# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# 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_20200824h
_audit_block_doi                 10.5517/ccdc.csd.cc2799c7
_database_code_depnum_ccdc_archive 'CCDC 2064518'
loop_
_audit_author_name
_audit_author_address
'qingzheng yang'
;beijing normal university
China
;
_audit_update_record             
;
2021-02-23 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_audit_creation_date             2020-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H24 B Cl2 F N2 O2'
_chemical_formula_sum            'C39 H24 B Cl2 F N2 O2'
_chemical_formula_weight         653.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1o1b1f1Cl1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.0101(4)
_cell_length_b                   10.3606(2)
_cell_length_c                   13.4292(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.414(4)
_cell_angle_gamma                90
_cell_volume                     1592.10(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8484
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.8450
_cell_measurement_theta_min      3.7690
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.734
_exptl_absorpt_coefficient_mu    2.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic purple'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10899
_diffrn_reflns_point_group_measured_fraction_full 0.749
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.931
_diffrn_reflns_theta_min         3.742
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  25.00   0.50    0.05    --  -47.95  74.00  87.00  158
  2  ω     50.00 102.00   0.50    0.05    --   47.95  74.00  87.00  104
  3  ω     99.00 175.00   0.50    0.10    --  104.75  74.00  87.00  152
  4  ω     91.00 178.00   0.50    0.10    --  104.75  15.00  30.00  174
  5  ω     76.00 108.00   0.50    0.10    --  104.75 -77.00 120.00   64
  6  ω     41.00  67.00   0.50    0.10    --  104.75 -61.00 120.00   52
  7  ω     32.00  63.00   0.50    0.10    --  104.75 -77.00 120.00   62
  8  ω     46.00  87.00   0.50    0.10    --  104.75 -74.00 -41.00   82
  9  ω     41.00  73.00   0.50    0.10    --  104.75 -61.00 -30.00   64
 10  ω    -22.00  69.00   0.50    0.05    --   47.95 -74.00 -41.00  182
 11  ω    -67.00 -30.00   0.50    0.10    -- -102.00  61.00 -60.00   74
 12  ω    -69.00 -43.00   0.50    0.10    -- -102.00  61.00 -30.00   52
 13  ω    -94.00 -54.00   0.50    0.10    -- -102.00  74.00  87.00   80
 14  ω    -68.00 -29.00   0.50    0.10    -- -102.00  61.00  90.00   78
 15  ω    -68.00 -35.00   0.50    0.10    -- -102.00  61.00 150.00   66
 16  ω   -111.00 -85.00   0.50    0.10    -- -102.00 -61.00  30.00   52
 17  ω    -97.00 -72.00   0.50    0.05    --  -47.95 -74.00 -41.00   50
 18  ω    -64.00 -31.00   0.50    0.10    -- -102.00  61.00-150.00   66
 19  ω    -98.00 -73.00   0.50    0.10    -- -102.00  77.00-180.00   50
 20  ω   -175.00-150.00   0.50    0.10    -- -102.00 -74.00 -41.00   50
 21  ω   -166.00-125.00   0.50    0.10    -- -102.00 -61.00  30.00   82
 22  ω   -147.00-114.00   0.50    0.10    -- -102.00 -45.00  30.00   66
 23  ω   -120.00 -72.00   0.50    0.05    --  -47.95-125.00 120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0728304000
_diffrn_orient_matrix_UB_12      -0.1117019000
_diffrn_orient_matrix_UB_13      -0.0099241000
_diffrn_orient_matrix_UB_21      -0.1077014000
_diffrn_orient_matrix_UB_22      -0.0477353000
_diffrn_orient_matrix_UB_23      -0.1077979000
_diffrn_orient_matrix_UB_31      0.0345703000
_diffrn_orient_matrix_UB_32      0.0859653000
_diffrn_orient_matrix_UB_33      -0.0728583000
_diffrn_oxdiff_digest_frames     
;
01253d1be5e7fe13239d19e6ac9d08b12500158acf9
;
_diffrn_oxdiff_digest_hkl        
;
0187ee5a653e87770dfb3c6430bb45c91775ff
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.394
_reflns_Friedel_fraction_full    0.467
_reflns_Friedel_fraction_max     0.424
_reflns_number_gt                4545
_reflns_number_total             4690
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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         0.210
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1241 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(10)
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         4690
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.033
_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)+(0.0468P)²+0.2951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0836
_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), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C28(H28), C29(H29), C31(H31),
  C32(H32), C35(H35), C36(H36), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.57590(7) 0.57082(8) 0.50194(6) 0.03976(19) Uani 1 1 d . . . . .
Cl2 Cl 0.20975(5) 0.40329(7) 0.69293(6) 0.03168(17) Uani 1 1 d . . . . .
F1 F 0.72055(14) -0.16087(16) 0.84235(12) 0.0251(3) Uani 1 1 d . . . . .
O1 O 0.62755(15) -0.02732(18) 0.91412(14) 0.0205(4) Uani 1 1 d . . . . .
O2 O 0.87594(17) 0.3320(2) 1.01954(16) 0.0297(4) Uani 1 1 d . . . . .
N1 N 0.70211(18) -0.2474(2) 0.99920(17) 0.0195(4) Uani 1 1 d . . . . .
N2 N 0.83236(17) -0.0673(2) 1.02862(17) 0.0204(4) Uani 1 1 d . . . . .
C1 C 0.2556(3) -0.1388(3) 0.6463(2) 0.0310(6) Uani 1 1 d . . . . .
H1 H 0.3161 -0.1162 0.6314 0.037 Uiso 1 1 calc R . . . .
C2 C 0.1429(3) -0.0940(4) 0.5765(2) 0.0382(7) Uani 1 1 d . . . . .
H2 H 0.1285 -0.0400 0.5159 0.046 Uiso 1 1 calc R . . . .
C3 C 0.0522(3) -0.1298(4) 0.5969(3) 0.0421(9) Uani 1 1 d . . . . .
H3 H -0.0230 -0.0994 0.5504 0.050 Uiso 1 1 calc R . . . .
C4 C 0.0734(3) -0.2104(4) 0.6859(3) 0.0405(8) Uani 1 1 d . . . . .
H4 H 0.0120 -0.2356 0.6985 0.049 Uiso 1 1 calc R . . . .
C5 C 0.1854(2) -0.2545(3) 0.7570(2) 0.0306(6) Uani 1 1 d . . . . .
H5 H 0.1988 -0.3088 0.8172 0.037 Uiso 1 1 calc R . . . .
C6 C 0.2783(2) -0.2175(3) 0.7387(2) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.3948(2) -0.2573(3) 0.8167(2) 0.0248(6) Uani 1 1 d . . . . .
C8 C 0.4922(2) -0.2847(3) 0.8872(2) 0.0222(5) Uani 1 1 d . . . . .
C9 C 0.6053(2) -0.3197(3) 0.9744(2) 0.0199(5) Uani 1 1 d . . . . .
C10 C 0.6371(2) -0.4268(3) 1.04651(19) 0.0213(5) Uani 1 1 d . . . . .
H10 H 0.5868 -0.4895 1.0483 0.026 Uiso 1 1 calc R . . . .
C11 C 0.7574(2) -0.4223(3) 1.1148(2) 0.0212(5) Uani 1 1 d . . . . .
H11 H 0.8028 -0.4823 1.1698 0.025 Uiso 1 1 calc R . . . .
C12 C 0.7979(2) -0.3106(3) 1.0856(2) 0.0196(5) Uani 1 1 d . . . . .
C13 C 0.9116(2) -0.2564(3) 1.1394(2) 0.0208(5) Uani 1 1 d . . . . .
C14 C 1.0099(2) -0.3345(3) 1.2244(2) 0.0210(5) Uani 1 1 d . . . . .
C15 C 1.0410(2) -0.4485(3) 1.1896(2) 0.0232(5) Uani 1 1 d . . . . .
H15 H 0.9995 -0.4749 1.1145 0.028 Uiso 1 1 calc R . . . .
C16 C 1.1335(2) -0.5223(3) 1.2668(2) 0.0256(6) Uani 1 1 d . . . . .
H16 H 1.1548 -0.5966 1.2423 0.031 Uiso 1 1 calc R . . . .
C17 C 1.1952(2) -0.4872(3) 1.3804(2) 0.0270(6) Uani 1 1 d . . . . .
C18 C 1.1626(2) -0.3759(3) 1.4148(2) 0.0287(6) Uani 1 1 d . . . . .
H18 H 1.2024 -0.3518 1.4906 0.034 Uiso 1 1 calc R . . . .
C19 C 1.0711(2) -0.2990(3) 1.3380(2) 0.0255(6) Uani 1 1 d . . . . .
H19 H 1.0510 -0.2239 1.3626 0.031 Uiso 1 1 calc R . . . .
C20 C 1.2940(3) -0.5710(4) 1.4634(3) 0.0378(7) Uani 1 1 d . . . . .
H20A H 1.2625 -0.6481 1.4782 0.057 Uiso 1 1 calc GR . . . .
H20B H 1.3380 -0.5245 1.5329 0.057 Uiso 1 1 calc GR . . . .
H20C H 1.3442 -0.5937 1.4320 0.057 Uiso 1 1 calc GR . . . .
C21 C 0.9275(2) -0.1308(3) 1.1137(2) 0.0214(5) Uani 1 1 d . . . . .
C22 C 1.0191(2) -0.0389(3) 1.1630(2) 0.0233(5) Uani 1 1 d . . . . .
H22 H 1.0942 -0.0549 1.2211 0.028 Uiso 1 1 calc R . . . .
C23 C 0.9780(2) 0.0773(3) 1.1102(2) 0.0232(5) Uani 1 1 d . . . . .
H23 H 1.0196 0.1543 1.1258 0.028 Uiso 1 1 calc R . . . .
C24 C 0.8582(2) 0.0578(3) 1.0260(2) 0.0204(5) Uani 1 1 d . . . . .
