ?
O2 C5 C6 121.11(17) . . ?
C4 C5 C6 122.85(19) . . ?
C5 C6 C1 117.42(18) . . ?
C5 C6 C7 118.50(18) . . ?
C1 C6 C7 123.94(18) . . ?
C8 C7 C6 119.15(17) . . ?
C8 C7 C10 123.33(17) . . ?
C6 C7 C10 117.47(17) . . ?
C7 C8 C9 119.81(17) . . ?
C7 C8 C16 125.74(17) . . ?
C9 C8 C16 114.35(16) . . ?
O1 C9 O2 117.13(17) . . ?
O1 C9 C8 125.36(18) . . ?
O2 C9 C8 117.50(17) . . ?
C11 C10 C15 119.39(18) . . ?
C11 C10 C7 123.18(18) . . ?
C15 C10 C7 117.42(17) . . ?
C12 C11 C10 120.12(19) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.55(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.75(19) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.26(19) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 119.91(19) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
F2 C16 F3 104.08(14) . . ?
F2 C16 C17 110.97(16) . . ?
F3 C16 C17 107.60(15) . . ?
F2 C16 C8 109.40(15) . . ?
F3 C16 C8 109.08(15) . . ?
C17 C16 C8 115.10(16) . . ?
C22 C17 C18 120.13(18) . . ?
C22 C17 C16 118.57(17) . . ?
C18 C17 C16 121.29(18) . . ?
C19 C18 C17 119.77(19) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.16(19) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.03(19) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.28(19) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 119.62(18) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C31 O4 C27 122.09(15) . . ?
C24 C23 C28 120.94(18) . . ?
C24 C23 H23 119.5 . . ?
C28 C23 H23 119.5 . . ?
C23 C24 C25 118.29(19) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
F4 C25 C26 117.76(17) . . ?
F4 C25 C24 118.45(18) . . ?
C26 C25 C24 123.77(18) . . ?
C25 C26 C27 116.50(18) . . ?
C25 C26 H26 121.8 . . ?
C27 C26 H26 121.8 . . ?
O4 C27 C26 115.65(17) . . ?
O4 C27 C28 121.37(17) . . ?
C26 C27 C28 122.98(18) . . ?
C27 C28 C23 117.50(17) . . ?
C27 C28 C29 118.68(17) . . ?
C23 C28 C29 123.81(17) . . ?
C30 C29 C28 118.95(17) . . ?
C30 C29 C32 123.74(18) . . ?
C28 C29 C32 117.31(16) . . ?
C29 C30 C31 120.98(18) . . ?
C29 C30 C38 126.45(18) . . ?
C31 C30 C38 112.56(17) . . ?
O3 C31 O4 116.74(18) . . ?
O3 C31 C30 125.35(19) . . ?
O4 C31 C30 117.90(17) . . ?
C33 C32 C37 119.50(18) . . ?
C33 C32 C29 120.90(18) . . ?
C37 C32 C29 119.60(17) . . ?
C32 C33 C34 119.96(19) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.17(19) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C36 C35 C34 119.88(19) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 120.4(2) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C36 C37 C32 120.02(19) . . ?
C36 C37 H37 120.0 . . ?
C32 C37 H37 120.0 . . ?
F6 C38 F5 103.81(16) . . ?
F6 C38 C39 107.87(16) . . ?
F5 C38 C39 109.71(16) . . ?
F6 C38 C30 110.78(16) . . ?
F5 C38 C30 108.17(16) . . ?
C39 C38 C30 115.83(17) . . ?
C44 C39 C40 119.49(19) . . ?
C44 C39 C38 120.75(18) . . ?
C40 C39 C38 119.68(18) . . ?
C39 C40 C41 120.09(19) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 H40 120.0 . . ?
C42 C41 C40 120.0(2) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 119.8(2) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C42 C43 C44 120.2(2) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C39 C44 C43 120.3(2) . . ?
C39 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C49 O6 C53 122.17(15) . . ?
C46 C45 C50 120.98(19) . . ?
C46 C45 H45 119.5 . . ?
C50 C45 H45 119.5 . . ?
C45 C46 C47 118.30(19) . . ?
C45 C46 H46 120.9 . . ?
C47 C46 H46 120.9 . . ?
F7 C47 C48 117.99(19) . . ?
F7 C47 C46 118.27(19) . . ?
C48 C47 C46 123.74(19) . . ?
C47 C48 C49 116.66(19) . . ?
C47 C48 H48 121.7 . . ?
C49 C48 H48 121.7 . . ?
O6 C49 C48 115.88(17) . . ?
O6 C49 C50 121.27(17) . . ?
C48 C49 C50 122.85(19) . . ?
C49 C50 C45 117.46(18) . . ?
C49 C50 C51 118.76(17) . . ?
C45 C50 C51 123.77(18) . . ?
C52 C51 C50 119.04(17) . . ?
C52 C51 C54 123.95(17) . . ?
C50 C51 C54 116.98(16) . . ?
C51 C52 C53 120.82(17) . . ?
C51 C52 C60 126.24(17) . . ?
C53 C52 C60 112.92(16) . . ?
O5 C53 O6 116.64(17) . . ?
O5 C53 C52 125.45(18) . . ?
O6 C53 C52 117.91(16) . . ?
C59 C54 C55 119.59(18) . . ?
C59 C54 C51 118.76(17) . . ?
C55 C54 C51 121.63(18) . . ?
C56 C55 C54 119.6(2) . . ?
C56 C55 H55 120.2 . . ?
C54 C55 H55 120.2 . . ?
C57 C56 C55 120.4(2) . . ?
C57 C56 H56 119.8 . . ?
C55 C56 H56 119.8 . . ?
C56 C57 C58 120.1(2) . . ?
C56 C57 H57 119.9 . . ?
C58 C57 H57 119.9 . . ?
C57 C58 C59 120.0(2) . . ?
C57 C58 H58 120.0 . . ?
C59 C58 H58 120.0 . . ?
C54 C59 C58 120.2(2) . . ?
C54 C59 H59 119.9 . . ?
C58 C59 H59 119.9 . . ?
F9 C60 F8 104.01(14) . . ?
F9 C60 C61 108.20(15) . . ?
F8 C60 C61 110.30(15) . . ?
F9 C60 C52 110.29(15) . . ?
F8 C60 C52 108.12(15) . . ?
C61 C60 C52 115.34(16) . . ?
C62 C61 C66 119.79(19) . . ?
C62 C61 C60 121.35(18) . . ?
C66 C61 C60 118.83(17) . . ?
C63 C62 C61 120.07(19) . . ?
C63 C62 H62 120.0 . . ?
C61 C62 H62 120.0 . . ?
C62 C63 C64 120.17(19) . . ?
