# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2257053'
loop_
_audit_author_name
_audit_author_address
'Chengyuan Wang'
;Anhui University
China
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_audit_creation_date             2021-10-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H19 F N2 O2'
_chemical_formula_sum            'C33 H19 F N2 O2'
_chemical_formula_weight         494.50
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1633(18)
_cell_length_b                   10.482(3)
_cell_length_c                   12.830(3)
_cell_angle_alpha                94.112(18)
_cell_angle_beta                 100.528(16)
_cell_angle_gamma                104.496(18)
_cell_volume                     1164.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9084
_cell_measurement_temperature    120
_cell_measurement_theta_max      70.02
_cell_measurement_theta_min      4.39
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8586
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         69.471
_diffrn_reflns_theta_min         5.287
_diffrn_ambient_temperature      120
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 300K'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
 1829 frames, detector distance = 60 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3353
_reflns_number_total             4158
_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       
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.0, Darmstadt 2021
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1965P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2365
_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), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C29(H29), C30(H30),
  C32(H32), C33(H33)
;
_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 1.41948(17) 1.24268(14) 0.23340(13) 0.0341(4) Uani 1 1 d . . . . .
O1 O 0.3660(2) 0.14991(18) 0.98660(14) 0.0320(5) Uani 1 1 d . . . . .
O2 O 0.2627(2) -0.07935(18) 0.65467(14) 0.0347(5) Uani 1 1 d . . . . .
N1 N 0.3142(2) 0.03362(19) 0.82092(15) 0.0197(5) Uani 1 1 d . . . . .
N2 N 0.8457(3) 0.6387(2) 0.16287(18) 0.0351(6) Uani 1 1 d . . . . .
C1 C 0.0408(3) -0.2967(3) 0.9278(2) 0.0319(6) Uani 1 1 d . . . . .
H1 H -0.018647 -0.369256 0.952504 0.038 Uiso 1 1 calc R U . . .
C2 C -0.0045(3) -0.1805(3) 0.9241(2) 0.0298(6) Uani 1 1 d . . . . .
H2 H -0.094938 -0.175258 0.945120 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0855(3) -0.0718(2) 0.88869(19) 0.0235(5) Uani 1 1 d . . . . .
H3 H 0.055274 0.006466 0.885763 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2205(2) -0.0797(2) 0.85774(17) 0.0192(5) Uani 1 1 d . . . . .
C5 C 0.2652(3) -0.1965(2) 0.8609(2) 0.0277(6) Uani 1 1 d . . . . .
H5 H 0.355881 -0.201832 0.840278 0.033 Uiso 1 1 calc R U . . .
C6 C 0.1735(3) -0.3057(3) 0.8952(2) 0.0338(6) Uani 1 1 d . . . . .
H6 H 0.201858 -0.384920 0.896156 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3858(3) 0.1478(2) 0.89550(18) 0.0208(5) Uani 1 1 d . . . . .
C8 C 0.4843(3) 0.2620(2) 0.85688(18) 0.0193(5) Uani 1 1 d . . . . .
C9 C 0.5515(3) 0.3777(2) 0.92607(19) 0.0239(5) Uani 1 1 d . . . . .
H9 H 0.537006 0.382262 0.995976 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6410(3) 0.4877(2) 0.8907(2) 0.0268(6) Uani 1 1 d . . . . .
H10 H 0.683371 0.566274 0.936801 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6675(3) 0.4815(2) 0.78876(19) 0.0203(5) Uani 1 1 d . . . . .
H11 H 0.726448 0.556444 0.766609 0.024 Uiso 1 1 calc R U . . .
C12 C 0.6066(2) 0.3628(2) 0.71653(17) 0.0181(5) Uani 1 1 d . . . . .
C13 C 0.5093(2) 0.2535(2) 0.75200(18) 0.0181(5) Uani 1 1 d . . . . .
C14 C 0.3310(3) 0.0216(2) 0.71447(18) 0.0221(5) Uani 1 1 d . . . . .
C15 C 0.4355(3) 0.1360(2) 0.68080(18) 0.0197(5) Uani 1 1 d . . . . .
C16 C 0.4619(3) 0.1257(2) 0.57867(19) 0.0242(5) Uani 1 1 d . . . . .
H16 H 0.412378 0.048581 0.532085 0.029 Uiso 1 1 calc R U . . .
C17 C 0.5627(3) 0.2305(2) 0.54431(18) 0.0229(5) Uani 1 1 d . . . . .
H17 H 0.582413 0.220266 0.476068 0.027 Uiso 1 1 calc R U . . .
C18 C 0.6340(3) 0.3497(2) 0.61031(18) 0.0191(5) Uani 1 1 d . . . . .
C19 C 0.7330(3) 0.4592(2) 0.56655(18) 0.0196(5) Uani 1 1 d . . . . .
C20 C 0.8794(3) 0.5322(2) 0.62175(18) 0.0199(5) Uani 1 1 d . . . . .
H20 H 0.918401 0.512397 0.688985 0.024 Uiso 1 1 calc R U . . .
C21 C 0.9675(3) 0.6337(2) 0.57795(18) 0.0200(5) Uani 1 1 d . . . . .
H21 H 1.063422 0.682934 0.617044 0.024 Uiso 1 1 calc R U . . .
C22 C 0.9134(3) 0.6630(2) 0.47474(18) 0.0199(5) Uani 1 1 d . . . . .
C23 C 0.7675(3) 0.5901(2) 0.41973(19) 0.0229(5) Uani 1 1 d . . . . .
H23 H 0.728685 0.609136 0.352204 0.027 Uiso 1 1 calc R U . . .
C24 C 0.6791(3) 0.4891(2) 0.46446(19) 0.0231(5) Uani 1 1 d . . . . .
H24 H 0.582549 0.440580 0.425862 0.028 Uiso 1 1 calc R U . . .
C25 C 1.0128(3) 0.7701(2) 0.43327(18) 0.0204(5) Uani 1 1 d . . . . .
H25 H 1.086192 0.831528 0.484917 0.025 Uiso 1 1 calc R U . . .
C26 C 1.0148(3) 0.7939(2) 0.33143(18) 0.0190(5) Uani 1 1 d . . . . .
C27 C 0.9180(3) 0.7044(2) 0.24033(19) 0.0227(5) Uani 1 1 d . . . . .
C28 C 1.1217(2) 0.9125(2) 0.30430(17) 0.0187(5) Uani 1 1 d . . . . .
C29 C 1.1497(3) 1.0363(2) 0.36379(19) 0.0242(5) Uani 1 1 d . . . . .
H29 H 1.100154 1.043938 0.420137 0.029 Uiso 1 1 calc R U . . .
C30 C 1.2496(3) 1.1472(2) 0.3402(2) 0.0258(6) Uani 1 1 d . . . . .
H30 H 1.268466 1.229291 0.380325 0.031 Uiso 1 1 calc R U . . .
C31 C 1.3212(3) 1.1336(2) 0.2556(2) 0.0226(5) Uani 1 1 d . . . . .
C32 C 1.2938(3) 1.0134(2) 0.19246(18) 0.0227(5) Uani 1 1 d . . . . .
H32 H 1.341852 1.007245 0.135117 0.027 Uiso 1 1 calc R U . . .
C33 C 1.1937(3) 0.9037(2) 0.21705(17) 0.0204(5) Uani 1 1 d . . . . .
H33 H 1.173225 0.822403 0.175360 0.025 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 C31 1.351(3) . ?
O1 C7 1.215(3) . ?
O2 C14 1.215(3) . ?
N1 C4 1.445(3) . ?
N1 C7 1.412(3) . ?
N1 C14 1.402(3) . ?
N2 C27 1.155(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(4) . ?
C1 C6 1.379(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 C5 1.386(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.484(3) . ?
C8 C9 1.382(3) . ?
C8 C13 1.406(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.420(3) . ?
C12 C13 1.423(3) . ?
C12 C18 1.433(3) . ?
C13 C15 1.416(3) . ?
C14 C15 1.481(3) . ?
C15 C16 1.377(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.401(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(3) . ?
C18 C19 1.488(3) . ?
C19 C20 1.396(3) . ?
C19 C24 1.399(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.411(3) . ?
C22 C23 1.391(3) . ?
C22 C25 1.457(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.391(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.350(3) . ?
C26 C27 1.442(3) . ?
C26 C28 1.484(3) . ?
C28 C29 1.397(3) . ?
C28 C33 1.408(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.379(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.383(4) . ?
C31 C32 1.389(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.376(3) . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C4 117.63(18) . . ?
C14 N1 C4 117.90(19) . . ?
C14 N1 C7 124.45(19) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(2) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 N1 120.0(2) . . ?
C3 C4 C5 120.2(2) . . ?
C5 C4 N1 119.8(2) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.1(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 N1 120.3(2) . . ?
O1 C7 C8 122.8(2) . . ?
N1 C7 C8 116.86(19) . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 C13 120.3(2) . . ?
C13 C8 C7 121.0(2) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 117.2(2) . . ?
C11 C12 C18 123.6(2) . . ?
C13 C12 C18 119.2(2) . . ?
C8 C13 C12 120.5(2) . . ?
C8 C13 C15 119.7(2) . . ?
C15 C13 C12 119.8(2) . . ?
O2 C14 N1 120.4(2) . . ?
O2 C14 C15 122.9(2) . . ?
N1 C14 C15 116.7(2) . . ?
C13 C15 C14 121.2(2) . . ?
C16 C15 C13 120.1(2) . . ?
C16 C15 C14 118.7(2) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.3 . . ?
C12 C18 C19 122.7(2) . . ?
C17 C18 C12 118.9(2) . . ?
C17 C18 C19 118.4(2) . . ?
C20 C19 C18 123.0(2) . . ?
C20 C19 C24 118.1(2) . . ?
C24 C19 C18 118.8(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.7(2) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C25 117.8(2) . . ?
C23 C22 C21 118.2(2) . . ?
C23 C22 C25 124.0(2) . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.8(2) . . ?
C24 C23 H23 119.6 . . ?
C19 C24 H24 119.5 . . ?
C23 C24 C19 121.1(2) . . ?
