# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_CityU-30
_database_code_depnum_ccdc_archive 'CCDC 2363533'
loop_
_audit_author_name
_audit_author_address
'Jinghang WU'
;City University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2024-06-18 deposited with the CCDC.	2024-10-10 downloaded from the CCDC.
;
_audit_creation_date             2024-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 B N O2'
_chemical_formula_sum            'C21 H14 B N O2'
_chemical_formula_weight         323.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O  B N'
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'
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      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                   6.41670(10)
_cell_length_b                   13.1842(4)
_cell_length_c                   13.6585(4)
_cell_angle_alpha                116.729(3)
_cell_angle_beta                 92.641(2)
_cell_angle_gamma                103.286(2)
_cell_volume                     989.45(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5570
_cell_measurement_temperature    300
_cell_measurement_theta_max      68.0500
_cell_measurement_theta_min      3.8990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Light
_exptl_crystal_F_000             336
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8380
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.315
_diffrn_reflns_theta_min         3.678
_diffrn_ambient_temperature      300
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  66.00   0.50    3.63    --   42.80 -65.00  30.00   70
  2  ω     30.00  68.00   0.50    3.63    --   42.80 -82.00-120.00   76
  3  ω     30.00  64.00   0.50    3.63    --   42.80 -82.00-150.00   68
  4  ω     12.00  66.00   0.50    3.63    --   42.80 -77.00-180.00  108
  5  ω    -41.00 -15.00   0.50    3.63    --   42.80 -65.00  30.00   52
  6  ω     32.00  58.00   0.50    3.63    --   42.80  82.00 150.00   52
  7  ω     35.00  70.00   0.50    3.63    --   42.80 -82.00 -30.00   70
  8  ω     45.00  70.00   0.50    3.63    --   42.80 -82.00  60.00   50
  9  ω     59.00 128.00   0.50    3.63    --   42.80  82.00 150.00  138
 10  ω    -18.00  22.00   0.50    3.63    --   42.80 -77.00  60.00   80
 11  ω     88.00 131.00   0.50    3.63    --   42.80 -21.00 150.00   86
 12  ω    -11.00  25.00   0.50    3.63    --   42.80 -65.00  30.00   72
 13  ω      9.00  35.00   0.50    3.63    --   42.80 -65.00 -60.00   52
 14  ω    -47.00  -6.00   0.50    3.63    --   42.80 -82.00 150.00   82
 15  ω    -46.00 -21.00   0.50    3.63    --   42.80 -21.00 150.00   50
 16  ω    -21.00   5.00   0.50    3.63    --   42.80 -82.00-120.00   52
 17  ω     53.00 124.00   0.50    3.63    --   42.80  65.00-120.00  142
 18  ω    -47.00  30.00   0.50    3.63    --   42.80 -82.00 -30.00  154
 19  ω      1.00  59.00   0.50    3.63    --   42.80 -82.00 150.00  116
 20  ω     37.00  85.00   0.50   14.50    --   94.00 -82.00  30.00   96
 21  ω     10.00 124.00   0.50   14.50    --   94.00 -33.00 150.00  228
 22  ω      5.00 183.00   0.50   14.50    --   94.00   8.00-120.00  356
 23  ω     49.00  89.00   0.50   14.50    --   94.00 -82.00 -90.00   80
 24  ω     99.00 128.00   0.50   14.50    --   94.00 -33.00 -60.00   58
 25  ω     83.00 109.00   0.50   14.50    --   94.00 -59.00  30.00   52
 26  ω     73.00 118.00   0.50   14.50    --   94.00 -82.00-150.00   90
 27  ω      5.00  30.00   0.50   14.50    --   94.00 -59.00  30.00   50
 28  ω     74.00 101.00   0.50   14.50    --   94.00 -82.00  90.00   54
 29  ω     36.00  66.00   0.50   14.50    --   94.00 -82.00   0.00   60
 30  ω     25.00  56.00   0.50   14.50    --   94.00 -82.00  90.00   62
 31  ω      5.00  73.00   0.50   14.50    --   94.00 -33.00 -60.00  136
 32  ω      6.00  57.00   0.50   14.50    --   94.00 -82.00 -60.00  102
 33  ω     73.00  99.00   0.50   14.50    --   94.00  68.00 -30.00   52
 34  ω    151.00 176.00   0.50   14.50    --   94.00  33.00 150.00   50
 35  ω     13.00  92.00   0.50   14.50    --   94.00 -82.00  60.00  158
 36  ω      6.00 120.00   0.50   14.50    --   94.00 -59.00 150.00  228
 37  ω    117.00 170.00   0.50   14.50    --   94.00  77.00-120.00  106
 38  ω     64.00  89.00   0.50   14.50    --   94.00 -82.00 -60.00   50
 39  ω     94.00 120.00   0.50   14.50    --   94.00  33.00 150.00   52
 40  ω     68.00  94.00   0.50   14.50    --   94.00 -82.00   0.00   52
 41  ω     31.00 104.00   0.50   14.50    --   94.00 -82.00 150.00  146
 42  ω      7.00  96.00   0.50   14.50    --   94.00 -82.00 -39.32  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0226748000
_diffrn_orient_matrix_UB_12      0.1321064000
_diffrn_orient_matrix_UB_13      0.0756757000
_diffrn_orient_matrix_UB_21      0.0239395000
_diffrn_orient_matrix_UB_22      0.0232083000
_diffrn_orient_matrix_UB_23      -0.1004081000
_diffrn_orient_matrix_UB_31      -0.2482369000
_diffrn_orient_matrix_UB_32      -0.0243109000
_diffrn_orient_matrix_UB_33      -0.0250049000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed 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                3170
_reflns_number_total             3489
_reflns_odcompleteness_completeness 97.29
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_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         0.249
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0075(11)
_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   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      0.973
_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)+(0.0922P)²+0.2346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1425
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C18(H18), C3(H3), C21(H21), C11(H11), C10(H10), C4(H4),
 C19(H19), C20(H20), C1(H1), C9(H9), C7(H7), C2(H2)
;
_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
O1 O 1.07965(16) 0.48815(9) 0.27745(8) 0.0460(3) Uani 1 1 d . . . . .
