# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 1576166'
_audit_update_record             
;
2017-09-23 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H27 B N2 O'
_chemical_formula_sum            'C39 H27 B N2 O'
_chemical_formula_weight         550.44

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   9.4745(19)
_cell_length_b                   16.609(3)
_cell_length_c                   18.798(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.49(3)
_cell_angle_gamma                90.00
_cell_volume                     2917.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13162
_cell_measurement_theta_min      3.085
_cell_measurement_theta_max      27.7

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9926
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19865
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4933
_reflns_number_gt                2659
_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)+(0.1171P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4933
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2146
_refine_ls_wR_factor_gt          0.1686
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
O O 1.0212(3) 0.19000(15) 0.12504(11) 0.0505(7) Uani 1 1 d . . .
N2 N 0.8460(3) 0.29385(16) 0.07676(13) 0.0395(7) Uani 1 1 d . . .
N1 N 0.8628(3) 0.35326(16) -0.02621(13) 0.0400(7) Uani 1 1 d . . .
C21 C 0.8961(4) 0.28568(19) 0.01437(17) 0.0393(8) Uani 1 1 d . . .
C14 C 0.7724(4) 0.36648(19) 0.07432(16) 0.0393(8) Uani 1 1 d . . .
C1 C 0.7880(4) 0.40555(19) 0.01225(16) 0.0396(8) Uani 1 1 d . . .
C2 C 0.7442(4) 0.4880(2) -0.00210(17) 0.0418(8) Uani 1 1 d . . .
C8 C 0.6284(4) 0.4765(2) 0.10829(17) 0.0436(9) Uani 1 1 d . . .
C13 C 0.6803(4) 0.3968(2) 0.12210(16) 0.0420(8) Uani 1 1 d . . .
C7 C 0.6651(4) 0.52318(19) 0.04869(18) 0.0418(8) Uani 1 1 d . . .
C15 C 0.8804(4) 0.36247(19) -0.10116(17) 0.0393(8) Uani 1 1 d . . .
C3 C 0.7825(4) 0.5357(2) -0.0576(2) 0.0538(10) Uani 1 1 d . . .
H3 H 0.8353 0.5132 -0.0902 0.065 Uiso 1 1 calc R . .
C12 C 0.6291(4) 0.3506(2) 0.17489(18) 0.0514(10) Uani 1 1 d . . .
H12 H 0.6590 0.2974 0.1818 0.062 Uiso 1 1 calc R . .
C34 C 0.9256(4) 0.2661(2) 0.21793(17) 0.0502(9) Uani 1 1 d . . .
C11 C 0.5366(4) 0.3815(3) 0.21651(19) 0.0575(11) Uani 1 1 d . . .
H11 H 0.5025 0.3492 0.2504 0.069 Uiso 1 1 calc R . .
C10 C 0.4939(4) 0.4612(3) 0.2080(2) 0.0605(11) Uani 1 1 d . . .
H10 H 0.4354 0.4834 0.2380 0.073 Uiso 1 1 calc R . .
C23 C 1.0348(4) 0.1679(2) 0.05822(18) 0.0448(9) Uani 1 1 d . . .
C28 C 0.7571(4) 0.1598(2) 0.12584(18) 0.0458(9) Uani 1 1 d . . .
C22 C 0.9740(4) 0.2148(2) -0.00168(17) 0.0421(8) Uani 1 1 d . . .
C20 C 0.7663(4) 0.3441(2) -0.15454(18) 0.0474(9) Uani 1 1 d . . .
H20 H 0.6801 0.3260 -0.1428 0.057 Uiso 1 1 calc R . .
C6 C 0.6238(4) 0.6038(2) 0.0375(2) 0.0540(10) Uani 1 1 d . . .
H6 H 0.5689 0.6274 0.0685 0.065 Uiso 1 1 calc R . .
C24 C 1.1152(4) 0.1001(2) 0.0487(2) 0.0575(10) Uani 1 1 d . . .
H24 H 1.1571 0.0703 0.0885 0.069 Uiso 1 1 calc R . .
C35 C 0.8691(5) 0.2433(2) 0.27830(19) 0.0655(12) Uani 1 1 d . . .
H35 H 0.7968 0.2049 0.2736 0.079 Uiso 1 1 calc R . .
