# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_170901
_database_code_depnum_ccdc_archive 'CCDC 1587223'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C108 H80 B4 N4 O20'
_chemical_formula_weight         1797.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   25.1180(18)
_cell_length_b                   5.8625(4)
_cell_length_c                   15.0463(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2215.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    11707
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      66.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8517
_exptl_absorpt_correction_T_max  0.8953
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11707
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         66.53
_reflns_number_total             3733
_reflns_number_gt                2720
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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     
'calc w=1/[σ²(Fo²)+(0.0303P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00159(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_number_reflns         3733
_refine_ls_number_parameters     309
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_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
O1 O 0.51568(8) 0.7688(4) 0.16108(19) 0.0568(7) Uani 1 1 d . . .
O2 O 0.58048(9) 0.4767(4) 0.14758(17) 0.0540(7) Uani 1 1 d . . .
N1 N 0.51914(9) 0.4619(4) 0.2721(2) 0.0452(7) Uani 1 1 d . . .
O3 O 0.58676(8) 0.7603(4) 0.26443(18) 0.0525(6) Uani 1 1 d . . .
O4 O 0.65468(10) 0.9990(4) 0.2715(2) 0.0756(9) Uani 1 1 d . . .
C14 C 0.43967(12) 0.9622(5) 0.1136(2) 0.0434(8) Uani 1 1 d . . .
O5 O 0.38383(10) 1.4909(4) -0.04550(19) 0.0621(7) Uani 1 1 d . . .
C18 C 0.45162(13) 1.3210(5) 0.0365(3) 0.0493(9) Uani 1 1 d . . .
H18 H 0.4730 1.4450 0.0220 0.059 Uiso 1 1 calc R . .
C6 C 0.43712(12) 0.6577(5) 0.2345(2) 0.0430(8) Uani 1 1 d . . .
C21 C 0.63024(13) 0.8569(6) 0.2296(3) 0.0549(10) Uani 1 1 d . . .
C2 C 0.52238(14) 0.1571(6) 0.3771(3) 0.0569(10) Uani 1 1 d . . .
H2 H 0.5414 0.0411 0.4049 0.068 Uiso 1 1 calc R . .
C13 C 0.46302(12) 0.7883(5) 0.1733(3) 0.0442(8) Uani 1 1 d . . .
C3 C 0.47035(15) 0.1931(6) 0.3966(3) 0.0590(10) Uani 1 1 d . . .
H3 H 0.4539 0.1074 0.4407 0.071 Uiso 1 1 calc R . .
C22 C 0.64618(12) 0.7697(6) 0.1424(3) 0.0515(9) Uani 1 1 d . . .
C15 C 0.38907(13) 0.9507(6) 0.0780(3) 0.0479(9) Uani 1 1 d . . .
H15 H 0.3678 0.8253 0.0913 0.057 Uiso 1 1 calc R . .
C19 C 0.47113(13) 1.1500(6) 0.0899(3) 0.0484(9) Uani 1 1 d . . .
H19 H 0.5059 1.1592 0.1107 0.058 Uiso 1 1 calc R . .
C7 C 0.37802(12) 0.6687(5) 0.2463(2) 0.0434(8) Uani 1 1 d . . .
C27 C 0.62255(13) 0.5762(6) 0.1070(3) 0.0509(9) Uani 1 1 d . . .
C8 C 0.34705(14) 0.4901(6) 0.2153(3) 0.0534(9) Uani 1 1 d . . .
H8 H 0.3635 0.3613 0.1918 0.064 Uiso 1 1 calc R . .
C5 C 0.46602(12) 0.4918(5) 0.2868(3) 0.0432(8) Uani 1 1 d . . .
B1 B 0.55127(16) 0.6198(7) 0.2087(3) 0.0482(10) Uani 1 1 d . . .
C1 C 0.54626(13) 0.2946(6) 0.3158(3) 0.0515(9) Uani 1 1 d . . .
H1 H 0.5822 0.2735 0.3034 0.062 Uiso 1 1 calc R . .
C17 C 0.39994(14) 1.3081(6) 0.0042(3) 0.0500(9) Uani 1 1 d . . .
C16 C 0.36881(14) 1.1200(5) 0.0230(3) 0.0505(9) Uani 1 1 d . . .
H16 H 0.3348 1.1068 -0.0009 0.061 Uiso 1 1 calc R . .
C24 C 0.70527(16) 0.7857(9) 0.0162(3) 0.0795(13) Uani 1 1 d . . .
H24 H 0.7319 0.8584 -0.0161 0.095 Uiso 1 1 calc R . .
C4 C 0.44190(14) 0.3556(6) 0.3514(2) 0.0529(10) Uani 1 1 d . . .
H4 H 0.4059 0.3753 0.3640 0.063 Uiso 1 1 calc R . .
C12 C 0.35261(14) 0.8556(6) 0.2832(3) 0.0581(10) Uani 1 1 d . . .
H12 H 0.3727 0.9751 0.3063 0.070 Uiso 1 1 calc R . .
C26 C 0.64187(15) 0.4791(7) 0.0286(3) 0.0672(11) Uani 1 1 d . . .
H26 H 0.6274 0.3446 0.0066 0.081 Uiso 1 1 calc R . .
C23 C 0.68793(15) 0.8754(8) 0.0952(3) 0.0670(12) Uani 1 1 d . . .
H23 H 0.7038 1.0065 0.1178 0.080 Uiso 1 1 calc R . .
C9 C 0.29185(15) 0.5006(7) 0.2188(3) 0.0663(12) Uani 1 1 d . . .
H9 H 0.2714 0.3797 0.1978 0.080 Uiso 1 1 calc R . .
C25 C 0.68278(17) 0.5865(9) -0.0151(3) 0.0809(14) Uani 1 1 d . . .
H25 H 0.6957 0.5230 -0.0675 0.097 Uiso 1 1 calc R . .
C10 C 0.26768(14) 0.6906(8) 0.2534(3) 0.0715(13) Uani 1 1 d . . .
H10 H 0.2307 0.6999 0.2546 0.086 Uiso 1 1 calc R . .
C20 C 0.32984(16) 1.4998(7) -0.0736(3) 0.0772(14) Uani 1 1 d . . .
H20A H 0.3228 1.3756 -0.1136 0.116 Uiso 1 1 calc R . .
H20B H 0.3233 1.6418 -0.1035 0.116 Uiso 1 1 calc R . .
H20C H 0.3069 1.4879 -0.0228 0.116 Uiso 1 1 calc R . .
C11 C 0.29757(15) 0.8659(7) 0.2860(3) 0.0687(12) Uani 1 1 d . . .
H11 H 0.2809 0.9930 0.3102 0.082 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
O1 C13 1.340(3) . ?
O1 B1 1.440(5) . ?
O2 C27 1.352(4) . ?
O2 B1 1.445(5) . ?
N1 C1 1.364(4) . ?
N1 C5 1.364(4) . ?
N1 B1 1.555(5) . ?
O3 C21 1.337(4) . ?
O3 B1 1.475(5) . ?
O4 C21 1.211(4) . ?
C14 C15 1.381(4) . ?
C14 C19 1.401(4) . ?
C14 C13 1.480(5) . ?
O5 C17 1.368(4) . ?
O5 C20 1.421(4) . ?
C18 C19 1.376(5) . ?
C18 C17 1.388(5) . ?
C18 H18 0.9300 . ?
C6 C13 1.363(5) . ?
C6 C5 1.447(4) . ?
C6 C7 1.497(4) . ?
C21 C22 1.465(5) . ?
C2 C3 1.356(5) . ?
C2 C1 1.364(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C22 C27 1.387(5) . ?
C22 C23 1.410(5) . ?
C15 C16 1.389(5) . ?
C15 H15 0.9300 . ?
C19 H19 0.9300 . ?
C7 C12 1.384(4) . ?
C7 C8 1.385(5) . ?
C27 C26 1.397(5) . ?
C8 C9 1.389(5) . ?
C8 H8 0.9300 . ?
C5 C4 1.396(4) . ?
C1 H1 0.9300 . ?
C17 C16 1.381(4) . ?
C16 H16 0.9300 . ?
C24 C23 1.371(6) . ?
C24 C25 1.380(6) . ?
C24 H24 0.9300 . ?
C4 H4 0.9300 . ?
C12 C11 1.385(5) . ?
C12 H12 0.9300 . ?
C26 C25 1.373(5) . ?
C26 H26 0.9300 . ?
C23 H23 0.9300 . ?
C9 C10 1.371(5) . ?
C9 H9 0.9300 . ?
C25 H25 0.9300 . ?
C10 C11 1.364(5) . ?
C10 H10 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C11 H11 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
C13 O1 B1 126.6(3) . . ?
C27 O2 B1 115.7(3) . . ?
C1 N1 C5 120.2(3) . . ?
C1 N1 B1 117.7(3) . . ?
C5 N1 B1 122.1(3) . . ?
C21 O3 B1 120.5(3) . . ?
C15 C14 C19 117.3(3) . . ?
C15 C14 C13 124.5(3) . . ?
C19 C14 C13 118.2(3) . . ?
C17 O5 C20 118.3(3) . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C13 C6 C5 120.4(3) . . ?
C13 C6 C7 122.0(3) . . ?
C5 C6 C7 117.5(3) . . ?
O4 C21 O3 120.1(4) . . ?
