# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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. 
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data_mo_20200714c_0m
_database_code_depnum_ccdc_archive 'CCDC 2043554'
loop_
_audit_author_name
_audit_author_address
liheng
;Anhui Normal University
China
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 B Cl2 F2 N2 O'
_chemical_formula_sum            'C16 H11 B Cl2 F2 N2 O'
_chemical_formula_weight         366.98
_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'
B B 0.0013 0.0007 '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                   6.5368(3)
_cell_length_b                   10.9882(6)
_cell_length_c                   12.5935(7)
_cell_angle_alpha                114.913(2)
_cell_angle_beta                 91.931(3)
_cell_angle_gamma                96.868(3)
_cell_volume                     810.95(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.15
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1365 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.8651.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22138
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         3.153
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2498
_reflns_number_total             3362
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.1057
_refine_ls_restrained_S_all      1.260
_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)+(0.0127P)²+2.7081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1792
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 0.8638(2) 0.72483(13) 1.01516(12) 0.0505(4) Uani 1 1 d . . . . .
Cl2 Cl 0.4167(3) 0.42493(16) 0.59634(14) 0.0686(5) Uani 1 1 d . . . . .
F1 F 0.6056(6) 0.9506(5) 0.6395(4) 0.0836(13) Uani 1 1 d . . . . .
F2 F 0.8201(6) 1.0487(3) 0.8047(4) 0.0790(12) Uani 1 1 d . . . . .
O1 O 1.0228(6) 0.8903(4) 0.5719(4) 0.0601(11) Uani 1 1 d . . . . .
N1 N 0.8259(6) 0.8138(4) 0.6828(3) 0.0352(9) Uani 1 1 d . . . . .
N2 N 0.5277(6) 0.8890(4) 0.7956(3) 0.0373(9) Uani 1 1 d . . . . .
C1 C 0.6264(10) 0.3379(5) 0.8505(6) 0.0567(16) Uani 1 1 d . . . . .
H1 H 0.624747 0.261093 0.864434 0.068 Uiso 1 1 calc R U . . .
C2 C 0.5297(10) 0.3258(6) 0.7481(6) 0.0567(15) Uani 1 1 d . . . . .
H2 H 0.460096 0.242464 0.693714 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5370(8) 0.4404(5) 0.7263(5) 0.0444(12) Uani 1 1 d . . . . .
C4 C 0.6412(7) 0.5655(5) 0.8059(4) 0.0364(11) Uani 1 1 d . . . . .
C5 C 0.7342(7) 0.5724(5) 0.9105(4) 0.0378(11) Uani 1 1 d . . . . .
C6 C 0.7254(9) 0.4594(5) 0.9332(5) 0.0508(14) Uani 1 1 d . . . . .
H6 H 0.786069 0.466059 1.003657 0.061 Uiso 1 1 calc R U . . .
C7 C 0.6575(7) 0.6862(4) 0.7797(4) 0.0323(10) Uani 1 1 d . . . . .
C8 C 0.5167(7) 0.7786(5) 0.8219(4) 0.0350(10) Uani 1 1 d . . . . .
C9 C 0.3493(8) 0.7821(5) 0.8887(4) 0.0427(12) Uani 1 1 d . . . . .
H9 H 0.306256 0.719653 0.918273 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2599(8) 0.8939(5) 0.9028(5) 0.0481(13) Uani 1 1 d . . . . .
H10 H 0.145773 0.921711 0.943873 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3721(8) 0.9579(5) 0.8443(5) 0.0458(13) Uani 1 1 d . . . . .
H11 H 0.344113 1.036494 0.839357 0.055 Uiso 1 1 calc R U . . .
C12 C 0.8096(7) 0.7039(4) 0.7128(4) 0.0332(10) Uani 1 1 d . . . . .
C13 C 0.9640(8) 0.6254(5) 0.6594(4) 0.0435(12) Uani 1 1 d . . . . .
H13 H 0.988867 0.546783 0.665182 0.052 Uiso 1 1 calc R U . . .
C14 C 1.0710(8) 0.6840(5) 0.5977(4) 0.0445(12) Uani 1 1 d . . . . .
H14 H 1.181195 0.653742 0.553794 0.053 Uiso 1 1 calc R U . . .
C15 C 0.9804(8) 0.7996(5) 0.6142(4) 0.0414(12) Uani 1 1 d . . . . .
C16 C 1.1648(11) 0.8590(8) 0.4813(7) 0.084(2) Uani 1 1 d . . . . .
H16A H 1.105021 0.778836 0.413267 0.126 Uiso 1 1 calc R U . . .
H16B H 1.292581 0.843769 0.510156 0.126 Uiso 1 1 calc R U . . .
H16C H 1.190975 0.933565 0.460373 0.126 Uiso 1 1 calc R U . . .
B1 B 0.6954(10) 0.9314(6) 0.7298(6) 0.0428(14) 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
C1 H1 0.9300 . ?
C1 C2 1.365(8) . ?
C1 C6 1.365(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(7) . ?
C3 Cl2 1.724(6) . ?
C3 C4 1.388(7) . ?
C4 C5 1.401(7) . ?
C4 C7 1.488(6) . ?
C5 Cl1 1.728(5) . ?
C5 C6 1.382(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.401(7) . ?
C7 C12 1.373(6) . ?
C8 N2 1.382(6) . ?
C8 C9 1.396(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(7) . ?
