# 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_compound2b
_database_code_depnum_ccdc_archive 'CCDC 1881761'
_audit_update_record             
;
2019-01-16 deposited with the CCDC.
2019-01-24 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            'C16 H20 B10 Cl2 N2'
_chemical_formula_weight         419.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.133(2)
_cell_length_b                   12.872(4)
_cell_length_c                   13.741(4)
_cell_angle_alpha                66.302(4)
_cell_angle_beta                 75.196(5)
_cell_angle_gamma                83.836(5)
_cell_volume                     1117.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2843
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      26.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.297
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6208
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            7071
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.664
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4112
_reflns_number_gt                3105
_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)+(0.1472P)²+0.2987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4112
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.2156
_refine_ls_wR_factor_gt          0.1943
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 1.2262(5) 0.8859(3) 0.2803(2) 0.0413(7) Uani 1 1 d . . . . .
B2 B 1.1821(5) 0.9437(3) 0.1473(2) 0.0437(7) Uani 1 1 d . . . . .
B3 B 0.9631(5) 0.8839(3) 0.1531(2) 0.0444(7) Uani 1 1 d . . . . .
B4 B 0.8723(5) 0.7886(3) 0.2908(3) 0.0418(7) Uani 1 1 d . . . . .
B5 B 1.3539(5) 0.8330(3) 0.1814(3) 0.0468(7) Uani 1 1 d . . . . .
B6 B 1.1912(5) 0.8320(3) 0.1021(3) 0.0481(8) Uani 1 1 d . . . . .
B7 B 0.9989(5) 0.7354(3) 0.1913(3) 0.0478(8) Uani 1 1 d . . . . .
B8 B 1.0468(5) 0.6771(3) 0.3238(2) 0.0429(7) Uani 1 1 d . . . . .
B9 B 1.2635(5) 0.7365(3) 0.3175(3) 0.0427(7) Uani 1 1 d . . . . .
B10 B 1.2409(5) 0.7040(3) 0.2076(3) 0.0478(8) Uani 1 1 d . . . . .
C1 C 0.9932(4) 0.9120(2) 0.2595(2) 0.0373(6) Uani 1 1 d . . . . .
C2 C 1.0430(4) 0.7884(2) 0.3610(2) 0.0357(6) Uani 1 1 d . . . . .
Cl1 Cl 0.6639(2) 0.66430(11) 1.00533(7) 0.1091(5) Uani 1 1 d . . . . .
Cl2 Cl 0.45520(15) 1.43169(8) 0.40954(9) 0.0759(4) Uani 1 1 d . . . . .
N1 N 0.9673(3) 0.78757(18) 0.46702(17) 0.0392(5) Uani 1 1 d . . . . .
N2 N 0.8834(3) 0.98976(19) 0.30087(18) 0.0428(6) Uani 1 1 d . . . . .
C3 C 0.9874(4) 0.6992(2) 0.5486(2) 0.0395(6) Uani 1 1 d . . . . .
C4 C 0.8408(4) 1.0857(2) 0.2363(2) 0.0434(6) Uani 1 1 d . . . . .
C5 C 0.9111(4) 0.6928(2) 0.6604(2) 0.0378(6) Uani 1 1 d . . . . .
C6 C 0.9171(5) 0.5903(2) 0.7475(2) 0.0468(7) Uani 1 1 d . . . . .
C7 C 0.8406(5) 0.5798(3) 0.8544(2) 0.0570(8) Uani 1 1 d . . . . .
C8 C 0.7624(5) 0.6741(3) 0.8716(2) 0.0537(8) Uani 1 1 d . . . . .
C9 C 0.7525(5) 0.7771(3) 0.7881(2) 0.0494(7) Uani 1 1 d . . . . .
C10 C 0.8275(4) 0.7866(2) 0.6815(2) 0.0417(6) Uani 1 1 d . . . . .
C11 C 0.7331(4) 1.1687(2) 0.2786(2) 0.0413(6) Uani 1 1 d . . . . .
C12 C 0.6621(4) 1.1394(3) 0.3916(3) 0.0472(7) Uani 1 1 d . . . . .
C13 C 0.5739(5) 1.2190(3) 0.4307(3) 0.0529(7) Uani 1 1 d . . . . .
C14 C 0.5556(4) 1.3297(2) 0.3587(3) 0.0492(7) Uani 1 1 d . . . . .
C15 C 0.6207(5) 1.3605(3) 0.2473(3) 0.0537(8) Uani 1 1 d . . . . .
C16 C 0.7084(5) 1.2789(3) 0.2080(3) 0.0503(7) Uani 1 1 d . . . . .
H9 H 1.349(4) 0.693(3) 0.377(3) 0.048(8) Uiso 1 1 d . . . . .
H13 H 0.972(5) 0.530(3) 0.732(3) 0.053(9) Uiso 1 1 d . . . . .
H10 H 1.311(4) 0.634(3) 0.195(2) 0.046(8) Uiso 1 1 d . . . . .
H8 H 0.990(4) 0.594(2) 0.390(2) 0.037(7) Uiso 1 1 d . . . . .
H3 H 0.867(5) 0.935(3) 0.110(3) 0.052(8) Uiso 1 1 d . . . . .
H7 H 0.921(4) 0.686(2) 0.166(2) 0.047(8) Uiso 1 1 d . . . . .
H20 H 0.769(5) 1.302(3) 0.124(3) 0.068(10) Uiso 1 1 d . . . . .
H14 H 0.854(5) 0.515(3) 0.916(3) 0.055(9) Uiso 1 1 d . . . . .
H15 H 0.702(4) 0.834(3) 0.803(2) 0.040(7) Uiso 1 1 d . . . . .
H17 H 0.678(5) 1.071(3) 0.438(3) 0.051(9) Uiso 1 1 d . . . . .
H4 H 0.724(5) 0.780(3) 0.335(3) 0.050(8) Uiso 1 1 d . . . . .
H2 H 1.217(6) 1.028(4) 0.099(3) 0.082(12) Uiso 1 1 d . . . . .
H1 H 1.272(4) 0.940(2) 0.318(2) 0.042(7) Uiso 1 1 d . . . . .
H18 H 0.528(5) 1.200(3) 0.515(3) 0.067(10) Uiso 1 1 d . . . . .
H11 H 1.052(5) 0.634(3) 0.539(3) 0.061(9) Uiso 1 1 d . . . . .
H6 H 1.246(5) 0.840(3) 0.017(3) 0.072(11) Uiso 1 1 d . . . . .
H5 H 1.517(6) 0.850(3) 0.154(3) 0.073(11) Uiso 1 1 d . . . . .
H16 H 0.828(5) 0.859(3) 0.620(3) 0.052(8) Uiso 1 1 d . . . . .
H12 H 0.878(5) 1.111(3) 0.160(3) 0.051(8) Uiso 1 1 d . . . . .
H19 H 0.601(5) 1.440(3) 0.195(3) 0.054(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C1 1.733(4) . ?
B1 C2 1.734(4) . ?
B1 B5 1.766(4) . ?
B1 B2 1.772(4) . ?
B1 B9 1.789(4) . ?
B2 C1 1.706(4) . ?
B2 B5 1.770(5) . ?
B2 B6 1.771(5) . ?
B2 B3 1.784(5) . ?
B3 C1 1.707(4) . ?
B3 B6 1.774(5) . ?
B3 B7 1.775(5) . ?
B3 B4 1.784(5) . ?
B4 C1 1.734(4) . ?
B4 C2 1.736(4) . ?
B4 B7 1.773(5) . ?
B4 B8 1.788(5) . ?
B5 B9 1.774(5) . ?
B5 B10 1.787(5) . ?
B5 B6 1.788(5) . ?
B6 B10 1.777(5) . ?
B6 B7 1.792(5) . ?
B7 B8 1.777(4) . ?
B7 B10 1.780(5) . ?
B8 C2 1.700(4) . ?
B8 B10 1.765(5) . ?
B8 B9 1.765(5) . ?
B9 C2 1.701(4) . ?
B9 B10 1.769(4) . ?
C1 N2 1.414(3) . ?
C1 C2 1.718(3) . ?
C2 N1 1.414(3) . ?
Cl1 C8 1.749(3) . ?
Cl2 C14 1.734(3) . ?
N1 C3 1.262(3) . ?
N2 C4 1.258(4) . ?
C3 C5 1.464(3) . ?
C4 C11 1.470(4) . ?
C5 C6 1.385(4) . ?
C5 C10 1.391(4) . ?
C6 C7 1.386(4) . ?
C7 C8 1.363(5) . ?
C8 C9 1.370(5) . ?
C9 C10 1.385(4) . ?
C11 C16 1.383(4) . ?
C11 C12 1.407(4) . ?
C12 C13 1.366(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.380(5) . ?
C15 C16 1.389(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
C1 B1 C2 59.42(16) . . ?
C1 B1 B5 105.0(2) . . ?
C2 B1 B5 104.7(2) . . ?
C1 B1 B2 58.24(17) . . ?
C2 B1 B2 105.8(2) . . ?
B5 B1 B2 60.03(18) . . ?
C1 B1 B9 105.5(2) . . ?
C2 B1 B9 57.71(17) . . ?
B5 B1 B9 59.85(18) . . ?
B2 B1 B9 107.7(2) . . ?
C1 B2 B5 106.0(2) . . ?
C1 B2 B6 105.4(2) . . ?
B5 B2 B6 60.6(2) . . ?
C1 B2 B1 59.71(17) . . ?
B5 B2 B1 59.81(18) . . ?
B6 B2 B1 108.4(2) . . ?
C1 B2 B3 58.52(17) . . ?
B5 B2 B3 108.3(2) . . ?
B6 B2 B3 59.84(19) . . ?
B1 B2 B3 108.2(2) . . ?
C1 B3 B6 105.2(2) . . ?
C1 B3 B7 105.8(2) . . ?
B6 B3 B7 60.6(2) . . ?
C1 B3 B4 59.50(16) . . ?
B6 B3 B4 108.2(2) . . ?
B7 B3 B4 59.73(18) . . ?
C1 B3 B2 58.45(17) . . ?
B6 B3 B2 59.72(19) . . ?
B7 B3 B2 108.1(2) . . ?
B4 B3 B2 107.8(2) . . ?
C1 B4 C2 59.37(15) . . ?
C1 B4 B7 104.8(2) . . ?
C2 B4 B7 104.6(2) . . ?
C1 B4 B3 58.04(16) . . ?
C2 B4 B3 105.6(2) . . ?
B7 B4 B3 59.88(18) . . ?
C1 B4 B8 105.4(2) . . ?
C2 B4 B8 57.66(16) . . ?
B7 B4 B8 59.89(18) . . ?
B3 B4 B8 107.5(2) . . ?
B1 B5 B2 60.16(18) . . ?
B1 B5 B9 60.71(17) . . ?
B2 B5 B9 108.5(2) . . ?
B1 B5 B10 108.0(2) . . ?
B2 B5 B10 107.5(3) . . ?
B9 B5 B10 59.57(18) . . ?
B1 B5 B6 107.9(2) . . ?
B2 B5 B6 59.72(19) . . ?
B9 B5 B6 107.6(2) . . ?
B10 B5 B6 59.63(19) . . ?
B2 B6 B3 60.44(19) . . ?
B2 B6 B10 107.9(2) . . ?
B3 B6 B10 107.8(2) . . ?
B2 B6 B5 59.65(19) . . ?
B3 B6 B5 108.0(2) . . ?
B10 B6 B5 60.2(2) . . ?
B2 B6 B7 108.0(2) . . ?
B3 B6 B7 59.72(19) . . ?
B10 B6 B7 59.8(2) . . ?
B5 B6 B7 107.9(2) . . ?
B4 B7 B3 60.39(18) . . ?
B4 B7 B8 60.48(17) . . ?
B3 B7 B8 108.4(2) . . ?
B4 B7 B10 107.9(2) . . ?
B3 B7 B10 107.6(2) . . ?
B8 B7 B10 59.48(19) . . ?
B4 B7 B6 107.9(2) . . ?
B3 B7 B6 59.63(19) . . ?
B8 B7 B6 107.4(2) . . ?
B10 B7 B6 59.7(2) . . ?
C2 B8 B10 105.5(2) . . ?
C2 B8 B9 58.77(17) . . ?
B10 B8 B9 60.16(19) . . ?
C2 B8 B7 105.9(2) . . ?
B10 B8 B7 60.35(19) . . ?
B9 B8 B7 108.6(2) . . ?
C2 B8 B4 59.63(16) . . ?
B10 B8 B4 108.0(2) . . ?
B9 B8 B4 108.3(2) . . ?
B7 B8 B4 59.63(18) . . ?
C2 B9 B8 58.71(17) . . ?
C2 B9 B10 105.3(2) . . ?
B8 B9 B10 59.92(19) . . ?
C2 B9 B5 105.8(2) . . ?
B8 B9 B5 108.5(2) . . ?
B10 B9 B5 60.60(19) . . ?
C2 B9 B1 59.52(17) . . ?
B8 B9 B1 108.1(2) . . ?
B10 B9 B1 107.8(2) . . ?
B5 B9 B1 59.44(18) . . ?
B8 B10 B9 59.92(18) . . ?
B8 B10 B6 108.6(2) . . ?
B9 B10 B6 108.3(2) . . ?
B8 B10 B7 60.17(19) . . ?
B9 B10 B7 108.2(2) . . ?
B6 B10 B7 60.5(2) . . ?
B8 B10 B5 107.9(2) . . ?
B9 B10 B5 59.83(19) . . ?
B6 B10 B5 60.2(2) . . ?
B7 B10 B5 108.4(2) . . ?
N2 C1 B2 126.5(2) . . ?
N2 C1 B3 126.2(2) . . ?
B2 C1 B3 63.04(19) . . ?
N2 C1 C2 112.7(2) . . ?
B2 C1 C2 109.6(2) . . ?
B3 C1 C2 109.85(19) . . ?
N2 C1 B1 115.3(2) . . ?
B2 C1 B1 62.05(18) . . ?
B3 C1 B1 113.7(2) . . ?
C2 C1 B1 60.33(16) . . ?
N2 C1 B4 114.8(2) . . ?
B2 C1 B4 113.9(2) . . ?
B3 C1 B4 62.46(17) . . ?
C2 C1 B4 60.37(16) . . ?
B1 C1 B4 112.5(2) . . ?
N1 C2 B8 126.2(2) . . ?
N1 C2 B9 125.5(2) . . ?
B8 C2 B9 62.53(18) . . ?
N1 C2 C1 113.04(19) . . ?
B8 C2 C1 110.06(19) . . ?
B9 C2 C1 110.2(2) . . ?
N1 C2 B1 114.9(2) . . ?
B8 C2 B1 113.8(2) . . ?
B9 C2 B1 62.77(18) . . ?
C1 C2 B1 60.25(16) . . ?
N1 C2 B4 115.6(2) . . ?
B8 C2 B4 62.71(18) . . ?
B9 C2 B4 113.9(2) . . ?
C1 C2 B4 60.26(16) . . ?
B1 C2 B4 112.4(2) . . ?
C3 N1 C2 118.8(2) . . ?
C4 N2 C1 120.1(2) . . ?
N1 C3 C5 121.4(2) . . ?
N2 C4 C11 120.5(3) . . ?
C6 C5 C10 119.0(2) . . ?
C6 C5 C3 119.5(2) . . ?
C10 C5 C3 121.5(2) . . ?
C5 C6 C7 121.2(3) . . ?
C8 C7 C6 117.9(3) . . ?
C7 C8 C9 122.9(3) . . ?
C7 C8 Cl1 119.3(2) . . ?
C9 C8 Cl1 117.7(2) . . ?
C8 C9 C10 118.7(3) . . ?
C9 C10 C5 120.2(3) . . ?
C16 C11 C12 118.7(3) . . ?
C16 C11 C4 120.4(3) . . ?
C12 C11 C4 120.8(2) . . ?
C13 C12 C11 120.5(3) . . ?
C12 C13 C14 119.8(3) . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 Cl2 119.6(2) . . ?
C13 C14 Cl2 119.5(3) . . ?
C14 C15 C16 118.9(3) . . ?
C11 C16 C15 121.0(3) . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_compound3b
_database_code_depnum_ccdc_archive 'CCDC 1881764'
_audit_update_record             
