# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_3aa
_database_code_depnum_ccdc_archive 'CCDC 1987436'
loop_
_audit_author_name
_audit_author_address
'Hoi Shan CHAN'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H21 B10 N'
_chemical_formula_weight         311.42

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   18.8752(10)
_cell_length_b                   7.2500(4)
_cell_length_c                   13.1539(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.9162(15)
_cell_angle_gamma                90
_cell_volume                     1786.95(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    167
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.058
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_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 D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28391
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.013
_diffrn_reflns_theta_max         25.240
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3235
_reflns_number_gt                2386
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0739P)²+0.8575P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3235
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.16094(9) 0.4089(3) 0.45751(13) 0.0454(5) Uani 1 1 d . . . . .
C1 C 0.30262(10) 0.5555(3) 0.55425(16) 0.0433(5) Uani 1 1 d . . . . .
H1 H 0.2676 0.5369 0.4819 0.052 Uiso 1 1 calc R U . . .
C2 C 0.37310(11) 0.4236(3) 0.58083(16) 0.0449(5) Uani 1 1 d . . . . .
C11 C 0.38734(14) 0.2763(4) 0.5045(2) 0.0735(8) Uani 1 1 d . . . . .
H11A H 0.4299 0.2100 0.5297 0.110 Uiso 1 1 calc R U . . .
H11B H 0.3477 0.1925 0.4953 0.110 Uiso 1 1 calc R U . . .
H11C H 0.3934 0.3329 0.4402 0.110 Uiso 1 1 calc R U . . .
C12 C 0.17949(10) 0.6421(3) 0.66091(14) 0.0358(5) Uani 1 1 d . . . . .
C13 C 0.16110(11) 0.7840(3) 0.72477(16) 0.0450(5) Uani 1 1 d . . . . .
H13A H 0.1974 0.8573 0.7574 0.054 Uiso 1 1 calc R U . . .
C14 C 0.09185(12) 0.8204(3) 0.74161(18) 0.0509(6) Uani 1 1 d . . . . .
H14A H 0.0822 0.9164 0.7848 0.061 Uiso 1 1 calc R U . . .
C15 C 0.03717(12) 0.7153(3) 0.69464(18) 0.0520(6) Uani 1 1 d . . . . .
H15A H -0.0098 0.7390 0.7054 0.062 Uiso 1 1 calc R U . . .
C16 C 0.05284(11) 0.5739(3) 0.63121(16) 0.0465(5) Uani 1 1 d . . . . .
H16A H 0.0158 0.5021 0.5995 0.056 Uiso 1 1 calc R U . . .
C17 C 0.12254(10) 0.5351(3) 0.61305(14) 0.0368(5) Uani 1 1 d . . . . .
C18 C 0.13107(10) 0.3769(3) 0.54320(15) 0.0382(5) Uani 1 1 d . . . . .
C19 C 0.10608(13) 0.2036(3) 0.56545(18) 0.0537(6) Uani 1 1 d . . . . .
H19A H 0.0846 0.1849 0.6247 0.064 Uiso 1 1 calc R U . . .
C20 C 0.11314(14) 0.0593(3) 0.4995(2) 0.0644(7) Uani 1 1 d . . . . .
H20A H 0.0969 -0.0579 0.5137 0.077 Uiso 1 1 calc R U . . .
C21 C 0.14451(13) 0.0918(4) 0.4124(2) 0.0611(7) Uani 1 1 d . . . . .
H21A H 0.1502 -0.0029 0.3664 0.073 Uiso 1 1 calc R U . . .
C22 C 0.16725(12) 0.2667(4) 0.39511(17) 0.0536(6) Uani 1 1 d . . . . .
H22A H 0.1885 0.2879 0.3360 0.064 Uiso 1 1 calc R U . . .
B3 B 0.38491(14) 0.6495(4) 0.5470(2) 0.0529(7) Uani 1 1 d . . . . .
H3 H 0.4053 0.6934 0.4759 0.063 Uiso 1 1 calc R U . . .
B4 B 0.31641(13) 0.7722(4) 0.5988(2) 0.0521(7) Uani 1 1 d . . . . .
H4 H 0.2924 0.8974 0.5620 0.062 Uiso 1 1 calc R U . . .
B5 B 0.26257(12) 0.6121(3) 0.65890(17) 0.0367(5) Uani 1 1 d . . . . .
B6 B 0.30080(12) 0.3911(3) 0.6461(2) 0.0433(6) Uani 1 1 d . . . . .
H6 H 0.2672 0.2667 0.6392 0.052 Uiso 1 1 calc R U . . .
B7 B 0.44022(13) 0.5444(4) 0.64760(19) 0.0466(6) Uani 1 1 d . . . . .
H7 H 0.4972 0.5197 0.6426 0.056 Uiso 1 1 calc R U . . .
B8 B 0.40491(14) 0.7678(4) 0.6624(2) 0.0593(8) Uani 1 1 d . . . . .
H8 H 0.4390 0.8912 0.6681 0.071 Uiso 1 1 calc R U . . .
B9 B 0.33101(14) 0.7456(4) 0.7326(2) 0.0545(7) Uani 1 1 d . . . . .
H9 H 0.3172 0.8550 0.7847 0.065 Uiso 1 1 calc R U . . .
B10 B 0.32047(14) 0.5103(4) 0.76118(19) 0.0511(7) Uani 1 1 d . . . . .
H10 H 0.2996 0.4658 0.8318 0.061 Uiso 1 1 calc R U . . .
B11 B 0.38855(13) 0.3868(4) 0.7094(2) 0.0502(7) Uani 1 1 d . . . . .
H11 H 0.4121 0.2602 0.7451 0.060 Uiso 1 1 calc R U . . .
B12 B 0.40739(14) 0.6060(4) 0.7627(2) 0.0564(7) Uani 1 1 d . . . . .
H12 H 0.4433 0.6239 0.8343 0.068 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C22 1.332(3) . ?
N1 C18 1.340(3) . ?
C1 C2 1.642(3) . ?
C1 B4 1.686(3) . ?
C1 B5 1.699(3) . ?
C1 B6 1.701(3) . ?
C1 B3 1.709(3) . ?
C2 C11 1.512(3) . ?
C2 B7 1.696(3) . ?
C2 B11 1.702(3) . ?
C2 B6 1.714(3) . ?
C2 B3 1.719(4) . ?
C12 C13 1.398(3) . ?
C12 C17 1.411(3) . ?
C12 B5 1.587(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.369(3) . ?
C15 C16 1.376(3) . ?
C16 C17 1.394(3) . ?
C17 C18 1.490(3) . ?
C18 C19 1.386(3) . ?
C19 C20 1.375(3) . ?
C20 C21 1.371(4) . ?
C21 C22 1.367(3) . ?
B3 B8 1.745(4) . ?
B3 B7 1.758(4) . ?
B3 B4 1.772(4) . ?
B4 B9 1.758(4) . ?
B4 B8 1.776(4) . ?
B4 B5 1.789(3) . ?
B5 B6 1.774(3) . ?
B5 B10 1.787(3) . ?
B5 B9 1.801(3) . ?
B6 B10 1.744(4) . ?
B6 B11 1.762(3) . ?
B7 B12 1.761(4) . ?
B7 B11 1.763(4) . ?
B7 B8 1.771(4) . ?
B8 B12 1.762(4) . ?
B8 B9 1.771(4) . ?
B9 B10 1.763(4) . ?
B9 B12 1.767(4) . ?
B10 B11 1.769(4) . ?
B10 B12 1.779(4) . ?
B11 B12 1.756(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
C22 N1 C18 117.56(19) . . ?
C2 C1 B4 112.44(16) . . ?
C2 C1 B5 113.35(16) . . ?
B4 C1 B5 63.80(14) . . ?
C2 C1 B6 61.66(13) . . ?
B4 C1 B6 114.95(17) . . ?
B5 C1 B6 62.90(13) . . ?
C2 C1 B3 61.68(14) . . ?
B4 C1 B3 62.92(16) . . ?
B5 C1 B3 116.44(17) . . ?
B6 C1 B3 114.54(17) . . ?
C11 C2 C1 118.33(19) . . ?
C11 C2 B7 121.82(18) . . ?
C1 C2 B7 110.18(17) . . ?
C11 C2 B11 121.7(2) . . ?
C1 C2 B11 109.91(16) . . ?
B7 C2 B11 62.51(15) . . ?
C11 C2 B6 116.84(19) . . ?
C1 C2 B6 60.87(13) . . ?
B7 C2 B6 113.70(17) . . ?
B11 C2 B6 62.11(14) . . ?
C11 C2 B3 117.5(2) . . ?
C1 C2 B3 61.10(14) . . ?
B7 C2 B3 61.96(15) . . ?
B11 C2 B3 113.25(18) . . ?
B6 C2 B3 113.38(17) . . ?
C13 C12 C17 116.22(18) . . ?
C13 C12 B5 115.37(18) . . ?
C17 C12 B5 128.21(17) . . ?
C14 C13 C12 123.2(2) . . ?
C15 C14 C13 119.9(2) . . ?
C14 C15 C16 118.9(2) . . ?
C15 C16 C17 122.0(2) . . ?
C16 C17 C12 119.77(19) . . ?
C16 C17 C18 115.81(18) . . ?
C12 C17 C18 124.42(17) . . ?
N1 C18 C19 121.51(19) . . ?
N1 C18 C17 118.26(18) . . ?
C19 C18 C17 120.19(18) . . ?
C20 C19 C18 119.7(2) . . ?
C21 C20 C19 118.7(2) . . ?
C22 C21 C20 118.3(2) . . ?
N1 C22 C21 124.2(2) . . ?
C1 B3 C2 57.22(13) . . ?
C1 B3 B8 104.48(19) . . ?
C2 B3 B8 105.32(19) . . ?
C1 B3 B7 104.27(18) . . ?
C2 B3 B7 58.38(14) . . ?
B8 B3 B7 60.73(16) . . ?
C1 B3 B4 57.91(14) . . ?
C2 B3 B4 104.80(17) . . ?
B8 B3 B4 60.65(16) . . ?
B7 B3 B4 108.8(2) . . ?
C1 B4 B9 104.16(18) . . ?
C1 B4 B3 59.17(14) . . ?
B9 B4 B3 107.23(19) . . ?
C1 B4 B8 104.10(18) . . ?
B9 B4 B8 60.12(16) . . ?
B3 B4 B8 58.90(16) . . ?
C1 B4 B5 58.44(13) . . ?
B9 B4 B5 61.02(15) . . ?
B3 B4 B5 108.88(18) . . ?
B8 B4 B5 109.41(19) . . ?
C12 B5 C1 125.72(17) . . ?
C12 B5 B6 122.67(17) . . ?
C1 B5 B6 58.61(13) . . ?
C12 B5 B10 124.06(17) . . ?
C1 B5 B10 102.65(16) . . ?
B6 B5 B10 58.66(14) . . ?
C12 B5 B4 122.24(17) . . ?
C1 B5 B4 57.76(14) . . ?
B6 B5 B4 106.57(16) . . ?
B10 B5 B4 105.79(17) . . ?
C12 B5 B9 124.30(18) . . ?
C1 B5 B9 101.86(16) . . ?
B6 B5 B9 105.26(17) . . ?
B10 B5 B9 58.86(15) . . ?
B4 B5 B9 58.66(15) . . ?
C1 B6 C2 57.47(13) . . ?
C1 B6 B10 104.39(17) . . ?
C2 B6 B10 105.52(17) . . ?
C1 B6 B11 104.47(16) . . ?
C2 B6 B11 58.62(13) . . ?
B10 B6 B11 60.59(15) . . ?
C1 B6 B5 58.49(13) . . ?
C2 B6 B5 106.32(16) . . ?
B10 B6 B5 61.06(14) . . ?
B11 B6 B5 109.94(18) . . ?
C2 B7 B3 59.66(14) . . ?
C2 B7 B12 104.94(17) . . ?
B3 B7 B12 107.40(19) . . ?
C2 B7 B11 58.92(14) . . ?
B3 B7 B11 108.47(17) . . ?
B12 B7 B11 59.77(16) . . ?
C2 B7 B8 105.17(17) . . ?
B3 B7 B8 59.27(16) . . ?
B12 B7 B8 59.86(17) . . ?
B11 B7 B8 107.81(18) . . ?
B3 B8 B12 107.92(19) . . ?
B3 B8 B9 107.92(18) . . ?
B12 B8 B9 60.04(16) . . ?
B3 B8 B7 60.00(15) . . ?
B12 B8 B7 59.80(15) . . ?
B9 B8 B7 107.8(2) . . ?
B3 B8 B4 60.44(16) . . ?
B12 B8 B4 107.66(19) . . ?
B9 B8 B4 59.45(15) . . ?
B7 B8 B4 108.07(19) . . ?
B4 B9 B10 108.15(19) . . ?
B4 B9 B12 108.20(19) . . ?
B10 B9 B12 60.51(16) . . ?
B4 B9 B8 60.43(16) . . ?
B10 B9 B8 108.37(19) . . ?
B12 B9 B8 59.74(16) . . ?
B4 B9 B5 60.32(14) . . ?
B10 B9 B5 60.18(14) . . ?
B12 B9 B5 108.99(19) . . ?
B8 B9 B5 109.09(19) . . ?
B6 B10 B9 108.19(18) . . ?
B6 B10 B11 60.21(15) . . ?
B9 B10 B11 107.57(19) . . ?
B6 B10 B12 107.60(17) . . ?
B9 B10 B12 59.85(16) . . ?
B11 B10 B12 59.33(15) . . ?
B6 B10 B5 60.28(13) . . ?
B9 B10 B5 60.96(14) . . ?
B11 B10 B5 109.01(17) . . ?
B12 B10 B5 109.09(19) . . ?
C2 B11 B12 104.89(18) . . ?
C2 B11 B6 59.26(14) . . ?
B12 B11 B6 107.84(18) . . ?
C2 B11 B7 58.57(13) . . ?
B12 B11 B7 60.05(16) . . ?
B6 B11 B7 108.14(17) . . ?
C2 B11 B10 104.94(17) . . ?
B12 B11 B10 60.62(16) . . ?
B6 B11 B10 59.20(14) . . ?
B7 B11 B10 108.48(19) . . ?
B11 B12 B7 60.18(15) . . ?
B11 B12 B8 108.52(19) . . ?
B7 B12 B8 60.35(16) . . ?
B11 B12 B9 107.98(18) . . ?
B7 B12 B9 108.34(19) . . ?
B8 B12 B9 60.22(16) . . ?
B11 B12 B10 60.05(16) . . ?
B7 B12 B10 108.13(18) . . ?
B8 B12 B10 108.05(18) . . ?
B9 B12 B10 59.63(15) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_3as
_database_code_depnum_ccdc_archive 'CCDC 1987438'
loop_
_audit_author_name
_audit_author_address
'Hoi Shan CHAN'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 B10 N2'
_chemical_formula_weight         300.40

