# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mo_20210311LJM923_0m
_audit_block_doi                 10.5517/ccdc.csd.cc27lj9p
_database_code_depnum_ccdc_archive 'CCDC 2073382'
loop_
_audit_author_name
_audit_author_address
'Jeray Liu'
;fudan university
China
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 F3 N O'
_chemical_formula_weight         301.26

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                   7.2327(11)
_cell_length_b                   7.6558(11)
_cell_length_c                   13.5621(18)
_cell_angle_alpha                100.334(4)
_cell_angle_beta                 95.405(4)
_cell_angle_gamma                109.676(4)
_cell_volume                     685.89(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1485
_cell_measurement_theta_min      2.9000
_cell_measurement_theta_max      20.0922

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18581
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_av_R_equivalents  0.2218
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_full        25.022
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2418
_reflns_number_gt                1047
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0790P)²] 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         2418
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1908
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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 0.2157(7) 0.4390(5) 0.0177(2) 0.1737(17) Uani 1 1 d . . . . .
F2 F 0.0575(6) 0.2046(6) 0.0739(2) 0.1751(17) Uani 1 1 d . . . . .
F3 F 0.3207(7) 0.2150(6) 0.0199(2) 0.1812(19) Uani 1 1 d . . . . .
O1 O 0.1286(4) 0.7919(4) 0.6075(2) 0.1010(10) Uani 1 1 d . . . . .
N1 N 0.3730(4) 0.7468(4) 0.5218(2) 0.0669(9) Uani 1 1 d . . . . .
C1 C 0.2403(11) 0.3198(9) 0.0734(4) 0.1201(19) Uani 1 1 d . . . . .
C2 C 0.3531(8) 0.4215(6) 0.1767(3) 0.0884(13) Uani 1 1 d . . . . .
C3 C 0.2574(6) 0.4729(6) 0.2524(3) 0.0805(12) Uani 1 1 d . . . . .
H8 H 0.119606 0.436810 0.239202 0.097 Uiso 1 1 calc R U . . .
C4 C 0.3586(6) 0.5770(5) 0.3484(3) 0.0689(10) Uani 1 1 d . . . . .
C5 C 0.2450(5) 0.6307(5) 0.4279(3) 0.0768(11) Uani 1 1 d . . . . .
H7 H 0.168019 0.699826 0.402036 0.092 Uiso 1 1 calc R U . . .
H6 H 0.152448 0.515752 0.441370 0.092 Uiso 1 1 calc R U . . .
C6 C 0.3048(6) 0.8185(5) 0.6044(3) 0.0751(11) Uani 1 1 d . . . . .
C7 C 0.4817(6) 0.9245(5) 0.6824(3) 0.0713(10) Uani 1 1 d . . . . .
C8 C 0.4967(7) 1.0227(6) 0.7803(3) 0.0915(13) Uani 1 1 d . . . . .
H5 H 0.384313 1.028979 0.806565 0.110 Uiso 1 1 calc R U . . .
C9 C 0.6834(8) 1.1110(7) 0.8378(3) 0.1004(15) Uani 1 1 d . . . . .
H1 H 0.698100 1.179904 0.903726 0.121 Uiso 1 1 calc R U . . .
C10 C 0.5567(8) 0.4716(6) 0.1951(3) 0.0945(14) Uani 1 1 d . . . . .
H2 H 0.623075 0.436155 0.144177 0.113 Uiso 1 1 calc R U . . .
C11 C 0.6611(6) 0.5752(6) 0.2901(3) 0.0828(12) Uani 1 1 d . . . . .
H10 H 0.798631 0.608634 0.302532 0.099 Uiso 1 1 calc R U . . .
C12 C 0.5661(5) 0.6307(5) 0.3673(2) 0.0647(10) Uani 1 1 d . . . . .
C13 C 0.6752(5) 0.7434(5) 0.4668(3) 0.0640(10) Uani 1 1 d . . . . .
H9 H 0.812848 0.778129 0.480144 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5812(5) 0.7975(5) 0.5390(3) 0.0612(9) Uani 1 1 d . . . . .
