# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1479644'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H42 B N3'
_chemical_formula_weight         371.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   10.9050(19)
_cell_length_b                   20.244(3)
_cell_length_c                   10.069(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.655(3)
_cell_angle_gamma                90
_cell_volume                     2222.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5459
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      28.15

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24152
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.853
_diffrn_reflns_theta_max         28.723
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2892
_reflns_number_gt                2069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1387P)²+17.0679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2892
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.1174
_refine_ls_wR_factor_ref         0.3235
_refine_ls_wR_factor_gt          0.2958
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.0000 0.1274(2) 0.7500 0.0141(9) Uani 1 2 d S T P . .
C1 C 0.0000 0.2297(2) 0.7500 0.0163(9) Uani 1 2 d S T P . .
C2 C 0.0499(3) 0.20491(17) 0.9880(3) 0.0207(7) Uani 1 1 d . . . . .
H2 H 0.1188 0.2355 0.9998 0.025 Uiso 1 1 calc R U . . .
C3 C 0.0779(3) 0.14311(18) 1.0687(3) 0.0244(8) Uani 1 1 d . . . . .
H3A H 0.0110 0.1126 1.0601 0.037 Uiso 1 1 calc R U . . .
H3B H 0.0889 0.1548 1.1605 0.037 Uiso 1 1 calc R U . . .
H3C H 0.1515 0.1229 1.0366 0.037 Uiso 1 1 calc R U . . .
C4 C -0.0650(5) 0.2384(2) 1.0426(4) 0.0408(11) Uani 1 1 d . . . . .
H4A H -0.0900 0.2734 0.9839 0.061 Uiso 1 1 calc R U . . .
H4B H -0.0470 0.2563 1.1290 0.061 Uiso 1 1 calc R U . . .
H4C H -0.1298 0.2066 1.0492 0.061 Uiso 1 1 calc R U . . .
C5 C 0.0974(5) 0.33418(19) 0.8146(4) 0.0373(10) Uani 1 1 d . . . . .
H5A H 0.0680 0.3523 0.8963 0.056 Uiso 1 1 calc R U . . .
H5B H 0.1231 0.3694 0.7573 0.056 Uiso 1 1 calc R U . . .
H5C H 0.1656 0.3055 0.8328 0.056 Uiso 1 1 calc R U . . .
C6 C -0.2320(3) 0.12192(18) 0.8387(5) 0.0352(10) Uani 1 1 d . . . . .
H6 H -0.2220 0.1692 0.8564 0.042 Uiso 1 1 calc R U . . .
C7 C -0.3023(4) 0.0845(2) 0.9417(5) 0.0363(10) Uani 1 1 d . . . . .
H7A H -0.3739 0.1091 0.9696 0.044 Uiso 1 1 calc R U . . .
H7B H -0.2512 0.0751 1.0189 0.044 Uiso 1 1 calc R U . . .
C8 C -0.3401(3) 0.01961(18) 0.8685(4) 0.0265(8) Uani 1 1 d . . . . .
H8A H -0.2999 -0.0184 0.9084 0.032 Uiso 1 1 calc R U . . .
H8B H -0.4281 0.0132 0.8712 0.032 Uiso 1 1 calc R U . . .
C9 C -0.2975(4) 0.0299(2) 0.7263(5) 0.0375(10) Uani 1 1 d . . . . .
H9 H -0.3409 0.0028 0.6603 0.045 Uiso 1 1 calc R U . . .
C10 C -0.1608(4) 0.0261(2) 0.7188(4) 0.0347(10) Uani 1 1 d . . . . .
H10A H -0.1339 0.0311 0.6278 0.042 Uiso 1 1 calc R U . . .
H10B H -0.1313 -0.0160 0.7527 0.042 Uiso 1 1 calc R U . . .
C11 C -0.1125(3) 0.08460(15) 0.8074(3) 0.0147(6) Uani 1 1 d . . . . .
H11 H -0.0835 0.0651 0.8911 0.018 Uiso 1 1 calc R U . . .
C12 C -0.3120(3) 0.1040(2) 0.7055(5) 0.0321(9) Uani 1 1 d . . . . .
H12A H -0.3965 0.1187 0.7101 0.039 Uiso 1 1 calc R U . . .
H12B H -0.2745 0.1196 0.6244 0.039 Uiso 1 1 calc R U . . .
N1 N 0.0398(2) 0.18887(12) 0.8457(3) 0.0141(6) Uani 1 1 d . . . . .
N2 N 0.0000 0.29696(19) 0.7500 0.0266(10) Uani 1 2 d S T P . .


_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 C11 1.614(4) 2_556 ?
B1 C11 1.614(4) . ?
B1 N1 1.630(4) . ?
B1 N1 1.630(4) 2_556 ?
B1 C1 2.071(6) . ?
C1 N1 1.338(4) 2_556 ?
C1 N1 1.338(4) . ?
C1 N2 1.362(6) . ?
C2 N1 1.472(4) . ?
C2 C3 1.521(5) . ?
C2 C4 1.532(5) . ?
C5 N2 1.450(4) . ?
C6 C7 1.502(6) . ?
C6 C11 1.542(4) . ?
C6 C12 1.632(7) . ?
C7 C8 1.559(6) . ?
C8 C9 1.525(6) . ?
C9 C10 1.496(6) . ?
C9 C12 1.522(6) . ?
C10 C11 1.571(5) . ?
N2 C5 1.450(4) 2_556 ?

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
C11 B1 C11 115.1(4) 2_556 . ?
C11 B1 N1 115.03(15) 2_556 . ?
C11 B1 N1 113.36(16) . . ?
C11 B1 N1 113.36(16) 2_556 2_556 ?
C11 B1 N1 115.03(15) . 2_556 ?
N1 B1 N1 80.4(3) . 2_556 ?
C11 B1 C1 122.45(18) 2_556 . ?
C11 B1 C1 122.45(18) . . ?
N1 B1 C1 40.21(14) . . ?
N1 B1 C1 40.21(14) 2_556 . ?
N1 C1 N1 103.8(4) 2_556 . ?
N1 C1 N2 128.12(18) 2_556 . ?
N1 C1 N2 128.12(18) . . ?
N1 C1 B1 51.88(18) 2_556 . ?
N1 C1 B1 51.88(18) . . ?
N2 C1 B1 180.0 . . ?
N1 C2 C3 110.5(3) . . ?
N1 C2 C4 113.3(3) . . ?
C3 C2 C4 109.4(3) . . ?
C7 C6 C11 109.5(3) . . ?
C7 C6 C12 100.5(3) . . ?
C11 C6 C12 99.7(3) . . ?
C6 C7 C8 103.4(3) . . ?
C9 C8 C7 104.3(3) . . ?
C10 C9 C8 110.8(4) . . ?
C10 C9 C12 98.4(3) . . ?
C8 C9 C12 103.4(4) . . ?
C9 C10 C11 105.0(3) . . ?
C6 C11 C10 101.9(3) . . ?
C6 C11 B1 117.2(3) . . ?
C10 C11 B1 116.9(3) . . ?
C9 C12 C6 93.0(3) . . ?
C1 N1 C2 125.8(3) . . ?
C1 N1 B1 87.9(2) . . ?
C2 N1 B1 139.5(2) . . ?
C1 N2 C5 121.3(2) . 2_556 ?
C1 N2 C5 121.3(2) . . ?
C5 N2 C5 117.4(4) 2_556 . ?