C11 N2 1.349(6) . ?
C11 H11 0.9300 . ?
C12 N1 1.402(5) . ?
C12 C13 1.407(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.362(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.405(7) . ?
C15 O1 1.321(6) . ?
C15 N1 1.332(6) . ?
C16 O1 1.449(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
B1 F1 1.367(7) . ?
B1 F2 1.374(7) . ?
B1 N1 1.550(7) . ?
B1 N2 1.539(7) . ?

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
C15 O1 C16 116.4(5) . . ?
C12 N1 B1 125.0(4) . . ?
C15 N1 C12 106.6(4) . . ?
C15 N1 B1 128.4(4) . . ?
C8 N2 B1 126.3(4) . . ?
C11 N2 C8 107.5(4) . . ?
C11 N2 B1 126.0(4) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C6 C1 C2 121.9(5) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.9(5) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 Cl2 118.9(4) . . ?
C4 C3 Cl2 119.6(4) . . ?
C4 C3 C2 121.5(5) . . ?
C3 C4 C5 117.1(4) . . ?
C3 C4 C7 121.3(5) . . ?
C5 C4 C7 121.5(4) . . ?
C4 C5 Cl1 120.1(3) . . ?
C6 C5 Cl1 118.3(4) . . ?
C6 C5 C4 121.6(5) . . ?
C1 C6 C5 118.9(5) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C4 119.9(4) . . ?
C12 C7 C4 119.1(4) . . ?
C12 C7 C8 121.0(4) . . ?
N2 C8 C7 120.2(4) . . ?
N2 C8 C9 107.9(4) . . ?
C9 C8 C7 131.9(4) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 C8 107.8(4) . . ?
C10 C9 H9 126.1 . . ?
C9 C10 H10 126.5 . . ?
C9 C10 C11 107.0(4) . . ?
C11 C10 H10 126.5 . . ?
N2 C11 C10 109.8(4) . . ?
N2 C11 H11 125.1 . . ?
C10 C11 H11 125.1 . . ?
N1 C12 C13 107.5(4) . . ?
C7 C12 N1 120.9(4) . . ?
C7 C12 C13 131.6(4) . . ?
C12 C13 H13 125.7 . . ?
C14 C13 C12 108.6(4) . . ?
C14 C13 H13 125.7 . . ?
C13 C14 H14 127.1 . . ?
C13 C14 C15 105.8(4) . . ?
C15 C14 H14 127.1 . . ?
O1 C15 N1 117.9(4) . . ?
O1 C15 C14 130.5(5) . . ?
N1 C15 C14 111.6(4) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 B1 F2 109.5(5) . . ?
F1 B1 N1 111.0(5) . . ?
F1 B1 N2 110.1(5) . . ?
F2 B1 N1 109.5(5) . . ?
F2 B1 N2 110.7(5) . . ?
N2 B1 N1 106.0(4) . . ?

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 C5 C6 C1 -179.0(4) . . . . ?
Cl2 C3 C4 C5 179.3(4) . . . . ?
Cl2 C3 C4 C7 -2.1(7) . . . . ?
F1 B1 N1 C12 -128.8(5) . . . . ?
F1 B1 N1 C15 55.8(7) . . . . ?
F1 B1 N2 C8 128.9(5) . . . . ?
F1 B1 N2 C11 -55.5(7) . . . . ?
F2 B1 N1 C12 110.2(5) . . . . ?
F2 B1 N1 C15 -65.2(7) . . . . ?
F2 B1 N2 C8 -109.9(5) . . . . ?
F2 B1 N2 C11 65.7(7) . . . . ?
O1 C15 N1 C12 178.4(5) . . . . ?
O1 C15 N1 B1 -5.5(8) . . . . ?
N1 C12 C13 C14 -0.5(6) . . . . ?
N1 C15 O1 C16 -169.1(5) . . . . ?
N1 B1 N2 C8 8.8(7) . . . . ?
N1 B1 N2 C11 -175.6(5) . . . . ?
N2 C8 C9 C10 -0.1(6) . . . . ?
N2 B1 N1 C12 -9.2(7) . . . . ?
N2 B1 N1 C15 175.4(5) . . . . ?
C1 C2 C3 Cl2 179.5(5) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C2 C1 C6 C5 -2.3(9) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C2 C3 C4 C7 177.0(5) . . . . ?
C3 C4 C5 Cl1 -179.1(4) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C3 C4 C7 C8 96.0(6) . . . . ?
C3 C4 C7 C12 -83.2(6) . . . . ?
C4 C5 C6 C1 1.1(8) . . . . ?
C4 C7 C8 N2 -178.4(4) . . . . ?
C4 C7 C8 C9 -0.3(8) . . . . ?
C4 C7 C12 N1 177.8(4) . . . . ?
C4 C7 C12 C13 0.4(8) . . . . ?
C5 C4 C7 C8 -85.5(6) . . . . ?
C5 C4 C7 C12 95.3(6) . . . . ?
C6 C1 C2 C3 1.6(9) . . . . ?
C7 C4 C5 Cl1 2.3(6) . . . . ?
C7 C4 C5 C6 -177.7(5) . . . . ?
C7 C8 N2 C11 178.4(4) . . . . ?
C7 C8 N2 B1 -5.3(7) . . . . ?
C7 C8 C9 C10 -178.4(5) . . . . ?
C7 C12 N1 C15 -177.3(4) . . . . ?
