# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1913373'
loop_
_audit_author_name
_audit_author_address
'Gengwen Tan'
;Nanjing University
China
;
_audit_update_record             
;
2019-05-01 deposited with the CCDC.	2019-09-18 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            'C23 H26 B N'
_chemical_formula_weight         327.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.4562(7)
_cell_length_b                   11.3431(9)
_cell_length_c                   11.8941(10)
_cell_angle_alpha                108.839(3)
_cell_angle_beta                 109.210(3)
_cell_angle_gamma                101.912(3)
_cell_volume                     955.21(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    7380
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      53.96

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.307
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6227
_exptl_absorpt_correction_T_max  0.7131
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12455
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.778
_diffrn_reflns_theta_max         53.967
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3465
_reflns_number_gt                2794
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0816P)²+0.2367P] 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         3465
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1459
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
B1 B 0.5020(2) 0.29408(17) 0.72190(17) 0.0334(4) Uani 1 1 d . . . . .
C1 C 0.2885(3) 0.18158(19) 0.8483(2) 0.0513(5) Uani 1 1 d . . . . .
H1A H 0.240426 0.136846 0.894176 0.077 Uiso 1 1 calc R U . . .
H1B H 0.189824 0.174943 0.771803 0.077 Uiso 1 1 calc R U . . .
H1C H 0.357371 0.275444 0.907984 0.077 Uiso 1 1 calc R U . . .
C2 C 0.5271(4) -0.1891(2) 0.8067(2) 0.0714(7) Uani 1 1 d . . . . .
H2A H 0.528590 -0.176574 0.892576 0.107 Uiso 1 1 calc R U . . .
H2B H 0.633737 -0.207931 0.803012 0.107 Uiso 1 1 calc R U . . .
H2C H 0.419826 -0.263791 0.737336 0.107 Uiso 1 1 calc R U . . .
C3 C 0.7445(2) 0.14925(19) 0.65439(19) 0.0494(5) Uani 1 1 d . . . . .
H3A H 0.836635 0.108302 0.662278 0.074 Uiso 1 1 calc R U . . .
H3B H 0.801664 0.246209 0.700281 0.074 Uiso 1 1 calc R U . . .
H3C H 0.671250 0.123822 0.561361 0.074 Uiso 1 1 calc R U . . .
C4 C 0.4088(2) 0.11607(16) 0.80351(16) 0.0387(4) Uani 1 1 d . . . . .
C5 C 0.4191(2) 0.00325(16) 0.82374(17) 0.0434(4) Uani 1 1 d . . . . .
H5 H 0.350700 -0.028544 0.864045 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5258(3) -0.06435(16) 0.78705(17) 0.0463(5) Uani 1 1 d . . . . .
C7 C 0.6283(2) -0.01330(16) 0.73270(17) 0.0457(5) Uani 1 1 d . . . . .
H7 H 0.701889 -0.058585 0.706649 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6280(2) 0.10231(16) 0.71459(16) 0.0385(4) Uani 1 1 d . . . . .
C9 C 0.5142(2) 0.16846(15) 0.74834(15) 0.0340(4) Uani 1 1 d . . . . .
C10 C 0.7358(2) 0.46441(18) 1.01017(17) 0.0441(4) Uani 1 1 d . . . . .
H10A H 0.836975 0.520753 1.095989 0.066 Uiso 1 1 calc R U . . .
H10B H 0.726578 0.371298 0.986611 0.066 Uiso 1 1 calc R U . . .
H10C H 0.625292 0.474405 1.014436 0.066 Uiso 1 1 calc R U . . .
C11 C 1.0592(3) 0.8096(2) 0.9085(3) 0.0738(7) Uani 1 1 d . . . . .
H11A H 1.092534 0.813564 0.837940 0.111 Uiso 1 1 calc R U . . .
H11B H 1.165622 0.824576 0.984674 0.111 Uiso 1 1 calc R U . . .
H11C H 1.008032 0.878466 0.933700 0.111 Uiso 1 1 calc R U . . .
C12 C 0.6091(2) 0.38318(17) 0.53691(17) 0.0439(4) Uani 1 1 d . . . . .
H12A H 0.588545 0.439111 0.489639 0.066 Uiso 1 1 calc R U . . .
H12B H 0.494332 0.318635 0.514704 0.066 Uiso 1 1 calc R U . . .
H12C H 0.685278 0.335860 0.511553 0.066 Uiso 1 1 calc R U . . .
C13 C 0.7645(2) 0.50554(15) 0.90792(16) 0.0358(4) Uani 1 1 d . . . . .
C14 C 0.8905(2) 0.62926(16) 0.94983(18) 0.0429(4) Uani 1 1 d . . . . .
H14 H 0.955988 0.684097 1.041358 0.052 Uiso 1 1 calc R U . . .
C15 C 0.9233(2) 0.67501(17) 0.86125(19) 0.0465(4) Uani 1 1 d . . . . .
C16 C 0.8287(2) 0.59276(17) 0.72901(18) 0.0435(4) Uani 1 1 d . . . . .
H16 H 0.852287 0.621464 0.667570 0.052 Uiso 1 1 calc R U . . .
C17 C 0.6999(2) 0.46920(16) 0.68277(16) 0.0367(4) Uani 1 1 d . . . . .
C18 C 0.6639(2) 0.42421(15) 0.77231(15) 0.0328(4) Uani 1 1 d . . . . .
C19 C 0.1722(2) 0.18106(17) 0.54118(17) 0.0426(4) Uani 1 1 d . . . . .
H19 H 0.186110 0.096816 0.521794 0.051 Uiso 1 1 calc R U . . .
C20 C 0.0124(2) 0.1906(2) 0.47123(19) 0.0511(5) Uani 1 1 d . . . . .
H20 H -0.080149 0.111172 0.402774 0.061 Uiso 1 1 calc R U . . .
C21 C 0.1116(3) 0.4125(2) 0.58976(19) 0.0492(5) Uani 1 1 d . . . . .
H21 H 0.090830 0.494429 0.609969 0.059 Uiso 1 1 calc R U . . .
C22 C 0.2783(2) 0.41386(16) 0.66269(17) 0.0394(4) Uani 1 1 d . . . . .
H22 H 0.369193 0.495630 0.728092 0.047 Uiso 1 1 calc R U . . .
C23 C 0.3130(2) 0.29569(15) 0.64043(15) 0.0341(4) Uani 1 1 d . . . . .
N1 N -0.0204(2) 0.30420(18) 0.49364(16) 0.0543(4) 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 C18 1.570(2) . ?
B1 C9 1.571(2) . ?
B1 C23 1.581(2) . ?
C1 C4 1.511(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C6 1.508(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.504(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.391(2) . ?
C4 C9 1.413(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C7 C8 1.396(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.417(2) . ?
C10 C13 1.506(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C15 1.505(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.507(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.391(2) . ?
C13 C18 1.410(2) . ?
C14 C15 1.394(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C16 C17 1.390(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.410(2) . ?
C19 C20 1.381(2) . ?
C19 C23 1.395(2) . ?
C19 H19 0.9500 . ?
C20 N1 1.335(2) . ?
C20 H20 0.9500 . ?
C21 N1 1.323(3) . ?
C21 C22 1.385(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(2) . ?
C22 H22 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
C18 B1 C9 125.66(14) . . ?
C18 B1 C23 115.02(13) . . ?
C9 B1 C23 119.30(14) . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C2 H2A 109.5 . . ?
C6 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C6 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C3 H3A 109.5 . . ?
C8 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C8 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 120.09(15) . . ?
C5 C4 C1 117.35(16) . . ?
C9 C4 C1 122.50(14) . . ?
C6 C5 C4 122.20(17) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C7 C6 C5 117.63(15) . . ?
