# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 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_bnencho
_audit_block_doi                 10.5517/ccdc.csd.cc26r404
_database_code_depnum_ccdc_archive 'CCDC 2048015'
loop_
_audit_author_name
_audit_author_address
'Jun Miao'
;Jilin University
China
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_audit_creation_date             2021-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 B O3'
_chemical_formula_sum            'C21 H21 B O3'
_chemical_formula_weight         332.19
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.1705(3)
_cell_length_b                   10.3149(5)
_cell_length_c                   23.0801(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.3500(10)
_cell_angle_gamma                90
_cell_volume                     1696.60(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.58
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_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    1.301
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            39529
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.583
_diffrn_reflns_theta_min         3.086
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5223
_reflns_number_total             5664
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.051
_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)+(0.0610P)²+0.4561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19),
 C21(H21)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C)
;
_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
O22 O 0.45857(7) 0.69856(5) 0.37129(2) 0.01383(11) Uani 1 1 d . . . . .
O23 O 0.75891(7) 0.77476(5) 0.37353(2) 0.01446(11) Uani 1 1 d . . . . .
O24 O 0.93533(11) 0.49295(6) 0.67203(3) 0.02622(15) Uani 1 1 d . . . . .
C1 C 0.77927(12) 0.82786(9) 0.27223(4) 0.02025(15) Uani 1 1 d . . . . .
H1A H 0.887312 0.885432 0.281248 0.030 Uiso 1 1 calc GR . . . .
H1B H 0.706936 0.856017 0.235896 0.030 Uiso 1 1 calc GR . . . .
H1C H 0.823356 0.738880 0.267736 0.030 Uiso 1 1 calc GR . . . .
C2 C 0.50379(12) 0.62677(8) 0.27526(3) 0.01894(15) Uani 1 1 d . . . . .
H2A H 0.621261 0.583471 0.289919 0.028 Uiso 1 1 calc GR . . . .
H2B H 0.509071 0.653017 0.234666 0.028 Uiso 1 1 calc GR . . . .
H2C H 0.398523 0.567017 0.277402 0.028 Uiso 1 1 calc GR . . . .
C3 C 0.29703(11) 0.81601(8) 0.28991(4) 0.01977(15) Uani 1 1 d . . . . .
H3A H 0.194201 0.753234 0.283600 0.030 Uiso 1 1 calc GR . . . .
H3B H 0.313431 0.859415 0.253048 0.030 Uiso 1 1 calc GR . . . .
H3C H 0.267313 0.880573 0.318662 0.030 Uiso 1 1 calc GR . . . .
C4 C 0.47664(10) 0.74612(7) 0.31223(3) 0.01277(13) Uani 1 1 d . . . . .
C5 C 0.65557(10) 0.83292(7) 0.32155(3) 0.01330(13) Uani 1 1 d . . . . .
C6 C 0.61574(12) 0.97327(8) 0.33676(4) 0.02108(16) Uani 1 1 d . . . . .
H6A H 0.534875 0.975358 0.368311 0.032 Uiso 1 1 calc GR . . . .
H6B H 0.552555 1.017104 0.302361 0.032 Uiso 1 1 calc GR . . . .
H6C H 0.734173 1.017597 0.349381 0.032 Uiso 1 1 calc GR . . . .
C7 C 0.69110(9) 0.63755(7) 0.46196(3) 0.01179(12) Uani 1 1 d . . . . .
C8 C 0.73712(10) 0.71257(7) 0.51252(3) 0.01262(13) Uani 1 1 d . . . . .
C9 C 0.71492(11) 0.85047(7) 0.51017(3) 0.01677(14) Uani 1 1 d . . . . .
H9 H 0.669633 0.890312 0.474234 0.020 Uiso 1 1 calc R . . . .
C10 C 0.75731(13) 0.92591(8) 0.55834(3) 0.02018(15) Uani 1 1 d . . . . .
H10 H 0.741166 1.017253 0.556052 0.024 Uiso 1 1 calc R . . . .
C11 C 0.82574(13) 0.86649(8) 0.61187(3) 0.02075(16) Uani 1 1 d . . . . .
H11 H 0.856138 0.919037 0.645393 0.025 Uiso 1 1 calc R . . . .
C12 C 0.84893(11) 0.73522(8) 0.61630(3) 0.01715(14) Uani 1 1 d . . . . .
H12 H 0.894927 0.698329 0.652820 0.021 Uiso 1 1 calc R . . . .
C13 C 0.80514(10) 0.65215(7) 0.56687(3) 0.01251(13) Uani 1 1 d . . . . .
C14 C 0.82993(9) 0.51573(7) 0.56915(3) 0.01189(12) Uani 1 1 d . . . . .
