# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ic22586
_database_code_depnum_ccdc_archive 'CCDC 2418957'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Phenanthridinium 6-tribromoborate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 B Br3 N'
_chemical_formula_weight         429.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   7.1182(3)
_cell_length_b                   10.1195(5)
_cell_length_c                   18.3253(9)
_cell_angle_alpha                89.6056(14)
_cell_angle_beta                 88.8595(13)
_cell_angle_gamma                89.3333(14)
_cell_volume                     1319.64(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9529
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      72.04

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.163
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    11.151
_shelx_estimated_absorpt_T_min   0.286
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7250
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21676
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.412
_diffrn_reflns_theta_max         72.180
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5088
_reflns_number_gt                5003
_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 APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0364P)²+1.3896P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5088
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
Br1 Br 0.74317(4) 0.97008(2) 0.55707(2) 0.01726(8) Uani 1 1 d . . . . .
Br2 Br 1.02007(3) 0.71445(2) 0.52547(2) 0.01682(8) Uani 1 1 d . . . . .
Br3 Br 0.55286(3) 0.68190(2) 0.52678(2) 0.01734(8) Uani 1 1 d . . . . .
N1 N 0.7426(3) 0.9536(2) 0.39165(11) 0.0134(4) Uani 1 1 d . . . . .
H1 H 0.728(4) 1.015(3) 0.4258(17) 0.014(7) Uiso 1 1 d . . . . .
B1 B 0.7711(4) 0.7994(3) 0.49973(15) 0.0140(5) Uani 1 1 d . . . . .
C1 C 0.7677(3) 0.8296(2) 0.41249(13) 0.0129(4) Uani 1 1 d . . . . .
C2 C 0.7841(3) 0.7315(2) 0.35611(13) 0.0126(5) Uani 1 1 d . . . . .
C3 C 0.8018(3) 0.5949(2) 0.37380(13) 0.0149(5) Uani 1 1 d . . . . .
H3 H 0.808905 0.568008 0.423450 0.018 Uiso 1 1 calc R U . . .
C4 C 0.8088(4) 0.5022(2) 0.32001(14) 0.0175(5) Uani 1 1 d . . . . .
H4 H 0.818806 0.411069 0.332387 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8011(4) 0.5412(3) 0.24631(14) 0.0186(5) Uani 1 1 d . . . . .
H5 H 0.806244 0.476101 0.209217 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7863(3) 0.6720(2) 0.22740(13) 0.0154(5) Uani 1 1 d . . . . .
H6 H 0.782960 0.696516 0.177295 0.018 Uiso 1 1 calc R U . . .
C7 C 0.7760(3) 0.7708(2) 0.28118(13) 0.0131(5) Uani 1 1 d . . . . .
C8 C 0.7491(3) 0.9085(2) 0.26317(13) 0.0135(5) Uani 1 1 d . . . . .
C9 C 0.7308(3) 0.9580(3) 0.19116(13) 0.0163(5) Uani 1 1 d . . . . .
H9 H 0.748567 0.900051 0.150996 0.020 Uiso 1 1 calc R U . . .
C10 C 0.6877(4) 1.0888(3) 0.17863(14) 0.0184(5) Uani 1 1 d . . . . .
H10 H 0.675058 1.120111 0.129959 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6622(4) 1.1766(2) 0.23700(14) 0.0183(5) Uani 1 1 d . . . . .
H11 H 0.629984 1.266384 0.227679 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6835(4) 1.1332(2) 0.30769(14) 0.0176(5) Uani 1 1 d . . . . .
H12 H 0.668820 1.192616 0.347351 0.021 Uiso 1 1 calc R U . . .
C13 C 0.7274(3) 0.9995(2) 0.32013(13) 0.0137(5) Uani 1 1 d . . . . .
Br4 Br 0.52719(4) 0.78404(3) 0.03116(2) 0.02016(8) Uani 1 1 d . . . . .
Br5 Br 0.06567(4) 0.82837(3) 0.04196(2) 0.02132(8) Uani 1 1 d . . . . .
Br6 Br 0.24950(4) 0.58452(2) -0.05431(2) 0.01795(8) Uani 1 1 d . . . . .
N2 N 0.2427(3) 0.4716(2) 0.10007(11) 0.0144(4) Uani 1 1 d . . . . .
H2 H 0.237(4) 0.442(3) 0.0533(19) 0.023(8) Uiso 1 1 d . . . . .
B2 B 0.2774(4) 0.6937(3) 0.03802(15) 0.0156(5) Uani 1 1 d . . . . .
C14 C 0.2672(3) 0.5993(2) 0.11040(13) 0.0138(5) Uani 1 1 d . . . . .
C15 C 0.2815(3) 0.6437(2) 0.18456(13) 0.0140(5) Uani 1 1 d . . . . .
C16 C 0.3023(3) 0.7793(2) 0.20043(14) 0.0167(5) Uani 1 1 d . . . . .
H16 H 0.311376 0.842027 0.161756 0.020 Uiso 1 1 calc R U . . .
C17 C 0.3094(3) 0.8205(2) 0.27152(14) 0.0167(5) Uani 1 1 d . . . . .
H17 H 0.320970 0.911897 0.281746 0.020 Uiso 1 1 calc R U . . .
C18 C 0.2999(4) 0.7290(3) 0.32907(14) 0.0192(5) Uani 1 1 d . . . . .
H18 H 0.305508 0.758744 0.378025 0.023 Uiso 1 1 calc R U . . .
C19 C 0.2826(4) 0.5969(3) 0.31529(13) 0.0175(5) Uani 1 1 d . . . . .
H19 H 0.278745 0.535621 0.354766 0.021 Uiso 1 1 calc R U . . .
C20 C 0.2703(3) 0.5509(2) 0.24293(13) 0.0150(5) Uani 1 1 d . . . . .
C21 C 0.2384(3) 0.4134(2) 0.22712(13) 0.0150(5) Uani 1 1 d . . . . .
C22 C 0.2107(3) 0.3135(3) 0.28089(13) 0.0170(5) Uani 1 1 d . . . . .
H22 H 0.219874 0.334634 0.331111 0.020 Uiso 1 1 calc R U . . .
C23 C 0.1707(4) 0.1868(3) 0.26088(14) 0.0191(5) Uani 1 1 d . . . . .
H23 H 0.150532 0.121605 0.297652 0.023 Uiso 1 1 calc R U . . .
C24 C 0.1591(4) 0.1513(3) 0.18710(14) 0.0185(5) Uani 1 1 d . . . . .
H24 H 0.132671 0.062762 0.174270 0.022 Uiso 1 1 calc R U . . .
C25 C 0.1860(3) 0.2453(3) 0.13375(14) 0.0172(5) Uani 1 1 d . . . . .
H25 H 0.178748 0.222492 0.083688 0.021 Uiso 1 1 calc R U . . .
C26 C 0.2243(3) 0.3757(2) 0.15405(13) 0.0140(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 2.034(3) . ?
Br2 B1 2.023(3) . ?
Br3 B1 2.019(3) . ?
N1 C1 1.320(3) . ?
N1 C13 1.394(3) . ?
B1 C1 1.626(3) . ?
C1 C2 1.440(3) . ?
C2 C3 1.422(3) . ?
C2 C7 1.429(3) . ?
C3 C4 1.366(4) . ?
C4 C5 1.406(4) . ?
C5 C6 1.369(4) . ?
C6 C7 1.409(3) . ?
C7 C8 1.441(3) . ?
C8 C13 1.402(3) . ?
C8 C9 1.416(3) . ?
C9 C10 1.374(4) . ?
C10 C11 1.403(4) . ?
C11 C12 1.376(4) . ?
C12 C13 1.402(3) . ?
Br4 B2 2.010(3) . ?
Br5 B2 2.021(3) . ?
Br6 B2 2.041(3) . ?
N2 C14 1.322(3) . ?
N2 C26 1.387(3) . ?
B2 C14 1.630(4) . ?
C14 C15 1.440(3) . ?
C15 C16 1.415(3) . ?
C15 C20 1.420(3) . ?
C16 C17 1.373(4) . ?
C17 C18 1.400(4) . ?
C18 C19 1.369(4) . ?
C19 C20 1.413(3) . ?
C20 C21 1.445(4) . ?
C21 C26 1.400(3) . ?
C21 C22 1.419(3) . ?
C22 C23 1.370(4) . ?
C23 C24 1.406(4) . ?
C24 C25 1.371(4) . ?
C25 C26 1.405(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 126.5(2) . . ?
C1 B1 Br3 108.83(16) . . ?
C1 B1 Br2 109.54(16) . . ?
Br3 B1 Br2 111.70(13) . . ?
C1 B1 Br1 110.50(17) . . ?
Br3 B1 Br1 108.30(12) . . ?
Br2 B1 Br1 107.97(12) . . ?
N1 C1 C2 117.3(2) . . ?
N1 C1 B1 117.4(2) . . ?
C2 C1 B1 125.2(2) . . ?
C3 C2 C7 119.2(2) . . ?
C3 C2 C1 121.0(2) . . ?
C7 C2 C1 119.8(2) . . ?
C4 C3 C2 120.5(2) . . ?
C3 C4 C5 120.1(2) . . ?
C6 C5 C4 120.8(2) . . ?
C5 C6 C7 120.9(2) . . ?
C6 C7 C2 118.4(2) . . ?
C6 C7 C8 122.2(2) . . ?
C2 C7 C8 119.3(2) . . ?
C13 C8 C9 117.0(2) . . ?
C13 C8 C7 118.7(2) . . ?
C9 C8 C7 124.2(2) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 C11 120.6(2) . . ?
C12 C11 C10 120.3(2) . . ?
C11 C12 C13 118.8(2) . . ?
N1 C13 C8 118.4(2) . . ?
N1 C13 C12 119.2(2) . . ?
C8 C13 C12 122.4(2) . . ?
C14 N2 C26 126.2(2) . . ?
C14 B2 Br4 110.23(16) . . ?
C14 B2 Br5 109.67(16) . . ?
Br4 B2 Br5 110.55(13) . . ?
C14 B2 Br6 110.63(17) . . ?
Br4 B2 Br6 107.66(13) . . ?
Br5 B2 Br6 108.05(12) . . ?
N2 C14 C15 117.4(2) . . ?
N2 C14 B2 117.2(2) . . ?
C15 C14 B2 125.4(2) . . ?
C16 C15 C20 119.2(2) . . ?
C16 C15 C14 120.9(2) . . ?
C20 C15 C14 119.8(2) . . ?
C17 C16 C15 120.2(2) . . ?
C16 C17 C18 120.6(2) . . ?
C19 C18 C17 120.4(2) . . ?
C18 C19 C20 120.7(2) . . ?
C19 C20 C15 118.8(2) . . ?
C19 C20 C21 121.8(2) . . ?
C15 C20 C21 119.4(2) . . ?
C26 C21 C22 117.0(2) . . ?
C26 C21 C20 118.5(2) . . ?
C22 C21 C20 124.5(2) . . ?
C23 C22 C21 120.5(2) . . ?
C22 C23 C24 121.4(2) . . ?
C25 C24 C23 119.6(2) . . ?
C24 C25 C26 119.2(2) . . ?
N2 C26 C21 118.7(2) . . ?
N2 C26 C25 118.9(2) . . ?
C21 C26 C25 122.4(2) . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.870
_refine_diff_density_rms         0.142



