# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_rei242
_database_code_depnum_ccdc_archive 'CCDC 1418724'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-09-23 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         ?
_chemical_formula_sum            'C27 H30 B2 D3 N2 O2'
_chemical_formula_weight         442.19

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'
D D 0.0000 0.0000 '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                   6.2435(5)
_cell_length_b                   13.8921(9)
_cell_length_c                   14.2338(10)
_cell_angle_alpha                100.533(4)
_cell_angle_beta                 92.139(5)
_cell_angle_gamma                100.164(5)
_cell_volume                     1191.63(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6417
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      25.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             470
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  1.00
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4727
_diffrn_reflns_av_unetI/netI     0.1908
_diffrn_reflns_av_R_equivalents  0.1367
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.919
_diffrn_reflns_theta_max         26.126
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4727
_reflns_number_gt                2146
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0688P)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         4727
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1799
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.928
_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 0.4617(7) 0.2001(3) 0.7898(3) 0.0254(11) Uani 1 1 d . . . . .
B2 B 0.4902(7) 0.2425(3) 0.9893(3) 0.0235(10) Uani 1 1 d . . . . .
C1 C 0.7186(6) 0.2201(3) 0.8328(2) 0.0287(9) Uani 1 1 d . . . . .
H1A H 0.7814 0.1597 0.8117 0.034 Uiso 1 1 calc R U . . .
H1B H 0.8043 0.2755 0.8074 0.034 Uiso 1 1 calc R U . . .
C2 C 0.7335(6) 0.2464(3) 0.9437(2) 0.0288(10) Uani 1 1 d . . . . .
H2A H 0.8216 0.3141 0.9650 0.035 Uiso 1 1 calc R U . . .
H2B H 0.8103 0.1991 0.9694 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3882(6) 0.3141(2) 0.9321(2) 0.0253(9) Uani 1 1 d . . . . .
C4 C 0.2666(6) 0.4469(3) 0.8940(2) 0.0353(10) Uani 1 1 d . . . . .
H4A H 0.3230 0.5195 0.9060 0.042 Uiso 1 1 calc R U . . .
H4B H 0.1053 0.4349 0.8859 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3607(6) 0.3943(3) 0.8064(3) 0.0318(10) Uani 1 1 d . . . . .
C6 C 0.5882(6) 0.4437(3) 0.7927(3) 0.0409(11) Uani 1 1 d . . . . .
H6A H 0.5849 0.5085 0.7752 0.061 Uiso 1 1 calc R U . . .
H6B H 0.6488 0.4015 0.7415 0.061 Uiso 1 1 calc R U . . .
H6C H 0.6794 0.4534 0.8524 0.061 Uiso 1 1 calc R U . . .
C7 C 0.2111(6) 0.3850(3) 0.7169(2) 0.0389(11) Uani 1 1 d . . . . .
H7A H 0.0707 0.3430 0.7229 0.058 Uiso 1 1 calc R U . . .
H7B H 0.2785 0.3547 0.6606 0.058 Uiso 1 1 calc R U . . .
H7C H 0.1879 0.4513 0.7096 0.058 Uiso 1 1 calc R U . . .
C8 C 0.3668(5) 0.1350(2) 0.9358(2) 0.0194(8) Uani 1 1 d . . . . .
C9 C 0.2205(6) -0.0264(3) 0.9038(2) 0.0286(9) Uani 1 1 d . . . . .
H9A H 0.0593 -0.0415 0.9026 0.034 Uiso 1 1 calc R U . . .
H9B H 0.2779 -0.0860 0.9141 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2933(6) 0.0033(2) 0.8102(2) 0.0226(9) Uani 1 1 d . . . . .
C11 C 0.5015(6) -0.0332(3) 0.7814(3) 0.0344(10) Uani 1 1 d . . . . .
H11A H 0.5553 -0.0048 0.7267 0.052 Uiso 1 1 calc R U . . .
H11B H 0.4712 -0.1061 0.7636 0.052 Uiso 1 1 calc R U . . .
H11C H 0.6122 -0.0122 0.8354 0.052 Uiso 1 1 calc R U . . .
C12 C 0.1131(6) -0.0347(3) 0.7307(3) 0.0389(11) Uani 1 1 d . . . . .
H12A H -0.0118 -0.0023 0.7463 0.058 Uiso 1 1 calc R U . . .
H12B H 0.0678 -0.1070 0.7241 0.058 Uiso 1 1 calc R U . . .
H12C H 0.1669 -0.0194 0.6703 0.058 Uiso 1 1 calc R U . . .
C13 C 0.4113(6) 0.1746(2) 0.6758(2) 0.0234(9) Uani 1 1 d . . . . .
C14 C 0.1989(6) 0.1559(3) 0.6356(2) 0.0313(10) Uani 1 1 d . . . . .
H14 H 0.0827 0.1577 0.6767 0.038 Uiso 1 1 calc R U . . .
C15 C 0.1500(6) 0.1348(3) 0.5371(3) 0.0340(10) Uani 1 1 d . . . . .
H15 H 0.0023 0.1218 0.5122 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3110(6) 0.1326(3) 0.4768(3) 0.0345(10) Uani 1 1 d . . . . .
H16 H 0.2782 0.1185 0.4094 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5225(7) 0.1510(3) 0.5142(3) 0.0457(12) Uani 1 1 d . . . . .
H17 H 0.6373 0.1496 0.4723 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5714(6) 0.1719(3) 0.6128(2) 0.0346(10) Uani 1 1 d . . . . .
H18 H 0.7196 0.1845 0.6370 0.042 Uiso 1 1 calc R U . . .
C19 C 0.4866(6) 0.2672(2) 1.1032(2) 0.0199(8) Uani 1 1 d . . . . .
C20 C 0.2973(6) 0.2577(2) 1.1502(2) 0.0263(9) Uani 1 1 d . . . . .
H20 H 0.1625 0.2345 1.1129 0.032 Uiso 1 1 calc R U . . .
C21 C 0.2932(6) 0.2800(3) 1.2486(2) 0.0309(10) Uani 1 1 d . . . . .
H21 H 0.1583 0.2728 1.2777 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4879(7) 0.3131(3) 1.3045(2) 0.0300(10) Uani 1 1 d . . . . .
H22 H 0.4879 0.3279 1.3723 0.036 Uiso 1 1 calc R U . . .
C23 C 0.6780(6) 0.3241(3) 1.2616(2) 0.0280(10) Uani 1 1 d . . . . .
H23 H 0.8116 0.3475 1.2998 0.034 Uiso 1 1 calc R U . . .
C24 C 0.6808(6) 0.3016(2) 1.1625(2) 0.0248(9) Uani 1 1 d . . . . .
H24 H 0.8166 0.3095 1.1342 0.030 Uiso 1 1 calc R U . . .
C25 C 0.0786(10) 0.4133(4) 0.4845(3) 0.0539(14) Uani 1 1 d . . . . .
D25 D 0.1330 0.3528 0.4739 0.065 Uiso 1 1 calc R U . . .
C26 C 0.1935(8) 0.4959(5) 0.4586(3) 0.0543(13) Uani 1 1 d . . . . .
D26 D 0.3276 0.4933 0.4297 0.065 Uiso 1 1 calc R U . . .
C27 C 0.1137(9) 0.5831(4) 0.4744(3) 0.0531(13) Uani 1 1 d . . . . .
D27 D 0.1933 0.6411 0.4567 0.064 Uiso 1 1 calc R U . . .
N1 N 0.3753(5) 0.29667(19) 0.83885(19) 0.0253(8) Uani 1 1 d . . . . .
N2 N 0.3445(4) 0.11377(19) 0.84246(18) 0.0181(7) Uani 1 1 d . . . . .
O1 O 0.3401(4) 0.40222(17) 0.97304(16) 0.0331(7) Uani 1 1 d . . . . .
O2 O 0.3079(4) 0.05786(16) 0.97840(15) 0.0250(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.588(5) . ?
B1 C13 1.603(5) . ?
B1 N2 1.611(5) . ?
B1 C1 1.653(5) . ?
B2 C3 1.593(5) . ?
B2 C8 1.594(5) . ?
B2 C19 1.596(5) . ?
B2 C2 1.671(5) . ?
C1 C2 1.550(4) . ?
C3 N1 1.302(4) . ?
C3 O1 1.345(4) . ?
C4 O1 1.476(4) . ?
C4 C5 1.519(5) . ?
C5 C6 1.500(5) . ?
C5 C7 1.523(4) . ?
C5 N1 1.527(4) . ?
C8 N2 1.304(4) . ?
C8 O2 1.329(4) . ?
C9 O2 1.440(4) . ?
C9 C10 1.526(5) . ?
C10 N2 1.492(4) . ?
C10 C12 1.518(4) . ?
C10 C11 1.520(5) . ?
C13 C18 1.368(5) . ?
C13 C14 1.387(5) . ?
C14 C15 1.389(5) . ?
C15 C16 1.346(5) . ?
C16 C17 1.368(5) . ?
C17 C18 1.392(5) . ?
C19 C20 1.377(5) . ?
C19 C24 1.408(4) . ?
C20 C21 1.380(5) . ?
C21 C22 1.385(5) . ?
C22 C23 1.352(5) . ?
C23 C24 1.389(4) . ?
C25 C27 1.360(6) 2_566 ?
C25 C26 1.361(6) . ?
C26 C27 1.373(6) . ?
C27 C25 1.360(6) 2_566 ?

