# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2024024'
loop_
_audit_author_name
_audit_author_address
'Aminophenylboronic acid'
;Dalian Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_audit_creation_date             2020-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 B2 N2 O2'
_chemical_formula_sum            'C12 H12 B2 N2 O2'
_chemical_formula_weight         237.86
_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'
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'

_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   15.0331(6)
_cell_length_b                   5.0718(3)
_cell_length_c                   15.8131(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.040(2)
_cell_angle_gamma                90
_cell_volume                     1125.29(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2387
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0736 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8514. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9851
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.265
_diffrn_reflns_theta_min         2.334
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                1961
_reflns_number_total             2790
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.284
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.4979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Rotating group:
 N1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2B), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.72713(7) 0.1226(2) 0.36265(7) 0.0194(3) Uani 1 1 d . . . . .
O2 O 0.88176(8) 0.2444(2) 0.36841(8) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.64862(10) 0.3610(3) 0.44679(9) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.62068(11) -0.2291(3) 0.23414(10) 0.0234(3) Uani 1 1 d . . . . .
H1A H 0.616547 -0.382255 0.206636 0.028 Uiso 1 1 d GR . . . .
C12 C 0.80658(11) 0.5064(3) 0.46194(11) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.55943(11) -0.0313(3) 0.34433(10) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.72332(12) 0.7204(3) 0.54992(11) 0.0226(4) Uani 1 1 d . . . . .
C7 C 0.72596(11) 0.5309(3) 0.48683(11) 0.0193(3) Uani 1 1 d . . . . .
C11 C 0.88264(11) 0.6802(3) 0.50114(11) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.55115(11) -0.2151(3) 0.27480(11) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.48489(11) -0.0294(3) 0.37819(11) 0.0235(4) Uani 1 1 d . . . . .
H5 H 0.487893 0.092886 0.424638 0.028 Uiso 1 1 calc R . . . .
C10 C 0.87982(12) 0.8711(3) 0.56277(11) 0.0229(4) Uani 1 1 d . . . . .
C9 C 0.80004(12) 0.8880(4) 0.58759(12) 0.0242(4) Uani 1 1 d . . . . .
C2 C 0.47194(11) -0.3808(3) 0.24191(11) 0.0229(4) Uani 1 1 d . . . . .
H2B H 0.466718 -0.499647 0.193932 0.028 Uiso 1 1 calc R . . . .
C3 C 0.40114(12) -0.3738(4) 0.27833(12) 0.0255(4) Uani 1 1 d . . . . .
H3 H 0.348220 -0.489976 0.256246 0.031 Uiso 1 1 calc R . . . .
C4 C 0.40728(12) -0.1972(4) 0.34712(12) 0.0274(4) Uani 1 1 d . . . . .
H4 H 0.358884 -0.191502 0.372583 0.033 Uiso 1 1 calc R . . . .
B2 B 0.80705(13) 0.2822(4) 0.39585(12) 0.0186(4) Uani 1 1 d . . . . .
B1 B 0.64718(12) 0.1552(4) 0.38585(12) 0.0187(4) Uani 1 1 d . . . . .
H1B H 0.6791(14) -0.192(4) 0.2726(14) 0.035(6) Uiso 1 1 d . . . . .
H11 H 0.9394(12) 0.663(4) 0.4847(12) 0.024(5) Uiso 1 1 d . . . . .
H2A H 0.5968(13) 0.397(4) 0.4615(13) 0.031(5) Uiso 1 1 d . . . . .
H8 H 0.6658(14) 0.728(4) 0.5666(12) 0.032(5) Uiso 1 1 d . . . . .
H9 H 0.7971(12) 1.022(4) 0.6321(12) 0.029(5) Uiso 1 1 d . . . . .
H10 H 0.9341(14) 0.987(4) 0.5909(13) 0.034(5) Uiso 1 1 d . . . . .
H2 H 0.8782(16) 0.090(5) 0.3359(17) 0.063(8) Uiso 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
O1 B2 1.386(2) . ?
O1 B1 1.3867(19) . ?
O2 B2 1.355(2) . ?
O2 H2 0.93(3) . ?
N2 C7 1.402(2) . ?
N2 B1 1.415(2) . ?
N2 H2A 0.908(19) . ?
N1 H1A 0.8816 . ?
N1 C1 1.4119(19) . ?
N1 H1B 0.89(2) . ?
C12 C7 1.408(2) . ?
C12 C11 1.400(2) . ?
C12 B2 1.546(2) . ?
C6 C1 1.412(2) . ?
C6 C5 1.405(2) . ?
C6 B1 1.563(2) . ?
C8 C7 1.396(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.991(19) . ?
C11 C10 1.385(2) . ?
C11 H11 0.980(17) . ?
C1 C2 1.396(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.384(2) . ?
C10 C9 1.392(2) . ?
C10 H10 0.97(2) . ?
C9 H9 0.990(19) . ?
C2 H2B 0.9500 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 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
B2 O1 B1 123.08(13) . . ?
B2 O2 H2 114.0(14) . . ?
C7 N2 B1 124.62(14) . . ?
C7 N2 H2A 114.2(12) . . ?
B1 N2 H2A 121.1(12) . . ?
H1A N1 H1B 113.6 . . ?
C1 N1 H1A 109.7 . . ?
C1 N1 H1B 112.8(13) . . ?
C7 C12 B2 117.85(14) . . ?
C11 C12 C7 117.97(15) . . ?
C11 C12 B2 124.14(14) . . ?
C1 C6 B1 123.46(14) . . ?
C5 C6 C1 116.22(15) . . ?
C5 C6 B1 120.27(14) . . ?
C7 C8 H8 118.0(11) . . ?
C9 C8 C7 119.82(15) . . ?
C9 C8 H8 122.2(11) . . ?
N2 C7 C12 118.49(14) . . ?
C8 C7 N2 120.93(14) . . ?
C8 C7 C12 120.58(15) . . ?
C12 C11 H11 118.5(11) . . ?
C10 C11 C12 121.68(15) . . ?
C10 C11 H11 119.9(11) . . ?
N1 C1 C6 120.99(14) . . ?
C2 C1 N1 118.15(15) . . ?
C2 C1 C6 120.80(14) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 C6 123.14(16) . . ?
C4 C5 H5 118.4 . . ?
C11 C10 C9 119.24(16) . . ?
C11 C10 H10 120.7(11) . . ?
C9 C10 H10 120.0(11) . . ?
C8 C9 C10 120.70(16) . . ?
C8 C9 H9 118.9(10) . . ?
C10 C9 H9 120.4(11) . . ?
C1 C2 H2B 119.6 . . ?
C3 C2 C1 120.75(16) . . ?
C3 C2 H2B 119.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.99(16) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.07(15) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
O1 B2 C12 118.16(14) . . ?
O2 B2 O1 120.09(15) . . ?
O2 B2 C12 121.73(15) . . ?
O1 B1 N2 117.72(15) . . ?
O1 B1 C6 119.84(15) . . ?
N2 B1 C6 122.44(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
