# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_Oxidation-Compound-5
_database_code_depnum_ccdc_archive 'CCDC 2144021'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2022-01-24 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2021-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Bi N O2'
_chemical_formula_sum            'C21 H18 Bi N O2'
_chemical_formula_weight         525.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H18BiNO2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6002(3)
_cell_length_b                   9.9556(3)
_cell_length_c                   17.0845(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.022(2)
_cell_angle_gamma                90
_cell_volume                     1798.51(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9412
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.7540
_cell_measurement_theta_min      1.8610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.816
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_recrystallization_method 
'recrystallized from THF/heptane by slowly evaporating the solvents'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10218
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         2.194
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

 # Type Start End Width tₑₓₚ ω θ κ φ Frames
#--------------------------------------------------------------------------
 1 ω 2.33 183.94 0.30 4.99 -- 28.00 73.57 -25.67 606
 2 ω 2.33 132.69 0.30 4.99 -- 28.00 73.57 64.33 435
 3 ω 2.33 71.26 0.30 4.99 -- 28.00 73.57 154.33 230
 4 ω 2.33 17.31 0.30 4.99 -- 28.00 73.57 -25.67 50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0614987000
_diffrn_orient_matrix_UB_12      0.0141026000
_diffrn_orient_matrix_UB_13      0.0170931000
_diffrn_orient_matrix_UB_21      0.0254152000
_diffrn_orient_matrix_UB_22      -0.0110631000
_diffrn_orient_matrix_UB_23      -0.0367807000
_diffrn_orient_matrix_UB_31      -0.0085118000
_diffrn_orient_matrix_UB_32      0.0689286000
_diffrn_orient_matrix_UB_33      -0.0093872000
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3510
_reflns_number_total             3814
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0228
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0189P)²+3.6739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0468
_refine_ls_wR_factor_ref         0.0480
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Bi1 Bi 0.75661(2) 0.44126(2) 0.72196(2) 0.02732(5) Uani 1 1 d . . . . .
O1 O 0.5751(3) 0.5049(3) 0.77787(15) 0.0348(6) Uani 1 1 d . . . . .
O2 O 0.3657(3) 0.4775(3) 0.76876(19) 0.0517(8) Uani 1 1 d . . . . .
N1 N 0.9359(3) 0.2882(3) 0.69647(16) 0.0270(6) Uani 1 1 d . . . . .
H1 H 0.902384 0.197488 0.686980 0.032 Uiso 1 1 calc R U . . .
C1 C 0.8054(3) 0.3251(3) 0.8324(2) 0.0274(7) Uani 1 1 d . . . . .
C2 C 0.7265(3) 0.3101(4) 0.8935(2) 0.0307(8) Uani 1 1 d . . . . .
H2 H 0.646595 0.349292 0.890172 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7673(4) 0.2366(4) 0.9596(2) 0.0347(9) Uani 1 1 d . . . . .
H3 H 0.715212 0.227767 1.000904 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8843(4) 0.1769(4) 0.9642(2) 0.0368(9) Uani 1 1 d . . . . .
H4 H 0.910313 0.126519 1.008216 0.044 Uiso 1 1 calc R U . . .
C5 C 0.9640(3) 0.1909(4) 0.9038(2) 0.0321(8) Uani 1 1 d . . . . .
H5 H 1.043054 0.149918 0.907351 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9254(3) 0.2665(4) 0.8378(2) 0.0272(7) Uani 1 1 d . . . . .
C7 C 1.0116(3) 0.2893(4) 0.7727(2) 0.0310(8) Uani 1 1 d . . . . .
H7A H 1.054311 0.375025 0.780026 0.037 Uiso 1 1 calc R U . . .
H7B H 1.075220 0.219208 0.773403 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6097(3) 0.2947(4) 0.6757(2) 0.0279(8) Uani 1 1 d . . . . .
C9 C 0.6252(4) 0.1866(4) 0.6258(2) 0.0346(8) Uani 1 1 d . . . . .
H9 H 0.703247 0.171084 0.605753 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5241(4) 0.1017(4) 0.6061(2) 0.0429(10) Uani 1 1 d . . . . .
H10 H 0.534651 0.029354 0.572753 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4085(4) 0.1240(5) 0.6355(3) 0.0479(12) Uani 1 1 d . . . . .
H11 H 0.341846 0.065275 0.623211 0.058 Uiso 1 1 calc R U . . .
C12 C 0.3912(4) 0.2337(5) 0.6832(2) 0.0415(10) Uani 1 1 d . . . . .
H12 H 0.312454 0.249457 0.702119 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4912(4) 0.3205(4) 0.7029(2) 0.0333(8) Uani 1 1 d . . . . .
C14 C 0.4722(4) 0.4417(4) 0.7529(2) 0.0357(9) Uani 1 1 d . . . . .
C15 C 1.0129(4) 0.3254(5) 0.6312(2) 0.0371(9) Uani 1 1 d . . . . .
H15A H 1.089331 0.271510 0.633719 0.045 Uiso 1 1 calc R U . . .
H15B H 1.037560 0.419042 0.636362 0.045 Uiso 1 1 calc R U . . .
C16 C 0.9409(3) 0.3042(4) 0.5533(2) 0.0331(8) Uani 1 1 d . . . . .
C17 C 0.9387(4) 0.1789(5) 0.5186(2) 0.0441(10) Uani 1 1 d . . . . .