C5 C 0.6609(5) 0.6486(2) -0.0168(2) 0.0643(12) Uani 1 1 d . . .
H5 H 0.6315 0.7019 -0.0222 0.077 Uiso 1 1 calc R . .
C16 C 1.0085(4) 0.3894(2) -0.1174(2) 0.0537(10) Uani 1 1 d . . .
H16 H 1.0843 0.4014 -0.0809 0.064 Uiso 1 1 calc R . .
C27 C 0.9932(5) 0.1885(2) -0.07056(19) 0.0587(11) Uani 1 1 d . . .
H27 H 0.9516 0.2172 -0.1111 0.070 Uiso 1 1 calc R . .
C26 C 1.0723(5) 0.1212(3) -0.0786(2) 0.0704(13) Uani 1 1 d . . .
H26 H 1.0849 0.1053 -0.1246 0.084 Uiso 1 1 calc R . .
C19 C 0.7833(5) 0.3532(3) -0.22616(19) 0.0659(12) Uani 1 1 d . . .
H19 H 0.7078 0.3413 -0.2629 0.079 Uiso 1 1 calc R . .
C9 C 0.5374(4) 0.5069(2) 0.15567(19) 0.0519(10) Uani 1 1 d . . .
H9 H 0.5068 0.5600 0.1505 0.062 Uiso 1 1 calc R . .
C32 C 0.6688(6) 0.0263(2) 0.1503(3) 0.0726(14) Uani 1 1 d . . .
H32 H 0.6811 -0.0215 0.1764 0.087 Uiso 1 1 calc R . .
C29 C 0.6321(4) 0.1688(2) 0.0755(2) 0.0579(10) Uani 1 1 d . . .
H29 H 0.6176 0.2169 0.0500 0.070 Uiso 1 1 calc R . .
C17 C 1.0227(5) 0.3983(3) -0.1886(2) 0.0712(13) Uani 1 1 d . . .
H17 H 1.1084 0.4172 -0.2003 0.085 Uiso 1 1 calc R . .
C25 C 1.1334(5) 0.0766(3) -0.0198(2) 0.0660(12) Uani 1 1 d . . .
H25 H 1.1866 0.0308 -0.0261 0.079 Uiso 1 1 calc R . .
C33 C 0.7715(5) 0.0862(2) 0.1626(2) 0.0600(11) Uani 1 1 d . . .
H33 H 0.8532 0.0772 0.1965 0.072 Uiso 1 1 calc R . .
C4 C 0.7424(5) 0.6155(2) -0.0643(2) 0.0606(11) Uani 1 1 d . . .
H4 H 0.7700 0.6470 -0.1005 0.073 Uiso 1 1 calc R . .
C36 C 0.9185(7) 0.2770(3) 0.3466(2) 0.0875(18) Uani 1 1 d . . .
H36 H 0.8778 0.2611 0.3862 0.105 Uiso 1 1 calc R . .
C31 C 0.5474(6) 0.0378(3) 0.0990(3) 0.0761(14) Uani 1 1 d . . .
H31 H 0.4792 -0.0027 0.0899 0.091 Uiso 1 1 calc R . .
C18 C 0.9111(6) 0.3795(3) -0.2427(2) 0.0764(14) Uani 1 1 d . . .
H18 H 0.9225 0.3847 -0.2907 0.092 Uiso 1 1 calc R . .
B B 0.8837(5) 0.2256(2) 0.1394(2) 0.0449(10) Uani 1 1 d . . .
C39 C 1.0326(5) 0.3238(3) 0.2291(2) 0.0719(13) Uani 1 1 d . . .
H39 H 1.0723 0.3415 0.1899 0.086 Uiso 1 1 calc R . .
C38 C 1.0832(6) 0.3566(3) 0.2971(3) 0.0942(17) Uani 1 1 d . . .
H38 H 1.1561 0.3947 0.3022 0.113 Uiso 1 1 calc R . .
C30 C 0.5281(5) 0.1089(3) 0.0618(2) 0.0681(12) Uani 1 1 d . . .
H30 H 0.4464 0.1171 0.0277 0.082 Uiso 1 1 calc R . .
C37 C 1.0268(8) 0.3333(3) 0.3551(3) 0.098(2) Uani 1 1 d . . .
H37 H 1.0606 0.3549 0.4004 0.118 Uiso 1 1 calc R . .


