# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1814128'
loop_
_audit_author_name
_audit_author_address
'haoran wang' 'Jilin University'
_audit_update_record             
;
2018-01-01 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 F2 N O'
_chemical_formula_weight         257.23

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8629(2)
_cell_length_b                   11.5405(7)
_cell_length_c                   13.9513(7)
_cell_angle_alpha                74.149(2)
_cell_angle_beta                 82.550(2)
_cell_angle_gamma                87.829(2)
_cell_volume                     593.24(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    199(2)
_cell_measurement_reflns_used    6666
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.603
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      199(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19845
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2682
_reflns_number_gt                1881
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0479P)²+0.0947P] 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         2682
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5912(4) 0.84787(11) 1.03021(8) 0.0970(4) Uani 1 1 d . . . . .
F2 F 0.3027(4) 0.57657(9) 0.85868(8) 0.0953(4) Uani 1 1 d . . . . .
O1 O 0.2722(3) 0.67650(8) 0.50409(7) 0.0507(3) Uani 1 1 d . . . . .
N1 N 0.0792(3) 0.85899(11) 0.42225(9) 0.0554(3) Uani 1 1 d . . . . .
C1 C 0.1911(4) 0.66818(13) 0.41283(10) 0.0463(3) Uani 1 1 d . . . . .
C2 C 0.2194(4) 0.56947(14) 0.37568(11) 0.0550(4) Uani 1 1 d . . . . .
H2 H 0.3023 0.4940 0.4125 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1194(4) 0.58687(16) 0.28115(12) 0.0608(4) Uani 1 1 d . . . . .
H3 H 0.1350 0.5216 0.2515 0.073 Uiso 1 1 calc R U . . .
C4 C -0.0032(4) 0.69757(17) 0.22847(12) 0.0621(4) Uani 1 1 d . . . . .
H4 H -0.0706 0.7060 0.1638 0.074 Uiso 1 1 calc R U . . .
C5 C -0.0298(4) 0.79533(15) 0.26753(11) 0.0590(4) Uani 1 1 d . . . . .
H5 H -0.1142 0.8707 0.2310 0.071 Uiso 1 1 calc R U . . .
C6 C 0.0716(4) 0.77977(13) 0.36245(10) 0.0479(3) Uani 1 1 d . . . . .
C7 C 0.1968(4) 0.79433(13) 0.50323(11) 0.0498(4) Uani 1 1 d . . . . .
C8 C 0.2515(4) 0.82930(14) 0.59154(11) 0.0545(4) Uani 1 1 d . . . . .
H8 H 0.2282 0.9120 0.5902 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3332(4) 0.75109(14) 0.67507(11) 0.0527(4) Uani 1 1 d . . . . .
H9 H 0.3513 0.6688 0.6748 0.063 Uiso 1 1 calc R U . . .
C10 C 0.3977(4) 0.77933(14) 0.76706(11) 0.0506(4) Uani 1 1 d . . . . .
C11 C 0.3848(5) 0.69058(14) 0.85723(12) 0.0603(4) Uani 1 1 d . . . . .
C12 C 0.4465(5) 0.71008(17) 0.94640(12) 0.0703(5) Uani 1 1 d . . . . .
H12 H 0.4349 0.6466 1.0067 0.084 Uiso 1 1 calc R U . . .
C13 C 0.5254(5) 0.82542(17) 0.94397(12) 0.0643(5) Uani 1 1 d . . . . .
C14 C 0.5440(5) 0.91802(16) 0.85837(13) 0.0638(4) Uani 1 1 d . . . . .
H14 H 0.5983 0.9973 0.8593 0.077 Uiso 1 1 calc R U . . .
C15 C 0.4822(4) 0.89423(15) 0.77033(12) 0.0588(4) Uani 1 1 d . . . . .
H15 H 0.4979 0.9581 0.7103 0.071 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 C13 1.3541(18) . ?
F2 C11 1.3592(19) . ?
O1 C7 1.3770(17) . ?
O1 C1 1.3787(16) . ?
N1 C7 1.2985(18) . ?
N1 C6 1.399(2) . ?
C1 C2 1.370(2) . ?
C1 C6 1.382(2) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.439(2) . ?
C8 C9 1.331(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.460(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 C15 1.392(2) . ?
C11 C12 1.374(2) . ?
C12 C13 1.367(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.364(2) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 H15 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
C7 O1 C1 104.11(10) . . ?
C7 N1 C6 104.47(12) . . ?
C2 C1 O1 127.92(13) . . ?
C2 C1 C6 124.43(13) . . ?
O1 C1 C6 107.65(12) . . ?
C1 C2 C3 115.64(14) . . ?
C1 C2 H2 122.2 . . ?
C3 C2 H2 122.2 . . ?
C2 C3 C4 121.53(16) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.71(15) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 117.61(15) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 119.08(14) . . ?
C1 C6 N1 108.95(12) . . ?
C5 C6 N1 131.97(14) . . ?
N1 C7 O1 114.81(13) . . ?
N1 C7 C8 128.55(14) . . ?
O1 C7 C8 116.63(12) . . ?
C9 C8 C7 122.99(14) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C8 C9 C10 126.38(15) . . ?
C8 C9 H9 116.8 . . ?
C10 C9 H9 116.8 . . ?
C11 C10 C15 115.72(14) . . ?
C11 C10 C9 121.05(14) . . ?
C15 C10 C9 123.22(14) . . ?
F2 C11 C12 117.32(15) . . ?
F2 C11 C10 118.35(14) . . ?
C12 C11 C10 124.32(16) . . ?
C13 C12 C11 116.65(16) . . ?
C13 C12 H12 121.7 . . ?
C11 C12 H12 121.7 . . ?
F1 C13 C14 118.90(17) . . ?
F1 C13 C12 118.33(16) . . ?
C14 C13 C12 122.76(15) . . ?
C13 C14 C15 118.65(16) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C10 121.89(16) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C1 C2 179.82(15) . . . . ?
C7 O1 C1 C6 -0.17(15) . . . . ?
O1 C1 C2 C3 -179.87(13) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
O1 C1 C6 C5 -179.78(13) . . . . ?
C2 C1 C6 N1 -179.70(14) . . . . ?
O1 C1 C6 N1 0.29(16) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 N1 179.59(15) . . . . ?
C7 N1 C6 C1 -0.30(16) . . . . ?
C7 N1 C6 C5 179.79(16) . . . . ?
C6 N1 C7 O1 0.20(17) . . . . ?
C6 N1 C7 C8 -178.63(15) . . . . ?
C1 O1 C7 N1 -0.02(17) . . . . ?
C1 O1 C7 C8 178.95(13) . . . . ?
N1 C7 C8 C9 171.51(17) . . . . ?
O1 C7 C8 C9 -7.3(2) . . . . ?
C7 C8 C9 C10 179.05(14) . . . . ?
C8 C9 C10 C11 161.84(17) . . . . ?
C8 C9 C10 C15 -19.5(3) . . . . ?
C15 C10 C11 F2 179.84(15) . . . . ?
C9 C10 C11 F2 -1.4(2) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C9 C10 C11 C12 179.21(16) . . . . ?
F2 C11 C12 C13 -179.38(16) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 F1 -179.36(15) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
F1 C13 C14 C15 178.96(15) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 0.8(3) . . . . ?
C11 C10 C15 C14 -0.9(2) . . . . ?
C9 C10 C15 C14 -179.59(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.95 2.63 3.5440(18) 161.1 2_666

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_ran12cult
_database_code_depnum_ccdc_archive 'CCDC 1850301'
loop_
_audit_author_name
_audit_author_address
'haoran wang'
;Jilin University
China
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-07-30
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C30 H20 F2 N2 O2'
_chemical_formula_sum            'C30 H20 F2 N2 O2'
_chemical_formula_weight         478.48
_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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   21.7576(3)
_cell_length_b                   9.38142(11)
_cell_length_c                   22.7647(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.6152(11)
_cell_angle_gamma                90
_cell_volume                     4581.40(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14729
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6460
_cell_measurement_theta_min      4.1110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25454
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         3.939
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 130.00   1.00    3.00    --  104.49 -61.00   0.00   98
  2  ω   -110.00 -15.00   1.00    2.00    --  -40.57 -37.00  60.00   95
  3  ω    -67.00  36.00   1.00    2.00    --  -40.57  37.00-120.00  103
  4  ω    -92.00  -2.00   1.00    2.00    --  -40.57 125.00 -60.00   90
  5  ω     46.00 166.00   1.00    3.00    --  104.49  15.00  90.00  120
  6  ω     33.00 111.00   1.00    3.00    --  104.49-111.00-180.00   78
  7  ω     32.00 109.00   1.00    3.00    --  104.49 -94.00   0.00   77
  8  ω     32.00 118.00   1.00    3.00    --  104.49 -45.00-150.00   86
  9  ω     75.00 160.00   1.00    3.00    --  104.49  30.00 150.00   85
 10  ω     48.00 109.00   1.00    3.00    --  104.49 -94.00-150.00   61
 11  ω     31.00 110.00   1.00    3.00    --  104.49 -30.00 120.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0024975000
_diffrn_orient_matrix_UB_12      0.1603444000
_diffrn_orient_matrix_UB_13      0.0150090000
_diffrn_orient_matrix_UB_21      0.0583615000
_diffrn_orient_matrix_UB_22      0.0158366000
_diffrn_orient_matrix_UB_23      -0.0295643000
_diffrn_orient_matrix_UB_31      -0.0416953000
_diffrn_orient_matrix_UB_32      0.0321648000
_diffrn_orient_matrix_UB_33      -0.0600910000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7580
_reflns_number_total             8266
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 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    ?
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         8266
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.027
_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)+(0.0496P)²+3.0996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
N10 \\sim C33: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02
3.a Ternary CH refined with riding coordinates:
 C19(H19), C38(H38), C46(H46), C55(H55), C18(H18), C44(H44), C47(H47), C63(H63)
3.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C30(H30), C34(H34), C40(H40), C41(H41), C42(H42), C43(H43),
 C45(H45), C48(H48), C49(H49), C56(H56), C59(H59), C61(H61), C62(H62), C64(H64),
  C69(H69), C22(H22), C26(H26), C27(H27), C37(H37), C50(H50), C51(H51),
 C54(H54), C58(H58), C60(H60), C65(H65), C66(H66), C67(H67), C68(H68), C70(H70),
  C71(H71), C72(H72)
;
_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 0.09876(5) 0.58029(13) 0.26812(5) 0.0372(3) Uani 1 1 d . . . . .
O3 O 0.01109(5) 0.22708(13) 0.01502(5) 0.0232(3) Uani 1 1 d . . . . .
F4 F 0.29398(5) 0.09612(12) -0.17445(5) 0.0340(3) Uani 1 1 d . . . . .
O5 O 0.10408(5) 0.59686(13) -0.09245(5) 0.0237(3) Uani 1 1 d . . . . .
N9 N 0.20280(6) 0.67894(16) -0.07460(6) 0.0218(3) Uani 1 1 d . . . . .
N12 N 0.10010(7) 0.15039(16) 0.07092(6) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.17282(8) 0.73200(18) -0.12943(7) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.11224(8) 0.68224(18) -0.13990(7) 0.0205(3) Uani 1 1 d . . . . .
C16 C 0.16135(8) 0.60238(18) -0.05559(7) 0.0213(3) Uani 1 1 d . . . . .
C17 C 0.04908(8) 0.07504(19) 0.08753(8) 0.0244(4) Uani 1 1 d . . . . .
C19 C 0.17362(7) 0.35588(18) -0.00152(7) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.194766 0.320888 0.038254 0.024 Uiso 1 1 calc R . . . .
C20 C 0.10620(8) 0.51589(17) 0.09036(7) 0.0209(3) Uani 1 1 d . . . . .