;
2019-01-16 deposited with the CCDC.
2019-01-24 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            'C16 H24 B10 Cl2 N2'
_chemical_formula_weight         423.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.3966(11)
_cell_length_b                   11.6224(18)
_cell_length_c                   13.104(2)
_cell_angle_alpha                85.700(2)
_cell_angle_beta                 82.407(2)
_cell_angle_gamma                85.925(2)
_cell_volume                     1111.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4425
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            8385
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.571
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5046
_reflns_number_gt                4109
_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)+(0.0960P)²+0.4816P] 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         5046
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1736
_refine_ls_wR_factor_gt          0.1610
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.3973(3) 0.43644(19) 0.68516(18) 0.0418(5) Uani 1 1 d . . . . .
B2 B 0.4872(3) 0.5077(2) 0.7822(2) 0.0455(5) Uani 1 1 d . . . . .
B3 B 0.2946(3) 0.54403(19) 0.87329(18) 0.0423(5) Uani 1 1 d . . . . .
B4 B 0.0976(3) 0.49650(18) 0.82562(17) 0.0383(4) Uani 1 1 d . . . . .
B5 B 0.2539(4) 0.5392(2) 0.61805(19) 0.0458(5) Uani 1 1 d . . . . .
B6 B 0.4558(3) 0.5820(2) 0.6627(2) 0.0481(5) Uani 1 1 d . . . . .
B7 B 0.3886(4) 0.6504(2) 0.7802(2) 0.0480(5) Uani 1 1 d . . . . .
B8 B 0.1460(3) 0.64427(19) 0.81020(19) 0.0448(5) Uani 1 1 d . . . . .
B9 B 0.0638(3) 0.5805(2) 0.7085(2) 0.0452(5) Uani 1 1 d . . . . .
B10 B 0.2492(4) 0.6711(2) 0.6807(2) 0.0480(5) Uani 1 1 d . . . . .
C1 C 0.3104(2) 0.42134(15) 0.81175(15) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.1581(3) 0.44300(16) 0.70780(15) 0.0381(4) Uani 1 1 d . . . . .
N1 N 0.3208(3) 0.30810(14) 0.85449(14) 0.0443(4) Uani 1 1 d . . . . .
N2 N 0.0656(3) 0.34838(16) 0.69002(15) 0.0471(4) Uani 1 1 d . . . . .
C3 C 0.1401(4) 0.2647(3) 0.6159(2) 0.0759(9) Uani 1 1 d . . . . .
H3A H 0.2550 0.2294 0.6345 0.091 Uiso 1 1 calc R U . . .
H3B H 0.1633 0.3034 0.5477 0.091 Uiso 1 1 calc R U . . .
C4 C 0.0069(3) 0.1731(2) 0.61476(17) 0.0519(5) Uani 1 1 d . . . . .
C5 C -0.1691(4) 0.2000(2) 0.59258(19) 0.0566(6) Uani 1 1 d . . . . .
H13 H -0.2067 0.2767 0.5775 0.068 Uiso 1 1 calc R U . . .
C6 C -0.2901(4) 0.1152(2) 0.59243(19) 0.0571(6) Uani 1 1 d . . . . .
H14 H -0.4083 0.1343 0.5772 0.069 Uiso 1 1 calc R U . . .
C7 C -0.2341(4) 0.0027(2) 0.61493(17) 0.0526(5) Uani 1 1 d . . . . .
C8 C -0.0610(4) -0.0277(2) 0.63763(19) 0.0596(6) Uani 1 1 d . . . . .
H15 H -0.0250 -0.1047 0.6529 0.071 Uiso 1 1 calc R U . . .
C9 C 0.0593(3) 0.0578(2) 0.63757(19) 0.0586(6) Uani 1 1 d . . . . .
H16 H 0.1772 0.0380 0.6530 0.070 Uiso 1 1 calc R U . . .
C10 C 0.2552(3) 0.28135(17) 0.96324(16) 0.0463(5) Uani 1 1 d . . . . .
H10A H 0.1325 0.3160 0.9792 0.056 Uiso 1 1 calc R U . . .
H10B H 0.3335 0.3140 1.0059 0.056 Uiso 1 1 calc R U . . .
C11 C 0.2545(3) 0.15243(16) 0.98721(15) 0.0388(4) Uani 1 1 d . . . . .
C12 C 0.2192(3) 0.07785(18) 0.91524(16) 0.0451(5) Uani 1 1 d . . . . .
H17 H 0.1974 0.1076 0.8498 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2158(3) -0.04033(18) 0.93932(16) 0.0455(5) Uani 1 1 d . . . . .
H18 H 0.1927 -0.0899 0.8907 0.055 Uiso 1 1 calc R U . . .
C14 C 0.2475(3) -0.08282(16) 1.03694(16) 0.0401(4) Uani 1 1 d . . . . .
C15 C 0.2826(3) -0.01128(19) 1.10928(16) 0.0469(5) Uani 1 1 d . . . . .
H19 H 0.3039 -0.0414 1.1747 0.056 Uiso 1 1 calc R U . . .
C16 C 0.2861(3) 0.10638(18) 1.08419(16) 0.0455(5) Uani 1 1 d . . . . .
H20 H 0.3101 0.1552 1.1332 0.055 Uiso 1 1 calc R U . . .
Cl1 Cl 0.24276(8) -0.23156(4) 1.06948(5) 0.05771(19) Uani 1 1 d . . . . .
Cl2 Cl -0.38931(14) -0.10398(8) 0.61709(7) 0.0945(3) Uani 1 1 d . . . . .
H1 H 0.469(3) 0.364(2) 0.6539(18) 0.050(6) Uiso 1 1 d . . . . .
H2 H 0.621(4) 0.470(2) 0.800(2) 0.065(8) Uiso 1 1 d . . . . .
H3 H 0.304(3) 0.538(2) 0.952(2) 0.055(7) Uiso 1 1 d . . . . .
H4 H -0.010(3) 0.461(2) 0.8754(19) 0.052(6) Uiso 1 1 d . . . . .
H5 H 0.241(3) 0.523(2) 0.544(2) 0.055(7) Uiso 1 1 d . . . . .
H6 H 0.568(4) 0.606(2) 0.610(2) 0.062(7) Uiso 1 1 d . . . . .
H7 H 0.459(4) 0.715(2) 0.803(2) 0.065(8) Uiso 1 1 d . . . . .
H8 H 0.056(3) 0.714(2) 0.8525(18) 0.050(6) Uiso 1 1 d . . . . .
H9 H -0.070(3) 0.593(2) 0.6851(19) 0.051(6) Uiso 1 1 d . . . . .
H10 H 0.232(4) 0.750(2) 0.637(2) 0.064(8) Uiso 1 1 d . . . . .
H11 H 0.425(4) 0.275(2) 0.835(2) 0.051(7) Uiso 1 1 d . . . . .
H12 H -0.006(4) 0.321(2) 0.742(2) 0.058(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C1 1.699(3) . ?
B1 C2 1.752(3) . ?
B1 B6 1.770(3) . ?
B1 B2 1.790(4) . ?
B1 B5 1.798(4) . ?
B2 C1 1.692(3) . ?
B2 B7 1.763(4) . ?
B2 B6 1.765(4) . ?
B2 B3 1.781(3) . ?
B3 C1 1.680(3) . ?
B3 B8 1.778(4) . ?
B3 B7 1.780(3) . ?
B3 B4 1.796(3) . ?
B4 C2 1.701(3) . ?
B4 C1 1.740(3) . ?
B4 B8 1.771(3) . ?
B4 B9 1.792(3) . ?
B5 C2 1.683(3) . ?
B5 B9 1.778(3) . ?
B5 B10 1.788(3) . ?
B5 B6 1.789(4) . ?
B6 B7 1.781(4) . ?
B6 B10 1.783(4) . ?
B7 B10 1.759(4) . ?
B7 B8 1.791(4) . ?
B8 B9 1.767(4) . ?
B8 B10 1.781(3) . ?
B9 C2 1.698(3) . ?
B9 B10 1.771(4) . ?
C1 N1 1.392(2) . ?
C1 C2 1.871(3) . ?
C2 N2 1.385(2) . ?
N1 C10 1.461(3) . ?
N2 C3 1.455(3) . ?
C3 C4 1.503(3) . ?
C4 C5 1.380(4) . ?
C4 C9 1.390(3) . ?
C5 C6 1.378(3) . ?
C6 C7 1.366(3) . ?
C7 C8 1.368(4) . ?
C7 Cl2 1.745(2) . ?
C8 C9 1.380(4) . ?
C10 C11 1.508(3) . ?
C11 C16 1.384(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.368(3) . ?
C14 Cl1 1.751(2) . ?
C15 C16 1.384(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 B1 C2 65.66(12) . . ?
C1 B1 B6 105.65(16) . . ?
C2 B1 B6 105.19(15) . . ?
C1 B1 B2 57.93(12) . . ?
C2 B1 B2 110.19(15) . . ?
B6 B1 B2 59.46(14) . . ?
C1 B1 B5 109.62(15) . . ?
C2 B1 B5 56.56(12) . . ?
B6 B1 B5 60.17(14) . . ?
B2 B1 B5 108.79(16) . . ?
C1 B2 B7 105.65(16) . . ?
C1 B2 B6 106.14(17) . . ?
B7 B2 B6 60.63(14) . . ?
C1 B2 B3 57.77(12) . . ?
B7 B2 B3 60.30(14) . . ?
B6 B2 B3 108.17(17) . . ?
C1 B2 B1 58.32(12) . . ?
B7 B2 B1 106.96(18) . . ?
B6 B2 B1 59.68(14) . . ?
B3 B2 B1 105.19(15) . . ?
C1 B3 B8 107.13(16) . . ?
C1 B3 B7 105.41(16) . . ?
B8 B3 B7 60.42(14) . . ?
C1 B3 B2 58.43(12) . . ?
B8 B3 B2 108.04(17) . . ?
B7 B3 B2 59.35(14) . . ?
C1 B3 B4 59.96(12) . . ?
B8 B3 B4 59.38(13) . . ?
B7 B3 B4 106.70(17) . . ?
B2 B3 B4 106.86(16) . . ?
C2 B4 C1 65.89(12) . . ?
C2 B4 B8 106.03(15) . . ?
C1 B4 B8 104.88(15) . . ?
C2 B4 B9 58.09(12) . . ?
C1 B4 B9 110.04(15) . . ?
B8 B4 B9 59.45(13) . . ?
C2 B4 B3 110.23(15) . . ?
C1 B4 B3 56.70(12) . . ?
B8 B4 B3 59.81(13) . . ?
B9 B4 B3 108.59(16) . . ?
C2 B5 B9 58.67(13) . . ?
C2 B5 B10 105.70(16) . . ?
B9 B5 B10 59.57(14) . . ?
C2 B5 B6 107.34(17) . . ?
B9 B5 B6 107.87(17) . . ?
B10 B5 B6 59.80(14) . . ?
C2 B5 B1 60.33(12) . . ?
B9 B5 B1 107.06(16) . . ?
B10 B5 B1 106.05(18) . . ?
B6 B5 B1 59.11(14) . . ?
B2 B6 B1 60.86(14) . . ?
B2 B6 B7 59.63(15) . . ?
B1 B6 B7 107.09(16) . . ?
B2 B6 B10 108.01(17) . . ?
B1 B6 B10 107.50(16) . . ?
B7 B6 B10 59.15(15) . . ?
B2 B6 B5 110.36(16) . . ?
B1 B6 B5 60.72(14) . . ?
B7 B6 B5 107.88(17) . . ?
B10 B6 B5 60.07(14) . . ?
B10 B7 B2 109.16(17) . . ?
B10 B7 B3 108.54(17) . . ?
B2 B7 B3 60.35(13) . . ?
B10 B7 B6 60.47(15) . . ?
B2 B7 B6 59.74(14) . . ?
B3 B7 B6 107.51(16) . . ?
B10 B7 B8 60.21(15) . . ?
B2 B7 B8 108.29(15) . . ?
B3 B7 B8 59.73(13) . . ?
B6 B7 B8 107.63(17) . . ?
B9 B8 B4 60.88(13) . . ?
B9 B8 B3 110.56(16) . . ?
B4 B8 B3 60.81(13) . . ?
B9 B8 B10 59.90(14) . . ?
B4 B8 B10 107.12(16) . . ?
B3 B8 B10 107.67(17) . . ?
B9 B8 B7 108.18(17) . . ?
B4 B8 B7 107.36(16) . . ?
B3 B8 B7 59.84(14) . . ?
B10 B8 B7 59.02(15) . . ?
C2 B9 B8 106.34(16) . . ?
C2 B9 B10 105.79(16) . . ?
B8 B9 B10 60.45(14) . . ?
C2 B9 B5 57.86(12) . . ?
B8 B9 B5 108.33(18) . . ?
B10 B9 B5 60.49(14) . . ?
C2 B9 B4 58.26(12) . . ?
B8 B9 B4 59.67(13) . . ?
B10 B9 B4 106.60(17) . . ?
B5 B9 B4 105.07(16) . . ?
B7 B10 B9 109.40(17) . . ?
B7 B10 B8 60.77(14) . . ?
B9 B10 B8 59.65(14) . . ?
B7 B10 B6 60.38(15) . . ?
B9 B10 B6 108.43(16) . . ?
B8 B10 B6 107.99(17) . . ?
B7 B10 B5 108.91(17) . . ?
B9 B10 B5 59.94(14) . . ?
B8 B10 B5 107.28(16) . . ?
B6 B10 B5 60.13(14) . . ?
N1 C1 B3 127.88(17) . . ?
N1 C1 B2 125.90(17) . . ?
B3 C1 B2 63.79(13) . . ?
N1 C1 B1 114.16(16) . . ?
B3 C1 B1 114.24(15) . . ?
B2 C1 B1 63.74(14) . . ?
N1 C1 B4 117.34(15) . . ?
B3 C1 B4 63.34(13) . . ?
B2 C1 B4 113.71(15) . . ?
B1 C1 B4 107.43(15) . . ?
N1 C1 C2 113.19(15) . . ?
B3 C1 C2 107.66(14) . . ?
B2 C1 C2 109.14(14) . . ?
B1 C1 C2 58.54(12) . . ?
B4 C1 C2 56.05(11) . . ?
N2 C2 B5 126.56(18) . . ?
N2 C2 B9 123.94(18) . . ?
B5 C2 B9 63.47(14) . . ?
N2 C2 B4 115.02(16) . . ?
B5 C2 B4 113.76(15) . . ?
B9 C2 B4 63.65(13) . . ?
N2 C2 B1 119.47(16) . . ?
B5 C2 B1 63.11(14) . . ?
B9 C2 B1 112.96(15) . . ?
B4 C2 B1 106.79(15) . . ?
N2 C2 C1 116.41(16) . . ?
B5 C2 C1 106.98(14) . . ?
B9 C2 C1 108.27(14) . . ?
B4 C2 C1 58.06(11) . . ?
B1 C2 C1 55.81(11) . . ?
C1 N1 C10 120.70(17) . . ?
C2 N2 C3 122.76(19) . . ?
N2 C3 C4 109.7(2) . . ?
C5 C4 C9 118.2(2) . . ?
C5 C4 C3 121.8(2) . . ?
C9 C4 C3 119.9(3) . . ?
C6 C5 C4 121.2(2) . . ?
C7 C6 C5 119.1(2) . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 Cl2 118.9(2) . . ?
C8 C7 Cl2 119.53(19) . . ?
C7 C8 C9 118.9(2) . . ?
C8 C9 C4 120.9(2) . . ?
N1 C10 C11 110.71(17) . . ?
C16 C11 C12 118.53(18) . . ?
C16 C11 C10 119.53(18) . . ?
C12 C11 C10 121.93(18) . . ?
C13 C12 C11 121.11(19) . . ?
C14 C13 C12 118.60(19) . . ?
C15 C14 C13 121.48(18) . . ?
C15 C14 Cl1 119.03(16) . . ?
C13 C14 Cl1 119.48(16) . . ?
C14 C15 C16 119.35(19) . . ?
C15 C16 C11 120.92(19) . . ?

