# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_hl-cor-11b-2ben_auto
_database_code_depnum_ccdc_archive 'CCDC 2337637'
loop_
_audit_author_name
_audit_author_address
'Lin Huang'
;Tianjin University
China
;
_audit_update_record             
;
2024-03-05 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-27
_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         'C33 H24 B N'
_chemical_formula_sum            'C33 H24 B N'
_chemical_formula_weight         445.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.69340(10)
_cell_length_b                   21.4946(4)
_cell_length_c                   12.5425(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.2760(10)
_cell_angle_gamma                90
_cell_volume                     2337.18(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.2230
_cell_measurement_theta_min      4.0980
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'fluorescent light yellow'
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16092
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.475
_diffrn_reflns_theta_min         4.089
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -38.00   0.50    1.50    --  -46.28 132.00  53.00   50
  2  ω   -102.00 -50.00   0.50    1.50    --  -46.28 137.00-130.00  104
  3  ω     36.00  61.00   0.50    1.50    --   46.28-132.00 -16.00   50
  4  ω     70.00 109.00   0.50    1.50    --   46.28 137.00-130.00   78
  5  ω     76.00 109.00   0.50    1.50    --   46.28 132.00  53.00   66
  6  ω     39.00  64.00   0.50    1.50    --   46.28-137.00 166.00   50
  7  ω   -116.00 -89.00   0.50    6.00    -- -100.00 132.00  53.00   54
  8  ω   -149.00-124.00   0.50    6.00    -- -100.00-132.00 -16.00   50
  9  ω   -147.00-121.00   0.50    6.00    -- -100.00-137.00 166.00   52
 10  ω   -114.00 -30.00   0.50    6.00    -- -100.00 137.00-130.00  168
 11  ω     70.00 155.00   0.50    6.00    --  105.53 137.00-130.00  170
 12  ω     51.00  76.00   0.50    6.00    --  105.53-132.00 -16.00   50
 13  ω     22.00 118.00   0.50    1.50    --   46.28  77.00 150.00  192
 14  ω     -6.00  24.00   0.50    1.50    --   46.28 -19.00-150.00   60
 15  ω    -27.00  11.00   0.50    1.50    --   46.28 -37.00-150.00   76
 16  ω    -71.00 -40.00   0.50    6.00    -- -100.00  61.00-180.00   62
 17  ω   -170.00 -82.00   0.50    6.00    -- -100.00 -61.00   0.00  176
 18  ω    -65.00 -33.00   0.50    6.00    -- -100.00  61.00 -90.00   64
 19  ω    -60.00 -34.00   0.50    6.00    -- -100.00  61.00  90.00   52
 20  ω    -53.00 -28.00   0.50    6.00    -- -100.00  45.00-120.00   50
 21  ω     60.00 103.00   0.50    6.00    --  105.53 -94.00-180.00   86
 22  ω     85.00 174.00   0.50    6.00    --  105.53  15.00-120.00  178
 23  ω     75.00 102.00   0.50    6.00    --  105.53 -94.00-150.00   54
 24  ω     39.00 111.00   0.50    6.00    --  105.53-125.00-150.00  144
 25  ω    125.00 150.00   0.50    6.00    --  105.53  45.00-150.00   50
 26  ω     32.00  67.00   0.50    6.00    --  105.53 -61.00 -60.00   70
 27  ω     79.00 104.00   0.50    6.00    --  105.53 -94.00   0.00   50
 28  ω     93.00 118.00   0.50    6.00    --  105.53  45.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0180320000
_diffrn_orient_matrix_UB_12      0.0679351000
_diffrn_orient_matrix_UB_13      0.0380855000
_diffrn_orient_matrix_UB_21      -0.0610101000
_diffrn_orient_matrix_UB_22      0.0228309000
_diffrn_orient_matrix_UB_23      -0.1116761000
_diffrn_orient_matrix_UB_31      -0.1659142000
_diffrn_orient_matrix_UB_32      -0.0010287000
_diffrn_orient_matrix_UB_33      0.0353475000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3485
_reflns_number_total             4554
_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 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0542
_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)+(0.1212P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1709
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C43(H43), C20(H20), C24(H24), C50(H50), C48(H48), C56(H56),
 C46(H46), C40(H40), C44(H44), C7(H7), C3(H3), C53(H53), C38(H38)
2.c Idealised Me refined as rotating group:
 C57(H57A,H57B,H57C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N45 N 0.85627(15) 0.41416(6) 0.31981(11) 0.0556(3) Uani 1 1 d . . . . .