####################################################################### 
# 
# 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_ic22223
_database_code_depnum_ccdc_archive 'CCDC 2418963'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        '2-isocyanobiphenyl?boron trichloride'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 B Cl3 N'
_chemical_formula_weight         296.37

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

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

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

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

_cell_length_a                   9.3124(6)
_cell_length_b                   9.8992(6)
_cell_length_c                   14.9871(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.038(2)
_cell_angle_gamma                90
_cell_volume                     1368.02(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9618
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.67

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.648
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8816
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33092
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.432
_diffrn_reflns_theta_max         28.738
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3550
_reflns_number_gt                3099
_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 APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0450P)²+0.5723P] 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         3550
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Cl1 Cl 0.63111(4) 0.52630(4) 0.36607(2) 0.02228(10) Uani 1 1 d . . . . .
Cl2 Cl 0.42134(5) 0.34935(4) 0.24212(2) 0.02678(11) Uani 1 1 d . . . . .
Cl3 Cl 0.30582(4) 0.55856(4) 0.36278(2) 0.02211(10) Uani 1 1 d . . . . .
N1 N 0.44579(13) 0.24945(12) 0.48095(8) 0.0183(2) Uani 1 1 d . . . . .
B1 B 0.45437(18) 0.44179(16) 0.34942(11) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.41722(16) 0.15331(13) 0.54455(9) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.53271(16) 0.10075(14) 0.60315(9) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.629602 0.127438 0.599192 0.024 Uiso 1 1 calc R U . . .
C3 C 0.50248(17) 0.00827(15) 0.66753(10) 0.0226(3) Uani 1 1 d . . . . .
H3 H 0.579164 -0.029179 0.708539 0.027 Uiso 1 1 calc R U . . .
C4 C 0.35988(18) -0.02958(15) 0.67200(10) 0.0252(3) Uani 1 1 d . . . . .
H4 H 0.339995 -0.093926 0.715674 0.030 Uiso 1 1 calc R U . . .
C5 C 0.24606(17) 0.02550(15) 0.61340(10) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.149314 -0.000754 0.618205 0.029 Uiso 1 1 calc R U . . .
C6 C 0.27173(16) 0.11876(14) 0.54763(9) 0.0194(3) Uani 1 1 d . . . . .
C7 C 0.15159(15) 0.18053(14) 0.48566(9) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.04326(18) 0.25245(17) 0.52029(10) 0.0278(3) Uani 1 1 d . . . . .
H8 H 0.045457 0.260001 0.583659 0.033 Uiso 1 1 calc R U . . .
C9 C -0.06795(18) 0.31320(19) 0.46269(11) 0.0306(4) Uani 1 1 d . . . . .
H9 H -0.141177 0.362582 0.486732 0.037 Uiso 1 1 calc R U . . .
C10 C -0.07221(17) 0.30185(16) 0.37018(11) 0.0260(3) Uani 1 1 d . . . . .
H10 H -0.148252 0.343522 0.330844 0.031 Uiso 1 1 calc R U . . .
C11 C 0.03472(16) 0.22952(15) 0.33503(10) 0.0224(3) Uani 1 1 d . . . . .
H11 H 0.031797 0.221660 0.271626 0.027 Uiso 1 1 calc R U . . .
C12 C 0.14560(16) 0.16888(14) 0.39237(10) 0.0205(3) Uani 1 1 d . . . . .
H12 H 0.218151 0.118949 0.368050 0.025 Uiso 1 1 calc R U . . .
C13 C 0.45408(15) 0.32990(14) 0.42767(9) 0.0187(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.8320(17) . ?
Cl2 B1 1.8384(16) . ?
Cl3 B1 1.8350(16) . ?
N1 C13 1.1380(18) . ?
N1 C1 1.3985(18) . ?
B1 C13 1.613(2) . ?
C1 C2 1.3909(19) . ?
C1 C6 1.404(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.4824(19) . ?
C7 C8 1.393(2) . ?
C7 C12 1.3963(19) . ?
C8 C9 1.389(2) . ?
C9 C10 1.386(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.384(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C1 172.96(14) . . ?
C13 B1 Cl1 107.90(10) . . ?
C13 B1 Cl3 105.97(10) . . ?
Cl1 B1 Cl3 111.97(8) . . ?
C13 B1 Cl2 106.08(10) . . ?
Cl1 B1 Cl2 112.56(8) . . ?
Cl3 B1 Cl2 111.87(9) . . ?
C2 C1 N1 118.74(13) . . ?
C2 C1 C6 123.53(13) . . ?
N1 C1 C6 117.68(12) . . ?
C3 C2 C1 118.16(14) . . ?
C2 C3 C4 119.96(14) . . ?
C5 C4 C3 120.87(14) . . ?
C4 C5 C6 121.00(14) . . ?
C5 C6 C1 116.47(13) . . ?
C5 C6 C7 121.78(13) . . ?
C1 C6 C7 121.73(13) . . ?
C8 C7 C12 119.06(13) . . ?
C8 C7 C6 119.99(13) . . ?
C12 C7 C6 120.95(13) . . ?
C9 C8 C7 120.37(14) . . ?
C10 C9 C8 120.07(14) . . ?
C9 C10 C11 119.97(14) . . ?
C12 C11 C10 120.01(14) . . ?
C11 C12 C7 120.51(13) . . ?
N1 C13 B1 176.06(15) . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.068



_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_ic22538
_database_code_depnum_ccdc_archive 'CCDC 2418960'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        '2-isocyanobiphenyl?boron tribromide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 B Br3 N'
_chemical_formula_weight         429.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.0581(4)
_cell_length_b                   10.2611(5)
_cell_length_c                   15.6575(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.2352(13)
_cell_angle_gamma                90
_cell_volume                     1446.69(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9352
_cell_measurement_theta_min      5.16
_cell_measurement_theta_max      69.88

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    10.172
_shelx_estimated_absorpt_T_min   0.311
_shelx_estimated_absorpt_T_max   0.630
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6733
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20617
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.163
_diffrn_reflns_theta_max         70.010
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2730
_reflns_number_gt                2680
_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 APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0336P)²+0.9665P] 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         2730
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Br1 Br 0.28239(2) 0.54758(2) 0.36505(2) 0.01894(9) Uani 1 1 d . . . . .
Br2 Br 0.64891(2) 0.53980(2) 0.36935(2) 0.01788(8) Uani 1 1 d . . . . .
Br3 Br 0.43964(3) 0.33926(2) 0.24014(2) 0.02295(9) Uani 1 1 d . . . . .
N1 N 0.45515(17) 0.25040(16) 0.47483(10) 0.0151(3) Uani 1 1 d . . . . .
B1 B 0.4609(2) 0.4377(2) 0.35147(15) 0.0166(4) Uani 1 1 d . . . . .
C1 C 0.4230(2) 0.15764(18) 0.53613(12) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.5378(2) 0.11478(19) 0.59553(12) 0.0180(4) Uani 1 1 d . . . . .
H2A H 0.637054 0.142925 0.592674 0.022 Uiso 1 1 calc R U . . .
C3 C 0.5030(2) 0.0297(2) 0.65906(13) 0.0203(4) Uani 1 1 d . . . . .
H3A H 0.578914 -0.000461 0.701033 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3578(2) -0.0118(2) 0.66170(13) 0.0222(4) Uani 1 1 d . . . . .
H4A H 0.335374 -0.071666 0.704733 0.027 Uiso 1 1 calc R U . . .
C5 C 0.2447(2) 0.0337(2) 0.60177(14) 0.0211(4) Uani 1 1 d . . . . .
H5A H 0.145604 0.005159 0.604875 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2745(2) 0.12038(19) 0.53731(12) 0.0166(4) Uani 1 1 d . . . . .
C7 C 0.1529(2) 0.17447(19) 0.47565(13) 0.0168(4) Uani 1 1 d . . . . .
C8 C 0.0354(2) 0.2396(2) 0.50672(13) 0.0243(5) Uani 1 1 d . . . . .
H8A H 0.031933 0.247605 0.566921 0.029 Uiso 1 1 calc R U . . .
C9 C -0.0771(2) 0.2933(3) 0.45005(14) 0.0286(5) Uani 1 1 d . . . . .
H9A H -0.157103 0.337878 0.471650 0.034 Uiso 1 1 calc R U . . .
C10 C -0.0729(2) 0.2820(2) 0.36209(13) 0.0221(4) Uani 1 1 d . . . . .
H10A H -0.149554 0.319228 0.323501 0.027 Uiso 1 1 calc R U . . .
C11 C 0.0433(2) 0.2162(2) 0.33058(13) 0.0194(4) Uani 1 1 d . . . . .
H11A H 0.045760 0.207482 0.270340 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1561(2) 0.16305(19) 0.38692(13) 0.0180(4) Uani 1 1 d . . . . .
H12A H 0.236068 0.118642 0.365085 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4632(2) 0.32977(19) 0.42454(12) 0.0157(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 2.001(2) . ?
Br2 B1 1.993(2) . ?
Br3 B1 2.006(2) . ?
N1 C13 1.141(3) . ?
N1 C1 1.405(3) . ?
B1 C13 1.591(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.400(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.491(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.398(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.387(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.387(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C1 171.5(2) . . ?
C13 B1 Br2 108.70(14) . . ?
C13 B1 Br1 105.27(14) . . ?
Br2 B1 Br1 112.15(11) . . ?
C13 B1 Br3 105.47(14) . . ?
Br2 B1 Br3 112.75(11) . . ?
Br1 B1 Br3 111.94(11) . . ?
C2 C1 C6 123.72(18) . . ?
C2 C1 N1 118.42(18) . . ?
C6 C1 N1 117.71(17) . . ?
C3 C2 C1 117.89(19) . . ?
C2 C3 C4 120.35(19) . . ?
C3 C4 C5 120.52(19) . . ?
C4 C5 C6 121.0(2) . . ?
C5 C6 C1 116.48(18) . . ?
C5 C6 C7 121.27(19) . . ?
C1 C6 C7 122.20(18) . . ?
C8 C7 C12 119.23(18) . . ?
C8 C7 C6 119.52(18) . . ?
C12 C7 C6 121.24(18) . . ?
C7 C8 C9 120.2(2) . . ?
C10 C9 C8 120.2(2) . . ?
C11 C10 C9 119.89(19) . . ?
C10 C11 C12 120.04(19) . . ?
C11 C12 C7 120.37(18) . . ?
N1 C13 B1 175.3(2) . . ?