_refine_diff_density_max         1.071
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_compound2c
_database_code_depnum_ccdc_archive 'CCDC 1881762'
_audit_update_record             
;
2019-01-16 deposited with the CCDC.
2019-01-24 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            'C18 H26 B10 N2'
_chemical_formula_weight         378.51

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

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

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

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

_cell_length_a                   7.4532(17)
_cell_length_b                   13.427(3)
_cell_length_c                   22.271(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.261(6)
_cell_angle_gamma                90
_cell_volume                     2227.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2762
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6227
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            14217
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.771
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5087
_reflns_number_gt                2985
_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)+(0.0618P)²+0.2553P] 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         5087
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 1.0173(2) 0.12297(12) 0.17507(7) 0.0446(4) Uani 1 1 d . . . . .
C2 C 0.8484(2) 0.21047(12) 0.17669(7) 0.0440(4) Uani 1 1 d . . . . .
N1 N 1.14389(18) 0.12500(11) 0.12942(6) 0.0493(4) Uani 1 1 d . . . . .
B11 B 0.6664(3) 0.16180(16) 0.21049(10) 0.0522(5) Uani 1 1 d . . . . .
B3 B 1.0362(3) 0.22255(17) 0.22464(9) 0.0523(5) Uani 1 1 d . . . . .
B7 B 0.8159(3) 0.24543(17) 0.24908(9) 0.0554(5) Uani 1 1 d . . . . .
B4 B 1.0971(3) 0.10000(18) 0.24642(10) 0.0569(6) Uani 1 1 d . . . . .
B10 B 0.7294(3) 0.03875(17) 0.23144(10) 0.0572(6) Uani 1 1 d . . . . .
B6 B 0.7959(3) 0.08720(15) 0.16254(10) 0.0472(5) Uani 1 1 d . . . . .
B8 B 0.9687(3) 0.17509(19) 0.29400(10) 0.0611(6) Uani 1 1 d . . . . .
B5 B 0.9488(3) 0.01605(17) 0.20748(10) 0.0548(5) Uani 1 1 d . . . . .
B12 B 0.7419(3) 0.13607(18) 0.28526(10) 0.0592(6) Uani 1 1 d . . . . .
B9 B 0.9158(3) 0.04678(19) 0.28329(10) 0.0622(6) Uani 1 1 d . . . . .
C4 C 1.2259(2) 0.12731(12) 0.02715(7) 0.0464(4) Uani 1 1 d . . . . .
C11 C 0.7743(2) 0.35706(12) 0.12580(8) 0.0470(4) Uani 1 1 d . . . . .
H14 H 0.7320 0.3809 0.1618 0.056 Uiso 1 1 calc R U . . .
C3 C 1.0949(2) 0.12412(13) 0.07419(8) 0.0495(4) Uani 1 1 d . . . . .
H13 H 0.9731 0.1214 0.0635 0.059 Uiso 1 1 calc R U . . .
C17 C 0.8077(2) 0.38700(13) 0.01663(8) 0.0487(4) Uani 1 1 d . . . . .
H19 H 0.8479 0.3219 0.0122 0.058 Uiso 1 1 calc R U . . .
C12 C 0.7627(2) 0.42110(12) 0.07289(8) 0.0433(4) Uani 1 1 d . . . . .
C15 C 0.7333(2) 0.54611(13) -0.02779(8) 0.0472(4) Uani 1 1 d . . . . .
C14 C 0.6907(2) 0.58033(13) 0.02832(9) 0.0546(5) Uani 1 1 d . . . . .
H21 H 0.6527 0.6458 0.0328 0.066 Uiso 1 1 calc R U . . .
C5 C 1.1693(3) 0.13339(14) -0.03270(8) 0.0588(5) Uani 1 1 d . . . . .
H18 H 1.0472 0.1336 -0.0430 0.071 Uiso 1 1 calc R U . . .
C13 C 0.7038(2) 0.51859(13) 0.07807(8) 0.0535(5) Uani 1 1 d . . . . .
H22 H 0.6727 0.5427 0.1154 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7933(2) 0.44869(13) -0.03248(8) 0.0521(4) Uani 1 1 d . . . . .
H20 H 0.8246 0.4246 -0.0698 0.063 Uiso 1 1 calc R U . . .
C9 C 1.4090(2) 0.12740(14) 0.04085(8) 0.0566(5) Uani 1 1 d . . . . .
H15 H 1.4503 0.1243 0.0808 0.068 Uiso 1 1 calc R U . . .
C6 C 1.2927(3) 0.13916(14) -0.07729(8) 0.0607(5) Uani 1 1 d . . . . .
H17 H 1.2520 0.1444 -0.1172 0.073 Uiso 1 1 calc R U . . .
C7 C 1.4743(3) 0.13733(14) -0.06392(9) 0.0583(5) Uani 1 1 d . . . . .
C8 C 1.5298(3) 0.13197(16) -0.00391(9) 0.0649(5) Uani 1 1 d . . . . .
H16 H 1.6520 0.1315 0.0063 0.078 Uiso 1 1 calc R U . . .
C18 C 0.7181(3) 0.61266(14) -0.08200(9) 0.0631(5) Uani 1 1 d . . . . .
H18A H 0.8336 0.6405 -0.0896 0.095 Uiso 1 1 calc R U . . .
H18B H 0.6346 0.6654 -0.0748 0.095 Uiso 1 1 calc R U . . .
H18C H 0.6763 0.5746 -0.1162 0.095 Uiso 1 1 calc R U . . .
C10 C 1.6083(3) 0.13985(19) -0.11283(10) 0.0909(8) Uani 1 1 d . . . . .
H10A H 1.6509 0.0736 -0.1200 0.136 Uiso 1 1 calc R U . . .
H10B H 1.7075 0.1817 -0.1006 0.136 Uiso 1 1 calc R U . . .
H10C H 1.5517 0.1658 -0.1490 0.136 Uiso 1 1 calc R U . . .
N2 N 0.83978(18) 0.27053(10) 0.12438(6) 0.0478(4) Uani 1 1 d . . . . .
H6 H 0.754(2) 0.0658(12) 0.1169(7) 0.048(4) Uiso 1 1 d . . . . .
H11 H 0.535(2) 0.1906(13) 0.1926(8) 0.064(5) Uiso 1 1 d . . . . .
H7 H 0.780(2) 0.3229(13) 0.2571(7) 0.049(5) Uiso 1 1 d . . . . .
H12 H 0.647(2) 0.1410(13) 0.3215(8) 0.061(5) Uiso 1 1 d . . . . .
H4 H 1.236(2) 0.0833(13) 0.2512(8) 0.064(5) Uiso 1 1 d . . . . .
H5 H 0.998(2) -0.0532(15) 0.1886(8) 0.067(5) Uiso 1 1 d . . . . .
H8 H 1.027(2) 0.2074(13) 0.3358(8) 0.062(5) Uiso 1 1 d . . . . .
H10 H 0.632(2) -0.0235(14) 0.2314(8) 0.071(6) Uiso 1 1 d . . . . .
H9 H 0.936(2) -0.0104(14) 0.3184(8) 0.068(5) Uiso 1 1 d . . . . .
H3 H 1.130(2) 0.2847(13) 0.2137(8) 0.061(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.414(2) . ?
C1 B5 1.695(3) . ?
C1 B4 1.703(3) . ?
C1 C2 1.723(2) . ?
C1 B6 1.730(3) . ?
C1 B3 1.736(3) . ?
C2 N2 1.416(2) . ?
C2 B7 1.706(3) . ?
C2 B11 1.707(3) . ?
C2 B6 1.727(3) . ?
C2 B3 1.734(3) . ?
N1 C3 1.269(2) . ?
B11 B12 1.771(3) . ?
B11 B10 1.775(3) . ?
B11 B6 1.777(3) . ?
B11 B7 1.779(3) . ?
B3 B8 1.763(3) . ?
B3 B4 1.770(3) . ?
B3 B7 1.777(3) . ?
B7 B8 1.761(3) . ?
B7 B12 1.773(3) . ?
B4 B9 1.760(3) . ?
B4 B8 1.770(4) . ?
B4 B5 1.780(3) . ?
B10 B6 1.756(3) . ?
B10 B5 1.767(3) . ?
B10 B12 1.773(3) . ?
B10 B9 1.775(3) . ?
B6 B5 1.767(3) . ?
B8 B12 1.773(3) . ?
B8 B9 1.781(4) . ?
B5 B9 1.765(3) . ?
B12 B9 1.768(4) . ?
C4 C5 1.385(2) . ?
C4 C9 1.387(2) . ?
C4 C3 1.461(2) . ?
C11 N2 1.261(2) . ?
C11 C12 1.459(2) . ?
C17 C16 1.373(2) . ?
C17 C12 1.387(2) . ?
C12 C13 1.387(2) . ?
C15 C14 1.380(2) . ?
C15 C16 1.388(2) . ?
C15 C18 1.503(2) . ?
C14 C13 1.384(2) . ?
C5 C6 1.382(3) . ?
C9 C8 1.371(3) . ?
C6 C7 1.375(3) . ?
C7 C8 1.385(3) . ?
C7 C10 1.507(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 B5 122.90(15) . . ?
N1 C1 B4 117.12(15) . . ?
B5 C1 B4 63.19(12) . . ?
N1 C1 C2 120.69(13) . . ?
B5 C1 C2 109.65(13) . . ?
B4 C1 C2 109.42(14) . . ?
N1 C1 B6 123.26(14) . . ?
B5 C1 B6 62.11(12) . . ?
B4 C1 B6 113.33(14) . . ?
C2 C1 B6 60.01(10) . . ?
N1 C1 B3 113.73(14) . . ?
B5 C1 B3 113.57(14) . . ?
B4 C1 B3 61.93(12) . . ?
C2 C1 B3 60.18(10) . . ?
B6 C1 B3 111.68(13) . . ?
N2 C2 B7 128.11(15) . . ?
N2 C2 B11 124.71(15) . . ?
B7 C2 B11 62.83(12) . . ?
N2 C2 C1 112.38(12) . . ?
B7 C2 C1 109.80(13) . . ?
B11 C2 C1 109.99(13) . . ?
N2 C2 B6 113.14(13) . . ?
B7 C2 B6 113.36(14) . . ?
B11 C2 B6 62.30(12) . . ?
C1 C2 B6 60.21(10) . . ?
N2 C2 B3 117.57(14) . . ?
B7 C2 B3 62.21(12) . . ?
B11 C2 B3 113.60(14) . . ?
C1 C2 B3 60.29(11) . . ?
B6 C2 B3 111.94(13) . . ?
C3 N1 C1 121.45(15) . . ?
C2 B11 B12 105.12(15) . . ?
C2 B11 B10 105.41(15) . . ?
B12 B11 B10 60.02(13) . . ?
C2 B11 B6 59.39(11) . . ?
B12 B11 B6 107.18(16) . . ?
B10 B11 B6 59.27(12) . . ?
C2 B11 B7 58.54(11) . . ?
B12 B11 B7 59.94(13) . . ?
B10 B11 B7 107.85(16) . . ?
B6 B11 B7 107.56(15) . . ?
C2 B3 C1 59.54(10) . . ?
C2 B3 B8 104.75(15) . . ?
C1 B3 B8 105.07(15) . . ?
C2 B3 B4 105.89(14) . . ?
C1 B3 B4 58.11(11) . . ?
B8 B3 B4 60.16(13) . . ?
C2 B3 B7 58.11(11) . . ?
C1 B3 B7 105.96(14) . . ?
B8 B3 B7 59.66(13) . . ?
B4 B3 B7 107.87(16) . . ?
C2 B7 B8 106.03(15) . . ?
C2 B7 B12 105.07(15) . . ?
B8 B7 B12 60.23(13) . . ?
C2 B7 B3 59.68(11) . . ?
B8 B7 B3 59.75(13) . . ?
B12 B7 B3 107.68(17) . . ?
C2 B7 B11 58.63(11) . . ?
B8 B7 B11 108.34(17) . . ?
B12 B7 B11 59.79(13) . . ?
B3 B7 B11 108.14(15) . . ?
C1 B4 B9 105.23(15) . . ?
C1 B4 B3 59.96(11) . . ?
B9 B4 B3 108.20(17) . . ?
C1 B4 B8 106.16(16) . . ?
B9 B4 B8 60.60(14) . . ?
B3 B4 B8 59.72(13) . . ?
C1 B4 B5 58.18(11) . . ?
B9 B4 B5 59.79(13) . . ?
B3 B4 B5 107.93(15) . . ?
B8 B4 B5 108.20(17) . . ?
B6 B10 B5 60.22(12) . . ?
B6 B10 B12 107.97(15) . . ?
B5 B10 B12 107.86(16) . . ?
B6 B10 B9 107.77(15) . . ?
B5 B10 B9 59.77(13) . . ?
B12 B10 B9 59.76(14) . . ?
B6 B10 B11 60.41(12) . . ?
B5 B10 B11 108.63(15) . . ?
B12 B10 B11 59.87(13) . . ?
B9 B10 B11 107.85(16) . . ?
C2 B6 C1 59.78(10) . . ?
C2 B6 B10 105.40(14) . . ?
C1 B6 B10 105.21(14) . . ?
C2 B6 B5 106.16(14) . . ?
C1 B6 B5 57.95(11) . . ?
B10 B6 B5 60.19(13) . . ?
C2 B6 B11 58.31(11) . . ?
C1 B6 B11 106.48(14) . . ?
B10 B6 B11 60.32(12) . . ?
B5 B6 B11 108.53(15) . . ?
B7 B8 B3 60.58(12) . . ?
B7 B8 B4 108.56(15) . . ?
B3 B8 B4 60.11(13) . . ?
B7 B8 B12 60.23(13) . . ?
B3 B8 B12 108.33(16) . . ?
B4 B8 B12 107.54(17) . . ?
B7 B8 B9 107.93(16) . . ?
B3 B8 B9 107.56(16) . . ?
B4 B8 B9 59.41(14) . . ?
B12 B8 B9 59.64(13) . . ?
C1 B5 B9 105.37(16) . . ?
C1 B5 B10 106.29(15) . . ?
B9 B5 B10 60.34(13) . . ?
C1 B5 B6 59.94(11) . . ?
B9 B5 B6 107.73(16) . . ?
B10 B5 B6 59.59(12) . . ?
C1 B5 B4 58.62(11) . . ?
B9 B5 B4 59.54(13) . . ?
B10 B5 B4 107.94(17) . . ?
B6 B5 B4 107.92(16) . . ?
B9 B12 B11 108.36(16) . . ?
B9 B12 B10 60.16(13) . . ?
B11 B12 B10 60.11(13) . . ?
B9 B12 B7 107.99(16) . . ?
B11 B12 B7 60.26(12) . . ?
B10 B12 B7 108.18(15) . . ?
B9 B12 B8 60.40(14) . . ?
B11 B12 B8 108.16(15) . . ?
B10 B12 B8 108.44(17) . . ?
B7 B12 B8 59.54(13) . . ?
B4 B9 B5 60.67(13) . . ?
B4 B9 B12 108.27(16) . . ?
B5 B9 B12 108.20(16) . . ?
B4 B9 B10 108.47(16) . . ?
B5 B9 B10 59.89(13) . . ?
B12 B9 B10 60.08(13) . . ?
B4 B9 B8 59.99(13) . . ?
B5 B9 B8 108.41(16) . . ?
B12 B9 B8 59.96(14) . . ?
B10 B9 B8 108.03(17) . . ?
C5 C4 C9 118.13(16) . . ?
C5 C4 C3 120.35(16) . . ?
C9 C4 C3 121.49(16) . . ?
N2 C11 C12 122.25(16) . . ?
N1 C3 C4 121.31(16) . . ?
C16 C17 C12 120.41(16) . . ?
C13 C12 C17 118.37(16) . . ?
C13 C12 C11 119.88(16) . . ?
C17 C12 C11 121.75(15) . . ?
C14 C15 C16 117.93(16) . . ?
C14 C15 C18 121.11(16) . . ?
C16 C15 C18 120.95(17) . . ?
C15 C14 C13 120.92(17) . . ?
C6 C5 C4 120.61(18) . . ?
C14 C13 C12 120.75(17) . . ?
C17 C16 C15 121.60(17) . . ?
C8 C9 C4 120.60(18) . . ?
C7 C6 C5 121.38(18) . . ?
C6 C7 C8 117.63(17) . . ?
C6 C7 C10 121.2(2) . . ?
C8 C7 C10 121.2(2) . . ?
C9 C8 C7 121.63(19) . . ?
C11 N2 C2 120.61(15) . . ?