C25 C 0.7656(2) 0.1422(3) 0.9511(2) 0.0200(5) Uani 1 1 d . . . . .
C26 C 0.7952(2) 0.2775(3) 0.9392(2) 0.0215(5) Uani 1 1 d . . . . .
C27 C 0.7325(2) 0.3467(3) 0.8281(2) 0.0198(5) Uani 1 1 d . . . . .
C28 C 0.7232(2) 0.4807(3) 0.8294(2) 0.0220(5) Uani 1 1 d . . . . .
H28 H 0.7514 0.5238 0.8982 0.026 Uiso 1 1 calc R . . . .
C29 C 0.6724(2) 0.5504(3) 0.7294(2) 0.0255(6) Uani 1 1 d . . . . .
H29 H 0.6639 0.6395 0.7298 0.031 Uiso 1 1 calc R . . . .
C30 C 0.6345(3) 0.4833(3) 0.6284(2) 0.0275(6) Uani 1 1 d . . . . .
C31 C 0.6428(2) 0.3507(3) 0.6246(2) 0.0267(6) Uani 1 1 d . . . . .
H31 H 0.6164 0.3081 0.5557 0.032 Uiso 1 1 calc R . . . .
C32 C 0.6914(2) 0.2821(3) 0.7256(2) 0.0241(6) Uani 1 1 d . . . . .
H32 H 0.6963 0.1926 0.7247 0.029 Uiso 1 1 calc R . . . .
C33 C 0.6519(2) 0.0957(3) 0.9054(2) 0.0198(5) Uani 1 1 d . . . . .
C34 C 0.5457(2) 0.1760(3) 0.8499(2) 0.0202(5) Uani 1 1 d . . . . .
C35 C 0.5397(2) 0.2973(3) 0.8919(2) 0.0214(5) Uani 1 1 d . . . . .
H35 H 0.6054 0.3312 0.9534 0.026 Uiso 1 1 calc R . . . .
C36 C 0.4365(2) 0.3678(3) 0.8428(2) 0.0231(5) Uani 1 1 d . . . . .
H36 H 0.4325 0.4484 0.8712 0.028 Uiso 1 1 calc R . . . .
C37 C 0.3396(2) 0.3161(3) 0.7506(2) 0.0242(5) Uani 1 1 d . . . . .
C38 C 0.3436(2) 0.1969(3) 0.7068(2) 0.0248(6) Uani 1 1 d . . . . .
H38 H 0.2780 0.1640 0.6444 0.030 Uiso 1 1 calc R . . . .
C39 C 0.4469(2) 0.1267(3) 0.7572(2) 0.0233(5) Uani 1 1 d . . . . .
H39 H 0.4502 0.0459 0.7288 0.028 Uiso 1 1 calc R . . . .
B1 B 0.7181(2) -0.1268(3) 0.9419(2) 0.0202(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 C30 1.748(3) . ?
Cl2 C37 1.739(3) . ?
F1 B1 1.397(3) . ?
O1 C33 1.332(3) . ?
O1 B1 1.473(3) . ?
O2 C26 1.227(3) . ?
N1 C9 1.363(3) . ?
N1 C12 1.397(3) . ?
N1 B1 1.533(4) . ?
N2 C21 1.387(3) . ?
N2 C24 1.344(3) . ?
N2 B1 1.516(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.392(4) . ?
C1 C6 1.393(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(4) . ?
C6 C7 1.433(4) . ?
C7 C8 1.201(4) . ?
C8 C9 1.424(4) . ?
C9 C10 1.401(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(4) . ?
C12 C13 1.417(4) . ?
C13 C14 1.485(4) . ?
C13 C21 1.387(4) . ?
C14 C15 1.399(4) . ?
C14 C19 1.393(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(4) . ?
C17 C18 1.383(4) . ?
C17 C20 1.511(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.396(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.419(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.371(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.439(3) . ?
C24 C25 1.441(4) . ?
C25 C26 1.482(4) . ?
C25 C33 1.391(4) . ?
C26 C27 1.499(4) . ?
C27 C28 1.395(4) . ?
C27 C32 1.389(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.385(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.389(4) . ?
C30 C31 1.381(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.389(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.475(4) . ?
C34 C35 1.395(4) . ?
C34 C39 1.392(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.388(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.387(4) . ?
C37 C38 1.380(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.389(4) . ?
C39 H39 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
C33 O1 B1 119.8(2) . . ?
C9 N1 C12 107.5(2) . . ?
C9 N1 B1 130.9(2) . . ?
C12 N1 B1 121.3(2) . . ?
C21 N2 B1 127.2(2) . . ?
C24 N2 C21 110.0(2) . . ?
C24 N2 B1 122.5(2) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.2(3) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C7 121.4(3) . . ?
C5 C6 C7 119.7(3) . . ?
C8 C7 C6 175.5(3) . . ?
C7 C8 C9 177.0(3) . . ?
N1 C9 C8 122.3(2) . . ?
N1 C9 C10 109.4(2) . . ?
C10 C9 C8 128.3(2) . . ?
C9 C10 H10 126.3 . . ?
C11 C10 C9 107.4(2) . . ?
C11 C10 H10 126.3 . . ?
C10 C11 H11 126.3 . . ?
C10 C11 C12 107.4(2) . . ?
C12 C11 H11 126.3 . . ?
N1 C12 C11 108.3(2) . . ?
N1 C12 C13 122.6(2) . . ?
C11 C12 C13 128.7(2) . . ?
C12 C13 C14 119.0(2) . . ?
C21 C13 C12 119.2(2) . . ?
C21 C13 C14 121.8(2) . . ?
C15 C14 C13 118.9(2) . . ?
C19 C14 C13 122.2(2) . . ?
C19 C14 C15 118.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C20 120.2(3) . . ?
C18 C17 C16 118.4(3) . . ?
C18 C17 C20 121.4(3) . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 C18 120.1(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 106.8(2) . . ?
C13 C21 N2 118.0(2) . . ?
C13 C21 C22 134.9(2) . . ?
C21 C22 H22 125.9 . . ?
C23 C22 C21 108.3(2) . . ?
C23 C22 H22 125.9 . . ?
C22 C23 H23 126.5 . . ?
C22 C23 C24 107.0(2) . . ?
C24 C23 H23 126.5 . . ?
N2 C24 C23 107.8(2) . . ?
N2 C24 C25 117.9(2) . . ?
C23 C24 C25 134.1(3) . . ?
C24 C25 C26 118.4(2) . . ?
C33 C25 C24 117.2(2) . . ?
C33 C25 C26 123.8(2) . . ?
O2 C26 C25 119.9(2) . . ?
O2 C26 C27 119.2(2) . . ?
C25 C26 C27 120.8(2) . . ?
C28 C27 C26 118.2(2) . . ?
C32 C27 C26 121.8(2) . . ?
C32 C27 C28 119.8(2) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 121.0 . . ?
C28 C29 C30 118.0(3) . . ?
C30 C29 H29 121.0 . . ?
C29 C30 Cl1 118.5(2) . . ?
C31 C30 Cl1 119.1(2) . . ?
C31 C30 C29 122.4(3) . . ?
C30 C31 H31 120.7 . . ?
C30 C31 C32 118.7(3) . . ?
C32 C31 H31 120.7 . . ?
C27 C32 C31 120.2(3) . . ?
C27 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
O1 C33 C25 122.7(2) . . ?
O1 C33 C34 112.3(2) . . ?
C25 C33 C34 124.9(2) . . ?
C35 C34 C33 121.5(2) . . ?
C39 C34 C33 119.3(2) . . ?
C39 C34 C35 119.1(2) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.6(2) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 120.5 . . ?
C37 C36 C35 118.9(3) . . ?
C37 C36 H36 120.5 . . ?
C36 C37 Cl2 118.4(2) . . ?
C38 C37 Cl2 120.0(2) . . ?
C38 C37 C36 121.6(2) . . ?
C37 C38 H38 120.5 . . ?
C37 C38 C39 119.0(2) . . ?
C39 C38 H38 120.5 . . ?
C34 C39 H39 119.6 . . ?
C38 C39 C34 120.8(3) . . ?
C38 C39 H39 119.6 . . ?
F1 B1 O1 108.3(2) . . ?
F1 B1 N1 110.1(2) . . ?
F1 B1 N2 112.2(2) . . ?
O1 B1 N1 114.5(2) . . ?
O1 B1 N2 106.5(2) . . ?
N2 B1 N1 105.2(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
Cl1 C30 C31 C32 178.9(2) . . . . ?
Cl2 C37 C38 C39 -177.3(2) . . . . ?
O1 C33 C34 C35 136.0(2) . . . . ?
O1 C33 C34 C39 -40.3(3) . . . . ?
O2 C26 C27 C28 -31.4(3) . . . . ?
O2 C26 C27 C32 144.0(3) . . . . ?
N1 C9 C10 C11 -2.1(3) . . . . ?
N1 C12 C13 C14 -175.5(2) . . . . ?
N1 C12 C13 C21 6.4(4) . . . . ?
N2 C21 C22 C23 1.6(3) . . . . ?
N2 C24 C25 C26 -174.3(2) . . . . ?
N2 C24 C25 C33 13.6(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C1 C6 C5 2.5(4) . . . . ?
C2 C1 C6 C7 -175.4(3) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 -1.7(5) . . . . ?
C4 C5 C6 C7 176.3(3) . . . . ?
C6 C1 C2 C3 -1.5(5) . . . . ?
C8 C9 C10 C11 178.1(2) . . . . ?
C9 N1 C12 C11 -1.1(3) . . . . ?
C9 N1 C12 C13 -174.3(2) . . . . ?
C9 N1 B1 F1 -77.0(3) . . . . ?
C9 N1 B1 O1 45.3(4) . . . . ?
C9 N1 B1 N2 161.9(2) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C10 C11 C12 N1 -0.2(3) . . . . ?
C10 C11 C12 C13 172.4(2) . . . . ?
C11 C12 C13 C14 12.8(4) . . . . ?
C11 C12 C13 C21 -165.3(2) . . . . ?
