# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_wa3222
_database_code_depnum_ccdc_archive 'CCDC 2338779'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 B2 Cl4'
_chemical_formula_sum            'C6 H4 B2 Cl4'
_chemical_formula_weight         239.51

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   3.9587(3)
_cell_length_b                   14.8849(9)
_cell_length_c                   8.3966(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.651(5)
_cell_angle_gamma                90
_cell_volume                     484.57(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    23411
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      26.1

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    1.154
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7798
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.692
_diffrn_reflns_theta_max         25.613
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             906
_reflns_number_gt                859
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_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)+(0.0706P)²+0.1510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         906
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
Cl1 Cl 0.19855(15) 0.40118(4) 0.41343(7) 0.0551(3) Uani 1 1 d . . . . .
Cl2 Cl 0.33015(19) 0.25259(4) 0.19506(8) 0.0662(3) Uani 1 1 d . . . . .
B1 B 0.3185(6) 0.36816(16) 0.2337(3) 0.0460(5) Uani 1 1 d . . . . .
C1 C 0.4140(5) 0.43682(13) 0.1115(2) 0.0419(5) Uani 1 1 d . . . . .
C2 C 0.4148(5) 0.52964(13) 0.1438(3) 0.0441(5) Uani 1 1 d . . . . .
H2 H 0.357059 0.550413 0.241947 0.053 Uiso 1 1 calc R U . . .
C3 C 0.4985(6) 0.59070(13) 0.0345(3) 0.0447(5) Uani 1 1 d . . . . .
H3 H 0.496907 0.653008 0.058889 0.054 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
Cl1 B1 1.742(3) . ?
Cl2 B1 1.753(3) . ?
B1 C1 1.548(3) . ?
C1 C3 1.401(3) 3_665 ?
C1 C2 1.408(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 B1 Cl1 122.25(17) . . ?
C1 B1 Cl2 120.42(18) . . ?
Cl1 B1 Cl2 117.33(14) . . ?
C3 C1 C2 117.66(19) 3_665 . ?
C3 C1 B1 121.57(18) 3_665 . ?
C2 C1 B1 120.77(19) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C1 121.67(19) . 3_665 ?
C2 C3 H3 119.2 . . ?
C1 C3 H3 119.2 3_665 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 B1 C1 C3 -178.34(16) . . . 3_665 ?
Cl2 B1 C1 C3 2.0(3) . . . 3_665 ?
Cl1 B1 C1 C2 1.5(3) . . . . ?
Cl2 B1 C1 C2 -178.18(16) . . . . ?
C3 C1 C2 C3 0.1(3) 3_665 . . . ?
B1 C1 C2 C3 -179.74(19) . . . . ?
C1 C2 C3 C1 -0.1(3) . . . 3_665 ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.066


####################################################################### 
# 
# 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_wa3051
_database_code_depnum_ccdc_archive 'CCDC 2338784'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 B N3'
_chemical_formula_sum            'C18 H18 B N3'
_chemical_formula_weight         287.16

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.2323(3)
_cell_length_b                   10.5998(4)
_cell_length_c                   20.4068(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1564.40(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    16518
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      28.0

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16518
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.771
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3587
_reflns_number_gt                3465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.994

_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_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)+(0.0513P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.064(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1358 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3587
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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
N1 N 0.5768(2) 0.65283(15) 0.65336(8) 0.0396(4) Uani 1 1 d . . . . .
N2 N 0.3339(2) 0.51709(16) 0.60820(8) 0.0412(4) Uani 1 1 d . . . . .
N3 N 0.8933(3) 0.5449(2) 0.35205(9) 0.0524(4) Uani 1 1 d . . . . .
H3A H 0.894(4) 0.614(3) 0.3238(15) 0.077(9) Uiso 1 1 d . . . . .
H3B H 0.952(4) 0.474(3) 0.3432(13) 0.072(9) Uiso 1 1 d . . . . .
B1 B 0.5056(3) 0.5815(2) 0.59971(10) 0.0409(4) Uani 1 1 d . . . . .
C1 C 0.4787(3) 0.66588(18) 0.71224(9) 0.0384(4) Uani 1 1 d . . . . .
C2 C 0.3085(3) 0.59770(17) 0.71931(9) 0.0378(4) Uani 1 1 d . . . . .
C3 C 0.2370(3) 0.52034(17) 0.66778(9) 0.0396(4) Uani 1 1 d . . . . .
C4 C 0.0747(3) 0.4537(2) 0.67788(11) 0.0490(5) Uani 1 1 d . . . . .
H4 H 0.026936 0.401888 0.643882 0.059 Uiso 1 1 calc R U . . .
C5 C -0.0199(3) 0.4620(2) 0.73757(11) 0.0549(5) Uani 1 1 d . . . . .
H5 H -0.130247 0.414766 0.743563 0.066 Uiso 1 1 calc R U . . .
C6 C 0.0432(3) 0.5362(2) 0.78723(11) 0.0512(5) Uani 1 1 d . . . . .
H6 H -0.023659 0.540784 0.827244 0.061 Uiso 1 1 calc R U . . .
C7 C 0.2081(3) 0.60670(18) 0.77938(9) 0.0425(4) Uani 1 1 d . . . . .
C8 C 0.2765(3) 0.6865(2) 0.82986(10) 0.0485(5) Uani 1 1 d . . . . .
H8 H 0.210615 0.693730 0.869957 0.058 Uiso 1 1 calc R U . . .
C9 C 0.4359(3) 0.7525(2) 0.82103(10) 0.0496(5) Uani 1 1 d . . . . .
H9 H 0.478667 0.806527 0.854956 0.060 Uiso 1 1 calc R U . . .
C10 C 0.5385(3) 0.74263(18) 0.76291(9) 0.0443(4) Uani 1 1 d . . . . .
H10 H 0.650145 0.789024 0.758272 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7537(3) 0.7199(2) 0.64889(11) 0.0480(5) Uani 1 1 d . . . . .
H11A H 0.731589 0.811092 0.650610 0.077 Uiso 1 1 calc R U . . .
H11B H 0.814637 0.698471 0.607463 0.077 Uiso 1 1 calc R U . . .
H11C H 0.833140 0.695083 0.685590 0.077 Uiso 1 1 calc R U . . .
C12 C 0.2445(3) 0.4502(2) 0.55399(11) 0.0563(6) Uani 1 1 d . . . . .
H12A H 0.237825 0.359983 0.564210 0.090 Uiso 1 1 calc R U . . .
H12B H 0.316466 0.462441 0.513803 0.090 Uiso 1 1 calc R U . . .
H12C H 0.119282 0.483430 0.547677 0.090 Uiso 1 1 calc R U . . .
C21 C 0.6126(3) 0.57213(19) 0.53275(9) 0.0417(4) Uani 1 1 d . . . . .
C22 C 0.7109(3) 0.4637(2) 0.51473(10) 0.0490(5) Uani 1 1 d . . . . .
H22 H 0.713521 0.394098 0.544032 0.059 Uiso 1 1 calc R U . . .
C23 C 0.8041(3) 0.4545(2) 0.45586(10) 0.0476(5) Uani 1 1 d . . . . .
H23 H 0.870788 0.379745 0.445818 0.057 Uiso 1 1 calc R U . . .
C24 C 0.8013(3) 0.55362(18) 0.41106(9) 0.0389(4) Uani 1 1 d . . . . .
C25 C 0.7013(3) 0.66141(18) 0.42740(9) 0.0430(4) Uani 1 1 d . . . . .
H25 H 0.694534 0.729401 0.397162 0.052 Uiso 1 1 calc R U . . .
C26 C 0.6114(3) 0.67080(19) 0.48720(10) 0.0442(4) Uani 1 1 d . . . . .
H26 H 0.547203 0.746406 0.497557 0.053 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
N1 C1 1.402(2) . ?
N1 B1 1.427(3) . ?
N1 C11 1.467(2) . ?
N2 C3 1.404(2) . ?
N2 B1 1.428(3) . ?
N2 C12 1.464(2) . ?
N3 C24 1.379(2) . ?
N3 H3A 0.93(3) . ?
N3 H3B 0.88(3) . ?
B1 C21 1.573(3) . ?
C1 C10 1.385(3) . ?
C1 C2 1.435(3) . ?
C2 C7 1.428(3) . ?
C2 C3 1.430(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.400(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.362(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.417(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.422(3) . ?
C8 C9 1.361(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C21 C26 1.399(3) . ?
C21 C22 1.400(3) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 B1 121.83(16) . . ?
C1 N1 C11 116.55(15) . . ?
B1 N1 C11 121.59(16) . . ?
C3 N2 B1 121.84(16) . . ?
C3 N2 C12 116.46(16) . . ?
B1 N2 C12 121.61(17) . . ?
C24 N3 H3A 119.5(19) . . ?
C24 N3 H3B 118.1(18) . . ?
H3A N3 H3B 122(3) . . ?
N1 B1 N2 118.31(17) . . ?
N1 B1 C21 121.51(18) . . ?
N2 B1 C21 120.18(17) . . ?
C10 C1 N1 122.66(17) . . ?
C10 C1 C2 119.27(17) . . ?
N1 C1 C2 118.07(16) . . ?
C7 C2 C3 119.06(17) . . ?
C7 C2 C1 119.27(17) . . ?
C3 C2 C1 121.67(16) . . ?
C4 C3 N2 122.65(17) . . ?
C4 C3 C2 119.29(17) . . ?
N2 C3 C2 118.05(16) . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.16(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 121.64(19) . . ?
C6 C7 C2 119.35(18) . . ?
C8 C7 C2 119.01(19) . . ?
C9 C8 C7 120.32(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.44(19) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C1 C10 C9 120.65(19) . . ?
C1 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C26 C21 C22 116.22(17) . . ?
C26 C21 B1 121.79(17) . . ?
C22 C21 B1 121.97(17) . . ?
C23 C22 C21 122.30(18) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C22 C23 C24 120.69(19) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
N3 C24 C25 120.96(18) . . ?
N3 C24 C23 121.06(19) . . ?
C25 C24 C23 117.98(17) . . ?
C26 C25 C24 120.88(17) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C21 121.90(18) . . ?
C25 C26 H26 119.1 . . ?
C21 C26 H26 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 B1 N2 -3.1(3) . . . . ?
C11 N1 B1 N2 178.98(17) . . . . ?
C1 N1 B1 C21 177.33(17) . . . . ?
C11 N1 B1 C21 -0.5(3) . . . . ?
C3 N2 B1 N1 -1.3(3) . . . . ?
C12 N2 B1 N1 175.1(2) . . . . ?
C3 N2 B1 C21 178.21(17) . . . . ?
C12 N2 B1 C21 -5.4(3) . . . . ?
B1 N1 C1 C10 -174.82(18) . . . . ?
C11 N1 C1 C10 3.2(3) . . . . ?
B1 N1 C1 C2 4.4(2) . . . . ?
C11 N1 C1 C2 -177.66(17) . . . . ?
C10 C1 C2 C7 -2.4(3) . . . . ?
N1 C1 C2 C7 178.42(16) . . . . ?
C10 C1 C2 C3 177.93(17) . . . . ?
N1 C1 C2 C3 -1.3(2) . . . . ?
B1 N2 C3 C4 -176.94(19) . . . . ?
C12 N2 C3 C4 6.5(3) . . . . ?
B1 N2 C3 C2 4.2(3) . . . . ?
C12 N2 C3 C2 -172.36(18) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
C1 C2 C3 C4 178.20(18) . . . . ?
C7 C2 C3 N2 177.37(16) . . . . ?
C1 C2 C3 N2 -2.9(3) . . . . ?
N2 C3 C4 C5 -178.50(19) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C8 179.1(2) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C3 C2 C7 C6 1.8(3) . . . . ?
C1 C2 C7 C6 -177.96(18) . . . . ?
C3 C2 C7 C8 -178.20(17) . . . . ?
C1 C2 C7 C8 2.1(3) . . . . ?
C6 C7 C8 C9 179.6(2) . . . . ?
C2 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
N1 C1 C10 C9 -179.86(17) . . . . ?
C2 C1 C10 C9 1.0(3) . . . . ?
C8 C9 C10 C1 0.8(3) . . . . ?
N1 B1 C21 C26 -77.3(3) . . . . ?
N2 B1 C21 C26 103.2(2) . . . . ?
N1 B1 C21 C22 104.1(2) . . . . ?
N2 B1 C21 C22 -75.4(3) . . . . ?
C26 C21 C22 C23 0.9(3) . . . . ?
B1 C21 C22 C23 179.6(2) . . . . ?
C21 C22 C23 C24 -1.0(3) . . . . ?
C22 C23 C24 N3 -179.7(2) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
N3 C24 C25 C26 -178.91(19) . . . . ?
C23 C24 C25 C26 1.7(3) . . . . ?
C24 C25 C26 C21 -1.8(3) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
B1 C21 C26 C25 -178.17(19) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.030


####################################################################### 
# 
# 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_wa3229
_database_code_depnum_ccdc_archive 'CCDC 2338782'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 B4 N2, C H2 Cl2'
_chemical_formula_sum            'C31 H30 B4 Cl2 N2'
_chemical_formula_weight         544.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   12.5056(7)
_cell_length_b                   23.4207(11)
_cell_length_c                   9.6710(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2832.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    20831
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      26.17

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26484
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.181
_diffrn_reflns_theta_max         25.707
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2734
_reflns_number_gt                2071
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_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)+(0.1163P)²+7.7718P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2734
_refine_ls_number_parameters     186
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2572
_refine_ls_wR_factor_gt          0.2302
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.047
_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
N1 N 0.5855(2) 0.62866(11) 0.6266(3) 0.0258(6) Uani 1 1 d . . . . .
B1 B 0.6540(3) 0.60152(16) 0.5250(4) 0.0268(8) Uani 1 1 d . . . . .
B2 B 0.5185(3) 0.59673(17) 0.7194(4) 0.0276(8) Uani 1 1 d . . . . .
C1 C 0.6632(2) 0.53533(13) 0.5298(3) 0.0248(7) Uani 1 1 d . . . . .
C2 C 0.6005(2) 0.50238(13) 0.6250(3) 0.0231(7) Uani 1 1 d . . . . .
C3 C 0.5286(2) 0.53025(13) 0.7174(3) 0.0245(7) Uani 1 1 d . . . . .
C4 C 0.4696(3) 0.49657(16) 0.8073(4) 0.0323(8) Uani 1 1 d . . . . .
H4 H 0.421745 0.514559 0.869959 0.039 Uiso 1 1 calc R U . . .
C5 C 0.4781(3) 0.43692(16) 0.8091(4) 0.0366(9) Uani 1 1 d . . . . .
H5 H 0.436173 0.415250 0.871970 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5464(3) 0.40988(15) 0.7207(4) 0.0323(8) Uani 1 1 d . . . . .
H6 H 0.551333 0.369406 0.721897 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6101(3) 0.44189(14) 0.6270(3) 0.0265(7) Uani 1 1 d . . . . .
C8 C 0.6825(3) 0.41508(14) 0.5356(4) 0.0315(8) Uani 1 1 d . . . . .
H8 H 0.689623 0.374699 0.537066 0.038 Uiso 1 1 calc R U . . .
C9 C 0.7419(3) 0.44626(15) 0.4457(4) 0.0338(8) Uani 1 1 d . . . . .
H9 H 0.790417 0.427664 0.384923 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7319(3) 0.50615(15) 0.4423(4) 0.0298(8) Uani 1 1 d . . . . .
H10 H 0.773495 0.527224 0.377870 0.036 Uiso 1 1 calc R U . . .
C11 C 0.7162(3) 0.63901(15) 0.4171(4) 0.0356(8) Uani 1 1 d . . . . .
H11A H 0.779595 0.655601 0.461126 0.053 Uiso 1 1 calc R U . . .
H11B H 0.669587 0.669688 0.383773 0.053 Uiso 1 1 calc R U . . .
H11C H 0.738369 0.615123 0.338933 0.053 Uiso 1 1 calc R U . . .
C12 C 0.4395(3) 0.62795(17) 0.8216(4) 0.0401(9) Uani 1 1 d . . . . .
H12A H 0.441114 0.669137 0.803831 0.060 Uiso 1 1 calc R U . . .
H12B H 0.461441 0.620559 0.917198 0.060 Uiso 1 1 calc R U . . .
H12C H 0.366742 0.613548 0.807200 0.060 Uiso 1 1 calc R U . . .
C13 C 0.5829(3) 0.69058(14) 0.6301(3) 0.0263(7) Uani 1 1 d . . . . .
C14 C 0.6591(3) 0.72022(14) 0.7035(4) 0.0333(8) Uani 1 1 d . . . . .
H14 H 0.711921 0.700026 0.754350 0.040 Uiso 1 1 calc R U . . .
C15 C 0.5057(3) 0.72020(15) 0.5585(4) 0.0363(9) Uani 1 1 d . . . . .
H15 H 0.452109 0.700005 0.508839 0.044 Uiso 1 1 calc R U . . .
C1L C 0.1067(14) 0.7208(6) 0.4233(16) 0.114(5) Uani 0.5 1 d . U P A -1
H1L1 H 0.096768 0.716229 0.524263 0.137 Uiso 0.5 1 calc R U P A -1
H1L2 H 0.112933 0.681836 0.384631 0.137 Uiso 0.5 1 calc R U P A -1
Cl1 Cl 0.2207(3) 0.750000 0.4032(3) 0.1195(11) Uani 1 2 d S T P . .
Cl2 Cl -0.0184(3) 0.750000 0.3570(4) 0.1372(13) 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
N1 B2 1.438(5) . ?
N1 B1 1.450(5) . ?
N1 C13 1.451(4) . ?
B1 C1 1.555(5) . ?
B1 C11 1.570(5) . ?
B2 C3 1.562(5) . ?
B2 C12 1.577(5) . ?
C1 C10 1.386(5) . ?
C1 C2 1.435(4) . ?
C2 C7 1.422(5) . ?
C2 C3 1.426(4) . ?
C3 C4 1.386(5) . ?
C4 C5 1.401(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.364(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.421(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(5) . ?
C8 C9 1.357(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.409(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.376(5) . ?
C13 C15 1.376(5) . ?
C14 C14 1.395(7) 7_575 ?
C14 H14 0.9500 . ?
C15 C15 1.396(7) 7_575 ?
C15 H15 0.9500 . ?
C1L Cl1 1.592(16) . ?
C1L Cl2 1.825(17) . ?
C1L H1L1 0.9900 . ?
C1L H1L2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B2 N1 B1 122.6(3) . . ?
B2 N1 C13 119.5(3) . . ?
B1 N1 C13 117.9(3) . . ?
N1 B1 C1 117.4(3) . . ?
N1 B1 C11 119.9(3) . . ?
C1 B1 C11 122.7(3) . . ?
N1 B2 C3 117.6(3) . . ?
N1 B2 C12 121.0(3) . . ?
C3 B2 C12 121.3(3) . . ?
C10 C1 C2 117.7(3) . . ?
C10 C1 B1 121.3(3) . . ?
C2 C1 B1 121.0(3) . . ?
C7 C2 C3 120.1(3) . . ?
C7 C2 C1 119.9(3) . . ?
C3 C2 C1 120.1(3) . . ?
C4 C3 C2 117.9(3) . . ?
C4 C3 B2 121.1(3) . . ?
C2 C3 B2 121.0(3) . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 C2 119.3(3) . . ?
C6 C7 C2 119.1(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C1 C10 C9 122.1(3) . . ?
C1 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
B1 C11 H11A 109.5 . . ?
B1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
B1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
B2 C12 H12A 109.5 . . ?
B2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
B2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C15 119.4(3) . . ?
C14 C13 N1 120.0(3) . . ?
C15 C13 N1 120.6(3) . . ?
C13 C14 C14 120.29(19) . 7_575 ?
C13 C14 H14 119.9 . . ?
C14 C14 H14 119.9 7_575 . ?
C13 C15 C15 120.3(2) . 7_575 ?
C13 C15 H15 119.9 . . ?
C15 C15 H15 119.9 7_575 . ?
Cl1 C1L Cl2 124.4(8) . . ?
Cl1 C1L H1L1 106.2 . . ?
Cl2 C1L H1L1 106.2 . . ?
Cl1 C1L H1L2 106.2 . . ?
Cl2 C1L H1L2 106.2 . . ?
H1L1 C1L H1L2 106.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B2 N1 B1 C1 -6.9(5) . . . . ?
C13 N1 B1 C1 175.2(3) . . . . ?
B2 N1 B1 C11 173.8(3) . . . . ?
C13 N1 B1 C11 -4.0(5) . . . . ?
B1 N1 B2 C3 5.3(5) . . . . ?
C13 N1 B2 C3 -176.8(3) . . . . ?
B1 N1 B2 C12 -175.8(3) . . . . ?
C13 N1 B2 C12 2.0(5) . . . . ?
N1 B1 C1 C10 -176.0(3) . . . . ?
C11 B1 C1 C10 3.3(5) . . . . ?
N1 B1 C1 C2 4.3(5) . . . . ?
C11 B1 C1 C2 -176.5(3) . . . . ?
C10 C1 C2 C7 0.0(4) . . . . ?
B1 C1 C2 C7 179.8(3) . . . . ?
C10 C1 C2 C3 180.0(3) . . . . ?
B1 C1 C2 C3 -0.3(4) . . . . ?
C7 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 179.9(3) . . . . ?
C7 C2 C3 B2 178.6(3) . . . . ?
C1 C2 C3 B2 -1.4(4) . . . . ?
N1 B2 C3 C4 177.6(3) . . . . ?
C12 B2 C3 C4 -1.2(5) . . . . ?
N1 B2 C3 C2 -1.0(5) . . . . ?
C12 B2 C3 C2 -179.8(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
B2 C3 C4 C5 -179.1(3) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 C8 179.2(3) . . . . ?
C5 C6 C7 C2 -1.0(5) . . . . ?
C3 C2 C7 C8 -179.4(3) . . . . ?
C1 C2 C7 C8 0.6(5) . . . . ?
C3 C2 C7 C6 0.8(5) . . . . ?
C1 C2 C7 C6 -179.2(3) . . . . ?
C6 C7 C8 C9 179.3(3) . . . . ?
C2 C7 C8 C9 -0.5(5) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C2 C1 C10 C9 -0.7(5) . . . . ?
B1 C1 C10 C9 179.6(3) . . . . ?
C8 C9 C10 C1 0.8(6) . . . . ?
B2 N1 C13 C14 97.4(4) . . . . ?
B1 N1 C13 C14 -84.6(4) . . . . ?
B2 N1 C13 C15 -83.7(4) . . . . ?
B1 N1 C13 C15 94.3(4) . . . . ?
C15 C13 C14 C14 -1.0(4) . . . 7_575 ?
N1 C13 C14 C14 177.87(19) . . . 7_575 ?
C14 C13 C15 C15 1.0(4) . . . 7_575 ?
N1 C13 C15 C15 -177.9(2) . . . 7_575 ?

