# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_xb7460_0m
_database_code_depnum_ccdc_archive 'CCDC 2026629'
loop_
_audit_author_name
_audit_author_address
subpc
;the cambridge crytallographic data centre
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2020-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H17 B N6 O2'
_chemical_formula_weight         516.32

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/n

loop_
_symmetry_equiv_pos_as_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                   15.606(3)
_cell_length_b                   9.991(2)
_cell_length_c                   16.737(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.846(4)
_cell_angle_gamma                90.00
_cell_volume                     2422.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    624
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      16.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12101
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.1031
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.42
_reflns_number_total             4446
_reflns_number_gt                2039
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0618P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0043(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4446
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1503
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.9891(3) 0.3367(5) 0.2398(3) 0.0527(12) Uani 1 1 d . . .
C1 C 0.9489(3) 0.2575(4) 0.3636(2) 0.0567(10) Uani 1 1 d . . .
C2 C 0.9875(3) 0.2754(4) 0.4570(2) 0.0591(11) Uani 1 1 d . . .
C3 C 0.9624(3) 0.2236(5) 0.5222(3) 0.0832(15) Uani 1 1 d . . .
H3 H 0.9090 0.1731 0.5100 0.100 Uiso 1 1 calc R . .
C4 C 1.0202(4) 0.2501(6) 0.6059(3) 0.0941(16) Uani 1 1 d . . .
H4 H 1.0058 0.2145 0.6508 0.113 Uiso 1 1 calc R . .
C5 C 1.0992(3) 0.3283(5) 0.6254(3) 0.0883(15) Uani 1 1 d . . .
H5 H 1.1342 0.3493 0.6825 0.106 Uiso 1 1 calc R . .
C6 C 1.1255(3) 0.3743(5) 0.5613(3) 0.0751(13) Uani 1 1 d . . .
H6 H 1.1802 0.4219 0.5742 0.090 Uiso 1 1 calc R . .
C7 C 1.0696(3) 0.3490(4) 0.4768(2) 0.0578(10) Uani 1 1 d . . .
C8 C 1.0820(3) 0.3722(4) 0.3969(2) 0.0559(10) Uani 1 1 d . . .
C9 C 1.1619(3) 0.3610(4) 0.3060(3) 0.0555(10) Uani 1 1 d . . .
C10 C 1.2393(3) 0.3214(4) 0.2838(2) 0.0559(10) Uani 1 1 d . . .
C11 C 1.3339(3) 0.3298(4) 0.3277(3) 0.0708(12) Uani 1 1 d . . .
H11 H 1.3583 0.3763 0.3794 0.085 Uiso 1 1 calc R . .
C12 C 1.3911(3) 0.2682(5) 0.2933(3) 0.0827(14) Uani 1 1 d . . .
H12 H 1.4548 0.2745 0.3214 0.099 Uiso 1 1 calc R . .
C13 C 1.3546(3) 0.1963(4) 0.2167(3) 0.0782(14) Uani 1 1 d . . .
H13 H 1.3946 0.1544 0.1950 0.094 Uiso 1 1 calc R . .
C14 C 1.2612(3) 0.1858(4) 0.1724(3) 0.0639(11) Uani 1 1 d . . .
H14 H 1.2377 0.1371 0.1215 0.077 Uiso 1 1 calc R . .
C15 C 1.2028(3) 0.2494(4) 0.2052(2) 0.0528(10) Uani 1 1 d . . .
C16 C 1.1032(2) 0.2459(4) 0.1806(2) 0.0524(10) Uani 1 1 d . . .
C17 C 0.9653(2) 0.1336(4) 0.1448(2) 0.0487(9) Uani 1 1 d . . .
C18 C 0.9057(2) 0.0175(4) 0.1262(2) 0.0478(9) Uani 1 1 d . . .
C19 C 0.8924(2) -0.0870(4) 0.0687(2) 0.0594(11) Uani 1 1 d . . .
H19 H 0.9216 -0.0882 0.0293 0.071 Uiso 1 1 calc R . .
C20 C 0.8348(3) -0.1892(4) 0.0716(3) 0.0637(11) Uani 1 1 d . . .