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_compound3a
_database_code_depnum_ccdc_archive 'CCDC 1881763'
_audit_update_record             
;
2019-01-16 deposited with the CCDC.
2019-01-24 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            'C12 H34 B10 N2'
_chemical_formula_weight         314.51

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   11.268(8)
_cell_length_b                   19.419(14)
_cell_length_c                   39.46(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8635(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    991
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.968
_exptl_crystal_F_000             2720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.049
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6177
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            15542
_diffrn_reflns_av_unetI/netI     0.1305
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.064
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4916
_reflns_number_gt                1484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.990

_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)+(0.0670P)²+0.1000P] 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_abs_structure_details 
; 
 Flack x determined using 490 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4916
_refine_ls_number_parameters     242
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.2822
_refine_ls_R_factor_gt           0.0960
_refine_ls_wR_factor_ref         0.2295
_refine_ls_wR_factor_gt          0.1791
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.194
_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 0.3535(6) 0.0103(4) 0.3358(2) 0.089(2) Uani 1 1 d . . . . .
H1 H 0.2564 0.0160 0.3363 0.107 Uiso 1 1 calc R U . . .
B2 B 0.4500(7) 0.0801(5) 0.3358(3) 0.105(3) Uani 1 1 d . . . . .
H2 H 0.4178 0.1336 0.3364 0.126 Uiso 1 1 calc R U . . .
B3 B 0.5778(7) 0.0556(4) 0.3126(2) 0.088(3) Uani 1 1 d . . . . .
H3 H 0.6277 0.0911 0.2962 0.105 Uiso 1 1 calc R U . . .
B4 B 0.5800(8) 0.0574(5) 0.3558(2) 0.103(3) Uani 1 1 d . . . . .
H4 H 0.6337 0.0961 0.3692 0.123 Uiso 1 1 calc R U . . .
B5 B 0.4384(8) 0.0288(5) 0.3711(2) 0.117(3) Uani 1 1 d . . . . .
H5 H 0.3992 0.0474 0.3950 0.140 Uiso 1 1 calc R U . . .
B6 B -0.0645(8) 0.0776(5) 0.4598(2) 0.103(3) Uani 1 1 d . . . . .
H6 H -0.1094 0.1279 0.4597 0.123 Uiso 1 1 calc R U . . .
B7 B 0.0901(8) 0.0667(6) 0.4608(3) 0.120(4) Uani 1 1 d . . . . .
H7 H 0.1521 0.1104 0.4619 0.145 Uiso 1 1 calc R U . . .
B8 B 0.1210(8) -0.0072(5) 0.4371(3) 0.104(3) Uani 1 1 d . . . . .
H8 H 0.2000 -0.0117 0.4208 0.124 Uiso 1 1 calc R U . . .
B9 B 0.1199(10) -0.0085(7) 0.4804(3) 0.132(4) Uani 1 1 d . . . . .
H9 H 0.2034 -0.0145 0.4945 0.159 Uiso 1 1 calc R U . . .
B10 B 0.0076(10) 0.0457(6) 0.4951(3) 0.135(4) Uani 1 1 d . . . . .
H10 H 0.0125 0.0757 0.5187 0.162 Uiso 1 1 calc R U . . .
N1 N 0.4020(6) 0.0559(4) 0.27081(18) 0.129(2) Uani 1 1 d D . . . .
H1A H 0.4488 0.0841 0.2606 0.155 Uiso 1 1 calc DR U . . .
C1 C 0.4358(6) 0.0310(4) 0.30263(19) 0.080(2) Uani 1 1 d . . . . .
C2 C 0.2965(9) 0.0375(5) 0.2548(3) 0.152(4) Uani 1 1 d . . . . .
H2A H 0.2329 0.0393 0.2713 0.182 Uiso 1 1 calc R U . . .
H2B H 0.3033 -0.0099 0.2472 0.182 Uiso 1 1 calc R U . . .
C3 C 0.2609(7) 0.0820(4) 0.22423(19) 0.098(2) Uani 1 1 d . U . . .
C4 C 0.1466(8) 0.0493(6) 0.2114(3) 0.173(4) Uani 1 1 d . . . . .
H4A H 0.0835 0.0586 0.2271 0.260 Uiso 1 1 calc R U . . .
H4B H 0.1573 0.0004 0.2094 0.260 Uiso 1 1 calc R U . . .
H4C H 0.1268 0.0682 0.1897 0.260 Uiso 1 1 calc R U . . .
C5 C 0.3584(9) 0.0687(8) 0.1980(3) 0.200(6) Uani 1 1 d . . . . .
H5A H 0.3705 0.1094 0.1846 0.301 Uiso 1 1 calc R U . . .
H5B H 0.3349 0.0314 0.1834 0.301 Uiso 1 1 calc R U . . .
H5C H 0.4309 0.0568 0.2093 0.301 Uiso 1 1 calc R U . . .
C6 C 0.2478(11) 0.1529(5) 0.2308(4) 0.218(6) Uani 1 1 d . U . . .
H6A H 0.2426 0.1603 0.2548 0.327 Uiso 1 1 calc R U . . .
H6B H 0.1768 0.1695 0.2201 0.327 Uiso 1 1 calc R U . . .
H6C H 0.3151 0.1774 0.2220 0.327 Uiso 1 1 calc R U . . .
C7 C 0.0121(7) 0.0472(3) 0.42665(19) 0.086(2) Uani 1 1 d . . . . .
C9 C -0.0041(7) 0.1604(4) 0.34964(19) 0.102(2) Uani 1 1 d D U . . .
C10 C -0.0244(9) 0.1031(5) 0.3223(3) 0.180(4) Uani 1 1 d D U . . .
H10A H -0.0758 0.1204 0.3049 0.269 Uiso 1 1 calc R U . . .
H10B H -0.0603 0.0636 0.3327 0.269 Uiso 1 1 calc R U . . .
H10C H 0.0504 0.0902 0.3126 0.269 Uiso 1 1 calc R U . . .
C12 C 0.1126(9) 0.1902(5) 0.3433(4) 0.216(6) Uani 1 1 d D U . . .
H12A H 0.1182 0.2340 0.3545 0.324 Uiso 1 1 calc R U . . .
H12B H 0.1236 0.1963 0.3194 0.324 Uiso 1 1 calc R U . . .
H12C H 0.1728 0.1599 0.3519 0.324 Uiso 1 1 calc R U . . .
C11 C -0.1036(8) 0.2107(5) 0.3447(3) 0.161(4) Uani 1 1 d D U . . .
H11A H -0.0884 0.2381 0.3249 0.242 Uiso 1 1 calc R U . . .
H11B H -0.1092 0.2401 0.3642 0.242 Uiso 1 1 calc R U . . .
H11C H -0.1768 0.1861 0.3419 0.242 Uiso 1 1 calc R U . . .
N2 N 0.0422(12) 0.0776(5) 0.3974(3) 0.097(4) Uani 0.685(15) 1 d D . P A 1
H2C H 0.1064 0.0671 0.3868 0.116 Uiso 0.685(15) 1 calc DR U P A 1
C8 C -0.0387(13) 0.1290(9) 0.3845(3) 0.114(4) Uani 0.685(15) 1 d D U P A 1
H8A H -0.0442 0.1660 0.4009 0.137 Uiso 0.685(15) 1 calc R U P A 1
H8B H -0.1168 0.1084 0.3825 0.137 Uiso 0.685(15) 1 calc R U P A 1
N2' N -0.046(2) 0.0772(12) 0.3921(6) 0.089(8) Uani 0.315(15) 1 d D . P A 2
H2' H -0.1184 0.0732 0.3855 0.106 Uiso 0.315(15) 1 calc DR U P A 2
C8' C 0.049(2) 0.1118(13) 0.3750(6) 0.107(6) Uani 0.315(15) 1 d D U P A 2
H8'1 H 0.0992 0.0786 0.3637 0.128 Uiso 0.315(15) 1 calc R U P A 2
H8'2 H 0.0966 0.1371 0.3912 0.128 Uiso 0.315(15) 1 calc R U P A 2