C62 C63 H63 119.9 . . ?
C64 C63 H63 119.9 . . ?
C65 C64 C63 119.9(2) . . ?
C65 C64 H64 120.1 . . ?
C63 C64 H64 120.1 . . ?
C64 C65 C66 120.2(2) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C65 C66 C61 119.91(19) . . ?
C65 C66 H66 120.0 . . ?
C61 C66 H66 120.0 . . ?

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 0.6(3) . . . . ?
C1 C2 C3 F1 -177.73(18) . . . . ?
C1 C2 C3 C4 2.0(3) . . . . ?
F1 C3 C4 C5 177.72(18) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C9 O2 C5 C4 -179.73(18) . . . . ?
C9 O2 C5 C6 -0.2(3) . . . . ?
C3 C4 C5 O2 178.91(18) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
O2 C5 C6 C1 -176.47(17) . . . . ?
C4 C5 C6 C1 3.0(3) . . . . ?
O2 C5 C6 C7 7.7(3) . . . . ?
C4 C5 C6 C7 -172.77(19) . . . . ?
C2 C1 C6 C5 -3.0(3) . . . . ?
C2 C1 C6 C7 172.54(19) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C1 C6 C7 C8 -176.96(19) . . . . ?
C5 C6 C7 C10 -178.95(17) . . . . ?
C1 C6 C7 C10 5.6(3) . . . . ?
C6 C7 C8 C9 -11.6(3) . . . . ?
C10 C7 C8 C9 165.74(18) . . . . ?
C6 C7 C8 C16 172.33(18) . . . . ?
C10 C7 C8 C16 -10.4(3) . . . . ?
C5 O2 C9 O1 165.87(18) . . . . ?
C5 O2 C9 C8 -12.8(3) . . . . ?
C7 C8 C9 O1 -159.7(2) . . . . ?
C16 C8 C9 O1 16.8(3) . . . . ?
C7 C8 C9 O2 18.8(3) . . . . ?
C16 C8 C9 O2 -164.67(16) . . . . ?
C8 C7 C10 C11 95.9(2) . . . . ?
C6 C7 C10 C11 -86.7(2) . . . . ?
C8 C7 C10 C15 -85.4(2) . . . . ?
C6 C7 C10 C15 91.9(2) . . . . ?
C15 C10 C11 C12 1.1(3) . . . . ?
C7 C10 C11 C12 179.69(19) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 1.9(3) . . . . ?
C13 C14 C15 C10 -1.0(3) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C7 C10 C15 C14 -179.23(18) . . . . ?
C7 C8 C16 F2 90.9(2) . . . . ?
C9 C8 C16 F2 -85.35(19) . . . . ?
C7 C8 C16 F3 -22.3(3) . . . . ?
C9 C8 C16 F3 161.40(16) . . . . ?
C7 C8 C16 C17 -143.34(19) . . . . ?
C9 C8 C16 C17 40.4(2) . . . . ?
F2 C16 C17 C22 -178.04(16) . . . . ?
F3 C16 C17 C22 -64.8(2) . . . . ?
C8 C16 C17 C22 57.0(2) . . . . ?
F2 C16 C17 C18 0.7(2) . . . . ?
F3 C16 C17 C18 113.94(19) . . . . ?
C8 C16 C17 C18 -124.23(19) . . . . ?
C22 C17 C18 C19 -0.4(3) . . . . ?
C16 C17 C18 C19 -179.11(17) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C18 C17 C22 C21 0.5(3) . . . . ?
C16 C17 C22 C21 179.29(17) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C28 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 F4 177.61(18) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
F4 C25 C26 C27 -176.68(17) . . . . ?
C24 C25 C26 C27 1.8(3) . . . . ?
C31 O4 C27 C26 179.89(17) . . . . ?
C31 O4 C27 C28 -1.1(3) . . . . ?
C25 C26 C27 O4 177.88(17) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
O4 C27 C28 C23 -179.33(17) . . . . ?
C26 C27 C28 C23 -0.3(3) . . . . ?
O4 C27 C28 C29 -0.2(3) . . . . ?
C26 C27 C28 C29 178.77(18) . . . . ?
C24 C23 C28 C27 1.3(3) . . . . ?
C24 C23 C28 C29 -177.72(19) . . . . ?
C27 C28 C29 C30 0.7(3) . . . . ?
C23 C28 C29 C30 179.71(18) . . . . ?
C27 C28 C29 C32 -179.34(17) . . . . ?
C23 C28 C29 C32 -0.3(3) . . . . ?
C28 C29 C30 C31 0.1(3) . . . . ?
C32 C29 C30 C31 -179.90(18) . . . . ?
C28 C29 C30 C38 -178.72(18) . . . . ?
C32 C29 C30 C38 1.3(3) . . . . ?
C27 O4 C31 O3 -178.49(17) . . . . ?
C27 O4 C31 C30 1.8(3) . . . . ?
C29 C30 C31 O3 179.0(2) . . . . ?
C38 C30 C31 O3 -2.0(3) . . . . ?
C29 C30 C31 O4 -1.3(3) . . . . ?
C38 C30 C31 O4 177.67(16) . . . . ?
C30 C29 C32 C33 -89.5(2) . . . . ?
C28 C29 C32 C33 90.4(2) . . . . ?
C30 C29 C32 C37 90.0(2) . . . . ?
C28 C29 C32 C37 -90.0(2) . . . . ?
C37 C32 C33 C34 -1.2(3) . . . . ?
C29 C32 C33 C34 178.29(18) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C33 C34 C35 C36 1.0(3) . . . . ?
C34 C35 C36 C37 -0.9(3) . . . . ?
C35 C36 C37 C32 -0.3(3) . . . . ?
C33 C32 C37 C36 1.4(3) . . . . ?
C29 C32 C37 C36 -178.15(18) . . . . ?
C29 C30 C38 F6 -8.3(3) . . . . ?
C31 C30 C38 F6 172.83(16) . . . . ?
C29 C30 C38 F5 -121.4(2) . . . . ?
C31 C30 C38 F5 59.7(2) . . . . ?
C29 C30 C38 C39 115.0(2) . . . . ?
C31 C30 C38 C39 -63.9(2) . . . . ?
F6 C38 C39 C44 -102.6(2) . . . . ?
F5 C38 C39 C44 9.9(3) . . . . ?
C30 C38 C39 C44 132.7(2) . . . . ?
F6 C38 C39 C40 74.1(2) . . . . ?
F5 C38 C39 C40 -173.45(17) . . . . ?
C30 C38 C39 C40 -50.7(2) . . . . ?
C44 C39 C40 C41 0.6(3) . . . . ?
C38 C39 C40 C41 -176.08(19) . . . . ?
C39 C40 C41 C42 -0.5(3) . . . . ?