_refine_diff_density_max         0.791
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.078


####################################################################### 
# 
# 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_wa3207
_database_code_depnum_ccdc_archive 'CCDC 2338781'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 B4 N2'
_chemical_formula_sum            'C26 H20 B4 N2'
_chemical_formula_weight         403.68

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           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                   3.9326(2)
_cell_length_b                   19.1064(14)
_cell_length_c                   13.7709(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.046(5)
_cell_angle_gamma                90
_cell_volume                     1034.72(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9038
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      25.95

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9038
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.525
_diffrn_reflns_theta_max         25.687
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1938
_reflns_number_gt                1655
_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+1.0108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1938
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_restrained_S_all      1.237
_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
N1 N 0.2441(6) 0.08237(11) 0.34195(16) 0.0237(5) Uani 1 1 d . . . . .
B1 B 0.3598(9) 0.05012(17) 0.2537(2) 0.0274(7) Uani 1 1 d . . . . .
H1 H 0.346(7) -0.0066(15) 0.2466(19) 0.025(7) Uiso 1 1 d . . . . .
B2 B 0.2589(9) 0.15691(17) 0.3502(2) 0.0273(7) Uani 1 1 d . . . . .
H2 H 0.151(7) 0.1833(13) 0.4154(18) 0.017(7) Uiso 1 1 d . . . . .
C1 C 0.5194(7) 0.09452(14) 0.17225(19) 0.0257(6) Uani 1 1 d . . . . .
C2 C 0.5421(7) 0.16908(14) 0.18169(19) 0.0250(6) Uani 1 1 d . . . . .
C3 C 0.4165(8) 0.20163(14) 0.2681(2) 0.0261(6) Uani 1 1 d . . . . .
C4 C 0.4440(8) 0.27374(15) 0.2756(2) 0.0312(7) Uani 1 1 d . . . . .
H4 H 0.362176 0.296354 0.332381 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5889(9) 0.31403(16) 0.2018(2) 0.0359(7) Uani 1 1 d . . . . .
H5 H 0.603941 0.363373 0.209131 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7096(8) 0.28308(16) 0.1190(2) 0.0333(7) Uani 1 1 d . . . . .
H6 H 0.808636 0.311135 0.069564 0.040 Uiso 1 1 calc R U . . .
C7 C 0.6881(8) 0.20967(15) 0.1064(2) 0.0294(7) Uani 1 1 d . . . . .
C8 C 0.8079(8) 0.17559(17) 0.0221(2) 0.0353(7) Uani 1 1 d . . . . .
H8 H 0.905551 0.202390 -0.028881 0.042 Uiso 1 1 calc R U . . .
C9 C 0.7852(8) 0.10474(17) 0.0129(2) 0.0372(8) Uani 1 1 d . . . . .
H9 H 0.864167 0.082558 -0.044519 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6453(8) 0.06447(16) 0.0882(2) 0.0312(7) Uani 1 1 d . . . . .
H10 H 0.636860 0.015032 0.081181 0.037 Uiso 1 1 calc R U . . .
C11 C 0.1179(7) 0.04073(14) 0.42178(19) 0.0233(6) Uani 1 1 d . . . . .
C12 C 0.1865(7) 0.05982(14) 0.51680(19) 0.0243(6) Uani 1 1 d . . . . .
H12 H 0.315756 0.100852 0.529310 0.029 Uiso 1 1 calc R U . . .
C13 C 0.0686(7) 0.01971(14) 0.5944(2) 0.0251(6) Uani 1 1 d . . . . .
H13 H 0.116718 0.033968 0.659067 0.030 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
N1 B2 1.430(4) . ?
N1 B1 1.437(4) . ?
N1 C11 1.445(3) . ?
B1 C1 1.540(4) . ?
B1 H1 1.09(3) . ?
B2 C3 1.547(4) . ?
B2 H2 1.11(3) . ?
C1 C10 1.385(4) . ?
C1 C2 1.433(4) . ?
C2 C7 1.417(4) . ?
C2 C3 1.431(4) . ?
C3 C4 1.386(4) . ?
C4 C5 1.397(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.416(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(4) . ?
C8 C9 1.362(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 C13 1.386(4) 3_556 ?
C12 C13 1.395(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B2 N1 B1 118.8(2) . . ?
B2 N1 C11 120.1(2) . . ?
B1 N1 C11 121.1(2) . . ?
N1 B1 C1 120.6(3) . . ?
N1 B1 H1 119.0(14) . . ?
C1 B1 H1 120.3(14) . . ?
N1 B2 C3 120.5(3) . . ?
N1 B2 H2 120.0(13) . . ?
C3 B2 H2 119.5(13) . . ?
C10 C1 C2 117.8(3) . . ?
C10 C1 B1 121.8(3) . . ?
C2 C1 B1 120.5(3) . . ?
C7 C2 C3 120.7(3) . . ?
C7 C2 C1 120.2(3) . . ?
C3 C2 C1 119.1(2) . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 B2 121.7(3) . . ?
C2 C3 B2 120.4(2) . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 122.5(3) . . ?
C8 C7 C2 119.0(3) . . ?
C6 C7 C2 118.5(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C1 C10 C9 122.1(3) . . ?
C1 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C13 118.3(2) . 3_556 ?
C12 C11 N1 120.5(2) . . ?
C13 C11 N1 121.2(2) 3_556 . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C11 C13 C12 120.7(3) 3_556 . ?
C11 C13 H13 119.6 3_556 . ?
C12 C13 H13 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B2 N1 B1 C1 4.1(4) . . . . ?
C11 N1 B1 C1 -175.2(3) . . . . ?
B1 N1 B2 C3 -3.6(4) . . . . ?
C11 N1 B2 C3 175.7(3) . . . . ?
N1 B1 C1 C10 177.3(3) . . . . ?
N1 B1 C1 C2 -2.6(4) . . . . ?
C10 C1 C2 C7 0.3(4) . . . . ?
B1 C1 C2 C7 -179.8(3) . . . . ?
C10 C1 C2 C3 -179.5(3) . . . . ?
B1 C1 C2 C3 0.4(4) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C7 C2 C3 B2 -179.7(3) . . . . ?
C1 C2 C3 B2 0.1(4) . . . . ?
N1 B2 C3 C4 -177.9(3) . . . . ?
N1 B2 C3 C2 1.5(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
B2 C3 C4 C5 179.4(3) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 179.7(3) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C3 C2 C7 C8 -179.8(3) . . . . ?
C1 C2 C7 C8 0.4(4) . . . . ?
C3 C2 C7 C6 0.6(4) . . . . ?
C1 C2 C7 C6 -179.2(3) . . . . ?
C6 C7 C8 C9 179.5(3) . . . . ?
C2 C7 C8 C9 -0.2(5) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C2 C1 C10 C9 -1.3(4) . . . . ?
B1 C1 C10 C9 178.8(3) . . . . ?
C8 C9 C10 C1 1.6(5) . . . . ?
B2 N1 C11 C12 -36.4(4) . . . . ?
B1 N1 C11 C12 142.9(3) . . . . ?
B2 N1 C11 C13 144.7(3) . . . 3_556 ?
B1 N1 C11 C13 -35.9(4) . . . 3_556 ?
C13 C11 C12 C13 -0.6(4) 3_556 . . . ?
N1 C11 C12 C13 -179.4(3) . . . . ?
C11 C12 C13 C11 0.6(4) . . . 3_556 ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.046


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

data_wa3236
_database_code_depnum_ccdc_archive 'CCDC 2338780'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 B2 N4, C H2 Cl2'
_chemical_formula_sum            'C31 H30 B2 Cl2 N4'
_chemical_formula_weight         551.11

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   12.6194(8)
_cell_length_b                   22.0063(13)
_cell_length_c                   9.7913(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2719.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8768
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      26.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8768
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.359
_diffrn_reflns_theta_max         25.623
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2590
_reflns_number_gt                2083
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_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)+(0.0578P)²+1.8884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2590
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.58311(17) 0.38652(10) 0.6269(2) 0.0263(5) Uani 1 1 d . . . . .
N1 N 0.51969(12) 0.42561(7) 0.71018(15) 0.0252(4) Uani 1 1 d . . . . .
N2 N 0.65818(12) 0.41380(7) 0.53590(16) 0.0260(4) Uani 1 1 d . . . . .
C1 C 0.53205(14) 0.48898(9) 0.70710(17) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.61199(14) 0.51423(9) 0.62025(18) 0.0237(4) Uani 1 1 d . . . . .
C3 C 0.67601(14) 0.47660(9) 0.53431(18) 0.0244(4) Uani 1 1 d . . . . .
C4 C 0.75324(16) 0.50284(10) 0.4533(2) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.795342 0.477987 0.395412 0.037 Uiso 1 1 calc R U . . .
C5 C 0.76992(16) 0.56588(10) 0.4558(2) 0.0337(5) Uani 1 1 d . . . . .
H5 H 0.823630 0.583102 0.399928 0.040 Uiso 1 1 calc R U . . .
C6 C 0.71019(16) 0.60300(10) 0.5374(2) 0.0315(5) Uani 1 1 d . . . . .
H6 H 0.723043 0.645530 0.538074 0.038 Uiso 1 1 calc R U . . .
C7 C 0.62924(14) 0.57821(9) 0.62079(19) 0.0271(4) Uani 1 1 d . . . . .
C8 C 0.56566(16) 0.61560(9) 0.7056(2) 0.0320(5) Uani 1 1 d . . . . .
H8 H 0.576426 0.658325 0.706678 0.038 Uiso 1 1 calc R U . . .
C9 C 0.48900(16) 0.59025(10) 0.7857(2) 0.0334(5) Uani 1 1 d . . . . .
H9 H 0.446441 0.615842 0.841330 0.040 Uiso 1 1 calc R U . . .
C10 C 0.47151(15) 0.52729(9) 0.7879(2) 0.0302(4) Uani 1 1 d . . . . .
H10 H 0.417874 0.510837 0.845030 0.036 Uiso 1 1 calc R U . . .
C11 C 0.44251(16) 0.40188(10) 0.8081(2) 0.0319(5) Uani 1 1 d . . . . .
H11A H 0.460590 0.416092 0.900084 0.048 Uiso 1 1 calc R U . . .
H11B H 0.443738 0.357363 0.806170 0.048 Uiso 1 1 calc R U . . .
H11C H 0.371512 0.416300 0.783751 0.048 Uiso 1 1 calc R U . . .
C12 C 0.71866(16) 0.37757(10) 0.4372(2) 0.0333(5) Uani 1 1 d . . . . .
H12A H 0.710202 0.394955 0.345729 0.050 Uiso 1 1 calc R U . . .
H12B H 0.692379 0.335668 0.437548 0.050 Uiso 1 1 calc R U . . .
H12C H 0.793799 0.377891 0.462496 0.050 Uiso 1 1 calc R U . . .
C13 C 0.57702(15) 0.31498(9) 0.63755(19) 0.0281(4) Uani 1 1 d . . . . .
C14 C 0.48827(16) 0.28147(9) 0.5977(2) 0.0320(5) Uani 1 1 d . . . . .
H14 H 0.426123 0.302443 0.569871 0.038 Uiso 1 1 calc R U . . .
C15 C 0.66498(16) 0.28156(9) 0.6819(2) 0.0317(5) Uani 1 1 d . . . . .
H15 H 0.726200 0.302591 0.712811 0.038 Uiso 1 1 calc R U . . .
C1L C 0.9371(4) 0.750000 0.5146(5) 0.0833(15) Uani 1 2 d S T P . .
H1L1 H 0.914329 0.786307 0.462588 0.100 Uiso 0.5 1 calc R U P . .
H1L2 H 0.914329 0.713693 0.462588 0.100 Uiso 0.5 1 calc R U P . .
Cl1 Cl 1.07564(10) 0.750000 0.52528(13) 0.0702(3) Uani 1 2 d S T P . .
Cl2 Cl 0.87385(10) 0.750000 0.67009(14) 0.0774(4) 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 N1 1.430(3) . ?
B1 N2 1.432(3) . ?
B1 C13 1.580(3) . ?
N1 C1 1.404(2) . ?
N1 C11 1.463(2) . ?
N2 C3 1.400(2) . ?
N2 C12 1.467(2) . ?
C1 C10 1.386(3) . ?
C1 C2 1.432(3) . ?
C2 C7 1.425(3) . ?
C2 C3 1.431(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.403(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.417(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.418(3) . ?
C8 C9 1.365(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.396(3) . ?
C13 C15 1.401(3) . ?
C14 C14 1.385(4) 7_565 ?
C14 H14 0.9500 . ?
C15 C15 1.389(4) 7_565 ?
C15 H15 0.9500 . ?
C1L Cl2 1.719(5) . ?
C1L Cl1 1.751(6) . ?
C1L H1L1 0.9900 . ?
C1L H1L2 0.9900 . ?

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
N1 B1 N2 118.21(18) . . ?
N1 B1 C13 122.30(17) . . ?
N2 B1 C13 119.42(17) . . ?
C1 N1 B1 121.53(16) . . ?
C1 N1 C11 116.27(15) . . ?
B1 N1 C11 122.12(17) . . ?
C3 N2 B1 121.80(16) . . ?
C3 N2 C12 116.45(16) . . ?
B1 N2 C12 121.73(16) . . ?
C10 C1 N1 122.07(17) . . ?
C10 C1 C2 119.44(18) . . ?
N1 C1 C2 118.47(16) . . ?
C7 C2 C3 119.21(17) . . ?
C7 C2 C1 119.27(17) . . ?
C3 C2 C1 121.51(18) . . ?
C4 C3 N2 122.13(18) . . ?
C4 C3 C2 119.58(18) . . ?
N2 C3 C2 118.29(16) . . ?
C3 C4 C5 120.55(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.18(19) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.25(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 121.48(19) . . ?
C6 C7 C2 119.23(18) . . ?
C8 C7 C2 119.29(18) . . ?
C9 C8 C7 120.03(18) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.60(18) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 120.36(18) . . ?
C1 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C15 116.41(18) . . ?
C14 C13 B1 123.15(17) . . ?
C15 C13 B1 120.35(17) . . ?
C14 C14 C13 121.87(12) 7_565 . ?
C14 C14 H14 119.1 7_565 . ?
C13 C14 H14 119.1 . . ?
C15 C15 C13 121.68(12) 7_565 . ?
C15 C15 H15 119.2 7_565 . ?
C13 C15 H15 119.2 . . ?
Cl2 C1L Cl1 114.2(3) . . ?
Cl2 C1L H1L1 108.7 . . ?
Cl1 C1L H1L1 108.7 . . ?
Cl2 C1L H1L2 108.7 . . ?
Cl1 C1L H1L2 108.7 . . ?
H1L1 C1L H1L2 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 B1 N1 C1 -1.9(3) . . . . ?
C13 B1 N1 C1 174.88(17) . . . . ?
N2 B1 N1 C11 -178.71(16) . . . . ?
C13 B1 N1 C11 -1.9(3) . . . . ?
N1 B1 N2 C3 4.8(3) . . . . ?
C13 B1 N2 C3 -172.12(16) . . . . ?
N1 B1 N2 C12 -173.75(16) . . . . ?
C13 B1 N2 C12 9.3(3) . . . . ?
B1 N1 C1 C10 -179.63(17) . . . . ?
C11 N1 C1 C10 -2.7(2) . . . . ?
B1 N1 C1 C2 -1.4(2) . . . . ?
C11 N1 C1 C2 175.53(15) . . . . ?
C10 C1 C2 C7 1.3(2) . . . . ?
N1 C1 C2 C7 -176.93(16) . . . . ?
C10 C1 C2 C3 -179.57(17) . . . . ?
N1 C1 C2 C3 2.2(2) . . . . ?
B1 N2 C3 C4 175.65(17) . . . . ?
C12 N2 C3 C4 -5.7(3) . . . . ?
B1 N2 C3 C2 -4.1(3) . . . . ?
C12 N2 C3 C2 174.54(16) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 -179.20(17) . . . . ?
C7 C2 C3 N2 179.64(16) . . . . ?
C1 C2 C3 N2 0.5(2) . . . . ?
N2 C3 C4 C5 -179.06(17) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 -179.57(18) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C1 C2 C7 C6 178.41(16) . . . . ?
C3 C2 C7 C8 179.82(16) . . . . ?
C1 C2 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C9 -179.38(18) . . . . ?
C2 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
N1 C1 C10 C9 177.57(17) . . . . ?
C2 C1 C10 C9 -0.6(3) . . . . ?
C8 C9 C10 C1 -0.4(3) . . . . ?
N1 B1 C13 C14 68.1(3) . . . . ?
N2 B1 C13 C14 -115.1(2) . . . . ?
N1 B1 C13 C15 -115.3(2) . . . . ?
N2 B1 C13 C15 61.4(3) . . . . ?
C15 C13 C14 C14 -2.1(2) . . . 7_565 ?
B1 C13 C14 C14 174.61(13) . . . 7_565 ?
C14 C13 C15 C15 2.1(2) . . . 7_565 ?
B1 C13 C15 C15 -174.72(12) . . . 7_565 ?