O4 C21 C22 124.6(3) . . ?
O3 C21 C22 115.2(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
O1 C13 C6 121.1(3) . . ?
O1 C13 C14 111.5(3) . . ?
C6 C13 C14 127.4(3) . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C27 C22 C23 119.0(4) . . ?
C27 C22 C21 120.8(3) . . ?
C23 C22 C21 120.1(4) . . ?
C14 C15 C16 122.2(3) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C18 C19 C14 121.4(3) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C12 C7 C8 118.3(3) . . ?
C12 C7 C6 122.6(3) . . ?
C8 C7 C6 119.0(3) . . ?
O2 C27 C22 121.0(3) . . ?
O2 C27 C26 118.5(4) . . ?
C22 C27 C26 120.6(4) . . ?
C7 C8 C9 120.9(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
N1 C5 C4 117.6(3) . . ?
N1 C5 C6 119.3(3) . . ?
C4 C5 C6 123.1(3) . . ?
O1 B1 O2 110.5(3) . . ?
O1 B1 O3 108.6(3) . . ?
O2 B1 O3 112.3(3) . . ?
O1 B1 N1 110.1(3) . . ?
O2 B1 N1 108.0(3) . . ?
O3 B1 N1 107.3(3) . . ?
C2 C1 N1 122.1(3) . . ?
C2 C1 H1 118.9 . . ?
N1 C1 H1 118.9 . . ?
O5 C17 C16 124.7(3) . . ?
O5 C17 C18 115.2(3) . . ?
C16 C17 C18 120.1(3) . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C23 C24 C25 119.4(4) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C7 C12 C11 120.4(4) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C25 C26 C27 118.6(4) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
C24 C23 C22 120.3(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C26 C25 C24 122.1(4) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.53
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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 1814822'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C1.72 H1.24 B0.07 N0.07 O0.21'
_chemical_formula_weight         26.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.8468(4)
_cell_length_b                   10.1242(4)
_cell_length_c                   10.1222(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.228(2)
_cell_angle_gamma                90.00
_cell_volume                     982.32(6)
_cell_formula_units_Z            29
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2418
_cell_measurement_theta_min      4.61
_cell_measurement_theta_max      66.02

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7994
_exptl_absorpt_correction_T_max  0.8465
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3197
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.61
_diffrn_reflns_theta_max         66.02
_reflns_number_total             2418
_reflns_number_gt                2322
_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)+(0.0518P)²+0.0724P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_number_reflns         2418
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
O1 O 0.27746(14) 0.74094(16) 0.24115(14) 0.0445(4) Uani 1 1 d . . .
O2 O 0.38524(14) 0.95371(16) 0.23549(15) 0.0438(3) Uani 1 1 d . . .
O3 O 0.52542(15) 0.76425(16) 0.27449(15) 0.0440(4) Uani 1 1 d . . .
N1 N 0.40776(16) 0.83941(19) 0.45640(17) 0.0398(4) Uani 1 1 d . . .
C8 C 0.19740(19) 0.7116(2) 0.44274(19) 0.0346(4) Uani 1 1 d . . .
C15 C 0.3103(2) 0.7915(2) 0.5198(2) 0.0368(4) Uani 1 1 d . . .
C1 C 0.08220(19) 0.6038(2) 0.22136(19) 0.0350(4) Uani 1 1 d . . .
C14 C 0.1101(2) 0.5800(2) 0.6191(2) 0.0416(5) Uani 1 1 d . . .
H14 H 0.2001 0.5492 0.6538 0.050 Uiso 1 1 calc R . .
C7 C 0.18887(18) 0.6888(2) 0.30908(19) 0.0341(4) Uani 1 1 d . . .
C13 C 0.0030(2) 0.5404(3) 0.6778(2) 0.0497(6) Uani 1 1 d . . .
H13 H 0.0219 0.4849 0.7530 0.060 Uiso 1 1 calc R . .
C2 C 0.0600(2) 0.4758(2) 0.2585(2) 0.0448(5) Uani 1 1 d . . .
H2 H 0.1115 0.4422 0.3402 0.054 Uiso 1 1 calc R . .
C21 C 0.6854(2) 0.8332(3) 0.1323(2) 0.0518(6) Uani 1 1 d . . .
H21 H 0.7399 0.7573 0.1467 0.062 Uiso 1 1 calc R . .
C10 C -0.0515(2) 0.7084(2) 0.4584(2) 0.0426(5) Uani 1 1 d . . .
H10 H -0.0705 0.7664 0.3852 0.051 Uiso 1 1 calc R . .
C6 C 0.0051(2) 0.6516(3) 0.0984(2) 0.0438(5) Uani 1 1 d . . .
H6 H 0.0219 0.7364 0.0706 0.053 Uiso 1 1 calc R . .
C9 C 0.08435(19) 0.6654(2) 0.50883(18) 0.0347(4) Uani 1 1 d . . .
C16 C 0.3232(2) 0.8243(3) 0.6567(2) 0.0534(6) Uani 1 1 d . . .
H16 H 0.2564 0.7947 0.7015 0.064 Uiso 1 1 calc R . .
C5 C -0.0957(2) 0.5750(3) 0.0173(2) 0.0543(6) Uani 1 1 d . . .
H5 H -0.1484 0.6090 -0.0637 0.065 Uiso 1 1 calc R . .
C19 C 0.5152(2) 0.9126(3) 0.5257(2) 0.0526(6) Uani 1 1 d . . .
H19 H 0.5813 0.9431 0.4805 0.063 Uiso 1 1 calc R . .
C17 C 0.4321(3) 0.8987(3) 0.7254(3) 0.0626(7) Uani 1 1 d . . .
H17 H 0.4398 0.9189 0.8165 0.075 Uiso 1 1 calc R . .
C24 C 0.5197(2) 1.0643(3) 0.0894(2) 0.0520(6) Uani 1 1 d . . .
H24 H 0.4653 1.1403 0.0751 0.062 Uiso 1 1 calc R . .
C4 C -0.1191(2) 0.4473(3) 0.0558(3) 0.0572(6) Uani 1 1 d . . .
H4 H -0.1884 0.3959 0.0019 0.069 Uiso 1 1 calc R . .
C20 C 0.57271(19) 0.8494(2) 0.19100(19) 0.0385(5) Uani 1 1 d . . .
C25 C 0.4917(2) 0.9627(2) 0.16871(19) 0.0392(5) Uani 1 1 d . . .
C12 C -0.1316(2) 0.5830(3) 0.6255(2) 0.0538(6) Uani 1 1 d . . .
H12 H -0.2036 0.5555 0.6645 0.065 Uiso 1 1 calc R . .
C3 C -0.0386(3) 0.3972(3) 0.1749(3) 0.0543(6) Uani 1 1 d . . .
H3 H -0.0507 0.3101 0.1991 0.065 Uiso 1 1 calc R . .
C11 C -0.1589(2) 0.6664(3) 0.5154(2) 0.0516(6) Uani 1 1 d . . .
H11 H -0.2497 0.6946 0.4792 0.062 Uiso 1 1 calc R . .
C23 C 0.6348(3) 1.0476(3) 0.0310(2) 0.0653(8) Uani 1 1 d . . .
H23 H 0.6580 1.1148 -0.0226 0.078 Uiso 1 1 calc R . .
C18 C 0.5307(3) 0.9437(3) 0.6590(3) 0.0629(7) Uani 1 1 d . . .
H18 H 0.6060 0.9941 0.7043 0.075 Uiso 1 1 calc R . .
C22 C 0.7135(3) 0.9354(4) 0.0507(2) 0.0647(8) Uani 1 1 d . . .
H22 H 0.7877 0.9271 0.0086 0.078 Uiso 1 1 calc R . .
B1 B 0.3975(2) 0.8231(3) 0.2986(2) 0.0384(5) 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
O1 C7 1.337(2) . ?
O1 B1 1.454(3) . ?
O2 C25 1.374(2) . ?
O2 B1 1.462(3) . ?
O3 C20 1.362(3) . ?
O3 B1 1.463(3) . ?
N1 C19 1.350(3) . ?
N1 C15 1.360(2) . ?
N1 B1 1.586(3) . ?
C8 C7 1.356(3) . ?
C8 C15 1.450(3) . ?
C8 C9 1.499(3) . ?
C15 C16 1.402(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.388(3) . ?
C1 C7 1.485(3) . ?
C14 C13 1.382(3) . ?
C14 C9 1.389(3) . ?
C14 H14 0.9300 . ?
C13 C12 1.380(4) . ?
C13 H13 0.9300 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C21 C20 1.383(3) . ?
C21 C22 1.391(4) . ?
C21 H21 0.9300 . ?
C10 C11 1.383(3) . ?
C10 C9 1.388(3) . ?
C10 H10 0.9300 . ?
C6 C5 1.374(3) . ?
C6 H6 0.9300 . ?
C16 C17 1.364(3) . ?
C16 H16 0.9300 . ?
C5 C4 1.384(4) . ?
C5 H5 0.9300 . ?
C19 C18 1.360(3) . ?
C19 H19 0.9300 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C24 C25 1.372(3) . ?
C24 C23 1.403(4) . ?
C24 H24 0.9300 . ?
C4 C3 1.379(4) . ?
C4 H4 0.9300 . ?
C20 C25 1.386(3) . ?
C12 C11 1.375(4) . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C23 C22 1.364(5) . ?
