# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_10d
_audit_block_doi                 10.5517/ccdc.csd.cc2bl6y3
_database_code_depnum_ccdc_archive 'CCDC 2162465'
loop_
_audit_author_name
_audit_author_address
'Bella Chan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-29 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            'C15 H23 B10 N'
_chemical_formula_weight         325.44

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

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

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

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

_cell_length_a                   16.1095(5)
_cell_length_b                   8.0730(2)
_cell_length_c                   14.4851(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.1354(19)
_cell_angle_gamma                90
_cell_volume                     1878.91(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    316
_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    1.150
_exptl_crystal_F_000             680
_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  0.6518
_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            38279
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         25.245
_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             3405
_reflns_number_gt                2181
_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)+(0.0719P)²+1.0245P] 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         3405
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1702
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.85969(12) 0.7134(3) 0.91677(14) 0.0532(6) Uani 1 1 d . . . . .
H1A H 0.8807 0.7258 0.8643 0.064 Uiso 1 1 calc R U . . .
C1 C 0.71607(14) 0.5702(3) 0.83668(16) 0.0448(6) Uani 1 1 d . . . . .
H1 H 0.7533 0.4829 0.7985 0.054 Uiso 1 1 calc R U . . .
C2 C 0.62611(15) 0.5106(3) 0.87209(18) 0.0513(7) Uani 1 1 d . . . . .
C11 C 0.5979(2) 0.3353(4) 0.8519(3) 0.0844(10) Uani 1 1 d . . . . .
H11A H 0.5448 0.3175 0.8763 0.127 Uiso 1 1 calc R U . . .
H11B H 0.5931 0.3176 0.7862 0.127 Uiso 1 1 calc R U . . .
H11C H 0.6378 0.2593 0.8803 0.127 Uiso 1 1 calc R U . . .
C12 C 0.91814(14) 0.7010(3) 0.99270(16) 0.0427(6) Uani 1 1 d . . . . .
C13 C 0.99704(15) 0.7642(4) 0.98585(17) 0.0527(7) Uani 1 1 d . . . . .
H13A H 1.0104 0.8121 0.9304 0.063 Uiso 1 1 calc R U . . .
C14 C 1.05626(15) 0.7583(3) 1.05852(18) 0.0523(7) Uani 1 1 d . . . . .
H14A H 1.1086 0.8026 1.0511 0.063 Uiso 1 1 calc R U . . .
C15 C 1.04031(13) 0.6879(3) 1.14310(16) 0.0394(6) Uani 1 1 d . . . . .
C16 C 0.96148(14) 0.6222(3) 1.14900(17) 0.0480(6) Uani 1 1 d . . . . .
H16A H 0.9485 0.5731 1.2042 0.058 Uiso 1 1 calc R U . . .
C17 C 0.90141(15) 0.6269(3) 1.07594(18) 0.0492(7) Uani 1 1 d . . . . .
H17A H 0.8494 0.5801 1.0825 0.059 Uiso 1 1 calc R U . . .
C18 C 1.10443(14) 0.6817(3) 1.22154(16) 0.0393(6) Uani 1 1 d . . . . .
C19 C 1.16616(15) 0.8027(3) 1.23273(18) 0.0482(6) Uani 1 1 d . . . . .
H19A H 1.1663 0.8899 1.1908 0.058 Uiso 1 1 calc R U . . .
C20 C 1.22708(16) 0.7959(3) 1.30475(19) 0.0558(7) Uani 1 1 d . . . . .
H20A H 1.2678 0.8776 1.3103 0.067 Uiso 1 1 calc R U . . .
C21 C 1.22793(18) 0.6690(4) 1.36838(18) 0.0572(7) Uani 1 1 d . . . . .
H21A H 1.2692 0.6636 1.4166 0.069 Uiso 1 1 calc R U . . .
C22 C 1.16662(16) 0.5504(3) 1.35928(17) 0.0536(7) Uani 1 1 d . . . . .
H22A H 1.1661 0.4651 1.4024 0.064 Uiso 1 1 calc R U . . .
C23 C 1.10586(15) 0.5558(3) 1.28715(17) 0.0463(6) Uani 1 1 d . . . . .
H23A H 1.0652 0.4738 1.2823 0.056 Uiso 1 1 calc R U . . .
B3 B 0.71145(17) 0.5362(4) 0.9507(2) 0.0476(7) Uani 1 1 d . . . . .
H3 H 0.7431 0.4335 0.9887 0.057 Uiso 1 1 calc R U . . .
B4 B 0.76946(16) 0.7088(4) 0.91200(19) 0.0413(7) Uani 1 1 d . . . . .
B5 B 0.71526(18) 0.7717(4) 0.8064(2) 0.0476(7) Uani 1 1 d . . . . .
H5 H 0.7503 0.8236 0.7508 0.057 Uiso 1 1 calc R U . . .
B6 B 0.62767(19) 0.6447(4) 0.7807(2) 0.0524(8) Uani 1 1 d . . . . .
H6 H 0.6056 0.6133 0.7092 0.063 Uiso 1 1 calc R U . . .
B7 B 0.61128(18) 0.6057(5) 0.9742(2) 0.0563(9) Uani 1 1 d . . . . .
H7 H 0.5774 0.5494 1.0295 0.068 Uiso 1 1 calc R U . . .
B8 B 0.69895(17) 0.7336(4) 0.9996(2) 0.0494(8) Uani 1 1 d . . . . .
H8 H 0.7218 0.7619 1.0712 0.059 Uiso 1 1 calc R U . . .
B9 B 0.70088(18) 0.8814(4) 0.9083(2) 0.0508(8) Uani 1 1 d . . . . .
H9 H 0.7250 1.0077 0.9200 0.061 Uiso 1 1 calc R U . . .
B10 B 0.6150(2) 0.8429(4) 0.8279(2) 0.0565(8) Uani 1 1 d . . . . .
H10 H 0.5838 0.9432 0.7875 0.068 Uiso 1 1 calc R U . . .
B11 B 0.55922(19) 0.6725(4) 0.8690(2) 0.0552(8) Uani 1 1 d . . . . .
H11 H 0.4914 0.6602 0.8555 0.066 Uiso 1 1 calc R U . . .
B12 B 0.60416(19) 0.8185(4) 0.9482(2) 0.0591(9) Uani 1 1 d . . . . .
H12 H 0.5656 0.9030 0.9865 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 C12 1.399(3) . ?
N1 B4 1.451(3) . ?
C1 C2 1.644(3) . ?
C1 B3 1.681(4) . ?
C1 B5 1.685(4) . ?
C1 B6 1.697(4) . ?
C1 B4 1.745(4) . ?
C2 C11 1.508(4) . ?
C2 B11 1.692(4) . ?
C2 B7 1.698(4) . ?
C2 B6 1.712(4) . ?
C2 B3 1.733(4) . ?
C12 C13 1.380(3) . ?
C12 C17 1.390(3) . ?
C13 C14 1.369(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.385(3) . ?
C15 C18 1.480(3) . ?
C16 C17 1.382(3) . ?
C18 C23 1.390(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.381(3) . ?
C20 C21 1.377(4) . ?
C21 C22 1.375(4) . ?
C22 C23 1.380(3) . ?
B3 B8 1.761(4) . ?
B3 B7 1.764(4) . ?
B3 B4 1.790(4) . ?
B4 B8 1.774(4) . ?
B4 B9 1.777(4) . ?
B4 B5 1.780(4) . ?
B5 B9 1.751(4) . ?
B5 B6 1.762(4) . ?
B5 B10 1.763(4) . ?
B6 B10 1.758(5) . ?
B6 B11 1.763(4) . ?
B7 B12 1.761(5) . ?
B7 B8 1.767(4) . ?
B7 B11 1.769(4) . ?
B8 B9 1.783(4) . ?
B8 B12 1.787(4) . ?
B9 B10 1.770(4) . ?
B9 B12 1.775(4) . ?
B10 B11 1.769(5) . ?
B10 B12 1.774(5) . ?
B11 B12 1.763(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 B4 130.6(2) . . ?
C2 C1 B3 62.82(15) . . ?
C2 C1 B5 111.93(19) . . ?
B3 C1 B5 114.4(2) . . ?
C2 C1 B6 61.63(16) . . ?
B3 C1 B6 115.6(2) . . ?
B5 C1 B6 62.80(17) . . ?
C2 C1 B4 113.48(19) . . ?
B3 C1 B4 62.95(16) . . ?
B5 C1 B4 62.48(16) . . ?
B6 C1 B4 115.5(2) . . ?
C11 C2 C1 118.3(2) . . ?
C11 C2 B11 122.5(2) . . ?
C1 C2 B11 109.9(2) . . ?
C11 C2 B7 122.3(3) . . ?
C1 C2 B7 108.78(19) . . ?
B11 C2 B7 62.90(18) . . ?
C11 C2 B6 117.7(2) . . ?
C1 C2 B6 60.73(16) . . ?
B11 C2 B6 62.36(18) . . ?
B7 C2 B6 113.5(2) . . ?
C11 C2 B3 117.0(2) . . ?
C1 C2 B3 59.63(15) . . ?
B11 C2 B3 113.5(2) . . ?
B7 C2 B3 61.88(17) . . ?
B6 C2 B3 112.2(2) . . ?
C13 C12 C17 117.3(2) . . ?
C13 C12 N1 119.2(2) . . ?
C17 C12 N1 123.5(2) . . ?
C14 C13 C12 121.7(2) . . ?
C13 C14 C15 121.9(2) . . ?
C16 C15 C14 116.1(2) . . ?
C16 C15 C18 122.1(2) . . ?
C14 C15 C18 121.8(2) . . ?
C17 C16 C15 122.5(2) . . ?
C16 C17 C12 120.5(2) . . ?
C23 C18 C19 117.1(2) . . ?
C23 C18 C15 121.7(2) . . ?
C19 C18 C15 121.2(2) . . ?
C20 C19 C18 121.4(2) . . ?
C21 C20 C19 120.5(3) . . ?
C22 C21 C20 118.8(2) . . ?
C21 C22 C23 121.1(3) . . ?
C22 C23 C18 121.1(2) . . ?
C1 B3 C2 57.55(15) . . ?
C1 B3 B8 105.2(2) . . ?
C2 B3 B8 105.3(2) . . ?
C1 B3 B7 104.1(2) . . ?
C2 B3 B7 58.09(16) . . ?
B8 B3 B7 60.15(18) . . ?
C1 B3 B4 60.29(15) . . ?
C2 B3 B4 107.15(19) . . ?
B8 B3 B4 59.95(16) . . ?
B7 B3 B4 108.6(2) . . ?
N1 B4 C1 119.6(2) . . ?
N1 B4 B8 130.8(2) . . ?
C1 B4 B8 101.95(18) . . ?
N1 B4 B9 126.9(2) . . ?
C1 B4 B9 101.92(19) . . ?
B8 B4 B9 60.29(17) . . ?
N1 B4 B5 117.5(2) . . ?
C1 B4 B5 57.09(15) . . ?
B8 B4 B5 106.4(2) . . ?
B9 B4 B5 58.98(16) . . ?
N1 B4 B3 123.3(2) . . ?
C1 B4 B3 56.76(15) . . ?
B8 B4 B3 59.21(16) . . ?
B9 B4 B3 106.40(19) . . ?
B5 B4 B3 104.85(19) . . ?
C1 B5 B9 105.6(2) . . ?
C1 B5 B6 58.96(16) . . ?
B9 B5 B6 108.7(2) . . ?
C1 B5 B10 105.0(2) . . ?
B9 B5 B10 60.50(17) . . ?
B6 B5 B10 59.81(18) . . ?
C1 B5 B4 60.43(15) . . ?
B9 B5 B4 60.44(16) . . ?
B6 B5 B4 110.6(2) . . ?
B10 B5 B4 109.9(2) . . ?
C1 B6 C2 57.64(15) . . ?
C1 B6 B10 104.7(2) . . ?
C2 B6 B10 105.4(2) . . ?
C1 B6 B5 58.25(16) . . ?
C2 B6 B5 105.1(2) . . ?
B10 B6 B5 60.12(18) . . ?
C1 B6 B11 104.2(2) . . ?
C2 B6 B11 58.27(17) . . ?
B10 B6 B11 60.35(18) . . ?
B5 B6 B11 107.8(2) . . ?
C2 B7 B12 105.4(2) . . ?
C2 B7 B3 60.03(16) . . ?
B12 B7 B3 108.4(2) . . ?
C2 B7 B8 106.6(2) . . ?
B12 B7 B8 60.86(18) . . ?
B3 B7 B8 59.82(17) . . ?
C2 B7 B11 58.40(17) . . ?
B12 B7 B11 59.94(19) . . ?
B3 B7 B11 108.3(2) . . ?
B8 B7 B11 108.9(2) . . ?
B3 B8 B7 60.03(17) . . ?
B3 B8 B4 60.83(16) . . ?
B7 B8 B4 109.2(2) . . ?
B3 B8 B9 107.4(2) . . ?
B7 B8 B9 107.0(2) . . ?
B4 B8 B9 59.94(16) . . ?
B3 B8 B12 107.4(2) . . ?
B7 B8 B12 59.41(18) . . ?
B4 B8 B12 108.5(2) . . ?
B9 B8 B12 59.62(18) . . ?
B5 B9 B10 60.09(17) . . ?
B5 B9 B12 107.6(2) . . ?
B10 B9 B12 60.06(18) . . ?
B5 B9 B4 60.58(16) . . ?
B10 B9 B4 109.7(2) . . ?
B12 B9 B4 108.9(2) . . ?
B5 B9 B8 107.3(2) . . ?
B10 B9 B8 108.4(2) . . ?
B12 B9 B8 60.28(17) . . ?
B4 B9 B8 59.77(16) . . ?
B6 B10 B5 60.07(17) . . ?
B6 B10 B11 59.97(18) . . ?
B5 B10 B11 107.5(2) . . ?
B6 B10 B9 108.0(2) . . ?
B5 B10 B9 59.41(17) . . ?
B11 B10 B9 107.9(2) . . ?
B6 B10 B12 107.7(2) . . ?
B5 B10 B12 107.1(2) . . ?
B11 B10 B12 59.69(19) . . ?
B9 B10 B12 60.10(18) . . ?
C2 B11 B6 59.37(17) . . ?
C2 B11 B12 105.6(2) . . ?
B6 B11 B12 107.9(2) . . ?
C2 B11 B7 58.70(17) . . ?
B6 B11 B7 107.7(2) . . ?
B12 B11 B7 59.80(19) . . ?
C2 B11 B10 105.7(2) . . ?
B6 B11 B10 59.68(18) . . ?
B12 B11 B10 60.28(19) . . ?
B7 B11 B10 107.8(2) . . ?
B7 B12 B11 60.26(18) . . ?
B7 B12 B10 108.0(2) . . ?
B11 B12 B10 60.03(19) . . ?
B7 B12 B9 107.7(2) . . ?
B11 B12 B9 108.0(2) . . ?
B10 B12 B9 59.85(18) . . ?
B7 B12 B8 59.73(17) . . ?
B11 B12 B8 108.2(2) . . ?
B10 B12 B8 108.1(2) . . ?
B9 B12 B8 60.10(17) . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041