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.052


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

data_wa3250
_database_code_depnum_ccdc_archive 'CCDC 2338788'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H48 B3 N3'
_chemical_formula_sum            'C48 H48 B3 N3'
_chemical_formula_weight         699.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   11.4766(6)
_cell_length_b                   13.7242(7)
_cell_length_c                   15.0142(8)
_cell_angle_alpha                102.326(4)
_cell_angle_beta                 106.309(4)
_cell_angle_gamma                107.834(4)
_cell_volume                     2041.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    31694
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      26.17

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31694
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.255
_diffrn_reflns_theta_max         25.795
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7667
_reflns_number_gt                5546
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_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)+3.2043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         7667
_refine_ls_number_parameters     497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0932
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   1.307
_refine_ls_restrained_S_all      1.307
_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
N1 N 0.7194(3) 0.4193(2) 0.79090(19) 0.0295(6) Uani 1 1 d . . . . .
N2 N 0.8148(3) 0.1244(2) 0.4280(2) 0.0368(7) Uani 1 1 d . . . . .
N3 N 0.7016(3) 0.2173(2) 0.3368(2) 0.0372(7) Uani 1 1 d . . . . .
B1 B 0.7207(3) 0.3644(3) 0.8630(3) 0.0272(8) Uani 1 1 d . . . . .
B2 B 0.7120(4) 0.5241(3) 0.8084(3) 0.0308(8) Uani 1 1 d . . . . .
B3 B 0.7540(4) 0.1999(3) 0.4274(3) 0.0342(9) Uani 1 1 d . . . . .
C1 C 0.7142(3) 0.4228(3) 0.9620(2) 0.0315(8) Uani 1 1 d . . . . .
C2 C 0.6916(3) 0.5208(3) 0.9754(2) 0.0325(8) Uani 1 1 d . . . . .
C3 C 0.6868(3) 0.5714(3) 0.9016(3) 0.0335(8) Uani 1 1 d . . . . .
C4 C 0.6649(4) 0.6668(3) 0.9171(3) 0.0458(10) Uani 1 1 d . . . . .
H4 H 0.662991 0.702318 0.869222 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6457(4) 0.7114(3) 1.0022(3) 0.0560(12) Uani 1 1 d . . . . .
H5 H 0.626653 0.774663 1.010018 0.067 Uiso 1 1 calc R U . . .
C6 C 0.6542(4) 0.6645(3) 1.0736(3) 0.0539(11) Uani 1 1 d . . . . .
H6 H 0.642832 0.696511 1.131550 0.065 Uiso 1 1 calc R U . . .
C7 C 0.6793(4) 0.5695(3) 1.0634(3) 0.0422(9) Uani 1 1 d . . . . .
C8 C 0.6970(4) 0.5230(3) 1.1387(3) 0.0548(12) Uani 1 1 d . . . . .
H8 H 0.689346 0.555266 1.198308 0.066 Uiso 1 1 calc R U . . .
C9 C 0.7246(5) 0.4332(3) 1.1276(3) 0.0579(12) Uani 1 1 d . . . . .
H9 H 0.739908 0.405031 1.180371 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7310(4) 0.3810(3) 1.0385(3) 0.0443(10) Uani 1 1 d . . . . .
H10 H 0.747068 0.316339 1.030887 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7283(3) 0.3674(3) 0.6995(2) 0.0298(7) Uani 1 1 d . . . . .
C12 C 0.6208(3) 0.2788(3) 0.6300(2) 0.0330(8) Uani 1 1 d . . . . .
H12 H 0.541472 0.253897 0.641809 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6276(3) 0.2255(3) 0.5425(2) 0.0325(8) Uani 1 1 d . . . . .
C14 C 0.7434(4) 0.2625(3) 0.5244(2) 0.0329(8) Uani 1 1 d . . . . .
C15 C 0.8515(4) 0.3530(3) 0.5948(3) 0.0380(8) Uani 1 1 d . . . . .
C16 C 0.8434(4) 0.4040(3) 0.6819(3) 0.0397(9) Uani 1 1 d . . . . .
H16 H 0.917637 0.464580 0.729894 0.048 Uiso 1 1 calc R U . . .
C17 C 0.5082(4) 0.1290(3) 0.4676(3) 0.0484(10) Uani 1 1 d . . . . .
H17A H 0.463787 0.151245 0.414395 0.073 Uiso 1 1 calc R U . . .
H17B H 0.447289 0.100860 0.499080 0.073 Uiso 1 1 calc R U . . .
H17C H 0.536034 0.072399 0.440577 0.073 Uiso 1 1 calc R U . . .
C18 C 0.9803(4) 0.3945(4) 0.5796(3) 0.0657(13) Uani 1 1 d . . . . .
H18A H 0.962060 0.387355 0.510236 0.099 Uiso 1 1 calc R U . . .
H18B H 1.032024 0.352186 0.598895 0.099 Uiso 1 1 calc R U . . .
H18C H 1.030154 0.470920 0.619953 0.099 Uiso 1 1 calc R U . . .
C19 C 0.8655(5) 0.0992(4) 0.5172(3) 0.0565(12) Uani 1 1 d . . . . .
H19A H 0.829268 0.020530 0.503014 0.085 Uiso 1 1 calc R U . . .
H19B H 0.839390 0.133752 0.568138 0.085 Uiso 1 1 calc R U . . .
H19C H 0.961974 0.126364 0.540412 0.085 Uiso 1 1 calc R U . . .
C20 C 0.6389(5) 0.2950(4) 0.3307(3) 0.0548(11) Uani 1 1 d . . . . .
H20A H 0.641290 0.329617 0.395822 0.082 Uiso 1 1 calc R U . . .
H20B H 0.547050 0.257149 0.284718 0.082 Uiso 1 1 calc R U . . .
H20C H 0.686313 0.350341 0.307525 0.082 Uiso 1 1 calc R U . . .
C21 C 0.8323(3) 0.0729(3) 0.3442(3) 0.0345(8) Uani 1 1 d . . . . .
C22 C 0.7775(3) 0.0910(3) 0.2552(2) 0.0327(8) Uani 1 1 d . . . . .
C23 C 0.7072(3) 0.1607(3) 0.2495(2) 0.0341(8) Uani 1 1 d . . . . .
C24 C 0.6464(4) 0.1693(3) 0.1596(3) 0.0438(9) Uani 1 1 d . . . . .
H24 H 0.596661 0.213380 0.155024 0.053 Uiso 1 1 calc R U . . .
C25 C 0.6581(4) 0.1130(3) 0.0751(3) 0.0501(11) Uani 1 1 d . . . . .
H25 H 0.615269 0.118941 0.013641 0.060 Uiso 1 1 calc R U . . .
C26 C 0.7294(4) 0.0502(3) 0.0793(3) 0.0507(11) Uani 1 1 d . . . . .
H26 H 0.737957 0.014690 0.021322 0.061 Uiso 1 1 calc R U . . .
C27 C 0.7906(4) 0.0372(3) 0.1687(3) 0.0415(9) Uani 1 1 d . . . . .
C28 C 0.8626(4) -0.0295(3) 0.1753(3) 0.0558(12) Uani 1 1 d . . . . .
H28 H 0.874288 -0.064105 0.118483 0.067 Uiso 1 1 calc R U . . .
C29 C 0.9151(4) -0.0449(4) 0.2605(3) 0.0580(12) Uani 1 1 d . . . . .
H29 H 0.963680 -0.089933 0.263193 0.070 Uiso 1 1 calc R U . . .
C30 C 0.8989(4) 0.0046(3) 0.3457(3) 0.0488(10) Uani 1 1 d . . . . .
H30 H 0.934148 -0.008966 0.404831 0.059 Uiso 1 1 calc R U . . .
C31 C 0.7312(3) 0.2506(2) 0.8457(2) 0.0271(7) Uani 1 1 d . . . . .
C32 C 0.6189(3) 0.1550(3) 0.8133(2) 0.0327(8) Uani 1 1 d . . . . .
C33 C 0.6300(4) 0.0557(3) 0.8037(3) 0.0392(9) Uani 1 1 d . . . . .
H33 H 0.552346 -0.008164 0.781279 0.047 Uiso 1 1 calc R U . . .
C34 C 0.7510(4) 0.0473(3) 0.8259(3) 0.0405(9) Uani 1 1 d . . . . .
C35 C 0.8624(4) 0.1416(3) 0.8592(3) 0.0421(9) Uani 1 1 d . . . . .
H35 H 0.946591 0.137515 0.875896 0.051 Uiso 1 1 calc R U . . .
C36 C 0.8546(3) 0.2427(3) 0.8690(2) 0.0332(8) Uani 1 1 d . . . . .
C37 C 0.4833(4) 0.1584(3) 0.7898(3) 0.0471(10) Uani 1 1 d . . . . .
H37A H 0.490337 0.232374 0.793985 0.071 Uiso 1 1 calc R U . . .
H37B H 0.446207 0.135982 0.836978 0.071 Uiso 1 1 calc R U . . .
H37C H 0.425676 0.109149 0.723211 0.071 Uiso 1 1 calc R U . . .
C38 C 0.7626(5) -0.0612(3) 0.8171(4) 0.0672(13) Uani 1 1 d . . . . .
H38A H 0.756133 -0.094631 0.750421 0.101 Uiso 1 1 calc R U . . .
H38B H 0.691219 -0.108598 0.830723 0.101 Uiso 1 1 calc R U . . .
H38C H 0.847810 -0.050352 0.864480 0.101 Uiso 1 1 calc R U . . .
C39 C 0.9785(4) 0.3425(3) 0.9055(3) 0.0488(10) Uani 1 1 d . . . . .
H39A H 1.055116 0.324211 0.929119 0.073 Uiso 1 1 calc R U . . .
H39B H 0.977930 0.396928 0.959381 0.073 Uiso 1 1 calc R U . . .
H39C H 0.983370 0.371627 0.851861 0.073 Uiso 1 1 calc R U . . .
C41 C 0.7256(3) 0.5898(3) 0.7353(3) 0.0331(8) Uani 1 1 d . . . . .
C42 C 0.8485(4) 0.6645(3) 0.7468(3) 0.0387(9) Uani 1 1 d . . . . .
C43 C 0.8571(4) 0.7211(3) 0.6806(3) 0.0412(9) Uani 1 1 d . . . . .
H43 H 0.941067 0.770152 0.688183 0.049 Uiso 1 1 calc R U . . .
C44 C 0.7464(4) 0.7076(3) 0.6041(3) 0.0423(9) Uani 1 1 d . . . . .
C45 C 0.6245(4) 0.6378(3) 0.5958(3) 0.0383(9) Uani 1 1 d . . . . .
H45 H 0.547274 0.630327 0.545378 0.046 Uiso 1 1 calc R U . . .
C46 C 0.6125(3) 0.5787(3) 0.6595(3) 0.0335(8) Uani 1 1 d . . . . .
C47 C 0.9712(4) 0.6871(3) 0.8320(3) 0.0525(11) Uani 1 1 d . . . . .
H47A H 1.046763 0.702112 0.811289 0.079 Uiso 1 1 calc R U . . .
H47B H 0.959948 0.623785 0.854129 0.079 Uiso 1 1 calc R U . . .
H47C H 0.986722 0.749992 0.885984 0.079 Uiso 1 1 calc R U . . .
C48 C 0.7602(4) 0.7691(4) 0.5323(3) 0.0606(12) Uani 1 1 d . . . . .
H48A H 0.805276 0.846942 0.568380 0.091 Uiso 1 1 calc R U . . .
H48B H 0.672469 0.754013 0.485721 0.091 Uiso 1 1 calc R U . . .
H48C H 0.811637 0.745929 0.496431 0.091 Uiso 1 1 calc R U . . .
C49 C 0.4791(3) 0.5040(3) 0.6506(3) 0.0424(9) Uani 1 1 d . . . . .
H49A H 0.411514 0.497882 0.590341 0.064 Uiso 1 1 calc R U . . .
H49B H 0.459459 0.533442 0.707511 0.064 Uiso 1 1 calc R U . . .
H49C H 0.479669 0.432255 0.648178 0.064 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
N1 B2 1.440(5) . ?
N1 B1 1.444(5) . ?
N1 C11 1.451(4) . ?
N2 C21 1.404(4) . ?
N2 B3 1.416(5) . ?
N2 C19 1.462(5) . ?
N3 C23 1.403(4) . ?
N3 B3 1.426(5) . ?
N3 C20 1.462(4) . ?
B1 C1 1.566(5) . ?
B1 C31 1.575(5) . ?
B2 C3 1.555(5) . ?
B2 C41 1.573(5) . ?
B3 C14 1.582(5) . ?
C1 C10 1.381(5) . ?
C1 C2 1.430(5) . ?
C2 C7 1.414(5) . ?
C2 C3 1.424(5) . ?
C3 C4 1.392(5) . ?
C4 C5 1.400(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.360(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.409(6) . ?
C8 C9 1.352(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.381(5) . ?
C11 C16 1.383(5) . ?
C12 C13 1.397(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(5) . ?
C13 C17 1.511(5) . ?
C14 C15 1.399(5) . ?
C15 C16 1.388(5) . ?
C15 C18 1.513(5) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C30 1.378(5) . ?
C21 C22 1.418(5) . ?
C22 C27 1.422(5) . ?
C22 C23 1.428(5) . ?
C23 C24 1.384(5) . ?
C24 C25 1.401(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.357(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.406(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.410(6) . ?
C28 C29 1.344(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.404(6) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.400(4) . ?
C31 C36 1.404(5) . ?
C32 C33 1.388(5) . ?
C32 C37 1.513(5) . ?
C33 C34 1.381(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(5) . ?
C34 C38 1.516(5) . ?
C35 C36 1.396(5) . ?
C35 H35 0.9500 . ?
C36 C39 1.499(5) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C41 C42 1.404(5) . ?
C41 C46 1.407(5) . ?
C42 C43 1.391(5) . ?
C42 C47 1.506(5) . ?
C43 C44 1.384(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.385(5) . ?
C44 C48 1.517(5) . ?
C45 C46 1.389(5) . ?
C45 H45 0.9500 . ?
C46 C49 1.510(5) . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B2 N1 B1 121.7(3) . . ?
B2 N1 C11 119.7(3) . . ?
B1 N1 C11 118.6(3) . . ?
C21 N2 B3 121.7(3) . . ?
C21 N2 C19 117.2(3) . . ?
B3 N2 C19 121.1(3) . . ?
C23 N3 B3 121.7(3) . . ?
C23 N3 C20 116.9(3) . . ?
B3 N3 C20 121.4(3) . . ?
N1 B1 C1 117.8(3) . . ?
N1 B1 C31 122.4(3) . . ?
C1 B1 C31 119.8(3) . . ?
N1 B2 C3 118.2(3) . . ?
N1 B2 C41 122.0(3) . . ?
C3 B2 C41 119.8(3) . . ?
N2 B3 N3 118.2(3) . . ?
N2 B3 C14 120.8(3) . . ?
N3 B3 C14 120.9(3) . . ?
C10 C1 C2 118.8(3) . . ?
C10 C1 B1 120.6(3) . . ?
C2 C1 B1 120.6(3) . . ?
C7 C2 C3 120.2(3) . . ?
C7 C2 C1 119.9(3) . . ?
C3 C2 C1 119.9(3) . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 B2 120.8(3) . . ?
C2 C3 B2 120.8(3) . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.3(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C8 122.5(4) . . ?
C6 C7 C2 118.6(4) . . ?
C8 C7 C2 118.8(4) . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C1 C10 C9 120.7(4) . . ?
C1 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C16 119.6(3) . . ?
C12 C11 N1 119.3(3) . . ?
C16 C11 N1 121.1(3) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 C17 120.7(3) . . ?
C12 C13 C17 119.4(3) . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 B3 120.3(3) . . ?
C15 C14 B3 120.5(3) . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 C18 118.8(4) . . ?
C14 C15 C18 121.1(3) . . ?
C11 C16 C15 120.7(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C30 C21 N2 122.2(3) . . ?
C30 C21 C22 119.4(3) . . ?
N2 C21 C22 118.4(3) . . ?
C21 C22 C27 119.4(3) . . ?
C21 C22 C23 121.7(3) . . ?
C27 C22 C23 118.9(3) . . ?
C24 C23 N3 122.4(3) . . ?
C24 C23 C22 119.7(3) . . ?
N3 C23 C22 117.9(3) . . ?
C23 C24 C25 120.0(4) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 121.4(4) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C28 122.1(4) . . ?
C26 C27 C22 119.2(4) . . ?
C28 C27 C22 118.6(4) . . ?
C29 C28 C27 121.2(4) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.7(4) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C21 C30 C29 120.6(4) . . ?
C21 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C32 C31 C36 117.9(3) . . ?
C32 C31 B1 121.1(3) . . ?
C36 C31 B1 120.8(3) . . ?
C33 C32 C31 120.6(3) . . ?
C33 C32 C37 118.9(3) . . ?
C31 C32 C37 120.5(3) . . ?
C34 C33 C32 121.7(3) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 117.9(3) . . ?
C33 C34 C38 121.4(4) . . ?
C35 C34 C38 120.6(4) . . ?
C34 C35 C36 121.8(3) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C35 C36 C31 120.0(3) . . ?
C35 C36 C39 119.7(3) . . ?
C31 C36 C39 120.3(3) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C42 C41 C46 118.4(3) . . ?
C42 C41 B2 121.4(3) . . ?
C46 C41 B2 120.1(3) . . ?
C43 C42 C41 120.0(3) . . ?
C43 C42 C47 119.2(3) . . ?
C41 C42 C47 120.7(3) . . ?
C44 C43 C42 121.5(3) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 118.4(3) . . ?
C43 C44 C48 120.0(4) . . ?
C45 C44 C48 121.6(4) . . ?
C44 C45 C46 121.5(3) . . ?
C44 C45 H45 119.2 . . ?
C46 C45 H45 119.2 . . ?
C45 C46 C41 120.0(3) . . ?
C45 C46 C49 121.1(3) . . ?
C41 C46 C49 118.9(3) . . ?
C42 C47 H47A 109.5 . . ?
C42 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C42 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C44 C48 H48A 109.5 . . ?
C44 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C44 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C46 C49 H49A 109.5 . . ?
C46 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C46 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B2 N1 B1 C1 -0.1(5) . . . . ?
C11 N1 B1 C1 178.7(3) . . . . ?
B2 N1 B1 C31 -178.9(3) . . . . ?
C11 N1 B1 C31 -0.1(5) . . . . ?
B1 N1 B2 C3 -7.9(5) . . . . ?
C11 N1 B2 C3 173.2(3) . . . . ?
B1 N1 B2 C41 173.4(3) . . . . ?
C11 N1 B2 C41 -5.4(5) . . . . ?
C21 N2 B3 N3 4.4(5) . . . . ?
C19 N2 B3 N3 -177.4(4) . . . . ?
C21 N2 B3 C14 -176.1(3) . . . . ?
C19 N2 B3 C14 2.2(6) . . . . ?
C23 N3 B3 N2 1.0(5) . . . . ?
C20 N3 B3 N2 -179.2(4) . . . . ?
C23 N3 B3 C14 -178.5(3) . . . . ?
C20 N3 B3 C14 1.3(6) . . . . ?
N1 B1 C1 C10 -172.2(3) . . . . ?
C31 B1 C1 C10 6.6(5) . . . . ?
N1 B1 C1 C2 7.4(5) . . . . ?
C31 B1 C1 C2 -173.8(3) . . . . ?
C10 C1 C2 C7 -3.6(5) . . . . ?
B1 C1 C2 C7 176.8(3) . . . . ?
C10 C1 C2 C3 173.9(3) . . . . ?
B1 C1 C2 C3 -5.7(5) . . . . ?
C7 C2 C3 C4 -2.4(5) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C7 C2 C3 B2 174.7(3) . . . . ?
C1 C2 C3 B2 -2.8(5) . . . . ?
N1 B2 C3 C4 -173.2(3) . . . . ?
C41 B2 C3 C4 5.4(5) . . . . ?
N1 B2 C3 C2 9.8(5) . . . . ?
C41 B2 C3 C2 -171.6(3) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
B2 C3 C4 C5 -178.2(4) . . . . ?
C3 C4 C5 C6 3.0(6) . . . . ?
C4 C5 C6 C7 -1.4(7) . . . . ?
C5 C6 C7 C8 175.8(4) . . . . ?
C5 C6 C7 C2 -2.1(6) . . . . ?
C3 C2 C7 C6 3.9(5) . . . . ?
C1 C2 C7 C6 -178.6(3) . . . . ?
C3 C2 C7 C8 -174.0(3) . . . . ?
C1 C2 C7 C8 3.5(5) . . . . ?
C6 C7 C8 C9 -178.2(4) . . . . ?
C2 C7 C8 C9 -0.3(6) . . . . ?
C7 C8 C9 C10 -2.7(7) . . . . ?
C2 C1 C10 C9 0.7(6) . . . . ?
B1 C1 C10 C9 -179.7(4) . . . . ?
C8 C9 C10 C1 2.5(7) . . . . ?
B2 N1 C11 C12 -108.2(4) . . . . ?
B1 N1 C11 C12 72.9(4) . . . . ?
B2 N1 C11 C16 73.1(4) . . . . ?
B1 N1 C11 C16 -105.7(4) . . . . ?
C16 C11 C12 C13 0.4(5) . . . . ?
N1 C11 C12 C13 -178.3(3) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C11 C12 C13 C17 -179.7(3) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C17 C13 C14 C15 179.1(3) . . . . ?
C12 C13 C14 B3 177.6(3) . . . . ?
C17 C13 C14 B3 -3.3(5) . . . . ?
N2 B3 C14 C13 -97.5(4) . . . . ?
N3 B3 C14 C13 82.0(5) . . . . ?
N2 B3 C14 C15 80.0(5) . . . . ?
N3 B3 C14 C15 -100.5(4) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
B3 C14 C15 C16 -176.7(3) . . . . ?
C13 C14 C15 C18 178.5(4) . . . . ?
B3 C14 C15 C18 0.9(6) . . . . ?
C12 C11 C16 C15 0.5(5) . . . . ?
N1 C11 C16 C15 179.2(3) . . . . ?
C14 C15 C16 C11 -1.1(6) . . . . ?
C18 C15 C16 C11 -178.8(4) . . . . ?
B3 N2 C21 C30 175.7(4) . . . . ?
C19 N2 C21 C30 -2.6(5) . . . . ?
B3 N2 C21 C22 -5.2(5) . . . . ?
C19 N2 C21 C22 176.5(3) . . . . ?
C30 C21 C22 C27 1.0(5) . . . . ?
N2 C21 C22 C27 -178.2(3) . . . . ?
C30 C21 C22 C23 179.8(3) . . . . ?
N2 C21 C22 C23 0.7(5) . . . . ?
B3 N3 C23 C24 174.0(3) . . . . ?
C20 N3 C23 C24 -5.8(5) . . . . ?
B3 N3 C23 C22 -5.3(5) . . . . ?
C20 N3 C23 C22 174.9(3) . . . . ?
C21 C22 C23 C24 -174.8(3) . . . . ?
C27 C22 C23 C24 4.0(5) . . . . ?
C21 C22 C23 N3 4.4(5) . . . . ?
C27 C22 C23 N3 -176.7(3) . . . . ?
N3 C23 C24 C25 178.4(3) . . . . ?
C22 C23 C24 C25 -2.4(5) . . . . ?
C23 C24 C25 C26 -0.6(6) . . . . ?
C24 C25 C26 C27 1.9(6) . . . . ?
C25 C26 C27 C28 178.4(4) . . . . ?
C25 C26 C27 C22 -0.2(6) . . . . ?
C21 C22 C27 C26 176.2(3) . . . . ?
C23 C22 C27 C26 -2.7(5) . . . . ?
C21 C22 C27 C28 -2.5(5) . . . . ?
C23 C22 C27 C28 178.6(3) . . . . ?
C26 C27 C28 C29 -176.8(4) . . . . ?
C22 C27 C28 C29 1.9(6) . . . . ?
C27 C28 C29 C30 0.4(7) . . . . ?
N2 C21 C30 C29 -179.6(4) . . . . ?
C22 C21 C30 C29 1.3(6) . . . . ?
C28 C29 C30 C21 -2.0(7) . . . . ?
N1 B1 C31 C32 -98.3(4) . . . . ?
C1 B1 C31 C32 83.0(4) . . . . ?
N1 B1 C31 C36 86.2(4) . . . . ?
C1 B1 C31 C36 -92.6(4) . . . . ?
C36 C31 C32 C33 -0.6(5) . . . . ?
B1 C31 C32 C33 -176.3(3) . . . . ?
C36 C31 C32 C37 178.3(3) . . . . ?
B1 C31 C32 C37 2.6(5) . . . . ?
C31 C32 C33 C34 0.3(5) . . . . ?
C37 C32 C33 C34 -178.7(3) . . . . ?
C32 C33 C34 C35 0.5(5) . . . . ?
C32 C33 C34 C38 178.8(4) . . . . ?
C33 C34 C35 C36 -1.1(5) . . . . ?
C38 C34 C35 C36 -179.3(4) . . . . ?
C34 C35 C36 C31 0.7(5) . . . . ?
C34 C35 C36 C39 179.9(3) . . . . ?
C32 C31 C36 C35 0.1(5) . . . . ?
B1 C31 C36 C35 175.8(3) . . . . ?
C32 C31 C36 C39 -179.1(3) . . . . ?
B1 C31 C36 C39 -3.4(5) . . . . ?
N1 B2 C41 C42 -91.5(4) . . . . ?
C3 B2 C41 C42 89.9(4) . . . . ?
N1 B2 C41 C46 91.8(4) . . . . ?
C3 B2 C41 C46 -86.8(4) . . . . ?
C46 C41 C42 C43 -3.5(5) . . . . ?
B2 C41 C42 C43 179.8(3) . . . . ?
C46 C41 C42 C47 174.6(3) . . . . ?
B2 C41 C42 C47 -2.2(5) . . . . ?
C41 C42 C43 C44 1.5(6) . . . . ?
C47 C42 C43 C44 -176.6(4) . . . . ?
C42 C43 C44 C45 1.7(6) . . . . ?
C42 C43 C44 C48 -178.8(4) . . . . ?
C43 C44 C45 C46 -2.8(6) . . . . ?
C48 C44 C45 C46 177.7(4) . . . . ?
C44 C45 C46 C41 0.8(5) . . . . ?
C44 C45 C46 C49 179.2(3) . . . . ?
C42 C41 C46 C45 2.4(5) . . . . ?
B2 C41 C46 C45 179.2(3) . . . . ?
C42 C41 C46 C49 -176.1(3) . . . . ?
B2 C41 C46 C49 0.7(5) . . . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.052



