# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_r20220701b
_database_code_depnum_ccdc_archive 'CCDC 2246187'
loop_
_audit_author_name
_audit_author_address
'Huina Zou'
;Nankai university
China
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-08-07 downloaded from the CCDC.
;
_audit_creation_date             2022-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 B Cl F2 N'
_chemical_formula_sum            'C19 H21 B Cl F2 N'
_chemical_formula_weight         347.63
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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           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                   8.2271(5)
_cell_length_b                   10.3968(7)
_cell_length_c                   21.4304(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.909(6)
_cell_angle_gamma                90
_cell_volume                     1819.75(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7166
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.9840
_cell_measurement_theta_min      1.9070
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.1339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            22992
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.942
_diffrn_reflns_theta_min         1.914
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0775146000
_diffrn_orient_matrix_UB_12      -0.0003075000
_diffrn_orient_matrix_UB_13      0.0184964000
_diffrn_orient_matrix_UB_21      0.0390295000
_diffrn_orient_matrix_UB_22      -0.0048331000
_diffrn_orient_matrix_UB_23      -0.0276756000
_diffrn_orient_matrix_UB_31      0.0031714000
_diffrn_orient_matrix_UB_32      0.0680499000
_diffrn_orient_matrix_UB_33      -0.0018556000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.796
_reflns_number_gt                6269
_reflns_number_total             11704
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_coef       0.0055(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         11704
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1428
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.024
_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)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1648
_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. Restrained distances
 B2-H2B = B2-H2A = B1-H1A = B1-H1B
 1 with sigma of 0.01
 H2B-H2A = H1A-H1B
 1.6 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8), C27(H27)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C24(H24), C25(H25), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.60684(17) 0.06245(14) 0.33084(5) 0.0471(4) Uani 1 1 d . . . . .
F1 F 0.2471(3) 0.3490(3) 0.07594(12) 0.0393(7) Uani 1 1 d . . . . .
F2 F 0.1528(3) 0.1534(3) 0.06229(12) 0.0387(7) Uani 1 1 d . . . . .
N1 N 0.7076(4) 0.2405(4) -0.00931(15) 0.0286(8) Uani 1 1 d . . . . .
C1 C 0.5168(6) 0.1071(5) 0.2559(2) 0.0333(11) Uani 1 1 d . . . . .
C2 C 0.4097(6) 0.2086(5) 0.2498(2) 0.0357(11) Uani 1 1 d . . . . .
H2 H 0.381894 0.252347 0.285957 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3423(5) 0.2466(5) 0.18993(19) 0.0321(10) Uani 1 1 d . . . . .
H3 H 0.268264 0.316970 0.185316 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3819(5) 0.1830(4) 0.13707(19) 0.0260(9) Uani 1 1 d . . . . .
C5 C 0.4876(6) 0.0781(5) 0.14436(19) 0.0344(11) Uani 1 1 d . . . . .
H5 H 0.513208 0.032355 0.108430 0.041 Uiso 1 1 calc R U . . .
C6 C 0.5566(6) 0.0397(5) 0.20454(19) 0.0343(11) Uani 1 1 d . . . . .
H6 H 0.629355 -0.031507 0.209766 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2993(5) 0.2225(5) 0.0729(2) 0.0296(10) Uani 1 1 d . . . . .
C8 C 0.3952(5) 0.2084(4) 0.01657(18) 0.0264(9) Uani 1 1 d . . . . .
H8 H 0.431626 0.116844 0.014501 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2871(5) 0.2377(5) -0.04163(19) 0.0304(10) Uani 1 1 d . . . . .
C10 C 0.2099(5) 0.2697(5) -0.08992(19) 0.0307(10) Uani 1 1 d . . . . .
C11 C 0.1229(5) 0.3139(4) -0.1486(2) 0.0281(10) Uani 1 1 d . . . . .
C12 C 0.0171(5) 0.4177(4) -0.15018(19) 0.0277(9) Uani 1 1 d . . . . .
H12 H -0.001142 0.458601 -0.111983 0.033 Uiso 1 1 calc R U . . .
C13 C -0.0626(6) 0.4631(5) -0.2065(2) 0.0365(11) Uani 1 1 d . . . . .
H13 H -0.137099 0.533011 -0.206682 0.044 Uiso 1 1 calc R U . . .
C14 C -0.0332(6) 0.4060(5) -0.2627(2) 0.0363(12) Uani 1 1 d . . . . .
H14 H -0.085493 0.438556 -0.301450 0.044 Uiso 1 1 calc R U . . .