C7 C12 N1 B1 6.5(7) . . . . ?
C7 C12 C13 C14 177.2(5) . . . . ?
C8 C7 C12 N1 -1.3(7) . . . . ?
C8 C7 C12 C13 -178.7(5) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
C9 C8 N2 C11 -0.1(6) . . . . ?
C9 C8 N2 B1 176.1(5) . . . . ?
C9 C10 C11 N2 -0.4(6) . . . . ?
C10 C11 N2 C8 0.3(6) . . . . ?
C10 C11 N2 B1 -176.0(5) . . . . ?
C12 C7 C8 N2 0.7(7) . . . . ?
C12 C7 C8 C9 178.8(5) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C13 C12 N1 C15 0.6(5) . . . . ?
C13 C12 N1 B1 -175.6(5) . . . . ?
C13 C14 C15 O1 -178.5(6) . . . . ?
C13 C14 C15 N1 0.3(6) . . . . ?
C14 C15 O1 C16 9.7(9) . . . . ?
C14 C15 N1 C12 -0.6(6) . . . . ?
C14 C15 N1 B1 175.5(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.091 0.329 0.761 21.6 0.8 ?
2 -0.091 0.671 0.239 21.6 0.7 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_mo_20201015f_0m
_database_code_depnum_ccdc_archive 'CCDC 2043557'
loop_
_audit_author_name
_audit_author_address
liheng
;Anhui Normal University
China
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2020-11-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 B Cl2 F2 N2 O'
_chemical_formula_sum            'C22 H15 B Cl2 F2 N2 O'
_chemical_formula_weight         443.07
_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'
B B 0.0013 0.0007 '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                   7.0336(2)
_cell_length_b                   11.3399(4)
_cell_length_c                   14.7341(5)
_cell_angle_alpha                70.1820(10)
_cell_angle_beta                 78.6320(10)
_cell_angle_gamma                82.1520(10)
_cell_volume                     1080.80(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8147
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0828 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.9278.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19948
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.978
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3516
_reflns_number_total             4950
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.036
_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)+(0.0706P)²+0.5989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C14, C13
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
3.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C9(H9), C10(H10), C2(H2), C6(H6), C19(H19), C21(H21), C1(H1),
 C20(H20), C18(H18), C17(H17), C16(H16), 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
Cl2 Cl 0.51846(11) 0.74966(6) 0.04212(5) 0.0596(2) Uani 1 1 d . . . . .
Cl1 Cl 0.78576(13) 0.58765(6) 0.38729(5) 0.0674(2) Uani 1 1 d . . . . .
F1 F 0.7952(2) 0.17197(12) 0.26545(11) 0.0563(4) Uani 1 1 d . . . . .
F2 F 0.6704(2) 0.25965(16) 0.12596(11) 0.0607(4) Uani 1 1 d . . . . .
O1 O 0.3675(2) 0.17329(14) 0.32586(13) 0.0455(4) Uani 1 1 d . . . . .
N1 N 0.5485(3) 0.34479(15) 0.25723(13) 0.0346(4) Uani 1 1 d . . . . .
N2 N 0.8818(3) 0.37946(17) 0.16507(14) 0.0388(4) Uani 1 1 d . . . . .
C22 C 0.8575(3) 0.5024(2) 0.16630(16) 0.0390(5) Uani 1 1 d . . . . .
C7 C 0.6802(3) 0.54780(18) 0.21048(15) 0.0353(4) Uani 1 1 d . . . . .
C8 C 0.5295(3) 0.47079(18) 0.25427(16) 0.0366(5) Uani 1 1 d . . . . .
C4 C 0.6550(3) 0.67885(18) 0.21376(16) 0.0361(5) Uani 1 1 d . . . . .
C11 C 0.3855(3) 0.2940(2) 0.30956(16) 0.0386(5) Uani 1 1 d . . . . .
C14 C 0.2866(4) -0.1001(2) 0.48633(17) 0.0458(5) Uani 1 1 d . U . . .
H14 H 0.337884 -0.070162 0.527182 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3454(4) 0.4932(2) 0.30635(19) 0.0454(5) Uani 1 1 d . . . . .
H9 H 0.295014 0.569421 0.315265 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5835(3) 0.7789(2) 0.14018(17) 0.0414(5) Uani 1 1 d . . . . .
C3 C 0.7008(3) 0.7080(2) 0.29154(17) 0.0416(5) Uani 1 1 d . . . . .
C10 C 0.2530(4) 0.3843(2) 0.34167(19) 0.0476(6) Uani 1 1 d . . . . .
H10 H 0.129812 0.371667 0.378808 0.057 Uiso 1 1 calc R U . . .
C2 C 0.6782(4) 0.8298(2) 0.2952(2) 0.0491(6) Uani 1 1 d . . . . .
H2 H 0.709763 0.846479 0.347789 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2036(3) -0.0145(2) 0.40843(17) 0.0424(5) Uani 1 1 d . U . . .
C6 C 0.5601(4) 0.9008(2) 0.1431(2) 0.0485(6) Uani 1 1 d . . . . .
H6 H 0.511815 0.965786 0.092964 0.058 Uiso 1 1 calc R U . . .
C19 C 1.0659(4) 0.3619(2) 0.12078(19) 0.0514(6) Uani 1 1 d . . . . .
H19 H 1.120646 0.287054 0.110634 0.062 Uiso 1 1 calc R U . . .