C23 C24 H24 119.5 . . ?
C22 C25 H25 115.0 . . ?
C26 C25 C22 130.0(2) . . ?
C26 C25 H25 115.0 . . ?
C25 C26 C27 123.0(2) . . ?
C25 C26 C28 122.4(2) . . ?
C27 C26 C28 114.52(19) . . ?
N2 C27 C26 175.2(2) . . ?
C29 C28 C26 120.23(19) . . ?
C29 C28 C33 118.7(2) . . ?
C33 C28 C26 121.1(2) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.0(2) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 H30 120.7 . . ?
C29 C30 C31 118.5(2) . . ?
C31 C30 H30 120.7 . . ?
F1 C31 C30 118.2(2) . . ?
F1 C31 C32 119.3(2) . . ?
C30 C31 C32 122.5(2) . . ?
C31 C32 H32 120.9 . . ?
C33 C32 C31 118.2(2) . . ?
C33 C32 H32 120.9 . . ?
C28 C33 H33 119.5 . . ?
C32 C33 C28 121.1(2) . . ?
C32 C33 H33 119.5 . . ?

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
F1 C31 C32 C33 179.76(18) . . . . ?
O1 C7 C8 C9 -2.7(4) . . . . ?
O1 C7 C8 C13 177.3(2) . . . . ?
O2 C14 C15 C13 178.0(2) . . . . ?
O2 C14 C15 C16 -2.9(4) . . . . ?
N1 C4 C5 C6 -179.2(2) . . . . ?
N1 C7 C8 C9 177.4(2) . . . . ?
N1 C7 C8 C13 -2.6(3) . . . . ?
N1 C14 C15 C13 -2.5(3) . . . . ?
N1 C14 C15 C16 176.5(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
C2 C3 C4 N1 180.0(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 N1 C7 O1 -1.2(3) . . . . ?
C4 N1 C7 C8 178.68(17) . . . . ?
C4 N1 C14 O2 3.2(3) . . . . ?
C4 N1 C14 C15 -176.25(17) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C7 N1 C4 C3 66.1(3) . . . . ?
C7 N1 C4 C5 -114.5(2) . . . . ?
C7 N1 C14 O2 -178.4(2) . . . . ?
C7 N1 C14 C15 2.1(3) . . . . ?
C7 C8 C9 C10 -178.2(2) . . . . ?
C7 C8 C13 C12 -178.71(18) . . . . ?
C7 C8 C13 C15 2.1(3) . . . . ?
C8 C9 C10 C11 -2.0(4) . . . . ?
C8 C13 C15 C14 0.4(3) . . . . ?
C8 C13 C15 C16 -178.6(2) . . . . ?
C9 C8 C13 C12 1.4(3) . . . . ?
C9 C8 C13 C15 -177.8(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 3.8(3) . . . . ?
C10 C11 C12 C18 -178.3(2) . . . . ?
C11 C12 C13 C8 -4.1(3) . . . . ?
C11 C12 C13 C15 175.1(2) . . . . ?
C11 C12 C18 C17 -177.0(2) . . . . ?
C11 C12 C18 C19 1.7(3) . . . . ?
C12 C13 C15 C14 -178.72(18) . . . . ?
C12 C13 C15 C16 2.2(3) . . . . ?
C12 C18 C19 C20 48.1(3) . . . . ?
C12 C18 C19 C24 -133.3(2) . . . . ?
C13 C8 C9 C10 1.7(4) . . . . ?
C13 C12 C18 C17 0.8(3) . . . . ?
C13 C12 C18 C19 179.50(18) . . . . ?
C13 C15 C16 C17 0.5(4) . . . . ?
C14 N1 C4 C3 -115.4(2) . . . . ?
C14 N1 C4 C5 63.9(3) . . . . ?
C14 N1 C7 O1 -179.5(2) . . . . ?
C14 N1 C7 C8 0.3(3) . . . . ?
C14 C15 C16 C17 -178.5(2) . . . . ?
C15 C16 C17 C18 -2.7(4) . . . . ?
C16 C17 C18 C12 2.0(3) . . . . ?
C16 C17 C18 C19 -176.8(2) . . . . ?
C17 C18 C19 C20 -133.1(2) . . . . ?
C17 C18 C19 C24 45.4(3) . . . . ?
C18 C12 C13 C8 178.0(2) . . . . ?
C18 C12 C13 C15 -2.9(3) . . . . ?
C18 C19 C20 C21 -179.8(2) . . . . ?
C18 C19 C24 C23 -179.7(2) . . . . ?
C19 C20 C21 C22 -2.0(3) . . . . ?
C20 C19 C24 C23 -1.1(3) . . . . ?
C20 C21 C22 C23 1.9(3) . . . . ?
C20 C21 C22 C25 -179.37(19) . . . . ?
C21 C22 C23 C24 -1.4(3) . . . . ?
C21 C22 C25 C26 157.9(2) . . . . ?
C22 C23 C24 C19 1.0(4) . . . . ?
C22 C25 C26 C27 -5.0(4) . . . . ?
C22 C25 C26 C28 177.5(2) . . . . ?
C23 C22 C25 C26 -23.5(4) . . . . ?
C24 C19 C20 C21 1.6(3) . . . . ?
C25 C22 C23 C24 180.0(2) . . . . ?
C25 C26 C28 C29 -41.4(3) . . . . ?
C25 C26 C28 C33 140.3(2) . . . . ?
C26 C28 C29 C30 179.5(2) . . . . ?
C26 C28 C33 C32 -179.46(19) . . . . ?
C27 C26 C28 C29 140.9(2) . . . . ?
C27 C26 C28 C33 -37.4(3) . . . . ?
C28 C29 C30 C31 0.4(4) . . . . ?
C29 C28 C33 C32 2.2(3) . . . . ?
C29 C30 C31 F1 -179.7(2) . . . . ?
C29 C30 C31 C32 1.3(4) . . . . ?
C30 C31 C32 C33 -1.3(4) . . . . ?
C31 C32 C33 C28 -0.5(3) . . . . ?
C33 C28 C29 C30 -2.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_STOE_detector_distance          '60.0 mm'
_STOE_detector_pixelsize_x       '0.172 mm'
_STOE_detector_pixelsize_y       '0.172 mm'
_STOE_detector_size_x            '8.4 cm'
_STOE_detector_size_y            '10.6 cm'
_STOE_evaluation_integration_A   6.7
_STOE_evaluation_integration_B   1.0
_STOE_evaluation_integration_EMS 0.020
_STOE_evaluation_LANA_BIS_l_even_max -
_STOE_evaluation_LANA_BIS_l_odd_max -
_STOE_evaluation_LANA_BOS_l_even_max 4
_STOE_evaluation_LANA_BOS_l_odd_max 1
_STOE_evaluation_LANA_completeness 95.2
_STOE_evaluation_LANA_DXS_max_order 3
_STOE_evaluation_LANA_DYS_max_order 3
_STOE_evaluation_LANA_FS_max_order 3
_STOE_evaluation_LANA_max_2theta_available 138.9
_STOE_evaluation_LANA_max_2theta_desired 138.9
_STOE_evaluation_LANA_mean_redundancy 2.1
_STOE_evaluation_LANA_number_refls_after_OR 8586
_STOE_evaluation_LANA_number_refls_outliers 1226
_STOE_evaluation_LANA_number_refls_total 9812
_STOE_evaluation_LANA_number_refls_unique 4158
_STOE_evaluation_LANA_number_refls_written 8586
_STOE_evaluation_LANA_OR_c1      0.035
_STOE_evaluation_LANA_OR_c2      0
_STOE_evaluation_LANA_OR_c3      0
_STOE_evaluation_LANA_OR_c4      0.7
_STOE_evaluation_LANA_point_group -1
_STOE_evaluation_LANA_table      
;
#----------------------------------------------------------------------------
2Theta          17.1   31.5   45.9   60.3   74.7   89.1  103.5  117.9  132.3
#----------------------------------------------------------------------------
<Resolution>    4.53   2.75   1.97   1.53   1.25   1.10   0.98   0.90   0.85
N(total)          96    342    605    767   1905   1824   1844   1583    846
<Redundancy>     1.7    2.0    1.8    1.6    2.6    2.3    2.2    2.0    1.6
Complet. [%%]    97.9  100.0   99.6   97.6   98.1   99.4   98.7   97.2   77.3
<I/sigma>      138.3   85.4   49.3   22.2   15.5   14.4    9.9    8.3    8.2
R(int)         0.030  0.044  0.067  0.099  0.052  0.040  0.041  0.044  0.041
#----------------------------------------------------------------------------
;
_STOE_measurement_identifier     1
_STOE_measurement_max_exposure_per_frame '0.5 s'
_STOE_measurement_mean_exposure_per_frame '0.4 s'
_STOE_measurement_min_exposure_per_frame '0.3 s'
_STOE_measurement_total_exposure_time '13 min'
_STOE_measurement_total_frame_number 1829
_STOE_measurement_total_run_number 30
_STOE_measurement_tube_power     '30.0 W'
####################################################################### 
# 
# 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_1_pl
_database_code_depnum_ccdc_archive 'CCDC 2257056'
loop_
_audit_author_name
_audit_author_address
'Chengyuan Wang'
;Anhui University
China
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_audit_creation_date             2023-04-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H23 F N2 O2'
_chemical_formula_sum            'C31 H23 F N2 O2'
_chemical_formula_weight         474.51
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   37.136(4)
_cell_length_b                   6.9430(9)
_cell_length_c                   18.752(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.959(10)
_cell_angle_gamma                90
_cell_volume                     4711.8(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3864
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      66.73
_cell_measurement_theta_min      3.47
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1350
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19072
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         69.684
_diffrn_reflns_theta_min         6.063
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4164
_reflns_number_total             4380
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.049
_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)+(0.1121P)²+6.1326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.1813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C01M(H01B,H01C), C01P(H01F,H01G), C01Y(H01H,H01J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00D(H00D), C00K(H00K), C00T(H00T), C00U(H00U),
 C00Z(H00Z), C01A(H01A), C01D(H01D), C01E(H01E), C01I(H01I), C01S(H01S),
 C01T(H01T), C01U(H01U)
2.c Idealised Me refined as rotating group:
 C020(H02A,H02B,H02C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F005 F 0.53820(4) 0.4284(2) 0.20041(7) 0.0455(4) Uani 1 1 d . . . . .