_refine_diff_density_max         0.566
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.173



_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_ic22408
_database_code_depnum_ccdc_archive 'CCDC 2418961'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H16 B2 Cl6 N2'
_chemical_formula_weight         590.73

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

_space_group_crystal_system      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                   16.4478(6)
_cell_length_b                   10.7938(4)
_cell_length_c                   13.9976(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.3459(13)
_cell_angle_gamma                90
_cell_volume                     2485.01(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9845
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      30.48

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.713
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9126
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47160
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         30.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7581
_reflns_number_gt                6831
_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 APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0352P)²+1.1032P] 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         7581
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.57370(2) 0.82364(3) 0.63248(2) 0.01725(7) Uani 1 1 d . . . . .
Cl2 Cl 0.61104(2) 0.97304(3) 0.45296(2) 0.01769(7) Uani 1 1 d . . . . .
N1 N 0.62152(6) 0.71248(9) 0.46217(7) 0.01363(17) Uani 1 1 d . . . . .
N2 N 0.72632(6) 0.82195(9) 0.54170(7) 0.01271(17) Uani 1 1 d . . . . .
B1 B 0.63298(7) 0.83408(12) 0.52211(9) 0.0137(2) Uani 1 1 d . . . . .
C1 C 0.54905(7) 0.66876(11) 0.42298(8) 0.0152(2) Uani 1 1 d . . . . .
C2 C 0.47824(7) 0.74240(12) 0.42650(9) 0.0181(2) Uani 1 1 d . . . . .
H2 H 0.479038 0.820422 0.457908 0.022 Uiso 1 1 calc R U . . .
C3 C 0.40802(7) 0.69974(13) 0.38386(9) 0.0209(2) Uani 1 1 d . . . . .
H3 H 0.359996 0.748504 0.386271 0.025 Uiso 1 1 calc R U . . .
C4 C 0.40667(7) 0.58489(13) 0.33683(10) 0.0223(2) Uani 1 1 d . . . . .
H4 H 0.358038 0.557233 0.306722 0.027 Uiso 1 1 calc R U . . .
C5 C 0.47527(8) 0.51211(12) 0.33405(9) 0.0202(2) Uani 1 1 d . . . . .
H5 H 0.473615 0.434708 0.301793 0.024 Uiso 1 1 calc R U . . .
C6 C 0.54806(7) 0.55117(11) 0.37859(8) 0.0156(2) Uani 1 1 d . . . . .
C7 C 0.61920(7) 0.47302(11) 0.38670(8) 0.0154(2) Uani 1 1 d . . . . .
C8 C 0.61892(7) 0.34765(11) 0.35789(9) 0.0187(2) Uani 1 1 d . . . . .
H8 H 0.573458 0.315555 0.323789 0.022 Uiso 1 1 calc R U . . .
C9 C 0.68364(8) 0.27151(11) 0.37860(9) 0.0202(2) Uani 1 1 d . . . . .
H9 H 0.682984 0.187831 0.357567 0.024 Uiso 1 1 calc R U . . .
C10 C 0.75065(8) 0.31631(11) 0.43053(9) 0.0197(2) Uani 1 1 d . . . . .
H10 H 0.793323 0.261531 0.448367 0.024 Uiso 1 1 calc R U . . .
C11 C 0.75472(7) 0.43914(11) 0.45566(9) 0.0170(2) Uani 1 1 d . . . . .
H11 H 0.800835 0.469556 0.489459 0.020 Uiso 1 1 calc R U . . .
C12 C 0.69039(7) 0.52053(10) 0.43132(8) 0.0143(2) Uani 1 1 d . . . . .
C13 C 0.69025(7) 0.64777(10) 0.45909(8) 0.01309(19) Uani 1 1 d . . . . .
C14 C 0.75781(7) 0.72562(10) 0.49562(8) 0.01299(19) Uani 1 1 d . . . . .
C15 C 0.84315(6) 0.71287(10) 0.48240(8) 0.01331(19) Uani 1 1 d . . . . .
C16 C 0.87726(7) 0.63398(11) 0.41196(9) 0.0165(2) Uani 1 1 d . . . . .
H16 H 0.842701 0.586645 0.371400 0.020 Uiso 1 1 calc R U . . .
C17 C 0.96010(7) 0.62610(12) 0.40248(9) 0.0202(2) Uani 1 1 d . . . . .
H17 H 0.982921 0.572636 0.355870 0.024 Uiso 1 1 calc R U . . .
C18 C 1.01120(7) 0.69737(12) 0.46193(10) 0.0213(2) Uani 1 1 d . . . . .
H18 H 1.068492 0.688179 0.457368 0.026 Uiso 1 1 calc R U . . .
C19 C 0.97958(7) 0.77990(12) 0.52634(9) 0.0184(2) Uani 1 1 d . . . . .
H19 H 1.015109 0.829178 0.564261 0.022 Uiso 1 1 calc R U . . .
C20 C 0.89470(7) 0.79211(11) 0.53668(8) 0.0139(2) Uani 1 1 d . . . . .
C21 C 0.85905(7) 0.88733(10) 0.59520(8) 0.01355(19) Uani 1 1 d . . . . .
C22 C 0.90623(7) 0.97195(11) 0.64881(9) 0.0176(2) Uani 1 1 d . . . . .
H22 H 0.963405 0.960749 0.653462 0.021 Uiso 1 1 calc R U . . .
C23 C 0.87032(8) 1.07026(12) 0.69428(9) 0.0196(2) Uani 1 1 d . . . . .
H23 H 0.902974 1.127302 0.729144 0.024 Uiso 1 1 calc R U . . .
C24 C 0.78545(7) 1.08727(11) 0.68969(9) 0.0188(2) Uani 1 1 d . . . . .
H24 H 0.761342 1.156009 0.721046 0.023 Uiso 1 1 calc R U . . .
C25 C 0.73748(7) 1.00528(11) 0.64027(9) 0.0166(2) Uani 1 1 d . . . . .
H25 H 0.680172 1.016070 0.638177 0.020 Uiso 1 1 calc R U . . .
C26 C 0.77394(7) 0.90476(10) 0.59257(8) 0.01312(19) Uani 1 1 d . . . . .
B2 B 0.83183(8) 0.95888(12) 0.26565(10) 0.0156(2) Uani 1 1 d . . . . .
Cl3 Cl 0.83874(2) 1.02020(3) 0.38867(2) 0.01955(7) Uani 1 1 d . . . . .
Cl4 Cl 0.74497(2) 0.84998(3) 0.25485(2) 0.02244(7) Uani 1 1 d . . . . .
Cl5 Cl 0.92661(2) 0.87768(3) 0.23519(2) 0.02223(7) Uani 1 1 d . . . . .
Cl6 Cl 0.81651(2) 1.09241(3) 0.18387(2) 0.02504(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.8353(13) . ?
Cl2 B1 1.8201(13) . ?
N1 C13 1.3297(14) . ?
N1 C1 1.3916(14) . ?
N1 B1 1.5685(16) . ?
N2 C14 1.3302(14) . ?
N2 C26 1.3830(14) . ?
N2 B1 1.5635(15) . ?
C1 C2 1.4112(16) . ?
C1 C6 1.4132(16) . ?
C2 C3 1.3762(17) . ?
C3 C4 1.4037(19) . ?
C4 C5 1.3756(18) . ?
C5 C6 1.4110(16) . ?
C6 C7 1.4463(16) . ?
C7 C8 1.4120(16) . ?
C7 C12 1.4197(16) . ?
C8 C9 1.3744(18) . ?
C9 C10 1.4026(18) . ?
C10 C11 1.3733(16) . ?
C11 C12 1.4153(16) . ?
C12 C13 1.4274(15) . ?
C13 C14 1.4817(15) . ?
C14 C15 1.4236(15) . ?
C15 C16 1.4209(15) . ?
C15 C20 1.4212(16) . ?
C16 C17 1.3724(16) . ?
C17 C18 1.4080(18) . ?
C18 C19 1.3721(17) . ?
C19 C20 1.4106(15) . ?
C20 C21 1.4412(15) . ?
C21 C22 1.4115(16) . ?
C21 C26 1.4128(15) . ?
C22 C23 1.3728(17) . ?
C23 C24 1.4091(17) . ?
C24 C25 1.3703(17) . ?
C25 C26 1.4097(15) . ?
B2 Cl5 1.8407(13) . ?
B2 Cl3 1.8477(14) . ?
B2 Cl4 1.8555(13) . ?
B2 Cl6 1.8568(14) . ?