_refine_diff_density_max         1.676
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.101

# start Validation Reply Form
_vrf_DIFMX01_1                   
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*2.00
            _refine_diff_density_max given =      1.676
            Test value =      1.400
RESPONSE: The overall quality of the crystal was very poor
;
_vrf_PLAT097_1                   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density
RESPONSE: The overall quality of the crystal was very poor
;
# end Validation Reply Form







_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1479645'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H42 B N3'
_chemical_formula_weight         347.38

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6721(4)
_cell_length_b                   9.9545(4)
_cell_length_c                   12.9081(5)
_cell_angle_alpha                80.504(2)
_cell_angle_beta                 81.237(2)
_cell_angle_gamma                62.372(2)
_cell_volume                     1081.91(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19774
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      23.36

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32013
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         23.357
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.807
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.807
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.807
_reflns_number_total             3156
_reflns_number_gt                2862
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.4751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3156
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.23423(18) 0.23146(17) 0.76122(12) 0.0145(3) Uani 1 1 d . . . . .
N1 N 0.42075(13) 0.13926(13) 0.78098(9) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.27677(13) 0.06487(12) 0.72848(9) 0.0143(3) Uani 1 1 d . . . . .
N3 N 0.53900(14) -0.13192(13) 0.76350(9) 0.0210(3) Uani 1 1 d . . . . .
C1 C 0.42147(15) 0.01474(15) 0.75567(10) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.53777(16) 0.14443(17) 0.83761(11) 0.0190(3) Uani 1 1 d . . . . .
H2 H 0.6093 0.0396 0.8628 0.023 Uiso 1 1 calc R U . . .
C3 C 0.63340(18) 0.2135(2) 0.76477(13) 0.0282(4) Uani 1 1 d . . . . .
H3A H 0.6800 0.1571 0.7047 0.042 Uiso 1 1 d R U . . .
H3B H 0.7142 0.2097 0.8018 0.042 Uiso 1 1 d R U . . .
H3C H 0.5655 0.3176 0.7417 0.042 Uiso 1 1 d R U . . .
C4 C 0.46433(17) 0.23421(18) 0.93271(12) 0.0254(4) Uani 1 1 d . . . . .
H4A H 0.3927 0.3370 0.9095 0.038 Uiso 1 1 d R U . . .
H4B H 0.5448 0.2349 0.9676 0.038 Uiso 1 1 d R U . . .
H4C H 0.4090 0.1876 0.9808 0.038 Uiso 1 1 d R U . . .
C5 C 0.22280(16) -0.00828(16) 0.66558(11) 0.0170(3) Uani 1 1 d . . . . .
H5 H 0.2208 -0.0982 0.7088 0.020 Uiso 1 1 calc R U . . .
C6 C 0.05750(18) 0.09976(19) 0.63843(14) 0.0306(4) Uani 1 1 d . . . . .
H6A H -0.0101 0.1254 0.7022 0.046 Uiso 1 1 d R U . . .
H6B H 0.0221 0.0514 0.5974 0.046 Uiso 1 1 d R U . . .
H6C H 0.0555 0.1909 0.5985 0.046 Uiso 1 1 d R U . . .
C7 C 0.32939(18) -0.06094(18) 0.56569(12) 0.0238(3) Uani 1 1 d . . . . .
H7A H 0.3265 0.0261 0.5194 0.036 Uiso 1 1 d R U . . .
H7B H 0.2938 -0.1160 0.5312 0.036 Uiso 1 1 d R U . . .
H7C H 0.4348 -0.1262 0.5834 0.036 Uiso 1 1 d R U . . .
C8 C 0.50092(19) -0.25896(17) 0.78977(12) 0.0260(4) Uani 1 1 d . . . . .
H8A H 0.4010 -0.2261 0.8300 0.039 Uiso 1 1 d R U . . .
H8B H 0.5795 -0.3404 0.8305 0.039 Uiso 1 1 d R U . . .
H8C H 0.4966 -0.2942 0.7260 0.039 Uiso 1 1 d R U . . .
C9 C 0.69859(17) -0.16931(18) 0.72113(12) 0.0261(4) Uani 1 1 d . . . . .
H9A H 0.7232 -0.2236 0.6607 0.039 Uiso 1 1 d R U . . .
H9B H 0.7692 -0.2318 0.7737 0.039 Uiso 1 1 d R U . . .
H9C H 0.7090 -0.0770 0.7007 0.039 Uiso 1 1 d R U . . .
C10 C 0.12169(15) 0.26816(15) 0.87043(10) 0.0143(3) Uani 1 1 d . . . . .
H10 H 0.1466 0.3350 0.9038 0.017 Uiso 1 1 calc R U . . .
C11 C 0.14829(16) 0.12801(16) 0.95035(11) 0.0187(3) Uani 1 1 d . . . . .
H11A H 0.1197 0.0612 0.9215 0.022 Uiso 1 1 calc R U . . .
H11B H 0.2587 0.0724 0.9617 0.022 Uiso 1 1 calc R U . . .
C12 C 0.05315(17) 0.17051(18) 1.05592(12) 0.0242(4) Uani 1 1 d . . . . .
H12A H 0.0714 0.0784 1.1031 0.029 Uiso 1 1 calc R U . . .
H12B H 0.0872 0.2307 1.0878 0.029 Uiso 1 1 calc R U . . .
C13 C -0.12116(17) 0.26139(17) 1.04142(12) 0.0227(3) Uani 1 1 d . . . . .
H13A H -0.1583 0.1961 1.0194 0.027 Uiso 1 1 calc R U . . .
H13B H -0.1780 0.2954 1.1083 0.027 Uiso 1 1 calc R U . . .
C14 C -0.15405(17) 0.39903(16) 0.95969(12) 0.0206(3) Uani 1 1 d . . . . .
H14A H -0.1324 0.4720 0.9868 0.025 Uiso 1 1 calc R U . . .
H14B H -0.2640 0.4480 0.9471 0.025 Uiso 1 1 calc R U . . .
C15 C -0.05441(16) 0.35428(16) 0.85568(11) 0.0173(3) Uani 1 1 d . . . . .
H15A H -0.0748 0.4456 0.8071 0.021 Uiso 1 1 calc R U . . .
H15B H -0.0845 0.2904 0.8247 0.021 Uiso 1 1 calc R U . . .
C16 C 0.19272(15) 0.37091(15) 0.66853(11) 0.0145(3) Uani 1 1 d . . . . .
H16 H 0.0893 0.3960 0.6480 0.017 Uiso 1 1 calc R U . . .
C17 C 0.17973(17) 0.51488(16) 0.70755(11) 0.0179(3) Uani 1 1 d . . . . .
H17A H 0.1010 0.5427 0.7670 0.021 Uiso 1 1 calc R U . . .
H17B H 0.2791 0.4921 0.7320 0.021 Uiso 1 1 calc R U . . .
C18 C 0.13640(17) 0.64970(16) 0.62244(12) 0.0213(3) Uani 1 1 d . . . . .
H18A H 0.1343 0.7356 0.6501 0.026 Uiso 1 1 calc R U . . .
H18B H 0.0325 0.6794 0.6026 0.026 Uiso 1 1 calc R U . . .
C19 C 0.25331(17) 0.60994(16) 0.52540(12) 0.0210(3) Uani 1 1 d . . . . .
H19A H 0.2203 0.6958 0.4711 0.025 Uiso 1 1 calc R U . . .
H19B H 0.3555 0.5894 0.5436 0.025 Uiso 1 1 calc R U . . .
C20 C 0.26467(18) 0.47078(17) 0.48351(11) 0.0213(3) Uani 1 1 d . . . . .
H20A H 0.3441 0.4434 0.4245 0.026 Uiso 1 1 calc R U . . .
H20B H 0.1653 0.4952 0.4583 0.026 Uiso 1 1 calc R U . . .
C21 C 0.30618(17) 0.33579(16) 0.56865(11) 0.0186(3) Uani 1 1 d . . . . .
H21A H 0.4111 0.3043 0.5874 0.022 Uiso 1 1 calc R U . . .
H21B H 0.3068 0.2511 0.5403 0.022 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C16 1.613(2) . ?
B1 C10 1.625(2) . ?
B1 N2 1.6259(18) . ?
B1 N1 1.6400(18) . ?
B1 C1 2.080(2) . ?
N1 C1 1.3296(18) . ?
N1 C2 1.4618(18) . ?
N2 C1 1.3324(18) . ?
N2 C5 1.4623(18) . ?
N3 C1 1.3715(18) . ?
N3 C9 1.4482(19) . ?
N3 C8 1.4500(19) . ?
C2 C4 1.522(2) . ?
C2 C3 1.524(2) . ?
C5 C6 1.512(2) . ?
C5 C7 1.522(2) . ?
C10 C11 1.5329(19) . ?
C10 C15 1.5372(19) . ?
C11 C12 1.526(2) . ?
C12 C13 1.524(2) . ?
C13 C14 1.521(2) . ?
C14 C15 1.528(2) . ?
C16 C21 1.5331(19) . ?
C16 C17 1.5413(19) . ?
C17 C18 1.522(2) . ?
C18 C19 1.523(2) . ?
C19 C20 1.520(2) . ?
C20 C21 1.524(2) . ?