_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_12c
_audit_block_doi                 10.5517/ccdc.csd.cc2bl717
_database_code_depnum_ccdc_archive 'CCDC 2162468'
loop_
_audit_author_name
_audit_author_address
'Bella Chan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-29 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 H27 B10 N O3 S'
_chemical_formula_weight         445.56

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.2450(4)
_cell_length_b                   13.3323(8)
_cell_length_c                   13.4099(8)
_cell_angle_alpha                112.5805(17)
_cell_angle_beta                 97.0506(17)
_cell_angle_gamma                96.4610(16)
_cell_volume                     1168.80(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    674
_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    1.266
_exptl_crystal_F_000             464
_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    0.161
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.655045
_exptl_absorpt_correction_T_max  0.745618
_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            4214
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_v_R_equivalents   ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.877
_diffrn_reflns_theta_max         25.250
_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             4214
_reflns_number_gt                3603
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+0.5865P] 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         4214
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71921(9) 0.38580(4) 0.45198(5) 0.03810(17) Uani 1 1 d . . . . .
N1 N 0.7874(3) 0.44844(14) 0.58405(14) 0.0379(4) Uani 1 1 d . . . . .
H1A H 0.8620 0.5110 0.6093 0.046 Uiso 1 1 calc R U . . .
O1 O 0.8101(3) 0.45444(14) 0.40567(14) 0.0492(4) Uani 1 1 d . . . . .
O2 O 0.5181(2) 0.35852(15) 0.42874(14) 0.0505(4) Uani 1 1 d . . . . .
O3 O 0.7519(3) 1.15001(15) 0.98939(18) 0.0687(6) Uani 1 1 d . . . . .
C1 C 0.6865(3) 0.50095(18) 0.78809(18) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.5076(3) 0.41258(18) 0.69863(19) 0.0396(5) Uani 1 1 d . . . . .
H2 H 0.4064 0.4414 0.6521 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7019(3) 0.61730(18) 0.80134(19) 0.0403(5) Uani 1 1 d . . . . .
H11A H 0.6905 0.6318 0.7385 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7307(4) 0.70078(19) 0.89720(19) 0.0429(6) Uani 1 1 d . . . . .
H12A H 0.7474 0.6833 0.9582 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7399(3) 0.81800(18) 0.92036(19) 0.0395(5) Uani 1 1 d . . . . .
C14 C 0.7261(4) 0.8585(2) 0.8392(2) 0.0507(6) Uani 1 1 d . . . . .
H14A H 0.7139 0.8101 0.7661 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7302(5) 0.9687(2) 0.8651(2) 0.0584(7) Uani 1 1 d . . . . .
H15A H 0.7203 0.9941 0.8093 0.070 Uiso 1 1 calc R U . . .
C16 C 0.7488(4) 1.0428(2) 0.9730(2) 0.0477(6) Uani 1 1 d . . . . .
C17 C 0.7628(4) 1.0046(2) 1.0545(2) 0.0526(6) Uani 1 1 d . . . . .
H17A H 0.7756 1.0533 1.1275 0.063 Uiso 1 1 calc R U . . .
C18 C 0.7578(4) 0.8935(2) 1.0274(2) 0.0529(7) Uani 1 1 d . . . . .
H18A H 0.7667 0.8684 1.0834 0.063 Uiso 1 1 calc R U . . .
C19 C 0.7684(5) 1.2290(2) 1.0981(3) 0.0694(9) Uani 1 1 d . . . . .
H19A H 0.7688 1.3008 1.0975 0.104 Uiso 1 1 calc R U . . .
H19B H 0.6636 1.2110 1.1291 0.104 Uiso 1 1 calc R U . . .
H19C H 0.8842 1.2289 1.1413 0.104 Uiso 1 1 calc R U . . .
C20 C 0.8110(3) 0.26189(18) 0.41234(18) 0.0370(5) Uani 1 1 d . . . . .
C21 C 1.0036(4) 0.2661(2) 0.4305(2) 0.0464(6) Uani 1 1 d . . . . .
H21A H 1.0855 0.3333 0.4576 0.056 Uiso 1 1 calc R U . . .
C22 C 1.0731(4) 0.1692(2) 0.4080(2) 0.0539(7) Uani 1 1 d . . . . .
H22A H 1.2030 0.1718 0.4201 0.065 Uiso 1 1 calc R U . . .
C23 C 0.9540(4) 0.0678(2) 0.3679(2) 0.0521(7) Uani 1 1 d . . . . .
C24 C 0.7637(4) 0.0663(2) 0.3485(2) 0.0579(7) Uani 1 1 d . . . . .
H24A H 0.6817 -0.0010 0.3200 0.070 Uiso 1 1 calc R U . . .
C25 C 0.6901(4) 0.1622(2) 0.3702(2) 0.0488(6) Uani 1 1 d . . . . .
H25A H 0.5603 0.1594 0.3565 0.059 Uiso 1 1 calc R U . . .
C26 C 1.0322(6) -0.0367(3) 0.3485(3) 0.0836(11) Uani 1 1 d . . . . .
H26A H 1.1676 -0.0197 0.3665 0.125 Uiso 1 1 calc R U . . .
H26B H 0.9850 -0.0707 0.3940 0.125 Uiso 1 1 calc R U . . .
H26C H 0.9938 -0.0865 0.2727 0.125 Uiso 1 1 calc R U . . .
B3 B 0.7304(4) 0.4054(2) 0.6629(2) 0.0347(6) Uani 1 1 d . . . . .
B4 B 0.8773(4) 0.4356(2) 0.7897(2) 0.0391(6) Uani 1 1 d . . . . .
H4 H 1.0246 0.4774 0.8066 0.047 Uiso 1 1 calc R U . . .
B5 B 0.7400(4) 0.4632(2) 0.8945(2) 0.0456(7) Uani 1 1 d . . . . .
H5 H 0.7987 0.5222 0.9792 0.055 Uiso 1 1 calc R U . . .
B6 B 0.5009(4) 0.4504(3) 0.8352(2) 0.0484(7) Uani 1 1 d . . . . .
H6 H 0.4030 0.5005 0.8798 0.058 Uiso 1 1 calc R U . . .
B7 B 0.5638(4) 0.2853(2) 0.6349(2) 0.0421(6) Uani 1 1 d . . . . .
H7 H 0.5035 0.2280 0.5498 0.051 Uiso 1 1 calc R U . . .
B8 B 0.8018(4) 0.2971(2) 0.6945(2) 0.0399(6) Uani 1 1 d . . . . .
H8 H 0.8990 0.2469 0.6493 0.048 Uiso 1 1 calc R U . . .
B9 B 0.8092(4) 0.3323(2) 0.8368(2) 0.0472(7) Uani 1 1 d . . . . .
H9 H 0.9120 0.3052 0.8842 0.057 Uiso 1 1 calc R U . . .
B10 B 0.5756(5) 0.3416(3) 0.8642(3) 0.0528(7) Uani 1 1 d . . . . .
H10 H 0.5262 0.3205 0.9292 0.063 Uiso 1 1 calc R U . . .
B11 B 0.4254(4) 0.3123(3) 0.7386(3) 0.0507(7) Uani 1 1 d . . . . .
H11 H 0.2767 0.2724 0.7202 0.061 Uiso 1 1 calc R U . . .
B12 B 0.6144(4) 0.2391(2) 0.7407(3) 0.0480(7) Uani 1 1 d . . . . .