C24 C 0.07493(8) 0.23462(18) 0.02950(7) 0.0211(3) Uani 1 1 d . . . . .
C25 C 0.18118(8) 0.29950(19) -0.10964(7) 0.0236(4) Uani 1 1 d . . . . .
H25 H 0.144470 0.353814 -0.122133 0.028 Uiso 1 1 calc R . . . .
C29 C 0.20404(8) 0.28503(17) -0.04879(7) 0.0202(3) Uani 1 1 d . . . . .
C30 C 0.28829(8) 0.13975(19) -0.07378(8) 0.0264(4) Uani 1 1 d . . . . .
H30 H 0.324962 0.084960 -0.061796 0.032 Uiso 1 1 calc R . . . .
C31 C 0.10091(9) 0.55527(19) 0.20943(7) 0.0260(4) Uani 1 1 d . . . . .
C34 C 0.06891(9) 0.7203(2) -0.18900(8) 0.0279(4) Uani 1 1 d . . . . .
H34 H 0.027225 0.686138 -0.194914 0.034 Uiso 1 1 calc R . . . .
C35 C 0.26418(8) 0.15822(18) -0.13304(8) 0.0250(4) Uani 1 1 d . . . . .
C36 C -0.00503(8) 0.12355(18) 0.05268(7) 0.0221(3) Uani 1 1 d . . . . .
C38 C 0.16827(7) 0.52334(18) 0.00173(7) 0.0203(3) Uani 1 1 d . . . . .
H38 H 0.200937 0.565812 0.032941 0.024 Uiso 1 1 calc R . . . .
C40 C 0.09021(10) 0.8110(2) -0.22876(8) 0.0336(4) Uani 1 1 d . . . . .
H40 H 0.062359 0.840692 -0.263250 0.040 Uiso 1 1 calc R . . . .
C41 C -0.06403(8) 0.0742(2) 0.05629(8) 0.0284(4) Uani 1 1 d . . . . .
H41 H -0.100172 0.108490 0.030971 0.034 Uiso 1 1 calc R . . . .
C42 C 0.04969(8) 0.5350(2) 0.10993(8) 0.0258(4) Uani 1 1 d . . . . .
H42 H 0.012217 0.533817 0.081710 0.031 Uiso 1 1 calc R . . . .
C43 C 0.21121(8) 0.23581(19) -0.15225(8) 0.0254(4) Uani 1 1 d . . . . .
H43 H 0.195440 0.245798 -0.193542 0.031 Uiso 1 1 calc R . . . .
C45 C 0.15121(10) 0.8601(2) -0.21985(9) 0.0368(5) Uani 1 1 d . . . . .
H45 H 0.164019 0.921164 -0.248830 0.044 Uiso 1 1 calc R . . . .
C46 C 0.10270(7) 0.34799(18) -0.00292(7) 0.0206(3) Uani 1 1 d . . . . .
H46 H 0.080964 0.350401 -0.045233 0.025 Uiso 1 1 calc R . . . .
C48 C 0.04660(8) 0.5558(2) 0.16965(8) 0.0275(4) Uani 1 1 d . . . . .
H48 H 0.007698 0.569932 0.182517 0.033 Uiso 1 1 calc R . . . .
C49 C 0.16013(8) 0.5125(2) 0.13258(8) 0.0263(4) Uani 1 1 d . . . . .
H49 H 0.199183 0.497202 0.120160 0.032 Uiso 1 1 calc R . . . .
C55 C 0.10484(7) 0.50349(18) 0.02387(7) 0.0199(3) Uani 1 1 d . . . . .
H55 H 0.071697 0.565382 0.001147 0.024 Uiso 1 1 calc R . . . .
C56 C 0.25743(8) 0.20361(19) -0.03187(8) 0.0237(4) Uani 1 1 d . . . . .
H56 H 0.273215 0.191277 0.009310 0.028 Uiso 1 1 calc R . . . .
C59 C 0.04611(10) -0.0299(2) 0.13002(8) 0.0320(4) Uani 1 1 d . . . . .
H59 H 0.082634 -0.066091 0.154153 0.038 Uiso 1 1 calc R . . . .
C61 C 0.19393(9) 0.8232(2) -0.17028(9) 0.0323(4) Uani 1 1 d . . . . .
H61 H 0.235497 0.858122 -0.164273 0.039 Uiso 1 1 calc R . . . .
C62 C -0.01280(10) -0.0795(2) 0.13551(9) 0.0370(5) Uani 1 1 d . . . . .
H62 H -0.016556 -0.150031 0.164643 0.044 Uiso 1 1 calc R . . . .
C64 C -0.06691(10) -0.0287(2) 0.09941(9) 0.0345(4) Uani 1 1 d . . . . .
H64 H -0.106318 -0.065530 0.104611 0.041 Uiso 1 1 calc R . . . .
C69 C 0.15790(8) 0.5312(2) 0.19291(8) 0.0290(4) Uani 1 1 d . . . . .
H69 H 0.194799 0.527358 0.221818 0.035 Uiso 1 1 calc R . . . .
O2 O 0.40855(5) 0.45375(13) 0.14126(5) 0.0241(3) Uani 1 1 d . . . . .
F6 F 0.19363(5) 0.87800(14) 0.19566(5) 0.0385(3) Uani 1 1 d . . . . .
O7 O 0.39958(6) 0.87976(14) -0.09253(6) 0.0292(3) Uani 1 1 d . . . . .
F8 F 0.41836(6) 0.29930(14) -0.21301(5) 0.0409(3) Uani 1 1 d . . . . .
N10 N 0.47027(7) 0.78170(15) -0.02006(6) 0.0227(3) Uani 1 1 d . U . . .
N11 N 0.31449(7) 0.41183(16) 0.08642(6) 0.0231(3) Uani 1 1 d . . . . .
C14 C 0.32338(8) 0.77607(18) 0.08978(8) 0.0229(3) Uani 1 1 d . . . . .
C18 C 0.38790(8) 0.57658(18) 0.04705(7) 0.0209(3) Uani 1 1 d . . . . .
H18 H 0.433038 0.561140 0.045308 0.025 Uiso 1 1 calc R . . . .
C21 C 0.36952(8) 0.50450(18) -0.06768(7) 0.0214(3) Uani 1 1 d . . . . .
C22 C 0.33403(8) 0.52026(19) -0.12376(8) 0.0261(4) Uani 1 1 d . . . . .
H22 H 0.297909 0.578811 -0.128492 0.031 Uiso 1 1 calc R . . . .
C23 C 0.31950(8) 0.33623(19) 0.14042(8) 0.0242(4) Uani 1 1 d . . . . .
C26 C 0.29257(9) 0.7889(2) 0.18705(8) 0.0282(4) Uani 1 1 d . . . . .
H26 H 0.301305 0.774145 0.228895 0.034 Uiso 1 1 calc R . . . .
C27 C 0.35005(9) 0.4526(2) -0.17303(8) 0.0281(4) Uani 1 1 d . . . . .
H27 H 0.325769 0.464779 -0.211440 0.034 Uiso 1 1 calc R . . . .
C28 C 0.36690(8) 0.47547(18) 0.08968(7) 0.0213(3) Uani 1 1 d . . . . .
C32 C 0.50185(8) 0.84766(19) -0.06138(8) 0.0253(4) Uani 1 1 d . . . . .
C33 C 0.41123(8) 0.80491(18) -0.04131(8) 0.0237(3) Uani 1 1 d . U . . .
C37 C 0.42129(9) 0.4172(2) -0.06128(8) 0.0300(4) Uani 1 1 d . . . . .
H37 H 0.445934 0.405439 -0.023011 0.036 Uiso 1 1 calc R . . . .
C39 C 0.45844(8) 0.90737(19) -0.10544(8) 0.0263(4) Uani 1 1 d . . . . .
C44 C 0.35824(8) 0.75166(18) -0.01430(7) 0.0222(3) Uani 1 1 d . . . . .
H44 H 0.318525 0.804313 -0.028278 0.027 Uiso 1 1 calc R . . . .
C47 C 0.34997(8) 0.58516(18) -0.01647(7) 0.0211(3) Uani 1 1 d . . . . .
H47 H 0.305448 0.561969 -0.014718 0.025 Uiso 1 1 calc R . . . .
C50 C 0.26597(8) 0.8337(2) 0.06490(8) 0.0266(4) Uani 1 1 d . . . . .
H50 H 0.256797 0.849186 0.023109 0.032 Uiso 1 1 calc R . . . .
C51 C 0.35554(9) 0.2163(2) 0.25095(8) 0.0327(4) Uani 1 1 d . . . . .
H51 H 0.366577 0.175062 0.289389 0.039 Uiso 1 1 calc R . . . .
C52 C 0.40221(9) 0.3670(2) -0.16481(8) 0.0288(4) Uani 1 1 d . . . . .
C53 C 0.37738(8) 0.36440(19) 0.17406(7) 0.0242(4) Uani 1 1 d . . . . .
C54 C 0.22172(9) 0.8691(2) 0.10018(8) 0.0301(4) Uani 1 1 d . . . . .
H54 H 0.182653 0.909057 0.083186 0.036 Uiso 1 1 calc R . . . .
C57 C 0.23644(9) 0.8445(2) 0.16023(8) 0.0285(4) Uani 1 1 d . . . . .
C58 C 0.27792(9) 0.2436(2) 0.16134(8) 0.0296(4) Uani 1 1 d . . . . .
H58 H 0.238255 0.222388 0.138635 0.036 Uiso 1 1 calc R . . . .
C60 C 0.33597(8) 0.75515(19) 0.15128(8) 0.0259(4) Uani 1 1 d . . . . .
H60 H 0.375156 0.716933 0.168943 0.031 Uiso 1 1 calc R . . . .
C63 C 0.37450(8) 0.74081(18) 0.05472(7) 0.0217(3) Uani 1 1 d . . . . .
H63 H 0.413674 0.793959 0.070309 0.026 Uiso 1 1 calc R . . . .
C65 C 0.39733(9) 0.3068(2) 0.22994(8) 0.0322(4) Uani 1 1 d . . . . .
H65 H 0.437098 0.327859 0.252462 0.039 Uiso 1 1 calc R . . . .
C66 C 0.29755(10) 0.1841(2) 0.21698(8) 0.0336(4) Uani 1 1 d . . . . .
H66 H 0.270772 0.119416 0.232559 0.040 Uiso 1 1 calc R . . . .
C67 C 0.47494(11) 0.9811(2) -0.15346(9) 0.0405(5) Uani 1 1 d . . . . .
H67 H 0.444777 1.023382 -0.183371 0.049 Uiso 1 1 calc R . . . .
C68 C 0.43800(9) 0.3461(2) -0.10985(9) 0.0347(4) Uani 1 1 d . . . . .
H68 H 0.473230 0.284842 -0.105130 0.042 Uiso 1 1 calc R . . . .
C70 C 0.53808(12) 0.9888(3) -0.15481(11) 0.0493(6) Uani 1 1 d . . . . .
H70 H 0.551738 1.037082 -0.186977 0.059 Uiso 1 1 calc R . . . .
C71 C 0.56541(9) 0.8576(2) -0.06323(12) 0.0422(5) Uani 1 1 d . . . . .
H71 H 0.595852 0.817298 -0.033020 0.051 Uiso 1 1 calc R . . . .
C72 C 0.58175(11) 0.9291(2) -0.11133(13) 0.0502(7) Uani 1 1 d . . . . .
H72 H 0.624614 0.937304 -0.114417 0.060 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 C31 1.3648(19) . ?
O3 C24 1.375(2) . ?
O3 C36 1.379(2) . ?
F4 C35 1.3611(19) . ?
O5 C15 1.3798(19) . ?
O5 C16 1.382(2) . ?
N9 C13 1.400(2) . ?
N9 C16 1.283(2) . ?
