# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20190121TF-2
_database_code_depnum_ccdc_archive 'CCDC 2192821'
loop_
_audit_author_name
_audit_author_address
'Prof. Yousuke Ooyama' 'Hiroshima University'
_audit_update_record             
;
2022-07-26 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 B N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         380.24

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7784(15)
_cell_length_b                   10.4451(12)
_cell_length_c                   15.3432(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.3580(10)
_cell_angle_gamma                90
_cell_volume                     1983.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6435
_cell_measurement_theta_min      2.3832
_cell_measurement_theta_max      27.7228
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered conforcal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            23781
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             4786
_reflns_number_gt                3874
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1045
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_number_reflns         4786
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+0.9172P] 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         0.282
_refine_diff_density_min         -0.238
_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 0.0033 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'

_computing_data_collection       'APEX2(Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

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 0.11017(11) 0.35815(14) 0.45181(10) 0.0250(3) Uani d . . . 1 . .
C C1 0.48299(10) 0.36827(12) 0.57072(8) 0.0233(2) Uani d . . . 1 . .
C C2 0.40112(11) 0.34833(13) 0.48915(8) 0.0290(3) Uani d . . . 1 . .
H H00H 0.3401 0.4035 0.4751 0.035 Uiso calc U . R 1 . .
C C3 0.40906(13) 0.25171(15) 0.43142(9) 0.0371(3) Uani d . . . 1 . .
H H00O 0.3534 0.2405 0.378 0.045 Uiso calc U . R 1 . .
C C4 0.49866(13) 0.16808(15) 0.44968(10) 0.0392(4) Uani d . . . 1 . .
H H00S 0.502 0.0999 0.4095 0.047 Uiso calc U . R 1 . .
C C5 0.58026(12) 0.18514(13) 0.52478(10) 0.0341(3) Uani d . . . 1 . .
H H00N 0.6408 0.1293 0.5362 0.041 Uiso calc U . R 1 . .
C C6 0.57598(11) 0.28622(12) 0.58685(8) 0.0261(3) Uani d . . . 1 . .
C C7 0.66131(10) 0.30863(12) 0.66183(9) 0.0273(3) Uani d . . . 1 . .
H H00I 0.7235 0.2556 0.6719 0.033 Uiso calc U . R 1 . .
C C8 0.65753(10) 0.40696(12) 0.72240(8) 0.0234(3) Uani d . . . 1 . .
C C9 0.74817(11) 0.43285(13) 0.79648(9) 0.0293(3) Uani d . . . 1 . .
H H00K 0.812 0.3833 0.8035 0.035 Uiso calc U . R 1 . .
C C10 0.74463(11) 0.52677(14) 0.85678(9) 0.0326(3) Uani d . . . 1 . .
H H00Q 0.8058 0.5433 0.9051 0.039 Uiso calc U . R 1 . .
C C11 0.64907(11) 0.59999(13) 0.84729(9) 0.0306(3) Uani d . . . 1 . .
H H00J 0.6459 0.6636 0.8908 0.037 Uiso calc U . R 1 . .
C C12 0.56176(10) 0.58071(12) 0.77690(8) 0.0261(3) Uani d . . . 1 . .
H H009 0.4992 0.6322 0.7719 0.031 Uiso calc U . R 1 . .
C C13 0.56182(10) 0.48455(11) 0.71007(8) 0.0217(2) Uani d . . . 1 . .
C C14 0.47513(10) 0.46447(11) 0.63362(8) 0.0215(2) Uani d . . . 1 . .
C C15 0.37433(10) 0.54626(12) 0.61659(8) 0.0236(3) Uani d . . . 1 . .
H H00A 0.3884 0.6217 0.6569 0.028 Uiso calc U . R 1 . .
H H00B 0.3574 0.5777 0.5538 0.028 Uiso calc U . R 1 . .
C C16 0.29846(11) 0.43179(14) 0.72531(9) 0.0303(3) Uani d . . . 1 . .
H H00G 0.3095 0.5059 0.7658 0.045 Uiso calc U . R 1 . .
H H00M 0.3628 0.3771 0.74 0.045 Uiso calc U . R 1 . .
H H00P 0.2357 0.3829 0.7325 0.045 Uiso calc U . R 1 . .
C C17 0.18327(10) 0.55946(12) 0.61107(8) 0.0257(3) Uani d . . . 1 . .