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
C13 N1 C1 122.37(10) . . ?
C13 N1 B1 110.94(9) . . ?
C1 N1 B1 126.48(9) . . ?
C14 N2 C26 122.28(10) . . ?
C14 N2 B1 111.42(9) . . ?
C26 N2 B1 126.06(9) . . ?
N2 B1 N1 97.96(8) . . ?
N2 B1 Cl2 110.71(8) . . ?
N1 B1 Cl2 112.48(8) . . ?
N2 B1 Cl1 111.92(8) . . ?
N1 B1 Cl1 109.65(8) . . ?
Cl2 B1 Cl1 113.18(6) . . ?
N1 C1 C2 120.02(11) . . ?
N1 C1 C6 119.05(10) . . ?
C2 C1 C6 120.93(11) . . ?
C3 C2 C1 119.14(12) . . ?
C2 C3 C4 120.65(12) . . ?
C5 C4 C3 120.46(11) . . ?
C4 C5 C6 120.72(12) . . ?
C5 C6 C1 118.04(11) . . ?
C5 C6 C7 122.98(11) . . ?
C1 C6 C7 118.82(10) . . ?
C8 C7 C12 118.24(11) . . ?
C8 C7 C6 122.36(11) . . ?
C12 C7 C6 119.25(10) . . ?
C9 C8 C7 120.77(11) . . ?
C8 C9 C10 120.56(11) . . ?
C11 C10 C9 120.17(12) . . ?
C10 C11 C12 120.16(11) . . ?
C11 C12 C7 119.68(10) . . ?
C11 C12 C13 122.29(11) . . ?
C7 C12 C13 117.69(10) . . ?
N1 C13 C12 121.13(10) . . ?
N1 C13 C14 109.08(10) . . ?
C12 C13 C14 129.58(10) . . ?
N2 C14 C15 121.71(10) . . ?
N2 C14 C13 108.50(9) . . ?
C15 C14 C13 129.67(10) . . ?
C16 C15 C20 119.66(10) . . ?
C16 C15 C14 122.82(10) . . ?
C20 C15 C14 117.25(10) . . ?
C17 C16 C15 120.04(11) . . ?
C16 C17 C18 119.90(11) . . ?
C19 C18 C17 121.04(11) . . ?
C18 C19 C20 120.49(11) . . ?
C19 C20 C15 118.46(10) . . ?
C19 C20 C21 122.09(10) . . ?
C15 C20 C21 119.31(10) . . ?
C22 C21 C26 117.98(10) . . ?
C22 C21 C20 122.64(10) . . ?
C26 C21 C20 119.12(10) . . ?
C23 C22 C21 120.66(11) . . ?
C22 C23 C24 120.56(11) . . ?
C25 C24 C23 120.41(11) . . ?
C24 C25 C26 119.40(11) . . ?
N2 C26 C25 120.01(10) . . ?
N2 C26 C21 119.03(10) . . ?
C25 C26 C21 120.96(10) . . ?
Cl5 B2 Cl3 109.82(7) . . ?
Cl5 B2 Cl4 109.40(7) . . ?
Cl3 B2 Cl4 110.23(7) . . ?
Cl5 B2 Cl6 109.80(7) . . ?
Cl3 B2 Cl6 107.69(7) . . ?
Cl4 B2 Cl6 109.88(7) . . ?

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.072



_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_ic22811
_database_code_depnum_ccdc_archive 'CCDC 2418958'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Phenanthridinium 6-trichloroborate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 B Cl3 N'
_chemical_formula_weight         296.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   17.5560(6)
_cell_length_b                   13.5459(5)
_cell_length_c                   10.4412(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2483.04(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9802
_cell_measurement_theta_min      4.93
_cell_measurement_theta_max      70.03

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    6.479
_shelx_estimated_absorpt_T_min   0.564
_shelx_estimated_absorpt_T_max   0.738
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8178
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23416
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.122
_diffrn_reflns_theta_max         70.106
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4650
_reflns_number_gt                4620
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.976

