# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_210316_cjf_2_bd_0m
_database_code_depnum_ccdc_archive 'CCDC 2095295'
loop_
_audit_author_name
_audit_author_address
'Ren-Xiao Liang'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 F3 N O'
_chemical_formula_sum            'C22 H14 F3 N O'
_chemical_formula_weight         365.34
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7165(13)
_cell_length_b                   11.402(2)
_cell_length_c                   15.962(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1768.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.821
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1202 before and 0.0447 after correction.
The Ratio of minimum to maximum transmission is 0.8822.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17842
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.256
_diffrn_reflns_theta_min         4.766
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3217
_reflns_number_total             3236
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+0.2077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0729
_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:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_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 0.33513(14) 0.22795(10) 0.64986(7) 0.0506(3) Uani 1 1 d . . . . .
F2 F 0.29270(14) 0.30980(10) 0.53156(8) 0.0533(3) Uani 1 1 d . . . . .
F3 F 0.48184(16) 0.21565(9) 0.54968(8) 0.0554(3) Uani 1 1 d . . . . .
O1 O 0.27689(14) 0.66503(12) 0.63554(10) 0.0486(4) Uani 1 1 d . . . . .
N1 N 0.35860(12) 0.47659(12) 0.65413(9) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.2753(2) 0.51569(17) 0.80072(13) 0.0417(4) Uani 1 1 d . . . . .
H1 H 0.196049 0.558323 0.783802 0.050 Uiso 1 1 calc R . . . .
C2 C 0.3065(2) 0.4981(2) 0.88449(14) 0.0512(5) Uani 1 1 d . . . . .
H2 H 0.247767 0.530430 0.926079 0.061 Uiso 1 1 calc R . . . .
C3 C 0.4208(3) 0.4346(2) 0.90914(12) 0.0523(6) Uani 1 1 d . . . . .
H3 H 0.438319 0.423047 0.967105 0.063 Uiso 1 1 calc R . . . .
C4 C 0.5102(2) 0.38751(18) 0.85020(11) 0.0411(4) Uani 1 1 d . . . . .
H4 H 0.589068 0.344291 0.867127 0.049 Uiso 1 1 calc R . . . .
C5 C 0.48169(17) 0.40514(14) 0.76611(10) 0.0296(3) Uani 1 1 d . . . . .
C6 C 0.36582(16) 0.46788(14) 0.74284(11) 0.0304(3) Uani 1 1 d . . . . .
C7 C 0.46371(16) 0.40020(13) 0.61654(10) 0.0258(3) Uani 1 1 d . . . . .
C8 C 0.56652(16) 0.37053(13) 0.68988(10) 0.0275(3) Uani 1 1 d . . . . .
H8 H 0.584692 0.284227 0.691000 0.033 Uiso 1 1 calc R . . . .
C9 C 0.34711(16) 0.58350(15) 0.61184(12) 0.0312(4) Uani 1 1 d . . . . .
C10 C 0.43909(16) 0.57485(14) 0.53836(10) 0.0278(3) Uani 1 1 d . . . . .
C11 C 0.51108(16) 0.47020(13) 0.54121(9) 0.0265(3) Uani 1 1 d . . . . .
C12 C 0.6042(2) 0.44206(17) 0.47918(12) 0.0389(4) Uani 1 1 d . . . . .
H12 H 0.653040 0.369905 0.480341 0.047 Uiso 1 1 calc R . . . .
C13 C 0.6243(2) 0.52241(19) 0.41499(12) 0.0440(5) Uani 1 1 d . . . . .
H13 H 0.687532 0.504334 0.371462 0.053 Uiso 1 1 calc R . . . .
C14 C 0.5543(2) 0.62855(17) 0.41287(11) 0.0408(4) Uani 1 1 d . . . . .
H14 H 0.571402 0.682554 0.368758 0.049 Uiso 1 1 calc R . . . .
C15 C 0.45967(19) 0.65608(16) 0.47477(11) 0.0362(4) Uani 1 1 d . . . . .
H15 H 0.410534 0.728096 0.473730 0.043 Uiso 1 1 calc R . . . .
C16 C 0.3931(2) 0.28759(16) 0.58707(11) 0.0380(4) Uani 1 1 d . . . . .
