# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 
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data_3a
_audit_block_doi                 10.5517/ccdc.csd.cc21x1vw
_database_code_depnum_ccdc_archive 'CCDC 1903798'
loop_
_audit_author_name
_audit_author_address
'tang bing'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-03-17 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-03-17
_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         'C26 H31 B Cl2 F2 N2'
_chemical_formula_sum            'C26 H31 B Cl2 F2 N2'
_chemical_formula_weight         491.24
_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'

_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                   11.2888(6)
_cell_length_b                   6.6366(3)
_cell_length_c                   36.0796(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.894(2)
_cell_angle_gamma                90
_cell_volume                     2688.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9760
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      26.860
_cell_measurement_theta_min      3.049
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0756 before and 0.0555 after correction. The Ratio of minimum to maximum transmission is 0.9206. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            87904
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.048
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4440
_reflns_number_total             6166
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.058
_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)+(0.0408P)²+2.6008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1483
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.21468(7) 0.90712(14) 0.48725(2) 0.0744(2) Uani 1 1 d . . . . .
Cl2 Cl 0.17847(8) 0.55543(15) 0.35109(3) 0.0866(3) Uani 1 1 d . . . . .
F1 F 0.66041(13) 0.8147(3) 0.45077(4) 0.0666(5) Uani 1 1 d . . . . .
F2 F 0.65172(12) 0.6408(2) 0.39697(4) 0.0577(4) Uani 1 1 d . . . . .
N1 N 0.50678(15) 0.5658(3) 0.43893(5) 0.0394(4) Uani 1 1 d . . . . .
N2 N 0.49870(15) 0.8874(3) 0.40375(5) 0.0387(4) Uani 1 1 d . . . . .
C1 C 0.5446(2) 0.3976(4) 0.45710(7) 0.0486(6) Uani 1 1 d . . . . .
H1 H 0.623909 0.358478 0.461481 0.058 Uiso 1 1 calc R . . . .
C2 C 0.4495(2) 0.2901(4) 0.46844(7) 0.0552(6) Uani 1 1 d . . . . .
H2 H 0.453218 0.168819 0.481425 0.066 Uiso 1 1 calc R . . . .
C3 C 0.3486(2) 0.3977(4) 0.45676(7) 0.0497(6) Uani 1 1 d . . . . .
H3 H 0.270924 0.362814 0.460516 0.060 Uiso 1 1 calc R . . . .
C4 C 0.38364(18) 0.5695(3) 0.43818(6) 0.0396(5) Uani 1 1 d . . . . .
C5 C 0.31917(17) 0.7269(3) 0.42005(6) 0.0393(5) Uani 1 1 d . . . . .
C6 C 0.37430(18) 0.8805(3) 0.40278(6) 0.0398(5) Uani 1 1 d . . . . .
C7 C 0.3286(2) 1.0494(4) 0.38267(7) 0.0533(6) Uani 1 1 d . . . . .
H7 H 0.248558 1.082618 0.377577 0.064 Uiso 1 1 calc R . . . .
C8 C 0.4223(2) 1.1555(4) 0.37200(8) 0.0595(7) Uani 1 1 d . . . . .
H8 H 0.417831 1.274330 0.358248 0.071 Uiso 1 1 calc R . . . .
C9 C 0.5271(2) 1.0540(4) 0.38541(7) 0.0472(6) Uani 1 1 d . . . . .
C10 C 0.6520(2) 1.1172(4) 0.38143(8) 0.0559(7) Uani 1 1 d . . . . .
H10A H 0.702515 1.073429 0.403330 0.067 Uiso 1 1 calc R . . . .
H10B H 0.655062 1.263165 0.380678 0.067 Uiso 1 1 calc R . . . .
C11 C 0.7026(2) 1.0341(4) 0.34682(8) 0.0565(7) Uani 1 1 d . . . . .
H11A H 0.704892 0.888200 0.348172 0.068 Uiso 1 1 calc R . . . .
H11B H 0.650473 1.071563 0.324848 0.068 Uiso 1 1 calc R . . . .
C12 C 0.8268(2) 1.1129(5) 0.34311(8) 0.0611(7) Uani 1 1 d . . . . .
H12A H 0.822815 1.257978 0.340039 0.073 Uiso 1 1 calc R . . . .
H12B H 0.876666 1.085018 0.366054 0.073 Uiso 1 1 calc R . . . .
C13 C 0.8850(2) 1.0236(5) 0.31095(8) 0.0628(7) Uani 1 1 d . . . . .
H13A H 0.835330 1.050931 0.287950 0.075 Uiso 1 1 calc R . . . .
H13B H 0.889807 0.878505 0.314042 0.075 Uiso 1 1 calc R . . . .
C14 C 1.0090(2) 1.1055(5) 0.30770(8) 0.0677(8) Uani 1 1 d . . . . .
H14A H 1.003908 1.250609 0.304683 0.081 Uiso 1 1 calc R . . . .
H14B H 1.058318 1.078532 0.330797 0.081 Uiso 1 1 calc R . . . .
C15 C 1.0696(3) 1.0187(5) 0.27579(8) 0.0671(8) Uani 1 1 d . . . . .
H15A H 1.019100 1.040823 0.252735 0.080 Uiso 1 1 calc R . . . .
H15B H 1.078146 0.874300 0.279318 0.080 Uiso 1 1 calc R . . . .