_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX5'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Refined as a 2-component inversion twin.,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)+40.2851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.64(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4650
_refine_ls_number_parameters     326
_refine_ls_number_restraints     376
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0847
_refine_ls_wR_factor_ref         0.2434
_refine_ls_wR_factor_gt          0.2433
_refine_ls_goodness_of_fit_ref   1.378
_refine_ls_restrained_S_all      1.327
_refine_ls_shift/su_max          0.014
_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
Cl1 Cl -0.46762(18) -0.2307(3) -0.2457(4) 0.0185(7) Uani 1 1 d . . . . .
Cl2 Cl -0.4679(2) -0.0063(3) -0.2115(4) 0.0232(8) Uani 1 1 d . . . . .
Cl3 Cl -0.4506(2) -0.1398(3) 0.0187(4) 0.0217(8) Uani 1 1 d . . . . .
N1 N -0.6165(7) -0.1249(10) -0.0044(12) 0.018(3) Uani 1 1 d . . . . .
H1 H -0.582591 -0.122500 0.057632 0.021 Uiso 1 1 calc R U . . .
C1 C -0.5904(8) -0.1255(11) -0.1211(14) 0.014(3) Uani 1 1 d . U . . .
C2 C -0.6446(7) -0.1210(10) -0.2246(15) 0.016(2) Uani 1 1 d . U . . .
C3 C -0.6193(9) -0.1142(11) -0.3517(14) 0.018(3) Uani 1 1 d . U . . .
H3 H -0.566437 -0.111686 -0.370545 0.021 Uiso 1 1 calc R U . . .
C4 C -0.6733(9) -0.1113(12) -0.4506(16) 0.020(3) Uani 1 1 d . U . . .
H4 H -0.656806 -0.105049 -0.536929 0.024 Uiso 1 1 calc R U . . .
C5 C -0.7509(9) -0.1176(11) -0.4235(15) 0.017(3) Uani 1 1 d . . . . .
H5 H -0.786679 -0.115617 -0.491676 0.020 Uiso 1 1 calc R U . . .
C6 C -0.7762(8) -0.1266(11) -0.2998(15) 0.016(3) Uani 1 1 d . . . . .
H6 H -0.829167 -0.132881 -0.283115 0.020 Uiso 1 1 calc R U . . .
C7 C -0.7239(8) -0.1265(10) -0.1973(15) 0.014(2) Uani 1 1 d . U . . .
C8 C -0.7490(9) -0.1326(11) -0.0643(15) 0.015(2) Uani 1 1 d . U . . .
C9 C -0.8266(8) -0.1320(11) -0.0265(16) 0.017(2) Uani 1 1 d . U . . .
H9 H -0.865520 -0.133117 -0.089758 0.020 Uiso 1 1 calc R U . . .
C10 C -0.8459(9) -0.1297(13) 0.1014(17) 0.024(4) Uani 1 1 d . . . . .
H10 H -0.897992 -0.128286 0.125747 0.029 Uiso 1 1 calc R U . . .
C11 C -0.7889(9) -0.1296(11) 0.1962(16) 0.020(3) Uani 1 1 d . U . . .
H11 H -0.802830 -0.132273 0.284107 0.024 Uiso 1 1 calc R U . . .
C12 C -0.7142(9) -0.1258(11) 0.1629(16) 0.019(3) Uani 1 1 d . U . . .
H12 H -0.675909 -0.121893 0.227062 0.023 Uiso 1 1 calc R U . . .
C13 C -0.6939(8) -0.1275(10) 0.0325(15) 0.015(2) Uani 1 1 d . U . . .
B1 B -0.4978(10) -0.1264(14) -0.1390(16) 0.019(4) Uani 1 1 d . . . . .
Cl4 Cl -0.0467(2) -0.2510(3) -0.7028(4) 0.0241(8) Uani 1 1 d . . . . .
Cl5 Cl -0.05306(18) -0.0284(3) -0.7428(3) 0.0204(8) Uani 1 1 d . . . . .
Cl6 Cl 0.04831(18) -0.1160(3) -0.5380(3) 0.0179(7) Uani 1 1 d . . . . .
N2 N -0.0956(7) -0.1175(9) -0.3983(12) 0.014(3) Uani 1 1 d . . . . .
H2 H -0.046762 -0.111257 -0.381158 0.017 Uiso 1 1 calc R U . . .
C14 C -0.1147(8) -0.1278(10) -0.5190(13) 0.012(2) Uani 1 1 d . U . . .
C15 C -0.1949(8) -0.1282(11) -0.5483(15) 0.015(2) Uani 1 1 d . U . . .
C16 C -0.2188(8) -0.1333(10) -0.6793(15) 0.016(2) Uani 1 1 d . U . . .
H16 H -0.182037 -0.134600 -0.746100 0.019 Uiso 1 1 calc R U . . .
C17 C -0.2952(8) -0.1364(10) -0.7081(16) 0.018(2) Uani 1 1 d . U . . .
H17 H -0.311058 -0.141499 -0.794773 0.022 Uiso 1 1 calc R U . . .
C18 C -0.3500(9) -0.1319(11) -0.6099(15) 0.018(2) Uani 1 1 d . U . . .
H18 H -0.402595 -0.130976 -0.631034 0.021 Uiso 1 1 calc R U . . .