_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 C1 1.654(11) . ?
B1 B4 1.706(12) 2_655 ?
B1 B5 1.728(11) . ?
B1 B2 1.738(12) . ?
B1 B3 1.753(10) 2_655 ?
B2 C1 1.629(11) . ?
B2 B5 1.717(14) . ?
B2 B4 1.722(13) . ?
B2 B3 1.773(11) . ?
B3 B4 1.708(11) . ?
B3 C1 1.716(10) . ?
B3 C1 1.732(10) 2_655 ?
B3 B1 1.753(10) 2_655 ?
B4 B1 1.706(12) 2_655 ?
B4 B5 1.791(13) 2_655 ?
B4 B5 1.794(12) . ?
B5 B5 1.783(19) 2_655 ?
B5 B4 1.791(13) 2_655 ?
B6 C7 1.675(11) . ?
B6 B9 1.687(15) 2 ?
B6 B10 1.726(13) . ?
B6 B8 1.755(13) 2 ?
B6 B7 1.755(13) . ?
B7 C7 1.652(12) . ?
B7 B9 1.686(16) . ?
B7 B10 1.693(16) . ?
B7 B8 1.748(13) . ?
B8 C7 1.671(12) . ?
B8 B9 1.709(14) . ?
B8 C7 1.738(12) 2 ?
B8 B6 1.755(13) 2 ?
B9 B6 1.687(15) 2 ?
B9 B10 1.711(15) 2 ?
B9 B10 1.746(15) . ?
B10 B9 1.711(15) 2 ?
B10 B10 1.78(2) 2 ?
N1 C2 1.394(9) . ?
N1 C1 1.399(9) . ?
C1 B3 1.732(10) 2_655 ?
C1 C1 1.882(13) 2_655 ?
C2 C3 1.537(11) . ?
C3 C6 1.409(11) . ?
C3 C4 1.523(10) . ?
C3 C5 1.532(13) . ?
C7 N2 1.342(12) . ?
C7 N2' 1.62(3) . ?
C7 B8 1.738(12) 2 ?
C7 C7 1.853(13) 2 ?
C9 C12 1.458(11) . ?
C9 C8' 1.50(2) . ?
C9 C11 1.500(10) . ?
C9 C8 1.554(14) . ?
C9 C10 1.566(11) . ?
N2 C8 1.444(15) . ?
N2' C8' 1.43(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 B1 B4 107.9(6) . 2_655 ?
C1 B1 B5 106.1(5) . . ?
B4 B1 B5 62.9(5) 2_655 . ?
C1 B1 B2 57.4(5) . . ?
B4 B1 B2 109.0(6) 2_655 . ?
B5 B1 B2 59.4(5) . . ?
C1 B1 B3 61.0(4) . 2_655 ?
B4 B1 B3 59.1(5) 2_655 2_655 ?
B5 B1 B3 109.2(6) . 2_655 ?
B2 B1 B3 107.1(5) . 2_655 ?
C1 B2 B5 107.8(7) . . ?
C1 B2 B4 107.6(6) . . ?
B5 B2 B4 62.9(6) . . ?
C1 B2 B1 58.7(5) . . ?
B5 B2 B1 60.0(5) . . ?
B4 B2 B1 109.4(7) . . ?
C1 B2 B3 60.4(4) . . ?
B5 B2 B3 109.0(7) . . ?
B4 B2 B3 58.5(4) . . ?
B1 B2 B3 107.3(6) . . ?
B4 B3 C1 104.4(6) . . ?
B4 B3 C1 104.3(6) . 2_655 ?
C1 B3 C1 66.2(5) . 2_655 ?
B4 B3 B1 59.1(5) . 2_655 ?
C1 B3 B1 109.2(6) . 2_655 ?
C1 B3 B1 56.6(4) 2_655 2_655 ?
B4 B3 B2 59.2(5) . . ?
C1 B3 B2 55.6(4) . . ?
C1 B3 B2 107.8(6) 2_655 . ?
B1 B3 B2 106.5(6) 2_655 . ?
B1 B4 B3 61.8(5) 2_655 . ?
B1 B4 B2 111.0(7) 2_655 . ?
B3 B4 B2 62.3(5) . . ?
B1 B4 B5 59.2(5) 2_655 2_655 ?
B3 B4 B5 108.4(7) . 2_655 ?
B2 B4 B5 107.2(6) . 2_655 ?
B1 B4 B5 107.9(6) 2_655 . ?
B3 B4 B5 108.5(6) . . ?
B2 B4 B5 58.4(5) . . ?
B5 B4 B5 59.7(6) 2_655 . ?
B2 B5 B1 60.6(5) . . ?
B2 B5 B5 107.7(5) . 2_655 ?
B1 B5 B5 107.5(6) . 2_655 ?
B2 B5 B4 106.1(6) . 2_655 ?
B1 B5 B4 58.0(5) . 2_655 ?
B5 B5 B4 60.3(6) 2_655 2_655 ?
B2 B5 B4 58.7(5) . . ?
B1 B5 B4 106.6(6) . . ?
B5 B5 B4 60.1(5) 2_655 . ?
B4 B5 B4 106.2(7) 2_655 . ?
C7 B6 B9 106.6(7) . 2 ?
C7 B6 B10 105.2(6) . . ?
B9 B6 B10 60.2(6) 2 . ?
C7 B6 B8 60.9(5) . 2 ?
B9 B6 B8 59.5(6) 2 2 ?
B10 B6 B8 107.7(7) . 2 ?
C7 B6 B7 57.5(5) . . ?
B9 B6 B7 105.2(7) 2 . ?
B10 B6 B7 58.2(7) . . ?
B8 B6 B7 106.1(6) 2 . ?
C7 B7 B9 106.3(7) . . ?
C7 B7 B10 107.7(7) . . ?
B9 B7 B10 62.2(7) . . ?
C7 B7 B8 58.8(5) . . ?
B9 B7 B8 59.6(5) . . ?
B10 B7 B8 109.9(8) . . ?
C7 B7 B6 58.8(5) . . ?
B9 B7 B6 108.1(8) . . ?
B10 B7 B6 60.1(5) . . ?
B8 B7 B6 106.6(6) . . ?
C7 B8 B9 104.5(7) . . ?
C7 B8 C7 65.8(5) . 2 ?
B9 B8 C7 102.9(7) . 2 ?
C7 B8 B7 57.7(5) . . ?
B9 B8 B7 58.4(6) . . ?
C7 B8 B7 108.7(7) 2 . ?
C7 B8 B6 110.6(6) . 2 ?
B9 B8 B6 58.3(6) . 2 ?
C7 B8 B6 57.3(5) 2 2 ?
B7 B8 B6 107.0(7) . 2 ?
B7 B9 B6 113.2(7) . 2 ?
B7 B9 B8 62.0(6) . . ?
B6 B9 B8 62.2(6) 2 . ?
B7 B9 B10 110.8(7) . 2 ?
B6 B9 B10 61.1(6) 2 2 ?
B8 B9 B10 110.6(8) . 2 ?
B7 B9 B10 59.1(6) . . ?
B6 B9 B10 111.8(9) 2 . ?
B8 B9 B10 109.2(8) . . ?
B10 B9 B10 62.1(8) 2 . ?
B7 B10 B9 106.9(7) . 2 ?
B7 B10 B6 61.8(6) . . ?
B9 B10 B6 58.8(6) 2 . ?
B7 B10 B9 58.7(7) . . ?
B9 B10 B9 103.9(8) 2 . ?
B6 B10 B9 106.8(7) . . ?
B7 B10 B10 107.0(6) . 2 ?
B9 B10 B10 59.9(8) 2 2 ?
B6 B10 B10 108.1(7) . 2 ?
B9 B10 B10 58.0(6) . 2 ?
C2 N1 C1 123.4(8) . . ?
N1 C1 B2 123.1(7) . . ?
N1 C1 B1 130.0(6) . . ?
B2 C1 B1 63.9(5) . . ?
N1 C1 B3 111.2(6) . . ?
B2 C1 B3 64.0(5) . . ?
B1 C1 B3 114.2(6) . . ?
N1 C1 B3 121.0(6) . 2_655 ?
B2 C1 B3 113.2(7) . 2_655 ?
B1 C1 B3 62.3(5) . 2_655 ?
B3 C1 B3 107.5(5) . 2_655 ?
N1 C1 C1 115.5(4) . 2_655 ?
B2 C1 C1 107.4(5) . 2_655 ?
B1 C1 C1 106.0(5) . 2_655 ?
B3 C1 C1 57.3(4) . 2_655 ?
B3 C1 C1 56.5(4) 2_655 2_655 ?
N1 C2 C3 115.7(8) . . ?
C6 C3 C4 112.3(7) . . ?
C6 C3 C5 111.4(10) . . ?
C4 C3 C5 108.1(8) . . ?
C6 C3 C2 115.7(9) . . ?
C4 C3 C2 104.2(7) . . ?
C5 C3 C2 104.4(7) . . ?
N2 C7 B7 117.8(9) . . ?
N2' C7 B7 144.9(10) . . ?
N2 C7 B8 107.7(8) . . ?
N2' C7 B8 137.0(12) . . ?
B7 C7 B8 63.5(6) . . ?
N2 C7 B6 130.4(7) . . ?
N2' C7 B6 108.8(11) . . ?
B7 C7 B6 63.7(5) . . ?
B8 C7 B6 114.1(7) . . ?
N2 C7 B8 128.2(9) . 2 ?
N2' C7 B8 90.6(10) . 2 ?
B7 C7 B8 111.7(7) . 2 ?
B8 C7 B8 107.1(6) . 2 ?
B6 C7 B8 61.8(5) . 2 ?
N2 C7 C7 118.2(5) . 2 ?
N2' C7 C7 107.2(8) . 2 ?
B7 C7 C7 107.8(6) . 2 ?
B8 C7 C7 58.9(5) . 2 ?
B6 C7 C7 105.8(5) . 2 ?
B8 C7 C7 55.4(5) 2 2 ?
C12 C9 C8' 90.3(11) . . ?
C12 C9 C11 113.1(7) . . ?
C8' C9 C11 142.5(12) . . ?
C12 C9 C8 122.2(9) . . ?
C11 C9 C8 100.6(8) . . ?
C12 C9 C10 107.2(8) . . ?
C8' C9 C10 94.1(12) . . ?
C11 C9 C10 105.3(7) . . ?
C8 C9 C10 107.1(9) . . ?
C7 N2 C8 116.6(12) . . ?
N2 C8 C9 115.1(11) . . ?
C8' N2' C7 105(2) . . ?
N2' C8' C9 108(2) . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.033

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

data_compound4a
_database_code_depnum_ccdc_archive 'CCDC 1881766'
_audit_update_record             
;
2019-01-16 deposited with the CCDC.
2019-01-24 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            'C13 H34 B10 N2'
_chemical_formula_weight         326.52

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'
N N 0.0061 0.0033 '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'