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

data_wa3220
_database_code_depnum_ccdc_archive 'CCDC 2338787'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 B N3'
_chemical_formula_sum            'C20 H22 B N3'
_chemical_formula_weight         315.21

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           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                   12.1715(4)
_cell_length_b                   18.8940(4)
_cell_length_c                   22.6103(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.011(2)
_cell_angle_gamma                90
_cell_volume                     5196.5(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    55832
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      26.43

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44476
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.156
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9168
_reflns_number_gt                7272
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_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)+(0.0713P)²+5.1073P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9168
_refine_ls_number_parameters     685
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.1970
_refine_ls_wR_factor_gt          0.1777
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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
N1 N 0.8446(2) 0.95648(15) 0.41133(12) 0.0549(7) Uani 1 1 d . . . . .
N2 N 0.83142(19) 0.83436(14) 0.37421(12) 0.0506(6) Uani 1 1 d . . . . .
N3 N 0.8420(7) 0.8369(3) 0.6758(2) 0.133(2) Uani 1 1 d D . . . .
H3A H 0.7696(18) 0.845(3) 0.686(2) 0.11(2) Uiso 1 1 d D . . . .
H3B H 0.9134(19) 0.841(3) 0.692(2) 0.103(19) Uiso 1 1 d D . . . .
B1 B 0.8368(3) 0.88108(19) 0.42292(17) 0.0491(8) Uani 1 1 d . . . . .
C1 C 0.8402(3) 0.98229(19) 0.35350(16) 0.0572(8) Uani 1 1 d . . . . .
C2 C 0.8356(2) 0.93425(18) 0.30619(15) 0.0514(8) Uani 1 1 d . . . . .
C3 C 0.8325(2) 0.85761(19) 0.31578(14) 0.0517(8) Uani 1 1 d . . . . .
C4 C 0.8309(2) 0.8138(2) 0.26866(15) 0.0569(8) Uani 1 1 d . . . . .
H4 H 0.830308 0.764092 0.274825 0.068 Uiso 1 1 calc R U . . .
C5 C 0.8300(3) 0.8408(2) 0.20969(16) 0.0688(10) Uani 1 1 d . . . . .
H5 H 0.828623 0.809193 0.177008 0.083 Uiso 1 1 calc R U . . .
C6 C 0.8310(3) 0.9115(2) 0.20045(17) 0.0647(9) Uani 1 1 d . . . . .
H6 H 0.829837 0.928937 0.161005 0.078 Uiso 1 1 calc R U . . .
C7 C 0.8337(3) 0.9589(2) 0.24662(17) 0.0641(9) Uani 1 1 d . . . . .
C8 C 0.8358(4) 1.0336(2) 0.2377(2) 0.0832(13) Uani 1 1 d . . . . .
H8 H 0.834337 1.051802 0.198510 0.100 Uiso 1 1 calc R U . . .
C9 C 0.8399(4) 1.0796(2) 0.2844(2) 0.0887(13) Uani 1 1 d . . . . .
H9 H 0.841320 1.129102 0.277149 0.106 Uiso 1 1 calc R U . . .
C10 C 0.8419(3) 1.0549(2) 0.34245(19) 0.0735(11) Uani 1 1 d . . . . .
H10 H 0.844481 1.087429 0.374487 0.088 Uiso 1 1 calc R U . . .
C11 C 0.8582(3) 1.00795(19) 0.45831(18) 0.0714(10) Uani 1 1 d . . . . .
H11A H 0.924275 1.036228 0.451997 0.107 Uiso 1 1 calc R U . . .
H11B H 0.865786 0.983445 0.496434 0.107 Uiso 1 1 calc R U . . .
H11C H 0.793811 1.039078 0.458344 0.107 Uiso 1 1 calc R U . . .
C12 C 0.8248(3) 0.75704(17) 0.38292(16) 0.0552(8) Uani 1 1 d . . . . .
H12A H 0.826898 0.746428 0.425368 0.083 Uiso 1 1 calc R U . . .
H12B H 0.887149 0.734132 0.364430 0.083 Uiso 1 1 calc R U . . .
H12C H 0.755929 0.739251 0.364732 0.083 Uiso 1 1 calc R U . . .
C21 C 0.8344(3) 0.85656(16) 0.48948(15) 0.0526(8) Uani 1 1 d . . . . .
C22 C 0.9308(3) 0.83437(17) 0.52029(17) 0.0590(9) Uani 1 1 d . . . . .
C23 C 0.9318(4) 0.8258(2) 0.58099(19) 0.0771(11) Uani 1 1 d . . . . .
H23 H 0.997431 0.810727 0.601248 0.093 Uiso 1 1 calc R U . . .
C24 C 0.8382(4) 0.8388(2) 0.6130(2) 0.0839(12) Uani 1 1 d . . . . .
C25 C 0.7392(4) 0.8534(2) 0.58154(18) 0.0749(11) Uani 1 1 d . . . . .
H25 H 0.672448 0.855954 0.602013 0.090 Uiso 1 1 calc R U . . .
C26 C 0.7382(3) 0.86413(18) 0.52144(16) 0.0566(8) Uani 1 1 d . . . . .
C27 C 1.0337(3) 0.8202(2) 0.4879(2) 0.0838(13) Uani 1 1 d . . . . .
H27A H 1.097421 0.823556 0.515436 0.126 Uiso 1 1 calc R U . . .
H27B H 1.040749 0.855108 0.456185 0.126 Uiso 1 1 calc R U . . .
H27C H 1.030265 0.772540 0.470728 0.126 Uiso 1 1 calc R U . . .
C28 C 0.6329(3) 0.8877(2) 0.49015(18) 0.0726(10) Uani 1 1 d . . . . .
H28A H 0.570019 0.867241 0.510003 0.109 Uiso 1 1 calc R U . . .
H28B H 0.632249 0.871606 0.448924 0.109 Uiso 1 1 calc R U . . .
H28C H 0.628090 0.939417 0.491198 0.109 Uiso 1 1 calc R U . . .
N1A N 0.43312(17) 0.64627(12) 0.71327(10) 0.0385(5) Uani 1 1 d . . . . .
N2A N 0.23521(17) 0.66477(13) 0.71962(10) 0.0408(5) Uani 1 1 d . . . . .
N3A N 0.3338(3) 0.85651(17) 0.48195(13) 0.0587(7) Uani 1 1 d D . . . .
H3AA H 0.317(3) 0.8344(18) 0.4471(9) 0.073(12) Uiso 1 1 d D . . . .
H3AB H 0.373(3) 0.8969(12) 0.4831(18) 0.080(13) Uiso 1 1 d D . . . .
B1A B 0.3349(2) 0.67880(18) 0.69030(14) 0.0393(7) Uani 1 1 d . . . . .
C1A C 0.4348(2) 0.60288(14) 0.76380(11) 0.0349(6) Uani 1 1 d . . . . .
C2A C 0.3330(2) 0.59000(14) 0.79150(11) 0.0354(6) Uani 1 1 d . . . . .
C3A C 0.2321(2) 0.62006(14) 0.76888(12) 0.0370(6) Uani 1 1 d . . . . .
C4A C 0.1353(2) 0.60489(17) 0.79716(13) 0.0469(7) Uani 1 1 d . . . . .
H4A H 0.067809 0.624414 0.782467 0.056 Uiso 1 1 calc R U . . .
C5A C 0.1365(3) 0.56120(18) 0.84702(14) 0.0537(8) Uani 1 1 d . . . . .
H5A H 0.069204 0.551153 0.865390 0.064 Uiso 1 1 calc R U . . .
C6A C 0.2312(3) 0.53267(17) 0.86996(14) 0.0529(8) Uani 1 1 d . . . . .
H6A H 0.229677 0.503592 0.904198 0.063 Uiso 1 1 calc R U . . .
C7A C 0.3324(2) 0.54632(15) 0.84278(12) 0.0429(6) Uani 1 1 d . . . . .
C8A C 0.4330(3) 0.51765(16) 0.86542(14) 0.0513(7) Uani 1 1 d . . . . .
H8A H 0.433657 0.488850 0.899873 0.062 Uiso 1 1 calc R U . . .
C9A C 0.5282(3) 0.53110(15) 0.83819(14) 0.0487(7) Uani 1 1 d . . . . .
H9A H 0.594902 0.511672 0.854101 0.058 Uiso 1 1 calc R U . . .
C10A C 0.5305(2) 0.57303(15) 0.78707(13) 0.0422(6) Uani 1 1 d . . . . .
H10A H 0.598153 0.580943 0.768383 0.051 Uiso 1 1 calc R U . . .
C11A C 0.5387(2) 0.65768(19) 0.68588(14) 0.0515(8) Uani 1 1 d . . . . .
H11D H 0.589396 0.681236 0.714172 0.077 Uiso 1 1 calc R U . . .
H11E H 0.527835 0.687455 0.650673 0.077 Uiso 1 1 calc R U . . .
H11F H 0.569607 0.611994 0.674448 0.077 Uiso 1 1 calc R U . . .
C12A C 0.1313(2) 0.6966(2) 0.69937(15) 0.0581(9) Uani 1 1 d . . . . .
H12D H 0.078864 0.659249 0.688072 0.087 Uiso 1 1 calc R U . . .
H12E H 0.143725 0.727018 0.665110 0.087 Uiso 1 1 calc R U . . .
H12F H 0.101543 0.725076 0.731336 0.087 Uiso 1 1 calc R U . . .
C21A C 0.3359(2) 0.72744(16) 0.63401(12) 0.0412(6) Uani 1 1 d . . . . .
C22A C 0.2996(2) 0.70109(16) 0.57838(12) 0.0412(6) Uani 1 1 d . . . . .
C23A C 0.3003(2) 0.74434(16) 0.52864(12) 0.0430(7) Uani 1 1 d . . . . .
H23A H 0.275250 0.725895 0.491481 0.052 Uiso 1 1 calc R U . . .
C24A C 0.3368(2) 0.81380(16) 0.53207(12) 0.0437(7) Uani 1 1 d . . . . .
C25A C 0.3736(3) 0.83974(17) 0.58664(14) 0.0504(7) Uani 1 1 d . . . . .
H25A H 0.398884 0.887213 0.589616 0.060 Uiso 1 1 calc R U . . .
C26A C 0.3741(3) 0.79755(17) 0.63710(13) 0.0489(7) Uani 1 1 d . . . . .
C27A C 0.2620(3) 0.62557(18) 0.57229(15) 0.0608(9) Uani 1 1 d . . . . .
H27D H 0.320280 0.593901 0.587398 0.091 Uiso 1 1 calc R U . . .
H27E H 0.245507 0.614998 0.530482 0.091 Uiso 1 1 calc R U . . .
H27F H 0.195794 0.618579 0.595007 0.091 Uiso 1 1 calc R U . . .
C28A C 0.4184(4) 0.8279(2) 0.69521(15) 0.0700(10) Uani 1 1 d . . . . .
H28D H 0.366900 0.817635 0.726451 0.105 Uiso 1 1 calc R U . . .
H28E H 0.427077 0.879216 0.691345 0.105 Uiso 1 1 calc R U . . .
H28F H 0.489852 0.806392 0.705407 0.105 Uiso 1 1 calc R U . . .
N1B N 0.37674(18) 0.41423(12) 0.63382(10) 0.0405(5) Uani 1 1 d . . . . .
N2B N 0.37334(17) 0.36091(12) 0.53534(9) 0.0367(5) Uani 1 1 d . . . . .
N3B N 0.8870(2) 0.3030(2) 0.64212(16) 0.0690(9) Uani 1 1 d D . . . .
H3BA H 0.893(4) 0.2552(6) 0.6448(19) 0.091(15) Uiso 1 1 d D . . . .
H3BB H 0.938(3) 0.328(2) 0.6223(19) 0.112(18) Uiso 1 1 d D . . . .
B1B B 0.4336(3) 0.37808(16) 0.58859(14) 0.0376(7) Uani 1 1 d . . . . .
C1B C 0.2657(2) 0.43286(14) 0.62717(12) 0.0388(6) Uani 1 1 d . . . . .
C2B C 0.2089(2) 0.41425(14) 0.57309(12) 0.0356(6) Uani 1 1 d . . . . .
C3B C 0.2616(2) 0.37726(14) 0.52678(12) 0.0366(6) Uani 1 1 d . . . . .
C4B C 0.2018(2) 0.35764(17) 0.47649(13) 0.0475(7) Uani 1 1 d . . . . .
H4B H 0.236439 0.332189 0.446060 0.057 Uiso 1 1 calc R U . . .
C5B C 0.0898(2) 0.37514(19) 0.47008(14) 0.0559(8) Uani 1 1 d . . . . .
H5B H 0.049306 0.360876 0.435410 0.067 Uiso 1 1 calc R U . . .
C6B C 0.0383(2) 0.41213(18) 0.51263(15) 0.0554(8) Uani 1 1 d . . . . .
H6B H -0.037009 0.424454 0.506870 0.067 Uiso 1 1 calc R U . . .
C7B C 0.0957(2) 0.43239(16) 0.56529(13) 0.0442(7) Uani 1 1 d . . . . .
C8B C 0.0442(2) 0.47001(17) 0.61092(15) 0.0524(8) Uani 1 1 d . . . . .
H8B H -0.030415 0.484075 0.605519 0.063 Uiso 1 1 calc R U . . .
C9B C 0.1000(3) 0.48632(18) 0.66242(15) 0.0543(8) Uani 1 1 d . . . . .
H9B H 0.063330 0.510722 0.692728 0.065 Uiso 1 1 calc R U . . .
C10B C 0.2105(2) 0.46759(17) 0.67122(14) 0.0491(7) Uani 1 1 d . . . . .
H10B H 0.248000 0.478734 0.707598 0.059 Uiso 1 1 calc R U . . .
C11B C 0.4328(3) 0.4341(2) 0.69002(15) 0.0684(11) Uani 1 1 d . . . . .
H11G H 0.430313 0.485641 0.694749 0.103 Uiso 1 1 calc R U . . .
H11H H 0.509488 0.418424 0.689885 0.103 Uiso 1 1 calc R U . . .
H11I H 0.395809 0.411527 0.722898 0.103 Uiso 1 1 calc R U . . .
C12B C 0.4261(2) 0.32461(18) 0.48652(13) 0.0515(8) Uani 1 1 d . . . . .
H12G H 0.390954 0.278538 0.479699 0.077 Uiso 1 1 calc R U . . .
H12H H 0.504317 0.317669 0.496702 0.077 Uiso 1 1 calc R U . . .
H12I H 0.418403 0.353382 0.450552 0.077 Uiso 1 1 calc R U . . .
C21B C 0.5576(2) 0.35676(14) 0.59914(12) 0.0385(6) Uani 1 1 d . . . . .
C22B C 0.5848(2) 0.29084(15) 0.62416(12) 0.0402(6) Uani 1 1 d . . . . .
C23B C 0.6935(2) 0.27314(16) 0.63780(12) 0.0457(7) Uani 1 1 d . . . . .
H23B H 0.710118 0.228564 0.655374 0.055 Uiso 1 1 calc R U . . .
C24B C 0.7779(2) 0.31959(17) 0.62615(13) 0.0479(7) Uani 1 1 d . . . . .
C25B C 0.7518(2) 0.38443(17) 0.60014(13) 0.0488(7) Uani 1 1 d . . . . .
H25B H 0.809279 0.416172 0.590971 0.059 Uiso 1 1 calc R U . . .
C26B C 0.6433(2) 0.40385(15) 0.58724(13) 0.0434(7) Uani 1 1 d . . . . .
C27B C 0.4953(3) 0.23859(17) 0.63771(15) 0.0539(8) Uani 1 1 d . . . . .
H27G H 0.526797 0.190942 0.640918 0.081 Uiso 1 1 calc R U . . .
H27H H 0.438675 0.239488 0.605841 0.081 Uiso 1 1 calc R U . . .
H27I H 0.462466 0.251404 0.675186 0.081 Uiso 1 1 calc R U . . .
C28B C 0.6190(3) 0.47563(17) 0.56110(17) 0.0622(9) Uani 1 1 d . . . . .
H28G H 0.574604 0.502958 0.588293 0.093 Uiso 1 1 calc R U . . .
H28H H 0.578461 0.470087 0.523167 0.093 Uiso 1 1 calc R U . . .
H28I H 0.688211 0.500593 0.554798 0.093 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
N1 C1 1.395(4) . ?
N1 C11 1.445(5) . ?
N1 B1 1.452(4) . ?
N2 C3 1.393(4) . ?
N2 B1 1.411(5) . ?
N2 C12 1.477(4) . ?
N3 C24 1.420(6) . ?
N3 H3A 0.928(10) . ?
N3 H3B 0.931(10) . ?
B1 C21 1.576(5) . ?
C1 C10 1.394(5) . ?
C1 C2 1.403(5) . ?
C2 C7 1.425(5) . ?
C2 C3 1.465(5) . ?
C3 C4 1.349(5) . ?
C4 C5 1.427(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.353(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.426(6) . ?
C8 C9 1.367(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C21 C26 1.405(5) . ?
C21 C22 1.408(4) . ?
C22 C23 1.382(5) . ?
C22 C27 1.497(5) . ?
C23 C24 1.392(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.405(6) . ?
C25 C26 1.374(5) . ?
C25 H25 0.9500 . ?
C26 C28 1.509(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1A C1A 1.406(3) . ?
N1A B1A 1.426(4) . ?
N1A C11A 1.462(3) . ?
N2A C3A 1.400(4) . ?
N2A B1A 1.428(4) . ?
N2A C12A 1.460(4) . ?
N3A C24A 1.391(4) . ?
N3A H3AA 0.908(10) . ?
N3A H3AB 0.899(10) . ?
B1A C21A 1.570(4) . ?
C1A C10A 1.382(4) . ?
C1A C2A 1.429(4) . ?
C2A C7A 1.424(4) . ?
C2A C3A 1.431(4) . ?
C3A C4A 1.390(4) . ?
C4A C5A 1.397(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.359(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.419(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.418(4) . ?
C8A C9A 1.355(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.402(4) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C21A C26A 1.405(4) . ?
C21A C22A 1.409(4) . ?
C22A C23A 1.390(4) . ?
C22A C27A 1.503(4) . ?
C23A C24A 1.387(4) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.387(4) . ?
C25A C26A 1.392(4) . ?
C25A H25A 0.9500 . ?
C26A C28A 1.515(4) . ?
C27A H27D 0.9800 . ?
C27A H27E 0.9800 . ?
C27A H27F 0.9800 . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 0.9800 . ?
N1B C1B 1.399(3) . ?
N1B B1B 1.428(4) . ?
N1B C11B 1.470(4) . ?
N2B C3B 1.401(3) . ?
N2B B1B 1.425(4) . ?
N2B C12B 1.467(4) . ?
N3B C24B 1.399(4) . ?
N3B H3BA 0.907(10) . ?
N3B H3BB 0.906(10) . ?
B1B C21B 1.573(4) . ?
C1B C10B 1.386(4) . ?
C1B C2B 1.428(4) . ?
C2B C7B 1.425(4) . ?
C2B C3B 1.430(4) . ?
C3B C4B 1.380(4) . ?
C4B C5B 1.406(4) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.360(5) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.412(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.417(4) . ?
