# Electronic Supplementary Material (ESI) for Materials Advances.
# 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. 
# 
#######################################################################

data_bb
_audit_block_doi                 10.5517/ccdc.csd.cc283ymz
_database_code_depnum_ccdc_archive 'CCDC 2089171'
loop_
_audit_author_name
_audit_author_address
'Jun Miao'
;Jilin University
China
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H30 B N O2'
_chemical_formula_sum            'C32 H30 B N O2'
_chemical_formula_weight         471.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3775(5)
_cell_length_b                   10.9532(9)
_cell_length_c                   16.1075(12)
_cell_angle_alpha                93.642(3)
_cell_angle_beta                 99.389(3)
_cell_angle_gamma                103.657(3)
_cell_volume                     1240.77(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28608
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.717
_diffrn_reflns_theta_min         2.578
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4647
_reflns_number_total             5241
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.345
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_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     329
_refine_ls_number_reflns         5241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0386
_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)+(0.0507P)²+0.5676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1071
_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:
 C008(H008), C00A(H00A), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V)
2.b Idealised Me refined as rotating group:
 C00W(H00b,H00e,H00f), C00X(H00q,H00s,H00w), C00Y(H00x,H00y,H), C00Z(H00z,Ha,Hb)
;
_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
O001 O 0.48604(12) 0.64980(8) 0.11217(5) 0.02131(19) Uani 1 1 d . . . . .
O002 O 0.79724(12) 0.75842(8) 0.14702(5) 0.02173(19) Uani 1 1 d . . . . .
N003 N 0.70815(13) 0.22289(9) 0.34684(6) 0.0169(2) Uani 1 1 d . . . . .
C004 C 0.69202(16) 0.55074(10) 0.21764(7) 0.0156(2) Uani 1 1 d . . . . .
C005 C 0.57943(15) 0.40812(10) 0.32197(7) 0.0155(2) Uani 1 1 d . . . . .
C006 C 0.56987(15) 0.51533(10) 0.27576(7) 0.0152(2) Uani 1 1 d . . . . .
C007 C 0.82969(16) 0.36954(10) 0.24834(7) 0.0160(2) Uani 1 1 d . . . . .
C008 C 0.89970(16) 0.32139(11) 0.48407(7) 0.0189(2) Uani 1 1 d . . . . .
H008 H 0.826019 0.381699 0.484726 0.023 Uiso 1 1 calc R . . . .
C009 C 0.54902(16) 0.11892(10) 0.32965(7) 0.0171(2) Uani 1 1 d . . . . .
C00A C 0.45854(16) 0.37827(11) 0.38274(7) 0.0180(2) Uani 1 1 d . . . . .
H00A H 0.464030 0.307946 0.413809 0.022 Uiso 1 1 calc R . . . .
C00B C 0.86028(16) 0.22841(11) 0.41582(7) 0.0170(2) Uani 1 1 d . . . . .
C00C C 0.33584(17) 0.44932(11) 0.39658(7) 0.0201(2) Uani 1 1 d . . . . .
H00C H 0.257095 0.428407 0.437377 0.024 Uiso 1 1 calc R . . . .
C00D C 0.32449(17) 0.55440(11) 0.35060(8) 0.0203(2) Uani 1 1 d . . . . .
H00D H 0.237691 0.602941 0.360633 0.024 Uiso 1 1 calc R . . . .
C00E C 0.70615(16) 0.33513(10) 0.30582(7) 0.0158(2) Uani 1 1 d . . . . .
C00F C 0.82602(16) 0.48112(11) 0.20601(7) 0.0160(2) Uani 1 1 d . . . . .
C00G C 0.52354(18) 0.02377(11) 0.38418(8) 0.0222(3) Uani 1 1 d . . . . .
H00G H 0.615098 0.029304 0.434042 0.027 Uiso 1 1 calc R . . . .
C00H C 1.07464(17) 0.44185(12) 0.13270(8) 0.0218(3) Uani 1 1 d . . . . .
H00H H 1.159218 0.466116 0.094662 0.026 Uiso 1 1 calc R . . . .
C00I C 0.97039(17) 0.14117(11) 0.41484(8) 0.0214(2) Uani 1 1 d . . . . .
H00I H 0.944676 0.077980 0.368314 0.026 Uiso 1 1 calc R . . . .
C00J C 0.43674(16) 0.58619(11) 0.29233(7) 0.0182(2) Uani 1 1 d . . . . .
H00J H 0.426856 0.656654 0.262008 0.022 Uiso 1 1 calc R . . . .
C00K C 0.95539(16) 0.51451(11) 0.14864(7) 0.0192(2) Uani 1 1 d . . . . .