_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                   8.829(5)
_cell_length_b                   11.088(5)
_cell_length_c                   12.660(6)
_cell_angle_alpha                107.034(9)
_cell_angle_beta                 98.560(9)
_cell_angle_gamma                109.841(6)
_cell_volume                     1071.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1560
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      21.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.012
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.052
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            6573
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         25.094
_diffrn_reflns_theta_full        25.094
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3727
_reflns_number_gt                1987
_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)+(0.0845P)²+0.4200P] 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         3727
_refine_ls_number_parameters     322
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.2288
_refine_ls_wR_factor_gt          0.2015
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.126
_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
C8 C 0.5639(7) 0.3289(6) 0.0679(5) 0.170(3) Uani 1 1 d . . . . .
H8A H 0.4967 0.2552 -0.0039 0.255 Uiso 1 1 calc R U . . .
H8B H 0.6403 0.4039 0.0537 0.255 Uiso 1 1 calc R U . . .
H8C H 0.4926 0.3601 0.1086 0.255 Uiso 1 1 calc R U . . .
N2 N 1.0280(3) 0.7491(2) 0.2735(2) 0.0693(7) Uani 1 1 d . . . . .
C2 C 1.0785(4) 0.5473(3) 0.2719(3) 0.0661(8) Uani 1 1 d . . . . .
B6 B 1.1828(6) 0.5003(5) 0.3664(5) 0.1009(15) Uani 1 1 d . . . . .
C1 C 1.1614(3) 0.7129(3) 0.3062(2) 0.0608(8) Uani 1 1 d . . . . .
N1 N 0.9057(3) 0.5058(2) 0.2214(2) 0.0764(8) Uani 1 1 d . . . . .
C3' C 0.8727(5) 0.6348(5) 0.2661(8) 0.071(2) Uani 0.680(13) 1 d . . P A 1
H3'A H 0.7765 0.6294 0.2137 0.086 Uiso 0.680(13) 1 calc R U P A 1
H3'B H 0.8526 0.6474 0.3411 0.086 Uiso 0.680(13) 1 calc R U P A 1
C3 C 0.8812(12) 0.6116(10) 0.1782(18) 0.077(5) Uani 0.320(13) 1 d . . P A 2
H3A H 0.7716 0.6125 0.1775 0.093 Uiso 0.320(13) 1 calc R U P A 2
H3B H 0.8969 0.5976 0.1020 0.093 Uiso 0.320(13) 1 calc R U P A 2
C9 C 1.0105(9) 0.8640(6) 0.3377(6) 0.090(2) Uani 0.515(4) 1 d . . P A 1
H9A H 1.1051 0.9171 0.4057 0.109 Uiso 0.515(4) 1 calc R U P A 1
H9B H 0.9093 0.8367 0.3623 0.109 Uiso 0.515(4) 1 calc R U P A 1
C10 C 1.0000(5) 0.9611(3) 0.2598(3) 0.1095(15) Uani 0.515(4) 1 d D . P A 1
C11 C 0.8301(10) 0.8812(8) 0.1745(8) 0.123(3) Uani 0.515(4) 1 d D . P A 1
H11A H 0.8317 0.8042 0.1158 0.185 Uiso 0.515(4) 1 calc R U P A 1
H11B H 0.8018 0.9400 0.1401 0.185 Uiso 0.515(4) 1 calc R U P A 1
H11C H 0.7483 0.8484 0.2130 0.185 Uiso 0.515(4) 1 calc R U P A 1
C13 C 0.9702(14) 1.0746(9) 0.3617(7) 0.156(4) Uani 0.515(4) 1 d D . P A 1
H13A H 0.9517 1.1415 0.3338 0.234 Uiso 0.515(4) 1 calc R U P A 1
H13B H 1.0674 1.1201 0.4268 0.234 Uiso 0.515(4) 1 calc R U P A 1
H13C H 0.8743 1.0285 0.3841 0.234 Uiso 0.515(4) 1 calc R U P A 1
C13' C 1.0177(12) 1.0156(9) 0.1500(7) 0.128(3) Uani 0.515(4) 1 d D . P A 1
H13D H 0.9320 0.9481 0.0817 0.192 Uiso 0.515(4) 1 calc R U P A 1
H13E H 1.1258 1.0284 0.1375 0.192 Uiso 0.515(4) 1 calc R U P A 1
H13F H 1.0056 1.1016 0.1678 0.192 Uiso 0.515(4) 1 calc R U P A 1
C9' C 1.0327(8) 0.8246(6) 0.1973(5) 0.0690(18) Uani 0.485(4) 1 d . . P A 3
H9'A H 0.9471 0.7669 0.1250 0.083 Uiso 0.485(4) 1 calc R U P A 3
H9'B H 1.1410 0.8517 0.1815 0.083 Uiso 0.485(4) 1 calc R U P A 3
C10' C 1.0000(5) 0.9611(3) 0.2598(3) 0.1095(15) Uani 0.485(4) 1 d D . P A 3
C12 C 1.1539(11) 1.0187(11) 0.2427(12) 0.140(4) Uani 0.485(4) 1 d D . P A 3
H12A H 1.1530 1.0839 0.2070 0.210 Uiso 0.485(4) 1 calc R U P A 3
H9'C H 1.1784 0.9476 0.1938 0.210 Uiso 0.485(4) 1 calc R U P A 3
H12B H 1.2380 1.0649 0.3153 0.210 Uiso 0.485(4) 1 calc R U P A 3
C12' C 1.1640(10) 1.0624(8) 0.3465(8) 0.113(3) Uani 0.485(4) 1 d D . P A 3
H12C H 1.1729 1.1547 0.3597 0.170 Uiso 0.485(4) 1 calc R U P A 3
H12D H 1.2547 1.0505 0.3178 0.170 Uiso 0.485(4) 1 calc R U P A 3
H12E H 1.1689 1.0468 0.4174 0.170 Uiso 0.485(4) 1 calc R U P A 3
C11' C 0.8409(10) 0.9383(10) 0.2726(10) 0.115(3) Uani 0.485(4) 1 d D . P A 3
H11D H 0.7592 0.8693 0.2031 0.172 Uiso 0.485(4) 1 calc R U P A 3
H11E H 0.8249 1.0225 0.2882 0.172 Uiso 0.485(4) 1 calc R U P A 3
H11F H 0.8282 0.9072 0.3352 0.172 Uiso 0.485(4) 1 calc R U P A 3
B9 B 1.3955(5) 0.6172(5) 0.2399(5) 0.0997(15) Uani 1 1 d . . . . .
C7 C 0.5393(7) 0.1776(5) 0.1789(4) 0.205(3) Uani 1 1 d . . . . .
H7A H 0.4668 0.0957 0.1140 0.308 Uiso 1 1 calc R U . . .
H7B H 0.4733 0.2200 0.2161 0.308 Uiso 1 1 calc R U . . .
H7C H 0.6020 0.1537 0.2320 0.308 Uiso 1 1 calc R U . . .
C6 C 0.7505(8) 0.2104(4) 0.0663(5) 0.184(3) Uani 1 1 d . . . . .
H6A H 0.7886 0.1569 0.1024 0.276 Uiso 1 1 calc R U . . .
H6B H 0.8450 0.2796 0.0592 0.276 Uiso 1 1 calc R U . . .
H6C H 0.6757 0.1510 -0.0086 0.276 Uiso 1 1 calc R U . . .
C5 C 0.6603(5) 0.2785(3) 0.1382(4) 0.1052(15) Uani 1 1 d . . . . .
C4 C 0.7836(4) 0.3968(3) 0.2447(3) 0.0940(12) Uani 1 1 d . . . . .
H4A H 0.7219 0.4364 0.2911 0.113 Uiso 1 1 calc R U . . .
H4B H 0.8431 0.3609 0.2895 0.113 Uiso 1 1 calc R U . . .
B2 B 1.3277(5) 0.7930(5) 0.4257(4) 0.0874(12) Uani 1 1 d . . . . .
B8 B 1.4764(6) 0.7274(6) 0.3843(5) 0.1101(17) Uani 1 1 d . . . . .
B10 B 1.3874(7) 0.5467(6) 0.3476(5) 0.1159(18) Uani 1 1 d . . . . .
B3 B 1.3564(4) 0.7666(4) 0.2852(4) 0.0777(11) Uani 1 1 d . . . . .
B5 B 1.2124(6) 0.4734(5) 0.2260(4) 0.0913(13) Uani 1 1 d . . . . .
B4 B 1.2003(5) 0.6112(4) 0.1878(3) 0.0677(9) Uani 1 1 d . . . . .
B1 B 1.1535(5) 0.6529(4) 0.4181(4) 0.0827(11) Uani 1 1 d . . . . .
B7 B 1.3496(7) 0.6555(6) 0.4640(5) 0.1136(17) Uani 1 1 d . . . . .
H4 H 1.137(3) 0.597(3) 0.107(2) 0.067(8) Uiso 1 1 d . . . . .
H3 H 1.403(4) 0.858(3) 0.258(2) 0.086(9) Uiso 1 1 d . . . . .
H5 H 1.146(4) 0.364(4) 0.160(3) 0.111(11) Uiso 1 1 d . . . . .
H6 H 1.118(4) 0.414(4) 0.384(3) 0.107(11) Uiso 1 1 d . . . . .
H1 H 1.060(4) 0.664(3) 0.456(3) 0.092(9) Uiso 1 1 d . . . . .
H8 H 1.609(5) 0.784(4) 0.410(3) 0.132(13) Uiso 1 1 d . . . . .
H2 H 1.349(5) 0.893(4) 0.476(3) 0.140(15) Uiso 1 1 d . . . . .
H7 H 1.396(5) 0.670(4) 0.558(4) 0.145(15) Uiso 1 1 d . . . . .
H10 H 1.484(5) 0.493(4) 0.367(3) 0.145(14) Uiso 1 1 d . . . . .
H9 H 1.476(4) 0.612(3) 0.177(3) 0.111(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C8 C5 1.489(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N2 C9 1.369(6) . ?
N2 C1 1.411(3) . ?
N2 C9' 1.447(6) . ?
N2 C3' 1.486(5) . ?
N2 C3 1.605(12) . ?
C2 N1 1.417(4) . ?
C2 C1 1.619(4) . ?
C2 B6 1.707(5) . ?
C2 B5 1.730(4) . ?
C2 B4 1.748(4) . ?
C2 B1 1.753(5) . ?
B6 B1 1.748(6) . ?
B6 B7 1.774(8) . ?
B6 B10 1.776(6) . ?
B6 B5 1.788(6) . ?
B6 H6 1.04(3) . ?
C1 B2 1.703(5) . ?
C1 B3 1.710(4) . ?
C1 B1 1.734(5) . ?
C1 B4 1.750(4) . ?
N1 C4 1.459(3) . ?
N1 C3 1.495(12) . ?
N1 C3' 1.519(6) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 C10 1.674(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.502(7) . ?
C10 C13 1.640(7) . ?
C10 C13' 1.679(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C9' C10' 1.633(7) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C10' C12 1.372(7) . ?
C10' C11' 1.383(6) . ?
C10' C12' 1.505(7) . ?
C12 H12A 0.9600 . ?
C12 H9'C 0.9600 . ?
C12 H12B 0.9600 . ?
C12' H12C 0.9600 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
B9 B4 1.723(6) . ?
B9 B8 1.749(8) . ?
B9 B3 1.756(6) . ?
B9 B10 1.758(6) . ?
B9 B5 1.785(6) . ?
B9 H9 1.15(3) . ?
C7 C5 1.533(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 C5 1.502(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 C4 1.510(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
B2 B1 1.742(6) . ?
B2 B8 1.776(7) . ?
B2 B3 1.788(6) . ?
B2 B7 1.789(7) . ?
B2 H2 1.05(4) . ?
B8 B7 1.763(6) . ?
B8 B3 1.767(6) . ?
B8 B10 1.768(8) . ?
B8 H8 1.07(4) . ?
B10 B7 1.765(8) . ?
B10 B5 1.768(8) . ?
B10 H10 1.23(4) . ?
B3 B4 1.740(6) . ?
B3 H3 1.13(3) . ?
B5 B4 1.762(5) . ?
B5 H5 1.14(3) . ?
B4 H4 1.03(3) . ?
B1 B7 1.730(7) . ?
B1 H1 1.04(3) . ?
B7 H7 1.14(4) . ?