C40 C41 C42 C43 0.1(3) . . . . ?
C41 C42 C43 C44 0.3(4) . . . . ?
C40 C39 C44 C43 -0.3(3) . . . . ?
C38 C39 C44 C43 176.4(2) . . . . ?
C42 C43 C44 C39 -0.2(4) . . . . ?
C50 C45 C46 C47 -0.7(3) . . . . ?
C45 C46 C47 F7 -179.63(18) . . . . ?
C45 C46 C47 C48 0.3(3) . . . . ?
F7 C47 C48 C49 -179.53(18) . . . . ?
C46 C47 C48 C49 0.6(3) . . . . ?
C53 O6 C49 C48 -178.60(18) . . . . ?
C53 O6 C49 C50 1.7(3) . . . . ?
C47 C48 C49 O6 179.28(18) . . . . ?
C47 C48 C49 C50 -1.0(3) . . . . ?
O6 C49 C50 C45 -179.69(18) . . . . ?
C48 C49 C50 C45 0.6(3) . . . . ?
O6 C49 C50 C51 -0.4(3) . . . . ?
C48 C49 C50 C51 179.96(19) . . . . ?
C46 C45 C50 C49 0.3(3) . . . . ?
C46 C45 C50 C51 -179.03(18) . . . . ?
C49 C50 C51 C52 -0.2(3) . . . . ?
C45 C50 C51 C52 179.06(18) . . . . ?
C49 C50 C51 C54 -178.19(17) . . . . ?
C45 C50 C51 C54 1.1(3) . . . . ?
C50 C51 C52 C53 -0.4(3) . . . . ?
C54 C51 C52 C53 177.36(17) . . . . ?
C50 C51 C52 C60 -178.61(18) . . . . ?
C54 C51 C52 C60 -0.8(3) . . . . ?
C49 O6 C53 O5 177.92(17) . . . . ?
C49 O6 C53 C52 -2.3(3) . . . . ?
C51 C52 C53 O5 -178.57(19) . . . . ?
C60 C52 C53 O5 -0.2(3) . . . . ?
C51 C52 C53 O6 1.7(3) . . . . ?
C60 C52 C53 O6 -179.91(16) . . . . ?
C52 C51 C54 C59 -88.5(2) . . . . ?
C50 C51 C54 C59 89.4(2) . . . . ?
C52 C51 C54 C55 92.8(2) . . . . ?
C50 C51 C54 C55 -89.4(2) . . . . ?
C59 C54 C55 C56 2.0(3) . . . . ?
C51 C54 C55 C56 -179.26(18) . . . . ?
C54 C55 C56 C57 -1.6(3) . . . . ?
C55 C56 C57 C58 -0.2(3) . . . . ?
C56 C57 C58 C59 1.6(3) . . . . ?
C55 C54 C59 C58 -0.6(3) . . . . ?
C51 C54 C59 C58 -179.39(18) . . . . ?
C57 C58 C59 C54 -1.2(3) . . . . ?
C51 C52 C60 F9 -8.0(3) . . . . ?
C53 C52 C60 F9 173.69(15) . . . . ?
C51 C52 C60 F8 -121.1(2) . . . . ?
C53 C52 C60 F8 60.6(2) . . . . ?
C51 C52 C60 C61 114.9(2) . . . . ?
C53 C52 C60 C61 -63.4(2) . . . . ?
F9 C60 C61 C62 -115.58(19) . . . . ?
F8 C60 C61 C62 -2.4(2) . . . . ?
C52 C60 C61 C62 120.39(19) . . . . ?
F9 C60 C61 C66 62.4(2) . . . . ?
F8 C60 C61 C66 175.56(17) . . . . ?
C52 C60 C61 C66 -61.6(2) . . . . ?
C66 C61 C62 C63 0.6(3) . . . . ?
C60 C61 C62 C63 178.60(18) . . . . ?
C61 C62 C63 C64 -0.1(3) . . . . ?
C62 C63 C64 C65 -0.5(3) . . . . ?
C63 C64 C65 C66 0.6(3) . . . . ?
C64 C65 C66 C61 -0.1(3) . . . . ?
C62 C61 C66 C65 -0.5(3) . . . . ?
C60 C61 C66 C65 -178.56(19) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_mo_210514_zpp_21dj_0m_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2108045'
loop_
_audit_author_name
_audit_author_address
'Piaopiao Zeng'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_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                   14.1040(6)
_cell_length_b                   15.1682(9)
_cell_length_c                   24.3684(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.661(2)
_cell_angle_gamma                90
_cell_volume                     5086.4(4)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    8257
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1215 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.8954.
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    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            54654
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.117
_diffrn_reflns_theta_min         1.998
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7583
_reflns_number_total             11216
_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 V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         11216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.031
_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)+(0.0354P)²+1.8931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1133
_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:
 C1(H1), C2(H2), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
  C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C48(H48), C55(H55), C56(H56),
  C57(H57), C58(H58), C59(H59), C62(H62), C63(H63), C64(H64), C65(H65), C66(H66)
;
_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 0.17583(10) 0.65520(8) 0.73083(6) 0.0409(3) Uani 1 1 d . . . . .
F2 F 0.40286(8) 0.13358(7) 0.73555(5) 0.0291(3) Uani 1 1 d . . . . .
F3 F 0.47064(8) 0.20573(8) 0.67726(5) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.18534(9) 0.20542(9) 0.70026(6) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.18597(9) 0.35056(9) 0.70347(6) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.38311(16) 0.50933(13) 0.75037(9) 0.0280(5) Uani 1 1 d . . . . .
H1 H 0.451843 0.511613 0.762438 0.034 Uiso 1 1 calc R . . . .
C2 C 0.32923(16) 0.58567(14) 0.75025(9) 0.0313(5) Uani 1 1 d . . . . .
H2 H 0.360100 0.640357 0.761710 0.038 Uiso 1 1 calc R . . . .
C3 C 0.22935(16) 0.58013(14) 0.73301(9) 0.0303(5) Uani 1 1 d . . . . .
C4 C 0.18043(16) 0.50282(14) 0.71758(9) 0.0298(5) Uani 1 1 d . . . . .
H4 H 0.111498 0.500932 0.707031 0.036 Uiso 1 1 calc R . . . .
C5 C 0.23624(14) 0.42766(13) 0.71810(8) 0.0251(4) Uani 1 1 d . . . . .
C6 C 0.33768(14) 0.42858(13) 0.73291(8) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.39002(14) 0.34796(13) 0.72566(8) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.33874(13) 0.27430(13) 0.70604(8) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.23340(14) 0.27144(13) 0.70265(8) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.49888(14) 0.35019(12) 0.74283(8) 0.0215(4) Uani 1 1 d . . . . .