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   19.063(3)
_cell_length_b                   6.8433(9)
_cell_length_c                   13.5027(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.491(9)
_cell_angle_gamma                90
_cell_volume                     1759.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    210
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.058
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26871
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.069
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3188
_reflns_number_gt                1844
_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 KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1251P)²+0.6397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.2419
_refine_ls_wR_factor_gt          0.1917
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36068(12) 0.3551(4) 0.75240(19) 0.0634(7) Uani 1 1 d . . . . .
N2 N 0.34606(14) 0.4050(5) 0.8461(2) 0.0866(9) Uani 1 1 d . . . . .
C1 C 0.20083(16) 0.4062(5) 0.7093(3) 0.0775(10) Uani 1 1 d . . . . .
H1 H 0.2341 0.2974 0.7487 0.093 Uiso 1 1 calc R U . . .
C2 C 0.12948(15) 0.4949(5) 0.7573(2) 0.0680(9) Uani 1 1 d . . . . .
C11 C 0.1122(2) 0.4242(8) 0.8607(3) 0.1300(19) Uani 1 1 d . . . . .
H11A H 0.0698 0.4857 0.8805 0.195 Uiso 1 1 calc R U . . .
H11B H 0.1059 0.2850 0.8597 0.195 Uiso 1 1 calc R U . . .
H11C H 0.1500 0.4574 0.9069 0.195 Uiso 1 1 calc R U . . .
C12 C 0.32344(14) 0.6017(4) 0.6289(2) 0.0519(7) Uani 1 1 d . . . . .
C13 C 0.34569(16) 0.7368(4) 0.5591(2) 0.0688(9) Uani 1 1 d . . . . .
H13A H 0.3120 0.8078 0.5226 0.083 Uiso 1 1 calc R U . . .
C14 C 0.41613(19) 0.7692(5) 0.5423(3) 0.0855(11) Uani 1 1 d . . . . .
H14A H 0.4289 0.8589 0.4945 0.103 Uiso 1 1 calc R U . . .
C15 C 0.46639(19) 0.6689(6) 0.5961(3) 0.0940(12) Uani 1 1 d . . . . .
H15A H 0.5137 0.6918 0.5863 0.113 Uiso 1 1 calc R U . . .
C16 C 0.44686(16) 0.5342(6) 0.6647(3) 0.0835(11) Uani 1 1 d . . . . .
H16A H 0.4810 0.4641 0.7009 0.100 Uiso 1 1 calc R U . . .
C17 C 0.37676(14) 0.5022(4) 0.6803(2) 0.0586(8) Uani 1 1 d . . . . .
C18 C 0.36101(19) 0.1608(5) 0.7404(3) 0.0860(11) Uani 1 1 d . . . . .
H18A H 0.3705 0.0950 0.6822 0.103 Uiso 1 1 calc R U . . .
C19 C 0.3452(2) 0.0769(7) 0.8269(4) 0.1100(15) Uani 1 1 d . . . . .
H19A H 0.3409 -0.0557 0.8406 0.132 Uiso 1 1 calc R U . . .
C20 C 0.3367(2) 0.2311(9) 0.8901(3) 0.1031(15) Uani 1 1 d . . . . .
H20A H 0.3258 0.2170 0.9561 0.124 Uiso 1 1 calc R U . . .
B3 B 0.20100(18) 0.6338(5) 0.7484(3) 0.0646(10) Uani 1 1 d . . . . .
H3 H 0.2337 0.6800 0.8134 0.077 Uiso 1 1 calc R U . . .
B4 B 0.24167(16) 0.5792(4) 0.6395(2) 0.0492(8) Uani 1 1 d . . . . .
B5 B 0.1887(2) 0.3902(6) 0.5861(3) 0.0824(13) Uani 1 1 d . . . . .
H5 H 0.2120 0.2753 0.5410 0.099 Uiso 1 1 calc R U . . .
B6 B 0.1192(2) 0.3373(6) 0.6631(4) 0.0860(14) Uani 1 1 d . . . . .
H6 H 0.0975 0.1891 0.6693 0.103 Uiso 1 1 calc R U . . .
B7 B 0.1185(2) 0.7302(5) 0.7284(3) 0.0761(12) Uani 1 1 d . . . . .
H7 H 0.0960 0.8393 0.7777 0.091 Uiso 1 1 calc R U . . .
B8 B 0.1872(2) 0.7855(5) 0.6513(4) 0.0854(14) Uani 1 1 d . . . . .
H8 H 0.2097 0.9334 0.6482 0.102 Uiso 1 1 calc R U . . .
B9 B 0.1776(2) 0.6327(8) 0.5458(3) 0.0985(17) Uani 1 1 d . . . . .
H9 H 0.1930 0.6787 0.4717 0.118 Uiso 1 1 calc R U . . .
B10 B 0.1036(2) 0.4874(10) 0.5594(4) 0.1106(19) Uani 1 1 d . . . . .
H10 H 0.0711 0.4392 0.4946 0.133 Uiso 1 1 calc R U . . .
B11 B 0.06632(18) 0.5459(5) 0.6711(3) 0.0651(10) Uani 1 1 d . . . . .
H11 H 0.0095 0.5343 0.6809 0.078 Uiso 1 1 calc R U . . .
B12 B 0.1029(2) 0.7335(7) 0.6019(4) 0.0930(15) Uani 1 1 d . . . . .
H12 H 0.0701 0.8478 0.5661 0.112 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.340(4) . ?
N1 N2 1.352(3) . ?
N1 C17 1.442(4) . ?
N2 C20 1.345(5) . ?
C1 B3 1.645(5) . ?
C1 C2 1.648(4) . ?
C1 B5 1.672(6) . ?
C1 B6 1.716(5) . ?
C1 B4 1.720(4) . ?
C2 C11 1.528(5) . ?
C2 B7 1.667(5) . ?
C2 B3 1.671(5) . ?
C2 B6 1.672(5) . ?
C2 B11 1.675(5) . ?
C12 C17 1.385(4) . ?
C12 C13 1.399(4) . ?
C12 B4 1.579(4) . ?
C13 C14 1.389(4) . ?
C14 C15 1.363(5) . ?
C15 C16 1.370(5) . ?
C16 C17 1.379(4) . ?
C18 C19 1.348(5) . ?
C19 C20 1.371(6) . ?
B3 B8 1.684(6) . ?
B3 B7 1.715(5) . ?
B3 B4 1.732(4) . ?
B4 B9 1.759(5) . ?
B4 B8 1.763(5) . ?
B4 B5 1.775(5) . ?
B5 B6 1.755(6) . ?
B5 B9 1.757(7) . ?
B5 B10 1.775(6) . ?
B6 B10 1.751(7) . ?
B6 B11 1.754(5) . ?
B7 B12 1.722(7) . ?
B7 B8 1.750(6) . ?
B7 B11 1.764(5) . ?
B8 B12 1.750(7) . ?
B8 B9 1.770(7) . ?
B9 B10 1.742(7) . ?
B9 B12 1.780(6) . ?
B10 B11 1.741(6) . ?
B10 B12 1.779(8) . ?
B11 B12 1.750(6) . ?

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
C18 N1 N2 111.5(3) . . ?
C18 N1 C17 127.5(3) . . ?
N2 N1 C17 121.0(3) . . ?
C20 N2 N1 103.1(3) . . ?
B3 C1 C2 61.0(2) . . ?
B3 C1 B5 112.3(3) . . ?
C2 C1 B5 109.5(3) . . ?
B3 C1 B6 111.5(3) . . ?
C2 C1 B6 59.6(2) . . ?
B5 C1 B6 62.4(3) . . ?
B3 C1 B4 61.91(19) . . ?
C2 C1 B4 111.3(2) . . ?
B5 C1 B4 63.1(2) . . ?
B6 C1 B4 114.5(3) . . ?
C11 C2 C1 117.2(3) . . ?
C11 C2 B7 119.3(3) . . ?
C1 C2 B7 111.2(2) . . ?
C11 C2 B3 117.1(3) . . ?
C1 C2 B3 59.43(18) . . ?
B7 C2 B3 61.8(2) . . ?
C11 C2 B6 117.9(3) . . ?
C1 C2 B6 62.2(2) . . ?
B7 C2 B6 115.8(3) . . ?
B3 C2 B6 112.4(2) . . ?
C11 C2 B11 121.6(3) . . ?
C1 C2 B11 112.6(3) . . ?
B7 C2 B11 63.7(2) . . ?
B3 C2 B11 113.3(3) . . ?
B6 C2 B11 63.2(2) . . ?
C17 C12 C13 115.2(3) . . ?
C17 C12 B4 127.8(3) . . ?
C13 C12 B4 117.1(3) . . ?
C14 C13 C12 122.6(3) . . ?
C15 C14 C13 119.6(3) . . ?
C14 C15 C16 119.6(3) . . ?
C15 C16 C17 120.3(3) . . ?
C16 C17 C12 122.7(3) . . ?
C16 C17 N1 116.8(3) . . ?
C12 C17 N1 120.6(2) . . ?
N1 C18 C19 108.4(4) . . ?
C18 C19 C20 104.4(4) . . ?
N2 C20 C19 112.7(4) . . ?
C1 B3 C2 59.6(2) . . ?
C1 B3 B8 109.6(3) . . ?
C2 B3 B8 107.9(3) . . ?
C1 B3 B7 108.9(3) . . ?
C2 B3 B7 59.0(2) . . ?
B8 B3 B7 62.0(2) . . ?
C1 B3 B4 61.17(19) . . ?
C2 B3 B4 109.6(3) . . ?
B8 B3 B4 62.1(2) . . ?
B7 B3 B4 113.0(3) . . ?
C12 B4 C1 126.1(2) . . ?
C12 B4 B3 122.4(2) . . ?
C1 B4 B3 56.92(19) . . ?
C12 B4 B9 124.9(3) . . ?
C1 B4 B9 102.7(3) . . ?
B3 B4 B9 104.1(2) . . ?
C12 B4 B8 121.1(2) . . ?
C1 B4 B8 102.7(2) . . ?
B3 B4 B8 57.6(2) . . ?
B9 B4 B8 60.3(3) . . ?
C12 B4 B5 125.5(2) . . ?
C1 B4 B5 57.1(2) . . ?
B3 B4 B5 103.5(2) . . ?
B9 B4 B5 59.6(3) . . ?
B8 B4 B5 107.0(3) . . ?
C1 B5 B6 60.0(2) . . ?
C1 B5 B9 104.8(3) . . ?
B6 B5 B9 107.2(3) . . ?
C1 B5 B10 105.3(3) . . ?
B6 B5 B10 59.5(3) . . ?
B9 B5 B10 59.1(3) . . ?
C1 B5 B4 59.8(2) . . ?
B6 B5 B4 109.9(3) . . ?
B9 B5 B4 59.7(2) . . ?
B10 B5 B4 107.9(3) . . ?
C2 B6 C1 58.2(2) . . ?
C2 B6 B10 103.9(3) . . ?
C1 B6 B10 104.4(3) . . ?
C2 B6 B11 58.5(2) . . ?
C1 B6 B11 105.6(3) . . ?
B10 B6 B11 59.6(3) . . ?
C2 B6 B5 104.6(2) . . ?
C1 B6 B5 57.6(2) . . ?
B10 B6 B5 60.8(3) . . ?
B11 B6 B5 108.6(3) . . ?
C2 B7 B3 59.2(2) . . ?
C2 B7 B12 105.0(3) . . ?
B3 B7 B12 106.2(3) . . ?
C2 B7 B8 105.0(2) . . ?
B3 B7 B8 58.1(2) . . ?
B12 B7 B8 60.5(3) . . ?
C2 B7 B11 58.3(2) . . ?
B3 B7 B11 106.9(2) . . ?
B12 B7 B11 60.3(2) . . ?
B8 B7 B11 108.4(3) . . ?
B3 B8 B12 106.3(3) . . ?
B3 B8 B7 59.9(2) . . ?
B12 B8 B7 58.9(3) . . ?
B3 B8 B4 60.3(2) . . ?
B12 B8 B4 109.7(3) . . ?
B7 B8 B4 109.8(3) . . ?
B3 B8 B9 105.6(3) . . ?
B12 B8 B9 60.8(3) . . ?
B7 B8 B9 107.3(3) . . ?
B4 B8 B9 59.7(2) . . ?
B10 B9 B5 61.0(3) . . ?
B10 B9 B4 110.2(3) . . ?
B5 B9 B4 60.7(2) . . ?
B10 B9 B8 108.0(3) . . ?
B5 B9 B8 107.6(3) . . ?
B4 B9 B8 60.0(2) . . ?
B10 B9 B12 60.7(3) . . ?
B5 B9 B12 108.7(3) . . ?
B4 B9 B12 108.5(3) . . ?
B8 B9 B12 59.1(3) . . ?
B11 B10 B9 108.9(3) . . ?
B11 B10 B6 60.3(2) . . ?
B9 B10 B6 108.0(3) . . ?
B11 B10 B5 108.3(3) . . ?
B9 B10 B5 59.9(2) . . ?
B6 B10 B5 59.7(3) . . ?
B11 B10 B12 59.6(2) . . ?
B9 B10 B12 60.7(3) . . ?
B6 B10 B12 107.5(3) . . ?
B5 B10 B12 108.0(3) . . ?
C2 B11 B10 104.2(3) . . ?
C2 B11 B12 103.5(3) . . ?
B10 B11 B12 61.3(3) . . ?
C2 B11 B6 58.3(2) . . ?
B10 B11 B6 60.1(3) . . ?
B12 B11 B6 108.7(3) . . ?
C2 B11 B7 57.9(2) . . ?
B10 B11 B7 107.5(3) . . ?
B12 B11 B7 58.7(3) . . ?
B6 B11 B7 107.1(3) . . ?
B7 B12 B8 60.6(3) . . ?
B7 B12 B11 61.1(2) . . ?
B8 B12 B11 109.1(3) . . ?
B7 B12 B10 107.7(3) . . ?
B8 B12 B10 107.2(3) . . ?
B11 B12 B10 59.1(2) . . ?
B7 B12 B9 108.1(3) . . ?
B8 B12 B9 60.2(2) . . ?
B11 B12 B9 106.7(3) . . ?
B10 B12 B9 58.6(3) . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_3ay
_database_code_depnum_ccdc_archive 'CCDC 1987441'
loop_
_audit_author_name
_audit_author_address
'Hoi Shan CHAN'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H34 B20 N2'
_chemical_formula_weight         494.67