H20 H 0.8236 -0.2592 0.0324 0.076 Uiso 1 1 calc R . .
C21 C 0.7933(3) -0.1906(4) 0.1309(3) 0.0661(11) Uani 1 1 d . . .
H21 H 0.7554 -0.2622 0.1313 0.079 Uiso 1 1 calc R . .
C22 C 0.8062(2) -0.0897(4) 0.1892(2) 0.0622(11) Uani 1 1 d . . .
H22 H 0.7786 -0.0926 0.2298 0.075 Uiso 1 1 calc R . .
C23 C 0.8618(2) 0.0177(4) 0.1863(2) 0.0503(10) Uani 1 1 d . . .
C24 C 0.8911(2) 0.1371(4) 0.2382(2) 0.0522(10) Uani 1 1 d . . .
C25 C 0.8760(3) 0.4524(4) 0.1175(2) 0.0568(10) Uani 1 1 d . . .
C26 C 0.7833(3) 0.4395(4) 0.1009(3) 0.0702(12) Uani 1 1 d . . .
H26 H 0.7638 0.4294 0.1468 0.084 Uiso 1 1 calc R . .
C27 C 0.7184(3) 0.4412(4) 0.0182(3) 0.0680(12) Uani 1 1 d . . .
H27 H 0.6560 0.4317 0.0083 0.082 Uiso 1 1 calc R . .
C28 C 0.7471(3) 0.4570(4) -0.0492(3) 0.0585(11) Uani 1 1 d . . .
C29 C 0.8390(3) 0.4682(4) -0.0342(3) 0.0752(13) Uani 1 1 d . . .
H29 H 0.8581 0.4779 -0.0803 0.090 Uiso 1 1 calc R . .
C30 C 0.9039(3) 0.4651(4) 0.0488(3) 0.0758(13) Uani 1 1 d . . .
H30 H 0.9663 0.4717 0.0584 0.091 Uiso 1 1 calc R . .
C31 C 0.6791(4) 0.4637(4) -0.1382(3) 0.0767(13) Uani 1 1 d . . .
H31 H 0.7013 0.4775 -0.1820 0.092 Uiso 1 1 calc R . .
N1 N 1.00317(19) 0.3308(3) 0.33281(18) 0.0523(8) Uani 1 1 d . . .
N2 N 1.1602(2) 0.3944(3) 0.38365(19) 0.0584(9) Uani 1 1 d . . .
N3 N 1.08388(19) 0.3249(3) 0.23788(18) 0.0497(8) Uani 1 1 d . . .
N4 N 1.0420(2) 0.1568(3) 0.12869(18) 0.0538(8) Uani 1 1 d . . .
N5 N 0.94394(19) 0.2080(3) 0.20397(18) 0.0491(8) Uani 1 1 d . . .
N6 N 0.88796(19) 0.1671(3) 0.31527(19) 0.0587(9) Uani 1 1 d . . .
O1 O 0.93779(18) 0.4568(3) 0.19973(15) 0.0701(8) Uani 1 1 d . . .
O2 O 0.5969(2) 0.4526(4) -0.1582(2) 0.1090(13) 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 O1 1.460(5) . ?
B1 N5 1.482(5) . ?
B1 N1 1.490(5) . ?
B1 N3 1.497(5) . ?
C1 N6 1.342(5) . ?
C1 N1 1.358(4) . ?
C1 C2 1.462(5) . ?
C2 C3 1.389(5) . ?
C2 C7 1.405(5) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.439(5) . ?
C8 N2 1.339(4) . ?
C8 N1 1.361(4) . ?
C9 N2 1.352(4) . ?
C9 N3 1.371(4) . ?
C9 C10 1.444(5) . ?
C10 C11 1.386(5) . ?
C10 C15 1.419(5) . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.453(5) . ?
C16 N4 1.357(4) . ?
C16 N3 1.360(4) . ?
C17 N4 1.343(4) . ?
C17 N5 1.375(4) . ?
C17 C18 1.446(5) . ?
C18 C19 1.382(5) . ?