C7 C6 C2 122.27(18) . . ?
C5 C6 C2 120.11(19) . . ?
C6 C7 C8 122.51(16) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C7 C8 C9 119.53(16) . . ?
C7 C8 C3 118.23(15) . . ?
C9 C8 C3 122.20(14) . . ?
C4 C9 C8 117.96(14) . . ?
C4 C9 B1 121.02(13) . . ?
C8 C9 B1 121.00(15) . . ?
C13 C10 H10A 109.5 . . ?
C13 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C13 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C11 H11A 109.5 . . ?
C15 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C15 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 H12A 109.5 . . ?
C17 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C17 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.69(15) . . ?
C14 C13 C10 118.41(15) . . ?
C18 C13 C10 121.88(15) . . ?
C13 C14 C15 121.82(16) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C15 C14 118.02(16) . . ?
C16 C15 C11 120.95(18) . . ?
C14 C15 C11 121.03(18) . . ?
C15 C16 C17 122.06(17) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C18 119.90(15) . . ?
C16 C17 C12 118.44(15) . . ?
C18 C17 C12 121.58(14) . . ?
C17 C18 C13 118.46(14) . . ?
C17 C18 B1 120.48(14) . . ?
C13 C18 B1 120.74(14) . . ?
C20 C19 C23 119.73(16) . . ?
C20 C19 H19 120.1 . . ?
C23 C19 H19 120.1 . . ?
N1 C20 C19 124.20(18) . . ?
N1 C20 H20 117.9 . . ?
C19 C20 H20 117.9 . . ?
N1 C21 C22 123.98(17) . . ?
N1 C21 H21 118.0 . . ?
C22 C21 H21 118.0 . . ?
C23 C22 C21 120.17(16) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C19 115.75(15) . . ?
C22 C23 B1 121.33(14) . . ?
C19 C23 B1 122.92(14) . . ?
C21 N1 C20 116.11(15) . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1913376'
loop_
_audit_author_name
_audit_author_address
'Gengwen Tan'
;Nanjing University
China
;
_audit_update_record             
;
2019-05-01 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 B O3'
_chemical_formula_weight         195.04

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.0306(5)
_cell_length_b                   11.4395(9)
_cell_length_c                   15.2784(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.144(3)
_cell_angle_gamma                90
_cell_volume                     1040.62(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3558
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   'SADABS (Bruker, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9178
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.234
_diffrn_reflns_theta_max         27.694
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2421
_reflns_number_gt                1905
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.4504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2421
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O3 O 0.34068(17) 0.53772(8) 0.64160(7) 0.0217(3) Uani 1 1 d . . . . .
O1 O 0.58511(18) 0.64665(9) 0.74045(7) 0.0233(3) Uani 1 1 d . . . . .
O2 O 0.33260(18) 0.74350(8) 0.62514(7) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.1697(2) 0.52182(12) 0.57025(10) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.2115(2) 0.45128(12) 0.50084(10) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.3528 0.4184 0.5016 0.023 Uiso 1 1 calc R U . . .
C10 C -0.0406(2) 0.56986(12) 0.56985(10) 0.0195(3) Uani 1 1 d . . . . .
H10 H -0.0680 0.6164 0.6169 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4408(2) 0.85588(12) 0.64759(10) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.6603(3) 0.75386(12) 0.78797(10) 0.0216(4) Uani 1 1 d . . . . .
C2 C 0.5211(3) 0.85876(12) 0.74775(10) 0.0215(3) Uani 1 1 d . . . . .
H2A H 0.3902 0.8655 0.7770 0.026 Uiso 1 1 calc R U . . .
H2B H 0.6101 0.9289 0.7615 0.026 Uiso 1 1 calc R U . . .
C5 C 0.9102(3) 0.76627(14) 0.78538(12) 0.0292(4) Uani 1 1 d . . . . .
H5A H 0.9872 0.6973 0.8097 0.044 Uiso 1 1 calc R U . . .
H5B H 0.9677 0.8331 0.8197 0.044 Uiso 1 1 calc R U . . .
H5C H 0.9336 0.7763 0.7251 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2593(3) 0.94795(13) 0.62255(12) 0.0281(4) Uani 1 1 d . . . . .
H7A H 0.1918 0.9374 0.5618 0.042 Uiso 1 1 calc R U . . .
H7B H 0.3252 1.0244 0.6300 0.042 Uiso 1 1 calc R U . . .
H7C H 0.1467 0.9401 0.6601 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6228(3) 0.73492(15) 0.88273(11) 0.0318(4) Uani 1 1 d . . . . .
H4A H 0.4656 0.7229 0.8837 0.048 Uiso 1 1 calc R U . . .
H4B H 0.6733 0.8024 0.9176 0.048 Uiso 1 1 calc R U . . .
H4C H 0.7056 0.6675 0.9068 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6246(3) 0.87076(15) 0.59122(11) 0.0289(4) Uani 1 1 d . . . . .
H6A H 0.7263 0.8058 0.6008 0.043 Uiso 1 1 calc R U . . .
H6B H 0.7051 0.9419 0.6075 0.043 Uiso 1 1 calc R U . . .
H6C H 0.5588 0.8740 0.5298 0.043 Uiso 1 1 calc R U . . .
B1 B 0.4192(3) 0.64699(14) 0.66926(11) 0.0184(4) 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
O3 B1 1.3790(18) . ?
O3 C9 1.3884(15) . ?
O1 B1 1.3558(18) . ?
O1 C1 1.4602(16) . ?
O2 B1 1.3542(19) . ?
O2 C3 1.4577(16) . ?
C9 C10 1.381(2) . ?
C9 C8 1.387(2) . ?
C8 C10 1.3905(18) 3_566 ?
C8 H8 0.9300 . ?
C10 C8 1.3905(18) 3_566 ?
C10 H10 0.9300 . ?
C3 C6 1.518(2) . ?
C3 C7 1.523(2) . ?
C3 C2 1.530(2) . ?
C1 C4 1.516(2) . ?
C1 C5 1.521(2) . ?
C1 C2 1.536(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
B1 O3 C9 122.37(11) . . ?
B1 O1 C1 121.86(11) . . ?
B1 O2 C3 118.63(11) . . ?
C10 C9 O3 121.22(13) . . ?
C10 C9 C8 120.43(13) . . ?
O3 C9 C8 118.27(13) . . ?
C10 C8 C9 119.50(14) 3_566 . ?
C10 C8 H8 120.2 3_566 . ?
C9 C8 H8 120.2 . . ?
C9 C10 C8 120.06(14) . 3_566 ?
C9 C10 H10 120.0 . . ?
C8 C10 H10 120.0 3_566 . ?
O2 C3 C6 107.78(13) . . ?
O2 C3 C7 105.91(11) . . ?
C6 C3 C7 109.90(13) . . ?
O2 C3 C2 108.24(12) . . ?
C6 C3 C2 114.92(12) . . ?
C7 C3 C2 109.68(13) . . ?
O1 C1 C4 105.85(13) . . ?
O1 C1 C5 107.23(13) . . ?
C4 C1 C5 109.71(13) . . ?
O1 C1 C2 110.51(11) . . ?
C4 C1 C2 109.79(14) . . ?
C5 C1 C2 113.44(13) . . ?
C3 C2 C1 116.70(12) . . ?
C3 C2 H2A 108.1 . . ?
C1 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
C1 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
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 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 B1 O2 125.35(13) . . ?
O1 B1 O3 114.64(13) . . ?