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
C16 B1 C10 115.99(11) . . ?
C16 B1 N2 117.39(11) . . ?
C10 B1 N2 112.14(11) . . ?
C16 B1 N1 114.01(11) . . ?
C10 B1 N1 112.59(11) . . ?
N2 B1 N1 79.45(9) . . ?
C16 B1 C1 126.28(11) . . ?
C10 B1 C1 117.68(10) . . ?
N2 B1 C1 39.82(7) . . ?
N1 B1 C1 39.71(6) . . ?
C1 N1 C2 126.39(11) . . ?
C1 N1 B1 88.28(10) . . ?
C2 N1 B1 141.61(11) . . ?
C1 N2 C5 127.29(11) . . ?
C1 N2 B1 88.78(10) . . ?
C5 N2 B1 141.24(11) . . ?
C1 N3 C9 122.12(12) . . ?
C1 N3 C8 120.02(12) . . ?
C9 N3 C8 116.02(12) . . ?
N1 C1 N2 103.27(11) . . ?
N1 C1 N3 128.21(13) . . ?
N2 C1 N3 128.35(13) . . ?
N1 C1 B1 52.00(8) . . ?
N2 C1 B1 51.39(8) . . ?
N3 C1 B1 173.49(11) . . ?
N1 C2 C4 112.24(11) . . ?
N1 C2 C3 110.86(12) . . ?
C4 C2 C3 109.25(13) . . ?
N2 C5 C6 109.52(11) . . ?
N2 C5 C7 112.99(11) . . ?
C6 C5 C7 110.25(12) . . ?
C11 C10 C15 107.58(11) . . ?
C11 C10 B1 114.54(11) . . ?
C15 C10 B1 114.39(11) . . ?
C12 C11 C10 112.40(12) . . ?
C13 C12 C11 110.88(12) . . ?
C14 C13 C12 111.49(12) . . ?
C13 C14 C15 111.77(11) . . ?
C14 C15 C10 112.23(11) . . ?
C21 C16 C17 108.85(11) . . ?
C21 C16 B1 114.89(11) . . ?
C17 C16 B1 111.57(11) . . ?
C18 C17 C16 112.74(11) . . ?
C17 C18 C19 111.16(12) . . ?
C20 C19 C18 110.49(12) . . ?
C19 C20 C21 111.23(12) . . ?
C20 C21 C16 113.41(11) . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1479646'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H42 B N3'
_chemical_formula_weight         395.42

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6645(7)
_cell_length_b                   11.0217(12)
_cell_length_c                   11.9242(9)
_cell_angle_alpha                81.971(4)
_cell_angle_beta                 73.936(4)
_cell_angle_gamma                81.185(5)
_cell_volume                     1199.80(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9577
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.69