C8B C9B 1.362(4) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.399(4) . ?
C9B H9B 0.9500 . ?
C10B H10B 0.9500 . ?
C11B H11G 0.9800 . ?
C11B H11H 0.9800 . ?
C11B H11I 0.9800 . ?
C12B H12G 0.9800 . ?
C12B H12H 0.9800 . ?
C12B H12I 0.9800 . ?
C21B C22B 1.403(4) . ?
C21B C26B 1.404(4) . ?
C22B C23B 1.389(4) . ?
C22B C27B 1.509(4) . ?
C23B C24B 1.384(4) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.391(4) . ?
C25B C26B 1.392(4) . ?
C25B H25B 0.9500 . ?
C26B C28B 1.504(4) . ?
C27B H27G 0.9800 . ?
C27B H27H 0.9800 . ?
C27B H27I 0.9800 . ?
C28B H28G 0.9800 . ?
C28B H28H 0.9800 . ?
C28B H28I 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
C1 N1 C11 117.0(3) . . ?
C1 N1 B1 120.8(3) . . ?
C11 N1 B1 122.3(3) . . ?
C3 N2 B1 122.8(3) . . ?
C3 N2 C12 116.2(3) . . ?
B1 N2 C12 121.1(3) . . ?
C24 N3 H3A 104(4) . . ?
C24 N3 H3B 112(4) . . ?
H3A N3 H3B 141(5) . . ?
N2 B1 N1 118.3(3) . . ?
N2 B1 C21 124.0(3) . . ?
N1 B1 C21 117.7(3) . . ?
C10 C1 N1 120.8(4) . . ?
C10 C1 C2 120.0(3) . . ?
N1 C1 C2 119.2(3) . . ?
C1 C2 C7 120.5(3) . . ?
C1 C2 C3 121.8(3) . . ?
C7 C2 C3 117.6(3) . . ?
C4 C3 N2 123.7(3) . . ?
C4 C3 C2 119.3(3) . . ?
N2 C3 C2 117.0(3) . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.7(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C2 120.2(4) . . ?
C6 C7 C8 122.5(4) . . ?
C2 C7 C8 117.3(4) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.9(4) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C1 119.9(4) . . ?
C9 C10 H10 120.0 . . ?
C1 C10 H10 120.0 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C26 C21 C22 118.1(3) . . ?
C26 C21 B1 120.4(3) . . ?
C22 C21 B1 121.1(3) . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 C27 119.2(3) . . ?
C21 C22 C27 120.5(3) . . ?
C22 C23 C24 121.1(4) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C25 118.4(4) . . ?
C23 C24 N3 121.1(5) . . ?
C25 C24 N3 120.5(5) . . ?
C26 C25 C24 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 121.0(3) . . ?
C25 C26 C28 119.0(3) . . ?
C21 C26 C28 119.9(3) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C1A N1A B1A 122.4(2) . . ?
C1A N1A C11A 116.3(2) . . ?
B1A N1A C11A 121.4(2) . . ?
C3A N2A B1A 121.9(2) . . ?
C3A N2A C12A 116.8(2) . . ?
B1A N2A C12A 121.3(2) . . ?
C24A N3A H3AA 116(2) . . ?
C24A N3A H3AB 118(3) . . ?
H3AA N3A H3AB 121(4) . . ?
N1A B1A N2A 117.8(3) . . ?
N1A B1A C21A 121.2(2) . . ?
N2A B1A C21A 121.0(2) . . ?
C10A C1A N1A 122.4(2) . . ?
C10A C1A C2A 119.8(3) . . ?
N1A C1A C2A 117.9(2) . . ?
C7A C2A C1A 119.0(2) . . ?
C7A C2A C3A 119.5(2) . . ?
C1A C2A C3A 121.5(2) . . ?
C4A C3A N2A 122.5(2) . . ?
C4A C3A C2A 119.0(3) . . ?
N2A C3A C2A 118.5(2) . . ?
C3A C4A C5A 120.6(3) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A C4A 121.8(3) . . ?
C6A C5A H5A 119.1 . . ?
C4A C5A H5A 119.1 . . ?
C5A C6A C7A 120.0(3) . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C8A C7A C6A 121.7(3) . . ?
C8A C7A C2A 119.1(3) . . ?
C6A C7A C2A 119.2(3) . . ?
C9A C8A C7A 120.4(3) . . ?
C9A C8A H8A 119.8 . . ?
C7A C8A H8A 119.8 . . ?
C8A C9A C10A 121.5(3) . . ?
C8A C9A H9A 119.2 . . ?
C10A C9A H9A 119.2 . . ?
C1A C10A C9A 120.2(3) . . ?
C1A C10A H10A 119.9 . . ?
C9A C10A H10A 119.9 . . ?
N1A C11A H11D 109.5 . . ?
N1A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
N1A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N2A C12A H12D 109.5 . . ?
N2A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
N2A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C26A C21A C22A 118.0(3) . . ?
C26A C21A B1A 121.6(2) . . ?
C22A C21A B1A 120.4(3) . . ?
C23A C22A C21A 120.3(3) . . ?
C23A C22A C27A 119.6(3) . . ?
C21A C22A C27A 120.1(3) . . ?
C24A C23A C22A 121.5(3) . . ?
C24A C23A H23A 119.3 . . ?
C22A C23A H23A 119.3 . . ?
C23A C24A C25A 118.5(3) . . ?
C23A C24A N3A 120.3(3) . . ?
C25A C24A N3A 121.2(3) . . ?
C24A C25A C26A 121.3(3) . . ?
C24A C25A H25A 119.4 . . ?
C26A C25A H25A 119.4 . . ?
C25A C26A C21A 120.5(3) . . ?
C25A C26A C28A 119.1(3) . . ?
C21A C26A C28A 120.5(3) . . ?
C22A C27A H27D 109.5 . . ?
C22A C27A H27E 109.5 . . ?
H27D C27A H27E 109.5 . . ?
C22A C27A H27F 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
C26A C28A H28D 109.5 . . ?
C26A C28A H28E 109.5 . . ?
H28D C28A H28E 109.5 . . ?
C26A C28A H28F 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
C1B N1B B1B 122.2(2) . . ?
C1B N1B C11B 116.5(2) . . ?
B1B N1B C11B 121.3(2) . . ?
C3B N2B B1B 122.3(2) . . ?
C3B N2B C12B 116.6(2) . . ?
B1B N2B C12B 121.1(2) . . ?
C24B N3B H3BA 108(3) . . ?
C24B N3B H3BB 114(3) . . ?
H3BA N3B H3BB 120(4) . . ?
N2B B1B N1B 117.8(2) . . ?
N2B B1B C21B 122.2(3) . . ?
N1B B1B C21B 120.0(2) . . ?
C10B C1B N1B 122.2(2) . . ?
C10B C1B C2B 120.0(3) . . ?
N1B C1B C2B 117.9(2) . . ?
C7B C2B C1B 119.0(2) . . ?
C7B C2B C3B 118.9(2) . . ?
C1B C2B C3B 122.1(2) . . ?
C4B C3B N2B 122.4(3) . . ?
C4B C3B C2B 119.8(2) . . ?
N2B C3B C2B 117.7(2) . . ?
C3B C4B C5B 120.3(3) . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B H4B 119.9 . . ?
C6B C5B C4B 121.2(3) . . ?
C6B C5B H5B 119.4 . . ?
C4B C5B H5B 119.4 . . ?
C5B C6B C7B 120.6(3) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B H6B 119.7 . . ?
C6B C7B C8B 122.1(3) . . ?
C6B C7B C2B 119.1(3) . . ?
C8B C7B C2B 118.8(3) . . ?
C9B C8B C7B 121.1(3) . . ?
C9B C8B H8B 119.5 . . ?
C7B C8B H8B 119.5 . . ?
C8B C9B C10B 120.8(3) . . ?
C8B C9B H9B 119.6 . . ?
C10B C9B H9B 119.6 . . ?
C1B C10B C9B 120.4(3) . . ?
C1B C10B H10B 119.8 . . ?
C9B C10B H10B 119.8 . . ?
N1B C11B H11G 109.5 . . ?
N1B C11B H11H 109.5 . . ?
H11G C11B H11H 109.5 . . ?
N1B C11B H11I 109.5 . . ?
H11G C11B H11I 109.5 . . ?
H11H C11B H11I 109.5 . . ?
N2B C12B H12G 109.5 . . ?
N2B C12B H12H 109.5 . . ?
H12G C12B H12H 109.5 . . ?
N2B C12B H12I 109.5 . . ?
H12G C12B H12I 109.5 . . ?
H12H C12B H12I 109.5 . . ?
C22B C21B C26B 118.3(2) . . ?
C22B C21B B1B 120.0(2) . . ?
C26B C21B B1B 121.6(2) . . ?
C23B C22B C21B 120.8(3) . . ?
C23B C22B C27B 119.1(3) . . ?
C21B C22B C27B 120.1(2) . . ?
C24B C23B C22B 120.9(3) . . ?
C24B C23B H23B 119.6 . . ?
C22B C23B H23B 119.6 . . ?
C23B C24B C25B 118.6(3) . . ?
C23B C24B N3B 120.8(3) . . ?
C25B C24B N3B 120.5(3) . . ?
C24B C25B C26B 121.5(3) . . ?
C24B C25B H25B 119.3 . . ?
C26B C25B H25B 119.3 . . ?
C25B C26B C21B 119.9(3) . . ?
C25B C26B C28B 119.4(3) . . ?
C21B C26B C28B 120.7(3) . . ?
C22B C27B H27G 109.5 . . ?
C22B C27B H27H 109.5 . . ?
H27G C27B H27H 109.5 . . ?
C22B C27B H27I 109.5 . . ?
H27G C27B H27I 109.5 . . ?
H27H C27B H27I 109.5 . . ?
C26B C28B H28G 109.5 . . ?
C26B C28B H28H 109.5 . . ?
H28G C28B H28H 109.5 . . ?
C26B C28B H28I 109.5 . . ?
H28G C28B H28I 109.5 . . ?
H28H C28B H28I 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 B1 N1 -0.4(4) . . . . ?
C12 N2 B1 N1 179.2(3) . . . . ?
C3 N2 B1 C21 179.3(3) . . . . ?
C12 N2 B1 C21 -1.1(4) . . . . ?
C1 N1 B1 N2 3.8(4) . . . . ?
C11 N1 B1 N2 -175.6(3) . . . . ?
C1 N1 B1 C21 -175.9(3) . . . . ?
C11 N1 B1 C21 4.7(4) . . . . ?
C11 N1 C1 C10 -3.9(5) . . . . ?
B1 N1 C1 C10 176.7(3) . . . . ?
C11 N1 C1 C2 175.1(3) . . . . ?
B1 N1 C1 C2 -4.3(4) . . . . ?
C10 C1 C2 C7 0.5(5) . . . . ?
N1 C1 C2 C7 -178.5(3) . . . . ?
C10 C1 C2 C3 -179.4(3) . . . . ?
N1 C1 C2 C3 1.6(4) . . . . ?
B1 N2 C3 C4 177.9(3) . . . . ?
C12 N2 C3 C4 -1.8(4) . . . . ?
B1 N2 C3 C2 -2.1(4) . . . . ?
C12 N2 C3 C2 178.2(2) . . . . ?
C1 C2 C3 C4 -178.4(3) . . . . ?
C7 C2 C3 C4 1.7(4) . . . . ?
C1 C2 C3 N2 1.6(4) . . . . ?
C7 C2 C3 N2 -178.3(2) . . . . ?
N2 C3 C4 C5 178.8(3) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C5 C6 C7 C2 0.1(5) . . . . ?
C5 C6 C7 C8 179.4(4) . . . . ?
C1 C2 C7 C6 179.0(3) . . . . ?
C3 C2 C7 C6 -1.1(4) . . . . ?
C1 C2 C7 C8 -0.4(5) . . . . ?
C3 C2 C7 C8 179.5(3) . . . . ?
C6 C7 C8 C9 -179.1(4) . . . . ?
C2 C7 C8 C9 0.2(6) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
C8 C9 C10 C1 0.2(7) . . . . ?
N1 C1 C10 C9 178.6(4) . . . . ?
C2 C1 C10 C9 -0.4(6) . . . . ?
N2 B1 C21 C26 -103.4(4) . . . . ?
N1 B1 C21 C26 76.3(4) . . . . ?
N2 B1 C21 C22 84.0(4) . . . . ?
N1 B1 C21 C22 -96.3(4) . . . . ?
C26 C21 C22 C23 -4.9(5) . . . . ?
B1 C21 C22 C23 167.9(3) . . . . ?
C26 C21 C22 C27 175.4(3) . . . . ?
B1 C21 C22 C27 -11.8(5) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C27 C22 C23 C24 179.6(4) . . . . ?
C22 C23 C24 C25 6.9(6) . . . . ?
C22 C23 C24 N3 -173.6(5) . . . . ?
C23 C24 C25 C26 -8.8(6) . . . . ?
N3 C24 C25 C26 171.7(5) . . . . ?
C24 C25 C26 C21 3.9(6) . . . . ?
C24 C25 C26 C28 -173.3(4) . . . . ?
C22 C21 C26 C25 3.0(5) . . . . ?
B1 C21 C26 C25 -169.8(3) . . . . ?
C22 C21 C26 C28 -179.9(3) . . . . ?
B1 C21 C26 C28 7.3(5) . . . . ?
C1A N1A B1A N2A -1.4(4) . . . . ?
C11A N1A B1A N2A 179.9(3) . . . . ?
C1A N1A B1A C21A 179.6(2) . . . . ?
C11A N1A B1A C21A 0.9(4) . . . . ?
C3A N2A B1A N1A -0.8(4) . . . . ?
C12A N2A B1A N1A 179.3(3) . . . . ?
C3A N2A B1A C21A 178.2(2) . . . . ?
C12A N2A B1A C21A -1.7(4) . . . . ?
B1A N1A C1A C10A -178.1(3) . . . . ?
C11A N1A C1A C10A 0.7(4) . . . . ?
B1A N1A C1A C2A 1.8(4) . . . . ?
C11A N1A C1A C2A -179.5(2) . . . . ?
C10A C1A C2A C7A -0.1(4) . . . . ?
N1A C1A C2A C7A -179.9(2) . . . . ?
C10A C1A C2A C3A 179.8(2) . . . . ?
N1A C1A C2A C3A 0.0(4) . . . . ?
B1A N2A C3A C4A -178.8(3) . . . . ?
C12A N2A C3A C4A 1.2(4) . . . . ?
B1A N2A C3A C2A 2.4(4) . . . . ?
C12A N2A C3A C2A -177.6(3) . . . . ?
C7A C2A C3A C4A -1.0(4) . . . . ?
C1A C2A C3A C4A 179.1(2) . . . . ?
C7A C2A C3A N2A 177.9(2) . . . . ?
C1A C2A C3A N2A -2.1(4) . . . . ?
N2A C3A C4A C5A -178.6(3) . . . . ?
C2A C3A C4A C5A 0.2(4) . . . . ?
C3A C4A C5A C6A 0.7(5) . . . . ?
C4A C5A C6A C7A -0.8(5) . . . . ?
C5A C6A C7A C8A 179.9(3) . . . . ?
C5A C6A C7A C2A 0.0(4) . . . . ?
C1A C2A C7A C8A 0.9(4) . . . . ?
C3A C2A C7A C8A -179.0(3) . . . . ?
C1A C2A C7A C6A -179.2(3) . . . . ?
C3A C2A C7A C6A 0.9(4) . . . . ?
C6A C7A C8A C9A 179.4(3) . . . . ?
C2A C7A C8A C9A -0.7(4) . . . . ?
C7A C8A C9A C10A -0.3(5) . . . . ?
N1A C1A C10A C9A 178.9(2) . . . . ?
C2A C1A C10A C9A -0.9(4) . . . . ?
C8A C9A C10A C1A 1.2(4) . . . . ?
N1A B1A C21A C26A -77.8(4) . . . . ?
N2A B1A C21A C26A 103.3(3) . . . . ?
N1A B1A C21A C22A 101.2(3) . . . . ?
N2A B1A C21A C22A -77.8(4) . . . . ?
C26A C21A C22A C23A -1.2(4) . . . . ?
B1A C21A C22A C23A 179.8(2) . . . . ?
C26A C21A C22A C27A 177.7(3) . . . . ?
B1A C21A C22A C27A -1.3(4) . . . . ?
C21A C22A C23A C24A 0.4(4) . . . . ?
C27A C22A C23A C24A -178.5(3) . . . . ?
C22A C23A C24A C25A 0.3(4) . . . . ?
C22A C23A C24A N3A -178.3(3) . . . . ?
C23A C24A C25A C26A -0.1(4) . . . . ?
N3A C24A C25A C26A 178.4(3) . . . . ?
C24A C25A C26A C21A -0.8(5) . . . . ?
C24A C25A C26A C28A 178.2(3) . . . . ?
C22A C21A C26A C25A 1.4(4) . . . . ?
B1A C21A C26A C25A -179.6(3) . . . . ?
C22A C21A C26A C28A -177.5(3) . . . . ?
B1A C21A C26A C28A 1.5(4) . . . . ?
C3B N2B B1B N1B -1.0(4) . . . . ?
C12B N2B B1B N1B 179.2(3) . . . . ?
C3B N2B B1B C21B 177.3(2) . . . . ?
C12B N2B B1B C21B -2.4(4) . . . . ?
C1B N1B B1B N2B -0.1(4) . . . . ?
C11B N1B B1B N2B -179.8(3) . . . . ?
C1B N1B B1B C21B -178.5(2) . . . . ?
C11B N1B B1B C21B 1.8(4) . . . . ?
B1B N1B C1B C10B 179.6(3) . . . . ?
C11B N1B C1B C10B -0.6(4) . . . . ?
B1B N1B C1B C2B 0.3(4) . . . . ?
C11B N1B C1B C2B -179.9(3) . . . . ?
C10B C1B C2B C7B 0.4(4) . . . . ?
N1B C1B C2B C7B 179.8(2) . . . . ?
C10B C1B C2B C3B -178.8(3) . . . . ?
N1B C1B C2B C3B 0.5(4) . . . . ?
B1B N2B C3B C4B -176.7(3) . . . . ?
C12B N2B C3B C4B 3.0(4) . . . . ?
B1B N2B C3B C2B 1.8(4) . . . . ?
C12B N2B C3B C2B -178.5(2) . . . . ?
C7B C2B C3B C4B -2.2(4) . . . . ?
C1B C2B C3B C4B 177.0(3) . . . . ?
C7B C2B C3B N2B 179.2(2) . . . . ?
C1B C2B C3B N2B -1.5(4) . . . . ?
N2B C3B C4B C5B 179.8(3) . . . . ?
C2B C3B C4B C5B 1.3(4) . . . . ?
C3B C4B C5B C6B 0.7(5) . . . . ?
C4B C5B C6B C7B -1.7(5) . . . . ?
C5B C6B C7B C8B -179.0(3) . . . . ?
C5B C6B C7B C2B 0.7(5) . . . . ?
C1B C2B C7B C6B -178.0(3) . . . . ?
C3B C2B C7B C6B 1.3(4) . . . . ?
C1B C2B C7B C8B 1.7(4) . . . . ?
C3B C2B C7B C8B -179.0(3) . . . . ?
C6B C7B C8B C9B 177.1(3) . . . . ?
C2B C7B C8B C9B -2.6(5) . . . . ?
C7B C8B C9B C10B 1.3(5) . . . . ?
N1B C1B C10B C9B 178.9(3) . . . . ?
C2B C1B C10B C9B -1.8(4) . . . . ?
C8B C9B C10B C1B 0.9(5) . . . . ?
N2B B1B C21B C22B -88.4(3) . . . . ?
N1B B1B C21B C22B 89.9(3) . . . . ?
N2B B1B C21B C26B 95.3(3) . . . . ?
N1B B1B C21B C26B -86.4(4) . . . . ?
C26B C21B C22B C23B 1.2(4) . . . . ?
B1B C21B C22B C23B -175.3(3) . . . . ?
C26B C21B C22B C27B 180.0(3) . . . . ?
B1B C21B C22B C27B 3.5(4) . . . . ?
C21B C22B C23B C24B -1.1(4) . . . . ?
C27B C22B C23B C24B -179.9(3) . . . . ?
C22B C23B C24B C25B -0.3(4) . . . . ?
C22B C23B C24B N3B 177.4(3) . . . . ?
C23B C24B C25B C26B 1.7(5) . . . . ?
N3B C24B C25B C26B -176.0(3) . . . . ?
C24B C25B C26B C21B -1.6(5) . . . . ?
C24B C25B C26B C28B 177.8(3) . . . . ?
C22B C21B C26B C25B 0.2(4) . . . . ?
B1B C21B C26B C25B 176.5(3) . . . . ?
C22B C21B C26B C28B -179.3(3) . . . . ?
B1B C21B C26B C28B -2.9(4) . . . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.049