H00K H 0.957726 0.588993 0.121226 0.023 Uiso 1 1 calc R . . . .
C00L C 1.04734(17) 0.32594(12) 0.55144(8) 0.0223(3) Uani 1 1 d . . . . .
H00L H 1.073605 0.389055 0.598058 0.027 Uiso 1 1 calc R . . . .
C00M C 0.95589(16) 0.29515(11) 0.22878(7) 0.0188(2) Uani 1 1 d . . . . .
H00M H 0.957795 0.220375 0.255362 0.023 Uiso 1 1 calc R . . . .
C00N C 1.11794(18) 0.14658(12) 0.48198(8) 0.0251(3) Uani 1 1 d . . . . .
H00N H 1.193121 0.087223 0.480997 0.030 Uiso 1 1 calc R . . . .
C00O C 0.40971(17) 0.10861(12) 0.25725(8) 0.0222(3) Uani 1 1 d . . . . .
H00O H 0.423314 0.171904 0.219436 0.027 Uiso 1 1 calc R . . . .
C00P C 1.15589(17) 0.23825(12) 0.55038(8) 0.0249(3) Uani 1 1 d . . . . .
H00P H 1.255903 0.241012 0.596381 0.030 Uiso 1 1 calc R . . . .
C00Q C 0.51131(17) 0.74453(11) 0.05260(7) 0.0204(2) Uani 1 1 d . . . . .
C00R C 1.07306(17) 0.32992(12) 0.17271(8) 0.0215(2) Uani 1 1 d . . . . .
H00R H 1.154717 0.278728 0.160213 0.026 Uiso 1 1 calc R . . . .
C00S C 0.70054(17) 0.83926(11) 0.09681(8) 0.0205(2) Uani 1 1 d . . . . .
C00T C 0.3651(2) -0.07861(12) 0.36574(9) 0.0286(3) Uani 1 1 d . . . . .
H00T H 0.350784 -0.142716 0.402947 0.034 Uiso 1 1 calc R . . . .
C00U C 0.25201(19) 0.00626(13) 0.24066(9) 0.0285(3) Uani 1 1 d . . . . .
H00U H 0.158284 0.001018 0.191625 0.034 Uiso 1 1 calc R . . . .
C00V C 0.22802(19) -0.08862(13) 0.29403(10) 0.0311(3) Uani 1 1 d . . . . .
H00V H 0.120201 -0.158728 0.281695 0.037 Uiso 1 1 calc R . . . .
C00W C 0.6728(2) 0.93985(12) 0.15969(9) 0.0306(3) Uani 1 1 d . . . . .
H00B H 0.588250 0.899785 0.196598 0.046 Uiso 1 1 calc GR . . . .
H00E H 0.616514 1.000282 0.128938 0.046 Uiso 1 1 calc GR . . . .
H00F H 0.795884 0.984300 0.194029 0.046 Uiso 1 1 calc GR . . . .
C00X C 0.8245(2) 0.89803(13) 0.03616(9) 0.0300(3) Uani 1 1 d . . . . .
H00Q H 0.933965 0.962422 0.067807 0.045 Uiso 1 1 calc GR . . . .
H00S H 0.750879 0.937254 -0.005629 0.045 Uiso 1 1 calc GR . . . .
H00W H 0.868806 0.832417 0.007113 0.045 Uiso 1 1 calc GR . . . .
C00Y C 0.3381(2) 0.79810(14) 0.04014(10) 0.0321(3) Uani 1 1 d . . . . .
H00X H 0.226055 0.731182 0.013820 0.048 Uiso 1 1 calc GR . . . .
H00Y H 0.357170 0.866255 0.003426 0.048 Uiso 1 1 calc GR . . . .
H H 0.319250 0.831463 0.095124 0.048 Uiso 1 1 calc GR . . . .
C00Z C 0.5264(2) 0.67509(13) -0.02996(8) 0.0316(3) Uani 1 1 d . . . . .
H00Z H 0.640852 0.643236 -0.021534 0.047 Uiso 1 1 calc GR . . . .
HA H 0.533770 0.733257 -0.073788 0.047 Uiso 1 1 calc GR . . . .
HB H 0.414424 0.604105 -0.047699 0.047 Uiso 1 1 calc GR . . . .
B010 B 0.66047(19) 0.65638(12) 0.15909(8) 0.0165(2) 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
O001 C00Q 1.4579(13) . ?
O001 B010 1.3654(15) . ?
O002 C00S 1.4656(14) . ?
O002 B010 1.3653(15) . ?
N003 C009 1.4051(15) . ?
N003 C00B 1.4319(14) . ?
N003 C00E 1.4342(14) . ?
C004 C006 1.4125(15) . ?
C004 C00F 1.4114(16) . ?