H17 H 0.980714 0.107787 0.544247 0.053 Uiso 1 1 calc R U . . .
C18 C 0.8752(4) 0.1576(6) 0.4463(3) 0.0563(13) Uani 1 1 d . . . . .
H18 H 0.874994 0.072907 0.423337 0.068 Uiso 1 1 calc R U . . .
C19 C 0.8128(4) 0.2616(6) 0.4086(3) 0.0586(14) Uani 1 1 d . . . . .
H19 H 0.771169 0.247883 0.359552 0.070 Uiso 1 1 calc R U . . .
C20 C 0.8111(4) 0.3867(6) 0.4430(3) 0.0514(12) Uani 1 1 d . . . . .
H20 H 0.767248 0.456838 0.417598 0.062 Uiso 1 1 calc R U . . .
C21 C 0.8747(4) 0.4077(4) 0.5152(3) 0.0411(10) Uani 1 1 d . . . . .
H21 H 0.873091 0.492042 0.538489 0.049 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
Bi1 O1 2.296(3) . ?
Bi1 N1 2.498(3) . ?
Bi1 C1 2.242(3) . ?
Bi1 C8 2.238(4) . ?
O1 C14 1.305(5) . ?
O2 C14 1.231(5) . ?
N1 H1 0.9800 . ?
N1 C7 1.481(4) . ?
N1 C15 1.475(4) . ?
C1 C2 1.392(5) . ?
C1 C6 1.396(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(5) . ?
C6 C7 1.506(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.389(5) . ?
C8 C13 1.395(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(5) . ?
C13 C14 1.499(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.502(5) . ?
C16 C17 1.381(6) . ?
C16 C21 1.382(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.364(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(6) . ?
C21 H21 0.9300 . ?

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
O1 Bi1 N1 155.61(9) . . ?
C1 Bi1 O1 86.74(11) . . ?
C1 Bi1 N1 72.45(11) . . ?
C8 Bi1 O1 75.19(12) . . ?
C8 Bi1 N1 93.42(11) . . ?
C8 Bi1 C1 94.28(12) . . ?
C14 O1 Bi1 115.9(2) . . ?
Bi1 N1 H1 108.7 . . ?
C7 N1 Bi1 102.4(2) . . ?
C7 N1 H1 108.7 . . ?
C15 N1 Bi1 116.6(2) . . ?
C15 N1 H1 108.7 . . ?
C15 N1 C7 111.6(3) . . ?
C2 C1 Bi1 124.8(3) . . ?
C2 C1 C6 119.9(3) . . ?
C6 C1 Bi1 115.3(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 119.0(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 121.4(3) . . ?
N1 C7 C6 109.2(3) . . ?
N1 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 Bi1 127.8(3) . . ?
C9 C8 C13 119.7(3) . . ?
C13 C8 Bi1 112.5(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.1(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(4) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C14 119.9(3) . . ?
C12 C13 C8 119.5(4) . . ?
C12 C13 C14 120.6(4) . . ?
O1 C14 C13 115.6(3) . . ?
O2 C14 O1 123.1(4) . . ?
O2 C14 C13 121.3(4) . . ?
N1 C15 H15A 109.4 . . ?
N1 C15 H15B 109.4 . . ?
N1 C15 C16 111.1(3) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 C21 118.5(4) . . ?
C21 C16 C15 121.4(4) . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(5) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.3(4) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.9(4) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.5(4) . . ?
C20 C21 H21 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 O1 C14 O2 -169.3(3) . . . . ?
Bi1 O1 C14 C13 10.9(4) . . . . ?
Bi1 N1 C7 C6 48.1(3) . . . . ?
Bi1 N1 C15 C16 -71.4(4) . . . . ?
Bi1 C1 C2 C3 -179.4(3) . . . . ?
Bi1 C1 C6 C5 -179.3(3) . . . . ?
Bi1 C1 C6 C7 2.2(4) . . . . ?
Bi1 C8 C9 C10 176.8(3) . . . . ?
Bi1 C8 C13 C12 -176.3(3) . . . . ?
Bi1 C8 C13 C14 4.0(4) . . . . ?
N1 C15 C16 C17 -84.7(4) . . . . ?
N1 C15 C16 C21 94.7(4) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C1 C6 C7 N1 -38.1(4) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
C2 C1 C6 C7 -177.1(3) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C4 C5 C6 C7 177.1(3) . . . . ?
C5 C6 C7 N1 143.4(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C7 N1 C15 C16 171.5(3) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C8 C13 C14 O1 -10.3(5) . . . . ?
C8 C13 C14 O2 169.9(4) . . . . ?
C9 C8 C13 C12 3.3(5) . . . . ?
C9 C8 C13 C14 -176.4(3) . . . . ?
C9 C10 C11 C12 1.9(6) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
C11 C12 C13 C8 -1.4(6) . . . . ?
C11 C12 C13 C14 178.3(3) . . . . ?
C12 C13 C14 O1 170.0(3) . . . . ?
C12 C13 C14 O2 -9.9(6) . . . . ?
C13 C8 C9 C10 -2.7(5) . . . . ?
C15 N1 C7 C6 173.5(3) . . . . ?
C15 C16 C17 C18 -178.7(4) . . . . ?
C15 C16 C21 C20 178.8(3) . . . . ?
C16 C17 C18 C19 -0.4(7) . . . . ?
