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

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1884516'
loop_
_audit_author_name
_audit_author_address
'Makoto Yamashita'
;Nagoya University
Japan
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H44 B2 N2 O2'
_chemical_formula_sum            'C28 H44 B2 N2 O2'
_chemical_formula_weight         462.27

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

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

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

_cell_length_a                   9.449(3)
_cell_length_b                   10.482(3)
_cell_length_c                   14.853(4)
_cell_angle_alpha                102.318(5)
_cell_angle_beta                 95.597(4)
_cell_angle_gamma                99.344(4)
_cell_volume                     1404.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    4214
_cell_measurement_theta_min      2.4524
_cell_measurement_theta_max      31.3328

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8823
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            11586
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             6206
_reflns_number_gt                3851
_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       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009(Wakita Nemoto et al.)'
_computing_publication_material  'Yadokari-XG 2009(Wakita,Nemoto et al.)'
_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)+(0.0616P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6206
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37147(14) 0.40687(14) 0.40377(9) 0.0172(3) Uani 1 1 d . . . . .
H1 H 0.3732 0.4990 0.4385 0.021 Uiso 1 1 calc R U . . .
H1A H 0.4095 0.3567 0.4470 0.021 Uiso 1 1 calc R U . . .
C2 C 0.21950(15) 0.33967(14) 0.35694(10) 0.0188(3) Uani 1 1 d . . . . .
H2 H 0.1691 0.2865 0.3960 0.023 Uiso 1 1 calc R U . . .
H2A H 0.1614 0.4059 0.3440 0.023 Uiso 1 1 calc R U . . .
N1 N 0.24469(12) 0.25374(11) 0.26989(8) 0.0158(3) Uani 1 1 d . . . . .
B1 B 0.38202(17) 0.30394(15) 0.24647(11) 0.0162(3) Uani 1 1 d . . . . .
N2 N 0.45573(12) 0.40533(11) 0.32509(8) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.11983(15) 0.17080(13) 0.21028(10) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.07038(15) 0.04267(14) 0.22383(10) 0.0184(3) Uani 1 1 d . . . . .
C5 C -0.05140(16) -0.03616(14) 0.16601(11) 0.0226(3) Uani 1 1 d . . . . .
H5 H -0.0858 -0.1228 0.1740 0.027 Uiso 1 1 calc R U . . .
C6 C -0.12307(16) 0.00960(15) 0.09718(11) 0.0246(4) Uani 1 1 d . . . . .
H6 H -0.2058 -0.0456 0.0582 0.030 Uiso 1 1 calc R U . . .
C7 C -0.07420(16) 0.13558(15) 0.08524(10) 0.0235(3) Uani 1 1 d . . . . .
H7 H -0.1240 0.1663 0.0378 0.028 Uiso 1 1 calc R U . . .
C8 C 0.04686(15) 0.21857(14) 0.14146(10) 0.0196(3) Uani 1 1 d . . . . .
C9 C 0.09166(17) 0.35866(14) 0.12801(11) 0.0242(3) Uani 1 1 d . . . . .
H9 H 0.1810 0.4024 0.1728 0.029 Uiso 1 1 calc R U . . .
C10 C 0.12800(19) 0.35778(17) 0.02960(11) 0.0331(4) Uani 1 1 d . . . . .
H10 H 0.0414 0.3171 -0.0157 0.050 Uiso 1 1 calc R U . . .
H10A H 0.2047 0.3064 0.0170 0.050 Uiso 1 1 calc R U . . .
H10B H 0.1612 0.4492 0.0246 0.050 Uiso 1 1 calc R U . . .
C11 C -0.0259(2) 0.44065(16) 0.15036(12) 0.0359(4) Uani 1 1 d . . . . .
H11 H -0.1133 0.4026 0.1053 0.054 Uiso 1 1 calc R U . . .
H11A H 0.0087 0.5326 0.1469 0.054 Uiso 1 1 calc R U . . .
H11B H -0.0486 0.4393 0.2132 0.054 Uiso 1 1 calc R U . . .
C12 C 0.14382(16) -0.00894(14) 0.30097(11) 0.0232(3) Uani 1 1 d . . . . .
H12 H 0.2418 0.0483 0.3226 0.028 Uiso 1 1 calc R U . . .
C13 C 0.16439(19) -0.15314(15) 0.26807(13) 0.0354(4) Uani 1 1 d . . . . .
H13 H 0.0698 -0.2128 0.2543 0.053 Uiso 1 1 calc R U . . .
H13A H 0.2247 -0.1769 0.3171 0.053 Uiso 1 1 calc R U . . .
H13B H 0.2118 -0.1617 0.2118 0.053 Uiso 1 1 calc R U . . .
C14 C 0.05871(18) 0.00188(16) 0.38421(11) 0.0304(4) Uani 1 1 d . . . . .
H14 H 0.0537 0.0952 0.4090 0.046 Uiso 1 1 calc R U . . .
H14A H 0.1076 -0.0324 0.4327 0.046 Uiso 1 1 calc R U . . .
H14B H -0.0395 -0.0502 0.3641 0.046 Uiso 1 1 calc R U . . .
C15 C 0.60668(14) 0.46307(13) 0.34835(9) 0.0152(3) Uani 1 1 d . . . . .
C16 C 0.70675(15) 0.38529(14) 0.37050(10) 0.0174(3) Uani 1 1 d . . . . .
C17 C 0.85293(15) 0.44516(15) 0.39461(10) 0.0220(3) Uani 1 1 d . . . . .
H17 H 0.9220 0.3938 0.4096 0.026 Uiso 1 1 calc R U . . .
C18 C 0.89806(16) 0.57801(15) 0.39688(11) 0.0250(4) Uani 1 1 d . . . . .
H18 H 0.9979 0.6172 0.4123 0.030 Uiso 1 1 calc R U . . .
C19 C 0.79821(16) 0.65387(15) 0.37674(10) 0.0239(3) Uani 1 1 d . . . . .
H19 H 0.8305 0.7454 0.3792 0.029 Uiso 1 1 calc R U . . .
C20 C 0.65130(15) 0.59959(13) 0.35286(10) 0.0180(3) Uani 1 1 d . . . . .
C21 C 0.54437(16) 0.68497(14) 0.32934(10) 0.0220(3) Uani 1 1 d . . . . .
H21 H 0.4461 0.6411 0.3380 0.026 Uiso 1 1 calc R U . . .
C22 C 0.5395(2) 0.69219(17) 0.22750(11) 0.0376(4) Uani 1 1 d . . . . .
H22 H 0.6350 0.7341 0.2169 0.056 Uiso 1 1 calc R U . . .
H22A H 0.4676 0.7449 0.2127 0.056 Uiso 1 1 calc R U . . .
H22B H 0.5128 0.6022 0.1876 0.056 Uiso 1 1 calc R U . . .
C23 C 0.57727(18) 0.82501(14) 0.39237(12) 0.0301(4) Uani 1 1 d . . . . .
H23 H 0.5867 0.8193 0.4576 0.045 Uiso 1 1 calc R U . . .
H23A H 0.4982 0.8716 0.3800 0.045 Uiso 1 1 calc R U . . .
H23B H 0.6680 0.8739 0.3800 0.045 Uiso 1 1 calc R U . . .
C24 C 0.66311(15) 0.23838(13) 0.36876(10) 0.0192(3) Uani 1 1 d . . . . .
H24 H 0.5550 0.2151 0.3585 0.023 Uiso 1 1 calc R U . . .
C25 C 0.71932(17) 0.15312(15) 0.28811(11) 0.0263(4) Uani 1 1 d . . . . .
H25 H 0.6816 0.1718 0.2294 0.039 Uiso 1 1 calc R U . . .
H25A H 0.6870 0.0589 0.2865 0.039 Uiso 1 1 calc R U . . .
H25B H 0.8254 0.1741 0.2968 0.039 Uiso 1 1 calc R U . . .
C26 C 0.71626(17) 0.20749(15) 0.46093(11) 0.0259(4) Uani 1 1 d . . . . .
H26 H 0.6758 0.1150 0.4602 0.039 Uiso 1 1 calc R U . . .
H26A H 0.6849 0.2670 0.5123 0.039 Uiso 1 1 calc R U . . .
H26B H 0.8222 0.2207 0.4694 0.039 Uiso 1 1 calc R U . . .
B2 B 0.44641(17) 0.26215(17) 0.14246(12) 0.0196(4) Uani 1 1 d . . . . .
O1 O 0.44498(11) 0.13751(10) 0.08997(7) 0.0249(3) Uani 1 1 d . . . . .
C27 C 0.39765(19) 0.02035(15) 0.12164(12) 0.0311(4) Uani 1 1 d . . . . .
H27 H 0.4074 0.0425 0.1897 0.047 Uiso 1 1 calc R U . . .
H27A H 0.4570 -0.0458 0.1008 0.047 Uiso 1 1 calc R U . . .
H27B H 0.2960 -0.0160 0.0961 0.047 Uiso 1 1 calc R U . . .
O2 O 0.50236(11) 0.36553(10) 0.10618(7) 0.0258(3) Uani 1 1 d . . . . .
C28 C 0.5544(2) 0.34051(17) 0.01753(11) 0.0351(4) Uani 1 1 d . . . . .
H28 H 0.6263 0.2830 0.0184 0.053 Uiso 1 1 calc R U . . .
H28A H 0.5991 0.4249 0.0050 0.053 Uiso 1 1 calc R U . . .
H28B H 0.4732 0.2966 -0.0313 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
C1 N2 1.4756(17) . ?
C1 C2 1.5199(19) . ?
C2 N1 1.4739(17) . ?
N1 B1 1.424(2) . ?
N1 C3 1.4375(17) . ?
B1 N2 1.432(2) . ?
B1 B2 1.712(2) . ?
N2 C15 1.4334(17) . ?
C3 C8 1.402(2) . ?
C3 C4 1.4116(19) . ?
C4 C5 1.393(2) . ?
C4 C12 1.523(2) . ?
C5 C6 1.383(2) . ?
C6 C7 1.381(2) . ?
C7 C8 1.394(2) . ?
C8 C9 1.522(2) . ?
C9 C11 1.531(2) . ?
C9 C10 1.532(2) . ?
C12 C14 1.534(2) . ?
C12 C13 1.536(2) . ?
C15 C16 1.4040(19) . ?
C15 C20 1.4098(19) . ?
C16 C17 1.399(2) . ?
C16 C24 1.5222(19) . ?
C17 C18 1.381(2) . ?
C18 C19 1.379(2) . ?
C19 C20 1.392(2) . ?
C20 C21 1.517(2) . ?
C21 C22 1.527(2) . ?
C21 C23 1.529(2) . ?
C24 C26 1.529(2) . ?
C24 C25 1.529(2) . ?
B2 O2 1.3649(19) . ?
B2 O1 1.368(2) . ?
O1 C27 1.4278(18) . ?
O2 C28 1.4368(18) . ?