H H00D 0.1998 0.6378 0.6483 0.031 Uiso calc U . R 1 . .
H H00E 0.1238 0.5144 0.6291 0.031 Uiso calc U . R 1 . .
C C18 0.14402(9) 0.59887(12) 0.51315(8) 0.0231(2) Uani d . . . 1 . .
C C19 0.13238(10) 0.72960(12) 0.49552(8) 0.0263(3) Uani d . . . 1 . .
H H00F 0.1562 0.789 0.5432 0.032 Uiso calc U . R 1 . .
C C20 0.08625(10) 0.77447(12) 0.40897(9) 0.0267(3) Uani d . . . 1 . .
C C21 0.05420(10) 0.68964(12) 0.33753(9) 0.0270(3) Uani d . . . 1 . .
H H00L 0.0236 0.72 0.2783 0.032 Uiso calc U . R 1 . .
C C22 0.06804(10) 0.55974(12) 0.35482(8) 0.0253(3) Uani d . . . 1 . .
H H00C 0.048 0.5015 0.3059 0.03 Uiso calc U . R 1 . .
C C23 0.11058(9) 0.51045(12) 0.44176(8) 0.0228(2) Uani d . . . 1 . .
C C24 0.07059(13) 0.91029(13) 0.39443(10) 0.0369(3) Uani d . . . 1 . .
N N1 0.27955(8) 0.47605(10) 0.63161(7) 0.0227(2) Uani d . . . 1 . .
N N2 0.05769(14) 1.01769(13) 0.38293(10) 0.0570(4) Uani d . . . 1 . .
O O1 0.04946(8) 0.29355(9) 0.37949(6) 0.0337(2) Uani d . . . 1 . .
H H1 0.0584 0.2144 0.3879 0.051 Uiso calc U . R 1 . .
O O2 0.16369(8) 0.29338(9) 0.52505(6) 0.0315(2) Uani d . . . 1 . .
H H2 0.2063 0.3431 0.5597 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 . 1.3442(16) ?
B1 O1 . 1.3644(17) ?
B1 C23 . 1.5985(18) ?
C1 C14 . 1.4139(17) ?
C1 C2 . 1.4335(17) ?
C1 C6 . 1.4358(18) ?
C2 C3 . 1.3631(19) ?
C2 H00H . 0.95 ?
C3 C4 . 1.412(2) ?
C3 H00O . 0.95 ?
C4 C5 . 1.360(2) ?
C4 H00S . 0.95 ?
C5 C6 . 1.4320(18) ?
C5 H00N . 0.95 ?
C6 C7 . 1.3947(18) ?
C7 C8 . 1.3939(18) ?
C7 H00I . 0.95 ?
C8 C9 . 1.4330(17) ?
C8 C13 . 1.4400(17) ?
C9 C10 . 1.3569(19) ?
C9 H00K . 0.95 ?
C10 C11 . 1.4174(19) ?
C10 H00Q . 0.95 ?
C11 C12 . 1.3617(18) ?
C11 H00J . 0.95 ?
C12 C13 . 1.4354(17) ?
C12 H009 . 0.95 ?
C13 C14 . 1.4152(16) ?
C14 C15 . 1.5134(17) ?
C15 N1 . 1.4819(16) ?
C15 H00A . 0.99 ?
C15 H00B . 0.99 ?
C16 N1 . 1.4719(15) ?
C16 H00G . 0.98 ?
C16 H00M . 0.98 ?
C16 H00P . 0.98 ?
C17 N1 . 1.4764(16) ?
C17 C18 . 1.5181(16) ?
C17 H00D . 0.99 ?
C17 H00E . 0.99 ?
C18 C19 . 1.3928(17) ?
C18 C23 . 1.4153(17) ?
C19 C20 . 1.3936(17) ?
C19 H00F . 0.95 ?
C20 C21 . 1.3898(18) ?
C20 C24 . 1.4423(18) ?
C21 C22 . 1.3854(17) ?
C21 H00L . 0.95 ?
C22 C23 . 1.4073(17) ?
C22 H00C . 0.95 ?
C24 N2 . 1.1412(19) ?
O1 H1 . 0.84 ?
O2 H2 . 0.84 ?

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 . . 119.99(12) ?
O2 B1 C23 . . 124.64(12) ?