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
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 N2 C1 124.0(4) . . ?
C1 N2 C9' 121.4(3) . . ?
C9 N2 C3' 102.8(4) . . ?
C1 N2 C3' 106.1(3) . . ?
C1 N2 C3 106.6(4) . . ?
N1 C2 C1 105.3(2) . . ?
N1 C2 B6 132.4(3) . . ?
C1 C2 B6 110.7(3) . . ?
N1 C2 B5 129.1(3) . . ?
C1 C2 B5 111.4(2) . . ?
B6 C2 B5 62.7(2) . . ?
N1 C2 B4 111.4(3) . . ?
C1 C2 B4 62.47(17) . . ?
B6 C2 B4 112.4(2) . . ?
B5 C2 B4 60.89(19) . . ?
N1 C2 B1 115.5(2) . . ?
C1 C2 B1 61.73(19) . . ?
B6 C2 B1 60.7(2) . . ?
B5 C2 B1 112.5(3) . . ?
B4 C2 B1 113.6(2) . . ?
C2 B6 B1 61.0(2) . . ?
C2 B6 B7 105.6(3) . . ?
B1 B6 B7 58.8(3) . . ?
C2 B6 B10 104.7(3) . . ?
B1 B6 B10 107.1(4) . . ?
B7 B6 B10 59.6(3) . . ?
C2 B6 B5 59.3(2) . . ?
B1 B6 B5 110.0(3) . . ?
B7 B6 B5 108.1(3) . . ?
B10 B6 B5 59.5(3) . . ?
C2 B6 H6 120(2) . . ?
B1 B6 H6 121.2(18) . . ?
B7 B6 H6 126.9(19) . . ?
B10 B6 H6 125.4(19) . . ?
B5 B6 H6 118.0(18) . . ?
N2 C1 C2 105.8(2) . . ?
N2 C1 B2 130.4(3) . . ?
C2 C1 B2 112.1(2) . . ?
N2 C1 B3 128.8(2) . . ?
C2 C1 B3 111.2(2) . . ?
B2 C1 B3 63.2(2) . . ?
N2 C1 B1 114.9(2) . . ?
C2 C1 B1 62.9(2) . . ?
B2 C1 B1 60.9(2) . . ?
B3 C1 B1 112.9(2) . . ?
N2 C1 B4 112.3(2) . . ?
C2 C1 B4 62.39(17) . . ?
B2 C1 B4 113.0(3) . . ?
B3 C1 B4 60.4(2) . . ?
B1 C1 B4 114.5(2) . . ?
C2 N1 C4 118.8(3) . . ?
C2 N1 C3 109.7(4) . . ?
C4 N1 C3 129.2(5) . . ?
C2 N1 C3' 105.2(3) . . ?
C4 N1 C3' 107.4(3) . . ?
N2 C3' N1 104.5(4) . . ?
N2 C3' H3'A 110.9 . . ?
N1 C3' H3'A 110.9 . . ?
N2 C3' H3'B 110.9 . . ?
N1 C3' H3'B 110.9 . . ?
H3'A C3' H3'B 108.9 . . ?
N1 C3 N2 100.1(9) . . ?
N1 C3 H3A 111.8 . . ?
N2 C3 H3A 111.8 . . ?
N1 C3 H3B 111.8 . . ?
N2 C3 H3B 111.8 . . ?
H3A C3 H3B 109.5 . . ?
N2 C9 C10 109.9(5) . . ?
N2 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C13 103.5(6) . . ?
C11 C10 C9 104.3(5) . . ?
C13 C10 C9 93.7(5) . . ?
C11 C10 C13' 75.5(5) . . ?
C13 C10 C13' 108.8(5) . . ?
C9 C10 C13' 157.0(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C13' H13D 109.5 . . ?
C10 C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C10 C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
N2 C9' C10' 108.2(4) . . ?
N2 C9' H9'A 110.1 . . ?
C10' C9' H9'A 110.1 . . ?
N2 C9' H9'B 110.1 . . ?
C10' C9' H9'B 110.1 . . ?
H9'A C9' H9'B 108.4 . . ?
C12 C10' C11' 162.4(6) . . ?
C12 C10' C12' 50.7(5) . . ?
C11' C10' C12' 127.2(7) . . ?
C12 C10' C9' 78.3(6) . . ?
C11' C10' C9' 116.5(5) . . ?
C12' C10' C9' 105.3(5) . . ?
C10' C12 H12A 109.5 . . ?
C10' C12 H9'C 109.5 . . ?
H12A C12 H9'C 109.5 . . ?
C10' C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H9'C C12 H12B 109.5 . . ?
C10' C12' H12C 109.5 . . ?
C10' C12' H12D 109.5 . . ?
H12C C12' H12D 109.5 . . ?
C10' C12' H12E 109.5 . . ?
H12C C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
B4 B9 B8 108.9(3) . . ?
B4 B9 B3 60.0(2) . . ?
B8 B9 B3 60.6(3) . . ?
B4 B9 B10 108.6(3) . . ?
B8 B9 B10 60.6(3) . . ?
B3 B9 B10 108.8(3) . . ?
B4 B9 B5 60.3(2) . . ?
B8 B9 B5 108.6(3) . . ?
B3 B9 B5 108.2(3) . . ?
B10 B9 B5 59.9(3) . . ?
B4 B9 H9 116.1(17) . . ?
B8 B9 H9 123.1(17) . . ?
B3 B9 H9 116.6(17) . . ?
B10 B9 H9 127.5(17) . . ?
B5 B9 H9 123.0(17) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C5 C6 108.7(4) . . ?
C8 C5 C4 110.4(4) . . ?
C6 C5 C4 110.4(4) . . ?
C8 C5 C7 109.1(5) . . ?
C6 C5 C7 111.3(4) . . ?
C4 C5 C7 106.9(3) . . ?
N1 C4 C5 114.2(3) . . ?
N1 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C1 B2 B1 60.4(2) . . ?
C1 B2 B8 104.0(3) . . ?
B1 B2 B8 106.7(3) . . ?
C1 B2 B3 58.6(2) . . ?
B1 B2 B3 108.8(3) . . ?
B8 B2 B3 59.4(2) . . ?
C1 B2 B7 104.5(3) . . ?
B1 B2 B7 58.7(3) . . ?
B8 B2 B7 59.3(3) . . ?
B3 B2 B7 107.0(3) . . ?
C1 B2 H2 116(2) . . ?
B1 B2 H2 120(2) . . ?
B8 B2 H2 129(2) . . ?
B3 B2 H2 117(2) . . ?
B7 B2 H2 131(2) . . ?
B9 B8 B7 108.7(4) . . ?
B9 B8 B3 59.9(3) . . ?
B7 B8 B3 109.1(3) . . ?
B9 B8 B10 60.0(3) . . ?
B7 B8 B10 60.0(3) . . ?
B3 B8 B10 107.9(4) . . ?
B9 B8 B2 108.8(3) . . ?
B7 B8 B2 60.7(3) . . ?
B3 B8 B2 60.6(2) . . ?
B10 B8 B2 108.4(3) . . ?
B9 B8 H8 114(2) . . ?
B7 B8 H8 128(2) . . ?
B3 B8 H8 117(2) . . ?
B10 B8 H8 121(2) . . ?
B2 B8 H8 126(2) . . ?
B9 B10 B7 108.2(3) . . ?
B9 B10 B8 59.4(3) . . ?
B7 B10 B8 59.8(3) . . ?
B9 B10 B5 60.8(3) . . ?
B7 B10 B5 109.4(3) . . ?
B8 B10 B5 108.4(3) . . ?
B9 B10 B6 108.5(3) . . ?
B7 B10 B6 60.1(3) . . ?
B8 B10 B6 107.5(3) . . ?
B5 B10 B6 60.6(3) . . ?
B9 B10 H10 119.8(18) . . ?
B7 B10 H10 119.4(19) . . ?
B8 B10 H10 116.9(19) . . ?
B5 B10 H10 125(2) . . ?
B6 B10 H10 125.9(18) . . ?
C1 B3 B4 60.93(18) . . ?
C1 B3 B9 105.2(3) . . ?
B4 B3 B9 59.0(2) . . ?
C1 B3 B8 104.1(3) . . ?
B4 B3 B8 107.3(3) . . ?
B9 B3 B8 59.5(3) . . ?
C1 B3 B2 58.2(2) . . ?
B4 B3 B2 109.4(3) . . ?
B9 B3 B2 108.0(3) . . ?
B8 B3 B2 60.0(3) . . ?
C1 B3 H3 120.0(15) . . ?
B4 B3 H3 119.9(15) . . ?
B9 B3 H3 126.4(14) . . ?
B8 B3 H3 126.2(15) . . ?
B2 B3 H3 119.3(14) . . ?
C2 B5 B4 60.08(18) . . ?
C2 B5 B10 104.0(3) . . ?
B4 B5 B10 106.4(3) . . ?
C2 B5 B9 103.8(3) . . ?
B4 B5 B9 58.1(2) . . ?
B10 B5 B9 59.3(3) . . ?
C2 B5 B6 58.0(2) . . ?
B4 B5 B6 108.0(3) . . ?
B10 B5 B6 59.9(3) . . ?
B9 B5 B6 106.8(4) . . ?
C2 B5 H5 114.2(18) . . ?
B4 B5 H5 119.4(18) . . ?
B10 B5 H5 130.4(18) . . ?
B9 B5 H5 132.7(17) . . ?
B6 B5 H5 116.8(17) . . ?
B9 B4 B3 60.9(3) . . ?
B9 B4 C2 105.6(3) . . ?
B3 B4 C2 104.0(3) . . ?
B9 B4 C1 105.0(3) . . ?
B3 B4 C1 58.69(19) . . ?
C2 B4 C1 55.14(16) . . ?
B9 B4 B5 61.6(2) . . ?
B3 B4 B5 110.0(3) . . ?
C2 B4 B5 59.04(18) . . ?
C1 B4 B5 104.0(3) . . ?
B9 B4 H4 131.5(14) . . ?
B3 B4 H4 124.7(14) . . ?
C2 B4 H4 116.6(14) . . ?
C1 B4 H4 118.1(14) . . ?
B5 B4 H4 122.4(15) . . ?
B7 B1 C1 105.8(3) . . ?
B7 B1 B2 62.0(3) . . ?
C1 B1 B2 58.7(2) . . ?
B7 B1 B6 61.3(3) . . ?
C1 B1 B6 103.6(3) . . ?
B2 B1 B6 110.3(3) . . ?
B7 B1 C2 105.5(3) . . ?
C1 B1 C2 55.32(17) . . ?
B2 B1 C2 104.2(3) . . ?
B6 B1 C2 58.4(2) . . ?
B7 B1 H1 135.6(17) . . ?
C1 B1 H1 113.0(17) . . ?
B2 B1 H1 123.1(17) . . ?
B6 B1 H1 125.4(17) . . ?
C2 B1 H1 113.8(17) . . ?
B1 B7 B8 107.8(3) . . ?
B1 B7 B10 108.4(4) . . ?
B8 B7 B10 60.2(3) . . ?
B1 B7 B6 59.8(3) . . ?
B8 B7 B6 107.8(4) . . ?
B10 B7 B6 60.2(3) . . ?
B1 B7 B2 59.3(2) . . ?
B8 B7 B2 60.0(3) . . ?
B10 B7 B2 108.0(3) . . ?
B6 B7 B2 106.9(3) . . ?
B1 B7 H7 118(2) . . ?
B8 B7 H7 125(2) . . ?
B10 B7 H7 125(2) . . ?
B6 B7 H7 121(2) . . ?
B2 B7 H7 121(2) . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_compound3d
_database_code_depnum_ccdc_archive 'CCDC 1881765'
_audit_update_record             
;
2019-01-16 deposited with the CCDC.
2019-01-24 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            'C18 H30 B10 N2 O2'
_chemical_formula_weight         414.54

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   26.797(6)
_cell_length_b                   7.6904(17)
_cell_length_c                   11.398(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2348.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9155
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            15891
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.520
_diffrn_reflns_theta_max         28.108
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5315
_reflns_number_gt                4827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.985