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 C1 C2 103.39(11) . . ?
N1 C2 C1 103.32(10) . . ?
B1 N1 C3 129.07(12) . . ?
B1 N1 C2 109.61(11) . . ?
C3 N1 C2 117.24(10) . . ?
N1 B1 N2 107.04(12) . . ?
N1 B1 B2 127.81(13) . . ?
N2 B1 B2 125.02(13) . . ?
B1 N2 C15 129.68(12) . . ?
B1 N2 C1 109.50(11) . . ?
C15 N2 C1 116.25(11) . . ?
C8 C3 C4 120.90(12) . . ?
C8 C3 N1 120.08(12) . . ?
C4 C3 N1 119.01(13) . . ?
C5 C4 C3 118.36(14) . . ?
C5 C4 C12 119.80(13) . . ?
C3 C4 C12 121.82(12) . . ?
C6 C5 C4 121.13(14) . . ?
C7 C6 C5 119.88(14) . . ?
C6 C7 C8 121.25(14) . . ?
C7 C8 C3 118.48(13) . . ?
C7 C8 C9 118.92(13) . . ?
C3 C8 C9 122.57(12) . . ?
C8 C9 C11 110.83(13) . . ?
C8 C9 C10 111.84(13) . . ?
C11 C9 C10 110.60(13) . . ?
C4 C12 C14 110.94(13) . . ?
C4 C12 C13 112.75(13) . . ?
C14 C12 C13 109.44(13) . . ?
C16 C15 C20 120.96(12) . . ?
C16 C15 N2 119.96(12) . . ?
C20 C15 N2 119.01(12) . . ?
C17 C16 C15 118.59(13) . . ?
C17 C16 C24 118.59(13) . . ?
C15 C16 C24 122.82(12) . . ?
C18 C17 C16 120.80(14) . . ?
C19 C18 C17 119.99(13) . . ?
C18 C19 C20 121.61(14) . . ?
C19 C20 C15 118.01(13) . . ?
C19 C20 C21 120.40(13) . . ?
C15 C20 C21 121.56(12) . . ?
C20 C21 C22 110.34(13) . . ?
C20 C21 C23 112.87(13) . . ?
C22 C21 C23 110.14(13) . . ?
C16 C24 C26 111.80(12) . . ?
C16 C24 C25 110.52(12) . . ?
C26 C24 C25 110.46(13) . . ?
O2 B2 O1 115.99(14) . . ?
O2 B2 B1 116.12(13) . . ?
O1 B2 B1 127.86(13) . . ?
B2 O1 C27 122.15(12) . . ?
B2 O2 C28 120.29(13) . . ?