C17 C 0.70150(16) 0.43645(16) 0.68340(10) 0.0304(4) Uani 1 1 d . . . . .
C18 C 0.70596(18) 0.55785(16) 0.69422(11) 0.0341(4) Uani 1 1 d . . . . .
H18 H 0.624315 0.599110 0.708477 0.041 Uiso 1 1 calc R . . . .
C19 C 0.8286(2) 0.6190(2) 0.68436(12) 0.0447(5) Uani 1 1 d . . . . .
H19 H 0.830238 0.701702 0.691258 0.054 Uiso 1 1 calc R . . . .
C20 C 0.9479(2) 0.5596(2) 0.66458(14) 0.0548(6) Uani 1 1 d . . . . .
H20 H 1.031653 0.601346 0.657520 0.066 Uiso 1 1 calc R . . . .
C21 C 0.9451(2) 0.4394(3) 0.65507(17) 0.0617(6) Uani 1 1 d . . . . .
H21 H 1.027766 0.398521 0.642512 0.074 Uiso 1 1 calc R . . . .
C22 C 0.8220(2) 0.3773(2) 0.66373(14) 0.0467(5) Uani 1 1 d . . . . .
H22 H 0.820787 0.294641 0.656160 0.056 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 C16 1.336(2) . ?
F2 C16 1.342(2) . ?
F3 C16 1.332(2) . ?
O1 C9 1.214(2) . ?
N1 C6 1.421(2) . ?
N1 C7 1.470(2) . ?
N1 C9 1.398(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(3) . ?
C1 C6 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 C6 1.385(2) . ?
C5 C8 1.522(2) . ?
C7 C8 1.576(2) . ?
C7 C11 1.515(2) . ?
C7 C16 1.530(2) . ?
C8 H8 1.0000 . ?
C8 C17 1.515(2) . ?
C9 C10 1.478(2) . ?
C10 C11 1.384(2) . ?
C10 C15 1.389(2) . ?
C11 C12 1.379(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.396(3) . ?
C17 C22 1.387(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.398(3) . ?
C22 H22 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
C6 N1 C7 109.33(13) . . ?
C9 N1 C6 123.09(15) . . ?
C9 N1 C7 112.02(13) . . ?
C2 C1 H1 121.7 . . ?
C2 C1 C6 116.56(19) . . ?
C6 C1 H1 121.7 . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.74(19) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.81(19) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C8 128.95(16) . . ?
C6 C5 C4 119.85(17) . . ?
C6 C5 C8 111.09(14) . . ?
C1 C6 N1 127.22(16) . . ?
C5 C6 N1 110.09(14) . . ?
C5 C6 C1 122.67(17) . . ?
N1 C7 C8 105.33(12) . . ?
N1 C7 C11 102.88(12) . . ?
N1 C7 C16 108.11(14) . . ?
C11 C7 C8 120.68(13) . . ?
C11 C7 C16 109.55(13) . . ?
C16 C7 C8 109.43(13) . . ?
C5 C8 C7 101.25(12) . . ?
C5 C8 H8 109.7 . . ?
C7 C8 H8 109.7 . . ?
C17 C8 C5 113.26(13) . . ?
C17 C8 C7 113.05(13) . . ?
C17 C8 H8 109.7 . . ?
O1 C9 N1 124.22(16) . . ?
O1 C9 C10 129.68(16) . . ?
N1 C9 C10 106.06(13) . . ?
C11 C10 C9 109.71(14) . . ?
C11 C10 C15 121.76(16) . . ?
C15 C10 C9 128.51(16) . . ?
C10 C11 C7 109.08(14) . . ?
C12 C11 C7 130.29(15) . . ?
C12 C11 C10 120.57(15) . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 117.95(17) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.61(17) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.33(16) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 121.1 . . ?
C14 C15 C10 117.75(17) . . ?
C14 C15 H15 121.1 . . ?
F1 C16 F2 106.59(16) . . ?
F1 C16 C7 112.69(14) . . ?
F2 C16 C7 111.76(14) . . ?
F3 C16 F1 107.20(15) . . ?
F3 C16 F2 106.92(15) . . ?
F3 C16 C7 111.35(16) . . ?
C18 C17 C8 120.69(15) . . ?