H12 H 0.5900 0.1511 0.7253 0.058 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
S1 O2 1.4260(19) . ?
S1 O1 1.4346(18) . ?
S1 N1 1.6232(18) . ?
S1 C20 1.764(2) . ?
N1 B3 1.462(3) . ?
O3 C16 1.357(3) . ?
O3 C19 1.413(4) . ?
C1 C11 1.482(3) . ?
C1 C2 1.642(3) . ?
C1 B5 1.703(3) . ?
C1 B4 1.717(3) . ?
C1 B6 1.730(4) . ?
C1 B3 1.767(3) . ?
C2 B11 1.696(4) . ?
C2 B7 1.704(3) . ?
C2 B6 1.711(4) . ?
C2 B3 1.742(3) . ?
C11 C12 1.311(3) . ?
C12 C13 1.464(3) . ?
C13 C18 1.381(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.371(4) . ?
C15 C16 1.383(4) . ?
C16 C17 1.369(4) . ?
C17 C18 1.379(4) . ?
C20 C25 1.376(3) . ?
C20 C21 1.378(3) . ?
C21 C22 1.377(4) . ?
C22 C23 1.388(4) . ?
C23 C24 1.367(4) . ?
C23 C26 1.506(4) . ?
C24 C25 1.382(4) . ?
B3 B4 1.766(4) . ?
B3 B8 1.766(3) . ?
B3 B7 1.777(4) . ?
B4 B5 1.769(4) . ?
B4 B8 1.769(4) . ?
B4 B9 1.770(4) . ?
B5 B10 1.775(4) . ?
B5 B9 1.775(4) . ?
B5 B6 1.775(4) . ?
B6 B10 1.762(4) . ?
B6 B11 1.771(4) . ?
B7 B11 1.762(4) . ?
B7 B12 1.766(4) . ?
B7 B8 1.773(4) . ?
B8 B9 1.773(4) . ?
B8 B12 1.777(4) . ?
B9 B12 1.767(4) . ?
B9 B10 1.783(5) . ?
B10 B11 1.768(5) . ?
B10 B12 1.776(4) . ?
B11 B12 1.772(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
O2 S1 O1 118.77(11) . . ?
O2 S1 N1 108.53(11) . . ?
O1 S1 N1 106.25(10) . . ?
O2 S1 C20 108.23(11) . . ?
O1 S1 C20 108.51(11) . . ?
N1 S1 C20 105.83(10) . . ?
B3 N1 S1 124.29(15) . . ?
C16 O3 C19 118.3(2) . . ?
C11 C1 C2 117.01(18) . . ?
C11 C1 B5 123.4(2) . . ?
C2 C1 B5 109.75(19) . . ?
C11 C1 B4 123.6(2) . . ?
C2 C1 B4 109.03(17) . . ?
B5 C1 B4 62.30(16) . . ?
C11 C1 B6 116.6(2) . . ?
C2 C1 B6 60.95(15) . . ?
B5 C1 B6 62.29(17) . . ?
B4 C1 B6 113.26(18) . . ?
C11 C1 B3 116.67(18) . . ?
C2 C1 B3 61.33(14) . . ?
B5 C1 B3 112.68(18) . . ?
B4 C1 B3 60.89(14) . . ?
B6 C1 B3 113.67(18) . . ?
C1 C2 B11 112.25(19) . . ?
C1 C2 B7 112.26(18) . . ?
B11 C2 B7 62.42(16) . . ?
C1 C2 B6 62.06(15) . . ?
B11 C2 B6 62.63(17) . . ?
B7 C2 B6 114.5(2) . . ?
C1 C2 B3 62.88(14) . . ?
B11 C2 B3 114.43(19) . . ?
B7 C2 B3 62.07(14) . . ?
B6 C2 B3 115.90(19) . . ?
C12 C11 C1 123.2(2) . . ?
C11 C12 C13 128.1(2) . . ?
C18 C13 C14 117.1(2) . . ?
C18 C13 C12 119.6(2) . . ?
C14 C13 C12 123.3(2) . . ?
C15 C14 C13 121.0(2) . . ?
C14 C15 C16 120.9(2) . . ?
O3 C16 C17 124.9(2) . . ?
O3 C16 C15 116.0(2) . . ?
C17 C16 C15 119.1(2) . . ?
C16 C17 C18 119.5(2) . . ?
C17 C18 C13 122.5(2) . . ?
C25 C20 C21 120.4(2) . . ?
C25 C20 S1 119.91(19) . . ?
C21 C20 S1 119.52(19) . . ?
C22 C21 C20 119.0(2) . . ?
C21 C22 C23 121.6(3) . . ?
C24 C23 C22 117.9(2) . . ?
C24 C23 C26 121.2(3) . . ?
C22 C23 C26 120.9(3) . . ?
C23 C24 C25 121.6(3) . . ?
C20 C25 C24 119.3(3) . . ?
N1 B3 C2 121.21(19) . . ?
N1 B3 B4 122.2(2) . . ?
C2 B3 B4 102.48(18) . . ?
N1 B3 B8 130.1(2) . . ?
C2 B3 B8 103.78(18) . . ?
B4 B3 B8 60.12(15) . . ?
N1 B3 C1 117.53(18) . . ?
C2 B3 C1 55.79(13) . . ?
B4 B3 C1 58.16(14) . . ?
B8 B3 C1 104.54(17) . . ?
N1 B3 B7 127.3(2) . . ?
C2 B3 B7 57.91(14) . . ?
B4 B3 B7 106.97(18) . . ?
B8 B3 B7 60.03(15) . . ?
C1 B3 B7 103.23(18) . . ?
C1 B4 B3 60.95(14) . . ?
C1 B4 B5 58.46(15) . . ?
B3 B4 B5 109.58(19) . . ?
C1 B4 B8 106.55(19) . . ?
B3 B4 B8 59.95(14) . . ?
B5 B4 B8 108.5(2) . . ?
C1 B4 B9 105.5(2) . . ?
B3 B4 B9 108.73(19) . . ?
B5 B4 B9 60.20(17) . . ?
B8 B4 B9 60.12(16) . . ?
C1 B5 B4 59.24(15) . . ?
C1 B5 B10 105.7(2) . . ?
B4 B5 B10 108.1(2) . . ?
C1 B5 B9 105.9(2) . . ?
B4 B5 B9 59.92(16) . . ?
B10 B5 B9 60.31(18) . . ?
C1 B5 B6 59.60(15) . . ?
B4 B5 B6 108.60(19) . . ?
B10 B5 B6 59.53(18) . . ?
B9 B5 B6 108.2(2) . . ?
C2 B6 C1 56.99(14) . . ?
C2 B6 B10 104.2(2) . . ?
C1 B6 B10 105.0(2) . . ?
C2 B6 B11 58.26(16) . . ?
C1 B6 B11 104.7(2) . . ?
B10 B6 B11 60.03(18) . . ?
C2 B6 B5 103.36(19) . . ?
C1 B6 B5 58.12(15) . . ?
B10 B6 B5 60.22(18) . . ?
B11 B6 B5 107.5(2) . . ?
C2 B7 B11 58.58(16) . . ?
C2 B7 B12 104.8(2) . . ?
B11 B7 B12 60.32(18) . . ?
C2 B7 B8 105.12(18) . . ?
B11 B7 B8 108.8(2) . . ?
B12 B7 B8 60.31(16) . . ?
C2 B7 B3 60.02(14) . . ?
B11 B7 B3 109.54(19) . . ?
B12 B7 B3 108.66(19) . . ?
B8 B7 B3 59.69(14) . . ?
B3 B8 B4 59.93(14) . . ?
B3 B8 B7 60.27(15) . . ?
B4 B8 B7 107.01(18) . . ?
B3 B8 B9 108.58(19) . . ?
B4 B8 B9 59.96(16) . . ?
B7 B8 B9 107.2(2) . . ?
B3 B8 B12 108.60(19) . . ?
B4 B8 B12 107.4(2) . . ?
B7 B8 B12 59.65(16) . . ?
B9 B8 B12 59.70(17) . . ?
B12 B9 B4 107.8(2) . . ?
B12 B9 B8 60.28(16) . . ?
B4 B9 B8 59.93(15) . . ?
B12 B9 B5 107.9(2) . . ?
B4 B9 B5 59.88(16) . . ?
B8 B9 B5 108.14(19) . . ?
B12 B9 B10 60.01(18) . . ?
B4 B9 B10 107.7(2) . . ?
B8 B9 B10 108.3(2) . . ?
B5 B9 B10 59.85(18) . . ?
B6 B10 B11 60.23(18) . . ?
B6 B10 B5 60.25(17) . . ?
B11 B10 B5 107.7(2) . . ?
B6 B10 B12 108.6(2) . . ?
B11 B10 B12 60.02(18) . . ?
B5 B10 B12 107.5(2) . . ?
B6 B10 B9 108.4(2) . . ?
B11 B10 B9 107.5(2) . . ?
B5 B10 B9 59.85(17) . . ?
B12 B10 B9 59.55(18) . . ?
C2 B11 B7 59.00(16) . . ?
C2 B11 B10 104.6(2) . . ?
B7 B11 B10 108.2(2) . . ?
C2 B11 B6 59.11(16) . . ?
B7 B11 B6 108.8(2) . . ?
B10 B11 B6 59.74(18) . . ?
C2 B11 B12 104.9(2) . . ?
B7 B11 B12 59.95(17) . . ?
B10 B11 B12 60.21(18) . . ?
B6 B11 B12 108.4(2) . . ?
B7 B12 B9 107.8(2) . . ?
B7 B12 B11 59.73(17) . . ?
B9 B12 B11 108.0(2) . . ?
B7 B12 B10 107.6(2) . . ?
B9 B12 B10 60.44(18) . . ?
B11 B12 B10 59.76(18) . . ?
B7 B12 B8 60.04(16) . . ?
B9 B12 B8 60.02(16) . . ?
B11 B12 B8 108.1(2) . . ?
B10 B12 B8 108.5(2) . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.043