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 C13 112.6(3) . . ?
N1 B1 N2 104.2(3) . . ?
C13 B1 N2 113.2(3) . . ?
N1 B1 C1 104.0(3) . . ?
C13 B1 C1 118.2(3) . . ?
N2 B1 C1 103.1(3) . . ?
C3 B2 C8 102.1(3) . . ?
C3 B2 C19 116.3(3) . . ?
C8 B2 C19 117.0(3) . . ?
C3 B2 C2 100.6(3) . . ?
C8 B2 C2 100.7(3) . . ?
C19 B2 C2 117.4(3) . . ?
C2 C1 B1 110.4(3) . . ?
C1 C2 B2 113.3(3) . . ?
N1 C3 O1 114.7(3) . . ?
N1 C3 B2 120.4(3) . . ?
O1 C3 B2 124.2(3) . . ?
O1 C4 C5 104.3(3) . . ?
C6 C5 C4 113.0(3) . . ?
C6 C5 C7 110.7(3) . . ?
C4 C5 C7 110.5(3) . . ?
C6 C5 N1 107.6(3) . . ?
C4 C5 N1 99.1(3) . . ?
C7 C5 N1 115.6(3) . . ?
N2 C8 O2 114.8(3) . . ?
N2 C8 B2 120.0(3) . . ?
O2 C8 B2 124.6(3) . . ?
O2 C9 C10 105.9(3) . . ?
N2 C10 C12 115.1(3) . . ?
N2 C10 C11 108.9(3) . . ?
C12 C10 C11 110.7(3) . . ?
N2 C10 C9 99.3(3) . . ?
C12 C10 C9 110.8(3) . . ?
C11 C10 C9 111.6(3) . . ?
C18 C13 C14 116.1(3) . . ?
C18 C13 B1 123.0(3) . . ?
C14 C13 B1 120.9(3) . . ?
C13 C14 C15 122.2(4) . . ?
C16 C15 C14 120.3(3) . . ?
C15 C16 C17 118.9(3) . . ?
C16 C17 C18 120.8(4) . . ?
C13 C18 C17 121.6(4) . . ?
C20 C19 C24 115.5(3) . . ?
C20 C19 B2 123.3(3) . . ?
C24 C19 B2 121.2(3) . . ?
C19 C20 C21 123.5(3) . . ?
C20 C21 C22 119.3(4) . . ?
C23 C22 C21 119.4(3) . . ?
C22 C23 C24 120.9(3) . . ?
C23 C24 C19 121.4(3) . . ?
C27 C25 C26 120.3(5) 2_566 . ?
C25 C26 C27 119.4(5) . . ?
C25 C27 C26 120.3(5) 2_566 . ?
C3 N1 C5 107.9(3) . . ?
C3 N1 B1 115.2(3) . . ?
C5 N1 B1 132.3(3) . . ?
C8 N2 C10 109.1(3) . . ?
C8 N2 B1 115.1(3) . . ?
C10 N2 B1 130.8(3) . . ?
C3 O1 C4 106.3(3) . . ?
C8 O2 C9 106.8(2) . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1418725'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H34 B2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         476.21

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.0335(18)
_cell_length_b                   13.357(2)
_cell_length_c                   17.045(3)
_cell_angle_alpha                73.663(4)
_cell_angle_beta                 81.968(4)
_cell_angle_gamma                79.686(4)
_cell_volume                     2575.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2626
_cell_measurement_theta_min      2.7898
_cell_measurement_theta_max      20.7571
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            9199
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.1475
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20

_refine_special_details          'Refined as a 3-component twin.'

