# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_cxy1565_0m
_database_code_depnum_ccdc_archive 'CCDC 2079260'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern Univeristy of Science and Technology
China
;
_audit_update_record             
;
2021-04-21 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_audit_creation_date             2020-12-29
_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 H13 Cl F3 N O'
_chemical_formula_sum            'C20 H13 Cl F3 N O'
_chemical_formula_weight         375.76
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   8.7814(3)
_cell_length_b                   9.6508(4)
_cell_length_c                   11.1942(4)
_cell_angle_alpha                102.0660(10)
_cell_angle_beta                 98.1170(10)
_cell_angle_gamma                113.2940(10)
_cell_volume                     825.21(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1107 before and 0.0523 after correction. The Ratio of minimum to maximum transmission is 0.9475. 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    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25592
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.577
_diffrn_reflns_theta_min         2.402
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4176
_reflns_number_total             5056
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0081(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         5056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.025
_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+0.3946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0963
_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:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C19(H19),
 C20(H20)
;
_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
Cl1 Cl 0.77377(4) 0.95563(4) -0.05686(3) 0.02193(9) Uani 1 1 d . . . . .
F1 F 0.60546(11) 0.83971(11) 0.59021(8) 0.0325(2) Uani 1 1 d . . . . .
F2 F 0.38242(11) 0.80061(9) 0.66270(7) 0.02237(17) Uani 1 1 d . . . . .
F3 F 0.51477(10) 0.65718(10) 0.68114(7) 0.02156(17) Uani 1 1 d . . . . .
O1 O 0.10118(11) 0.40903(11) 0.05336(8) 0.01831(19) Uani 1 1 d . . . . .
N1 N 0.16261(12) 0.41188(11) 0.31799(9) 0.01252(19) Uani 1 1 d . . . . .
C1 C 0.61933(15) 0.82544(14) -0.00062(11) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.44955(16) 0.79666(14) -0.03986(11) 0.0162(2) Uani 1 1 d . . . . .
H2 H 0.418057 0.847613 -0.096102 0.019 Uiso 1 1 calc R . . . .
C3 C 0.32666(15) 0.69218(14) 0.00448(11) 0.0150(2) Uani 1 1 d . . . . .
H3 H 0.209656 0.669425 -0.022994 0.018 Uiso 1 1 calc R . . . .
C4 C 0.37448(15) 0.62044(14) 0.08935(11) 0.0137(2) Uani 1 1 d . . . . .
C5 C 0.23560(15) 0.50511(14) 0.13086(11) 0.0138(2) Uani 1 1 d . . . . .
C6 C 0.26643(15) 0.51930(13) 0.26507(11) 0.0132(2) Uani 1 1 d . . . . .
C7 C 0.21465(14) 0.46754(13) 0.44665(11) 0.0123(2) Uani 1 1 d . . . . .
C8 C 0.11875(15) 0.37489(13) 0.52227(11) 0.0130(2) Uani 1 1 d . . . . .
C9 C 0.00196(16) 0.21663(14) 0.46145(12) 0.0165(2) Uani 1 1 d . . . . .
C10 C -0.09672(17) 0.12778(15) 0.52963(13) 0.0211(3) Uani 1 1 d . . . . .
H10 H -0.176658 0.021163 0.488633 0.025 Uiso 1 1 calc R . . . .
C11 C -0.08007(17) 0.19268(15) 0.65674(13) 0.0198(2) Uani 1 1 d . . . . .
H11 H -0.149164 0.131013 0.701769 0.024 Uiso 1 1 calc R . . . .
C12 C 0.54612(16) 0.65207(15) 0.12821(11) 0.0162(2) Uani 1 1 d . . . . .
H12 H 0.578725 0.603726 0.186306 0.019 Uiso 1 1 calc R . . . .
C13 C 0.66950(15) 0.75404(15) 0.08224(12) 0.0169(2) Uani 1 1 d . . . . .
H13 H 0.786125 0.774419 0.107179 0.020 Uiso 1 1 calc R . . . .
C14 C 0.35762(15) 0.61465(14) 0.47630(11) 0.0137(2) Uani 1 1 d . . . . .
C15 C 0.46309(16) 0.72535(14) 0.60123(12) 0.0168(2) Uani 1 1 d . . . . .
C16 C 0.38846(15) 0.64539(14) 0.36329(11) 0.0144(2) Uani 1 1 d . . . . .