O1 B1 C23 . . 115.37(11) ?
C14 C1 C2 . . 122.62(12) ?
C14 C1 C6 . . 120.16(11) ?
C2 C1 C6 . . 117.22(11) ?
C3 C2 C1 . . 121.27(13) ?
C3 C2 H00H . . 119.4 ?
C1 C2 H00H . . 119.4 ?
C2 C3 C4 . . 121.10(13) ?
C2 C3 H00O . . 119.5 ?
C4 C3 H00O . . 119.5 ?
C5 C4 C3 . . 120.03(13) ?
C5 C4 H00S . . 120.0 ?
C3 C4 H00S . . 120.0 ?
C4 C5 C6 . . 120.81(14) ?
C4 C5 H00N . . 119.6 ?
C6 C5 H00N . . 119.6 ?
C7 C6 C5 . . 121.43(13) ?
C7 C6 C1 . . 119.10(11) ?
C5 C6 C1 . . 119.46(12) ?
C8 C7 C6 . . 121.62(12) ?
C8 C7 H00I . . 119.2 ?
C6 C7 H00I . . 119.2 ?
C7 C8 C9 . . 120.87(12) ?
C7 C8 C13 . . 119.72(11) ?
C9 C8 C13 . . 119.41(11) ?
C10 C9 C8 . . 121.35(12) ?
C10 C9 H00K . . 119.3 ?
C8 C9 H00K . . 119.3 ?
C9 C10 C11 . . 119.58(12) ?
C9 C10 H00Q . . 120.2 ?
C11 C10 H00Q . . 120.2 ?
C12 C11 C10 . . 121.15(12) ?
C12 C11 H00J . . 119.4 ?
C10 C11 H00J . . 119.4 ?
C11 C12 C13 . . 121.63(12) ?
C11 C12 H009 . . 119.2 ?
C13 C12 H009 . . 119.2 ?
C14 C13 C12 . . 123.83(11) ?
C14 C13 C8 . . 119.35(11) ?
C12 C13 C8 . . 116.81(11) ?
C13 C14 C1 . . 119.84(11) ?
C13 C14 C15 . . 121.14(11) ?
C1 C14 C15 . . 119.00(11) ?
N1 C15 C14 . . 112.78(10) ?
N1 C15 H00A . . 109.0 ?
C14 C15 H00A . . 109.0 ?
N1 C15 H00B . . 109.0 ?
C14 C15 H00B . . 109.0 ?
H00A C15 H00B . . 107.8 ?
N1 C16 H00G . . 109.5 ?
N1 C16 H00M . . 109.5 ?
H00G C16 H00M . . 109.5 ?
N1 C16 H00P . . 109.5 ?
H00G C16 H00P . . 109.5 ?
H00M C16 H00P . . 109.5 ?
N1 C17 C18 . . 115.12(10) ?
N1 C17 H00D . . 108.5 ?
C18 C17 H00D . . 108.5 ?
N1 C17 H00E . . 108.5 ?
C18 C17 H00E . . 108.5 ?
H00D C17 H00E . . 107.5 ?
C19 C18 C23 . . 119.49(11) ?
C19 C18 C17 . . 116.82(11) ?
C23 C18 C17 . . 123.45(11) ?
C20 C19 C18 . . 120.95(12) ?
C20 C19 H00F . . 119.5 ?
C18 C19 H00F . . 119.5 ?
C21 C20 C19 . . 120.62(12) ?
C21 C20 C24 . . 120.17(12) ?
C19 C20 C24 . . 119.20(12) ?
C22 C21 C20 . . 118.34(11) ?
C22 C21 H00L . . 120.8 ?
C20 C21 H00L . . 120.8 ?
C21 C22 C23 . . 122.73(12) ?
C21 C22 H00C . . 118.6 ?
C23 C22 H00C . . 118.6 ?
C22 C23 C18 . . 117.80(11) ?
C22 C23 B1 . . 116.48(11) ?
C18 C23 B1 . . 125.61(11) ?
N2 C24 C20 . . 179.7(2) ?
C16 N1 C17 . . 108.67(10) ?
C16 N1 C15 . . 111.39(9) ?
C17 N1 C15 . . 110.17(10) ?
B1 O1 H1 . . 109.5 ?
B1 O2 H2 . . 109.5 ?