C15 C 0.78326(9) 0.43910(7) 0.51827(3) 0.01171(12) Uani 1 1 d . . . . .
C16 C 0.80606(11) 0.30097(7) 0.51669(3) 0.01519(13) Uani 1 1 d . . . . .
H16 H 0.855095 0.256827 0.551173 0.018 Uiso 1 1 calc R . . . .
C17 C 0.75903(11) 0.23124(7) 0.46681(3) 0.01714(14) Uani 1 1 d . . . . .
H17 H 0.777721 0.140054 0.467104 0.021 Uiso 1 1 calc R . . . .
C18 C 0.68278(11) 0.29321(7) 0.41469(3) 0.01688(14) Uani 1 1 d . . . . .
H18 H 0.648339 0.243648 0.380477 0.020 Uiso 1 1 calc R . . . .
C19 C 0.65917(10) 0.42437(7) 0.41395(3) 0.01463(13) Uani 1 1 d . . . . .
H19 H 0.607921 0.465399 0.378908 0.018 Uiso 1 1 calc R . . . .
C20 C 0.70984(9) 0.50173(7) 0.46478(3) 0.01153(12) Uani 1 1 d . . . . .
C21 C 0.90812(10) 0.44812(7) 0.62309(3) 0.01531(13) Uani 1 1 d . . . . .
H21 H 0.940729 0.359592 0.618961 0.018 Uiso 1 1 calc R . . . .
B25 B 0.63293(11) 0.70561(7) 0.40166(3) 0.01218(14) 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
O22 C4 1.4678(8) . ?
O22 B25 1.3660(9) . ?
O23 C5 1.4667(8) . ?
O23 B25 1.3698(9) . ?
O24 C21 1.2162(9) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C5 1.5195(11) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C4 1.5226(10) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C4 1.5156(10) . ?
C4 C5 1.5598(10) . ?
C5 C6 1.5240(11) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.4086(9) . ?
C7 C20 1.4082(10) . ?
C7 B25 1.5733(10) . ?
C8 C9 1.4317(10) . ?
C8 C13 1.4369(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.3637(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.4173(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.3667(11) . ?
C12 H12 0.9500 . ?
C12 C13 1.4335(10) . ?
C13 C14 1.4186(10) . ?
C14 C15 1.4243(9) . ?
C14 C21 1.4819(9) . ?
C15 C16 1.4351(10) . ?
C15 C20 1.4405(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.3676(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.4176(10) . ?
C18 H18 0.9500 . ?
C18 C19 1.3634(10) . ?
C19 H19 0.9500 . ?
C19 C20 1.4321(9) . ?
C21 H21 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
B25 O22 C4 106.80(5) . . ?
B25 O23 C5 107.50(5) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C1 H1A 109.5 . . ?
C5 C1 H1B 109.5 . . ?
C5 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
O22 C4 C2 106.27(6) . . ?
O22 C4 C3 108.40(6) . . ?
O22 C4 C5 102.68(5) . . ?
C2 C4 C5 112.78(6) . . ?
C3 C4 C2 110.53(6) . . ?
C3 C4 C5 115.40(6) . . ?
O23 C5 C1 108.34(6) . . ?
O23 C5 C4 102.21(5) . . ?
O23 C5 C6 106.91(6) . . ?
C1 C5 C4 114.61(6) . . ?
C1 C5 C6 110.18(6) . . ?
C6 C5 C4 113.88(6) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 B25 120.17(6) . . ?
C20 C7 C8 119.72(6) . . ?
C20 C7 B25 119.96(6) . . ?
C7 C8 C9 119.97(6) . . ?
C7 C8 C13 120.72(6) . . ?
C9 C8 C13 119.31(6) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.48(7) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.24(7) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.41(7) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.24(7) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 117.32(6) . . ?
C14 C13 C8 119.44(6) . . ?
C14 C13 C12 123.22(6) . . ?
C13 C14 C15 120.19(6) . . ?
C13 C14 C21 122.15(6) . . ?
C15 C14 C21 117.64(6) . . ?
C14 C15 C16 123.71(6) . . ?
C14 C15 C20 119.21(6) . . ?
C16 C15 C20 117.08(6) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.70(7) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.89(7) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.58(7) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.52(7) . . ?
C20 C19 H19 119.2 . . ?
C7 C20 C15 120.65(6) . . ?
C7 C20 C19 120.14(6) . . ?
C19 C20 C15 119.20(6) . . ?
O24 C21 C14 127.46(7) . . ?
O24 C21 H21 116.3 . . ?
C14 C21 H21 116.3 . . ?
O22 B25 O23 113.49(6) . . ?
O22 B25 C7 124.63(6) . . ?
O23 B25 C7 121.84(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