C15 C 0.0705(6) 0.3033(5) -0.2625(2) 0.0389(12) Uani 1 1 d . . . . .
H15 H 0.089588 0.263915 -0.300966 0.047 Uiso 1 1 calc R U . . .
C16 C 0.1485(5) 0.2564(5) -0.20544(19) 0.0341(11) Uani 1 1 d . . . . .
H16 H 0.219788 0.184541 -0.205383 0.041 Uiso 1 1 calc R U . . .
C17 C 0.6592(6) 0.2122(6) -0.0771(2) 0.0486(15) Uani 1 1 d . . . . .
H17A H 0.623173 0.291720 -0.099142 0.073 Uiso 1 1 calc R U . . .
H17B H 0.569360 0.149683 -0.081439 0.073 Uiso 1 1 calc R U . . .
H17C H 0.753089 0.176586 -0.095386 0.073 Uiso 1 1 calc R U . . .
C18 C 0.8442(5) 0.3353(5) -0.0033(2) 0.0389(12) Uani 1 1 d . . . . .
H18A H 0.877250 0.353877 0.041259 0.058 Uiso 1 1 calc R U . . .
H18B H 0.807761 0.414836 -0.025200 0.058 Uiso 1 1 calc R U . . .
H18C H 0.937388 0.299548 -0.021968 0.058 Uiso 1 1 calc R U . . .
C19 C 0.7712(6) 0.1196(5) 0.0222(2) 0.0407(12) Uani 1 1 d . . . . .
H19A H 0.867729 0.090405 0.003496 0.061 Uiso 1 1 calc R U . . .
H19B H 0.686230 0.053111 0.016667 0.061 Uiso 1 1 calc R U . . .
H19C H 0.801370 0.135853 0.067146 0.061 Uiso 1 1 calc R U . . .
B1 B 0.5585(6) 0.3004(5) 0.0237(2) 0.0285(11) Uani 1 1 d D . . . .
H1A H 0.604(6) 0.322(4) 0.0684(9) 0.050(15) Uiso 1 1 d D . . . .
H1B H 0.532(6) 0.386(2) 0.0029(15) 0.044(14) Uiso 1 1 d D . . . .
Cl2 Cl -0.12462(17) 0.36676(17) 0.17510(5) 0.0584(4) Uani 1 1 d . . . . .
F3 F 0.3085(3) 0.4442(3) 0.45432(11) 0.0390(7) Uani 1 1 d . . . . .
F4 F 0.3494(3) 0.2423(3) 0.43299(12) 0.0389(7) Uani 1 1 d . . . . .
N2 N -0.1832(4) 0.3346(3) 0.51644(15) 0.0269(8) Uani 1 1 d . . . . .
C20 C -0.0256(5) 0.3585(6) 0.25126(19) 0.0367(11) Uani 1 1 d . . . . .
C21 C 0.0738(6) 0.4597(5) 0.2749(2) 0.0347(11) Uani 1 1 d . . . . .
H21 H 0.087715 0.533429 0.249925 0.042 Uiso 1 1 calc R U . . .
C22 C 0.1524(6) 0.4509(5) 0.33585(19) 0.0320(10) Uani 1 1 d . . . . .
H22 H 0.220862 0.519294 0.352488 0.038 Uiso 1 1 calc R U . . .
C23 C 0.1327(5) 0.3446(4) 0.37256(18) 0.0261(9) Uani 1 1 d . . . . .
C24 C 0.0342(5) 0.2440(5) 0.34799(19) 0.0325(10) Uani 1 1 d . . . . .
H24 H 0.020885 0.170111 0.372964 0.039 Uiso 1 1 calc R U . . .
C25 C -0.0454(6) 0.2507(5) 0.2867(2) 0.0386(12) Uani 1 1 d . . . . .
H25 H -0.112488 0.181732 0.269816 0.046 Uiso 1 1 calc R U . . .
C26 C 0.2249(5) 0.3314(4) 0.4381(2) 0.0298(10) Uani 1 1 d . . . . .
C27 C 0.1260(5) 0.2920(4) 0.49010(18) 0.0271(9) Uani 1 1 d . . . . .
H27 H 0.064899 0.212284 0.475491 0.033 Uiso 1 1 calc R U . . .
C28 C 0.2338(5) 0.2573(5) 0.5471(2) 0.0306(10) Uani 1 1 d . . . . .
C29 C 0.3135(5) 0.2255(5) 0.59514(19) 0.0315(10) Uani 1 1 d . . . . .
