# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2260760'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;
_audit_creation_date             2022-10-14
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2022,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C24 H15 F2 N O'
_chemical_formula_moiety         'C24 H15 F2 N O'
_chemical_formula_weight         371.37
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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                   8.7520(7)
_cell_length_b                   9.0608(6)
_cell_length_c                   11.3766(9)
_cell_angle_alpha                88.991(3)
_cell_angle_beta                 76.810(3)
_cell_angle_gamma                82.972(3)
_cell_volume                     871.72(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    6713
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.19
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0727 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.9449.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.982
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            19045
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         28.446
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4364
_reflns_number_gt                3360
_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       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_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)+(0.0409P)²+0.3483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 1.35476(11) 0.00721(11) 0.21490(8) 0.0349(2) Uani 1 1 d . . . . .
F2 F 0.45710(11) 0.81393(10) 0.98807(8) 0.0327(2) Uani 1 1 d . . . . .
O1 O 0.18341(12) 0.40016(12) 0.59490(10) 0.0276(2) Uani 1 1 d . . . . .
N1 N 0.62928(14) 0.14081(13) 0.45733(11) 0.0217(3) Uani 1 1 d . . . . .
C1 C 1.20672(18) 0.05733(17) 0.27922(13) 0.0251(3) Uani 1 1 d . . . . .
C2 C 1.18318(18) 0.19264(17) 0.33780(13) 0.0247(3) Uani 1 1 d . . . . .
H2 H 1.267787 0.250639 0.332779 0.030 Uiso 1 1 calc R U . . .
C3 C 1.03232(17) 0.24209(16) 0.40449(13) 0.0234(3) Uani 1 1 d . . . . .
H3 H 1.013271 0.335422 0.445292 0.028 Uiso 1 1 calc R U . . .
C4 C 0.90840(17) 0.15636(15) 0.41227(12) 0.0200(3) Uani 1 1 d . . . . .
C5 C 0.93808(18) 0.02129(16) 0.34896(13) 0.0241(3) Uani 1 1 d . . . . .
H5 H 0.854138 -0.037033 0.352143 0.029 Uiso 1 1 calc R U . . .
C6 C 1.08752(19) -0.02904(16) 0.28174(13) 0.0264(3) Uani 1 1 d . . . . .
H6 H 1.107160 -0.120746 0.238534 0.032 Uiso 1 1 calc R U . . .
C7 C 0.74688(16) 0.20602(15) 0.48499(12) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.71779(17) 0.31456(15) 0.57556(12) 0.0199(3) Uani 1 1 d . . . . .
H8 H 0.803829 0.355775 0.594938 0.024 Uiso 1 1 calc R U . . .
C9 C 0.56401(17) 0.36297(15) 0.63776(12) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.44159(16) 0.29954(15) 0.60468(12) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.48201(17) 0.18899(16) 0.51558(13) 0.0222(3) Uani 1 1 d . . . . .
H11 H 0.398541 0.144829 0.494893 0.027 Uiso 1 1 calc R U . . .
C12 C 0.53443(16) 0.48178(15) 0.73146(12) 0.0193(3) Uani 1 1 d . . . . .
C13 C 0.62999(17) 0.48058(16) 0.81468(13) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.713009 0.401804 0.812139 0.026 Uiso 1 1 calc R U . . .
C14 C 0.60547(18) 0.59258(16) 0.90088(13) 0.0245(3) Uani 1 1 d . . . . .
H14 H 0.670303 0.591315 0.957528 0.029 Uiso 1 1 calc R U . . .
C15 C 0.48465(17) 0.70569(16) 0.90218(13) 0.0239(3) Uani 1 1 d . . . . .
C16 C 0.38952(17) 0.71308(16) 0.82097(13) 0.0237(3) Uani 1 1 d . . . . .
H16 H 0.308834 0.793912 0.822891 0.028 Uiso 1 1 calc R U . . .
C17 C 0.41425(17) 0.59955(15) 0.73612(13) 0.0221(3) Uani 1 1 d . . . . .
H17 H 0.348300 0.601912 0.680189 0.027 Uiso 1 1 calc R U . . .
C18 C 0.26821(17) 0.34077(15) 0.65815(13) 0.0210(3) Uani 1 1 d . . . . .
C19 C 0.20031(16) 0.29871(15) 0.78492(13) 0.0208(3) Uani 1 1 d . . . . .
C20 C 0.05062(17) 0.36688(16) 0.84276(14) 0.0257(3) Uani 1 1 d . . . . .
H20 H -0.002315 0.443785 0.803635 0.031 Uiso 1 1 calc R U . . .
C21 C -0.02042(18) 0.32226(18) 0.95707(14) 0.0296(3) Uani 1 1 d . . . . .
H21 H -0.121524 0.369514 0.996851 0.035 Uiso 1 1 calc R U . . .
C22 C 0.05597(18) 0.20841(18) 1.01374(14) 0.0288(3) Uani 1 1 d . . . . .
H22 H 0.006050 0.176658 1.091543 0.035 Uiso 1 1 calc R U . . .
C23 C 0.20490(18) 0.14101(17) 0.95701(14) 0.0274(3) Uani 1 1 d . . . . .
H23 H 0.257023 0.063552 0.996161 0.033 Uiso 1 1 calc R U . . .
C24 C 0.27786(17) 0.18664(16) 0.84307(13) 0.0237(3) Uani 1 1 d . . . . .
H24 H 0.380560 0.141518 0.804768 0.028 Uiso 1 1 calc R U . . .