N12 C17 1.420(2) . ?
N12 C24 1.281(2) . ?
C13 C15 1.381(2) . ?
C13 C61 1.397(3) . ?
C15 C34 1.383(2) . ?
C16 C38 1.486(2) . ?
C17 C36 1.382(3) . ?
C17 C59 1.389(3) . ?
C19 C29 1.509(2) . ?
C19 C38 1.578(2) . ?
C19 C46 1.540(2) . ?
C20 C42 1.388(2) . ?
C20 C49 1.387(2) . ?
C20 C55 1.514(2) . ?
C24 C46 1.480(2) . ?
C25 C29 1.398(2) . ?
C25 C43 1.392(2) . ?
C29 C56 1.390(2) . ?
C30 C35 1.374(3) . ?
C30 C56 1.391(2) . ?
C31 C48 1.364(3) . ?
C31 C69 1.373(3) . ?
C34 C40 1.378(3) . ?
C35 C43 1.371(3) . ?
C36 C41 1.380(2) . ?
C38 C55 1.558(2) . ?
C40 C45 1.387(3) . ?
C41 C64 1.386(3) . ?
C42 C48 1.386(3) . ?
C45 C61 1.381(3) . ?
C46 C55 1.579(2) . ?
C49 C69 1.393(2) . ?
C59 C62 1.389(3) . ?
C62 C64 1.402(3) . ?
O2 C28 1.373(2) . ?
O2 C53 1.374(2) . ?
F6 C57 1.367(2) . ?
O7 C33 1.348(2) . ?
O7 C39 1.385(2) . ?
F8 C52 1.364(2) . ?
N10 C32 1.398(2) . ?
N10 C33 1.313(2) . ?
N11 C23 1.408(2) . ?
N11 C28 1.278(2) . ?
C14 C50 1.392(3) . ?
C14 C60 1.395(2) . ?
C14 C63 1.510(2) . ?
C18 C28 1.483(2) . ?
C18 C47 1.543(2) . ?
C18 C63 1.583(2) . ?
C21 C22 1.385(2) . ?
C21 C37 1.381(3) . ?
C21 C47 1.509(2) . ?
C22 C27 1.383(3) . ?
C23 C53 1.386(3) . ?
C23 C58 1.394(3) . ?
C26 C57 1.374(3) . ?
C26 C60 1.383(3) . ?
C27 C52 1.377(3) . ?
C32 C39 1.377(3) . ?
C32 C71 1.394(3) . ?
C33 C44 1.481(2) . ?
C37 C68 1.390(3) . ?
C39 C67 1.390(3) . ?
C44 C47 1.572(2) . ?
C44 C63 1.555(2) . ?
C50 C54 1.393(2) . ?
C51 C65 1.386(3) . ?
C51 C66 1.398(3) . ?
C52 C68 1.373(3) . ?
C53 C65 1.384(2) . ?
C54 C57 1.371(3) . ?
C58 C66 1.385(3) . ?
C67 C70 1.381(3) . ?
C70 C72 1.372(4) . ?
C71 C72 1.381(4) . ?

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
C24 O3 C36 103.82(13) . . ?
C15 O5 C16 103.45(12) . . ?
C16 N9 C13 104.51(14) . . ?
C24 N12 C17 104.25(14) . . ?
C15 C13 N9 108.84(14) . . ?
C15 C13 C61 120.18(16) . . ?
C61 C13 N9 130.96(16) . . ?
O5 C15 C13 107.77(14) . . ?
O5 C15 C34 128.52(15) . . ?
C13 C15 C34 123.66(16) . . ?
O5 C16 C38 117.58(14) . . ?
N9 C16 O5 115.43(14) . . ?
N9 C16 C38 126.97(15) . . ?
C36 C17 N12 108.18(15) . . ?
C36 C17 C59 119.92(17) . . ?
C59 C17 N12 131.90(17) . . ?
C29 C19 C38 121.11(13) . . ?
C29 C19 C46 121.44(14) . . ?
C46 C19 C38 88.13(12) . . ?
C42 C20 C55 117.42(15) . . ?
C49 C20 C42 118.23(15) . . ?
C49 C20 C55 124.34(15) . . ?
O3 C24 C46 113.44(14) . . ?
N12 C24 O3 115.80(15) . . ?
N12 C24 C46 130.58(15) . . ?
C43 C25 C29 121.20(16) . . ?
C25 C29 C19 122.55(15) . . ?
C56 C29 C19 119.37(14) . . ?
C56 C29 C25 118.07(15) . . ?
C35 C30 C56 118.05(16) . . ?
F1 C31 C69 118.47(16) . . ?
C48 C31 F1 118.80(16) . . ?
C48 C31 C69 122.73(16) . . ?
C40 C34 C15 115.56(17) . . ?
F4 C35 C30 118.55(16) . . ?
F4 C35 C43 118.59(16) . . ?
C43 C35 C30 122.86(16) . . ?
O3 C36 C17 107.94(14) . . ?
O3 C36 C41 127.51(16) . . ?
C41 C36 C17 124.55(17) . . ?
C16 C38 C19 116.94(13) . . ?
C16 C38 C55 112.23(13) . . ?
C55 C38 C19 88.41(12) . . ?
C34 C40 C45 121.85(17) . . ?
C36 C41 C64 115.37(18) . . ?
C48 C42 C20 121.58(16) . . ?
C35 C43 C25 118.24(16) . . ?
C61 C45 C40 122.22(18) . . ?
C19 C46 C55 89.01(12) . . ?
C24 C46 C19 121.03(14) . . ?
C24 C46 C55 117.37(13) . . ?
C31 C48 C42 118.18(16) . . ?
C20 C49 C69 121.01(16) . . ?
C20 C55 C38 116.36(13) . . ?
C20 C55 C46 116.85(13) . . ?
C38 C55 C46 87.48(12) . . ?
C29 C56 C30 121.57(16) . . ?
C62 C59 C17 116.81(18) . . ?
C45 C61 C13 116.51(17) . . ?
C59 C62 C64 122.06(18) . . ?
C41 C64 C62 121.28(18) . . ?
C31 C69 C49 118.20(16) . . ?
C28 O2 C53 103.89(13) . . ?
C33 O7 C39 103.53(14) . . ?
C33 N10 C32 103.84(14) . . ?
C28 N11 C23 104.27(14) . . ?
C50 C14 C60 118.41(16) . . ?
C50 C14 C63 124.07(15) . . ?
C60 C14 C63 117.46(15) . . ?
C28 C18 C47 118.15(14) . . ?
C28 C18 C63 117.90(13) . . ?
C47 C18 C63 88.45(12) . . ?
C22 C21 C47 118.21(15) . . ?
C37 C21 C22 118.68(16) . . ?
C37 C21 C47 123.10(15) . . ?
C27 C22 C21 121.40(16) . . ?
C53 C23 N11 108.49(15) . . ?
C53 C23 C58 120.78(16) . . ?
C58 C23 N11 130.72(17) . . ?
C57 C26 C60 117.98(17) . . ?
C52 C27 C22 118.10(16) . . ?
O2 C28 C18 115.03(14) . . ?
N11 C28 O2 115.80(15) . . ?
N11 C28 C18 129.07(15) . . ?
C39 C32 N10 108.41(15) . . ?
C39 C32 C71 120.94(19) . . ?
C71 C32 N10 130.65(19) . . ?
O7 C33 C44 119.19(15) . . ?
N10 C33 O7 115.84(15) . . ?
N10 C33 C44 124.94(16) . . ?
C21 C37 C68 121.16(16) . . ?
O7 C39 C67 128.98(18) . . ?
C32 C39 O7 108.38(15) . . ?
C32 C39 C67 122.63(18) . . ?
C33 C44 C47 114.52(14) . . ?
C33 C44 C63 112.33(14) . . ?
C63 C44 C47 88.41(12) . . ?
C18 C47 C44 88.97(12) . . ?
C21 C47 C18 121.47(14) . . ?
C21 C47 C44 118.47(14) . . ?
C14 C50 C54 121.18(16) . . ?
C65 C51 C66 121.64(17) . . ?
F8 C52 C27 118.64(16) . . ?
F8 C52 C68 118.95(17) . . ?
C68 C52 C27 122.41(17) . . ?
O2 C53 C23 107.54(14) . . ?
O2 C53 C65 129.08(17) . . ?
C65 C53 C23 123.37(18) . . ?
C57 C54 C50 117.76(17) . . ?
F6 C57 C26 117.90(16) . . ?
F6 C57 C54 118.75(16) . . ?
C54 C57 C26 123.34(17) . . ?
C66 C58 C23 116.43(18) . . ?
C26 C60 C14 121.32(17) . . ?
C14 C63 C18 115.91(14) . . ?
C14 C63 C44 117.15(14) . . ?
C44 C63 C18 88.13(12) . . ?
C53 C65 C51 115.69(18) . . ?
C58 C66 C51 122.07(18) . . ?
C70 C67 C39 115.6(2) . . ?
C52 C68 C37 118.22(17) . . ?
C72 C70 C67 122.3(2) . . ?
C72 C71 C32 116.4(2) . . ?
C70 C72 C71 122.1(2) . . ?

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 C48 C42 177.85(16) . . . . ?
F1 C31 C69 C49 -176.97(16) . . . . ?
O3 C24 C46 C19 -168.80(14) . . . . ?
O3 C24 C46 C55 84.42(17) . . . . ?
O3 C36 C41 C64 -178.52(16) . . . . ?
F4 C35 C43 C25 -179.71(15) . . . . ?
O5 C15 C34 C40 178.23(17) . . . . ?
O5 C16 C38 C19 74.63(19) . . . . ?
O5 C16 C38 C55 -25.4(2) . . . . ?
N9 C13 C15 O5 -0.73(19) . . . . ?
N9 C13 C15 C34 176.80(16) . . . . ?
N9 C13 C61 C45 -177.44(18) . . . . ?
N9 C16 C38 C19 -106.94(19) . . . . ?
N9 C16 C38 C55 153.02(16) . . . . ?
N12 C17 C36 O3 -0.11(18) . . . . ?
N12 C17 C36 C41 179.89(16) . . . . ?
N12 C17 C59 C62 178.69(18) . . . . ?
N12 C24 C46 C19 16.3(3) . . . . ?
N12 C24 C46 C55 -90.4(2) . . . . ?
C13 N9 C16 O5 -0.16(19) . . . . ?
C13 N9 C16 C38 -178.62(16) . . . . ?
C13 C15 C34 C40 1.2(3) . . . . ?
C15 O5 C16 N9 -0.27(19) . . . . ?
C15 O5 C16 C38 178.33(14) . . . . ?
C15 C13 C61 C45 0.6(3) . . . . ?
C15 C34 C40 C45 0.1(3) . . . . ?
C16 O5 C15 C13 0.60(17) . . . . ?
C16 O5 C15 C34 -176.77(18) . . . . ?
C16 N9 C13 C15 0.54(19) . . . . ?
C16 N9 C13 C61 178.79(19) . . . . ?
C16 C38 C55 C20 -142.02(15) . . . . ?
C16 C38 C55 C46 99.11(14) . . . . ?
C17 N12 C24 O3 0.14(19) . . . . ?
C17 N12 C24 C46 174.90(17) . . . . ?
C17 C36 C41 C64 1.5(3) . . . . ?
C17 C59 C62 C64 1.1(3) . . . . ?
C19 C29 C56 C30 -178.00(16) . . . . ?
C19 C38 C55 C20 99.41(15) . . . . ?
C19 C38 C55 C46 -19.46(11) . . . . ?
C19 C46 C55 C20 -98.46(15) . . . . ?
C19 C46 C55 C38 19.96(12) . . . . ?
C20 C42 C48 C31 -0.8(3) . . . . ?