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29777
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         28.761
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6192
_reflns_number_gt                4668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.5711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6192
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1442
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.26418(16) 0.19660(15) 0.26456(13) 0.0109(3) Uani 1 1 d . . . . .
N1 N 0.39146(12) 0.23050(11) 0.31768(10) 0.0110(2) Uani 1 1 d . . . . .
N2 N 0.39713(12) 0.20617(11) 0.14506(10) 0.0109(2) Uani 1 1 d . . . . .
N3 N 0.62377(12) 0.24698(12) 0.17907(10) 0.0138(3) Uani 1 1 d . . . . .
H3 H 0.6532 0.2985 0.2127 0.017 Uiso 1 1 calc R U . . .
C1 C 0.48099(14) 0.23047(12) 0.21196(12) 0.0109(3) Uani 1 1 d . . . . .
C2 C 0.43490(15) 0.23101(13) 0.42596(12) 0.0129(3) Uani 1 1 d . . . . .
H2 H 0.5307 0.1831 0.4179 0.015 Uiso 1 1 calc R U . . .
C3 C 0.32832(17) 0.17082(15) 0.53049(12) 0.0183(3) Uani 1 1 d . . . . .
H3A H 0.2328 0.2140 0.5368 0.027 Uiso 1 1 d R U . . .
H3B H 0.3564 0.1746 0.6010 0.027 Uiso 1 1 d R U . . .
H3C H 0.3284 0.0862 0.5195 0.027 Uiso 1 1 d R U . . .
C4 C 0.44637(17) 0.36336(14) 0.44452(13) 0.0180(3) Uani 1 1 d . . . . .
H4A H 0.5134 0.3994 0.3773 0.027 Uiso 1 1 d R U . . .
H4B H 0.4801 0.3628 0.5132 0.027 Uiso 1 1 d R U . . .
H4C H 0.3527 0.4110 0.4546 0.027 Uiso 1 1 d R U . . .
C5 C 0.39612(14) 0.26009(13) 0.03119(11) 0.0112(3) Uani 1 1 d . . . . .
C6 C 0.29564(16) 0.22657(14) -0.02028(12) 0.0147(3) Uani 1 1 d . . . . .
H6 H 0.2366 0.1666 0.0193 0.018 Uiso 1 1 calc R U . . .
C7 C 0.28286(16) 0.28158(14) -0.12964(13) 0.0174(3) Uani 1 1 d . . . . .
H7 H 0.2149 0.2588 -0.1623 0.021 Uiso 1 1 calc R U . . .
C8 C 0.37131(16) 0.37052(14) -0.19048(13) 0.0177(3) Uani 1 1 d . . . . .
H8 H 0.3628 0.4076 -0.2636 0.021 Uiso 1 1 calc R U . . .
C9 C 0.47261(16) 0.40333(14) -0.14067(13) 0.0166(3) Uani 1 1 d . . . . .
H9 H 0.5327 0.4621 -0.1814 0.020 Uiso 1 1 calc R U . . .
C10 C 0.48531(15) 0.34954(13) -0.03089(12) 0.0136(3) Uani 1 1 d . . . . .
H10 H 0.5531 0.3729 0.0015 0.016 Uiso 1 1 calc R U . . .
C11 C 0.72986(15) 0.17909(15) 0.08735(13) 0.0169(3) Uani 1 1 d . . . . .
H11 H 0.6859 0.1771 0.0229 0.020 Uiso 1 1 calc R U . . .
C12 C 0.77001(18) 0.04688(16) 0.13545(16) 0.0260(4) Uani 1 1 d . . . . .
H12A H 0.8099 0.0473 0.2007 0.039 Uiso 1 1 d R U . . .
H12B H 0.8405 0.0048 0.0751 0.039 Uiso 1 1 d R U . . .
H12C H 0.6848 0.0051 0.1608 0.039 Uiso 1 1 d R U . . .
C13 C 0.86140(17) 0.24915(17) 0.04109(15) 0.0269(4) Uani 1 1 d . . . . .
H13A H 0.8319 0.3320 0.0120 0.040 Uiso 1 1 d R U . . .
H13B H 0.9296 0.2083 -0.0213 0.040 Uiso 1 1 d R U . . .
H13C H 0.9060 0.2512 0.1033 0.040 Uiso 1 1 d R U . . .
C14 C 0.22517(14) 0.05736(13) 0.30990(12) 0.0118(3) Uani 1 1 d . . . . .
H14 H 0.1721 0.0582 0.3928 0.014 Uiso 1 1 calc R U . . .
C15 C 0.35623(15) -0.04238(13) 0.30548(13) 0.0154(3) Uani 1 1 d . . . . .
H15A H 0.4099 -0.0492 0.2244 0.018 Uiso 1 1 calc R U . . .
H15B H 0.4202 -0.0177 0.3459 0.018 Uiso 1 1 calc R U . . .
C16 C 0.31024(16) -0.16856(14) 0.36223(13) 0.0172(3) Uani 1 1 d . . . . .
H16A H 0.3955 -0.2293 0.3545 0.021 Uiso 1 1 calc R U . . .
H16B H 0.2650 -0.1640 0.4452 0.021 Uiso 1 1 calc R U . . .
C17 C 0.20400(17) -0.20968(14) 0.30528(14) 0.0185(3) Uani 1 1 d . . . . .
H17A H 0.1700 -0.2856 0.3480 0.022 Uiso 1 1 calc R U . . .
H17B H 0.2537 -0.2262 0.2253 0.022 Uiso 1 1 calc R U . . .
C18 C 0.07383(16) -0.11124(14) 0.30440(14) 0.0179(3) Uani 1 1 d . . . . .
H18A H 0.0158 -0.1034 0.3842 0.021 Uiso 1 1 calc R U . . .
H18B H 0.0137 -0.1366 0.2609 0.021 Uiso 1 1 calc R U . . .
C19 C 0.12329(16) 0.01404(13) 0.24819(13) 0.0155(3) Uani 1 1 d . . . . .
H19A H 0.0388 0.0751 0.2518 0.019 Uiso 1 1 calc R U . . .
H19B H 0.1732 0.0079 0.1662 0.019 Uiso 1 1 calc R U . . .
C20 C 0.13003(14) 0.30349(13) 0.26335(12) 0.0116(3) Uani 1 1 d . . . . .
H20 H 0.0883 0.2883 0.2012 0.014 Uiso 1 1 calc R U . . .
C21 C 0.00718(16) 0.29794(14) 0.37784(13) 0.0161(3) Uani 1 1 d . . . . .
H21A H -0.0251 0.2167 0.3928 0.019 Uiso 1 1 calc R U . . .
H21B H 0.0450 0.3094 0.4425 0.019 Uiso 1 1 calc R U . . .
C22 C -0.12310(16) 0.39562(14) 0.37391(14) 0.0186(3) Uani 1 1 d . . . . .
H22A H -0.1689 0.3786 0.3159 0.022 Uiso 1 1 calc R U . . .
H22B H -0.1937 0.3915 0.4497 0.022 Uiso 1 1 calc R U . . .
C23 C -0.07644(16) 0.52527(14) 0.34306(13) 0.0164(3) Uani 1 1 d . . . . .
H23A H -0.1596 0.5848 0.3366 0.020 Uiso 1 1 calc R U . . .
H23B H -0.0399 0.5458 0.4052 0.020 Uiso 1 1 calc R U . . .
C24 C 0.04091(16) 0.53280(13) 0.22778(13) 0.0153(3) Uani 1 1 d . . . . .
H24A H 0.0720 0.6145 0.2115 0.018 Uiso 1 1 calc R U . . .
H24B H 0.0016 0.5196 0.1645 0.018 Uiso 1 1 calc R U . . .
C25 C 0.17159(15) 0.43586(13) 0.23296(13) 0.0145(3) Uani 1 1 d . . . . .
H25A H 0.2159 0.4541 0.2914 0.017 Uiso 1 1 calc R U . . .
H25B H 0.2430 0.4410 0.1576 0.017 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C20 1.614(2) . ?
B1 C14 1.619(2) . ?
B1 N2 1.6367(18) . ?
B1 N1 1.6407(18) . ?
N1 C1 1.3169(18) . ?
N1 C2 1.4650(17) . ?
N2 C1 1.3598(17) . ?
N2 C5 1.4061(17) . ?
N3 C1 1.3596(17) . ?
N3 C11 1.4765(19) . ?
C2 C3 1.5240(19) . ?
C2 C4 1.531(2) . ?
C5 C6 1.3998(19) . ?
C5 C10 1.4023(19) . ?
C6 C7 1.389(2) . ?
C7 C8 1.390(2) . ?
C8 C9 1.390(2) . ?
C9 C10 1.389(2) . ?
C11 C13 1.520(2) . ?
C11 C12 1.523(2) . ?
C14 C15 1.539(2) . ?
C14 C19 1.5434(19) . ?
C15 C16 1.533(2) . ?
C16 C17 1.528(2) . ?
C17 C18 1.532(2) . ?
C18 C19 1.5332(19) . ?
C20 C25 1.5403(19) . ?
C20 C21 1.5424(19) . ?
C21 C22 1.533(2) . ?
C22 C23 1.530(2) . ?
C23 C24 1.522(2) . ?
C24 C25 1.534(2) . ?