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 C1 C2 N1 26.24(13) . . . . ?
C1 C2 N1 B1 -23.15(15) . . . . ?
C1 C2 N1 C3 177.46(11) . . . . ?
C3 N1 B1 N2 166.55(13) . . . . ?
C2 N1 B1 N2 10.33(16) . . . . ?
C3 N1 B1 B2 -9.4(2) . . . . ?
C2 N1 B1 B2 -165.60(14) . . . . ?
N1 B1 N2 C15 162.15(13) . . . . ?
B2 B1 N2 C15 -21.8(2) . . . . ?
N1 B1 N2 C1 7.52(16) . . . . ?
B2 B1 N2 C1 -176.40(13) . . . . ?
C2 C1 N2 B1 -21.39(14) . . . . ?
C2 C1 N2 C15 -179.82(11) . . . . ?
B1 N1 C3 C8 -65.0(2) . . . . ?
C2 N1 C3 C8 89.67(16) . . . . ?
B1 N1 C3 C4 116.55(16) . . . . ?
C2 N1 C3 C4 -88.75(16) . . . . ?
C8 C3 C4 C5 1.1(2) . . . . ?
N1 C3 C4 C5 179.51(12) . . . . ?
C8 C3 C4 C12 -177.19(13) . . . . ?
N1 C3 C4 C12 1.2(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C12 C4 C5 C6 178.00(14) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C3 0.7(2) . . . . ?
C6 C7 C8 C9 -177.24(14) . . . . ?
C4 C3 C8 C7 -1.3(2) . . . . ?
N1 C3 C8 C7 -179.69(12) . . . . ?
C4 C3 C8 C9 176.61(13) . . . . ?
N1 C3 C8 C9 -1.8(2) . . . . ?
C7 C8 C9 C11 63.56(18) . . . . ?
C3 C8 C9 C11 -114.34(16) . . . . ?
C7 C8 C9 C10 -60.35(18) . . . . ?
C3 C8 C9 C10 121.75(16) . . . . ?
C5 C4 C12 C14 -77.57(17) . . . . ?
C3 C4 C12 C14 100.70(16) . . . . ?
C5 C4 C12 C13 45.59(19) . . . . ?
C3 C4 C12 C13 -136.14(14) . . . . ?
B1 N2 C15 C16 -66.37(19) . . . . ?
C1 N2 C15 C16 86.86(16) . . . . ?
B1 N2 C15 C20 116.63(16) . . . . ?
C1 N2 C15 C20 -90.13(15) . . . . ?
C20 C15 C16 C17 -1.9(2) . . . . ?
N2 C15 C16 C17 -178.80(12) . . . . ?
C20 C15 C16 C24 178.56(13) . . . . ?
N2 C15 C16 C24 1.6(2) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C24 C16 C17 C18 179.78(13) . . . . ?
C16 C17 C18 C19 1.1(2) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
C18 C19 C20 C15 -0.9(2) . . . . ?
C18 C19 C20 C21 -178.87(14) . . . . ?
C16 C15 C20 C19 2.2(2) . . . . ?
N2 C15 C20 C19 179.19(12) . . . . ?
C16 C15 C20 C21 -179.86(13) . . . . ?
N2 C15 C20 C21 -2.9(2) . . . . ?
C19 C20 C21 C22 83.72(17) . . . . ?
C15 C20 C21 C22 -94.14(16) . . . . ?
C19 C20 C21 C23 -39.99(19) . . . . ?
C15 C20 C21 C23 142.15(14) . . . . ?
C17 C16 C24 C26 54.13(17) . . . . ?
C15 C16 C24 C26 -126.30(15) . . . . ?
C17 C16 C24 C25 -69.34(17) . . . . ?
C15 C16 C24 C25 110.23(15) . . . . ?
N1 B1 B2 O2 129.30(16) . . . . ?
N2 B1 B2 O2 -46.0(2) . . . . ?
N1 B1 B2 O1 -48.7(2) . . . . ?
N2 B1 B2 O1 136.03(16) . . . . ?
O2 B2 O1 C27 176.21(13) . . . . ?
B1 B2 O1 C27 -5.8(2) . . . . ?
O1 B2 O2 C28 0.5(2) . . . . ?
B1 B2 O2 C28 -177.76(13) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.069

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1884518'
loop_
_audit_author_name
_audit_author_address
'Makoto Yamashita'
;Nagoya University
Japan
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H78 B4 N4'
_chemical_formula_sum            'C52 H78 B4 N4'
_chemical_formula_weight         802.42

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

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

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

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

_cell_length_a                   48.944(3)
_cell_length_b                   12.4873(3)
_cell_length_c                   21.7020(14)
_cell_angle_alpha                90
_cell_angle_beta                 129.509(10)
_cell_angle_gamma                90
_cell_volume                     10233.3(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    12172
_cell_measurement_theta_min      2.5030
_cell_measurement_theta_max      30.4400

