# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2548600'
loop_
_audit_author_name
_audit_author_address
'Apurba Kumar Pal'
;Indian Institute of science Bangalore India
India
;
_audit_update_record             
;
2026-04-23 deposited with the CCDC.	2026-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2025/1
_shelx_SHELXL_version_number     2025/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 B N2 O2'
_chemical_formula_sum            'C23 H29 B N2 O2'
_chemical_formula_weight         376.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4446(3)
_cell_length_b                   8.6250(3)
_cell_length_c                   23.8746(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.6120(10)
_cell_angle_gamma                90
_cell_volume                     2113.95(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    132(2)
_cell_measurement_reflns_used    2562
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       bloc
_exptl_crystal_colour            white
_exptl_crystal_density_meas      1.18
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   0.654827
_exptl_transmission_factor_max   0.715682
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      132(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Smart APEX 3'
_diffrn_measurement_method       'φ and ω Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28847
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4847
_reflns_number_gt                3856
_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 Apex 3'
_computing_cell_refinement       'Bruker Apex 3'
_computing_data_reduction        'Bruker Apex 3'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2025/1 (Sheldrick, 2025)'
_computing_molecular_graphics    'ORTEP 3 for windows'
_computing_publication_material  WinGx
_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)+(0.1000P)²] 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         4847
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2018
_refine_ls_wR_factor_gt          0.1907
_refine_ls_goodness_of_fit_ref   1.341
_refine_ls_restrained_S_all      1.341
_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
O1 O 0.89807(13) -0.04592(15) 0.56973(6) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.70774(15) 0.60627(19) 0.37420(7) 0.0243(4) Uani 1 1 d . . . . .
C1 C 0.78140(16) 0.6283(2) 0.32976(8) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.79742(14) -0.15135(17) 0.48753(7) 0.0372(4) Uani 1 1 d . . . . .
N2 N 0.78977(15) 0.57049(19) 0.42675(7) 0.0253(4) Uani 1 1 d . . . . .
H2 H 0.836221 0.644141 0.446354 0.030 Uiso 1 1 calc R U . . .
C2 C 0.75489(19) 0.5413(2) 0.28030(9) 0.0285(5) Uani 1 1 d . . . . .
H2A H 0.684419 0.469913 0.274655 0.034 Uiso 1 1 calc R U . . .
B2 B 0.5738(2) 0.6276(3) 0.37149(10) 0.0285(5) Uani 1 1 d . . . . .
C3 C 0.8317(2) 0.5585(3) 0.23880(9) 0.0328(5) Uani 1 1 d . . . . .
H3 H 0.812071 0.500282 0.204503 0.039 Uiso 1 1 calc R U . . .
C4 C 0.9361(2) 0.6596(2) 0.24711(9) 0.0314(5) Uani 1 1 d . . . . .
H4 H 0.989941 0.668293 0.219227 0.038 Uiso 1 1 calc R U . . .
C5 C 0.96198(19) 0.7483(2) 0.29643(10) 0.0319(5) Uani 1 1 d . . . . .
H5 H 1.032847 0.819110 0.302099 0.038 Uiso 1 1 calc R U . . .
C6 C 0.88477(18) 0.7336(2) 0.33722(9) 0.0270(4) Uani 1 1 d . . . . .
H6 H 0.902066 0.795568 0.370650 0.032 Uiso 1 1 calc R U . . .
C7 C 0.50261(19) 0.5958(3) 0.42327(9) 0.0331(5) Uani 1 1 d . . . . .
H7 H 0.566220 0.550365 0.455532 0.040 Uiso 1 1 calc R U . . .
C8 C 0.3932(2) 0.4776(3) 0.40323(10) 0.0406(6) Uani 1 1 d . . . . .
H8A H 0.433531 0.375852 0.398229 0.049 Uiso 1 1 calc R U . . .
H8B H 0.341188 0.465706 0.433698 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3018(3) 0.5183(4) 0.34837(13) 0.0605(8) Uani 1 1 d . . . . .
H9A H 0.239965 0.598103 0.356852 0.073 Uiso 1 1 calc R U . . .
H9B H 0.250430 0.424867 0.334592 0.073 Uiso 1 1 calc R U . . .
C10 C 0.3669(2) 0.5781(4) 0.30048(11) 0.0479(6) Uani 1 1 d . . . . .
H10A H 0.299586 0.627726 0.271376 0.057 Uiso 1 1 calc R U . . .
H10B H 0.401706 0.488342 0.282243 0.057 Uiso 1 1 calc R U . . .
C11 C 0.4784(2) 0.6952(3) 0.31855(10) 0.0366(5) Uani 1 1 d . . . . .
H11 H 0.526213 0.711894 0.286418 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4553(2) 0.7530(3) 0.44165(10) 0.0401(6) Uani 1 1 d . . . . .
H12A H 0.401607 0.734755 0.471142 0.048 Uiso 1 1 calc R U . . .
H12B H 0.532119 0.814512 0.459408 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3756(2) 0.8487(3) 0.39361(12) 0.0510(7) Uani 1 1 d . . . . .
H13A H 0.368295 0.956052 0.407365 0.061 Uiso 1 1 calc R U . . .
H13B H 0.286555 0.805048 0.384378 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4330(2) 0.8539(3) 0.33906(12) 0.0479(7) Uani 1 1 d . . . . .