_reflns_number_total             9199
_reflns_number_gt                5395
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1718
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.2381
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         9199
_refine_ls_number_parameters     659
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0889P)²+3.4210P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.7239(6) 0.4884(5) 0.1460(4) 0.0234(15) Uani d . . . 1 . .
B B2 0.6533(5) 0.3093(5) 0.1296(4) 0.0206(14) Uani d . . . 1 . .
B B3 0.2278(5) 0.1992(5) 0.4471(4) 0.0242(15) Uani d . . . 1 . .
B B4 0.1542(6) 0.1163(5) 0.3335(4) 0.0242(15) Uani d . . . 1 . .
C C1 0.5957(4) 0.5148(4) 0.1084(3) 0.0224(13) Uani d . . . 1 . .
H H1 0.6046 0.5637 0.0523 0.027 Uiso calc U . R 1 . .
C C2 0.5608(4) 0.4129(4) 0.0979(4) 0.0231(13) Uani d . . . 1 . .
H H2A 0.5523 0.4221 0.0393 0.028 Uiso calc U . R 1 . .
H H2B 0.4862 0.4018 0.1293 0.028 Uiso calc U . R 1 . .
C C3 0.7972(4) 0.4256(4) 0.0841(3) 0.0206(13) Uani d . . . 1 . .
C C4 0.9270(5) 0.3833(5) -0.0143(4) 0.0299(14) Uani d . . . 1 . .
H H4A 1.0009 0.3449 0.0045 0.036 Uiso calc U . R 1 . .
H H4B 0.9377 0.4164 -0.0741 0.036 Uiso calc U . R 1 . .
C C5 0.8386(5) 0.3082(5) 0.0047(3) 0.0247(14) Uani d . . . 1 . .
C C6 0.7621(6) 0.3328(7) -0.0639(4) 0.056(2) Uani d . . . 1 . .
H H6A 0.7046 0.2854 -0.0484 0.084 Uiso calc U . R 1 . .
H H6B 0.8076 0.3227 -0.1142 0.084 Uiso calc U . R 1 . .
H H6C 0.7247 0.4061 -0.0734 0.084 Uiso calc U . R 1 . .
C C7 0.8967(6) 0.1957(5) 0.0229(4) 0.048(2) Uani d . . . 1 . .
H H7A 0.9304 0.1776 0.0752 0.072 Uiso calc U . R 1 . .
H H7B 0.9564 0.1875 -0.0212 0.072 Uiso calc U . R 1 . .
H H7C 0.8411 0.1488 0.0267 0.072 Uiso calc U . R 1 . .
C C8 0.7005(4) 0.3959(4) 0.2274(3) 0.0214(13) Uani d . . . 1 . .
C C9 0.6442(6) 0.3164(5) 0.3579(4) 0.0353(16) Uani d . . . 1 . .
H H9A 0.5655 0.3413 0.3776 0.042 Uiso calc U . R 1 . .
H H9B 0.6876 0.282 0.4061 0.042 Uiso calc U . R 1 . .
C C10 0.6448(5) 0.2391(5) 0.3060(3) 0.0278(14) Uani d . . . 1 . .
C C11 0.7393(6) 0.1463(5) 0.3269(4) 0.0411(17) Uani d . . . 1 . .
H H11A 0.7452 0.1032 0.2881 0.062 Uiso calc U . R 1 . .
H H11B 0.7223 0.1033 0.3828 0.062 Uiso calc U . R 1 . .
H H11C 0.8114 0.1726 0.3231 0.062 Uiso calc U . R 1 . .
C C12 0.5303(5) 0.2020(5) 0.3142(4) 0.0345(16) Uani d . . . 1 . .
H H12A 0.4726 0.2627 0.2948 0.052 Uiso calc U . R 1 . .
H H12B 0.5094 0.1676 0.372 0.052 Uiso calc U . R 1 . .
H H12C 0.535 0.1518 0.2812 0.052 Uiso calc U . R 1 . .
C C13 0.7790(4) 0.5860(4) 0.1527(3) 0.0212(13) Uani d . . . 1 . .
C C14 0.7767(5) 0.6779(5) 0.0873(4) 0.0297(14) Uani d . . . 1 . .
H H14 0.7402 0.682 0.0404 0.036 Uiso calc U . R 1 . .
C C15 0.8265(5) 0.7625(5) 0.0899(4) 0.0386(17) Uani d . . . 1 . .
H H15 0.8232 0.8238 0.045 0.046 Uiso calc U . R 1 . .
C C16 0.8798(5) 0.7589(6) 0.1560(5) 0.0443(19) Uani d . . . 1 . .
H H16 0.9147 0.8169 0.1569 0.053 Uiso calc U . R 1 . .
C C17 0.8830(6) 0.6706(6) 0.2218(4) 0.0439(18) Uani d . . . 1 . .
H H17 0.9196 0.6681 0.2684 0.053 Uiso calc U . R 1 . .
C C18 0.8331(5) 0.5855(5) 0.2203(4) 0.0325(15) Uani d . . . 1 . .
H H18 0.8357 0.5254 0.2662 0.039 Uiso calc U . R 1 . .
C C19 0.6219(5) 0.1995(4) 0.1209(3) 0.0237(13) Uani d . . . 1 . .
C C20 0.6904(6) 0.1021(5) 0.1454(3) 0.0315(15) Uani d . . . 1 . .
H H20 0.7583 0.0981 0.1693 0.038 Uiso calc U . R 1 . .
C C21 0.6606(7) 0.0104(5) 0.1353(4) 0.0446(19) Uani d . . . 1 . .
H H21 0.7083 -0.0549 0.153 0.054 Uiso calc U . R 1 . .
C C22 0.5646(7) 0.0127(6) 0.1005(4) 0.050(2) Uani d . . . 1 . .
H H22 0.5453 -0.05 0.0936 0.06 Uiso calc U . R 1 . .
C C23 0.4954(6) 0.1090(6) 0.0752(4) 0.0411(17) Uani d . . . 1 . .
H H23 0.4283 0.1126 0.0505 0.049 Uiso calc U . R 1 . .
C C24 0.5242(5) 0.1992(5) 0.0861(3) 0.0274(14) Uani d . . . 1 . .
H H24 0.4753 0.2639 0.069 0.033 Uiso calc U . R 1 . .
C C25 0.5095(5) 0.5738(4) 0.1598(3) 0.0230(13) Uani d . . . 1 . .
C C26 0.4439(5) 0.5232(5) 0.2297(4) 0.0314(15) Uani d . . . 1 . .
H H26 0.4523 0.4483 0.2457 0.038 Uiso calc U . R 1 . .
C C27 0.3672(5) 0.5795(5) 0.2762(4) 0.0353(16) Uani d . . . 1 . .
H H27 0.3253 0.5427 0.3238 0.042 Uiso calc U . R 1 . .
C C28 0.3514(5) 0.6878(5) 0.2542(4) 0.0380(16) Uani d . . . 1 . .
H H28 0.298 0.7262 0.2856 0.046 Uiso calc U . R 1 . .
C C29 0.4146(5) 0.7402(5) 0.1854(4) 0.0367(16) Uani d . . . 1 . .
H H29 0.4044 0.8151 0.1693 0.044 Uiso calc U . R 1 . .
C C30 0.4926(5) 0.6837(4) 0.1400(4) 0.0272(14) Uani d . . . 1 . .
H H30 0.5362 0.7212 0.0937 0.033 Uiso calc U . R 1 . .
C C31 0.0957(4) 0.1619(5) 0.4782(3) 0.0242(13) Uani d . . . 1 . .
H H31 0.1027 0.1042 0.5302 0.029 Uiso calc U . R 1 . .
C C32 0.0612(5) 0.1137(5) 0.4136(3) 0.0261(14) Uani d . . . 1 . .
H H32A -0.0124 0.153 0.3948 0.031 Uiso calc U . R 1 . .
H H32B 0.0502 0.0396 0.4404 0.031 Uiso calc U . R 1 . .