C20 C49 C69 C31 -1.0(3) . . . . ?
C24 O3 C36 C17 0.18(17) . . . . ?
C24 O3 C36 C41 -179.82(17) . . . . ?
C24 N12 C17 C36 -0.01(18) . . . . ?
C24 N12 C17 C59 -179.64(19) . . . . ?
C24 C46 C55 C20 26.4(2) . . . . ?
C24 C46 C55 C38 144.82(14) . . . . ?
C25 C29 C56 C30 1.1(3) . . . . ?
C29 C19 C38 C16 31.9(2) . . . . ?
C29 C19 C38 C55 146.11(14) . . . . ?
C29 C19 C46 C24 92.70(19) . . . . ?
C29 C19 C46 C55 -145.55(15) . . . . ?
C29 C25 C43 C35 -0.1(3) . . . . ?
C30 C35 C43 C25 0.7(3) . . . . ?
C34 C40 C45 C61 -1.1(3) . . . . ?
C35 C30 C56 C29 -0.6(3) . . . . ?
C36 O3 C24 N12 -0.21(18) . . . . ?
C36 O3 C24 C46 -175.88(13) . . . . ?
C36 C17 C59 C62 -0.9(3) . . . . ?
C36 C41 C64 C62 -1.2(3) . . . . ?
C38 C19 C29 C25 -61.4(2) . . . . ?
C38 C19 C29 C56 117.59(17) . . . . ?
C38 C19 C46 C24 -141.43(15) . . . . ?
C38 C19 C46 C55 -19.68(11) . . . . ?
C40 C45 C61 C13 0.7(3) . . . . ?
C42 C20 C49 C69 -1.5(3) . . . . ?
C42 C20 C55 C38 164.01(15) . . . . ?
C42 C20 C55 C46 -94.69(18) . . . . ?
C43 C25 C29 C19 178.32(16) . . . . ?
C43 C25 C29 C56 -0.7(3) . . . . ?
C46 C19 C29 C25 47.5(2) . . . . ?
C46 C19 C29 C56 -133.49(17) . . . . ?
C46 C19 C38 C16 -94.28(15) . . . . ?
C46 C19 C38 C55 19.96(11) . . . . ?
C48 C31 C69 C49 2.8(3) . . . . ?
C49 C20 C42 C48 2.4(3) . . . . ?
C49 C20 C55 C38 -14.5(2) . . . . ?
C49 C20 C55 C46 86.8(2) . . . . ?
C55 C20 C42 C48 -176.19(16) . . . . ?
C55 C20 C49 C69 177.01(17) . . . . ?
C56 C30 C35 F4 -179.96(15) . . . . ?
C56 C30 C35 C43 -0.3(3) . . . . ?
C59 C17 C36 O3 179.57(15) . . . . ?
C59 C17 C36 C41 -0.4(3) . . . . ?
C59 C62 C64 C41 -0.1(3) . . . . ?
C61 C13 C15 O5 -179.20(16) . . . . ?
C61 C13 C15 C34 -1.7(3) . . . . ?
C69 C31 C48 C42 -1.9(3) . . . . ?
O2 C53 C65 C51 -178.30(17) . . . . ?
O7 C33 C44 C47 110.94(17) . . . . ?
O7 C33 C44 C63 -150.18(15) . . . . ?
O7 C39 C67 C70 -178.77(18) . . . . ?
F8 C52 C68 C37 179.29(18) . . . . ?
N10 C32 C39 O7 -0.09(19) . . . . ?
N10 C32 C39 C67 -179.94(17) . . . . ?
N10 C32 C71 C72 178.91(18) . . . . ?
N10 C33 C44 C47 -67.0(2) . . . . ?
N10 C33 C44 C63 31.8(2) . . . . ?
N11 C23 C53 O2 -1.14(19) . . . . ?
N11 C23 C53 C65 179.89(17) . . . . ?
N11 C23 C58 C66 179.11(18) . . . . ?
C14 C50 C54 C57 -0.4(3) . . . . ?
C21 C22 C27 C52 0.8(3) . . . . ?
C21 C37 C68 C52 1.1(3) . . . . ?
C22 C21 C37 C68 0.1(3) . . . . ?
C22 C21 C47 C18 -178.38(16) . . . . ?
C22 C21 C47 C44 -70.4(2) . . . . ?
C22 C27 C52 F8 179.78(16) . . . . ?
C22 C27 C52 C68 0.6(3) . . . . ?
C23 N11 C28 O2 -0.76(19) . . . . ?
C23 N11 C28 C18 -176.78(16) . . . . ?
C23 C53 C65 C51 0.4(3) . . . . ?
C23 C58 C66 C51 0.8(3) . . . . ?
C27 C52 C68 C37 -1.5(3) . . . . ?
C28 O2 C53 C23 0.67(17) . . . . ?
C28 O2 C53 C65 179.56(18) . . . . ?
C28 N11 C23 C53 1.15(18) . . . . ?
C28 N11 C23 C58 -177.43(19) . . . . ?
C28 C18 C47 C21 -97.33(19) . . . . ?
C28 C18 C47 C44 139.44(15) . . . . ?
C28 C18 C63 C14 -20.4(2) . . . . ?
C28 C18 C63 C44 -139.87(15) . . . . ?
C32 N10 C33 O7 -0.1(2) . . . . ?
C32 N10 C33 C44 177.91(16) . . . . ?
C32 C39 C67 C70 1.1(3) . . . . ?
C32 C71 C72 C70 0.7(3) . . . . ?
C33 O7 C39 C32 0.02(18) . . . . ?
C33 O7 C39 C67 179.86(19) . . . . ?
C33 N10 C32 C39 0.12(19) . . . . ?
C33 N10 C32 C71 -179.19(19) . . . . ?
C33 C44 C47 C18 95.20(15) . . . . ?
C33 C44 C47 C21 -30.5(2) . . . . ?
C33 C44 C63 C14 143.93(15) . . . . ?
C33 C44 C63 C18 -97.73(15) . . . . ?
C37 C21 C22 C27 -1.1(3) . . . . ?
C37 C21 C47 C18 1.0(3) . . . . ?
C37 C21 C47 C44 108.91(19) . . . . ?
C39 O7 C33 N10 0.1(2) . . . . ?
C39 O7 C33 C44 -178.08(15) . . . . ?
C39 C32 C71 C72 -0.3(3) . . . . ?
C39 C67 C70 C72 -0.7(3) . . . . ?
C47 C18 C28 O2 168.50(14) . . . . ?
C47 C18 C28 N11 -15.5(3) . . . . ?
C47 C18 C63 C14 100.89(15) . . . . ?
C47 C18 C63 C44 -18.57(12) . . . . ?
C47 C21 C22 C27 178.31(16) . . . . ?
C47 C21 C37 C68 -179.24(18) . . . . ?
C47 C44 C63 C14 -100.12(15) . . . . ?
C47 C44 C63 C18 18.21(12) . . . . ?
C50 C14 C60 C26 0.7(3) . . . . ?
C50 C14 C63 C18 -110.25(19) . . . . ?
C50 C14 C63 C44 -8.2(2) . . . . ?
C50 C54 C57 F6 -179.78(17) . . . . ?
C50 C54 C57 C26 0.9(3) . . . . ?
C53 O2 C28 N11 0.08(19) . . . . ?
C53 O2 C28 C18 176.66(14) . . . . ?
C53 C23 C58 C66 0.7(3) . . . . ?
C57 C26 C60 C14 -0.2(3) . . . . ?
C58 C23 C53 O2 177.61(15) . . . . ?
C58 C23 C53 C65 -1.4(3) . . . . ?
C60 C14 C50 C54 -0.4(3) . . . . ?
C60 C14 C63 C18 72.7(2) . . . . ?
C60 C14 C63 C44 174.77(15) . . . . ?
C60 C26 C57 F6 -179.91(16) . . . . ?
C60 C26 C57 C54 -0.6(3) . . . . ?
C63 C14 C50 C54 -177.38(17) . . . . ?
C63 C14 C60 C26 177.92(16) . . . . ?
C63 C18 C28 O2 -87.11(18) . . . . ?
C63 C18 C28 N11 88.9(2) . . . . ?
C63 C18 C47 C21 141.58(15) . . . . ?
C63 C18 C47 C44 18.35(12) . . . . ?
C63 C44 C47 C18 -18.70(12) . . . . ?
C63 C44 C47 C21 -144.44(15) . . . . ?
C65 C51 C66 C58 -1.8(3) . . . . ?
C66 C51 C65 C53 1.1(3) . . . . ?
C67 C70 C72 C71 -0.1(3) . . . . ?
C71 C32 C39 O7 179.30(16) . . . . ?
C71 C32 C39 C67 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.708
####################################################################### 
# 
# 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_ran1cult
_database_code_depnum_ccdc_archive 'CCDC 1942462'
loop_
_audit_author_name
_audit_author_address
'haoran wang'
;Jilin University
China
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-07-23
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C30 H18 F4 N2 O2'
_chemical_formula_sum            'C30 H18 F4 N2 O2'
_chemical_formula_weight         514.46
_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                   8.8798(6)
_cell_length_b                   12.2737(10)
_cell_length_c                   13.1272(12)
_cell_angle_alpha                63.758(8)
_cell_angle_beta                 80.374(7)
_cell_angle_gamma                68.947(7)
_cell_volume                     1197.55(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1451
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.445
_cell_measurement_theta_min      3.213
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6410
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.498
_diffrn_reflns_theta_min         3.754
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3462
_reflns_number_total             4215
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.097
_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)+(0.0531P)²+0.1894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F1A-C36
 1.34 with sigma of 0.02
 F1-C32 \\sim F1A-C36
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C10)
4. Others
 Fixed Sof: F1(0.92) F1A(0.08) H32(0.1) H36(0.9)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
5.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C23(H23), C24(H24), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36), C43(H43), C45(H45), C46(H46)
;
_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 0.56356(13) 0.57363(10) 0.38019(10) 0.0318(3) Uani 0.92 1 d D . P A 1
F1A F 0.4790(14) 0.9625(10) 0.4045(12) 0.035(3) Uani 0.08 1 d D . P B 2
F2 F 0.93681(13) 0.79473(13) 0.23244(10) 0.0446(3) Uani 1 1 d . . . . .
F3 F 0.30713(17) 0.78165(11) 0.15864(10) 0.0452(3) Uani 1 1 d . . . . .
F4 F 0.30418(18) 1.20401(12) -0.06160(10) 0.0515(3) Uani 1 1 d . . . . .
O1 O -0.00399(14) 0.67685(11) 0.51445(10) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.21779(14) 0.66608(11) 0.69101(10) 0.0256(3) Uani 1 1 d . . . . .
N1 N -0.14234(16) 0.83286(13) 0.57181(11) 0.0212(2) Uani 1 1 d . . . . .
N2 N 0.22197(17) 0.84539(13) 0.69664(11) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.08474(19) 0.86726(15) 0.44273(14) 0.0210(3) Uani 1 1 d . . . . .
H1 H 0.023433 0.960966 0.405577 0.025 Uiso 1 1 calc R . . . .
C2 C 0.23668(19) 0.84130(14) 0.50842(13) 0.0199(3) Uani 1 1 d . . . . .
H2 H 0.264658 0.922037 0.479309 0.024 Uiso 1 1 calc R . . . .
C3 C 0.34190(19) 0.75740(14) 0.44573(13) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.351179 0.665487 0.494109 0.024 Uiso 1 1 calc R . . . .
C4 C 0.20059(19) 0.81966(15) 0.35760(13) 0.0206(3) Uani 1 1 d . . . . .
H4 H 0.172440 0.753563 0.346798 0.025 Uiso 1 1 calc R . . . .
C10 C -0.02272(19) 0.79171(15) 0.50985(14) 0.0212(2) Uani 1 1 d . . . . .