_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_11d
_audit_block_doi                 10.5517/ccdc.csd.cc2bl706
_database_code_depnum_ccdc_archive 'CCDC 2162467'
loop_
_audit_author_name
_audit_author_address
'Bella Chan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-29 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            'C11 H20 B10 N O2'
_chemical_formula_weight         306.38

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

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

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

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

_cell_length_a                   12.4337(5)
_cell_length_b                   25.7985(10)
_cell_length_c                   11.6316(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.754(2)
_cell_angle_gamma                90
_cell_volume                     3590.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    283
_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    1.133
_exptl_crystal_F_000             1272
_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    0.065
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6354
_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            25793
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         25.249
_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             3250
_reflns_number_gt                2000
_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)+(0.1248P)²+3.4851P] 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         3250
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.2458
_refine_ls_wR_factor_gt          0.2062
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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 0.3137(2) 0.31727(10) 0.9124(2) 0.0682(8) Uani 1 1 d . . . . .
H1A H 0.3804 0.3104 0.9547 0.082 Uiso 1 1 calc R U . . .
O1 O 0.0599(2) 0.17568(10) 0.4686(2) 0.0836(8) Uani 1 1 d . . . . .
O2 O 0.23749(19) 0.15394(8) 0.4939(2) 0.0750(7) Uani 1 1 d . . . . .
C1 C 0.2732(3) 0.42056(15) 1.1629(4) 0.0805(11) Uani 0.5 1 d . . P . .
B3' B 0.2732(3) 0.42056(15) 1.1629(4) 0.0805(11) Uani 0.5 1 d . . P . .
C2 C 0.2452(3) 0.36316(12) 1.0967(3) 0.0680(9) Uani 1 1 d . . . . .
H2 H 0.2724 0.3228 1.1173 0.082 Uiso 1 1 calc R U . . .
C11 C 0.3279(6) 0.4258(3) 1.2851(5) 0.081(2) Uani 0.5 1 d . . P . .
H11A H 0.3360 0.4619 1.3056 0.121 Uiso 0.5 1 calc R U P . .
H11B H 0.2846 0.4091 1.3313 0.121 Uiso 0.5 1 calc R U P . .
H11C H 0.4004 0.4099 1.3018 0.121 Uiso 0.5 1 calc R U P . .
C11' C 0.0644(9) 0.3905(4) 1.1778(10) 0.132(4) Uani 0.5 1 d . . P . .
H11D H 0.0125 0.4187 1.1687 0.197 Uiso 0.5 1 calc R U P . .
H11E H 0.0245 0.3589 1.1507 0.197 Uiso 0.5 1 calc R U P . .
H11F H 0.1047 0.3870 1.2605 0.197 Uiso 0.5 1 calc R U P . .
C12 C 0.2732(2) 0.28416(11) 0.8179(3) 0.0573(8) Uani 1 1 d . . . . .
C13 C 0.1594(3) 0.27733(12) 0.7624(3) 0.0692(9) Uani 1 1 d . . . . .
H13A H 0.1068 0.2954 0.7904 0.083 Uiso 1 1 calc R U . . .
C14 C 0.1245(3) 0.24434(12) 0.6672(3) 0.0682(9) Uani 1 1 d . . . . .
H14A H 0.0484 0.2405 0.6315 0.082 Uiso 1 1 calc R U . . .
C15 C 0.1998(2) 0.21647(10) 0.6227(3) 0.0535(7) Uani 1 1 d . . . . .
C16 C 0.3121(2) 0.22303(11) 0.6773(3) 0.0575(8) Uani 1 1 d . . . . .
H16A H 0.3642 0.2049 0.6488 0.069 Uiso 1 1 calc R U . . .
C17 C 0.3485(2) 0.25578(11) 0.7728(3) 0.0586(8) Uani 1 1 d . . . . .
H17A H 0.4248 0.2592 0.8083 0.070 Uiso 1 1 calc R U . . .
C18 C 0.1572(3) 0.18087(11) 0.5220(3) 0.0591(8) Uani 1 1 d . . . . .
C19 C 0.2022(4) 0.11708(15) 0.3966(3) 0.0948(12) Uani 1 1 d . . . . .
H19A H 0.2666 0.0999 0.3840 0.142 Uiso 1 1 calc R U . . .
H19B H 0.1533 0.0919 0.4164 0.142 Uiso 1 1 calc R U . . .
H19C H 0.1635 0.1351 0.3251 0.142 Uiso 1 1 calc R U . . .
B3 B 0.1388(4) 0.40018(16) 1.1110(4) 0.0854(12) Uani 0.5 1 d . . P . .
C1' C 0.1388(4) 0.40018(16) 1.1110(4) 0.0854(12) Uani 0.5 1 d . . P . .
B4 B 0.1724(4) 0.46285(17) 1.0919(4) 0.0885(14) Uani 1 1 d . . . . .
H4 H 0.1420 0.5015 1.1079 0.106 Uiso 1 1 calc R U . . .
B5 B 0.3049(5) 0.46249(18) 1.0651(5) 0.1092(19) Uani 1 1 d . . . . .
H5 H 0.3581 0.4968 1.0683 0.131 Uiso 1 1 calc R U . . .
B6 B 0.3509(4) 0.39842(18) 1.0715(4) 0.0877(14) Uani 1 1 d . . . . .
H6 H 0.4374 0.3859 1.0809 0.105 Uiso 1 1 calc R U . . .
B7 B 0.1298(3) 0.36313(18) 0.9838(4) 0.0792(12) Uani 1 1 d . . . . .
H7 H 0.0822 0.3292 0.9401 0.095 Uiso 1 1 calc R U . . .
B8 B 0.0821(5) 0.4279(2) 0.9756(4) 0.1071(19) Uani 1 1 d . . . . .
H8 H -0.0008 0.4411 0.9230 0.128 Uiso 1 1 calc R U . . .
B9 B 0.1858(6) 0.46709(19) 0.9452(5) 0.117(2) Uani 1 1 d . . . . .
H9 H 0.1648 0.5030 0.8930 0.141 Uiso 1 1 calc R U . . .
B10 B 0.2956(5) 0.42740(17) 0.9330(5) 0.1046(18) Uani 1 1 d . . . . .
H10 H 0.3476 0.4374 0.8734 0.125 Uiso 1 1 calc R U . . .
B11 B 0.2629(3) 0.36188(14) 0.9530(3) 0.0622(9) Uani 1 1 d . . . . .
B12 B 0.1594(5) 0.40565(19) 0.8770(4) 0.1001(17) Uani 1 1 d . . . . .
H12 H 0.1207 0.4010 0.7806 0.120 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 C12 1.375(4) . ?
N1 B11 1.452(4) . ?
O1 C18 1.208(4) . ?
O2 C18 1.328(4) . ?
O2 C19 1.452(4) . ?
C1 C11 1.405(7) . ?
C1 C2 1.662(5) . ?
C1 B5 1.691(7) . ?
C1 B4 1.698(6) . ?
C1 B3 1.699(6) . ?
C1 B6 1.716(6) . ?
C2 B7 1.661(6) . ?
C2 B3 1.676(5) . ?
C2 B6 1.688(6) . ?
C2 B11 1.744(5) . ?
C12 C17 1.398(4) . ?
C12 C13 1.398(4) . ?
C13 C14 1.370(4) . ?
C14 C15 1.387(4) . ?
C15 C16 1.379(4) . ?
C15 C18 1.470(4) . ?
C16 C17 1.371(4) . ?
B3 B8 1.699(6) . ?
B3 B4 1.700(6) . ?
B3 B7 1.740(6) . ?
B4 B8 1.754(7) . ?
B4 B5 1.758(7) . ?
B4 B9 1.762(7) . ?
B5 B9 1.741(9) . ?
B5 B6 1.744(7) . ?
B5 B10 1.760(7) . ?
B6 B10 1.739(7) . ?
B6 B11 1.779(6) . ?
B7 B8 1.767(7) . ?
B7 B12 1.769(7) . ?
B7 B11 1.786(5) . ?
B8 B9 1.748(9) . ?
B8 B12 1.779(7) . ?
B9 B10 1.743(8) . ?
B9 B12 1.763(7) . ?
B10 B12 1.735(8) . ?
B10 B11 1.768(6) . ?
B11 B12 1.760(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
C12 N1 B11 130.9(3) . . ?
C18 O2 C19 116.5(3) . . ?
C11 C1 C2 122.5(4) . . ?
C11 C1 B5 118.8(5) . . ?
C2 C1 B5 108.4(3) . . ?
C11 C1 B4 121.4(4) . . ?
C2 C1 B4 108.2(3) . . ?
B5 C1 B4 62.5(3) . . ?
C11 C1 B3 123.2(5) . . ?
C2 C1 B3 59.8(2) . . ?
B5 C1 B3 110.2(4) . . ?
B4 C1 B3 60.0(3) . . ?
C11 C1 B6 117.3(4) . . ?
C2 C1 B6 59.9(2) . . ?
B5 C1 B6 61.6(3) . . ?
B4 C1 B6 112.2(3) . . ?
B3 C1 B6 110.0(3) . . ?
B7 C2 C1 113.2(3) . . ?
B7 C2 B3 62.8(2) . . ?
C1 C2 B3 61.2(2) . . ?
B7 C2 B6 114.1(3) . . ?
C1 C2 B6 61.6(2) . . ?
B3 C2 B6 112.5(3) . . ?
B7 C2 B11 63.2(2) . . ?
C1 C2 B11 113.3(3) . . ?
B3 C2 B11 114.5(3) . . ?
B6 C2 B11 62.4(2) . . ?
N1 C12 C17 119.2(3) . . ?
N1 C12 C13 123.5(3) . . ?
C17 C12 C13 117.3(3) . . ?
C14 C13 C12 120.7(3) . . ?
C13 C14 C15 121.7(3) . . ?
C16 C15 C14 117.8(3) . . ?
C16 C15 C18 123.0(3) . . ?
C14 C15 C18 119.2(3) . . ?
C17 C16 C15 121.3(3) . . ?
C16 C17 C12 121.3(3) . . ?
O1 C18 O2 122.0(3) . . ?
O1 C18 C15 125.0(3) . . ?
O2 C18 C15 113.0(3) . . ?
C2 B3 C1 59.0(2) . . ?
C2 B3 B8 106.7(3) . . ?
C1 B3 B8 108.6(4) . . ?
C2 B3 B4 107.5(3) . . ?
C1 B3 B4 60.0(3) . . ?
B8 B3 B4 62.2(3) . . ?
C2 B3 B7 58.2(2) . . ?
C1 B3 B7 107.6(3) . . ?
B8 B3 B7 61.8(3) . . ?
B4 B3 B7 111.9(3) . . ?
C1 B4 B3 60.0(2) . . ?
C1 B4 B8 106.2(3) . . ?
B3 B4 B8 58.9(3) . . ?
C1 B4 B5 58.6(3) . . ?
B3 B4 B5 107.1(3) . . ?
B8 B4 B5 107.2(3) . . ?
C1 B4 B9 105.0(3) . . ?
B3 B4 B9 106.1(3) . . ?
B8 B4 B9 59.6(3) . . ?
B5 B4 B9 59.3(3) . . ?
C1 B5 B9 106.2(4) . . ?
C1 B5 B6 59.9(3) . . ?
B9 B5 B6 107.2(4) . . ?
C1 B5 B4 58.9(3) . . ?
B9 B5 B4 60.5(3) . . ?
B6 B5 B4 108.1(3) . . ?
C1 B5 B10 106.6(3) . . ?
B9 B5 B10 59.7(3) . . ?
B6 B5 B10 59.5(3) . . ?
B4 B5 B10 108.3(4) . . ?
C2 B6 C1 58.4(2) . . ?
C2 B6 B10 105.2(3) . . ?
C1 B6 B10 106.5(3) . . ?
C2 B6 B5 104.9(3) . . ?
C1 B6 B5 58.5(2) . . ?
B10 B6 B5 60.7(3) . . ?
C2 B6 B11 60.3(2) . . ?
C1 B6 B11 109.0(3) . . ?
B10 B6 B11 60.3(3) . . ?
B5 B6 B11 110.1(4) . . ?
C2 B7 B3 59.0(2) . . ?
C2 B7 B8 104.3(3) . . ?
B3 B7 B8 58.0(2) . . ?
C2 B7 B12 104.8(3) . . ?
B3 B7 B12 106.2(3) . . ?
B8 B7 B12 60.4(3) . . ?
C2 B7 B11 60.7(2) . . ?
B3 B7 B11 109.4(3) . . ?
B8 B7 B11 108.8(4) . . ?
B12 B7 B11 59.3(2) . . ?
B3 B8 B9 106.7(4) . . ?
B3 B8 B4 58.9(3) . . ?
B9 B8 B4 60.4(3) . . ?
B3 B8 B7 60.2(3) . . ?
B9 B8 B7 107.6(3) . . ?
B4 B8 B7 108.0(3) . . ?
B3 B8 B12 107.5(3) . . ?
B9 B8 B12 60.0(3) . . ?
B4 B8 B12 108.5(4) . . ?
B7 B8 B12 59.8(3) . . ?
B5 B9 B10 60.7(3) . . ?
B5 B9 B8 108.2(3) . . ?
B10 B9 B8 108.3(3) . . ?
B5 B9 B4 60.2(3) . . ?
B10 B9 B4 108.9(4) . . ?
B8 B9 B4 60.0(3) . . ?
B5 B9 B12 108.2(3) . . ?
B10 B9 B12 59.3(3) . . ?
B8 B9 B12 60.9(3) . . ?
B4 B9 B12 109.0(4) . . ?
B12 B10 B6 108.0(3) . . ?
B12 B10 B9 60.9(3) . . ?
B6 B10 B9 107.4(3) . . ?
B12 B10 B5 108.7(4) . . ?
B6 B10 B5 59.8(3) . . ?
B9 B10 B5 59.6(3) . . ?
B12 B10 B11 60.3(3) . . ?
B6 B10 B11 61.0(2) . . ?
B9 B10 B11 109.8(4) . . ?
B5 B10 B11 109.9(3) . . ?
N1 B11 C2 120.4(3) . . ?
N1 B11 B12 132.0(3) . . ?
C2 B11 B12 101.7(3) . . ?
N1 B11 B10 125.4(3) . . ?
C2 B11 B10 101.6(3) . . ?
B12 B11 B10 58.9(3) . . ?
N1 B11 B6 116.2(3) . . ?
C2 B11 B6 57.2(2) . . ?
B12 B11 B6 105.1(3) . . ?
B10 B11 B6 58.7(3) . . ?
N1 B11 B7 126.0(3) . . ?
C2 B11 B7 56.1(2) . . ?
B12 B11 B7 59.8(3) . . ?
B10 B11 B7 105.5(3) . . ?
B6 B11 B7 104.1(3) . . ?
B10 B12 B11 60.8(3) . . ?
B10 B12 B9 59.8(3) . . ?
B11 B12 B9 109.2(4) . . ?
B10 B12 B7 107.7(3) . . ?
B11 B12 B7 60.8(2) . . ?
B9 B12 B7 106.9(3) . . ?
B10 B12 B8 107.3(4) . . ?
B11 B12 B8 109.5(3) . . ?
B9 B12 B8 59.1(3) . . ?
B7 B12 B8 59.8(3) . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.043

_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_23d
_audit_block_doi                 10.5517/ccdc.csd.cc2bl728
_database_code_depnum_ccdc_archive 'CCDC 2162469'
loop_
_audit_author_name
_audit_author_address
'Bella Chan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-29 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 H23 B10 N'
_chemical_formula_weight         289.41