C23 H23 0.9300 . ?
C18 H18 0.9300 . ?
C22 H22 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
C7 O1 B1 125.93(15) . . ?
C25 O2 B1 106.17(17) . . ?
C20 O3 B1 105.99(16) . . ?
C19 N1 C15 120.31(18) . . ?
C19 N1 B1 116.25(17) . . ?
C15 N1 B1 123.29(16) . . ?
C7 C8 C15 119.77(17) . . ?
C7 C8 C9 120.64(17) . . ?
C15 C8 C9 119.36(16) . . ?
N1 C15 C16 117.86(18) . . ?
N1 C15 C8 118.83(17) . . ?
C16 C15 C8 123.30(18) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 C7 121.03(18) . . ?
C6 C1 C7 120.07(19) . . ?
C13 C14 C9 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O1 C7 C8 123.20(17) . . ?
O1 C7 C1 112.13(15) . . ?
C8 C7 C1 124.68(17) . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C20 C21 C22 117.1(3) . . ?
C20 C21 H21 121.5 . . ?
C22 C21 H21 121.5 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C10 C9 C14 118.30(18) . . ?
C10 C9 C8 119.31(18) . . ?
C14 C9 C8 122.38(17) . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N1 C19 C18 122.6(2) . . ?
N1 C19 H19 118.7 . . ?
C18 C19 H19 118.7 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C25 C24 C23 116.5(3) . . ?
C25 C24 H24 121.7 . . ?
C23 C24 H24 121.7 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O3 C20 C21 127.8(2) . . ?
O3 C20 C25 111.04(16) . . ?
C21 C20 C25 121.1(2) . . ?
C24 C25 O2 128.0(2) . . ?
C24 C25 C20 122.06(19) . . ?
O2 C25 C20 109.93(18) . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C22 C23 C24 121.7(2) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C19 C18 C17 118.4(2) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C23 C22 C21 121.6(2) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
O1 B1 O2 111.36(17) . . ?
O1 B1 O3 110.66(19) . . ?
O2 B1 O3 106.49(16) . . ?
O1 B1 N1 108.72(15) . . ?
O2 B1 N1 109.00(19) . . ?
O3 B1 N1 110.60(17) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        66.02
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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 1814823'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 B N O4'
_chemical_formula_weight         421.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   pn21a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.1106(9)
_cell_length_b                   9.7939(6)
_cell_length_c                   15.4646(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2137.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3599
_cell_measurement_theta_min      4.24
_cell_measurement_theta_max      65.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8429
_exptl_absorpt_correction_T_max  0.8832
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12385
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.24
_diffrn_reflns_theta_max         65.98
_reflns_number_total             3599
_reflns_number_gt                2624
_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)+(0.0469P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         3599
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_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
O2 O 0.62706(17) 0.4409(2) 0.36610(12) 0.0642(6) Uani 1 1 d . . .
O1 O 0.49892(14) 0.4549(2) 0.26243(11) 0.0567(5) Uani 1 1 d . . .
N1 N 0.64810(18) 0.3400(2) 0.22056(15) 0.0524(6) Uani 1 1 d . . .
O3 O 0.53904(15) 0.2442(2) 0.33303(14) 0.0644(6) Uani 1 1 d . . .
O4 O 0.20353(16) 0.9077(2) 0.16976(16) 0.0783(7) Uani 1 1 d . . .
C5 C 0.6474(2) 0.4108(3) 0.14492(18) 0.0496(7) Uani 1 1 d . . .
C13 C 0.5041(2) 0.5300(3) 0.19014(17) 0.0460(7) Uani 1 1 d . . .
C14 C 0.4249(2) 0.6274(3) 0.18327(16) 0.0453(7) Uani 1 1 d . . .
C17 C 0.2726(2) 0.8097(3) 0.1761(2) 0.0558(8) Uani 1 1 d . . .
C6 C 0.5742(2) 0.5113(3) 0.13078(17) 0.0465(7) Uani 1 1 d . . .
C7 C 0.5706(2) 0.5817(3) 0.04475(17) 0.0477(7) Uani 1 1 d . . .
C12 C 0.4940(2) 0.5571(3) -0.01039(19) 0.0529(8) Uani 1 1 d . . .
H12 H 0.4450 0.4966 0.0071 0.064 Uiso 1 1 calc R . .
C26 C 0.6132(2) 0.3616(4) 0.43845(18) 0.0607(8) Uani 1 1 d . . .
C11 C 0.4891(2) 0.6202(3) -0.08997(19) 0.0607(8) Uani 1 1 d . . .
H11 H 0.4368 0.6036 -0.1272 0.073 Uiso 1 1 calc R . .
C20 C 0.3355(2) 0.5911(3) 0.2126(2) 0.0570(8) Uani 1 1 d . . .
H20 H 0.3263 0.5027 0.2365 0.068 Uiso 1 1 calc R . .
C21 C 0.5625(2) 0.2465(4) 0.4191(2) 0.0612(8) Uani 1 1 d . . .
C16 C 0.3614(2) 0.8489(3) 0.14827(19) 0.0555(7) Uani 1 1 d . . .
H16 H 0.3710 0.9389 0.1272 0.067 Uiso 1 1 calc R . .
C15 C 0.4355(2) 0.7593(3) 0.15076(19) 0.0536(8) Uani 1 1 d . . .
H15 H 0.4958 0.7875 0.1299 0.064 Uiso 1 1 calc R . .
C8 C 0.6411(2) 0.6706(3) 0.0180(2) 0.0576(8) Uani 1 1 d . . .
H8 H 0.6934 0.6887 0.0549 0.069 Uiso 1 1 calc R . .
C4 C 0.7184(2) 0.3798(4) 0.0843(2) 0.0638(8) Uani 1 1 d . . .
H4 H 0.7196 0.4274 0.0308 0.077 Uiso 1 1 calc R . .
C9 C 0.6359(2) 0.7328(4) -0.0620(2) 0.0639(9) Uani 1 1 d . . .
H9 H 0.6848 0.7933 -0.0797 0.077 Uiso 1 1 calc R . .
C1 C 0.7147(2) 0.2416(3) 0.2355(2) 0.0626(8) Uani 1 1 d . . .
H1 H 0.7124 0.1923 0.2884 0.075 Uiso 1 1 calc R . .
C19 C 0.2594(2) 0.6797(3) 0.2081(2) 0.0599(8) Uani 1 1 d . . .
H19 H 0.1985 0.6512 0.2269 0.072 Uiso 1 1 calc R . .
C10 C 0.5613(3) 0.7085(3) -0.1156(2) 0.0662(9) Uani 1 1 d . . .
H10 H 0.5585 0.7516 -0.1705 0.079 Uiso 1 1 calc R . .
B1 B 0.5758(3) 0.3720(4) 0.2967(2) 0.0548(9) Uani 1 1 d . . .
C2 C 0.7833(3) 0.2120(4) 0.1782(2) 0.0734(10) Uani 1 1 d . . .
H2 H 0.8293 0.1439 0.1907 0.088 Uiso 1 1 calc R . .
C3 C 0.7859(3) 0.2825(4) 0.1006(2) 0.0753(10) Uani 1 1 d . . .
H3 H 0.8339 0.2636 0.0592 0.090 Uiso 1 1 calc R . .
C22 C 0.5407(3) 0.1503(4) 0.4800(3) 0.0908(13) Uani 1 1 d . . .
H22 H 0.5056 0.0705 0.4662 0.109 Uiso 1 1 calc R . .
C25 C 0.6447(3) 0.3886(5) 0.5208(2) 0.0816(12) Uani 1 1 d . . .
H25 H 0.6799 0.4686 0.5342 0.098 Uiso 1 1 calc R . .
C24 C 0.6219(3) 0.2912(6) 0.5840(3) 0.0955(16) Uani 1 1 d . . .
H24 H 0.6411 0.3061 0.6421 0.115 Uiso 1 1 calc R . .
C23 C 0.5731(4) 0.1763(6) 0.5639(3) 0.1025(16) Uani 1 1 d . . .
H23 H 0.5604 0.1115 0.6082 0.123 Uiso 1 1 calc R . .
C18 C 0.1114(3) 0.8739(6) 0.1980(4) 0.1211(18) Uani 1 1 d . . .
H18A H 0.0884 0.7946 0.1656 0.182 Uiso 1 1 calc R . .
H18B H 0.0689 0.9516 0.1882 0.182 Uiso 1 1 calc R . .
H18C H 0.1129 0.8522 0.2599 0.182 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
O2 C26 1.376(3) . ?
O2 B1 1.460(4) . ?
O1 C13 1.340(3) . ?
O1 B1 1.455(4) . ?
N1 C5 1.360(3) . ?
N1 C1 1.365(4) . ?
N1 B1 1.589(4) . ?
O3 C21 1.372(4) . ?
O3 B1 1.467(4) . ?
O4 C17 1.371(4) . ?
O4 C18 1.411(4) . ?
C5 C4 1.405(4) . ?
C5 C6 1.444(4) . ?
C13 C6 1.362(4) . ?
C13 C14 1.474(4) . ?
C14 C20 1.386(4) . ?
C14 C15 1.395(4) . ?
C17 C19 1.378(4) . ?
C17 C16 1.379(4) . ?
C6 C7 1.499(3) . ?
C7 C8 1.385(4) . ?
