# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_111
_database_code_depnum_ccdc_archive 'CCDC 2047058'
loop_
_audit_author_name
_audit_author_address
'Sheng Zhang'
;Nanyang Normal University
China
;
_audit_update_record             
;
2020-11-29 deposited with the CCDC.	2021-02-05 downloaded from the CCDC.
;
_audit_creation_date             2020-11-08
_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         'C20 H11 F3 N2'
_chemical_formula_sum            'C20 H11 F3 N2'
_chemical_formula_weight         336.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2360(8)
_cell_length_b                   17.7645(14)
_cell_length_c                   18.4265(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3023.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5419
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.617
_cell_measurement_theta_min      3.123
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1015 before and 0.0686 after correction.
The Ratio of minimum to maximum transmission is 0.9316.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1677
_diffrn_reflns_av_unetI/netI     0.0888
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45226
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.666
_diffrn_reflns_theta_min         3.123
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1707
_reflns_number_total             3506
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1866
_refine_ls_R_factor_gt           0.0795
_refine_ls_restrained_S_all      1.014
_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)+(0.0751P)²+1.7329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C17(H17), C12(H12), C11(H11), C10(H10),
 C18(H18), C20(H20), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.2900(4) 0.5597(2) 0.48237(13) 0.1433(14) Uani 1 1 d . . . . .
F3 F 0.3141(4) 0.66427(18) 0.53121(14) 0.1364(13) Uani 1 1 d . . . . .
N1 N 0.6324(2) 0.73399(12) 0.23927(11) 0.0331(6) Uani 1 1 d . . . . .
F2 F 0.4763(3) 0.58560(18) 0.54144(13) 0.1160(11) Uani 1 1 d . . . . .
N2 N 0.6394(3) 0.75312(15) 0.11820(13) 0.0479(7) Uani 1 1 d . . . . .
C16 C 0.7297(3) 0.79357(15) 0.22743(15) 0.0351(7) Uani 1 1 d . . . . .
C14 C 0.5844(3) 0.71251(16) 0.17048(15) 0.0364(7) Uani 1 1 d . . . . .
C8 C 0.4274(3) 0.61667(15) 0.22496(14) 0.0339(7) Uani 1 1 d . . . . .
C5 C 0.5739(3) 0.70229(15) 0.30307(14) 0.0330(7) Uani 1 1 d . . . . .
C13 C 0.4847(3) 0.65104(16) 0.16287(14) 0.0355(7) Uani 1 1 d . . . . .
C4 C 0.4707(3) 0.64441(15) 0.29645(14) 0.0326(7) Uani 1 1 d . . . . .
C3 C 0.4119(3) 0.61593(16) 0.36031(15) 0.0408(8) Uani 1 1 d . . . . .
H3 H 0.343179 0.577749 0.357571 0.049 Uiso 1 1 calc R . . . .
C6 C 0.6139(3) 0.72910(17) 0.37114(15) 0.0432(8) Uani 1 1 d . . . . .
H6 H 0.681984 0.767473 0.374807 0.052 Uiso 1 1 calc R . . . .
C7 C 0.5536(4) 0.69936(18) 0.43297(16) 0.0486(9) Uani 1 1 d . . . . .
H7 H 0.580995 0.717438 0.478305 0.058 Uiso 1 1 calc R . . . .
C15 C 0.7289(3) 0.80383(17) 0.15250(16) 0.0436(8) Uani 1 1 d . . . . .
C9 C 0.3286(3) 0.55744(17) 0.21501(17) 0.0450(8) Uani 1 1 d . . . . .
H9 H 0.288928 0.533606 0.255302 0.054 Uiso 1 1 calc R . . . .
C17 C 0.8180(3) 0.83657(17) 0.27216(17) 0.0450(8) Uani 1 1 d . . . . .
H17 H 0.820816 0.828884 0.322060 0.054 Uiso 1 1 calc R . . . .
C2 C 0.4525(3) 0.64270(17) 0.42758(16) 0.0437(8) Uani 1 1 d . . . . .
C12 C 0.4455(4) 0.62602(18) 0.09379(17) 0.0507(9) Uani 1 1 d . . . . .