C11 C 0.55769(14) 0.37780(14) 0.70727(9) 0.0287(5) Uani 1 1 d . . . . .
H11 H 0.529215 0.396189 0.670040 0.034 Uiso 1 1 calc R . . . .
C12 C 0.65763(15) 0.37856(15) 0.72597(9) 0.0302(5) Uani 1 1 d . . . . .
H12 H 0.697470 0.397415 0.701431 0.036 Uiso 1 1 calc R . . . .
C13 C 0.69994(15) 0.35218(13) 0.77998(9) 0.0276(5) Uani 1 1 d . . . . .
H13 H 0.768678 0.351625 0.792292 0.033 Uiso 1 1 calc R . . . .
C14 C 0.64202(15) 0.32659(13) 0.81603(9) 0.0288(5) Uani 1 1 d . . . . .
H14 H 0.670941 0.310123 0.853586 0.035 Uiso 1 1 calc R . . . .
C15 C 0.54141(15) 0.32480(13) 0.79760(8) 0.0263(4) Uani 1 1 d . . . . .
H15 H 0.501801 0.306284 0.822350 0.032 Uiso 1 1 calc R . . . .
C16 C 0.38139(13) 0.18852(13) 0.68959(8) 0.0226(4) Uani 1 1 d . . . . .
C17 C 0.32010(13) 0.14185(12) 0.63968(8) 0.0206(4) Uani 1 1 d . . . . .
C18 C 0.29119(14) 0.05489(13) 0.64332(9) 0.0245(4) Uani 1 1 d . . . . .
H18 H 0.309251 0.023862 0.677906 0.029 Uiso 1 1 calc R . . . .
C19 C 0.23589(15) 0.01356(13) 0.59632(9) 0.0273(5) Uani 1 1 d . . . . .
H19 H 0.216276 -0.045986 0.598668 0.033 Uiso 1 1 calc R . . . .
C20 C 0.20918(14) 0.05884(13) 0.54597(9) 0.0273(5) Uani 1 1 d . . . . .
H20 H 0.170576 0.030590 0.513951 0.033 Uiso 1 1 calc R . . . .
C21 C 0.23863(14) 0.14506(13) 0.54226(9) 0.0262(4) Uani 1 1 d . . . . .
H21 H 0.220775 0.175781 0.507550 0.031 Uiso 1 1 calc R . . . .
C22 C 0.29423(14) 0.18705(13) 0.58905(8) 0.0232(4) Uani 1 1 d . . . . .
H22 H 0.314440 0.246350 0.586433 0.028 Uiso 1 1 calc R . . . .
F4 F 0.48759(9) -0.15074(8) 0.57370(5) 0.0334(3) Uani 1 1 d . . . . .
F5 F 0.65534(10) 0.38208(8) 0.59764(5) 0.0378(3) Uani 1 1 d . . . . .
F6 F 0.78119(8) 0.33004(8) 0.57152(5) 0.0364(3) Uani 1 1 d . . . . .
O3 O 0.48392(10) 0.29953(9) 0.54657(7) 0.0339(4) Uani 1 1 d . . . . .
O4 O 0.49204(9) 0.15587(9) 0.55653(6) 0.0250(3) Uani 1 1 d . . . . .
C23 C 0.69192(14) -0.00356(13) 0.58482(9) 0.0246(4) Uani 1 1 d . . . . .
H23 H 0.760799 -0.006046 0.591458 0.030 Uiso 1 1 calc R . . . .
C24 C 0.63961(15) -0.08050(14) 0.58484(9) 0.0284(5) Uani 1 1 d . . . . .
H24 H 0.671556 -0.135925 0.590940 0.034 Uiso 1 1 calc R . . . .
C25 C 0.53962(14) -0.07481(13) 0.57577(8) 0.0255(4) Uani 1 1 d . . . . .
C26 C 0.48925(14) 0.00299(13) 0.56743(8) 0.0245(4) Uani 1 1 d . . . . .
H26 H 0.420541 0.004861 0.562346 0.029 Uiso 1 1 calc R . . . .
C27 C 0.54392(14) 0.07909(12) 0.56681(8) 0.0211(4) Uani 1 1 d . . . . .
C28 C 0.64467(13) 0.07846(12) 0.57512(8) 0.0211(4) Uani 1 1 d . . . . .
C29 C 0.69512(14) 0.16188(13) 0.57251(8) 0.0208(4) Uani 1 1 d . . . . .
C30 C 0.64223(14) 0.23736(13) 0.56264(8) 0.0223(4) Uani 1 1 d . . . . .
C31 C 0.53617(15) 0.23584(13) 0.55476(8) 0.0246(4) Uani 1 1 d . . . . .
C32 C 0.80348(13) 0.15874(12) 0.58101(8) 0.0218(4) Uani 1 1 d . . . . .
C33 C 0.84739(14) 0.14820(13) 0.53574(8) 0.0250(4) Uani 1 1 d . . . . .
H33 H 0.808614 0.141260 0.498857 0.030 Uiso 1 1 calc R . . . .
C34 C 0.94823(15) 0.14781(14) 0.54440(9) 0.0288(5) Uani 1 1 d . . . . .
H34 H 0.978235 0.140631 0.513379 0.035 Uiso 1 1 calc R . . . .
C35 C 1.00483(15) 0.15783(13) 0.59798(9) 0.0277(5) Uani 1 1 d . . . . .
H35 H 1.073664 0.158500 0.603736 0.033 Uiso 1 1 calc R . . . .
C36 C 0.96124(14) 0.16684(13) 0.64309(9) 0.0282(5) Uani 1 1 d . . . . .
H36 H 1.000281 0.172894 0.679973 0.034 Uiso 1 1 calc R . . . .
C37 C 0.86104(14) 0.16714(13) 0.63500(8) 0.0257(4) Uani 1 1 d . . . . .
H37 H 0.831510 0.173088 0.666294 0.031 Uiso 1 1 calc R . . . .
C38 C 0.68154(15) 0.32965(13) 0.55736(9) 0.0261(4) Uani 1 1 d . . . . .
C39 C 0.65016(13) 0.37260(12) 0.50030(8) 0.0224(4) Uani 1 1 d . . . . .
C40 C 0.66022(15) 0.32729(14) 0.45264(9) 0.0298(5) Uani 1 1 d . . . . .
H40 H 0.682950 0.268149 0.455647 0.036 Uiso 1 1 calc R . . . .
C41 C 0.63718(16) 0.36807(14) 0.40049(9) 0.0307(5) Uani 1 1 d . . . . .
H41 H 0.644613 0.337012 0.367844 0.037 Uiso 1 1 calc R . . . .
C42 C 0.60353(16) 0.45354(14) 0.39599(9) 0.0317(5) Uani 1 1 d . . . . .