C21 C 1.0314(4) 0.5593(2) 0.12121(19) 0.0495(6) Uani 1 1 d . . . . .
H21 H 1.055060 0.641595 0.112198 0.059 Uiso 1 1 calc R U . . .
C1 C 0.6091(4) 0.9252(2) 0.2208(2) 0.0509(6) Uani 1 1 d . . . . .
H1 H 0.594970 1.007156 0.222644 0.061 Uiso 1 1 calc R U . . .
C20 C 1.1616(4) 0.4707(3) 0.0926(2) 0.0574(7) Uani 1 1 d . . . . .
H20 H 1.288904 0.481956 0.060531 0.069 Uiso 1 1 calc R U . . .
C18 C 0.1359(4) -0.0614(2) 0.34715(19) 0.0479(6) Uani 1 1 d . . . . .
H18 H 0.081213 -0.006386 0.294387 0.057 Uiso 1 1 calc R U . . .
C17 C 0.1481(4) -0.1891(2) 0.3630(2) 0.0533(6) Uani 1 1 d . . . . .
H17 H 0.103569 -0.219570 0.320450 0.064 Uiso 1 1 calc R U . . .
C16 C 0.2256(4) -0.2712(2) 0.4414(2) 0.0552(7) Uani 1 1 d . . . . .
H16 H 0.231900 -0.357299 0.452495 0.066 Uiso 1 1 calc R U . . .
C12 C 0.1899(4) 0.1243(2) 0.3900(2) 0.0546(7) Uani 1 1 d . . . . .
H12A H 0.077327 0.164045 0.359263 0.065 Uiso 1 1 calc R U . . .
H12B H 0.176646 0.141544 0.451189 0.065 Uiso 1 1 calc R U . . .
B1 B 0.7256(4) 0.2834(2) 0.20211(18) 0.0373(5) Uani 1 1 d . . . . .
C15 C 0.2940(4) -0.2264(3) 0.5037(2) 0.0596(7) Uani 1 1 d . . . . .
H15 H 0.345105 -0.281954 0.557381 0.071 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
Cl2 C5 1.741(2) . ?
Cl1 C3 1.736(2) . ?
F1 B1 1.385(3) . ?
F2 B1 1.374(3) . ?
O1 C11 1.327(3) . ?
O1 C12 1.459(3) . ?
N1 C8 1.403(2) . ?
N1 C11 1.331(3) . ?
N1 B1 1.563(3) . ?
N2 C22 1.387(3) . ?
N2 C19 1.351(3) . ?
N2 B1 1.543(3) . ?
C22 C7 1.406(3) . ?
C22 C21 1.400(3) . ?
C7 C8 1.379(3) . ?
C7 C4 1.489(3) . ?
C8 C9 1.407(3) . ?
C4 C5 1.393(3) . ?
C4 C3 1.399(3) . ?
C11 C10 1.426(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.398(3) . ?
C14 C15 1.362(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(3) . ?
C5 C6 1.384(3) . ?
C3 C2 1.387(3) . ?
C10 H10 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.367(4) . ?
C13 C18 1.374(3) . ?
C13 C12 1.497(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.380(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.382(4) . ?
C1 H1 0.9300 . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.380(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.371(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.374(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C15 H15 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
C11 O1 C12 115.12(17) . . ?
C8 N1 B1 124.51(17) . . ?
C11 N1 C8 106.95(17) . . ?
C11 N1 B1 128.43(17) . . ?
C22 N2 B1 126.59(18) . . ?
C19 N2 C22 106.86(19) . . ?
C19 N2 B1 126.47(19) . . ?
N2 C22 C7 120.12(19) . . ?
N2 C22 C21 108.4(2) . . ?
C21 C22 C7 131.5(2) . . ?
C22 C7 C4 120.24(18) . . ?
C8 C7 C22 120.75(19) . . ?
C8 C7 C4 118.98(19) . . ?
N1 C8 C9 107.82(18) . . ?
C7 C8 N1 121.37(19) . . ?
C7 C8 C9 130.71(19) . . ?
C5 C4 C7 121.97(19) . . ?
C5 C4 C3 116.37(19) . . ?
C3 C4 C7 121.65(19) . . ?
O1 C11 N1 119.31(19) . . ?
O1 C11 C10 129.6(2) . . ?
N1 C11 C10 111.12(19) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C15 C14 C13 121.4(2) . . ?
C8 C9 H9 125.7 . . ?
C10 C9 C8 108.6(2) . . ?
C10 C9 H9 125.7 . . ?
C4 C5 Cl2 119.11(16) . . ?
C6 C5 Cl2 118.82(19) . . ?
C6 C5 C4 122.1(2) . . ?
C4 C3 Cl1 119.00(17) . . ?
C2 C3 Cl1 118.92(19) . . ?
C2 C3 C4 122.1(2) . . ?
C11 C10 H10 127.3 . . ?
C9 C10 C11 105.5(2) . . ?
C9 C10 H10 127.3 . . ?
C3 C2 H2 120.3 . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.3 . . ?
C14 C13 C12 122.0(2) . . ?
C18 C13 C14 117.9(2) . . ?
C18 C13 C12 120.1(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 H6 120.3 . . ?
N2 C19 H19 124.7 . . ?
N2 C19 C20 110.6(2) . . ?
C20 C19 H19 124.7 . . ?
C22 C21 H21 126.3 . . ?
C20 C21 C22 107.3(2) . . ?