C22 C17 C8 120.31(17) . . ?
C22 C17 C18 118.96(17) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.67(18) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 119.9(2) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_210317_cjf_1_4_cf3_0m
_database_code_depnum_ccdc_archive 'CCDC 2095296'
loop_
_audit_author_name
_audit_author_address
'Ren-Xiao Liang'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H9 F6 N O'
_chemical_formula_sum            'C17 H9 F6 N O'
_chemical_formula_weight         357.25
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.5776(5)
_cell_length_b                   6.1725(3)
_cell_length_c                   12.0797(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.532(2)
_cell_angle_gamma                90
_cell_volume                     752.05(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9802
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.13
_cell_measurement_theta_min      3.84
_shelx_estimated_absorpt_T_max   0.691
_shelx_estimated_absorpt_T_min   0.625
_exptl_absorpt_coefficient_mu    1.329
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1828 before and 0.0991 after correction.
The Ratio of minimum to maximum transmission is 0.7820.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11014
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.124
_diffrn_reflns_theta_min         3.837
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2694
_reflns_number_total             2740
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.074
_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)+(0.0350P)²+0.1522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C14(H14), C15(H15)
;
_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 0.34688(16) 0.5990(3) 0.87160(14) 0.0537(5) Uani 1 1 d . . . . .
F2 F 0.18900(13) 0.4203(3) 0.75267(13) 0.0439(4) Uani 1 1 d . . . . .
F3 F 0.37069(17) 0.2594(3) 0.84334(14) 0.0527(5) Uani 1 1 d . . . . .
F4 F 0.86061(19) 0.6378(4) 1.05797(13) 0.0640(6) Uani 1 1 d . . . . .
F5 F 0.96034(17) 0.7335(4) 0.93893(16) 0.0740(7) Uani 1 1 d . . . . .
F6 F 0.7949(2) 0.9190(4) 0.9590(2) 0.0763(7) Uani 1 1 d . . . . .
O1 O 0.47937(16) 0.0818(3) 0.53719(14) 0.0341(4) Uani 1 1 d . . . . .
N1 N 0.35547(18) 0.3231(3) 0.60940(16) 0.0284(4) Uani 1 1 d . . . . .
C1 C 0.1784(2) 0.2309(4) 0.4244(2) 0.0318(5) Uani 1 1 d . . . . .
H1 H 0.210384 0.088672 0.419000 0.038 Uiso 1 1 calc R . . . .
C2 C 0.0655(2) 0.3104(5) 0.3426(2) 0.0359(5) Uani 1 1 d . . . . .
H2 H 0.019596 0.221363 0.279097 0.043 Uiso 1 1 calc R . . . .
C3 C 0.0188(2) 0.5171(4) 0.3520(2) 0.0348(6) Uani 1 1 d . . . . .
H3 H -0.060151 0.565823 0.296283 0.042 Uiso 1 1 calc R . . . .
C4 C 0.0857(2) 0.6545(4) 0.4420(2) 0.0324(5) Uani 1 1 d . . . . .
H4 H 0.053603 0.796396 0.448029 0.039 Uiso 1 1 calc R . . . .
C5 C 0.2004(2) 0.5795(4) 0.52249(19) 0.0286(5) Uani 1 1 d . . . . .
C6 C 0.2417(2) 0.3684(4) 0.51379(19) 0.0270(5) Uani 1 1 d . . . . .
C7 C 0.3787(2) 0.5033(4) 0.6924(2) 0.0290(5) Uani 1 1 d . . . . .
C8 C 0.3004(2) 0.6952(4) 0.6222(2) 0.0308(5) Uani 1 1 d . . . . .
H8A H 0.255848 0.780732 0.668960 0.037 Uiso 1 1 calc R . . . .
H8B H 0.358692 0.791682 0.593816 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4713(2) 0.2230(4) 0.60456(19) 0.0276(5) Uani 1 1 d . . . . .
C10 C 0.5794(2) 0.3286(4) 0.69669(18) 0.0284(5) Uani 1 1 d . . . . .
C11 C 0.5295(2) 0.5038(4) 0.74188(19) 0.0292(5) Uani 1 1 d . . . . .
C12 C 0.6118(2) 0.6362(4) 0.8250(2) 0.0336(5) Uani 1 1 d . . . . .