O2 B1 O3 120.00(12) . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1913377'
loop_
_audit_author_name
_audit_author_address
'Gengwen Tan'
;Nanjing University
China
;
_audit_update_record             
;
2019-05-01 deposited with the CCDC.	2019-09-18 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            'C23 H36 B N O5'
_chemical_formula_weight         417.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   10.0847(14)
_cell_length_b                   15.143(3)
_cell_length_c                   31.376(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4791.4(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      49.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.407
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.2346
_exptl_absorpt_correction_T_max  0.2690
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43613
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         4.535
_diffrn_reflns_theta_max         53.000
_diffrn_reflns_theta_full        53.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4199
_reflns_number_gt                2592
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+6.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4199
_refine_ls_number_parameters     304
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.135
_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
C1 C 0.5166(7) 0.7198(5) 0.2300(2) 0.082(2) Uani 0.6 1 d . U P A 1
H1A H 0.479139 0.667824 0.215753 0.122 Uiso 0.6 1 calc R U P A 1
H1B H 0.451121 0.767571 0.229997 0.122 Uiso 0.6 1 calc R U P A 1
H1C H 0.596319 0.739055 0.214696 0.122 Uiso 0.6 1 calc R U P A 1
C2 C 0.6130(9) 0.7605(6) 0.3067(3) 0.095(3) Uani 0.6 1 d . U P A 1
H2A H 0.694301 0.783700 0.293825 0.142 Uiso 0.6 1 calc R U P A 1
H2B H 0.549602 0.808766 0.310918 0.142 Uiso 0.6 1 calc R U P A 1
H2C H 0.633967 0.733509 0.334306 0.142 Uiso 0.6 1 calc R U P A 1
C6 C 0.6971(18) 0.4620(10) 0.2871(5) 0.109(5) Uani 0.4 1 d . U P B 1
H6A H 0.773248 0.464115 0.267684 0.164 Uiso 0.4 1 calc R U P B 1
H6B H 0.717238 0.422724 0.311025 0.164 Uiso 0.4 1 calc R U P B 1
H6C H 0.619390 0.439615 0.271705 0.164 Uiso 0.4 1 calc R U P B 1
C7 C 0.7876(9) 0.5796(8) 0.3303(3) 0.113(3) Uani 0.6 1 d . U P B 1
H7A H 0.865490 0.586174 0.311901 0.170 Uiso 0.6 1 calc R U P B 1
H7B H 0.769334 0.635835 0.344641 0.170 Uiso 0.6 1 calc R U P B 1
H7C H 0.804926 0.533896 0.351726 0.170 Uiso 0.6 1 calc R U P B 1
C3 C 0.5554(3) 0.6946(3) 0.27884(14) 0.0729(12) Uani 1 1 d D . . . .
C4 C 0.6423(4) 0.6174(3) 0.26866(13) 0.0880(13) Uani 1 1 d . . . . .
H4A H 0.601675 0.584827 0.244613 0.106 Uiso 1 1 calc DR U . . .
H4B H 0.728730 0.640364 0.258583 0.106 Uiso 1 1 calc R U . . .
C5 C 0.6685(5) 0.5532(3) 0.30352(14) 0.0936(16) Uani 1 1 d . . . . .
C8 C 0.2352(3) 0.4506(2) 0.37555(10) 0.0512(8) Uani 1 1 d . . . . .
C9 C 0.2370(3) 0.3848(2) 0.41199(10) 0.0534(8) Uani 1 1 d . . . . .
H9A H 0.160694 0.344192 0.408864 0.064 Uiso 1 1 calc R U . . .
H9B H 0.319050 0.349061 0.410093 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2308(3) 0.4277(2) 0.45542(10) 0.0526(8) Uani 1 1 d . . . . .
H10 H 0.143261 0.457402 0.459794 0.063 Uiso 1 1 calc R U . . .
C11 C 0.3429(3) 0.4930(2) 0.46013(10) 0.0550(9) Uani 1 1 d . . . . .
H11A H 0.428345 0.460829 0.459356 0.066 Uiso 1 1 calc R U . . .
H11B H 0.335797 0.522397 0.488224 0.066 Uiso 1 1 calc R U . . .
C12 C 0.3425(3) 0.5633(2) 0.42506(10) 0.0525(8) Uani 1 1 d . . . . .
C13 C 0.2741(4) 0.4020(3) 0.33460(11) 0.0745(11) Uani 1 1 d . . . . .
H13A H 0.266516 0.442254 0.310280 0.112 Uiso 1 1 calc R U . . .
H13B H 0.214975 0.351385 0.330373 0.112 Uiso 1 1 calc R U . . .
H13C H 0.365861 0.381135 0.336960 0.112 Uiso 1 1 calc R U . . .
C14 C 0.0957(3) 0.4900(3) 0.36949(13) 0.0753(12) Uani 1 1 d . . . . .
H14A H 0.061149 0.509687 0.397090 0.113 Uiso 1 1 calc R U . . .
H14B H 0.036597 0.444882 0.357580 0.113 Uiso 1 1 calc R U . . .
H14C H 0.100449 0.540327 0.349937 0.113 Uiso 1 1 calc R U . . .
C15 C 0.4738(4) 0.6135(2) 0.42789(12) 0.0704(11) Uani 1 1 d . . . . .
H15A H 0.547160 0.573475 0.421045 0.106 Uiso 1 1 calc R U . . .
H15B H 0.485382 0.636498 0.456852 0.106 Uiso 1 1 calc R U . . .
H15C H 0.473105 0.662692 0.407596 0.106 Uiso 1 1 calc R U . . .
C16 C 0.2284(4) 0.6295(2) 0.43082(13) 0.0746(11) Uani 1 1 d . . . . .
H16A H 0.212930 0.660740 0.403925 0.112 Uiso 1 1 calc R U . . .
H16B H 0.251870 0.672142 0.453064 0.112 Uiso 1 1 calc R U . . .
H16C H 0.147771 0.597782 0.439134 0.112 Uiso 1 1 calc R U . . .
C17 C 0.1795(4) 0.3548(2) 0.52152(12) 0.0601(9) Uani 1 1 d . . . . .
C18 C 0.2010(4) 0.2715(3) 0.54552(12) 0.0661(10) Uani 1 1 d . . . . .
C19 C 0.3039(5) 0.2148(3) 0.53546(13) 0.0776(12) Uani 1 1 d . . . . .
H19 H 0.365769 0.231349 0.514060 0.093 Uiso 1 1 calc R U . . .
C20 C 0.3184(6) 0.1352(3) 0.55578(17) 0.1070(18) Uani 1 1 d . . . . .
H20 H 0.390796 0.097337 0.549269 0.128 Uiso 1 1 calc R U . . .
C21 C 0.2285(7) 0.1122(4) 0.5849(2) 0.125(2) Uani 1 1 d . . . . .
H21 H 0.237109 0.055710 0.597768 0.150 Uiso 1 1 calc R U . . .
C22 C 0.1260(6) 0.1636(5) 0.59727(19) 0.137(3) Uani 1 1 d . . . . .
H22 H 0.064944 0.144592 0.618426 0.165 Uiso 1 1 calc R U . . .
C23 C 0.1131(4) 0.2492(4) 0.57687(15) 0.115(2) Uani 1 1 d . . . . .
H23 H 0.044942 0.288945 0.585155 0.138 Uiso 1 1 calc R U . . .
B1 B 0.4469(4) 0.5942(3) 0.32709(12) 0.0502(9) Uani 1 1 d . . . . .
