# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_11_a
_database_code_depnum_ccdc_archive 'CCDC 1978990'
loop_
_audit_author_name
_audit_author_address
'Liang Xu'
;Shihezi University
China
;
_audit_update_record             
;
2020-01-20 deposited with the CCDC.	2020-06-15 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            'C30 H25 B N2 O'
_chemical_formula_weight         440.33

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                   17.6430(5)
_cell_length_b                   8.5349(3)
_cell_length_c                   15.3612(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.4470(10)
_cell_angle_gamma                90
_cell_volume                     2302.66(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8335
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.67

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             928
_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    0.076
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6636
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_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 D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27450
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         26.734
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4885
_reflns_number_gt                3976
_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 APEX3'
_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    ?
_computing_publication_material  ?
_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)+(0.0297P)²+0.8391P] 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         4885
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.17159(6) 0.98532(12) 0.34190(8) 0.0441(3) Uani 1 1 d . . . . .
N1 N 0.12901(6) 0.45827(13) 0.36799(7) 0.0258(2) Uani 1 1 d . . . . .
B1 B 0.20358(8) 0.54879(17) 0.33900(10) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.20407(8) 0.85982(16) 0.33286(9) 0.0289(3) Uani 1 1 d . . . . .
C2 C 0.28741(8) 0.85992(16) 0.31697(9) 0.0298(3) Uani 1 1 d . . . . .
H2A H 0.293181 0.907274 0.259133 0.036 Uiso 1 1 calc R U . . .
H2AB H 0.305914 0.750500 0.315863 0.036 Uiso 1 1 calc R U . . .
N2 N 0.16713(6) 0.71959(13) 0.33525(7) 0.0253(2) Uani 1 1 d . . . . .
C3 C 0.33608(8) 0.95140(18) 0.38763(9) 0.0337(3) Uani 1 1 d . . . . .
H3A H 0.312942 1.055820 0.394488 0.040 Uiso 1 1 calc R U . . .
H3AB H 0.335801 0.895399 0.444042 0.040 Uiso 1 1 calc R U . . .
C4 C 0.41736(8) 0.97241(17) 0.36699(9) 0.0305(3) Uani 1 1 d . . . . .
C5 C 0.47531(9) 0.88216(18) 0.40832(10) 0.0384(4) Uani 1 1 d . . . . .
H5 H 0.463526 0.804957 0.449503 0.046 Uiso 1 1 calc R U . . .
C7 C 0.56816(9) 1.0139(2) 0.33092(11) 0.0443(4) Uani 1 1 d . . . . .
H7 H 0.619522 1.027800 0.318707 0.053 Uiso 1 1 calc R U . . .
C6 C 0.55006(9) 0.9027(2) 0.39057(12) 0.0440(4) Uani 1 1 d . . . . .
H6 H 0.589085 0.839847 0.419614 0.053 Uiso 1 1 calc R U . . .
C8 C 0.51124(10) 1.1051(2) 0.28898(12) 0.0498(4) Uani 1 1 d . . . . .
H8 H 0.523360 1.182300 0.247956 0.060 Uiso 1 1 calc R U . . .
C9 C 0.43636(9) 1.0839(2) 0.30684(11) 0.0420(4) Uani 1 1 d . . . . .
H9 H 0.397428 1.146540 0.277471 0.050 Uiso 1 1 calc R U . . .
C10 C 0.11942(9) 0.30889(16) 0.38829(9) 0.0307(3) Uani 1 1 d . . . . .
H10 H 0.161618 0.239339 0.390924 0.037 Uiso 1 1 calc R U . . .
C11 C 0.04797(9) 0.25248(18) 0.40587(10) 0.0367(4) Uani 1 1 d . . . . .
H11 H 0.042321 0.145795 0.421662 0.044 Uiso 1 1 calc R U . . .
C12 C -0.01371(9) 0.35003(19) 0.40045(10) 0.0375(4) Uani 1 1 d . . . . .