C16 C 1.1914(3) 1.1092(6) 0.27215(8) 0.0697(8) Uani 1 1 d . . . . .
H16A H 1.183143 1.254137 0.269468 0.084 Uiso 1 1 calc R . . . .
H16B H 1.242589 1.083258 0.294921 0.084 Uiso 1 1 calc R . . . .
C17 C 1.2509(2) 1.0277(5) 0.23949(8) 0.0632(7) Uani 1 1 d . . . . .
H17A H 1.198802 1.050618 0.216788 0.076 Uiso 1 1 calc R . . . .
H17B H 1.260985 0.883288 0.242501 0.076 Uiso 1 1 calc R . . . .
C18 C 1.3712(2) 1.1218(5) 0.23526(8) 0.0645(7) Uani 1 1 d . . . . .
H18A H 1.361170 1.266283 0.232375 0.077 Uiso 1 1 calc R . . . .
H18B H 1.423410 1.098297 0.257914 0.077 Uiso 1 1 calc R . . . .
C19 C 1.4304(3) 1.0413(5) 0.20255(9) 0.0709(8) Uani 1 1 d . . . . .
H19A H 1.443514 0.897701 0.205931 0.085 Uiso 1 1 calc R . . . .
H19B H 1.376951 1.059835 0.179998 0.085 Uiso 1 1 calc R . . . .
C20 C 1.5480(3) 1.1413(6) 0.19755(12) 0.0975(12) Uani 1 1 d . . . . .
H20A H 1.578182 1.089818 0.175505 0.146 Uiso 1 1 calc GR . . . .
H20B H 1.603878 1.113531 0.218815 0.146 Uiso 1 1 calc GR . . . .
H20C H 1.536527 1.284273 0.195154 0.146 Uiso 1 1 calc GR . . . .
C21 C 0.18662(18) 0.7246(4) 0.41965(7) 0.0459(6) Uani 1 1 d . . . . .
C22 C 0.1306(2) 0.7969(4) 0.44956(9) 0.0608(7) Uani 1 1 d . . . . .
C23 C 0.0079(3) 0.7856(6) 0.44967(12) 0.0885(11) Uani 1 1 d . . . . .
H23 H -0.028418 0.834266 0.469866 0.106 Uiso 1 1 calc R . . . .
C24 C -0.0592(3) 0.7023(7) 0.41981(14) 0.1032(14) Uani 1 1 d . . . . .
H24 H -0.141307 0.693606 0.420072 0.124 Uiso 1 1 calc R . . . .
C25 C -0.0081(3) 0.6314(6) 0.38955(12) 0.0888(11) Uani 1 1 d . . . . .
H25 H -0.054768 0.575656 0.369387 0.107 Uiso 1 1 calc R . . . .
C26 C 0.1146(2) 0.6441(4) 0.38951(9) 0.0623(7) Uani 1 1 d . . . . .
B1 B 0.5850(2) 0.7269(4) 0.42286(7) 0.0408(6) 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
Cl1 C22 1.738(3) . ?
Cl2 C26 1.730(3) . ?
F1 B1 1.379(3) . ?
F2 B1 1.382(3) . ?
N1 C1 1.342(3) . ?
N1 C4 1.388(3) . ?
N1 B1 1.537(3) . ?
N2 C6 1.402(3) . ?
N2 C9 1.344(3) . ?
N2 B1 1.556(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.400(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.376(3) . ?
C5 C21 1.495(3) . ?
C6 C7 1.404(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.403(4) . ?
C9 C10 1.493(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.529(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.515(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.512(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.517(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.512(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.519(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.515(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.517(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.512(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.511(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.391(4) . ?
C21 C26 1.395(4) . ?
C22 C23 1.387(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.368(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.369(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.388(4) . ?

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
C1 N1 C4 106.99(19) . . ?
C1 N1 B1 126.62(19) . . ?
C4 N1 B1 126.37(19) . . ?
C6 N2 B1 124.64(18) . . ?
C9 N2 C6 107.66(19) . . ?
C9 N2 B1 127.70(19) . . ?
N1 C1 H1 124.6 . . ?
N1 C1 C2 110.8(2) . . ?
C2 C1 H1 124.6 . . ?
C1 C2 H2 126.7 . . ?
C3 C2 C1 106.6(2) . . ?
C3 C2 H2 126.7 . . ?
C2 C3 H3 126.1 . . ?
C2 C3 C4 107.7(2) . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C3 107.9(2) . . ?
N1 C4 C5 119.67(19) . . ?
C5 C4 C3 132.4(2) . . ?
C4 C5 C21 118.0(2) . . ?
C6 C5 C4 121.86(19) . . ?
C6 C5 C21 120.1(2) . . ?
N2 C6 C7 107.5(2) . . ?
C5 C6 N2 120.8(2) . . ?
C5 C6 C7 131.7(2) . . ?
C6 C7 H7 126.1 . . ?
C8 C7 C6 107.7(2) . . ?
C8 C7 H7 126.1 . . ?
C7 C8 H8 126.1 . . ?
C7 C8 C9 107.8(2) . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C8 109.3(2) . . ?
N2 C9 C10 123.6(2) . . ?
C8 C9 C10 127.1(2) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C9 C10 C11 114.4(2) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 112.0(2) . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.3(2) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C12 C13 C14 113.3(2) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.5(3) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C14 C15 C16 113.5(3) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.8(3) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C16 C17 C18 113.9(3) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.9(3) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.7(3) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C5 121.6(2) . . ?