C1A C 0.504(3) 0.7616(12) 0.2477(6) 0.070(4) Uiso 0.2 1 d D U P A 2
H1AA H 0.588426 0.784632 0.236972 0.105 Uiso 0.2 1 d R U P A 2
H1AB H 0.490908 0.701262 0.237260 0.105 Uiso 0.2 1 d DR U P A 2
H1AC H 0.431270 0.799191 0.237788 0.105 Uiso 0.2 1 d R U P A 2
C2A C 0.590660 0.785140 0.290190 0.133 Uiso 0.2 1 d . . P A 2
H2AA H 0.561930 0.824760 0.268160 0.199 Uiso 0.2 1 d R U P A 2
H2AB H 0.548230 0.800600 0.316540 0.199 Uiso 0.2 1 d R U P A 2
H2AC H 0.685080 0.789500 0.293460 0.199 Uiso 0.2 1 d R U P A 2
C6A C 0.7562(15) 0.4767(11) 0.3007(5) 0.064(4) Uiso 0.3 1 d . . P B 2
H6AA H 0.830303 0.489614 0.281505 0.096 Uiso 0.3 1 d R U P B 2
H6AB H 0.790747 0.460219 0.328820 0.096 Uiso 0.3 1 d R U P B 2
H6AC H 0.703766 0.427824 0.289127 0.096 Uiso 0.3 1 d R U P B 2
C7A C 0.776(2) 0.6175(13) 0.3438(7) 0.050(5) Uiso 0.2 1 d . . P B 2
H7AA H 0.861867 0.632304 0.331100 0.075 Uiso 0.2 1 d R U P B 2
H7AB H 0.728443 0.672018 0.350977 0.075 Uiso 0.2 1 d R U P B 2
H7AC H 0.789877 0.582657 0.369727 0.075 Uiso 0.2 1 d R U P B 2
C1B C 0.518(3) 0.7670(17) 0.2536(8) 0.071(4) Uiso 0.2 1 d . U P A 3
H1BA H 0.598093 0.789803 0.239418 0.107 Uiso 0.2 1 d R U P A 3
H1BB H 0.462222 0.737074 0.232580 0.107 Uiso 0.2 1 d R U P A 3
H1BC H 0.469298 0.816078 0.266381 0.107 Uiso 0.2 1 d R U P A 3
C2B C 0.637(3) 0.7444(18) 0.3231(7) 0.059(6) Uiso 0.2 1 d . . P A 3
H2BA H 0.660599 0.699663 0.344377 0.089 Uiso 0.2 1 d R U P A 3
H2BB H 0.717489 0.774320 0.313250 0.089 Uiso 0.2 1 d R U P A 3
H2BC H 0.576890 0.787750 0.335995 0.089 Uiso 0.2 1 d R U P A 3
C6B C 0.6177(16) 0.4542(10) 0.2735(5) 0.081(4) Uiso 0.3 1 d . . P B 3
H6BA H 0.529107 0.461930 0.261206 0.121 Uiso 0.3 1 d R U P B 3
H6BB H 0.681715 0.443001 0.250617 0.121 Uiso 0.3 1 d R U P B 3
H6BC H 0.616944 0.404091 0.293226 0.121 Uiso 0.3 1 d R U P B 3
C7B C 0.7761(16) 0.5261(12) 0.3147(5) 0.036(4) Uiso 0.2 1 d . . P B 3
H7BA H 0.841467 0.537627 0.292326 0.053 Uiso 0.2 1 d R U P B 3
H7BB H 0.801482 0.557762 0.340720 0.053 Uiso 0.2 1 d R U P B 3
H7BC H 0.772750 0.462538 0.320617 0.053 Uiso 0.2 1 d R U P B 3
N1 N 0.3437(2) 0.51445(16) 0.38413(8) 0.0459(6) Uani 1 1 d . . . . .
O1 O 0.4361(2) 0.66241(17) 0.29914(8) 0.0745(8) Uani 1 1 d . . . . .
O2 O 0.5562(2) 0.54412(14) 0.33150(7) 0.0568(6) Uani 1 1 d . . . . .
O3 O 0.3344(2) 0.58184(14) 0.35073(7) 0.0563(6) Uani 1 1 d . . . . .
O4 O 0.2488(2) 0.35613(15) 0.48595(7) 0.0631(7) Uani 1 1 d . . . . .
O5 O 0.1080(3) 0.4143(2) 0.53208(10) 0.1040(11) 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
C1 C3 1.628(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.448(10) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C6 C5 1.502(14) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C5 1.520(11) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C3 O1 1.446(4) . ?
C3 C2A 1.460(4) . ?
C3 C1B 1.40(2) . ?
C3 C4 1.497(5) . ?
C3 C1A 1.499(9) . ?
C3 C2B 1.78(2) . ?
C4 C5 1.487(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7B 1.212(16) . ?
C5 O2 1.440(4) . ?
C5 C6A 1.460(16) . ?
C5 C6B 1.843(16) . ?
C5 C7A 1.93(2) . ?
C8 N1 1.484(4) . ?
C8 C9 1.517(4) . ?
C8 C13 1.532(5) . ?
C8 C14 1.540(4) . ?
C9 C10 1.511(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O4 1.458(3) . ?
C10 C11 1.509(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.531(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N1 1.482(4) . ?
C12 C15 1.530(4) . ?
C12 C16 1.536(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O5 1.201(4) . ?
C17 O4 1.316(4) . ?
C17 C18 1.485(5) . ?
C18 C23 1.366(5) . ?
C18 C19 1.384(5) . ?
C19 C20 1.372(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.332(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.353(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.451(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
B1 O2 1.345(4) . ?
B1 O1 1.359(4) . ?
B1 O3 1.369(4) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9599 . ?
C2A H2AC 0.9600 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C2B H2BA 0.9800 . ?
C2B H2BB 0.9800 . ?
C2B H2BC 0.9800 . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C6B H6BC 0.9800 . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
N1 O3 1.466(3) . ?

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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C3 O1 107.5(5) . . ?
O1 C3 C2A 114.3(3) . . ?
O1 C3 C1B 107.0(13) . . ?
C2 C3 C4 115.6(5) . . ?
O1 C3 C4 108.5(3) . . ?
C2A C3 C4 130.0(3) . . ?
C1B C3 C4 130.2(12) . . ?
C2 C3 C1 120.3(5) . . ?
O1 C3 C1 107.1(4) . . ?
C4 C3 C1 97.0(4) . . ?
O1 C3 C1A 103.2(12) . . ?
C2A C3 C1A 66.9(11) . . ?
C4 C3 C1A 126.3(6) . . ?
O1 C3 C2B 100.6(9) . . ?
C1B C3 C2B 103.5(15) . . ?
C4 C3 C2B 103.1(9) . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 H4A 108.0 . . ?
C3 C4 H4A 108.0 . . ?
C5 C4 H4B 108.0 . . ?
C3 C4 H4B 108.0 . . ?
H4A C4 H4B 107.2 . . ?
C7B C5 O2 119.7(8) . . ?
O2 C5 C6A 116.0(7) . . ?
C7B C5 C4 126.4(9) . . ?
O2 C5 C4 111.8(3) . . ?
C6A C5 C4 125.6(7) . . ?
O2 C5 C6 105.9(7) . . ?
C4 C5 C6 112.4(7) . . ?
O2 C5 C7 108.0(5) . . ?
C4 C5 C7 112.0(5) . . ?
C6 C5 C7 106.3(9) . . ?
C7B C5 C6B 97.0(10) . . ?
O2 C5 C6B 90.9(6) . . ?
C4 C5 C6B 96.1(6) . . ?
O2 C5 C7A 95.2(7) . . ?
C6A C5 C7A 95.7(10) . . ?
C4 C5 C7A 104.6(7) . . ?
N1 C8 C9 106.4(2) . . ?
N1 C8 C13 106.0(3) . . ?
C9 C8 C13 108.2(3) . . ?
N1 C8 C14 116.4(3) . . ?
C9 C8 C14 111.0(3) . . ?
C13 C8 C14 108.5(3) . . ?
C10 C9 C8 113.3(3) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O4 C10 C11 109.3(3) . . ?
O4 C10 C9 105.5(2) . . ?
C11 C10 C9 109.8(3) . . ?
O4 C10 H10 110.7 . . ?