C17 C16 C21 C20 -1.9(6) . . . . ?
C17 C18 C19 C20 -1.1(7) . . . . ?
C18 C19 C20 C21 1.1(7) . . . . ?
C19 C20 C21 C16 0.4(6) . . . . ?
C21 C16 C17 C18 1.9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.620
_oxdiff_exptl_absorpt_empirical_full_min 0.698
####################################################################### 
# 
# 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_Oxidation-Compound5-THF
_database_code_depnum_ccdc_archive 'CCDC 2144022'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2022-01-24 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2021-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Bi N O2, C4 H8 O'
_chemical_formula_sum            'C25 H26 Bi N O3'
_chemical_formula_weight         597.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H26Bi1N1O3
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'
Bi Bi -4.1077 10.2566 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.3430(4)
_cell_length_b                   9.6973(2)
_cell_length_c                   15.3553(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.472(2)
_cell_angle_gamma                90
_cell_volume                     2230.73(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11138
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.7810
_cell_measurement_theta_min      2.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_recrystallization_method 'Recrystallized from THF/heptane'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.701
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.33 183.94   0.30    1.99    --   28.00  73.57 -25.67  606
  2  ω      2.33 132.69   0.30    1.98    --   28.00  73.57  64.33  435
  3  ω      2.33  71.26   0.30    1.98    --   28.00  73.57 154.33  230
  4  ω      2.33  17.31   0.30    1.98    --   28.00  73.57 -25.67   50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0466230000
_diffrn_orient_matrix_UB_12      -0.0023729000
_diffrn_orient_matrix_UB_13      0.0180046000
_diffrn_orient_matrix_UB_21      -0.0081370000
_diffrn_orient_matrix_UB_22      0.0005987000
_diffrn_orient_matrix_UB_23      0.0437630000
_diffrn_orient_matrix_UB_31      -0.0015911000
_diffrn_orient_matrix_UB_32      -0.0730739000
_diffrn_orient_matrix_UB_33      -0.0002317000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4137
_reflns_number_total             4521
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0230
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0206P)²+4.5843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0496
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Bi1 Bi 0.73732(2) 0.81519(2) 0.71331(2) 0.01996(5) Uani 1 1 d . . . . .
O1 O 0.79519(16) 0.8737(2) 0.85961(16) 0.0231(5) Uani 1 1 d . . . . .
O2 O 0.88434(18) 0.8037(3) 0.98504(17) 0.0366(7) Uani 1 1 d . . . . .
O3 O 0.3409(2) 0.3130(4) 0.8679(2) 0.0588(9) Uani 1 1 d . . . . .
N1 N 0.66375(19) 0.6523(3) 0.59490(18) 0.0198(6) Uani 1 1 d . . . . .
H1 H 0.694333 0.563240 0.605871 0.024 Uiso 1 1 calc R U . . .
C1 C 0.6412(2) 0.6877(4) 0.7705(2) 0.0217(7) Uani 1 1 d . . . . .
C2 C 0.6418(2) 0.6774(4) 0.8609(2) 0.0264(8) Uani 1 1 d . . . . .
H2 H 0.684170 0.725765 0.902097 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5800(3) 0.5957(4) 0.8902(3) 0.0322(9) Uani 1 1 d . . . . .
H3 H 0.580658 0.589504 0.950737 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5174(3) 0.5237(4) 0.8293(3) 0.0372(10) Uani 1 1 d . . . . .
H4 H 0.476237 0.467838 0.848961 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5156(2) 0.5341(4) 0.7391(3) 0.0323(9) Uani 1 1 d . . . . .
H5 H 0.473017 0.485341 0.698384 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5768(2) 0.6166(4) 0.7088(2) 0.0228(7) Uani 1 1 d . . . . .
C7 C 0.5729(2) 0.6356(4) 0.6109(2) 0.0256(8) Uani 1 1 d . . . . .
H7A H 0.544493 0.556064 0.578264 0.031 Uiso 1 1 calc R U . . .
H7B H 0.537395 0.716425 0.589499 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8532(2) 0.6715(3) 0.7592(2) 0.0207(7) Uani 1 1 d . . . . .
C9 C 0.8905(2) 0.5781(4) 0.7087(2) 0.0259(8) Uani 1 1 d . . . . .
H9 H 0.867523 0.570218 0.647682 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9620(2) 0.4969(4) 0.7498(3) 0.0277(8) Uani 1 1 d . . . . .
H10 H 0.987094 0.435235 0.715733 0.033 Uiso 1 1 calc R U . . .
C11 C 0.9967(2) 0.5060(4) 0.8406(3) 0.0309(9) Uani 1 1 d . . . . .
H11 H 1.043799 0.449633 0.867815 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9603(2) 0.6006(4) 0.8906(2) 0.0265(8) Uani 1 1 d . . . . .
H12 H 0.983371 0.607549 0.951640 0.032 Uiso 1 1 calc R U . . .
C13 C 0.8899(2) 0.6850(3) 0.8506(2) 0.0213(7) Uani 1 1 d . . . . .
C14 C 0.8553(2) 0.7931(4) 0.9041(2) 0.0241(8) Uani 1 1 d . . . . .
C15 C 0.6623(3) 0.6931(4) 0.5019(2) 0.0296(8) Uani 1 1 d . . . . .
H15A H 0.642772 0.788156 0.492495 0.036 Uiso 1 1 calc R U . . .