C7 C12 1.397(4) . ?
C12 C11 1.379(4) . ?
C12 H12 0.9500 . ?
C26 C21 1.369(5) . ?
C26 C25 1.375(4) . ?
C11 C10 1.393(5) . ?
C11 H11 0.9500 . ?
C20 C19 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.368(4) . ?
C16 C15 1.366(4) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C8 C9 1.381(4) . ?
C8 H8 0.9500 . ?
C4 C3 1.371(5) . ?
C4 H4 0.9500 . ?
C9 C10 1.361(5) . ?
C9 H9 0.9500 . ?
C1 C2 1.345(4) . ?
C1 H1 0.9500 . ?
C19 H19 0.9500 . ?
C10 H10 0.9500 . ?
C2 C3 1.385(5) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C22 C23 1.399(6) . ?
C22 H22 0.9500 . ?
C25 C24 1.403(6) . ?
C25 H25 0.9500 . ?
C24 C23 1.355(7) . ?
C24 H24 0.9500 . ?
C23 H23 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C26 O2 B1 105.5(2) . . ?
C13 O1 B1 124.7(2) . . ?
C5 N1 C1 120.7(3) . . ?
C5 N1 B1 122.1(3) . . ?
C1 N1 B1 117.1(3) . . ?
C21 O3 B1 105.8(2) . . ?
C17 O4 C18 117.9(3) . . ?
N1 C5 C4 117.3(3) . . ?
N1 C5 C6 118.9(3) . . ?
C4 C5 C6 123.8(3) . . ?
O1 C13 C6 121.9(3) . . ?
O1 C13 C14 112.0(2) . . ?
C6 C13 C14 126.1(2) . . ?
C20 C14 C15 117.0(3) . . ?
C20 C14 C13 120.0(3) . . ?
C15 C14 C13 122.9(3) . . ?
O4 C17 C19 125.2(3) . . ?
O4 C17 C16 115.3(3) . . ?
C19 C17 C16 119.4(3) . . ?
C13 C6 C5 120.6(3) . . ?
C13 C6 C7 120.8(3) . . ?
C5 C6 C7 118.2(2) . . ?
C8 C7 C12 118.8(3) . . ?
C8 C7 C6 121.9(3) . . ?
C12 C7 C6 119.3(3) . . ?
C11 C12 C7 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C21 C26 C25 122.0(3) . . ?
C21 C26 O2 111.2(3) . . ?
C25 C26 O2 126.8(3) . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C19 C20 C14 122.0(3) . . ?
C19 C20 H20 119.0 . . ?
C14 C20 H20 119.0 . . ?
C22 C21 C26 122.3(4) . . ?
C22 C21 O3 127.1(4) . . ?
C26 C21 O3 110.6(3) . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C2 C1 N1 122.4(3) . . ?
C2 C1 H1 118.8 . . ?
N1 C1 H1 118.8 . . ?
C17 C19 C20 119.6(3) . . ?
C17 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
O1 B1 O2 112.3(3) . . ?
O1 B1 O3 110.6(3) . . ?
O2 B1 O3 106.7(2) . . ?
O1 B1 N1 108.6(2) . . ?
O2 B1 N1 108.5(3) . . ?
O3 B1 N1 110.0(3) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C21 C22 C23 116.1(4) . . ?
C21 C22 H22 121.9 . . ?
C23 C22 H22 121.9 . . ?
C26 C25 C24 116.1(4) . . ?
C26 C25 H25 121.9 . . ?
C24 C25 H25 121.9 . . ?
C23 C24 C25 121.5(4) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C23 C22 122.0(4) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        65.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_exp_8721
_database_code_depnum_ccdc_archive 'CCDC 1814825'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H36 B2 N2 O8'
_chemical_formula_weight         838.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C12/c1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   39.352(3)
_cell_length_b                   13.0080(6)
_cell_length_c                   16.4737(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.835(7)
_cell_angle_gamma                90.00
_cell_volume                     8388.9(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7529
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      67.24

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3488
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9446
_exptl_absorpt_correction_T_max  0.9513
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27620
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         67.24
_reflns_number_total             7529
_reflns_number_gt                4733
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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     
'calc w=1/[σ²(Fo²)+(0.0302P)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         7529
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.42269(9) 0.3608(3) 0.2634(2) 0.0574(9) Uani 1 1 d . . .
B2 B 0.21287(8) 0.4514(2) 0.46685(18) 0.0456(7) Uani 1 1 d . . .
N1 N 0.40952(6) 0.39815(18) 0.17565(14) 0.0571(6) Uani 1 1 d . . .
N2 N 0.21215(5) 0.33418(15) 0.44013(12) 0.0438(5) Uani 1 1 d . . .
O1 O 0.43807(5) 0.26160(15) 0.25625(12) 0.0665(6) Uani 1 1 d . . .
O2 O 0.44809(5) 0.43299(15) 0.29910(12) 0.0672(6) Uani 1 1 d . . .
O3 O 0.39323(5) 0.35929(14) 0.31139(11) 0.0576(5) Uani 1 1 d . . .
O4 O 0.37178(5) 0.31060(17) 0.42445(12) 0.0745(6) Uani 1 1 d . . .
O5 O 0.24587(4) 0.49166(12) 0.45322(10) 0.0498(4) Uani 1 1 d . . .
O6 O 0.18602(5) 0.50281(13) 0.41279(10) 0.0513(5) Uani 1 1 d . . .
O7 O 0.20888(4) 0.45795(13) 0.55249(10) 0.0507(5) Uani 1 1 d . . .
O8 O 0.13787(5) 0.58949(14) 0.38832(11) 0.0602(5) Uani 1 1 d . . .
C1 C 0.39525(8) 0.3294(2) 0.12072(19) 0.0677(8) Uani 1 1 d . . .
H1 H 0.3935 0.2610 0.1365 0.081 Uiso 1 1 calc R . .
C2 C 0.38339(9) 0.3565(3) 0.04353(19) 0.0755(10) Uani 1 1 d . . .
H2 H 0.3735 0.3080 0.0069 0.091 Uiso 1 1 calc R . .
C3 C 0.38633(8) 0.4585(3) 0.02066(19) 0.0715(9) Uani 1 1 d . . .
H3 H 0.3789 0.4790 -0.0323 0.086 Uiso 1 1 calc R . .
C4 C 0.40014(8) 0.5290(2) 0.07625(17) 0.0611(8) Uani 1 1 d . . .
H4 H 0.4018 0.5974 0.0608 0.073 Uiso 1 1 calc R . .
C5 C 0.41172(7) 0.4998(2) 0.15531(17) 0.0540(7) Uani 1 1 d . . .
C6 C 0.42674(7) 0.5714(2) 0.21684(16) 0.0513(7) Uani 1 1 d . . .
C7 C 0.42394(7) 0.6833(2) 0.19804(15) 0.0520(7) Uani 1 1 d . . .
C8 C 0.45294(8) 0.7440(2) 0.19759(17) 0.0630(8) Uani 1 1 d . . .
H8 H 0.4744 0.7140 0.2064 0.076 Uiso 1 1 calc R . .
C9 C 0.45011(9) 0.8490(2) 0.18418(19) 0.0723(9) Uani 1 1 d . . .
H9 H 0.4697 0.8892 0.1851 0.087 Uiso 1 1 calc R . .
C10 C 0.41833(10) 0.8940(3) 0.16939(18) 0.0733(9) Uani 1 1 d . . .
H10 H 0.4164 0.9646 0.1612 0.088 Uiso 1 1 calc R . .
C11 C 0.38966(9) 0.8342(2) 0.16683(17) 0.0663(8) Uani 1 1 d . . .
H11 H 0.3682 0.8639 0.1550 0.080 Uiso 1 1 calc R . .
C12 C 0.39230(8) 0.7300(2) 0.18164(16) 0.0581(7) Uani 1 1 d . . .
H12 H 0.3726 0.6904 0.1806 0.070 Uiso 1 1 calc R . .
C13 C 0.44393(7) 0.5345(2) 0.28617(17) 0.0558(7) Uani 1 1 d . . .
C14 C 0.46097(8) 0.5961(2) 0.35452(17) 0.0591(8) Uani 1 1 d . . .
C15 C 0.49219(8) 0.5638(3) 0.39249(19) 0.0739(9) Uani 1 1 d . . .
H15 H 0.5027 0.5058 0.3734 0.089 Uiso 1 1 calc R . .
C16 C 0.50791(10) 0.6176(3) 0.4588(2) 0.0920(12) Uani 1 1 d . . .
H16 H 0.5290 0.5960 0.4837 0.110 Uiso 1 1 calc R . .
C17 C 0.49244(11) 0.7022(3) 0.4874(2) 0.0949(13) Uani 1 1 d . . .
H17 H 0.5030 0.7383 0.5317 0.114 Uiso 1 1 calc R . .
C18 C 0.46148(10) 0.7337(3) 0.4511(2) 0.0945(12) Uani 1 1 d . . .
H18 H 0.4509 0.7908 0.4713 0.113 Uiso 1 1 calc R . .
C19 C 0.44562(9) 0.6814(3) 0.38423(19) 0.0770(10) Uani 1 1 d . . .
H19 H 0.4246 0.7039 0.3595 0.092 Uiso 1 1 calc R . .
C20 C 0.39340(7) 0.2996(2) 0.37740(17) 0.0539(7) Uani 1 1 d . . .