O001 O 0.20958(4) 0.47757(17) -0.65091(6) 0.0182(3) Uani 1 1 d . . . . .
O004 O 0.14782(3) 0.6440(2) -0.47631(7) 0.0242(3) Uani 1 1 d . . . . .
N008 N 0.17912(4) 0.5700(2) -0.56388(7) 0.0147(3) Uani 1 1 d . . . . .
N01G N 0.42566(5) 0.9870(3) -0.08184(12) 0.0356(5) Uani 1 1 d . . . . .
C009 C 0.31988(5) 0.6989(2) -0.21728(8) 0.0146(4) Uani 1 1 d . . . . .
H009 H 0.305496 0.809706 -0.226311 0.018 Uiso 1 1 calc R U . . .
C00A C 0.34956(5) 0.6933(2) -0.15718(8) 0.0149(4) Uani 1 1 d . . . . .
H00A H 0.354974 0.800395 -0.126899 0.018 Uiso 1 1 calc R U . . .
C00C C 0.21068(5) 0.5085(2) -0.58633(9) 0.0127(4) Uani 1 1 d . . . . .
C00D C 0.36257(5) 0.3699(2) -0.18945(9) 0.0157(4) Uani 1 1 d . . . . .
H00D H 0.376673 0.258226 -0.180119 0.019 Uiso 1 1 calc R U . . .
C00E C 0.24516(5) 0.4873(2) -0.52894(8) 0.0118(3) Uani 1 1 d . . . . .
C00H C 0.31121(4) 0.5414(2) -0.26444(8) 0.0132(3) Uani 1 1 d . . . . .
C00K C 0.31059(5) 0.4226(2) -0.49533(9) 0.0149(4) Uani 1 1 d . . . . .
H00K H 0.332340 0.389187 -0.509025 0.018 Uiso 1 1 calc R U . . .
C00L C 0.27756(5) 0.5491(2) -0.32499(8) 0.0127(3) Uani 1 1 d . . . . .
C00N C 0.37135(4) 0.5278(2) -0.14185(8) 0.0140(4) Uani 1 1 d . . . . .
C00P C 0.27834(4) 0.5073(2) -0.39981(8) 0.0114(3) Uani 1 1 d . . . . .
C00T C 0.33327(5) 0.3773(2) -0.25009(9) 0.0149(4) Uani 1 1 d . . . . .
H00T H 0.328304 0.272021 -0.281401 0.018 Uiso 1 1 calc R U . . .
C00U C 0.27734(5) 0.4374(2) -0.54897(8) 0.0135(3) Uani 1 1 d . . . . .
H00U H 0.277189 0.413421 -0.597833 0.016 Uiso 1 1 calc R U . . .
C00V C 0.17700(5) 0.5985(2) -0.49106(9) 0.0148(4) Uani 1 1 d . . . . .
C00Z C 0.21157(5) 0.6151(2) -0.36288(9) 0.0156(4) Uani 1 1 d . . . . .
H00Z H 0.189625 0.649865 -0.350252 0.019 Uiso 1 1 calc R U . . .
C010 C 0.42446(5) 0.6348(3) -0.03840(9) 0.0163(4) Uani 1 1 d . . . . .
C012 C 0.21176(4) 0.5757(2) -0.43471(8) 0.0120(3) Uani 1 1 d . . . . .
C018 C 0.24491(4) 0.5224(2) -0.45454(8) 0.0109(3) Uani 1 1 d . . . . .
C01A C 0.31106(4) 0.4571(2) -0.42285(9) 0.0132(3) Uani 1 1 d . . . . .
H01A H 0.333248 0.447492 -0.388241 0.016 Uiso 1 1 calc R U . . .
C01D C 0.24439(5) 0.6031(2) -0.30854(8) 0.0153(4) Uani 1 1 d . . . . .
H01D H 0.243859 0.631976 -0.260357 0.018 Uiso 1 1 calc R U . . .
C01E C 0.40131(5) 0.5021(2) -0.07696(9) 0.0160(4) Uani 1 1 d . . . . .
H01E H 0.404950 0.376391 -0.059726 0.019 Uiso 1 1 calc R U . . .
C01F C 0.42408(5) 0.8306(3) -0.06305(10) 0.0214(4) Uani 1 1 d . . . . .
C01H C 0.45365(5) 0.5853(3) 0.02740(9) 0.0187(4) Uani 1 1 d . . . . .
C01I C 0.48496(5) 0.7005(3) 0.04864(9) 0.0218(4) Uani 1 1 d . . . . .
H01I H 0.486794 0.813557 0.023097 0.026 Uiso 1 1 calc R U . . .
C01M C 0.14569(5) 0.6140(3) -0.62067(9) 0.0210(4) Uani 1 1 d . . . . .
H01B H 0.153074 0.642143 -0.666003 0.025 Uiso 1 1 calc R U . . .
H01C H 0.134417 0.729449 -0.606328 0.025 Uiso 1 1 calc R U . . .
C01P C 0.11700(5) 0.4568(3) -0.63505(10) 0.0246(4) Uani 1 1 d . . . . .
H01F H 0.106905 0.437563 -0.592149 0.030 Uiso 1 1 calc R U . . .
H01G H 0.128180 0.336895 -0.645607 0.030 Uiso 1 1 calc R U . . .
C01S C 0.45103(5) 0.4181(3) 0.06731(10) 0.0282(5) Uani 1 1 d . . . . .
H01S H 0.430001 0.341588 0.054846 0.034 Uiso 1 1 calc R U . . .
C01T C 0.51359(5) 0.6496(3) 0.10742(10) 0.0263(4) Uani 1 1 d . . . . .
H01T H 0.534420 0.727025 0.121369 0.032 Uiso 1 1 calc R U . . .
C01U C 0.47960(6) 0.3650(4) 0.12550(11) 0.0347(5) Uani 1 1 d . . . . .
H01U H 0.478121 0.252346 0.151494 0.042 Uiso 1 1 calc R U . . .
C01W C 0.51016(5) 0.4829(4) 0.14388(10) 0.0300(5) Uani 1 1 d . . . . .
C01Y C 0.08605(6) 0.5150(3) -0.70056(12) 0.0328(5) Uani 1 1 d . . . . .
H01H H 0.076838 0.641289 -0.691533 0.039 Uiso 1 1 calc R U . . .
H01J H 0.096074 0.523641 -0.743971 0.039 Uiso 1 1 calc R U . . .
C020 C 0.05451(7) 0.3735(5) -0.71420(15) 0.0549(8) Uani 1 1 d . . . . .
H02A H 0.044648 0.363460 -0.671200 0.082 Uiso 1 1 calc R U . . .
H02B H 0.063252 0.249602 -0.725569 0.082 Uiso 1 1 calc R U . . .
H02C H 0.035531 0.417180 -0.754520 0.082 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
F005 C01W 1.362(2) . ?
O001 C00C 1.222(2) . ?
O004 C00V 1.219(2) . ?
N008 C00C 1.398(2) . ?
N008 C00V 1.399(2) . ?
N008 C01M 1.475(2) . ?
N01G C01F 1.147(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.389(2) . ?
C009 C00H 1.398(2) . ?
C00A H00A 0.9300 . ?
C00A C00N 1.397(2) . ?
C00C C00E 1.484(2) . ?
C00D H00D 0.9300 . ?
C00D C00N 1.405(2) . ?
C00D C00T 1.387(2) . ?
C00E C00U 1.375(2) . ?
C00E C018 1.419(2) . ?
C00H C00L 1.489(2) . ?
C00H C00T 1.394(2) . ?
C00K H00K 0.9300 . ?
C00K C00U 1.411(2) . ?
C00K C01A 1.376(2) . ?
C00L C00P 1.439(2) . ?
C00L C01D 1.387(2) . ?
C00N C01E 1.464(2) . ?
C00P C018 1.426(2) . ?
C00P C01A 1.421(2) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00V C012 1.482(2) . ?
C00Z H00Z 0.9300 . ?
C00Z C012 1.376(2) . ?
C00Z C01D 1.405(2) . ?
C010 C01E 1.354(2) . ?
C010 C01F 1.435(3) . ?
C010 C01H 1.488(2) . ?
C012 C018 1.412(2) . ?
C01A H01A 0.9300 . ?
C01D H01D 0.9300 . ?
C01E H01E 0.9300 . ?
C01H C01I 1.394(3) . ?
C01H C01S 1.396(3) . ?
C01I H01I 0.9300 . ?
C01I C01T 1.395(3) . ?
C01M H01B 0.9700 . ?
C01M H01C 0.9700 . ?
C01M C01P 1.507(3) . ?
C01P H01F 0.9700 . ?
C01P H01G 0.9700 . ?
C01P C01Y 1.536(3) . ?
C01S H01S 0.9300 . ?
C01S C01U 1.390(3) . ?
C01T H01T 0.9300 . ?
C01T C01W 1.365(3) . ?
C01U H01U 0.9300 . ?
C01U C01W 1.379(3) . ?
C01Y H01H 0.9700 . ?
C01Y H01J 0.9700 . ?
C01Y C020 1.506(3) . ?
C020 H02A 0.9600 . ?
C020 H02B 0.9600 . ?
C020 H02C 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
C00C N008 C00V 124.85(13) . . ?
C00C N008 C01M 118.21(13) . . ?
C00V N008 C01M 116.92(14) . . ?
C00A C009 H009 119.4 . . ?
C00A C009 C00H 121.29(15) . . ?
C00H C009 H009 119.4 . . ?
C009 C00A H00A 119.7 . . ?
C009 C00A C00N 120.52(15) . . ?
C00N C00A H00A 119.7 . . ?
O001 C00C N008 120.56(15) . . ?
O001 C00C C00E 122.21(15) . . ?
N008 C00C C00E 117.22(14) . . ?
C00N C00D H00D 119.4 . . ?
C00T C00D H00D 119.4 . . ?