C11 C -0.12740(19) 0.63970(15) 0.58671(14) 0.0214(3) Uani 1 1 d . . . . .
C12 C -0.21277(19) 0.73589(15) 0.62276(14) 0.0211(3) Uani 1 1 d . . . . .
C13 C -0.3449(2) 0.72783(16) 0.69547(15) 0.0269(4) Uani 1 1 d . . . . .
H13 H -0.403521 0.793755 0.720085 0.032 Uiso 1 1 calc R . . . .
C14 C -0.3865(2) 0.61792(17) 0.73011(15) 0.0285(4) Uani 1 1 d . . . . .
H14 H -0.474886 0.607271 0.781115 0.034 Uiso 1 1 calc R . . . .
C15 C -0.3014(2) 0.52216(16) 0.69183(15) 0.0281(4) Uani 1 1 d . . . . .
H15 H -0.335007 0.449049 0.716562 0.034 Uiso 1 1 calc R . . . .
C16 C -0.1696(2) 0.53081(16) 0.61902(15) 0.0269(4) Uani 1 1 d . . . . .
H16 H -0.111923 0.465998 0.592902 0.032 Uiso 1 1 calc R . . . .
C20 C 0.22872(19) 0.78674(15) 0.63369(14) 0.0221(3) Uani 1 1 d . . . . .
C21 C 0.2025(2) 0.64767(16) 0.80388(14) 0.0246(4) Uani 1 1 d . . . . .
C22 C 0.2052(2) 0.75775(16) 0.80768(15) 0.0249(4) Uani 1 1 d . . . . .
C23 C 0.1918(2) 0.76693(19) 0.91107(16) 0.0343(4) Uani 1 1 d . . . . .
H23 H 0.192535 0.842154 0.915077 0.041 Uiso 1 1 calc R . . . .
C24 C 0.1775(3) 0.6616(2) 1.00743(16) 0.0401(5) Uani 1 1 d . . . . .
H24 H 0.168528 0.664299 1.079474 0.048 Uiso 1 1 calc R . . . .
C25 C 0.1760(3) 0.5512(2) 1.00154(17) 0.0409(5) Uani 1 1 d . . . . .
H25 H 0.165521 0.480915 1.069857 0.049 Uiso 1 1 calc R . . . .
C26 C 0.1892(3) 0.54073(19) 0.89884(17) 0.0370(4) Uani 1 1 d . . . . .
H26 H 0.189089 0.465569 0.894418 0.044 Uiso 1 1 calc R . . . .
C31 C 0.50488(19) 0.76654(15) 0.39878(13) 0.0204(3) Uani 1 1 d . . . . .
C32 C 0.6085(2) 0.67386(16) 0.36379(14) 0.0246(4) Uani 1 1 d D . . . .
H32 H 0.577152 0.601969 0.378254 0.029 Uiso 0.1 1 calc R . P A 2
C33 C 0.7548(2) 0.67949(18) 0.30907(15) 0.0293(4) Uani 1 1 d . . . . .
H33 H 0.822985 0.613685 0.286818 0.035 Uiso 1 1 calc R . . . .
C34 C 0.7963(2) 0.78479(19) 0.28859(15) 0.0306(4) Uani 1 1 d . . . . .
C35 C 0.7021(2) 0.88007(18) 0.32206(15) 0.0306(4) Uani 1 1 d . . . . .
H35 H 0.735045 0.951260 0.307530 0.037 Uiso 1 1 calc R . . . .
C36 C 0.5570(2) 0.86896(16) 0.37797(15) 0.0260(4) Uani 1 1 d D . . . .
H36 H 0.491367 0.933340 0.402729 0.031 Uiso 0.9 1 calc R . P B 1
C41 C 0.22353(19) 0.92547(15) 0.24596(14) 0.0213(3) Uani 1 1 d . . . . .
C42 C 0.2777(2) 0.90121(17) 0.15060(15) 0.0294(4) Uani 1 1 d . . . . .
C43 C 0.3047(3) 0.99212(19) 0.04622(16) 0.0389(5) Uani 1 1 d . . . . .
H43 H 0.340635 0.972130 -0.017703 0.047 Uiso 1 1 calc R . . . .
C44 C 0.2772(3) 1.11297(18) 0.03921(15) 0.0341(4) Uani 1 1 d . . . . .
C45 C 0.2242(2) 1.14429(17) 0.12985(15) 0.0308(4) Uani 1 1 d . . . . .
H45 H 0.205752 1.228559 0.122632 0.037 Uiso 1 1 calc R . . . .
C46 C 0.1980(2) 1.04998(16) 0.23228(15) 0.0259(4) Uani 1 1 d . . . . .
H46 H 0.161359 1.070889 0.295669 0.031 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 C32 1.345(2) . ?
F1A C36 1.273(10) . ?
F2 C34 1.356(2) . ?
F3 C42 1.352(2) . ?
F4 C44 1.355(2) . ?
O1 C10 1.334(2) . ?
O1 C11 1.392(2) . ?
O2 C20 1.365(2) . ?
O2 C21 1.387(2) . ?
N1 C10 1.317(2) . ?
N1 C12 1.395(2) . ?
N2 C20 1.297(2) . ?
N2 C22 1.400(2) . ?
C1 C2 1.582(2) . ?
C1 C4 1.552(2) . ?
C1 C10 1.476(2) . ?
C2 C3 1.553(2) . ?
C2 C20 1.476(2) . ?
C3 C4 1.585(2) . ?
C3 C31 1.498(2) . ?
C4 C41 1.511(2) . ?
C11 C12 1.387(2) . ?
C11 C16 1.383(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.401(3) . ?
C15 C16 1.385(3) . ?
C21 C22 1.383(2) . ?
C21 C26 1.381(3) . ?
C22 C23 1.393(2) . ?
C23 C24 1.381(3) . ?
C24 C25 1.396(3) . ?
C25 C26 1.392(3) . ?
C31 C32 1.386(2) . ?
C31 C36 1.393(2) . ?
C32 C33 1.385(3) . ?
C33 C34 1.371(3) . ?
C34 C35 1.374(3) . ?
C35 C36 1.393(3) . ?
C41 C42 1.383(2) . ?
C41 C46 1.393(2) . ?
C42 C43 1.382(3) . ?
C43 C44 1.376(3) . ?
C44 C45 1.368(3) . ?
C45 C46 1.383(2) . ?

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
C10 O1 C11 104.26(13) . . ?
C20 O2 C21 103.95(12) . . ?
C10 N1 C12 104.68(13) . . ?
C20 N2 C22 104.65(13) . . ?
C4 C1 C2 89.06(12) . . ?
C10 C1 C2 115.06(13) . . ?
C10 C1 C4 116.06(13) . . ?
C3 C2 C1 88.72(11) . . ?
C20 C2 C1 117.92(13) . . ?
C20 C2 C3 120.60(13) . . ?
C2 C3 C4 88.93(11) . . ?
C31 C3 C2 120.78(13) . . ?
C31 C3 C4 117.25(13) . . ?
C1 C4 C3 88.65(11) . . ?
C41 C4 C1 114.50(13) . . ?
C41 C4 C3 114.98(13) . . ?
O1 C10 C1 122.94(14) . . ?
N1 C10 O1 115.40(14) . . ?
N1 C10 C1 121.64(14) . . ?
C12 C11 O1 107.91(14) . . ?
C16 C11 O1 129.60(15) . . ?
C16 C11 C12 122.47(16) . . ?
C11 C12 N1 107.75(14) . . ?
C13 C12 N1 130.30(15) . . ?
C13 C12 C11 121.94(15) . . ?
C12 C13 C14 116.07(16) . . ?
C13 C14 C15 121.67(16) . . ?
C16 C15 C14 122.01(16) . . ?
C11 C16 C15 115.82(16) . . ?
O2 C20 C2 118.52(14) . . ?
N2 C20 O2 115.22(15) . . ?
N2 C20 C2 126.15(14) . . ?
C22 C21 O2 107.68(14) . . ?
C26 C21 O2 128.48(16) . . ?
C26 C21 C22 123.84(17) . . ?
C21 C22 N2 108.50(14) . . ?
C21 C22 C23 120.52(16) . . ?
C23 C22 N2 130.98(16) . . ?
C24 C23 C22 116.88(18) . . ?
C23 C24 C25 121.58(18) . . ?
C26 C25 C24 122.15(18) . . ?
C21 C26 C25 115.04(18) . . ?
C32 C31 C3 119.23(14) . . ?
C32 C31 C36 116.05(16) . . ?
C36 C31 C3 124.48(15) . . ?
F1 C32 C31 118.72(15) . . ?
F1 C32 C33 117.15(15) . . ?
C33 C32 C31 124.09(16) . . ?
C34 C33 C32 116.66(16) . . ?
F2 C34 C33 118.05(17) . . ?
F2 C34 C35 118.86(17) . . ?
C33 C34 C35 123.10(17) . . ?
C34 C35 C36 117.89(16) . . ?
F1A C36 C31 125.1(6) . . ?
F1A C36 C35 112.7(6) . . ?
C31 C36 C35 122.16(17) . . ?
C42 C41 C4 120.55(14) . . ?
C42 C41 C46 115.85(16) . . ?
C46 C41 C4 123.56(15) . . ?
F3 C42 C41 118.81(16) . . ?
F3 C42 C43 117.24(16) . . ?
C43 C42 C41 123.96(16) . . ?
C44 C43 C42 116.90(17) . . ?
F4 C44 C43 118.41(17) . . ?
F4 C44 C45 119.00(17) . . ?
C45 C44 C43 122.59(17) . . ?
C44 C45 C46 118.23(16) . . ?
C45 C46 C41 122.46(16) . . ?

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 177.38(15) . . . . ?
F2 C34 C35 C36 178.96(15) . . . . ?
F3 C42 C43 C44 -178.88(18) . . . . ?
F4 C44 C45 C46 -179.67(17) . . . . ?
O1 C11 C12 N1 0.44(17) . . . . ?
O1 C11 C12 C13 179.50(15) . . . . ?
O1 C11 C16 C15 -179.17(15) . . . . ?
O2 C21 C22 N2 0.11(19) . . . . ?
O2 C21 C22 C23 179.96(16) . . . . ?
O2 C21 C26 C25 179.78(18) . . . . ?
N1 C12 C13 C14 178.93(16) . . . . ?
N2 C22 C23 C24 -179.63(18) . . . . ?
C1 C2 C3 C4 16.03(11) . . . . ?
C1 C2 C3 C31 137.49(14) . . . . ?
C1 C2 C20 O2 64.77(19) . . . . ?
C1 C2 C20 N2 -111.10(18) . . . . ?
C1 C4 C41 C42 -158.90(15) . . . . ?
C1 C4 C41 C46 23.3(2) . . . . ?
C2 C1 C4 C3 16.03(11) . . . . ?
C2 C1 C4 C41 -100.93(14) . . . . ?
C2 C1 C10 O1 -89.98(18) . . . . ?
C2 C1 C10 N1 88.40(18) . . . . ?
C2 C3 C4 C1 -16.34(11) . . . . ?
C2 C3 C4 C41 100.18(14) . . . . ?
C2 C3 C31 C32 167.28(14) . . . . ?
C2 C3 C31 C36 -18.6(2) . . . . ?
C3 C2 C20 O2 -41.7(2) . . . . ?
C3 C2 C20 N2 142.39(16) . . . . ?
C3 C4 C41 C42 100.51(18) . . . . ?
C3 C4 C41 C46 -77.2(2) . . . . ?
C3 C31 C32 F1 -4.4(2) . . . . ?
C3 C31 C32 C33 173.38(15) . . . . ?
C3 C31 C36 F1A 6.1(8) . . . . ?
C3 C31 C36 C35 -172.34(16) . . . . ?
C4 C1 C2 C3 -16.37(11) . . . . ?