C C33 0.2060(4) 0.2745(4) 0.3582(3) 0.0217(13) Uani d . . . 1 . .
C C34 0.1447(5) 0.4212(4) 0.2617(3) 0.0292(14) Uani d . . . 1 . .
H H34A 0.186 0.4746 0.2216 0.035 Uiso calc U . R 1 . .
H H34B 0.066 0.4543 0.2735 0.035 Uiso calc U . R 1 . .
C C35 0.1450(5) 0.3259(5) 0.2278(3) 0.0262(14) Uani d . . . 1 . .
C C36 0.2381(5) 0.3234(5) 0.1577(3) 0.0374(16) Uani d . . . 1 . .
H H36A 0.3117 0.3207 0.1772 0.056 Uiso calc U . R 1 . .
H H36B 0.2237 0.3871 0.1126 0.056 Uiso calc U . R 1 . .
H H36C 0.2389 0.2609 0.1382 0.056 Uiso calc U . R 1 . .
C C37 0.0302(5) 0.3240(5) 0.2022(4) 0.0339(15) Uani d . . . 1 . .
H H37A 0.0341 0.2631 0.18 0.051 Uiso calc U . R 1 . .
H H37B 0.0083 0.389 0.1601 0.051 Uiso calc U . R 1 . .
H H37C -0.0263 0.3185 0.2501 0.051 Uiso calc U . R 1 . .
C C38 0.2976(4) 0.0929(5) 0.4289(3) 0.0235(13) Uani d . . . 1 . .
C C39 0.4201(5) -0.0580(5) 0.4378(4) 0.0289(14) Uani d . . . 1 . .
H H39A 0.4273 -0.1256 0.481 0.035 Uiso calc U . R 1 . .
H H39B 0.4951 -0.0497 0.4063 0.035 Uiso calc U . R 1 . .
C C40 0.3310(5) -0.0551(4) 0.3808(4) 0.0276(14) Uani d . . . 1 . .
C C41 0.3907(6) -0.0738(5) 0.3010(4) 0.0413(17) Uani d . . . 1 . .
H H41A 0.3349 -0.0819 0.2673 0.062 Uiso calc U . R 1 . .
H H41B 0.4464 -0.1381 0.3126 0.062 Uiso calc U . R 1 . .
H H41C 0.4295 -0.0136 0.2714 0.062 Uiso calc U . R 1 . .
C C42 0.2489(6) -0.1328(5) 0.4212(4) 0.0401(17) Uani d . . . 1 . .
H H42A 0.2134 -0.1187 0.4731 0.06 Uiso calc U . R 1 . .
H H42B 0.2901 -0.2048 0.4319 0.06 Uiso calc U . R 1 . .
H H42C 0.1902 -0.1251 0.3846 0.06 Uiso calc U . R 1 . .
C C43 0.2849(5) 0.2423(5) 0.5095(3) 0.0254(14) Uani d . . . 1 . .
C C44 0.3434(5) 0.3289(5) 0.4838(4) 0.0325(15) Uani d . . . 1 . .
H H44 0.3495 0.3645 0.427 0.039 Uiso calc U . R 1 . .
C C45 0.3932(6) 0.3655(5) 0.5369(4) 0.0452(18) Uani d . . . 1 . .
H H45 0.4324 0.4248 0.5166 0.054 Uiso calc U . R 1 . .
C C46 0.3851(5) 0.3148(6) 0.6198(4) 0.0444(19) Uani d . . . 1 . .
H H46 0.4165 0.34 0.6575 0.053 Uiso calc U . R 1 . .
C C47 0.3314(5) 0.2279(6) 0.6468(4) 0.0397(17) Uani d . . . 1 . .
H H47 0.3275 0.1914 0.7034 0.048 Uiso calc U . R 1 . .
C C48 0.2825(5) 0.1921(5) 0.5928(4) 0.0335(15) Uani d . . . 1 . .
H H48 0.2462 0.131 0.6135 0.04 Uiso calc U . R 1 . .
C C49 0.1253(5) 0.0676(4) 0.2641(3) 0.0248(13) Uani d . . . 1 . .
C C50 0.1962(5) 0.0655(5) 0.1917(4) 0.0303(14) Uani d . . . 1 . .
H H50 0.2631 0.0973 0.1817 0.036 Uiso calc U . R 1 . .
C C51 0.1720(6) 0.0183(5) 0.1340(4) 0.0379(16) Uani d . . . 1 . .
H H51 0.2227 0.0173 0.0861 0.046 Uiso calc U . R 1 . .
C C52 0.0742(6) -0.0270(5) 0.1466(4) 0.0423(18) Uani d . . . 1 . .
H H52 0.0562 -0.0582 0.1072 0.051 Uiso calc U . R 1 . .
C C53 0.0031(6) -0.0262(5) 0.2173(4) 0.0398(17) Uani d . . . 1 . .
H H53 -0.0639 -0.058 0.2268 0.048 Uiso calc U . R 1 . .
C C54 0.0281(5) 0.0206(5) 0.2752(4) 0.0310(15) Uani d . . . 1 . .
H H54 -0.0225 0.0203 0.3232 0.037 Uiso calc U . R 1 . .
C C55 0.0131(5) 0.2517(5) 0.4987(4) 0.0266(14) Uani d . . . 1 . .
C C56 -0.0490(5) 0.3279(5) 0.4405(4) 0.0374(16) Uani d . . . 1 . .
H H56 -0.0429 0.3212 0.386 0.045 Uiso calc U . R 1 . .
C C57 -0.1199(6) 0.4136(6) 0.4605(4) 0.0471(19) Uani d . . . 1 . .
H H57 -0.1607 0.4646 0.4194 0.056 Uiso calc U . R 1 . .
C C58 -0.1315(5) 0.4253(6) 0.5387(4) 0.0440(18) Uani d . . . 1 . .
H H58 -0.1778 0.4851 0.5516 0.053 Uiso calc U . R 1 . .
C C59 -0.0755(5) 0.3496(6) 0.5977(4) 0.0456(19) Uani d . . . 1 . .
H H59 -0.0855 0.3554 0.6526 0.055 Uiso calc U . R 1 . .
C C60 -0.0036(5) 0.2637(5) 0.5784(4) 0.0338(15) Uani d . . . 1 . .
H H60 0.0347 0.2122 0.6205 0.041 Uiso calc U . R 1 . .
N N1 0.7715(4) 0.3381(3) 0.0784(3) 0.0197(10) Uani d . . . 1 . .
N N2 0.6714(4) 0.3093(4) 0.2212(3) 0.0215(11) Uani d . . . 1 . .
N N3 0.1751(4) 0.2368(4) 0.3027(3) 0.0230(11) Uani d . . . 1 . .
N N4 0.2706(4) 0.0551(3) 0.3731(3) 0.0218(11) Uani d . . . 1 . .
O O1 0.8819(3) 0.4632(3) 0.0302(2) 0.0253(9) Uani d . . . 1 . .
O O2 0.6970(3) 0.4039(3) 0.3044(2) 0.0264(9) Uani d . . . 1 . .
O O3 0.2015(3) 0.3794(3) 0.3370(2) 0.0258(9) Uani d . . . 1 . .
O O4 0.3792(3) 0.0301(3) 0.4742(2) 0.0267(9) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C3 . 1.601(9) ?
B1 C13 . 1.603(8) ?
B1 C8 . 1.607(8) ?
B1 C1 . 1.692(8) ?
B2 N2 . 1.607(7) ?
B2 N1 . 1.610(7) ?
B2 C2 . 1.625(8) ?
B2 C19 . 1.629(8) ?
B3 C33 . 1.592(9) ?
B3 C38 . 1.601(9) ?
B3 C43 . 1.620(8) ?
B3 C31 . 1.719(8) ?
B4 N3 . 1.601(8) ?
B4 C49 . 1.604(9) ?
B4 N4 . 1.621(8) ?
B4 C32 . 1.637(8) ?
C1 C25 . 1.519(8) ?
C1 C2 . 1.557(7) ?
C3 N1 . 1.293(7) ?
C3 O1 . 1.340(6) ?
C4 O1 . 1.464(7) ?
C4 C5 . 1.531(7) ?
C5 C7 . 1.505(9) ?
C5 N1 . 1.508(7) ?
C5 C6 . 1.517(8) ?
C8 N2 . 1.302(7) ?
C8 O2 . 1.341(6) ?
C9 O2 . 1.451(6) ?
C9 C10 . 1.536(8) ?
C10 N2 . 1.512(7) ?
C10 C12 . 1.522(8) ?
C10 C11 . 1.523(8) ?
C13 C18 . 1.398(8) ?