_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
O C23 1.335(4) . ?
O B 1.495(5) . ?
N2 C21 1.342(4) . ?
N2 C14 1.390(4) . ?
N2 B 1.632(4) . ?
N1 C21 1.365(4) . ?
N1 C1 1.396(4) . ?
N1 C15 1.454(4) . ?
C21 C22 1.448(5) . ?
C14 C1 1.364(4) . ?
C14 C13 1.443(4) . ?
C1 C2 1.443(5) . ?
C2 C3 1.404(5) . ?
C2 C7 1.432(5) . ?
C8 C13 1.422(5) . ?
C8 C9 1.429(5) . ?
C8 C7 1.451(5) . ?
C13 C12 1.403(5) . ?
C7 C6 1.401(5) . ?
C15 C16 1.374(5) . ?
C15 C20 1.383(5) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C12 C11 1.368(5) . ?
C12 H12 0.9300 . ?
C34 C35 1.385(5) . ?
C34 C39 1.386(6) . ?
C34 B 1.611(5) . ?
C11 C10 1.386(5) . ?
C11 H11 0.9300 . ?
C10 C9 1.359(5) . ?
C10 H10 0.9300 . ?
C23 C24 1.388(5) . ?
C23 C22 1.411(5) . ?
C28 C29 1.397(5) . ?
C28 C33 1.399(5) . ?
C28 B 1.611(6) . ?
C22 C27 1.406(5) . ?
C20 C19 1.390(5) . ?
C20 H20 0.9300 . ?
C6 C5 1.355(6) . ?
C6 H6 0.9300 . ?
C24 C25 1.382(5) . ?
C24 H24 0.9300 . ?
C35 C36 1.408(6) . ?
C35 H35 0.9300 . ?
C5 C4 1.386(6) . ?
C5 H5 0.9300 . ?
C16 C17 1.375(5) . ?
C16 H16 0.9300 . ?
C27 C26 1.368(5) . ?
C27 H27 0.9300 . ?
C26 C25 1.377(6) . ?
C26 H26 0.9300 . ?
C19 C18 1.370(6) . ?
C19 H19 0.9300 . ?
C9 H9 0.9300 . ?
C32 C33 1.384(6) . ?
C32 C31 1.387(7) . ?
C32 H32 0.9300 . ?
C29 C30 1.394(6) . ?
C29 H29 0.9300 . ?
C17 C18 1.377(6) . ?
C17 H17 0.9300 . ?
C25 H25 0.9300 . ?
C33 H33 0.9300 . ?
C4 H4 0.9300 . ?
C36 C37 1.378(8) . ?
C36 H36 0.9300 . ?
C31 C30 1.368(6) . ?
C31 H31 0.9300 . ?
C18 H18 0.9300 . ?
C39 C38 1.398(6) . ?
C39 H39 0.9300 . ?
C38 C37 1.349(7) . ?
C38 H38 0.9300 . ?
C30 H30 0.9300 . ?
C37 H37 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
C23 O B 120.1(3) . . ?
C21 N2 C14 107.8(3) . . ?
C21 N2 B 119.6(3) . . ?
C14 N2 B 132.5(3) . . ?
C21 N1 C1 108.2(3) . . ?
C21 N1 C15 125.1(3) . . ?
C1 N1 C15 125.8(3) . . ?
N2 C21 N1 108.8(3) . . ?
N2 C21 C22 122.0(3) . . ?
N1 C21 C22 129.1(3) . . ?
C1 C14 N2 108.4(3) . . ?
C1 C14 C13 121.9(3) . . ?
N2 C14 C13 129.3(3) . . ?
C14 C1 N1 106.4(3) . . ?
C14 C1 C2 122.9(3) . . ?
N1 C1 C2 130.4(3) . . ?
C3 C2 C7 119.5(3) . . ?
C3 C2 C1 124.9(3) . . ?
C7 C2 C1 115.4(3) . . ?
C13 C8 C9 116.1(3) . . ?
C13 C8 C7 121.3(3) . . ?
C9 C8 C7 122.6(3) . . ?
C12 C13 C8 119.3(3) . . ?
C12 C13 C14 124.4(3) . . ?
C8 C13 C14 116.0(3) . . ?
C6 C7 C2 117.0(3) . . ?