C21 C 0.42030(7) 0.2200(2) 0.38688(16) 0.0517(7) Uani 1 1 d . . .
C22 C 0.44065(8) 0.2022(2) 0.32454(18) 0.0588(8) Uani 1 1 d . . .
C23 C 0.46361(9) 0.1207(3) 0.3307(2) 0.0809(10) Uani 1 1 d . . .
H23 H 0.4765 0.1062 0.2879 0.097 Uiso 1 1 calc R . .
C24 C 0.46717(10) 0.0616(3) 0.4003(2) 0.0847(11) Uani 1 1 d . . .
H24 H 0.4826 0.0073 0.4044 0.102 Uiso 1 1 calc R . .
C25 C 0.44818(9) 0.0818(3) 0.4637(2) 0.0771(10) Uani 1 1 d . . .
H25 H 0.4514 0.0432 0.5113 0.093 Uiso 1 1 calc R . .
C26 C 0.42441(8) 0.1593(2) 0.45658(18) 0.0657(8) Uani 1 1 d . . .
H26 H 0.4109 0.1714 0.4988 0.079 Uiso 1 1 calc R . .
C27 C 0.19130(7) 0.2679(2) 0.47454(16) 0.0522(7) Uani 1 1 d . . .
H27 H 0.1793 0.2909 0.5168 0.063 Uiso 1 1 calc R . .
C28 C 0.18733(7) 0.1687(2) 0.44924(17) 0.0566(7) Uani 1 1 d . . .
H28 H 0.1735 0.1236 0.4749 0.068 Uiso 1 1 calc R . .
C29 C 0.20439(7) 0.1368(2) 0.38448(18) 0.0582(7) Uani 1 1 d . . .
H29 H 0.2014 0.0701 0.3646 0.070 Uiso 1 1 calc R . .
C30 C 0.22571(7) 0.20331(19) 0.34930(16) 0.0517(7) Uani 1 1 d . . .
H30 H 0.2371 0.1813 0.3057 0.062 Uiso 1 1 calc R . .
C31 C 0.23036(6) 0.30325(19) 0.37827(14) 0.0431(6) Uani 1 1 d . . .
C32 C 0.25416(6) 0.37515(18) 0.34736(14) 0.0420(6) Uani 1 1 d . . .
C33 C 0.27035(6) 0.34635(19) 0.27214(15) 0.0431(6) Uani 1 1 d . . .
C34 C 0.29587(7) 0.2719(2) 0.27450(16) 0.0553(7) Uani 1 1 d . . .
H34 H 0.3029 0.2394 0.3236 0.066 Uiso 1 1 calc R . .
C35 C 0.31082(8) 0.2456(2) 0.20516(17) 0.0622(8) Uani 1 1 d . . .
H35 H 0.3279 0.1960 0.2078 0.075 Uiso 1 1 calc R . .
C36 C 0.30047(8) 0.2929(2) 0.13196(17) 0.0626(8) Uani 1 1 d . . .
H36 H 0.3105 0.2751 0.0852 0.075 Uiso 1 1 calc R . .
C37 C 0.27527(8) 0.3664(2) 0.12840(16) 0.0596(8) Uani 1 1 d . . .
H37 H 0.2682 0.3983 0.0790 0.071 Uiso 1 1 calc R . .
C38 C 0.26040(7) 0.39315(19) 0.19816(15) 0.0499(7) Uani 1 1 d . . .
H38 H 0.2435 0.4433 0.1952 0.060 Uiso 1 1 calc R . .
C39 C 0.26179(6) 0.46416(19) 0.38807(14) 0.0435(6) Uani 1 1 d . . .
C40 C 0.28814(7) 0.54044(19) 0.36988(15) 0.0445(6) Uani 1 1 d . . .
C41 C 0.31882(7) 0.5137(2) 0.34074(16) 0.0510(7) Uani 1 1 d . . .
H41 H 0.3236 0.4449 0.3315 0.061 Uiso 1 1 calc R . .
C42 C 0.34228(7) 0.5879(2) 0.32537(17) 0.0590(8) Uani 1 1 d . . .
H42 H 0.3626 0.5688 0.3052 0.071 Uiso 1 1 calc R . .
C43 C 0.33597(8) 0.6899(2) 0.33961(18) 0.0643(8) Uani 1 1 d . . .
H43 H 0.3518 0.7398 0.3285 0.077 Uiso 1 1 calc R . .
C44 C 0.30619(8) 0.7176(2) 0.37027(18) 0.0630(8) Uani 1 1 d . . .
H44 H 0.3020 0.7864 0.3807 0.076 Uiso 1 1 calc R . .
C45 C 0.28224(7) 0.6437(2) 0.38585(17) 0.0550(7) Uani 1 1 d . . .
H45 H 0.2622 0.6632 0.4070 0.066 Uiso 1 1 calc R . .
C46 C 0.15809(7) 0.54567(19) 0.43722(16) 0.0459(6) Uani 1 1 d . . .
C47 C 0.15377(7) 0.53650(18) 0.52468(15) 0.0449(6) Uani 1 1 d . . .
C48 C 0.12368(7) 0.5698(2) 0.55412(18) 0.0598(8) Uani 1 1 d . . .
H48 H 0.1068 0.6009 0.5189 0.072 Uiso 1 1 calc R . .
C49 C 0.11883(8) 0.5568(2) 0.63523(19) 0.0687(9) Uani 1 1 d . . .
H49 H 0.0986 0.5783 0.6546 0.082 Uiso 1 1 calc R . .
C50 C 0.14416(8) 0.5116(2) 0.68756(18) 0.0647(8) Uani 1 1 d . . .
H50 H 0.1408 0.5025 0.7422 0.078 Uiso 1 1 calc R . .
C51 C 0.17426(7) 0.47982(19) 0.65982(15) 0.0525(7) Uani 1 1 d . . .
H51 H 0.1914 0.4510 0.6958 0.063 Uiso 1 1 calc R . .
C52 C 0.17899(7) 0.49093(18) 0.57782(15) 0.0441(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.436(4) . ?
B1 O2 1.451(4) . ?
B1 O3 1.468(4) . ?
B1 N1 1.562(4) . ?
B2 O7 1.438(3) . ?
B2 O5 1.439(3) . ?
B2 O6 1.472(3) . ?
B2 N2 1.586(3) . ?
N1 C1 1.353(3) . ?
N1 C5 1.368(3) . ?
N2 C27 1.354(3) . ?
N2 C31 1.365(3) . ?
O1 C22 1.360(3) . ?
O2 C13 1.345(3) . ?
O3 C20 1.335(3) . ?
O4 C20 1.216(3) . ?
O5 C39 1.345(3) . ?
O6 C46 1.331(3) . ?
O7 C52 1.357(3) . ?
O8 C46 1.215(3) . ?
C1 C2 1.356(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.369(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.457(4) . ?
C6 C13 1.355(4) . ?
C6 C7 1.490(4) . ?
C7 C12 1.387(4) . ?
C7 C8 1.388(4) . ?
C8 C9 1.386(4) . ?
C9 C10 1.380(4) . ?
C10 C11 1.368(4) . ?
C11 C12 1.379(4) . ?
C13 C14 1.485(4) . ?
C14 C19 1.376(4) . ?
C14 C15 1.386(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.365(5) . ?
C17 C18 1.365(5) . ?
C18 C19 1.388(4) . ?
C20 C21 1.478(4) . ?
C21 C22 1.384(4) . ?
C21 C26 1.389(4) . ?
C22 C23 1.390(4) . ?
C23 C24 1.376(4) . ?
C24 C25 1.369(4) . ?
C25 C26 1.372(4) . ?
C27 C28 1.360(3) . ?
C28 C29 1.381(4) . ?
C29 C30 1.373(3) . ?
C30 C31 1.391(3) . ?
C31 C32 1.452(3) . ?
C32 C39 1.356(3) . ?
C32 C33 1.497(3) . ?
C33 C38 1.383(3) . ?
C33 C34 1.393(3) . ?
C34 C35 1.380(3) . ?
C35 C36 1.378(4) . ?
C36 C37 1.375(4) . ?
C37 C38 1.386(3) . ?
C39 C40 1.488(3) . ?
C40 C41 1.388(3) . ?
C40 C45 1.393(3) . ?
C41 C42 1.377(3) . ?
C42 C43 1.375(4) . ?
C43 C44 1.370(4) . ?
C44 C45 1.388(4) . ?
C46 C47 1.473(3) . ?
C47 C52 1.388(3) . ?
C47 C48 1.393(3) . ?
C48 C49 1.379(4) . ?
C49 C50 1.381(4) . ?
C50 C51 1.376(4) . ?
C51 C52 1.390(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
O1 B1 O2 109.6(3) . . ?
O1 B1 O3 113.2(3) . . ?
O2 B1 O3 109.8(3) . . ?
O1 B1 N1 107.9(2) . . ?
O2 B1 N1 108.9(2) . . ?
O3 B1 N1 107.2(2) . . ?
O7 B2 O5 108.8(2) . . ?
O7 B2 O6 115.1(2) . . ?
O5 B2 O6 110.1(2) . . ?
O7 B2 N2 109.2(2) . . ?
O5 B2 N2 107.3(2) . . ?
O6 B2 N2 106.1(2) . . ?
C1 N1 C5 120.5(3) . . ?