C00T C00D C00N 121.27(15) . . ?
C00U C00E C00C 119.24(14) . . ?
C00U C00E C018 120.66(15) . . ?
C018 C00E C00C 120.08(15) . . ?
C009 C00H C00L 119.29(14) . . ?
C00T C00H C009 118.38(15) . . ?
C00T C00H C00L 122.20(14) . . ?
C00U C00K H00K 119.8 . . ?
C01A C00K H00K 119.8 . . ?
C01A C00K C00U 120.43(15) . . ?
C00P C00L C00H 122.62(14) . . ?
C01D C00L C00H 118.39(14) . . ?
C01D C00L C00P 118.97(14) . . ?
C00A C00N C00D 118.01(15) . . ?
C00A C00N C01E 124.63(15) . . ?
C00D C00N C01E 117.23(15) . . ?
C018 C00P C00L 118.80(15) . . ?
C01A C00P C00L 123.46(14) . . ?
C01A C00P C018 117.71(14) . . ?
C00D C00T C00H 120.51(15) . . ?
C00D C00T H00T 119.7 . . ?
C00H C00T H00T 119.7 . . ?
C00E C00U C00K 119.94(14) . . ?
C00E C00U H00U 120.0 . . ?
C00K C00U H00U 120.0 . . ?
O004 C00V N008 120.37(15) . . ?
O004 C00V C012 122.86(15) . . ?
N008 C00V C012 116.75(14) . . ?
C012 C00Z H00Z 119.9 . . ?
C012 C00Z C01D 120.27(15) . . ?
C01D C00Z H00Z 119.9 . . ?
C01E C010 C01F 120.89(15) . . ?
C01E C010 C01H 122.90(16) . . ?
C01F C010 C01H 116.00(15) . . ?
C00Z C012 C00V 118.80(15) . . ?
C00Z C012 C018 120.39(15) . . ?
C018 C012 C00V 120.76(14) . . ?
C00E C018 C00P 119.88(15) . . ?
C012 C018 C00E 120.16(14) . . ?
C012 C018 C00P 119.95(14) . . ?
C00K C01A C00P 121.38(15) . . ?
C00K C01A H01A 119.3 . . ?
C00P C01A H01A 119.3 . . ?
C00L C01D C00Z 121.61(14) . . ?
C00L C01D H01D 119.2 . . ?
C00Z C01D H01D 119.2 . . ?
C00N C01E H01E 115.3 . . ?
C010 C01E C00N 129.37(16) . . ?
C010 C01E H01E 115.3 . . ?
N01G C01F C010 176.6(2) . . ?
C01I C01H C010 120.68(16) . . ?
C01I C01H C01S 118.54(16) . . ?
C01S C01H C010 120.72(16) . . ?
C01H C01I H01I 119.3 . . ?
C01H C01I C01T 121.33(18) . . ?
C01T C01I H01I 119.3 . . ?
N008 C01M H01B 108.5 . . ?
N008 C01M H01C 108.5 . . ?
N008 C01M C01P 115.22(15) . . ?
H01B C01M H01C 107.5 . . ?
C01P C01M H01B 108.5 . . ?
C01P C01M H01C 108.5 . . ?
C01M C01P H01F 109.9 . . ?
C01M C01P H01G 109.9 . . ?
C01M C01P C01Y 108.95(17) . . ?
H01F C01P H01G 108.3 . . ?
C01Y C01P H01F 109.9 . . ?
C01Y C01P H01G 109.9 . . ?
C01H C01S H01S 119.7 . . ?
C01U C01S C01H 120.56(18) . . ?
C01U C01S H01S 119.7 . . ?
C01I C01T H01T 121.0 . . ?
C01W C01T C01I 118.08(18) . . ?
C01W C01T H01T 121.0 . . ?
C01S C01U H01U 120.7 . . ?
C01W C01U C01S 118.7(2) . . ?
C01W C01U H01U 120.7 . . ?
F005 C01W C01T 118.98(19) . . ?
F005 C01W C01U 118.2(2) . . ?
C01T C01W C01U 122.82(18) . . ?
C01P C01Y H01H 109.2 . . ?
C01P C01Y H01J 109.2 . . ?
H01H C01Y H01J 107.9 . . ?
C020 C01Y C01P 112.2(2) . . ?
C020 C01Y H01H 109.2 . . ?
C020 C01Y H01J 109.2 . . ?
C01Y C020 H02A 109.5 . . ?
C01Y C020 H02B 109.5 . . ?
C01Y C020 H02C 109.5 . . ?
H02A C020 H02B 109.5 . . ?
H02A C020 H02C 109.5 . . ?
H02B C020 H02C 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
O001 C00C C00E C00U 2.2(2) . . . . ?
O001 C00C C00E C018 -179.15(14) . . . . ?
O004 C00V C012 C00Z -2.8(3) . . . . ?
O004 C00V C012 C018 179.91(15) . . . . ?
N008 C00C C00E C00U -176.49(13) . . . . ?
N008 C00C C00E C018 2.2(2) . . . . ?
N008 C00V C012 C00Z 175.64(14) . . . . ?
N008 C00V C012 C018 -1.7(2) . . . . ?
N008 C01M C01P C01Y -174.05(15) . . . . ?
C009 C00A C00N C00D 0.8(2) . . . . ?
C009 C00A C00N C01E -174.98(15) . . . . ?
C009 C00H C00L C00P 128.66(16) . . . . ?
C009 C00H C00L C01D -49.9(2) . . . . ?
C009 C00H C00T C00D 1.4(2) . . . . ?
C00A C009 C00H C00L 175.64(14) . . . . ?
C00A C009 C00H C00T -0.4(2) . . . . ?
C00A C00N C01E C010 -31.8(3) . . . . ?
C00C N008 C00V O004 -176.65(15) . . . . ?
C00C N008 C00V C012 4.9(2) . . . . ?
C00C N008 C01M C01P 99.42(18) . . . . ?
C00C C00E C00U C00K 178.02(14) . . . . ?
C00C C00E C018 C00P -178.21(13) . . . . ?
C00C C00E C018 C012 0.7(2) . . . . ?
C00D C00N C01E C010 152.41(18) . . . . ?
C00H C009 C00A C00N -0.8(2) . . . . ?
C00H C00L C00P C018 -178.60(13) . . . . ?
C00H C00L C00P C01A -0.7(2) . . . . ?
C00H C00L C01D C00Z 179.47(15) . . . . ?
C00L C00H C00T C00D -174.46(14) . . . . ?
C00L C00P C018 C00E 178.19(14) . . . . ?
C00L C00P C018 C012 -0.7(2) . . . . ?
C00L C00P C01A C00K -178.50(15) . . . . ?
C00N C00D C00T C00H -1.4(2) . . . . ?
C00P C00L C01D C00Z 0.9(2) . . . . ?
C00T C00D C00N C00A 0.2(2) . . . . ?
C00T C00D C00N C01E 176.35(14) . . . . ?
C00T C00H C00L C00P -55.5(2) . . . . ?
C00T C00H C00L C01D 125.97(17) . . . . ?
C00U C00E C018 C00P 0.4(2) . . . . ?
C00U C00E C018 C012 179.32(14) . . . . ?
C00U C00K C01A C00P 0.4(2) . . . . ?
C00V N008 C00C O001 176.15(15) . . . . ?
C00V N008 C00C C00E -5.1(2) . . . . ?
C00V N008 C01M C01P -82.33(19) . . . . ?
C00V C012 C018 C00E -0.9(2) . . . . ?
C00V C012 C018 C00P 177.95(13) . . . . ?
C00Z C012 C018 C00E -178.19(14) . . . . ?
C00Z C012 C018 C00P 0.7(2) . . . . ?
C010 C01H C01I C01T -175.95(16) . . . . ?
C010 C01H C01S C01U 175.27(19) . . . . ?
C012 C00Z C01D C00L -0.9(3) . . . . ?
C018 C00E C00U C00K -0.6(2) . . . . ?
C018 C00P C01A C00K -0.6(2) . . . . ?
C01A C00K C00U C00E 0.2(2) . . . . ?
C01A C00P C018 C00E 0.2(2) . . . . ?
C01A C00P C018 C012 -178.72(14) . . . . ?
C01D C00L C00P C018 -0.1(2) . . . . ?
C01D C00L C00P C01A 177.81(15) . . . . ?
C01D C00Z C012 C00V -177.21(14) . . . . ?
C01D C00Z C012 C018 0.1(2) . . . . ?
C01E C010 C01H C01I 155.18(18) . . . . ?
C01E C010 C01H C01S -22.0(3) . . . . ?
C01F C010 C01E C00N -5.9(3) . . . . ?
C01F C010 C01H C01I -19.7(2) . . . . ?
C01F C010 C01H C01S 163.16(18) . . . . ?
C01H C010 C01E C00N 179.54(15) . . . . ?
C01H C01I C01T C01W 0.0(3) . . . . ?
C01H C01S C01U C01W 1.3(3) . . . . ?
C01I C01H C01S C01U -1.9(3) . . . . ?
C01I C01T C01W F005 178.53(17) . . . . ?
C01I C01T C01W C01U -0.7(3) . . . . ?
C01M N008 C00C O001 -5.7(2) . . . . ?
C01M N008 C00C C00E 172.97(14) . . . . ?
C01M N008 C00V O004 5.2(2) . . . . ?
C01M N008 C00V C012 -173.25(13) . . . . ?
C01M C01P C01Y C020 -174.8(2) . . . . ?
C01S C01H C01I C01T 1.3(3) . . . . ?
C01S C01U C01W F005 -179.2(2) . . . . ?
C01S C01U C01W C01T 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_cu_20211019f6_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2257055'
loop_
_audit_author_name
_audit_author_address
'Chengyuan Wang'
;Anhui University
China
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_audit_creation_date             2021-10-27
_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         'C37 H27 F N2 O2'
_chemical_formula_sum            'C37 H27 F N2 O2'
_chemical_formula_weight         550.60
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2811(2)
_cell_length_b                   11.3035(3)
_cell_length_c                   16.0055(3)
_cell_angle_alpha                74.7870(10)
_cell_angle_beta                 78.6230(10)
_cell_angle_gamma                81.7740(10)
_cell_volume                     1410.67(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      67.96
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.7497
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1434 before and 0.0763 after correction.