C12 N1 C9 C8 -178.2(2) . . . . ?
C12 N1 C9 C10 1.9(3) . . . . ?
C12 N1 B1 F1 95.7(3) . . . . ?
C12 N1 B1 O1 -141.9(2) . . . . ?
C12 N1 B1 N2 -25.4(3) . . . . ?
C12 C13 C14 C15 63.6(3) . . . . ?
C12 C13 C14 C19 -115.5(3) . . . . ?
C12 C13 C21 N2 -5.6(3) . . . . ?
C12 C13 C21 C22 166.0(3) . . . . ?
C13 C14 C15 C16 179.0(2) . . . . ?
C13 C14 C19 C18 179.7(3) . . . . ?
C13 C21 C22 C23 -170.6(3) . . . . ?
C14 C13 C21 N2 176.4(2) . . . . ?
C14 C13 C21 C22 -12.0(4) . . . . ?
C14 C15 C16 C17 1.8(4) . . . . ?
C15 C14 C19 C18 0.7(4) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C17 C20 178.5(3) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C14 0.7(4) . . . . ?
C19 C14 C15 C16 -1.9(4) . . . . ?
C20 C17 C18 C19 -179.8(3) . . . . ?
C21 N2 C24 C23 2.6(3) . . . . ?
C21 N2 C24 C25 -173.4(2) . . . . ?
C21 N2 B1 F1 -91.7(3) . . . . ?
C21 N2 B1 O1 149.9(2) . . . . ?
C21 N2 B1 N1 28.0(3) . . . . ?
C21 C13 C14 C15 -118.4(3) . . . . ?
C21 C13 C14 C19 62.5(3) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 N2 -1.5(3) . . . . ?
C22 C23 C24 C25 173.5(3) . . . . ?
C23 C24 C25 C26 11.0(4) . . . . ?
C23 C24 C25 C33 -161.1(3) . . . . ?
C24 N2 C21 C13 171.1(2) . . . . ?
C24 N2 C21 C22 -2.7(3) . . . . ?
C24 N2 B1 F1 82.4(3) . . . . ?
C24 N2 B1 O1 -35.9(3) . . . . ?
C24 N2 B1 N1 -157.8(2) . . . . ?
C24 C25 C26 O2 -31.1(3) . . . . ?
C24 C25 C26 C27 145.2(2) . . . . ?
C24 C25 C33 O1 -10.6(3) . . . . ?
C24 C25 C33 C34 164.9(2) . . . . ?
C25 C26 C27 C28 152.3(2) . . . . ?
C25 C26 C27 C32 -32.3(4) . . . . ?
C25 C33 C34 C35 -39.9(3) . . . . ?
C25 C33 C34 C39 143.8(3) . . . . ?
C26 C25 C33 O1 177.8(2) . . . . ?
C26 C25 C33 C34 -6.7(4) . . . . ?
C26 C27 C28 C29 176.1(2) . . . . ?
C26 C27 C32 C31 -174.3(2) . . . . ?
C27 C28 C29 C30 -2.0(4) . . . . ?
C28 C27 C32 C31 1.0(4) . . . . ?
C28 C29 C30 Cl1 -177.3(2) . . . . ?
C28 C29 C30 C31 1.8(4) . . . . ?
C29 C30 C31 C32 -0.3(4) . . . . ?
C30 C31 C32 C27 -1.2(4) . . . . ?
C32 C27 C28 C29 0.6(4) . . . . ?
C33 O1 B1 F1 -82.1(3) . . . . ?
C33 O1 B1 N1 154.5(2) . . . . ?
C33 O1 B1 N2 38.7(3) . . . . ?
C33 C25 C26 O2 140.4(3) . . . . ?
C33 C25 C26 C27 -43.3(3) . . . . ?
C33 C34 C35 C36 -175.9(2) . . . . ?
C33 C34 C39 C38 176.5(2) . . . . ?
C34 C35 C36 C37 -0.4(4) . . . . ?
C35 C34 C39 C38 0.1(4) . . . . ?
C35 C36 C37 Cl2 177.90(19) . . . . ?
C35 C36 C37 C38 -0.1(4) . . . . ?
C36 C37 C38 C39 0.7(4) . . . . ?
C37 C38 C39 C34 -0.7(4) . . . . ?
C39 C34 C35 C36 0.4(4) . . . . ?
B1 O1 C33 C25 -18.5(3) . . . . ?
B1 O1 C33 C34 165.5(2) . . . . ?
B1 N1 C9 C8 -4.7(4) . . . . ?
B1 N1 C9 C10 175.4(2) . . . . ?
B1 N1 C12 C11 -175.3(2) . . . . ?
B1 N1 C12 C13 11.5(4) . . . . ?
B1 N2 C21 C13 -14.1(4) . . . . ?
B1 N2 C21 C22 172.1(2) . . . . ?
B1 N2 C24 C23 -172.4(2) . . . . ?
B1 N2 C24 C25 11.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.704
####################################################################### 
# 
# 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_20200910a
_audit_block_doi                 10.5517/ccdc.csd.cc2799f9
_database_code_depnum_ccdc_archive 'CCDC 2064520'
loop_
_audit_author_name
_audit_author_address
'qingzheng yang'
;beijing normal university
China
;
_audit_update_record             
;
2021-02-23 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_audit_creation_date             2020-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H24 B Cl2 F N2 O2'
_chemical_formula_sum            'C39 H24 B Cl2 F N2 O2'
_chemical_formula_weight         653.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1o1B1F1Cl1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.1863(4)
_cell_length_b                   10.3824(2)
_cell_length_c                   13.6545(5)
_cell_angle_alpha                90
_cell_angle_beta                 118.391(5)
_cell_angle_gamma                90
_cell_volume                     1644.54(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5900
_cell_measurement_temperature    301.13(11)
_cell_measurement_theta_max      74.2960
_cell_measurement_theta_min      3.6570
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.568
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark purple'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12505
_diffrn_reflns_point_group_measured_fraction_full 0.799
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.897
_diffrn_reflns_theta_min         3.680
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.13(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -26.00   0.50    0.10    --  -47.95  48.00 113.00   50
  2  ω    -17.00  25.00   0.50    0.10    --  -47.95  48.00 113.00   84
  3  ω   -118.00 -66.00   0.50    0.10    --  -47.95 -48.00 -34.00  104
  4  ω    -63.00 -35.00   0.50    0.10    --  -47.95 -48.00 -34.00   56
  5  ω     -8.00  17.00   0.50    0.10    --   47.95 -48.00 -34.00   50
  6  ω     91.00 177.00   0.50    0.50    --  104.75  48.00 113.00  172
  7  ω    -24.00  28.00   0.50    0.10    --  -47.95  19.00 -90.00  104
  8  ω   -119.00 -74.00   0.50    0.10    --  -47.95-125.00 -90.00   90
  9  ω   -119.00 -72.00   0.50    0.10    --  -47.95-125.00  90.00   94
 10  ω     72.00 101.00   0.50    0.10    --   47.95  48.00 113.00   58
 11  ω   -102.00 -29.00   0.50    0.50    -- -102.00  77.00-180.00  146
 12  ω    -60.00 -32.00   0.50    0.50    -- -102.00  61.00-120.00   56
 13  ω   -175.00 -86.00   0.50    0.50    -- -102.00 -61.00  60.00  178
 14  ω   -154.00-118.00   0.50    0.50    -- -102.00 -61.00  90.00   72
 15  ω    -68.00 -42.00   0.50    0.50    -- -102.00  61.00  60.00   52
 16  ω   -113.00 -86.00   0.50    0.50    -- -102.00 -61.00  90.00   54
 17  ω    -99.00 -74.00   0.50    0.50    -- -102.00  77.00  30.00   50
 18  ω    -54.00 -29.00   0.50    0.50    -- -102.00  77.00  30.00   50
 19  ω   -172.00-111.00   0.50    0.50    -- -102.00 -48.00 -34.00  122
 20  ω     70.00 109.00   0.50    0.50    --  104.75 -94.00 150.00   78
 21  ω     33.00  58.00   0.50    0.50    --  104.75 -94.00 150.00   50
 22  ω     32.00  72.00   0.50    0.50    --  104.75 -61.00 -30.00   80
 23  ω    140.00 177.00   0.50    0.50    --  104.75  30.00-150.00   74
 24  ω    104.00 137.00   0.50    0.50    --  104.75  30.00-150.00   66
 25  ω     32.00  70.00   0.50    0.50    --  104.75 -61.00-180.00   76
 26  ω     38.00  73.00   0.50    0.50    --  104.75 -61.00 -90.00   70
 27  ω     40.00  68.00   0.50    0.50    --  104.75 -61.00-150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1185525000
_diffrn_orient_matrix_UB_12      0.0667912000
_diffrn_orient_matrix_UB_13      -0.0505932000
_diffrn_orient_matrix_UB_21      0.0211400000
_diffrn_orient_matrix_UB_22      0.0570855000
_diffrn_orient_matrix_UB_23      -0.0928604000
_diffrn_orient_matrix_UB_31      -0.0559526000
_diffrn_orient_matrix_UB_32      -0.1196093000
_diffrn_orient_matrix_UB_33      -0.0725162000
_diffrn_oxdiff_digest_frames     
;
01906ab4e2db5f3a4dd2677f18248a3c6902192a947
;
_diffrn_oxdiff_digest_hkl        
;
01f5f7f023d13b77755e295b4c11405112017d
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.484
_reflns_Friedel_fraction_full    0.574
_reflns_Friedel_fraction_max     0.524
_reflns_number_gt                4498
_reflns_number_total             5178
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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         0.165
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(13)
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.034
_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)+(0.0548P)²+0.0287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1063
_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), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C28(H28), C29(H29), C31(H31),
  C32(H32), C35(H35), C36(H36), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.08011(14) -0.19495(14) -0.99424(10) 0.1083(5) Uani 1 1 d . . . . .