C30 C 0.3981(5) 0.1748(4) 0.65301(19) 0.0290(10) Uani 1 1 d . . . . .
C31 C 0.5268(5) 0.2408(5) 0.68787(18) 0.0302(10) Uani 1 1 d . . . . .
H31 H 0.564559 0.319877 0.672760 0.036 Uiso 1 1 calc R U . . .
C32 C 0.5991(6) 0.1907(5) 0.7444(2) 0.0369(12) Uani 1 1 d . . . . .
H32 H 0.686088 0.236232 0.767873 0.044 Uiso 1 1 calc R U . . .
C33 C 0.5466(6) 0.0761(5) 0.7670(2) 0.0380(12) Uani 1 1 d . . . . .
H33 H 0.596559 0.042694 0.805909 0.046 Uiso 1 1 calc R U . . .
C34 C 0.4199(6) 0.0097(5) 0.7323(2) 0.0374(11) Uani 1 1 d . . . . .
H34 H 0.383354 -0.069578 0.747715 0.045 Uiso 1 1 calc R U . . .
C35 C 0.3463(5) 0.0575(5) 0.67571(19) 0.0318(10) Uani 1 1 d . . . . .
H35 H 0.260615 0.010721 0.652203 0.038 Uiso 1 1 calc R U . . .
C36 C -0.1580(6) 0.2471(5) 0.5713(2) 0.0376(11) Uani 1 1 d . . . . .
H36A H -0.264144 0.215240 0.581078 0.056 Uiso 1 1 calc R U . . .
H36B H -0.103347 0.293834 0.607668 0.056 Uiso 1 1 calc R U . . .
H36C H -0.089693 0.174315 0.561529 0.056 Uiso 1 1 calc R U . . .
C37 C -0.2992(6) 0.4385(5) 0.5309(2) 0.0394(12) Uani 1 1 d . . . . .
H37A H -0.406105 0.400628 0.535552 0.059 Uiso 1 1 calc R U . . .
H37B H -0.311219 0.501161 0.496460 0.059 Uiso 1 1 calc R U . . .
H37C H -0.256052 0.481696 0.570038 0.059 Uiso 1 1 calc R U . . .
C38 C -0.2635(6) 0.2603(5) 0.4614(2) 0.0410(12) Uani 1 1 d . . . . .
H38A H -0.192583 0.188650 0.452291 0.061 Uiso 1 1 calc R U . . .
H38B H -0.281776 0.316879 0.424699 0.061 Uiso 1 1 calc R U . . .
H38C H -0.368686 0.226523 0.471260 0.061 Uiso 1 1 calc R U . . .
B2 B -0.0126(6) 0.4015(5) 0.5018(3) 0.0319(12) Uani 1 1 d D . . . .
H2A H -0.040(6) 0.460(3) 0.4649(12) 0.045(14) Uiso 1 1 d D . . . .
H2B H 0.029(5) 0.457(3) 0.5388(12) 0.043(14) Uiso 1 1 d 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 C1 1.749(4) . ?
F1 C7 1.388(5) . ?
F2 C7 1.398(5) . ?
N1 C17 1.489(5) . ?
N1 C18 1.489(6) . ?
N1 C19 1.491(6) . ?
N1 B1 1.613(6) . ?
C1 C2 1.370(7) . ?
C1 C6 1.377(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(6) . ?
C4 C5 1.392(6) . ?
C4 C7 1.516(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.526(6) . ?
C8 H8 1.0000 . ?
C8 C9 1.474(5) . ?
C8 B1 1.642(6) . ?
C9 C10 1.195(5) . ?
C10 C11 1.445(6) . ?
C11 C12 1.385(6) . ?
C11 C16 1.396(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.367(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(6) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
B1 H1A 1.010(13) . ?
B1 H1B 1.007(13) . ?
Cl2 C20 1.736(4) . ?
F3 C26 1.383(5) . ?
F4 C26 1.395(5) . ?
N2 C36 1.482(5) . ?
N2 C37 1.498(6) . ?
N2 C38 1.495(5) . ?
N2 B2 1.630(6) . ?
C20 C21 1.391(7) . ?
C20 C25 1.375(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(6) . ?
C23 C24 1.388(6) . ?
C23 C26 1.520(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.396(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.513(6) . ?
C27 H27 1.0000 . ?
C27 C28 1.466(5) . ?
C27 B2 1.652(7) . ?
C28 C29 1.198(5) . ?