H15B H 0.620444 0.635448 0.461213 0.036 Uiso 1 1 calc R U . . .
C16 C 0.7536(3) 0.6778(4) 0.4835(2) 0.0268(8) Uani 1 1 d . . . . .
C17 C 0.7819(3) 0.5525(4) 0.4560(2) 0.0339(9) Uani 1 1 d . . . . .
H17 H 0.742404 0.478513 0.446271 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8671(3) 0.5356(5) 0.4429(3) 0.0416(10) Uani 1 1 d . . . . .
H18 H 0.885137 0.450778 0.424546 0.050 Uiso 1 1 calc R U . . .
C19 C 0.9260(3) 0.6458(5) 0.4572(3) 0.0416(10) Uani 1 1 d . . . . .
H19 H 0.983292 0.635570 0.447204 0.050 Uiso 1 1 calc R U . . .
C20 C 0.8999(3) 0.7703(5) 0.4861(3) 0.0400(10) Uani 1 1 d . . . . .
H20 H 0.940038 0.843273 0.497347 0.048 Uiso 1 1 calc R U . . .
C21 C 0.8139(3) 0.7869(4) 0.4985(2) 0.0324(9) Uani 1 1 d . . . . .
H21 H 0.796145 0.871673 0.517051 0.039 Uiso 1 1 calc R U . . .
C22 C 0.2551(4) 0.3457(5) 0.8800(3) 0.0554(14) Uani 1 1 d . . . . .
H22A H 0.248338 0.444975 0.882520 0.066 Uiso 1 1 calc R U . . .
H22B H 0.246387 0.306760 0.935669 0.066 Uiso 1 1 calc R U . . .
C23 C 0.1875(3) 0.2877(5) 0.8034(3) 0.0480(12) Uani 1 1 d . . . . .
H23A H 0.158256 0.360542 0.764546 0.058 Uiso 1 1 calc R U . . .
H23B H 0.142751 0.234239 0.824383 0.058 Uiso 1 1 calc R U . . .
C24 C 0.2424(3) 0.1972(5) 0.7559(3) 0.0457(11) Uani 1 1 d . . . . .
H24A H 0.244896 0.103160 0.777791 0.055 Uiso 1 1 calc R U . . .
H24B H 0.218773 0.197221 0.691965 0.055 Uiso 1 1 calc R U . . .
C25 C 0.3326(4) 0.2652(6) 0.7792(4) 0.0571(14) Uani 1 1 d . . . . .
H25A H 0.379447 0.199699 0.775655 0.069 Uiso 1 1 calc R U . . .
H25B H 0.335873 0.341445 0.739117 0.069 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
Bi1 O1 2.301(2) . ?
Bi1 N1 2.488(3) . ?
Bi1 C1 2.244(3) . ?
Bi1 C8 2.249(3) . ?
O1 C14 1.287(4) . ?
O2 C14 1.231(4) . ?
O3 C22 1.404(6) . ?
O3 C25 1.418(6) . ?
N1 H1 0.9800 . ?
N1 C7 1.476(4) . ?
N1 C15 1.478(4) . ?
C1 C2 1.390(5) . ?
C1 C6 1.394(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(5) . ?
C6 C7 1.503(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.393(5) . ?
C8 C13 1.402(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(5) . ?
C13 C14 1.497(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.496(5) . ?
C16 C17 1.385(5) . ?
C16 C21 1.391(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(6) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.500(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.508(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.505(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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
O1 Bi1 N1 152.70(9) . . ?
C1 Bi1 O1 84.35(11) . . ?
C1 Bi1 N1 72.74(11) . . ?
C1 Bi1 C8 94.47(12) . . ?
C8 Bi1 O1 74.62(11) . . ?
C8 Bi1 N1 92.22(11) . . ?
C14 O1 Bi1 116.7(2) . . ?
C22 O3 C25 108.0(4) . . ?
Bi1 N1 H1 108.0 . . ?
C7 N1 Bi1 104.1(2) . . ?
C7 N1 H1 108.0 . . ?
C7 N1 C15 111.8(3) . . ?
C15 N1 Bi1 116.5(2) . . ?
C15 N1 H1 108.0 . . ?
C2 C1 Bi1 124.6(3) . . ?
C2 C1 C6 119.6(3) . . ?
C6 C1 Bi1 115.8(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 119.3(3) . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 121.4(3) . . ?
N1 C7 C6 110.1(3) . . ?
N1 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 Bi1 128.4(3) . . ?
C9 C8 C13 119.6(3) . . ?
C13 C8 Bi1 112.0(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.1(3) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C14 120.1(3) . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 C14 120.3(3) . . ?
O1 C14 C13 115.6(3) . . ?
O2 C14 O1 123.1(3) . . ?
O2 C14 C13 121.2(3) . . ?
N1 C15 H15A 109.7 . . ?
N1 C15 H15B 109.7 . . ?
N1 C15 C16 109.6(3) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 C21 118.5(4) . . ?
C21 C16 C15 120.6(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.3(4) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
O3 C22 H22A 110.0 . . ?
O3 C22 H22B 110.0 . . ?
O3 C22 C23 108.7(4) . . ?
H22A C22 H22B 108.3 . . ?
C23 C22 H22A 110.0 . . ?
C23 C22 H22B 110.0 . . ?
C22 C23 H23A 111.1 . . ?