Cl2 Cl -0.28946(8) -0.02770(12) -0.81076(10) 0.0882(3) Uani 1 1 d . . . . .
F1 F 0.21403(17) 0.5334(2) -0.65920(16) 0.0609(5) Uani 1 1 d . . . . .
O1 O 0.12320(17) 0.39986(19) -0.58899(18) 0.0487(5) Uani 1 1 d . . . . .
O2 O 0.3669(2) 0.0422(2) -0.4860(2) 0.0766(8) Uani 1 1 d . . . . .
N1 N 0.1963(2) 0.6193(2) -0.5050(2) 0.0442(5) Uani 1 1 d . . . . .
N2 N 0.3247(2) 0.4396(2) -0.4773(2) 0.0475(6) Uani 1 1 d . . . . .
C1 C -0.2412(4) 0.5191(5) -0.8529(4) 0.0897(14) Uani 1 1 d . . . . .
H1 H -0.1807 0.4974 -0.8667 0.108 Uiso 1 1 calc R . . . .
C2 C -0.3530(6) 0.4772(6) -0.9251(4) 0.118(2) Uani 1 1 d . . . . .
H2 H -0.3673 0.4272 -0.9868 0.142 Uiso 1 1 calc R . . . .
C3 C -0.4423(6) 0.5107(8) -0.9041(6) 0.130(3) Uani 1 1 d . . . . .
H3 H -0.5168 0.4821 -0.9508 0.156 Uiso 1 1 calc R . . . .
C4 C -0.4211(4) 0.5837(9) -0.8171(6) 0.131(3) Uani 1 1 d . . . . .
H4 H -0.4822 0.6078 -0.8050 0.157 Uiso 1 1 calc R . . . .
C5 C -0.3122(3) 0.6251(6) -0.7440(4) 0.0877(13) Uani 1 1 d . . . . .
H5 H -0.3000 0.6751 -0.6829 0.105 Uiso 1 1 calc R . . . .
C6 C -0.2208(3) 0.5921(4) -0.7617(3) 0.0629(9) Uani 1 1 d . . . . .
C7 C -0.1065(3) 0.6299(3) -0.6826(3) 0.0555(7) Uani 1 1 d . . . . .
C8 C -0.0105(3) 0.6558(3) -0.6133(3) 0.0508(7) Uani 1 1 d . . . . .
C9 C 0.1012(2) 0.6909(3) -0.5285(2) 0.0459(6) Uani 1 1 d . . . . .
C10 C 0.1332(3) 0.7975(3) -0.4578(2) 0.0489(6) Uani 1 1 d . . . . .
H10 H 0.0838 0.8602 -0.4558 0.059 Uiso 1 1 calc R . . . .
C11 C 0.2508(3) 0.7931(3) -0.3916(2) 0.0491(6) Uani 1 1 d . . . . .
H11 H 0.2956 0.8528 -0.3375 0.059 Uiso 1 1 calc R . . . .
C12 C 0.2906(2) 0.6821(3) -0.4207(2) 0.0467(6) Uani 1 1 d . . . . .
C13 C 0.4035(3) 0.6284(3) -0.3689(3) 0.0480(6) Uani 1 1 d . . . . .
C14 C 0.5010(2) 0.7068(3) -0.2858(3) 0.0492(7) Uani 1 1 d . . . . .
C15 C 0.5314(3) 0.8192(4) -0.3216(3) 0.0586(8) Uani 1 1 d . . . . .
H15 H 0.4904 0.8443 -0.3958 0.070 Uiso 1 1 calc R . . . .
C16 C 0.6226(3) 0.8930(4) -0.2468(4) 0.0665(9) Uani 1 1 d . . . . .
H16 H 0.6437 0.9662 -0.2720 0.080 Uiso 1 1 calc R . . . .
C17 C 0.6831(3) 0.8608(4) -0.1354(4) 0.0689(10) Uani 1 1 d . . . . .
C18 C 0.6507(4) 0.7513(5) -0.1005(3) 0.0752(11) Uani 1 1 d . . . . .
H18 H 0.6896 0.7286 -0.0257 0.090 Uiso 1 1 calc R . . . .
C19 C 0.5609(3) 0.6739(4) -0.1750(3) 0.0654(9) Uani 1 1 d . . . . .
H19 H 0.5413 0.5996 -0.1498 0.079 Uiso 1 1 calc R . . . .
C20 C 0.7814(4) 0.9443(6) -0.0543(5) 0.1105(19) Uani 1 1 d . . . . .
H20A H 0.8411 0.9466 -0.0754 0.166 Uiso 1 1 calc GR . . . .
H20B H 0.8116 0.9091 0.0193 0.166 Uiso 1 1 calc GR . . . .
H20C H 0.7537 1.0301 -0.0553 0.166 Uiso 1 1 calc GR . . . .
C21 C 0.4188(2) 0.5040(3) -0.3948(3) 0.0501(7) Uani 1 1 d . . . . .
C22 C 0.5093(3) 0.4122(3) -0.3479(3) 0.0577(8) Uani 1 1 d . . . . .
H22 H 0.5840 0.4283 -0.2920 0.069 Uiso 1 1 calc R . . . .
C23 C 0.4686(3) 0.2971(3) -0.3983(3) 0.0577(7) Uani 1 1 d . . . . .
H23 H 0.5097 0.2203 -0.3828 0.069 Uiso 1 1 calc R . . . .
C24 C 0.3505(2) 0.3156(3) -0.4797(3) 0.0481(6) Uani 1 1 d . . . . .
C25 C 0.2592(3) 0.2315(3) -0.5530(3) 0.0468(6) Uani 1 1 d . . . . .
C26 C 0.2890(3) 0.0958(3) -0.5652(3) 0.0510(7) Uani 1 1 d . . . . .
C27 C 0.2289(3) 0.0274(3) -0.6737(3) 0.0485(6) Uani 1 1 d . . . . .
C28 C 0.2223(3) -0.1059(3) -0.6733(3) 0.0538(7) Uani 1 1 d . . . . .
H28 H 0.2511 -0.1495 -0.6059 0.065 Uiso 1 1 calc R . . . .
C29 C 0.1735(3) -0.1748(3) -0.7714(3) 0.0622(8) Uani 1 1 d . . . . .
H29 H 0.1665 -0.2639 -0.7709 0.075 Uiso 1 1 calc R . . . .
C30 C 0.1355(4) -0.1088(4) -0.8701(3) 0.0668(9) Uani 1 1 d . . . . .
C31 C 0.1429(4) 0.0233(4) -0.8726(3) 0.0701(9) Uani 1 1 d . . . . .
H31 H 0.1173 0.0663 -0.9400 0.084 Uiso 1 1 calc R . . . .
C32 C 0.1884(3) 0.0912(3) -0.7743(3) 0.0587(8) Uani 1 1 d . . . . .
H32 H 0.1919 0.1806 -0.7754 0.070 Uiso 1 1 calc R . . . .
C33 C 0.1470(2) 0.2774(3) -0.5981(2) 0.0453(6) Uani 1 1 d . . . . .
C34 C 0.0422(2) 0.1981(3) -0.6536(2) 0.0451(6) Uani 1 1 d . . . . .
C35 C 0.0352(3) 0.0771(3) -0.6131(3) 0.0497(7) Uani 1 1 d . . . . .
H35 H 0.0993 0.0429 -0.5521 0.060 Uiso 1 1 calc R . . . .
C36 C -0.0668(3) 0.0072(3) -0.6629(3) 0.0560(7) Uani 1 1 d . . . . .
H36 H -0.0712 -0.0735 -0.6357 0.067 Uiso 1 1 calc R . . . .
C37 C -0.1611(3) 0.0588(3) -0.7531(3) 0.0572(8) Uani 1 1 d . . . . .
C38 C -0.1560(3) 0.1776(4) -0.7946(3) 0.0644(9) Uani 1 1 d . . . . .
H38 H -0.2203 0.2110 -0.8559 0.077 Uiso 1 1 calc R . . . .
C39 C -0.0546(3) 0.2468(3) -0.7446(3) 0.0561(7) Uani 1 1 d . . . . .
H39 H -0.0512 0.3275 -0.7723 0.067 Uiso 1 1 calc R . . . .
B1 B 0.2117(3) 0.4987(3) -0.5621(3) 0.0456(7) 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 C30 1.741(4) . ?
Cl2 C37 1.739(3) . ?
F1 B1 1.389(4) . ?
O1 C33 1.329(4) . ?
O1 B1 1.463(4) . ?
O2 C26 1.216(4) . ?
N1 C9 1.359(4) . ?
N1 C12 1.391(4) . ?
N1 B1 1.539(4) . ?
N2 C21 1.388(4) . ?
N2 C24 1.336(4) . ?
N2 B1 1.516(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.397(8) . ?
C1 C6 1.370(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.321(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(6) . ?
C6 C7 1.430(5) . ?
C7 C8 1.196(5) . ?
C8 C9 1.422(5) . ?
C9 C10 1.396(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.400(4) . ?
C12 C13 1.423(4) . ?
C13 C14 1.489(4) . ?
C13 C21 1.379(5) . ?
C14 C15 1.396(5) . ?
C14 C19 1.376(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(6) . ?
C17 C18 1.376(6) . ?
C17 C20 1.515(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.392(5) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.420(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.356(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.433(4) . ?
C24 C25 1.438(4) . ?
C25 C26 1.493(4) . ?
C25 C33 1.389(4) . ?
C26 C27 1.487(5) . ?
C27 C28 1.387(4) . ?
C27 C32 1.383(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.378(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.376(5) . ?
C30 C31 1.377(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.471(4) . ?
C34 C35 1.393(4) . ?
C34 C39 1.386(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.388(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.376(5) . ?
C37 C38 1.372(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.379(5) . ?
C39 H39 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
C33 O1 B1 119.9(2) . . ?
C9 N1 C12 107.5(2) . . ?
C9 N1 B1 130.9(2) . . ?
C12 N1 B1 121.3(2) . . ?
C21 N2 B1 126.8(2) . . ?