C37 C 0.71351(17) 0.32420(7) 0.30170(11) 0.0478(3) Uani 1 1 d . . . . .
C23 C 0.41502(17) 0.29047(7) 0.33296(11) 0.0505(4) Uani 1 1 d . . . . .
C17 C 0.67490(18) 0.25805(7) 0.28911(11) 0.0494(3) Uani 1 1 d . . . . .
C9 C 0.51996(17) 0.24638(7) 0.29533(11) 0.0509(4) Uani 1 1 d . . . . .
C47 C 0.46217(17) 0.34789(7) 0.37196(12) 0.0504(4) Uani 1 1 d . . . . .
C33 C 0.61423(17) 0.36665(6) 0.34741(11) 0.0489(3) Uani 1 1 d . . . . .
C35 C 0.97362(17) 0.33964(8) 0.20961(12) 0.0548(4) Uani 1 1 d . . . . .
C5 C 0.85450(17) 0.35702(7) 0.27666(11) 0.0505(4) Uani 1 1 d . . . . .
C19 C 0.28873(17) 0.25810(9) 0.37070(12) 0.0585(4) Uani 1 1 d . . . . .
C39 C 0.4586(2) 0.18647(7) 0.31294(12) 0.0598(4) Uani 1 1 d . . . . .
C41 C 0.7700(2) 0.20263(8) 0.29518(13) 0.0600(4) Uani 1 1 d . . . . .
H41 H 0.874921 0.206238 0.286471 0.072 Uiso 1 1 calc R U . . .
C43 C 0.35880(19) 0.37557(8) 0.44368(14) 0.0614(4) Uani 1 1 d . . . . .
H43 H 0.376422 0.416364 0.466097 0.074 Uiso 1 1 calc R U . . .
C20 C 0.96812(19) 0.28500(9) 0.14627(12) 0.0630(4) Uani 1 1 d . . . . .
H20 H 0.884769 0.258000 0.148177 0.076 Uiso 1 1 calc R U . . .
C18 C 0.3151(2) 0.19379(9) 0.35735(13) 0.0648(5) Uani 1 1 d . . . . .
C22 C 0.20097(18) 0.28119(10) 0.44884(14) 0.0665(5) Uani 1 1 d . . . . .
C16 C 1.09799(19) 0.38146(10) 0.20035(14) 0.0648(5) Uani 1 1 d . . . . .
C12 C 0.5494(3) 0.13462(8) 0.32970(14) 0.0693(5) Uani 1 1 d . . . . .
C24 C 1.0972(2) 0.43876(10) 0.25553(17) 0.0733(5) Uani 1 1 d . . . . .
H24 H 1.180700 0.465720 0.253870 0.088 Uiso 1 1 calc R U . . .
C6 C 0.7335(2) 0.44840(8) 0.49653(15) 0.0678(5) Uani 1 1 d . . . . .
H6A H 0.801716 0.484157 0.501848 0.081 Uiso 1 1 calc R U . . .
H6B H 0.637178 0.460802 0.524666 0.081 Uiso 1 1 calc R U . . .
C8 C 0.6200(2) 0.48992(8) 0.30410(15) 0.0672(5) Uani 1 1 d . . . . .
H8A H 0.519884 0.497940 0.330666 0.081 Uiso 1 1 calc R U . . .
H8B H 0.683126 0.526534 0.319066 0.081 Uiso 1 1 calc R U . . .
C50 C 0.2361(2) 0.34416(10) 0.47987(15) 0.0691(5) Uani 1 1 d . . . . .
H50 H 0.173537 0.364245 0.526040 0.083 Uiso 1 1 calc R U . . .
C48 C 0.9759(2) 0.45426(9) 0.31038(16) 0.0677(5) Uani 1 1 d . . . . .
H48 H 0.973578 0.493185 0.342609 0.081 Uiso 1 1 calc R U . . .
C56 C 0.7090(3) 0.14447(8) 0.31357(15) 0.0708(5) Uani 1 1 d . . . . .
H56 H 0.774577 0.110238 0.315556 0.085 Uiso 1 1 calc R U . . .
C46 C 1.0840(2) 0.27175(12) 0.08264(14) 0.0771(6) Uani 1 1 d . . . . .
H46 H 1.079089 0.235535 0.041958 0.093 Uiso 1 1 calc R U . . .