C13 C14 . 1.405(8) ?
C14 C15 . 1.384(8) ?
C15 C16 . 1.357(9) ?
C16 C17 . 1.380(10) ?
C17 C18 . 1.385(8) ?
C19 C24 . 1.390(8) ?
C19 C20 . 1.397(8) ?
C20 C21 . 1.397(9) ?
C21 C22 . 1.362(10) ?
C22 C23 . 1.393(10) ?
C23 C24 . 1.377(8) ?
C25 C30 . 1.394(8) ?
C25 C26 . 1.405(8) ?
C26 C27 . 1.389(8) ?
C27 C28 . 1.373(9) ?
C28 C29 . 1.387(9) ?
C29 C30 . 1.387(8) ?
C31 C55 . 1.503(8) ?
C31 C32 . 1.556(7) ?
C33 N3 . 1.311(7) ?
C33 O3 . 1.339(6) ?
C34 O3 . 1.461(6) ?
C34 C35 . 1.538(8) ?
C35 C37 . 1.512(8) ?
C35 N3 . 1.516(7) ?
C35 C36 . 1.523(8) ?
C38 N4 . 1.297(7) ?
C38 O4 . 1.347(6) ?
C39 O4 . 1.459(7) ?
C39 C40 . 1.534(8) ?
C40 N4 . 1.500(7) ?
C40 C41 . 1.511(8) ?
C40 C42 . 1.517(8) ?
C43 C48 . 1.388(8) ?
C43 C44 . 1.395(8) ?
C44 C45 . 1.387(8) ?
C45 C46 . 1.383(9) ?
C46 C47 . 1.364(9) ?
C47 C48 . 1.386(8) ?
C49 C54 . 1.390(8) ?
C49 C50 . 1.402(8) ?
C50 C51 . 1.394(8) ?
C51 C52 . 1.382(9) ?
C52 C53 . 1.378(9) ?
C53 C54 . 1.397(8) ?
C55 C56 . 1.394(8) ?
C55 C60 . 1.395(8) ?
C56 C57 . 1.395(9) ?
C57 C58 . 1.369(9) ?
C58 C59 . 1.365(9) ?
C59 C60 . 1.397(9) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 B1 C13 . . 113.4(5) ?
C3 B1 C8 . . 102.9(5) ?
C13 B1 C8 . . 119.2(5) ?
C3 B1 C1 . . 100.6(4) ?
C13 B1 C1 . . 117.7(5) ?
C8 B1 C1 . . 100.2(4) ?
N2 B2 N1 . . 103.0(4) ?
N2 B2 C2 . . 105.2(4) ?
N1 B2 C2 . . 105.0(4) ?
N2 B2 C19 . . 114.8(5) ?
N1 B2 C19 . . 112.7(5) ?
C2 B2 C19 . . 114.9(5) ?
C33 B3 C38 . . 103.8(5) ?
C33 B3 C43 . . 118.9(5) ?
C38 B3 C43 . . 113.6(5) ?
C33 B3 C31 . . 99.9(4) ?
C38 B3 C31 . . 100.5(5) ?
C43 B3 C31 . . 117.5(5) ?
N3 B4 C49 . . 115.3(5) ?
N3 B4 N4 . . 103.4(4) ?
C49 B4 N4 . . 112.2(5) ?
N3 B4 C32 . . 103.8(5) ?
C49 B4 C32 . . 117.0(5) ?
N4 B4 C32 . . 103.6(4) ?
C25 C1 C2 . . 115.0(4) ?
C25 C1 B1 . . 110.1(4) ?
C2 C1 B1 . . 110.8(4) ?
C1 C2 B2 . . 112.1(4) ?
N1 C3 O1 . . 115.2(5) ?
N1 C3 B1 . . 121.2(5) ?
O1 C3 B1 . . 123.3(5) ?
O1 C4 C5 . . 105.7(4) ?
C7 C5 N1 . . 113.8(5) ?
C7 C5 C6 . . 111.6(6) ?
N1 C5 C6 . . 109.2(5) ?
C7 C5 C4 . . 109.9(5) ?
N1 C5 C4 . . 99.8(4) ?
C6 C5 C4 . . 111.9(5) ?
N2 C8 O2 . . 115.0(5) ?
N2 C8 B1 . . 119.8(5) ?
O2 C8 B1 . . 124.8(5) ?
O2 C9 C10 . . 106.0(4) ?
N2 C10 C12 . . 111.6(5) ?
N2 C10 C11 . . 110.5(5) ?
C12 C10 C11 . . 111.3(5) ?
N2 C10 C9 . . 100.0(4) ?
C12 C10 C9 . . 112.3(5) ?
C11 C10 C9 . . 110.7(5) ?
C18 C13 C14 . . 116.4(5) ?
C18 C13 B1 . . 123.8(5) ?
C14 C13 B1 . . 119.8(5) ?
C15 C14 C13 . . 121.4(6) ?
C16 C15 C14 . . 120.7(6) ?
C15 C16 C17 . . 119.7(6) ?
C16 C17 C18 . . 120.2(6) ?
C17 C18 C13 . . 121.5(6) ?
C24 C19 C20 . . 116.2(5) ?
C24 C19 B2 . . 120.4(5) ?
C20 C19 B2 . . 123.3(5) ?
C21 C20 C19 . . 121.1(6) ?
C22 C21 C20 . . 121.4(7) ?
C21 C22 C23 . . 118.5(6) ?
C24 C23 C22 . . 120.1(7) ?
C23 C24 C19 . . 122.7(6) ?
C30 C25 C26 . . 116.0(5) ?
C30 C25 C1 . . 120.7(5) ?
C26 C25 C1 . . 123.3(5) ?
C27 C26 C25 . . 121.9(6) ?
C28 C27 C26 . . 120.7(6) ?
C27 C28 C29 . . 118.9(6) ?
C30 C29 C28 . . 120.3(6) ?
C29 C30 C25 . . 122.3(6) ?
C55 C31 C32 . . 115.9(5) ?
C55 C31 B3 . . 110.2(5) ?
C32 C31 B3 . . 109.4(4) ?
C31 C32 B4 . . 113.8(4) ?
N3 C33 O3 . . 114.4(5) ?
N3 C33 B3 . . 120.0(5) ?
O3 C33 B3 . . 125.0(5) ?
O3 C34 C35 . . 105.7(4) ?
C37 C35 N3 . . 112.2(5) ?
C37 C35 C36 . . 111.7(5) ?
N3 C35 C36 . . 110.1(5) ?
C37 C35 C34 . . 111.8(5) ?
N3 C35 C34 . . 99.9(4) ?
C36 C35 C34 . . 110.6(5) ?
N4 C38 O4 . . 114.4(5) ?
N4 C38 B3 . . 121.1(5) ?
O4 C38 B3 . . 124.2(5) ?
O4 C39 C40 . . 105.5(4) ?
N4 C40 C41 . . 113.9(5) ?
N4 C40 C42 . . 109.4(5) ?
C41 C40 C42 . . 112.3(5) ?
N4 C40 C39 . . 99.8(4) ?
C41 C40 C39 . . 109.0(5) ?
C42 C40 C39 . . 111.9(5) ?
C48 C43 C44 . . 115.2(6) ?
C48 C43 B3 . . 121.7(5) ?
C44 C43 B3 . . 123.1(5) ?
C45 C44 C43 . . 123.4(6) ?
C46 C45 C44 . . 119.2(6) ?
C47 C46 C45 . . 119.0(6) ?
C46 C47 C48 . . 121.1(6) ?
C47 C48 C43 . . 122.2(6) ?
C54 C49 C50 . . 116.2(5) ?
C54 C49 B4 . . 120.3(5) ?
C50 C49 B4 . . 123.4(5) ?
C51 C50 C49 . . 122.4(6) ?
C52 C51 C50 . . 119.9(6) ?
C53 C52 C51 . . 118.9(6) ?
C52 C53 C54 . . 120.9(6) ?
C49 C54 C53 . . 121.6(6) ?
C56 C55 C60 . . 116.3(6) ?
C56 C55 C31 . . 123.0(5) ?
C60 C55 C31 . . 120.7(5) ?
C55 C56 C57 . . 121.6(6) ?
C58 C57 C56 . . 120.8(7) ?
C59 C58 C57 . . 119.0(6) ?
C58 C59 C60 . . 120.7(6) ?
C55 C60 C59 . . 121.6(6) ?
C3 N1 C5 . . 109.8(4) ?
C3 N1 B2 . . 113.5(4) ?
C5 N1 B2 . . 133.1(4) ?
C8 N2 C10 . . 109.6(5) ?
C8 N2 B2 . . 114.7(4) ?
C10 N2 B2 . . 134.9(4) ?
C33 N3 C35 . . 109.9(4) ?
C33 N3 B4 . . 115.3(4) ?
C35 N3 B4 . . 133.5(4) ?
C38 N4 C40 . . 110.3(5) ?
C38 N4 B4 . . 114.1(5) ?
C40 N4 B4 . . 131.7(4) ?
C3 O1 C4 . . 106.7(4) ?
C8 O2 C9 . . 107.0(4) ?
C33 O3 C34 . . 107.5(4) ?
C38 O4 C39 . . 106.9(4) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1418726'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H36 B2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         490.24