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.042
_exptl_crystal_F_000             3504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.96871
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            52062
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_limit_h_min       -63
_diffrn_reflns_limit_h_max       63
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11742
_reflns_number_gt                7067
_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       'RIGAKU CrystalClear'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009(Wakita Nemoto et al.)'
_computing_publication_material  'Yadokari-XG 2009(Wakita,Nemoto et al.)'
_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)+(0.0454P)²+7.4978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         11742
_refine_ls_number_parameters     565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.13909(6) 0.32459(18) 0.30195(14) 0.0210(5) Uani 1 1 d . . . . .
B2 B 0.12918(7) 0.2996(2) 0.21434(15) 0.0270(6) Uani 1 1 d . . . . .
B3 B 0.12348(7) 0.2806(2) 0.13918(15) 0.0277(6) Uani 1 1 d . . . . .
H3 H 0.1434(6) 0.349(2) 0.1911(15) 0.062(8) Uiso 1 1 d . . . . .
B4 B 0.11900(6) 0.26393(19) 0.05720(14) 0.0223(5) Uani 1 1 d . . . . .
C1 C 0.15377(5) 0.30331(16) 0.42832(12) 0.0225(4) Uani 1 1 d . . . . .
H1 H 0.176913 0.288742 0.481263 0.027 Uiso 1 1 calc R U . . .
H1A H 0.134657 0.277690 0.428412 0.027 Uiso 1 1 calc R U . . .
C2 C 0.14952(5) 0.42312(16) 0.40864(12) 0.0237(5) Uani 1 1 d . . . . .
H2 H 0.132260 0.456302 0.412417 0.028 Uiso 1 1 calc R U . . .
H2A H 0.172468 0.460886 0.445375 0.028 Uiso 1 1 calc R U . . .
C3 C 0.12314(5) 0.52582(16) 0.28343(11) 0.0215(4) Uani 1 1 d . . . . .
C4 C 0.08678(5) 0.54903(17) 0.23705(12) 0.0269(5) Uani 1 1 d . . . . .
C5 C 0.07463(6) 0.64652(18) 0.19760(13) 0.0334(5) Uani 1 1 d . . . . .
H5 H 0.050181 0.663165 0.166279 0.040 Uiso 1 1 calc R U . . .
C6 C 0.09687(6) 0.71999(18) 0.20235(13) 0.0324(5) Uani 1 1 d . . . . .
H6 H 0.087869 0.786443 0.174987 0.039 Uiso 1 1 calc R U . . .
C7 C 0.13228(6) 0.69620(17) 0.24712(12) 0.0276(5) Uani 1 1 d . . . . .
H7 H 0.147561 0.746232 0.249546 0.033 Uiso 1 1 calc R U . . .
C8 C 0.14617(5) 0.59984(16) 0.28908(12) 0.0225(5) Uani 1 1 d . . . . .
C9 C 0.18560(5) 0.57878(17) 0.33899(12) 0.0248(5) Uani 1 1 d . . . . .
H9 H 0.190869 0.507653 0.365637 0.030 Uiso 1 1 calc R U . . .
C10 C 0.19616(6) 0.57354(18) 0.28625(13) 0.0324(5) Uani 1 1 d . . . . .
H10 H 0.181799 0.519305 0.244654 0.049 Uiso 1 1 calc R U . . .
H10A H 0.221265 0.554457 0.318976 0.049 Uiso 1 1 calc R U . . .
H10B H 0.192201 0.643506 0.261308 0.049 Uiso 1 1 calc R U . . .
C11 C 0.20743(6) 0.66348(19) 0.40397(13) 0.0355(6) Uani 1 1 d . . . . .
H11 H 0.203478 0.733544 0.379159 0.053 Uiso 1 1 calc R U . . .
H11A H 0.232615 0.645020 0.437486 0.053 Uiso 1 1 calc R U . . .
H11B H 0.200226 0.666215 0.436981 0.053 Uiso 1 1 calc R U . . .
C12 C 0.06087(6) 0.46882(19) 0.22697(14) 0.0339(5) Uani 1 1 d . . . . .
H12 H 0.074942 0.412370 0.268812 0.041 Uiso 1 1 calc R U . . .
C13 C 0.03982(7) 0.4143(2) 0.14548(16) 0.0517(7) Uani 1 1 d . . . . .
H13 H 0.026006 0.468042 0.103217 0.078 Uiso 1 1 calc R U . . .
H13A H 0.023781 0.361077 0.140455 0.078 Uiso 1 1 calc R U . . .
H13B H 0.056182 0.378667 0.140504 0.078 Uiso 1 1 calc R U . . .
C14 C 0.03588(6) 0.5190(2) 0.23810(16) 0.0470(7) Uani 1 1 d . . . . .
H14 H 0.049673 0.558657 0.288572 0.070 Uiso 1 1 calc R U . . .
H14A H 0.022282 0.462459 0.239153 0.070 Uiso 1 1 calc R U . . .
H14B H 0.019612 0.567988 0.193739 0.070 Uiso 1 1 calc R U . . .
C15 C 0.15071(5) 0.13629(16) 0.36292(12) 0.0230(5) Uani 1 1 d . . . . .
C16 C 0.18265(6) 0.07866(17) 0.40767(13) 0.0261(5) Uani 1 1 d . . . . .
C17 C 0.18115(6) -0.03269(17) 0.40782(14) 0.0330(5) Uani 1 1 d . . . . .
H17 H 0.202549 -0.072693 0.438335 0.040 Uiso 1 1 calc R U . . .
C18 C 0.14914(6) -0.08615(17) 0.36445(13) 0.0327(5) Uani 1 1 d . . . . .
H18 H 0.148606 -0.162170 0.365117 0.039 Uiso 1 1 calc R U . . .
C19 C 0.11827(6) -0.02910(17) 0.32061(13) 0.0316(5) Uani 1 1 d . . . . .
H19 H 0.096353 -0.066411 0.290182 0.038 Uiso 1 1 calc R U . . .
C20 C 0.11814(6) 0.08240(17) 0.31942(12) 0.0282(5) Uani 1 1 d . . . . .
C21 C 0.21832(5) 0.13387(17) 0.45674(13) 0.0297(5) Uani 1 1 d . . . . .
H21 H 0.214018 0.212529 0.446215 0.036 Uiso 1 1 calc R U . . .
C22 C 0.23993(7) 0.0973(2) 0.43203(18) 0.0495(7) Uani 1 1 d . . . . .
H22 H 0.244751 0.020362 0.442322 0.074 Uiso 1 1 calc R U . . .
H22A H 0.262358 0.136656 0.462946 0.074 Uiso 1 1 calc R U . . .
H22B H 0.226520 0.111254 0.374978 0.074 Uiso 1 1 calc R U . . .
C23 C 0.23874(6) 0.11597(19) 0.54612(14) 0.0411(6) Uani 1 1 d . . . . .
H23 H 0.225405 0.146781 0.561432 0.062 Uiso 1 1 calc R U . . .
H23A H 0.261962 0.150680 0.576646 0.062 Uiso 1 1 calc R U . . .
H23B H 0.241927 0.038985 0.557497 0.062 Uiso 1 1 calc R U . . .
C24 C 0.08300(6) 0.1406(2) 0.27197(15) 0.0458(7) Uani 1 1 d . . . . .
H24 H 0.088058 0.219178 0.279552 0.055 Uiso 1 1 calc R U . . .
C25 C 0.06081(7) 0.1164(2) 0.18271(16) 0.0653(9) Uani 1 1 d . . . . .
H25 H 0.073410 0.141478 0.164047 0.098 Uiso 1 1 calc R U . . .
H25A H 0.037958 0.153162 0.153024 0.098 Uiso 1 1 calc R U . . .
H25B H 0.056874 0.038986 0.173968 0.098 Uiso 1 1 calc R U . . .
C26 C 0.06284(7) 0.1137(2) 0.30233(18) 0.0569(8) Uani 1 1 d . . . . .
H26 H 0.057000 0.037248 0.294406 0.085 Uiso 1 1 calc R U . . .
H26A H 0.040968 0.155860 0.272686 0.085 Uiso 1 1 calc R U . . .
H26B H 0.077649 0.130853 0.359331 0.085 Uiso 1 1 calc R U . . .
C27 C 0.10248(6) 0.19020(17) -0.06264(13) 0.0305(5) Uani 1 1 d . . . . .
H27 H 0.077558 0.194588 -0.112345 0.037 Uiso 1 1 calc R U . . .
H27A H 0.114334 0.130826 -0.067725 0.037 Uiso 1 1 calc R U . . .
C28 C 0.12172(6) 0.29606(17) -0.04635(13) 0.0289(5) Uani 1 1 d . . . . .
H28 H 0.144289 0.283982 -0.036114 0.035 Uiso 1 1 calc R U . . .
H28A H 0.106822 0.345509 -0.092207 0.035 Uiso 1 1 calc R U . . .
C29 C 0.08956(5) 0.07905(16) 0.01206(12) 0.0241(5) Uani 1 1 d . . . . .
C30 C 0.11200(6) -0.00643(17) 0.05904(13) 0.0275(5) Uani 1 1 d . . . . .
C31 C 0.09666(6) -0.09918(18) 0.06141(14) 0.0344(6) Uani 1 1 d . . . . .
H31 H 0.111320 -0.158377 0.092704 0.041 Uiso 1 1 calc R U . . .
C32 C 0.06062(6) -0.10616(18) 0.01911(14) 0.0373(6) Uani 1 1 d . . . . .