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

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

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

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

_cell_length_a                   11.1641(3)
_cell_length_b                   11.5247(3)
_cell_length_c                   12.2762(5)
_cell_angle_alpha                85.6539(17)
_cell_angle_beta                 71.2257(14)
_cell_angle_gamma                82.6628(11)
_cell_volume                     1482.19(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    68
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.054
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23235
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.753
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5369
_reflns_number_gt                3557
_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 KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1384P)²+0.5259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5369
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2502
_refine_ls_wR_factor_gt          0.2206
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.38669(19) 0.58398(16) 0.25672(17) 0.0457(5) Uani 1 1 d . . . . .
N2 N 0.4526(2) 0.57432(19) 0.15649(18) 0.0530(6) Uani 1 1 d . . . . .
C1 C 0.6926(3) 0.3244(3) 0.2805(3) 0.0779(10) Uani 1 1 d . . . . .
C2 C 0.5534(3) 0.3997(3) 0.3433(3) 0.0732(9) Uani 1 1 d . . . . .
H2 H 0.5428 0.4960 0.3405 0.088 Uiso 1 1 calc R U . . .
C11 C 0.8032(4) 0.3936(4) 0.2147(5) 0.1268(18) Uani 1 1 d . . . . .
H11A H 0.8779 0.3404 0.1826 0.190 Uiso 1 1 calc R U . . .
H11B H 0.7821 0.4401 0.1538 0.190 Uiso 1 1 calc R U . . .
H11C H 0.8191 0.4439 0.2662 0.190 Uiso 1 1 calc R U . . .
C12 C 0.3001(2) 0.3967(2) 0.3250(2) 0.0488(6) Uani 1 1 d . . . . .
C13 C 0.2801(2) 0.5156(2) 0.29131(19) 0.0418(6) Uani 1 1 d . . . . .
C14 C 0.1612(2) 0.5741(2) 0.2957(2) 0.0463(6) Uani 1 1 d . . . . .
C15 C 0.0590(3) 0.5068(2) 0.3306(2) 0.0615(8) Uani 1 1 d . . . . .
H15A H -0.0217 0.5419 0.3335 0.074 Uiso 1 1 calc R U . . .
C16 C 0.0748(3) 0.3899(3) 0.3608(3) 0.0685(9) Uani 1 1 d . . . . .
H16A H 0.0054 0.3466 0.3822 0.082 Uiso 1 1 calc R U . . .
C17 C 0.1924(3) 0.3368(2) 0.3595(2) 0.0626(8) Uani 1 1 d . . . . .
H17A H 0.2005 0.2582 0.3824 0.075 Uiso 1 1 calc R U . . .
C18 C 0.5595(2) 0.6402(2) 0.1215(2) 0.0476(6) Uani 1 1 d . . . . .
C19 C 0.6371(3) 0.6289(3) 0.0094(2) 0.0698(9) Uani 1 1 d . . . . .
H19A H 0.6173 0.5818 -0.0392 0.084 Uiso 1 1 calc R U . . .
C20 C 0.7441(3) 0.6870(4) -0.0309(3) 0.0873(11) Uani 1 1 d . . . . .
H20A H 0.7970 0.6789 -0.1066 0.105 Uiso 1 1 calc R U . . .
C21 C 0.7726(3) 0.7576(3) 0.0417(3) 0.0848(11) Uani 1 1 d . . . . .
H21A H 0.8444 0.7976 0.0145 0.102 Uiso 1 1 calc R U . . .
C22 C 0.6957(3) 0.7687(3) 0.1533(3) 0.0773(10) Uani 1 1 d . . . . .
H22A H 0.7158 0.8156 0.2019 0.093 Uiso 1 1 calc R U . . .
C23 C 0.5891(3) 0.7110(2) 0.1938(3) 0.0591(7) Uani 1 1 d . . . . .
H23A H 0.5367 0.7192 0.2696 0.071 Uiso 1 1 calc R U . . .
C24 C 0.3494(4) 0.9711(4) 0.1013(5) 0.1328(19) Uani 1 1 d . . . . .
H24A H 0.3346 1.0340 0.0496 0.199 Uiso 1 1 calc R U . . .
H24B H 0.3815 1.0002 0.1564 0.199 Uiso 1 1 calc R U . . .
H24C H 0.4105 0.9113 0.0583 0.199 Uiso 1 1 calc R U . . .
C31 C 0.2243(3) 0.9197(3) 0.1642(3) 0.0799(11) Uani 1 1 d . . . . .
C32 C 0.2336(3) 0.8105(2) 0.2563(3) 0.0629(8) Uani 1 1 d . . . . .
H32 H 0.3259 0.7778 0.2678 0.075 Uiso 1 1 calc R U . . .
B3 B 0.5736(3) 0.3265(3) 0.2246(3) 0.0582(8) Uani 1 1 d . . . . .
H3 H 0.5766 0.3718 0.1418 0.070 Uiso 1 1 calc R U . . .
B4 B 0.6713(4) 0.1979(4) 0.2279(4) 0.0849(13) Uani 1 1 d . . . . .
H4 H 0.7374 0.1569 0.1498 0.102 Uiso 1 1 calc R U . . .
B5 B 0.7121(5) 0.1964(4) 0.3554(4) 0.0912(14) Uani 1 1 d . . . . .
H5 H 0.8047 0.1551 0.3606 0.109 Uiso 1 1 calc R U . . .
B6 B 0.6368(5) 0.3246(4) 0.4285(4) 0.0942(15) Uani 1 1 d . . . . .
H6 H 0.6797 0.3672 0.4819 0.113 Uiso 1 1 calc R U . . .
B7 B 0.4291(3) 0.3299(2) 0.3349(3) 0.0535(8) Uani 1 1 d . . . . .
B8 B 0.5069(4) 0.1981(3) 0.2636(3) 0.0722(10) Uani 1 1 d . . . . .
H8 H 0.4647 0.1564 0.2091 0.087 Uiso 1 1 calc R U . . .
B9 B 0.5909(5) 0.1147(3) 0.3484(4) 0.0906(14) Uani 1 1 d . . . . .
H9 H 0.6032 0.0185 0.3503 0.109 Uiso 1 1 calc R U . . .
B10 B 0.5695(5) 0.1939(4) 0.4723(3) 0.0955(15) Uani 1 1 d . . . . .
H10 H 0.5681 0.1494 0.5551 0.115 Uiso 1 1 calc R U . . .
B11 B 0.4709(4) 0.3244(3) 0.4639(3) 0.0758(12) Uani 1 1 d . . . . .
H11 H 0.4049 0.3664 0.5414 0.091 Uiso 1 1 calc R U . . .
B12 B 0.4417(4) 0.1946(3) 0.4159(3) 0.0788(12) Uani 1 1 d . . . . .
H12 H 0.3569 0.1503 0.4619 0.095 Uiso 1 1 calc R U . . .
B33 B 0.1646(4) 0.9447(3) 0.3051(4) 0.0757(11) Uani 1 1 d . . . . .
H33 H 0.2056 1.0021 0.3481 0.091 Uiso 1 1 calc R U . . .
B34 B 0.0807(3) 1.0015(3) 0.2117(3) 0.0715(11) Uani 1 1 d . . . . .
H34 H 0.0647 1.0960 0.1931 0.086 Uiso 1 1 calc R U . . .
B35 B 0.1111(4) 0.9003(3) 0.1051(3) 0.0783(12) Uani 1 1 d . . . . .
H35 H 0.1158 0.9288 0.0164 0.094 Uiso 1 1 calc R U . . .
B36 B 0.2108(3) 0.7796(3) 0.1338(3) 0.0675(10) Uani 1 1 d . . . . .
H36 H 0.2814 0.7295 0.0641 0.081 Uiso 1 1 calc R U . . .
B37 B 0.1034(3) 0.8149(3) 0.3732(3) 0.0601(9) Uani 1 1 d . . . . .
H37 H 0.1033 0.7876 0.4610 0.072 Uiso 1 1 calc R U . . .
B38 B 0.0010(3) 0.9355(3) 0.3449(3) 0.0651(9) Uani 1 1 d . . . . .
H38 H -0.0678 0.9868 0.4146 0.078 Uiso 1 1 calc R U . . .
B39 B -0.0343(3) 0.9076(3) 0.2205(3) 0.0656(9) Uani 1 1 d . . . . .
H39 H -0.1262 0.9401 0.2081 0.079 Uiso 1 1 calc R U . . .
B40 B 0.0472(3) 0.7685(3) 0.1713(3) 0.0671(10) Uani 1 1 d . . . . .
H40 H 0.0084 0.7111 0.1265 0.081 Uiso 1 1 calc R U . . .
B41 B 0.1318(3) 0.7088(3) 0.2670(2) 0.0477(7) Uani 1 1 d . . . . .
B42 B -0.0202(3) 0.7914(3) 0.3209(3) 0.0588(8) Uani 1 1 d . . . . .
H42 H -0.1033 0.7488 0.3746 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.218(3) . ?
N1 C13 1.443(3) . ?
N2 C18 1.428(3) . ?
C1 C11 1.525(5) . ?
C1 C2 1.657(4) . ?
C1 B3 1.677(5) . ?
C1 B5 1.706(5) . ?
C1 B4 1.712(5) . ?
C1 B6 1.720(6) . ?
C2 B3 1.676(5) . ?
C2 B11 1.711(5) . ?
C2 B7 1.724(5) . ?
C2 B6 1.730(5) . ?
C12 C17 1.393(4) . ?
C12 C13 1.412(3) . ?
C12 B7 1.580(4) . ?
C13 C14 1.397(3) . ?
C14 C15 1.395(3) . ?
C14 B41 1.582(4) . ?
C15 C16 1.375(4) . ?
C16 C17 1.371(4) . ?
C18 C19 1.375(4) . ?
C18 C23 1.390(4) . ?
C19 C20 1.376(4) . ?
C20 C21 1.384(5) . ?
C21 C22 1.369(5) . ?
C22 C23 1.369(4) . ?
C24 C31 1.532(5) . ?
C31 C32 1.643(4) . ?
C31 B33 1.675(6) . ?
C31 B35 1.691(6) . ?
C31 B34 1.701(5) . ?
C31 B36 1.720(5) . ?
C32 B36 1.675(5) . ?
C32 B37 1.681(4) . ?
C32 B33 1.698(5) . ?
C32 B41 1.704(4) . ?
B3 B8 1.709(5) . ?
B3 B4 1.731(5) . ?
B3 B7 1.739(5) . ?
B4 B8 1.745(6) . ?
B4 B9 1.750(6) . ?
B4 B5 1.764(6) . ?
B5 B6 1.759(5) . ?
B5 B10 1.769(7) . ?
B5 B9 1.771(7) . ?
B6 B10 1.741(7) . ?
B6 B11 1.760(7) . ?
B7 B11 1.785(5) . ?
B7 B8 1.790(4) . ?
B7 B12 1.801(4) . ?
B8 B9 1.770(6) . ?
B8 B12 1.774(6) . ?
B9 B10 1.767(6) . ?
B9 B12 1.773(6) . ?
B10 B11 1.763(5) . ?
B10 B12 1.774(7) . ?
B11 B12 1.754(5) . ?
B33 B34 1.744(6) . ?
B33 B38 1.748(5) . ?
B33 B37 1.764(5) . ?
B34 B35 1.741(6) . ?
B34 B39 1.754(5) . ?
B34 B38 1.758(5) . ?
B35 B36 1.755(5) . ?
B35 B39 1.775(5) . ?
B35 B40 1.786(5) . ?
B36 B40 1.753(5) . ?
B36 B41 1.780(4) . ?
B37 B42 1.755(5) . ?
B37 B38 1.771(5) . ?
B37 B41 1.781(5) . ?
B38 B39 1.756(5) . ?
B38 B42 1.767(5) . ?
B39 B42 1.778(5) . ?
B39 B40 1.784(5) . ?