C20 C21 H21 126.3 . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C19 C20 H20 126.6 . . ?
C21 C20 C19 106.8(2) . . ?
C21 C20 H20 126.6 . . ?
C13 C18 H18 119.6 . . ?
C13 C18 C17 120.7(2) . . ?
C17 C18 H18 119.6 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
O1 C12 C13 107.78(19) . . ?
O1 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?
F1 B1 N1 110.22(18) . . ?
F1 B1 N2 110.17(19) . . ?
F2 B1 F1 109.41(19) . . ?
F2 B1 N1 109.94(19) . . ?
F2 B1 N2 111.35(19) . . ?
N2 B1 N1 105.71(16) . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?

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
Cl2 C5 C6 C1 179.32(19) . . . . ?
Cl1 C3 C2 C1 -179.2(2) . . . . ?
O1 C11 C10 C9 178.6(2) . . . . ?
N1 C8 C9 C10 0.6(3) . . . . ?
N1 C11 C10 C9 -0.4(3) . . . . ?
N2 C22 C7 C8 0.9(3) . . . . ?
N2 C22 C7 C4 178.71(19) . . . . ?
N2 C22 C21 C20 0.0(3) . . . . ?
N2 C19 C20 C21 0.4(3) . . . . ?
C22 N2 C19 C20 -0.4(3) . . . . ?
C22 N2 B1 F1 -128.8(2) . . . . ?
C22 N2 B1 F2 109.6(2) . . . . ?
C22 N2 B1 N1 -9.7(3) . . . . ?
C22 C7 C8 N1 0.7(3) . . . . ?
C22 C7 C8 C9 176.5(2) . . . . ?
C22 C7 C4 C5 90.7(3) . . . . ?
C22 C7 C4 C3 -89.8(3) . . . . ?
C22 C21 C20 C19 -0.2(3) . . . . ?
C7 C22 C21 C20 178.4(3) . . . . ?
C7 C8 C9 C10 -175.6(2) . . . . ?
C7 C4 C5 Cl2 0.9(3) . . . . ?
C7 C4 C5 C6 -179.9(2) . . . . ?
C7 C4 C3 Cl1 -0.9(3) . . . . ?
C7 C4 C3 C2 179.9(2) . . . . ?
C8 N1 C11 O1 -178.3(2) . . . . ?
C8 N1 C11 C10 0.8(3) . . . . ?
C8 N1 B1 F1 130.2(2) . . . . ?
C8 N1 B1 F2 -109.1(2) . . . . ?
C8 N1 B1 N2 11.2(3) . . . . ?
C8 C7 C4 C5 -91.5(3) . . . . ?
C8 C7 C4 C3 88.1(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C4 C7 C8 N1 -177.07(19) . . . . ?
C4 C7 C8 C9 -1.3(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C3 C2 C1 0.0(4) . . . . ?
C11 O1 C12 C13 -174.2(2) . . . . ?
C11 N1 C8 C7 175.8(2) . . . . ?
C11 N1 C8 C9 -0.8(2) . . . . ?
C11 N1 B1 F1 -54.2(3) . . . . ?
C11 N1 B1 F2 66.4(3) . . . . ?
C11 N1 B1 N2 -173.3(2) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C14 C13 C12 O1 89.5(3) . . . . ?
C5 C4 C3 Cl1 178.64(17) . . . . ?
C5 C4 C3 C2 -0.6(3) . . . . ?
C5 C6 C1 C2 -0.7(4) . . . . ?
C3 C4 C5 Cl2 -178.69(17) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C2 C1 C6 0.7(4) . . . . ?
C13 C14 C15 C16 2.6(4) . . . . ?
C13 C18 C17 C16 1.0(4) . . . . ?
C19 N2 C22 C7 -178.4(2) . . . . ?
C19 N2 C22 C21 0.2(3) . . . . ?
C19 N2 B1 F1 54.8(3) . . . . ?
C19 N2 B1 F2 -66.8(3) . . . . ?
C19 N2 B1 N1 173.8(2) . . . . ?
C21 C22 C7 C8 -177.3(2) . . . . ?
C21 C22 C7 C4 0.5(4) . . . . ?
C18 C13 C12 O1 -89.6(3) . . . . ?
C18 C17 C16 C15 -0.9(4) . . . . ?
C17 C16 C15 C14 -0.8(4) . . . . ?
C12 O1 C11 N1 175.6(2) . . . . ?
C12 O1 C11 C10 -3.3(4) . . . . ?
C12 C13 C18 C17 179.8(2) . . . . ?
B1 N1 C8 C7 -7.8(3) . . . . ?
B1 N1 C8 C9 175.5(2) . . . . ?
B1 N1 C11 O1 5.5(3) . . . . ?
B1 N1 C11 C10 -175.4(2) . . . . ?
B1 N2 C22 C7 4.6(3) . . . . ?
B1 N2 C22 C21 -176.8(2) . . . . ?
B1 N2 C19 C20 176.6(2) . . . . ?
C15 C14 C13 C18 -2.4(4) . . . . ?