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.498(2)
_cell_length_b                   9.090(2)
_cell_length_c                   30.647(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.119(3)
_cell_angle_gamma                90
_cell_volume                     2639.1(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6659
_cell_measurement_theta_min      2.6071
_cell_measurement_theta_max      24.9652
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.360
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS V2012/1'
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            4811
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       36

_refine_special_details          'Refined as a 2-component twin.'

_reflns_number_total             4811
_reflns_number_gt                3214
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1579
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         4811
_refine_ls_number_parameters     339
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0855P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.365
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 -0.0052(3) 0.6950(3) 0.11270(9) 0.0312(6) Uani d . . . 1 . .
B B2 0.2135(3) 0.6811(3) 0.17800(9) 0.0312(6) Uani d . . . 1 . .
C C1 0.0568(2) 0.7138(2) 0.19118(7) 0.0288(5) Uani d . . . 1 . .
C C2 -0.1308(2) 0.7419(3) 0.23151(7) 0.0344(6) Uani d . . . 1 . .
H H2A -0.1492 0.8399 0.244 0.041 Uiso calc U . R 1 . .
H H2B -0.1779 0.6663 0.2486 0.041 Uiso calc U . R 1 . .
C C3 -0.1857(2) 0.7357(3) 0.18285(8) 0.0320(6) Uani d . . . 1 . .
C C4 -0.2716(3) 0.8738(3) 0.17117(8) 0.0382(6) Uani d . . . 1 . .
H H4A -0.2081 0.9584 0.1701 0.057 Uiso calc U . R 1 . .
H H4B -0.3391 0.8909 0.1934 0.057 Uiso calc U . R 1 . .
H H4C -0.3229 0.8607 0.1425 0.057 Uiso calc U . R 1 . .
C C5 -0.2725(3) 0.5983(3) 0.17177(8) 0.0383(6) Uani d . . . 1 . .
H H5A -0.2949 0.5935 0.1401 0.057 Uiso calc U . R 1 . .
H H5B -0.3602 0.602 0.1867 0.057 Uiso calc U . R 1 . .
H H5C -0.2183 0.511 0.1814 0.057 Uiso calc U . R 1 . .
C C6 0.2291(2) 0.7902(3) 0.13774(7) 0.0309(6) Uani d . . . 1 . .
C C7 0.3249(3) 0.9227(3) 0.08553(8) 0.0405(6) Uani d . . . 1 . .
H H7A 0.3788 0.8639 0.0652 0.049 Uiso calc U . R 1 . .
H H7B 0.3562 1.0264 0.0843 0.049 Uiso calc U . R 1 . .
C C8 0.1657(3) 0.9107(3) 0.07319(7) 0.0360(6) Uani d . . . 1 . .
C C9 0.0946(3) 1.0578(3) 0.07967(9) 0.0442(7) Uani d . . . 1 . .
H H9A -0.0078 1.0467 0.0744 0.066 Uiso calc U . R 1 . .
H H9B 0.1287 1.1298 0.0591 0.066 Uiso calc U . R 1 . .
H H9C 0.1171 1.092 0.1097 0.066 Uiso calc U . R 1 . .
C C10 0.1360(3) 0.8506(3) 0.02731(8) 0.0435(7) Uani d . . . 1 . .
H H10A 0.1789 0.753 0.0253 0.065 Uiso calc U . R 1 . .
H H10B 0.1761 0.917 0.0063 0.065 Uiso calc U . R 1 . .
H H10C 0.0337 0.843 0.0207 0.065 Uiso calc U . R 1 . .
C C11 0.0663(2) 0.5314(3) 0.11567(7) 0.0327(6) Uani d . . . 1 . .
H H11A -0.0082 0.4581 0.1204 0.039 Uiso calc U . R 1 . .
H H11B 0.1054 0.5086 0.0874 0.039 Uiso calc U . R 1 . .
C C12 0.1859(2) 0.5154(3) 0.15283(7) 0.0323(6) Uani d . . . 1 . .
H H12 0.1495 0.4475 0.1751 0.039 Uiso calc U . R 1 . .
C C13 0.3184(2) 0.4471(3) 0.13821(7) 0.0306(6) Uani d . . . 1 . .
C C14 0.3868(2) 0.5003(3) 0.10295(7) 0.0349(6) Uani d . . . 1 . .
H H14 0.3497 0.5848 0.0879 0.042 Uiso calc U . R 1 . .
C C15 0.5066(2) 0.4352(3) 0.08896(8) 0.0361(6) Uani d . . . 1 . .
H H15 0.5499 0.4758 0.0647 0.043 Uiso calc U . R 1 . .
C C16 0.5650(3) 0.3113(3) 0.10965(8) 0.0365(6) Uani d . . . 1 . .
C C17 0.6966(3) 0.2421(3) 0.09456(9) 0.0487(7) Uani d . . . 1 . .
H H17A 0.686 0.2278 0.0628 0.073 Uiso calc U . R 1 . .
H H17B 0.7122 0.1468 0.109 0.073 Uiso calc U . R 1 . .
H H17C 0.7774 0.3066 0.102 0.073 Uiso calc U . R 1 . .
C C18 0.4982(3) 0.2561(3) 0.14520(8) 0.0404(7) Uani d . . . 1 . .
H H18 0.5354 0.1714 0.16 0.048 Uiso calc U . R 1 . .
C C19 0.3780(3) 0.3229(3) 0.15928(8) 0.0376(6) Uani d . . . 1 . .
H H19 0.3353 0.2833 0.1838 0.045 Uiso calc U . R 1 . .
C C20 -0.1295(2) 0.7137(3) 0.07451(7) 0.0332(6) Uani d . . . 1 . .
C C21 -0.2125(2) 0.8398(3) 0.06846(8) 0.0353(6) Uani d . . . 1 . .
H H21 -0.1975 0.9193 0.0884 0.042 Uiso calc U . R 1 . .
C C22 -0.3163(3) 0.8535(3) 0.03438(8) 0.0401(6) Uani d . . . 1 . .
H H22 -0.3723 0.9401 0.0318 0.048 Uiso calc U . R 1 . .
C C23 -0.3383(3) 0.7417(3) 0.00425(8) 0.0447(7) Uani d . . . 1 . .
H H23 -0.4089 0.7507 -0.0192 0.054 Uiso calc U . R 1 . .
C C24 -0.2565(3) 0.6166(3) 0.00857(8) 0.0425(7) Uani d . . . 1 . .
H H24 -0.2699 0.5395 -0.0122 0.051 Uiso calc U . R 1 . .
C C25 -0.1549(3) 0.6024(3) 0.04301(7) 0.0366(6) Uani d . . . 1 . .
H H25 -0.1005 0.5147 0.0455 0.044 Uiso calc U . R 1 . .
C C26 0.3313(2) 0.6900(3) 0.21805(7) 0.0295(5) Uani d . . . 1 . .
C C27 0.4119(2) 0.8162(3) 0.22727(8) 0.0338(6) Uani d . . . 1 . .
H H27 0.4015 0.8978 0.2079 0.041 Uiso calc U . R 1 . .
C C28 0.5061(3) 0.8261(3) 0.26355(8) 0.0359(6) Uani d . . . 1 . .
H H28 0.5604 0.9132 0.2684 0.043 Uiso calc U . R 1 . .
C C29 0.5225(3) 0.7120(3) 0.29283(8) 0.0381(6) Uani d . . . 1 . .
H H29 0.5872 0.7192 0.3179 0.046 Uiso calc U . R 1 . .
C C30 0.4430(3) 0.5868(3) 0.28504(8) 0.0375(6) Uani d . . . 1 . .
H H30 0.4517 0.5073 0.3052 0.045 Uiso calc U . R 1 . .
C C31 0.3508(3) 0.5757(3) 0.24835(8) 0.0361(6) Uani d . . . 1 . .
H H31 0.2988 0.4873 0.2435 0.043 Uiso calc U . R 1 . .
N N1 -0.04817(19) 0.7289(2) 0.16161(6) 0.0296(5) Uani d . . . 1 . .
N N2 0.1261(2) 0.8038(2) 0.10750(6) 0.0311(5) Uani d . . . 1 . .
O O1 0.02021(16) 0.71392(17) 0.23239(5) 0.0318(4) Uani d . . . 1 . .
O O2 0.34607(16) 0.86605(18) 0.12970(5) 0.0355(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 N2 . 1.609(3) ?
B1 C20 . 1.610(4) ?
B1 N1 . 1.611(3) ?
B1 C11 . 1.634(4) ?
B2 C1 . 1.598(4) ?
B2 C6 . 1.598(4) ?
B2 C26 . 1.602(3) ?
B2 C12 . 1.704(4) ?
C1 N1 . 1.305(3) ?
C1 O1 . 1.334(3) ?
C2 O1 . 1.455(3) ?
C2 C3 . 1.545(3) ?
C3 N1 . 1.502(3) ?
C3 C5 . 1.521(3) ?
C3 C4 . 1.526(3) ?
C6 N2 . 1.304(3) ?
C6 O2 . 1.345(3) ?
C7 O2 . 1.449(3) ?
C7 C8 . 1.536(3) ?
C8 N2 . 1.499(3) ?
C8 C10 . 1.516(3) ?
C8 C9 . 1.517(4) ?
C11 C12 . 1.557(3) ?
C12 C13 . 1.500(3) ?
C13 C14 . 1.388(3) ?
C13 C19 . 1.400(3) ?
C14 C15 . 1.378(3) ?
C15 C16 . 1.389(3) ?
C16 C18 . 1.393(4) ?
C16 C17 . 1.501(3) ?
C18 C19 . 1.388(3) ?
C20 C21 . 1.396(3) ?
C20 C25 . 1.407(3) ?
C21 C22 . 1.389(3) ?
C22 C23 . 1.379(4) ?
C23 C24 . 1.378(4) ?
C24 C25 . 1.384(3) ?
C26 C31 . 1.397(3) ?
C26 C27 . 1.397(3) ?
C27 C28 . 1.379(3) ?
C28 C29 . 1.373(3) ?
C29 C30 . 1.378(4) ?
C30 C31 . 1.378(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 B1 C20 . . 113.33(19) ?
N2 B1 N1 . . 102.97(18) ?
C20 B1 N1 . . 115.8(2) ?
N2 B1 C11 . . 104.04(19) ?
C20 B1 C11 . . 114.6(2) ?
N1 B1 C11 . . 104.72(18) ?
C1 B2 C6 . . 102.69(19) ?
C1 B2 C26 . . 114.15(19) ?
C6 B2 C26 . . 117.5(2) ?
C1 B2 C12 . . 99.39(18) ?
C6 B2 C12 . . 102.64(18) ?
C26 B2 C12 . . 117.9(2) ?
N1 C1 O1 . . 114.8(2) ?
N1 C1 B2 . . 121.5(2) ?
O1 C1 B2 . . 123.4(2) ?
O1 C2 C3 . . 105.97(17) ?
N1 C3 C5 . . 110.10(19) ?
N1 C3 C4 . . 113.56(19) ?
C5 C3 C4 . . 110.5(2) ?
N1 C3 C2 . . 100.17(17) ?
C5 C3 C2 . . 112.7(2) ?
C4 C3 C2 . . 109.5(2) ?
N2 C6 O2 . . 114.1(2) ?
N2 C6 B2 . . 120.1(2) ?
O2 C6 B2 . . 125.7(2) ?
O2 C7 C8 . . 105.83(18) ?
N2 C8 C10 . . 112.2(2) ?
N2 C8 C9 . . 110.07(19) ?
C10 C8 C9 . . 112.6(2) ?
N2 C8 C7 . . 99.51(19) ?
C10 C8 C7 . . 111.6(2) ?
C9 C8 C7 . . 110.2(2) ?
C12 C11 B1 . . 113.86(19) ?
C13 C12 C11 . . 113.82(18) ?
C13 C12 B2 . . 113.34(18) ?
C11 C12 B2 . . 109.20(19) ?
C14 C13 C19 . . 116.4(2) ?
C14 C13 C12 . . 122.6(2) ?
C19 C13 C12 . . 121.1(2) ?
C15 C14 C13 . . 122.4(2) ?
C14 C15 C16 . . 121.2(2) ?
C15 C16 C18 . . 117.3(2) ?
C15 C16 C17 . . 120.9(2) ?
C18 C16 C17 . . 121.8(2) ?
C19 C18 C16 . . 121.1(2) ?
C18 C19 C13 . . 121.6(2) ?
C21 C20 C25 . . 115.6(2) ?
C21 C20 B1 . . 124.1(2) ?
C25 C20 B1 . . 120.2(2) ?
C22 C21 C20 . . 122.5(2) ?
C23 C22 C21 . . 120.2(3) ?
C24 C23 C22 . . 119.1(2) ?
C23 C24 C25 . . 120.5(3) ?
C24 C25 C20 . . 122.2(2) ?
C31 C26 C27 . . 115.6(2) ?
C31 C26 B2 . . 121.6(2) ?
C27 C26 B2 . . 122.6(2) ?
C28 C27 C26 . . 122.1(2) ?
C29 C28 C27 . . 120.9(2) ?
C28 C29 C30 . . 118.4(2) ?
C29 C30 C31 . . 120.7(2) ?
C30 C31 C26 . . 122.3(2) ?
C1 N1 C3 . . 110.35(18) ?
C1 N1 B1 . . 113.21(19) ?
C3 N1 B1 . . 134.21(18) ?
C6 N2 C8 . . 110.30(19) ?
C6 N2 B1 . . 114.76(19) ?
C8 N2 B1 . . 134.67(19) ?
C1 O1 C2 . . 107.81(17) ?
C6 O2 C7 . . 107.00(18) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1418727'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H33 B2 Br N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         555.11