H12 H 0.484952 0.648916 0.052944 0.061 Uiso 1 1 calc R . . . .
C11 C 0.3495(4) 0.56818(19) 0.08581(18) 0.0576(10) Uani 1 1 d . . . . .
H11 H 0.324051 0.551575 0.039668 0.069 Uiso 1 1 calc R . . . .
C10 C 0.2899(4) 0.53424(18) 0.14667(18) 0.0532(9) Uani 1 1 d . . . . .
H10 H 0.223241 0.495439 0.141122 0.064 Uiso 1 1 calc R . . . .
C18 C 0.9015(4) 0.89122(18) 0.2392(2) 0.0550(9) Uani 1 1 d . . . . .
H18 H 0.961851 0.920781 0.267864 0.066 Uiso 1 1 calc R . . . .
C20 C 0.8130(4) 0.8599(2) 0.1205(2) 0.0630(10) Uani 1 1 d . . . . .
H20 H 0.811498 0.867672 0.070622 0.076 Uiso 1 1 calc R . . . .
C1 C 0.3839(5) 0.6128(2) 0.49441(19) 0.0649(11) Uani 1 1 d . . . . .
C19 C 0.8983(4) 0.9035(2) 0.1652(2) 0.0665(11) Uani 1 1 d . . . . .
H19 H 0.954481 0.941736 0.145272 0.080 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 C1 1.301(4) . ?
F3 C1 1.308(4) . ?
N1 C16 1.406(3) . ?
N1 C14 1.396(3) . ?
N1 C5 1.411(3) . ?
F2 C1 1.309(4) . ?
N2 C14 1.306(4) . ?
N2 C15 1.376(4) . ?
C16 C15 1.393(4) . ?
C16 C17 1.388(4) . ?
C14 C13 1.435(4) . ?
C8 C13 1.401(4) . ?
C8 C4 1.462(4) . ?
C8 C9 1.405(4) . ?
C5 C4 1.407(4) . ?
C5 C6 1.392(4) . ?
C13 C12 1.396(4) . ?
C4 C3 1.391(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.380(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(4) . ?
C7 H7 0.9300 . ?
C7 C2 1.376(4) . ?
C15 C20 1.394(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(4) . ?
C2 C1 1.484(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.365(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.387(5) . ?
C10 H10 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.382(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.378(5) . ?
C19 H19 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
C16 N1 C5 132.4(2) . . ?
C14 N1 C16 105.5(2) . . ?
C14 N1 C5 121.7(2) . . ?
C14 N2 C15 104.8(2) . . ?
C15 C16 N1 104.4(2) . . ?
C17 C16 N1 134.3(3) . . ?
C17 C16 C15 121.3(3) . . ?
N1 C14 C13 120.0(2) . . ?
N2 C14 N1 113.3(3) . . ?
N2 C14 C13 126.7(3) . . ?
C13 C8 C4 119.1(3) . . ?
C13 C8 C9 117.7(3) . . ?
C9 C8 C4 123.2(3) . . ?
C4 C5 N1 118.6(2) . . ?
C6 C5 N1 120.8(3) . . ?
C6 C5 C4 120.5(3) . . ?
C8 C13 C14 119.6(2) . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 C8 120.5(3) . . ?
C5 C4 C8 120.6(2) . . ?
C3 C4 C8 122.2(3) . . ?
C3 C4 C5 117.2(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.1 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C2 119.8(3) . . ?
C2 C7 H7 120.1 . . ?
N2 C15 C16 111.9(2) . . ?
N2 C15 C20 127.5(3) . . ?
C16 C15 C20 120.6(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C16 C17 H17 121.5 . . ?
C18 C17 C16 117.0(3) . . ?
C18 C17 H17 121.5 . . ?
C3 C2 C1 120.4(3) . . ?
C7 C2 C3 120.1(3) . . ?
C7 C2 C1 119.5(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C17 C18 H18 118.9 . . ?
C17 C18 C19 122.2(3) . . ?
C19 C18 H18 118.9 . . ?