B40 B42 1.772(5) . ?
B40 B41 1.781(4) . ?
B41 B42 1.784(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
N2 N1 C13 114.4(2) . . ?
N1 N2 C18 115.0(2) . . ?
C11 C1 C2 117.5(3) . . ?
C11 C1 B3 117.1(3) . . ?
C2 C1 B3 60.35(18) . . ?
C11 C1 B5 122.7(3) . . ?
C2 C1 B5 111.2(3) . . ?
B3 C1 B5 111.9(3) . . ?
C11 C1 B4 120.7(4) . . ?
C2 C1 B4 110.5(3) . . ?
B3 C1 B4 61.4(2) . . ?
B5 C1 B4 62.2(2) . . ?
C11 C1 B6 119.9(3) . . ?
C2 C1 B6 61.6(2) . . ?
B3 C1 B6 111.5(3) . . ?
B5 C1 B6 61.8(2) . . ?
B4 C1 B6 112.4(3) . . ?
C1 C2 B3 60.4(2) . . ?
C1 C2 B11 109.9(2) . . ?
B3 C2 B11 110.8(2) . . ?
C1 C2 B7 111.4(2) . . ?
B3 C2 B7 61.51(19) . . ?
B11 C2 B7 62.6(2) . . ?
C1 C2 B6 61.0(2) . . ?
B3 C2 B6 111.1(2) . . ?
B11 C2 B6 61.5(2) . . ?
B7 C2 B6 113.8(3) . . ?
C17 C12 C13 115.5(2) . . ?
C17 C12 B7 118.2(2) . . ?
C13 C12 B7 126.1(2) . . ?
C14 C13 C12 124.0(2) . . ?
C14 C13 N1 117.1(2) . . ?
C12 C13 N1 118.7(2) . . ?
C15 C14 C13 116.3(2) . . ?
C15 C14 B41 117.5(2) . . ?
C13 C14 B41 126.2(2) . . ?
C16 C15 C14 121.6(3) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C12 122.2(2) . . ?
C19 C18 C23 119.8(2) . . ?
C19 C18 N2 116.2(2) . . ?
C23 C18 N2 124.0(2) . . ?
C18 C19 C20 120.2(3) . . ?
C19 C20 C21 119.6(3) . . ?
C22 C21 C20 120.3(3) . . ?
C21 C22 C23 120.3(3) . . ?
C22 C23 C18 119.8(3) . . ?
C24 C31 C32 115.5(3) . . ?
C24 C31 B33 115.1(4) . . ?
C32 C31 B33 61.6(2) . . ?
C24 C31 B35 125.5(3) . . ?
C32 C31 B35 109.0(2) . . ?
B33 C31 B35 112.8(3) . . ?
C24 C31 B34 123.9(3) . . ?
C32 C31 B34 110.1(2) . . ?
B33 C31 B34 62.2(2) . . ?
B35 C31 B34 61.8(2) . . ?
C24 C31 B36 117.9(3) . . ?
C32 C31 B36 59.68(18) . . ?
B33 C31 B36 112.5(2) . . ?
B35 C31 B36 61.9(2) . . ?
B34 C31 B36 112.5(3) . . ?
C31 C32 B36 62.5(2) . . ?
C31 C32 B37 111.9(2) . . ?
B36 C32 B37 115.2(2) . . ?
C31 C32 B33 60.1(2) . . ?
B36 C32 B33 113.7(2) . . ?
B37 C32 B33 62.9(2) . . ?
C31 C32 B41 114.3(2) . . ?
B36 C32 B41 63.59(18) . . ?
B37 C32 B41 63.48(18) . . ?
B33 C32 B41 115.8(2) . . ?
C2 B3 C1 59.24(19) . . ?
C2 B3 B8 109.1(2) . . ?
C1 B3 B8 108.6(2) . . ?
C2 B3 B4 108.7(2) . . ?
C1 B3 B4 60.3(2) . . ?
B8 B3 B4 61.0(2) . . ?
C2 B3 B7 60.61(19) . . ?
C1 B3 B7 109.7(2) . . ?
B8 B3 B7 62.54(19) . . ?
B4 B3 B7 112.5(3) . . ?
C1 B4 B3 58.31(19) . . ?
C1 B4 B8 105.3(2) . . ?
B3 B4 B8 58.9(2) . . ?
C1 B4 B9 105.6(3) . . ?
B3 B4 B9 106.8(3) . . ?
B8 B4 B9 60.9(3) . . ?
C1 B4 B5 58.8(2) . . ?
B3 B4 B5 106.7(3) . . ?
B8 B4 B5 109.1(3) . . ?
B9 B4 B5 60.5(3) . . ?
C1 B5 B6 59.5(2) . . ?
C1 B5 B4 59.1(2) . . ?
B6 B5 B4 108.1(3) . . ?
C1 B5 B10 105.0(3) . . ?
B6 B5 B10 59.1(3) . . ?
B4 B5 B10 107.2(3) . . ?
C1 B5 B9 105.0(3) . . ?
B6 B5 B9 107.3(3) . . ?
B4 B5 B9 59.3(3) . . ?
B10 B5 B9 59.9(3) . . ?
C1 B6 C2 57.4(2) . . ?
C1 B6 B10 105.6(3) . . ?
C2 B6 B10 105.9(3) . . ?
C1 B6 B5 58.7(2) . . ?
C2 B6 B5 105.4(3) . . ?
B10 B6 B5 60.7(3) . . ?
C1 B6 B11 104.8(3) . . ?
C2 B6 B11 58.7(2) . . ?
B10 B6 B11 60.5(3) . . ?
B5 B6 B11 108.7(3) . . ?
C12 B7 C2 123.6(2) . . ?
C12 B7 B3 124.0(2) . . ?
C2 B7 B3 57.89(19) . . ?
C12 B7 B11 122.6(2) . . ?
C2 B7 B11 58.3(2) . . ?
B3 B7 B11 104.6(2) . . ?
C12 B7 B8 124.8(2) . . ?
C2 B7 B8 103.4(2) . . ?
B3 B7 B8 57.9(2) . . ?
B11 B7 B8 105.4(2) . . ?
C12 B7 B12 124.6(3) . . ?
C2 B7 B12 103.4(2) . . ?
B3 B7 B12 104.2(2) . . ?
B11 B7 B12 58.6(2) . . ?
B8 B7 B12 59.2(2) . . ?
B3 B8 B4 60.1(2) . . ?
B3 B8 B9 106.9(3) . . ?
B4 B8 B9 59.7(2) . . ?
B3 B8 B12 106.6(3) . . ?
B4 B8 B12 108.0(3) . . ?
B9 B8 B12 60.0(2) . . ?
B3 B8 B7 59.57(19) . . ?
B4 B8 B7 109.4(3) . . ?
B9 B8 B7 109.3(3) . . ?
B12 B8 B7 60.69(18) . . ?
B4 B9 B10 108.0(3) . . ?
B4 B9 B8 59.4(2) . . ?
B10 B9 B8 107.9(2) . . ?
B4 B9 B5 60.1(3) . . ?
B10 B9 B5 60.0(3) . . ?
B8 B9 B5 107.6(3) . . ?
B4 B9 B12 107.8(3) . . ?
B10 B9 B12 60.1(2) . . ?
B8 B9 B12 60.1(2) . . ?
B5 B9 B12 108.1(3) . . ?
B6 B10 B11 60.3(2) . . ?
B6 B10 B9 108.3(3) . . ?
B11 B10 B9 107.6(3) . . ?
B6 B10 B5 60.1(3) . . ?
B11 B10 B5 108.1(3) . . ?
B9 B10 B5 60.1(3) . . ?
B6 B10 B12 108.1(3) . . ?
B11 B10 B12 59.4(2) . . ?
B9 B10 B12 60.1(2) . . ?
B5 B10 B12 108.2(3) . . ?
C2 B11 B12 106.0(2) . . ?
C2 B11 B6 59.8(2) . . ?
B12 B11 B6 108.2(3) . . ?
C2 B11 B10 105.7(3) . . ?
B12 B11 B10 60.6(2) . . ?
B6 B11 B10 59.2(3) . . ?
C2 B11 B7 59.07(18) . . ?
B12 B11 B7 61.18(19) . . ?
B6 B11 B7 109.4(3) . . ?
B10 B11 B7 109.9(2) . . ?
B11 B12 B9 107.7(3) . . ?
B11 B12 B10 60.0(2) . . ?
B9 B12 B10 59.8(2) . . ?
B11 B12 B8 107.4(3) . . ?
B9 B12 B8 59.9(2) . . ?
B10 B12 B8 107.4(3) . . ?
B11 B12 B7 60.26(18) . . ?
B9 B12 B7 108.7(3) . . ?
B10 B12 B7 108.7(3) . . ?
B8 B12 B7 60.09(18) . . ?
C31 B33 C32 58.3(2) . . ?
C31 B33 B34 59.6(2) . . ?
C32 B33 B34 105.6(3) . . ?
C31 B33 B38 106.8(3) . . ?
C32 B33 B38 104.9(3) . . ?
B34 B33 B38 60.5(2) . . ?
C31 B33 B37 106.4(3) . . ?
C32 B33 B37 58.05(18) . . ?
B34 B33 B37 109.0(3) . . ?
B38 B33 B37 60.6(2) . . ?
C31 B34 B35 58.8(2) . . ?
C31 B34 B33 58.2(2) . . ?
B35 B34 B33 107.1(3) . . ?
C31 B34 B39 106.2(2) . . ?
B35 B34 B39 61.0(2) . . ?
B33 B34 B39 107.8(2) . . ?
C31 B34 B38 105.2(2) . . ?
B35 B34 B38 108.5(3) . . ?
B33 B34 B38 59.9(2) . . ?
B39 B34 B38 60.0(2) . . ?
C31 B35 B34 59.4(2) . . ?
C31 B35 B36 59.9(2) . . ?
B34 B35 B36 108.9(3) . . ?
C31 B35 B39 105.7(3) . . ?
B34 B35 B39 59.9(2) . . ?
B36 B35 B39 107.7(2) . . ?
C31 B35 B40 105.8(2) . . ?
B34 B35 B40 108.2(2) . . ?
B36 B35 B40 59.31(19) . . ?
B39 B35 B40 60.1(2) . . ?
C32 B36 C31 57.9(2) . . ?
C32 B36 B40 104.9(2) . . ?
C31 B36 B40 106.0(2) . . ?
C32 B36 B35 104.6(2) . . ?
C31 B36 B35 58.2(2) . . ?
B40 B36 B35 61.2(2) . . ?
C32 B36 B41 58.99(17) . . ?
C31 B36 B41 106.8(2) . . ?
B40 B36 B41 60.53(18) . . ?
B35 B36 B41 109.9(2) . . ?
C32 B37 B42 104.6(2) . . ?
C32 B37 B33 59.03(19) . . ?
B42 B37 B33 107.4(2) . . ?
C32 B37 B38 104.6(2) . . ?
B42 B37 B38 60.15(19) . . ?
B33 B37 B38 59.27(19) . . ?
C32 B37 B41 58.88(18) . . ?
B42 B37 B41 60.61(18) . . ?
B33 B37 B41 108.8(2) . . ?
B38 B37 B41 109.2(2) . . ?
B33 B38 B39 107.5(3) . . ?
B33 B38 B34 59.7(2) . . ?
B39 B38 B34 59.9(2) . . ?
B33 B38 B42 107.6(2) . . ?
B39 B38 B42 60.6(2) . . ?
B34 B38 B42 108.3(3) . . ?
B33 B38 B37 60.16(19) . . ?
B39 B38 B37 108.1(2) . . ?
B34 B38 B37 108.0(2) . . ?
B42 B38 B37 59.48(19) . . ?
B34 B39 B38 60.1(2) . . ?
B34 B39 B35 59.1(2) . . ?
B38 B39 B35 107.1(3) . . ?
B34 B39 B42 108.0(2) . . ?
B38 B39 B42 60.0(2) . . ?
B35 B39 B42 107.5(2) . . ?
B34 B39 B40 107.8(2) . . ?
B38 B39 B40 107.7(2) . . ?
B35 B39 B40 60.3(2) . . ?
B42 B39 B40 59.67(19) . . ?
B36 B40 B42 107.6(3) . . ?
B36 B40 B41 60.50(18) . . ?
B42 B40 B41 60.29(18) . . ?
B36 B40 B39 107.4(3) . . ?
B42 B40 B39 59.99(19) . . ?
B41 B40 B39 108.9(2) . . ?
B36 B40 B35 59.5(2) . . ?
B42 B40 B35 107.2(3) . . ?
B41 B40 B35 108.4(3) . . ?
B39 B40 B35 59.6(2) . . ?
C14 B41 C32 124.0(2) . . ?
C14 B41 B36 123.5(2) . . ?
C32 B41 B36 57.42(19) . . ?
C14 B41 B37 120.9(2) . . ?
C32 B41 B37 57.63(18) . . ?
B36 B41 B37 105.5(2) . . ?
C14 B41 B40 125.9(2) . . ?
C32 B41 B40 102.5(2) . . ?
B36 B41 B40 58.97(19) . . ?
B37 B41 B40 106.1(2) . . ?
C14 B41 B42 124.5(2) . . ?
C32 B41 B42 102.4(2) . . ?
B36 B41 B42 105.9(2) . . ?
B37 B41 B42 58.98(19) . . ?
B40 B41 B42 59.61(18) . . ?
B37 B42 B38 60.38(19) . . ?
B37 B42 B40 107.7(2) . . ?
B38 B42 B40 107.7(2) . . ?
B37 B42 B39 107.8(2) . . ?
B38 B42 B39 59.4(2) . . ?
B40 B42 B39 60.33(19) . . ?
B37 B42 B41 60.41(18) . . ?
B38 B42 B41 109.2(2) . . ?
B40 B42 B41 60.10(17) . . ?
B39 B42 B41 109.0(2) . . ?