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.5066(6)
_cell_length_b                   9.2480(5)
_cell_length_c                   30.632(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.399(3)
_cell_angle_gamma                90
_cell_volume                     2685.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1996
_cell_measurement_theta_min      2.5748
_cell_measurement_theta_max      21.9480
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152

_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.85

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            17487
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.1149
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_full        30.05
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       41

_refine_special_details          
;
;

_reflns_number_total             7720
_reflns_number_gt                4301
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1268
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_number_reflns         7720
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.702
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 -0.0083(3) 0.7999(3) 0.61258(11) 0.0200(7) Uani d . . . 1 . .
B B2 0.2107(3) 0.8140(3) 0.67851(10) 0.0172(7) Uani d . . . 1 . .
Br Br1 0.71939(4) 1.26691(3) 0.59158(2) 0.03804(12) Uani d . . . 1 . .
C C1 -0.1330(3) 0.7807(3) 0.57442(9) 0.0207(6) Uani d . . . 1 . .
C C2 -0.2155(3) 0.6555(3) 0.56776(9) 0.0243(7) Uani d . . . 1 . .
H H2 -0.1982 0.5764 0.5872 0.029 Uiso calc U . R 1 . .
C C3 -0.3207(3) 0.6416(3) 0.53420(10) 0.0277(7) Uani d . . . 1 . .
H H3 -0.375 0.5555 0.5315 0.033 Uiso calc U . R 1 . .
C C4 -0.3467(3) 0.7535(3) 0.50457(10) 0.0338(8) Uani d . . . 1 . .
H H4 -0.418 0.7449 0.4812 0.041 Uiso calc U . R 1 . .
C C5 -0.2663(3) 0.8781(3) 0.50973(10) 0.0328(8) Uani d . . . 1 . .
H H5 -0.2821 0.9553 0.4895 0.039 Uiso calc U . R 1 . .
C C6 -0.1634(3) 0.8919(3) 0.54389(9) 0.0266(7) Uani d . . . 1 . .
H H6 -0.1115 0.9796 0.5468 0.032 Uiso calc U . R 1 . .
C C7 0.1654(3) 0.5911(3) 0.57279(9) 0.0234(7) Uani d . . . 1 . .
C C8 0.0944(4) 0.4454(3) 0.57805(11) 0.0365(8) Uani d . . . 1 . .
H H8A 0.117 0.4092 0.6078 0.055 Uiso calc U . R 1 . .
H H8B 0.1284 0.3766 0.5569 0.055 Uiso calc U . R 1 . .
H H8C -0.0081 0.4565 0.5728 0.055 Uiso calc U . R 1 . .
C C9 0.1374(4) 0.6525(3) 0.52714(10) 0.0353(8) Uani d . . . 1 . .
H H9A 0.0354 0.657 0.5196 0.053 Uiso calc U . R 1 . .
H H9B 0.1812 0.5903 0.5061 0.053 Uiso calc U . R 1 . .
H H9C 0.1775 0.75 0.5261 0.053 Uiso calc U . R 1 . .
C C10 0.3243(3) 0.5780(3) 0.58544(9) 0.0293(7) Uani d . . . 1 . .
H H10A 0.3549 0.4758 0.5843 0.035 Uiso calc U . R 1 . .
H H10B 0.3789 0.6356 0.5653 0.035 Uiso calc U . R 1 . .
C C11 0.2274(3) 0.7075(3) 0.63788(9) 0.0185(6) Uani d . . . 1 . .
C C12 0.0532(3) 0.7802(3) 0.69138(9) 0.0172(6) Uani d . . . 1 . .
C C13 -0.1342(3) 0.7506(3) 0.73158(9) 0.0253(7) Uani d . . . 1 . .
H H13A -0.1817 0.8249 0.7485 0.03 Uiso calc U . R 1 . .
H H13B -0.1523 0.6543 0.7441 0.03 Uiso calc U . R 1 . .
C C14 -0.1887(3) 0.7563(3) 0.68260(9) 0.0204(6) Uani d . . . 1 . .
C C15 -0.2764(3) 0.8903(3) 0.67165(10) 0.0293(7) Uani d . . . 1 . .
H H15A -0.2218 0.9766 0.6806 0.044 Uiso calc U . R 1 . .
H H15B -0.3626 0.8871 0.6873 0.044 Uiso calc U . R 1 . .
H H15C -0.3016 0.8937 0.64 0.044 Uiso calc U . R 1 . .
C C16 -0.2731(3) 0.6203(3) 0.67045(10) 0.0290(7) Uani d . . . 1 . .
H H16A -0.3218 0.6321 0.6413 0.043 Uiso calc U . R 1 . .
H H16B -0.3427 0.604 0.6919 0.043 Uiso calc U . R 1 . .
H H16C -0.2091 0.5372 0.6703 0.043 Uiso calc U . R 1 . .
C C17 0.0620(3) 0.9609(3) 0.61607(9) 0.0195(6) Uani d . . . 1 . .
H H17A 0.1015 0.9842 0.5879 0.023 Uiso calc U . R 1 . .
H H17B -0.0129 1.0323 0.6207 0.023 Uiso calc U . R 1 . .
C C18 0.1812(3) 0.9761(3) 0.65382(8) 0.0187(6) Uani d . . . 1 . .
H H18 0.1441 1.0419 0.6762 0.022 Uiso calc U . R 1 . .
C C19 0.3131(3) 1.0454(3) 0.63932(8) 0.0193(6) Uani d . . . 1 . .
C C20 0.3814(3) 0.9930(3) 0.60403(9) 0.0217(6) Uani d . . . 1 . .
H H20 0.3444 0.9096 0.5891 0.026 Uiso calc U . R 1 . .
C C21 0.5017(3) 1.0573(3) 0.58959(9) 0.0222(6) Uani d . . . 1 . .
H H21 0.5462 1.0187 0.5654 0.027 Uiso calc U . R 1 . .
C C22 0.5543(3) 1.1784(3) 0.61126(10) 0.0235(7) Uani d . . . 1 . .
C C23 0.4922(3) 1.2346(3) 0.64696(10) 0.0296(7) Uani d . . . 1 . .
H H23 0.5309 1.3172 0.6619 0.036 Uiso calc U . R 1 . .
C C24 0.3715(3) 1.1675(3) 0.66060(9) 0.0263(7) Uani d . . . 1 . .
H H24 0.3279 1.2059 0.685 0.032 Uiso calc U . R 1 . .
C C25 0.3286(3) 0.8050(3) 0.71886(9) 0.0178(6) Uani d . . . 1 . .
C C26 0.3472(3) 0.9179(3) 0.74928(9) 0.0237(7) Uani d . . . 1 . .
H H26 0.2943 1.0043 0.7443 0.028 Uiso calc U . R 1 . .
C C27 0.4397(3) 0.9082(3) 0.78621(10) 0.0300(7) Uani d . . . 1 . .
H H27 0.4473 0.986 0.8065 0.036 Uiso calc U . R 1 . .
C C28 0.5215(3) 0.7853(3) 0.79385(10) 0.0273(7) Uani d . . . 1 . .
H H28 0.5868 0.7789 0.8189 0.033 Uiso calc U . R 1 . .
C C29 0.5061(3) 0.6725(3) 0.76436(9) 0.0244(7) Uani d . . . 1 . .
H H29 0.5608 0.5873 0.7691 0.029 Uiso calc U . R 1 . .
C C30 0.4115(3) 0.6830(3) 0.72805(9) 0.0204(6) Uani d . . . 1 . .
H H30 0.4026 0.6035 0.7084 0.025 Uiso calc U . R 1 . .
N N1 0.1244(2) 0.6935(2) 0.60757(7) 0.0191(5) Uani d . . . 1 . .
N N2 -0.0505(2) 0.7638(2) 0.66171(7) 0.0169(5) Uani d . . . 1 . .
O O1 0.3449(2) 0.6339(2) 0.63007(6) 0.0237(5) Uani d . . . 1 . .
O O2 0.01677(19) 0.77866(19) 0.73282(6) 0.0198(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C1 . 1.609(4) ?
B1 N1 . 1.615(4) ?
B1 N2 . 1.622(4) ?
B1 C17 . 1.632(4) ?
B2 C11 . 1.605(4) ?
B2 C25 . 1.606(4) ?
B2 C12 . 1.608(4) ?
B2 C18 . 1.693(4) ?
Br1 C22 . 1.908(3) ?
C1 C2 . 1.405(4) ?
C1 C6 . 1.405(4) ?
C2 C3 . 1.384(4) ?
C3 C4 . 1.386(4) ?
C4 C5 . 1.385(4) ?
C5 C6 . 1.382(4) ?
C7 N1 . 1.499(3) ?
C7 C9 . 1.514(4) ?
C7 C8 . 1.522(4) ?
C7 C10 . 1.535(4) ?
C10 O1 . 1.461(3) ?
C11 N1 . 1.303(3) ?
C11 O1 . 1.345(3) ?
C12 N2 . 1.298(3) ?
C12 O2 . 1.341(3) ?
C13 O2 . 1.456(3) ?
C13 C14 . 1.550(4) ?
C14 N2 . 1.506(3) ?
C14 C15 . 1.517(4) ?
C14 C16 . 1.523(4) ?
C17 C18 . 1.562(4) ?
C18 C19 . 1.505(4) ?
C19 C20 . 1.390(4) ?
C19 C24 . 1.398(4) ?
C20 C21 . 1.391(4) ?
C21 C22 . 1.376(4) ?
C22 C23 . 1.383(4) ?
C23 C24 . 1.396(4) ?
C25 C30 . 1.392(4) ?
C25 C26 . 1.402(4) ?
C26 C27 . 1.381(4) ?
C27 C28 . 1.386(4) ?
C28 C29 . 1.380(4) ?
C29 C30 . 1.378(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 B1 N1 . . 113.6(2) ?
C1 B1 N2 . . 115.5(2) ?
N1 B1 N2 . . 102.3(2) ?
C1 B1 C17 . . 115.0(2) ?
N1 B1 C17 . . 104.1(2) ?
N2 B1 C17 . . 104.8(2) ?
C11 B2 C25 . . 117.4(2) ?
C11 B2 C12 . . 102.7(2) ?
C25 B2 C12 . . 114.2(2) ?
C11 B2 C18 . . 102.7(2) ?
C25 B2 C18 . . 118.1(2) ?
C12 B2 C18 . . 99.0(2) ?
C2 C1 C6 . . 115.0(3) ?
C2 C1 B1 . . 124.6(2) ?
C6 C1 B1 . . 120.4(3) ?
C3 C2 C1 . . 123.2(3) ?
C2 C3 C4 . . 120.0(3) ?
C5 C4 C3 . . 118.5(3) ?
C6 C5 C4 . . 121.0(3) ?
C5 C6 C1 . . 122.3(3) ?
N1 C7 C9 . . 112.5(2) ?
N1 C7 C8 . . 110.0(2) ?
C9 C7 C8 . . 112.4(2) ?
N1 C7 C10 . . 100.1(2) ?
C9 C7 C10 . . 111.3(3) ?
C8 C7 C10 . . 109.8(2) ?
O1 C10 C7 . . 105.5(2) ?
N1 C11 O1 . . 114.4(2) ?
N1 C11 B2 . . 120.0(2) ?
O1 C11 B2 . . 125.6(2) ?
N2 C12 O2 . . 115.1(2) ?
N2 C12 B2 . . 121.5(2) ?
O2 C12 B2 . . 123.1(2) ?
O2 C13 C14 . . 106.0(2) ?
N2 C14 C15 . . 110.6(2) ?
N2 C14 C16 . . 113.2(2) ?
C15 C14 C16 . . 110.5(2) ?
N2 C14 C13 . . 100.1(2) ?
C15 C14 C13 . . 112.3(2) ?
C16 C14 C13 . . 109.8(2) ?
C18 C17 B1 . . 113.6(2) ?
C19 C18 C17 . . 113.1(2) ?
C19 C18 B2 . . 113.3(2) ?
C17 C18 B2 . . 109.7(2) ?
C20 C19 C24 . . 116.8(3) ?
C20 C19 C18 . . 122.1(2) ?
C24 C19 C18 . . 121.1(3) ?
C19 C20 C21 . . 122.9(3) ?
C22 C21 C20 . . 118.2(3) ?
C21 C22 C23 . . 121.7(3) ?
C21 C22 Br1 . . 118.3(2) ?
C23 C22 Br1 . . 120.0(2) ?
C22 C23 C24 . . 118.7(3) ?
C23 C24 C19 . . 121.7(3) ?
C30 C25 C26 . . 115.4(3) ?
C30 C25 B2 . . 123.3(2) ?
C26 C25 B2 . . 121.2(2) ?
C27 C26 C25 . . 122.4(3) ?
C26 C27 C28 . . 120.4(3) ?
C29 C28 C27 . . 118.6(3) ?
C30 C29 C28 . . 120.3(3) ?
C29 C30 C25 . . 123.0(3) ?
C11 N1 C7 . . 110.2(2) ?
C11 N1 B1 . . 114.9(2) ?
C7 N1 B1 . . 134.4(2) ?
C12 N2 C14 . . 110.4(2) ?
C12 N2 B1 . . 113.4(2) ?
C14 N2 B1 . . 133.6(2) ?
C11 O1 C10 . . 107.0(2) ?
C12 O2 C13 . . 107.6(2) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1418728'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H39 B2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         505.27