C29 C30 1.447(5) . ?
C30 C31 1.399(6) . ?
C30 C35 1.398(7) . ?
C31 H31 0.9500 . ?
C31 C32 1.385(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.375(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.389(7) . ?
C34 H34 0.9500 . ?
C34 C35 1.381(6) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
B2 H2A 1.005(13) . ?
B2 H2B 1.009(13) . ?

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
C17 N1 C19 108.3(4) . . ?
C17 N1 B1 112.1(3) . . ?
C18 N1 C17 109.0(4) . . ?
C18 N1 C19 107.4(3) . . ?
C18 N1 B1 108.2(4) . . ?
C19 N1 B1 111.8(4) . . ?
C2 C1 Cl1 119.2(4) . . ?
C2 C1 C6 121.9(4) . . ?
C6 C1 Cl1 118.9(4) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.1(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 C7 119.3(4) . . ?
C5 C4 C7 121.3(4) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.7(5) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
F1 C7 F2 103.3(3) . . ?
F1 C7 C4 108.7(4) . . ?
F1 C7 C8 108.7(4) . . ?
F2 C7 C4 106.9(4) . . ?
F2 C7 C8 109.9(3) . . ?
C4 C7 C8 118.2(3) . . ?
C7 C8 H8 108.2 . . ?
C7 C8 B1 111.4(3) . . ?
C9 C8 C7 109.4(3) . . ?
C9 C8 H8 108.2 . . ?
C9 C8 B1 111.2(4) . . ?
B1 C8 H8 108.2 . . ?
C10 C9 C8 174.0(5) . . ?
C9 C10 C11 176.9(5) . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 C16 118.2(4) . . ?
C16 C11 C10 120.8(4) . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(4) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.7(4) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.9(4) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 B1 C8 113.0(4) . . ?
N1 B1 H1A 107(3) . . ?
N1 B1 H1B 107(3) . . ?
C8 B1 H1A 115(3) . . ?
C8 B1 H1B 110(3) . . ?
H1A B1 H1B 105.2(17) . . ?
C36 N2 C37 108.1(3) . . ?
C36 N2 C38 108.3(4) . . ?
C36 N2 B2 111.9(3) . . ?
C37 N2 B2 108.5(3) . . ?
C38 N2 C37 107.7(3) . . ?
C38 N2 B2 112.2(3) . . ?
C21 C20 Cl2 119.6(4) . . ?
C25 C20 Cl2 119.1(4) . . ?
C25 C20 C21 121.2(4) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 C20 118.7(5) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.1(4) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 119.4(4) . . ?
C22 C23 C26 121.4(4) . . ?
C24 C23 C26 119.1(4) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.4(5) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 C24 119.2(5) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
F3 C26 F4 103.6(3) . . ?
F3 C26 C23 109.5(4) . . ?
F3 C26 C27 109.9(4) . . ?
F4 C26 C23 106.1(3) . . ?
F4 C26 C27 110.1(4) . . ?
C27 C26 C23 116.9(3) . . ?
C26 C27 H27 106.8 . . ?
C26 C27 B2 111.6(4) . . ?
C28 C27 C26 110.8(3) . . ?
C28 C27 H27 106.8 . . ?
C28 C27 B2 113.7(4) . . ?
B2 C27 H27 106.8 . . ?
C29 C28 C27 175.8(5) . . ?
C28 C29 C30 173.7(5) . . ?
C31 C30 C29 122.3(4) . . ?
C35 C30 C29 118.7(4) . . ?
C35 C30 C31 118.9(4) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.1(5) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.6 . . ?
C33 C32 C31 120.9(4) . . ?
C33 C32 H32 119.6 . . ?
C32 C33 H33 120.3 . . ?
C32 C33 C34 119.3(4) . . ?
C34 C33 H33 120.3 . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.8(5) . . ?
C35 C34 H34 119.6 . . ?
C30 C35 H35 120.0 . . ?
C34 C35 C30 120.0(4) . . ?
C34 C35 H35 120.0 . . ?
N2 C36 H36A 109.5 . . ?
N2 C36 H36B 109.5 . . ?
N2 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N2 C37 H37A 109.5 . . ?
N2 C37 H37B 109.5 . . ?
N2 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N2 C38 H38A 109.5 . . ?
N2 C38 H38B 109.5 . . ?
N2 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 B2 C27 111.2(4) . . ?
N2 B2 H2A 107(3) . . ?
N2 B2 H2B 108(3) . . ?