_refine_diff_density_max         0.858
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_3ax
_database_code_depnum_ccdc_archive 'CCDC 1987440'
loop_
_audit_author_name
_audit_author_address
'Hoi Shan CHAN'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H29 B20 N'
_chemical_formula_weight         415.57

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

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

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

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

_cell_length_a                   12.1083(4)
_cell_length_b                   15.2069(5)
_cell_length_c                   13.3711(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.9866(17)
_cell_angle_gamma                90
_cell_volume                     2458.67(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1107
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.052
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29884
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.684
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4446
_reflns_number_gt                3689
_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 KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1152P)²+0.8062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4446
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1767
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.87296(19) 0.09963(12) 0.50438(17) 0.0755(7) Uani 1 1 d . . . . .
C1 C 0.81930(18) -0.10547(12) 0.55798(16) 0.0508(5) Uani 1 1 d . . . . .
H1 H 0.8885 -0.0586 0.5640 0.061 Uiso 1 1 calc R U . . .
C2 C 0.79868(16) -0.16974(12) 0.45854(14) 0.0452(5) Uani 1 1 d . . . . .
C11 C 0.8768(2) -0.15879(16) 0.37402(18) 0.0662(6) Uani 1 1 d . . . . .
H11A H 0.8566 -0.1993 0.3211 0.099 Uiso 1 1 calc R U . . .
H11B H 0.8719 -0.0997 0.3489 0.099 Uiso 1 1 calc R U . . .
H11C H 0.9512 -0.1704 0.3987 0.099 Uiso 1 1 calc R U . . .
C12 C 0.66920(14) 0.01750(11) 0.65338(13) 0.0371(4) Uani 1 1 d . . . . .
C13 C 0.58797(16) 0.01998(13) 0.72341(15) 0.0486(5) Uani 1 1 d . . . . .
H13A H 0.5540 -0.0322 0.7413 0.058 Uiso 1 1 calc R U . . .
C14 C 0.55657(17) 0.09762(13) 0.76700(16) 0.0524(5) Uani 1 1 d . . . . .
H14A H 0.5028 0.0971 0.8142 0.063 Uiso 1 1 calc R U . . .
C15 C 0.60445(15) 0.17587(12) 0.74092(15) 0.0457(5) Uani 1 1 d . . . . .
H15A H 0.5815 0.2277 0.7704 0.055 Uiso 1 1 calc R U . . .
C16 C 0.68644(14) 0.17957(11) 0.67145(13) 0.0369(4) Uani 1 1 d . . . . .
C17 C 0.71744(14) 0.09846(11) 0.62931(12) 0.0351(4) Uani 1 1 d . . . . .
C18 C 0.80367(17) 0.09921(11) 0.55896(15) 0.0463(5) Uani 1 1 d . . . . .
C19 C 0.8520(2) 0.40461(17) 0.40852(18) 0.0692(7) Uani 1 1 d . . . . .
H19A H 0.8366 0.4633 0.3854 0.104 Uiso 1 1 calc R U . . .
H19B H 0.9297 0.3929 0.4058 0.104 Uiso 1 1 calc R U . . .
H19C H 0.8111 0.3635 0.3666 0.104 Uiso 1 1 calc R U . . .
C21 C 0.83719(15) 0.29916(11) 0.57030(15) 0.0430(4) Uani 1 1 d . . . . .
H21 H 0.8743 0.2446 0.5298 0.052 Uiso 1 1 calc R U . . .
C22 C 0.81803(16) 0.39534(12) 0.51555(15) 0.0462(5) Uani 1 1 d . . . . .
B3 B 0.71026(19) -0.08664(13) 0.47710(16) 0.0435(5) Uani 1 1 d . . . . .
H3 H 0.7051 -0.0279 0.4291 0.052 Uiso 1 1 calc R U . . .
B4 B 0.69409(16) -0.07514(13) 0.60486(15) 0.0373(4) Uani 1 1 d . . . . .
B5 B 0.7800(2) -0.15839(15) 0.66239(17) 0.0519(6) Uani 1 1 d . . . . .
H5 H 0.8193 -0.1483 0.7376 0.062 Uiso 1 1 calc R U . . .
B6 B 0.8478(2) -0.21582(15) 0.56813(18) 0.0519(6) Uani 1 1 d . . . . .
H6 H 0.9316 -0.2429 0.5811 0.062 Uiso 1 1 calc R U . . .
B7 B 0.6617(2) -0.18747(17) 0.43178(19) 0.0569(6) Uani 1 1 d . . . . .
H7 H 0.6240 -0.1962 0.3558 0.068 Uiso 1 1 calc R U . . .
B8 B 0.59322(19) -0.13065(17) 0.5254(2) 0.0570(6) Uani 1 1 d . . . . .
H8 H 0.5100 -0.1030 0.5109 0.068 Uiso 1 1 calc R U . . .
B9 B 0.6372(2) -0.17738(15) 0.6428(2) 0.0591(7) Uani 1 1 d . . . . .
H9 H 0.5824 -0.1805 0.7058 0.071 Uiso 1 1 calc R U . . .
B10 B 0.7317(3) -0.26287(15) 0.6199(2) 0.0653(7) Uani 1 1 d . . . . .
H10 H 0.7386 -0.3217 0.6677 0.078 Uiso 1 1 calc R U . . .
B11 B 0.7468(2) -0.26890(14) 0.48943(18) 0.0516(6) Uani 1 1 d . . . . .
H11 H 0.7645 -0.3309 0.4510 0.062 Uiso 1 1 calc R U . . .
B12 B 0.6164(2) -0.24572(18) 0.5360(2) 0.0690(8) Uani 1 1 d . . . . .
H12 H 0.5479 -0.2932 0.5292 0.083 Uiso 1 1 calc R U . . .
B23 B 0.70554(18) 0.32936(14) 0.53469(16) 0.0438(5) Uani 1 1 d . . . . .
H23 H 0.6549 0.2978 0.4741 0.053 Uiso 1 1 calc R U . . .
B24 B 0.73499(16) 0.27427(13) 0.64993(15) 0.0379(4) Uani 1 1 d . . . . .
B25 B 0.86913(18) 0.30971(14) 0.69469(17) 0.0469(5) Uani 1 1 d . . . . .
H25 H 0.9241 0.2653 0.7390 0.056 Uiso 1 1 calc R U . . .
B26 B 0.92202(18) 0.38423(14) 0.60730(19) 0.0486(5) Uani 1 1 d . . . . .
H26 H 1.0108 0.3881 0.5939 0.058 Uiso 1 1 calc R U . . .
B27 B 0.70133(19) 0.44386(15) 0.5555(2) 0.0531(6) Uani 1 1 d . . . . .
H27 H 0.6473 0.4875 0.5092 0.064 Uiso 1 1 calc R U . . .
B28 B 0.64838(18) 0.36952(14) 0.64326(18) 0.0459(5) Uani 1 1 d . . . . .
H28 H 0.5593 0.3651 0.6549 0.055 Uiso 1 1 calc R U . . .
B29 B 0.7499(2) 0.35754(15) 0.74338(17) 0.0486(5) Uani 1 1 d . . . . .
H29 H 0.7268 0.3453 0.8206 0.058 Uiso 1 1 calc R U . . .
B30 B 0.8660(2) 0.42468(16) 0.71729(19) 0.0551(6) Uani 1 1 d . . . . .
H30 H 0.9182 0.4557 0.7771 0.066 Uiso 1 1 calc R U . . .
B31 B 0.8351(2) 0.47751(15) 0.6012(2) 0.0536(6) Uani 1 1 d . . . . .
H31 H 0.8676 0.5431 0.5845 0.064 Uiso 1 1 calc R U . . .
B32 B 0.7290(2) 0.46147(15) 0.6853(2) 0.0564(6) Uani 1 1 d . . . . .
H32 H 0.6921 0.5168 0.7247 0.068 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.140(3) . ?
C1 C2 1.659(3) . ?
C1 B3 1.687(3) . ?
C1 B5 1.701(3) . ?
C1 B6 1.717(3) . ?
C1 B4 1.733(3) . ?
C2 C11 1.520(3) . ?
C2 B3 1.683(3) . ?
C2 B11 1.693(3) . ?
C2 B7 1.701(3) . ?
C2 B6 1.703(3) . ?
C12 C13 1.393(2) . ?
C12 C17 1.407(2) . ?
C12 B4 1.586(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.376(3) . ?
C15 C16 1.396(2) . ?
C16 C17 1.415(2) . ?
C16 B24 1.588(2) . ?
C17 C18 1.441(2) . ?
C19 C22 1.516(3) . ?
C21 C22 1.647(3) . ?
C21 B25 1.696(3) . ?
C21 B23 1.703(3) . ?
C21 B26 1.709(3) . ?
C21 B24 1.716(3) . ?
C22 B31 1.701(3) . ?
C22 B27 1.705(3) . ?
C22 B26 1.720(3) . ?
C22 B23 1.722(3) . ?
B3 B8 1.723(3) . ?
B3 B4 1.738(3) . ?
B3 B7 1.740(3) . ?
B4 B9 1.785(3) . ?
B4 B5 1.787(3) . ?
B4 B8 1.788(3) . ?
B5 B9 1.759(4) . ?
B5 B6 1.770(3) . ?
B5 B10 1.777(3) . ?
B6 B10 1.752(4) . ?
B6 B11 1.766(3) . ?
B7 B12 1.763(4) . ?
B7 B8 1.763(3) . ?
B7 B11 1.763(3) . ?
B8 B12 1.777(4) . ?
B8 B9 1.779(4) . ?
B9 B10 1.769(4) . ?
B9 B12 1.773(4) . ?
B10 B12 1.763(5) . ?
B10 B11 1.766(4) . ?
B11 B12 1.763(4) . ?
B23 B28 1.750(3) . ?
B23 B27 1.765(3) . ?
B23 B24 1.774(3) . ?
B24 B29 1.782(3) . ?
B24 B25 1.785(3) . ?
B24 B28 1.788(3) . ?
B25 B29 1.770(3) . ?
B25 B26 1.771(3) . ?
B25 B30 1.775(3) . ?
B26 B30 1.762(3) . ?
B26 B31 1.766(3) . ?
B27 B32 1.770(4) . ?
B27 B28 1.773(3) . ?
B27 B31 1.776(3) . ?
B28 B29 1.779(3) . ?
B28 B32 1.779(3) . ?
B29 B32 1.773(3) . ?
B29 B30 1.786(3) . ?
B30 B31 1.770(4) . ?
B30 B32 1.782(4) . ?
B31 B32 1.768(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
C2 C1 B3 60.40(12) . . ?
C2 C1 B5 110.02(15) . . ?
B3 C1 B5 111.31(16) . . ?
C2 C1 B6 60.58(12) . . ?
B3 C1 B6 111.34(16) . . ?
B5 C1 B6 62.38(13) . . ?
C2 C1 B4 110.41(15) . . ?
B3 C1 B4 61.09(12) . . ?
B5 C1 B4 62.71(12) . . ?
B6 C1 B4 114.05(16) . . ?
C11 C2 C1 117.25(17) . . ?
C11 C2 B3 116.91(16) . . ?
C1 C2 B3 60.64(12) . . ?
C11 C2 B11 122.14(17) . . ?
C1 C2 B11 111.81(15) . . ?
B3 C2 B11 112.71(15) . . ?
C11 C2 B7 119.94(18) . . ?
C1 C2 B7 111.50(15) . . ?
B3 C2 B7 61.89(13) . . ?
B11 C2 B7 62.61(14) . . ?
C11 C2 B6 118.79(18) . . ?
C1 C2 B6 61.41(12) . . ?
B3 C2 B6 112.23(15) . . ?
B11 C2 B6 62.67(13) . . ?
B7 C2 B6 114.14(17) . . ?
C13 C12 C17 116.48(16) . . ?
C13 C12 B4 117.04(15) . . ?
C17 C12 B4 126.41(15) . . ?
C14 C13 C12 121.80(17) . . ?
C15 C14 C13 120.27(17) . . ?
C14 C15 C16 121.80(17) . . ?
C15 C16 C17 116.28(16) . . ?
C15 C16 B24 116.11(15) . . ?
C17 C16 B24 127.60(15) . . ?
C12 C17 C16 123.35(15) . . ?
C12 C17 C18 118.66(15) . . ?
C16 C17 C18 117.99(15) . . ?
N1 C18 C17 179.0(3) . . ?
C22 C21 B25 111.83(15) . . ?
C22 C21 B23 61.84(12) . . ?
B25 C21 B23 114.28(15) . . ?
C22 C21 B26 61.64(12) . . ?
B25 C21 B26 62.71(13) . . ?
B23 C21 B26 114.62(15) . . ?
C22 C21 B24 112.47(14) . . ?
B25 C21 B24 63.08(12) . . ?
B23 C21 B24 62.49(12) . . ?
B26 C21 B24 115.42(15) . . ?
C19 C22 C21 117.61(17) . . ?
C19 C22 B31 122.56(17) . . ?
C21 C22 B31 110.11(16) . . ?
C19 C22 B27 121.72(19) . . ?
C21 C22 B27 110.18(15) . . ?
B31 C22 B27 62.89(14) . . ?
C19 C22 B26 117.27(18) . . ?
C21 C22 B26 60.97(12) . . ?
B31 C22 B26 62.15(13) . . ?
B27 C22 B26 114.00(17) . . ?
C19 C22 B23 116.74(17) . . ?
C21 C22 B23 60.69(11) . . ?
B31 C22 B23 113.42(16) . . ?
B27 C22 B23 61.99(13) . . ?
B26 C22 B23 113.09(15) . . ?
C2 B3 C1 58.97(12) . . ?
C2 B3 B8 107.79(15) . . ?
C1 B3 B8 108.97(16) . . ?
C2 B3 B4 108.99(15) . . ?
C1 B3 B4 60.76(12) . . ?
B8 B3 B4 62.19(13) . . ?
C2 B3 B7 59.55(12) . . ?
C1 B3 B7 108.23(15) . . ?
B8 B3 B7 61.22(14) . . ?
B4 B3 B7 112.17(16) . . ?
C12 B4 C1 124.93(15) . . ?
C12 B4 B3 121.64(15) . . ?
C1 B4 B3 58.16(12) . . ?
C12 B4 B9 124.96(16) . . ?
C1 B4 B9 103.23(15) . . ?
B3 B4 B9 104.87(15) . . ?
C12 B4 B5 124.88(15) . . ?
C1 B4 B5 57.76(12) . . ?
B3 B4 B5 105.01(14) . . ?
B9 B4 B5 59.02(14) . . ?
C12 B4 B8 121.58(16) . . ?
C1 B4 B8 104.06(15) . . ?
B3 B4 B8 58.48(13) . . ?
B9 B4 B8 59.72(15) . . ?
B5 B4 B8 106.59(15) . . ?
C1 B5 B9 105.68(17) . . ?
C1 B5 B6 59.27(12) . . ?
B9 B5 B6 107.56(17) . . ?
C1 B5 B10 105.19(16) . . ?
B9 B5 B10 60.04(15) . . ?
B6 B5 B10 59.21(15) . . ?
C1 B5 B4 59.53(12) . . ?
B9 B5 B4 60.43(13) . . ?
B6 B5 B4 108.92(15) . . ?
B10 B5 B4 108.73(17) . . ?
C2 B6 C1 58.01(12) . . ?
C2 B6 B10 104.83(17) . . ?
C1 B6 B10 105.55(17) . . ?
C2 B6 B11 58.37(12) . . ?
C1 B6 B11 105.63(16) . . ?
B10 B6 B11 60.24(15) . . ?
C2 B6 B5 104.80(15) . . ?
C1 B6 B5 58.35(12) . . ?
B10 B6 B5 60.58(14) . . ?
B11 B6 B5 108.51(17) . . ?
C2 B7 B3 58.56(12) . . ?
C2 B7 B12 104.67(17) . . ?
B3 B7 B12 106.31(17) . . ?
C2 B7 B8 105.21(15) . . ?
B3 B7 B8 58.92(13) . . ?
B12 B7 B8 60.51(15) . . ?
C2 B7 B11 58.48(12) . . ?
B3 B7 B11 106.69(16) . . ?
B12 B7 B11 60.01(15) . . ?
B8 B7 B11 108.63(18) . . ?
B3 B8 B7 59.86(13) . . ?
B3 B8 B12 106.43(17) . . ?
B7 B8 B12 59.73(15) . . ?
B3 B8 B9 105.77(17) . . ?
B7 B8 B9 107.49(18) . . ?
B12 B8 B9 59.83(16) . . ?
B3 B8 B4 59.32(12) . . ?
B7 B8 B4 108.75(16) . . ?
B12 B8 B4 108.50(18) . . ?
B9 B8 B4 60.05(13) . . ?
B5 B9 B10 60.47(15) . . ?
B5 B9 B12 108.26(18) . . ?
B10 B9 B12 59.70(16) . . ?
B5 B9 B8 108.22(16) . . ?
B10 B9 B8 107.89(18) . . ?
B12 B9 B8 60.03(16) . . ?
B5 B9 B4 60.56(12) . . ?
B10 B9 B4 109.17(17) . . ?
B12 B9 B4 108.81(18) . . ?
B8 B9 B4 60.23(13) . . ?
B6 B10 B12 108.28(18) . . ?
B6 B10 B11 60.28(14) . . ?
B12 B10 B11 59.96(15) . . ?
B6 B10 B9 107.93(16) . . ?
B12 B10 B9 60.26(16) . . ?
B11 B10 B9 108.12(19) . . ?
B6 B10 B5 60.21(14) . . ?
B12 B10 B5 107.93(17) . . ?
B11 B10 B5 108.25(16) . . ?
B9 B10 B5 59.50(14) . . ?
C2 B11 B7 58.91(13) . . ?
C2 B11 B12 104.98(16) . . ?
B7 B11 B12 59.98(16) . . ?
C2 B11 B10 104.70(15) . . ?
B7 B11 B10 107.86(17) . . ?
B12 B11 B10 59.95(17) . . ?
C2 B11 B6 58.96(12) . . ?
B7 B11 B6 108.09(15) . . ?
B12 B11 B6 107.63(17) . . ?
B10 B11 B6 59.48(15) . . ?
B7 B12 B10 107.99(18) . . ?
B7 B12 B11 60.01(14) . . ?
B10 B12 B11 60.09(16) . . ?
B7 B12 B9 107.77(17) . . ?
B10 B12 B9 60.03(16) . . ?
B11 B12 B9 108.03(19) . . ?
B7 B12 B8 59.76(15) . . ?
B10 B12 B8 108.24(17) . . ?
B11 B12 B8 108.03(17) . . ?
B9 B12 B8 60.14(15) . . ?
C21 B23 C22 57.47(11) . . ?
C21 B23 B28 105.49(15) . . ?
C22 B23 B28 105.67(15) . . ?
C21 B23 B27 104.85(15) . . ?
C22 B23 B27 58.53(12) . . ?
B28 B23 B27 60.58(13) . . ?
C21 B23 B24 59.13(11) . . ?
C22 B23 B24 106.24(15) . . ?
B28 B23 B24 60.96(12) . . ?
B27 B23 B24 109.57(16) . . ?
C16 B24 C21 126.75(15) . . ?
C16 B24 B23 121.76(15) . . ?
C21 B24 B23 58.38(11) . . ?
C16 B24 B29 122.86(16) . . ?
C21 B24 B29 103.19(14) . . ?
B23 B24 B29 106.39(15) . . ?
C16 B24 B25 123.52(16) . . ?
C21 B24 B25 57.89(12) . . ?
B23 B24 B25 106.68(14) . . ?
B29 B24 B25 59.52(12) . . ?
C16 B24 B28 121.49(15) . . ?
C21 B24 B28 103.32(14) . . ?
B23 B24 B28 58.88(12) . . ?
B29 B24 B28 59.80(12) . . ?
B25 B24 B28 107.05(14) . . ?
C21 B25 B29 104.53(15) . . ?
C21 B25 B26 59.02(12) . . ?
B29 B25 B26 108.03(16) . . ?
C21 B25 B30 104.74(16) . . ?
B29 B25 B30 60.50(13) . . ?
B26 B25 B30 59.59(13) . . ?
C21 B25 B24 59.03(11) . . ?
B29 B25 B24 60.15(12) . . ?
B26 B25 B24 109.02(16) . . ?
B30 B25 B24 109.11(16) . . ?
C21 B26 C22 57.40(11) . . ?
C21 B26 B30 104.72(15) . . ?
C22 B26 B30 105.17(16) . . ?
C21 B26 B31 104.30(15) . . ?
C22 B26 B31 58.39(13) . . ?
B30 B26 B31 60.23(14) . . ?
C21 B26 B25 58.28(12) . . ?
C22 B26 B25 104.89(15) . . ?
B30 B26 B25 60.30(13) . . ?
B31 B26 B25 108.01(16) . . ?
C22 B27 B23 59.47(12) . . ?
C22 B27 B32 104.79(17) . . ?
B23 B27 B32 107.37(16) . . ?
C22 B27 B28 105.41(15) . . ?
B23 B27 B28 59.32(12) . . ?
B32 B27 B28 60.30(13) . . ?
C22 B27 B31 58.44(12) . . ?
B23 B27 B31 107.77(16) . . ?
B32 B27 B31 59.79(15) . . ?
B28 B27 B31 108.11(17) . . ?
B23 B28 B27 60.11(13) . . ?
B23 B28 B29 107.50(15) . . ?
B27 B28 B29 107.67(16) . . ?
B23 B28 B32 107.58(16) . . ?
B27 B28 B32 59.77(14) . . ?
B29 B28 B32 59.78(14) . . ?
B23 B28 B24 60.16(12) . . ?
B27 B28 B24 108.56(15) . . ?
B29 B28 B24 59.93(12) . . ?
B32 B28 B24 108.07(16) . . ?
B25 B29 B32 107.80(16) . . ?
B25 B29 B28 108.06(15) . . ?
B32 B29 B28 60.12(14) . . ?
B25 B29 B24 60.33(12) . . ?
B32 B29 B24 108.61(16) . . ?
B28 B29 B24 60.27(12) . . ?
B25 B29 B30 59.87(13) . . ?
B32 B29 B30 60.07(14) . . ?
B28 B29 B30 108.33(17) . . ?
B24 B29 B30 108.75(16) . . ?
B26 B30 B31 59.98(13) . . ?
B26 B30 B25 60.10(13) . . ?
B31 B30 B25 107.65(16) . . ?
B26 B30 B32 107.65(18) . . ?
B31 B30 B32 59.69(14) . . ?
B25 B30 B32 107.24(16) . . ?
B26 B30 B29 107.73(15) . . ?
B31 B30 B29 107.35(17) . . ?
B25 B30 B29 59.62(13) . . ?
B32 B30 B29 59.61(14) . . ?
C22 B31 B26 59.46(12) . . ?
C22 B31 B32 105.07(16) . . ?
B26 B31 B32 108.13(17) . . ?
C22 B31 B30 105.65(15) . . ?
B26 B31 B30 59.79(14) . . ?
B32 B31 B30 60.48(15) . . ?
C22 B31 B27 58.67(13) . . ?
B26 B31 B27 108.36(15) . . ?
B32 B31 B27 59.92(14) . . ?
B30 B31 B27 108.54(17) . . ?
B31 B32 B27 60.29(14) . . ?
B31 B32 B29 108.03(16) . . ?
B27 B32 B29 108.06(16) . . ?
B31 B32 B28 108.22(16) . . ?
B27 B32 B28 59.93(13) . . ?
B29 B32 B28 60.10(13) . . ?
B31 B32 B30 59.83(14) . . ?
B27 B32 B30 108.31(16) . . ?
B29 B32 B30 60.33(14) . . ?
B28 B32 B30 108.52(16) . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_3aq
_database_code_depnum_ccdc_archive 'CCDC 1987437'
loop_
_audit_author_name
_audit_author_address
'Hoi Shan CHAN'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 B10 N2'
_chemical_formula_weight         312.41