####################################################################### 
# 
# 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_wa3201
_database_code_depnum_ccdc_archive 'CCDC 2338785'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 B3 N3, C4 H8 O'
_chemical_formula_sum            'C34 H36 B3 N3 O'
_chemical_formula_weight         535.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   11.5196(3)
_cell_length_b                   23.1323(6)
_cell_length_c                   10.7965(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2877.00(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    37275
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.17

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37275
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.586
_diffrn_reflns_theta_max         27.750
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3397
_reflns_number_gt                2942
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_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)+(0.0611P)²+1.9218P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0090(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3397
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1684
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.58982(14) 0.62400(7) 0.62244(15) 0.0326(4) Uani 0.5 1 d . . P A 1
N1 N 0.66509(14) 0.59649(7) 0.53417(15) 0.0341(4) Uani 0.5 1 d . . P A 1
N2 N 0.52194(14) 0.58834(7) 0.70515(15) 0.0337(4) Uani 0.5 1 d . . P A 1
N1' N 0.58982(14) 0.62400(7) 0.62244(15) 0.0326(4) Uani 0.5 1 d . . P A 2
B1' B 0.66509(14) 0.59649(7) 0.53417(15) 0.0341(4) Uani 0.5 1 d . . P A 2
B2' B 0.52194(14) 0.58834(7) 0.70515(15) 0.0337(4) Uani 0.5 1 d . . P A 2
C1 C 0.67689(13) 0.53316(7) 0.53070(15) 0.0306(4) Uani 1 1 d . . . . .
C2 C 0.60999(13) 0.49886(7) 0.61478(15) 0.0298(4) Uani 1 1 d . . . . .
C3 C 0.53148(14) 0.52499(7) 0.70040(15) 0.0317(4) Uani 1 1 d . . . . .
C4 C 0.46769(15) 0.49002(8) 0.77885(17) 0.0386(4) Uani 1 1 d . . . . .
H4 H 0.415001 0.507125 0.835762 0.046 Uiso 1 1 calc R U . . .
C5 C 0.47961(16) 0.42947(8) 0.77569(18) 0.0426(4) Uani 1 1 d . . . . .
H5 H 0.435027 0.406249 0.830505 0.051 Uiso 1 1 calc R U . . .
C6 C 0.55449(16) 0.40379(8) 0.69477(18) 0.0405(4) Uani 1 1 d . . . . .
H6 H 0.561450 0.362874 0.693783 0.049 Uiso 1 1 calc R U . . .
C7 C 0.62189(14) 0.43741(7) 0.61232(16) 0.0340(4) Uani 1 1 d . . . . .
C8 C 0.69997(16) 0.41191(8) 0.52769(18) 0.0402(4) Uani 1 1 d . . . . .
H8 H 0.708711 0.371081 0.525986 0.048 Uiso 1 1 calc R U . . .
C9 C 0.76297(17) 0.44537(8) 0.44835(18) 0.0419(4) Uani 1 1 d . . . . .
H9 H 0.815274 0.427576 0.391999 0.050 Uiso 1 1 calc R U . . .
C10 C 0.75145(15) 0.50589(8) 0.44895(17) 0.0370(4) Uani 1 1 d . . . . .
H10 H 0.795547 0.528397 0.392358 0.044 Uiso 1 1 calc R U . . .
C11 C 0.73425(18) 0.63264(10) 0.44213(18) 0.0493(5) Uani 1 1 d . . . . .
H11A H 0.710737 0.673235 0.448817 0.074 Uiso 1 1 calc R U . A 1
H11B H 0.719232 0.618767 0.357879 0.074 Uiso 1 1 calc R U . A 1
H11C H 0.817271 0.629170 0.460506 0.074 Uiso 1 1 calc R U . A 1
C12 C 0.44256(18) 0.61574(10) 0.8010(2) 0.0505(5) Uani 1 1 d . . . . .
H12A H 0.449643 0.657912 0.796790 0.076 Uiso 1 1 calc R U . A 1
H12B H 0.464804 0.602437 0.883867 0.076 Uiso 1 1 calc R U . A 1
H12C H 0.362037 0.604541 0.784228 0.076 Uiso 1 1 calc R U . A 1
C13 C 0.58424(14) 0.68882(7) 0.62858(16) 0.0341(4) Uani 1 1 d . . . . .
C14 C 0.67230(16) 0.71995(8) 0.6852(2) 0.0437(5) Uani 1 1 d . . . . .
H14 H 0.733850 0.699822 0.724856 0.052 Uiso 1 1 calc R U . . .
C15 C 0.49391(17) 0.72007(8) 0.5759(2) 0.0458(5) Uani 1 1 d . . . . .
H15 H 0.430809 0.699958 0.539134 0.055 Uiso 1 1 calc R U . . .
O21 O 0.2087(4) 0.750000 0.4566(4) 0.1157(13) Uani 1 2 d S T P . .
C22 C 0.0927(7) 0.750000 0.4938(5) 0.176(4) Uani 1 2 d S T P . .
H22A H 0.077852 0.784593 0.545415 0.211 Uiso 0.5 1 calc R U P . .
H22B H 0.077852 0.715407 0.545415 0.211 Uiso 0.5 1 calc R U P . .
C23 C 0.0139(5) 0.750000 0.3902(6) 0.1132(19) Uani 1 2 d S T P . .
H23A H -0.036033 0.784840 0.391082 0.136 Uiso 0.5 1 calc R U P . .
H23B H -0.036033 0.715160 0.391082 0.136 Uiso 0.5 1 calc R U P . .
C24 C 0.0920(5) 0.750000 0.2800(5) 0.1009(16) Uani 1 2 d S T P . .
H24A H 0.078492 0.715211 0.228564 0.121 Uiso 0.5 1 calc R U P . .
H24B H 0.078492 0.784789 0.228564 0.121 Uiso 0.5 1 calc R U P . .
C25 C 0.2092(5) 0.750000 0.3294(5) 0.1025(16) Uani 1 2 d S T P . .
H25A H 0.250999 0.715378 0.299151 0.123 Uiso 0.5 1 calc R U P . .
H25B H 0.250999 0.784622 0.299151 0.123 Uiso 0.5 1 calc R U 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 N1 1.437(2) . ?
B1 N2 1.445(2) . ?
B1 C13 1.502(2) . ?
N1 C1 1.472(2) . ?
N1 C11 1.524(3) . ?
N2 C3 1.471(2) . ?
N2 C12 1.520(2) . ?
N1' B1' 1.437(2) . ?
N1' B2' 1.445(2) . ?
N1' C13 1.502(2) . ?
B1' C1 1.472(2) . ?
B1' C11 1.524(3) . ?
B2' C3 1.471(2) . ?
B2' C12 1.520(2) . ?
C1 C10 1.384(2) . ?
C1 C2 1.431(2) . ?
C2 C3 1.427(2) . ?
C2 C7 1.428(2) . ?
C3 C4 1.382(2) . ?
C4 C5 1.408(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.364(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.411(2) . ?
C8 C9 1.364(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.406(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.386(2) . ?
C13 C15 1.389(2) . ?
C14 C14 1.390(4) 7_575 ?
C14 H14 0.9500 . ?
C15 C15 1.385(4) 7_575 ?
C15 H15 0.9500 . ?
O21 C25 1.374(6) . ?
O21 C22 1.395(8) . ?
C22 C23 1.441(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.492(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.451(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