C22 C23 H23B 111.1 . . ?
C22 C23 C24 103.5(4) . . ?
H23A C23 H23B 109.0 . . ?
C24 C23 H23A 111.1 . . ?
C24 C23 H23B 111.1 . . ?
C23 C24 H24A 111.3 . . ?
C23 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
C25 C24 C23 102.1(4) . . ?
C25 C24 H24A 111.3 . . ?
C25 C24 H24B 111.3 . . ?
O3 C25 C24 105.0(4) . . ?
O3 C25 H25A 110.7 . . ?
O3 C25 H25B 110.7 . . ?
C24 C25 H25A 110.7 . . ?
C24 C25 H25B 110.7 . . ?
H25A C25 H25B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 O1 C14 O2 -171.6(3) . . . . ?
Bi1 O1 C14 C13 9.5(4) . . . . ?
Bi1 N1 C7 C6 -44.3(3) . . . . ?
Bi1 N1 C15 C16 73.1(3) . . . . ?
Bi1 C1 C2 C3 -179.8(3) . . . . ?
Bi1 C1 C6 C5 179.2(3) . . . . ?
Bi1 C1 C6 C7 -3.3(4) . . . . ?
Bi1 C8 C9 C10 -179.4(3) . . . . ?
Bi1 C8 C13 C12 178.0(3) . . . . ?
Bi1 C8 C13 C14 -4.1(4) . . . . ?
O3 C22 C23 C24 10.1(5) . . . . ?
N1 C15 C16 C17 86.2(4) . . . . ?
N1 C15 C16 C21 -90.1(4) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C1 C6 C7 N1 35.6(4) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
C2 C1 C6 C7 176.0(3) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C4 C5 C6 C7 -176.6(4) . . . . ?
C5 C6 C7 N1 -146.9(3) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
C7 N1 C15 C16 -167.3(3) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C8 C13 C14 O1 -3.6(5) . . . . ?
C8 C13 C14 O2 177.5(3) . . . . ?
C9 C8 C13 C12 -3.0(5) . . . . ?
C9 C8 C13 C14 174.9(3) . . . . ?
C9 C10 C11 C12 -1.5(6) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C12 C13 C8 2.1(5) . . . . ?
C11 C12 C13 C14 -175.8(3) . . . . ?
C12 C13 C14 O1 174.3(3) . . . . ?
C12 C13 C14 O2 -4.7(5) . . . . ?
C13 C8 C9 C10 1.7(5) . . . . ?
C15 N1 C7 C6 -171.0(3) . . . . ?
C15 C16 C17 C18 -177.0(3) . . . . ?
C15 C16 C21 C20 176.5(3) . . . . ?
C16 C17 C18 C19 -0.1(6) . . . . ?
C17 C16 C21 C20 0.1(6) . . . . ?
C17 C18 C19 C20 1.4(6) . . . . ?
C18 C19 C20 C21 -1.9(7) . . . . ?
C19 C20 C21 C16 1.1(6) . . . . ?
C21 C16 C17 C18 -0.6(6) . . . . ?
C22 O3 C25 C24 -30.8(5) . . . . ?
C22 C23 C24 C25 -27.3(5) . . . . ?
C23 C24 C25 O3 35.9(5) . . . . ?
C25 O3 C22 C23 12.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.786
####################################################################### 
# 
# 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_bismatrneF2-Compoud-8b
_database_code_depnum_ccdc_archive 'CCDC 2144020'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2022-01-24 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2021-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Bi F2 N'
_chemical_formula_sum            'C21 H18 Bi F2 N'
_chemical_formula_weight         531.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H18Bi1F2N1
_chemical_oxdiff_usercomment     BismatoraneF2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.0487(3)
_cell_length_b                   13.9834(4)
_cell_length_c                   12.3014(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.586(3)
_cell_angle_gamma                90
_cell_volume                     1693.31(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8948
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.6110
_cell_measurement_theta_min      2.0690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.084
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method 'Recrystallized from CH2Cl2/heptane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

 # Type Start End Width tₑₓₚ ω θ κ φ Frames
#--------------------------------------------------------------------------
 1 ω 2.33 183.94 0.30 4.99 -- 28.00 73.57 -25.67 606
 2 ω 2.33 132.69 0.30 4.99 -- 28.00 73.57 64.33 435
 3 ω 2.33 71.26 0.30 4.99 -- 28.00 73.57 154.33 230
 4 ω 2.33 11.32 0.30 4.99 -- 28.00 73.57 -25.67 30
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0142762000
_diffrn_orient_matrix_UB_12      0.0489804000
_diffrn_orient_matrix_UB_13      0.0121253000
_diffrn_orient_matrix_UB_21      0.0691747000
_diffrn_orient_matrix_UB_22      -0.0079324000
_diffrn_orient_matrix_UB_23      -0.0020881000
_diffrn_orient_matrix_UB_31      -0.0142983000
_diffrn_orient_matrix_UB_32      0.0105819000
_diffrn_orient_matrix_UB_33      -0.0575376000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3466
_reflns_number_total             3716
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.144
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0214P)²+3.6859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0469
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Bi1 Bi 0.29539(2) 0.60129(2) 0.70502(2) 0.01934(5) Uani 1 1 d . . . . .
F1 F 0.1907(3) 0.57254(18) 0.8314(2) 0.0412(6) Uani 1 1 d . . . . .