C19 C -0.3279(8) -0.1290(11) -0.4837(16) 0.017(2) Uani 1 1 d . U . . .
H19 H -0.365434 -0.127804 -0.418117 0.020 Uiso 1 1 calc R U . . .
C20 C -0.2494(9) -0.1277(11) -0.4504(14) 0.015(2) Uani 1 1 d . U . . .
C21 C -0.2249(9) -0.1226(11) -0.3194(15) 0.015(2) Uani 1 1 d . U . . .
C22 C -0.2743(8) -0.1217(11) -0.2116(16) 0.018(3) Uani 1 1 d . . . . .
H22 H -0.327848 -0.124680 -0.223806 0.022 Uiso 1 1 calc R U . . .
C23 C -0.2452(10) -0.1166(12) -0.0905(15) 0.021(3) Uani 1 1 d . . . . .
H23 H -0.279255 -0.120328 -0.019978 0.025 Uiso 1 1 calc R U . . .
C24 C -0.1652(8) -0.1059(10) -0.0652(14) 0.013(3) Uani 1 1 d . U . . .
H24 H -0.146652 -0.096434 0.019394 0.016 Uiso 1 1 calc R U . . .
C25 C -0.1170(9) -0.1100(11) -0.1678(14) 0.015(3) Uani 1 1 d . U . . .
H25 H -0.063451 -0.108991 -0.154806 0.018 Uiso 1 1 calc R U . . .
C26 C -0.1468(8) -0.1156(11) -0.2924(14) 0.013(2) Uani 1 1 d . U . . .
B2 B -0.0452(10) -0.1287(13) -0.6224(17) 0.017(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.876(19) . ?
Cl2 B1 1.870(18) . ?
Cl3 B1 1.852(18) . ?
N1 C1 1.30(2) . ?
N1 C13 1.413(18) . ?
C1 C2 1.44(2) . ?
C1 B1 1.64(2) . ?
C2 C3 1.40(2) . ?
C2 C7 1.423(18) . ?
C3 C4 1.40(2) . ?
C4 C5 1.39(2) . ?
C5 C6 1.37(2) . ?
C6 C7 1.41(2) . ?
C7 C8 1.46(2) . ?
C8 C13 1.40(2) . ?
C8 C9 1.42(2) . ?
C9 C10 1.38(2) . ?
C10 C11 1.41(2) . ?
C11 C12 1.36(2) . ?
C12 C13 1.41(2) . ?
Cl4 B2 1.858(18) . ?
Cl5 B2 1.856(17) . ?
Cl6 B2 1.871(18) . ?
N2 C14 1.311(19) . ?
N2 C26 1.425(18) . ?
C14 C15 1.440(19) . ?
C14 B2 1.63(2) . ?
C15 C20 1.40(2) . ?
C15 C16 1.43(2) . ?
C16 C17 1.37(2) . ?
C17 C18 1.41(2) . ?
C18 C19 1.37(2) . ?
C19 C20 1.42(2) . ?
C20 C21 1.44(2) . ?
C21 C26 1.40(2) . ?
C21 C22 1.42(2) . ?
C22 C23 1.37(2) . ?
C23 C24 1.43(2) . ?
C24 C25 1.37(2) . ?
C25 C26 1.41(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 126.4(12) . . ?
N1 C1 C2 118.0(13) . . ?
N1 C1 B1 117.2(13) . . ?
C2 C1 B1 124.8(13) . . ?
C3 C2 C7 120.2(13) . . ?
C3 C2 C1 120.3(13) . . ?
C7 C2 C1 119.5(14) . . ?
C4 C3 C2 119.1(14) . . ?
C5 C4 C3 120.6(15) . . ?
C6 C5 C4 120.9(15) . . ?
C5 C6 C7 120.2(14) . . ?
C6 C7 C2 119.0(14) . . ?
C6 C7 C8 121.7(13) . . ?
C2 C7 C8 119.3(13) . . ?
C13 C8 C9 117.5(14) . . ?
C13 C8 C7 118.4(14) . . ?
C9 C8 C7 123.7(14) . . ?
C10 C9 C8 120.3(14) . . ?
C9 C10 C11 120.5(15) . . ?
C12 C11 C10 120.4(16) . . ?
C11 C12 C13 119.4(15) . . ?
C8 C13 C12 121.6(14) . . ?
C8 C13 N1 117.9(14) . . ?
C12 C13 N1 120.4(14) . . ?
C1 B1 Cl3 110.1(11) . . ?
C1 B1 Cl2 108.6(12) . . ?
Cl3 B1 Cl2 108.6(9) . . ?
C1 B1 Cl1 110.8(12) . . ?
Cl3 B1 Cl1 109.1(9) . . ?
Cl2 B1 Cl1 109.6(8) . . ?
C14 N2 C26 125.9(12) . . ?
N2 C14 C15 117.0(13) . . ?
N2 C14 B2 116.5(13) . . ?
C15 C14 B2 126.2(13) . . ?
C20 C15 C16 119.8(13) . . ?
C20 C15 C14 120.8(14) . . ?
C16 C15 C14 119.3(13) . . ?
C17 C16 C15 119.7(14) . . ?
C16 C17 C18 120.5(15) . . ?
C19 C18 C17 120.5(14) . . ?
C18 C19 C20 120.5(14) . . ?
C15 C20 C19 119.0(13) . . ?
C15 C20 C21 119.5(14) . . ?
C19 C20 C21 121.5(14) . . ?
C26 C21 C22 115.9(14) . . ?
C26 C21 C20 119.1(14) . . ?
C22 C21 C20 125.0(14) . . ?
C23 C22 C21 120.4(14) . . ?
C22 C23 C24 122.8(14) . . ?
C25 C24 C23 117.2(14) . . ?
C24 C25 C26 119.8(13) . . ?
C21 C26 C25 123.6(13) . . ?
C21 C26 N2 117.4(13) . . ?
C25 C26 N2 119.0(12) . . ?
C14 B2 Cl5 112.8(11) . . ?
C14 B2 Cl4 107.2(10) . . ?
Cl5 B2 Cl4 110.2(9) . . ?
C14 B2 Cl6 110.1(11) . . ?
Cl5 B2 Cl6 108.5(8) . . ?
Cl4 B2 Cl6 107.9(9) . . ?