O2 O 0.72214(17) 0.37392(9) 0.18830(8) 0.0457(3) Uani 1 1 d . . . . .
N1 N 0.80032(19) 0.59415(10) 0.27775(9) 0.0404(3) Uani 1 1 d . . . . .
C5 C 1.0025(2) 0.41270(13) 0.31914(12) 0.0430(3) Uani 1 1 d . . . . .
C17 C 0.6201(2) 0.96725(12) 0.56500(12) 0.0419(3) Uani 1 1 d . . . . .
C16 C 0.4598(2) 0.93086(12) 0.38246(12) 0.0427(3) Uani 1 1 d . . . . .
C6 C 0.7906(3) 0.34557(12) 0.26705(12) 0.0441(3) Uani 1 1 d . . . . .
C15 C 0.5776(2) 0.89984(12) 0.44886(12) 0.0422(3) Uani 1 1 d . . . . .
C12 C 0.6102(2) 0.58479(12) 0.31241(12) 0.0437(3) Uani 1 1 d . . . . .
H12 H 0.524664 0.510330 0.296944 0.052 Uiso 1 1 calc R U . . .
C8 C 0.9495(2) 0.48656(13) 0.09471(12) 0.0437(3) Uani 1 1 d . . . . .
C14 C 0.6588(2) 0.79324(12) 0.39322(12) 0.0424(3) Uani 1 1 d . . . . .
C13 C 0.5354(2) 0.68206(13) 0.37068(13) 0.0470(4) Uani 1 1 d . . . . .
H13 H 0.402421 0.672719 0.394671 0.056 Uiso 1 1 calc R U . . .
C18 C 0.7418(3) 0.93862(14) 0.63484(14) 0.0524(4) Uani 1 1 d . . . . .
H18 H 0.794316 0.872791 0.602451 0.063 Uiso 1 1 calc R U . . .
C3 C 1.1094(3) 0.39832(16) 0.39913(14) 0.0557(4) Uani 1 1 d . . . . .
H3 H 1.251372 0.443215 0.433759 0.067 Uiso 1 1 calc R U . . .
C21 C 0.5862(3) 1.13576(14) 0.73609(13) 0.0534(4) Uani 1 1 d . . . . .
H21 H 0.534199 1.201404 0.771454 0.064 Uiso 1 1 calc R U . . .
C11 C 0.8590(3) 0.80188(14) 0.35914(16) 0.0587(4) Uani 1 1 d . . . . .
H11 H 0.949048 0.875448 0.374776 0.070 Uiso 1 1 calc R U . . .
C10 C 0.9245(3) 0.70199(14) 0.30232(16) 0.0567(4) Uani 1 1 d . . . . .
H10 H 1.059541 0.709313 0.280097 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6776(3) 0.26220(15) 0.29387(15) 0.0591(4) Uani 1 1 d . . . . .
H4 H 0.535132 0.217985 0.259577 0.071 Uiso 1 1 calc R U . . .
C19 C 0.7821(3) 1.00528(17) 0.74688(15) 0.0615(5) Uani 1 1 d . . . . .
H19 H 0.861903 0.984882 0.790295 0.074 Uiso 1 1 calc R U . . .
C20 C 0.7043(3) 1.10529(17) 0.79836(14) 0.0634(5) Uani 1 1 d . . . . .
H20 H 0.733947 1.150751 0.875421 0.076 Uiso 1 1 calc R U . . .