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
C20 B1 C14 117.09(11) . . ?
C20 B1 N2 113.14(11) . . ?
C14 B1 N2 113.82(11) . . ?
C20 B1 N1 115.60(11) . . ?
C14 B1 N1 112.00(11) . . ?
N2 B1 N1 79.57(9) . . ?
C1 N1 C2 124.83(11) . . ?
C1 N1 B1 89.26(10) . . ?
C2 N1 B1 143.91(11) . . ?
C1 N2 C5 126.96(11) . . ?
C1 N2 B1 87.97(10) . . ?
C5 N2 B1 130.17(11) . . ?
C1 N3 C11 121.95(12) . . ?
N1 C1 N3 128.12(12) . . ?
N1 C1 N2 103.16(11) . . ?
N3 C1 N2 128.69(13) . . ?
N1 C2 C3 110.66(11) . . ?
N1 C2 C4 109.90(11) . . ?
C3 C2 C4 111.08(12) . . ?
C6 C5 C10 118.49(12) . . ?
C6 C5 N2 117.90(12) . . ?
C10 C5 N2 123.54(12) . . ?
C7 C6 C5 120.94(13) . . ?
C6 C7 C8 120.23(13) . . ?
C9 C8 C7 119.22(13) . . ?
C10 C9 C8 120.94(13) . . ?
C9 C10 C5 120.16(13) . . ?
N3 C11 C13 108.25(13) . . ?
N3 C11 C12 110.71(13) . . ?
C13 C11 C12 112.06(13) . . ?
C15 C14 C19 108.08(12) . . ?
C15 C14 B1 115.43(11) . . ?
C19 C14 B1 114.00(11) . . ?
C16 C15 C14 112.04(12) . . ?
C17 C16 C15 111.46(12) . . ?
C16 C17 C18 111.58(12) . . ?
C17 C18 C19 111.10(12) . . ?
C18 C19 C14 112.14(11) . . ?
C25 C20 C21 109.12(12) . . ?
C25 C20 B1 115.02(11) . . ?
C21 C20 B1 113.30(11) . . ?
C22 C21 C20 113.07(12) . . ?
C23 C22 C21 111.10(12) . . ?
C24 C23 C22 110.73(12) . . ?
C23 C24 C25 110.93(12) . . ?
C24 C25 C20 112.67(11) . . ?

_refine_diff_density_max         0.574
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1479647'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H71 B2 N3'
_chemical_formula_weight         627.62

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.0277(8)
_cell_length_b                   27.932(2)
_cell_length_c                   12.7490(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.522(2)
_cell_angle_gamma                90
_cell_volume                     3847.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7299
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.68