C11 C10 H10 110.7 . . ?
C9 C10 H10 110.7 . . ?
C10 C11 C12 112.5(3) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 C15 106.9(3) . . ?
N1 C12 C11 106.0(2) . . ?
C15 C12 C11 107.5(3) . . ?
N1 C12 C16 115.7(3) . . ?
C15 C12 C16 108.5(3) . . ?
C11 C12 C16 111.8(3) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 O4 122.8(3) . . ?
O5 C17 C18 125.8(4) . . ?
O4 C17 C18 111.4(3) . . ?
C23 C18 C19 119.8(4) . . ?
C23 C18 C17 118.7(4) . . ?
C19 C18 C17 121.4(3) . . ?
C20 C19 C18 121.3(5) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 118.4(6) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C22 124.5(6) . . ?
C20 C21 H21 117.7 . . ?
C22 C21 H21 117.7 . . ?
C21 C22 C23 117.1(5) . . ?
C21 C22 H22 121.4 . . ?
C23 C22 H22 121.4 . . ?
C18 C23 C22 118.7(5) . . ?
C18 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
O2 B1 O1 124.1(3) . . ?
O2 B1 O3 123.1(3) . . ?
O1 B1 O3 112.8(3) . . ?
C3 C1A H1AA 99.5 . . ?
C3 C1A H1AB 68.6 . . ?
H1AA C1A H1AB 109.5 . . ?
C3 C1A H1AC 149.2 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C3 C2A H2AA 109.7 . . ?
C3 C2A H2AB 109.3 . . ?
H2AA C2A H2AB 109.5 . . ?
C3 C2A H2AC 109.4 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C5 C6A H6AA 109.9 . . ?
C5 C6A H6AB 111.3 . . ?
H6AA C6A H6AB 109.5 . . ?
C5 C6A H6AC 107.1 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C5 C7A H7AA 110.2 . . ?
C5 C7A H7AB 107.6 . . ?
H7AA C7A H7AB 109.5 . . ?
C5 C7A H7AC 110.6 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C3 C1B H1BA 108.3 . . ?
C3 C1B H1BB 99.9 . . ?
H1BA C1B H1BB 109.5 . . ?
C3 C1B H1BC 119.6 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C3 C2B H2BA 110.5 . . ?
C3 C2B H2BB 109.3 . . ?
H2BA C2B H2BB 109.5 . . ?
C3 C2B H2BC 108.6 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
C5 C6B H6BA 111.0 . . ?
C5 C6B H6BB 109.4 . . ?
H6BA C6B H6BB 109.5 . . ?
C5 C6B H6BC 108.0 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C5 C7B H7BA 109.5 . . ?
C5 C7B H7BB 108.0 . . ?
H7BA C7B H7BB 109.5 . . ?
C5 C7B H7BC 110.9 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
O3 N1 C12 105.8(2) . . ?
O3 N1 C8 106.0(2) . . ?
C12 N1 C8 118.4(2) . . ?
B1 O1 C3 118.3(3) . . ?
B1 O2 C5 121.9(3) . . ?
B1 O3 N1 115.5(2) . . ?
C17 O4 C10 120.2(3) . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1913374'
loop_
_audit_author_name
_audit_author_address
'Gengwen Tan'
;Nanjing University
China
;
_audit_update_record             
;
2019-05-01 deposited with the CCDC.	2019-09-18 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 H40 B2 N O2'
_chemical_formula_weight         468.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.3885(5)
_cell_length_b                   10.4150(5)
_cell_length_c                   14.9188(7)
_cell_angle_alpha                105.469(2)
_cell_angle_beta                 96.649(2)
_cell_angle_gamma                90.638(2)
_cell_volume                     1395.13(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      53.85

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_F_000             506
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50543
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.694
_diffrn_reflns_theta_max         52.999
_diffrn_reflns_theta_full        52.999
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             4747
_reflns_number_gt                3457
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0419P)²+2.2040P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0055(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4747
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.1639
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.2947(2) 0.27176(18) 0.69540(13) 0.0390(5) Uani 1 1 d . . . . .
O2 O 0.1894(2) 0.43188(19) 0.81421(14) 0.0419(5) Uani 1 1 d . . . . .
N1 N 0.3932(2) 0.4970(2) 0.75150(15) 0.0293(5) Uani 1 1 d . . . . .
C2 C 0.6087(3) 0.5619(2) 0.70048(17) 0.0286(6) Uani 1 1 d . . . . .
H2 H 0.687874 0.535718 0.666460 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6917(3) 0.9967(3) 0.89935(18) 0.0324(6) Uani 1 1 d . . . . .
C1 C 0.5104(3) 0.4670(3) 0.70222(18) 0.0289(6) Uani 1 1 d . . . . .
H1 H 0.522027 0.377206 0.668695 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5990(3) 0.6995(3) 0.74737(17) 0.0274(6) Uani 1 1 d . . . . .
C4 C 0.4760(3) 0.7263(3) 0.79616(18) 0.0312(6) Uani 1 1 d . . . . .
H4 H 0.460714 0.815866 0.828516 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6716(3) 1.0582(3) 0.75372(18) 0.0307(6) Uani 1 1 d . . . . .
C15 C 0.6921(3) 0.9574(3) 0.80091(18) 0.0281(6) Uani 1 1 d . . . . .
C5 C 0.3803(3) 0.6295(3) 0.79827(19) 0.0328(6) Uani 1 1 d . . . . .
H5 H 0.301520 0.653206 0.833071 0.039 Uiso 1 1 calc R U . . .
C6 C 0.8351(3) 0.7675(2) 0.68083(18) 0.0285(6) Uani 1 1 d . . . . .
C11 C 0.9793(3) 0.7858(3) 0.72280(19) 0.0319(6) Uani 1 1 d . . . . .
C7 C 0.8103(3) 0.7120(3) 0.58289(18) 0.0316(6) Uani 1 1 d . . . . .
C17 C 0.6480(3) 1.1880(3) 0.8028(2) 0.0356(7) Uani 1 1 d . . . . .
H17 H 0.632794 1.253352 0.769204 0.043 Uiso 1 1 calc R U . . .
C9 C 1.0660(3) 0.6995(3) 0.5716(2) 0.0398(7) Uani 1 1 d . . . . .
C19 C 0.6691(3) 1.1287(3) 0.9458(2) 0.0381(7) Uani 1 1 d . . . . .
H19 H 0.669808 1.152526 1.011880 0.046 Uiso 1 1 calc R U . . .
C12 C 0.6613(3) 0.6895(3) 0.52957(19) 0.0398(7) Uani 1 1 d . . . . .
H12A H 0.653710 0.739565 0.482245 0.060 Uiso 1 1 calc R U . . .
H12B H 0.590547 0.720211 0.573153 0.060 Uiso 1 1 calc R U . . .
H12C H 0.643057 0.594266 0.498714 0.060 Uiso 1 1 calc R U . . .
C23 C 0.7195(4) 0.9010(3) 0.9594(2) 0.0435(8) Uani 1 1 d . . . . .
H23A H 0.810098 0.927606 1.000521 0.065 Uiso 1 1 calc R U . . .
H23B H 0.725411 0.810543 0.919009 0.065 Uiso 1 1 calc R U . . .
H23C H 0.640846 0.903012 0.997543 0.065 Uiso 1 1 calc R U . . .
C10 C 1.0909(3) 0.7518(3) 0.6682(2) 0.0388(7) Uani 1 1 d . . . . .
H10 H 1.187057 0.764948 0.697884 0.047 Uiso 1 1 calc R U . . .
C8 C 0.9257(3) 0.6792(3) 0.5308(2) 0.0384(7) Uani 1 1 d . . . . .
H8 H 0.906493 0.641610 0.464991 0.046 Uiso 1 1 calc R U . . .