C15 C20 H20 121.0 . . ?
C19 C20 C15 117.9(3) . . ?
C19 C20 H20 121.0 . . ?
F1 C1 F3 105.5(4) . . ?
F1 C1 F2 106.3(3) . . ?
F1 C1 C2 113.8(3) . . ?
F3 C1 F2 103.6(3) . . ?
F3 C1 C2 113.0(3) . . ?
F2 C1 C2 113.8(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?

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
N1 C16 C15 N2 -1.3(3) . . . . ?
N1 C16 C15 C20 179.1(3) . . . . ?
N1 C16 C17 C18 179.5(3) . . . . ?
N1 C14 C13 C8 4.9(4) . . . . ?
N1 C14 C13 C12 -175.2(3) . . . . ?
N1 C5 C4 C8 1.3(4) . . . . ?
N1 C5 C4 C3 -178.1(2) . . . . ?
N1 C5 C6 C7 178.2(3) . . . . ?
N2 C14 C13 C8 -175.3(3) . . . . ?
N2 C14 C13 C12 4.6(5) . . . . ?
N2 C15 C20 C19 -178.3(3) . . . . ?
C16 N1 C14 N2 -1.2(3) . . . . ?
C16 N1 C14 C13 178.6(2) . . . . ?
C16 N1 C5 C4 176.5(3) . . . . ?
C16 N1 C5 C6 -1.6(4) . . . . ?
C16 C15 C20 C19 1.2(5) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C14 N1 C16 C15 1.4(3) . . . . ?
C14 N1 C16 C17 -176.5(3) . . . . ?
C14 N1 C5 C4 3.8(4) . . . . ?
C14 N1 C5 C6 -174.3(3) . . . . ?
C14 N2 C15 C16 0.6(4) . . . . ?
C14 N2 C15 C20 -179.9(3) . . . . ?
C14 C13 C12 C11 -179.2(3) . . . . ?
C8 C13 C12 C11 0.7(5) . . . . ?
C8 C4 C3 C2 -179.6(3) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C5 N1 C16 C15 -172.2(3) . . . . ?
C5 N1 C16 C17 9.9(5) . . . . ?
C5 N1 C14 N2 173.2(2) . . . . ?
C5 N1 C14 C13 -7.0(4) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C5 C6 C7 C2 -0.2(5) . . . . ?
C13 C8 C4 C5 -3.2(4) . . . . ?
C13 C8 C4 C3 176.2(3) . . . . ?
C13 C8 C9 C10 0.0(4) . . . . ?
C13 C12 C11 C10 0.3(5) . . . . ?
C4 C8 C13 C14 0.0(4) . . . . ?
C4 C8 C13 C12 -179.9(3) . . . . ?
C4 C8 C9 C10 179.0(3) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C4 C3 C2 C7 0.2(5) . . . . ?
C4 C3 C2 C1 177.9(3) . . . . ?
C3 C2 C1 F1 2.1(5) . . . . ?
C3 C2 C1 F3 -118.2(4) . . . . ?
C3 C2 C1 F2 124.0(4) . . . . ?
C6 C5 C4 C8 179.4(3) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
C6 C7 C2 C3 0.0(5) . . . . ?
C6 C7 C2 C1 -177.8(3) . . . . ?
C7 C2 C1 F1 179.8(4) . . . . ?
C7 C2 C1 F3 59.5(5) . . . . ?
C7 C2 C1 F2 -58.3(5) . . . . ?
C15 N2 C14 N1 0.4(3) . . . . ?
C15 N2 C14 C13 -179.4(3) . . . . ?
C15 C16 C17 C18 1.8(4) . . . . ?
C15 C20 C19 C18 0.8(6) . . . . ?
C9 C8 C13 C14 179.1(3) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
C9 C8 C4 C5 177.8(3) . . . . ?
C9 C8 C4 C3 -2.8(4) . . . . ?
C17 C16 C15 N2 177.0(3) . . . . ?
C17 C16 C15 C20 -2.6(5) . . . . ?
C17 C18 C19 C20 -1.5(6) . . . . ?
C12 C11 C10 C9 -1.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