H32 H 0.050600 -0.170329 0.020520 0.045 Uiso 1 1 calc R U . . .
C33 C 0.03911(6) -0.02004(18) -0.02524(14) 0.0357(6) Uani 1 1 d . . . . .
H33 H 0.014361 -0.025230 -0.053460 0.043 Uiso 1 1 calc R U . . .
C34 C 0.05298(5) 0.07428(17) -0.02943(13) 0.0285(5) Uani 1 1 d . . . . .
C35 C 0.02938(6) 0.17037(19) -0.07421(14) 0.0354(6) Uani 1 1 d . . . . .
H35 H 0.043560 0.224187 -0.077421 0.043 Uiso 1 1 calc R U . . .
C36 C 0.01902(8) 0.2219(3) -0.02827(16) 0.0752(11) Uani 1 1 d . . . . .
H36 H 0.003681 0.172982 -0.027137 0.113 Uiso 1 1 calc R U . . .
H36A H 0.006301 0.288867 -0.054535 0.113 Uiso 1 1 calc R U . . .
H36B H 0.040382 0.237041 0.026487 0.113 Uiso 1 1 calc R U . . .
H36C H 0.1426(6) 0.2219(19) 0.2009(13) 0.046(7) Uiso 1 1 d . . . . .
C37 C -0.00300(7) 0.1443(2) -0.15882(15) 0.0561(8) Uani 1 1 d . . . . .
H37 H 0.004167 0.104980 -0.185555 0.084 Uiso 1 1 calc R U . . .
H37A H -0.014871 0.210924 -0.187887 0.084 Uiso 1 1 calc R U . . .
H37B H -0.019294 0.100239 -0.157868 0.084 Uiso 1 1 calc R U . . .
C38 C 0.15173(6) 0.00064(19) 0.10640(14) 0.0358(6) Uani 1 1 d . . . . .
H38 H 0.158081 0.078263 0.112979 0.043 Uiso 1 1 calc R U . . .
C39 C 0.17271(7) -0.0478(3) 0.19000(16) 0.0712(10) Uani 1 1 d . . . . .
H39 H 0.164426 -0.016955 0.217054 0.107 Uiso 1 1 calc R U . . .
H39A H 0.197938 -0.032040 0.220842 0.107 Uiso 1 1 calc R U . . .
H39B H 0.169182 -0.125589 0.185642 0.107 Uiso 1 1 calc R U . . .
C40 C 0.16273(7) -0.0515(2) 0.06153(17) 0.0481(7) Uani 1 1 d . . . . .
H40 H 0.156865 -0.127952 0.054205 0.072 Uiso 1 1 calc R U . . .
H40A H 0.188301 -0.042859 0.092335 0.072 Uiso 1 1 calc R U . . .
H40B H 0.150084 -0.017262 0.009233 0.072 Uiso 1 1 calc R U . . .
C41 C 0.14749(5) 0.43754(16) 0.05795(12) 0.0221(4) Uani 1 1 d . . . . .
C42 C 0.12869(5) 0.53364(16) 0.03776(11) 0.0217(4) Uani 1 1 d . . . . .
C43 C 0.14817(6) 0.62848(17) 0.06919(12) 0.0254(5) Uani 1 1 d . . . . .
H43 H 0.136096 0.694527 0.057384 0.030 Uiso 1 1 calc R U . . .
C44 C 0.18464(6) 0.62817(17) 0.11709(12) 0.0277(5) Uani 1 1 d . . . . .
H44 H 0.197305 0.693874 0.136270 0.033 Uiso 1 1 calc R U . . .
C45 C 0.20271(6) 0.53298(18) 0.13715(12) 0.0299(5) Uani 1 1 d . . . . .
H45 H 0.227824 0.533615 0.170544 0.036 Uiso 1 1 calc R U . . .
C46 C 0.18464(5) 0.43557(17) 0.10909(12) 0.0261(5) Uani 1 1 d . . . . .
C47 C 0.08862(5) 0.53599(17) -0.01512(13) 0.0279(5) Uani 1 1 d . . . . .
H47 H 0.079476 0.467885 -0.046528 0.033 Uiso 1 1 calc R U . . .
C48 C 0.07698(7) 0.5391(2) 0.03532(16) 0.0464(7) Uani 1 1 d . . . . .
H48 H 0.086556 0.476632 0.070762 0.070 Uiso 1 1 calc R U . . .
H48A H 0.051058 0.537839 0.000273 0.070 Uiso 1 1 calc R U . . .
H48B H 0.085829 0.604707 0.067397 0.070 Uiso 1 1 calc R U . . .
C49 C 0.07165(6) 0.62859(19) -0.07454(13) 0.0361(6) Uani 1 1 d . . . . .
H49 H 0.078005 0.696432 -0.045587 0.054 Uiso 1 1 calc R U . . .
H49A H 0.045848 0.620190 -0.111280 0.054 Uiso 1 1 calc R U . . .
H49B H 0.080198 0.628653 -0.104908 0.054 Uiso 1 1 calc R U . . .
C50 C 0.20516(6) 0.33109(19) 0.13647(14) 0.0372(6) Uani 1 1 d . . . . .
H50 H 0.187623 0.271657 0.106538 0.045 Uiso 1 1 calc R U . . .
C51 C 0.22523(7) 0.3123(2) 0.22562(15) 0.0480(7) Uani 1 1 d . . . . .
H51 H 0.243142 0.368362 0.256653 0.072 Uiso 1 1 calc R U . . .
H51A H 0.236835 0.242159 0.240964 0.072 Uiso 1 1 calc R U . . .
H51B H 0.208570 0.314442 0.236313 0.072 Uiso 1 1 calc R U . . .
C52 C 0.23042(7) 0.3256(2) 0.11853(16) 0.0567(8) Uani 1 1 d . . . . .
H52 H 0.217209 0.336026 0.061177 0.085 Uiso 1 1 calc R U . . .
H52A H 0.242011 0.255385 0.134477 0.085 Uiso 1 1 calc R U . . .
H52B H 0.248376 0.381820 0.148351 0.085 Uiso 1 1 calc R U . . .
N1 N 0.13652(4) 0.42656(13) 0.32619(9) 0.0199(4) Uani 1 1 d . . . . .
N2 N 0.15159(4) 0.25107(13) 0.36467(9) 0.0215(4) Uani 1 1 d . . . . .
N3 N 0.12824(4) 0.33946(13) 0.02482(10) 0.0237(4) Uani 1 1 d . . . . .
N4 N 0.10430(4) 0.17403(13) 0.00680(10) 0.0247(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.414(3) . ?
B1 N2 1.418(3) . ?
B1 B2 1.666(3) . ?
B2 B3 1.489(4) . ?
B2 H3 1.25(3) . ?
B2 H36C 1.30(2) . ?
B3 B4 1.661(3) . ?
B3 H3 1.25(3) . ?
B3 H36C 1.27(2) . ?
B4 N4 1.405(3) . ?
B4 N3 1.412(3) . ?
C1 N2 1.469(2) . ?
C1 C2 1.533(3) . ?
C1 H1 0.9900 . ?
C1 H1A 0.9900 . ?
C2 N1 1.470(2) . ?
C2 H2 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C8 1.401(3) . ?
C3 C4 1.409(3) . ?
C3 N1 1.433(2) . ?
C4 C5 1.386(3) . ?
C4 C12 1.519(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.519(3) . ?
C9 C11 1.527(3) . ?
C9 C10 1.528(3) . ?
C9 H9 1.0000 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C14 1.524(3) . ?
C12 C13 1.528(3) . ?
C12 H12 1.0000 . ?
C13 H13 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C20 1.404(3) . ?
C15 C16 1.405(3) . ?
C15 N2 1.434(2) . ?
C16 C17 1.393(3) . ?
C16 C21 1.514(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.366(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(3) . ?
C19 H19 0.9500 . ?
C20 C24 1.514(3) . ?
C21 C22 1.529(3) . ?
C21 C23 1.531(3) . ?
C21 H21 1.0000 . ?
C22 H22 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 H23 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 C25 1.532(4) . ?
C24 C26 1.532(4) . ?
C24 H24 1.0000 . ?
C25 H25 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 H26 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C27 N4 1.466(3) . ?
C27 C28 1.528(3) . ?
C27 H27 0.9900 . ?
C27 H27A 0.9900 . ?
C28 N3 1.468(2) . ?
C28 H28 0.9900 . ?
C28 H28A 0.9900 . ?
C29 C30 1.400(3) . ?
C29 C34 1.403(3) . ?
C29 N4 1.430(3) . ?
C30 C31 1.399(3) . ?
C30 C38 1.517(3) . ?
C31 C32 1.379(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.379(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.513(3) . ?
C35 C37 1.512(3) . ?
C35 C36 1.519(3) . ?
C35 H35 1.0000 . ?
C36 H36 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C37 H37 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C38 C40 1.526(3) . ?
C38 C39 1.530(4) . ?
C38 H38 1.0000 . ?
C39 H39 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C40 H40 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C41 C42 1.402(3) . ?
C41 C46 1.404(3) . ?
C41 N3 1.429(2) . ?
C42 C43 1.396(3) . ?
C42 C47 1.517(3) . ?
C43 C44 1.380(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.377(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.396(3) . ?
C45 H45 0.9500 . ?