C15 C 0.2530(2) 0.14902(10) 0.42052(15) 0.0765(6) Uani 1 1 d . . . . .
C40 C 1.2158(2) 0.36492(13) 0.13392(17) 0.0825(7) Uani 1 1 d . . . . .
H40 H 1.299563 0.391403 0.128921 0.099 Uiso 1 1 calc R U . . .
C44 C 1.2089(2) 0.31117(14) 0.07741(16) 0.0871(7) Uani 1 1 d . . . . .
H44 H 1.288330 0.300751 0.034993 0.105 Uiso 1 1 calc R U . . .
C7 C 0.1150(2) 0.23508(13) 0.50213(16) 0.0804(6) Uani 1 1 d . . . . .
H7 H 0.040898 0.247905 0.547243 0.097 Uiso 1 1 calc R U . . .
C3 C 0.1392(2) 0.17238(13) 0.48822(17) 0.0869(7) Uani 1 1 d . . . . .
H3 H 0.080127 0.144139 0.523731 0.104 Uiso 1 1 calc R U . . .
C53 C 0.4745(3) 0.08402(9) 0.38300(19) 0.0879(7) Uani 1 1 d . . . . .
H53 H 0.523521 0.045562 0.388547 0.105 Uiso 1 1 calc R U . . .
C57 C 0.5980(3) 0.48178(10) 0.18341(17) 0.0817(6) Uani 1 1 d . . . . .
H57A H 0.536882 0.515459 0.152992 0.123 Uiso 1 1 calc R U . . .
H57B H 0.546450 0.443064 0.167112 0.123 Uiso 1 1 calc R U . . .
H57C H 0.696820 0.481694 0.153971 0.123 Uiso 1 1 calc R U . . .
B59 B 0.6987(2) 0.43177(8) 0.37100(15) 0.0549(4) Uani 1 1 d . . . . .
C38 C 0.3360(3) 0.09079(11) 0.42492(19) 0.0915(7) Uani 1 1 d . . . . .
H38 H 0.293107 0.056756 0.457583 0.110 Uiso 1 1 calc R U . . .
C36 C 0.8045(3) 0.39771(11) 0.56748(18) 0.0917(7) Uani 1 1 d . . . . .
H36A H 0.898151 0.383546 0.539401 0.138 Uiso 1 1 calc R U . . .
H36B H 0.733565 0.363605 0.569797 0.138 Uiso 1 1 calc R U . . .
H36C H 0.827108 0.413732 0.638369 0.138 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N45 C5 1.342(2) . ?
N45 C48 1.363(2) . ?
N45 B59 1.601(2) . ?
C37 C17 1.467(2) . ?
C37 C33 1.407(2) . ?
C37 C5 1.468(2) . ?
C23 C9 1.420(2) . ?
C23 C47 1.379(2) . ?
C23 C19 1.411(2) . ?
C17 C9 1.378(2) . ?
C17 C41 1.449(2) . ?
C9 C39 1.417(2) . ?
C47 C33 1.437(2) . ?
C47 C43 1.446(2) . ?
C33 B59 1.598(2) . ?
C35 C5 1.432(2) . ?
C35 C20 1.417(3) . ?
C35 C16 1.417(2) . ?
C19 C18 1.413(3) . ?
C19 C22 1.379(3) . ?
C39 C18 1.413(3) . ?
C39 C12 1.373(3) . ?
C41 H41 0.9300 . ?
C41 C56 1.384(3) . ?
C43 H43 0.9300 . ?
C43 C50 1.368(3) . ?
C20 H20 0.9300 . ?
C20 C46 1.361(2) . ?
C18 C15 1.381(3) . ?
C22 C50 1.435(3) . ?
C22 C7 1.436(3) . ?
C16 C24 1.413(3) . ?
C16 C40 1.413(3) . ?
C12 C56 1.433(3) . ?
C12 C53 1.455(3) . ?
C24 H24 0.9300 . ?
C24 C48 1.343(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 B59 1.621(3) . ?
C6 C36 1.509(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C57 1.522(3) . ?
C8 B59 1.628(2) . ?
C50 H50 0.9300 . ?
C48 H48 0.9300 . ?
C56 H56 0.9300 . ?
C46 H46 0.9300 . ?
C46 C44 1.383(3) . ?
C15 C3 1.441(4) . ?
C15 C38 1.444(4) . ?
C40 H40 0.9300 . ?
C40 C44 1.354(4) . ?
C44 H44 0.9300 . ?