C15 C14 C13 C12 178.4(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 115.1 43.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_mo_20201012a_0m
_database_code_depnum_ccdc_archive 'CCDC 2043558'
loop_
_audit_author_name
_audit_author_address
liheng
;Anhui Normal University
China
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2020-11-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 B Cl2 F2 N2 O3 S'
_chemical_formula_sum            'C22 H15 B Cl2 F2 N2 O3 S'
_chemical_formula_weight         507.13
_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'
B B 0.0013 0.0007 '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'
S S 0.1246 0.1234 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.0000(6)
_cell_length_b                   12.6326(5)
_cell_length_c                   14.1556(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.884(2)
_cell_angle_gamma                90
_cell_volume                     2306.47(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9353
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.07
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1253 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.9250.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            78020
_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         27.543
_diffrn_reflns_theta_min         2.901
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3131
_reflns_number_total             5325
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.019
_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)+(0.0603P)²+2.3064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1671
_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:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C20(H20), C9(H9), C11(H11), C10(H10), C21(H21), C22(H22),
 C6(H6), C2(H2), C1(H1)
;
_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
S1 S -0.07978(7) 0.57213(8) 0.61729(8) 0.0700(3) Uani 1 1 d . . . . .
Cl1 Cl 0.37246(10) 0.85293(8) 0.02183(8) 0.0891(4) Uani 1 1 d . . . . .
Cl2 Cl 0.60803(9) 0.60373(11) 0.33704(10) 0.1038(4) Uani 1 1 d . . . . .
F1 F 0.10986(14) 0.61080(16) 0.14716(15) 0.0702(5) Uani 1 1 d . . . . .
F2 F 0.22232(16) 0.53432(15) 0.29167(15) 0.0714(6) Uani 1 1 d . . . . .
O2 O 0.06484(16) 0.73025(17) 0.47554(16) 0.0571(5) Uani 1 1 d . . . . .
O1 O 0.16079(16) 0.76283(17) 0.32895(16) 0.0572(5) Uani 1 1 d . . . . .
N1 N 0.26595(18) 0.70689(19) 0.24916(18) 0.0468(6) Uani 1 1 d . . . . .
N2 N 0.2722(2) 0.54897(19) 0.14760(19) 0.0527(6) Uani 1 1 d . . . . .
O3 O -0.09594(18) 0.7512(2) 0.4714(2) 0.0796(8) Uani 1 1 d . . . . .
C12 C 0.3561(2) 0.7433(2) 0.2386(2) 0.0469(7) Uani 1 1 d . . . . .
C7 C 0.4024(2) 0.6868(2) 0.1859(2) 0.0467(7) Uani 1 1 d . . . . .
C4 C 0.4977(2) 0.7296(2) 0.1771(2) 0.0504(7) Uani 1 1 d . . . . .
C8 C 0.3613(2) 0.5891(2) 0.1401(2) 0.0472(7) Uani 1 1 d . . . . .
C15 C 0.2426(2) 0.7778(3) 0.3055(2) 0.0504(7) Uani 1 1 d . . . . .
C13 C 0.3839(2) 0.8411(2) 0.2910(2) 0.0536(7) Uani 1 1 d . . . . .
H13 H 0.440457 0.882651 0.296049 0.064 Uiso 1 1 calc R U . . .
C19 C 0.0127(2) 0.6183(3) 0.5764(2) 0.0528(7) Uani 1 1 d . . . . .
C18 C -0.0137(2) 0.7058(3) 0.5041(3) 0.0562(8) Uani 1 1 d . . . . .
C14 C 0.3140(3) 0.8638(3) 0.3325(2) 0.0565(8) Uani 1 1 d . . . . .
H14 H 0.312893 0.923219 0.370779 0.068 Uiso 1 1 calc R U . . .
C20 C 0.1024(2) 0.5613(3) 0.6166(2) 0.0561(8) Uani 1 1 d . . . . .
H20 H 0.161314 0.574598 0.603323 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3933(3) 0.5190(3) 0.0820(2) 0.0585(8) Uani 1 1 d . . . . .
H9 H 0.450889 0.526493 0.065310 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1443(3) 0.8435(3) 0.3945(3) 0.0613(8) Uani 1 1 d . . . . .
H16A H 0.140049 0.912810 0.363696 0.074 Uiso 1 1 calc R U . . .
H16B H 0.201647 0.843690 0.460871 0.074 Uiso 1 1 calc R U . . .
C11 C 0.2507(3) 0.4568(3) 0.0952(3) 0.0658(9) Uani 1 1 d . . . . .
H11 H 0.194628 0.413375 0.088016 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4923(3) 0.8053(3) 0.1041(3) 0.0636(9) Uani 1 1 d . . . . .
C17 C 0.0451(3) 0.8188(3) 0.4069(3) 0.0642(9) Uani 1 1 d . . . . .
H17A H 0.022703 0.879478 0.434925 0.077 Uiso 1 1 calc R U . . .
H17B H -0.008840 0.801341 0.341032 0.077 Uiso 1 1 calc R U . . .
C10 C 0.3228(3) 0.4358(3) 0.0539(3) 0.0707(10) Uani 1 1 d . . . . .
H10 H 0.324225 0.377217 0.014712 0.085 Uiso 1 1 calc R U . . .
C21 C 0.0942(3) 0.4798(3) 0.6809(3) 0.0692(9) Uani 1 1 d . . . . .
H21 H 0.147818 0.433093 0.715193 0.083 Uiso 1 1 calc R U . . .
C3 C 0.5961(3) 0.6963(3) 0.2435(3) 0.0681(10) Uani 1 1 d . . . . .
C22 C 0.0005(3) 0.4762(3) 0.6879(3) 0.0725(10) Uani 1 1 d . . . . .