C46 C50 1.518(3) . ?
C47 C48 1.522(3) . ?
C47 C49 1.525(3) . ?
C47 H47 1.0000 . ?
C48 H48 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C49 H49 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C50 C52 1.516(3) . ?
C50 C51 1.531(3) . ?
C50 H50 1.0000 . ?
C51 H51 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C52 H52 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 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
N1 B1 N2 108.19(18) . . ?
N1 B1 B2 124.27(19) . . ?
N2 B1 B2 127.54(19) . . ?
B3 B2 B1 175.0(2) . . ?
B3 B2 H3 53.3(12) . . ?
B1 B2 H3 122.3(12) . . ?
B3 B2 H36C 53.6(10) . . ?
B1 B2 H36C 124.9(10) . . ?
H3 B2 H36C 77.9(15) . . ?
B2 B3 B4 176.8(2) . . ?
B2 B3 H3 53.7(12) . . ?
B4 B3 H3 123.2(12) . . ?
B2 B3 H36C 55.7(10) . . ?
B4 B3 H36C 124.4(11) . . ?
H3 B3 H36C 79.4(14) . . ?
N4 B4 N3 108.30(18) . . ?
N4 B4 B3 125.98(19) . . ?
N3 B4 B3 125.69(19) . . ?
N2 C1 C2 104.81(15) . . ?
N2 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
N2 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
H1 C1 H1A 108.9 . . ?
N1 C2 C1 104.16(15) . . ?
N1 C2 H2 110.9 . . ?
C1 C2 H2 110.9 . . ?
N1 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
H2 C2 H2A 108.9 . . ?
C8 C3 C4 120.46(18) . . ?
C8 C3 N1 120.20(17) . . ?
C4 C3 N1 119.32(18) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C12 119.99(19) . . ?
C3 C4 C12 121.79(19) . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C3 118.70(19) . . ?
C7 C8 C9 118.99(18) . . ?
C3 C8 C9 122.31(18) . . ?
C8 C9 C11 111.33(17) . . ?
C8 C9 C10 110.81(17) . . ?
C11 C9 C10 110.48(17) . . ?
C8 C9 H9 108.0 . . ?
C11 C9 H9 108.0 . . ?
C10 C9 H9 108.0 . . ?
C9 C10 H10 109.5 . . ?
C9 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C11 H11 109.5 . . ?
C9 C11 H11A 109.5 . . ?
H11 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C12 C14 112.8(2) . . ?
C4 C12 C13 110.31(19) . . ?
C14 C12 C13 110.40(19) . . ?
C4 C12 H12 107.7 . . ?
C14 C12 H12 107.7 . . ?
C13 C12 H12 107.7 . . ?
C12 C13 H13 109.5 . . ?
C12 C13 H13A 109.5 . . ?
H13 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C14 H14 109.5 . . ?
C12 C14 H14A 109.5 . . ?
H14 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C20 C15 C16 120.51(19) . . ?
C20 C15 N2 119.95(18) . . ?
C16 C15 N2 119.49(18) . . ?
C17 C16 C15 118.41(19) . . ?
C17 C16 C21 119.49(19) . . ?
C15 C16 C21 122.08(18) . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C15 118.5(2) . . ?
C19 C20 C24 118.8(2) . . ?
C15 C20 C24 122.68(19) . . ?
C16 C21 C22 111.25(18) . . ?
C16 C21 C23 110.85(18) . . ?
C22 C21 C23 111.2(2) . . ?
C16 C21 H21 107.8 . . ?
C22 C21 H21 107.8 . . ?
C23 C21 H21 107.8 . . ?
C21 C22 H22 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C23 H23 109.5 . . ?
C21 C23 H23A 109.5 . . ?
H23 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C24 C25 110.5(2) . . ?
C20 C24 C26 111.5(2) . . ?
C25 C24 C26 111.6(2) . . ?
C20 C24 H24 107.7 . . ?
C25 C24 H24 107.7 . . ?
C26 C24 H24 107.7 . . ?
C24 C25 H25 109.5 . . ?
C24 C25 H25A 109.5 . . ?
H25 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C26 H26 109.5 . . ?
C24 C26 H26A 109.5 . . ?
H26 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N4 C27 C28 104.82(16) . . ?
N4 C27 H27 110.8 . . ?
C28 C27 H27 110.8 . . ?
N4 C27 H27A 110.8 . . ?
C28 C27 H27A 110.8 . . ?
H27 C27 H27A 108.9 . . ?
N3 C28 C27 104.61(16) . . ?
N3 C28 H28 110.8 . . ?
C27 C28 H28 110.8 . . ?
N3 C28 H28A 110.8 . . ?
C27 C28 H28A 110.8 . . ?
H28 C28 H28A 108.9 . . ?
C30 C29 C34 121.63(19) . . ?
C30 C29 N4 119.25(18) . . ?
C34 C29 N4 119.12(19) . . ?
C31 C30 C29 117.85(19) . . ?
C31 C30 C38 120.7(2) . . ?
C29 C30 C38 121.49(19) . . ?
C32 C31 C30 121.1(2) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 C33 120.0(2) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C34 121.2(2) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C29 118.1(2) . . ?
C33 C34 C35 120.57(19) . . ?
C29 C34 C35 121.29(19) . . ?
C37 C35 C34 113.0(2) . . ?
C37 C35 C36 111.0(2) . . ?
C34 C35 C36 110.6(2) . . ?
C37 C35 H35 107.3 . . ?
C34 C35 H35 107.3 . . ?
C36 C35 H35 107.3 . . ?
C35 C36 H36 109.5 . . ?
C35 C36 H36A 109.5 . . ?
H36 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C37 H37 109.5 . . ?
C35 C37 H37A 109.5 . . ?
H37 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C30 C38 C40 111.3(2) . . ?
C30 C38 C39 112.6(2) . . ?
C40 C38 C39 110.2(2) . . ?
C30 C38 H38 107.5 . . ?
C40 C38 H38 107.5 . . ?
C39 C38 H38 107.5 . . ?
C38 C39 H39 109.5 . . ?
C38 C39 H39A 109.5 . . ?
H39 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C40 H40 109.5 . . ?
C38 C40 H40A 109.5 . . ?
H40 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C42 C41 C46 121.64(19) . . ?
C42 C41 N3 118.98(17) . . ?
C46 C41 N3 119.37(18) . . ?
C43 C42 C41 117.69(18) . . ?
C43 C42 C47 120.38(19) . . ?
C41 C42 C47 121.92(18) . . ?
C44 C43 C42 121.3(2) . . ?
C44 C43 H43 119.3 . . ?
C42 C43 H43 119.3 . . ?
C45 C44 C43 120.2(2) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C44 C45 C46 120.9(2) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C45 C46 C41 118.18(19) . . ?
C45 C46 C50 120.03(19) . . ?
C41 C46 C50 121.74(19) . . ?
C42 C47 C48 110.58(18) . . ?
C42 C47 C49 113.63(17) . . ?
C48 C47 C49 109.70(18) . . ?
C42 C47 H47 107.6 . . ?
C48 C47 H47 107.6 . . ?
C49 C47 H47 107.6 . . ?
C47 C48 H48 109.5 . . ?
C47 C48 H48A 109.5 . . ?
H48 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C49 H49 109.5 . . ?
C47 C49 H49A 109.5 . . ?
H49 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
H49 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C52 C50 C46 112.5(2) . . ?
C52 C50 C51 110.2(2) . . ?
C46 C50 C51 111.04(19) . . ?
C52 C50 H50 107.6 . . ?
C46 C50 H50 107.6 . . ?
C51 C50 H50 107.6 . . ?
C50 C51 H51 109.5 . . ?
C50 C51 H51A 109.5 . . ?
H51 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C52 H52 109.5 . . ?
C50 C52 H52A 109.5 . . ?
H52 C52 H52A 109.5 . . ?
C50 C52 H52B 109.5 . . ?
H52 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
B1 N1 C3 130.57(16) . . ?
B1 N1 C2 110.77(16) . . ?
C3 N1 C2 118.64(15) . . ?
B1 N2 C15 129.38(17) . . ?
B1 N2 C1 110.13(16) . . ?
C15 N2 C1 116.87(15) . . ?
B4 N3 C41 129.77(17) . . ?
B4 N3 C28 110.68(17) . . ?
C41 N3 C28 118.56(16) . . ?
B4 N4 C29 129.44(17) . . ?
B4 N4 C27 110.88(17) . . ?
C29 N4 C27 119.50(16) . . ?