C1 N1 B1 119.3(3) . . ?
C5 N1 B1 120.2(2) . . ?
C27 N2 C31 120.8(2) . . ?
C27 N2 B2 119.4(2) . . ?
C31 N2 B2 119.6(2) . . ?
C22 O1 B1 116.1(2) . . ?
C13 O2 B1 120.2(2) . . ?
C20 O3 B1 120.5(2) . . ?
C39 O5 B2 121.9(2) . . ?
C46 O6 B2 124.9(2) . . ?
C52 O7 B2 120.3(2) . . ?
N1 C1 C2 122.3(3) . . ?
C1 C2 C3 118.3(3) . . ?
C4 C3 C2 119.8(3) . . ?
C3 C4 C5 121.0(3) . . ?
N1 C5 C4 118.1(3) . . ?
N1 C5 C6 118.6(2) . . ?
C4 C5 C6 123.3(3) . . ?
C13 C6 C5 119.5(3) . . ?
C13 C6 C7 122.8(3) . . ?
C5 C6 C7 117.7(2) . . ?
C12 C7 C8 118.2(3) . . ?
C12 C7 C6 120.9(3) . . ?
C8 C7 C6 120.9(3) . . ?
C9 C8 C7 120.5(3) . . ?
C10 C9 C8 120.2(3) . . ?
C11 C10 C9 119.6(3) . . ?
C10 C11 C12 120.4(3) . . ?
C11 C12 C7 121.0(3) . . ?
O2 C13 C6 121.6(3) . . ?
O2 C13 C14 111.8(3) . . ?
C6 C13 C14 126.6(3) . . ?
C19 C14 C15 119.0(3) . . ?
C19 C14 C13 121.6(3) . . ?
C15 C14 C13 119.3(3) . . ?
C14 C15 C16 120.4(4) . . ?
C17 C16 C15 120.0(4) . . ?
C18 C17 C16 120.0(4) . . ?
C17 C18 C19 120.7(4) . . ?
C14 C19 C18 120.0(4) . . ?
O4 C20 O3 120.3(3) . . ?
O4 C20 C21 123.7(3) . . ?
O3 C20 C21 115.9(2) . . ?
C22 C21 C26 119.4(3) . . ?
C22 C21 C20 120.1(3) . . ?
C26 C21 C20 120.5(3) . . ?
O1 C22 C21 121.2(3) . . ?
O1 C22 C23 119.2(3) . . ?
C21 C22 C23 119.6(3) . . ?
C24 C23 C22 119.9(3) . . ?
C25 C24 C23 120.7(3) . . ?
C24 C25 C26 119.8(3) . . ?
C25 C26 C21 120.6(3) . . ?
N2 C27 C28 122.1(3) . . ?
C27 C28 C29 118.2(3) . . ?
C30 C29 C28 120.2(3) . . ?
C29 C30 C31 120.6(3) . . ?
N2 C31 C30 118.1(2) . . ?
N2 C31 C32 118.6(2) . . ?
C30 C31 C32 123.3(2) . . ?
C39 C32 C31 119.6(2) . . ?
C39 C32 C33 122.1(2) . . ?
C31 C32 C33 118.2(2) . . ?
C38 C33 C34 118.0(2) . . ?
C38 C33 C32 120.9(2) . . ?
C34 C33 C32 121.1(2) . . ?
C35 C34 C33 121.1(3) . . ?
C36 C35 C34 120.1(3) . . ?
C37 C36 C35 119.7(3) . . ?
C36 C37 C38 120.2(3) . . ?
C33 C38 C37 121.0(3) . . ?
O5 C39 C32 121.6(2) . . ?
O5 C39 C40 112.0(2) . . ?
C32 C39 C40 126.4(2) . . ?
C41 C40 C45 118.4(2) . . ?
C41 C40 C39 123.4(2) . . ?
C45 C40 C39 118.2(2) . . ?
C42 C41 C40 120.7(3) . . ?
C43 C42 C41 120.6(3) . . ?
C44 C43 C42 119.5(3) . . ?
C43 C44 C45 120.6(3) . . ?
C44 C45 C40 120.2(3) . . ?
O8 C46 O6 120.1(2) . . ?
O8 C46 C47 123.6(3) . . ?
O6 C46 C47 116.3(2) . . ?
C52 C47 C48 119.4(2) . . ?
C52 C47 C46 120.4(2) . . ?
C48 C47 C46 120.1(3) . . ?
C49 C48 C47 120.4(3) . . ?
C48 C49 C50 119.6(3) . . ?
C51 C50 C49 120.8(3) . . ?
C50 C51 C52 119.8(3) . . ?
O7 C52 C47 121.8(2) . . ?
O7 C52 C51 118.1(2) . . ?
C47 C52 C51 120.0(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.24
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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 1814824'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 B N2 O3'
_chemical_formula_weight         434.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3039(3)
_cell_length_b                   15.2929(4)
_cell_length_c                   14.3427(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.422(3)
_cell_angle_gamma                90.00
_cell_volume                     2260.02(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4356
_cell_measurement_theta_min      4.23
_cell_measurement_theta_max      71.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.1875
_exptl_absorpt_correction_T_max  0.9551
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14300
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.23
_diffrn_reflns_theta_max         71.42
_reflns_number_total             4356
_reflns_number_gt                3439
_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)+(0.0482P)²+0.5798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4356
_refine_ls_number_parameters     301
_refine_ls_number_restraints     960
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_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
O3 O 0.37628(11) 0.30019(8) 0.49015(8) 0.0446(3) Uani 1 1 d U . .
O2 O 0.21405(11) 0.34106(8) 0.38372(8) 0.0468(3) Uani 1 1 d U . .
C32 C -0.4404(2) 0.03792(17) 0.6375(2) 0.0998(10) Uani 1 1 d U . .
H32A H -0.4454 0.0702 0.6947 0.150 Uiso 1 1 calc R . .
H32B H -0.4863 -0.0164 0.6439 0.150 Uiso 1 1 calc R . .
H32C H -0.4789 0.0715 0.5880 0.150 Uiso 1 1 calc R . .
C33 C -0.2678(2) -0.06938(14) 0.6072(2) 0.0858(8) Uani 1 1 d U . .
H33A H -0.2119 -0.0757 0.5544 0.129 Uiso 1 1 calc R . .
H33B H -0.3434 -0.1052 0.5987 0.129 Uiso 1 1 calc R . .
H33C H -0.2223 -0.0873 0.6627 0.129 Uiso 1 1 calc R . .
N2 N -0.30623(16) 0.02049(11) 0.61612(15) 0.0688(5) Uani 1 1 d U . .
C2 C -0.21771(17) 0.08709(11) 0.61166(13) 0.0461(4) Uani 1 1 d U . .
C3 C -0.25701(17) 0.17496(12) 0.61485(14) 0.0485(4) Uani 1 1 d U . .
H3 H -0.3447 0.1880 0.6208 0.058 Uiso 1 1 d R . .
C4 C -0.16804(17) 0.24173(11) 0.60983(13) 0.0452(4) Uani 1 1 d U . .
H4 H -0.1967 0.2993 0.6118 0.054 Uiso 1 1 d R . .
C5 C -0.03580(16) 0.22583(10) 0.60023(11) 0.0386(4) Uani 1 1 d U . .
C6 C 0.00290(16) 0.13861(10) 0.59577(12) 0.0421(4) Uani 1 1 d U . .
H6 H 0.0903 0.1258 0.5874 0.051 Uiso 1 1 d R . .
C7 C -0.08429(17) 0.07110(11) 0.60245(13) 0.0459(4) Uani 1 1 d U . .
H7 H -0.0549 0.0136 0.6025 0.055 Uiso 1 1 d R . .
C8 C 0.05945(16) 0.29625(10) 0.58741(12) 0.0402(4) Uani 1 1 d U . .
C9 C 0.05744(16) 0.37632(10) 0.62973(12) 0.0410(4) Uani 1 1 d U . .
C10 C 0.14986(17) 0.44221(11) 0.60312(12) 0.0442(4) Uani 1 1 d U . .
N1 N 0.23388(14) 0.42511(9) 0.53254(10) 0.0452(4) Uani 1 1 d U . .
B1 B 0.24272(19) 0.33298(13) 0.48394(14) 0.0435(4) Uani 1 1 d U . .
O1 O 0.15292(12) 0.27371(8) 0.52821(9) 0.0525(3) Uani 1 1 d U . .
C14 C -0.03462(16) 0.39477(10) 0.70746(12) 0.0407(4) Uani 1 1 d U . .
C15 C -0.12357(18) 0.46286(11) 0.70267(13) 0.0487(4) Uani 1 1 d U . .
H15 H -0.1245 0.4987 0.6503 0.058 Uiso 1 1 d R . .
C16 C -0.20853(19) 0.47891(13) 0.77460(15) 0.0568(5) Uani 1 1 d U . .
H16 H -0.2694 0.5236 0.7695 0.068 Uiso 1 1 d R . .
C17 C -0.2060(2) 0.42714(14) 0.85304(15) 0.0588(5) Uani 1 1 d U . .
H17 H -0.2619 0.4387 0.9021 0.071 Uiso 1 1 d R . .
C18 C -0.11868(19) 0.35904(13) 0.85938(13) 0.0545(5) Uani 1 1 d U . .
H18 H -0.1177 0.3240 0.9124 0.065 Uiso 1 1 d R . .