C18 C 0.6458(3) 1.2259(3) 0.8990(2) 0.0380(7) Uani 1 1 d . . . . .
C14 C 1.0155(3) 0.8388(3) 0.8276(2) 0.0419(7) Uani 1 1 d . . . . .
H14A H 1.119947 0.844571 0.843961 0.063 Uiso 1 1 calc R U . . .
H14B H 0.972651 0.778639 0.858639 0.063 Uiso 1 1 calc R U . . .
H14C H 0.977360 0.927660 0.848376 0.063 Uiso 1 1 calc R U . . .
C25 C 0.1967(3) 0.1655(3) 0.7027(2) 0.0402(7) Uani 1 1 d . . . . .
C21 C 0.6671(4) 1.0286(3) 0.6483(2) 0.0449(8) Uani 1 1 d . . . . .
H21A H 0.755707 0.986773 0.629165 0.067 Uiso 1 1 calc R U . . .
H21B H 0.658158 1.111978 0.629835 0.067 Uiso 1 1 calc R U . . .
H21C H 0.584554 0.968064 0.617807 0.067 Uiso 1 1 calc R U . . .
C27 C 0.0545(3) 0.2270(3) 0.7257(2) 0.0447(8) Uani 1 1 d . . . . .
H27A H 0.008224 0.250502 0.669413 0.054 Uiso 1 1 calc R U . . .
H27B H -0.008322 0.157717 0.737348 0.054 Uiso 1 1 calc R U . . .
C28 C 0.0593(3) 0.3508(3) 0.8091(2) 0.0428(8) Uani 1 1 d . . . . .
C26 C 0.2702(3) 0.1019(3) 0.7750(2) 0.0465(8) Uani 1 1 d . . . . .
H26A H 0.354986 0.056895 0.751559 0.070 Uiso 1 1 calc R U . . .
H26B H 0.203617 0.036805 0.786630 0.070 Uiso 1 1 calc R U . . .
H26C H 0.299722 0.171012 0.833476 0.070 Uiso 1 1 calc R U . . .
C22 C 0.6162(4) 1.3669(3) 0.9494(2) 0.0583(10) Uani 1 1 d . . . . .
H22A H 0.607861 1.421450 0.904832 0.087 Uiso 1 1 calc R U . . .
H22B H 0.695150 1.403507 0.999099 0.087 Uiso 1 1 calc R U . . .
H22C H 0.526319 1.367604 0.976946 0.087 Uiso 1 1 calc R U . . .
C13 C 1.1898(4) 0.6692(3) 0.5137(3) 0.0590(10) Uani 1 1 d . . . . .
H13A H 1.164042 0.590133 0.461018 0.088 Uiso 1 1 calc R U . . .
H13B H 1.274854 0.652246 0.552885 0.088 Uiso 1 1 calc R U . . .
H13C H 1.210498 0.745429 0.489807 0.088 Uiso 1 1 calc R U . . .
B1 B 0.7084(3) 0.8074(3) 0.7437(2) 0.0273(7) Uani 1 1 d . . . . .
C29 C 0.0600(4) 0.3198(4) 0.9030(2) 0.0575(10) Uani 1 1 d . . . . .
H29A H 0.142918 0.266920 0.913326 0.086 Uiso 1 1 calc R U . . .
H29B H -0.028538 0.269282 0.903112 0.086 Uiso 1 1 calc R U . . .
H29C H 0.066255 0.403374 0.953030 0.086 Uiso 1 1 calc R U . . .
B2 B 0.2866(3) 0.3940(3) 0.7537(2) 0.0316(7) Uani 1 1 d . . . . .
C24 C 0.1775(4) 0.0660(3) 0.6065(2) 0.0575(10) Uani 1 1 d . . . . .
H24A H 0.135907 0.109969 0.559760 0.086 Uiso 1 1 calc R U . . .
H24B H 0.113195 -0.008461 0.607154 0.086 Uiso 1 1 calc R U . . .
H24C H 0.270965 0.032289 0.590645 0.086 Uiso 1 1 calc R U . . .
C30 C -0.0629(4) 0.4395(4) 0.7948(3) 0.0668(11) Uani 1 1 d . . . . .
H30A H -0.057878 0.517925 0.848989 0.100 Uiso 1 1 calc R U . . .
H30B H -0.154596 0.389948 0.788203 0.100 Uiso 1 1 calc R U . . .
H30C H -0.055481 0.468221 0.738019 0.100 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 B2 1.345(4) . ?
O1 C25 1.466(3) . ?
O2 B2 1.347(4) . ?
O2 C28 1.460(3) . ?
N1 C5 1.384(3) . ?
N1 C1 1.386(3) . ?
N1 B2 1.468(4) . ?
C2 C1 1.352(3) . ?
C2 C3 1.427(4) . ?
C2 H2 0.9500 . ?
C20 C19 1.396(4) . ?
C20 C15 1.416(4) . ?
C20 C23 1.513(4) . ?
C1 H1 0.9500 . ?
C3 C4 1.426(4) . ?
C3 B1 1.529(4) . ?
C4 C5 1.352(4) . ?
C4 H4 0.9500 . ?
C16 C17 1.389(4) . ?
C16 C15 1.415(4) . ?
C16 C21 1.515(4) . ?
C15 B1 1.587(4) . ?
C5 H5 0.9500 . ?
C6 C11 1.412(4) . ?
C6 C7 1.411(4) . ?
C6 B1 1.591(4) . ?
C11 C10 1.393(4) . ?
C11 C14 1.510(4) . ?
C7 C8 1.399(4) . ?
C7 C12 1.509(4) . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C9 C8 1.375(4) . ?
C9 C10 1.388(4) . ?
C9 C13 1.514(4) . ?
C19 C18 1.380(4) . ?
C19 H19 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C10 H10 0.9500 . ?
C8 H8 0.9500 . ?
C18 C22 1.506(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C25 C26 1.515(4) . ?
C25 C24 1.520(4) . ?
C25 C27 1.522(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C27 C28 1.531(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.518(4) . ?
C28 C30 1.512(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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 C25 117.8(2) . . ?
B2 O2 C28 121.9(2) . . ?
C5 N1 C1 116.8(2) . . ?
C5 N1 B2 121.2(2) . . ?
C1 N1 B2 122.0(2) . . ?
C1 C2 C3 123.0(2) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C19 C20 C15 120.5(2) . . ?
C19 C20 C23 116.9(2) . . ?
C15 C20 C23 122.6(2) . . ?
C2 C1 N1 121.9(2) . . ?
C2 C1 H1 119.0 . . ?
N1 C1 H1 119.0 . . ?
C2 C3 C4 113.3(2) . . ?
C2 C3 B1 123.1(2) . . ?
C4 C3 B1 123.7(2) . . ?
C5 C4 C3 122.7(2) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 C21 117.4(2) . . ?
C15 C16 C21 122.0(2) . . ?
C20 C15 C16 116.9(2) . . ?
C20 C15 B1 122.7(2) . . ?
C16 C15 B1 120.4(2) . . ?
C4 C5 N1 122.3(2) . . ?
C4 C5 H5 118.9 . . ?
N1 C5 H5 118.9 . . ?
C11 C6 C7 117.3(2) . . ?
C11 C6 B1 120.0(2) . . ?
C7 C6 B1 122.6(2) . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 C14 118.7(3) . . ?
C6 C11 C14 120.9(2) . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 C12 117.3(2) . . ?
C6 C7 C12 122.4(2) . . ?
C16 C17 C18 122.5(3) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C8 C9 C10 117.7(3) . . ?
C8 C9 C13 121.6(3) . . ?
C10 C9 C13 120.7(3) . . ?
C20 C19 C18 122.4(3) . . ?