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.8862(4)
_cell_length_b                   21.9850(11)
_cell_length_c                   14.0495(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.2349(19)
_cell_angle_gamma                90
_cell_volume                     2728.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4501
_cell_measurement_theta_min      2.4848
_cell_measurement_theta_max      22.3431
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1084

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            44526
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             6540
_reflns_number_gt                4342
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1777
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_number_reflns         6540
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0960P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.504
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 -0.0676(2) 0.20189(9) 0.01667(15) 0.0160(4) Uani d . . . 1 . .
B B2 0.1420(2) 0.11966(9) 0.10585(15) 0.0171(4) Uani d . . . 1 . .
C C1 0.1860(2) 0.19028(9) 0.10315(13) 0.0161(4) Uani d . . . 1 . .
C C2 0.3280(2) 0.27499(9) 0.09873(17) 0.0276(5) Uani d . . . 1 . .
H H2A 0.3925 0.2789 0.0459 0.033 Uiso calc U . R 1 . .
H H2B 0.3688 0.3018 0.152 0.033 Uiso calc U . R 1 . .
C C3 0.1632(2) 0.29226(8) 0.06409(14) 0.0204(4) Uani d . . . 1 . .
C C4 0.1041(3) 0.33698(10) 0.13443(17) 0.0311(5) Uani d . . . 1 . .
H H4A 0.0044 0.352 0.1081 0.047 Uiso calc U . R 1 . .
H H4B 0.1745 0.3713 0.1448 0.047 Uiso calc U . R 1 . .
H H4C 0.0957 0.3164 0.1955 0.047 Uiso calc U . R 1 . .
C C5 0.1492(3) 0.31913(10) -0.03617(15) 0.0301(5) Uani d . . . 1 . .
H H5A 0.1885 0.2901 -0.0802 0.045 Uiso calc U . R 1 . .
H H5B 0.2074 0.357 -0.0357 0.045 Uiso calc U . R 1 . .
H H5C 0.0425 0.3276 -0.0572 0.045 Uiso calc U . R 1 . .
C C6 -0.0233(2) 0.12270(8) 0.14012(13) 0.0174(4) Uani d . . . 1 . .
C C7 -0.2383(2) 0.09260(11) 0.1968(2) 0.0387(6) Uani d . . . 1 . .
H H7A -0.267 0.0993 0.2622 0.046 Uiso calc U . R 1 . .
H H7B -0.2946 0.0569 0.1686 0.046 Uiso calc U . R 1 . .
C C8 -0.2748(2) 0.14928(9) 0.13445(14) 0.0199(4) Uani d . . . 1 . .
C C9 -0.3926(2) 0.13558(12) 0.05137(16) 0.0338(5) Uani d . . . 1 . .
H H9A -0.4129 0.1724 0.0127 0.051 Uiso calc U . R 1 . .
H H9B -0.4862 0.122 0.0758 0.051 Uiso calc U . R 1 . .
H H9C -0.3551 0.1035 0.0117 0.051 Uiso calc U . R 1 . .
C C10 -0.3216(2) 0.20098(10) 0.19709(15) 0.0260(5) Uani d . . . 1 . .
H H10A -0.2386 0.2101 0.2468 0.039 Uiso calc U . R 1 . .
H H10B -0.4114 0.1889 0.2272 0.039 Uiso calc U . R 1 . .
H H10C -0.345 0.2372 0.1576 0.039 Uiso calc U . R 1 . .
C C11 -0.1939(2) 0.25059(8) -0.02502(14) 0.0186(4) Uani d . . . 1 . .
C C12 -0.2420(2) 0.29959(9) 0.02820(15) 0.0216(4) Uani d . . . 1 . .
H H12 -0.1961 0.3054 0.0918 0.026 Uiso calc U . R 1 . .
C C13 -0.3535(2) 0.33976(9) -0.00824(16) 0.0263(5) Uani d . . . 1 . .
H H13 -0.381 0.3729 0.0296 0.032 Uiso calc U . R 1 . .
C C14 -0.4254(2) 0.33156(10) -0.10026(16) 0.0280(5) Uani d . . . 1 . .
H H14 -0.5023 0.3589 -0.1257 0.034 Uiso calc U . R 1 . .
C C15 -0.3834(2) 0.28327(10) -0.15414(15) 0.0273(5) Uani d . . . 1 . .
H H15 -0.4331 0.2767 -0.2166 0.033 Uiso calc U . R 1 . .
C C16 -0.2686(2) 0.24416(9) -0.11745(14) 0.0226(4) Uani d . . . 1 . .
H H16 -0.2397 0.2119 -0.1566 0.027 Uiso calc U . R 1 . .
C C17 0.2583(2) 0.07452(8) 0.16729(14) 0.0184(4) Uani d . . . 1 . .
C C18 0.2811(2) 0.01481(9) 0.13815(15) 0.0260(5) Uani d . . . 1 . .
H H18 0.2295 0.0012 0.0793 0.031 Uiso calc U . R 1 . .
C C19 0.3765(3) -0.02548(10) 0.19210(17) 0.0308(5) Uani d . . . 1 . .
H H19 0.3896 -0.0657 0.1695 0.037 Uiso calc U . R 1 . .
C C20 0.4523(2) -0.00722(10) 0.27842(16) 0.0280(5) Uani d . . . 1 . .
H H20 0.5175 -0.0345 0.3156 0.034 Uiso calc U . R 1 . .
C C21 0.4315(2) 0.05156(10) 0.30985(15) 0.0264(5) Uani d . . . 1 . .
H H21 0.4824 0.0647 0.3693 0.032 Uiso calc U . R 1 . .
C C22 0.3371(2) 0.09150(9) 0.25522(14) 0.0223(4) Uani d . . . 1 . .
H H22 0.3253 0.1317 0.2781 0.027 Uiso calc U . R 1 . .
C C23 -0.0198(2) 0.15034(8) -0.05916(13) 0.0177(4) Uani d . . . 1 . .
H H23 -0.1144 0.1288 -0.0855 0.021 Uiso calc U . R 1 . .
C C24 0.0906(2) 0.10139(8) -0.00922(13) 0.0178(4) Uani d . . . 1 . .
H H24 0.0357 0.0617 -0.0107 0.021 Uiso calc U . R 1 . .
C C25 0.2162(2) 0.09651(9) -0.07706(14) 0.0214(4) Uani d . . . 1 . .
H H25 0.3122 0.0771 -0.048 0.026 Uiso calc U . R 1 . .
C C26 0.2332(2) 0.16269(9) -0.10958(14) 0.0234(4) Uani d . . . 1 . .
H H26A 0.2999 0.1667 -0.1613 0.028 Uiso calc U . R 1 . .
H H26B 0.2671 0.1904 -0.056 0.028 Uiso calc U . R 1 . .
C C27 0.0642(2) 0.17036(9) -0.14567(13) 0.0211(4) Uani d . . . 1 . .
H H27 0.0358 0.2117 -0.1714 0.025 Uiso calc U . R 1 . .
C C28 0.0469(2) 0.11885(9) -0.22075(15) 0.0263(5) Uani d . . . 1 . .
H H28A 0.0844 0.1317 -0.2815 0.032 Uiso calc U . R 1 . .
H H28B -0.06 0.1058 -0.2339 0.032 Uiso calc U . R 1 . .
C C29 0.1470(2) 0.06731(9) -0.17138(15) 0.0271(5) Uani d . . . 1 . .
H H29A 0.0851 0.0313 -0.1589 0.032 Uiso calc U . R 1 . .
H H29B 0.2269 0.0549 -0.2113 0.032 Uiso calc U . R 1 . .
C C30 1.0435(4) 0.00069(12) 0.40853(19) 0.0531(8) Uani d . . . 1 . .
H H30 1.0736 0.0013 0.3457 0.064 Uiso calc U . R 1 . .
C C31 0.8942(4) 0.00763(12) 0.4224(2) 0.0544(8) Uani d . . . 1 . .
H H31 0.8203 0.0128 0.3689 0.065 Uiso calc U . R 1 . .
C C32 0.8509(4) 0.00712(12) 0.5135(2) 0.0533(7) Uani d . . . 1 . .
H H32 0.7472 0.0122 0.5225 0.064 Uiso calc U . R 1 . .
N N1 0.08903(17) 0.23069(7) 0.06585(11) 0.0158(3) Uani d . . . 1 . .
N N2 -0.12228(16) 0.16133(7) 0.10183(11) 0.0172(3) Uani d . . . 1 . .
O O1 0.32400(14) 0.21229(6) 0.13083(10) 0.0212(3) Uani d . . . 1 . .
O O2 -0.07673(14) 0.08268(6) 0.19991(10) 0.0215(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 N2 . 1.609(3) ?
B1 N1 . 1.614(2) ?
B1 C11 . 1.615(3) ?
B1 C23 . 1.643(3) ?
B2 C6 . 1.596(3) ?
B2 C1 . 1.603(3) ?
B2 C17 . 1.613(3) ?
B2 C24 . 1.680(3) ?
C1 N1 . 1.307(2) ?
C1 O1 . 1.336(2) ?
C2 O1 . 1.452(2) ?
C2 C3 . 1.539(3) ?
C3 N1 . 1.507(2) ?
C3 C5 . 1.520(3) ?
C3 C4 . 1.527(3) ?
C6 N2 . 1.297(2) ?
C6 O2 . 1.338(2) ?
C7 O2 . 1.448(3) ?
C7 C8 . 1.537(3) ?
C8 N2 . 1.501(2) ?
C8 C9 . 1.511(3) ?
C8 C10 . 1.523(3) ?
C11 C16 . 1.400(3) ?
C11 C12 . 1.404(3) ?
C12 C13 . 1.383(3) ?
C13 C14 . 1.390(3) ?
C14 C15 . 1.379(3) ?
C15 C16 . 1.390(3) ?
C17 C18 . 1.397(3) ?
C17 C22 . 1.403(3) ?
C18 C19 . 1.392(3) ?
C19 C20 . 1.381(3) ?
C20 C21 . 1.385(3) ?
C21 C22 . 1.387(3) ?
C23 C27 . 1.557(3) ?
C23 C24 . 1.569(2) ?
C24 C25 . 1.548(3) ?
C25 C26 . 1.537(3) ?
C25 C29 . 1.539(3) ?
C26 C27 . 1.542(3) ?
C27 C28 . 1.544(3) ?
C28 C29 . 1.556(3) ?
C30 C31 . 1.370(5) ?
C30 C32 3_756 1.374(4) ?
C31 C32 . 1.376(4) ?
C32 C30 3_756 1.374(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 B1 N1 . . 102.42(14) ?
N2 B1 C11 . . 112.50(15) ?
N1 B1 C11 . . 115.36(15) ?
N2 B1 C23 . . 102.72(14) ?
N1 B1 C23 . . 106.06(14) ?
C11 B1 C23 . . 116.16(16) ?
C6 B2 C1 . . 101.62(14) ?
C6 B2 C17 . . 114.91(16) ?
C1 B2 C17 . . 117.70(16) ?
C6 B2 C24 . . 97.90(14) ?
C1 B2 C24 . . 104.50(15) ?
C17 B2 C24 . . 117.33(15) ?
N1 C1 O1 . . 114.51(16) ?
N1 C1 B2 . . 121.07(16) ?
O1 C1 B2 . . 124.22(16) ?
O1 C2 C3 . . 106.14(15) ?
N1 C3 C5 . . 111.86(16) ?
N1 C3 C4 . . 112.71(16) ?
C5 C3 C4 . . 110.48(17) ?
N1 C3 C2 . . 100.14(14) ?
C5 C3 C2 . . 111.62(17) ?
C4 C3 C2 . . 109.65(17) ?
N2 C6 O2 . . 114.83(16) ?
N2 C6 B2 . . 120.48(16) ?
O2 C6 B2 . . 124.24(16) ?
O2 C7 C8 . . 106.62(16) ?
N2 C8 C9 . . 111.85(16) ?
N2 C8 C10 . . 110.92(15) ?
C9 C8 C10 . . 112.67(17) ?
N2 C8 C7 . . 100.12(15) ?
C9 C8 C7 . . 111.35(19) ?
C10 C8 C7 . . 109.24(18) ?
C16 C11 C12 . . 115.51(17) ?
C16 C11 B1 . . 120.68(17) ?
C12 C11 B1 . . 123.74(17) ?
C13 C12 C11 . . 122.66(19) ?
C12 C13 C14 . . 119.99(19) ?
C15 C14 C13 . . 119.08(19) ?
C14 C15 C16 . . 120.3(2) ?
C15 C16 C11 . . 122.44(19) ?
C18 C17 C22 . . 115.71(18) ?
C18 C17 B2 . . 121.75(17) ?
C22 C17 B2 . . 122.47(17) ?
C19 C18 C17 . . 122.53(19) ?
C20 C19 C18 . . 120.2(2) ?
C19 C20 C21 . . 118.83(19) ?
C20 C21 C22 . . 120.5(2) ?
C21 C22 C17 . . 122.21(19) ?
C27 C23 C24 . . 102.34(14) ?
C27 C23 B1 . . 119.39(15) ?
C24 C23 B1 . . 112.10(15) ?
C25 C24 C23 . . 103.28(15) ?
C25 C24 B2 . . 118.05(15) ?
C23 C24 B2 . . 110.96(15) ?
C26 C25 C29 . . 100.47(16) ?
C26 C25 C24 . . 102.59(15) ?
C29 C25 C24 . . 108.15(16) ?
C25 C26 C27 . . 94.46(15) ?
C26 C27 C28 . . 99.52(15) ?
C26 C27 C23 . . 104.16(15) ?
C28 C27 C23 . . 107.79(16) ?
C27 C28 C29 . . 102.70(16) ?
C25 C29 C28 . . 103.64(16) ?
C31 C30 C32 . 3_756 119.3(3) ?
C30 C31 C32 . . 120.3(3) ?
C30 C32 C31 3_756 . 120.4(3) ?
C1 N1 C3 . . 110.27(15) ?
C1 N1 B1 . . 113.91(15) ?
C3 N1 B1 . . 134.71(15) ?
C6 N2 C8 . . 110.61(15) ?
C6 N2 B1 . . 115.16(15) ?
C8 N2 B1 . . 132.91(15) ?
C1 O1 C2 . . 107.81(14) ?
C6 O2 C7 . . 107.48(15) ?