F2 F 0.3353(3) 0.45484(16) 0.74838(19) 0.0435(6) Uani 1 1 d . . . . .
N1 N 0.4000(3) 0.71595(19) 0.5898(2) 0.0192(5) Uani 1 1 d . . . . .
C1 C 0.1653(3) 0.7340(3) 0.6837(3) 0.0234(7) Uani 1 1 d . . . . .
C2 C 0.0688(4) 0.7548(3) 0.7480(3) 0.0307(8) Uani 1 1 d . . . . .
H2 H 0.054096 0.712175 0.802404 0.037 Uiso 1 1 calc R U . . .
C3 C -0.0046(4) 0.8388(3) 0.7304(4) 0.0385(10) Uani 1 1 d . . . . .
H3 H -0.068514 0.852974 0.773250 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0171(4) 0.9020(3) 0.6490(4) 0.0364(10) Uani 1 1 d . . . . .
H4 H -0.033205 0.958232 0.636802 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1121(4) 0.8823(3) 0.5864(3) 0.0306(8) Uani 1 1 d . . . . .
H5 H 0.126001 0.925405 0.532192 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1882(3) 0.7983(3) 0.6029(3) 0.0241(7) Uani 1 1 d . . . . .
C7 C 0.2896(4) 0.7772(2) 0.5310(3) 0.0238(7) Uani 1 1 d . . . . .
H7A H 0.244138 0.745511 0.463610 0.029 Uiso 1 1 calc R U . . .
H7B H 0.327364 0.836767 0.510293 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4540(3) 0.6538(2) 0.5124(3) 0.0223(7) Uani 1 1 d . . . . .
H8A H 0.538122 0.624547 0.550182 0.027 Uiso 1 1 calc R U . . .
H8B H 0.472988 0.691491 0.451077 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3512(4) 0.5771(2) 0.4689(3) 0.0229(7) Uani 1 1 d . . . . .
C10 C 0.3375(4) 0.5411(3) 0.3618(3) 0.0288(8) Uani 1 1 d . . . . .
H10 H 0.391567 0.565194 0.315075 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2440(4) 0.4698(3) 0.3242(3) 0.0340(9) Uani 1 1 d . . . . .
H11 H 0.234966 0.446942 0.252094 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1642(4) 0.4325(3) 0.3930(3) 0.0333(9) Uani 1 1 d . . . . .
H12 H 0.101820 0.384477 0.367197 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1767(4) 0.4662(3) 0.5003(3) 0.0285(8) Uani 1 1 d . . . . .
H13 H 0.123969 0.440801 0.547333 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2687(3) 0.5383(2) 0.5362(3) 0.0221(7) Uani 1 1 d . . . . .
C15 C 0.4965(3) 0.6351(2) 0.8024(3) 0.0198(6) Uani 1 1 d . . . . .
C16 C 0.5512(4) 0.5810(3) 0.8963(3) 0.0237(7) Uani 1 1 d . . . . .
H16 H 0.505483 0.527647 0.915280 0.028 Uiso 1 1 calc R U . . .
C17 C 0.6746(4) 0.6085(3) 0.9606(3) 0.0280(8) Uani 1 1 d . . . . .
H17 H 0.712560 0.573788 1.023758 0.034 Uiso 1 1 calc R U . . .
C18 C 0.7413(4) 0.6877(3) 0.9305(3) 0.0307(8) Uani 1 1 d . . . . .
H18 H 0.823336 0.706704 0.974511 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6870(3) 0.7393(3) 0.8350(3) 0.0251(7) Uani 1 1 d . . . . .
H19 H 0.733882 0.791755 0.815266 0.030 Uiso 1 1 calc R U . . .
C20 C 0.5629(3) 0.7131(2) 0.7687(3) 0.0197(6) Uani 1 1 d . . . . .
C21 C 0.5041(4) 0.7701(2) 0.6661(3) 0.0235(7) Uani 1 1 d . . . . .
H21A H 0.464331 0.828521 0.687628 0.028 Uiso 1 1 calc R U . . .
H21B H 0.576417 0.787577 0.628224 0.028 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
Bi1 F1 2.084(2) . ?
Bi1 F2 2.134(2) . ?
Bi1 N1 2.507(3) . ?
Bi1 C1 2.255(4) . ?
Bi1 C14 2.222(3) . ?
Bi1 C15 2.184(3) . ?
N1 C7 1.471(4) . ?
N1 C8 1.470(4) . ?
N1 C21 1.467(4) . ?
C1 C2 1.400(5) . ?
C1 C6 1.392(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(5) . ?
C6 C7 1.506(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(5) . ?
C9 C10 1.391(5) . ?
C9 C14 1.393(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(5) . ?
C15 C16 1.398(5) . ?
C15 C20 1.384(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.394(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(4) . ?
C20 C21 1.510(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
F1 Bi1 F2 74.11(10) . . ?
F1 Bi1 N1 151.31(9) . . ?
F1 Bi1 C1 82.99(11) . . ?
F1 Bi1 C14 129.53(11) . . ?
F1 Bi1 C15 100.55(11) . . ?
F2 Bi1 N1 132.52(10) . . ?
F2 Bi1 C1 153.46(12) . . ?
F2 Bi1 C14 80.49(11) . . ?
F2 Bi1 C15 87.92(12) . . ?
C1 Bi1 N1 72.95(11) . . ?