C6 C7 C8 122.0(3) . . ?
C2 C7 C8 121.0(3) . . ?
C16 C15 C20 121.6(3) . . ?
C16 C15 N1 119.8(3) . . ?
C20 C15 N1 118.6(3) . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C11 C12 C13 121.9(4) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C35 C34 C39 115.8(4) . . ?
C35 C34 B 124.5(4) . . ?
C39 C34 B 119.5(3) . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
O C23 C24 119.0(3) . . ?
O C23 C22 120.6(3) . . ?
C24 C23 C22 120.3(3) . . ?
C29 C28 C33 115.5(4) . . ?
C29 C28 B 124.1(3) . . ?
C33 C28 B 120.3(4) . . ?
C27 C22 C23 117.7(3) . . ?
C27 C22 C21 126.3(3) . . ?
C23 C22 C21 115.9(3) . . ?
C15 C20 C19 118.5(4) . . ?
C15 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C5 C6 C7 122.5(4) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C34 C35 C36 121.6(5) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C15 C16 C17 118.9(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C26 C27 C22 120.8(4) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C27 C26 C25 121.1(4) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C10 C9 C8 122.7(4) . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C33 C32 C31 119.7(4) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C30 C29 C28 122.9(4) . . ?
C30 C29 H29 118.5 . . ?
C28 C29 H29 118.5 . . ?
C16 C17 C18 120.5(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C32 C33 C28 122.5(4) . . ?
C32 C33 H33 118.8 . . ?
C28 C33 H33 118.8 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C37 C36 C35 120.3(5) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C30 C31 C32 120.0(5) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O B C34 103.9(3) . . ?
O B C28 110.6(3) . . ?
C34 B C28 119.5(3) . . ?
O B N2 103.7(3) . . ?
C34 B N2 111.3(3) . . ?
C28 B N2 106.8(3) . . ?
C34 C39 C38 122.7(5) . . ?
C34 C39 H39 118.6 . . ?
C38 C39 H39 118.6 . . ?
C37 C38 C39 120.3(6) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C31 C30 C29 119.3(5) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C38 C37 C36 119.2(5) . . ?
C38 C37 H37 120.4 . . ?
C36 C37 H37 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_z1
_database_code_depnum_ccdc_archive 'CCDC 1576167'
_audit_update_record             
;
2017-09-23 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H27 N O'
_chemical_formula_sum            'C39 H29 B N2 O'
_chemical_formula_weight         552.45

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.144(2)
_cell_length_b                   11.510(2)
_cell_length_c                   14.188(3)
_cell_angle_alpha                77.15(3)
_cell_angle_beta                 77.52(3)
_cell_angle_gamma                69.49(3)
_cell_volume                     1495.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11427
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14740
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6776
_reflns_number_gt                4569
_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)+(0.0601P)²+0.2734P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6776
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
O O 0.58764(12) 0.83326(10) 0.09218(8) 0.0370(3) Uani 1 1 d . . .
N2 N 0.66049(13) 0.64282(12) 0.21121(9) 0.0307(3) Uani 1 1 d . . .
N1 N 0.78779(13) 0.46001(12) 0.16751(10) 0.0335(3) Uani 1 1 d . . .
C21 C 0.69921(15) 0.57649(14) 0.13762(11) 0.0315(3) Uani 1 1 d . . .
C8 C 0.72470(15) 0.56681(14) 0.29001(11) 0.0318(3) Uani 1 1 d . . .
C22 C 0.65393(16) 0.63189(15) 0.04259(12) 0.0342(3) Uani 1 1 d . . .
C28 C 0.57746(15) 0.87355(14) 0.25835(11) 0.0320(3) Uani 1 1 d . . .
C1 C 0.80418(16) 0.45266(14) 0.26357(12) 0.0334(3) Uani 1 1 d . . .
C23 C 0.59951(16) 0.76394(15) 0.02431(12) 0.0344(4) Uani 1 1 d . . .
C33 C 0.47735(17) 0.92998(16) 0.33218(12) 0.0382(4) Uani 1 1 d . . .
H33 H 0.3923 0.9114 0.3504 0.046 Uiso 1 1 calc R . .
C9 C 0.71076(17) 0.60521(14) 0.38544(12) 0.0334(3) Uani 1 1 d . . .
