# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2012120'
loop_
_audit_author_name
_audit_author_address
'Liuzhou Gao'
;Nanjing University
China
;
_audit_update_record             
;
2020-06-25 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H34 B2 N2 O5'
_chemical_formula_weight         416.12

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.4551(6)
_cell_length_b                   20.4059(10)
_cell_length_c                   12.3794(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.643(2)
_cell_angle_gamma                90
_cell_volume                     3029.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.912
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            21721
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.978
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.006
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5314
_reflns_number_gt                4497
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.2000P)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         5314
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.2286
_refine_ls_wR_factor_gt          0.2138
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
B1 B 0.55105(15) 0.63582(9) 0.68722(17) 0.0217(4) Uani 1 1 d . . . . .
C1 C 1.22330(14) 0.78980(9) 0.63311(16) 0.0277(4) Uani 1 1 d . . . . .
C2 C 1.18258(14) 0.78139(9) 0.50404(16) 0.0281(4) Uani 1 1 d . . . . .
C3 C 1.23399(18) 0.82813(10) 0.4374(2) 0.0411(5) Uani 1 1 d . . . . .
H3A H 1.202789 0.820267 0.358664 0.062 Uiso 1 1 calc R U . . .
H3B H 1.313166 0.821373 0.456412 0.062 Uiso 1 1 calc R U . . .
H3C H 1.218671 0.872437 0.454649 0.062 Uiso 1 1 calc R U . . .
C4 C 1.19040(17) 0.71139(10) 0.46566(18) 0.0360(5) Uani 1 1 d . . . . .
H4A H 1.156395 0.682458 0.507949 0.054 Uiso 1 1 calc R U . . .
H4B H 1.267337 0.699656 0.477387 0.054 Uiso 1 1 calc R U . . .
H4C H 1.152425 0.707752 0.387359 0.054 Uiso 1 1 calc R U . . .
C5 C 1.31773(15) 0.74527(11) 0.69096(17) 0.0368(5) Uani 1 1 d . . . . .
H5A H 1.339062 0.754409 0.769958 0.055 Uiso 1 1 calc R U . . .
H5B H 1.380226 0.752562 0.660972 0.055 Uiso 1 1 calc R U . . .
H5C H 1.294117 0.700454 0.678830 0.055 Uiso 1 1 calc R U . . .
C6 C 1.25118(18) 0.86009(11) 0.6700(2) 0.0462(6) Uani 1 1 d . . . . .
H6A H 1.193309 0.888567 0.628487 0.069 Uiso 1 1 calc R U . . .
H6B H 1.320801 0.872154 0.656186 0.069 Uiso 1 1 calc R U . . .
H6C H 1.257091 0.864035 0.748663 0.069 Uiso 1 1 calc R U . . .
B2 B 1.03596(17) 0.78486(9) 0.57867(19) 0.0247(4) Uani 1 1 d . . . . .
C8 C 0.83493(14) 0.80133(8) 0.49119(15) 0.0233(4) Uani 1 1 d . . . . .
H8 H 0.852516 0.814333 0.426008 0.028 Uiso 1 1 calc R U . . .
C9 C 0.72843(14) 0.79885(8) 0.48962(15) 0.0232(4) Uani 1 1 d . . . . .
H9 H 0.675110 0.812248 0.425286 0.028 Uiso 1 1 calc R U . . .
C10 C 0.69030(13) 0.77486(7) 0.58931(15) 0.0206(4) Uani 1 1 d . . . . .
C11 C 0.78907(14) 0.77117(8) 0.69144(15) 0.0241(4) Uani 1 1 d . . . . .
H11 H 0.776103 0.766496 0.761585 0.029 Uiso 1 1 calc R U . . .
C12 C 0.89380(14) 0.77435(8) 0.68519(15) 0.0248(4) Uani 1 1 d . . . . .
H12 H 0.950791 0.768804 0.750764 0.030 Uiso 1 1 calc R U . . .
C13 C 0.60862(14) 0.82209(8) 0.61182(15) 0.0237(4) Uani 1 1 d . . . . .