C22 C21 C26 117.5(2) . . ?
C26 C21 C5 120.9(2) . . ?
C21 C22 Cl1 119.79(18) . . ?
C23 C22 Cl1 119.1(3) . . ?
C23 C22 C21 121.1(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.5(3) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 120.6 . . ?
C24 C25 C26 118.8(3) . . ?
C26 C25 H25 120.6 . . ?
C21 C26 Cl2 119.85(19) . . ?
C25 C26 Cl2 118.5(3) . . ?
C25 C26 C21 121.6(3) . . ?
F1 B1 F2 109.24(19) . . ?
F1 B1 N1 110.7(2) . . ?
F1 B1 N2 110.2(2) . . ?
F2 B1 N1 109.9(2) . . ?
F2 B1 N2 110.09(19) . . ?
N1 B1 N2 106.60(17) . . ?

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 C22 C23 C24 178.9(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
N1 C4 C5 C6 -0.2(3) . . . . ?
N1 C4 C5 C21 179.6(2) . . . . ?
N2 C6 C7 C8 -0.3(3) . . . . ?
N2 C9 C10 C11 90.3(3) . . . . ?
C1 N1 C4 C3 0.3(3) . . . . ?
C1 N1 C4 C5 -178.5(2) . . . . ?
C1 N1 B1 F1 -61.5(3) . . . . ?
C1 N1 B1 F2 59.3(3) . . . . ?
C1 N1 B1 N2 178.6(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 N1 -0.4(3) . . . . ?
C2 C3 C4 C5 178.2(2) . . . . ?
C3 C4 C5 C6 -178.6(2) . . . . ?
C3 C4 C5 C21 1.1(4) . . . . ?
C4 N1 C1 C2 -0.1(3) . . . . ?
C4 N1 B1 F1 116.8(2) . . . . ?
C4 N1 B1 F2 -122.5(2) . . . . ?
C4 N1 B1 N2 -3.1(3) . . . . ?
C4 C5 C6 N2 -1.9(3) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C4 C5 C21 C22 82.8(3) . . . . ?
C4 C5 C21 C26 -95.4(3) . . . . ?
C5 C6 C7 C8 179.1(3) . . . . ?
C5 C21 C22 Cl1 4.0(4) . . . . ?
C5 C21 C22 C23 -177.0(3) . . . . ?
C5 C21 C26 Cl2 -2.8(4) . . . . ?
C5 C21 C26 C25 176.6(3) . . . . ?
C6 N2 C9 C8 -0.7(3) . . . . ?
C6 N2 C9 C10 178.1(2) . . . . ?
C6 N2 B1 F1 -119.3(2) . . . . ?
C6 N2 B1 F2 120.2(2) . . . . ?
C6 N2 B1 N1 0.9(3) . . . . ?
C6 C5 C21 C22 -97.5(3) . . . . ?
C6 C5 C21 C26 84.3(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 N2 0.5(3) . . . . ?
C7 C8 C9 C10 -178.2(3) . . . . ?
C8 C9 C10 C11 -91.1(3) . . . . ?
C9 N2 C6 C5 -178.8(2) . . . . ?
C9 N2 C6 C7 0.6(3) . . . . ?
C9 N2 B1 F1 61.0(3) . . . . ?
C9 N2 B1 F2 -59.6(3) . . . . ?
C9 N2 B1 N1 -178.8(2) . . . . ?
C9 C10 C11 C12 176.7(2) . . . . ?
C10 C11 C12 C13 175.6(3) . . . . ?
C11 C12 C13 C14 179.7(3) . . . . ?
C12 C13 C14 C15 179.9(3) . . . . ?
C13 C14 C15 C16 177.6(3) . . . . ?
C14 C15 C16 C17 -178.1(3) . . . . ?
C15 C16 C17 C18 178.6(3) . . . . ?
C16 C17 C18 C19 -179.7(3) . . . . ?
C17 C18 C19 C20 177.7(3) . . . . ?
C21 C5 C6 N2 178.3(2) . . . . ?
C21 C5 C6 C7 -1.0(4) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C22 C21 C26 Cl2 178.9(2) . . . . ?
C22 C21 C26 C25 -1.6(4) . . . . ?
C22 C23 C24 C25 -0.7(7) . . . . ?
C23 C24 C25 C26 0.3(7) . . . . ?
C24 C25 C26 Cl2 -179.7(3) . . . . ?
C24 C25 C26 C21 0.9(6) . . . . ?
C26 C21 C22 Cl1 -177.7(2) . . . . ?
C26 C21 C22 C23 1.3(4) . . . . ?
B1 N1 C1 C2 178.5(2) . . . . ?
B1 N1 C4 C3 -178.2(2) . . . . ?
B1 N1 C4 C5 3.0(3) . . . . ?
B1 N2 C6 C5 1.4(3) . . . . ?
B1 N2 C6 C7 -179.2(2) . . . . ?
B1 N2 C9 C8 179.1(2) . . . . ?
B1 N2 C9 C10 -2.2(4) . . . . ?