C18 C23 1.412(5) . ?
C19 C20 1.373(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.393(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.446(5) . ?
C24 N6 1.344(4) . ?
C24 N5 1.363(4) . ?
C25 O1 1.356(4) . ?
C25 C26 1.375(5) . ?
C25 C30 1.377(5) . ?
C26 C27 1.378(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.368(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.366(5) . ?
C28 C31 1.474(5) . ?
C29 C30 1.382(5) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 O2 1.204(5) . ?
C31 H31 0.9300 . ?

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
O1 B1 N5 115.5(3) . . ?
O1 B1 N1 110.8(3) . . ?
N5 B1 N1 104.6(3) . . ?
O1 B1 N3 115.6(4) . . ?
N5 B1 N3 104.3(3) . . ?
N1 B1 N3 104.9(3) . . ?
N6 C1 N1 122.4(3) . . ?
N6 C1 C2 130.1(4) . . ?
N1 C1 C2 105.8(3) . . ?
C3 C2 C7 120.5(4) . . ?
C3 C2 C1 132.1(4) . . ?
C7 C2 C1 107.0(3) . . ?
C4 C3 C2 117.3(4) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 122.2(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 118.9(4) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C2 120.7(4) . . ?
C6 C7 C8 132.0(4) . . ?
C2 C7 C8 106.9(3) . . ?
N2 C8 N1 122.2(3) . . ?
N2 C8 C7 128.8(3) . . ?
N1 C8 C7 106.8(3) . . ?
N2 C9 N3 122.4(3) . . ?
N2 C9 C10 129.2(3) . . ?
N3 C9 C10 106.4(3) . . ?
C11 C10 C15 120.1(4) . . ?
C11 C10 C9 132.5(4) . . ?
C15 C10 C9 107.0(3) . . ?
C12 C11 C10 118.8(4) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 121.7(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 118.4(4) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 C16 132.1(4) . . ?
C10 C15 C16 107.0(3) . . ?
N4 C16 N3 123.0(3) . . ?
N4 C16 C15 128.4(4) . . ?
N3 C16 C15 106.3(3) . . ?
N4 C17 N5 121.6(3) . . ?
N4 C17 C18 130.2(4) . . ?
N5 C17 C18 106.3(3) . . ?
C19 C18 C23 120.6(4) . . ?
C19 C18 C17 132.4(4) . . ?
C23 C18 C17 106.8(3) . . ?
C20 C19 C18 117.9(4) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C21 C20 C19 121.6(4) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C22 C21 C20 121.7(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 118.1(4) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C22 C23 C18 119.9(4) . . ?
C22 C23 C24 132.5(4) . . ?
C18 C23 C24 107.5(3) . . ?
N6 C24 N5 122.1(3) . . ?
N6 C24 C23 130.1(4) . . ?
N5 C24 C23 106.4(3) . . ?
O1 C25 C26 120.3(4) . . ?
O1 C25 C30 121.2(4) . . ?
C26 C25 C30 118.4(4) . . ?
C25 C26 C27 121.7(4) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C28 C27 C26 119.1(4) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C29 C28 C27 120.1(4) . . ?
C29 C28 C31 119.6(4) . . ?
C27 C28 C31 120.3(4) . . ?
C28 C29 C30 120.6(4) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C25 C30 C29 120.0(4) . . ?
C25 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
O2 C31 C28 124.6(5) . . ?
O2 C31 H31 117.7 . . ?
C28 C31 H31 117.7 . . ?
C1 N1 C8 111.9(3) . . ?
C1 N1 B1 123.2(3) . . ?
C8 N1 B1 123.4(3) . . ?
C8 N2 C9 117.6(3) . . ?
C16 N3 C9 112.2(3) . . ?
C16 N3 B1 122.8(3) . . ?
C9 N3 B1 122.8(3) . . ?
C17 N4 C16 116.9(3) . . ?
C24 N5 C17 111.6(3) . . ?
C24 N5 B1 123.5(3) . . ?
C17 N5 B1 123.7(3) . . ?
C1 N6 C24 117.3(3) . . ?
C25 O1 B1 120.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