H12 H 0.578165 0.756384 0.856432 0.040 Uiso 1 1 calc R . . . .
C13 C 0.7473(2) 0.5851(5) 0.8608(2) 0.0363(5) Uani 1 1 d . . . . .
C14 C 0.7969(2) 0.4058(5) 0.8172(2) 0.0368(6) Uani 1 1 d . . . . .
H14 H 0.888841 0.372907 0.845055 0.044 Uiso 1 1 calc R . . . .
C15 C 0.7128(2) 0.2754(4) 0.7335(2) 0.0334(5) Uani 1 1 d . . . . .
H15 H 0.745475 0.153768 0.702483 0.040 Uiso 1 1 calc R . . . .
C16 C 0.3210(2) 0.4436(5) 0.7907(2) 0.0368(6) Uani 1 1 d . . . . .
C17 C 0.8402(2) 0.7199(5) 0.9524(2) 0.0452(7) 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 C16 1.338(3) . ?
F2 C16 1.340(3) . ?
F3 C16 1.331(3) . ?
F4 C17 1.328(4) . ?
F5 C17 1.332(3) . ?
F6 C17 1.330(4) . ?
O1 C9 1.213(3) . ?
N1 C6 1.422(3) . ?
N1 C7 1.468(3) . ?
N1 C9 1.389(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.390(3) . ?
C1 C6 1.378(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 C6 1.389(3) . ?
C5 C8 1.521(3) . ?
C7 C8 1.544(3) . ?
C7 C11 1.525(3) . ?
C7 C16 1.534(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.485(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.385(3) . ?
C11 C12 1.381(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.403(3) . ?
C13 C14 1.394(4) . ?
C13 C17 1.492(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(4) . ?
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
C6 N1 C7 109.43(18) . . ?
C9 N1 C6 126.46(19) . . ?
C9 N1 C7 113.43(18) . . ?
C2 C1 H1 121.6 . . ?
C6 C1 H1 121.6 . . ?
C6 C1 C2 116.8(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 C8 130.7(2) . . ?
C6 C5 C8 109.92(19) . . ?
C1 C6 N1 127.4(2) . . ?
C1 C6 C5 123.2(2) . . ?
C5 C6 N1 109.36(19) . . ?
N1 C7 C8 104.74(18) . . ?
N1 C7 C11 102.08(18) . . ?
N1 C7 C16 108.82(19) . . ?
C11 C7 C8 122.6(2) . . ?
C11 C7 C16 108.04(19) . . ?
C16 C7 C8 109.68(19) . . ?
C5 C8 C7 101.82(19) . . ?
C5 C8 H8A 111.4 . . ?
C5 C8 H8B 111.4 . . ?
C7 C8 H8A 111.4 . . ?
C7 C8 H8B 111.4 . . ?
H8A C8 H8B 109.3 . . ?
O1 C9 N1 126.1(2) . . ?
O1 C9 C10 128.7(2) . . ?
N1 C9 C10 105.25(19) . . ?
C11 C10 C9 109.82(19) . . ?
C15 C10 C9 128.1(2) . . ?
C15 C10 C11 122.0(2) . . ?
C10 C11 C7 108.77(19) . . ?
C12 C11 C7 129.9(2) . . ?
C12 C11 C10 121.1(2) . . ?
C11 C12 H12 121.5 . . ?
C11 C12 C13 116.9(2) . . ?
C13 C12 H12 121.5 . . ?
C12 C13 C17 119.1(2) . . ?
C14 C13 C12 121.9(2) . . ?
C14 C13 C17 118.9(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 117.7(2) . . ?
C10 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
F1 C16 F2 106.8(2) . . ?
F1 C16 C7 110.6(2) . . ?
F2 C16 C7 112.16(19) . . ?
F3 C16 F1 107.4(2) . . ?
F3 C16 F2 107.0(2) . . ?
F3 C16 C7 112.6(2) . . ?
F4 C17 F5 104.8(2) . . ?
F4 C17 F6 104.6(3) . . ?
F4 C17 C13 112.3(3) . . ?
F5 C17 C13 112.6(2) . . ?
F6 C17 F5 108.8(3) . . ?
F6 C17 C13 113.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
