# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_bNCSBA
_database_code_depnum_ccdc_archive 'CCDC 2109188'
loop_
_audit_author_name
_audit_author_address
'Yuji Kubo'
;Tokyo metropolitan university
Japan
;
_audit_update_record             
;
2021-09-11 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H21 B N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         416.27

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   7.6398(2)
_cell_length_b                   9.7054(3)
_cell_length_c                   15.9804(5)
_cell_angle_alpha                94.283(2)
_cell_angle_beta                 100.6460(10)
_cell_angle_gamma                108.9560(10)
_cell_volume                     1089.73(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7918
_cell_measurement_theta_min      2.8440
_cell_measurement_theta_max      72.4062
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436

_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            10082
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         72.39
_diffrn_reflns_theta_full        72.39
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             4160
_reflns_number_gt                3747
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1110
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_number_reflns         4160
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.4189P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 -0.2996(2) 0.90972(16) 0.05063(9) 0.0255(3) Uani d . . . 1 . .
O O1 -0.28197(14) 1.05480(10) 0.06217(7) 0.0314(2) Uani d . . . 1 . .
H H1 -0.168(3) 1.1063(13) 0.0785(13) 0.047 Uiso calc U . R 1 . .
C C1 -0.13259(19) 0.85057(14) 0.08205(8) 0.0256(3) Uani d . . . 1 . .
N N1 0.04402(17) 0.30474(13) 0.11094(8) 0.0333(3) Uani d . . . 1 . .
O O2 -0.46979(14) 0.80993(10) 0.01017(7) 0.0325(2) Uani d . . . 1 . .
H H2A -0.547(2) 0.8543(12) -0.0063(12) 0.049 Uiso calc U . R 1 . .
C C2 0.0573(2) 0.94121(14) 0.10933(9) 0.0294(3) Uani d . . . 1 . .
H H2 0.089585 1.044546 0.110281 0.035 Uiso calc U . R 1 . .
N N2 0.98641(16) 0.44726(12) 0.34489(8) 0.0309(3) Uani d . . . 1 . .
C C5 -0.0321(2) 0.64111(15) 0.10824(9) 0.0296(3) Uani d . . . 1 . .
H H5 -0.064851 0.537894 0.108024 0.036 Uiso calc U . R 1 . .
C C4 0.15816(19) 0.73287(14) 0.13488(8) 0.0256(3) Uani d . . . 1 . .
C C3 0.1995(2) 0.88432(15) 0.13502(9) 0.0302(3) Uani d . . . 1 . .
H H3 0.327365 0.949125 0.153046 0.036 Uiso calc U . R 1 . .
C C6 -0.1729(2) 0.69939(15) 0.08222(9) 0.0291(3) Uani d . . . 1 . .
H H6 -0.300813 0.634751 0.06393 0.035 Uiso calc U . R 1 . .
C C7 0.31702(19) 0.68323(14) 0.16647(8) 0.0258(3) Uani d . . . 1 . .
H H7 0.435349 0.760468 0.187642 0.031 Uiso calc U . R 1 . .
C C8 0.32407(18) 0.54680(14) 0.17064(8) 0.0247(3) Uani d . . . 1 . .
C C9 0.16413(19) 0.41523(14) 0.13547(9) 0.0264(3) Uani d . . . 1 . .
C C10 0.49548(18) 0.51920(14) 0.21557(9) 0.0247(3) Uani d . . . 1 . .
C C11 0.61180(18) 0.61152(13) 0.29022(9) 0.0243(3) Uani d . . . 1 . .
H H11 0.580574 0.692247 0.311929 0.029 Uiso calc U . R 1 . .
C C12 0.77165(18) 0.58784(14) 0.33322(9) 0.0253(3) Uani d . . . 1 . .
H H12 0.848267 0.65179 0.384139 0.03 Uiso calc U . R 1 . .
C C13 0.82127(18) 0.47005(14) 0.30212(9) 0.0272(3) Uani d . . . 1 . .
C C14 0.70313(19) 0.37538(14) 0.22847(10) 0.0315(3) Uani d . . . 1 . .
H H14 0.733474 0.294015 0.207033 0.038 Uiso calc U . R 1 . .