C4 C1 C2 C20 -140.73(14) . . . . ?
C4 C1 C10 O1 12.1(2) . . . . ?
C4 C1 C10 N1 -169.57(14) . . . . ?
C4 C3 C31 C32 -86.32(18) . . . . ?
C4 C3 C31 C36 87.84(19) . . . . ?
C4 C41 C42 F3 1.1(3) . . . . ?
C4 C41 C42 C43 -178.64(17) . . . . ?
C4 C41 C46 C45 178.18(16) . . . . ?
C10 O1 C11 C12 -0.77(16) . . . . ?
C10 O1 C11 C16 177.42(16) . . . . ?
C10 N1 C12 C11 0.08(17) . . . . ?
C10 N1 C12 C13 -178.87(17) . . . . ?
C10 C1 C2 C3 102.14(14) . . . . ?
C10 C1 C2 C20 -22.22(19) . . . . ?
C10 C1 C4 C3 -101.58(14) . . . . ?
C10 C1 C4 C41 141.45(14) . . . . ?
C11 O1 C10 N1 0.89(18) . . . . ?
C11 O1 C10 C1 179.36(14) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 N1 C10 O1 -0.63(18) . . . . ?
C12 N1 C10 C1 -179.12(14) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
C16 C11 C12 N1 -177.91(15) . . . . ?
C16 C11 C12 C13 1.2(2) . . . . ?
C20 O2 C21 C22 -0.04(17) . . . . ?
C20 O2 C21 C26 -179.05(18) . . . . ?
C20 N2 C22 C21 -0.14(18) . . . . ?
C20 N2 C22 C23 -179.97(19) . . . . ?
C20 C2 C3 C4 138.10(14) . . . . ?
C20 C2 C3 C31 -100.45(18) . . . . ?
C21 O2 C20 N2 -0.06(19) . . . . ?
C21 O2 C20 C2 -176.38(14) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 N2 C20 O2 0.13(19) . . . . ?
C22 N2 C20 C2 176.12(15) . . . . ?
C22 C21 C26 C25 0.9(3) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C24 C25 C26 C21 -0.5(3) . . . . ?
C26 C21 C22 N2 179.19(17) . . . . ?
C26 C21 C22 C23 -1.0(3) . . . . ?
C31 C3 C4 C1 -140.82(13) . . . . ?
C31 C3 C4 C41 -24.30(19) . . . . ?
C31 C32 C33 C34 -0.5(3) . . . . ?
C32 C31 C36 F1A -179.6(8) . . . . ?
C32 C31 C36 C35 2.0(2) . . . . ?
C32 C33 C34 F2 -178.27(15) . . . . ?
C32 C33 C34 C35 1.6(3) . . . . ?
C33 C34 C35 C36 -0.9(3) . . . . ?
C34 C35 C36 F1A -179.6(7) . . . . ?
C34 C35 C36 C31 -1.0(3) . . . . ?
C36 C31 C32 F1 -179.07(14) . . . . ?
C36 C31 C32 C33 -1.3(2) . . . . ?
C41 C42 C43 C44 0.8(3) . . . . ?
C42 C41 C46 C45 0.3(3) . . . . ?
C42 C43 C44 F4 179.32(18) . . . . ?
C42 C43 C44 C45 -0.6(3) . . . . ?
C43 C44 C45 C46 0.2(3) . . . . ?
C44 C45 C46 C41 -0.1(3) . . . . ?
C46 C41 C42 F3 179.00(16) . . . . ?
C46 C41 C42 C43 -0.7(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_dboaf24yellow
_database_code_depnum_ccdc_archive 'CCDC 1942071'
loop_
_audit_author_name
_audit_author_address
'haoran wang'
;Jilin University
China
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-01-22
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C30 H18 F4 N2 O2'
_chemical_formula_sum            'C30 H18 F4 N2 O2'
_chemical_formula_weight         514.46
_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                   9.1590(3)
_cell_length_b                   12.2660(5)
_cell_length_c                   12.8671(6)
_cell_angle_alpha                107.066(4)
_cell_angle_beta                 107.962(4)
_cell_angle_gamma                106.939(4)
_cell_volume                     1193.03(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4099
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.1380
_cell_measurement_theta_min      4.0080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_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  0.0281
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10672
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.781
_diffrn_reflns_theta_min         3.982
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -53.00   0.50    0.50    --    0.00 -72.00 -60.00   72
  2  ω    -35.00   7.00   0.50    0.50    --    0.00 -72.00 -60.00   84
  3  ω      0.00  80.00   0.50    0.50    --    0.00  19.00 -90.00  160
  4  ω     38.00  93.00   0.50    1.28    --    5.00  72.00 -30.00  110
  5  ω     61.00  88.00   0.50    1.28    --    5.00  38.00 150.00   54
  6  ω     -8.00  29.00   0.50    1.28    --    5.00  72.00 -30.00   74
  7  ω     -6.00  23.00   0.50    1.28    --    5.00  38.00 150.00   58
  8  ω   -105.00 -10.00   0.50    1.28    --  -98.80  19.00  60.00  190
  9  ω   -112.00 -25.00   0.50    1.28    --  -98.80  72.00 -30.00  174
 10  ω   -104.00 -17.00   0.50    1.28    --  -98.80  72.00  60.00  174
 11  ω    -58.00 -31.00   0.50    1.28    --  -98.80  72.00 120.00   54
 12  ω   -105.00 -30.00   0.50    1.28    --  -98.80  57.00 -60.00  150
 13  ω   -111.00 -78.00   0.50    1.28    --  -98.80  72.00 120.00   66
 14  ω   -112.00  -9.00   0.50    1.28    --  -98.80  57.00-180.00  206
 15  ω   -106.00 -10.00   0.50    1.28    --  -98.80  19.00 -30.00  192
 16  ω   -117.00 -85.00   0.50    1.28    --  -98.80 -72.00  90.00   64
 17  ω   -170.00-145.00   0.50    1.28    --  -98.80 -72.00  90.00   50
 18  ω   -108.00 -34.00   0.50    1.28    --  -98.80  72.00-180.00  148
 19  ω    -90.00 -34.00   0.50    1.28    --  -98.80  72.00   0.00  112
 20  ω   -102.00 -49.00   0.50    1.28    --  -98.80  72.00-120.00  106
 21  ω   -146.00 -12.00   0.50    1.28    --  -98.80   0.00  90.00  268
 22  ω   -185.00-160.00   0.50    1.28    --  -98.80 -72.00 -90.00   50
 23  ω    -93.00 -66.00   0.50    1.28    --  -98.80  72.00-150.00   54
 24  ω   -187.00-161.00   0.50    1.28    --  -98.80   0.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0459115000
_diffrn_orient_matrix_UB_12      -0.0434321000
_diffrn_orient_matrix_UB_13      -0.1355215000
_diffrn_orient_matrix_UB_21      0.0392570000
_diffrn_orient_matrix_UB_22      0.1359266000
_diffrn_orient_matrix_UB_23      0.0142463000
_diffrn_orient_matrix_UB_31      0.1852278000
_diffrn_orient_matrix_UB_32      0.0243641000
_diffrn_orient_matrix_UB_33      0.0262603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3608
_reflns_number_total             4551
_reflns_odcompleteness_completeness 98.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_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         0.224
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4551
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.055
_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)+(0.0584P)²+0.4090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1276
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
N2 \\sim C24: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Sof(F1)=Sof(H13)=1-FVAR(1)
 Sof(F1A)=Sof(H17)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C19(H19), C20(H20), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29)
;
_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 0.8651(4) 0.4652(3) 0.9835(3) 0.0764(13) Uani 0.452(4) 1 d . . P A 2
F1A F 0.4575(3) 0.06184(18) 0.73825(18) 0.0435(7) Uani 0.548(4) 1 d . . P A 1
F2 F 0.6932(3) 0.1951(2) 1.14847(16) 0.1105(7) Uani 1 1 d . . . . .
F3 F -0.00584(16) 0.22810(13) 0.84899(12) 0.0580(4) Uani 1 1 d . . . . .
F4 F 0.49933(15) 0.46538(10) 0.85190(11) 0.0503(3) Uani 1 1 d . . . . .
O1 O 0.76668(16) 0.16582(12) 0.49014(12) 0.0412(3) Uani 1 1 d . . . . .
O2 O 0.47995(17) 0.27368(12) 0.42347(12) 0.0425(3) Uani 1 1 d . . . . .
N1 N 0.89726(19) 0.35966(14) 0.64088(14) 0.0363(3) Uani 1 1 d . . . . .
N2 N 0.31197(18) 0.06715(13) 0.33438(13) 0.0335(3) Uani 1 1 d . U . . .
C1 C 0.8985(2) 0.23455(18) 0.47274(17) 0.0375(4) Uani 1 1 d . . . . .
C2 C 0.9471(3) 0.1974(2) 0.38137(19) 0.0460(5) Uani 1 1 d . . . . .
H2 H 0.889808 0.116873 0.319305 0.055 Uiso 1 1 calc R . . . .
C3 C 1.0865(3) 0.2879(2) 0.3884(2) 0.0499(5) Uani 1 1 d . . . . .
H3 H 1.124378 0.267893 0.329196 0.060 Uiso 1 1 calc R . . . .
C4 C 1.1718(3) 0.4084(2) 0.4821(2) 0.0500(5) Uani 1 1 d . . . . .
H4 H 1.265762 0.466298 0.484115 0.060 Uiso 1 1 calc R . . . .
C5 C 1.1201(3) 0.4441(2) 0.5723(2) 0.0459(5) Uani 1 1 d . . . . .
H5 H 1.176531 0.524618 0.634283 0.055 Uiso 1 1 calc R . . . .
C6 C 0.9806(2) 0.35407(18) 0.56572(17) 0.0375(4) Uani 1 1 d . . . . .
C7 C 0.7765(2) 0.24891(18) 0.59269(17) 0.0380(4) Uani 1 1 d . . . . .
C8 C 0.6507(2) 0.19855(17) 0.63517(16) 0.0349(4) Uani 1 1 d . . . . .
H8 H 0.660000 0.127200 0.651722 0.042 Uiso 1 1 calc R . . . .
C9 C 0.6508(2) 0.29726(17) 0.74341(17) 0.0357(4) Uani 1 1 d . . . . .
H9 H 0.737171 0.381061 0.768490 0.043 Uiso 1 1 calc R . . . .
C10 C 0.4726(2) 0.27931(16) 0.65737(16) 0.0335(4) Uani 1 1 d . . . . .
H10 H 0.485848 0.350115 0.634875 0.040 Uiso 1 1 calc R . . . .
C11 C 0.4620(2) 0.16701(16) 0.55616(16) 0.0338(4) Uani 1 1 d . . . . .
H11 H 0.386740 0.087926 0.550600 0.041 Uiso 1 1 calc R . . . .
C12 C 0.6621(2) 0.26738(19) 0.84972(17) 0.0393(4) Uani 1 1 d . . . . .
C13 C 0.5638(3) 0.1524(2) 0.84103(19) 0.0455(5) Uani 1 1 d . . . . .
H13 H 0.488841 0.089232 0.764627 0.055 Uiso 0.452(4) 1 calc R . P A 2
C14 C 0.5707(3) 0.1262(3) 0.9390(2) 0.0622(7) Uani 1 1 d . . . . .
H14 H 0.501350 0.048118 0.929548 0.075 Uiso 1 1 calc R . . . .
C15 C 0.6832(4) 0.2193(4) 1.0508(2) 0.0731(8) Uani 1 1 d . . . . .
C16 C 0.7859(3) 0.3344(3) 1.0677(2) 0.0702(8) Uani 1 1 d . . . . .
H16 H 0.862478 0.396028 1.144518 0.084 Uiso 1 1 calc R . . . .