C004 B010 1.5737(16) . ?
C005 C006 1.4391(15) . ?
C005 C00A 1.4312(16) . ?
C005 C00E 1.4094(16) . ?
C006 C00J 1.4344(16) . ?
C007 C00E 1.4099(16) . ?
C007 C00F 1.4403(15) . ?
C007 C00M 1.4322(16) . ?
C008 C00B 1.3943(17) . ?
C008 C00L 1.3958(17) . ?
C009 C00G 1.4038(16) . ?
C009 C00O 1.4022(16) . ?
C00A C00C 1.3606(17) . ?
C00B C00I 1.3936(16) . ?
C00C C00D 1.4192(16) . ?
C00D C00J 1.3590(17) . ?
C00F C00K 1.4368(16) . ?
C00G C00T 1.3918(18) . ?
C00H C00K 1.3608(17) . ?
C00H C00R 1.4195(17) . ?
C00I C00N 1.3910(17) . ?
C00L C00P 1.3893(18) . ?
C00M C00R 1.3604(17) . ?
C00N C00P 1.3880(19) . ?
C00O C00U 1.3880(18) . ?
C00Q C00S 1.5590(17) . ?
C00Q C00Y 1.5174(17) . ?
C00Q C00Z 1.5230(18) . ?
C00S C00W 1.5211(18) . ?
C00S C00X 1.5160(17) . ?
C00T C00V 1.385(2) . ?
C00U C00V 1.388(2) . ?

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
B010 O001 C00Q 107.42(9) . . ?
B010 O002 C00S 106.94(9) . . ?
C009 N003 C00B 120.82(9) . . ?
C009 N003 C00E 120.29(9) . . ?
C00B N003 C00E 117.95(9) . . ?
C006 C004 B010 119.43(10) . . ?
C00F C004 C006 119.44(10) . . ?
C00F C004 B010 120.72(10) . . ?
C00A C005 C006 118.84(10) . . ?
C00E C005 C006 119.26(10) . . ?
C00E C005 C00A 121.90(10) . . ?
C004 C006 C005 120.52(10) . . ?
C004 C006 C00J 121.51(10) . . ?
C00J C006 C005 117.95(10) . . ?
C00E C007 C00F 119.24(10) . . ?
C00E C007 C00M 122.09(10) . . ?
C00M C007 C00F 118.64(10) . . ?
C00B C008 C00L 120.06(11) . . ?
C00G C009 N003 121.47(10) . . ?
C00O C009 N003 120.31(10) . . ?
C00O C009 C00G 118.22(11) . . ?
C00C C00A C005 120.85(11) . . ?
C008 C00B N003 120.24(10) . . ?
C00I C00B N003 120.11(11) . . ?
C00I C00B C008 119.65(11) . . ?
C00A C00C C00D 120.56(11) . . ?
C00J C00D C00C 120.56(11) . . ?
C005 C00E N003 120.05(10) . . ?
C005 C00E C007 120.87(10) . . ?
C007 C00E N003 119.07(10) . . ?
C004 C00F C007 120.46(10) . . ?
C004 C00F C00K 121.58(10) . . ?
C00K C00F C007 117.88(10) . . ?
C00T C00G C009 120.49(12) . . ?
C00K C00H C00R 120.22(11) . . ?
C00N C00I C00B 120.03(12) . . ?
C00D C00J C006 121.24(11) . . ?
C00H C00K C00F 121.48(11) . . ?
C00P C00L C008 120.05(12) . . ?
C00R C00M C007 121.02(11) . . ?
C00P C00N C00I 120.35(12) . . ?
C00U C00O C009 120.23(12) . . ?
C00N C00P C00L 119.86(11) . . ?
O001 C00Q C00S 102.17(9) . . ?
O001 C00Q C00Y 108.60(10) . . ?
O001 C00Q C00Z 106.03(10) . . ?
C00Y C00Q C00S 115.47(10) . . ?
C00Y C00Q C00Z 110.27(11) . . ?
C00Z C00Q C00S 113.45(11) . . ?
C00M C00R C00H 120.71(11) . . ?
O002 C00S C00Q 102.38(9) . . ?
O002 C00S C00W 106.18(10) . . ?
O002 C00S C00X 108.90(10) . . ?
C00W C00S C00Q 113.42(10) . . ?
C00X C00S C00Q 114.08(10) . . ?
C00X C00S C00W 111.11(11) . . ?
C00V C00T C00G 121.12(12) . . ?
C00O C00U C00V 121.54(12) . . ?
C00T C00V C00U 118.40(12) . . ?
O001 B010 C004 120.82(10) . . ?
O002 B010 O001 113.35(10) . . ?
O002 B010 C004 125.79(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