C24 N2 C21 110.2(2) . . ?
C24 N2 B1 122.7(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 119.9(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(6) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.3(7) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 121.3(4) . . ?
C5 C6 C7 119.6(4) . . ?
C8 C7 C6 176.5(4) . . ?
C7 C8 C9 177.1(3) . . ?
N1 C9 C8 122.3(3) . . ?
N1 C9 C10 109.2(3) . . ?
C10 C9 C8 128.5(3) . . ?
C9 C10 H10 126.2 . . ?
C11 C10 C9 107.7(3) . . ?
C11 C10 H10 126.2 . . ?
C10 C11 H11 126.3 . . ?
C10 C11 C12 107.4(3) . . ?
C12 C11 H11 126.3 . . ?
N1 C12 C11 108.2(2) . . ?
N1 C12 C13 122.7(3) . . ?
C11 C12 C13 128.8(3) . . ?
C12 C13 C14 119.0(3) . . ?
C21 C13 C12 119.1(3) . . ?
C21 C13 C14 121.9(3) . . ?
C15 C14 C13 118.5(3) . . ?
C19 C14 C13 122.6(3) . . ?
C19 C14 C15 118.9(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C20 120.8(4) . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C20 121.2(4) . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.3(4) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 C18 120.2(3) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 106.1(3) . . ?
C13 C21 N2 118.4(3) . . ?
C13 C21 C22 135.0(3) . . ?
C21 C22 H22 125.7 . . ?
C23 C22 C21 108.5(3) . . ?
C23 C22 H22 125.7 . . ?
C22 C23 H23 126.4 . . ?
C22 C23 C24 107.3(3) . . ?
C24 C23 H23 126.4 . . ?
N2 C24 C23 107.8(3) . . ?
N2 C24 C25 117.6(3) . . ?
C23 C24 C25 134.4(3) . . ?
C24 C25 C26 118.2(3) . . ?
C33 C25 C24 117.6(3) . . ?
C33 C25 C26 123.8(3) . . ?
O2 C26 C25 119.2(3) . . ?
O2 C26 C27 119.5(3) . . ?
C27 C26 C25 121.2(3) . . ?
C28 C27 C26 118.6(3) . . ?
C32 C27 C26 122.1(3) . . ?
C32 C27 C28 119.1(3) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(3) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 120.7 . . ?
C30 C29 C28 118.6(3) . . ?
C30 C29 H29 120.7 . . ?
C29 C30 Cl1 119.1(3) . . ?
C29 C30 C31 121.5(4) . . ?
C31 C30 Cl1 119.3(3) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 C30 119.3(4) . . ?
C32 C31 H31 120.4 . . ?
C27 C32 H32 119.8 . . ?
C31 C32 C27 120.5(3) . . ?
C31 C32 H32 119.8 . . ?
O1 C33 C25 122.4(3) . . ?
O1 C33 C34 112.2(2) . . ?
C25 C33 C34 125.3(3) . . ?
C35 C34 C33 121.6(3) . . ?
C39 C34 C33 119.8(3) . . ?
C39 C34 C35 118.5(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.6(3) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 120.4 . . ?
C37 C36 C35 119.2(3) . . ?
C37 C36 H36 120.4 . . ?
C36 C37 Cl2 118.4(3) . . ?
C38 C37 Cl2 120.3(3) . . ?
C38 C37 C36 121.3(3) . . ?
C37 C38 H38 120.4 . . ?
C37 C38 C39 119.3(3) . . ?
C39 C38 H38 120.4 . . ?
C34 C39 H39 119.4 . . ?
C38 C39 C34 121.1(3) . . ?
C38 C39 H39 119.4 . . ?
F1 B1 O1 108.6(3) . . ?
F1 B1 N1 109.9(2) . . ?
F1 B1 N2 112.0(3) . . ?
O1 B1 N1 114.6(2) . . ?
O1 B1 N2 106.6(2) . . ?
N2 B1 N1 105.1(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
Cl1 C30 C31 C32 -179.0(3) . . . . ?
Cl2 C37 C38 C39 177.3(3) . . . . ?
O1 C33 C34 C35 -135.7(3) . . . . ?
O1 C33 C34 C39 40.6(4) . . . . ?
O2 C26 C27 C28 29.3(5) . . . . ?
O2 C26 C27 C32 -145.2(3) . . . . ?
N1 C9 C10 C11 1.7(3) . . . . ?
N1 C12 C13 C14 175.1(3) . . . . ?
N1 C12 C13 C21 -6.7(4) . . . . ?
N2 C21 C22 C23 -2.0(4) . . . . ?
N2 C24 C25 C26 174.0(3) . . . . ?
N2 C24 C25 C33 -13.2(4) . . . . ?
C1 C2 C3 C4 1.2(10) . . . . ?
C2 C1 C6 C5 -1.2(7) . . . . ?
C2 C1 C6 C7 176.2(4) . . . . ?
C2 C3 C4 C5 -1.9(11) . . . . ?
C3 C4 C5 C6 1.1(10) . . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C4 C5 C6 C7 -176.9(5) . . . . ?
C6 C1 C2 C3 0.4(8) . . . . ?
C8 C9 C10 C11 -178.4(3) . . . . ?
C9 N1 C12 C11 1.0(3) . . . . ?
C9 N1 C12 C13 174.7(3) . . . . ?
C9 N1 B1 F1 77.5(4) . . . . ?
C9 N1 B1 O1 -45.1(4) . . . . ?
C9 N1 B1 N2 -161.8(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 N1 0.0(3) . . . . ?
C10 C11 C12 C13 -173.1(3) . . . . ?
C11 C12 C13 C14 -12.6(5) . . . . ?
C11 C12 C13 C21 165.6(3) . . . . ?
C12 N1 C9 C8 178.5(3) . . . . ?
C12 N1 C9 C10 -1.7(3) . . . . ?
C12 N1 B1 F1 -95.3(3) . . . . ?
C12 N1 B1 O1 142.0(3) . . . . ?
C12 N1 B1 N2 25.3(3) . . . . ?
C12 C13 C14 C15 -64.9(4) . . . . ?
C12 C13 C14 C19 114.0(4) . . . . ?
C12 C13 C21 N2 5.1(4) . . . . ?
C12 C13 C21 C22 -166.0(4) . . . . ?
C13 C14 C15 C16 -179.1(3) . . . . ?
C13 C14 C19 C18 -179.4(4) . . . . ?
C13 C21 C22 C23 169.8(4) . . . . ?
C14 C13 C21 N2 -176.8(3) . . . . ?
C14 C13 C21 C22 12.0(6) . . . . ?
C14 C15 C16 C17 -2.0(5) . . . . ?
C15 C14 C19 C18 -0.4(6) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C15 C16 C17 C20 -178.9(4) . . . . ?
C16 C17 C18 C19 1.0(6) . . . . ?
C17 C18 C19 C14 -1.1(6) . . . . ?
C19 C14 C15 C16 1.9(5) . . . . ?
C20 C17 C18 C19 -179.6(4) . . . . ?
C21 N2 C24 C23 -2.3(3) . . . . ?
C21 N2 C24 C25 174.1(3) . . . . ?
C21 N2 B1 F1 90.6(4) . . . . ?
C21 N2 B1 O1 -150.8(3) . . . . ?
C21 N2 B1 N1 -28.7(4) . . . . ?
C21 C13 C14 C15 117.0(4) . . . . ?
C21 C13 C14 C19 -64.0(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 N2 1.0(4) . . . . ?
C22 C23 C24 C25 -174.5(3) . . . . ?
C23 C24 C25 C26 -10.8(5) . . . . ?
C23 C24 C25 C33 162.0(3) . . . . ?
C24 N2 C21 C13 -170.8(3) . . . . ?
C24 N2 C21 C22 2.7(3) . . . . ?
C24 N2 B1 F1 -82.8(3) . . . . ?
C24 N2 B1 O1 35.8(4) . . . . ?
C24 N2 B1 N1 157.9(3) . . . . ?
C24 C25 C26 O2 32.8(4) . . . . ?
C24 C25 C26 C27 -144.3(3) . . . . ?
C24 C25 C33 O1 10.0(4) . . . . ?
C24 C25 C33 C34 -165.7(3) . . . . ?
C25 C26 C27 C28 -153.6(3) . . . . ?
C25 C26 C27 C32 31.9(4) . . . . ?
C25 C33 C34 C35 40.4(4) . . . . ?
C25 C33 C34 C39 -143.4(3) . . . . ?
C26 C25 C33 O1 -177.7(3) . . . . ?
C26 C25 C33 C34 6.6(5) . . . . ?
C26 C27 C28 C29 -176.2(3) . . . . ?
C26 C27 C32 C31 174.0(3) . . . . ?
C27 C28 C29 C30 2.5(5) . . . . ?
C28 C27 C32 C31 -0.5(5) . . . . ?
C28 C29 C30 Cl1 176.9(3) . . . . ?
C28 C29 C30 C31 -1.5(6) . . . . ?
C29 C30 C31 C32 -0.5(6) . . . . ?
C30 C31 C32 C27 1.5(6) . . . . ?
C32 C27 C28 C29 -1.6(5) . . . . ?
C33 O1 B1 F1 82.0(3) . . . . ?
C33 O1 B1 N1 -154.6(3) . . . . ?
C33 O1 B1 N2 -38.8(4) . . . . ?
C33 C25 C26 O2 -139.4(3) . . . . ?
C33 C25 C26 C27 43.5(4) . . . . ?
C33 C34 C35 C36 176.2(3) . . . . ?
C33 C34 C39 C38 -176.5(3) . . . . ?
C34 C35 C36 C37 0.0(5) . . . . ?
C35 C34 C39 C38 -0.1(5) . . . . ?
C35 C36 C37 Cl2 -177.5(2) . . . . ?
C35 C36 C37 C38 0.2(5) . . . . ?
C36 C37 C38 C39 -0.4(6) . . . . ?
C37 C38 C39 C34 0.4(6) . . . . ?