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72347
_diffrn_reflns_av_unetI/netI     0.1462
_diffrn_reflns_av_R_equivalents  0.2339
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         28.748
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9953
_reflns_number_gt                5538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+2.2440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9953
_refine_ls_number_parameters     422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1851
_refine_ls_R_factor_gt           0.0914
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.6040(2) 0.05586(10) 0.7490(2) 0.0131(6) Uani 1 1 d . . . . .
B2 B 0.8608(3) 0.17364(10) 0.8908(2) 0.0133(6) Uani 1 1 d . . . . .
N1 N 0.66310(17) 0.08177(7) 0.86430(14) 0.0110(4) Uani 1 1 d . . . . .
N2 N 0.72922(17) 0.07947(7) 0.72315(14) 0.0111(4) Uani 1 1 d . . . . .
N3 N 0.86314(17) 0.12329(7) 0.87178(14) 0.0105(4) Uani 1 1 d . . . . .
C1 C 0.7567(2) 0.09681(8) 0.82336(17) 0.0106(5) Uani 1 1 d . . . . .
C2 C 0.6478(2) 0.08655(9) 0.97534(17) 0.0148(5) Uani 1 1 d . . . . .
H2 H 0.7169 0.1056 1.0143 0.018 Uiso 1 1 calc R U . . .
C3 C 0.5278(2) 0.11265(10) 0.9807(2) 0.0254(6) Uani 1 1 d . . . . .
H3A H 0.5234 0.1419 0.9405 0.038 Uiso 1 1 d R U . . .
H3B H 0.5259 0.1199 1.0540 0.038 Uiso 1 1 d R U . . .
H3C H 0.4586 0.0927 0.9512 0.038 Uiso 1 1 d R U . . .
C4 C 0.6502(3) 0.03782(10) 1.0303(2) 0.0255(6) Uani 1 1 d . . . . .
H4A H 0.5910 0.0169 0.9875 0.038 Uiso 1 1 d R U . . .
H4B H 0.6298 0.0418 1.0995 0.038 Uiso 1 1 d R U . . .
H4C H 0.7314 0.0241 1.0383 0.038 Uiso 1 1 d R U . . .
C5 C 0.7778(2) 0.08945(8) 0.63171(17) 0.0115(5) Uani 1 1 d . . . . .
C6 C 0.7613(3) 0.05536(10) 0.5511(2) 0.0261(6) Uani 1 1 d . . . . .
H6 H 0.7176 0.0275 0.5584 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8091(3) 0.06229(11) 0.4600(2) 0.0300(7) Uani 1 1 d . . . . .
H7 H 0.7963 0.0388 0.4072 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8752(2) 0.10283(9) 0.44443(18) 0.0146(5) Uani 1 1 d . . . . .
C9 C 0.8885(2) 0.13738(9) 0.52425(19) 0.0185(6) Uani 1 1 d . . . . .
H9 H 0.9313 0.1654 0.5162 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8395(2) 0.13125(9) 0.61607(19) 0.0182(6) Uani 1 1 d . . . . .
H10 H 0.8483 0.1554 0.6672 0.022 Uiso 1 1 calc R U . . .
C11 C 0.9258(2) 0.10874(9) 0.34172(18) 0.0176(5) Uani 1 1 d . . . . .
C12 C 0.9922(3) 0.06298(11) 0.3195(2) 0.0325(7) Uani 1 1 d . . . . .
H12A H 1.0281 0.0675 0.2576 0.049 Uiso 1 1 d R U . . .
H12B H 0.9346 0.0368 0.3071 0.049 Uiso 1 1 d R U . . .
H12C H 1.0563 0.0559 0.3804 0.049 Uiso 1 1 d R U . . .
C13 C 0.8169(2) 0.11861(10) 0.24883(19) 0.0251(6) Uani 1 1 d . . . . .
H13A H 0.7732 0.1466 0.2645 0.038 Uiso 1 1 d R U . . .
H13B H 0.7619 0.0916 0.2395 0.038 Uiso 1 1 d R U . . .
H13C H 0.8475 0.1238 0.1843 0.038 Uiso 1 1 d R U . . .
C14 C 1.0169(3) 0.15029(11) 0.3480(2) 0.0282(7) Uani 1 1 d . . . . .
H14A H 0.9765 0.1796 0.3600 0.042 Uiso 1 1 d R U . . .
H14B H 1.0463 0.1525 0.2821 0.042 Uiso 1 1 d R U . . .
H14C H 1.0856 0.1448 0.4061 0.042 Uiso 1 1 d R U . . .
C15 C 0.9769(2) 0.09297(8) 0.90672(18) 0.0142(5) Uani 1 1 d . . . . .
H15 H 1.0454 0.1152 0.9317 0.017 Uiso 1 1 calc R U . . .
C16 C 0.9645(2) 0.06238(9) 1.00233(19) 0.0204(6) Uani 1 1 d . . . . .
H16A H 0.9410 0.0821 1.0567 0.031 Uiso 1 1 d R U . . .
H16B H 1.0421 0.0471 1.0306 0.031 Uiso 1 1 d R U . . .
H16C H 0.9022 0.0384 0.9800 0.031 Uiso 1 1 d R U . . .
C17 C 1.0140(2) 0.06334(10) 0.8184(2) 0.0241(6) Uani 1 1 d . . . . .
H17A H 0.9523 0.0393 0.7953 0.036 Uiso 1 1 d R U . . .
H17B H 1.0923 0.0483 0.8451 0.036 Uiso 1 1 d R U . . .
H17C H 1.0208 0.0836 0.7590 0.036 Uiso 1 1 d R U . . .
C18 C 0.9843(2) 0.20338(9) 0.93515(18) 0.0157(5) Uani 1 1 d . . . . .
H18 H 0.9572 0.2368 0.9341 0.019 Uiso 1 1 calc R U . . .
C19 C 1.0801(2) 0.20225(9) 0.8615(2) 0.0209(6) Uani 1 1 d . . . . .
H19A H 1.0997 0.1692 0.8487 0.025 Uiso 1 1 calc R U . . .
H19B H 1.0433 0.2164 0.7930 0.025 Uiso 1 1 calc R U . . .
C20 C 1.2005(2) 0.22901(10) 0.9081(2) 0.0298(7) Uani 1 1 d . . . . .
H20A H 1.2607 0.2233 0.8634 0.036 Uiso 1 1 calc R U . . .
H20B H 1.1843 0.2631 0.9080 0.036 Uiso 1 1 calc R U . . .
C21 C 1.2535(2) 0.21266(10) 1.0217(2) 0.0315(7) Uani 1 1 d . . . . .
H21A H 1.2735 0.1789 1.0214 0.038 Uiso 1 1 calc R U . . .
H21B H 1.3292 0.2301 1.0493 0.038 Uiso 1 1 calc R U . . .
C22 C 1.1614(3) 0.22108(10) 1.0937(2) 0.0286(7) Uani 1 1 d . . . . .
H22A H 1.1427 0.2550 1.0951 0.034 Uiso 1 1 calc R U . . .
H22B H 1.1976 0.2111 1.1661 0.034 Uiso 1 1 calc R U . . .
C23 C 1.0422(2) 0.19311(9) 1.05376(19) 0.0196(6) Uani 1 1 d . . . . .
H23A H 0.9827 0.2012 1.0976 0.023 Uiso 1 1 calc R U . . .
H23B H 1.0596 0.1591 1.0623 0.023 Uiso 1 1 calc R U . . .
C24 C 0.7324(2) 0.20121(8) 0.86906(18) 0.0138(5) Uani 1 1 d . . . . .
H24 H 0.6664 0.1777 0.8460 0.017 Uiso 1 1 calc R U . . .
C25 C 0.7110(2) 0.22467(9) 0.97410(19) 0.0179(5) Uani 1 1 d . . . . .
H25A H 0.7121 0.2000 1.0279 0.021 Uiso 1 1 calc R U . . .