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

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

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

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

_cell_length_a                   11.3782(12)
_cell_length_b                   11.4876(11)
_cell_length_c                   13.5646(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1773.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    349
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5181
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67985
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.1414
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         25.233
_diffrn_reflns_theta_full        25.233
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3218
_reflns_number_gt                2380
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1321P)²+0.8621P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.030(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 774 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -5.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3218
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2336
_refine_ls_wR_factor_gt          0.2131
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4685(4) 0.9142(4) 0.1951(3) 0.0532(12) Uani 1 1 d . . . . .
N2 N 0.5764(4) 0.7379(4) 0.2036(3) 0.0564(12) Uani 1 1 d . . . . .
C1 C 0.2377(7) 0.9123(7) 0.3037(6) 0.087(2) Uani 1 1 d . . . . .
H1 H 0.300077 0.967917 0.263466 0.104 Uiso 1 1 calc R U . . .
C2 C 0.2265(9) 0.9188(8) 0.4193(6) 0.100(3) Uani 1 1 d . . . . .
C11 C 0.3097(10) 1.0037(11) 0.4727(9) 0.166(6) Uani 1 1 d . . . . .
H11A H 0.370473 0.960558 0.505437 0.249 Uiso 1 1 calc R U . . .
H11B H 0.344438 1.055659 0.425480 0.249 Uiso 1 1 calc R U . . .
H11C H 0.266074 1.047864 0.520307 0.249 Uiso 1 1 calc R U . . .
C12 C 0.2714(4) 0.7352(4) 0.1528(3) 0.0411(11) Uani 1 1 d . . . . .
C13 C 0.1931(5) 0.6724(5) 0.0902(4) 0.0545(15) Uani 1 1 d . . . . .
H13A H 0.114391 0.666028 0.107937 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2307(6) 0.6213(5) 0.0046(4) 0.0656(17) Uani 1 1 d . . . . .
H14A H 0.176647 0.583024 -0.035357 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3459(6) 0.6253(6) -0.0232(5) 0.0710(18) Uani 1 1 d . . . . .
H15A H 0.370849 0.588945 -0.080774 0.085 Uiso 1 1 calc R U . . .
C16 C 0.4241(5) 0.6843(5) 0.0355(4) 0.0565(15) Uani 1 1 d . . . . .
H16A H 0.502723 0.687246 0.017017 0.068 Uiso 1 1 calc R U . . .
C17 C 0.3889(4) 0.7402(4) 0.1225(3) 0.0399(11) Uani 1 1 d . . . . .
C18 C 0.4835(4) 0.8010(4) 0.1791(3) 0.0402(12) Uani 1 1 d . . . . .
C19 C 0.5561(5) 0.9669(5) 0.2443(5) 0.0637(17) Uani 1 1 d . . . . .
H19A H 0.549820 1.046070 0.257450 0.076 Uiso 1 1 calc R U . . .
C20 C 0.6536(6) 0.9092(7) 0.2755(5) 0.0695(18) Uani 1 1 d . . . . .
H20A H 0.712619 0.946643 0.310783 0.083 Uiso 1 1 calc R U . . .
C21 C 0.6605(5) 0.7947(6) 0.2529(5) 0.0648(17) Uani 1 1 d . . . . .
H21A H 0.726861 0.753515 0.272590 0.078 Uiso 1 1 calc R U . . .
B3 B 0.1232(11) 0.9733(12) 0.3624(11) 0.131(5) Uani 1 1 d . . . . .
H3 H 0.104381 1.067172 0.364541 0.157 Uiso 1 1 calc R U . . .
B4 B 0.1081(9) 0.8910(10) 0.2572(8) 0.109(4) Uani 1 1 d . . . . .
H4 H 0.077657 0.930626 0.187969 0.131 Uiso 1 1 calc R U . . .
B5 B 0.2151(5) 0.7784(5) 0.2520(4) 0.0440(13) Uani 1 1 d . . . . .
B6 B 0.2943(7) 0.8051(9) 0.3610(5) 0.080(3) Uani 1 1 d . . . . .
H6 H 0.389263 0.787251 0.363037 0.096 Uiso 1 1 calc R U . . .
B7 B 0.0936(8) 0.8790(11) 0.4653(8) 0.102(3) Uani 1 1 d . . . . .
H7 H 0.051386 0.904595 0.534930 0.122 Uiso 1 1 calc R U . . .
B8 B 0.0160(8) 0.8726(15) 0.3567(10) 0.141(6) Uani 1 1 d . . . . .
H8 H -0.076722 0.899468 0.354209 0.169 Uiso 1 1 calc R U . . .
B9 B 0.0683(8) 0.7540(13) 0.2896(9) 0.136(6) Uani 1 1 d . . . . .
H9 H 0.007383 0.702715 0.243981 0.163 Uiso 1 1 calc R U . . .
B10 B 0.1932(11) 0.6937(8) 0.3585(8) 0.110(4) Uani 1 1 d . . . . .
H10 H 0.217264 0.600918 0.358718 0.132 Uiso 1 1 calc R U . . .
B11 B 0.2098(9) 0.7865(11) 0.4642(7) 0.102(3) Uani 1 1 d . . . . .
H11 H 0.250038 0.758462 0.534048 0.122 Uiso 1 1 calc R U . . .
B12 B 0.0706(13) 0.7408(11) 0.4234(10) 0.156(7) Uani 1 1 d . . . . .
H12 H 0.016665 0.676849 0.463458 0.187 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.329(6) . ?
N1 C19 1.344(7) . ?
N2 C18 1.323(6) . ?
N2 C21 1.338(7) . ?
C1 C2 1.575(11) . ?
C1 B6 1.592(13) . ?
C1 B4 1.622(13) . ?
C1 B3 1.680(12) . ?
C1 B5 1.710(9) . ?
C2 B3 1.539(17) . ?
C2 C11 1.540(12) . ?
C2 B11 1.648(15) . ?
C2 B7 1.699(13) . ?
C2 B6 1.711(12) . ?
C12 C17 1.400(7) . ?
C12 C13 1.427(7) . ?
C12 B5 1.570(8) . ?
C13 C14 1.370(8) . ?
C14 C15 1.364(9) . ?
C15 C16 1.373(8) . ?
C16 C17 1.402(7) . ?
C17 C18 1.495(7) . ?
C19 C20 1.360(9) . ?
C20 C21 1.353(9) . ?
B3 B8 1.682(19) . ?
B3 B4 1.720(16) . ?
B3 B7 1.80(2) . ?
B4 B9 1.695(19) . ?
B4 B8 1.721(17) . ?
B4 B5 1.778(10) . ?
B5 B6 1.758(9) . ?
B5 B10 1.760(10) . ?
B5 B9 1.769(9) . ?
B6 B11 1.713(11) . ?
B6 B10 1.722(14) . ?
B7 B11 1.696(15) . ?
B7 B12 1.707(15) . ?
B7 B8 1.719(16) . ?
B8 B9 1.743(16) . ?
B8 B12 1.87(2) . ?
B9 B12 1.82(2) . ?
B9 B10 1.837(18) . ?
B10 B12 1.736(14) . ?
B10 B11 1.797(16) . ?
B11 B12 1.759(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N1 C19 115.2(5) . . ?
C18 N2 C21 115.5(5) . . ?
C2 C1 B6 65.4(6) . . ?
C2 C1 B4 108.7(7) . . ?
B6 C1 B4 116.2(7) . . ?
C2 C1 B3 56.3(7) . . ?
B6 C1 B3 113.9(8) . . ?
B4 C1 B3 62.8(6) . . ?
C2 C1 B5 116.0(6) . . ?
B6 C1 B5 64.2(4) . . ?
B4 C1 B5 64.4(5) . . ?
B3 C1 B5 117.0(6) . . ?
B3 C2 C11 116.6(9) . . ?
B3 C2 C1 65.3(7) . . ?
C11 C2 C1 116.6(8) . . ?
B3 C2 B11 118.2(9) . . ?
C11 C2 B11 118.7(10) . . ?
C1 C2 B11 109.5(6) . . ?
B3 C2 B7 67.3(8) . . ?
C11 C2 B7 123.0(7) . . ?
C1 C2 B7 115.1(7) . . ?
B11 C2 B7 60.9(6) . . ?
B3 C2 B6 115.0(7) . . ?
C11 C2 B6 115.1(8) . . ?
C1 C2 B6 57.8(5) . . ?
B11 C2 B6 61.3(5) . . ?
B7 C2 B6 111.5(7) . . ?
C17 C12 C13 116.2(5) . . ?
C17 C12 B5 128.9(4) . . ?
C13 C12 B5 114.5(4) . . ?
C14 C13 C12 121.8(5) . . ?
C15 C14 C13 121.3(5) . . ?
C14 C15 C16 118.6(6) . . ?
C15 C16 C17 122.0(5) . . ?
C12 C17 C16 120.1(4) . . ?
C12 C17 C18 123.7(4) . . ?
C16 C17 C18 116.2(4) . . ?
N2 C18 N1 126.7(5) . . ?
N2 C18 C17 116.6(4) . . ?
N1 C18 C17 116.6(5) . . ?
N1 C19 C20 122.7(5) . . ?
C21 C20 C19 116.8(6) . . ?
N2 C21 C20 123.1(6) . . ?
C2 B3 C1 58.4(6) . . ?
C2 B3 B8 107.3(11) . . ?
C1 B3 B8 104.7(7) . . ?
C2 B3 B4 105.6(8) . . ?
C1 B3 B4 57.0(5) . . ?
B8 B3 B4 60.8(7) . . ?
C2 B3 B7 60.6(8) . . ?
C1 B3 B7 105.2(9) . . ?
B8 B3 B7 59.1(8) . . ?
B4 B3 B7 107.1(9) . . ?
C1 B4 B9 106.4(8) . . ?
C1 B4 B3 60.3(6) . . ?
B9 B4 B3 108.8(9) . . ?
C1 B4 B8 105.5(7) . . ?
B9 B4 B8 61.3(7) . . ?
B3 B4 B8 58.5(7) . . ?
C1 B4 B5 60.2(4) . . ?
B9 B4 B5 61.2(5) . . ?
B3 B4 B5 111.4(8) . . ?
B8 B4 B5 111.0(8) . . ?
C12 B5 C1 125.0(5) . . ?
C12 B5 B6 124.5(5) . . ?
C1 B5 B6 54.6(5) . . ?
C12 B5 B10 125.9(5) . . ?
C1 B5 B10 100.5(5) . . ?
B6 B5 B10 58.6(5) . . ?
C12 B5 B9 125.6(5) . . ?
C1 B5 B9 99.6(5) . . ?
B6 B5 B9 105.6(6) . . ?
B10 B5 B9 62.7(7) . . ?
C12 B5 B4 122.9(5) . . ?
C1 B5 B4 55.4(5) . . ?
B6 B5 B4 101.0(5) . . ?
B10 B5 B4 105.8(6) . . ?
B9 B5 B4 57.1(7) . . ?
C1 B6 C2 56.8(5) . . ?
C1 B6 B11 105.6(7) . . ?
C2 B6 B11 57.6(6) . . ?
C1 B6 B10 107.2(6) . . ?
C2 B6 B10 106.0(6) . . ?
B11 B6 B10 63.1(6) . . ?
C1 B6 B5 61.1(4) . . ?
C2 B6 B5 106.9(6) . . ?
B11 B6 B5 112.2(6) . . ?
B10 B6 B5 60.8(5) . . ?
B11 B7 C2 58.1(6) . . ?
B11 B7 B12 62.2(8) . . ?
C2 B7 B12 105.4(7) . . ?
B11 B7 B8 111.5(7) . . ?
C2 B7 B8 98.9(7) . . ?
B12 B7 B8 66.2(9) . . ?
B11 B7 B3 103.0(7) . . ?
C2 B7 B3 52.1(6) . . ?
B12 B7 B3 109.3(8) . . ?
B8 B7 B3 57.1(8) . . ?
B3 B8 B7 63.8(8) . . ?
B3 B8 B4 60.7(8) . . ?
B7 B8 B4 110.7(7) . . ?
B3 B8 B9 108.3(7) . . ?
B7 B8 B9 107.8(9) . . ?
B4 B8 B9 58.6(6) . . ?
B3 B8 B12 107.1(9) . . ?
B7 B8 B12 56.6(7) . . ?
B4 B8 B12 106.1(7) . . ?
B9 B8 B12 60.4(8) . . ?
B4 B9 B8 60.1(8) . . ?
B4 B9 B5 61.7(5) . . ?
B8 B9 B5 110.4(7) . . ?
B4 B9 B12 109.4(7) . . ?
B8 B9 B12 63.2(7) . . ?
B5 B9 B12 106.7(8) . . ?
B4 B9 B10 106.0(6) . . ?
B8 B9 B10 107.0(7) . . ?
B5 B9 B10 58.4(5) . . ?
B12 B9 B10 56.7(7) . . ?
B6 B10 B12 107.2(7) . . ?
B6 B10 B5 60.7(4) . . ?
B12 B10 B5 111.0(8) . . ?
B6 B10 B11 58.2(6) . . ?
B12 B10 B11 59.7(6) . . ?
B5 B10 B11 108.2(6) . . ?
B6 B10 B9 104.3(6) . . ?
B12 B10 B9 61.2(8) . . ?
B5 B10 B9 58.9(5) . . ?
B11 B10 B9 105.3(6) . . ?
C2 B11 B7 61.0(7) . . ?
C2 B11 B6 61.1(6) . . ?
B7 B11 B6 111.5(8) . . ?
C2 B11 B12 105.2(9) . . ?
B7 B11 B12 59.2(6) . . ?
B6 B11 B12 106.6(7) . . ?
C2 B11 B10 105.3(6) . . ?
B7 B11 B10 107.2(8) . . ?
B6 B11 B10 58.7(5) . . ?
B12 B11 B10 58.4(6) . . ?
B7 B12 B10 109.6(8) . . ?
B7 B12 B11 58.6(7) . . ?
B10 B12 B11 61.9(7) . . ?
B7 B12 B9 104.8(10) . . ?
B10 B12 B9 62.1(6) . . ?
B11 B12 B9 107.6(6) . . ?
B7 B12 B8 57.2(7) . . ?
B10 B12 B8 105.9(8) . . ?
B11 B12 B8 102.1(8) . . ?
B9 B12 B8 56.3(8) . . ?

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058

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

data_3at
_database_code_depnum_ccdc_archive 'CCDC 1987439'
loop_
_audit_author_name
_audit_author_address
'Hoi Shan CHAN'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23.25 B10 N'
_chemical_formula_weight         349.71

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

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

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

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

_cell_length_a                   10.6954(6)
_cell_length_b                   10.2783(6)
_cell_length_c                   18.0417(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1983.33(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    260
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             729
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_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 D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44175
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1899
_reflns_number_gt                1517
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1517P)²+0.9328P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1899
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2543
_refine_ls_wR_factor_gt          0.2376
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6323(2) 0.1415(2) 0.61956(13) 0.0549(7) Uani 0.5 1 d . . P . .
C22 C 0.6323(2) 0.1415(2) 0.61956(13) 0.0549(7) Uani 0.5 1 d . . P . .
C1 C 0.7285(3) 0.2500 0.46364(18) 0.0433(8) Uani 1 2 d S T P . .
H1 H 0.6977 0.2500 0.5218 0.052 Uiso 1 2 calc R U P . .
C2 C 0.8305(3) 0.1655(3) 0.41354(17) 0.0583(8) Uani 0.5 1 d . . P . .
B9 B 0.8305(3) 0.1655(3) 0.41354(17) 0.0583(8) Uani 0.5 1 d . . P . .
C11 C 0.9221(5) 0.0884(7) 0.4526(4) 0.0686(16) Uani 0.5 1 d . . P . .
H11A H 0.9750 0.0448 0.4175 0.103 Uiso 0.5 1 calc R U P . .
H11B H 0.9721 0.1440 0.4834 0.103 Uiso 0.5 1 calc R U P . .
H11C H 0.8803 0.0251 0.4828 0.103 Uiso 0.5 1 calc R U P . .
C12 C 0.4569(3) 0.2500 0.47669(19) 0.0469(9) Uani 1 2 d S T P . .
C13 C 0.3449(4) 0.2500 0.4389(2) 0.0646(11) Uani 1 2 d S T P . .
H13A H 0.3458 0.2500 0.3873 0.077 Uiso 1 2 calc R U P . .
C14 C 0.2309(4) 0.2500 0.4754(3) 0.0754(14) Uani 1 2 d S T P . .
H14A H 0.1568 0.2500 0.4484 0.091 Uiso 1 2 calc R U P . .
C15 C 0.2272(4) 0.2500 0.5504(3) 0.0669(12) Uani 1 2 d S T P . .
H15A H 0.1506 0.2500 0.5748 0.080 Uiso 1 2 calc R U P . .
C16 C 0.3357(4) 0.2500 0.5906(2) 0.0593(10) Uani 1 2 d S T P . .
H16A H 0.3324 0.2500 0.6421 0.071 Uiso 1 2 calc R U P . .
C17 C 0.4514(3) 0.2500 0.5546(2) 0.0458(8) Uani 1 2 d S T P . .
C18 C 0.5671(3) 0.2500 0.59949(19) 0.0490(9) Uani 1 2 d S T P . .
C19 C 0.7462(2) 0.1817(3) 0.65234(13) 0.0555(7) Uani 1 1 d . . . . .
C20 C 0.8488(3) 0.1130(5) 0.67900(18) 0.0894(13) Uani 1 1 d . . . . .
H20A H 0.8495 0.0225 0.6795 0.107 Uiso 1 1 calc R U . . .
C21 C 0.9488(3) 0.1832(5) 0.70453(18) 0.129(3) Uani 1 1 d . . . . .
H21 H 1.0185 0.1392 0.7224 0.155 Uiso 1 1 calc R U . . .
B3 B 0.6786(3) 0.1106(3) 0.42277(17) 0.0514(8) Uani 1 1 d . . . . .
H3 H 0.6301 0.0275 0.4483 0.062 Uiso 1 1 calc R U . . .
B4 B 0.5802(4) 0.2500 0.4282(2) 0.0451(9) Uani 1 2 d S T P . .
B5 B 0.8530(5) 0.2500 0.3323(3) 0.0673(13) Uani 1 2 d S T P . .
H5 H 0.9203 0.2500 0.2862 0.081 Uiso 1 2 calc R U P . .
B6 B 0.7557(3) 0.1102(4) 0.33606(19) 0.0651(10) Uani 1 1 d . . . . .
H6 H 0.7618 0.0263 0.2984 0.078 Uiso 1 1 calc R U . . .
B7 B 0.5979(3) 0.1638(3) 0.34283(16) 0.0571(9) Uani 1 1 d . . . . .
H7 H 0.5204 0.1076 0.3188 0.069 Uiso 1 1 calc R U . . .
B8 B 0.7051(5) 0.2500 0.2864(2) 0.0665(13) Uani 1 2 d S T P . .
H8 H 0.6973 0.2500 0.2256 0.080 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.364(3) . ?
N1 C19 1.416(4) . ?
C1 B9 1.662(4) 7_565 ?
C1 C2 1.662(4) 7_565 ?
C1 C2 1.662(4) . ?
C1 B3 1.697(3) 7_565 ?
C1 B3 1.697(3) . ?
C1 B4 1.710(5) . ?
C2 C11 1.444(7) . ?
C2 B6 1.708(5) . ?
C2 B5 1.720(5) . ?
C2 B3 1.729(4) . ?
C2 B9 1.737(7) 7_565 ?
C2 C2 1.737(7) 7_565 ?
C12 C13 1.378(5) . ?
C12 C17 1.407(5) . ?
C12 B4 1.583(5) . ?
C13 C14 1.386(6) . ?
C14 C15 1.354(7) . ?
C15 C16 1.367(6) . ?
C16 C17 1.398(5) . ?
C17 C18 1.479(5) . ?
C18 C22 1.364(3) 7_565 ?
C18 N1 1.364(3) 7_565 ?
C19 C20 1.391(4) . ?
C19 C19 1.404(6) 7_565 ?
C20 C21 1.369(6) . ?
C21 C21 1.373(11) 7_565 ?
B3 B7 1.767(4) . ?
B3 B6 1.769(4) . ?
B3 B4 1.780(4) . ?
B4 B3 1.780(4) 7_565 ?
B4 B7 1.787(4) 7_565 ?
B4 B7 1.787(4) . ?
B5 B9 1.720(5) 7_565 ?
B5 C2 1.720(5) 7_565 ?
B5 B6 1.775(5) . ?
B5 B6 1.775(5) 7_565 ?
B5 B8 1.785(7) . ?
B6 B8 1.778(5) . ?
B6 B7 1.779(5) . ?
B7 B8 1.771(5) . ?
B7 B7 1.772(7) 7_565 ?
B8 B7 1.771(5) 7_565 ?
B8 B6 1.778(5) 7_565 ?