C14 C 0.63050(14) 0.70606(7) 0.56433(15) 0.0211(4) Uani 1 1 d . . . . .
C15 C 0.71236(16) 0.65495(8) 0.54644(17) 0.0304(4) Uani 1 1 d . . . . .
H15A H 0.774111 0.652137 0.612312 0.046 Uiso 1 1 calc R U . . .
H15B H 0.738972 0.667181 0.483352 0.046 Uiso 1 1 calc R U . . .
H15C H 0.675841 0.613165 0.532313 0.046 Uiso 1 1 calc R U . . .
C16 C 0.52834(15) 0.71007(8) 0.46336(16) 0.0273(4) Uani 1 1 d . . . . .
H16A H 0.487874 0.669537 0.455807 0.041 Uiso 1 1 calc R U . . .
H16B H 0.551770 0.717924 0.396704 0.041 Uiso 1 1 calc R U . . .
H16C H 0.481137 0.745285 0.474079 0.041 Uiso 1 1 calc R U . . .
C17 C 0.47383(15) 0.53442(8) 0.67384(15) 0.0258(4) Uani 1 1 d . . . . .
C18 C 0.50243(15) 0.55962(8) 0.79779(15) 0.0253(4) Uani 1 1 d . . . . .
C19 C 0.60997(17) 0.53259(9) 0.87105(17) 0.0344(5) Uani 1 1 d . . . . .
H19A H 0.667439 0.536628 0.833074 0.052 Uiso 1 1 calc R U . . .
H19B H 0.600141 0.487224 0.886604 0.052 Uiso 1 1 calc R U . . .
H19C H 0.630914 0.556664 0.940184 0.052 Uiso 1 1 calc R U . . .
C20 C 0.40920(18) 0.55064(9) 0.85396(19) 0.0358(5) Uani 1 1 d . . . . .
H20A H 0.431436 0.568800 0.928202 0.054 Uiso 1 1 calc R U . . .
H20B H 0.393735 0.504768 0.858291 0.054 Uiso 1 1 calc R U . . .
H20C H 0.343418 0.572657 0.810921 0.054 Uiso 1 1 calc R U . . .
C21 C 0.51707(19) 0.46623(8) 0.66011(17) 0.0361(5) Uani 1 1 d . . . . .
H21A H 0.497039 0.454719 0.582034 0.054 Uiso 1 1 calc R U . . .
H21B H 0.484762 0.435271 0.700635 0.054 Uiso 1 1 calc R U . . .
H21C H 0.596752 0.465583 0.688978 0.054 Uiso 1 1 calc R U . . .
C22 C 0.35273(17) 0.54021(10) 0.61057(18) 0.0388(5) Uani 1 1 d . . . . .
H22A H 0.326448 0.583401 0.620641 0.058 Uiso 1 1 calc R U . . .
H22B H 0.310115 0.508387 0.638488 0.058 Uiso 1 1 calc R U . . .
H22C H 0.344374 0.532519 0.532229 0.058 Uiso 1 1 calc R U . . .
N1 N 0.92298(12) 0.78562(7) 0.58486(13) 0.0250(4) Uani 1 1 d . . . . .
N2 N 0.54620(14) 0.85989(8) 0.62774(15) 0.0365(4) Uani 1 1 d . . . . .
O1 O 1.12365(9) 0.77244(6) 0.66899(11) 0.0268(3) Uani 1 1 d . . . . .
O2 O 1.06309(10) 0.79678(6) 0.48067(11) 0.0300(3) Uani 1 1 d . . . . .
O3 O 0.59602(10) 0.69338(5) 0.66478(10) 0.0231(3) Uani 1 1 d . . . . .
O4 O 0.53538(10) 0.58097(5) 0.62261(10) 0.0252(3) Uani 1 1 d . . . . .
O5 O 0.51920(10) 0.62979(5) 0.78441(10) 0.0240(3) 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
B1 O3 1.362(2) . ?
B1 O5 1.370(2) . ?
B1 O4 1.359(2) . ?