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      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                   12.3559(8)
_cell_length_b                   10.0473(6)
_cell_length_c                   13.8323(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.944(4)
_cell_angle_gamma                90
_cell_volume                     1714.92(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    41
_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    1.121
_exptl_crystal_F_000             608
_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    0.056
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6201
_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            25516
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.1110
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.650
_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             3106
_reflns_number_gt                1949
_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)+(0.1162P)²+1.4997P] 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         3106
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.2654
_refine_ls_wR_factor_gt          0.2369
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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 0.9382(2) 0.2608(4) 0.6973(2) 0.0535(10) Uani 1 1 d . . . . .
H1A H 0.9149 0.2446 0.7536 0.064 Uiso 1 1 calc R U . . .
C1 C 0.7585(3) 0.3971(4) 0.6202(2) 0.0406(9) Uani 1 1 d . . . . .
H1 H 0.7563 0.4590 0.6857 0.049 Uiso 1 1 calc R U . . .
C2 C 0.7270(3) 0.4636(4) 0.5141(2) 0.0434(9) Uani 1 1 d . . . . .
C11 C 0.6955(4) 0.6097(4) 0.5096(3) 0.0678(13) Uani 1 1 d . . . . .
H11A H 0.6793 0.6347 0.4434 0.102 Uiso 1 1 calc R U . . .
H11B H 0.6327 0.6238 0.5464 0.102 Uiso 1 1 calc R U . . .
H11C H 0.7544 0.6628 0.5360 0.102 Uiso 1 1 calc R U . . .
C12 C 1.0532(3) 0.2730(4) 0.6880(3) 0.0454(10) Uani 1 1 d . . . . .
H12A H 1.0638 0.3303 0.6319 0.054 Uiso 1 1 calc R U . . .
C13 C 1.1156(3) 0.3363(4) 0.7747(3) 0.0490(10) Uani 1 1 d . . . . .
H13A H 1.1088 0.4325 0.7735 0.059 Uiso 1 1 calc R U . . .
H13B H 1.0902 0.3029 0.8353 0.059 Uiso 1 1 calc R U . . .
C14 C 1.2296(3) 0.2941(3) 0.7608(3) 0.0420(9) Uani 1 1 d . . . . .
C15 C 1.3267(3) 0.3485(4) 0.7953(3) 0.0545(11) Uani 1 1 d . . . . .
H15A H 1.3269 0.4240 0.8343 0.065 Uiso 1 1 calc R U . . .
C16 C 1.4228(3) 0.2915(4) 0.7722(3) 0.0610(12) Uani 1 1 d . . . . .
H16A H 1.4880 0.3286 0.7953 0.073 Uiso 1 1 calc R U . . .
C17 C 1.4230(3) 0.1793(4) 0.7148(3) 0.0610(12) Uani 1 1 d . . . . .
H17A H 1.4885 0.1403 0.7003 0.073 Uiso 1 1 calc R U . . .
C18 C 1.3267(3) 0.1246(4) 0.6786(3) 0.0558(11) Uani 1 1 d . . . . .
H18A H 1.3273 0.0503 0.6385 0.067 Uiso 1 1 calc R U . . .
C19 C 1.2305(3) 0.1804(4) 0.7020(3) 0.0442(9) Uani 1 1 d . . . . .
C20 C 1.1154(3) 0.1431(4) 0.6716(3) 0.0541(11) Uani 1 1 d . . . . .
H20A H 1.0892 0.0716 0.7113 0.065 Uiso 1 1 calc R U . . .
H20B H 1.1093 0.1164 0.6042 0.065 Uiso 1 1 calc R U . . .
B3 B 0.8594(3) 0.4254(4) 0.5464(3) 0.0444(11) Uani 1 1 d . . . . .
H3 H 0.9228 0.5010 0.5597 0.053 Uiso 1 1 calc R U . . .
B4 B 0.8604(3) 0.2744(4) 0.6171(3) 0.0419(10) Uani 1 1 d . . . . .
B5 B 0.7202(4) 0.2363(4) 0.6268(3) 0.0443(11) Uani 1 1 d . . . . .
H5 H 0.6939 0.1878 0.6930 0.053 Uiso 1 1 calc R U . . .
B6 B 0.6380(4) 0.3560(5) 0.5648(3) 0.0473(11) Uani 1 1 d . . . . .
H6 H 0.5586 0.3853 0.5903 0.057 Uiso 1 1 calc R U . . .
B7 B 0.8019(4) 0.3917(4) 0.4293(3) 0.0452(11) Uani 1 1 d . . . . .
H7 H 0.8292 0.4435 0.3649 0.054 Uiso 1 1 calc R U . . .
B8 B 0.8833(4) 0.2710(4) 0.4920(3) 0.0476(11) Uani 1 1 d . . . . .
H8 H 0.9639 0.2438 0.4680 0.057 Uiso 1 1 calc R U . . .
B9 B 0.7947(4) 0.1524(4) 0.5408(3) 0.0494(11) Uani 1 1 d . . . . .
H9 H 0.8159 0.0464 0.5484 0.059 Uiso 1 1 calc R U . . .
B10 B 0.6596(4) 0.2008(5) 0.5101(3) 0.0522(12) Uani 1 1 d . . . . .
H10 H 0.5941 0.1275 0.4987 0.063 Uiso 1 1 calc R U . . .
B11 B 0.6639(4) 0.3495(5) 0.4406(3) 0.0499(12) Uani 1 1 d . . . . .
H11 H 0.6011 0.3740 0.3841 0.060 Uiso 1 1 calc R U . . .
B12 B 0.7624(4) 0.2239(4) 0.4263(3) 0.0532(13) Uani 1 1 d . . . . .
H12 H 0.7642 0.1651 0.3594 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 B4 1.437(5) . ?
N1 C12 1.439(5) . ?
C1 C2 1.641(5) . ?
C1 B3 1.676(5) . ?
C1 B5 1.687(6) . ?
C1 B6 1.691(5) . ?
C1 B4 1.764(5) . ?
C2 C11 1.519(5) . ?
C2 B7 1.693(5) . ?
C2 B11 1.696(5) . ?
C2 B3 1.716(6) . ?
C2 B6 1.718(6) . ?
C12 C13 1.530(5) . ?
C12 C20 1.537(5) . ?
C13 C14 1.493(5) . ?
C14 C15 1.381(5) . ?
C14 C19 1.403(5) . ?
C15 C16 1.371(6) . ?
C16 C17 1.379(6) . ?
C17 C18 1.381(6) . ?
C18 C19 1.369(5) . ?
C19 C20 1.509(5) . ?
B3 B8 1.755(6) . ?
B3 B7 1.767(6) . ?
B3 B4 1.806(6) . ?
B4 B8 1.768(6) . ?
B4 B9 1.785(6) . ?
B4 B5 1.785(6) . ?
B5 B9 1.757(6) . ?
B5 B6 1.767(6) . ?
B5 B10 1.780(6) . ?
B6 B10 1.759(7) . ?
B6 B11 1.764(6) . ?
B7 B12 1.755(6) . ?
B7 B11 1.772(6) . ?
B7 B8 1.773(6) . ?
B8 B12 1.773(7) . ?
B8 B9 1.775(6) . ?
B9 B12 1.766(6) . ?
B9 B10 1.769(7) . ?
B10 B12 1.778(7) . ?
B10 B11 1.779(7) . ?
B11 B12 1.771(7) . ?

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
B4 N1 C12 123.2(3) . . ?
C2 C1 B3 62.3(2) . . ?
C2 C1 B5 112.6(3) . . ?
B3 C1 B5 114.5(3) . . ?
C2 C1 B6 62.1(2) . . ?
B3 C1 B6 115.5(3) . . ?
B5 C1 B6 63.1(3) . . ?
C2 C1 B4 113.5(3) . . ?
B3 C1 B4 63.3(2) . . ?
B5 C1 B4 62.3(2) . . ?
B6 C1 B4 115.5(3) . . ?
C11 C2 C1 118.6(3) . . ?
C11 C2 B7 122.2(3) . . ?
C1 C2 B7 109.5(3) . . ?
C11 C2 B11 121.3(3) . . ?
C1 C2 B11 110.0(3) . . ?
B7 C2 B11 63.1(2) . . ?
C11 C2 B3 117.8(3) . . ?
C1 C2 B3 59.9(2) . . ?
B7 C2 B3 62.4(2) . . ?
B11 C2 B3 114.1(3) . . ?
C11 C2 B6 117.2(3) . . ?
C1 C2 B6 60.4(2) . . ?
B7 C2 B6 113.5(3) . . ?
B11 C2 B6 62.2(2) . . ?
B3 C2 B6 112.0(3) . . ?
N1 C12 C13 115.1(3) . . ?
N1 C12 C20 116.4(3) . . ?
C13 C12 C20 103.5(3) . . ?
C14 C13 C12 102.8(3) . . ?
C15 C14 C19 119.4(4) . . ?
C15 C14 C13 130.7(4) . . ?
C19 C14 C13 109.9(3) . . ?
C16 C15 C14 120.1(4) . . ?
C15 C16 C17 120.3(4) . . ?
C16 C17 C18 120.4(4) . . ?
C19 C18 C17 119.6(4) . . ?
C18 C19 C14 120.2(4) . . ?
C18 C19 C20 130.5(4) . . ?
C14 C19 C20 109.2(3) . . ?
C19 C20 C12 102.7(3) . . ?
C1 B3 C2 57.9(2) . . ?
C1 B3 B8 105.0(3) . . ?
C2 B3 B8 105.4(3) . . ?
C1 B3 B7 104.5(3) . . ?
C2 B3 B7 58.2(2) . . ?
B8 B3 B7 60.4(2) . . ?
C1 B3 B4 60.8(2) . . ?
C2 B3 B4 108.0(3) . . ?
B8 B3 B4 59.5(2) . . ?
B7 B3 B4 109.1(3) . . ?
N1 B4 C1 119.8(3) . . ?
N1 B4 B8 128.3(3) . . ?
C1 B4 B8 100.8(3) . . ?
N1 B4 B9 131.1(3) . . ?
C1 B4 B9 101.0(3) . . ?
B8 B4 B9 60.0(2) . . ?
N1 B4 B5 122.3(3) . . ?
C1 B4 B5 56.8(2) . . ?
B8 B4 B5 105.9(3) . . ?
B9 B4 B5 58.9(2) . . ?
N1 B4 B3 118.9(3) . . ?
C1 B4 B3 56.0(2) . . ?
B8 B4 B3 58.8(2) . . ?
B9 B4 B3 105.5(3) . . ?
B5 B4 B3 104.0(3) . . ?
C1 B5 B9 105.4(3) . . ?
C1 B5 B6 58.6(2) . . ?
B9 B5 B6 107.8(3) . . ?
C1 B5 B10 104.4(3) . . ?
B9 B5 B10 60.0(3) . . ?
B6 B5 B10 59.4(3) . . ?
C1 B5 B4 61.0(2) . . ?
B9 B5 B4 60.5(2) . . ?
B6 B5 B4 110.7(3) . . ?
B10 B5 B4 109.8(3) . . ?
C1 B6 C2 57.6(2) . . ?
C1 B6 B10 105.2(3) . . ?
C2 B6 B10 105.6(3) . . ?
C1 B6 B11 104.5(3) . . ?
C2 B6 B11 58.3(2) . . ?
B10 B6 B11 60.7(3) . . ?
C1 B6 B5 58.4(2) . . ?
C2 B6 B5 105.2(3) . . ?
B10 B6 B5 60.6(3) . . ?
B11 B6 B5 108.6(3) . . ?
C2 B7 B12 105.4(3) . . ?
C2 B7 B3 59.4(2) . . ?
B12 B7 B3 107.7(3) . . ?
C2 B7 B11 58.5(2) . . ?
B12 B7 B11 60.3(3) . . ?
B3 B7 B11 107.9(3) . . ?
C2 B7 B8 105.6(3) . . ?
B12 B7 B8 60.3(3) . . ?
B3 B7 B8 59.5(2) . . ?
B11 B7 B8 108.5(3) . . ?
B3 B8 B4 61.7(2) . . ?
B3 B8 B7 60.1(2) . . ?
B4 B8 B7 110.5(3) . . ?
B3 B8 B12 107.4(3) . . ?
B4 B8 B12 109.5(3) . . ?
B7 B8 B12 59.3(2) . . ?
B3 B8 B9 108.1(3) . . ?
B4 B8 B9 60.5(2) . . ?
B7 B8 B9 107.4(3) . . ?
B12 B8 B9 59.7(3) . . ?
B5 B9 B12 108.1(3) . . ?
B5 B9 B10 60.6(3) . . ?
B12 B9 B10 60.4(3) . . ?
B5 B9 B8 106.8(3) . . ?
B12 B9 B8 60.1(3) . . ?
B10 B9 B8 108.5(3) . . ?
B5 B9 B4 60.5(2) . . ?
B12 B9 B4 109.0(3) . . ?
B10 B9 B4 110.3(3) . . ?
B8 B9 B4 59.5(2) . . ?
B6 B10 B9 107.6(3) . . ?
B6 B10 B12 107.1(3) . . ?
B9 B10 B12 59.7(3) . . ?
B6 B10 B11 59.8(3) . . ?
B9 B10 B11 107.9(3) . . ?
B12 B10 B11 59.7(3) . . ?
B6 B10 B5 59.9(2) . . ?
B9 B10 B5 59.3(2) . . ?
B12 B10 B5 106.5(3) . . ?
B11 B10 B5 107.4(3) . . ?
C2 B11 B6 59.5(2) . . ?
C2 B11 B12 104.5(3) . . ?
B6 B11 B12 107.1(3) . . ?
C2 B11 B7 58.4(2) . . ?
B6 B11 B7 107.5(3) . . ?
B12 B11 B7 59.4(3) . . ?
C2 B11 B10 105.6(3) . . ?
B6 B11 B10 59.5(3) . . ?
B12 B11 B10 60.1(3) . . ?
B7 B11 B10 107.7(3) . . ?
B7 B12 B9 108.7(3) . . ?
B7 B12 B11 60.3(3) . . ?
B9 B12 B11 108.3(3) . . ?
B7 B12 B8 60.3(3) . . ?
B9 B12 B8 60.2(2) . . ?
B11 B12 B8 108.6(3) . . ?
B7 B12 B10 108.5(3) . . ?
B9 B12 B10 59.9(3) . . ?
B11 B12 B10 60.2(3) . . ?
B8 B12 B10 108.2(3) . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058

_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_III
_audit_block_doi                 10.5517/ccdc.csd.cc2bl739
_database_code_depnum_ccdc_archive 'CCDC 2162470'
loop_
_audit_author_name
_audit_author_address
'Bella Chan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-29 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            'C20 H40 B10 Ir N O2'
_chemical_formula_weight         626.83

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'