H42 H 0.587684 0.481490 0.360259 0.038 Uiso 1 1 calc R . . . .
C43 C 0.5929(2) 0.49843(15) 0.44340(10) 0.0440(6) Uani 1 1 d . . . . .
H43 H 0.569420 0.557328 0.440307 0.053 Uiso 1 1 calc R . . . .
C44 C 0.61626(18) 0.45811(14) 0.49541(10) 0.0378(6) Uani 1 1 d . . . . .
H44 H 0.608932 0.489439 0.527979 0.045 Uiso 1 1 calc R . . . .
F7 F 1.12624(10) 0.35868(8) 0.55456(6) 0.0417(3) Uani 1 1 d . . . . .
F8 F 0.95100(8) 0.88546(7) 0.57124(5) 0.0294(3) Uani 1 1 d . . . . .
F9 F 0.85060(8) 0.82637(7) 0.61639(5) 0.0289(3) Uani 1 1 d . . . . .
O5 O 1.13534(10) 0.80638(9) 0.59817(6) 0.0272(3) Uani 1 1 d . . . . .
O6 O 1.12485(10) 0.66366(9) 0.58261(6) 0.0274(3) Uani 1 1 d . . . . .
C45 C 0.93553(15) 0.49781(13) 0.58324(8) 0.0248(4) Uani 1 1 d . . . . .
H45 H 0.870684 0.492928 0.588048 0.030 Uiso 1 1 calc R . . . .
C46 C 0.98435(15) 0.42313(14) 0.57271(9) 0.0284(5) Uani 1 1 d . . . . .
H46 H 0.954238 0.366842 0.570608 0.034 Uiso 1 1 calc R . . . .
C47 C 1.07834(16) 0.43227(14) 0.56527(9) 0.0296(5) Uani 1 1 d . . . . .
C48 C 1.12610(15) 0.51153(14) 0.56800(9) 0.0287(5) Uani 1 1 d . . . . .
H48 H 1.190502 0.515632 0.562362 0.034 Uiso 1 1 calc R . . . .
C49 C 1.07568(14) 0.58525(13) 0.57939(8) 0.0238(4) Uani 1 1 d . . . . .
C50 C 0.98039(14) 0.58128(12) 0.58699(8) 0.0215(4) Uani 1 1 d . . . . .
C51 C 0.93345(13) 0.66263(12) 0.59886(8) 0.0203(4) Uani 1 1 d . . . . .
C52 C 0.98404(14) 0.73996(12) 0.60238(8) 0.0209(4) Uani 1 1 d . . . . .
C53 C 1.08458(14) 0.74168(13) 0.59479(8) 0.0234(4) Uani 1 1 d . . . . .
C54 C 0.83248(13) 0.65497(12) 0.60844(8) 0.0209(4) Uani 1 1 d . . . . .
C55 C 0.75128(15) 0.66048(13) 0.56429(9) 0.0289(5) Uani 1 1 d . . . . .
H55 H 0.758950 0.668617 0.526846 0.035 Uiso 1 1 calc R . . . .
C56 C 0.65885(16) 0.65400(14) 0.57527(11) 0.0377(6) Uani 1 1 d . . . . .
H56 H 0.603269 0.659230 0.545327 0.045 Uiso 1 1 calc R . . . .
C57 C 0.64741(16) 0.64008(15) 0.62922(11) 0.0384(6) Uani 1 1 d . . . . .
H57 H 0.584037 0.635957 0.636434 0.046 Uiso 1 1 calc R . . . .
C58 C 0.72785(16) 0.63208(14) 0.67290(10) 0.0344(5) Uani 1 1 d . . . . .
H58 H 0.719847 0.620930 0.709976 0.041 Uiso 1 1 calc R . . . .
C59 C 0.82036(14) 0.64033(13) 0.66264(9) 0.0252(4) Uani 1 1 d . . . . .
H59 H 0.875608 0.635929 0.692865 0.030 Uiso 1 1 calc R . . . .
C60 C 0.94774(14) 0.83026(13) 0.61559(8) 0.0230(4) Uani 1 1 d . . . . .
C61 C 1.00114(13) 0.87087(12) 0.67005(8) 0.0210(4) Uani 1 1 d . . . . .
C62 C 1.04819(14) 0.95108(13) 0.67105(9) 0.0244(4) Uani 1 1 d . . . . .
H62 H 1.048448 0.981060 0.636856 0.029 Uiso 1 1 calc R . . . .
C63 C 1.09479(15) 0.98762(13) 0.72172(9) 0.0273(5) Uani 1 1 d . . . . .
H63 H 1.127131 1.042666 0.722297 0.033 Uiso 1 1 calc R . . . .
C64 C 1.09450(15) 0.94429(13) 0.77161(9) 0.0273(5) Uani 1 1 d . . . . .
H64 H 1.127059 0.969281 0.806393 0.033 Uiso 1 1 calc R . . . .
C65 C 1.04677(17) 0.86456(14) 0.77078(9) 0.0330(5) Uani 1 1 d . . . . .
H65 H 1.046013 0.835052 0.805071 0.040 Uiso 1 1 calc R . . . .
C66 C 1.00013(16) 0.82765(14) 0.72018(9) 0.0318(5) Uani 1 1 d . . . . .
H66 H 0.967430 0.772809 0.719692 0.038 Uiso 1 1 calc R . . . .


_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 C3 1.361(2) . ?
F2 C16 1.375(2) . ?
F3 C16 1.382(2) . ?
O1 C9 1.204(2) . ?
O2 C5 1.373(2) . ?
O2 C9 1.376(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(3) . ?
C1 C6 1.404(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 C4 1.371(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 C6 1.397(3) . ?
C6 C7 1.459(3) . ?
C7 C8 1.360(3) . ?
C7 C10 1.501(3) . ?
C8 C9 1.471(3) . ?
C8 C16 1.524(3) . ?
C10 C11 1.389(3) . ?
C10 C15 1.392(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.506(3) . ?
C17 C18 1.389(3) . ?
C17 C22 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(3) . ?
C22 H22 0.9500 . ?
F4 C25 1.361(2) . ?
F5 C38 1.375(2) . ?
F6 C38 1.372(2) . ?
O3 C31 1.205(2) . ?
O4 C27 1.369(2) . ?
O4 C31 1.368(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(3) . ?
C23 C28 1.407(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.381(3) . ?
C25 C26 1.370(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.390(3) . ?
C27 C28 1.391(3) . ?
C28 C29 1.460(3) . ?
C29 C30 1.359(3) . ?
C29 C32 1.497(3) . ?
C30 C31 1.466(3) . ?
C30 C38 1.522(3) . ?
C32 C33 1.388(3) . ?