H22 H -0.017499 0.426900 0.726874 0.087 Uiso 1 1 calc R U . . .
B1 B 0.2131(3) 0.5973(3) 0.2095(3) 0.0534(9) Uani 1 1 d . . . . .
C6 C 0.5815(4) 0.8456(4) 0.0966(4) 0.0972(15) Uani 1 1 d . . . . .
H6 H 0.577066 0.896233 0.047331 0.117 Uiso 1 1 calc R U . . .
C2 C 0.6855(3) 0.7372(4) 0.2371(5) 0.0977(16) Uani 1 1 d . . . . .
H2 H 0.750559 0.715502 0.282778 0.117 Uiso 1 1 calc R U . . .
C1 C 0.6764(4) 0.8094(5) 0.1631(5) 0.1112(19) Uani 1 1 d . . . . .
H1 H 0.736105 0.835182 0.157267 0.133 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
S1 C19 1.713(3) . ?
S1 C22 1.690(4) . ?
Cl1 C5 1.735(4) . ?
Cl2 C3 1.726(4) . ?
F1 B1 1.381(4) . ?
F2 B1 1.373(4) . ?
O2 C18 1.347(4) . ?
O2 C17 1.436(4) . ?
O1 C15 1.324(3) . ?
O1 C16 1.455(4) . ?
N1 C12 1.405(3) . ?
N1 C15 1.322(4) . ?
N1 B1 1.567(4) . ?
N2 C8 1.387(4) . ?
N2 C11 1.350(4) . ?
N2 B1 1.547(4) . ?
O3 C18 1.205(4) . ?
C12 C7 1.365(4) . ?
C12 C13 1.415(4) . ?
C7 C4 1.488(4) . ?
C7 C8 1.409(4) . ?
C4 C5 1.388(5) . ?
C4 C3 1.397(5) . ?
C8 C9 1.395(4) . ?
C15 C14 1.424(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.353(4) . ?
C19 C18 1.453(5) . ?
C19 C20 1.366(4) . ?
C14 H14 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.408(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.498(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.375(5) . ?
C5 C6 1.391(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C10 H10 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.354(5) . ?
C3 C2 1.389(5) . ?
C22 H22 0.9300 . ?
C6 H6 0.9300 . ?
C6 C1 1.374(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.357(7) . ?
C1 H1 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
C22 S1 C19 91.60(17) . . ?
C18 O2 C17 114.7(2) . . ?
C15 O1 C16 115.3(2) . . ?
C12 N1 B1 124.7(2) . . ?
C15 N1 C12 106.6(2) . . ?
C15 N1 B1 128.4(2) . . ?
C8 N2 B1 126.4(2) . . ?
C11 N2 C8 106.8(3) . . ?
C11 N2 B1 126.7(3) . . ?
N1 C12 C13 107.7(3) . . ?
C7 C12 N1 121.7(3) . . ?
C7 C12 C13 130.6(3) . . ?
C12 C7 C4 119.2(3) . . ?
C12 C7 C8 120.9(3) . . ?
C8 C7 C4 119.9(3) . . ?
C5 C4 C7 121.4(3) . . ?
C5 C4 C3 117.5(3) . . ?
C3 C4 C7 121.1(3) . . ?
N2 C8 C7 120.2(3) . . ?
N2 C8 C9 108.5(3) . . ?
C9 C8 C7 131.3(3) . . ?
O1 C15 C14 128.9(3) . . ?
N1 C15 O1 119.7(3) . . ?
N1 C15 C14 111.5(3) . . ?
C12 C13 H13 125.8 . . ?
C14 C13 C12 108.4(3) . . ?
C14 C13 H13 125.8 . . ?
C18 C19 S1 118.6(2) . . ?
C20 C19 S1 111.9(3) . . ?
C20 C19 C18 129.5(3) . . ?
O2 C18 C19 111.8(3) . . ?
O3 C18 O2 123.0(3) . . ?
O3 C18 C19 125.2(3) . . ?
C15 C14 H14 127.1 . . ?
C13 C14 C15 105.8(3) . . ?
C13 C14 H14 127.1 . . ?
C19 C20 H20 124.4 . . ?
C19 C20 C21 111.2(3) . . ?
C21 C20 H20 124.4 . . ?
C8 C9 H9 126.4 . . ?
C10 C9 C8 107.1(3) . . ?
C10 C9 H9 126.4 . . ?
O1 C16 H16A 110.0 . . ?
O1 C16 H16B 110.0 . . ?
O1 C16 C17 108.2(3) . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
N2 C11 H11 124.6 . . ?
N2 C11 C10 110.8(3) . . ?
C10 C11 H11 124.6 . . ?
C4 C5 Cl1 119.8(3) . . ?
C4 C5 C6 121.2(4) . . ?
C6 C5 Cl1 119.0(3) . . ?
O2 C17 C16 107.4(3) . . ?
O2 C17 H17A 110.2 . . ?
O2 C17 H17B 110.2 . . ?
C16 C17 H17A 110.2 . . ?
C16 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C9 C10 H10 126.6 . . ?
C11 C10 C9 106.8(3) . . ?
C11 C10 H10 126.6 . . ?
C20 C21 H21 123.3 . . ?
C22 C21 C20 113.4(3) . . ?
C22 C21 H21 123.3 . . ?
C4 C3 Cl2 119.7(3) . . ?
C2 C3 Cl2 118.8(4) . . ?