C1 O1 1.470(2) . ?
C1 C5 1.506(3) . ?
C1 C6 1.517(3) . ?
C1 C2 1.550(3) . ?
C2 O2 1.471(2) . ?
C2 C4 1.517(3) . ?
C2 C3 1.512(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
B2 O1 1.360(2) . ?
B2 O2 1.366(2) . ?
B2 N1 1.430(2) . ?
C8 C9 1.322(2) . ?
C8 N1 1.401(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.518(2) . ?
C9 H9 0.9300 . ?
C10 C13 1.481(2) . ?
C10 C11 1.510(2) . ?
C10 C14 1.580(2) . ?
C11 C12 1.329(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.404(2) . ?
C12 H12 0.9300 . ?
C13 N2 1.149(2) . ?
C14 O3 1.444(2) . ?
C14 C16 1.527(2) . ?
C14 C15 1.516(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O4 1.468(2) . ?
C17 C21 1.518(2) . ?
C17 C22 1.505(3) . ?
C17 C18 1.565(3) . ?
C18 O5 1.4629(19) . ?
C18 C20 1.517(3) . ?
C18 C19 1.505(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
O3 B1 O5 119.27(15) . . ?
O3 B1 O4 126.31(17) . . ?
O5 B1 O4 114.41(14) . . ?
O1 C1 C5 109.02(15) . . ?
O1 C1 C6 106.28(15) . . ?
C5 C1 C6 109.96(17) . . ?
O1 C1 C2 102.51(14) . . ?
C5 C1 C2 114.83(16) . . ?
C6 C1 C2 113.55(17) . . ?
O2 C2 C4 106.64(15) . . ?
O2 C2 C3 108.23(14) . . ?
C4 C2 C3 110.53(17) . . ?
O2 C2 C1 102.21(14) . . ?
C4 C2 C1 113.35(15) . . ?
C3 C2 C1 115.09(17) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 B2 O2 115.29(16) . . ?
O1 B2 N1 122.82(17) . . ?
O2 B2 N1 121.89(17) . . ?
C9 C8 N1 124.16(16) . . ?
C9 C8 H8 117.9 . . ?
N1 C8 H8 117.9 . . ?
C8 C9 C10 122.20(16) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C13 C10 C11 108.70(14) . . ?
C13 C10 C9 108.93(13) . . ?
C11 C10 C9 109.51(13) . . ?
C13 C10 C14 107.67(13) . . ?
C11 C10 C14 110.75(13) . . ?
C9 C10 C14 111.21(14) . . ?
C12 C11 C10 122.67(16) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 N1 123.49(16) . . ?
C11 C12 H12 118.3 . . ?
N1 C12 H12 118.3 . . ?
N2 C13 C10 178.29(18) . . ?
O3 C14 C16 109.81(13) . . ?
O3 C14 C15 111.74(14) . . ?
C16 C14 C15 111.24(15) . . ?
O3 C14 C10 102.97(12) . . ?
C16 C14 C10 110.94(13) . . ?
C15 C14 C10 109.86(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C21 107.60(14) . . ?
O4 C17 C22 106.93(14) . . ?
C21 C17 C22 110.46(16) . . ?
O4 C17 C18 101.75(13) . . ?
C21 C17 C18 114.64(15) . . ?
C22 C17 C18 114.56(16) . . ?
O5 C18 C20 108.69(14) . . ?
O5 C18 C19 107.21(14) . . ?
C20 C18 C19 110.27(16) . . ?
O5 C18 C17 102.25(13) . . ?
C20 C18 C17 114.18(16) . . ?
C19 C18 C17 113.61(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 N1 C8 115.97(14) . . ?
C12 N1 B2 122.61(16) . . ?
C8 N1 B2 121.34(15) . . ?
B2 O1 C1 105.26(14) . . ?
B2 O2 C2 105.47(14) . . ?
B1 O3 C14 124.35(13) . . ?
B1 O4 C17 106.71(13) . . ?
B1 O5 C18 105.74(12) . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046