The Ratio of minimum to maximum transmission is 0.8097.
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    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            47918
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         2.902
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3818
_reflns_number_total             4973
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         4973
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.108
_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)+(0.1077P)²+0.6877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.2090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C1B \\sim C4-C1A
 with sigma of 0.02
 C4-C2B \\sim C4-C2A
 with sigma of 0.02
 C4-C3B \\sim C4-C3A
 with sigma of 0.02
3. Rigid bond restraints
 C10, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C2A \\sim C2B \\sim C1B \\sim C1A \\sim C4 \\sim C3B \\sim C3A: within 2A with
sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C2A) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1A)
\\sim Ueq, Uanis(C3B) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4) \\sim Ueq:
with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(H2BC)=
 Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(H3BC)=1-FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C20(H20), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C33(H33), C34(H34),
  C36(H36), C37(H37)
6.b Idealised Me refined as rotating group:
 C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,H2BC), C3B(H3BA,H3BB,H3BC), C1A(H1AA,H1AB,
 H1AC), C3A(H3AA,H3AB,H3AC), C2A(H2AA,H2AB,H2AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.7264(3) 0.8488(3) 0.04879(16) 0.1204(9) Uani 1 1 d . . . . .
O1 O -0.1908(2) 0.92496(19) 0.67759(14) 0.0703(6) Uani 1 1 d . . . . .
O2 O -0.1438(3) 0.5098(2) 0.78600(16) 0.0814(7) Uani 1 1 d . . . . .
N1 N -0.1697(2) 0.7173(2) 0.73098(14) 0.0516(5) Uani 1 1 d . . . . .
N2 N 1.1896(4) 0.5465(3) 0.4144(2) 0.0969(11) Uani 1 1 d . . . . .
C1B C -0.9115(8) 0.6447(6) 0.9323(6) 0.0727(10) Uani 0.508(7) 1 d D U P A 2
H1BA H -1.015405 0.641626 0.971671 0.109 Uiso 0.508(7) 1 calc GR . P A 2
H1BB H -0.841836 0.570210 0.949835 0.109 Uiso 0.508(7) 1 calc GR . P A 2
H1BC H -0.930355 0.653036 0.873657 0.109 Uiso 0.508(7) 1 calc GR . P A 2
C2B C -0.9503(8) 0.8332(7) 0.8788(5) 0.0694(10) Uani 0.508(7) 1 d D U P A 2
H2BA H -0.969768 0.788106 0.839166 0.104 Uiso 0.508(7) 1 calc GR . P A 2
H2BB H -0.907176 0.909330 0.845732 0.104 Uiso 0.508(7) 1 calc GR . P A 2
H2BC H -1.052423 0.850325 0.915953 0.104 Uiso 0.508(7) 1 calc GR . P A 2
C3B C -0.8243(8) 0.7526(8) 1.0298(4) 0.0687(10) Uani 0.508(7) 1 d D U P A 2
H3BA H -0.935923 0.762951 1.059752 0.103 Uiso 0.508(7) 1 calc GR . P A 2
H3BB H -0.764281 0.817605 1.032873 0.103 Uiso 0.508(7) 1 calc GR . P A 2
H3BC H -0.771795 0.674590 1.057225 0.103 Uiso 0.508(7) 1 calc GR . P A 2
C4 C -0.8256(4) 0.7569(3) 0.9351(2) 0.0644(6) Uani 1 1 d D U . . .
C5 C -0.6249(4) 0.7744(4) 0.7906(2) 0.0882(12) Uani 1 1 d . . . . .
H5 H -0.715337 0.800633 0.761635 0.106 Uiso 1 1 calc R . . . .
C6 C -0.4699(4) 0.7648(4) 0.7417(2) 0.0897(12) Uani 1 1 d . . . . .
H6 H -0.456773 0.785059 0.680734 0.108 Uiso 1 1 calc R . . . .
C7 C -0.3334(3) 0.7252(3) 0.78269(17) 0.0542(6) Uani 1 1 d . . . . .
C8 C -0.3560(3) 0.7022(4) 0.87136(19) 0.0795(10) Uani 1 1 d . . . . .
H8 H -0.264842 0.679828 0.899992 0.095 Uiso 1 1 calc R . . . .
C9 C -0.5130(3) 0.7115(4) 0.9198(2) 0.0797(10) Uani 1 1 d . . . . .
H9 H -0.524641 0.693336 0.980694 0.096 Uiso 1 1 calc R . . . .
C10 C -0.6521(3) 0.7464(3) 0.88190(17) 0.0560(6) Uani 1 1 d . U . . .
C11 C -0.1079(3) 0.8261(2) 0.67883(17) 0.0512(6) Uani 1 1 d . . . . .
C12 C -0.0817(3) 0.5992(3) 0.73802(18) 0.0556(6) Uani 1 1 d . . . . .
C13 C 0.0583(3) 0.8165(2) 0.62618(16) 0.0446(5) Uani 1 1 d . . . . .
C14 C 0.1230(3) 0.9203(2) 0.57306(17) 0.0510(6) Uani 1 1 d . . . . .
H14 H 0.061605 0.996380 0.570808 0.061 Uiso 1 1 calc R . . . .
C15 C 0.2805(3) 0.9139(2) 0.52192(18) 0.0515(6) Uani 1 1 d . . . . .
H15 H 0.321452 0.985924 0.485978 0.062 Uiso 1 1 calc R . . . .
C16 C 0.3764(3) 0.8033(2) 0.52360(15) 0.0436(5) Uani 1 1 d . . . . .
C17 C 0.3125(3) 0.6926(2) 0.57881(15) 0.0417(5) Uani 1 1 d . . . . .
C18 C 0.1520(3) 0.7004(2) 0.63001(15) 0.0413(5) Uani 1 1 d . . . . .
C19 C 0.0852(3) 0.5930(2) 0.68485(16) 0.0474(6) Uani 1 1 d . . . . .
C20 C 0.1754(3) 0.4802(2) 0.68867(18) 0.0551(6) Uani 1 1 d . . . . .
H20 H 0.131774 0.409571 0.725338 0.066 Uiso 1 1 calc R . . . .
C21 C 0.3320(3) 0.4713(2) 0.63776(18) 0.0540(6) Uani 1 1 d . . . . .
H21 H 0.391578 0.394520 0.640262 0.065 Uiso 1 1 calc R . . . .
C22 C 0.3989(3) 0.5740(2) 0.58433(16) 0.0467(6) Uani 1 1 d . . . . .
H22 H 0.503392 0.565893 0.550819 0.056 Uiso 1 1 calc R . . . .
C23 C 0.5422(3) 0.8038(2) 0.46687(16) 0.0452(5) Uani 1 1 d . . . . .
C24 C 0.6861(3) 0.7448(2) 0.49823(16) 0.0471(6) Uani 1 1 d . . . . .
H24 H 0.678945 0.701724 0.556751 0.056 Uiso 1 1 calc R . . . .
C25 C 0.8383(3) 0.7487(2) 0.44456(16) 0.0484(6) Uani 1 1 d . . . . .
H25 H 0.931777 0.708391 0.467465 0.058 Uiso 1 1 calc R . . . .
C26 C 0.8545(3) 0.8126(2) 0.35602(16) 0.0472(6) Uani 1 1 d . . . . .
C27 C 0.7104(3) 0.8737(2) 0.32515(17) 0.0528(6) Uani 1 1 d . . . . .
H27 H 0.717794 0.918011 0.266912 0.063 Uiso 1 1 calc R . . . .
C28 C 0.5579(3) 0.8698(2) 0.37876(17) 0.0507(6) Uani 1 1 d . . . . .
H28 H 0.464570 0.911285 0.356242 0.061 Uiso 1 1 calc R . . . .
C29 C 1.0112(3) 0.8222(2) 0.29481(16) 0.0509(6) Uani 1 1 d . . . . .
H29 H 1.011883 0.889406 0.246593 0.061 Uiso 1 1 calc R . . . .
C30 C 1.1544(3) 0.7495(2) 0.29700(16) 0.0500(6) Uani 1 1 d . . . . .
C31 C 1.1701(3) 0.6381(3) 0.36379(19) 0.0616(7) Uani 1 1 d . . . . .
C32 C 1.3062(3) 0.7757(3) 0.23100(16) 0.0520(6) Uani 1 1 d . . . . .
C33 C 1.4182(3) 0.6808(3) 0.20884(19) 0.0637(7) Uani 1 1 d . . . . .
H33 H 1.397925 0.599569 0.235702 0.076 Uiso 1 1 calc R . . . .
C34 C 1.5601(4) 0.7053(4) 0.1472(2) 0.0759(9) Uani 1 1 d . . . . .
H34 H 1.634843 0.641521 0.132254 0.091 Uiso 1 1 calc R . . . .
C35 C 1.5874(4) 0.8249(4) 0.1091(2) 0.0778(10) Uani 1 1 d . . . . .
C36 C 1.4813(4) 0.9212(3) 0.1288(2) 0.0755(9) Uani 1 1 d . . . . .
H36 H 1.503447 1.001958 0.101534 0.091 Uiso 1 1 calc R . . . .
C37 C 1.3400(3) 0.8965(3) 0.19028(18) 0.0618(7) Uani 1 1 d . . . . .
H37 H 1.266571 0.961388 0.204591 0.074 Uiso 1 1 calc R . . . .