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.056

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1884517'
loop_
_audit_author_name
_audit_author_address
'Makoto Yamashita'
;Nagoya University
Japan
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H38 B2 Br2 N2'
_chemical_formula_sum            'C26 H38 B2 Br2 N2'
_chemical_formula_weight         560.02

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'
Br Br -0.2901 2.4595 '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                   9.5962(19)
_cell_length_b                   16.165(3)
_cell_length_c                   18.035(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.959(3)
_cell_angle_gamma                90
_cell_volume                     2793.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5663
_cell_measurement_theta_min      2.6714
_cell_measurement_theta_max      31.3277

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.917
_shelx_estimated_absorpt_T_min   0.593
_shelx_estimated_absorpt_T_max   0.703
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8413
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            22590
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.275
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6402
_reflns_number_gt                3918
_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       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009(Wakita Nemoto et al.)'
_computing_publication_material  'Yadokari-XG 2009(Wakita,Nemoto et al.)'
_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)+(0.0538P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6402
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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 0.0819(4) 0.1149(2) 0.7228(2) 0.0162(8) Uani 1 1 d . . . . .
N1 N -0.0476(3) 0.10649(16) 0.75635(16) 0.0182(7) Uani 1 1 d . . . . .
N2 N 0.1305(3) 0.03462(16) 0.70534(16) 0.0178(6) Uani 1 1 d . . . . .
C1 C -0.0964(4) 0.01975(19) 0.7506(2) 0.0212(8) Uani 1 1 d . . . . .
H1 H -0.164792 0.012357 0.708129 0.025 Uiso 1 1 calc R U . . .
H1A H -0.139129 0.001747 0.796754 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0399(3) -0.0279(2) 0.7385(2) 0.0215(8) Uani 1 1 d . . . . .
H2 H 0.082232 -0.048644 0.786172 0.026 Uiso 1 1 calc R U . . .
H2A H 0.022757 -0.075240 0.704395 0.026 Uiso 1 1 calc R U . . .
C3 C -0.1378(3) 0.1682(2) 0.7850(2) 0.0177(8) Uani 1 1 d . . . . .
C4 C -0.2188(3) 0.2196(2) 0.7371(2) 0.0190(8) Uani 1 1 d . . . . .
C5 C -0.3010(4) 0.2808(2) 0.7680(2) 0.0232(8) Uani 1 1 d . . . . .
H5 H -0.355749 0.316197 0.736200 0.028 Uiso 1 1 calc R U . . .
C6 C -0.3038(4) 0.2904(2) 0.8435(2) 0.0234(8) Uani 1 1 d . . . . .
H6 H -0.359230 0.332913 0.863427 0.028 Uiso 1 1 calc R U . . .
C7 C -0.2258(4) 0.2382(2) 0.8911(2) 0.0231(8) Uani 1 1 d . . . . .
H7 H -0.229655 0.244492 0.943366 0.028 Uiso 1 1 calc R U . . .
C8 C -0.1417(3) 0.1766(2) 0.8621(2) 0.0198(8) Uani 1 1 d . . . . .
C9 C -0.0597(4) 0.1210(2) 0.9158(2) 0.0232(8) Uani 1 1 d . . . . .
H9 H -0.012555 0.078019 0.886096 0.028 Uiso 1 1 calc R U . . .
C10 C 0.0536(5) 0.1693(3) 0.9598(3) 0.0478(12) Uani 1 1 d . . . . .
H10 H 0.115031 0.196205 0.925363 0.072 Uiso 1 1 calc R U . . .
H10A H 0.108367 0.131266 0.992065 0.072 Uiso 1 1 calc R U . . .
H10B H 0.010203 0.211351 0.990209 0.072 Uiso 1 1 calc R U . . .
C11 C -0.1548(5) 0.0762(3) 0.9684(2) 0.0436(12) Uani 1 1 d . . . . .
H11 H -0.204734 0.116952 0.997250 0.065 Uiso 1 1 calc R U . . .
H11A H -0.098314 0.040692 1.002211 0.065 Uiso 1 1 calc R U . . .
H11B H -0.222314 0.042156 0.939387 0.065 Uiso 1 1 calc R U . . .
C12 C -0.2228(4) 0.2103(2) 0.6531(2) 0.0252(9) Uani 1 1 d . . . . .
H12 H -0.157436 0.164674 0.640865 0.030 Uiso 1 1 calc R U . . .
C13 C -0.1739(4) 0.2895(2) 0.6153(2) 0.0301(9) Uani 1 1 d . . . . .
H13 H -0.240163 0.334294 0.623660 0.045 Uiso 1 1 calc R U . . .
H13A H -0.169089 0.279762 0.561906 0.045 Uiso 1 1 calc R U . . .
H13B H -0.081414 0.305020 0.636361 0.045 Uiso 1 1 calc R U . . .
C14 C -0.3697(4) 0.1859(2) 0.6235(2) 0.0292(9) Uani 1 1 d . . . . .
H14 H -0.398599 0.135225 0.648308 0.044 Uiso 1 1 calc R U . . .
H14A H -0.369109 0.176138 0.569848 0.044 Uiso 1 1 calc R U . . .
H14B H -0.435148 0.230560 0.633328 0.044 Uiso 1 1 calc R U . . .
C15 C 0.2694(3) 0.00904(19) 0.6898(2) 0.0188(8) Uani 1 1 d . . . . .
C16 C 0.2940(3) -0.02279(19) 0.6188(2) 0.0178(8) Uani 1 1 d . . . . .
C17 C 0.4278(4) -0.0512(2) 0.6061(2) 0.0243(9) Uani 1 1 d . . . . .
H17 H 0.446441 -0.072628 0.558608 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5342(4) -0.0491(2) 0.6609(2) 0.0228(8) Uani 1 1 d . . . . .
H18 H 0.624191 -0.069618 0.651090 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5090(4) -0.0169(2) 0.7298(2) 0.0239(9) Uani 1 1 d . . . . .
H19 H 0.582454 -0.015373 0.767205 0.029 Uiso 1 1 calc R U . . .
C20 C 0.3773(4) 0.0136(2) 0.7458(2) 0.0197(8) Uani 1 1 d . . . . .
C21 C 0.3566(4) 0.0475(2) 0.8228(2) 0.0236(8) Uani 1 1 d . . . . .
H21 H 0.257705 0.066721 0.824335 0.028 Uiso 1 1 calc R U . . .
C22 C 0.4524(4) 0.1224(2) 0.8402(2) 0.0365(11) Uani 1 1 d . . . . .
H22 H 0.550088 0.104648 0.841070 0.055 Uiso 1 1 calc R U . . .
H22A H 0.431832 0.145279 0.888802 0.055 Uiso 1 1 calc R U . . .
H22B H 0.436043 0.164798 0.801953 0.055 Uiso 1 1 calc R U . . .
C23 C 0.3810(4) -0.0192(2) 0.8833(2) 0.0372(10) Uani 1 1 d . . . . .
H23 H 0.318605 -0.066140 0.872567 0.056 Uiso 1 1 calc R U . . .
H23A H 0.361806 0.004208 0.931817 0.056 Uiso 1 1 calc R U . . .
H23B H 0.478164 -0.037950 0.883797 0.056 Uiso 1 1 calc R U . . .
C24 C 0.1792(4) -0.0279(2) 0.5582(2) 0.0234(8) Uani 1 1 d . . . . .
H24 H 0.097267 0.003993 0.574914 0.028 Uiso 1 1 calc R U . . .
C25 C 0.1326(4) -0.1175(2) 0.5447(2) 0.0309(10) Uani 1 1 d . . . . .
H25 H 0.209435 -0.149281 0.525041 0.046 Uiso 1 1 calc R U . . .
H25A H 0.052248 -0.118558 0.508931 0.046 Uiso 1 1 calc R U . . .
H25B H 0.106258 -0.142116 0.591682 0.046 Uiso 1 1 calc R U . . .
C26 C 0.2244(4) 0.0111(2) 0.4854(2) 0.0277(9) Uani 1 1 d . . . . .
H26 H 0.257117 0.067708 0.495064 0.042 Uiso 1 1 calc R U . . .
H26A H 0.144826 0.012194 0.449111 0.042 Uiso 1 1 calc R U . . .
H26B H 0.299969 -0.021728 0.465750 0.042 Uiso 1 1 calc R U . . .
B2 B 0.1625(4) 0.2036(2) 0.7038(3) 0.0243(10) Uani 1 1 d . . . . .
Br1 Br 0.18987(5) 0.29078(2) 0.77299(3) 0.03688(14) Uani 1 1 d . . . . .
Br2 Br 0.22930(5) 0.22096(2) 0.60633(2) 0.03817(15) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.417(5) . ?
B1 N2 1.420(4) . ?
B1 B2 1.674(5) . ?
N1 C3 1.434(4) . ?
N1 C1 1.480(4) . ?
N2 C15 1.437(4) . ?
N2 C2 1.480(4) . ?
C1 C2 1.543(4) . ?
C1 H1 0.9900 . ?
C1 H1A 0.9900 . ?
C2 H2 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C8 1.400(5) . ?
C3 C4 1.404(5) . ?
C4 C5 1.398(4) . ?
C4 C12 1.521(5) . ?
C5 C6 1.373(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.513(5) . ?
C9 C10 1.527(5) . ?
C9 C11 1.532(5) . ?
C9 H9 1.0000 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C14 1.533(5) . ?
C12 C13 1.534(5) . ?
C12 H12 1.0000 . ?
C13 H13 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.410(5) . ?
C15 C20 1.411(5) . ?
C16 C17 1.394(5) . ?
C16 C24 1.514(5) . ?
C17 C18 1.384(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.516(5) . ?
C21 C22 1.542(5) . ?
C21 C23 1.543(5) . ?
C21 H21 1.0000 . ?
C22 H22 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 H23 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 C25 1.532(5) . ?
C24 C26 1.538(5) . ?
C24 H24 1.0000 . ?
C25 H25 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 H26 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
B2 Br1 1.892(4) . ?
B2 Br2 1.922(5) . ?