C39 C34 C35 C36 -0.1(4) . . . . ?
B1 O1 C33 C25 19.0(4) . . . . ?
B1 O1 C33 C34 -164.8(2) . . . . ?
B1 N1 C9 C8 4.8(5) . . . . ?
B1 N1 C9 C10 -175.3(3) . . . . ?
B1 N1 C12 C11 175.4(2) . . . . ?
B1 N1 C12 C13 -10.9(4) . . . . ?
B1 N2 C21 C13 15.2(5) . . . . ?
B1 N2 C21 C22 -171.3(3) . . . . ?
B1 N2 C24 C23 172.0(3) . . . . ?
B1 N2 C24 C25 -11.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.273
_oxdiff_exptl_absorpt_empirical_full_min 0.567
####################################################################### 
# 
# 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_20191216a
_database_code_depnum_ccdc_archive 'CCDC 2064515'
loop_
_audit_author_name
_audit_author_address
'qingzheng yang'
;beijing normal university
China
;
_audit_update_record             
;
2021-02-23 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_audit_creation_date             2019-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            P1
_chemical_name_systematic        M1
_chemical_formula_moiety         'C31 H19 B Cl3 F N2 O2'
_chemical_formula_sum            'C31 H19 B Cl3 F N2 O2'
_chemical_formula_weight         587.64
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1o1F1Cl1B1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.6816(3)
_cell_length_b                   20.2007(5)
_cell_length_c                   12.8842(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.368(2)
_cell_angle_gamma                90
_cell_volume                     2693.14(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5697
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.8470
_cell_measurement_theta_min      4.1470
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    3.418
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic purple'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10769
_diffrn_reflns_point_group_measured_fraction_full 0.704
_diffrn_reflns_point_group_measured_fraction_max 0.676
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.024
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  26.00   1.00    1.00    --  -41.49  77.00  30.00   94
  2  ω     37.00  72.00   1.00    1.00    --   41.49-125.00 -60.00   35
  3  ω     15.00 122.00   1.00    1.00    --   41.49  19.00-120.00  107
  4  ω    106.00 177.00   1.00    2.00    --  104.69  45.00-150.00   71
  5  ω    115.00 163.00   1.00    2.00    --  104.69 125.00   0.00   48
  6  ω     40.00 100.00   1.00    2.00    --  104.69 -30.00  30.00   60
  7  ω     74.00 170.00   1.00    2.00    --  104.69  77.00 -30.00   96
  8  ω     58.00 114.00   1.00    2.00    --  104.69 -61.00-150.00   56
  9  ω    131.00 156.00   1.00    2.00    --  104.69 125.00 -30.00   25
 10  ω     38.00 118.00   1.00    2.00    --  104.69-125.00  60.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1261907000
_diffrn_orient_matrix_UB_12      -0.0183310000
_diffrn_orient_matrix_UB_13      -0.0304874000
_diffrn_orient_matrix_UB_21      0.0123228000
_diffrn_orient_matrix_UB_22      -0.0624933000
_diffrn_orient_matrix_UB_23      0.0704509000
_diffrn_orient_matrix_UB_31      -0.0779259000
_diffrn_orient_matrix_UB_32      -0.0397263000
_diffrn_orient_matrix_UB_33      -0.0966597000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.354
_reflns_Friedel_fraction_full    0.392
_reflns_Friedel_fraction_max     0.365
_reflns_number_gt                6763
_reflns_number_total             7161
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.184
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.004(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     723
_refine_ls_number_reflns         7161
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.070
_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)+(0.0329P)²+0.4067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0798
_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:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15),
 C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34), C38(H38), C39(H39), C41(H41), C42(H42), C45(H45),
 C46(H46), C51(H51), C52(H52), C54(H54), C55(H55), C58(H58), C59(H59), C61(H61),
  C62(H62)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C43(H43A,H43B,H43C)
;
_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
B1 B 0.9692(4) 0.4280(2) 0.8983(3) 0.0200(8) Uani 1 1 d . . . . .
C1 C 1.2115(3) 0.41138(19) 0.9026(3) 0.0212(7) Uani 1 1 d . . . . .
C2 C 1.2939(3) 0.3604(2) 0.8921(3) 0.0245(8) Uani 1 1 d . . . . .
H2 H 1.3834 0.3623 0.9047 0.029 Uiso 1 1 calc R . . . .
C3 C 1.2153(3) 0.30570(19) 0.8590(3) 0.0229(7) Uani 1 1 d . . . . .
H3 H 1.2433 0.2636 0.8464 0.028 Uiso 1 1 calc R . . . .
C4 C 1.0860(3) 0.32492(18) 0.8478(3) 0.0213(7) Uani 1 1 d . . . . .
C5 C 0.9700(3) 0.28730(19) 0.8219(3) 0.0201(7) Uani 1 1 d . . . . .
C6 C 0.9716(3) 0.21615(19) 0.7949(3) 0.0212(7) Uani 1 1 d . . . . .
C7 C 1.0408(3) 0.1919(2) 0.7231(3) 0.0253(8) Uani 1 1 d . . . . .
H7 H 1.0855 0.2211 0.6896 0.030 Uiso 1 1 calc R . . . .
C8 C 1.0426(4) 0.1247(2) 0.7020(3) 0.0288(8) Uani 1 1 d . . . . .
H8 H 1.0890 0.1095 0.6545 0.035 Uiso 1 1 calc R . . . .
C9 C 0.9767(4) 0.0793(2) 0.7503(3) 0.0275(8) Uani 1 1 d . . . . .
C10 C 0.9052(4) 0.1033(2) 0.8189(3) 0.0277(8) Uani 1 1 d . . . . .
H10 H 0.8592 0.0740 0.8511 0.033 Uiso 1 1 calc R . . . .
C11 C 0.9019(3) 0.1708(2) 0.8400(3) 0.0227(7) Uani 1 1 d . . . . .
H11 H 0.8522 0.1859 0.8851 0.027 Uiso 1 1 calc R . . . .
C12 C 0.9842(4) 0.0059(2) 0.7296(4) 0.0379(10) Uani 1 1 d . . . . .
H12A H 0.9604 -0.0021 0.6538 0.057 Uiso 1 1 calc GR . . . .
H12B H 0.9262 -0.0174 0.7629 0.057 Uiso 1 1 calc GR . . . .
H12C H 1.0709 -0.0093 0.7590 0.057 Uiso 1 1 calc GR . . . .
C13 C 0.8542(3) 0.31835(18) 0.8216(3) 0.0189(7) Uani 1 1 d . . . . .
C14 C 0.7221(3) 0.29953(19) 0.7842(3) 0.0226(7) Uani 1 1 d . . . . .
H14 H 0.6919 0.2575 0.7612 0.027 Uiso 1 1 calc R . . . .
C15 C 0.6473(3) 0.35412(19) 0.7878(3) 0.0217(7) Uani 1 1 d . . . . .
H15 H 0.5575 0.3557 0.7699 0.026 Uiso 1 1 calc R . . . .
C16 C 0.7333(3) 0.40827(19) 0.8244(3) 0.0194(7) Uani 1 1 d . . . . .
C17 C 0.7163(3) 0.47844(18) 0.8319(3) 0.0181(7) Uani 1 1 d . . . . .
C18 C 0.5824(3) 0.50319(18) 0.8237(3) 0.0204(7) Uani 1 1 d . . . . .
C19 C 0.5572(3) 0.55979(18) 0.8889(3) 0.0208(7) Uani 1 1 d . . . . .
C20 C 0.4385(3) 0.59222(19) 0.8549(3) 0.0223(7) Uani 1 1 d . . . . .
H20 H 0.3795 0.5780 0.7931 0.027 Uiso 1 1 calc R . . . .
C21 C 0.4073(3) 0.6453(2) 0.9121(3) 0.0260(8) Uani 1 1 d . . . . .
H21 H 0.3280 0.6665 0.8892 0.031 Uiso 1 1 calc R . . . .
C22 C 0.4958(4) 0.66603(19) 1.0034(3) 0.0243(7) Uani 1 1 d . . . . .
C23 C 0.6134(3) 0.6335(2) 1.0418(3) 0.0230(7) Uani 1 1 d . . . . .
H23 H 0.6705 0.6471 1.1051 0.028 Uiso 1 1 calc R . . . .
C24 C 0.6432(3) 0.58098(19) 0.9842(3) 0.0216(7) Uani 1 1 d . . . . .
H24 H 0.7217 0.5592 1.0087 0.026 Uiso 1 1 calc R . . . .
C25 C 0.8233(3) 0.51868(18) 0.8375(3) 0.0181(7) Uani 1 1 d . . . . .
C26 C 0.8179(3) 0.59107(18) 0.8284(3) 0.0198(7) Uani 1 1 d . . . . .
C27 C 0.7155(3) 0.62367(19) 0.7586(3) 0.0204(7) Uani 1 1 d . . . . .
H27 H 0.6559 0.5996 0.7077 0.024 Uiso 1 1 calc R . . . .
C28 C 0.7023(3) 0.6919(2) 0.7648(3) 0.0219(7) Uani 1 1 d . . . . .
H28 H 0.6335 0.7136 0.7191 0.026 Uiso 1 1 calc R . . . .
C29 C 0.7926(3) 0.72704(18) 0.8399(3) 0.0217(7) Uani 1 1 d . . . . .
C30 C 0.8981(3) 0.69602(19) 0.9059(3) 0.0225(7) Uani 1 1 d . . . . .
H30 H 0.9595 0.7207 0.9544 0.027 Uiso 1 1 calc R . . . .
C31 C 0.9119(3) 0.6285(2) 0.8996(3) 0.0222(7) Uani 1 1 d . . . . .
H31 H 0.9838 0.6077 0.9427 0.027 Uiso 1 1 calc R . . . .
Cl1 Cl 1.25380(8) 0.48981(5) 0.94803(7) 0.02638(18) Uani 1 1 d . . . . .