C7 H7 0.9300 . ?
C7 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C53 H53 0.9300 . ?
C53 C38 1.357(4) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C38 H38 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

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
C5 N45 C48 121.99(15) . . ?
C5 N45 B59 113.18(12) . . ?
C48 N45 B59 124.52(14) . . ?
C17 C37 C5 129.10(13) . . ?
C33 C37 C17 122.01(13) . . ?
C33 C37 C5 108.83(13) . . ?
C47 C23 C9 122.27(14) . . ?
C47 C23 C19 122.72(15) . . ?
C19 C23 C9 108.52(14) . . ?
C9 C17 C37 112.78(13) . . ?
C9 C17 C41 113.80(14) . . ?
C41 C17 C37 131.78(14) . . ?
C17 C9 C23 123.51(13) . . ?
C17 C9 C39 123.70(15) . . ?
C39 C9 C23 107.22(14) . . ?
C23 C47 C33 115.40(13) . . ?
C23 C47 C43 114.01(14) . . ?
C33 C47 C43 129.94(15) . . ?
C37 C33 C47 120.49(14) . . ?
C37 C33 B59 110.85(13) . . ?
C47 C33 B59 128.57(13) . . ?
C20 C35 C5 123.38(15) . . ?
C20 C35 C16 118.29(15) . . ?
C16 C35 C5 118.18(16) . . ?
N45 C5 C37 109.77(13) . . ?
N45 C5 C35 119.26(14) . . ?
C35 C5 C37 130.71(14) . . ?
C23 C19 C18 107.79(15) . . ?
C22 C19 C23 123.15(17) . . ?
C22 C19 C18 122.65(16) . . ?
C18 C39 C9 108.28(15) . . ?
C12 C39 C9 122.89(17) . . ?
C12 C39 C18 123.00(17) . . ?
C17 C41 H41 119.1 . . ?
C56 C41 C17 121.82(17) . . ?
C56 C41 H41 119.1 . . ?
C47 C43 H43 118.7 . . ?
C50 C43 C47 122.63(17) . . ?
C50 C43 H43 118.7 . . ?
C35 C20 H20 119.8 . . ?
C46 C20 C35 120.44(19) . . ?
C46 C20 H20 119.8 . . ?
C39 C18 C19 108.14(14) . . ?
C15 C18 C19 122.68(19) . . ?
C15 C18 C39 122.86(19) . . ?
C19 C22 C50 114.48(16) . . ?
C19 C22 C7 114.7(2) . . ?
C50 C22 C7 129.23(18) . . ?
C24 C16 C35 118.77(16) . . ?
C24 C16 C40 122.55(19) . . ?
C40 C16 C35 118.7(2) . . ?
C39 C12 C56 114.21(16) . . ?
C39 C12 C53 113.9(2) . . ?
C56 C12 C53 130.25(19) . . ?
C16 C24 H24 120.0 . . ?
C48 C24 C16 119.97(17) . . ?
C48 C24 H24 120.0 . . ?
H6A C6 H6B 107.3 . . ?
B59 C6 H6A 108.1 . . ?
B59 C6 H6B 108.1 . . ?
C36 C6 H6A 108.1 . . ?
C36 C6 H6B 108.1 . . ?
C36 C6 B59 116.87(15) . . ?
H8A C8 H8B 107.4 . . ?
C57 C8 H8A 108.2 . . ?
C57 C8 H8B 108.2 . . ?
C57 C8 B59 116.19(15) . . ?
B59 C8 H8A 108.2 . . ?
B59 C8 H8B 108.2 . . ?
C43 C50 C22 122.08(17) . . ?
C43 C50 H50 119.0 . . ?
C22 C50 H50 119.0 . . ?
N45 C48 H48 119.3 . . ?
C24 C48 N45 121.39(18) . . ?
C24 C48 H48 119.3 . . ?
C41 C56 C12 122.96(16) . . ?
C41 C56 H56 118.5 . . ?
C12 C56 H56 118.5 . . ?
C20 C46 H46 119.4 . . ?
C20 C46 C44 121.2(2) . . ?
C44 C46 H46 119.4 . . ?
C18 C15 C3 114.2(2) . . ?
C18 C15 C38 114.2(2) . . ?
C3 C15 C38 130.0(2) . . ?
C16 C40 H40 119.4 . . ?
C44 C40 C16 121.1(2) . . ?
C44 C40 H40 119.4 . . ?