C1A C -0.8877(9) 0.6293(7) 0.9726(6) 0.0745(10) Uani 0.492(7) 1 d D U P A 1
H1AA H -1.003776 0.637961 0.995592 0.112 Uiso 0.492(7) 1 calc GR . P A 1
H1AB H -0.828516 0.583934 1.018817 0.112 Uiso 0.492(7) 1 calc GR . P A 1
H1AC H -0.869716 0.585843 0.926959 0.112 Uiso 0.492(7) 1 calc GR . P A 1
C3A C -0.8286(8) 0.8161(8) 1.0125(5) 0.0684(10) Uani 0.492(7) 1 d D U P A 1
H3AA H -0.936187 0.813193 1.048409 0.103 Uiso 0.492(7) 1 calc GR . P A 1
H3AB H -0.804292 0.900223 0.989936 0.103 Uiso 0.492(7) 1 calc GR . P A 1
H3AC H -0.747052 0.771459 1.047228 0.103 Uiso 0.492(7) 1 calc GR . P A 1
C2A C -0.9270(9) 0.8784(7) 0.8928(5) 0.0672(10) Uani 0.492(7) 1 d D U P A 1
H2AA H -0.922994 0.882940 0.831659 0.101 Uiso 0.492(7) 1 calc GR . P A 1
H2AB H -0.880269 0.948191 0.898635 0.101 Uiso 0.492(7) 1 calc GR . P A 1
H2AC H -1.039993 0.878528 0.922059 0.101 Uiso 0.492(7) 1 calc GR . P A 1


_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 C35 1.357(3) . ?
O1 C11 1.222(3) . ?
O2 C12 1.209(3) . ?
N1 C7 1.447(3) . ?
N1 C11 1.395(3) . ?
N1 C12 1.414(3) . ?
N2 C31 1.148(4) . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C1B C4 1.555(7) . ?
C2B H2BA 0.9600 . ?
C2B H2BB 0.9600 . ?
C2B H2BC 0.9600 . ?
C2B C4 1.526(7) . ?
C3B H3BA 0.9600 . ?
C3B H3BB 0.9600 . ?
C3B H3BC 0.9600 . ?
C3B C4 1.506(7) . ?
C4 C10 1.525(4) . ?
C4 C1A 1.530(7) . ?
C4 C3A 1.550(7) . ?
C4 C2A 1.568(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(4) . ?
C5 C10 1.390(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(4) . ?
C7 C8 1.354(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(4) . ?
C11 C13 1.471(3) . ?
C12 C19 1.476(3) . ?
C13 C14 1.365(4) . ?
C13 C18 1.420(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.400(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(3) . ?
C16 C17 1.432(3) . ?
C16 C23 1.489(3) . ?
C17 C18 1.421(3) . ?
C17 C22 1.417(3) . ?
C18 C19 1.412(3) . ?
C19 C20 1.375(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.395(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.364(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.396(3) . ?
C23 C28 1.402(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.401(3) . ?
C26 C27 1.401(3) . ?
C26 C29 1.463(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.343(3) . ?
C30 C31 1.431(4) . ?
C30 C32 1.484(3) . ?
C32 C33 1.386(4) . ?
C32 C37 1.393(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.387(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.360(5) . ?
C35 C36 1.362(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.382(4) . ?
C37 H37 0.9300 . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 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
C11 N1 C7 118.2(2) . . ?
C11 N1 C12 124.3(2) . . ?
C12 N1 C7 117.5(2) . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C4 C1B H1BA 109.5 . . ?
C4 C1B H1BB 109.5 . . ?
C4 C1B H1BC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
C4 C2B H2BA 109.5 . . ?
C4 C2B H2BB 109.5 . . ?
C4 C2B H2BC 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
C4 C3B H3BA 109.5 . . ?
C4 C3B H3BB 109.5 . . ?
C4 C3B H3BC 109.5 . . ?
C2B C4 C1B 85.0(5) . . ?
C3B C4 C1B 108.2(4) . . ?
C3B C4 C2B 126.5(5) . . ?
C3B C4 C10 112.8(3) . . ?
C10 C4 C1B 106.9(3) . . ?
C10 C4 C2B 111.9(3) . . ?
C10 C4 C1A 110.2(4) . . ?
C10 C4 C3A 111.5(3) . . ?
C10 C4 C2A 110.4(3) . . ?
C1A C4 C3A 108.3(4) . . ?
C1A C4 C2A 126.9(5) . . ?
C3A C4 C2A 86.7(5) . . ?
C6 C5 H5 118.8 . . ?
C6 C5 C10 122.5(3) . . ?
C10 C5 H5 118.8 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 N1 120.1(2) . . ?
C8 C7 N1 121.4(2) . . ?
C8 C7 C6 118.4(3) . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 118.6 . . ?
C10 C9 C8 122.7(3) . . ?
C10 C9 H9 118.6 . . ?
C5 C10 C4 121.7(2) . . ?
C9 C10 C4 122.9(2) . . ?
C9 C10 C5 115.4(3) . . ?
O1 C11 N1 120.3(2) . . ?
O1 C11 C13 122.1(2) . . ?
N1 C11 C13 117.5(2) . . ?
O2 C12 N1 119.9(2) . . ?
O2 C12 C19 123.3(3) . . ?
N1 C12 C19 116.7(2) . . ?
C14 C13 C11 119.7(2) . . ?
C14 C13 C18 119.7(2) . . ?
C18 C13 C11 120.6(2) . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.5(2) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 119.0(2) . . ?
C15 C16 C23 118.4(2) . . ?
C17 C16 C23 122.6(2) . . ?
C18 C17 C16 118.9(2) . . ?
C22 C17 C16 123.7(2) . . ?
C22 C17 C18 117.4(2) . . ?
C13 C18 C17 120.0(2) . . ?
C19 C18 C13 119.7(2) . . ?
C19 C18 C17 120.3(2) . . ?
C18 C19 C12 121.0(2) . . ?
C20 C19 C12 119.1(2) . . ?
C20 C19 C18 119.9(2) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.3(2) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.4(2) . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C16 122.9(2) . . ?
C24 C23 C28 117.7(2) . . ?
C28 C23 C16 119.4(2) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.6(2) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C29 124.6(2) . . ?
C27 C26 C25 117.2(2) . . ?
C27 C26 C29 118.2(2) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 C26 121.8(2) . . ?
C28 C27 H27 119.1 . . ?
C23 C28 H28 119.7 . . ?
C27 C28 C23 120.6(2) . . ?
C27 C28 H28 119.7 . . ?
C26 C29 H29 114.8 . . ?
C30 C29 C26 130.4(2) . . ?
C30 C29 H29 114.8 . . ?
C29 C30 C31 121.6(2) . . ?
C29 C30 C32 123.7(2) . . ?
C31 C30 C32 114.8(2) . . ?
N2 C31 C30 176.4(3) . . ?
C33 C32 C30 121.0(3) . . ?
C33 C32 C37 118.4(2) . . ?
C37 C32 C30 120.6(2) . . ?
C32 C33 H33 119.5 . . ?
C32 C33 C34 120.9(3) . . ?
C34 C33 H33 119.5 . . ?
C33 C34 H34 120.8 . . ?
C35 C34 C33 118.4(3) . . ?
C35 C34 H34 120.8 . . ?
F1 C35 C34 118.4(3) . . ?
F1 C35 C36 118.8(3) . . ?
C34 C35 C36 122.8(3) . . ?
C35 C36 H36 120.7 . . ?
C35 C36 C37 118.7(3) . . ?
C37 C36 H36 120.7 . . ?
C32 C37 H37 119.6 . . ?
C36 C37 C32 120.7(3) . . ?
C36 C37 H37 119.6 . . ?
C4 C1A H1AA 109.5 . . ?
C4 C1A H1AB 109.5 . . ?
C4 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C4 C3A H3AA 109.5 . . ?
C4 C3A H3AB 109.5 . . ?
C4 C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C4 C2A H2AA 109.5 . . ?
C4 C2A H2AB 109.5 . . ?
C4 C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 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
F1 C35 C36 C37 -180.0(3) . . . . ?
O1 C11 C13 C14 -0.8(4) . . . . ?
O1 C11 C13 C18 179.2(2) . . . . ?
O2 C12 C19 C18 -179.8(3) . . . . ?
O2 C12 C19 C20 0.7(4) . . . . ?
N1 C7 C8 C9 179.2(3) . . . . ?
N1 C11 C13 C14 179.0(2) . . . . ?
N1 C11 C13 C18 -1.0(3) . . . . ?
N1 C12 C19 C18 0.1(4) . . . . ?
N1 C12 C19 C20 -179.4(2) . . . . ?
C1B C4 C10 C5 75.3(5) . . . . ?
C1B C4 C10 C9 -106.1(5) . . . . ?
C2B C4 C10 C5 -16.1(5) . . . . ?
C2B C4 C10 C9 162.5(5) . . . . ?
C3B C4 C10 C5 -166.0(5) . . . . ?
C3B C4 C10 C9 12.7(5) . . . . ?
C5 C6 C7 N1 -178.9(3) . . . . ?
C5 C6 C7 C8 -3.2(6) . . . . ?
C6 C5 C10 C4 -179.6(4) . . . . ?
C6 C5 C10 C9 1.6(6) . . . . ?
C6 C7 C8 C9 3.6(6) . . . . ?
C7 N1 C11 O1 0.2(4) . . . . ?
C7 N1 C11 C13 -179.6(2) . . . . ?
C7 N1 C12 O2 0.0(4) . . . . ?
C7 N1 C12 C19 -180.0(2) . . . . ?
C7 C8 C9 C10 -1.4(6) . . . . ?
C8 C9 C10 C4 -180.0(3) . . . . ?
C8 C9 C10 C5 -1.2(6) . . . . ?
C10 C5 C6 C7 0.5(7) . . . . ?
C11 N1 C7 C6 65.0(4) . . . . ?
C11 N1 C7 C8 -110.6(3) . . . . ?
C11 N1 C12 O2 178.8(3) . . . . ?
C11 N1 C12 C19 -1.1(4) . . . . ?
C11 C13 C14 C15 -179.7(2) . . . . ?
C11 C13 C18 C17 -180.0(2) . . . . ?
C11 C13 C18 C19 0.0(3) . . . . ?
C12 N1 C7 C6 -116.1(3) . . . . ?
C12 N1 C7 C8 68.4(4) . . . . ?
C12 N1 C11 O1 -178.6(2) . . . . ?
C12 N1 C11 C13 1.5(4) . . . . ?
C12 C19 C20 C21 178.7(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C13 C18 C19 C12 0.4(4) . . . . ?