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
C18 N1 C19 108.2(2) . . ?
B9 C1 C2 0.0 7_565 7_565 ?
B9 C1 C2 63.0 7_565 . ?
C2 C1 C2 63.0(3) 7_565 . ?
B9 C1 B3 61.92(17) 7_565 7_565 ?
C2 C1 B3 61.92(17) 7_565 7_565 ?
C2 C1 B3 114.3(2) . 7_565 ?
B9 C1 B3 114.3(2) 7_565 . ?
C2 C1 B3 114.3(2) 7_565 . ?
C2 C1 B3 61.92(17) . . ?
B3 C1 B3 115.1(3) 7_565 . ?
B9 C1 B4 113.9(2) 7_565 . ?
C2 C1 B4 113.9(2) 7_565 . ?
C2 C1 B4 113.9(2) . . ?
B3 C1 B4 62.99(15) 7_565 . ?
B3 C1 B4 62.99(15) . . ?
C11 C2 C1 117.9(3) . . ?
C11 C2 B6 122.3(4) . . ?
C1 C2 B6 108.1(2) . . ?
C11 C2 B5 126.7(4) . . ?
C1 C2 B5 106.9(2) . . ?
B6 C2 B5 62.4(2) . . ?
C11 C2 B3 114.3(3) . . ?
C1 C2 B3 60.05(16) . . ?
B6 C2 B3 61.95(18) . . ?
B5 C2 B3 112.2(3) . . ?
C11 C2 B9 123.3(3) . 7_565 ?
C1 C2 B9 58.50(13) . 7_565 ?
B6 C2 B9 109.44(17) . 7_565 ?
B5 C2 B9 59.68(13) . 7_565 ?
B3 C2 B9 109.06(15) . 7_565 ?
C11 C2 C2 123.3(3) . 7_565 ?
C1 C2 C2 58.50(13) . 7_565 ?
B6 C2 C2 109.44(17) . 7_565 ?
B5 C2 C2 59.68(13) . 7_565 ?
B3 C2 C2 109.06(15) . 7_565 ?
B9 C2 C2 0.0 7_565 7_565 ?
C13 C12 C17 117.3(3) . . ?
C13 C12 B4 116.8(3) . . ?
C17 C12 B4 125.9(3) . . ?
C12 C13 C14 122.0(4) . . ?
C15 C14 C13 120.0(4) . . ?
C14 C15 C16 120.4(4) . . ?
C15 C16 C17 120.3(4) . . ?
C16 C17 C12 120.1(3) . . ?
C16 C17 C18 119.1(3) . . ?
C12 C17 C18 120.8(3) . . ?
C22 C18 N1 0.0 7_565 7_565 ?
C22 C18 N1 109.7 7_565 . ?
N1 C18 N1 109.7(3) 7_565 . ?
C22 C18 C17 124.95(17) 7_565 . ?
N1 C18 C17 124.95(17) 7_565 . ?
N1 C18 C17 124.95(17) . . ?
C20 C19 C19 120.5(2) . 7_565 ?
C20 C19 N1 132.5(3) . . ?
C19 C19 N1 106.94(16) 7_565 . ?
C21 C20 C19 117.7(4) . . ?
C20 C21 C21 121.8(3) . 7_565 ?
C1 B3 C2 58.03(18) . . ?
C1 B3 B7 104.3(2) . . ?
C2 B3 B7 106.2(2) . . ?
C1 B3 B6 103.8(2) . . ?
C2 B3 B6 58.45(18) . . ?
B7 B3 B6 60.42(18) . . ?
C1 B3 B4 58.84(18) . . ?
C2 B3 B4 107.3(2) . . ?
B7 B3 B4 60.49(19) . . ?
B6 B3 B4 109.0(2) . . ?
C12 B4 C1 124.5(3) . . ?
C12 B4 B3 121.51(16) . 7_565 ?
C1 B4 B3 58.16(15) . 7_565 ?
C12 B4 B3 121.52(16) . . ?
C1 B4 B3 58.17(15) . . ?
B3 B4 B3 107.2(3) 7_565 . ?
C12 B4 B7 124.4(2) . 7_565 ?
C1 B4 B7 102.9(2) . 7_565 ?
B3 B4 B7 59.40(16) 7_565 7_565 ?
B3 B4 B7 106.8(2) . 7_565 ?
C12 B4 B7 124.4(2) . . ?
C1 B4 B7 102.9(2) . . ?
B3 B4 B7 106.8(2) 7_565 . ?
B3 B4 B7 59.40(16) . . ?
B7 B4 B7 59.4(3) 7_565 . ?
C2 B5 B9 60.6 . 7_565 ?
C2 B5 C2 60.6(3) . 7_565 ?
B9 B5 C2 0.0 7_565 7_565 ?
C2 B5 B6 58.48(18) . . ?
B9 B5 B6 107.1(3) 7_565 . ?
C2 B5 B6 107.1(3) 7_565 . ?
C2 B5 B6 107.1(3) . 7_565 ?
B9 B5 B6 58.48(18) 7_565 7_565 ?
C2 B5 B6 58.48(18) 7_565 7_565 ?
B6 B5 B6 108.1(3) . 7_565 ?
C2 B5 B8 105.8(3) . . ?
B9 B5 B8 105.8(3) 7_565 . ?
C2 B5 B8 105.8(3) 7_565 . ?
B6 B5 B8 59.9(2) . . ?
B6 B5 B8 59.9(2) 7_565 . ?
C2 B6 B3 59.60(18) . . ?
C2 B6 B5 59.2(2) . . ?
B3 B6 B5 107.8(2) . . ?
C2 B6 B8 106.6(3) . . ?
B3 B6 B8 107.6(2) . . ?
B5 B6 B8 60.3(2) . . ?
C2 B6 B7 106.6(2) . . ?
B3 B6 B7 59.74(17) . . ?
B5 B6 B7 107.9(3) . . ?
B8 B6 B7 59.7(2) . . ?
B3 B7 B8 108.0(3) . . ?
B3 B7 B7 108.03(15) . 7_565 ?
B8 B7 B7 59.99(13) . 7_565 ?
B3 B7 B6 59.83(18) . . ?
B8 B7 B6 60.1(2) . . ?
B7 B7 B6 108.04(17) 7_565 . ?
B3 B7 B4 60.11(16) . . ?
B8 B7 B4 108.4(2) . . ?
B7 B7 B4 60.28(13) 7_565 . ?
B6 B7 B4 108.3(2) . . ?
B7 B8 B7 60.0(3) . 7_565 ?
B7 B8 B6 60.19(18) . . ?
B7 B8 B6 108.1(3) 7_565 . ?
B7 B8 B6 108.1(3) . 7_565 ?
B7 B8 B6 60.18(18) 7_565 7_565 ?
B6 B8 B6 107.9(3) . 7_565 ?
B7 B8 B5 107.9(3) . . ?
B7 B8 B5 107.9(3) 7_565 . ?
B6 B8 B5 59.77(19) . . ?
B6 B8 B5 59.77(19) 7_565 . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.066

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_B
_database_code_depnum_ccdc_archive 'CCDC 1987442'
loop_
_audit_author_name
_audit_author_address
'Hoi Shan CHAN'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H35 B10 F3 Ir N O2'
_chemical_formula_weight         750.85