C46 C44 H44 119.9 . . ?
C40 C44 C46 120.15(18) . . ?
C40 C44 H44 119.9 . . ?
C22 C7 H7 119.1 . . ?
C3 C7 C22 121.8(2) . . ?
C3 C7 H7 119.1 . . ?
C15 C3 H3 118.9 . . ?
C7 C3 C15 122.27(19) . . ?
C7 C3 H3 118.9 . . ?
C12 C53 H53 118.7 . . ?
C38 C53 C12 122.5(2) . . ?
C38 C53 H53 118.7 . . ?
C8 C57 H57A 109.5 . . ?
C8 C57 H57B 109.5 . . ?
C8 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
N45 B59 C6 109.78(14) . . ?
N45 B59 C8 108.32(14) . . ?
C33 B59 N45 96.54(12) . . ?
C33 B59 C6 115.02(14) . . ?
C33 B59 C8 114.03(14) . . ?
C6 B59 C8 111.86(14) . . ?
C15 C38 H38 118.9 . . ?
C53 C38 C15 122.24(19) . . ?
C53 C38 H38 118.9 . . ?
C6 C36 H36A 109.5 . . ?
C6 C36 H36B 109.5 . . ?
C6 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C37 C17 C9 C23 -13.07(19) . . . . ?
C37 C17 C9 C39 -163.34(13) . . . . ?
C37 C17 C41 C56 159.58(16) . . . . ?
C37 C33 B59 N45 3.77(16) . . . . ?
C37 C33 B59 C6 -111.66(15) . . . . ?
C37 C33 B59 C8 117.20(15) . . . . ?
C23 C9 C39 C18 2.03(16) . . . . ?
C23 C9 C39 C12 -151.70(15) . . . . ?
C23 C47 C33 C37 -9.6(2) . . . . ?
C23 C47 C33 B59 174.27(14) . . . . ?
C23 C47 C43 C50 7.8(2) . . . . ?
C23 C19 C18 C39 0.89(17) . . . . ?
C23 C19 C18 C15 153.57(16) . . . . ?
C23 C19 C22 C50 7.2(2) . . . . ?
C23 C19 C22 C7 -159.63(15) . . . . ?
C17 C37 C33 C47 -7.5(2) . . . . ?
C17 C37 C33 B59 169.30(13) . . . . ?
C17 C37 C5 N45 -167.55(14) . . . . ?
C17 C37 C5 C35 18.5(3) . . . . ?
C17 C9 C39 C18 156.38(14) . . . . ?
C17 C9 C39 C12 2.7(2) . . . . ?
C17 C41 C56 C12 -1.1(3) . . . . ?
C9 C23 C47 C33 15.2(2) . . . . ?
C9 C23 C47 C43 -156.49(14) . . . . ?
C9 C23 C19 C18 0.37(16) . . . . ?
C9 C23 C19 C22 152.78(15) . . . . ?
C9 C17 C41 C56 -4.5(2) . . . . ?
C9 C39 C18 C19 -1.82(17) . . . . ?
C9 C39 C18 C15 -154.44(16) . . . . ?
C9 C39 C12 C56 -8.0(2) . . . . ?
C9 C39 C12 C53 159.00(16) . . . . ?
C47 C23 C9 C17 -3.6(2) . . . . ?
C47 C23 C9 C39 150.86(14) . . . . ?
C47 C23 C19 C18 -151.82(14) . . . . ?
C47 C23 C19 C22 0.6(2) . . . . ?
C47 C33 B59 N45 -179.78(14) . . . . ?
C47 C33 B59 C6 64.8(2) . . . . ?
C47 C33 B59 C8 -66.4(2) . . . . ?
C47 C43 C50 C22 -0.1(3) . . . . ?
C33 C37 C17 C9 18.34(19) . . . . ?
C33 C37 C17 C41 -145.89(16) . . . . ?
C33 C37 C5 N45 9.65(17) . . . . ?
C33 C37 C5 C35 -164.30(15) . . . . ?
C33 C47 C43 C50 -162.43(16) . . . . ?
C35 C20 C46 C44 -0.5(3) . . . . ?
C35 C16 C24 C48 -3.8(3) . . . . ?
C35 C16 C40 C44 1.9(3) . . . . ?
C5 N45 C48 C24 1.2(3) . . . . ?
C5 N45 B59 C33 2.24(16) . . . . ?
C5 N45 B59 C6 121.82(15) . . . . ?