H12 H -0.062237 0.310731 0.411564 0.045 Uiso 1 1 calc R U . . .
C13 C -0.00530(8) 0.50934(18) 0.37830(9) 0.0321(3) Uani 1 1 d . . . . .
C14 C 0.06856(7) 0.55806(16) 0.36410(8) 0.0263(3) Uani 1 1 d . . . . .
C15 C 0.08860(8) 0.71263(16) 0.34425(8) 0.0264(3) Uani 1 1 d . . . . .
C16 C 0.03138(8) 0.82278(18) 0.33626(10) 0.0336(3) Uani 1 1 d . . . . .
H16 H 0.042097 0.928675 0.322834 0.040 Uiso 1 1 calc R U . . .
C17 C -0.04382(9) 0.7752(2) 0.34844(11) 0.0409(4) Uani 1 1 d . . . . .
H17 H -0.083184 0.851390 0.341917 0.049 Uiso 1 1 calc R U . . .
C18 C -0.06264(9) 0.6255(2) 0.36908(11) 0.0407(4) Uani 1 1 d . . . . .
H18 H -0.113865 0.599510 0.377172 0.049 Uiso 1 1 calc R U . . .
C19 C 0.21792(7) 0.48326(15) 0.24361(9) 0.0245(3) Uani 1 1 d . . . . .
C20 C 0.24159(8) 0.32789(16) 0.23284(9) 0.0297(3) Uani 1 1 d . . . . .
H20 H 0.250253 0.262744 0.282940 0.036 Uiso 1 1 calc R U . . .
C21 C 0.25271(8) 0.26664(18) 0.15158(10) 0.0355(3) Uani 1 1 d . . . . .
H21 H 0.269412 0.161429 0.146833 0.043 Uiso 1 1 calc R U . . .
C22 C 0.23968(9) 0.3576(2) 0.07758(10) 0.0398(4) Uani 1 1 d . . . . .
H22 H 0.247631 0.315835 0.021833 0.048 Uiso 1 1 calc R U . . .
C23 C 0.21491(9) 0.51006(19) 0.08528(10) 0.0390(4) Uani 1 1 d . . . . .
H23 H 0.204851 0.572954 0.034470 0.047 Uiso 1 1 calc R U . . .
C24 C 0.20463(8) 0.57196(17) 0.16723(9) 0.0309(3) Uani 1 1 d . . . . .
H24 H 0.188133 0.677436 0.171309 0.037 Uiso 1 1 calc R U . . .
C25 C 0.27183(8) 0.53250(15) 0.41598(9) 0.0261(3) Uani 1 1 d . . . . .
C26 C 0.26388(9) 0.59968(17) 0.49787(9) 0.0328(3) Uani 1 1 d . . . . .
H26 H 0.216829 0.647412 0.507830 0.039 Uiso 1 1 calc R U . . .
C27 C 0.32229(10) 0.59879(19) 0.56472(10) 0.0412(4) Uani 1 1 d . . . . .
H27 H 0.315724 0.649336 0.618587 0.049 Uiso 1 1 calc R U . . .
C28 C 0.38995(10) 0.5246(2) 0.55314(11) 0.0445(4) Uani 1 1 d . . . . .
H28 H 0.429850 0.522177 0.599219 0.053 Uiso 1 1 calc R U . . .
C29 C 0.39931(9) 0.4540(2) 0.47420(11) 0.0430(4) Uani 1 1 d . . . . .
H29 H 0.445490 0.401055 0.466159 0.052 Uiso 1 1 calc R U . . .
C30 C 0.34137(8) 0.46007(18) 0.40627(10) 0.0343(3) Uani 1 1 d . . . . .
H30 H 0.349389 0.413545 0.351715 0.041 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 C1 1.2287(17) . ?
N1 C10 1.3271(18) . ?
N1 C14 1.3618(17) . ?