C32 C37 1.392(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.381(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.379(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.383(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.511(3) . ?
C39 C40 1.383(3) . ?
C39 C44 1.378(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.386(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.377(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.377(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.380(3) . ?
C44 H44 0.9500 . ?
F7 C47 1.359(2) . ?
F8 C60 1.376(2) . ?
F9 C60 1.376(2) . ?
O5 C53 1.207(2) . ?
O6 C49 1.370(2) . ?
O6 C53 1.373(2) . ?
C45 H45 0.9500 . ?
C45 C46 1.379(3) . ?
C45 C50 1.409(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.384(3) . ?
C47 C48 1.372(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.385(3) . ?
C49 C50 1.398(3) . ?
C50 C51 1.459(3) . ?
C51 C52 1.366(3) . ?
C51 C54 1.497(3) . ?
C52 C53 1.470(3) . ?
C52 C60 1.521(3) . ?
C54 C55 1.391(3) . ?
C54 C59 1.386(3) . ?
C55 H55 0.9500 . ?
C55 C56 1.391(3) . ?
C56 H56 0.9500 . ?
C56 C57 1.376(3) . ?
C57 H57 0.9500 . ?
C57 C58 1.380(3) . ?
C58 H58 0.9500 . ?
C58 C59 1.387(3) . ?
C59 H59 0.9500 . ?
C60 C61 1.506(3) . ?
C61 C62 1.384(3) . ?
C61 C66 1.389(3) . ?
C62 H62 0.9500 . ?
C62 C63 1.381(3) . ?
C63 H63 0.9500 . ?
C63 C64 1.383(3) . ?
C64 H64 0.9500 . ?
C64 C65 1.382(3) . ?
C65 H65 0.9500 . ?
C65 C66 1.382(3) . ?
C66 H66 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
C5 O2 C9 121.43(15) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.0(2) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
F1 C3 C2 118.74(19) . . ?
F1 C3 C4 117.62(19) . . ?
C4 C3 C2 123.64(19) . . ?
C3 C4 H4 121.6 . . ?
C3 C4 C5 116.8(2) . . ?
C5 C4 H4 121.6 . . ?
O2 C5 C4 116.04(18) . . ?
O2 C5 C6 121.11(17) . . ?
C4 C5 C6 122.85(19) . . ?
C1 C6 C7 123.94(18) . . ?
C5 C6 C1 117.42(18) . . ?
C5 C6 C7 118.50(18) . . ?
C6 C7 C10 117.47(17) . . ?
C8 C7 C6 119.15(17) . . ?
C8 C7 C10 123.33(17) . . ?
C7 C8 C9 119.81(17) . . ?
C7 C8 C16 125.74(17) . . ?
C9 C8 C16 114.35(16) . . ?
O1 C9 O2 117.13(17) . . ?
O1 C9 C8 125.36(18) . . ?
O2 C9 C8 117.50(17) . . ?
C11 C10 C7 123.18(18) . . ?
C11 C10 C15 119.39(18) . . ?
C15 C10 C7 117.42(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.12(19) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.55(19) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.75(19) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.26(19) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.91(19) . . ?
C14 C15 H15 120.0 . . ?
F2 C16 F3 104.08(14) . . ?
F2 C16 C8 109.40(15) . . ?
F2 C16 C17 110.97(16) . . ?
F3 C16 C8 109.08(15) . . ?
F3 C16 C17 107.60(15) . . ?
C17 C16 C8 115.10(16) . . ?
C18 C17 C16 121.29(18) . . ?
C22 C17 C16 118.57(17) . . ?
C22 C17 C18 120.13(18) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.77(19) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.16(19) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.03(19) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.28(19) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 119.62(18) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C31 O4 C27 122.09(15) . . ?
C24 C23 H23 119.5 . . ?
C24 C23 C28 120.94(18) . . ?
C28 C23 H23 119.5 . . ?
C23 C24 H24 120.9 . . ?
C23 C24 C25 118.29(19) . . ?
C25 C24 H24 120.9 . . ?
F4 C25 C24 118.45(18) . . ?
F4 C25 C26 117.76(17) . . ?
C26 C25 C24 123.77(18) . . ?
C25 C26 H26 121.8 . . ?
C25 C26 C27 116.50(18) . . ?
C27 C26 H26 121.8 . . ?
O4 C27 C26 115.65(17) . . ?
O4 C27 C28 121.37(17) . . ?
C26 C27 C28 122.98(18) . . ?
C23 C28 C29 123.81(17) . . ?
C27 C28 C23 117.50(17) . . ?
C27 C28 C29 118.68(17) . . ?
C28 C29 C32 117.31(16) . . ?
C30 C29 C28 118.95(17) . . ?
C30 C29 C32 123.74(18) . . ?
C29 C30 C31 120.98(18) . . ?
C29 C30 C38 126.45(18) . . ?
C31 C30 C38 112.56(17) . . ?
O3 C31 O4 116.74(18) . . ?
O3 C31 C30 125.35(19) . . ?
O4 C31 C30 117.90(17) . . ?
C33 C32 C29 120.90(18) . . ?
C33 C32 C37 119.50(18) . . ?
C37 C32 C29 119.60(17) . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 119.96(19) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.17(19) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.1 . . ?
C36 C35 C34 119.88(19) . . ?
C36 C35 H35 120.1 . . ?
C35 C36 H36 119.8 . . ?
C35 C36 C37 120.4(2) . . ?
C37 C36 H36 119.8 . . ?
C32 C37 H37 120.0 . . ?
C36 C37 C32 120.02(19) . . ?
C36 C37 H37 120.0 . . ?
F5 C38 C30 108.17(16) . . ?
F5 C38 C39 109.71(16) . . ?
F6 C38 F5 103.81(16) . . ?
F6 C38 C30 110.78(16) . . ?
F6 C38 C39 107.87(16) . . ?
C39 C38 C30 115.83(17) . . ?
C40 C39 C38 119.68(18) . . ?
C44 C39 C38 120.75(18) . . ?
C44 C39 C40 119.49(19) . . ?
C39 C40 H40 120.0 . . ?
C39 C40 C41 120.09(19) . . ?
C41 C40 H40 120.0 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.0(2) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 120.1 . . ?
C41 C42 C43 119.8(2) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 119.9 . . ?
C42 C43 C44 120.2(2) . . ?
C44 C43 H43 119.9 . . ?
C39 C44 C43 120.3(2) . . ?
C39 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C49 O6 C53 122.17(15) . . ?
C46 C45 H45 119.5 . . ?
C46 C45 C50 120.98(19) . . ?
C50 C45 H45 119.5 . . ?
C45 C46 H46 120.9 . . ?
C45 C46 C47 118.30(19) . . ?
C47 C46 H46 120.9 . . ?