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
N1 B1 N2 118.91(14) . . ?
N1 B1 C13 119.81(14) . . ?
N2 B1 C13 121.27(14) . . ?
B1 N1 C1 120.89(14) . . ?
B1 N1 C11 120.33(16) . . ?
C1 N1 C11 118.78(15) . . ?
B1 N2 C3 120.45(14) . . ?
B1 N2 C12 120.55(15) . . ?
C3 N2 C12 118.97(15) . . ?
B1' N1' B2' 118.91(14) . . ?
B1' N1' C13 119.81(14) . . ?
B2' N1' C13 121.27(14) . . ?
N1' B1' C1 120.89(14) . . ?
N1' B1' C11 120.33(16) . . ?
C1 B1' C11 118.78(15) . . ?
N1' B2' C3 120.45(14) . . ?
N1' B2' C12 120.55(15) . . ?
C3 B2' C12 118.97(15) . . ?
C10 C1 C2 119.08(15) . . ?
C10 C1 N1 121.83(15) . . ?
C2 C1 N1 119.08(14) . . ?
C10 C1 B1' 121.83(15) . . ?
C2 C1 B1' 119.08(14) . . ?
C3 C2 C7 119.62(15) . . ?
C3 C2 C1 121.15(14) . . ?
C7 C2 C1 119.23(15) . . ?
C4 C3 C2 119.06(15) . . ?
C4 C3 N2 121.46(15) . . ?
C2 C3 N2 119.46(14) . . ?
C4 C3 B2' 121.46(15) . . ?
C2 C3 B2' 119.46(14) . . ?
C3 C4 C5 121.02(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 120.69(17) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.73(16) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 121.84(16) . . ?
C8 C7 C2 119.29(16) . . ?
C6 C7 C2 118.87(16) . . ?
C9 C8 C7 120.57(16) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.79(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C1 C10 C9 121.03(17) . . ?
C1 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C15 117.29(16) . . ?
C14 C13 N1' 120.44(15) . . ?
C15 C13 N1' 122.24(15) . . ?
C14 C13 B1 120.44(15) . . ?
C15 C13 B1 122.24(15) . . ?
C13 C14 C14 121.30(10) . 7_575 ?
C13 C14 H14 119.4 . . ?
C14 C14 H14 119.4 7_575 . ?
C15 C15 C13 121.37(10) 7_575 . ?
C15 C15 H15 119.3 7_575 . ?
C13 C15 H15 119.3 . . ?
C25 O21 C22 106.9(4) . . ?
O21 C22 C23 112.3(5) . . ?
O21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
O21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 C24 103.8(4) . . ?
C22 C23 H23A 111.0 . . ?
C24 C23 H23A 111.0 . . ?
C22 C23 H23B 111.0 . . ?
C24 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
C25 C24 C23 105.6(4) . . ?
C25 C24 H24A 110.6 . . ?
C23 C24 H24A 110.6 . . ?
C25 C24 H24B 110.6 . . ?
C23 C24 H24B 110.6 . . ?
H24A C24 H24B 108.8 . . ?
O21 C25 C24 111.3(4) . . ?
O21 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
O21 C25 H25B 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 B1 N1 C1 -2.4(2) . . . . ?
C13 B1 N1 C1 176.71(14) . . . . ?
N2 B1 N1 C11 177.56(15) . . . . ?
C13 B1 N1 C11 -3.3(2) . . . . ?
N1 B1 N2 C3 1.1(2) . . . . ?
C13 B1 N2 C3 -178.00(14) . . . . ?
N1 B1 N2 C12 179.15(16) . . . . ?
C13 B1 N2 C12 0.1(2) . . . . ?
B2' N1' B1' C1 -2.4(2) . . . . ?
C13 N1' B1' C1 176.71(14) . . . . ?
B2' N1' B1' C11 177.56(15) . . . . ?
C13 N1' B1' C11 -3.3(2) . . . . ?
B1' N1' B2' C3 1.1(2) . . . . ?
C13 N1' B2' C3 -178.00(14) . . . . ?
B1' N1' B2' C12 179.15(16) . . . . ?
C13 N1' B2' C12 0.1(2) . . . . ?
B1 N1 C1 C10 -178.05(15) . . . . ?
C11 N1 C1 C10 2.0(2) . . . . ?
B1 N1 C1 C2 1.5(2) . . . . ?
C11 N1 C1 C2 -178.44(15) . . . . ?
N1' B1' C1 C10 -178.05(15) . . . . ?
C11 B1' C1 C10 2.0(2) . . . . ?
N1' B1' C1 C2 1.5(2) . . . . ?
C11 B1' C1 C2 -178.44(15) . . . . ?
C10 C1 C2 C3 -179.68(15) . . . . ?
N1 C1 C2 C3 0.7(2) . . . . ?
B1' C1 C2 C3 0.7(2) . . . . ?
C10 C1 C2 C7 0.0(2) . . . . ?
N1 C1 C2 C7 -179.52(14) . . . . ?
B1' C1 C2 C7 -179.52(14) . . . . ?
C7 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C3 C4 179.25(15) . . . . ?
C7 C2 C3 N2 178.24(14) . . . . ?
C1 C2 C3 N2 -2.0(2) . . . . ?
C7 C2 C3 B2' 178.24(14) . . . . ?
C1 C2 C3 B2' -2.0(2) . . . . ?
B1 N2 C3 C4 179.80(15) . . . . ?
C12 N2 C3 C4 1.7(2) . . . . ?
B1 N2 C3 C2 1.1(2) . . . . ?
C12 N2 C3 C2 -176.99(15) . . . . ?
N1' B2' C3 C4 179.80(15) . . . . ?
C12 B2' C3 C4 1.7(2) . . . . ?
N1' B2' C3 C2 1.1(2) . . . . ?
C12 B2' C3 C2 -176.99(15) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
N2 C3 C4 C5 -178.38(16) . . . . ?
B2' C3 C4 C5 -178.38(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 -179.99(17) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C3 C2 C7 C8 -179.79(15) . . . . ?
C1 C2 C7 C8 0.5(2) . . . . ?
C3 C2 C7 C6 0.4(2) . . . . ?
C1 C2 C7 C6 -179.30(15) . . . . ?
C6 C7 C8 C9 179.31(17) . . . . ?
C2 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C2 C1 C10 C9 -0.6(3) . . . . ?
N1 C1 C10 C9 178.96(16) . . . . ?
B1' C1 C10 C9 178.96(16) . . . . ?
C8 C9 C10 C1 0.6(3) . . . . ?
B1' N1' C13 C14 -76.8(2) . . . . ?
B2' N1' C13 C14 102.3(2) . . . . ?
B1' N1' C13 C15 101.5(2) . . . . ?
B2' N1' C13 C15 -79.5(2) . . . . ?
N1 B1 C13 C14 -76.8(2) . . . . ?
N2 B1 C13 C14 102.3(2) . . . . ?
N1 B1 C13 C15 101.5(2) . . . . ?
N2 B1 C13 C15 -79.5(2) . . . . ?
C15 C13 C14 C14 -2.3(2) . . . 7_575 ?
N1' C13 C14 C14 176.02(10) . . . 7_575 ?
B1 C13 C14 C14 176.02(10) . . . 7_575 ?
C14 C13 C15 C15 2.4(2) . . . 7_575 ?
N1' C13 C15 C15 -175.98(11) . . . 7_575 ?
B1 C13 C15 C15 -175.98(11) . . . 7_575 ?
C25 O21 C22 C23 0.000(1) . . . . ?
O21 C22 C23 C24 0.000(1) . . . . ?
C22 C23 C24 C25 0.000(1) . . . . ?
C22 O21 C25 C24 0.000(1) . . . . ?
C23 C24 C25 O21 0.000(0) . . . . ?

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.044


####################################################################### 
# 
# 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_wa3069
_database_code_depnum_ccdc_archive 'CCDC 2338786'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H44 B3 N3, C6 H14 '
_chemical_formula_sum            'C52 H58 B3 N3'
_chemical_formula_weight         757.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.9643(12)
_cell_length_b                   22.2064(11)
_cell_length_c                   11.8863(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.641(6)
_cell_angle_gamma                90
_cell_volume                     4447.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17580
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.06