C13 C18 C19 C20 179.9(2) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C14 C13 C18 C19 -179.9(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C14 C15 C16 C23 179.6(2) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C15 C16 C17 C22 178.8(2) . . . . ?
C15 C16 C23 C24 130.5(3) . . . . ?
C15 C16 C23 C28 -47.1(3) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C16 C17 C18 C19 179.7(2) . . . . ?
C16 C17 C22 C21 -179.7(2) . . . . ?
C16 C23 C24 C25 -178.8(2) . . . . ?
C16 C23 C28 C27 178.9(2) . . . . ?
C17 C16 C23 C24 -50.1(3) . . . . ?
C17 C16 C23 C28 132.3(2) . . . . ?
C17 C18 C19 C12 -179.6(2) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C13 C14 C15 0.2(4) . . . . ?
C18 C17 C22 C21 -1.1(4) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C17 0.2(4) . . . . ?
C22 C17 C18 C13 -179.0(2) . . . . ?
C22 C17 C18 C19 1.0(3) . . . . ?
C23 C16 C17 C18 -179.2(2) . . . . ?
C23 C16 C17 C22 -0.6(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C23 C28 C27 1.1(4) . . . . ?
C24 C25 C26 C27 1.1(4) . . . . ?
C24 C25 C26 C29 179.5(2) . . . . ?
C25 C26 C27 C28 -1.1(4) . . . . ?
C25 C26 C29 C30 22.9(4) . . . . ?
C26 C27 C28 C23 0.0(4) . . . . ?
C26 C29 C30 C31 4.1(5) . . . . ?
C26 C29 C30 C32 -177.0(3) . . . . ?
C27 C26 C29 C30 -158.7(3) . . . . ?
C28 C23 C24 C25 -1.2(4) . . . . ?
C29 C26 C27 C28 -179.7(2) . . . . ?
C29 C30 C32 C33 -148.8(3) . . . . ?
C29 C30 C32 C37 31.7(4) . . . . ?
C30 C32 C33 C34 -180.0(3) . . . . ?
C30 C32 C37 C36 180.0(3) . . . . ?
C31 C30 C32 C33 30.2(4) . . . . ?
C31 C30 C32 C37 -149.4(3) . . . . ?
C32 C33 C34 C35 0.3(5) . . . . ?
C33 C32 C37 C36 0.4(4) . . . . ?
C33 C34 C35 F1 180.0(3) . . . . ?
C33 C34 C35 C36 -0.1(5) . . . . ?
C34 C35 C36 C37 0.1(5) . . . . ?
C35 C36 C37 C32 -0.3(5) . . . . ?
C37 C32 C33 C34 -0.4(4) . . . . ?
C1A C4 C10 C5 102.0(5) . . . . ?
C1A C4 C10 C9 -79.3(5) . . . . ?
C3A C4 C10 C5 -137.6(5) . . . . ?
C3A C4 C10 C9 41.1(5) . . . . ?
C2A C4 C10 C5 -43.0(5) . . . . ?
C2A C4 C10 C9 135.7(5) . . . . ?

_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_cu_20211018f5_0m_a_pl
_database_code_depnum_ccdc_archive 'CCDC 2257054'
loop_
_audit_author_name
_audit_author_address
'Chengyuan Wang'
;Anhui University
China
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_audit_creation_date             2021-10-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H21 F N2 O2'
_chemical_formula_sum            'C34 H21 F N2 O2'
_chemical_formula_weight         508.53
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9696(7)
_cell_length_b                   9.4974(10)
_cell_length_c                   19.8317(19)
_cell_angle_alpha                100.243(5)
_cell_angle_beta                 99.253(6)
_cell_angle_gamma                96.028(6)
_cell_volume                     1262.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7921
_cell_measurement_temperature    300.15
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  0.7383
_exptl_absorpt_correction_T_min  0.5755
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1308 before and 0.0840 after correction.
The Ratio of minimum to maximum transmission is 0.7795.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25743
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.560
_diffrn_reflns_theta_min         2.303
_diffrn_ambient_temperature      300.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3535
_reflns_number_total             4640
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1572P)²+0.0072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2072
_refine_ls_wR_factor_ref         0.2270
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C30(H30), C31(H31),
  C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.1487(4) -0.5770(2) -0.15034(10) 0.1141(8) Uani 1 1 d . . . . .
O1 O 0.2852(3) 0.94836(15) 0.48428(8) 0.0567(5) Uani 1 1 d . . . . .
O2 O 0.2805(2) 0.66360(15) 0.64605(7) 0.0490(4) Uani 1 1 d . . . . .
N1 N 0.5592(4) -0.0607(3) 0.08172(15) 0.0902(8) Uani 1 1 d . . . . .
N2 N 0.2941(3) 0.80939(16) 0.56679(8) 0.0395(4) Uani 1 1 d . . . . .
C1 C 0.3109(6) 1.2979(3) 0.78640(18) 0.0922(11) Uani 1 1 d . . . . .
H1A H 0.310862 1.384922 0.768107 0.138 Uiso 1 1 calc R U . . .
H1B H 0.426794 1.305837 0.821123 0.138 Uiso 1 1 calc R U . . .
H1C H 0.196727 1.283505 0.807036 0.138 Uiso 1 1 calc R U . . .
C2 C 0.3085(4) 1.1711(2) 0.72812(14) 0.0596(7) Uani 1 1 d . . . . .
C3 C 0.1573(4) 1.1365(3) 0.67192(15) 0.0620(7) Uani 1 1 d . . . . .
H3 H 0.056895 1.193689 0.669536 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1499(4) 1.0183(2) 0.61832(13) 0.0506(5) Uani 1 1 d . . . . .
H4 H 0.044834 0.995927 0.581048 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3009(3) 0.9344(2) 0.62122(11) 0.0424(5) Uani 1 1 d . . . . .
C6 C 0.4554(3) 0.9689(2) 0.67676(11) 0.0468(5) Uani 1 1 d . . . . .
H6 H 0.557648 0.913378 0.678648 0.056 Uiso 1 1 calc R U . . .
C7 C 0.4589(4) 1.0861(2) 0.72974(12) 0.0558(6) Uani 1 1 d . . . . .
H7 H 0.563695 1.108247 0.767087 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2889(3) 0.8288(2) 0.49812(11) 0.0412(5) Uani 1 1 d . . . . .
C9 C 0.2862(3) 0.6992(2) 0.44441(10) 0.0391(5) Uani 1 1 d . . . . .
C10 C 0.3066(4) 0.7134(2) 0.37798(11) 0.0484(5) Uani 1 1 d . . . . .
H10 H 0.330972 0.805068 0.368109 0.058 Uiso 1 1 calc R U . . .
C11 C 0.2909(4) 0.5914(2) 0.32512(12) 0.0514(6) Uani 1 1 d . . . . .
H11 H 0.306321 0.603783 0.280728 0.062 Uiso 1 1 calc R U . . .
C12 C 0.2534(3) 0.4534(2) 0.33696(11) 0.0446(5) Uani 1 1 d . . . . .
C13 C 0.2435(3) 0.4349(2) 0.40681(10) 0.0391(5) Uani 1 1 d . . . . .
C14 C 0.2616(3) 0.5596(2) 0.46016(10) 0.0361(4) Uani 1 1 d . . . . .
C15 C 0.2239(3) 0.2983(2) 0.42628(11) 0.0440(5) Uani 1 1 d . . . . .
H15 H 0.211951 0.215017 0.392332 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2220(3) 0.2863(2) 0.49390(11) 0.0450(5) Uani 1 1 d . . . . .
H16 H 0.210191 0.195368 0.505387 0.054 Uiso 1 1 calc R U . . .
C17 C 0.2379(3) 0.4101(2) 0.54601(11) 0.0406(5) Uani 1 1 d . . . . .
H17 H 0.234734 0.401104 0.591770 0.049 Uiso 1 1 calc R U . . .
C18 C 0.2582(3) 0.54446(19) 0.52949(10) 0.0358(4) Uani 1 1 d . . . . .
C19 C 0.2783(3) 0.6724(2) 0.58577(10) 0.0372(5) Uani 1 1 d . . . . .
C20 C 0.2174(3) 0.3283(2) 0.27740(11) 0.0445(5) Uani 1 1 d . . . . .
C21 C 0.0420(4) 0.2351(3) 0.26244(13) 0.0561(6) Uani 1 1 d . . . . .
H21 H -0.049723 0.247786 0.291468 0.067 Uiso 1 1 calc R U . . .
C22 C 0.0027(4) 0.1239(3) 0.20495(12) 0.0566(6) Uani 1 1 d . . . . .
H22 H -0.117283 0.064535 0.195285 0.068 Uiso 1 1 calc R U . . .
C23 C 0.1372(3) 0.0978(2) 0.16098(11) 0.0470(5) Uani 1 1 d . . . . .
C24 C 0.3144(3) 0.1915(2) 0.17654(11) 0.0486(5) Uani 1 1 d . . . . .
H24 H 0.407758 0.177256 0.148278 0.058 Uiso 1 1 calc R U . . .
C25 C 0.3524(3) 0.3049(2) 0.23325(11) 0.0473(5) Uani 1 1 d . . . . .
H25 H 0.470131 0.366671 0.242123 0.057 Uiso 1 1 calc R U . . .
C26 C 0.0776(3) -0.0232(2) 0.10143(12) 0.0500(5) Uani 1 1 d . . . . .
H26 H -0.057394 -0.050616 0.088949 0.060 Uiso 1 1 calc R U . . .
C27 C 0.1823(3) -0.1014(2) 0.06165(11) 0.0481(5) Uani 1 1 d . . . . .
C28 C 0.3916(4) -0.0749(3) 0.07398(13) 0.0594(6) Uani 1 1 d . . . . .
C29 C 0.0926(4) -0.2258(2) 0.00426(12) 0.0527(6) Uani 1 1 d . . . . .
C30 C -0.0955(4) -0.2946(3) 0.00082(15) 0.0668(7) Uani 1 1 d . . . . .
H30 H -0.167898 -0.261483 0.034433 0.080 Uiso 1 1 calc R U . . .
C31 C -0.1768(5) -0.4114(3) -0.05165(17) 0.0779(9) Uani 1 1 d . . . . .
