# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_compound_1b
_database_code_depnum_ccdc_archive 'CCDC 2121000'
loop_
_audit_author_name
_audit_author_address
'Hiroto Yoshida'
;Hiroshima University
Japan
;
_audit_update_record             
;
2021-11-09 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 B N2 O Si'
_chemical_formula_weight         280.20

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.094(10)
_cell_length_b                   12.199(12)
_cell_length_c                   22.35(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3024(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4636
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.78

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33837
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.822
_diffrn_reflns_theta_max         28.004
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3637
_reflns_number_gt                2571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+1.2730P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3637
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Si1 Si 0.75214(4) 0.37501(4) 0.35840(2) 0.02231(13) Uani 1 1 d . . . . .
O1 O 1.00385(10) 0.40226(10) 0.55836(5) 0.0280(3) Uani 1 1 d . . . . .
N2 N 0.73410(12) 0.23734(11) 0.47242(6) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.6764 0.2015 0.4538 0.028 Uiso 1 1 calc R U . . .
N1 N 0.88393(12) 0.37968(11) 0.47645(6) 0.0229(3) Uani 1 1 d . . . . .
H1 H 0.9203 0.4356 0.4593 0.028 Uiso 1 1 calc R U . . .
C1 C 0.91998(15) 0.35273(13) 0.53309(7) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.85453(14) 0.26213(13) 0.56130(7) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.76422(14) 0.20517(13) 0.53018(8) 0.0224(4) Uani 1 1 d . . . . .
C6 C 0.82399(18) 0.14482(16) 0.64695(9) 0.0358(5) Uani 1 1 d . . . . .
H6 H 0.8437 0.1246 0.6868 0.043 Uiso 1 1 calc R U . . .
C4 C 0.70617(17) 0.11698(14) 0.55790(8) 0.0292(4) Uani 1 1 d . . . . .
H4 H 0.6457 0.0775 0.5369 0.035 Uiso 1 1 calc R U . . .
C5 C 0.73626(17) 0.08705(16) 0.61555(9) 0.0343(4) Uani 1 1 d . . . . .
H5 H 0.6968 0.0267 0.6339 0.041 Uiso 1 1 calc R U . . .
C8 C 0.88957(17) 0.43749(16) 0.32342(8) 0.0334(4) Uani 1 1 d . . . . .
H8A H 0.9515 0.3810 0.3183 0.050 Uiso 1 1 calc R U . . .
H8B H 0.9206 0.4957 0.3494 0.050 Uiso 1 1 calc R U . . .
H8C H 0.8684 0.4684 0.2843 0.050 Uiso 1 1 calc R U . . .
C7 C 0.88209(16) 0.23129(16) 0.62002(8) 0.0308(4) Uani 1 1 d . . . . .
H7 H 0.9418 0.2707 0.6416 0.037 Uiso 1 1 calc R U . . .
C9 C 0.69898(17) 0.25970(15) 0.30979(9) 0.0345(4) Uani 1 1 d . . . . .
H9A H 0.6622 0.2896 0.2734 0.052 Uiso 1 1 calc R U . . .
H9B H 0.6393 0.2160 0.3316 0.052 Uiso 1 1 calc R U . . .
H9C H 0.7676 0.2132 0.2989 0.052 Uiso 1 1 calc R U . . .
C10 C 0.58037(18) 0.52564(15) 0.31022(9) 0.0348(4) Uani 1 1 d . . . . .
H10 H 0.6074 0.4991 0.2726 0.042 Uiso 1 1 calc R U . . .
C11 C 0.63070(15) 0.48257(14) 0.36247(8) 0.0254(4) Uani 1 1 d . . . . .
C12 C 0.58691(17) 0.52403(15) 0.41657(9) 0.0333(4) Uani 1 1 d . . . . .
H12 H 0.6190 0.4966 0.4530 0.040 Uiso 1 1 calc R U . . .
C13 C 0.49792(18) 0.60412(17) 0.41865(11) 0.0430(5) Uani 1 1 d . . . . .
H13 H 0.4696 0.6306 0.4561 0.052 Uiso 1 1 calc R U . . .
C14 C 0.45094(19) 0.64494(16) 0.36608(11) 0.0443(5) Uani 1 1 d . . . . .
H14 H 0.3903 0.6999 0.3672 0.053 Uiso 1 1 calc R U . . .
C15 C 0.49201(19) 0.60604(16) 0.31183(10) 0.0433(5) Uani 1 1 d . . . . .
H15 H 0.4598 0.6343 0.2756 0.052 Uiso 1 1 calc R U . . .
B1 B 0.79145(17) 0.32461(15) 0.44222(9) 0.0220(4) 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
Si1 C9 1.873(2) . ?
Si1 C8 1.875(2) . ?
Si1 C11 1.883(2) . ?
Si1 B1 2.019(3) . ?
O1 C1 1.245(2) . ?
N2 C3 1.390(2) . ?
N2 B1 1.412(2) . ?
N2 H2 0.8800 . ?
N1 C1 1.368(2) . ?
N1 B1 1.445(2) . ?
N1 H1 0.8800 . ?
C1 C2 1.465(2) . ?
C2 C7 1.399(3) . ?
C2 C3 1.404(2) . ?
C3 C4 1.398(2) . ?
C6 C7 1.375(3) . ?
C6 C5 1.392(3) . ?
C6 H6 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.387(3) . ?
C10 C11 1.397(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C9 Si1 C8 108.63(10) . . ?
C9 Si1 C11 109.03(10) . . ?
C8 Si1 C11 108.59(10) . . ?
C9 Si1 B1 112.18(10) . . ?
C8 Si1 B1 109.57(9) . . ?
C11 Si1 B1 108.78(8) . . ?
C3 N2 B1 123.27(15) . . ?
C3 N2 H2 118.4 . . ?
B1 N2 H2 118.4 . . ?
C1 N1 B1 125.86(15) . . ?
C1 N1 H1 117.1 . . ?
B1 N1 H1 117.1 . . ?
O1 C1 N1 121.45(15) . . ?
O1 C1 C2 122.78(16) . . ?
N1 C1 C2 115.77(15) . . ?
C7 C2 C3 119.18(16) . . ?
C7 C2 C1 119.88(16) . . ?
C3 C2 C1 120.93(16) . . ?
N2 C3 C4 121.19(16) . . ?
N2 C3 C2 119.47(15) . . ?
C4 C3 C2 119.35(17) . . ?
C7 C6 C5 119.72(18) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C5 C4 C3 120.37(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.39(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 C2 120.96(18) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 121.79(19) . . ?
C15 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 116.62(18) . . ?
C10 C11 Si1 120.51(15) . . ?
C12 C11 Si1 122.87(14) . . ?
C13 C12 C11 122.02(19) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 119.95(19) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
N2 B1 N1 114.65(16) . . ?
N2 B1 Si1 125.16(13) . . ?
N1 B1 Si1 120.19(13) . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049