_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_5a
_audit_block_doi                 10.5517/ccdc.csd.cc21x1yz
_database_code_depnum_ccdc_archive 'CCDC 1903801'
loop_
_audit_author_name
_audit_author_address
'tang bing'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-03-17 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-03-17
_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         'C22 H17 B Br Cl2 F2 N3'
_chemical_formula_sum            'C22 H17 B Br Cl2 F2 N3'
_chemical_formula_weight         523.01
_chemical_absolute_configuration ?
_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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.0040(14)
_cell_length_b                   14.206(3)
_cell_length_c                   22.139(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2202.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9784
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.662
_shelx_estimated_absorpt_T_min   0.617
_exptl_absorpt_coefficient_mu    2.141
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1091 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7188.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            95463
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.634
_diffrn_reflns_theta_min         3.012
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.898
_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                   ?
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                3946
_reflns_number_total             5041
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.139
_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)+(0.0578P)²+3.2731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1652
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.99(2)
 0.01(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Riding coordinates:
 N1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C6(H6), C7(H7), C11(H11), C12(H12), C19(H19),
 C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Br1 Br 0.36461(19) 0.69452(10) 0.11406(5) 0.1004(4) Uani 1 1 d . . . . .
Cl1 Cl 0.9436(4) 0.69745(14) 0.46209(8) 0.0695(6) Uani 1 1 d . . . . .
Cl2 Cl 0.6195(6) 0.36608(18) 0.52199(11) 0.1041(11) Uani 1 1 d . . . . .
F1 F 0.8123(6) 0.5334(2) 0.25332(15) 0.0457(9) Uani 1 1 d . . . . .
F2 F 0.6483(6) 0.4000(2) 0.27062(16) 0.0471(9) Uani 1 1 d . . . . .
N1 N 1.0235(10) 0.3766(5) 0.2152(2) 0.0592(17) Uani 1 1 d . . . . .
H1 H 0.930382 0.415529 0.210703 0.071 Uiso 1 1 d R . . . .
N2 N 0.8976(7) 0.4407(3) 0.3403(2) 0.0343(11) Uani 1 1 d . . . . .
N3 N 0.5917(7) 0.5318(3) 0.3364(2) 0.0341(11) Uani 1 1 d . . . . .
C1 C 1.1121(14) 0.3298(6) 0.1694(3) 0.070(2) Uani 1 1 d . . . . .
H1A H 1.085083 0.336216 0.128479 0.085 Uiso 1 1 calc R . . . .
C2 C 1.2446(13) 0.2730(6) 0.1932(4) 0.067(2) Uani 1 1 d . . . . .
H2 H 1.322498 0.231269 0.172208 0.081 Uiso 1 1 calc R . . . .
C3 C 1.2440(11) 0.2881(5) 0.2554(4) 0.0574(19) Uani 1 1 d . . . . .
H3 H 1.324026 0.258951 0.283205 0.069 Uiso 1 1 calc R . . . .
C4 C 1.1054(9) 0.3532(4) 0.2687(3) 0.0416(14) Uani 1 1 d . . . . .
C5 C 1.0518(9) 0.3875(4) 0.3271(3) 0.0393(14) Uani 1 1 d . . . . .
C6 C 1.1594(11) 0.3717(5) 0.3803(3) 0.0522(16) Uani 1 1 d . . . . .
H6 H 1.272521 0.337617 0.382929 0.063 Uiso 1 1 calc R . . . .
C7 C 1.0695(12) 0.4147(5) 0.4265(3) 0.0553(18) Uani 1 1 d . . . . .
H7 H 1.108786 0.414967 0.466676 0.066 Uiso 1 1 calc R . . . .
C8 C 0.9030(10) 0.4597(4) 0.4029(2) 0.0384(14) Uani 1 1 d . . . . .
C9 C 0.7620(9) 0.5114(4) 0.4304(2) 0.0379(14) Uani 1 1 d . . . . .
C10 C 0.6074(10) 0.5458(4) 0.3987(2) 0.0384(14) Uani 1 1 d . . . . .
C11 C 0.4452(11) 0.5985(5) 0.4160(3) 0.0500(17) Uani 1 1 d . . . . .
H11 H 0.416015 0.617904 0.455043 0.060 Uiso 1 1 calc R . . . .
C12 C 0.3395(11) 0.6161(5) 0.3660(3) 0.0489(16) Uani 1 1 d . . . . .
H12 H 0.225388 0.649514 0.364738 0.059 Uiso 1 1 calc R . . . .
C13 C 0.4326(9) 0.5749(4) 0.3163(3) 0.0395(14) Uani 1 1 d . . . . .
C14 C 0.3768(11) 0.5759(5) 0.2510(3) 0.0489(15) Uani 1 1 d . . . . .
H14A H 0.327045 0.514356 0.240377 0.059 Uiso 1 1 calc R . . . .
H14B H 0.490343 0.586553 0.226863 0.059 Uiso 1 1 calc R . . . .
C15 C 0.2307(13) 0.6488(6) 0.2346(4) 0.065(2) Uani 1 1 d . . . . .
H15A H 0.117725 0.639127 0.259178 0.079 Uiso 1 1 calc R . . . .
H15B H 0.281287 0.710587 0.244079 0.079 Uiso 1 1 calc R . . . .
C16 C 0.1746(14) 0.6465(7) 0.1693(4) 0.074(2) Uani 1 1 d . . . . .
H16A H 0.058469 0.682882 0.164378 0.088 Uiso 1 1 calc R . . . .
H16B H 0.145800 0.581944 0.158307 0.088 Uiso 1 1 calc R . . . .