C14 Bi1 N1 73.16(11) . . ?
C14 Bi1 C1 105.00(12) . . ?
C15 Bi1 N1 74.02(11) . . ?
C15 Bi1 C1 109.67(12) . . ?
C15 Bi1 C14 121.55(12) . . ?
C7 N1 Bi1 106.8(2) . . ?
C8 N1 Bi1 103.84(19) . . ?
C8 N1 C7 111.4(3) . . ?
C21 N1 Bi1 107.10(18) . . ?
C21 N1 C7 112.6(3) . . ?
C21 N1 C8 114.3(3) . . ?
C2 C1 Bi1 123.8(3) . . ?
C6 C1 Bi1 116.1(2) . . ?
C6 C1 C2 120.1(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C7 121.4(3) . . ?
C5 C6 C7 119.7(3) . . ?
N1 C7 C6 110.9(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
N1 C8 C9 109.5(3) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 C14 117.7(3) . . ?
C14 C9 C8 120.8(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(4) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 Bi1 115.2(2) . . ?
C13 C14 Bi1 122.4(3) . . ?
C13 C14 C9 122.3(3) . . ?
C16 C15 Bi1 120.2(2) . . ?
C20 C15 Bi1 117.0(2) . . ?
C20 C15 C16 122.7(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 117.4(3) . . ?
C15 C20 C21 122.3(3) . . ?
C19 C20 C21 120.3(3) . . ?
N1 C21 C20 111.8(3) . . ?
N1 C21 H21A 109.2 . . ?
N1 C21 H21B 109.2 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C7 C6 36.3(3) . . . . ?
Bi1 N1 C8 C9 43.1(3) . . . . ?
Bi1 N1 C21 C20 28.2(3) . . . . ?
Bi1 C1 C2 C3 178.8(3) . . . . ?
Bi1 C1 C6 C5 -179.3(2) . . . . ?
Bi1 C1 C6 C7 2.7(4) . . . . ?
Bi1 C15 C16 C17 -175.5(3) . . . . ?
Bi1 C15 C20 C19 175.5(2) . . . . ?
Bi1 C15 C20 C21 -3.2(4) . . . . ?
N1 C8 C9 C10 146.9(3) . . . . ?
N1 C8 C9 C14 -34.6(4) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C1 C6 C7 N1 -29.1(4) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
C2 C1 C6 C7 -178.9(3) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C4 C5 C6 C7 178.5(3) . . . . ?
C5 C6 C7 N1 153.0(3) . . . . ?
C6 C1 C2 C3 0.6(5) . . . . ?
C7 N1 C8 C9 -71.6(3) . . . . ?
C7 N1 C21 C20 145.4(3) . . . . ?
C8 N1 C7 C6 149.1(3) . . . . ?
C8 N1 C21 C20 -86.2(3) . . . . ?
C8 C9 C10 C11 179.1(3) . . . . ?
C8 C9 C14 Bi1 2.2(4) . . . . ?
C8 C9 C14 C13 -178.0(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C9 C14 Bi1 -179.2(2) . . . . ?
C10 C9 C14 C13 0.6(5) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C12 C13 C14 Bi1 178.6(3) . . . . ?
C12 C13 C14 C9 -1.2(5) . . . . ?
C14 C9 C10 C11 0.4(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C15 C20 C21 N1 -19.8(4) . . . . ?
C16 C15 C20 C19 -2.4(5) . . . . ?
C16 C15 C20 C21 179.0(3) . . . . ?
C16 C17 C18 C19 -1.2(6) . . . . ?
C17 C18 C19 C20 1.1(6) . . . . ?
C18 C19 C20 C15 0.7(5) . . . . ?
C18 C19 C20 C21 179.4(3) . . . . ?
C19 C20 C21 N1 161.6(3) . . . . ?
C20 C15 C16 C17 2.3(5) . . . . ?
C21 N1 C7 C6 -81.0(3) . . . . ?
C21 N1 C8 C9 159.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.396
_oxdiff_exptl_absorpt_empirical_full_min 0.716
####################################################################### 
# 
# 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_Compound9
_database_code_depnum_ccdc_archive 'CCDC 2144024'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2022-01-24 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2021-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Bi Cl2 N'
_chemical_formula_sum            'C21 H18 Bi Cl2 N'
_chemical_formula_weight         564.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H18Bi1Cl2N1
_chemical_oxdiff_usercomment     Bismatrane_SO2Cl2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3127(2)
_cell_length_b                   9.8342(2)
_cell_length_c                   11.5270(2)
_cell_angle_alpha                81.331(2)
_cell_angle_beta                 87.085(2)
_cell_angle_gamma                86.766(2)
_cell_volume                     929.21(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5558
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.7460
_cell_measurement_theta_min      2.0970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5574
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         1.789
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

 # Type Start End Width tₑₓₚ ω θ κ φ Frames
#--------------------------------------------------------------------------
 1 ω 2.33 183.94 0.30 4.99 -- 28.00 73.57 -25.67 606
 2 ω 2.33 132.69 0.30 4.99 -- 28.00 73.57 64.33 435
 3 ω 2.33 71.26 0.30 4.99 -- 28.00 73.57 154.33 230
 4 ω 2.33 17.31 0.30 4.99 -- 28.00 73.57 -25.67 50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065984000
_diffrn_orient_matrix_UB_12      -0.0130456000
_diffrn_orient_matrix_UB_13      -0.0589625000
_diffrn_orient_matrix_UB_21      -0.0000014000
_diffrn_orient_matrix_UB_22      0.0718271000
_diffrn_orient_matrix_UB_23      -0.0200360000
_diffrn_orient_matrix_UB_31      0.0852868000
_diffrn_orient_matrix_UB_32      -0.0026067000
_diffrn_orient_matrix_UB_33      0.0018803000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3636
_reflns_number_total             3747
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0213
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0291P)²+2.3093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Bi1 Bi 0.44175(2) 0.49307(2) 0.71389(2) 0.01857(6) Uani 1 1 d . . . . .