C1 C 0.9962(4) 0.31354(17) 0.42637(16) 0.0670(5) Uani 1 1 d . . . . .
H1 H 1.063798 0.301669 0.480493 0.080 Uiso 1 1 calc R U . . .
C9 C 0.7930(3) 0.4814(2) 0.01908(16) 0.0703(6) Uani 1 1 d . . . . .
H9 H 0.649205 0.468099 0.029902 0.084 Uiso 1 1 calc R U . . .
B1 B 0.8929(3) 0.47652(15) 0.20313(13) 0.0422(4) Uani 1 1 d . . . . .
C7 C 1.1581(3) 0.5047(2) 0.07274(15) 0.0683(5) Uani 1 1 d . . . . .
H7 H 1.269463 0.507665 0.120874 0.082 Uiso 1 1 calc R U . . .
C2 C 0.7861(4) 0.24696(17) 0.37469(17) 0.0703(5) Uani 1 1 d . . . . .
H2 H 0.715191 0.190584 0.394236 0.084 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
O1 C5 1.3667(17) . ?
O1 B1 1.4673(19) . ?
O2 C6 1.3722(17) . ?
O2 B1 1.4572(19) . ?
N1 C12 1.3281(19) . ?
N1 C10 1.339(2) . ?
N1 B1 1.690(2) . ?
C5 C6 1.389(2) . ?
C5 C3 1.370(2) . ?
C17 C16 1.437(2) 2_676 ?
C17 C15 1.400(2) . ?
C17 C18 1.433(2) . ?
C16 C15 1.405(2) . ?
C16 C21 1.428(2) 2_676 ?
C6 C4 1.374(2) . ?
C15 C14 1.4957(19) . ?
C12 C13 1.381(2) . ?
C8 C9 1.375(2) . ?
C8 B1 1.596(2) . ?
C8 C7 1.376(2) . ?
C14 C13 1.381(2) . ?
C14 C11 1.384(2) . ?
C18 C19 1.353(2) . ?
C3 C1 1.393(3) . ?
C21 C20 1.359(2) . ?
C11 C10 1.371(2) . ?
C4 C2 1.392(3) . ?
C19 C20 1.408(3) . ?
C1 C2 1.377(3) . ?
C9 C7 1.386(2) 2_765 ?

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 O1 B1 105.32(11) . . ?
C6 O2 B1 105.29(11) . . ?
C12 N1 C10 118.53(13) . . ?
C12 N1 B1 123.25(12) . . ?
C10 N1 B1 118.21(12) . . ?
O1 C5 C6 110.50(12) . . ?
O1 C5 C3 127.91(15) . . ?
C3 C5 C6 121.58(14) . . ?
C15 C17 C16 119.67(13) . 2_676 ?
C15 C17 C18 122.34(14) . . ?
C18 C17 C16 117.99(14) . 2_676 ?
C15 C16 C17 119.26(13) . 2_676 ?
C15 C16 C21 122.53(14) . 2_676 ?
C21 C16 C17 118.20(14) 2_676 2_676 ?
O2 C6 C5 110.54(12) . . ?
O2 C6 C4 127.84(15) . . ?
C4 C6 C5 121.60(15) . . ?
C17 C15 C16 121.07(13) . . ?
C17 C15 C14 120.18(13) . . ?
C16 C15 C14 118.75(13) . . ?
N1 C12 C13 122.14(13) . . ?
C9 C8 B1 121.81(14) . . ?
C9 C8 C7 115.80(14) . . ?
C7 C8 B1 122.36(14) . . ?
C13 C14 C15 121.69(13) . . ?
C13 C14 C11 117.31(14) . . ?
C11 C14 C15 120.98(13) . . ?
C12 C13 C14 119.81(14) . . ?
C19 C18 C17 121.42(15) . . ?
C5 C3 C1 117.14(17) . . ?
C20 C21 C16 121.39(15) . 2_676 ?
C10 C11 C14 119.97(14) . . ?
N1 C10 C11 122.17(15) . . ?
C6 C4 C2 116.96(18) . . ?
C18 C19 C20 120.60(15) . . ?
C21 C20 C19 120.39(16) . . ?
C2 C1 C3 121.28(16) . . ?
C8 C9 C7 122.29(16) . 2_765 ?
O1 B1 N1 105.26(11) . . ?
O1 B1 C8 115.02(12) . . ?
O2 B1 O1 106.89(11) . . ?
O2 B1 N1 105.07(11) . . ?
O2 B1 C8 117.99(13) . . ?
C8 B1 N1 105.41(11) . . ?
C8 C7 C9 121.90(16) . 2_765 ?
C1 C2 C4 121.44(17) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.177 0.000 0.000 242.4 56.7 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 2.227
_oxdiff_exptl_absorpt_empirical_full_min 0.629