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

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

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

_cell_length_a                   11.8280(4)
_cell_length_b                   12.7569(4)
_cell_length_c                   18.5339(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.0763(12)
_cell_angle_gamma                90
_cell_volume                     2753.42(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    551
_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    1.512
_exptl_crystal_F_000             1240
_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    4.867
_shelx_estimated_absorpt_T_min   0.246
_shelx_estimated_absorpt_T_max   0.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4839
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(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            41394
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         25.250
_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             4977
_reflns_number_gt                4186
_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)+(0.0226P)²+3.7447P] 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         4977
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0533
_refine_ls_wR_factor_gt          0.0498
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.23806(2) 0.33951(2) 0.15292(2) 0.02869(6) Uani 1 1 d . . . . .
N1 N 0.2266(3) 0.4071(2) 0.25742(16) 0.0343(8) Uani 1 1 d . . . . .
H1A H 0.2933 0.4389 0.2734 0.041 Uiso 1 1 calc R U . . .
H1B H 0.1734 0.4570 0.2494 0.041 Uiso 1 1 calc R U . . .
O1 O 0.4337(3) 0.0793(2) 0.24128(17) 0.0526(8) Uani 1 1 d . . . . .
O2 O 0.2931(2) 0.19476(19) 0.20737(14) 0.0337(6) Uani 1 1 d . . . . .
B3 B 0.4987(4) 0.2890(4) 0.1280(2) 0.0355(10) Uani 1 1 d . . . . .
H3 H 0.4563 0.2498 0.0777 0.043 Uiso 1 1 calc R U . . .
B4 B 0.4159(4) 0.3690(3) 0.1785(2) 0.0303(10) Uani 1 1 d . . . . .
B5 B 0.4880(4) 0.3534(3) 0.2731(2) 0.0356(10) Uani 1 1 d . . . . .
H5 H 0.4378 0.3572 0.3177 0.043 Uiso 1 1 calc R U . . .
B6 B 0.6053(4) 0.2659(4) 0.2780(3) 0.0425(12) Uani 1 1 d . . . . .
H6 H 0.6305 0.2121 0.3244 0.051 Uiso 1 1 calc R U . . .
B7 B 0.6418(4) 0.3368(4) 0.1385(3) 0.0496(13) Uani 1 1 d . . . . .
H7 H 0.6924 0.3304 0.0942 0.059 Uiso 1 1 calc R U . . .
B8 B 0.5244(4) 0.4248(4) 0.1333(3) 0.0416(12) Uani 1 1 d . . . . .
H8 H 0.4995 0.4770 0.0860 0.050 Uiso 1 1 calc R U . . .
B9 B 0.5163(4) 0.4655(4) 0.2241(3) 0.0429(12) Uani 1 1 d . . . . .
H9 H 0.4858 0.5438 0.2365 0.051 Uiso 1 1 calc R U . . .
B10 B 0.6304(4) 0.4013(4) 0.2847(3) 0.0501(13) Uani 1 1 d . . . . .
H10 H 0.6730 0.4381 0.3360 0.060 Uiso 1 1 calc R U . . .
B11 B 0.7071(4) 0.3228(5) 0.2316(3) 0.0557(15) Uani 1 1 d . . . . .
H11 H 0.7997 0.3079 0.2481 0.067 Uiso 1 1 calc R U . . .
B12 B 0.6524(4) 0.4449(5) 0.1973(3) 0.0526(14) Uani 1 1 d . . . . .
H12 H 0.7100 0.5109 0.1914 0.063 Uiso 1 1 calc R U . . .
C1 C 0.4823(3) 0.2545(3) 0.2135(2) 0.0314(8) Uani 1 1 d . . . . .
C2 C 0.6107(3) 0.2321(3) 0.1891(2) 0.0454(11) Uani 1 1 d . . . . .
C11 C 0.6453(5) 0.1235(5) 0.1722(3) 0.0841(18) Uani 1 1 d . . . . .
H11A H 0.7205 0.1250 0.1594 0.126 Uiso 1 1 calc R U . . .
H11B H 0.6463 0.0798 0.2145 0.126 Uiso 1 1 calc R U . . .
H11C H 0.5914 0.0959 0.1319 0.126 Uiso 1 1 calc R U . . .
C12 C 0.3981(3) 0.1665(3) 0.2211(2) 0.0341(9) Uani 1 1 d . . . . .
C13 C 0.0786(4) 0.2738(4) 0.0802(2) 0.0450(11) Uani 1 1 d . . . . .
C14 C 0.0150(5) 0.1758(4) 0.0948(3) 0.0755(17) Uani 1 1 d . . . . .
H14A H 0.0505 0.1160 0.0766 0.113 Uiso 1 1 calc R U . . .
H14B H 0.0175 0.1683 0.1466 0.113 Uiso 1 1 calc R U . . .
H14C H -0.0635 0.1807 0.0706 0.113 Uiso 1 1 calc R U . . .
C15 C 0.0541(3) 0.3759(4) 0.0982(2) 0.0410(10) Uani 1 1 d . . . . .
C16 C -0.0464(4) 0.4120(4) 0.1307(3) 0.0606(14) Uani 1 1 d . . . . .
H16A H -0.0423 0.4866 0.1375 0.091 Uiso 1 1 calc R U . . .
H16B H -0.1163 0.3943 0.0983 0.091 Uiso 1 1 calc R U . . .
H16C H -0.0450 0.3783 0.1771 0.091 Uiso 1 1 calc R U . . .
C17 C 0.1411(3) 0.4447(3) 0.0770(2) 0.0377(9) Uani 1 1 d . . . . .
C18 C 0.1377(4) 0.5621(3) 0.0798(3) 0.0548(12) Uani 1 1 d . . . . .
H18A H 0.0833 0.5838 0.1096 0.082 Uiso 1 1 calc R U . . .
H18B H 0.2124 0.5883 0.1004 0.082 Uiso 1 1 calc R U . . .
H18C H 0.1151 0.5893 0.0311 0.082 Uiso 1 1 calc R U . . .
C19 C 0.2114(3) 0.3818(3) 0.0380(2) 0.0390(10) Uani 1 1 d . . . . .
C20 C 0.2948(4) 0.4214(4) -0.0076(2) 0.0580(13) Uani 1 1 d . . . . .
H20A H 0.3017 0.4962 -0.0025 0.087 Uiso 1 1 calc R U . . .
H20B H 0.3684 0.3895 0.0085 0.087 Uiso 1 1 calc R U . . .
H20C H 0.2678 0.4040 -0.0580 0.087 Uiso 1 1 calc R U . . .
C21 C 0.1788(4) 0.2754(3) 0.0446(2) 0.0411(10) Uani 1 1 d . . . . .
C22 C 0.2236(5) 0.1821(4) 0.0097(3) 0.0678(15) Uani 1 1 d . . . . .
H22A H 0.1869 0.1198 0.0233 0.102 Uiso 1 1 calc R U . . .
H22B H 0.2077 0.1898 -0.0426 0.102 Uiso 1 1 calc R U . . .
H22C H 0.3050 0.1767 0.0260 0.102 Uiso 1 1 calc R U . . .
C23 C 0.2003(3) 0.3416(3) 0.3192(2) 0.0371(9) Uani 1 1 d . . . . .
H23A H 0.2534 0.2820 0.3260 0.045 Uiso 1 1 calc R U . . .
C24 C 0.0793(4) 0.3001(4) 0.3016(2) 0.0477(11) Uani 1 1 d . . . . .
H24A H 0.0719 0.2549 0.2589 0.057 Uiso 1 1 calc R U . . .
H24B H 0.0263 0.3581 0.2900 0.057 Uiso 1 1 calc R U . . .
C25 C 0.0489(5) 0.2385(4) 0.3660(3) 0.0682(15) Uani 1 1 d . . . . .
H25A H -0.0305 0.2159 0.3543 0.082 Uiso 1 1 calc R U . . .
H25B H 0.0968 0.1765 0.3742 0.082 Uiso 1 1 calc R U . . .
C26 C 0.0654(6) 0.3034(5) 0.4348(3) 0.0872(19) Uani 1 1 d . . . . .
H26A H 0.0491 0.2609 0.4752 0.105 Uiso 1 1 calc R U . . .
H26B H 0.0119 0.3617 0.4284 0.105 Uiso 1 1 calc R U . . .
C27 C 0.1870(5) 0.3448(5) 0.4529(3) 0.0742(16) Uani 1 1 d . . . . .
H27A H 0.1942 0.3899 0.4956 0.089 Uiso 1 1 calc R U . . .
H27B H 0.2398 0.2866 0.4646 0.089 Uiso 1 1 calc R U . . .
C28 C 0.2182(4) 0.4057(4) 0.3892(2) 0.0535(12) Uani 1 1 d . . . . .
H28A H 0.2980 0.4270 0.4010 0.064 Uiso 1 1 calc R U . . .
H28B H 0.1715 0.4685 0.3815 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 B4 2.107(4) . ?
Ir1 C17 2.129(4) . ?
Ir1 N1 2.146(3) . ?
Ir1 O2 2.150(2) . ?
Ir1 C19 2.166(4) . ?
Ir1 C21 2.168(4) . ?
Ir1 C13 2.278(4) . ?
Ir1 C15 2.282(4) . ?
N1 C23 1.494(5) . ?
O1 C12 1.225(4) . ?