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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.8847(19)
_cell_length_b                   12.2650(17)
_cell_length_c                   12.2774(16)
_cell_angle_alpha                90.795(4)
_cell_angle_beta                 114.061(4)
_cell_angle_gamma                106.385(4)
_cell_volume                     1550.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1489
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    4.350
_shelx_estimated_absorpt_T_min   0.220
_shelx_estimated_absorpt_T_max   0.355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3060
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52092
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5575
_reflns_number_gt                5410
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0001P)²+30.0490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5575
_refine_ls_number_parameters     394
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1460
_refine_ls_goodness_of_fit_ref   1.315
_refine_ls_restrained_S_all      1.314
_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
Ir1 Ir 0.18109(4) 0.34535(3) 0.21351(4) 0.02721(14) Uani 1 1 d . . . . .
N1 N 0.3351(8) 0.4983(8) 0.2597(9) 0.037(2) Uani 1 1 d . . . . .
C1 C 0.4648(10) 0.1713(9) 0.2512(10) 0.034(2) Uani 1 1 d . . . . .
C2 C 0.4866(13) 0.0425(9) 0.2684(11) 0.043(3) Uani 1 1 d . . . . .
C11 C 0.3709(13) -0.0603(12) 0.2573(15) 0.064(4) Uani 1 1 d . . . . .
H11A H 0.303545 -0.075215 0.176641 0.096 Uiso 1 1 calc R U . . .
H11B H 0.338287 -0.043088 0.313079 0.096 Uiso 1 1 calc R U . . .
H11C H 0.398618 -0.126906 0.275425 0.096 Uiso 1 1 calc R U . . .
C12 C 0.3299(10) 0.1837(9) 0.2204(10) 0.036(2) Uani 1 1 d . . . . .
C13 C 0.0004(10) 0.2128(9) 0.1763(10) 0.035(2) Uani 1 1 d . U . . .
C14 C -0.0250(10) 0.3171(9) 0.1389(11) 0.036(2) Uani 1 1 d . U . . .
C15 C 0.0401(11) 0.4044(10) 0.2431(11) 0.039(2) Uani 1 1 d . U . . .
C16 C 0.1014(13) 0.3504(10) 0.3505(11) 0.044(3) Uani 1 1 d . U . . .
C17 C 0.0737(10) 0.2348(9) 0.3048(10) 0.036(2) Uani 1 1 d . . . . .
C18 C -0.0598(11) 0.0977(10) 0.1008(12) 0.045(3) Uani 1 1 d . . . . .
H18A H -0.083659 0.106848 0.017573 0.068 Uiso 1 1 calc R U . . .
H18B H -0.135803 0.056355 0.110753 0.068 Uiso 1 1 calc R U . . .
H18C H 0.001276 0.055550 0.125334 0.068 Uiso 1 1 calc R U . . .
C19 C -0.1109(12) 0.3301(12) 0.0129(12) 0.053(3) Uani 1 1 d . . . . .
H19A H -0.093710 0.291375 -0.044214 0.079 Uiso 1 1 calc R U . . .
H19B H -0.093496 0.410153 0.004858 0.079 Uiso 1 1 calc R U . . .
H19C H -0.200327 0.297026 -0.002216 0.079 Uiso 1 1 calc R U . . .
C20 C 0.0351(14) 0.5245(11) 0.2476(15) 0.058(4) Uani 1 1 d . . . . .
H20A H 0.011129 0.546028 0.168331 0.088 Uiso 1 1 calc R U . . .
H20B H 0.118885 0.575610 0.301453 0.088 Uiso 1 1 calc R U . . .
H20C H -0.027988 0.529093 0.275910 0.088 Uiso 1 1 calc R U . . .
C21 C 0.1575(14) 0.4046(13) 0.4750(12) 0.062(4) Uani 1 1 d . U . . .
H21A H 0.208804 0.482800 0.482597 0.093 Uiso 1 1 calc R U . . .
H21B H 0.211491 0.363673 0.526283 0.093 Uiso 1 1 calc R U . . .
H21C H 0.089204 0.403087 0.498273 0.093 Uiso 1 1 calc R U . . .
C22 C 0.1205(12) 0.1485(10) 0.3830(12) 0.047(3) Uani 1 1 d . . . . .
H22A H 0.050828 0.100231 0.398116 0.070 Uiso 1 1 calc R U . . .
H22B H 0.191502 0.188178 0.458133 0.070 Uiso 1 1 calc R U . . .
H22C H 0.148818 0.102072 0.342480 0.070 Uiso 1 1 calc R U . . .
C23 C 0.4023(12) 0.5586(11) 0.3728(12) 0.049(3) Uani 1 1 d . . . . .
H23 H 0.378724 0.532366 0.433598 0.059 Uiso 1 1 calc R U . . .
C24 C 0.5050(12) 0.6582(11) 0.3994(14) 0.055(3) Uani 1 1 d . . . . .
H24 H 0.550533 0.697964 0.477489 0.066 Uiso 1 1 calc R U . . .
C25 C 0.5390(13) 0.6975(11) 0.3108(15) 0.058(4) Uani 1 1 d . . . . .
H25 H 0.606404 0.765639 0.327705 0.070 Uiso 1 1 calc R U . . .
C26 C 0.4745(12) 0.6373(11) 0.1969(14) 0.052(3) Uani 1 1 d . . . . .
H26 H 0.498461 0.663298 0.136321 0.063 Uiso 1 1 calc R U . . .
C27 C 0.3711(10) 0.5351(9) 0.1724(11) 0.036(2) Uani 1 1 d . . . . .
C28 C 0.2990(10) 0.4564(9) 0.0580(10) 0.035(2) Uani 1 1 d . . . . .
C29 C 0.3244(12) 0.4766(12) -0.0429(12) 0.048(3) Uani 1 1 d . . . . .
H29 H 0.385165 0.543897 -0.042774 0.057 Uiso 1 1 calc R U . . .
C30 C 0.2524(16) 0.3886(14) -0.1472(12) 0.058(4) Uani 1 1 d . . . . .
H30 H 0.270878 0.395174 -0.213977 0.069 Uiso 1 1 calc R U . . .
C31 C 0.1699(11) 0.3082(14) -0.1468(11) 0.050(3) Uani 1 1 d . . . . .
C32 C 0.1410(13) 0.2830(13) -0.0448(12) 0.053(4) Uani 1 1 d . . . . .
H32 H 0.079304 0.213805 -0.051103 0.064 Uiso 1 1 calc R U . . .
C34 C 0.0956(18) 0.2056(15) -0.2542(13) 0.068(4) Uani 1 1 d . . . . .
O1 O 0.2336(8) 0.1065(7) 0.1559(10) 0.060(3) Uani 1 1 d . . . . .
O2 O 0.3398(7) 0.2798(6) 0.2701(7) 0.0366(17) Uani 1 1 d . . . . .
F1 F -0.0163(13) 0.1341(10) -0.2643(10) 0.116(4) Uani 1 1 d . . . . .
F2 F 0.0638(16) 0.2442(10) -0.3557(9) 0.139(6) Uani 1 1 d . . . . .
F3 F 0.1593(15) 0.1338(13) -0.2570(14) 0.153(6) Uani 1 1 d . . . . .
B3 B 0.4758(16) 0.0953(13) 0.1386(15) 0.049(3) Uani 1 1 d . . . . .
H3 H 0.394744 0.057871 0.049713 0.059 Uiso 1 1 calc R U . . .
B4 B 0.5552(17) 0.2462(14) 0.1842(19) 0.064(5) Uani 1 1 d . . . . .
H4 H 0.527297 0.308291 0.122915 0.077 Uiso 1 1 calc R U . . .
B5 B 0.6021(14) 0.2781(13) 0.3410(19) 0.065(5) Uani 1 1 d . . . . .
H5 H 0.604592 0.359608 0.381852 0.078 Uiso 1 1 calc R U . . .
B6 B 0.5524(15) 0.1478(15) 0.3913(14) 0.054(4) Uani 1 1 d . . . . .
H6 H 0.520888 0.144477 0.464246 0.065 Uiso 1 1 calc R U . . .
B7 B 0.5937(17) 0.0296(16) 0.2147(18) 0.063(5) Uani 1 1 d . . . . .
H7 H 0.592203 -0.051169 0.173217 0.076 Uiso 1 1 calc R U . . .
B8 B 0.637(2) 0.1549(18) 0.162(2) 0.078(6) Uani 1 1 d . . . . .
H8 H 0.663425 0.157107 0.085430 0.094 Uiso 1 1 calc R U . . .
B9 B 0.7176(19) 0.2687(17) 0.287(3) 0.094(8) Uani 1 1 d . . . . .
H9 H 0.796806 0.344896 0.292879 0.113 Uiso 1 1 calc R U . . .
B10 B 0.7165(17) 0.207(2) 0.416(2) 0.090(7) Uani 1 1 d . . . . .
H10 H 0.795273 0.242025 0.506505 0.108 Uiso 1 1 calc R U . . .
B11 B 0.6367(17) 0.0541(17) 0.3707(18) 0.069(5) Uani 1 1 d . . . . .
H11 H 0.660458 -0.009997 0.430593 0.082 Uiso 1 1 calc R U . . .
B12 B 0.7385(18) 0.1323(19) 0.306(2) 0.086(7) Uani 1 1 d . . . . .
H12 H 0.832739 0.120098 0.325165 0.103 Uiso 1 1 calc R U . . .
C33 C 0.1958(7) 0.3506(6) 0.0512(7) 0.0104(15) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C33 2.070(8) . ?
Ir1 N1 2.092(9) . ?
Ir1 O2 2.119(7) . ?
Ir1 C15 2.154(10) . ?
Ir1 C14 2.155(10) . ?
Ir1 C13 2.161(10) . ?
Ir1 C17 2.226(10) . ?
Ir1 C16 2.249(11) . ?
N1 C27 1.347(14) . ?
N1 C23 1.360(15) . ?
C1 C12 1.543(14) . ?
C1 C2 1.674(14) . ?
C1 B6 1.687(18) . ?
C1 B4 1.691(18) . ?
C1 B5 1.697(17) . ?
C1 B3 1.726(18) . ?
C2 C11 1.538(17) . ?
C2 B11 1.67(2) . ?
C2 B7 1.696(19) . ?
C2 B3 1.698(18) . ?
C2 B6 1.724(19) . ?
C12 O1 1.209(13) . ?
C12 O2 1.273(13) . ?
C13 C17 1.434(16) . ?
C13 C14 1.435(15) . ?
C13 C18 1.489(15) . ?
C14 C15 1.438(16) . ?
C14 C19 1.507(16) . ?
C15 C16 1.490(17) . ?
C15 C20 1.492(16) . ?
C16 C17 1.414(16) . ?
C16 C21 1.454(18) . ?
C17 C22 1.509(15) . ?
C23 C24 1.382(17) . ?
C24 C25 1.36(2) . ?
C25 C26 1.37(2) . ?
C26 C27 1.410(15) . ?
C27 C28 1.467(16) . ?
C28 C29 1.400(16) . ?
C28 C33 1.487(12) . ?
C29 C30 1.44(2) . ?
C30 C31 1.18(2) . ?
C31 C32 1.444(16) . ?
C31 C34 1.57(2) . ?
C32 C33 1.242(17) . ?
C34 F2 1.286(18) . ?
C34 F3 1.32(2) . ?
C34 F1 1.326(19) . ?
B3 B8 1.75(2) . ?
B3 B7 1.75(2) . ?
B3 B4 1.78(2) . ?
B4 B9 1.76(3) . ?
B4 B8 1.76(2) . ?
B4 B5 1.77(3) . ?
B5 B6 1.75(3) . ?
B5 B10 1.77(3) . ?
B5 B9 1.78(3) . ?
B6 B10 1.77(3) . ?
B6 B11 1.80(2) . ?
B7 B8 1.70(3) . ?
B7 B12 1.72(3) . ?
B7 B11 1.77(3) . ?
B8 B12 1.76(3) . ?
B8 B9 1.79(3) . ?
B9 B12 1.77(3) . ?
B9 B10 1.77(4) . ?
B10 B12 1.77(3) . ?
B10 B11 1.80(3) . ?
B11 B12 1.78(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
C33 Ir1 N1 80.9(3) . . ?
C33 Ir1 O2 85.3(3) . . ?
N1 Ir1 O2 79.8(3) . . ?
C33 Ir1 C15 121.7(4) . . ?
N1 Ir1 C15 101.4(4) . . ?
O2 Ir1 C15 152.9(4) . . ?
C33 Ir1 C14 96.4(4) . . ?
N1 Ir1 C14 130.1(4) . . ?
O2 Ir1 C14 150.1(4) . . ?
C15 Ir1 C14 39.0(4) . . ?
C33 Ir1 C13 105.6(4) . . ?
N1 Ir1 C13 166.7(4) . . ?
O2 Ir1 C13 111.9(3) . . ?
C15 Ir1 C13 65.3(4) . . ?
C14 Ir1 C13 38.8(4) . . ?
C33 Ir1 C17 141.5(4) . . ?
N1 Ir1 C17 137.4(4) . . ?
O2 Ir1 C17 97.1(4) . . ?
C15 Ir1 C17 63.6(4) . . ?
C14 Ir1 C17 63.5(4) . . ?
C13 Ir1 C17 38.1(4) . . ?
C33 Ir1 C16 160.4(4) . . ?
N1 Ir1 C16 105.7(4) . . ?
O2 Ir1 C16 113.8(4) . . ?
C15 Ir1 C16 39.5(4) . . ?
C14 Ir1 C16 65.1(5) . . ?
C13 Ir1 C16 64.4(4) . . ?
C17 Ir1 C16 36.8(4) . . ?
C27 N1 C23 119.2(10) . . ?
C27 N1 Ir1 117.2(7) . . ?
C23 N1 Ir1 123.5(8) . . ?
C12 C1 C2 120.0(9) . . ?
C12 C1 B6 118.9(10) . . ?
C2 C1 B6 61.7(8) . . ?
C12 C1 B4 119.0(10) . . ?
C2 C1 B4 109.9(9) . . ?
B6 C1 B4 114.3(11) . . ?
C12 C1 B5 120.6(9) . . ?
C2 C1 B5 111.0(9) . . ?
B6 C1 B5 62.4(10) . . ?
B4 C1 B5 63.2(11) . . ?
C12 C1 B3 115.4(10) . . ?
C2 C1 B3 59.9(7) . . ?
B6 C1 B3 113.8(9) . . ?
B4 C1 B3 63.0(9) . . ?
B5 C1 B3 115.3(10) . . ?
C11 C2 C1 118.3(10) . . ?
C11 C2 B11 120.0(11) . . ?
C1 C2 B11 111.5(10) . . ?
C11 C2 B7 122.0(11) . . ?
C1 C2 B7 109.9(10) . . ?
B11 C2 B7 63.2(11) . . ?
C11 C2 B3 116.0(11) . . ?
C1 C2 B3 61.6(7) . . ?
B11 C2 B3 115.9(12) . . ?
B7 C2 B3 62.2(9) . . ?
C11 C2 B6 117.2(12) . . ?
C1 C2 B6 59.5(7) . . ?
B11 C2 B6 63.9(9) . . ?
B7 C2 B6 114.0(11) . . ?
B3 C2 B6 113.4(10) . . ?
O1 C12 O2 129.4(10) . . ?
O1 C12 C1 119.3(10) . . ?
O2 C12 C1 111.2(9) . . ?
C17 C13 C14 107.0(10) . . ?
C17 C13 C18 125.5(10) . . ?
C14 C13 C18 126.4(10) . . ?
C17 C13 Ir1 73.4(6) . . ?
C14 C13 Ir1 70.3(6) . . ?
C18 C13 Ir1 130.7(8) . . ?
C13 C14 C15 108.3(10) . . ?
C13 C14 C19 125.4(11) . . ?
C15 C14 C19 126.3(11) . . ?
C13 C14 Ir1 70.8(6) . . ?
C15 C14 Ir1 70.5(6) . . ?
C19 C14 Ir1 126.7(8) . . ?
C14 C15 C16 108.0(10) . . ?
C14 C15 C20 126.8(11) . . ?
C16 C15 C20 124.8(11) . . ?
C14 C15 Ir1 70.5(6) . . ?
C16 C15 Ir1 73.7(6) . . ?
C20 C15 Ir1 127.0(8) . . ?
C17 C16 C21 129.1(12) . . ?
C17 C16 C15 105.2(10) . . ?
C21 C16 C15 124.9(12) . . ?
C17 C16 Ir1 70.7(6) . . ?
C21 C16 Ir1 133.8(9) . . ?
C15 C16 Ir1 66.8(6) . . ?
C16 C17 C13 111.3(10) . . ?
C16 C17 C22 123.3(11) . . ?
C13 C17 C22 125.4(10) . . ?
C16 C17 Ir1 72.5(6) . . ?
C13 C17 Ir1 68.5(6) . . ?
C22 C17 Ir1 124.7(8) . . ?
N1 C23 C24 121.3(13) . . ?
C25 C24 C23 119.6(13) . . ?
C24 C25 C26 120.2(12) . . ?
C25 C26 C27 119.2(13) . . ?
N1 C27 C26 120.5(11) . . ?
N1 C27 C28 113.6(9) . . ?
C26 C27 C28 125.8(11) . . ?
C29 C28 C27 122.8(10) . . ?
C29 C28 C33 119.5(11) . . ?
C27 C28 C33 117.7(9) . . ?
C28 C29 C30 117.2(11) . . ?
C31 C30 C29 119.3(12) . . ?
C30 C31 C32 125.3(14) . . ?
C30 C31 C34 121.2(13) . . ?
C32 C31 C34 112.7(13) . . ?
C33 C32 C31 122.3(13) . . ?
F2 C34 F3 106.8(15) . . ?
F2 C34 F1 102.9(15) . . ?
F3 C34 F1 101.7(16) . . ?
F2 C34 C31 110.2(14) . . ?
F3 C34 C31 116.1(14) . . ?
F1 C34 C31 117.8(12) . . ?
C12 O2 Ir1 121.5(7) . . ?
C2 B3 C1 58.5(7) . . ?
C2 B3 B8 104.2(12) . . ?
C1 B3 B8 104.2(12) . . ?
C2 B3 B7 58.8(8) . . ?
C1 B3 B7 104.9(11) . . ?
B8 B3 B7 58.3(10) . . ?
C2 B3 B4 104.5(11) . . ?
C1 B3 B4 57.6(8) . . ?
B8 B3 B4 59.9(10) . . ?
B7 B3 B4 106.0(12) . . ?
C1 B4 B9 105.3(14) . . ?
C1 B4 B8 105.0(11) . . ?
B9 B4 B8 61.2(12) . . ?
C1 B4 B5 58.6(8) . . ?
B9 B4 B5 60.5(12) . . ?
B8 B4 B5 109.1(14) . . ?
C1 B4 B3 59.4(8) . . ?
B9 B4 B3 108.5(12) . . ?
B8 B4 B3 59.0(10) . . ?
B5 B4 B3 108.6(11) . . ?
C1 B5 B6 58.5(8) . . ?
C1 B5 B10 104.6(11) . . ?
B6 B5 B10 60.3(11) . . ?
C1 B5 B4 58.3(8) . . ?
B6 B5 B4 107.1(11) . . ?
B10 B5 B4 107.0(13) . . ?
C1 B5 B9 104.2(12) . . ?
B6 B5 B9 107.9(12) . . ?
B10 B5 B9 59.8(12) . . ?
B4 B5 B9 59.4(12) . . ?
C1 B6 C2 58.8(7) . . ?
C1 B6 B5 59.1(9) . . ?
C2 B6 B5 106.1(11) . . ?
C1 B6 B10 105.1(13) . . ?
C2 B6 B10 103.8(12) . . ?
B5 B6 B10 60.3(11) . . ?
C1 B6 B11 105.1(11) . . ?
C2 B6 B11 56.7(9) . . ?
B5 B6 B11 109.2(13) . . ?
B10 B6 B11 60.7(11) . . ?
C2 B7 B8 106.2(11) . . ?
C2 B7 B12 105.4(12) . . ?
B8 B7 B12 62.0(13) . . ?
C2 B7 B3 58.9(8) . . ?
B8 B7 B3 60.7(10) . . ?
B12 B7 B3 110.1(13) . . ?
C2 B7 B11 57.8(9) . . ?
B8 B7 B11 111.3(15) . . ?
B12 B7 B11 61.4(12) . . ?
B3 B7 B11 108.6(11) . . ?
B7 B8 B3 61.0(10) . . ?
B7 B8 B4 109.1(11) . . ?
B3 B8 B4 61.1(9) . . ?
B7 B8 B12 59.5(12) . . ?
B3 B8 B12 108.4(13) . . ?
B4 B8 B12 107.1(15) . . ?
B7 B8 B9 107.8(16) . . ?
B3 B8 B9 108.7(12) . . ?
B4 B8 B9 59.3(11) . . ?
B12 B8 B9 59.5(13) . . ?
B4 B9 B12 107.2(14) . . ?
B4 B9 B10 107.7(12) . . ?
B12 B9 B10 60.0(13) . . ?
B4 B9 B5 60.2(10) . . ?
B12 B9 B5 107.8(14) . . ?
B10 B9 B5 59.8(12) . . ?
B4 B9 B8 59.5(12) . . ?
B12 B9 B8 59.5(13) . . ?
B10 B9 B8 107.3(14) . . ?
B5 B9 B8 107.6(12) . . ?
B12 B10 B9 59.9(13) . . ?
B12 B10 B6 107.7(13) . . ?
B9 B10 B6 107.5(13) . . ?
B12 B10 B5 108.1(16) . . ?
B9 B10 B5 60.3(12) . . ?
B6 B10 B5 59.4(9) . . ?
B12 B10 B11 59.9(12) . . ?
B9 B10 B11 108.1(15) . . ?
B6 B10 B11 60.5(10) . . ?
B5 B10 B11 108.3(12) . . ?
C2 B11 B7 59.0(9) . . ?
C2 B11 B12 103.7(13) . . ?
B7 B11 B12 58.1(12) . . ?
C2 B11 B6 59.4(8) . . ?
B7 B11 B6 107.1(11) . . ?
B12 B11 B6 105.8(13) . . ?
C2 B11 B10 104.4(11) . . ?
B7 B11 B10 105.5(15) . . ?
B12 B11 B10 59.1(12) . . ?
B6 B11 B10 58.9(10) . . ?
B7 B12 B8 58.5(12) . . ?
B7 B12 B9 108.2(14) . . ?
B8 B12 B9 61.0(14) . . ?
B7 B12 B10 109.0(13) . . ?
B8 B12 B10 108.7(13) . . ?
B9 B12 B10 60.1(14) . . ?
B7 B12 B11 60.5(11) . . ?
B8 B12 B11 107.7(12) . . ?
B9 B12 B11 109.3(13) . . ?
B10 B12 B11 61.0(13) . . ?
C32 C33 C28 116.1(9) . . ?
C32 C33 Ir1 133.4(7) . . ?
C28 C33 Ir1 110.4(6) . . ?

_refine_diff_density_max         4.117
_refine_diff_density_min         -2.616
_refine_diff_density_rms         0.190


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    Moisture-sensitive