C17 C 0.7724(3) 0.3569(2) 0.9661(2) 0.0537(6) Uani 1 1 d . . . . .
H17 H 0.840593 0.435860 0.976627 0.064 Uiso 0.548(4) 1 calc R . P A 1
C18 C 0.3355(2) 0.25977(16) 0.70055(16) 0.0326(4) Uani 1 1 d . . . . .
C19 C 0.1894(2) 0.15087(18) 0.65019(17) 0.0384(4) Uani 1 1 d . . . . .
H19 H 0.168366 0.084106 0.581630 0.046 Uiso 1 1 calc R . . . .
C20 C 0.0731(2) 0.13840(19) 0.69925(18) 0.0433(5) Uani 1 1 d . . . . .
H20 H -0.024299 0.064344 0.664795 0.052 Uiso 1 1 calc R . . . .
C21 C 0.1059(2) 0.2385(2) 0.80001(18) 0.0419(4) Uani 1 1 d . . . . .
C22 C 0.2478(3) 0.34971(19) 0.85347(18) 0.0421(4) Uani 1 1 d . . . . .
H22 H 0.268151 0.416776 0.921482 0.051 Uiso 1 1 calc R . . . .
C23 C 0.3577(2) 0.35638(16) 0.80107(17) 0.0360(4) Uani 1 1 d . . . . .
C24 C 0.4147(2) 0.16650(17) 0.43542(17) 0.0364(4) Uani 1 1 d . U . . .
C25 C 0.4093(2) 0.23759(17) 0.29955(17) 0.0361(4) Uani 1 1 d . . . . .
C26 C 0.4282(3) 0.3096(2) 0.23595(19) 0.0470(5) Uani 1 1 d . . . . .
H26 H 0.496540 0.395452 0.274056 0.056 Uiso 1 1 calc R . . . .
C27 C 0.3393(3) 0.2461(2) 0.1119(2) 0.0514(5) Uani 1 1 d . . . . .
H27 H 0.348576 0.290524 0.064978 0.062 Uiso 1 1 calc R . . . .
C28 C 0.2363(3) 0.1176(2) 0.05531(19) 0.0505(5) Uani 1 1 d . . . . .
H28 H 0.179247 0.078291 -0.028304 0.061 Uiso 1 1 calc R . . . .
C29 C 0.2167(3) 0.04680(19) 0.12062(18) 0.0442(5) Uani 1 1 d . . . . .
H29 H 0.147255 -0.038862 0.083025 0.053 Uiso 1 1 calc R . . . .
C30 C 0.3056(2) 0.11009(17) 0.24444(16) 0.0354(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.260(4) . ?
F1A C13 1.282(3) . ?
F2 C15 1.356(3) . ?
F3 C21 1.352(2) . ?
F4 C23 1.360(2) . ?
O1 C1 1.380(2) . ?
O1 C7 1.368(2) . ?
O2 C24 1.352(2) . ?
O2 C25 1.393(2) . ?
N1 C6 1.403(2) . ?
N1 C7 1.288(2) . ?
N2 C24 1.307(2) . ?
N2 C30 1.398(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.385(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C7 C8 1.477(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.554(2) . ?
C8 C11 1.570(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.572(3) . ?
C9 C12 1.498(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.547(2) . ?
C10 C18 1.508(2) . ?
C11 H11 0.9800 . ?
C11 C24 1.476(3) . ?
C12 C13 1.385(3) . ?
C12 C17 1.387(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.367(4) . ?
C15 C16 1.359(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(3) . ?
C18 C23 1.384(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(3) . ?
C21 C22 1.374(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.370(3) . ?
C25 C26 1.379(3) . ?
C25 C30 1.385(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.394(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.387(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.382(3) . ?

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 O1 C1 103.88(15) . . ?
C24 O2 C25 104.14(14) . . ?
C7 N1 C6 104.52(16) . . ?
C24 N2 C30 104.89(15) . . ?
O1 C1 C2 128.82(18) . . ?
O1 C1 C6 107.71(16) . . ?
C2 C1 C6 123.47(18) . . ?
C1 C2 H2 122.2 . . ?
C1 C2 C3 115.6(2) . . ?
C3 C2 H2 122.2 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.79(19) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.70(19) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.6 . . ?
C6 C5 C4 116.8(2) . . ?
C6 C5 H5 121.6 . . ?
C1 C6 N1 108.36(16) . . ?
C5 C6 N1 130.99(18) . . ?
C5 C6 C1 120.65(18) . . ?
O1 C7 C8 115.69(16) . . ?
N1 C7 O1 115.52(16) . . ?
N1 C7 C8 128.76(17) . . ?
C7 C8 H8 111.1 . . ?
C7 C8 C9 115.06(15) . . ?
C7 C8 C11 116.70(15) . . ?
C9 C8 H8 111.1 . . ?
C9 C8 C11 90.35(13) . . ?
C11 C8 H8 111.1 . . ?
C8 C9 H9 110.8 . . ?
C8 C9 C10 88.83(13) . . ?
C10 C9 H9 110.8 . . ?
C12 C9 C8 116.64(15) . . ?
C12 C9 H9 110.8 . . ?
C12 C9 C10 117.21(14) . . ?
C9 C10 H10 109.4 . . ?
C11 C10 C9 90.51(13) . . ?
C11 C10 H10 109.4 . . ?
C18 C10 C9 117.68(15) . . ?
C18 C10 H10 109.4 . . ?
C18 C10 C11 119.15(15) . . ?
C8 C11 H11 109.8 . . ?
C10 C11 C8 89.13(13) . . ?
C10 C11 H11 109.8 . . ?
C24 C11 C8 119.37(15) . . ?
C24 C11 C10 117.33(15) . . ?
C24 C11 H11 109.8 . . ?
C13 C12 C9 123.81(18) . . ?
C13 C12 C17 115.1(2) . . ?
C17 C12 C9 121.03(19) . . ?
F1A C13 C12 121.03(19) . . ?
F1A C13 C14 115.2(2) . . ?
C12 C13 H13 118.1 . . ?
C14 C13 C12 123.8(2) . . ?
C14 C13 H13 118.1 . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 H14 121.2 . . ?
F2 C15 C14 118.5(3) . . ?
F2 C15 C16 118.8(3) . . ?
C16 C15 C14 122.6(2) . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.6(2) . . ?
C17 C16 H16 121.2 . . ?
F1 C17 C12 119.9(3) . . ?
F1 C17 C16 116.8(3) . . ?
C12 C17 C16 123.3(3) . . ?
C12 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
C19 C18 C10 125.43(16) . . ?
C19 C18 C23 116.22(16) . . ?
C23 C18 C10 118.32(16) . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.79(18) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 120.9 . . ?
C21 C20 C19 118.22(18) . . ?
C21 C20 H20 120.9 . . ?
F3 C21 C20 119.06(18) . . ?
F3 C21 C22 118.17(18) . . ?
C20 C21 C22 122.77(18) . . ?
C21 C22 H22 121.8 . . ?
C23 C22 C21 116.34(18) . . ?
C23 C22 H22 121.8 . . ?
F4 C23 C18 117.64(16) . . ?
F4 C23 C22 117.70(17) . . ?
C22 C23 C18 124.66(18) . . ?
O2 C24 C11 120.20(16) . . ?
N2 C24 O2 115.13(16) . . ?
N2 C24 C11 124.66(16) . . ?
C26 C25 O2 129.41(17) . . ?
C26 C25 C30 122.83(18) . . ?
C30 C25 O2 107.74(15) . . ?
C25 C26 H26 122.1 . . ?
C25 C26 C27 115.89(19) . . ?
C27 C26 H26 122.1 . . ?
C26 C27 H27 119.1 . . ?
C26 C27 C28 121.8(2) . . ?
C28 C27 H27 119.1 . . ?
C27 C28 H28 119.2 . . ?
C29 C28 C27 121.6(2) . . ?
C29 C28 H28 119.2 . . ?
C28 C29 H29 121.7 . . ?
C30 C29 C28 116.56(19) . . ?
C30 C29 H29 121.7 . . ?
C25 C30 N2 108.10(16) . . ?
C29 C30 N2 130.61(17) . . ?
C29 C30 C25 121.28(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.525
_oxdiff_exptl_absorpt_empirical_full_min 0.730
####################################################################### 
# 
# 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_ran2cult
_database_code_depnum_ccdc_archive 'CCDC 1942461'
loop_
_audit_author_name
_audit_author_address
'haoran wang'
;Jilin University
China
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-07-23
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C30 H18 F4 N2 O2'
_chemical_formula_sum            'C30 H18 F4 N2 O2'
_chemical_formula_weight         514.46
_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           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                   12.9258(2)
_cell_length_b                   11.10764(16)
_cell_length_c                   8.24353(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.3647(16)
_cell_angle_gamma                90
_cell_volume                     1160.36(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1242
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.246
_cell_measurement_theta_min      2.145
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6028
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.420
_diffrn_reflns_theta_min         5.295
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2007
_reflns_number_total             2073
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.053
_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)+(0.0368P)²+0.6349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0808
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C15(H15), C16(H16), C18(H18), C19(H19)
;
_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 0.29311(6) 0.64528(7) -0.01505(9) 0.0242(2) Uani 1 1 d . . . . .
F2 F 0.07091(6) 0.35306(7) 0.14264(10) 0.0249(2) Uani 1 1 d . . . . .
O3 O -0.21410(7) 0.67602(8) 0.51126(11) 0.0200(2) Uani 1 1 d . . . . .
N4 N -0.22741(8) 0.51440(9) 0.34315(13) 0.0169(2) Uani 1 1 d . . . . .
C5 C 0.11547(10) 0.66099(11) 0.27182(15) 0.0164(3) Uani 1 1 d . . . . .
H5 H 0.092805 0.717762 0.343642 0.020 Uiso 1 1 calc R . . . .
C6 C 0.07486(9) 0.54459(11) 0.26359(14) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.18854(10) 0.69635(12) 0.17737(15) 0.0184(3) Uani 1 1 d . . . . .
H7 H 0.215623 0.776085 0.183826 0.022 Uiso 1 1 calc R . . . .
C8 C 0.18257(10) 0.49644(12) 0.05882(15) 0.0184(3) Uani 1 1 d . . . . .
H8 H 0.205090 0.440174 -0.013798 0.022 Uiso 1 1 calc R . . . .
C9 C -0.04848(9) 0.58293(10) 0.47896(15) 0.0141(3) Uani 1 1 d . . . . .
H9 H -0.016069 0.664952 0.484571 0.017 Uiso 1 1 calc R . . . .
C10 C 0.11022(10) 0.46667(11) 0.15459(15) 0.0164(3) Uani 1 1 d . . . . .
C11 C -0.16541(10) 0.58780(11) 0.43711(15) 0.0154(3) Uani 1 1 d . . . . .
C12 C -0.00046(9) 0.49692(11) 0.36564(14) 0.0135(3) Uani 1 1 d . . . . .
H12 H -0.058336 0.451251 0.292860 0.016 Uiso 1 1 calc R . . . .
C13 C -0.32930(10) 0.55469(11) 0.35073(15) 0.0177(3) Uani 1 1 d . . . . .
C14 C 0.22026(9) 0.61264(12) 0.07469(15) 0.0176(3) Uani 1 1 d . . . . .
C15 C -0.51473(11) 0.57301(14) 0.30821(19) 0.0286(3) Uani 1 1 d . . . . .
H15 H -0.583481 0.545944 0.259022 0.034 Uiso 1 1 calc R . . . .
C16 C -0.50420(11) 0.67302(14) 0.4125(2) 0.0308(3) Uani 1 1 d . . . . .
H16 H -0.565914 0.712295 0.431903 0.037 Uiso 1 1 calc R . . . .
C17 C -0.32047(10) 0.65401(12) 0.45431(16) 0.0195(3) Uani 1 1 d . . . . .