C C15 0.54238(19) 0.39903(14) 0.18645(10) 0.0300(3) Uani d . . . 1 . .
H H15 0.462513 0.332588 0.137016 0.036 Uiso calc U . R 1 . .
C C16 0.9907(2) 0.30110(15) 0.34384(11) 0.0332(3) Uani d . . . 1 . .
C C17 0.8459(3) 0.1911(2) 0.3651(2) 0.0772(8) Uani d . . . 1 . .
H H17 0.743043 0.212253 0.381545 0.093 Uiso calc U . R 1 . .
C C18 0.8515(3) 0.0493(2) 0.3624(3) 0.1024(12) Uani d . . . 1 . .
H H18 0.750908 -0.026521 0.376296 0.123 Uiso calc U . R 1 . .
C C19 1.0006(3) 0.01711(18) 0.33979(18) 0.0670(7) Uani d . . . 1 . .
H H19 1.002583 -0.080455 0.33757 0.08 Uiso calc U . R 1 . .
C C20 1.1467(2) 0.12738(16) 0.32048(10) 0.0340(3) Uani d . . . 1 . .
H H20 1.25141 0.106452 0.305981 0.041 Uiso calc U . R 1 . .
C C21 1.14187(18) 0.26868(14) 0.32204(8) 0.0248(3) Uani d . . . 1 . .
H H21 1.24288 0.344126 0.308066 0.03 Uiso calc U . R 1 . .
C C22 1.14908(19) 0.56617(14) 0.38919(9) 0.0261(3) Uani d . . . 1 . .
C C23 1.20121(18) 0.70181(14) 0.35903(8) 0.0240(3) Uani d . . . 1 . .
H H23 1.125968 0.715587 0.308163 0.029 Uiso calc U . R 1 . .
C C24 1.36227(19) 0.81639(15) 0.40300(9) 0.0282(3) Uani d . . . 1 . .
H H24 1.394801 0.908978 0.382716 0.034 Uiso calc U . R 1 . .
C C25 1.4769(2) 0.79764(17) 0.47643(10) 0.0388(4) Uani d . . . 1 . .
H H25 1.588518 0.875835 0.505861 0.047 Uiso calc U . R 1 . .
C C26 1.4250(3) 0.66268(18) 0.50576(10) 0.0477(5) Uani d . . . 1 . .
H H26 1.502159 0.648372 0.555827 0.057 Uiso calc U . R 1 . .
C C27 1.2630(3) 0.54858(17) 0.46347(9) 0.0391(4) Uani d . . . 1 . .
H H27 1.228809 0.457303 0.485177 0.047 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 O2 . 1.3506(18) ?
B1 O1 . 1.3652(17) ?
B1 C1 . 1.579(2) ?
O1 H1 . 0.83(2) ?
C1 C2 . 1.3956(19) ?
C1 C6 . 1.3982(18) ?
N1 C9 . 1.1449(18) ?
O2 H2A . 0.85(2) ?
C2 C3 . 1.383(2) ?
C2 H2 . 0.95 ?
N2 C13 . 1.4117(17) ?
N2 C22 . 1.4137(18) ?
N2 C16 . 1.4286(16) ?
C5 C6 . 1.3839(19) ?
C5 C4 . 1.4004(19) ?
C5 H5 . 0.95 ?
C4 C3 . 1.3993(18) ?
C4 C7 . 1.4661(18) ?
C3 H3 . 0.95 ?
C6 H6 . 0.95 ?
C7 C8 . 1.3487(18) ?
C7 H7 . 0.95 ?
C8 C9 . 1.4369(18) ?
C8 C10 . 1.4871(18) ?
C10 C11 . 1.3954(19) ?
C10 C15 . 1.3989(18) ?
C11 C12 . 1.3828(18) ?
C11 H11 . 0.95 ?
C12 C13 . 1.4014(18) ?
C12 H12 . 0.95 ?
C13 C14 . 1.397(2) ?
C14 C15 . 1.383(2) ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
C16 C17 . 1.380(2) ?
C16 C21 . 1.3863(18) ?
C17 C18 . 1.388(2) ?
C17 H17 . 0.95 ?
C18 C19 . 1.376(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.373(2) ?
C19 H19 . 0.95 ?