C15 C 0.6469(5) 0.9108(5) 0.6429(3) 0.0652(10) Uani 1 1 d . . . . .
C16 C 0.8487(7) 1.0992(6) 0.7993(3) 0.0969(14) Uani 1 1 d . . . . .
H4 H 0.973257 1.159775 0.840022 0.116 Uiso 1 1 calc R U . . .
C17 C 0.8346(6) 0.9991(5) 0.7011(3) 0.0785(12) Uani 1 1 d . . . . .
H3 H 0.947196 0.991605 0.675490 0.094 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 C1 1.329(6) . ?
F2 C1 1.321(7) . ?
F3 C1 1.301(7) . ?
O1 C6 1.227(4) . ?
N1 C6 1.365(5) . ?
N1 C14 1.407(4) . ?
N1 C5 1.445(5) . ?
C1 C2 1.483(6) . ?
C2 C3 1.364(6) . ?
C2 C10 1.376(6) . ?
C3 C4 1.386(5) . ?
C3 H8 0.9300 . ?
C4 C12 1.401(5) . ?
C4 C5 1.497(5) . ?
C5 H7 0.9700 . ?
C5 H6 0.9700 . ?
C6 C7 1.467(5) . ?
C7 C8 1.379(5) . ?
C7 C15 1.382(5) . ?
C8 C9 1.373(6) . ?
C8 H5 0.9300 . ?
C9 C16 1.372(6) . ?
C9 H1 0.9300 . ?
C10 C11 1.380(5) . ?
C10 H2 0.9300 . ?
C11 C12 1.387(5) . ?
C11 H10 0.9300 . ?
C12 C13 1.453(5) . ?
C13 C14 1.327(4) . ?
C13 H9 0.9300 . ?
C14 C15 1.457(5) . ?
C15 C17 1.383(5) . ?
C16 C17 1.388(5) . ?
C16 H4 0.9300 . ?
C17 H3 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
C6 N1 C14 112.4(3) . . ?
C6 N1 C5 123.6(3) . . ?
C14 N1 C5 123.9(3) . . ?
F3 C1 F2 105.4(5) . . ?
F3 C1 F1 105.9(5) . . ?
F2 C1 F1 104.4(5) . . ?
F3 C1 C2 115.0(5) . . ?
F2 C1 C2 113.2(5) . . ?
F1 C1 C2 112.0(4) . . ?
C3 C2 C10 119.8(4) . . ?
C3 C2 C1 120.4(5) . . ?
C10 C2 C1 119.8(5) . . ?
C2 C3 C4 122.2(4) . . ?
C2 C3 H8 118.9 . . ?
C4 C3 H8 118.9 . . ?
C3 C4 C12 118.4(3) . . ?
C3 C4 C5 119.6(3) . . ?
C12 C4 C5 122.0(3) . . ?
N1 C5 C4 112.7(3) . . ?
N1 C5 H7 109.0 . . ?
C4 C5 H7 109.0 . . ?
N1 C5 H6 109.0 . . ?
C4 C5 H6 109.0 . . ?
H7 C5 H6 107.8 . . ?
O1 C6 N1 124.1(4) . . ?
O1 C6 C7 130.2(4) . . ?
N1 C6 C7 105.8(3) . . ?
C8 C7 C15 121.8(4) . . ?
C8 C7 C6 129.8(4) . . ?
C15 C7 C6 108.4(3) . . ?
C9 C8 C7 117.7(4) . . ?
C9 C8 H5 121.1 . . ?
C7 C8 H5 121.1 . . ?
C16 C9 C8 121.0(4) . . ?
C16 C9 H1 119.5 . . ?
C8 C9 H1 119.5 . . ?
C2 C10 C11 119.2(4) . . ?
C2 C10 H2 120.4 . . ?
C11 C10 H2 120.4 . . ?
C10 C11 C12 121.7(4) . . ?
C10 C11 H10 119.2 . . ?
C12 C11 H10 119.2 . . ?