F7 C47 C46 118.27(19) . . ?
F7 C47 C48 117.99(19) . . ?
C48 C47 C46 123.74(19) . . ?
C47 C48 H48 121.7 . . ?
C47 C48 C49 116.66(19) . . ?
C49 C48 H48 121.7 . . ?
O6 C49 C48 115.88(17) . . ?
O6 C49 C50 121.27(17) . . ?
C48 C49 C50 122.85(19) . . ?
C45 C50 C51 123.77(18) . . ?
C49 C50 C45 117.46(18) . . ?
C49 C50 C51 118.76(17) . . ?
C50 C51 C54 116.98(16) . . ?
C52 C51 C50 119.04(17) . . ?
C52 C51 C54 123.95(17) . . ?
C51 C52 C53 120.82(17) . . ?
C51 C52 C60 126.24(17) . . ?
C53 C52 C60 112.92(16) . . ?
O5 C53 O6 116.64(17) . . ?
O5 C53 C52 125.45(18) . . ?
O6 C53 C52 117.91(16) . . ?
C55 C54 C51 121.63(18) . . ?
C59 C54 C51 118.76(17) . . ?
C59 C54 C55 119.59(18) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 C54 119.6(2) . . ?
C56 C55 H55 120.2 . . ?
C55 C56 H56 119.8 . . ?
C57 C56 C55 120.4(2) . . ?
C57 C56 H56 119.8 . . ?
C56 C57 H57 119.9 . . ?
C56 C57 C58 120.1(2) . . ?
C58 C57 H57 119.9 . . ?
C57 C58 H58 120.0 . . ?
C57 C58 C59 120.0(2) . . ?
C59 C58 H58 120.0 . . ?
C54 C59 C58 120.2(2) . . ?
C54 C59 H59 119.9 . . ?
C58 C59 H59 119.9 . . ?
F8 C60 C52 108.12(15) . . ?
F8 C60 C61 110.30(15) . . ?
F9 C60 F8 104.01(14) . . ?
F9 C60 C52 110.29(15) . . ?
F9 C60 C61 108.20(15) . . ?
C61 C60 C52 115.34(16) . . ?
C62 C61 C60 121.35(18) . . ?
C62 C61 C66 119.79(19) . . ?
C66 C61 C60 118.83(17) . . ?
C61 C62 H62 120.0 . . ?
C63 C62 C61 120.07(19) . . ?
C63 C62 H62 120.0 . . ?
C62 C63 H63 119.9 . . ?
C62 C63 C64 120.17(19) . . ?
C64 C63 H63 119.9 . . ?
C63 C64 H64 120.1 . . ?
C65 C64 C63 119.9(2) . . ?
C65 C64 H64 120.1 . . ?
C64 C65 H65 119.9 . . ?
C64 C65 C66 120.2(2) . . ?
C66 C65 H65 119.9 . . ?
C61 C66 H66 120.0 . . ?
C65 C66 C61 119.91(19) . . ?
C65 C66 H66 120.0 . . ?

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 C3 C4 C5 177.72(18) . . . . ?
F2 C16 C17 C18 0.7(2) . . . . ?
F2 C16 C17 C22 -178.04(16) . . . . ?
F3 C16 C17 C18 113.94(19) . . . . ?
F3 C16 C17 C22 -64.8(2) . . . . ?
O2 C5 C6 C1 -176.47(17) . . . . ?
O2 C5 C6 C7 7.7(3) . . . . ?
C1 C2 C3 F1 -177.73(18) . . . . ?
C1 C2 C3 C4 2.0(3) . . . . ?
C1 C6 C7 C8 -176.96(19) . . . . ?
C1 C6 C7 C10 5.6(3) . . . . ?
C2 C1 C6 C5 -3.0(3) . . . . ?
C2 C1 C6 C7 172.54(19) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C3 C4 C5 O2 178.91(18) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 3.0(3) . . . . ?
C4 C5 C6 C7 -172.77(19) . . . . ?
C5 O2 C9 O1 165.87(18) . . . . ?
C5 O2 C9 C8 -12.8(3) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C5 C6 C7 C10 -178.95(17) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C7 C8 C9 -11.6(3) . . . . ?
C6 C7 C8 C16 172.33(18) . . . . ?
C6 C7 C10 C11 -86.7(2) . . . . ?
C6 C7 C10 C15 91.9(2) . . . . ?
C7 C8 C9 O1 -159.7(2) . . . . ?
C7 C8 C9 O2 18.8(3) . . . . ?
C7 C8 C16 F2 90.9(2) . . . . ?
C7 C8 C16 F3 -22.3(3) . . . . ?
C7 C8 C16 C17 -143.34(19) . . . . ?
C7 C10 C11 C12 179.69(19) . . . . ?
C7 C10 C15 C14 -179.23(18) . . . . ?
C8 C7 C10 C11 95.9(2) . . . . ?
C8 C7 C10 C15 -85.4(2) . . . . ?
C8 C16 C17 C18 -124.23(19) . . . . ?
C8 C16 C17 C22 57.0(2) . . . . ?
C9 O2 C5 C4 -179.73(18) . . . . ?
C9 O2 C5 C6 -0.2(3) . . . . ?
C9 C8 C16 F2 -85.35(19) . . . . ?
C9 C8 C16 F3 161.40(16) . . . . ?
C9 C8 C16 C17 40.4(2) . . . . ?
C10 C7 C8 C9 165.74(18) . . . . ?
C10 C7 C8 C16 -10.4(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 1.9(3) . . . . ?
C13 C14 C15 C10 -1.0(3) . . . . ?
C15 C10 C11 C12 1.1(3) . . . . ?
C16 C8 C9 O1 16.8(3) . . . . ?
C16 C8 C9 O2 -164.67(16) . . . . ?
C16 C17 C18 C19 -179.11(17) . . . . ?
C16 C17 C22 C21 179.29(17) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C17 C22 C21 0.5(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C22 C17 C18 C19 -0.4(3) . . . . ?
F4 C25 C26 C27 -176.68(17) . . . . ?
F5 C38 C39 C40 -173.45(17) . . . . ?
F5 C38 C39 C44 9.9(3) . . . . ?
F6 C38 C39 C40 74.1(2) . . . . ?
F6 C38 C39 C44 -102.6(2) . . . . ?
O4 C27 C28 C23 -179.33(17) . . . . ?
O4 C27 C28 C29 -0.2(3) . . . . ?
C23 C24 C25 F4 177.61(18) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
C23 C28 C29 C30 179.71(18) . . . . ?
C23 C28 C29 C32 -0.3(3) . . . . ?
C24 C23 C28 C27 1.3(3) . . . . ?
C24 C23 C28 C29 -177.72(19) . . . . ?