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_F_000             1624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.279
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35029
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.248
_diffrn_reflns_theta_max         25.749
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8344
_reflns_number_gt                4774
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_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)+(0.0759P)²+2.9948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         8344
_refine_ls_number_parameters     531
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1938
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.029
_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 0.74140(18) 0.57801(15) 0.4355(3) 0.0342(7) Uani 1 1 d . . . . .
B2 B 0.65777(18) 0.86790(14) 0.5209(3) 0.0333(7) Uani 1 1 d . . . . .
B3 B 0.80565(19) 0.87100(15) 0.5099(3) 0.0356(7) Uani 1 1 d . . . . .
N1 N 0.67256(13) 0.54087(11) 0.4338(2) 0.0390(6) Uani 1 1 d . . . . .
N2 N 0.81588(13) 0.54952(10) 0.4305(2) 0.0386(6) Uani 1 1 d . . . . .
N3 N 0.73214(12) 0.83806(10) 0.50473(18) 0.0324(5) Uani 1 1 d . . . . .
C1 C 0.67753(18) 0.47775(14) 0.4295(2) 0.0435(7) Uani 1 1 d . . . . .
C2 C 0.75311(19) 0.45161(13) 0.4211(2) 0.0434(7) Uani 1 1 d . . . . .
C3 C 0.82296(19) 0.48696(13) 0.4210(2) 0.0445(7) Uani 1 1 d . . . . .
C4 C 0.8948(2) 0.45888(16) 0.4133(3) 0.0586(9) Uani 1 1 d . . . . .
H4 H 0.941581 0.482395 0.413794 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8993(3) 0.39619(18) 0.4050(3) 0.0715(11) Uani 1 1 d . . . . .
H5 H 0.949298 0.377711 0.400148 0.086 Uiso 1 1 calc R U . . .
C6 C 0.8336(3) 0.36132(17) 0.4036(3) 0.0724(12) Uani 1 1 d . . . . .
H6 H 0.837921 0.318883 0.396325 0.087 Uiso 1 1 calc R U . . .
C7 C 0.7590(2) 0.38755(15) 0.4129(3) 0.0583(9) Uani 1 1 d . . . . .
C8 C 0.6901(3) 0.35276(17) 0.4150(3) 0.0744(12) Uani 1 1 d . . . . .
H8 H 0.693280 0.310231 0.408117 0.089 Uiso 1 1 calc R U . . .
C9 C 0.6190(3) 0.37868(18) 0.4267(3) 0.0731(12) Uani 1 1 d . . . . .
H9 H 0.573534 0.354079 0.430399 0.088 Uiso 1 1 calc R U . . .
C10 C 0.6121(2) 0.44142(16) 0.4333(3) 0.0604(9) Uani 1 1 d . . . . .
H10 H 0.561920 0.459050 0.440400 0.073 Uiso 1 1 calc R U . . .
C11 C 0.59328(17) 0.56608(16) 0.4349(3) 0.0553(9) Uani 1 1 d . . . . .
H11A H 0.558180 0.550281 0.370330 0.083 Uiso 1 1 calc R U . . .
H11B H 0.595886 0.610055 0.429460 0.083 Uiso 1 1 calc R U . . .
H11C H 0.572480 0.554846 0.505519 0.083 Uiso 1 1 calc R U . . .
C12 C 0.89004(18) 0.58362(16) 0.4389(3) 0.0619(10) Uani 1 1 d . . . . .
H12A H 0.926982 0.567580 0.501218 0.093 Uiso 1 1 calc R U . . .
H12B H 0.879220 0.626095 0.453442 0.093 Uiso 1 1 calc R U . . .
H12C H 0.913640 0.580050 0.367766 0.093 Uiso 1 1 calc R U . . .
C21 C 0.73505(15) 0.64819(12) 0.4481(2) 0.0337(6) Uani 1 1 d . . . . .
C22 C 0.71122(15) 0.67337(12) 0.5465(2) 0.0361(6) Uani 1 1 d . . . . .
H22 H 0.696139 0.647365 0.603795 0.043 Uiso 1 1 calc R U . . .
C23 C 0.70893(16) 0.73493(13) 0.5631(2) 0.0363(6) Uani 1 1 d . . . . .
H23 H 0.691971 0.750447 0.630827 0.044 Uiso 1 1 calc R U . . .
C24 C 0.73110(14) 0.77408(12) 0.4820(2) 0.0308(6) Uani 1 1 d . . . . .
C25 C 0.75374(15) 0.75063(12) 0.3831(2) 0.0341(6) Uani 1 1 d . . . . .
H25 H 0.768295 0.776912 0.325884 0.041 Uiso 1 1 calc R U . . .
C26 C 0.75529(15) 0.68888(12) 0.3669(2) 0.0348(6) Uani 1 1 d . . . . .
H26 H 0.770702 0.673715 0.298011 0.042 Uiso 1 1 calc R U . . .
C31 C 0.66163(16) 0.93487(13) 0.5602(2) 0.0381(7) Uani 1 1 d . . . . .
C32 C 0.73569(17) 0.96648(13) 0.5755(2) 0.0382(7) Uani 1 1 d . . . . .
C33 C 0.80700(17) 0.93757(13) 0.5505(2) 0.0407(7) Uani 1 1 d . . . . .
C34 C 0.87654(19) 0.97006(14) 0.5638(3) 0.0522(8) Uani 1 1 d . . . . .
H34 H 0.924078 0.951352 0.546681 0.063 Uiso 1 1 calc R U . . .
C35 C 0.8795(2) 1.03002(16) 0.6021(3) 0.0631(10) Uani 1 1 d . . . . .
H35 H 0.928653 1.051025 0.611431 0.076 Uiso 1 1 calc R U . . .
C36 C 0.8117(2) 1.05797(15) 0.6257(3) 0.0594(9) Uani 1 1 d . . . . .
H36 H 0.814008 1.098538 0.651241 0.071 Uiso 1 1 calc R U . . .
C37 C 0.73779(19) 1.02731(14) 0.6127(3) 0.0468(8) Uani 1 1 d . . . . .
C38 C 0.6664(2) 1.05546(15) 0.6353(3) 0.0543(9) Uani 1 1 d . . . . .
H38 H 0.667441 1.095840 0.661810 0.065 Uiso 1 1 calc R U . . .
C39 C 0.5960(2) 1.02510(15) 0.6193(3) 0.0541(9) Uani 1 1 d . . . . .
H39 H 0.548330 1.044565 0.633678 0.065 Uiso 1 1 calc R U . . .
C40 C 0.59398(18) 0.96554(14) 0.5818(3) 0.0474(8) Uani 1 1 d . . . . .
H40 H 0.544358 0.945296 0.570640 0.057 Uiso 1 1 calc R U . . .
C41 C 0.57513(15) 0.83623(12) 0.4906(2) 0.0336(6) Uani 1 1 d . . . . .
C42 C 0.54418(16) 0.83149(12) 0.3757(2) 0.0358(6) Uani 1 1 d . . . . .
C43 C 0.46838(16) 0.80892(13) 0.3464(3) 0.0409(7) Uani 1 1 d . . . . .
H43 H 0.448803 0.805850 0.268449 0.049 Uiso 1 1 calc R U . . .
C44 C 0.42012(16) 0.79069(13) 0.4264(3) 0.0427(7) Uani 1 1 d . . . . .
C45 C 0.45100(17) 0.79492(13) 0.5398(3) 0.0436(7) Uani 1 1 d . . . . .
H45 H 0.419431 0.782130 0.596301 0.052 Uiso 1 1 calc R U . . .
C46 C 0.52688(16) 0.81738(13) 0.5729(2) 0.0375(7) Uani 1 1 d . . . . .
C47 C 0.59098(18) 0.85274(16) 0.2831(3) 0.0499(8) Uani 1 1 d . . . . .
H47A H 0.604854 0.895276 0.295088 0.075 Uiso 1 1 calc R U . . .
H47B H 0.558940 0.847961 0.209557 0.075 Uiso 1 1 calc R U . . .
H47C H 0.639597 0.828792 0.284272 0.075 Uiso 1 1 calc R U . . .
C48 C 0.33737(19) 0.76777(17) 0.3915(3) 0.0659(10) Uani 1 1 d . . . . .
H48A H 0.317433 0.784528 0.317338 0.099 Uiso 1 1 calc R U . . .
H48B H 0.302580 0.780149 0.447614 0.099 Uiso 1 1 calc R U . . .
H48C H 0.338249 0.723722 0.386740 0.099 Uiso 1 1 calc R U . . .
C49 C 0.55579(18) 0.82184(16) 0.6974(2) 0.0496(8) Uani 1 1 d . . . . .
H49A H 0.575516 0.782472 0.725357 0.074 Uiso 1 1 calc R U . . .
H49B H 0.511924 0.834420 0.738962 0.074 Uiso 1 1 calc R U . . .
H49C H 0.598729 0.851509 0.708969 0.074 Uiso 1 1 calc R U . . .
C51 C 0.88483(15) 0.84190(12) 0.4763(2) 0.0346(6) Uani 1 1 d . . . . .
C52 C 0.91147(16) 0.85561(13) 0.3717(2) 0.0392(7) Uani 1 1 d . . . . .
C53 C 0.98381(17) 0.83283(14) 0.3459(3) 0.0450(7) Uani 1 1 d . . . . .
H53 H 1.001382 0.842593 0.275105 0.054 Uiso 1 1 calc R U . . .
C54 C 1.03103(17) 0.79615(14) 0.4211(3) 0.0482(8) Uani 1 1 d . . . . .
C55 C 1.00401(17) 0.78308(14) 0.5234(3) 0.0494(8) Uani 1 1 d . . . . .
H55 H 1.035355 0.758054 0.575757 0.059 Uiso 1 1 calc R U . . .
C56 C 0.93283(16) 0.80517(13) 0.5524(2) 0.0403(7) Uani 1 1 d . . . . .
C57 C 0.8630(2) 0.89428(16) 0.2858(3) 0.0568(9) Uani 1 1 d . . . . .
H57A H 0.809119 0.898453 0.306827 0.085 Uiso 1 1 calc R U . . .
H57B H 0.860810 0.875449 0.210907 0.085 Uiso 1 1 calc R U . . .
H57C H 0.887573 0.934151 0.283592 0.085 Uiso 1 1 calc R U . . .
C58 C 1.1094(2) 0.77215(19) 0.3906(4) 0.0778(12) Uani 1 1 d . . . . .
H58A H 1.152247 0.784608 0.448382 0.117 Uiso 1 1 calc R U . . .
H58B H 1.119399 0.788238 0.316815 0.117 Uiso 1 1 calc R U . . .
H58C H 1.107301 0.728086 0.386958 0.117 Uiso 1 1 calc R U . . .
C59 C 0.90724(19) 0.79077(18) 0.6665(3) 0.0603(10) Uani 1 1 d . . . . .
H59A H 0.865303 0.760202 0.657746 0.090 Uiso 1 1 calc R U . . .
H59B H 0.887049 0.827342 0.699321 0.090 Uiso 1 1 calc R U . . .
H59C H 0.952693 0.775376 0.716613 0.090 Uiso 1 1 calc R U . . .
C61 C 0.3768(6) 0.9747(4) 0.7335(7) 0.194(4) Uani 1 1 d D . . . .
H61A H 0.431697 0.974496 0.769951 0.292 Uiso 1 1 calc R U . . .
H61B H 0.375409 0.990965 0.656675 0.292 Uiso 1 1 calc R U . . .
H61C H 0.344117 0.999745 0.777566 0.292 Uiso 1 1 calc R U . . .
C62 C 0.3464(7) 0.9139(4) 0.7280(10) 0.306(11) Uani 1 1 d D . . . .
H62A H 0.383331 0.890055 0.687158 0.367 Uiso 1 1 calc R U . . .
H62B H 0.352340 0.898750 0.806887 0.367 Uiso 1 1 calc R U . . .
C63 C 0.2661(8) 0.8969(7) 0.6789(12) 0.364(13) Uani 1 1 d D . . . .
H63A H 0.254233 0.913285 0.601286 0.437 Uiso 1 1 calc R U . . .
H63B H 0.260053 0.852614 0.676145 0.437 Uiso 1 1 calc R U . . .
C64 C 0.2146(9) 0.9235(6) 0.7547(10) 0.329(12) Uani 1 1 d D . . . .
H64A H 0.206438 0.967228 0.741565 0.395 Uiso 1 1 calc R U . . .
H64B H 0.233362 0.915949 0.835479 0.395 Uiso 1 1 calc R U . . .
C65 C 0.1427(7) 0.8870(5) 0.7133(12) 0.289(8) Uani 1 1 d D . . . .
H65A H 0.148580 0.845337 0.742579 0.347 Uiso 1 1 calc R U . . .
H65B H 0.135820 0.885529 0.629524 0.347 Uiso 1 1 calc R U . . .
C66 C 0.0713(5) 0.9172(5) 0.7562(9) 0.214(5) Uani 1 1 d D . . . .
H66A H 0.023169 0.894307 0.730423 0.321 Uiso 1 1 calc R U . . .
H66B H 0.078698 0.918338 0.839162 0.321 Uiso 1 1 calc R U . . .
H66C H 0.065989 0.958366 0.726565 0.321 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 N2 1.420(4) . ?
B1 N1 1.428(4) . ?
B1 C21 1.571(4) . ?
B2 N3 1.457(4) . ?
B2 C31 1.558(4) . ?
B2 C41 1.572(4) . ?
B3 N3 1.441(4) . ?
B3 C33 1.554(4) . ?
B3 C51 1.583(4) . ?
N1 C1 1.405(4) . ?
N1 C11 1.458(4) . ?
N2 C3 1.400(4) . ?
N2 C12 1.462(4) . ?
N3 C24 1.446(3) . ?
C1 C10 1.377(4) . ?
C1 C2 1.421(4) . ?
C2 C3 1.422(4) . ?
C2 C7 1.430(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.398(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.355(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.410(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(5) . ?
C8 C9 1.358(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C21 C26 1.394(4) . ?
C21 C22 1.398(4) . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(4) . ?
C25 C26 1.385(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C40 1.384(4) . ?
C31 C32 1.432(4) . ?
C32 C37 1.421(4) . ?
C32 C33 1.431(4) . ?
C33 C34 1.376(4) . ?
C34 C35 1.406(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.365(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.420(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.416(4) . ?
C38 C39 1.365(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.395(4) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.408(4) . ?
C41 C46 1.410(4) . ?
C42 C43 1.387(4) . ?
C42 C47 1.506(4) . ?
C43 C44 1.385(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.392(4) . ?
C44 C48 1.506(4) . ?
C45 C46 1.394(4) . ?
C45 H45 0.9500 . ?
C46 C49 1.508(4) . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C51 C52 1.405(4) . ?
C51 C56 1.406(4) . ?
C52 C53 1.394(4) . ?
C52 C57 1.504(4) . ?
C53 C54 1.392(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.379(4) . ?
C54 C58 1.515(4) . ?
C55 C56 1.383(4) . ?
C55 H55 0.9500 . ?
C56 C59 1.505(4) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C61 C62 1.443(7) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C62 C63 1.467(7) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.452(8) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 C65 1.500(8) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 C66 1.523(7) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 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
N2 B1 N1 118.2(3) . . ?
N2 B1 C21 121.1(2) . . ?
N1 B1 C21 120.6(2) . . ?
N3 B2 C31 117.8(2) . . ?
N3 B2 C41 121.9(2) . . ?
C31 B2 C41 120.1(2) . . ?
N3 B3 C33 118.5(2) . . ?
N3 B3 C51 122.5(3) . . ?
C33 B3 C51 118.9(2) . . ?
C1 N1 B1 121.6(2) . . ?
C1 N1 C11 116.3(2) . . ?
B1 N1 C11 122.1(2) . . ?
C3 N2 B1 122.0(2) . . ?
C3 N2 C12 116.0(2) . . ?
B1 N2 C12 121.9(2) . . ?
B3 N3 C24 119.9(2) . . ?
B3 N3 B2 121.5(2) . . ?
C24 N3 B2 118.6(2) . . ?
C10 C1 N1 122.1(3) . . ?
C10 C1 C2 120.0(3) . . ?
N1 C1 C2 117.9(3) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 C7 119.0(3) . . ?
C1 C2 C7 118.8(3) . . ?
C4 C3 N2 122.5(3) . . ?
C4 C3 C2 119.5(3) . . ?
N2 C3 C2 117.9(3) . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 122.1(4) . . ?
C8 C7 C2 118.8(4) . . ?
C6 C7 C2 119.1(4) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C1 C10 C9 120.6(4) . . ?
C1 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C26 C21 C22 116.0(3) . . ?
C26 C21 B1 123.5(2) . . ?
C22 C21 B1 120.5(2) . . ?
C23 C22 C21 122.1(3) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 118.8(3) . . ?
C25 C24 N3 122.1(2) . . ?
C23 C24 N3 119.1(2) . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 122.4(3) . . ?
C25 C26 H26 118.8 . . ?
C21 C26 H26 118.8 . . ?
C40 C31 C32 118.0(3) . . ?
C40 C31 B2 121.2(3) . . ?
C32 C31 B2 120.8(2) . . ?
C37 C32 C33 120.0(3) . . ?
C37 C32 C31 119.7(3) . . ?
C33 C32 C31 120.3(3) . . ?
C34 C33 C32 118.4(3) . . ?
C34 C33 B3 121.1(3) . . ?
C32 C33 B3 120.6(3) . . ?
C33 C34 C35 122.2(3) . . ?
C33 C34 H34 118.9 . . ?
C35 C34 H34 118.9 . . ?
C36 C35 C34 119.8(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 121.0(3) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C36 C37 C38 122.1(3) . . ?
C36 C37 C32 118.7(3) . . ?
C38 C37 C32 119.2(3) . . ?
C39 C38 C37 120.6(3) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 120.1(3) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C31 C40 C39 122.4(3) . . ?
C31 C40 H40 118.8 . . ?
C39 C40 H40 118.8 . . ?
C42 C41 C46 118.0(3) . . ?
C42 C41 B2 118.6(2) . . ?
C46 C41 B2 123.2(2) . . ?
C43 C42 C41 120.1(3) . . ?
C43 C42 C47 118.8(3) . . ?
C41 C42 C47 121.1(3) . . ?
C44 C43 C42 122.5(3) . . ?
C44 C43 H43 118.7 . . ?
C42 C43 H43 118.7 . . ?
C43 C44 C45 117.3(3) . . ?
C43 C44 C48 121.1(3) . . ?
C45 C44 C48 121.6(3) . . ?
C44 C45 C46 122.0(3) . . ?
C44 C45 H45 119.0 . . ?
C46 C45 H45 119.0 . . ?
C45 C46 C41 120.1(3) . . ?
C45 C46 C49 119.0(3) . . ?
C41 C46 C49 120.8(3) . . ?
C42 C47 H47A 109.5 . . ?
C42 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C42 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C44 C48 H48A 109.5 . . ?
C44 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C44 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C46 C49 H49A 109.5 . . ?
C46 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C46 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C52 C51 C56 118.3(2) . . ?
C52 C51 B3 120.3(2) . . ?
C56 C51 B3 121.3(2) . . ?
C53 C52 C51 119.8(3) . . ?
C53 C52 C57 119.0(3) . . ?
C51 C52 C57 121.2(3) . . ?
C54 C53 C52 121.8(3) . . ?
C54 C53 H53 119.1 . . ?
C52 C53 H53 119.1 . . ?
C55 C54 C53 117.6(3) . . ?
C55 C54 C58 121.8(3) . . ?
C53 C54 C58 120.5(3) . . ?
C54 C55 C56 122.3(3) . . ?
C54 C55 H55 118.9 . . ?
C56 C55 H55 118.9 . . ?
C55 C56 C51 120.2(3) . . ?
C55 C56 C59 120.0(3) . . ?
C51 C56 C59 119.8(2) . . ?
C52 C57 H57A 109.5 . . ?
C52 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C52 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C54 C58 H58A 109.5 . . ?
C54 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C54 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C56 C59 H59A 109.5 . . ?
C56 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C56 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C62 C61 H61A 109.5 . . ?
C62 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C62 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C63 C62 C61 124.7(12) . . ?
C63 C62 H62A 106.2 . . ?
C61 C62 H62A 106.2 . . ?
C63 C62 H62B 106.2 . . ?
C61 C62 H62B 106.2 . . ?
H62A C62 H62B 106.4 . . ?
C64 C63 C62 104.2(12) . . ?
C64 C63 H63A 110.9 . . ?
C62 C63 H63A 110.9 . . ?
C64 C63 H63B 110.9 . . ?
C62 C63 H63B 110.9 . . ?
H63A C63 H63B 108.9 . . ?
C63 C64 C65 95.8(9) . . ?
C63 C64 H64A 112.6 . . ?
C65 C64 H64A 112.6 . . ?
C63 C64 H64B 112.6 . . ?
C65 C64 H64B 112.6 . . ?
H64A C64 H64B 110.1 . . ?
C64 C65 C66 107.5(10) . . ?
C64 C65 H65A 110.2 . . ?
C66 C65 H65A 110.2 . . ?
C64 C65 H65B 110.2 . . ?
C66 C65 H65B 110.2 . . ?
H65A C65 H65B 108.5 . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 B1 N1 C1 1.1(4) . . . . ?
C21 B1 N1 C1 -176.1(3) . . . . ?
N2 B1 N1 C11 -178.0(3) . . . . ?
C21 B1 N1 C11 4.8(4) . . . . ?
N1 B1 N2 C3 1.8(4) . . . . ?
C21 B1 N2 C3 179.0(3) . . . . ?
N1 B1 N2 C12 -176.1(3) . . . . ?
C21 B1 N2 C12 1.1(4) . . . . ?
C33 B3 N3 C24 -171.8(2) . . . . ?
C51 B3 N3 C24 8.0(4) . . . . ?
C33 B3 N3 B2 8.8(4) . . . . ?
C51 B3 N3 B2 -171.4(2) . . . . ?
C31 B2 N3 B3 -8.2(4) . . . . ?
C41 B2 N3 B3 166.8(3) . . . . ?
C31 B2 N3 C24 172.4(2) . . . . ?
C41 B2 N3 C24 -12.6(4) . . . . ?
B1 N1 C1 C10 176.9(3) . . . . ?
C11 N1 C1 C10 -4.0(4) . . . . ?
B1 N1 C1 C2 -3.0(4) . . . . ?
C11 N1 C1 C2 176.1(3) . . . . ?
C10 C1 C2 C3 -177.7(3) . . . . ?
N1 C1 C2 C3 2.1(4) . . . . ?
C10 C1 C2 C7 2.1(4) . . . . ?
N1 C1 C2 C7 -178.0(3) . . . . ?
B1 N2 C3 C4 178.4(3) . . . . ?
C12 N2 C3 C4 -3.6(4) . . . . ?
B1 N2 C3 C2 -2.7(4) . . . . ?
C12 N2 C3 C2 175.4(3) . . . . ?
C1 C2 C3 C4 179.6(3) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 N2 0.6(4) . . . . ?
C7 C2 C3 N2 -179.2(3) . . . . ?
N2 C3 C4 C5 179.4(3) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C7 -1.2(6) . . . . ?
C5 C6 C7 C8 -178.2(4) . . . . ?
C5 C6 C7 C2 1.4(5) . . . . ?
C3 C2 C7 C8 178.9(3) . . . . ?
C1 C2 C7 C8 -0.9(5) . . . . ?
C3 C2 C7 C6 -0.6(5) . . . . ?
C1 C2 C7 C6 179.5(3) . . . . ?
C6 C7 C8 C9 178.4(4) . . . . ?
C2 C7 C8 C9 -1.2(5) . . . . ?
C7 C8 C9 C10 2.1(6) . . . . ?
N1 C1 C10 C9 178.8(3) . . . . ?
C2 C1 C10 C9 -1.3(5) . . . . ?
C8 C9 C10 C1 -0.8(6) . . . . ?
N2 B1 C21 C26 63.6(4) . . . . ?
N1 B1 C21 C26 -119.2(3) . . . . ?
N2 B1 C21 C22 -113.6(3) . . . . ?
N1 B1 C21 C22 63.5(4) . . . . ?
C26 C21 C22 C23 -0.9(4) . . . . ?
B1 C21 C22 C23 176.6(2) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C25 1.5(4) . . . . ?
C22 C23 C24 N3 -176.7(2) . . . . ?
B3 N3 C24 C25 -60.5(3) . . . . ?
B2 N3 C24 C25 118.9(3) . . . . ?
B3 N3 C24 C23 117.6(3) . . . . ?
B2 N3 C24 C23 -63.0(3) . . . . ?
C23 C24 C25 C26 -1.1(4) . . . . ?
N3 C24 C25 C26 177.1(2) . . . . ?
C24 C25 C26 C21 -0.4(4) . . . . ?
C22 C21 C26 C25 1.4(4) . . . . ?
B1 C21 C26 C25 -176.0(3) . . . . ?
N3 B2 C31 C40 -177.4(3) . . . . ?
C41 B2 C31 C40 7.5(4) . . . . ?
N3 B2 C31 C32 2.4(4) . . . . ?
C41 B2 C31 C32 -172.7(2) . . . . ?
C40 C31 C32 C37 0.6(4) . . . . ?
B2 C31 C32 C37 -179.2(3) . . . . ?
C40 C31 C32 C33 -177.8(3) . . . . ?
B2 C31 C32 C33 2.4(4) . . . . ?
C37 C32 C33 C34 0.2(4) . . . . ?
C31 C32 C33 C34 178.5(3) . . . . ?
C37 C32 C33 B3 179.9(3) . . . . ?
C31 C32 C33 B3 -1.8(4) . . . . ?
N3 B3 C33 C34 175.9(3) . . . . ?
C51 B3 C33 C34 -3.9(4) . . . . ?
N3 B3 C33 C32 -3.8(4) . . . . ?
C51 B3 C33 C32 176.5(3) . . . . ?
C32 C33 C34 C35 0.7(5) . . . . ?
B3 C33 C34 C35 -179.0(3) . . . . ?
C33 C34 C35 C36 -0.9(5) . . . . ?
C34 C35 C36 C37 0.2(5) . . . . ?
C35 C36 C37 C38 -179.2(3) . . . . ?
C35 C36 C37 C32 0.6(5) . . . . ?
C33 C32 C37 C36 -0.8(4) . . . . ?
C31 C32 C37 C36 -179.1(3) . . . . ?
C33 C32 C37 C38 179.0(3) . . . . ?
C31 C32 C37 C38 0.6(4) . . . . ?
C36 C37 C38 C39 178.4(3) . . . . ?
C32 C37 C38 C39 -1.4(5) . . . . ?
C37 C38 C39 C40 0.8(5) . . . . ?
C32 C31 C40 C39 -1.1(4) . . . . ?
B2 C31 C40 C39 178.7(3) . . . . ?
C38 C39 C40 C31 0.4(5) . . . . ?
N3 B2 C41 C42 -75.8(3) . . . . ?
C31 B2 C41 C42 99.1(3) . . . . ?
N3 B2 C41 C46 110.4(3) . . . . ?
C31 B2 C41 C46 -74.7(4) . . . . ?
C46 C41 C42 C43 0.1(4) . . . . ?
B2 C41 C42 C43 -174.0(3) . . . . ?
C46 C41 C42 C47 177.8(3) . . . . ?
B2 C41 C42 C47 3.7(4) . . . . ?
C41 C42 C43 C44 0.4(4) . . . . ?
C47 C42 C43 C44 -177.4(3) . . . . ?
C42 C43 C44 C45 -0.9(4) . . . . ?
C42 C43 C44 C48 178.5(3) . . . . ?
C43 C44 C45 C46 1.0(4) . . . . ?
C48 C44 C45 C46 -178.5(3) . . . . ?
C44 C45 C46 C41 -0.5(4) . . . . ?
C44 C45 C46 C49 178.8(3) . . . . ?
C42 C41 C46 C45 -0.1(4) . . . . ?
B2 C41 C46 C45 173.8(3) . . . . ?
C42 C41 C46 C49 -179.3(3) . . . . ?
B2 C41 C46 C49 -5.5(4) . . . . ?
N3 B3 C51 C52 103.2(3) . . . . ?
C33 B3 C51 C52 -77.0(3) . . . . ?
N3 B3 C51 C56 -81.0(4) . . . . ?
C33 B3 C51 C56 98.8(3) . . . . ?
C56 C51 C52 C53 0.0(4) . . . . ?
B3 C51 C52 C53 175.9(3) . . . . ?
C56 C51 C52 C57 179.6(3) . . . . ?
B3 C51 C52 C57 -4.5(4) . . . . ?
C51 C52 C53 C54 0.4(4) . . . . ?
C57 C52 C53 C54 -179.2(3) . . . . ?
C52 C53 C54 C55 -0.3(5) . . . . ?
C52 C53 C54 C58 -179.9(3) . . . . ?
C53 C54 C55 C56 -0.1(5) . . . . ?
C58 C54 C55 C56 179.5(3) . . . . ?
C54 C55 C56 C51 0.5(5) . . . . ?
C54 C55 C56 C59 -178.4(3) . . . . ?
C52 C51 C56 C55 -0.5(4) . . . . ?
B3 C51 C56 C55 -176.3(3) . . . . ?
C52 C51 C56 C59 178.5(3) . . . . ?
B3 C51 C56 C59 2.6(4) . . . . ?
C61 C62 C63 C64 -67.1(17) . . . . ?
C62 C63 C64 C65 -163.9(11) . . . . ?
C63 C64 C65 C66 -164.8(11) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.045