H16 H 0.477412 0.736653 0.355302 0.017 Uiso 1 1 calc R . . . .
C17 C -0.00916(18) 0.14599(15) 0.32550(12) 0.0213(3) Uani 1 1 d . . . . .
H17A H -0.121795 0.053519 0.287439 0.026 Uiso 1 1 calc R . . . .
H17B H 0.080601 0.108787 0.321072 0.026 Uiso 1 1 calc R . . . .
C18 C 0.01271(16) 0.26246(14) 0.25068(12) 0.0165(2) Uani 1 1 d . . . . .
H18A H 0.027229 0.219139 0.167024 0.020 Uiso 1 1 calc R . . . .
H18B H -0.090881 0.280698 0.237354 0.020 Uiso 1 1 calc R . . . .
C19 C 0.03802(16) 0.34807(15) 0.71767(12) 0.0175(2) Uani 1 1 d . . . . .
H19 H 0.051775 0.392385 0.804908 0.021 Uiso 1 1 calc R . . . .
C20 C 0.13589(16) 0.43827(14) 0.65023(11) 0.0160(2) Uani 1 1 d . . . . .
H20 H 0.215718 0.544749 0.691894 0.019 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
Cl1 C1 1.7431(12) . ?
F1 C15 1.3436(14) . ?
F2 C15 1.3559(15) . ?
F3 C15 1.3441(15) . ?
O1 C5 1.2307(15) . ?
N1 C6 1.3852(14) . ?
N1 C7 1.3668(14) . ?
N1 C18 1.4643(15) . ?
C1 C2 1.3890(17) . ?
C1 C13 1.3860(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3884(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3967(17) . ?
C4 C5 1.4982(16) . ?
C4 C12 1.3962(16) . ?
C5 C6 1.4556(16) . ?
C6 C16 1.3837(16) . ?
C7 C8 1.4654(15) . ?
C7 C14 1.4063(15) . ?
C8 C9 1.4062(16) . ?
C8 C20 1.3959(16) . ?
C9 C10 1.3933(17) . ?
C9 C17 1.5039(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3909(18) . ?
C11 H11 0.9500 . ?
C11 C19 1.3900(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3904(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.4771(17) . ?
C14 C16 1.3971(16) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5068(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19 0.9500 . ?
C19 C20 1.3902(17) . ?
C20 H20 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 C18 126.88(10) . . ?
C7 N1 C6 110.19(9) . . ?
C7 N1 C18 122.87(10) . . ?
C2 C1 Cl1 119.01(10) . . ?
C13 C1 Cl1 119.08(9) . . ?
C13 C1 C2 121.91(11) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.89(11) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.21(11) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 117.78(10) . . ?
C12 C4 C3 119.87(11) . . ?
C12 C4 C5 122.29(11) . . ?
O1 C5 C4 119.86(10) . . ?
O1 C5 C6 123.44(11) . . ?
C6 C5 C4 116.64(10) . . ?
N1 C6 C5 124.46(10) . . ?
C16 C6 N1 107.28(10) . . ?
C16 C6 C5 127.90(11) . . ?
N1 C7 C8 119.47(10) . . ?
N1 C7 C14 106.62(10) . . ?
C14 C7 C8 133.89(10) . . ?
C9 C8 C7 117.96(10) . . ?
C20 C8 C7 122.79(10) . . ?
C20 C8 C9 119.23(11) . . ?
C8 C9 C17 119.13(11) . . ?
C10 C9 C8 119.22(11) . . ?
C10 C9 C17 121.62(11) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.06(12) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C19 C11 C10 119.77(11) . . ?
C19 C11 H11 120.1 . . ?
C4 C12 H12 119.9 . . ?
C13 C12 C4 120.27(11) . . ?
C13 C12 H12 119.9 . . ?
C1 C13 C12 118.83(11) . . ?
C1 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C7 C14 C15 129.20(10) . . ?
C16 C14 C7 108.04(10) . . ?
C16 C14 C15 122.76(10) . . ?
F1 C15 F2 105.69(10) . . ?
F1 C15 F3 106.57(10) . . ?
F1 C15 C14 110.85(10) . . ?
F2 C15 C14 113.52(11) . . ?
F3 C15 F2 105.73(10) . . ?
F3 C15 C14 113.88(10) . . ?
C6 C16 C14 107.86(10) . . ?
C6 C16 H16 126.1 . . ?