Cl2 Cl 0.45760(9) 0.73442(5) 1.07147(8) 0.0311(2) Uani 1 1 d . . . . .
Cl3 Cl 0.77611(9) 0.81220(4) 0.85134(7) 0.02724(19) Uani 1 1 d . . . . .
F1 F 0.98623(18) 0.43383(11) 1.00931(15) 0.0223(4) Uani 1 1 d . . . . .
N1 N 1.0867(3) 0.39261(16) 0.8746(2) 0.0204(6) Uani 1 1 d . . . . .
N2 N 0.8545(3) 0.38455(15) 0.8480(2) 0.0189(6) Uani 1 1 d . . . . .
O1 O 0.9429(2) 0.49388(13) 0.85048(18) 0.0203(5) Uani 1 1 d . . . . .
O2 O 0.4908(2) 0.47357(14) 0.7658(2) 0.0280(6) Uani 1 1 d . . . . .
B2 B 0.3432(4) 0.6026(2) 0.4944(3) 0.0204(8) Uani 1 1 d . . . . .
C32 C 0.4151(3) 0.5594(2) 0.3249(3) 0.0229(7) Uani 1 1 d . . . . .
C33 C 0.4381(4) 0.4988(2) 0.2831(3) 0.0271(8) Uani 1 1 d . . . . .
H33 H 0.4755 0.4915 0.2261 0.033 Uiso 1 1 calc R . . . .
C34 C 0.3943(3) 0.4513(2) 0.3429(3) 0.0257(8) Uani 1 1 d . . . . .
H34 H 0.3973 0.4057 0.3336 0.031 Uiso 1 1 calc R . . . .
C35 C 0.3445(3) 0.48396(19) 0.4203(3) 0.0207(7) Uani 1 1 d . . . . .
C36 C 0.2861(3) 0.45825(18) 0.4999(3) 0.0195(7) Uani 1 1 d . . . . .
C37 C 0.2702(3) 0.38596(19) 0.5077(3) 0.0199(7) Uani 1 1 d . . . . .
C38 C 0.2125(3) 0.34824(19) 0.4177(3) 0.0225(7) Uani 1 1 d . . . . .
H38 H 0.1798 0.3691 0.3522 0.027 Uiso 1 1 calc R . . . .
C39 C 0.2036(3) 0.28024(19) 0.4249(3) 0.0225(8) Uani 1 1 d . . . . .
H39 H 0.1633 0.2561 0.3643 0.027 Uiso 1 1 calc R . . . .
C40 C 0.2539(3) 0.24702(19) 0.5212(3) 0.0225(7) Uani 1 1 d . . . . .
C41 C 0.3088(4) 0.2850(2) 0.6116(3) 0.0254(8) Uani 1 1 d . . . . .
H41 H 0.3416 0.2640 0.6769 0.031 Uiso 1 1 calc R . . . .
C42 C 0.3154(3) 0.3534(2) 0.6058(3) 0.0234(7) Uani 1 1 d . . . . .
H42 H 0.3500 0.3779 0.6674 0.028 Uiso 1 1 calc R . . . .
C43 C 0.2499(4) 0.1726(2) 0.5247(3) 0.0295(8) Uani 1 1 d . . . . .
H43A H 0.1660 0.1574 0.4865 0.044 Uiso 1 1 calc GR . . . .
H43B H 0.2671 0.1582 0.5979 0.044 Uiso 1 1 calc GR . . . .
H43C H 0.3142 0.1548 0.4921 0.044 Uiso 1 1 calc GR . . . .
C44 C 0.2380(3) 0.50106(19) 0.5645(3) 0.0207(7) Uani 1 1 d . . . . .
C45 C 0.1560(3) 0.4933(2) 0.6361(3) 0.0209(7) Uani 1 1 d . . . . .
H45 H 0.1310 0.4533 0.6606 0.025 Uiso 1 1 calc R . . . .
C46 C 0.1205(3) 0.55530(19) 0.6623(3) 0.0213(7) Uani 1 1 d . . . . .
H46 H 0.0671 0.5652 0.7073 0.026 Uiso 1 1 calc R . . . .
C47 C 0.1820(3) 0.60188(19) 0.6067(3) 0.0198(7) Uani 1 1 d . . . . .
C48 C 0.1815(3) 0.67278(19) 0.5991(3) 0.0185(7) Uani 1 1 d . . . . .
C49 C 0.1271(3) 0.70945(18) 0.6780(3) 0.0190(7) Uani 1 1 d . . . . .
C50 C 0.2000(3) 0.76632(19) 0.7392(3) 0.0202(7) Uani 1 1 d . . . . .
C51 C 0.1365(3) 0.8073(2) 0.7963(3) 0.0224(7) Uani 1 1 d . . . . .
H51 H 0.0495 0.8001 0.7925 0.027 Uiso 1 1 calc R . . . .
C52 C 0.2010(3) 0.8586(2) 0.8587(3) 0.0245(8) Uani 1 1 d . . . . .
H52 H 0.1583 0.8860 0.8967 0.029 Uiso 1 1 calc R . . . .
C53 C 0.3310(3) 0.86784(18) 0.8630(3) 0.0217(7) Uani 1 1 d . . . . .
C54 C 0.3979(3) 0.82708(19) 0.8091(3) 0.0236(8) Uani 1 1 d . . . . .
H54 H 0.4854 0.8338 0.8144 0.028 Uiso 1 1 calc R . . . .
C55 C 0.3319(3) 0.77639(18) 0.7472(3) 0.0200(7) Uani 1 1 d . . . . .
H55 H 0.3754 0.7486 0.7104 0.024 Uiso 1 1 calc R . . . .
C56 C 0.2290(3) 0.70151(19) 0.5191(3) 0.0195(7) Uani 1 1 d . . . . .
C57 C 0.2241(3) 0.77300(19) 0.4965(3) 0.0209(7) Uani 1 1 d . . . . .
C58 C 0.1161(3) 0.8112(2) 0.4995(3) 0.0234(7) Uani 1 1 d . . . . .
H58 H 0.0421 0.7907 0.5095 0.028 Uiso 1 1 calc R . . . .
C59 C 0.1178(4) 0.8794(2) 0.4878(3) 0.0286(8) Uani 1 1 d . . . . .
H59 H 0.0460 0.9048 0.4904 0.034 Uiso 1 1 calc R . . . .
C60 C 0.2292(4) 0.9090(2) 0.4722(3) 0.0292(8) Uani 1 1 d . . . . .
C61 C 0.3363(4) 0.8725(2) 0.4657(3) 0.0273(8) Uani 1 1 d . . . . .
H61 H 0.4093 0.8933 0.4540 0.033 Uiso 1 1 calc R . . . .
C62 C 0.3329(3) 0.8042(2) 0.4771(3) 0.0232(7) Uani 1 1 d . . . . .
H62 H 0.4038 0.7789 0.4718 0.028 Uiso 1 1 calc R . . . .
Cl4 Cl 0.45074(8) 0.63549(5) 0.28196(7) 0.02710(19) Uani 1 1 d . . . . .
Cl5 Cl 0.41268(9) 0.93250(5) 0.93982(7) 0.0294(2) Uani 1 1 d . . . . .
Cl6 Cl 0.23376(12) 0.99492(5) 0.45955(9) 0.0434(3) Uani 1 1 d . . . . .
F2 F 0.46456(19) 0.61458(11) 0.56354(16) 0.0236(4) Uani 1 1 d . . . . .
N3 N 0.3583(3) 0.55271(15) 0.4072(2) 0.0195(6) Uani 1 1 d . . . . .
N4 N 0.2532(3) 0.56830(15) 0.5525(2) 0.0188(6) Uani 1 1 d . . . . .
O3 O 0.2856(2) 0.66601(13) 0.45478(18) 0.0198(5) Uani 1 1 d . . . . .
O4 O 0.0287(2) 0.68979(14) 0.6992(2) 0.0243(5) 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
B1 F1 1.401(4) . ?
B1 N1 1.539(5) . ?
B1 N2 1.516(5) . ?
B1 O1 1.463(5) . ?
C1 C2 1.384(5) . ?
C1 Cl1 1.711(4) . ?
C1 N1 1.346(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.407(5) . ?
C4 C5 1.421(5) . ?
C4 N1 1.410(5) . ?
C5 C6 1.480(5) . ?
C5 C13 1.386(5) . ?
C6 C7 1.408(5) . ?
C6 C11 1.396(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(6) . ?
C9 C10 1.391(6) . ?
C9 C12 1.512(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(6) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.425(5) . ?
C13 N2 1.380(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.431(5) . ?
C16 C17 1.435(5) . ?
C16 N2 1.342(4) . ?
C17 C18 1.494(5) . ?
C17 C25 1.389(5) . ?
C18 C19 1.483(5) . ?
C18 O2 1.229(4) . ?
C19 C20 1.398(5) . ?
C19 C24 1.405(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(6) . ?
C22 C23 1.394(5) . ?
C22 Cl2 1.738(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.467(5) . ?
C25 O1 1.344(4) . ?
C26 C27 1.397(5) . ?
C26 C31 1.402(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.381(5) . ?
C29 C30 1.382(5) . ?
C29 Cl3 1.739(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.376(5) . ?
C31 H31 0.9300 . ?
B2 F2 1.400(4) . ?
B2 N3 1.547(5) . ?
B2 N4 1.524(5) . ?
B2 O3 1.457(5) . ?
C32 C33 1.382(6) . ?
C32 Cl4 1.709(4) . ?
C32 N3 1.353(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.384(6) . ?
C34 H34 0.9300 . ?
C34 C35 1.405(5) . ?
C35 C36 1.424(5) . ?
C35 N3 1.411(5) . ?
C36 C37 1.476(5) . ?
C36 C44 1.384(5) . ?
C37 C38 1.397(5) . ?
C37 C42 1.399(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.382(5) . ?
C39 H39 0.9300 . ?
C39 C40 1.395(5) . ?
C40 C41 1.396(5) . ?
C40 C43 1.505(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.388(6) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 C45 1.430(5) . ?