C5 N45 B59 C8 -115.78(15) . . . . ?
C5 C37 C17 C9 -164.78(14) . . . . ?
C5 C37 C17 C41 31.0(2) . . . . ?
C5 C37 C33 C47 175.09(13) . . . . ?
C5 C37 C33 B59 -8.13(17) . . . . ?
C5 C35 C20 C46 178.76(15) . . . . ?
C5 C35 C16 C24 -1.4(2) . . . . ?
C5 C35 C16 C40 -179.67(14) . . . . ?
C19 C23 C9 C17 -155.90(14) . . . . ?
C19 C23 C9 C39 -1.48(16) . . . . ?
C19 C23 C47 C33 163.69(13) . . . . ?
C19 C23 C47 C43 -8.0(2) . . . . ?
C19 C18 C15 C3 10.0(2) . . . . ?
C19 C18 C15 C38 -157.06(17) . . . . ?
C19 C22 C50 C43 -7.4(3) . . . . ?
C19 C22 C7 C3 10.3(2) . . . . ?
C39 C18 C15 C3 158.75(16) . . . . ?
C39 C18 C15 C38 -8.3(2) . . . . ?
C39 C12 C56 C41 7.3(2) . . . . ?
C39 C12 C53 C38 -8.4(3) . . . . ?
C41 C17 C9 C23 154.14(14) . . . . ?
C41 C17 C9 C39 3.9(2) . . . . ?
C43 C47 C33 C37 160.55(15) . . . . ?
C43 C47 C33 B59 -15.6(3) . . . . ?
C20 C35 C5 N45 -168.94(15) . . . . ?
C20 C35 C5 C37 4.5(3) . . . . ?
C20 C35 C16 C24 174.22(16) . . . . ?
C20 C35 C16 C40 -4.1(2) . . . . ?
C20 C46 C44 C40 -1.8(3) . . . . ?
C18 C19 C22 C50 155.65(16) . . . . ?
C18 C19 C22 C7 -11.2(2) . . . . ?
C18 C39 C12 C56 -157.96(15) . . . . ?
C18 C39 C12 C53 9.1(2) . . . . ?
C18 C15 C3 C7 -10.8(3) . . . . ?
C18 C15 C38 C53 8.9(3) . . . . ?
C22 C19 C18 C39 -151.69(15) . . . . ?
C22 C19 C18 C15 1.0(3) . . . . ?
C22 C7 C3 C15 0.7(3) . . . . ?
C16 C35 C5 N45 6.4(2) . . . . ?
C16 C35 C5 C37 179.88(15) . . . . ?
C16 C35 C20 C46 3.4(2) . . . . ?
C16 C24 C48 N45 4.1(3) . . . . ?
C16 C40 C44 C46 1.0(3) . . . . ?
C12 C39 C18 C19 151.87(15) . . . . ?
C12 C39 C18 C15 -0.7(3) . . . . ?
C12 C53 C38 C15 -0.5(3) . . . . ?
C24 C16 C40 C44 -176.29(19) . . . . ?
C50 C22 C7 C3 -154.2(2) . . . . ?
C48 N45 C5 C37 178.78(14) . . . . ?
C48 N45 C5 C35 -6.5(2) . . . . ?
C48 N45 B59 C33 176.06(14) . . . . ?
C48 N45 B59 C6 -64.4(2) . . . . ?
C48 N45 B59 C8 58.0(2) . . . . ?
C56 C12 C53 C38 156.0(2) . . . . ?
C40 C16 C24 C48 174.43(17) . . . . ?
C7 C22 C50 C43 157.17(18) . . . . ?
C3 C15 C38 C53 -155.7(2) . . . . ?
C53 C12 C56 C41 -157.13(19) . . . . ?
C57 C8 B59 N45 52.6(2) . . . . ?
C57 C8 B59 C33 -53.6(2) . . . . ?
C57 C8 B59 C6 173.74(16) . . . . ?
B59 N45 C5 C37 -7.23(17) . . . . ?
B59 N45 C5 C35 167.51(13) . . . . ?
B59 N45 C48 C24 -172.11(17) . . . . ?
C38 C15 C3 C7 153.8(2) . . . . ?
C36 C6 B59 N45 -60.6(2) . . . . ?
C36 C6 B59 C33 46.9(2) . . . . ?
C36 C6 B59 C8 179.11(18) . . . . ?

_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 4.098
_oxdiff_exptl_absorpt_empirical_full_min 0.271