C14 C16 H16 126.1 . . ?
C9 C17 H17A 109.2 . . ?
C9 C17 H17B 109.2 . . ?
C9 C17 C18 112.10(11) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
N1 C18 C17 110.11(10) . . ?
N1 C18 H18A 109.6 . . ?
N1 C18 H18B 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.2 . . ?
C11 C19 H19 120.2 . . ?
C11 C19 C20 119.64(12) . . ?
C20 C19 H19 120.2 . . ?
C8 C20 H20 119.5 . . ?
C19 C20 C8 121.06(11) . . ?
C19 C20 H20 119.5 . . ?

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
Cl1 C1 C2 C3 179.61(9) . . . . ?
Cl1 C1 C13 C12 179.08(9) . . . . ?
O1 C5 C6 N1 11.17(19) . . . . ?
O1 C5 C6 C16 -161.20(13) . . . . ?
N1 C6 C16 C14 -0.41(14) . . . . ?
N1 C7 C8 C9 14.57(16) . . . . ?
N1 C7 C8 C20 -163.88(11) . . . . ?
N1 C7 C14 C15 179.88(12) . . . . ?
N1 C7 C14 C16 0.38(13) . . . . ?
C1 C2 C3 C4 1.44(18) . . . . ?
C2 C1 C13 C12 -0.71(18) . . . . ?
C2 C3 C4 C5 -178.21(11) . . . . ?
C2 C3 C4 C12 -0.97(18) . . . . ?
C3 C4 C5 O1 42.18(16) . . . . ?
C3 C4 C5 C6 -135.03(12) . . . . ?
C3 C4 C12 C13 -0.35(18) . . . . ?
C4 C5 C6 N1 -171.73(11) . . . . ?
C4 C5 C6 C16 15.90(18) . . . . ?
C4 C12 C13 C1 1.18(18) . . . . ?
C5 C4 C12 C13 176.75(11) . . . . ?
C5 C6 C16 C14 173.00(12) . . . . ?
C6 N1 C7 C8 177.89(10) . . . . ?
C6 N1 C7 C14 -0.65(13) . . . . ?
C6 N1 C18 C17 150.67(12) . . . . ?
C7 N1 C6 C5 -173.03(11) . . . . ?
C7 N1 C6 C16 0.67(13) . . . . ?
C7 N1 C18 C17 -32.35(16) . . . . ?
C7 C8 C9 C10 -177.07(12) . . . . ?
C7 C8 C9 C17 4.91(17) . . . . ?
C7 C8 C20 C19 177.63(11) . . . . ?
C7 C14 C15 F1 169.16(12) . . . . ?
C7 C14 C15 F2 -72.07(16) . . . . ?
C7 C14 C15 F3 49.00(18) . . . . ?
C7 C14 C16 C6 0.02(14) . . . . ?
C8 C7 C14 C15 1.6(2) . . . . ?
C8 C7 C14 C16 -177.86(12) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C8 C9 C17 C18 -36.97(17) . . . . ?
C9 C8 C20 C19 -0.80(18) . . . . ?
C9 C10 C11 C19 -0.7(2) . . . . ?
C9 C17 C18 N1 48.35(15) . . . . ?
C10 C9 C17 C18 145.06(13) . . . . ?
C10 C11 C19 C20 1.4(2) . . . . ?
C11 C19 C20 C8 -0.61(19) . . . . ?
C12 C4 C5 O1 -134.98(13) . . . . ?
C12 C4 C5 C6 47.81(16) . . . . ?
C13 C1 C2 C3 -0.60(19) . . . . ?
C14 C7 C8 C9 -167.37(13) . . . . ?
C14 C7 C8 C20 14.2(2) . . . . ?
C15 C14 C16 C6 -179.51(11) . . . . ?
C16 C14 C15 F1 -11.41(17) . . . . ?
C16 C14 C15 F2 107.36(13) . . . . ?
C16 C14 C15 F3 -131.57(12) . . . . ?
C17 C9 C10 C11 177.28(13) . . . . ?
C18 N1 C6 C5 4.27(19) . . . . ?
C18 N1 C6 C16 177.97(11) . . . . ?
C18 N1 C7 C8 0.46(17) . . . . ?
C18 N1 C7 C14 -178.08(11) . . . . ?
C20 C8 C9 C10 1.43(18) . . . . ?
C20 C8 C9 C17 -176.59(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