C17 C 0.7844(10) 0.5320(4) 0.4967(2) 0.0402(14) Uani 1 1 d . . . . .
C18 C 0.8708(11) 0.6156(4) 0.5149(2) 0.0462(15) Uani 1 1 d . . . . .
C19 C 0.9087(12) 0.6357(6) 0.5755(3) 0.0570(19) Uani 1 1 d . . . . .
H19 H 0.967676 0.691734 0.586760 0.068 Uiso 1 1 calc R . . . .
C20 C 0.8562(13) 0.5704(6) 0.6178(3) 0.067(2) Uani 1 1 d . . . . .
H20 H 0.883310 0.581920 0.658296 0.080 Uiso 1 1 calc R . . . .
C21 C 0.7650(14) 0.4887(6) 0.6025(3) 0.069(2) Uani 1 1 d . . . . .
H21 H 0.728041 0.445852 0.632053 0.083 Uiso 1 1 calc R . . . .
C22 C 0.7286(12) 0.4708(5) 0.5416(3) 0.0567(19) Uani 1 1 d . . . . .
B1 B 0.7351(10) 0.4765(5) 0.2988(3) 0.0329(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
Br1 C16 1.932(10) . ?
Cl1 C18 1.726(6) . ?
Cl2 C22 1.729(8) . ?
F1 B1 1.400(7) . ?
F2 B1 1.393(7) . ?
N1 H1 0.8604 . ?
N1 C1 1.362(9) . ?
N1 C4 1.358(9) . ?
N2 C5 1.351(8) . ?
N2 C8 1.411(7) . ?
N2 B1 1.549(8) . ?
N3 C10 1.397(7) . ?
N3 C13 1.347(8) . ?
N3 B1 1.523(8) . ?
C1 H1A 0.9300 . ?
C1 C2 1.338(12) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(9) . ?
C4 C5 1.432(8) . ?
C5 C6 1.417(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.348(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.429(10) . ?
C8 C9 1.374(9) . ?
C9 C10 1.379(9) . ?
C9 C17 1.504(7) . ?
C10 C11 1.414(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.355(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.406(9) . ?
C13 C14 1.499(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.499(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.498(12) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.392(9) . ?
C17 C22 1.379(9) . ?
C18 C19 1.398(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.368(12) . ?
C21 H21 0.9300 . ?
C21 C22 1.394(10) . ?

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
C1 N1 H1 125.0 . . ?
C4 N1 H1 125.3 . . ?
C4 N1 C1 109.7(7) . . ?
C5 N2 C8 107.4(5) . . ?
C5 N2 B1 130.0(5) . . ?
C8 N2 B1 122.6(5) . . ?
C10 N3 B1 124.1(5) . . ?
C13 N3 C10 109.0(5) . . ?
C13 N3 B1 126.9(5) . . ?
N1 C1 H1A 125.7 . . ?
C2 C1 N1 108.5(7) . . ?
C2 C1 H1A 125.7 . . ?
C1 C2 H2 126.4 . . ?
C1 C2 C3 107.1(6) . . ?
C3 C2 H2 126.4 . . ?
C2 C3 H3 125.7 . . ?
C4 C3 C2 108.5(7) . . ?
C4 C3 H3 125.7 . . ?
N1 C4 C3 106.1(6) . . ?
N1 C4 C5 126.4(6) . . ?
C3 C4 C5 127.5(6) . . ?
N2 C5 C4 126.6(5) . . ?
N2 C5 C6 109.5(5) . . ?
C6 C5 C4 123.9(6) . . ?
C5 C6 H6 125.9 . . ?
C7 C6 C5 108.1(6) . . ?
C7 C6 H6 125.9 . . ?
C6 C7 H7 126.1 . . ?
C6 C7 C8 107.8(6) . . ?
C8 C7 H7 126.1 . . ?
N2 C8 C7 107.2(5) . . ?
C9 C8 N2 121.2(6) . . ?
C9 C8 C7 131.6(5) . . ?
C8 C9 C10 121.8(5) . . ?
C8 C9 C17 117.5(6) . . ?
C10 C9 C17 120.7(5) . . ?
N3 C10 C11 106.2(5) . . ?
C9 C10 N3 120.9(5) . . ?
C9 C10 C11 132.8(5) . . ?
C10 C11 H11 125.8 . . ?
C12 C11 C10 108.4(5) . . ?
C12 C11 H11 125.8 . . ?
C11 C12 H12 126.0 . . ?
C11 C12 C13 108.0(6) . . ?
C13 C12 H12 126.0 . . ?
N3 C13 C12 108.4(6) . . ?
N3 C13 C14 122.6(5) . . ?
C12 C13 C14 129.0(6) . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C13 C14 C15 114.7(6) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.4(7) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
Br1 C16 H16A 108.5 . . ?
Br1 C16 H16B 108.5 . . ?
C15 C16 Br1 115.0(7) . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C9 119.6(5) . . ?
C22 C17 C9 123.5(6) . . ?
C22 C17 C18 116.8(5) . . ?
C17 C18 Cl1 120.4(4) . . ?
C17 C18 C19 122.4(6) . . ?
C19 C18 Cl1 117.1(6) . . ?
C18 C19 H19 121.1 . . ?
C20 C19 C18 117.8(7) . . ?
C20 C19 H19 121.1 . . ?
C19 C20 H20 119.0 . . ?