_refine_diff_density_max         1.451
_refine_diff_density_min         -1.308
_refine_diff_density_rms         0.190



####################################################################### 
# 
# 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_ic22870
_database_code_depnum_ccdc_archive 'CCDC 2418959'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        '2-isocyanobiphenyl?boron triiodide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 B I3 N'
_chemical_formula_weight         570.72

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'
I I -0.4742 1.8119 '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                   8.5624(3)
_cell_length_b                   10.9109(4)
_cell_length_c                   16.6083(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.5760(15)
_cell_angle_gamma                90
_cell_volume                     1548.58(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.448
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    6.037
_shelx_estimated_absorpt_T_min   0.465
_shelx_estimated_absorpt_T_max   0.752
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8167
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29882
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         30.566
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4748
_reflns_number_gt                4406
_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 APEX5'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4748
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   0.687
_refine_ls_restrained_S_all      0.687
_refine_ls_shift/su_max          0.018
_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
I1 I 0.24684(2) 0.53063(2) 0.36887(2) 0.02101(6) Uani 1 1 d . . . . .
I2 I 0.46439(2) 0.32508(2) 0.23898(2) 0.02179(6) Uani 1 1 d . . . . .
I3 I 0.67887(2) 0.55176(2) 0.36994(2) 0.01984(6) Uani 1 1 d . . . . .
N1 N 0.4699(2) 0.25628(17) 0.46832(12) 0.0176(3) Uani 1 1 d . . . . .
B1 B 0.4709(3) 0.4319(2) 0.35342(15) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.4754(3) 0.33189(19) 0.42079(14) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.1719(3) 0.1542(2) 0.38404(14) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.263201 0.117830 0.364670 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0535(3) 0.1954(2) 0.32963(15) 0.0228(4) Uani 1 1 d . . . . .
H3 H 0.063808 0.186712 0.273298 0.027 Uiso 1 1 calc R U . . .
C4 C -0.0800(3) 0.2493(2) 0.35748(16) 0.0239(4) Uani 1 1 d . . . . .
H4 H -0.161054 0.277362 0.320363 0.029 Uiso 1 1 calc R U . . .
C5 C -0.0940(3) 0.2619(2) 0.43990(16) 0.0260(5) Uani 1 1 d . . . . .
H5 H -0.184343 0.300032 0.458987 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0229(3) 0.2193(2) 0.49486(15) 0.0224(4) Uani 1 1 d . . . . .
H6 H 0.010899 0.226731 0.551130 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1575(3) 0.16589(19) 0.46742(14) 0.0176(4) Uani 1 1 d . . . . .
C8 C 0.2824(2) 0.12491(19) 0.52689(13) 0.0172(4) Uani 1 1 d . . . . .
C9 C 0.2503(3) 0.0458(2) 0.58961(16) 0.0232(4) Uani 1 1 d . . . . .
H9 H 0.148186 0.012341 0.591697 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3647(3) 0.0148(2) 0.64917(15) 0.0249(5) Uani 1 1 d . . . . .
H10 H 0.339439 -0.038872 0.691460 0.030 Uiso 1 1 calc R U . . .
C11 C 0.5162(3) 0.0615(2) 0.64771(14) 0.0219(4) Uani 1 1 d . . . . .
H11 H 0.593226 0.040612 0.689093 0.026 Uiso 1 1 calc R U . . .
C12 C 0.5536(3) 0.1388(2) 0.58526(13) 0.0199(4) Uani 1 1 d . . . . .
H12 H 0.656538 0.170483 0.582595 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4362(3) 0.16870(19) 0.52663(13) 0.0172(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 B1 2.229(2) . ?
I2 B1 2.227(2) . ?
I3 B1 2.213(2) . ?
N1 C1 1.145(3) . ?
N1 C13 1.403(3) . ?
B1 C1 1.561(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.404(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.388(4) . ?
C5 C6 1.392(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.479(3) . ?
C8 C9 1.393(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.390(4) . ?
C10 C11 1.395(4) . ?
C11 C12 1.390(3) . ?
C12 C13 1.394(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 170.3(2) . . ?
C1 B1 I3 109.90(15) . . ?
C1 B1 I2 104.13(14) . . ?
I3 B1 I2 113.09(11) . . ?
C1 B1 I1 103.79(14) . . ?
I3 B1 I1 113.06(11) . . ?
I2 B1 I1 112.03(11) . . ?
N1 C1 B1 175.8(2) . . ?
C3 C2 C7 120.4(2) . . ?
C4 C3 C2 120.1(2) . . ?
C3 C4 C5 119.6(2) . . ?
C6 C5 C4 120.7(2) . . ?
C5 C6 C7 120.1(2) . . ?
C2 C7 C6 119.1(2) . . ?
C2 C7 C8 121.8(2) . . ?
C6 C7 C8 119.1(2) . . ?
C9 C8 C13 116.3(2) . . ?
C9 C8 C7 121.2(2) . . ?
C13 C8 C7 122.4(2) . . ?
C8 C9 C10 121.3(2) . . ?
C11 C10 C9 120.9(2) . . ?
C12 C11 C10 119.5(2) . . ?
C11 C12 C13 118.3(2) . . ?
N1 C13 C12 118.1(2) . . ?
N1 C13 C8 117.9(2) . . ?
C12 C13 C8 123.7(2) . . ?