N1 B1 1.6240(18) . ?
B1 N2 1.5921(17) . ?
B1 C19 1.611(2) . ?
B1 C25 1.612(2) . ?
C1 N2 1.3649(17) . ?
C1 C2 1.5133(19) . ?
C2 C3 1.532(2) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
N2 C15 1.4067(17) . ?
C3 C4 1.509(2) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.385(2) . ?
C4 C9 1.389(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C7 C6 1.378(2) . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.399(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.366(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.413(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4045(19) . ?
C13 C18 1.414(2) . ?
C14 C15 1.4067(19) . ?
C15 C16 1.3764(19) . ?
C16 C17 1.417(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.365(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.3973(19) . ?
C19 C20 1.4048(19) . ?
C20 C21 1.384(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.394(2) . ?
C25 C26 1.4016(19) . ?
C26 C27 1.384(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.378(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(2) . ?
C29 H29 0.9500 . ?
C30 H30 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
C10 N1 C14 119.63(12) . . ?
C10 N1 B1 130.25(11) . . ?
C14 N1 B1 109.99(11) . . ?
N2 B1 C19 112.51(11) . . ?
N2 B1 C25 112.12(11) . . ?
C19 B1 C25 117.81(11) . . ?
N2 B1 N1 96.35(10) . . ?
C19 B1 N1 106.59(10) . . ?
C25 B1 N1 109.03(11) . . ?
O1 C1 N2 122.17(13) . . ?
O1 C1 C2 119.23(13) . . ?
N2 C1 C2 118.59(12) . . ?
C1 C2 C3 111.94(11) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2AB 109.2 . . ?
C3 C2 H2AB 109.2 . . ?
H2A C2 H2AB 107.9 . . ?
C1 N2 C15 121.13(11) . . ?
C1 N2 B1 127.71(11) . . ?
C15 N2 B1 110.85(10) . . ?
C4 C3 C2 113.05(12) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3AB 109.0 . . ?
C2 C3 H3AB 109.0 . . ?
H3A C3 H3AB 107.8 . . ?
C5 C4 C9 118.13(14) . . ?
C5 C4 C3 120.84(14) . . ?
C9 C4 C3 121.03(13) . . ?
C6 C5 C4 121.02(15) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C6 C7 C8 119.63(15) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C6 C5 120.27(15) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C7 C8 C9 119.91(16) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 121.05(15) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
N1 C10 C11 120.87(14) . . ?
N1 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.36(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.99(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 116.27(13) . . ?
C14 C13 C18 116.27(14) . . ?
C12 C13 C18 127.47(14) . . ?
N1 C14 C13 122.84(13) . . ?
N1 C14 C15 112.59(12) . . ?
C13 C14 C15 124.57(13) . . ?
C16 C15 N2 133.10(13) . . ?
C16 C15 C14 117.55(13) . . ?
N2 C15 C14 109.34(11) . . ?
C15 C16 C17 118.71(14) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 123.42(14) . . ?
C18 C17 H17 118.3 . . ?
C16 C17 H17 118.3 . . ?
C17 C18 C13 119.46(14) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
C24 C19 C20 116.14(13) . . ?
C24 C19 B1 123.19(12) . . ?
C20 C19 B1 120.60(12) . . ?
C21 C20 C19 122.13(14) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C22 C21 C20 120.30(14) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.30(14) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C24 120.27(15) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 121.84(14) . . ?
C23 C24 H24 119.1 . . ?
C19 C24 H24 119.1 . . ?
C30 C25 C26 116.19(13) . . ?
C30 C25 B1 124.29(12) . . ?
C26 C25 B1 119.46(12) . . ?
C27 C26 C25 122.19(15) . . ?
C27 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C28 C27 C26 120.00(15) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 119.49(14) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C28 C29 C30 120.20(15) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 121.85(15) . . ?
C29 C30 H30 119.1 . . ?
C25 C30 H30 119.1 . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.037