C44 N4 1.381(5) . ?
C45 H45 0.9300 . ?
C45 C46 1.375(5) . ?
C46 H46 0.9300 . ?
C46 C47 1.436(5) . ?
C47 C48 1.435(5) . ?
C47 N4 1.337(5) . ?
C48 C49 1.487(5) . ?
C48 C56 1.385(5) . ?
C49 C50 1.498(5) . ?
C49 O4 1.217(4) . ?
C50 C51 1.390(5) . ?
C50 C55 1.401(5) . ?
C51 H51 0.9300 . ?
C51 C52 1.386(5) . ?
C52 H52 0.9300 . ?
C52 C53 1.389(5) . ?
C53 C54 1.385(5) . ?
C53 Cl5 1.737(4) . ?
C54 H54 0.9300 . ?
C54 C55 1.379(5) . ?
C55 H55 0.9300 . ?
C56 C57 1.472(5) . ?
C56 O3 1.347(4) . ?
C57 C58 1.397(5) . ?
C57 C62 1.398(5) . ?
C58 H58 0.9300 . ?
C58 C59 1.387(6) . ?
C59 H59 0.9300 . ?
C59 C60 1.390(6) . ?
C60 C61 1.381(6) . ?
C60 Cl6 1.744(4) . ?
C61 H61 0.9300 . ?
C61 C62 1.390(6) . ?
C62 H62 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
F1 B1 N1 109.6(3) . . ?
F1 B1 N2 111.8(3) . . ?
F1 B1 O1 108.4(3) . . ?
N2 B1 N1 105.0(3) . . ?
O1 B1 N1 114.8(3) . . ?
O1 B1 N2 107.3(3) . . ?
C2 C1 Cl1 127.1(3) . . ?
N1 C1 C2 112.1(3) . . ?
N1 C1 Cl1 120.8(3) . . ?
C1 C2 H2 127.1 . . ?
C1 C2 C3 105.7(3) . . ?
C3 C2 H2 127.1 . . ?
C2 C3 H3 125.8 . . ?
C2 C3 C4 108.4(3) . . ?
C4 C3 H3 125.8 . . ?
C3 C4 C5 130.8(4) . . ?
C3 C4 N1 107.3(3) . . ?
N1 C4 C5 121.9(3) . . ?
C4 C5 C6 121.0(3) . . ?
C13 C5 C4 118.9(3) . . ?
C13 C5 C6 120.1(3) . . ?
C7 C6 C5 122.0(3) . . ?
C11 C6 C5 120.2(3) . . ?
C11 C6 C7 117.8(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C12 120.8(4) . . ?
C10 C9 C8 118.2(4) . . ?
C10 C9 C12 121.0(4) . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.7(4) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.3(4) . . ?
C10 C11 H11 119.3 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 C14 133.5(3) . . ?
N2 C13 C5 119.4(3) . . ?
N2 C13 C14 106.4(3) . . ?
C13 C14 H14 125.9 . . ?
C15 C14 C13 108.1(3) . . ?
C15 C14 H14 125.9 . . ?
C14 C15 H15 126.4 . . ?
C14 C15 C16 107.1(3) . . ?
C16 C15 H15 126.4 . . ?
C15 C16 C17 134.1(3) . . ?
N2 C16 C15 107.8(3) . . ?
N2 C16 C17 117.9(3) . . ?
C16 C17 C18 117.4(3) . . ?
C25 C17 C16 117.7(3) . . ?
C25 C17 C18 124.6(3) . . ?
C19 C18 C17 121.6(3) . . ?
O2 C18 C17 119.0(3) . . ?
O2 C18 C19 119.4(3) . . ?
C20 C19 C18 117.5(3) . . ?
C20 C19 C24 118.5(3) . . ?
C24 C19 C18 124.0(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.0(3) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C23 121.7(4) . . ?
C21 C22 Cl2 118.4(3) . . ?
C23 C22 Cl2 119.9(3) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.7(3) . . ?
C24 C23 H23 120.6 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.1(3) . . ?
C23 C24 H24 119.4 . . ?
C17 C25 C26 124.3(3) . . ?
O1 C25 C17 122.2(3) . . ?
O1 C25 C26 113.5(3) . . ?
C27 C26 C25 122.0(3) . . ?
C27 C26 C31 119.1(3) . . ?
C31 C26 C25 118.6(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.5 . . ?
C29 C28 C27 119.1(3) . . ?
C29 C28 H28 120.5 . . ?
C28 C29 C30 121.3(3) . . ?
C28 C29 Cl3 120.0(3) . . ?
C30 C29 Cl3 118.7(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.7(3) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 H31 119.9 . . ?
C30 C31 C26 120.3(3) . . ?
C30 C31 H31 119.9 . . ?
C1 N1 B1 128.2(3) . . ?
C1 N1 C4 106.5(3) . . ?
C4 N1 B1 123.0(3) . . ?
C13 N2 B1 128.2(3) . . ?
C16 N2 B1 121.5(3) . . ?
C16 N2 C13 110.3(3) . . ?
C25 O1 B1 117.9(3) . . ?
F2 B2 N3 109.1(3) . . ?
F2 B2 N4 111.3(3) . . ?
F2 B2 O3 108.3(3) . . ?
N4 B2 N3 104.7(3) . . ?
O3 B2 N3 115.4(3) . . ?
O3 B2 N4 108.0(3) . . ?
C33 C32 Cl4 126.5(3) . . ?
N3 C32 C33 112.0(3) . . ?
N3 C32 Cl4 121.5(3) . . ?
C32 C33 H33 126.9 . . ?
C32 C33 C34 106.2(3) . . ?
C34 C33 H33 126.9 . . ?
C33 C34 H34 126.0 . . ?
C33 C34 C35 108.0(4) . . ?
C35 C34 H34 126.0 . . ?
C34 C35 C36 130.6(4) . . ?
C34 C35 N3 107.9(3) . . ?
N3 C35 C36 121.5(3) . . ?
C35 C36 C37 119.2(3) . . ?
C44 C36 C35 119.9(3) . . ?
C44 C36 C37 120.7(3) . . ?
C38 C37 C36 121.2(3) . . ?
C38 C37 C42 118.4(3) . . ?
C42 C37 C36 120.4(3) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 C37 120.7(4) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 119.3 . . ?
C38 C39 C40 121.3(4) . . ?
C40 C39 H39 119.3 . . ?
C39 C40 C41 117.8(4) . . ?
C39 C40 C43 120.0(3) . . ?
C41 C40 C43 122.1(4) . . ?
C40 C41 H41 119.4 . . ?
C42 C41 C40 121.2(4) . . ?
C42 C41 H41 119.4 . . ?
C37 C42 H42 119.8 . . ?
C41 C42 C37 120.4(4) . . ?
C41 C42 H42 119.8 . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C36 C44 C45 134.2(4) . . ?
N4 C44 C36 118.4(3) . . ?
N4 C44 C45 106.7(3) . . ?
C44 C45 H45 126.0 . . ?
C46 C45 C44 107.9(3) . . ?
C46 C45 H45 126.0 . . ?
C45 C46 H46 126.7 . . ?
C45 C46 C47 106.7(3) . . ?
C47 C46 H46 126.7 . . ?
C48 C47 C46 133.9(3) . . ?
N4 C47 C46 108.5(3) . . ?
N4 C47 C48 117.6(3) . . ?
C47 C48 C49 116.5(3) . . ?
C56 C48 C47 118.2(3) . . ?
C56 C48 C49 125.3(3) . . ?
C48 C49 C50 120.1(3) . . ?
O4 C49 C48 119.8(3) . . ?
O4 C49 C50 119.8(3) . . ?
C51 C50 C49 118.5(3) . . ?
C51 C50 C55 119.2(3) . . ?
C55 C50 C49 122.1(3) . . ?
C50 C51 H51 119.5 . . ?
C52 C51 C50 121.0(3) . . ?
C52 C51 H51 119.5 . . ?
C51 C52 H52 120.9 . . ?
C51 C52 C53 118.2(3) . . ?
C53 C52 H52 120.9 . . ?
C52 C53 Cl5 118.7(3) . . ?
C54 C53 C52 122.3(3) . . ?
C54 C53 Cl5 119.0(3) . . ?
C53 C54 H54 120.7 . . ?
C55 C54 C53 118.6(3) . . ?
C55 C54 H54 120.7 . . ?
C50 C55 H55 119.6 . . ?
C54 C55 C50 120.7(3) . . ?
C54 C55 H55 119.6 . . ?
C48 C56 C57 123.8(3) . . ?
O3 C56 C48 122.6(3) . . ?
O3 C56 C57 113.6(3) . . ?
C58 C57 C56 121.8(3) . . ?
C58 C57 C62 119.0(4) . . ?
C62 C57 C56 119.1(3) . . ?
C57 C58 H58 119.5 . . ?
C59 C58 C57 120.9(4) . . ?
C59 C58 H58 119.5 . . ?
C58 C59 H59 120.7 . . ?
C58 C59 C60 118.5(4) . . ?
C60 C59 H59 120.7 . . ?
C59 C60 Cl6 119.1(3) . . ?
C61 C60 C59 122.0(4) . . ?
C61 C60 Cl6 118.8(3) . . ?
C60 C61 H61 120.6 . . ?
C60 C61 C62 118.7(4) . . ?
C62 C61 H61 120.6 . . ?
C57 C62 H62 119.6 . . ?
C61 C62 C57 120.7(4) . . ?
C61 C62 H62 119.6 . . ?
C32 N3 B2 130.7(3) . . ?
C32 N3 C35 105.8(3) . . ?
C35 N3 B2 121.4(3) . . ?
C44 N4 B2 127.4(3) . . ?
C47 N4 B2 122.4(3) . . ?
C47 N4 C44 110.1(3) . . ?
C56 O3 B2 117.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.313
_oxdiff_exptl_absorpt_empirical_full_min 0.598
_exptl_crystal_recrystallization_method 'Vapour deposition'