C20 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C17 C18 C19 117.2(3) . . ?
C17 C18 C22 120.9(3) . . ?
C19 C18 C22 121.9(3) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C25 C26 107.3(2) . . ?
O1 C25 C24 105.6(2) . . ?
C26 C25 C24 110.2(3) . . ?
O1 C25 C27 107.8(2) . . ?
C26 C25 C27 115.1(3) . . ?
C24 C25 C27 110.3(3) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C28 C27 C25 117.3(2) . . ?
C28 C27 H27A 108.0 . . ?
C25 C27 H27A 108.0 . . ?
C28 C27 H27B 108.0 . . ?
C25 C27 H27B 108.0 . . ?
H27A C27 H27B 107.2 . . ?
O2 C28 C29 107.3(3) . . ?
O2 C28 C30 105.0(2) . . ?
C29 C28 C30 110.0(3) . . ?
O2 C28 C27 109.3(2) . . ?
C29 C28 C27 114.0(3) . . ?
C30 C28 C27 110.9(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 B1 C15 119.6(2) . . ?
C3 B1 C6 119.3(2) . . ?
C15 B1 C6 121.1(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O1 B2 O2 126.3(2) . . ?
O1 B2 N1 117.4(2) . . ?
O2 B2 N1 116.3(2) . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1913375'
loop_
_audit_author_name
_audit_author_address
'Gengwen Tan'
;Nanjing University
China
;
_audit_update_record             
;
2019-05-01 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H44 B2 N O2'
_chemical_formula_weight         496.30

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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   7.3012(19)
_cell_length_b                   14.676(4)
_cell_length_c                   28.022(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3002.6(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4098
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      25.23

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_F_000             1076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19848
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.776
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_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             2658
_reflns_number_gt                1845
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'w=1/[σ²(Fo²)+(0.0799P)²+2.1626P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.003
_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
C16 C 0.7125(11) 0.5573(4) 0.2422(2) 0.082(2) Uani 0.6 1 d . . P A 1
H16A H 0.636745 0.527039 0.219053 0.123 Uiso 0.6 1 d R U P A 1
H16B H 0.838926 0.549739 0.233663 0.123 Uiso 0.6 1 d R U P A 1
H16C H 0.691285 0.531309 0.273123 0.123 Uiso 0.6 1 d R U P A 1
O1 O 0.6450(3) 0.68683(13) 0.19166(6) 0.0478(6) Uani 1 1 d . . . . .
N1 N 0.750000 0.750000 0.11752(9) 0.0311(7) Uani 1 2 d S T P . .
C1 C 0.6681(3) 0.68087(16) 0.09136(8) 0.0316(6) Uani 1 1 d . . . . .
H1 H 0.609075 0.634309 0.107814 0.038 Uiso 1 1 calc R U . . .
C2 C 0.6697(3) 0.67781(15) 0.04300(8) 0.0293(6) Uani 1 1 d . . . . .
C3 C 0.750000 0.750000 0.01485(11) 0.0276(7) Uani 1 2 d S T P . .
C4 C 0.5713(4) 0.59810(17) 0.02064(9) 0.0386(7) Uani 1 1 d . . . . .
H4A H 0.506228 0.565081 0.044869 0.058 Uiso 1 1 calc R U . . .
H4B H 0.658871 0.558549 0.005674 0.058 Uiso 1 1 calc R U . . .
H4C H 0.486268 0.619969 -0.002842 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7703(3) 0.65675(15) -0.06941(8) 0.0272(6) Uani 1 1 d . . . . .
C6 C 0.6389(3) 0.62657(16) -0.10289(8) 0.0279(6) Uani 1 1 d . . . . .
C7 C 0.6582(4) 0.54240(17) -0.12526(8) 0.0339(6) Uani 1 1 d . . . . .
H7 H 0.567321 0.522927 -0.146150 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8087(4) 0.48662(17) -0.11742(9) 0.0371(7) Uani 1 1 d . . . . .
C9 C 0.9416(4) 0.51796(17) -0.08602(9) 0.0373(7) Uani 1 1 d . . . . .
H9 H 1.046454 0.483102 -0.081331 0.045 Uiso 1 1 calc R U . . .
C10 C 0.9234(3) 0.59984(16) -0.06129(8) 0.0315(6) Uani 1 1 d . . . . .
C11 C 0.4695(4) 0.68154(18) -0.11361(9) 0.0363(6) Uani 1 1 d . . . . .
H11A H 0.399147 0.651371 -0.137860 0.055 Uiso 1 1 calc R U . . .
H11B H 0.504314 0.741006 -0.124626 0.055 Uiso 1 1 calc R U . . .
H11C H 0.397077 0.687259 -0.085170 0.055 Uiso 1 1 calc R U . . .
C12 C 0.8278(5) 0.39456(19) -0.14119(12) 0.0568(9) Uani 1 1 d . . . . .
H12A H 0.854032 0.349181 -0.117479 0.085 Uiso 1 1 calc R U . . .
H12B H 0.925923 0.396630 -0.163970 0.085 Uiso 1 1 calc R U . . .
H12C H 0.715603 0.379454 -0.157197 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0710(4) 0.62451(18) -0.02572(10) 0.0413(7) Uani 1 1 d . . . . .
H13A H 1.177762 0.588012 -0.031539 0.062 Uiso 1 1 calc R U . . .
H13B H 1.027147 0.613389 0.006053 0.062 Uiso 1 1 calc R U . . .
H13C H 1.101655 0.687786 -0.029086 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6625(6) 0.6723(3) 0.24257(11) 0.0738(12) Uani 1 1 d . . . . .
C14 C 0.4801(7) 0.6574(3) 0.26325(13) 0.0967(16) Uani 1 1 d . . . . .
H14A H 0.492361 0.640654 0.296207 0.145 Uiso 1 1 calc R U . . .
H14B H 0.419152 0.609444 0.246219 0.145 Uiso 1 1 calc R U . . .
H14C H 0.409580 0.712442 0.260838 0.145 Uiso 1 1 calc R U . . .
B1 B 0.750000 0.750000 -0.04041(14) 0.0283(8) Uani 1 2 d S T P . .
B2 B 0.750000 0.750000 0.16936(14) 0.0380(10) Uani 1 2 d S T P . .
C16' C 0.8365(16) 0.6272(6) 0.2539(3) 0.078(3) Uani 0.4 1 d . . P A 2
H16D H 0.834662 0.564952 0.243432 0.116 Uiso 0.4 1 d R U P A 2
H16E H 0.932892 0.659312 0.237772 0.116 Uiso 0.4 1 d R U P A 2
H16F H 0.857402 0.629232 0.287712 0.116 Uiso 0.4 1 d R U P A 2
C17 C 0.6935(10) 0.7862(4) 0.26411(19) 0.0499(15) Uani 0.5 1 d . . P A 2
H17A H 0.712229 0.784964 0.298022 0.060 Uiso 0.5 1 d R U P A 2
H17B H 0.584429 0.820634 0.257782 0.060 Uiso 0.5 1 d R U P A 2


_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
C16 C15 1.728(8) . ?
C16 H16A 0.9601 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9601 . ?
O1 B2 1.355(3) . ?
O1 C15 1.448(3) . ?
N1 C1 1.387(3) . ?
N1 C1 1.387(3) 2_665 ?
N1 B2 1.453(5) . ?
C1 C2 1.356(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.445(3) . ?
C2 C4 1.509(3) . ?
C3 B1 1.548(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.413(3) . ?
C5 C10 1.414(3) . ?
C5 B1 1.599(3) . ?
C6 C7 1.393(3) . ?
C6 C11 1.507(3) . ?
C7 C8 1.388(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.388(4) . ?
C8 C12 1.513(4) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9300 . ?
C10 C13 1.512(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C17 1.357(7) 2_665 ?