H31 H -0.303629 -0.456262 -0.054058 0.093 Uiso 1 1 calc R U . . .
C32 C -0.0679(6) -0.4596(3) -0.09978(15) 0.0807(10) Uani 1 1 d . . . . .
C33 C 0.1130(7) -0.3947(3) -0.09955(16) 0.0886(11) Uani 1 1 d . . . . .
H33 H 0.181789 -0.427768 -0.134313 0.106 Uiso 1 1 calc R U . . .
C34 C 0.1953(5) -0.2781(3) -0.04688(15) 0.0736(8) Uani 1 1 d . . . . .
H34 H 0.321696 -0.233979 -0.045780 0.088 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 C32 1.362(3) . ?
O1 C8 1.216(2) . ?
O2 C19 1.211(2) . ?
N1 C28 1.143(4) . ?
N2 C5 1.447(2) . ?
N2 C8 1.402(3) . ?
N2 C19 1.415(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.510(3) . ?
C2 C3 1.371(4) . ?
C2 C7 1.388(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 C6 1.377(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.474(3) . ?
C9 C10 1.376(3) . ?
C9 C14 1.415(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.400(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C12 C13 1.438(3) . ?
C12 C20 1.488(3) . ?
C13 C14 1.421(3) . ?
C13 C15 1.418(3) . ?
C14 C18 1.411(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.403(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(3) . ?
C18 C19 1.475(3) . ?
C20 C21 1.388(3) . ?
C20 C25 1.393(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.391(3) . ?
C23 C24 1.401(3) . ?
C23 C26 1.465(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.341(3) . ?
C27 C28 1.428(4) . ?
C27 C29 1.490(3) . ?
C29 C30 1.388(4) . ?
C29 C34 1.384(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.379(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.360(5) . ?
C32 C33 1.342(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.382(4) . ?
C34 H34 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C5 118.92(15) . . ?
C8 N2 C19 123.70(16) . . ?
C19 N2 C5 117.21(16) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 C7 118.0(2) . . ?
C7 C2 C1 121.1(3) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 N2 120.06(19) . . ?
C6 C5 N2 120.22(18) . . ?
C6 C5 C4 119.7(2) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.1(2) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.1(2) . . ?
C6 C7 H7 119.4 . . ?
O1 C8 N2 120.52(18) . . ?
O1 C8 C9 122.22(19) . . ?
N2 C8 C9 117.26(16) . . ?
C10 C9 C8 119.88(17) . . ?
C10 C9 C14 119.37(19) . . ?
C14 C9 C8 120.75(18) . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.67(19) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.9(2) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 118.64(19) . . ?
C11 C12 C20 119.60(19) . . ?
C13 C12 C20 121.72(18) . . ?
C14 C13 C12 118.83(17) . . ?
C15 C13 C12 123.54(18) . . ?
C15 C13 C14 117.59(18) . . ?
C9 C14 C13 120.36(18) . . ?
C18 C14 C9 119.72(18) . . ?
C18 C14 C13 119.91(17) . . ?
C13 C15 H15 119.3 . . ?
C16 C15 C13 121.48(18) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.42(18) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.00(18) . . ?
C18 C17 H17 120.0 . . ?
C14 C18 C19 120.82(16) . . ?
C17 C18 C14 120.59(18) . . ?
C17 C18 C19 118.59(17) . . ?
O2 C19 N2 120.16(17) . . ?
O2 C19 C18 122.61(17) . . ?
N2 C19 C18 117.23(17) . . ?
C21 C20 C12 120.24(19) . . ?
C21 C20 C25 118.1(2) . . ?
C25 C20 C12 121.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.0 . . ?
C21 C22 C23 122.0(2) . . ?
C23 C22 H22 119.0 . . ?
C22 C23 C24 117.2(2) . . ?
C22 C23 C26 116.7(2) . . ?
C24 C23 C26 126.0(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24 119.5 . . ?
C20 C25 H25 119.4 . . ?
C24 C25 C20 121.2(2) . . ?
C24 C25 H25 119.4 . . ?
C23 C26 H26 114.2 . . ?
C27 C26 C23 131.7(2) . . ?
C27 C26 H26 114.2 . . ?
C26 C27 C28 121.6(2) . . ?
C26 C27 C29 123.4(2) . . ?
C28 C27 C29 114.9(2) . . ?
N1 C28 C27 176.3(3) . . ?
C30 C29 C27 121.2(2) . . ?
C34 C29 C27 121.1(3) . . ?
C34 C29 C30 117.7(2) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 121.1(3) . . ?
C31 C30 H30 119.5 . . ?
C30 C31 H31 120.7 . . ?
C32 C31 C30 118.6(3) . . ?
C32 C31 H31 120.7 . . ?
C31 C32 F1 117.9(4) . . ?
C33 C32 F1 119.6(3) . . ?
C33 C32 C31 122.5(3) . . ?
C32 C33 H33 120.5 . . ?
C32 C33 C34 119.0(3) . . ?
C34 C33 H33 120.5 . . ?
C29 C34 H34 119.5 . . ?
C33 C34 C29 121.0(3) . . ?
C33 C34 H34 119.5 . . ?

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
F1 C32 C33 C34 -178.3(3) . . . . ?
O1 C8 C9 C10 8.9(3) . . . . ?
O1 C8 C9 C14 -170.6(2) . . . . ?
N2 C5 C6 C7 -178.17(19) . . . . ?
N2 C8 C9 C10 -171.65(19) . . . . ?
N2 C8 C9 C14 8.8(3) . . . . ?
C1 C2 C3 C4 -178.6(2) . . . . ?
C1 C2 C7 C6 179.2(2) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C2 C7 C6 -0.8(4) . . . . ?
C3 C4 C5 N2 178.78(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 N2 C8 O1 -1.8(3) . . . . ?
C5 N2 C8 C9 178.75(17) . . . . ?
C5 N2 C19 O2 -3.6(3) . . . . ?
C5 N2 C19 C18 176.08(16) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C7 C2 C3 C4 1.4(4) . . . . ?
C8 N2 C5 C4 60.6(3) . . . . ?
C8 N2 C5 C6 -120.6(2) . . . . ?
C8 N2 C19 O2 -178.72(18) . . . . ?
C8 N2 C19 C18 0.9(3) . . . . ?
C8 C9 C10 C11 -175.6(2) . . . . ?
C8 C9 C14 C13 174.95(17) . . . . ?
C8 C9 C14 C18 -6.1(3) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C9 C14 C18 C17 -178.85(18) . . . . ?
C9 C14 C18 C19 0.6(3) . . . . ?
C10 C9 C14 C13 -4.6(3) . . . . ?
C10 C9 C14 C18 174.34(18) . . . . ?
C10 C11 C12 C13 -4.3(4) . . . . ?
C10 C11 C12 C20 173.6(2) . . . . ?
C11 C12 C13 C14 3.5(3) . . . . ?
C11 C12 C13 C15 -174.0(2) . . . . ?
C11 C12 C20 C21 -121.1(3) . . . . ?
C11 C12 C20 C25 55.7(3) . . . . ?
C12 C13 C14 C9 0.8(3) . . . . ?
C12 C13 C14 C18 -178.11(18) . . . . ?
C12 C13 C15 C16 177.65(19) . . . . ?
C12 C20 C21 C22 176.2(2) . . . . ?
C12 C20 C25 C24 -177.53(19) . . . . ?
C13 C12 C20 C21 56.7(3) . . . . ?
C13 C12 C20 C25 -126.5(2) . . . . ?
C13 C14 C18 C17 0.1(3) . . . . ?
C13 C14 C18 C19 179.53(17) . . . . ?
C13 C15 C16 C17 0.6(3) . . . . ?
C14 C9 C10 C11 4.0(3) . . . . ?
C14 C13 C15 C16 0.1(3) . . . . ?
C14 C18 C19 O2 -178.27(18) . . . . ?
C14 C18 C19 N2 2.1(3) . . . . ?
C15 C13 C14 C9 178.52(18) . . . . ?
C15 C13 C14 C18 -0.4(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C16 C17 C18 C14 0.6(3) . . . . ?
C16 C17 C18 C19 -178.88(17) . . . . ?
C17 C18 C19 O2 1.2(3) . . . . ?
C17 C18 C19 N2 -178.48(17) . . . . ?
C19 N2 C5 C4 -114.8(2) . . . . ?
C19 N2 C5 C6 64.0(3) . . . . ?
C19 N2 C8 O1 173.25(19) . . . . ?
C19 N2 C8 C9 -6.2(3) . . . . ?
C20 C12 C13 C14 -174.28(18) . . . . ?
C20 C12 C13 C15 8.2(3) . . . . ?
C20 C21 C22 C23 1.8(4) . . . . ?
C21 C20 C25 C24 -0.6(3) . . . . ?
C21 C22 C23 C24 -1.3(4) . . . . ?
C21 C22 C23 C26 -179.7(2) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C22 C23 C26 C27 -159.0(3) . . . . ?
C23 C24 C25 C20 1.0(3) . . . . ?
C23 C26 C27 C28 0.6(4) . . . . ?
C23 C26 C27 C29 177.5(2) . . . . ?
C24 C23 C26 C27 22.9(4) . . . . ?
C25 C20 C21 C22 -0.8(4) . . . . ?
C26 C23 C24 C25 178.1(2) . . . . ?
C26 C27 C29 C30 -18.8(4) . . . . ?
C26 C27 C29 C34 162.2(2) . . . . ?
C27 C29 C30 C31 -178.8(2) . . . . ?
C27 C29 C34 C33 179.1(2) . . . . ?
C28 C27 C29 C30 158.3(2) . . . . ?
C28 C27 C29 C34 -20.7(3) . . . . ?
C29 C30 C31 C32 0.9(4) . . . . ?
C30 C29 C34 C33 0.1(4) . . . . ?
C30 C31 C32 F1 178.6(2) . . . . ?
C30 C31 C32 C33 -2.4(5) . . . . ?
C31 C32 C33 C34 2.7(5) . . . . ?
C32 C33 C34 C29 -1.5(5) . . . . ?
C34 C29 C30 C31 0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