O2 C12 1.275(4) . ?
B3 C1 1.687(6) . ?
B3 C2 1.743(6) . ?
B3 B8 1.758(7) . ?
B3 B7 1.778(6) . ?
B3 B4 1.787(6) . ?
B4 C1 1.730(6) . ?
B4 B8 1.797(6) . ?
B4 B9 1.814(6) . ?
B4 B5 1.823(6) . ?
B5 C1 1.671(6) . ?
B5 B9 1.758(6) . ?
B5 B10 1.769(7) . ?
B5 B6 1.770(7) . ?
B6 C2 1.714(7) . ?
B6 C1 1.720(6) . ?
B6 B10 1.753(7) . ?
B6 B11 1.754(7) . ?
B7 C2 1.708(6) . ?
B7 B12 1.749(8) . ?
B7 B11 1.772(7) . ?
B7 B8 1.776(7) . ?
B8 B12 1.771(7) . ?
B8 B9 1.779(7) . ?
B9 B12 1.784(7) . ?
B9 B10 1.795(7) . ?
B10 B11 1.762(8) . ?
B10 B12 1.773(7) . ?
B11 C2 1.716(7) . ?
B11 B12 1.763(8) . ?
C1 C12 1.523(5) . ?
C1 C2 1.683(5) . ?
C2 C11 1.493(7) . ?
C13 C15 1.388(6) . ?
C13 C21 1.454(6) . ?
C13 C14 1.507(6) . ?
C15 C17 1.458(6) . ?
C15 C16 1.496(6) . ?
C17 C19 1.438(5) . ?
C17 C18 1.500(6) . ?
C19 C21 1.423(6) . ?
C19 C20 1.494(6) . ?
C21 C22 1.496(6) . ?
C23 C24 1.507(6) . ?
C23 C28 1.517(6) . ?
C24 C25 1.524(6) . ?
C25 C26 1.503(8) . ?
C26 C27 1.514(8) . ?
C27 C28 1.512(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
B4 Ir1 C17 115.93(16) . . ?
B4 Ir1 N1 86.76(14) . . ?
C17 Ir1 N1 103.42(13) . . ?
B4 Ir1 O2 80.76(13) . . ?
C17 Ir1 O2 159.31(13) . . ?
N1 Ir1 O2 89.02(10) . . ?
B4 Ir1 C19 98.29(15) . . ?
C17 Ir1 C19 39.11(15) . . ?
N1 Ir1 C19 140.02(14) . . ?
O2 Ir1 C19 130.96(13) . . ?
B4 Ir1 C21 115.08(16) . . ?
C17 Ir1 C21 64.91(15) . . ?
N1 Ir1 C21 157.87(14) . . ?
O2 Ir1 C21 97.63(13) . . ?
C19 Ir1 C21 38.34(16) . . ?
B4 Ir1 C13 152.80(17) . . ?
C17 Ir1 C13 63.01(16) . . ?
N1 Ir1 C13 120.36(14) . . ?
O2 Ir1 C13 96.48(13) . . ?
C19 Ir1 C13 63.08(15) . . ?
C21 Ir1 C13 38.09(15) . . ?
B4 Ir1 C15 154.19(16) . . ?
C17 Ir1 C15 38.39(15) . . ?
N1 Ir1 C15 96.54(14) . . ?
O2 Ir1 C15 124.77(13) . . ?
C19 Ir1 C15 63.18(15) . . ?
C21 Ir1 C15 62.37(15) . . ?
C13 Ir1 C15 35.43(16) . . ?
C23 N1 Ir1 121.5(2) . . ?
C12 O2 Ir1 122.7(2) . . ?
C1 B3 C2 58.7(2) . . ?
C1 B3 B8 104.6(3) . . ?
C2 B3 B8 105.7(3) . . ?
C1 B3 B7 104.5(3) . . ?
C2 B3 B7 58.0(3) . . ?
B8 B3 B7 60.3(3) . . ?
C1 B3 B4 59.6(2) . . ?
C2 B3 B4 108.8(3) . . ?
B8 B3 B4 60.9(3) . . ?
B7 B3 B4 110.2(3) . . ?
C1 B4 B3 57.3(2) . . ?
C1 B4 B8 101.2(3) . . ?
B3 B4 B8 58.8(3) . . ?
C1 B4 B9 100.4(3) . . ?
B3 B4 B9 104.9(3) . . ?
B8 B4 B9 59.0(3) . . ?
C1 B4 B5 56.0(2) . . ?
B3 B4 B5 103.5(3) . . ?
B8 B4 B5 103.8(3) . . ?
B9 B4 B5 57.8(2) . . ?
C1 B4 Ir1 107.7(2) . . ?
B3 B4 Ir1 113.4(3) . . ?
B8 B4 Ir1 137.1(3) . . ?
B9 B4 Ir1 140.6(3) . . ?
B5 B4 Ir1 118.5(3) . . ?
C1 B5 B9 105.2(3) . . ?
C1 B5 B10 105.6(3) . . ?
B9 B5 B10 61.2(3) . . ?
C1 B5 B6 59.9(2) . . ?
B9 B5 B6 108.7(3) . . ?
B10 B5 B6 59.4(3) . . ?
C1 B5 B4 59.2(2) . . ?
B9 B5 B4 60.8(2) . . ?
B10 B5 B4 110.7(3) . . ?
B6 B5 B4 110.4(3) . . ?
C2 B6 C1 58.7(2) . . ?
C2 B6 B10 106.4(3) . . ?
C1 B6 B10 104.2(3) . . ?
C2 B6 B11 59.3(3) . . ?
C1 B6 B11 105.4(3) . . ?
B10 B6 B11 60.3(3) . . ?
C2 B6 B5 105.7(3) . . ?
C1 B6 B5 57.2(2) . . ?
B10 B6 B5 60.3(3) . . ?
B11 B6 B5 108.3(4) . . ?
C2 B7 B12 105.9(4) . . ?
C2 B7 B11 59.1(3) . . ?
B12 B7 B11 60.1(3) . . ?
C2 B7 B8 106.4(3) . . ?
B12 B7 B8 60.3(3) . . ?
B11 B7 B8 108.7(4) . . ?
C2 B7 B3 60.0(3) . . ?
B12 B7 B3 107.5(4) . . ?
B11 B7 B3 108.5(3) . . ?
B8 B7 B3 59.3(3) . . ?
B3 B8 B12 107.4(4) . . ?
B3 B8 B7 60.4(3) . . ?
B12 B8 B7 59.1(3) . . ?
B3 B8 B9 107.6(3) . . ?
B12 B8 B9 60.3(3) . . ?
B7 B8 B9 107.7(4) . . ?
B3 B8 B4 60.4(2) . . ?
B12 B8 B4 110.0(3) . . ?
B7 B8 B4 109.9(3) . . ?
B9 B8 B4 61.0(3) . . ?
B5 B9 B8 107.3(3) . . ?
B5 B9 B12 106.7(4) . . ?
B8 B9 B12 59.6(3) . . ?
B5 B9 B10 59.7(3) . . ?
B8 B9 B10 107.4(4) . . ?
B12 B9 B10 59.4(3) . . ?
B5 B9 B4 61.3(2) . . ?
B8 B9 B4 60.0(2) . . ?
B12 B9 B4 108.6(4) . . ?
B10 B9 B4 110.0(3) . . ?
B6 B10 B11 59.9(3) . . ?
B6 B10 B5 60.3(3) . . ?
B11 B10 B5 108.0(4) . . ?
B6 B10 B12 107.1(4) . . ?
B11 B10 B12 59.8(3) . . ?
B5 B10 B12 106.6(3) . . ?
B6 B10 B9 107.8(3) . . ?
B11 B10 B9 108.3(4) . . ?
B5 B10 B9 59.1(3) . . ?
B12 B10 B9 60.0(3) . . ?
C2 B11 B6 59.2(3) . . ?
C2 B11 B10 105.9(3) . . ?
B6 B11 B10 59.8(3) . . ?
C2 B11 B12 104.9(4) . . ?
B6 B11 B12 107.6(4) . . ?
B10 B11 B12 60.4(3) . . ?
C2 B11 B7 58.6(3) . . ?
B6 B11 B7 107.4(3) . . ?
B10 B11 B7 107.9(4) . . ?
B12 B11 B7 59.3(3) . . ?
B7 B12 B11 60.6(3) . . ?
B7 B12 B8 60.6(3) . . ?
B11 B12 B8 109.3(4) . . ?
B7 B12 B10 108.4(4) . . ?
B11 B12 B10 59.8(3) . . ?
B8 B12 B10 108.8(3) . . ?
B7 B12 B9 108.7(3) . . ?
B11 B12 B9 108.8(3) . . ?
B8 B12 B9 60.0(3) . . ?
B10 B12 B9 60.6(3) . . ?
C12 C1 B5 116.5(3) . . ?
C12 C1 C2 122.4(3) . . ?
B5 C1 C2 111.8(3) . . ?
C12 C1 B3 117.6(3) . . ?
B5 C1 B3 115.2(3) . . ?
C2 C1 B3 62.3(2) . . ?
C12 C1 B6 119.0(3) . . ?
B5 C1 B6 62.9(3) . . ?
C2 C1 B6 60.5(3) . . ?
B3 C1 B6 114.1(3) . . ?
C12 C1 B4 113.3(3) . . ?
B5 C1 B4 64.8(2) . . ?
C2 C1 B4 114.5(3) . . ?
B3 C1 B4 63.1(2) . . ?
B6 C1 B4 117.5(3) . . ?
C11 C2 C1 120.5(4) . . ?
C11 C2 B7 121.1(4) . . ?
C1 C2 B7 107.8(3) . . ?
C11 C2 B6 119.5(4) . . ?
C1 C2 B6 60.8(2) . . ?
B7 C2 B6 112.2(4) . . ?
C11 C2 B11 122.5(4) . . ?
C1 C2 B11 108.7(3) . . ?
B7 C2 B11 62.3(3) . . ?
B6 C2 B11 61.5(3) . . ?
C11 C2 B3 117.1(4) . . ?
C1 C2 B3 59.0(2) . . ?
B7 C2 B3 62.0(3) . . ?
B6 C2 B3 111.5(3) . . ?
B11 C2 B3 112.7(4) . . ?
O1 C12 O2 126.1(4) . . ?
O1 C12 C1 120.2(4) . . ?
O2 C12 C1 113.7(3) . . ?
C15 C13 C21 108.5(4) . . ?
C15 C13 C14 127.1(4) . . ?
C21 C13 C14 124.4(4) . . ?
C15 C13 Ir1 72.5(2) . . ?
C21 C13 Ir1 66.9(2) . . ?
C14 C13 Ir1 125.9(3) . . ?
C13 C15 C17 108.3(4) . . ?
C13 C15 C16 126.9(4) . . ?
C17 C15 C16 124.8(4) . . ?
C13 C15 Ir1 72.1(2) . . ?
C17 C15 Ir1 65.1(2) . . ?
C16 C15 Ir1 130.3(3) . . ?
C19 C17 C15 107.3(4) . . ?
C19 C17 C18 126.6(4) . . ?
C15 C17 C18 124.6(4) . . ?
C19 C17 Ir1 71.8(2) . . ?
C15 C17 Ir1 76.5(2) . . ?
C18 C17 Ir1 128.4(3) . . ?
C21 C19 C17 107.4(3) . . ?
C21 C19 C20 125.9(4) . . ?
C17 C19 C20 126.3(4) . . ?
C21 C19 Ir1 70.9(2) . . ?
C17 C19 Ir1 69.1(2) . . ?
C20 C19 Ir1 130.1(3) . . ?
C19 C21 C13 107.9(4) . . ?
C19 C21 C22 126.9(4) . . ?
C13 C21 C22 124.4(4) . . ?
C19 C21 Ir1 70.7(2) . . ?
C13 C21 Ir1 75.0(2) . . ?
C22 C21 Ir1 128.3(3) . . ?
N1 C23 C24 110.4(3) . . ?
N1 C23 C28 109.7(3) . . ?
C24 C23 C28 111.1(3) . . ?
C23 C24 C25 110.9(4) . . ?
C26 C25 C24 111.6(4) . . ?
C25 C26 C27 110.9(4) . . ?
C28 C27 C26 111.1(5) . . ?
C27 C28 C23 112.0(4) . . ?