C2 C3 C4 121.5(4) . . ?
S1 C22 H22 124.0 . . ?
C21 C22 S1 111.9(3) . . ?
C21 C22 H22 124.0 . . ?
F1 B1 N1 110.6(3) . . ?
F1 B1 N2 110.1(3) . . ?
F2 B1 F1 110.1(3) . . ?
F2 B1 N1 109.5(3) . . ?
F2 B1 N2 110.9(3) . . ?
N2 B1 N1 105.7(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 C5 118.9(5) . . ?
C1 C6 H6 120.5 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2 120.5 . . ?
C6 C1 H1 119.1 . . ?
C2 C1 C6 121.9(4) . . ?
C2 C1 H1 119.1 . . ?

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
S1 C19 C18 O2 -177.2(2) . . . . ?
S1 C19 C18 O3 1.7(5) . . . . ?
S1 C19 C20 C21 0.0(4) . . . . ?
Cl1 C5 C6 C1 178.7(3) . . . . ?
Cl2 C3 C2 C1 179.5(3) . . . . ?
O1 C15 C14 C13 179.3(3) . . . . ?
O1 C16 C17 O2 74.4(3) . . . . ?
N1 C12 C7 C4 179.8(3) . . . . ?
N1 C12 C7 C8 -0.3(4) . . . . ?
N1 C12 C13 C14 0.3(3) . . . . ?
N1 C15 C14 C13 -0.9(4) . . . . ?
N2 C8 C9 C10 0.1(4) . . . . ?
N2 C11 C10 C9 0.1(4) . . . . ?
C12 N1 C15 O1 -179.1(3) . . . . ?
C12 N1 C15 C14 1.1(3) . . . . ?
C12 N1 B1 F1 -126.0(3) . . . . ?
C12 N1 B1 F2 112.6(3) . . . . ?
C12 N1 B1 N2 -6.9(4) . . . . ?
C12 C7 C4 C5 -81.7(4) . . . . ?
C12 C7 C4 C3 97.0(4) . . . . ?
C12 C7 C8 N2 0.4(4) . . . . ?
C12 C7 C8 C9 178.9(3) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C7 C12 C13 C14 -179.3(3) . . . . ?
C7 C4 C5 Cl1 0.7(4) . . . . ?
C7 C4 C5 C6 179.6(3) . . . . ?
C7 C4 C3 Cl2 0.3(4) . . . . ?
C7 C4 C3 C2 -178.8(3) . . . . ?
C7 C8 C9 C10 -178.5(3) . . . . ?
C4 C7 C8 N2 -179.7(3) . . . . ?
C4 C7 C8 C9 -1.2(5) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C4 C3 C2 C1 -1.4(6) . . . . ?
C8 N2 C11 C10 0.0(4) . . . . ?
C8 N2 B1 F1 126.6(3) . . . . ?
C8 N2 B1 F2 -111.4(3) . . . . ?
C8 N2 B1 N1 7.2(4) . . . . ?
C8 C7 C4 C5 98.4(4) . . . . ?
C8 C7 C4 C3 -82.9(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C15 O1 C16 C17 175.8(3) . . . . ?
C15 N1 C12 C7 178.8(3) . . . . ?
C15 N1 C12 C13 -0.9(3) . . . . ?
C15 N1 B1 F1 60.7(4) . . . . ?
C15 N1 B1 F2 -60.7(4) . . . . ?
C15 N1 B1 N2 179.8(3) . . . . ?
C13 C12 C7 C4 -0.7(5) . . . . ?
C13 C12 C7 C8 179.2(3) . . . . ?
C19 S1 C22 C21 0.3(3) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C18 O2 C17 C16 172.7(3) . . . . ?
C18 C19 C20 C21 -177.4(3) . . . . ?
C20 C19 C18 O2 0.1(5) . . . . ?
C20 C19 C18 O3 179.0(3) . . . . ?
C20 C21 C22 S1 -0.4(4) . . . . ?
C16 O1 C15 N1 177.7(3) . . . . ?
C16 O1 C15 C14 -2.5(4) . . . . ?
C11 N2 C8 C7 178.7(3) . . . . ?
C11 N2 C8 C9 -0.1(3) . . . . ?
C11 N2 B1 F1 -57.4(4) . . . . ?
C11 N2 B1 F2 64.7(4) . . . . ?
C11 N2 B1 N1 -176.8(3) . . . . ?
C5 C4 C3 Cl2 179.1(2) . . . . ?
C5 C4 C3 C2 0.0(5) . . . . ?
C5 C6 C1 C2 -1.3(7) . . . . ?
C17 O2 C18 O3 3.2(5) . . . . ?
C17 O2 C18 C19 -177.8(3) . . . . ?
C3 C4 C5 Cl1 -178.1(2) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C3 C2 C1 C6 2.1(7) . . . . ?
C22 S1 C19 C18 177.6(3) . . . . ?
C22 S1 C19 C20 -0.2(3) . . . . ?
B1 N1 C12 C7 4.2(4) . . . . ?
B1 N1 C12 C13 -175.4(3) . . . . ?
B1 N1 C15 O1 -4.8(5) . . . . ?
B1 N1 C15 C14 175.4(3) . . . . ?
B1 N2 C8 C7 -4.6(4) . . . . ?
B1 N2 C8 C9 176.6(3) . . . . ?
B1 N2 C11 C10 -176.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