C19 C -0.03318(17) 0.34306(11) 0.78726(12) 0.0459(4) Uani 1 1 d U . .
H19 H 0.0258 0.2972 0.7921 0.055 Uiso 1 1 d R . .
C20 C 0.1586(2) 0.52490(12) 0.64633(15) 0.0586(5) Uani 1 1 d U . .
H20 H 0.1025 0.5388 0.6946 0.070 Uiso 1 1 d R . .
C21 C 0.2449(2) 0.58607(13) 0.61670(16) 0.0677(6) Uani 1 1 d U . .
H21 H 0.2505 0.6397 0.6471 0.081 Uiso 1 1 d R . .
C22 C 0.3264(2) 0.56744(13) 0.54271(16) 0.0645(6) Uani 1 1 d U . .
H22 H 0.3854 0.6088 0.5215 0.077 Uiso 1 1 d R . .
C23 C 0.31861(19) 0.48692(12) 0.50338(14) 0.0548(5) Uani 1 1 d U . .
H23 H 0.3722 0.4745 0.4532 0.066 Uiso 1 1 d R . .
C25 C 0.41008(16) 0.27624(10) 0.40199(11) 0.0377(4) Uani 1 1 d U . .
C26 C 0.31303(16) 0.30007(10) 0.33896(12) 0.0399(4) Uani 1 1 d U . .
C28 C 0.52035(17) 0.23351(11) 0.37403(13) 0.0453(4) Uani 1 1 d U . .
H28 H 0.5858 0.2187 0.4162 0.054 Uiso 1 1 d R . .
C29 C 0.53060(19) 0.21351(13) 0.27976(14) 0.0543(5) Uani 1 1 d U . .
H29 H 0.6038 0.1843 0.2585 0.065 Uiso 1 1 d R . .
C30 C 0.4341(2) 0.23582(14) 0.21752(14) 0.0583(5) Uani 1 1 d U . .
H30 H 0.4432 0.2207 0.1551 0.070 Uiso 1 1 d R . .
C31 C 0.32309(19) 0.28013(12) 0.24597(13) 0.0506(4) Uani 1 1 d U . .
H31 H 0.2589 0.2963 0.2034 0.061 Uiso 1 1 d 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
O3 C25 1.3640(19) . ?
O3 B1 1.467(2) . ?
O2 C26 1.362(2) . ?
O2 B1 1.470(2) . ?
C32 N2 1.443(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 N2 1.436(3) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N2 C2 1.369(2) . ?
C2 C7 1.404(2) . ?
C2 C3 1.404(2) . ?
C3 C4 1.374(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(2) . ?
C5 C8 1.469(2) . ?
C6 C7 1.372(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.334(2) . ?
C8 C9 1.367(2) . ?
C9 C10 1.440(2) . ?
C9 C14 1.496(2) . ?
C10 N1 1.362(2) . ?
C10 C20 1.411(2) . ?
N1 C23 1.355(2) . ?
N1 B1 1.575(2) . ?
B1 O1 1.445(2) . ?
C14 C15 1.389(2) . ?
C14 C19 1.391(2) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.361(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 C28 1.373(2) . ?
C25 C26 1.392(2) . ?
C26 C31 1.373(2) . ?
C28 C29 1.391(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.374(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.394(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O3 B1 106.35(13) . . ?
C26 O2 B1 106.04(13) . . ?
N2 C32 H32A 109.5 . . ?
N2 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N2 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N2 C33 H33A 109.5 . . ?
N2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C2 N2 C33 121.56(17) . . ?
C2 N2 C32 120.81(17) . . ?
C33 N2 C32 117.44(17) . . ?
N2 C2 C7 121.88(16) . . ?
N2 C2 C3 121.20(16) . . ?
C7 C2 C3 116.92(15) . . ?
C4 C3 C2 121.10(16) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.95(16) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 116.89(15) . . ?
C4 C5 C8 122.66(15) . . ?
C6 C5 C8 120.26(15) . . ?
C7 C6 C5 121.94(16) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C2 121.17(16) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 118.9 . . ?
O1 C8 C9 121.84(15) . . ?
O1 C8 C5 112.11(14) . . ?
C9 C8 C5 126.06(15) . . ?
C8 C9 C10 119.80(15) . . ?
C8 C9 C14 120.77(15) . . ?
C10 C9 C14 119.33(14) . . ?
N1 C10 C20 117.36(16) . . ?
N1 C10 C9 119.20(15) . . ?
C20 C10 C9 123.44(16) . . ?
C23 N1 C10 120.66(15) . . ?
C23 N1 B1 116.61(15) . . ?
C10 N1 B1 122.67(14) . . ?
O1 B1 O3 111.24(15) . . ?
O1 B1 O2 110.95(15) . . ?
O3 B1 O2 105.65(14) . . ?
O1 B1 N1 109.10(14) . . ?
O3 B1 N1 109.65(14) . . ?
O2 B1 N1 110.22(15) . . ?
C8 O1 B1 125.81(14) . . ?
C15 C14 C19 118.04(16) . . ?
C15 C14 C9 121.77(16) . . ?
C19 C14 C9 120.19(15) . . ?
C16 C15 C14 121.22(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.0 . . ?
C17 C16 C15 120.06(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 119.79(18) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.15(18) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C14 120.73(17) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.5 . . ?
C21 C20 C10 121.24(19) . . ?
C21 C20 H20 119.2 . . ?
C10 C20 H20 119.6 . . ?
C20 C21 C22 119.88(19) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 118.03(18) . . ?
C23 C22 H22 121.3 . . ?
C21 C22 H22 120.7 . . ?
N1 C23 C22 122.77(19) . . ?
N1 C23 H23 118.9 . . ?
C22 C23 H23 118.3 . . ?
O3 C25 C28 128.03(15) . . ?
O3 C25 C26 110.16(14) . . ?
C28 C25 C26 121.80(16) . . ?
O2 C26 C31 128.49(16) . . ?
O2 C26 C25 110.56(14) . . ?
C31 C26 C25 120.93(16) . . ?
C25 C28 C29 117.22(17) . . ?
C25 C28 H28 121.5 . . ?
C29 C28 H28 121.2 . . ?
C30 C29 C28 121.15(18) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 121.47(18) . . ?
C29 C30 H30 119.1 . . ?
C31 C30 H30 119.5 . . ?
C26 C31 C30 117.42(18) . . ?
C26 C31 H31 121.3 . . ?
C30 C31 H31 121.3 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        71.42
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1814826'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.95 H2.42 B0.11 N0.21 O0.53'
_chemical_formula_weight         50.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3317(13)
_cell_length_b                   15.4676(14)
_cell_length_c                   15.5196(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.330(10)
_cell_angle_gamma                90.00
_cell_volume                     2480.1(5)
_cell_formula_units_Z            38
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4319
_cell_measurement_theta_min      4.03
_cell_measurement_theta_max      66.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8032
_exptl_absorpt_correction_T_max  0.8357
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14026
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_sigmaI/netI    0.1240
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.03
_diffrn_reflns_theta_max         66.04
_reflns_number_total             4319
_reflns_number_gt                1999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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     
'calc w=1/[σ²(Fo²)+(0.1363P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0036(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4319
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.0854
_refine_ls_wR_factor_ref         0.2909
_refine_ls_wR_factor_gt          0.2409
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.120
_refine_ls_shift/su_mean         0.006

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
O1 O 0.1043(3) 0.6977(2) 0.0286(2) 0.0777(10) Uani 1 1 d . . .
O2 O 0.1977(3) 0.6219(2) -0.0874(2) 0.0765(10) Uani 1 1 d . . .
O3 O 0.3268(3) 0.6592(2) 0.0381(2) 0.0805(10) Uani 1 1 d . . .
N1 N 0.1665(4) 0.5457(2) 0.0487(2) 0.0673(10) Uani 1 1 d . . .
C6 C 0.0213(4) 0.6191(3) 0.1458(3) 0.0595(11) Uani 1 1 d . . .
C7 C 0.0260(4) 0.6918(3) 0.0964(3) 0.0634(12) Uani 1 1 d . . .
C14 C -0.0547(4) 0.7695(3) 0.1078(3) 0.0607(11) Uani 1 1 d . . .
C5 C 0.0926(4) 0.5424(3) 0.1210(3) 0.0629(12) Uani 1 1 d . . .
C16 C -0.0754(5) 0.9258(3) 0.1005(3) 0.0754(14) Uani 1 1 d . . .
H16 H -0.0351 0.9808 0.0949 0.091 Uiso 1 1 calc R . .
C17 C -0.2094(5) 0.9204(3) 0.1138(3) 0.0785(15) Uani 1 1 d . . .
C15 C -0.0021(4) 0.8516(3) 0.0954(3) 0.0667(12) Uani 1 1 d . . .
H15 H 0.0876 0.8566 0.0830 0.080 Uiso 1 1 calc R . .
C8 C -0.0576(5) 0.6154(3) 0.2255(3) 0.0655(12) Uani 1 1 d . . .
C27 C 0.3926(5) 0.7024(3) -0.1011(4) 0.0756(14) Uani 1 1 d . . .
C19 C -0.1851(5) 0.7655(3) 0.1253(3) 0.0749(14) Uani 1 1 d . . .
H19 H -0.2237 0.7109 0.1363 0.090 Uiso 1 1 calc R . .