_refine_diff_density_max         0.573
_refine_diff_density_min         -1.403
_refine_diff_density_rms         0.164



_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_ic22876
_database_code_depnum_ccdc_archive 'CCDC 2418962'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Phenanthridinium 6-triiodoborate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 B I3 N'
_chemical_formula_weight         570.72

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'
I I -0.4742 1.8119 '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                   9.7914(6)
_cell_length_b                   10.8546(6)
_cell_length_c                   14.0091(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.1323(19)
_cell_angle_gamma                90
_cell_volume                     1449.97(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9780
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.54

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.614
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    6.447
_shelx_estimated_absorpt_T_min   0.445
_shelx_estimated_absorpt_T_max   0.627
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32829
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_max         30.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4361
_reflns_number_gt                4238
_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 APEX5'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4361
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_restrained_S_all      0.858
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.07936(2) 0.30661(2) 0.32485(2) 0.01657(8) Uani 1 1 d . . . . .
I2 I 0.09189(2) 0.29869(2) 0.58038(2) 0.01525(8) Uani 1 1 d . . . . .
I3 I 0.14392(2) 0.04424(2) 0.41141(2) 0.01608(8) Uani 1 1 d . . . . .
N1 N 0.2349(2) 0.3831(2) 0.32535(15) 0.0128(4) Uani 1 1 d . . . . .
H1 H 0.145(4) 0.396(4) 0.293(3) 0.019 Uiso 1 1 d . U . . .
B1 B 0.1198(3) 0.2471(2) 0.4308(2) 0.0127(4) Uani 1 1 d . . . . .
C1 C 0.2561(3) 0.3144(2) 0.40552(17) 0.0112(4) Uani 1 1 d . . . . .
C2 C 0.3990(3) 0.3049(2) 0.46198(19) 0.0119(4) Uani 1 1 d . . . . .
C3 C 0.4336(3) 0.2292(2) 0.54668(18) 0.0137(4) Uani 1 1 d . . . . .
H3 H 0.362163 0.182838 0.566064 0.016 Uiso 1 1 calc R U . . .
C4 C 0.5683(3) 0.2222(2) 0.60056(19) 0.0156(4) Uani 1 1 d . . . . .
H4 H 0.589999 0.171596 0.657319 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6753(3) 0.2901(2) 0.5721(2) 0.0166(5) Uani 1 1 d . . . . .
H5 H 0.768575 0.285368 0.610376 0.020 Uiso 1 1 calc R U . . .
C6 C 0.6466(3) 0.3626(2) 0.49007(18) 0.0142(4) Uani 1 1 d . . . . .
H6 H 0.719911 0.407516 0.471800 0.017 Uiso 1 1 calc R U . . .
C7 C 0.5074(2) 0.3709(2) 0.43208(17) 0.0109(4) Uani 1 1 d . . . . .
C8 C 0.4754(3) 0.4428(2) 0.34301(18) 0.0115(4) Uani 1 1 d . . . . .
C9 C 0.5738(3) 0.5107(2) 0.30652(19) 0.0149(4) Uani 1 1 d . . . . .
H9 H 0.668931 0.512046 0.341653 0.018 Uiso 1 1 calc R U . . .
C10 C 0.5337(3) 0.5764(2) 0.2193(2) 0.0183(5) Uani 1 1 d . . . . .
H10 H 0.601911 0.622017 0.195519 0.022 Uiso 1 1 calc R U . . .
C11 C 0.3940(3) 0.5760(2) 0.16619(19) 0.0179(5) Uani 1 1 d . . . . .
H11 H 0.367646 0.620334 0.106373 0.021 Uiso 1 1 calc R U . . .
C12 C 0.2949(3) 0.5106(2) 0.20138(18) 0.0154(4) Uani 1 1 d . . . . .
H12 H 0.199679 0.509785 0.166229 0.018 Uiso 1 1 calc R U . . .
C13 C 0.3361(3) 0.4458(2) 0.28912(18) 0.0120(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 B1 2.260(3) . ?
I2 B1 2.245(3) . ?
I3 B1 2.238(3) . ?
N1 C1 1.324(3) . ?
N1 C13 1.390(3) . ?
B1 C1 1.630(4) . ?
C1 C2 1.446(3) . ?
C2 C7 1.420(3) . ?
C2 C3 1.420(3) . ?
C3 C4 1.365(3) . ?
C4 C5 1.410(4) . ?
C5 C6 1.368(4) . ?
C6 C7 1.422(3) . ?
C7 C8 1.445(3) . ?
C8 C9 1.399(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.392(4) . ?
C10 C11 1.401(4) . ?
C11 C12 1.381(4) . ?
C12 C13 1.394(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 126.7(2) . . ?
C1 B1 I3 107.49(15) . . ?
C1 B1 I2 111.72(15) . . ?
I3 B1 I2 113.40(11) . . ?
C1 B1 I1 110.88(16) . . ?
I3 B1 I1 107.51(11) . . ?
I2 B1 I1 105.78(11) . . ?
N1 C1 C2 116.7(2) . . ?
N1 C1 B1 117.3(2) . . ?
C2 C1 B1 126.0(2) . . ?
C7 C2 C3 119.1(2) . . ?
C7 C2 C1 119.9(2) . . ?
C3 C2 C1 121.0(2) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C4 C5 120.1(2) . . ?
C6 C5 C4 120.9(2) . . ?
C5 C6 C7 120.2(2) . . ?
C2 C7 C6 118.9(2) . . ?
C2 C7 C8 119.8(2) . . ?
C6 C7 C8 121.3(2) . . ?
C9 C8 C13 117.3(2) . . ?
C9 C8 C7 124.6(2) . . ?
C13 C8 C7 118.1(2) . . ?
C10 C9 C8 120.7(2) . . ?
C9 C10 C11 120.7(2) . . ?
C12 C11 C10 119.6(2) . . ?
C11 C12 C13 119.2(2) . . ?
N1 C13 C12 118.8(2) . . ?
N1 C13 C8 118.7(2) . . ?
C12 C13 C8 122.6(2) . . ?

_refine_diff_density_max         0.835
_refine_diff_density_min         -3.317
_refine_diff_density_rms         0.231