C21 C20 C19 122.1(6) . . ?
C21 C20 H20 119.0 . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.7(7) . . ?
C22 C21 H21 120.7 . . ?
C17 C22 Cl2 119.1(5) . . ?
C17 C22 C21 122.1(7) . . ?
C21 C22 Cl2 118.7(6) . . ?
F1 B1 N2 109.5(5) . . ?
F1 B1 N3 110.5(5) . . ?
F2 B1 F1 107.2(5) . . ?
F2 B1 N2 109.3(5) . . ?
F2 B1 N3 111.1(5) . . ?
N3 B1 N2 109.3(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 C18 C19 C20 -178.4(6) . . . . ?
N1 C1 C2 C3 -2.6(11) . . . . ?
N1 C4 C5 N2 8.0(11) . . . . ?
N1 C4 C5 C6 -170.2(7) . . . . ?
N2 C5 C6 C7 0.7(8) . . . . ?
N2 C8 C9 C10 1.1(10) . . . . ?
N2 C8 C9 C17 -177.2(6) . . . . ?
N3 C10 C11 C12 -0.8(7) . . . . ?
N3 C13 C14 C15 -163.2(6) . . . . ?
C1 N1 C4 C3 -1.8(9) . . . . ?
C1 N1 C4 C5 -179.8(7) . . . . ?
C1 C2 C3 C4 1.5(10) . . . . ?
C2 C3 C4 N1 0.2(9) . . . . ?
C2 C3 C4 C5 178.1(7) . . . . ?
C3 C4 C5 N2 -169.5(7) . . . . ?
C3 C4 C5 C6 12.3(11) . . . . ?
C4 N1 C1 C2 2.9(10) . . . . ?
C4 C5 C6 C7 179.2(6) . . . . ?
C5 N2 C8 C7 -0.1(7) . . . . ?
C5 N2 C8 C9 -178.8(6) . . . . ?
C5 N2 B1 F1 -60.5(8) . . . . ?
C5 N2 B1 F2 56.7(8) . . . . ?
C5 N2 B1 N3 178.4(5) . . . . ?
C5 C6 C7 C8 -0.7(9) . . . . ?
C6 C7 C8 N2 0.5(8) . . . . ?
C6 C7 C8 C9 179.1(7) . . . . ?
C7 C8 C9 C10 -177.3(7) . . . . ?
C7 C8 C9 C17 4.4(11) . . . . ?
C8 N2 C5 C4 -178.8(6) . . . . ?
C8 N2 C5 C6 -0.4(7) . . . . ?
C8 N2 B1 F1 120.7(6) . . . . ?
C8 N2 B1 F2 -122.1(6) . . . . ?
C8 N2 B1 N3 -0.4(8) . . . . ?
C8 C9 C10 N3 -2.2(9) . . . . ?
C8 C9 C10 C11 179.0(7) . . . . ?
C8 C9 C17 C18 93.3(8) . . . . ?
C8 C9 C17 C22 -84.8(9) . . . . ?
C9 C10 C11 C12 178.2(7) . . . . ?
C9 C17 C18 Cl1 2.5(10) . . . . ?
C9 C17 C18 C19 -175.2(7) . . . . ?
C9 C17 C22 Cl2 -2.2(10) . . . . ?
C9 C17 C22 C21 174.8(8) . . . . ?
C10 N3 C13 C12 -1.3(7) . . . . ?
C10 N3 C13 C14 178.1(6) . . . . ?
C10 N3 B1 F1 -121.2(6) . . . . ?
C10 N3 B1 F2 119.9(6) . . . . ?
C10 N3 B1 N2 -0.7(8) . . . . ?
C10 C9 C17 C18 -85.0(8) . . . . ?
C10 C9 C17 C22 96.9(8) . . . . ?
C10 C11 C12 C13 0.0(8) . . . . ?
C11 C12 C13 N3 0.8(8) . . . . ?
C11 C12 C13 C14 -178.6(7) . . . . ?
C12 C13 C14 C15 16.1(11) . . . . ?
C13 N3 C10 C9 -177.8(6) . . . . ?
C13 N3 C10 C11 1.3(7) . . . . ?
C13 N3 B1 F1 58.6(8) . . . . ?
C13 N3 B1 F2 -60.3(8) . . . . ?
C13 N3 B1 N2 179.1(5) . . . . ?
C13 C14 C15 C16 -178.7(7) . . . . ?
C14 C15 C16 Br1 -73.2(9) . . . . ?
C17 C9 C10 N3 176.0(5) . . . . ?
C17 C9 C10 C11 -2.8(11) . . . . ?
C17 C18 C19 C20 -0.6(12) . . . . ?
C18 C17 C22 Cl2 179.7(6) . . . . ?
C18 C17 C22 C21 -3.3(12) . . . . ?
C18 C19 C20 C21 -1.7(14) . . . . ?
C19 C20 C21 C22 1.4(14) . . . . ?
C20 C21 C22 Cl2 178.2(7) . . . . ?
C20 C21 C22 C17 1.2(13) . . . . ?
C22 C17 C18 Cl1 -179.3(6) . . . . ?
C22 C17 C18 C19 3.0(11) . . . . ?
B1 N2 C5 C4 2.3(10) . . . . ?
B1 N2 C5 C6 -179.3(6) . . . . ?
B1 N2 C8 C7 179.0(6) . . . . ?