C23 C 0.2581(6) 0.6711(4) -0.2249(4) 0.0943(18) Uani 1 1 d . . .
H23 H 0.1830 0.6449 -0.2490 0.113 Uiso 1 1 calc R . .
C22 C 0.2839(5) 0.6660(3) -0.1369(3) 0.0716(14) Uani 1 1 d . . .
N2 N -0.2858(5) 0.9929(3) 0.1158(4) 0.123(2) Uani 1 1 d . . .
C2 C 0.2239(6) 0.3970(3) 0.0635(4) 0.0901(17) Uani 1 1 d . . .
H2 H 0.2664 0.3473 0.0415 0.108 Uiso 1 1 calc R . .
C13 C -0.1616(5) 0.5602(3) 0.2339(4) 0.0850(16) Uani 1 1 d . . .
H13 H -0.1836 0.5231 0.1874 0.102 Uiso 1 1 calc R . .
C18 C -0.2606(5) 0.8382(3) 0.1274(4) 0.0827(16) Uani 1 1 d . . .
H18 H -0.3506 0.8325 0.1384 0.099 Uiso 1 1 calc R . .
C4 C 0.0905(5) 0.4649(3) 0.1670(3) 0.0779(14) Uani 1 1 d . . .
H4 H 0.0422 0.4616 0.2188 0.093 Uiso 1 1 calc R . .
C10 C -0.0995(7) 0.6651(4) 0.3706(4) 0.103(2) Uani 1 1 d . . .
H10 H -0.0778 0.7011 0.4181 0.124 Uiso 1 1 calc R . .
C26 C 0.4805(6) 0.7462(4) -0.1557(5) 0.100(2) Uani 1 1 d . . .
H26 H 0.5570 0.7713 -0.1324 0.120 Uiso 1 1 calc R . .
C12 C -0.2347(6) 0.5575(4) 0.3082(4) 0.0997(19) Uani 1 1 d . . .
H12 H -0.3062 0.5191 0.3118 0.120 Uiso 1 1 calc R . .
C9 C -0.0272(6) 0.6676(3) 0.2961(3) 0.0808(15) Uani 1 1 d . . .
H9 H 0.0448 0.7057 0.2928 0.097 Uiso 1 1 calc R . .
C3 C 0.1562(6) 0.3934(3) 0.1395(4) 0.0869(16) Uani 1 1 d . . .
H3 H 0.1551 0.3417 0.1726 0.104 Uiso 1 1 calc R . .
C1 C 0.2282(5) 0.4740(3) 0.0207(3) 0.0849(15) Uani 1 1 d . . .
H1 H 0.2766 0.4773 -0.0311 0.102 Uiso 1 1 calc R . .
B1 B 0.1995(6) 0.6345(4) 0.0049(4) 0.0683(15) Uani 1 1 d . . .
C24 C 0.3443(8) 0.7151(4) -0.2760(5) 0.115(2) Uani 1 1 d . . .
H24 H 0.3277 0.7203 -0.3360 0.138 Uiso 1 1 calc R . .
O4 O 0.5184(4) 0.7180(3) 0.0266(3) 0.1316(18) Uani 1 1 d . . .
C20 C -0.2450(7) 1.0750(4) 0.0846(6) 0.144(3) Uani 1 1 d . . .
H20A H -0.2113 1.1096 0.1327 0.217 Uiso 1 1 calc R . .
H20B H -0.3187 1.1050 0.0581 0.217 Uiso 1 1 calc R . .
H20C H -0.1768 1.0670 0.0417 0.217 Uiso 1 1 calc R . .
C28 C 0.4185(6) 0.6954(3) -0.0093(4) 0.0847(16) Uani 1 1 d . . .
C11 C -0.2054(7) 0.6085(5) 0.3750(5) 0.112(2) Uani 1 1 d . . .
H11 H -0.2564 0.6065 0.4256 0.134 Uiso 1 1 calc R . .
C25 C 0.4552(9) 0.7521(4) -0.2411(6) 0.127(3) Uani 1 1 d . . .
H25 H 0.5138 0.7818 -0.2776 0.152 Uiso 1 1 calc R . .
C21 C -0.4218(7) 0.9851(5) 0.1336(8) 0.213(6) Uani 1 1 d . . .
H21A H -0.4643 0.9531 0.0868 0.320 Uiso 1 1 calc R . .
H21B H -0.4603 1.0428 0.1382 0.320 Uiso 1 1 calc R . .
H21C H -0.4336 0.9539 0.1880 0.320 Uiso 1 1 calc R . .
O5 O 0.5344(14) 0.5467(11) 0.1389(10) 0.411(8) Uiso 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
O1 C7 1.333(5) . ?
O1 B1 1.437(6) . ?
O2 C22 1.361(5) . ?
O2 B1 1.446(6) . ?
O3 C28 1.326(6) . ?
O3 B1 1.461(7) . ?
N1 C1 1.352(6) . ?
N1 C5 1.363(5) . ?
N1 B1 1.571(6) . ?
C6 C7 1.363(6) . ?
C6 C5 1.449(6) . ?
C6 C8 1.486(6) . ?
C7 C14 1.473(6) . ?
C14 C19 1.378(6) . ?
C14 C15 1.396(6) . ?
C5 C4 1.396(6) . ?
C16 C15 1.377(6) . ?
C16 C17 1.404(6) . ?
C16 H16 0.9500 . ?
C17 N2 1.372(6) . ?
C17 C18 1.394(6) . ?
C15 H15 0.9500 . ?
C8 C13 1.378(6) . ?
C8 C9 1.395(7) . ?
C27 C22 1.371(7) . ?
C27 C26 1.419(7) . ?
C27 C28 1.452(8) . ?
C19 C18 1.369(6) . ?
C19 H19 0.9500 . ?
C23 C24 1.377(8) . ?
C23 C22 1.392(7) . ?
C23 H23 0.9500 . ?
N2 C20 1.423(7) . ?
N2 C21 1.439(7) . ?
C2 C1 1.364(7) . ?
C2 C3 1.375(7) . ?
C2 H2 0.9500 . ?
C13 C12 1.382(7) . ?
C13 H13 0.9500 . ?
C18 H18 0.9500 . ?
C4 C3 1.366(6) . ?
C4 H4 0.9500 . ?
C10 C9 1.380(7) . ?
C10 C11 1.403(9) . ?
C10 H10 0.9500 . ?
C26 C25 1.353(10) . ?
C26 H26 0.9500 . ?
C12 C11 1.336(9) . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C3 H3 0.9500 . ?
C1 H1 0.9500 . ?
C24 C25 1.387(10) . ?
C24 H24 0.9500 . ?
O4 C28 1.221(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C11 H11 0.9500 . ?
C25 H25 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C7 O1 B1 125.2(4) . . ?
C22 O2 B1 119.1(4) . . ?
C28 O3 B1 124.0(5) . . ?
C1 N1 C5 120.1(4) . . ?
C1 N1 B1 118.3(4) . . ?
C5 N1 B1 120.9(4) . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 C8 121.5(4) . . ?
C5 C6 C8 118.1(4) . . ?
O1 C7 C6 121.6(4) . . ?
O1 C7 C14 112.7(4) . . ?
C6 C7 C14 125.7(4) . . ?
C19 C14 C15 116.7(4) . . ?
C19 C14 C7 122.8(4) . . ?
C15 C14 C7 120.3(4) . . ?
N1 C5 C4 117.6(4) . . ?
N1 C5 C6 118.5(4) . . ?
C4 C5 C6 123.9(4) . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
N2 C17 C18 121.5(5) . . ?
N2 C17 C16 121.5(5) . . ?
C18 C17 C16 116.9(4) . . ?
C16 C15 C14 122.4(4) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C13 C8 C9 117.1(5) . . ?
C13 C8 C6 122.3(4) . . ?
C9 C8 C6 120.6(4) . . ?
C22 C27 C26 118.7(6) . . ?
C22 C27 C28 120.9(5) . . ?
C26 C27 C28 120.5(6) . . ?
C18 C19 C14 121.7(4) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C24 C23 C22 118.2(7) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
O2 C22 C27 120.9(5) . . ?
O2 C22 C23 117.3(5) . . ?
C27 C22 C23 121.7(5) . . ?
C17 N2 C20 123.3(5) . . ?
C17 N2 C21 119.9(5) . . ?
C20 N2 C21 115.6(5) . . ?
C1 C2 C3 118.1(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C8 C13 C12 121.9(6) . . ?
C8 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C19 C18 C17 121.9(4) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C3 C4 C5 121.8(4) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C9 C10 C11 119.0(6) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C25 C26 C27 119.8(7) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C11 C12 C13 120.4(6) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C10 C9 C8 121.4(6) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
N1 C1 C2 122.8(5) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
O1 B1 O2 109.9(4) . . ?
O1 B1 O3 110.4(4) . . ?
O2 B1 O3 113.1(4) . . ?
O1 B1 N1 109.4(4) . . ?
O2 B1 N1 108.0(4) . . ?
O3 B1 N1 105.9(4) . . ?
C23 C24 C25 121.0(7) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C28 O3 118.2(6) . . ?
O4 C28 C27 125.3(5) . . ?
O3 C28 C27 116.6(5) . . ?
C12 C11 C10 120.3(6) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C26 C25 C24 120.6(6) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.04
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.052