_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)+(0.0694P)²+0.1968P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0046(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2100 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5315
_refine_ls_number_parameters     340
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.83729(8) 0.5748(3) 0.89439(17) 0.0364(4) Uani 1 1 d . . . . .
C2 C 0.81342(7) 0.7301(3) 1.01518(17) 0.0324(4) Uani 1 1 d . . . . .
B3 B 0.81080(8) 0.5088(3) 1.02709(19) 0.0343(4) Uani 1 1 d . . . . .
B4 B 0.79669(10) 0.4086(3) 0.8879(2) 0.0426(5) Uani 1 1 d . . . . .
B5 B 0.79616(11) 0.5801(4) 0.7828(2) 0.0447(6) Uani 1 1 d . . . . .
B6 B 0.81113(9) 0.7725(3) 0.8646(2) 0.0373(5) Uani 1 1 d . . . . .
B7 B 0.75959(8) 0.6458(3) 1.0680(2) 0.0354(5) Uani 1 1 d . . . . .
B8 B 0.74852(9) 0.4497(4) 0.9915(2) 0.0403(5) Uani 1 1 d . . . . .
B9 B 0.73912(10) 0.5003(4) 0.8401(2) 0.0459(6) Uani 1 1 d . . . . .
B10 B 0.74880(9) 0.7287(4) 0.8229(2) 0.0409(5) Uani 1 1 d . . . . .
B11 B 0.76062(8) 0.8190(3) 0.9642(2) 0.0350(5) Uani 1 1 d . . . . .
B12 B 0.71708(9) 0.6447(4) 0.9488(2) 0.0412(5) Uani 1 1 d . . . . .
C3 C 0.91802(10) 0.4492(5) 0.9561(3) 0.0685(9) Uani 1 1 d . . . . .
H3A H 0.9030 0.3345 0.9582 0.082 Uiso 1 1 calc R U . . .
H3B H 0.9180 0.4953 1.0353 0.082 Uiso 1 1 calc R U . . .
C4 C 0.97112(9) 0.4342(4) 0.9132(2) 0.0518(6) Uani 1 1 d . . . . .
C5 C 1.00916(11) 0.5046(4) 0.9780(2) 0.0596(7) Uani 1 1 d . . . . .
H5 H 1.0016 0.5686 1.0449 0.072 Uiso 1 1 calc R U . . .
C6 C 1.05870(10) 0.4825(4) 0.9460(2) 0.0530(6) Uani 1 1 d . . . . .
H6 H 1.0841 0.5303 0.9914 0.064 Uiso 1 1 calc R U . . .
C7 C 1.06990(8) 0.3889(3) 0.84638(19) 0.0406(5) Uani 1 1 d . . . . .
C8 C 1.03213(9) 0.3180(3) 0.7790(2) 0.0491(5) Uani 1 1 d . . . . .
H8 H 1.0397 0.2547 0.7118 0.059 Uiso 1 1 calc R U . . .
C9 C 0.98304(9) 0.3422(4) 0.8124(3) 0.0539(6) Uani 1 1 d . . . . .
H9 H 0.9576 0.2960 0.7665 0.065 Uiso 1 1 calc R U . . .
C10 C 1.15799(9) 0.4217(4) 0.8752(3) 0.0627(7) Uani 1 1 d . . . . .
H10A H 1.1567 0.5464 0.8761 0.094 Uiso 1 1 calc R U . . .
H10B H 1.1889 0.3845 0.8406 0.094 Uiso 1 1 calc R U . . .
H10C H 1.1558 0.3785 0.9541 0.094 Uiso 1 1 calc R U . . .
C11 C 0.85893(8) 0.9983(3) 1.0740(2) 0.0448(5) Uani 1 1 d . . . . .
H11A H 0.8380 1.0545 1.1321 0.054 Uiso 1 1 calc R U . . .
H11B H 0.8498 1.0430 0.9973 0.054 Uiso 1 1 calc R U . . .
C12 C 0.91316(8) 1.0390(3) 1.0988(2) 0.0392(4) Uani 1 1 d . . . . .
C13 C 0.92767(10) 1.1334(3) 1.1970(2) 0.0485(5) Uani 1 1 d . . . . .
H13 H 0.9034 1.1749 1.2482 0.058 Uiso 1 1 calc R U . . .
C14 C 0.97736(10) 1.1669(4) 1.2202(2) 0.0540(6) Uani 1 1 d . . . . .
H14 H 0.9862 1.2313 1.2860 0.065 Uiso 1 1 calc R U . . .
C15 C 1.01408(9) 1.1045(3) 1.1453(2) 0.0467(5) Uani 1 1 d . . . . .
C16 C 1.00063(9) 1.0128(4) 1.0459(2) 0.0473(5) Uani 1 1 d . . . . .
H16 H 1.0249 0.9722 0.9943 0.057 Uiso 1 1 calc R U . . .
C17 C 0.95041(9) 0.9818(3) 1.0239(2) 0.0454(5) Uani 1 1 d . . . . .
H17 H 0.9415 0.9207 0.9567 0.054 Uiso 1 1 calc R U . . .
C18 C 1.10061(11) 1.0721(6) 1.1034(3) 0.0782(10) Uani 1 1 d . . . . .
H18A H 1.0984 0.9475 1.1031 0.117 Uiso 1 1 calc R U . . .
H18B H 1.1327 1.1067 1.1328 0.117 Uiso 1 1 calc R U . . .
H18C H 1.0965 1.1151 1.0250 0.117 Uiso 1 1 calc R U . . .
N1 N 0.88832(7) 0.5620(3) 0.88092(19) 0.0462(5) Uani 1 1 d D . . . .
N2 N 0.85085(7) 0.8104(2) 1.07736(17) 0.0396(4) Uani 1 1 d D . . . .
O1 O 1.11749(6) 0.3562(3) 0.80852(17) 0.0562(5) Uani 1 1 d . . . . .
O2 O 1.06269(8) 1.1412(3) 1.1763(2) 0.0672(6) Uani 1 1 d . . . . .
H7'' H 0.7519(10) 0.669(4) 1.157(2) 0.044(7) Uiso 1 1 d . . . . .
H8'' H 0.7296(9) 0.343(3) 1.031(2) 0.045(7) Uiso 1 1 d . . . . .
H3'' H 0.8344(9) 0.453(3) 1.088(2) 0.036(6) Uiso 1 1 d . . . . .
H12' H 0.6779(10) 0.664(4) 0.962(2) 0.045(7) Uiso 1 1 d . . . . .
H5'' H 0.8129(10) 0.573(4) 0.698(2) 0.048(7) Uiso 1 1 d . . . . .
H11' H 0.7510(10) 0.952(4) 0.987(2) 0.043(7) Uiso 1 1 d . . . . .
H9'' H 0.7131(10) 0.435(4) 0.790(2) 0.049(7) Uiso 1 1 d . . . . .
H10' H 0.7321(10) 0.801(4) 0.759(2) 0.046(7) Uiso 1 1 d . . . . .
H4'' H 0.8115(11) 0.281(4) 0.861(3) 0.058(8) Uiso 1 1 d . . . . .
H6'' H 0.8365(11) 0.869(4) 0.833(3) 0.058(8) Uiso 1 1 d . . . . .
H2 H 0.8592(9) 0.758(3) 1.1468(19) 0.041(6) Uiso 1 1 d D . . . .
H1 H 0.9026(10) 0.647(3) 0.836(3) 0.056(8) Uiso 1 1 d 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
C1 N1 1.380(3) . ?
C1 B4 1.680(4) . ?
C1 B5 1.684(3) . ?
C1 B6 1.709(3) . ?
C1 B3 1.746(3) . ?
C1 C2 1.932(3) . ?
C2 N2 1.374(3) . ?
C2 B11 1.675(3) . ?
C2 B7 1.692(3) . ?
C2 B3 1.709(3) . ?
C2 B6 1.749(3) . ?
B3 B8 1.776(3) . ?
B3 B7 1.792(3) . ?
B3 B4 1.804(3) . ?
B4 B8 1.778(4) . ?
B4 B9 1.781(4) . ?
B4 B5 1.782(4) . ?
B5 B10 1.768(4) . ?
B5 B9 1.772(4) . ?
B5 B6 1.795(4) . ?
B6 B10 1.769(3) . ?
B6 B11 1.803(3) . ?
B7 B8 1.767(4) . ?
B7 B12 1.773(3) . ?
B7 B11 1.781(3) . ?
B8 B9 1.787(4) . ?
B8 B12 1.788(4) . ?
B9 B12 1.765(4) . ?
B9 B10 1.787(4) . ?
B10 B11 1.782(3) . ?
B10 B12 1.789(4) . ?
B11 B12 1.786(4) . ?
C3 N1 1.456(3) . ?
C3 C4 1.509(3) . ?
C4 C5 1.370(4) . ?
C4 C9 1.387(4) . ?
C5 C6 1.387(4) . ?
C6 C7 1.378(3) . ?
C7 O1 1.370(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.382(3) . ?
C10 O1 1.418(3) . ?
C11 N2 1.462(3) . ?
C11 C12 1.513(3) . ?
C12 C17 1.385(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.382(4) . ?
C14 C15 1.388(4) . ?
C15 O2 1.378(3) . ?
C15 C16 1.383(4) . ?
C16 C17 1.389(3) . ?
C18 O2 1.416(4) . ?

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 C1 B4 125.65(19) . . ?
N1 C1 B5 124.51(18) . . ?
B4 C1 B5 63.96(15) . . ?
N1 C1 B6 116.62(18) . . ?
B4 C1 B6 113.73(17) . . ?
B5 C1 B6 63.86(14) . . ?
N1 C1 B3 118.60(17) . . ?
B4 C1 B3 63.52(13) . . ?
B5 C1 B3 113.28(17) . . ?
B6 C1 B3 105.31(15) . . ?
N1 C1 C2 116.85(17) . . ?
B4 C1 C2 106.71(15) . . ?
B5 C1 C2 107.86(14) . . ?
B6 C1 C2 57.01(11) . . ?
B3 C1 C2 55.09(11) . . ?
N2 C2 B11 127.71(18) . . ?
N2 C2 B7 127.64(17) . . ?
B11 C2 B7 63.87(13) . . ?
N2 C2 B3 115.88(16) . . ?
B11 C2 B3 113.52(16) . . ?
B7 C2 B3 63.58(13) . . ?
N2 C2 B6 116.61(17) . . ?
B11 C2 B6 63.49(13) . . ?
B7 C2 B6 113.00(15) . . ?
B3 C2 B6 105.21(15) . . ?
N2 C2 C1 113.81(15) . . ?
B11 C2 C1 106.55(14) . . ?
B7 C2 C1 107.39(14) . . ?
B3 C2 C1 56.93(11) . . ?
B6 C2 C1 55.07(11) . . ?
C2 B3 C1 67.98(13) . . ?
C2 B3 B8 105.99(16) . . ?
C1 B3 B8 105.00(15) . . ?
C2 B3 B7 57.76(12) . . ?
C1 B3 B7 111.47(15) . . ?
B8 B3 B7 59.36(14) . . ?
C2 B3 B4 111.36(15) . . ?
C1 B3 B4 56.46(13) . . ?
B8 B3 B4 59.54(14) . . ?
B7 B3 B4 108.63(16) . . ?
C1 B4 B8 107.78(18) . . ?
C1 B4 B9 105.86(18) . . ?
B8 B4 B9 60.28(15) . . ?
C1 B4 B5 58.12(14) . . ?
B8 B4 B5 108.02(18) . . ?
B9 B4 B5 59.65(15) . . ?
C1 B4 B3 60.02(13) . . ?
B8 B4 B3 59.45(14) . . ?
B9 B4 B3 106.33(18) . . ?
B5 B4 B3 106.06(18) . . ?
C1 B5 B10 106.87(17) . . ?
C1 B5 B9 106.13(17) . . ?
B10 B5 B9 60.63(16) . . ?
C1 B5 B4 57.92(13) . . ?
B10 B5 B4 108.10(18) . . ?
B9 B5 B4 60.17(15) . . ?
C1 B5 B6 58.75(13) . . ?
B10 B5 B6 59.52(14) . . ?
B9 B5 B6 106.68(18) . . ?
B4 B5 B6 105.05(16) . . ?
C1 B6 C2 67.92(12) . . ?
C1 B6 B10 105.75(18) . . ?
C2 B6 B10 105.15(16) . . ?
C1 B6 B5 57.39(14) . . ?
C2 B6 B5 111.34(16) . . ?
B10 B6 B5 59.50(15) . . ?
C1 B6 B11 111.04(16) . . ?
C2 B6 B11 56.27(12) . . ?
B10 B6 B11 59.87(13) . . ?
B5 B6 B11 108.83(18) . . ?
C2 B7 B8 107.13(16) . . ?
C2 B7 B12 106.08(16) . . ?
B8 B7 B12 60.67(14) . . ?
C2 B7 B11 57.60(12) . . ?
B8 B7 B11 108.26(16) . . ?
B12 B7 B11 60.32(14) . . ?
C2 B7 B3 58.65(12) . . ?
B8 B7 B3 59.89(14) . . ?
B12 B7 B3 106.85(17) . . ?
B11 B7 B3 104.76(15) . . ?
B7 B8 B3 60.75(13) . . ?
B7 B8 B4 110.96(17) . . ?
B3 B8 B4 61.01(14) . . ?
B7 B8 B9 108.30(18) . . ?
B3 B8 B9 107.28(18) . . ?
B4 B8 B9 59.95(15) . . ?
B7 B8 B12 59.83(14) . . ?
B3 B8 B12 106.87(17) . . ?
B4 B8 B12 108.06(18) . . ?
B9 B8 B12 59.19(15) . . ?
B12 B9 B5 109.23(19) . . ?
B12 B9 B4 108.92(18) . . ?
B5 B9 B4 60.18(15) . . ?
B12 B9 B10 60.47(15) . . ?
B5 B9 B10 59.58(15) . . ?
B4 B9 B10 107.28(18) . . ?
B12 B9 B8 60.43(16) . . ?
B5 B9 B8 108.05(17) . . ?
B4 B9 B8 59.77(14) . . ?
B10 B9 B8 107.44(18) . . ?
B5 B10 B6 60.98(15) . . ?
B5 B10 B11 110.97(16) . . ?
B6 B10 B11 61.01(13) . . ?
B5 B10 B9 59.79(16) . . ?
B6 B10 B9 107.15(17) . . ?
B11 B10 B9 108.02(17) . . ?
B5 B10 B12 108.34(18) . . ?
B6 B10 B12 107.58(16) . . ?
B11 B10 B12 60.01(14) . . ?
B9 B10 B12 59.17(16) . . ?
C2 B11 B7 58.53(12) . . ?
C2 B11 B10 107.74(17) . . ?
B7 B11 B10 107.84(18) . . ?
C2 B11 B12 106.25(17) . . ?
B7 B11 B12 59.60(14) . . ?
B10 B11 B12 60.19(14) . . ?
C2 B11 B6 60.23(12) . . ?
B7 B11 B6 106.38(16) . . ?
B10 B11 B6 59.12(14) . . ?
B12 B11 B6 106.25(18) . . ?
B9 B12 B7 109.02(18) . . ?
B9 B12 B11 108.82(18) . . ?
B7 B12 B11 60.08(13) . . ?
B9 B12 B8 60.39(15) . . ?
B7 B12 B8 59.50(14) . . ?
B11 B12 B8 107.15(16) . . ?
B9 B12 B10 60.36(15) . . ?
B7 B12 B10 107.91(16) . . ?
B11 B12 B10 59.81(14) . . ?
B8 B12 B10 107.32(17) . . ?
N1 C3 C4 111.7(2) . . ?
C5 C4 C9 118.5(2) . . ?
C5 C4 C3 119.8(3) . . ?
C9 C4 C3 121.6(3) . . ?
C4 C5 C6 121.5(2) . . ?
C7 C6 C5 119.3(3) . . ?
O1 C7 C6 124.0(2) . . ?
O1 C7 C8 115.7(2) . . ?
C6 C7 C8 120.3(2) . . ?
C9 C8 C7 119.4(2) . . ?
C8 C9 C4 121.0(3) . . ?
N2 C11 C12 109.97(18) . . ?
C17 C12 C13 117.4(2) . . ?
C17 C12 C11 120.8(2) . . ?
C13 C12 C11 121.8(2) . . ?
C14 C13 C12 121.4(2) . . ?
C13 C14 C15 120.1(2) . . ?
O2 C15 C16 124.1(2) . . ?
O2 C15 C14 116.2(2) . . ?
C16 C15 C14 119.7(2) . . ?
C15 C16 C17 119.2(2) . . ?
C12 C17 C16 122.2(2) . . ?
C1 N1 C3 121.26(19) . . ?
C2 N2 C11 122.59(18) . . ?
C7 O1 C10 118.6(2) . . ?
C15 O2 C18 116.8(2) . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037