H14A H 0.508447 0.925454 0.345301 0.057 Uiso 1 1 calc R U . . .
H14B H 0.366773 0.898120 0.308161 0.057 Uiso 1 1 calc R U . . .
C15 C 0.79706(16) 0.4218(2) 0.44713(8) 0.0222(4) Uani 1 1 d . . . . .
C16 C 0.74820(18) 0.2936(2) 0.41363(8) 0.0265(4) Uani 1 1 d . . . . .
H16 H 0.704933 0.308035 0.375363 0.032 Uiso 1 1 calc R U . . .
C17 C 0.76340(18) 0.1464(2) 0.43663(9) 0.0267(4) Uani 1 1 d . . . . .
H17 H 0.730383 0.060087 0.413712 0.032 Uiso 1 1 calc R U . . .
C18 C 0.82613(16) 0.1213(2) 0.49275(8) 0.0227(4) Uani 1 1 d . . . . .
C19 C 0.87416(17) 0.2495(2) 0.52590(8) 0.0226(4) Uani 1 1 d . . . . .
H19 H 0.917429 0.234691 0.564153 0.027 Uiso 1 1 calc R U . . .
C20 C 0.85934(17) 0.3967(2) 0.50365(8) 0.0218(4) Uani 1 1 d . . . . .
H20 H 0.891741 0.482625 0.526863 0.026 Uiso 1 1 calc R U . . .
C21 C 0.83804(18) -0.0373(2) 0.51503(9) 0.0264(4) Uani 1 1 d . . . . .
C22 C 0.9132(2) -0.2006(2) 0.59378(9) 0.0293(5) Uani 1 1 d . . . . .
H22A H 0.969975 -0.263561 0.573705 0.035 Uiso 1 1 calc R U . . .
H22B H 0.827378 -0.252366 0.589628 0.035 Uiso 1 1 calc R U . . .
C23 C 0.9732(2) -0.1858(3) 0.65554(10) 0.0401(5) Uani 1 1 d . . . . .
H23A H 0.988526 -0.289266 0.672395 0.060 Uiso 1 1 calc R U . . .
H23B H 0.914202 -0.128078 0.675401 0.060 Uiso 1 1 calc R U . . .
H23C H 1.056240 -0.130281 0.659235 0.060 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 C21 1.343(2) . ?
O1 C22 1.450(2) . ?
N1 B2 1.401(3) . ?
N1 N2 1.417(2) . ?
N1 C1 1.433(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.397(3) . ?
O2 C21 1.215(2) . ?
N2 C15 1.369(3) . ?
C2 C3 1.393(3) . ?
B2 C11 1.570(3) . ?
B2 C7 1.579(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.380(3) . ?
C7 C12 1.534(3) . ?
C7 C8 1.541(3) . ?
C8 C9 1.513(4) . ?
C9 C10 1.524(4) . ?
C10 C11 1.541(3) . ?
C11 C14 1.557(4) . ?
C12 C13 1.529(4) . ?
C13 C14 1.532(3) . ?
C15 C20 1.403(3) . ?
C15 C16 1.405(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.396(3) . ?
C18 C19 1.398(3) . ?
C18 C21 1.465(3) . ?
C19 C20 1.374(3) . ?
C22 C23 1.498(3) . ?

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
C21 O1 C22 115.69(15) . . ?
B2 N1 N2 120.38(16) . . ?
B2 N1 C1 128.03(16) . . ?
N2 N1 C1 111.39(14) . . ?
C2 C1 C6 119.33(17) . . ?
C2 C1 N1 120.64(17) . . ?
C6 C1 N1 119.97(17) . . ?
C15 N2 N1 120.25(15) . . ?
C1 C2 C3 119.91(18) . . ?
N1 B2 C11 124.49(18) . . ?
N1 B2 C7 123.44(19) . . ?
C11 B2 C7 111.97(17) . . ?
C4 C3 C2 120.5(2) . . ?
C3 C4 C5 119.64(18) . . ?
C6 C5 C4 120.01(18) . . ?
C5 C6 C1 120.55(19) . . ?
C12 C7 C8 114.46(18) . . ?
C12 C7 B2 107.07(18) . . ?
C8 C7 B2 107.51(18) . . ?
C9 C8 C7 115.4(2) . . ?
C8 C9 C10 115.5(2) . . ?
C9 C10 C11 115.5(2) . . ?
C10 C11 C14 113.95(19) . . ?
C10 C11 B2 108.47(19) . . ?
C14 C11 B2 104.95(19) . . ?
C13 C12 C7 115.0(2) . . ?
C12 C13 C14 114.18(19) . . ?
C13 C14 C11 115.5(2) . . ?
N2 C15 C20 118.18(17) . . ?
N2 C15 C16 123.00(18) . . ?
C20 C15 C16 118.80(18) . . ?
C17 C16 C15 119.63(18) . . ?
C16 C17 C18 121.56(18) . . ?
C17 C18 C19 118.50(18) . . ?
C17 C18 C21 119.13(17) . . ?
C19 C18 C21 122.37(18) . . ?
C20 C19 C18 120.58(18) . . ?
C19 C20 C15 120.93(17) . . ?
O2 C21 O1 122.34(19) . . ?
O2 C21 C18 124.20(19) . . ?
O1 C21 C18 113.46(16) . . ?
O1 C22 C23 107.85(17) . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.063