B1 N2 C8 C9 0.2(9) . . . . ?
B1 N3 C10 C9 2.0(9) . . . . ?
B1 N3 C10 C11 -178.9(6) . . . . ?
B1 N3 C13 C12 178.9(6) . . . . ?
B1 N3 C13 C14 -1.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.99(2)
2 0.01(2)

####################################################################### 
# 
# 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_4e
_audit_block_doi                 10.5517/ccdc.csd.cc21x1xy
_database_code_depnum_ccdc_archive 'CCDC 1903800'
loop_
_audit_author_name
_audit_author_address
'tang bing'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-03-17 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-03-17
_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         'C31 H25 B Cl2 F2 N2'
_chemical_formula_sum            'C31 H25 B Cl2 F2 N2'
_chemical_formula_weight         545.24
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   7.2552(4)
_cell_length_b                   16.7595(9)
_cell_length_c                   22.7809(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2770.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9718
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1470 before and 0.0628 after correction. The Ratio of minimum to maximum transmission is 0.8011. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.21
_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  0.0588
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            135158
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.584
_diffrn_reflns_theta_min         3.018
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2587
_reflns_number_total             3130
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.332
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.291
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.1217
_refine_ls_restrained_S_all      1.291
_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)+(0.0307P)²+5.7465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2182
_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:
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.9261(3) 0.60820(12) 0.52084(8) 0.1232(8) Uani 1 1 d . . . . .
F1 F 0.8358(4) 0.69390(14) 0.29557(9) 0.0598(7) Uani 1 1 d . . . . .
N1 N 0.6055(5) 0.71001(19) 0.37102(12) 0.0463(8) Uani 1 1 d . . . . .
C1 C 0.750000 0.750000 0.6494(3) 0.125(5) Uani 1 2 d S T P . .
H1 H 0.750002 0.749999 0.690223 0.150 Uiso 1 2 calc RS T P . .
C2 C 0.8310(9) 0.6892(5) 0.6199(2) 0.111(3) Uani 1 1 d . . . . .
H2 H 0.887758 0.648157 0.640555 0.133 Uiso 1 1 calc R . . . .
C3 C 0.8298(7) 0.6878(4) 0.55883(19) 0.0831(17) Uani 1 1 d . . . . .
C4 C 0.750000 0.750000 0.5277(2) 0.0603(17) Uani 1 2 d S T P . .
C5 C 0.750000 0.750000 0.4618(2) 0.0515(14) Uani 1 2 d S T P . .
C6 C 0.6070(6) 0.7134(3) 0.43257(15) 0.0499(10) Uani 1 1 d . . . . .
C7 C 0.4502(6) 0.6732(3) 0.45230(18) 0.0677(13) Uani 1 1 d . . . . .
H7 H 0.415357 0.666702 0.491298 0.081 Uiso 1 1 calc R . . . .
C8 C 0.3572(7) 0.6450(4) 0.40475(18) 0.0742(15) Uani 1 1 d . . . . .
H8 H 0.248381 0.615658 0.405222 0.089 Uiso 1 1 calc R . . . .
C9 C 0.4572(6) 0.6687(3) 0.35466(17) 0.0582(11) Uani 1 1 d . . . . .
C10 C 0.4200(7) 0.6500(3) 0.29126(18) 0.0719(14) Uani 1 1 d . . . . .
H10A H 0.387752 0.699042 0.271125 0.086 Uiso 1 1 calc R . . . .
H10B H 0.532273 0.629731 0.273588 0.086 Uiso 1 1 calc R . . . .
C11 C 0.2708(7) 0.5911(3) 0.28194(19) 0.0687(13) Uani 1 1 d . . . . .
H11A H 0.157033 0.611983 0.298164 0.082 Uiso 1 1 calc R . . . .
H11B H 0.300722 0.542403 0.302899 0.082 Uiso 1 1 calc R . . . .
C12 C 0.2418(6) 0.5718(3) 0.21774(18) 0.0566(10) Uani 1 1 d . . . . .
C13 C 0.1456(9) 0.6222(4) 0.1822(2) 0.101(2) Uani 1 1 d . . . . .
H13 H 0.098177 0.669415 0.197411 0.121 Uiso 1 1 calc R . . . .
C14 C 0.1176(10) 0.6037(5) 0.1236(2) 0.115(3) Uani 1 1 d . . . . .
H14 H 0.049999 0.638334 0.100075 0.139 Uiso 1 1 calc R . . . .
C15 C 0.1877(8) 0.5357(4) 0.1000(2) 0.0829(16) Uani 1 1 d . . . . .
H15 H 0.168367 0.523345 0.060696 0.100 Uiso 1 1 calc R . . . .
C16 C 0.2861(8) 0.4862(3) 0.1350(2) 0.0787(15) Uani 1 1 d . . . . .
H16 H 0.335938 0.439593 0.119503 0.094 Uiso 1 1 calc R . . . .
C17 C 0.3129(7) 0.5043(3) 0.1932(2) 0.0690(13) Uani 1 1 d . . . . .
H17 H 0.381207 0.469538 0.216437 0.083 Uiso 1 1 calc R . . . .
B1 B 0.750000 0.750000 0.3307(2) 0.0424(13) Uani 1 2 d S T P . .


_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 C3 1.737(6) . ?
F1 B1 1.383(4) . ?
N1 C6 1.403(4) . ?