_refine_diff_density_max         0.758
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.084

_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_11c
_audit_block_doi                 10.5517/ccdc.csd.cc2bl6z4
_database_code_depnum_ccdc_archive 'CCDC 2162466'
loop_
_audit_author_name
_audit_author_address
'Bella Chan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-29 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 H27 B10 N O2 S'
_chemical_formula_weight         417.55

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.0638(3)
_cell_length_b                   14.7743(8)
_cell_length_c                   22.2684(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.3578(15)
_cell_angle_gamma                90
_cell_volume                     2322.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    129
_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    1.194
_exptl_crystal_F_000             872
_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    0.154
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6443
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(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            84704
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.1066
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.292
_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             4213
_reflns_number_gt                2883
_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)+(0.0627P)²+1.3903P] 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         4213
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
S1 S 0.22940(8) 0.44308(4) 0.44582(3) 0.0382(2) Uani 1 1 d . . . . .
N1 N 0.1596(3) 0.38316(14) 0.50080(9) 0.0412(5) Uani 1 1 d . . . . .
H1A H 0.0808 0.4089 0.5238 0.049 Uiso 1 1 calc R U . . .
O1 O 0.1882(2) 0.53565(11) 0.46073(7) 0.0436(4) Uani 1 1 d . . . . .
O2 O 0.4200(2) 0.41956(13) 0.43434(8) 0.0497(5) Uani 1 1 d . . . . .
C1 C 0.3530(3) 0.27622(16) 0.58398(11) 0.0371(6) Uani 1 1 d . . . . .
C2 C 0.4461(3) 0.25694(18) 0.51875(11) 0.0407(6) Uani 1 1 d . . . . .
H2 H 0.5489 0.3052 0.5013 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4032(4) 0.36464(18) 0.61545(12) 0.0506(7) Uani 1 1 d . . . . .
H11A H 0.4796 0.4002 0.5890 0.061 Uiso 1 1 calc R U . . .
H11B H 0.2868 0.3979 0.6210 0.061 Uiso 1 1 calc R U . . .
C12 C 0.5085(4) 0.35752(17) 0.67569(12) 0.0434(6) Uani 1 1 d . . . . .
C13 C 0.4146(5) 0.3482(3) 0.72820(15) 0.0729(10) Uani 1 1 d . . . . .
H13A H 0.2832 0.3440 0.7270 0.087 Uiso 1 1 calc R U . . .
C14 C 0.5150(7) 0.3449(3) 0.78306(15) 0.0922(12) Uani 1 1 d . . . . .
H14A H 0.4486 0.3378 0.8179 0.111 Uiso 1 1 calc R U . . .
C15 C 0.7067(6) 0.3518(3) 0.78763(16) 0.0792(11) Uani 1 1 d . . . . .
C16 C 0.7975(5) 0.3619(2) 0.73540(17) 0.0758(10) Uani 1 1 d . . . . .
H16A H 0.9288 0.3668 0.7370 0.091 Uiso 1 1 calc R U . . .
C17 C 0.7015(4) 0.3651(2) 0.67994(13) 0.0572(8) Uani 1 1 d . . . . .
H17A H 0.7690 0.3726 0.6453 0.069 Uiso 1 1 calc R U . . .
C18 C 0.8119(8) 0.3485(3) 0.84816(18) 0.141(2) Uani 1 1 d . . . . .
H18A H 0.9454 0.3543 0.8427 0.211 Uiso 1 1 calc R U . . .
H18B H 0.7699 0.3972 0.8728 0.211 Uiso 1 1 calc R U . . .
H18C H 0.7870 0.2918 0.8674 0.211 Uiso 1 1 calc R U . . .
C19 C 0.0847(3) 0.41675(17) 0.38218(11) 0.0392(6) Uani 1 1 d . . . . .
C20 C 0.1641(4) 0.4003(3) 0.32814(13) 0.0712(10) Uani 1 1 d . . . . .
H20A H 0.2949 0.3952 0.3260 0.085 Uiso 1 1 calc R U . . .
C21 C 0.0484(5) 0.3915(3) 0.27678(14) 0.0820(11) Uani 1 1 d . . . . .
H21A H 0.1031 0.3804 0.2402 0.098 Uiso 1 1 calc R U . . .
C22 C -0.1438(5) 0.3987(2) 0.27847(13) 0.0609(8) Uani 1 1 d . . . . .
C23 C -0.2189(4) 0.4130(2) 0.33344(14) 0.0636(9) Uani 1 1 d . . . . .
H23A H -0.3498 0.4169 0.3358 0.076 Uiso 1 1 calc R U . . .
C24 C -0.1081(4) 0.4219(2) 0.38482(12) 0.0519(7) Uani 1 1 d . . . . .
H24A H -0.1636 0.4314 0.4215 0.062 Uiso 1 1 calc R U . . .
C25 C -0.2680(6) 0.3921(3) 0.22190(16) 0.0988(13) Uani 1 1 d . . . . .
H25A H -0.3984 0.3987 0.2317 0.148 Uiso 1 1 calc R U . . .
H25B H -0.2348 0.4393 0.1946 0.148 Uiso 1 1 calc R U . . .
H25C H -0.2500 0.3343 0.2034 0.148 Uiso 1 1 calc R U . . .
B3 B 0.2131(4) 0.2904(2) 0.51668(13) 0.0381(7) Uani 1 1 d . . . . .
B4 B 0.1261(4) 0.2377(2) 0.58106(14) 0.0460(8) Uani 1 1 d . . . . .
H4 H 0.0116 0.2693 0.6057 0.055 Uiso 1 1 calc R U . . .
B5 B 0.3115(4) 0.1770(2) 0.61908(16) 0.0499(8) Uani 1 1 d . . . . .
H5 H 0.3166 0.1685 0.6682 0.060 Uiso 1 1 calc R U . . .
B6 B 0.5198(4) 0.1926(2) 0.57897(15) 0.0460(8) Uani 1 1 d . . . . .
H6 H 0.6617 0.1952 0.6011 0.055 Uiso 1 1 calc R U . . .
B7 B 0.2928(5) 0.2048(2) 0.46885(15) 0.0526(8) Uani 1 1 d . . . . .
H7 H 0.2896 0.2143 0.4198 0.063 Uiso 1 1 calc R U . . .
B8 B 0.0856(5) 0.1891(2) 0.50909(16) 0.0553(9) Uani 1 1 d . . . . .
H8 H -0.0559 0.1876 0.4866 0.066 Uiso 1 1 calc R U . . .
B9 B 0.1450(5) 0.1190(2) 0.57182(18) 0.0604(10) Uani 1 1 d . . . . .
H9 H 0.0415 0.0718 0.5901 0.072 Uiso 1 1 calc R U . . .
B10 B 0.3891(5) 0.0916(2) 0.57028(17) 0.0564(9) Uani 1 1 d . . . . .
H10 H 0.4457 0.0267 0.5873 0.068 Uiso 1 1 calc R U . . .
B11 B 0.4793(5) 0.1453(2) 0.50664(16) 0.0534(9) Uani 1 1 d . . . . .
H11 H 0.5964 0.1166 0.4817 0.064 Uiso 1 1 calc R U . . .
B12 B 0.2488(5) 0.0986(2) 0.50254(18) 0.0620(10) Uani 1 1 d . . . . .
H12 H 0.2138 0.0381 0.4756 0.074 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
S1 O2 1.4241(17) . ?
S1 O1 1.4398(18) . ?
S1 N1 1.605(2) . ?
S1 C19 1.757(2) . ?
N1 B3 1.461(4) . ?
C1 C11 1.518(4) . ?
C1 C2 1.644(3) . ?
C1 B5 1.693(4) . ?
C1 B4 1.700(4) . ?
C1 B6 1.714(4) . ?
C1 B3 1.773(4) . ?
C2 B11 1.689(4) . ?
C2 B7 1.704(4) . ?
C2 B6 1.707(4) . ?
C2 B3 1.718(3) . ?
C11 C12 1.511(4) . ?
C12 C17 1.368(4) . ?
C12 C13 1.375(4) . ?
C13 C14 1.388(5) . ?
C14 C15 1.357(5) . ?
C15 C16 1.359(5) . ?
C15 C18 1.513(5) . ?
C16 C17 1.385(4) . ?
C19 C24 1.368(3) . ?
C19 C20 1.370(4) . ?
C20 C21 1.384(4) . ?
C21 C22 1.364(4) . ?
C22 C23 1.370(4) . ?
C22 C25 1.508(4) . ?
C23 C24 1.366(4) . ?
B3 B8 1.751(4) . ?
B3 B7 1.761(4) . ?
B3 B4 1.764(4) . ?
B4 B8 1.768(5) . ?
B4 B9 1.772(5) . ?
B4 B5 1.773(4) . ?
B5 B9 1.767(5) . ?
B5 B10 1.767(5) . ?
B5 B6 1.767(4) . ?
B6 B10 1.762(5) . ?
B6 B11 1.768(5) . ?
B7 B8 1.762(5) . ?
B7 B11 1.768(5) . ?
B7 B12 1.771(5) . ?
B8 B12 1.775(5) . ?
B8 B9 1.776(5) . ?
B9 B12 1.761(5) . ?
B9 B10 1.773(5) . ?
B10 B11 1.766(5) . ?
B10 B12 1.774(5) . ?
B11 B12 1.767(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.35(11) . . ?
O2 S1 N1 108.96(11) . . ?
O1 S1 N1 106.07(11) . . ?
O2 S1 C19 108.91(11) . . ?
O1 S1 C19 106.26(11) . . ?
N1 S1 C19 107.85(12) . . ?
B3 N1 S1 128.12(17) . . ?
C11 C1 C2 117.6(2) . . ?
C11 C1 B5 125.0(2) . . ?
C2 C1 B5 109.9(2) . . ?
C11 C1 B4 120.6(2) . . ?
C2 C1 B4 108.6(2) . . ?
B5 C1 B4 63.02(17) . . ?
C11 C1 B6 120.2(2) . . ?
C2 C1 B6 61.08(16) . . ?
B5 C1 B6 62.51(17) . . ?
B4 C1 B6 113.9(2) . . ?
C11 C1 B3 113.6(2) . . ?
C2 C1 B3 60.21(14) . . ?
B5 C1 B3 113.0(2) . . ?
B4 C1 B3 61.02(16) . . ?
B6 C1 B3 113.0(2) . . ?
C1 C2 B11 111.9(2) . . ?
C1 C2 B7 112.8(2) . . ?
B11 C2 B7 62.80(19) . . ?
C1 C2 B6 61.48(16) . . ?
B11 C2 B6 62.75(18) . . ?
B7 C2 B6 115.2(2) . . ?
C1 C2 B3 63.63(15) . . ?
B11 C2 B3 114.6(2) . . ?
B7 C2 B3 61.96(17) . . ?
B6 C2 B3 116.2(2) . . ?
C12 C11 C1 116.6(2) . . ?
C17 C12 C13 117.6(3) . . ?
C17 C12 C11 120.6(3) . . ?
C13 C12 C11 121.7(3) . . ?
C12 C13 C14 120.4(3) . . ?
C15 C14 C13 122.4(3) . . ?
C14 C15 C16 116.6(3) . . ?
C14 C15 C18 121.1(4) . . ?
C16 C15 C18 122.3(4) . . ?
C15 C16 C17 122.4(3) . . ?
C12 C17 C16 120.6(3) . . ?
C24 C19 C20 119.5(2) . . ?
C24 C19 S1 120.02(19) . . ?
C20 C19 S1 120.2(2) . . ?
C19 C20 C21 119.6(3) . . ?
C22 C21 C20 121.6(3) . . ?
C21 C22 C23 117.3(3) . . ?
C21 C22 C25 121.2(3) . . ?
C23 C22 C25 121.5(3) . . ?
C24 C23 C22 122.3(3) . . ?
C23 C24 C19 119.7(3) . . ?
N1 B3 C2 121.0(2) . . ?
N1 B3 B8 130.6(2) . . ?
C2 B3 B8 104.2(2) . . ?
N1 B3 B7 127.8(2) . . ?
C2 B3 B7 58.63(16) . . ?
B8 B3 B7 60.24(19) . . ?
N1 B3 B4 121.0(2) . . ?
C2 B3 B4 102.5(2) . . ?
B8 B3 B4 60.39(19) . . ?
B7 B3 B4 107.7(2) . . ?
N1 B3 C1 116.4(2) . . ?
C2 B3 C1 56.16(14) . . ?
B8 B3 C1 104.3(2) . . ?
B7 B3 C1 104.2(2) . . ?
B4 B3 C1 57.43(15) . . ?
C1 B4 B3 61.55(15) . . ?
C1 B4 B8 106.7(2) . . ?
B3 B4 B8 59.43(18) . . ?
C1 B4 B9 105.1(2) . . ?
B3 B4 B9 108.2(2) . . ?
B8 B4 B9 60.2(2) . . ?
C1 B4 B5 58.30(16) . . ?
B3 B4 B5 109.6(2) . . ?
B8 B4 B5 108.4(2) . . ?
B9 B4 B5 59.81(19) . . ?
C1 B5 B9 105.6(2) . . ?
C1 B5 B10 105.7(2) . . ?
B9 B5 B10 60.2(2) . . ?
C1 B5 B6 59.33(16) . . ?
B9 B5 B6 108.0(2) . . ?
B10 B5 B6 59.78(18) . . ?
C1 B5 B4 58.69(16) . . ?
B9 B5 B4 60.05(19) . . ?
B10 B5 B4 108.0(2) . . ?
B6 B5 B4 107.8(2) . . ?
C2 B6 C1 57.44(15) . . ?
C2 B6 B10 104.1(2) . . ?
C1 B6 B10 105.1(2) . . ?
C2 B6 B5 103.7(2) . . ?
C1 B6 B5 58.17(16) . . ?
B10 B6 B5 60.11(19) . . ?
C2 B6 B11 58.12(17) . . ?
C1 B6 B11 105.0(2) . . ?
B10 B6 B11 60.1(2) . . ?
B5 B6 B11 107.6(2) . . ?
C2 B7 B3 59.41(16) . . ?
C2 B7 B8 104.3(2) . . ?
B3 B7 B8 59.60(18) . . ?
C2 B7 B11 58.19(17) . . ?
B3 B7 B11 108.6(2) . . ?
B8 B7 B11 108.1(3) . . ?
C2 B7 B12 104.0(2) . . ?
B3 B7 B12 108.3(2) . . ?
B8 B7 B12 60.3(2) . . ?
B11 B7 B12 59.9(2) . . ?
B3 B8 B7 60.16(18) . . ?
B3 B8 B4 60.17(17) . . ?
B7 B8 B4 107.5(2) . . ?
B3 B8 B12 108.6(2) . . ?
B7 B8 B12 60.1(2) . . ?
B4 B8 B12 107.4(2) . . ?
B3 B8 B9 108.6(2) . . ?
B7 B8 B9 107.6(2) . . ?
B4 B8 B9 59.98(19) . . ?
B12 B8 B9 59.5(2) . . ?
B12 B9 B5 108.3(2) . . ?
B12 B9 B4 107.9(3) . . ?
B5 B9 B4 60.13(18) . . ?
B12 B9 B10 60.3(2) . . ?
B5 B9 B10 59.90(19) . . ?
B4 B9 B10 107.8(2) . . ?
B12 B9 B8 60.2(2) . . ?
B5 B9 B8 108.4(2) . . ?
B4 B9 B8 59.80(19) . . ?
B10 B9 B8 108.5(3) . . ?
B6 B10 B11 60.16(19) . . ?
B6 B10 B5 60.11(18) . . ?
B11 B10 B5 107.7(2) . . ?
B6 B10 B9 108.1(2) . . ?
B11 B10 B9 107.2(2) . . ?
B5 B10 B9 59.89(19) . . ?
B6 B10 B12 108.4(2) . . ?
B11 B10 B12 59.9(2) . . ?
B5 B10 B12 107.7(2) . . ?
B9 B10 B12 59.5(2) . . ?
C2 B11 B10 104.7(2) . . ?
C2 B11 B12 104.8(2) . . ?
B10 B11 B12 60.3(2) . . ?
C2 B11 B7 59.01(17) . . ?
B10 B11 B7 108.6(2) . . ?
B12 B11 B7 60.1(2) . . ?
C2 B11 B6 59.14(17) . . ?
B10 B11 B6 59.79(19) . . ?
B12 B11 B6 108.4(2) . . ?
B7 B11 B6 109.1(2) . . ?
B9 B12 B11 107.7(2) . . ?
B9 B12 B7 107.9(2) . . ?
B11 B12 B7 59.93(19) . . ?
B9 B12 B10 60.2(2) . . ?
B11 B12 B10 59.8(2) . . ?
B7 B12 B10 108.1(2) . . ?
B9 B12 B8 60.3(2) . . ?
B11 B12 B8 107.6(2) . . ?
B7 B12 B8 59.60(19) . . ?
B10 B12 B8 108.5(2) . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6