C27 B2 H2A 113(3) . . ?
C27 B2 H2B 110(3) . . ?
H2A B2 H2B 106.9(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 177.9(4) . . . . ?
Cl1 C1 C6 C5 -178.2(4) . . . . ?
F1 C7 C8 C9 -61.9(4) . . . . ?
F1 C7 C8 B1 61.5(4) . . . . ?
F2 C7 C8 C9 50.5(5) . . . . ?
F2 C7 C8 B1 173.9(3) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C1 C6 C5 1.3(8) . . . . ?
C2 C3 C4 C5 1.4(7) . . . . ?
C2 C3 C4 C7 176.8(4) . . . . ?
C3 C4 C5 C6 -1.7(7) . . . . ?
C3 C4 C7 F1 24.1(5) . . . . ?
C3 C4 C7 F2 -86.7(5) . . . . ?
C3 C4 C7 C8 148.7(4) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C4 C7 C8 C9 173.6(4) . . . . ?
C4 C7 C8 B1 -63.0(5) . . . . ?
C5 C4 C7 F1 -160.6(4) . . . . ?
C5 C4 C7 F2 88.5(5) . . . . ?
C5 C4 C7 C8 -36.0(6) . . . . ?
C6 C1 C2 C3 -1.6(7) . . . . ?
C7 C4 C5 C6 -177.0(4) . . . . ?
C7 C8 B1 N1 149.0(3) . . . . ?
C9 C8 B1 N1 -88.7(4) . . . . ?
C10 C11 C12 C13 177.9(4) . . . . ?
C10 C11 C16 C15 -176.7(4) . . . . ?
C11 C12 C13 C14 -1.7(7) . . . . ?
C12 C11 C16 C15 0.6(7) . . . . ?
C12 C13 C14 C15 1.7(8) . . . . ?
C13 C14 C15 C16 -0.6(8) . . . . ?
C14 C15 C16 C11 -0.6(8) . . . . ?
C16 C11 C12 C13 0.6(7) . . . . ?
C17 N1 B1 C8 56.3(5) . . . . ?
C18 N1 B1 C8 176.5(3) . . . . ?
C19 N1 B1 C8 -65.4(4) . . . . ?
Cl2 C20 C21 C22 -179.7(4) . . . . ?
Cl2 C20 C25 C24 180.0(4) . . . . ?
F3 C26 C27 C28 -66.2(5) . . . . ?
F3 C26 C27 B2 61.6(4) . . . . ?
F4 C26 C27 C28 47.2(5) . . . . ?
F4 C26 C27 B2 175.0(3) . . . . ?
C20 C21 C22 C23 -0.2(7) . . . . ?
C21 C20 C25 C24 0.9(7) . . . . ?
C21 C22 C23 C24 0.8(7) . . . . ?
C21 C22 C23 C26 176.9(4) . . . . ?
C22 C23 C24 C25 -0.5(7) . . . . ?
C22 C23 C26 F3 6.7(6) . . . . ?
C22 C23 C26 F4 -104.5(5) . . . . ?
C22 C23 C26 C27 132.3(4) . . . . ?
C23 C24 C25 C20 -0.3(7) . . . . ?
C23 C26 C27 C28 168.3(4) . . . . ?
C23 C26 C27 B2 -63.9(5) . . . . ?
C24 C23 C26 F3 -177.1(4) . . . . ?
C24 C23 C26 F4 71.7(5) . . . . ?
C24 C23 C26 C27 -51.5(6) . . . . ?
C25 C20 C21 C22 -0.7(7) . . . . ?
C26 C23 C24 C25 -176.8(4) . . . . ?
C26 C27 B2 N2 141.2(3) . . . . ?
C28 C27 B2 N2 -92.6(4) . . . . ?
C29 C30 C31 C32 177.2(4) . . . . ?
C29 C30 C35 C34 -177.0(4) . . . . ?
C30 C31 C32 C33 0.2(7) . . . . ?
C31 C30 C35 C34 1.2(7) . . . . ?
C31 C32 C33 C34 0.3(7) . . . . ?
C32 C33 C34 C35 -0.1(7) . . . . ?
C33 C34 C35 C30 -0.7(7) . . . . ?
C35 C30 C31 C32 -1.0(7) . . . . ?
C36 N2 B2 C27 57.1(5) . . . . ?
C37 N2 B2 C27 176.2(3) . . . . ?
C38 N2 B2 C27 -64.9(5) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.527
_oxdiff_exptl_absorpt_empirical_full_min 0.471