N1 C9 1.333(5) . ?
N1 B1 1.546(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.355(8) 2_665 ?
C1 C2 1.355(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(7) . ?
C3 C4 1.388(6) . ?
C4 C5 1.501(7) . ?
C5 C6 1.376(5) 2_665 ?
C5 C6 1.376(5) . ?
C6 C7 1.397(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.361(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.409(6) . ?
C9 C10 1.503(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.480(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.513(6) . ?
C12 C13 1.363(7) . ?
C12 C17 1.364(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.359(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.353(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(7) . ?
C17 H17 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 B1 124.8(3) . . ?
C9 N1 C6 107.9(3) . . ?
C9 N1 B1 127.4(3) . . ?
C2 C1 H1 119.8 2_665 . ?
C2 C1 H1 119.8 . . ?
C2 C1 C2 120.5(7) 2_665 . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(7) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 Cl1 120.6(5) . . ?
C4 C3 Cl1 119.3(3) . . ?
C4 C3 C2 120.1(6) . . ?
C3 C4 C3 118.5(6) . 2_665 ?
C3 C4 C5 120.8(3) . . ?
C3 C4 C5 120.8(3) 2_665 . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 C4 118.9(2) 2_665 . ?
C6 C5 C6 122.2(5) 2_665 . ?
C5 C6 N1 120.5(4) . . ?
C5 C6 C7 132.3(4) . . ?
C7 C6 N1 107.2(4) . . ?
C6 C7 H7 125.8 . . ?
C8 C7 C6 108.4(4) . . ?
C8 C7 H7 125.8 . . ?
C7 C8 H8 126.5 . . ?
C7 C8 C9 106.9(4) . . ?
C9 C8 H8 126.5 . . ?
N1 C9 C8 109.6(4) . . ?
N1 C9 C10 121.5(4) . . ?
C8 C9 C10 128.8(4) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.1(4) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C12 112.5(4) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 C17 117.7(4) . . ?
C17 C12 C11 121.4(4) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(5) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.9(6) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.6(5) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(5) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 121.7(5) . . ?
C12 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
F1 B1 F1 109.2(4) 2_665 . ?
F1 B1 N1 110.75(15) . . ?
F1 B1 N1 109.48(16) . 2_665 ?
F1 B1 N1 110.74(15) 2_665 2_665 ?
F1 B1 N1 109.48(16) 2_665 . ?
N1 B1 N1 107.2(4) . 2_665 ?

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 C3 C4 C3 178.6(5) . . . 2_665 ?
Cl1 C3 C4 C5 -1.4(5) . . . . ?
N1 C6 C7 C8 0.9(6) . . . . ?
N1 C9 C10 C11 168.8(4) . . . . ?
C1 C2 C3 Cl1 -177.6(4) . . . . ?
C1 C2 C3 C4 1.8(8) . . . . ?
C2 C1 C2 C3 -0.9(4) 2_665 . . . ?
C2 C3 C4 C3 -0.9(4) . . . 2_665 ?
C2 C3 C4 C5 179.1(4) . . . . ?
C3 C4 C5 C6 88.5(3) . . . . ?
C3 C4 C5 C6 -91.5(3) 2_665 . . . ?
C3 C4 C5 C6 88.5(3) 2_665 . . 2_665 ?
C3 C4 C5 C6 -91.5(3) . . . 2_665 ?
C4 C5 C6 N1 -177.9(3) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C5 C6 C7 C8 -177.1(4) . . . . ?
C6 N1 C9 C8 0.7(5) . . . . ?
C6 N1 C9 C10 -176.6(4) . . . . ?
C6 N1 B1 F1 -118.1(4) . . . 2_665 ?
C6 N1 B1 F1 121.5(4) . . . . ?
C6 N1 B1 N1 2.1(3) . . . 2_665 ?
C6 C5 C6 N1 2.1(3) 2_665 . . . ?
C6 C5 C6 C7 179.8(6) 2_665 . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 N1 -0.2(6) . . . . ?
C7 C8 C9 C10 176.8(5) . . . . ?
C8 C9 C10 C11 -7.9(8) . . . . ?
C9 N1 C6 C5 177.3(3) . . . . ?
C9 N1 C6 C7 -1.0(5) . . . . ?
C9 N1 B1 F1 -60.4(5) . . . . ?
C9 N1 B1 F1 60.0(4) . . . 2_665 ?
C9 N1 B1 N1 -179.8(4) . . . 2_665 ?
C9 C10 C11 C12 -178.1(5) . . . . ?
C10 C11 C12 C13 -79.1(7) . . . . ?
C10 C11 C12 C17 100.0(6) . . . . ?
C11 C12 C13 C14 -179.2(6) . . . . ?
C11 C12 C17 C16 179.6(5) . . . . ?
C12 C13 C14 C15 -1.0(12) . . . . ?
C13 C12 C17 C16 -1.3(8) . . . . ?
C13 C14 C15 C16 -0.2(11) . . . . ?
C14 C15 C16 C17 0.6(9) . . . . ?
C15 C16 C17 C12 0.2(9) . . . . ?
C17 C12 C13 C14 1.7(10) . . . . ?
B1 N1 C6 C5 -4.3(5) . . . . ?
B1 N1 C6 C7 177.4(3) . . . . ?
B1 N1 C9 C8 -177.7(3) . . . . ?
B1 N1 C9 C10 5.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