C24 C 0.56388(18) 0.82593(17) -0.06722(13) 0.0420(4) Uani 1 1 d . . .
H24 H 0.5299 0.9133 -0.0795 0.050 Uiso 1 1 calc R . .
C27 C 0.66614(19) 0.56519(17) -0.03226(13) 0.0457(4) Uani 1 1 d . . .
H27 H 0.6999 0.4778 -0.0211 0.055 Uiso 1 1 calc R . .
C15 C 0.84857(16) 0.35785(14) 0.11117(12) 0.0324(3) Uani 1 1 d . . .
C34 C 0.39033(16) 0.77520(15) 0.21987(12) 0.0347(4) Uani 1 1 d . . .
C2 C 0.89098(17) 0.33991(15) 0.32135(13) 0.0367(4) Uani 1 1 d . . .
C35 C 0.27874(18) 0.88392(17) 0.19569(15) 0.0476(4) Uani 1 1 d . . .
H35 H 0.2996 0.9570 0.1647 0.057 Uiso 1 1 calc R . .
B B 0.55056(18) 0.78369(16) 0.19737(13) 0.0317(4) Uani 1 1 d . . .
C25 C 0.5789(2) 0.75803(19) -0.13942(14) 0.0506(5) Uani 1 1 d . . .
H25 H 0.5555 0.7998 -0.2006 0.061 Uiso 1 1 calc R . .
C32 C 0.4997(2) 1.01271(17) 0.37941(13) 0.0466(4) Uani 1 1 d . . .
H32 H 0.4296 1.0497 0.4278 0.056 Uiso 1 1 calc R . .
C29 C 0.70253(18) 0.90555(17) 0.23467(14) 0.0460(4) Uani 1 1 d . . .
H29 H 0.7717 0.8715 0.1847 0.055 Uiso 1 1 calc R . .
C16 C 0.97911(18) 0.34519(16) 0.05284(13) 0.0420(4) Uani 1 1 d . . .
H16 H 1.0296 0.3992 0.0517 0.050 Uiso 1 1 calc R . .
C7 C 0.8340(2) 0.29882(18) 0.41578(15) 0.0496(5) Uani 1 1 d . . .
H7 H 0.7405 0.3404 0.4406 0.060 Uiso 1 1 calc R . .
C14 C 0.58475(19) 0.62935(18) 0.44916(13) 0.0452(4) Uani 1 1 d . . .
H14 H 0.5031 0.6271 0.4308 0.054 Uiso 1 1 calc R . .
C3 C 1.03053(19) 0.27591(18) 0.28616(15) 0.0503(5) Uani 1 1 d . . .
H3 H 1.0708 0.3029 0.2234 0.060 Uiso 1 1 calc R . .
C31 C 0.6252(2) 1.04049(17) 0.35516(14) 0.0502(5) Uani 1 1 d . . .
H31 H 0.6410 1.0955 0.3873 0.060 Uiso 1 1 calc R . .
C26 C 0.6288(2) 0.6276(2) -0.12174(14) 0.0525(5) Uani 1 1 d . . .
H26 H 0.6369 0.5824 -0.1707 0.063 Uiso 1 1 calc R . .
C20 C 0.77418(19) 0.27806(17) 0.11514(15) 0.0471(4) Uani 1 1 d . . .
H20 H 0.6879 0.2859 0.1566 0.056 Uiso 1 1 calc R . .
C17 C 1.0334(2) 0.2508(2) -0.00390(16) 0.0578(5) Uani 1 1 d . . .
H17 H 1.1219 0.2399 -0.0428 0.069 Uiso 1 1 calc R . .
C36 C 0.13849(19) 0.8866(2) 0.21622(17) 0.0591(6) Uani 1 1 d . . .
H36 H 0.0667 0.9610 0.2000 0.071 Uiso 1 1 calc R . .
C18 C 0.9568(2) 0.17309(19) -0.00287(16) 0.0594(6) Uani 1 1 d . . .
H18 H 0.9922 0.1117 -0.0430 0.071 Uiso 1 1 calc R . .
C4 C 1.1103(2) 0.17276(19) 0.34302(19) 0.0620(6) Uani 1 1 d . . .
H4 H 1.2032 0.1297 0.3182 0.074 Uiso 1 1 calc R . .
C39 C 0.35278(19) 0.66907(17) 0.26338(14) 0.0468(4) Uani 1 1 d . . .