H25B H 0.7782 0.2467 1.0003 0.021 Uiso 1 1 calc R U . . .
C26 C 0.5885(2) 0.25161(10) 0.9585(2) 0.0252(6) Uani 1 1 d . . . . .
H26A H 0.5809 0.2669 1.0252 0.030 Uiso 1 1 calc R U . . .
H26B H 0.5206 0.2292 0.9392 0.030 Uiso 1 1 calc R U . . .
C27 C 0.5804(3) 0.28944(9) 0.8712(2) 0.0259(6) Uani 1 1 d . . . . .
H27A H 0.4999 0.3048 0.8600 0.031 Uiso 1 1 calc R U . . .
H27B H 0.6430 0.3137 0.8938 0.031 Uiso 1 1 calc R U . . .
C28 C 0.5991(2) 0.26718(9) 0.7669(2) 0.0247(6) Uani 1 1 d . . . . .
H28A H 0.5976 0.2921 0.7137 0.030 Uiso 1 1 calc R U . . .
H28B H 0.5316 0.2453 0.7407 0.030 Uiso 1 1 calc R U . . .
C29 C 0.7222(2) 0.24009(9) 0.78148(19) 0.0189(6) Uani 1 1 d . . . . .
H29A H 0.7900 0.2626 0.8008 0.023 Uiso 1 1 calc R U . . .
H29B H 0.7293 0.2252 0.7142 0.023 Uiso 1 1 calc R U . . .
C30 C 0.4814(2) 0.07994(9) 0.67904(18) 0.0150(5) Uani 1 1 d . . . . .
H30 H 0.4782 0.0689 0.6055 0.018 Uiso 1 1 calc R U . . .
C31 C 0.4812(2) 0.13473(9) 0.6729(2) 0.0215(6) Uani 1 1 d . . . . .
H31A H 0.4852 0.1476 0.7442 0.026 Uiso 1 1 calc R U . . .
H31B H 0.5547 0.1452 0.6484 0.026 Uiso 1 1 calc R U . . .
C32 C 0.3673(3) 0.15496(10) 0.5983(2) 0.0295(7) Uani 1 1 d . . . . .
H32A H 0.3693 0.1896 0.6018 0.035 Uiso 1 1 calc R U . . .
H32B H 0.3682 0.1455 0.5252 0.035 Uiso 1 1 calc R U . . .
C33 C 0.2494(3) 0.13677(11) 0.6295(2) 0.0344(8) Uani 1 1 d . . . . .
H33A H 0.2447 0.1488 0.6999 0.041 Uiso 1 1 calc R U . . .
H33B H 0.1782 0.1487 0.5789 0.041 Uiso 1 1 calc R U . . .
C34 C 0.2466(2) 0.08250(11) 0.6307(2) 0.0292(7) Uani 1 1 d . . . . .
H34A H 0.2456 0.0704 0.5592 0.035 Uiso 1 1 calc R U . . .
H34B H 0.1719 0.0717 0.6526 0.035 Uiso 1 1 calc R U . . .
C35 C 0.3596(2) 0.06297(10) 0.7077(2) 0.0203(6) Uani 1 1 d . . . . .
H35A H 0.3570 0.0283 0.7064 0.024 Uiso 1 1 calc R U . . .
H35B H 0.3569 0.0733 0.7799 0.024 Uiso 1 1 calc R U . . .
C36 C 0.6019(2) -0.00229(8) 0.75741(18) 0.0137(5) Uani 1 1 d . . . . .
H36 H 0.5485 -0.0095 0.8083 0.016 Uiso 1 1 calc R U . . .
C37 C 0.5445(2) -0.02928(8) 0.65373(19) 0.0165(5) Uani 1 1 d . . . . .
H37A H 0.4639 -0.0157 0.6242 0.020 Uiso 1 1 calc R U . . .
H37B H 0.5965 -0.0249 0.6015 0.020 Uiso 1 1 calc R U . . .
C38 C 0.5302(2) -0.08271(9) 0.6731(2) 0.0209(6) Uani 1 1 d . . . . .
H38A H 0.4726 -0.0873 0.7206 0.025 Uiso 1 1 calc R U . . .
H38B H 0.4965 -0.0984 0.6058 0.025 Uiso 1 1 calc R U . . .
C39 C 0.6541(3) -0.10541(9) 0.7226(2) 0.0290(7) Uani 1 1 d . . . . .
H39A H 0.6412 -0.1387 0.7394 0.035 Uiso 1 1 calc R U . . .
H39B H 0.7081 -0.1046 0.6712 0.035 Uiso 1 1 calc R U . . .
C40 C 0.7157(2) -0.07925(9) 0.8240(2) 0.0234(6) Uani 1 1 d . . . . .
H40A H 0.7975 -0.0925 0.8497 0.028 Uiso 1 1 calc R U . . .
H40B H 0.6676 -0.0841 0.8790 0.028 Uiso 1 1 calc R U . . .
C41 C 0.7269(2) -0.02560(8) 0.8040(2) 0.0175(5) Uani 1 1 d . . . . .
H41A H 0.7826 -0.0207 0.7549 0.021 Uiso 1 1 calc R U . . .
H41B H 0.7628 -0.0100 0.8710 0.021 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C30 1.610(4) . ?
B1 N2 1.622(3) . ?
B1 C36 1.628(4) . ?
B1 N1 1.651(3) . ?
B2 N3 1.428(3) . ?
B2 C24 1.587(4) . ?
B2 C18 1.599(4) . ?
N1 C1 1.315(3) . ?
N1 C2 1.465(3) . ?
N2 C1 1.343(3) . ?
N2 C5 1.405(3) . ?
N3 C1 1.420(3) . ?
N3 C15 1.506(3) . ?
C2 C3 1.524(3) . ?
C2 C4 1.529(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.386(3) . ?
C5 C10 1.386(3) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(3) . ?
C8 C11 1.532(3) . ?
C9 C10 1.395(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C14 1.526(4) . ?
C11 C12 1.527(4) . ?
C11 C13 1.534(3) . ?
C12 H12A 0.9601 . ?
C12 H12B 0.9601 . ?
C12 H12C 0.9601 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9601 . ?
C14 H14B 0.9601 . ?
C14 H14C 0.9601 . ?
C15 C16 1.517(3) . ?
C15 C17 1.518(3) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.546(3) . ?
C18 C19 1.548(3) . ?
C18 H18 0.9800 . ?
C19 C20 1.536(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.520(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.517(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.527(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C29 1.545(3) . ?
C24 C25 1.551(3) . ?
C24 H24 0.9800 . ?
C25 C26 1.525(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.525(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.519(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.533(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.532(3) . ?
C30 C35 1.536(3) . ?
C30 H30 0.9800 . ?
C31 C32 1.524(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.521(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.517(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.525(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C41 1.534(3) . ?
C36 C37 1.543(3) . ?
C36 H36 0.9800 . ?
C37 C38 1.526(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.523(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.522(4) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.529(3) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?