C15 C16' 1.468(10) . ?
C15 C14 1.469(5) . ?
C15 C17 1.791(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16' C17 1.321(10) 2_665 ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9598 . ?
C16' H17B 0.965(12) 2_665 ?
C17 C17 1.345(13) 2_665 ?
C17 H17A 0.9601 . ?
C17 H17B 0.9601 . ?

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
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 110.4 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
B2 O1 C15 120.3(3) . . ?
C1 N1 C1 116.2(3) . 2_665 ?
C1 N1 B2 121.90(13) . . ?
C1 N1 B2 121.90(13) 2_665 . ?
C2 C1 N1 123.3(2) . . ?
C2 C1 H1 118.4 . . ?
N1 C1 H1 118.4 . . ?
C1 C2 C3 121.7(2) . . ?
C1 C2 C4 115.9(2) . . ?
C3 C2 C4 122.3(2) . . ?
C2 C3 C2 113.8(3) 2_665 . ?
C2 C3 B1 123.08(14) 2_665 . ?
C2 C3 B1 123.08(14) . . ?
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 . . ?
C6 C5 C10 117.3(2) . . ?
C6 C5 B1 122.9(2) . . ?
C10 C5 B1 119.8(2) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 C11 117.9(2) . . ?
C5 C6 C11 121.5(2) . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 117.3(2) . . ?
C7 C8 C12 122.0(3) . . ?
C9 C8 C12 120.7(3) . . ?
C8 C9 C10 122.3(2) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C9 C10 C5 120.3(2) . . ?
C9 C10 C13 117.8(2) . . ?
C5 C10 C13 121.9(2) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C15 O1 116.1(4) 2_665 . ?
C17 C15 C16' 55.6(5) 2_665 . ?
O1 C15 C16' 110.8(4) . . ?
C17 C15 C14 126.4(4) 2_665 . ?
O1 C15 C14 109.3(3) . . ?
C16' C15 C14 129.2(5) . . ?
O1 C15 C16 99.0(3) . . ?
C14 C15 C16 92.8(4) . . ?
C17 C15 C17 48.2(5) 2_665 . ?
O1 C15 C17 101.9(3) . . ?
C16' C15 C17 103.8(5) . . ?
C14 C15 C17 96.9(4) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 B1 C5 120.56(14) . 2_665 ?
C3 B1 C5 120.56(14) . . ?
C5 B1 C5 118.9(3) 2_665 . ?
O1 B2 O1 125.1(3) 2_665 . ?
O1 B2 N1 117.45(17) 2_665 . ?
O1 B2 N1 117.46(17) . . ?
C17 C16' C15 57.9(5) 2_665 . ?
C17 C16' H16D 168.4 2_665 . ?
C15 C16' H16D 110.5 . . ?
C17 C16' H16E 75.6 2_665 . ?
C15 C16' H16E 108.1 . . ?
H16D C16' H16E 109.5 . . ?
C17 C16' H16F 77.5 2_665 . ?
C15 C16' H16F 109.7 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C17 C16' H17B 46.5(4) 2_665 2_665 ?
C15 C16' H17B 100.6(7) . 2_665 ?
H16D C16' H17B 142.9 . 2_665 ?
H16E C16' H17B 39.2 . 2_665 ?
H16F C16' H17B 76.7 . 2_665 ?
C16' C17 C15 143.5(6) 2_665 . ?
C17 C17 C15 48.8(4) 2_665 . ?
C15 C17 C15 111.5(4) 2_665 . ?
C16' C17 H17A 104.8 2_665 . ?
C17 C17 H17A 84.2 2_665 . ?
C15 C17 H17A 109.8 2_665 . ?
C15 C17 H17A 109.5 . . ?
C16' C17 H17B 46.8 2_665 . ?
C17 C17 H17B 157.6 2_665 . ?
C15 C17 H17B 108.9 2_665 . ?
C15 C17 H17B 108.9 . . ?
H17A C17 H17B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C1 C2 1.67(18) 2_665 . . . ?
B2 N1 C1 C2 -178.33(18) . . . . ?
N1 C1 C2 C3 -3.3(4) . . . . ?
N1 C1 C2 C4 -179.2(2) . . . . ?
C1 C2 C3 C2 1.59(17) . . . 2_665 ?
C4 C2 C3 C2 177.2(3) . . . 2_665 ?
C1 C2 C3 B1 -178.41(17) . . . . ?
C4 C2 C3 B1 -2.8(3) . . . . ?
C10 C5 C6 C7 2.4(3) . . . . ?
B1 C5 C6 C7 -176.5(2) . . . . ?
C10 C5 C6 C11 179.1(2) . . . . ?
B1 C5 C6 C11 0.3(3) . . . . ?
C5 C6 C7 C8 -2.7(4) . . . . ?
C11 C6 C7 C8 -179.6(2) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C6 C7 C8 C12 179.0(2) . . . . ?
C7 C8 C9 C10 3.0(4) . . . . ?
C12 C8 C9 C10 -176.1(2) . . . . ?
C8 C9 C10 C5 -3.3(4) . . . . ?
C8 C9 C10 C13 176.3(2) . . . . ?
C6 C5 C10 C9 0.5(3) . . . . ?
B1 C5 C10 C9 179.4(2) . . . . ?
C6 C5 C10 C13 -179.0(2) . . . . ?
B1 C5 C10 C13 -0.2(3) . . . . ?
B2 O1 C15 C17 -10.2(5) . . . 2_665 ?
B2 O1 C15 C16' -71.1(5) . . . . ?
B2 O1 C15 C14 140.6(3) . . . . ?
B2 O1 C15 C16 -123.2(3) . . . . ?
B2 O1 C15 C17 38.8(4) . . . . ?
C2 C3 B1 C5 -35.16(15) 2_665 . . 2_665 ?
C2 C3 B1 C5 144.84(15) . . . 2_665 ?
C2 C3 B1 C5 144.84(15) 2_665 . . . ?
C2 C3 B1 C5 -35.16(15) . . . . ?
C6 C5 B1 C3 122.43(18) . . . . ?
C10 C5 B1 C3 -56.4(2) . . . . ?
C6 C5 B1 C5 -57.57(18) . . . 2_665 ?
C10 C5 B1 C5 123.6(2) . . . 2_665 ?
C15 O1 B2 O1 -10.8(2) . . . 2_665 ?
C15 O1 B2 N1 169.2(2) . . . . ?
C1 N1 B2 O1 170.95(16) . . . 2_665 ?
C1 N1 B2 O1 -9.05(16) 2_665 . . 2_665 ?
C1 N1 B2 O1 -9.05(16) . . . . ?
C1 N1 B2 O1 170.95(16) 2_665 . . . ?
O1 C15 C16' C17 108.1(5) . . . 2_665 ?
C14 C15 C16' C17 -111.7(6) . . . 2_665 ?
C17 C15 C16' C17 -0.6(4) . . . 2_665 ?
C17 C15 C17 C16' 137.9(13) 2_665 . . 2_665 ?
O1 C15 C17 C16' 23.3(12) . . . 2_665 ?
C16' C15 C17 C16' 138.5(11) . . . 2_665 ?
C14 C15 C17 C16' -88.2(12) . . . 2_665 ?
O1 C15 C17 C17 -114.6(3) . . . 2_665 ?
C16' C15 C17 C17 0.6(5) . . . 2_665 ?
C14 C15 C17 C17 133.9(4) . . . 2_665 ?
C17 C15 C17 C15 58.8(6) 2_665 . . 2_665 ?
O1 C15 C17 C15 -55.8(4) . . . 2_665 ?
C16' C15 C17 C15 59.4(6) . . . 2_665 ?
C14 C15 C17 C15 -167.3(4) . . . 2_665 ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051