C18 C -0.42801(10) 0.51193(13) 0.27414(17) 0.0239(3) Uani 1 1 d . . . . .
H18 H -0.435583 0.444330 0.202171 0.029 Uiso 1 1 calc R . . . .
C19 C -0.40595(11) 0.71677(13) 0.48875(19) 0.0274(3) Uani 1 1 d . . . . .
H19 H -0.398058 0.785010 0.559590 0.033 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 C14 1.3565(14) . ?
F2 C10 1.3567(14) . ?
O3 C11 1.3717(15) . ?
O3 C17 1.3843(15) . ?
N4 C11 1.2893(17) . ?
N4 C13 1.4040(16) . ?
C5 C6 1.3920(17) . ?
C5 C7 1.3936(18) . ?
C6 C10 1.3883(17) . ?
C6 C12 1.5030(16) . ?
C7 C14 1.3733(19) . ?
C8 C10 1.3777(18) . ?
C8 C14 1.3766(18) . ?
C9 C11 1.4835(17) . ?
C9 C12 1.5489(16) . ?
C9 C12 1.5839(16) 3_566 ?
C13 C17 1.3859(19) . ?
C13 C18 1.3910(19) . ?
C15 C16 1.395(2) . ?
C15 C18 1.386(2) . ?
C16 C19 1.389(2) . ?
C17 C19 1.3824(18) . ?

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 O3 C17 103.59(10) . . ?
C11 N4 C13 104.43(10) . . ?
C6 C5 C7 121.67(12) . . ?
C5 C6 C12 125.42(11) . . ?
C10 C6 C5 116.20(11) . . ?
C10 C6 C12 118.35(11) . . ?
C14 C7 C5 118.10(12) . . ?
C14 C8 C10 115.98(11) . . ?
C11 C9 C12 115.77(10) . 3_566 ?
C11 C9 C12 113.15(10) . . ?
C12 C9 C12 89.93(9) . 3_566 ?
F2 C10 C6 117.42(11) . . ?
F2 C10 C8 117.94(11) . . ?
C8 C10 C6 124.64(12) . . ?
O3 C11 C9 117.28(10) . . ?
N4 C11 O3 115.72(11) . . ?
N4 C11 C9 126.93(11) . . ?
C6 C12 C9 116.78(9) . 3_566 ?
C6 C12 C9 120.07(10) . . ?
C9 C12 C9 90.07(9) . 3_566 ?
C17 C13 N4 108.49(11) . . ?
C17 C13 C18 120.55(12) . . ?
C18 C13 N4 130.96(12) . . ?
F1 C14 C7 118.61(11) . . ?
F1 C14 C8 118.00(11) . . ?
C7 C14 C8 123.39(11) . . ?
C18 C15 C16 122.03(13) . . ?
C19 C16 C15 121.80(13) . . ?
O3 C17 C13 107.77(11) . . ?
C19 C17 O3 128.46(13) . . ?
C19 C17 C13 123.77(13) . . ?
C15 C18 C13 116.56(13) . . ?
C17 C19 C16 115.28(13) . . ?

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
O3 C17 C19 C16 179.91(13) . . . . ?
N4 C13 C17 O3 0.03(14) . . . . ?
N4 C13 C17 C19 179.58(12) . . . . ?
N4 C13 C18 C15 179.96(13) . . . . ?
C5 C6 C10 F2 -179.22(10) . . . . ?
C5 C6 C10 C8 1.14(18) . . . . ?
C5 C6 C12 C9 -100.53(14) . . . 3_566 ?
C5 C6 C12 C9 6.55(17) . . . . ?
C5 C7 C14 F1 -178.55(10) . . . . ?
C5 C7 C14 C8 0.90(19) . . . . ?
C6 C5 C7 C14 -0.12(18) . . . . ?
C7 C5 C6 C10 -0.83(17) . . . . ?
C7 C5 C6 C12 177.28(11) . . . . ?
C10 C6 C12 C9 -175.38(11) . . . . ?
C10 C6 C12 C9 77.54(14) . . . 3_566 ?
C10 C8 C14 F1 178.83(10) . . . . ?
C10 C8 C14 C7 -0.63(19) . . . . ?
C11 O3 C17 C13 0.15(13) . . . . ?
C11 O3 C17 C19 -179.37(13) . . . . ?
C11 N4 C13 C17 -0.22(13) . . . . ?
C11 N4 C13 C18 179.43(13) . . . . ?
C11 C9 C12 C6 120.40(11) . . . . ?
C11 C9 C12 C9 -118.18(11) . . . 3_566 ?
C12 C6 C10 F2 2.54(16) . . . . ?
C12 C6 C10 C8 -177.10(11) . . . . ?
C12 C9 C11 O3 -169.21(10) . . . . ?
C12 C9 C11 O3 88.97(13) 3_566 . . . ?
C12 C9 C11 N4 -87.81(15) 3_566 . . . ?
C12 C9 C11 N4 14.02(17) . . . . ?
C12 C9 C12 C6 -121.42(12) 3_566 . . . ?
C12 C9 C12 C9 0.001(0) 3_566 . . 3_566 ?
C13 N4 C11 O3 0.34(14) . . . . ?
C13 N4 C11 C9 177.16(11) . . . . ?
C13 C17 C19 C16 0.5(2) . . . . ?
C14 C8 C10 F2 179.92(10) . . . . ?
C14 C8 C10 C6 -0.44(19) . . . . ?
C15 C16 C19 C17 -0.3(2) . . . . ?
C16 C15 C18 C13 0.6(2) . . . . ?
C17 O3 C11 N4 -0.32(14) . . . . ?
C17 O3 C11 C9 -177.46(10) . . . . ?
C17 C13 C18 C15 -0.44(19) . . . . ?
C18 C13 C17 O3 -179.65(11) . . . . ?
C18 C13 C17 C19 -0.1(2) . . . . ?
C18 C15 C16 C19 -0.3(2) . . . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1814882'
loop_
_audit_author_name
_audit_author_address
'haoran wang' 'Jilin University'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 F N O'
_chemical_formula_weight         239.24

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'
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'
F F 0.0727 0.0534 '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                   6.6501(4)
_cell_length_b                   26.3347(15)
_cell_length_c                   7.4237(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.269(3)
_cell_angle_gamma                90
_cell_volume                     1175.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6037
_cell_measurement_theta_min      6.8
_cell_measurement_theta_max      68.15

_exptl_crystal_description       0.13
_exptl_crystal_colour            0.12
_exptl_crystal_density_meas      0.08
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.793
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11905
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.806
_diffrn_reflns_theta_max         68.259
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2114
_reflns_number_gt                1833
_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       'Bruker APEX-II CCD'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1136P)²+0.3718P] 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         2114
_refine_ls_number_parameters     163
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.2322
_refine_ls_wR_factor_gt          0.2251
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003

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 1.1970(5) 0.30622(9) 0.7283(4) 0.1375(10) Uani 1 1 d . . . . .
O1 O 0.6683(3) 0.59589(7) 0.7331(3) 0.0846(6) Uani 1 1 d . . . . .
N1 N 0.3917(4) 0.56625(8) 0.7997(4) 0.0770(7) Uani 1 1 d . U . . .
C1 C 0.5383(5) 0.63658(10) 0.7343(4) 0.0750(7) Uani 1 1 d . . . . .
C2 C 0.5637(6) 0.68685(12) 0.7025(6) 0.1027(11) Uani 1 1 d . . . . .
H8 H 0.6796 0.6985 0.6749 0.123 Uiso 1 1 calc R U . . .
C3 C 0.4073(6) 0.71905(12) 0.7140(6) 0.1049(11) Uani 1 1 d . . . . .
H3 H 0.4190 0.7537 0.6959 0.126 Uiso 1 1 calc R U . . .
C4 C 0.2339(6) 0.70177(13) 0.7514(5) 0.0963(10) Uani 1 1 d . . . . .
H4 H 0.1307 0.7249 0.7565 0.116 Uiso 1 1 calc R U . . .
C5 C 0.2096(5) 0.65108(12) 0.7813(5) 0.0863(9) Uani 1 1 d . . . . .
H5 H 0.0914 0.6394 0.8054 0.104 Uiso 1 1 calc R U . . .
C6 C 0.3673(4) 0.61839(10) 0.7742(4) 0.0712(7) Uani 1 1 d . . . . .
C7 C 0.5657(5) 0.55535(9) 0.7754(4) 0.0746(7) Uani 1 1 d . U . . .
C8 C 0.6576(5) 0.50591(10) 0.7829(4) 0.0781(8) Uani 1 1 d . . . . .
H8A H 0.5893 0.4789 0.8155 0.094 Uiso 1 1 calc R U . . .
C9 C 0.8334(5) 0.49533(10) 0.7471(4) 0.0747(7) Uani 1 1 d . . . . .
H9 H 0.9026 0.5228 0.7185 0.090 Uiso 1 1 calc R U . . .
C10 C 0.9296(4) 0.44516(9) 0.7476(4) 0.0694(7) Uani 1 1 d . . . . .
C11 C 0.8473(6) 0.40101(10) 0.7923(5) 0.0862(9) Uani 1 1 d . . . . .
H11 H 0.7289 0.4030 0.8273 0.103 Uiso 1 1 calc R U . . .
C12 C 0.9369(6) 0.35424(11) 0.7862(6) 0.1003(10) Uani 1 1 d . . . . .
H12 H 0.8802 0.3248 0.8165 0.120 Uiso 1 1 calc R U . . .
C13 C 1.1099(6) 0.35196(12) 0.7349(5) 0.0943(10) Uani 1 1 d . . . . .
C14 C 1.1957(6) 0.39404(15) 0.6900(6) 0.0984(10) Uani 1 1 d . . . . .
H14 H 1.3143 0.3916 0.6554 0.118 Uiso 1 1 calc R U . . .
C15 C 1.1049(5) 0.44032(12) 0.6964(5) 0.0868(9) Uani 1 1 d . . . . .
H15 H 1.1634 0.4693 0.6654 0.104 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 C13 1.346(4) . ?
O1 C7 1.374(3) . ?
O1 C1 1.379(3) . ?
N1 C7 1.277(4) . ?
N1 C6 1.386(3) . ?
C1 C2 1.368(4) . ?
C1 C6 1.377(4) . ?
C2 C3 1.373(5) . ?
C2 H8 0.9300 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.429(4) . ?
C8 C9 1.334(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.467(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.377(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.352(5) . ?
C14 C15 1.370(5) . ?
C14 H14 0.9300 . ?
C15 H15 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 O1 C1 103.2(2) . . ?
C7 N1 C6 105.3(2) . . ?
C2 C1 C6 123.2(3) . . ?
C2 C1 O1 128.8(3) . . ?
C6 C1 O1 108.0(2) . . ?
C1 C2 C3 115.7(3) . . ?
C1 C2 H8 122.1 . . ?
C3 C2 H8 122.1 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 117.2(3) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 N1 131.4(2) . . ?
C1 C6 N1 108.3(2) . . ?
N1 C7 O1 115.2(2) . . ?
N1 C7 C8 126.7(3) . . ?
O1 C7 C8 118.1(3) . . ?
C9 C8 C7 125.4(3) . . ?
C9 C8 H8A 117.3 . . ?
C7 C8 H8A 117.3 . . ?
C8 C9 C10 127.3(3) . . ?
C8 C9 H9 116.4 . . ?
C10 C9 H9 116.4 . . ?
C15 C10 C11 117.1(3) . . ?
C15 C10 C9 120.1(3) . . ?
C11 C10 C9 122.7(3) . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
F1 C13 C14 119.4(3) . . ?
F1 C13 C12 118.6(3) . . ?
C14 C13 C12 122.0(3) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C10 122.0(3) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.037