C20 C21 . 1.3821(19) ?
C20 H20 . 0.95 ?
C21 H21 . 0.95 ?
C22 C27 . 1.393(2) ?
C22 C23 . 1.3961(18) ?
C23 C24 . 1.3854(19) ?
C23 H23 . 0.95 ?
C24 C25 . 1.390(2) ?
C24 H24 . 0.95 ?
C25 C26 . 1.384(3) ?
C25 H25 . 0.95 ?
C26 C27 . 1.380(2) ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 B1 O1 . . 118.48(12) ?
O2 B1 C1 . . 117.58(12) ?
O1 B1 C1 . . 123.94(12) ?
B1 O1 H1 . . 109.5 ?
C2 C1 C6 . . 116.98(12) ?
C2 C1 B1 . . 123.59(12) ?
C6 C1 B1 . . 119.42(12) ?
B1 O2 H2A . . 109.5 ?
C3 C2 C1 . . 121.64(12) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C13 N2 C22 . . 121.53(10) ?
C13 N2 C16 . . 119.71(12) ?
C22 N2 C16 . . 118.76(11) ?
C6 C5 C4 . . 120.62(12) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C3 C4 C5 . . 117.71(12) ?
C3 C4 C7 . . 117.24(12) ?
C5 C4 C7 . . 124.99(12) ?
C2 C3 C4 . . 121.07(13) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C5 C6 C1 . . 121.97(13) ?
C5 C6 H6 . . 119.0 ?
C1 C6 H6 . . 119.0 ?
C8 C7 C4 . . 131.10(12) ?
C8 C7 H7 . . 114.5 ?
C4 C7 H7 . . 114.5 ?
C7 C8 C9 . . 123.01(12) ?
C7 C8 C10 . . 122.93(12) ?
C9 C8 C10 . . 114.01(11) ?
N1 C9 C8 . . 174.85(14) ?
C11 C10 C15 . . 118.01(12) ?
C11 C10 C8 . . 120.26(11) ?
C15 C10 C8 . . 121.70(12) ?
C12 C11 C10 . . 121.30(12) ?
C12 C11 H11 . . 119.3 ?
C10 C11 H11 . . 119.3 ?
C11 C12 C13 . . 120.38(13) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 118.56(12) ?
C14 C13 N2 . . 120.89(12) ?
C12 C13 N2 . . 120.54(13) ?
C15 C14 C13 . . 120.60(12) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C14 C15 C10 . . 121.08(13) ?
C14 C15 H15 . . 119.5 ?
C10 C15 H15 . . 119.5 ?
C17 C16 C21 . . 119.28(13) ?
C17 C16 N2 . . 120.59(13) ?
C21 C16 N2 . . 120.13(12) ?
C16 C17 C18 . . 119.64(16) ?
C16 C17 H17 . . 120.2 ?
C18 C17 H17 . . 120.2 ?
C19 C18 C17 . . 120.96(17) ?
C19 C18 H18 . . 119.5 ?
C17 C18 H18 . . 119.5 ?
C20 C19 C18 . . 119.34(15) ?
C20 C19 H19 . . 120.3 ?
C18 C19 H19 . . 120.3 ?
C19 C20 C21 . . 120.29(14) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C20 C21 C16 . . 120.48(13) ?
C20 C21 H21 . . 119.8 ?
C16 C21 H21 . . 119.8 ?
C27 C22 C23 . . 118.67(13) ?
C27 C22 N2 . . 120.10(12) ?
C23 C22 N2 . . 121.21(12) ?
C24 C23 C22 . . 120.24(12) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 120.86(13) ?
C23 C24 H24 . . 119.6 ?
C25 C24 H24 . . 119.6 ?
C26 C25 C24 . . 118.62(14) ?
C26 C25 H25 . . 120.7 ?
C24 C25 H25 . . 120.7 ?
C27 C26 C25 . . 121.07(14) ?
C27 C26 H26 . . 119.5 ?
C25 C26 H26 . . 119.5 ?
C26 C27 C22 . . 120.53(14) ?
C26 C27 H27 . . 119.7 ?
C22 C27 H27 . . 119.7 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile, water, hexane, dichloromethane'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
_exptl_crystal_preparation       Luminescent