H39 H 0.4241 0.5943 0.2797 0.056 Uiso 1 1 calc R . .
C10 C 0.8312(2) 0.60879(19) 0.41430(15) 0.0502(5) Uani 1 1 d . . .
H10 H 0.9173 0.5924 0.3721 0.060 Uiso 1 1 calc R . .
C30 C 0.7271(2) 0.98594(19) 0.28283(16) 0.0526(5) Uani 1 1 d . . .
H30 H 0.8129 1.0033 0.2663 0.063 Uiso 1 1 calc R . .
C13 C 0.5787(2) 0.6569(2) 0.54024(15) 0.0563(5) Uani 1 1 d . . .
H13 H 0.4930 0.6732 0.5827 0.068 Uiso 1 1 calc R . .
C19 C 0.8289(2) 0.18506(19) 0.05652(17) 0.0593(6) Uani 1 1 d . . .
H19 H 0.7785 0.1309 0.0577 0.071 Uiso 1 1 calc R . .
C12 C 0.6972(3) 0.66038(19) 0.56836(15) 0.0583(5) Uani 1 1 d . . .
H12 H 0.6925 0.6788 0.6298 0.070 Uiso 1 1 calc R . .
C6 C 0.9152(3) 0.1966(2) 0.47307(17) 0.0654(6) Uani 1 1 d . . .
H6 H 0.8766 0.1703 0.5366 0.079 Uiso 1 1 calc R . .
C38 C 0.2114(2) 0.6703(2) 0.28372(18) 0.0634(6) Uani 1 1 d . . .
H38 H 0.1898 0.5971 0.3130 0.076 Uiso 1 1 calc R . .
C11 C 0.8238(3) 0.6366(2) 0.50541(17) 0.0630(6) Uani 1 1 d . . .
H11 H 0.9049 0.6394 0.5243 0.076 Uiso 1 1 calc R . .
C37 C 0.1046(2) 0.7795(2) 0.26055(18) 0.0641(6) Uani 1 1 d . . .
H37 H 0.0101 0.7811 0.2746 0.077 Uiso 1 1 calc R . .
C5 C 1.0525(3) 0.13361(19) 0.4365(2) 0.0700(7) Uani 1 1 d . . .
H5 H 1.1065 0.0643 0.4750 0.084 Uiso 1 1 calc R . .


_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
O C23 1.3425(19) . ?
O B 1.491(2) . ?
N2 C21 1.3396(19) . ?
N2 C8 1.385(2) . ?
N2 B 1.612(2) . ?
N1 C21 1.361(2) . ?
N1 C1 1.389(2) . ?
N1 C15 1.4486(19) . ?
C21 C22 1.454(2) . ?
C8 C1 1.365(2) . ?
C8 C9 1.479(2) . ?
C22 C27 1.404(2) . ?
C22 C23 1.407(2) . ?
C28 C33 1.390(2) . ?
C28 C29 1.395(2) . ?
C28 B 1.610(2) . ?
C1 C2 1.473(2) . ?
C23 C24 1.391(2) . ?
C33 C32 1.381(2) . ?
C33 H33 0.9300 . ?
C9 C14 1.375(2) . ?
C9 C10 1.386(2) . ?
C24 C25 1.374(3) . ?
C24 H24 0.9300 . ?
C27 C26 1.372(3) . ?
C27 H27 0.9300 . ?
C15 C20 1.364(2) . ?
C15 C16 1.380(2) . ?
C34 C39 1.381(2) . ?
C34 C35 1.396(2) . ?
C34 B 1.621(2) . ?
C2 C3 1.387(2) . ?
C2 C7 1.388(3) . ?
C35 C36 1.380(3) . ?
C35 H35 0.9300 . ?
C25 C26 1.388(3) . ?
C25 H25 0.9300 . ?
C32 C31 1.375(3) . ?
C32 H32 0.9300 . ?
C29 C30 1.379(3) . ?
C29 H29 0.9300 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9300 . ?
C7 C6 1.381(3) . ?
C7 H7 0.9300 . ?
C14 C13 1.381(3) . ?
C14 H14 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C31 C30 1.374(3) . ?
C31 H31 0.9300 . ?
C26 H26 0.9300 . ?
C20 C19 1.388(3) . ?