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 108.2(3) . . ?
N1 B1 B2 126.5(3) . . ?
N2 B1 B2 125.2(3) . . ?
B1 N1 C3 130.2(3) . . ?
B1 N1 C1 110.0(3) . . ?
C3 N1 C1 119.3(3) . . ?
B1 N2 C15 128.7(3) . . ?
B1 N2 C2 109.1(3) . . ?
C15 N2 C2 116.9(3) . . ?
N1 C1 C2 102.4(3) . . ?
N1 C1 H1 111.3 . . ?
C2 C1 H1 111.3 . . ?
N1 C1 H1A 111.3 . . ?
C2 C1 H1A 111.3 . . ?
H1 C1 H1A 109.2 . . ?
N2 C2 C1 103.7(3) . . ?
N2 C2 H2 111.0 . . ?
C1 C2 H2 111.0 . . ?
N2 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
H2 C2 H2A 109.0 . . ?
C8 C3 C4 120.7(3) . . ?
C8 C3 N1 118.3(3) . . ?
C4 C3 N1 121.0(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C12 118.8(3) . . ?
C3 C4 C12 122.6(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 119.1(3) . . ?
C3 C8 C9 122.6(3) . . ?
C7 C8 C9 118.3(3) . . ?
C8 C9 C10 111.2(3) . . ?
C8 C9 C11 111.8(3) . . ?
C10 C9 C11 110.6(4) . . ?
C8 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C11 C9 H9 107.7 . . ?
C9 C10 H10 109.5 . . ?
C9 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C11 H11 109.5 . . ?
C9 C11 H11A 109.5 . . ?
H11 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C12 C14 110.4(3) . . ?
C4 C12 C13 111.5(3) . . ?
C14 C12 C13 110.9(3) . . ?
C4 C12 H12 108.0 . . ?
C14 C12 H12 108.0 . . ?
C13 C12 H12 108.0 . . ?
C12 C13 H13 109.5 . . ?
C12 C13 H13A 109.5 . . ?
H13 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C14 H14 109.5 . . ?
C12 C14 H14A 109.5 . . ?
H14 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C16 C15 C20 121.2(3) . . ?
C16 C15 N2 118.8(3) . . ?
C20 C15 N2 119.9(3) . . ?
C17 C16 C15 117.9(3) . . ?
C17 C16 C24 120.3(3) . . ?
C15 C16 C24 121.8(3) . . ?
C18 C17 C16 121.8(4) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 121.3(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 118.1(3) . . ?
C19 C20 C21 118.6(3) . . ?
C15 C20 C21 123.3(3) . . ?
C20 C21 C22 111.5(3) . . ?
C20 C21 C23 111.8(3) . . ?
C22 C21 C23 109.7(3) . . ?
C20 C21 H21 107.9 . . ?
C22 C21 H21 107.9 . . ?
C23 C21 H21 107.9 . . ?
C21 C22 H22 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C23 H23 109.5 . . ?
C21 C23 H23A 109.5 . . ?
H23 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C16 C24 C25 111.2(3) . . ?
C16 C24 C26 111.6(3) . . ?
C25 C24 C26 110.2(3) . . ?
C16 C24 H24 107.9 . . ?
C25 C24 H24 107.9 . . ?
C26 C24 H24 107.9 . . ?
C24 C25 H25 109.5 . . ?
C24 C25 H25A 109.5 . . ?
H25 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C26 H26 109.5 . . ?
C24 C26 H26A 109.5 . . ?
H26 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
B1 B2 Br1 123.5(3) . . ?
B1 B2 Br2 119.5(3) . . ?
Br1 B2 Br2 116.9(2) . . ?

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.112