C24 C25 C26 C27 1.8(3) . . . . ?
C25 C26 C27 O4 177.88(17) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C26 C27 C28 C23 -0.3(3) . . . . ?
C26 C27 C28 C29 178.77(18) . . . . ?
C27 O4 C31 O3 -178.49(17) . . . . ?
C27 O4 C31 C30 1.8(3) . . . . ?
C27 C28 C29 C30 0.7(3) . . . . ?
C27 C28 C29 C32 -179.34(17) . . . . ?
C28 C23 C24 C25 -0.8(3) . . . . ?
C28 C29 C30 C31 0.1(3) . . . . ?
C28 C29 C30 C38 -178.72(18) . . . . ?
C28 C29 C32 C33 90.4(2) . . . . ?
C28 C29 C32 C37 -90.0(2) . . . . ?
C29 C30 C31 O3 179.0(2) . . . . ?
C29 C30 C31 O4 -1.3(3) . . . . ?
C29 C30 C38 F5 -121.4(2) . . . . ?
C29 C30 C38 F6 -8.3(3) . . . . ?
C29 C30 C38 C39 115.0(2) . . . . ?
C29 C32 C33 C34 178.29(18) . . . . ?
C29 C32 C37 C36 -178.15(18) . . . . ?
C30 C29 C32 C33 -89.5(2) . . . . ?
C30 C29 C32 C37 90.0(2) . . . . ?
C30 C38 C39 C40 -50.7(2) . . . . ?
C30 C38 C39 C44 132.7(2) . . . . ?
C31 O4 C27 C26 179.89(17) . . . . ?
C31 O4 C27 C28 -1.1(3) . . . . ?
C31 C30 C38 F5 59.7(2) . . . . ?
C31 C30 C38 F6 172.83(16) . . . . ?
C31 C30 C38 C39 -63.9(2) . . . . ?
C32 C29 C30 C31 -179.90(18) . . . . ?
C32 C29 C30 C38 1.3(3) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C33 C32 C37 C36 1.4(3) . . . . ?
C33 C34 C35 C36 1.0(3) . . . . ?
C34 C35 C36 C37 -0.9(3) . . . . ?
C35 C36 C37 C32 -0.3(3) . . . . ?
C37 C32 C33 C34 -1.2(3) . . . . ?
C38 C30 C31 O3 -2.0(3) . . . . ?
C38 C30 C31 O4 177.67(16) . . . . ?
C38 C39 C40 C41 -176.08(19) . . . . ?
C38 C39 C44 C43 176.4(2) . . . . ?
C39 C40 C41 C42 -0.5(3) . . . . ?
C40 C39 C44 C43 -0.3(3) . . . . ?
C40 C41 C42 C43 0.1(3) . . . . ?
C41 C42 C43 C44 0.3(4) . . . . ?
C42 C43 C44 C39 -0.2(4) . . . . ?
C44 C39 C40 C41 0.6(3) . . . . ?
F7 C47 C48 C49 -179.53(18) . . . . ?
F8 C60 C61 C62 -2.4(2) . . . . ?
F8 C60 C61 C66 175.56(17) . . . . ?
F9 C60 C61 C62 -115.58(19) . . . . ?
F9 C60 C61 C66 62.4(2) . . . . ?
O6 C49 C50 C45 -179.69(18) . . . . ?
O6 C49 C50 C51 -0.4(3) . . . . ?
C45 C46 C47 F7 -179.63(18) . . . . ?
C45 C46 C47 C48 0.3(3) . . . . ?
C45 C50 C51 C52 179.06(18) . . . . ?
C45 C50 C51 C54 1.1(3) . . . . ?
C46 C45 C50 C49 0.3(3) . . . . ?
C46 C45 C50 C51 -179.03(18) . . . . ?
C46 C47 C48 C49 0.6(3) . . . . ?
C47 C48 C49 O6 179.28(18) . . . . ?
C47 C48 C49 C50 -1.0(3) . . . . ?
C48 C49 C50 C45 0.6(3) . . . . ?
C48 C49 C50 C51 179.96(19) . . . . ?
C49 O6 C53 O5 177.92(17) . . . . ?
C49 O6 C53 C52 -2.3(3) . . . . ?
C49 C50 C51 C52 -0.2(3) . . . . ?
C49 C50 C51 C54 -178.19(17) . . . . ?
C50 C45 C46 C47 -0.7(3) . . . . ?
C50 C51 C52 C53 -0.4(3) . . . . ?
C50 C51 C52 C60 -178.61(18) . . . . ?
C50 C51 C54 C55 -89.4(2) . . . . ?
C50 C51 C54 C59 89.4(2) . . . . ?
C51 C52 C53 O5 -178.57(19) . . . . ?
C51 C52 C53 O6 1.7(3) . . . . ?
C51 C52 C60 F8 -121.1(2) . . . . ?
C51 C52 C60 F9 -8.0(3) . . . . ?
C51 C52 C60 C61 114.9(2) . . . . ?
C51 C54 C55 C56 -179.26(18) . . . . ?
C51 C54 C59 C58 -179.39(18) . . . . ?
C52 C51 C54 C55 92.8(2) . . . . ?
C52 C51 C54 C59 -88.5(2) . . . . ?
C52 C60 C61 C62 120.39(19) . . . . ?
C52 C60 C61 C66 -61.6(2) . . . . ?
C53 O6 C49 C48 -178.60(18) . . . . ?
C53 O6 C49 C50 1.7(3) . . . . ?
C53 C52 C60 F8 60.6(2) . . . . ?
C53 C52 C60 F9 173.69(15) . . . . ?
C53 C52 C60 C61 -63.4(2) . . . . ?
C54 C51 C52 C53 177.36(17) . . . . ?
C54 C51 C52 C60 -0.8(3) . . . . ?
C54 C55 C56 C57 -1.6(3) . . . . ?
C55 C54 C59 C58 -0.6(3) . . . . ?
C55 C56 C57 C58 -0.2(3) . . . . ?
C56 C57 C58 C59 1.6(3) . . . . ?
C57 C58 C59 C54 -1.2(3) . . . . ?
C59 C54 C55 C56 2.0(3) . . . . ?
C60 C52 C53 O5 -0.2(3) . . . . ?
C60 C52 C53 O6 -179.91(16) . . . . ?
C60 C61 C62 C63 178.60(18) . . . . ?
C60 C61 C66 C65 -178.56(19) . . . . ?
C61 C62 C63 C64 -0.1(3) . . . . ?
C62 C61 C66 C65 -0.5(3) . . . . ?
C62 C63 C64 C65 -0.5(3) . . . . ?
C63 C64 C65 C66 0.6(3) . . . . ?
C64 C65 C66 C61 -0.1(3) . . . . ?
C66 C61 C62 C63 0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