C20 H20 0.9300 . ?
C17 C18 1.371(3) . ?
C17 H17 0.9300 . ?
C36 C37 1.376(3) . ?
C36 H36 0.9300 . ?
C18 C19 1.366(3) . ?
C18 H18 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C39 C38 1.396(3) . ?
C39 H39 0.9300 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C30 H30 0.9300 . ?
C13 C12 1.362(3) . ?
C13 H13 0.9300 . ?
C19 H19 0.9300 . ?
C12 C11 1.374(3) . ?
C12 H12 0.9300 . ?
C6 C5 1.372(3) . ?
C6 H6 0.9300 . ?
C38 C37 1.370(3) . ?
C38 H38 0.9300 . ?
C11 H11 0.9300 . ?
C37 H37 0.9300 . ?
C5 H5 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
C23 O B 119.03(13) . . ?
C21 N2 C8 108.11(12) . . ?
C21 N2 B 119.33(13) . . ?
C8 N2 B 132.49(12) . . ?
C21 N1 C1 108.55(12) . . ?
C21 N1 C15 126.06(13) . . ?
C1 N1 C15 125.30(13) . . ?
N2 C21 N1 108.59(13) . . ?
N2 C21 C22 121.61(13) . . ?
N1 C21 C22 129.71(14) . . ?
C1 C8 N2 108.39(14) . . ?
C1 C8 C9 126.38(15) . . ?
N2 C8 C9 125.22(13) . . ?
C27 C22 C23 118.42(15) . . ?
C27 C22 C21 125.48(15) . . ?
C23 C22 C21 116.04(14) . . ?
C33 C28 C29 115.84(15) . . ?
C33 C28 B 123.45(14) . . ?
C29 C28 B 120.59(14) . . ?
C8 C1 N1 106.35(14) . . ?
C8 C1 C2 129.39(15) . . ?
N1 C1 C2 124.26(14) . . ?
O C23 C24 118.37(15) . . ?
O C23 C22 121.33(15) . . ?
C24 C23 C22 120.21(15) . . ?
C32 C33 C28 122.31(17) . . ?
C32 C33 H33 118.8 . . ?
C28 C33 H33 118.8 . . ?
C14 C9 C10 118.88(16) . . ?
C14 C9 C8 122.28(15) . . ?
C10 C9 C8 118.70(15) . . ?
C25 C24 C23 119.96(17) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C27 C22 120.67(17) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C20 C15 C16 121.42(15) . . ?
C20 C15 N1 119.35(14) . . ?
C16 C15 N1 119.21(14) . . ?
C39 C34 C35 116.14(16) . . ?
C39 C34 B 125.54(15) . . ?
C35 C34 B 118.31(15) . . ?
C3 C2 C7 118.51(17) . . ?
C3 C2 C1 122.18(16) . . ?
C7 C2 C1 119.26(15) . . ?
C36 C35 C34 122.17(18) . . ?
C36 C35 H35 118.9 . . ?
C34 C35 H35 118.9 . . ?
O B C28 105.94(13) . . ?
O B N2 103.73(12) . . ?
C28 B N2 112.68(13) . . ?
O B C34 110.80(14) . . ?
C28 B C34 114.87(13) . . ?
N2 B C34 108.24(13) . . ?
C24 C25 C26 120.53(18) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C31 C32 C33 120.20(17) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C30 C29 C28 122.28(17) . . ?
C30 C29 H29 118.9 . . ?
C28 C29 H29 118.9 . . ?
C15 C16 C17 118.79(17) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C6 C7 C2 120.46(19) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C9 C14 C13 120.39(18) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C30 C31 C32 119.14(17) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 H31 120.4 . . ?
C27 C26 C25 120.18(17) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C15 C20 C19 119.11(17) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C18 C17 C16 120.06(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C37 C36 C35 120.20(19) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C19 C18 C17 120.61(17) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C34 C39 C38 122.22(17) . . ?
C34 C39 H39 118.9 . . ?
C38 C39 H39 118.9 . . ?
C11 C10 C9 120.21(18) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C31 C30 C29 120.20(18) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C12 C13 C14 120.60(19) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C18 C19 C20 119.96(18) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C13 C12 C11 119.65(19) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C37 C38 C39 119.9(2) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C38 C37 C36 119.34(18) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052