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
C30 B1 N2 111.82(19) . . ?
C30 B1 C36 115.6(2) . . ?
N2 B1 C36 116.30(19) . . ?
C30 B1 N1 116.64(19) . . ?
N2 B1 N1 78.59(15) . . ?
C36 B1 N1 112.78(19) . . ?
N3 B2 C24 119.6(2) . . ?
N3 B2 C18 121.9(2) . . ?
C24 B2 C18 118.5(2) . . ?
C1 N1 C2 127.27(19) . . ?
C1 N1 B1 89.32(16) . . ?
C2 N1 B1 143.04(19) . . ?
C1 N2 C5 131.8(2) . . ?
C1 N2 B1 89.58(16) . . ?
C5 N2 B1 136.93(18) . . ?
C1 N3 B2 123.1(2) . . ?
C1 N3 C15 113.79(18) . . ?
B2 N3 C15 123.08(19) . . ?
N1 C1 N2 102.51(19) . . ?
N1 C1 N3 129.8(2) . . ?
N2 C1 N3 127.7(2) . . ?
N1 C2 C3 110.85(19) . . ?
N1 C2 C4 111.50(19) . . ?
C3 C2 C4 110.0(2) . . ?
N1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C4 C2 H2 108.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.4 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 117.9(2) . . ?
C6 C5 N2 117.6(2) . . ?
C10 C5 N2 124.5(2) . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 122.4(2) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C7 C8 C9 116.5(2) . . ?
C7 C8 C11 120.3(2) . . ?
C9 C8 C11 123.2(2) . . ?
C8 C9 C10 121.8(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C5 C10 C9 120.5(2) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C14 C11 C12 108.1(2) . . ?
C14 C11 C8 112.7(2) . . ?
C12 C11 C8 109.8(2) . . ?
C14 C11 C13 108.0(2) . . ?
C12 C11 C13 109.7(2) . . ?
C8 C11 C13 108.4(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.0 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.7 . . ?
C11 C14 H14B 109.6 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.1 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C16 110.51(19) . . ?
N3 C15 C17 114.78(19) . . ?
C16 C15 C17 111.7(2) . . ?
N3 C15 H15 106.4 . . ?
C16 C15 H15 106.4 . . ?
C17 C15 H15 106.4 . . ?
C15 C16 H16A 109.7 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.1 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.3 . . ?
C15 C17 H17B 109.4 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.7 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 113.0(2) . . ?
C23 C18 B2 113.92(19) . . ?
C19 C18 B2 114.3(2) . . ?
C23 C18 H18 104.8 . . ?
C19 C18 H18 104.8 . . ?
B2 C18 H18 104.8 . . ?
C20 C19 C18 113.4(2) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 111.1(2) . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 110.7(2) . . ?
C22 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 C23 110.8(2) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 C18 113.0(2) . . ?
C22 C23 H23A 109.0 . . ?
C18 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C18 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C29 C24 C25 108.97(19) . . ?
C29 C24 B2 113.7(2) . . ?
C25 C24 B2 109.77(19) . . ?
C29 C24 H24 108.1 . . ?
C25 C24 H24 108.1 . . ?
B2 C24 H24 108.1 . . ?
C26 C25 C24 112.3(2) . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C24 C25 H25B 109.1 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 C27 111.0(2) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C28 C27 C26 110.9(2) . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.0 . . ?
C27 C28 C29 111.6(2) . . ?
C27 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?
C28 C29 C24 111.7(2) . . ?
C28 C29 H29A 109.3 . . ?
C24 C29 H29A 109.3 . . ?
C28 C29 H29B 109.3 . . ?
C24 C29 H29B 109.3 . . ?
H29A C29 H29B 107.9 . . ?
C31 C30 C35 109.1(2) . . ?
C31 C30 B1 116.0(2) . . ?
C35 C30 B1 114.6(2) . . ?
C31 C30 H30 105.4 . . ?
C35 C30 H30 105.4 . . ?
B1 C30 H30 105.4 . . ?
C32 C31 C30 113.2(2) . . ?
C32 C31 H31A 108.9 . . ?
C30 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C33 C32 C31 110.7(2) . . ?
C33 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 C32 110.9(2) . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 108.0 . . ?
C33 C34 C35 110.4(2) . . ?
C33 C34 H34A 109.6 . . ?
C35 C34 H34A 109.6 . . ?
C33 C34 H34B 109.6 . . ?
C35 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
C34 C35 C30 112.2(2) . . ?
C34 C35 H35A 109.2 . . ?
C30 C35 H35A 109.2 . . ?
C34 C35 H35B 109.2 . . ?
C30 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?
C41 C36 C37 107.93(19) . . ?
C41 C36 B1 115.2(2) . . ?
C37 C36 B1 116.10(19) . . ?
C41 C36 H36 105.6 . . ?
C37 C36 H36 105.6 . . ?
B1 C36 H36 105.6 . . ?
C38 C37 C36 112.1(2) . . ?
C38 C37 H37A 109.2 . . ?
C36 C37 H37A 109.2 . . ?
C38 C37 H37B 109.2 . . ?
C36 C37 H37B 109.2 . . ?
H37A C37 H37B 107.9 . . ?
C39 C38 C37 111.2(2) . . ?
C39 C38 H38A 109.4 . . ?
C37 C38 H38A 109.4 . . ?
C39 C38 H38B 109.4 . . ?
C37 C38 H38B 109.4 . . ?
H38A C38 H38B 108.0 . . ?
C40 C39 C38 111.3(2) . . ?
C40 C39 H39A 109.4 . . ?
C38 C39 H39A 109.4 . . ?
C40 C39 H39B 109.4 . . ?
C38 C39 H39B 109.4 . . ?
H39A C39 H39B 108.0 . . ?
C39 C40 C41 111.5(2) . . ?
C39 C40 H40A 109.3 . . ?
C41 C40 H40A 109.3 . . ?
C39 C40 H40B 109.3 . . ?
C41 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
C40 C41 C36 112.6(2) . . ?
C40 C41 H41A 109.1 . . ?
C36 C41 H41A 109.1 . . ?
C40 C41 H41B 109.1 . . ?
C36 C41 H41B 109.1 . . ?
H41A C41 H41B 107.8 . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.065

_shelxl_version_number           2014-3