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 1.3622(16) . ?
F2 C15 1.3576(16) . ?
O1 C18 1.2209(17) . ?
N1 C7 1.3456(18) . ?
N1 C11 1.3318(19) . ?
C1 C2 1.376(2) . ?
C1 C6 1.374(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C5 1.397(2) . ?
C4 C7 1.4863(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3958(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.3916(19) . ?
C9 C10 1.4008(19) . ?
C9 C12 1.4861(19) . ?
C10 C11 1.393(2) . ?
C10 C18 1.503(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(2) . ?
C12 C17 1.396(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(2) . ?
C15 C16 1.374(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.491(2) . ?
C19 C20 1.398(2) . ?
C19 C24 1.394(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(2) . ?
C24 H24 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
C11 N1 C7 117.44(12) . . ?
F1 C1 C2 118.52(14) . . ?
F1 C1 C6 118.43(13) . . ?
C6 C1 C2 123.04(14) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.17(14) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.82(13) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.63(13) . . ?
C3 C4 C7 121.63(12) . . ?
C5 C4 C7 119.74(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.17(14) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.12(13) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
N1 C7 C4 115.80(12) . . ?
N1 C7 C8 121.76(13) . . ?
C8 C7 C4 122.44(13) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.65(13) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 117.28(13) . . ?
C8 C9 C12 120.07(12) . . ?
C10 C9 C12 122.61(13) . . ?
C9 C10 C18 125.17(13) . . ?
C11 C10 C9 118.09(13) . . ?
C11 C10 C18 116.75(12) . . ?
N1 C11 C10 124.69(13) . . ?
N1 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
C13 C12 C9 120.57(13) . . ?
C17 C12 C9 120.95(13) . . ?
C17 C12 C13 118.45(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.03(13) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.24(14) . . ?
C15 C14 H14 120.9 . . ?
F2 C15 C14 118.73(13) . . ?
F2 C15 C16 118.43(13) . . ?
C16 C15 C14 122.83(13) . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.30(13) . . ?
C17 C16 H16 120.9 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.12(14) . . ?
C16 C17 H17 119.4 . . ?
O1 C18 C10 119.46(13) . . ?
O1 C18 C19 120.89(13) . . ?
C19 C18 C10 119.50(12) . . ?
C20 C19 C18 118.65(13) . . ?
C24 C19 C18 121.42(13) . . ?
C24 C19 C20 119.78(13) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.95(14) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.08(14) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.18(14) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.06(14) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 120.0 . . ?
C23 C24 C19 119.93(14) . . ?
C23 C24 H24 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -179.18(12) . . . . ?
F1 C1 C6 C5 178.88(13) . . . . ?
F2 C15 C16 C17 -177.70(13) . . . . ?
O1 C18 C19 C20 -19.6(2) . . . . ?
O1 C18 C19 C24 156.01(14) . . . . ?
N1 C7 C8 C9 -2.3(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C2 C3 C4 C7 178.85(13) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C3 C4 C7 N1 160.33(13) . . . . ?
C3 C4 C7 C8 -19.0(2) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C4 C7 C8 C9 176.96(12) . . . . ?
C5 C4 C7 N1 -19.15(19) . . . . ?
C5 C4 C7 C8 161.51(13) . . . . ?
C6 C1 C2 C3 1.4(2) . . . . ?
C7 N1 C11 C10 -1.5(2) . . . . ?
C7 C4 C5 C6 -179.15(13) . . . . ?
C7 C8 C9 C10 -0.63(19) . . . . ?
C7 C8 C9 C12 -178.19(12) . . . . ?
C8 C9 C10 C11 2.38(19) . . . . ?
C8 C9 C10 C18 -177.86(12) . . . . ?
C8 C9 C12 C13 -43.12(19) . . . . ?
C8 C9 C12 C17 134.79(14) . . . . ?
C9 C10 C11 N1 -1.4(2) . . . . ?
C9 C10 C18 O1 114.11(16) . . . . ?
C9 C10 C18 C19 -70.29(18) . . . . ?
C9 C12 C13 C14 178.64(13) . . . . ?
C9 C12 C17 C16 -177.93(13) . . . . ?
C10 C9 C12 C13 139.46(14) . . . . ?
C10 C9 C12 C17 -42.63(19) . . . . ?
C10 C18 C19 C20 164.89(13) . . . . ?
C10 C18 C19 C24 -19.5(2) . . . . ?
C11 N1 C7 C4 -176.01(12) . . . . ?
C11 N1 C7 C8 3.33(19) . . . . ?
C11 C10 C18 O1 -66.12(18) . . . . ?
C11 C10 C18 C19 109.48(15) . . . . ?
C12 C9 C10 C11 179.87(13) . . . . ?
C12 C9 C10 C18 -0.4(2) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C12 C17 C16 0.0(2) . . . . ?
C13 C14 C15 F2 178.38(13) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C14 C15 C16 C17 1.6(2) . . . . ?
C15 C16 C17 C12 -1.1(2) . . . . ?
C17 C12 C13 C14 0.7(2) . . . . ?
C18 C10 C11 N1 178.79(13) . . . . ?
C18 C19 C20 C21 175.23(13) . . . . ?
C18 C19 C24 C23 -174.18(13) . . . . ?
C19 C20 C21 C22 -0.9(2) . . . . ?
C20 C19 C24 C23 1.4(2) . . . . ?
C20 C21 C22 C23 1.2(2) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C19 -1.0(2) . . . . ?
C24 C19 C20 C21 -0.4(2) . . . . ?