C11 C12 C4 118.8(3) . . ?
C11 C12 C13 122.1(3) . . ?
C4 C12 C13 119.1(3) . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H9 119.5 . . ?
C12 C13 H9 119.5 . . ?
C13 C14 N1 121.2(3) . . ?
C13 C14 C15 133.8(3) . . ?
N1 C14 C15 105.1(3) . . ?
C7 C15 C17 120.3(3) . . ?
C7 C15 C14 108.4(3) . . ?
C17 C15 C14 131.3(4) . . ?
C9 C16 C17 121.7(4) . . ?
C9 C16 H4 119.2 . . ?
C17 C16 H4 119.2 . . ?
C15 C17 C16 117.5(4) . . ?
C15 C17 H3 121.2 . . ?
C16 C17 H3 121.2 . . ?

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
F3 C1 C2 C3 -154.5(5) . . . . ?
F2 C1 C2 C3 -33.2(7) . . . . ?
F1 C1 C2 C3 84.5(7) . . . . ?
F3 C1 C2 C10 28.4(8) . . . . ?
F2 C1 C2 C10 149.6(5) . . . . ?
F1 C1 C2 C10 -92.7(7) . . . . ?
C10 C2 C3 C4 0.7(6) . . . . ?
C1 C2 C3 C4 -176.4(4) . . . . ?
C2 C3 C4 C12 0.1(6) . . . . ?
C2 C3 C4 C5 179.4(4) . . . . ?
C6 N1 C5 C4 177.9(3) . . . . ?
C14 N1 C5 C4 -2.7(5) . . . . ?
C3 C4 C5 N1 -177.1(3) . . . . ?
C12 C4 C5 N1 2.1(5) . . . . ?
C14 N1 C6 O1 -179.5(4) . . . . ?
C5 N1 C6 O1 0.0(6) . . . . ?
C14 N1 C6 C7 -0.1(4) . . . . ?
C5 N1 C6 C7 179.4(3) . . . . ?
O1 C6 C7 C8 0.1(7) . . . . ?
N1 C6 C7 C8 -179.2(4) . . . . ?
O1 C6 C7 C15 179.1(4) . . . . ?
N1 C6 C7 C15 -0.2(4) . . . . ?
C15 C7 C8 C9 1.3(6) . . . . ?
C6 C7 C8 C9 -179.8(4) . . . . ?
C7 C8 C9 C16 -1.0(7) . . . . ?
C3 C2 C10 C11 -0.6(7) . . . . ?
C1 C2 C10 C11 176.5(4) . . . . ?
C2 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 C4 1.1(6) . . . . ?
C10 C11 C12 C13 -178.6(4) . . . . ?
C3 C4 C12 C11 -1.0(5) . . . . ?
C5 C4 C12 C11 179.8(4) . . . . ?
C3 C4 C12 C13 178.7(3) . . . . ?
C5 C4 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C14 178.8(4) . . . . ?
C4 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 N1 0.4(5) . . . . ?
C12 C13 C14 C15 -178.7(4) . . . . ?
C6 N1 C14 C13 -179.0(3) . . . . ?
C5 N1 C14 C13 1.5(5) . . . . ?
C6 N1 C14 C15 0.4(4) . . . . ?
C5 N1 C14 C15 -179.1(3) . . . . ?
C8 C7 C15 C17 -1.0(6) . . . . ?
C6 C7 C15 C17 179.9(4) . . . . ?
C8 C7 C15 C14 179.5(4) . . . . ?
C6 C7 C15 C14 0.4(4) . . . . ?
C13 C14 C15 C7 178.7(4) . . . . ?
N1 C14 C15 C7 -0.5(4) . . . . ?
C13 C14 C15 C17 -0.7(7) . . . . ?
N1 C14 C15 C17 -179.9(4) . . . . ?
C8 C9 C16 C17 0.4(7) . . . . ?
C7 C15 C17 C16 0.3(6) . . . . ?
C14 C15 C17 C16 179.7(4) . . . . ?
C9 C16 C17 C15 0.0(7) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.036