Cl1 Cl 0.16992(13) 0.37061(11) 0.71482(10) 0.0332(2) Uani 1 1 d . . . . .
Cl2 Cl 0.79209(12) 0.82765(10) 0.97427(8) 0.02444(19) Uani 1 1 d . . . . .
N1 N 0.6155(4) 0.7016(3) 0.6993(3) 0.0167(6) Uani 1 1 d . . . . .
C1 C 0.3757(4) 0.6386(4) 0.5505(3) 0.0196(7) Uani 1 1 d . . . . .
C2 C 0.2390(5) 0.6320(4) 0.4882(4) 0.0230(8) Uani 1 1 d . . . . .
H2 H 0.167077 0.563404 0.513069 0.028 Uiso 1 1 calc R U . . .
C3 C 0.2082(5) 0.7268(4) 0.3888(4) 0.0258(9) Uani 1 1 d . . . . .
H3 H 0.116234 0.721468 0.347419 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3143(5) 0.8290(4) 0.3517(4) 0.0254(8) Uani 1 1 d . . . . .
H4 H 0.291833 0.894075 0.286485 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4545(5) 0.8352(4) 0.4110(4) 0.0239(8) Uani 1 1 d . . . . .
H5 H 0.526814 0.903110 0.384601 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4865(4) 0.7391(4) 0.5105(3) 0.0181(7) Uani 1 1 d . . . . .
C7 C 0.6414(4) 0.7433(4) 0.5718(3) 0.0188(7) Uani 1 1 d . . . . .
H7A H 0.722710 0.681726 0.541357 0.023 Uiso 1 1 calc R U . . .
H7B H 0.679951 0.835827 0.556628 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5134(5) 0.8060(4) 0.7524(3) 0.0190(7) Uani 1 1 d . . . . .
H8A H 0.445230 0.856681 0.693105 0.023 Uiso 1 1 calc R U . . .
H8B H 0.581795 0.870768 0.778918 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4088(4) 0.7422(4) 0.8545(3) 0.0198(7) Uani 1 1 d . . . . .
C10 C 0.3674(5) 0.8141(4) 0.9475(4) 0.0245(8) Uani 1 1 d . . . . .
H10 H 0.414634 0.896809 0.950954 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2565(5) 0.7638(5) 1.0351(4) 0.0297(9) Uani 1 1 d . . . . .
H11 H 0.229751 0.812418 1.097131 0.036 Uiso 1 1 calc R U . . .
C12 C 0.1856(5) 0.6409(5) 1.0299(4) 0.0302(9) Uani 1 1 d . . . . .
H12 H 0.109460 0.607659 1.087578 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2284(5) 0.5674(4) 0.9384(4) 0.0266(9) Uani 1 1 d . . . . .
H13 H 0.182716 0.483712 0.936087 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3392(5) 0.6178(4) 0.8501(3) 0.0207(8) Uani 1 1 d . . . . .
C15 C 0.7692(4) 0.6661(4) 0.7603(3) 0.0192(7) Uani 1 1 d . . . . .
H15A H 0.823621 0.588806 0.728897 0.023 Uiso 1 1 calc R U . . .
H15B H 0.743555 0.636007 0.842932 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8850(4) 0.7810(4) 0.7504(3) 0.0190(7) Uani 1 1 d . . . . .
C17 C 0.9023(5) 0.8612(4) 0.8385(3) 0.0202(7) Uani 1 1 d . . . . .
C18 C 1.0058(5) 0.9673(4) 0.8245(4) 0.0260(9) Uani 1 1 d . . . . .
H18 H 1.013870 1.019676 0.884583 0.031 Uiso 1 1 calc R U . . .
C19 C 1.0981(5) 0.9964(4) 0.7210(4) 0.0289(9) Uani 1 1 d . . . . .
H19 H 1.166858 1.069096 0.710692 0.035 Uiso 1 1 calc R U . . .
C20 C 1.0868(5) 0.9166(5) 0.6337(4) 0.0279(9) Uani 1 1 d . . . . .
H20 H 1.149667 0.934399 0.564485 0.034 Uiso 1 1 calc R U . . .
C21 C 0.9827(4) 0.8104(4) 0.6483(4) 0.0237(8) Uani 1 1 d . . . . .
H21 H 0.977339 0.756861 0.588732 0.028 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
Bi1 Cl1 2.6185(10) . ?
Bi1 N1 2.555(3) . ?
Bi1 C1 2.258(4) . ?
Bi1 C14 2.241(4) . ?
Cl2 C17 1.770(4) . ?
N1 C7 1.474(4) . ?
N1 C8 1.479(5) . ?
N1 C15 1.488(5) . ?
C1 C2 1.384(5) . ?
C1 C6 1.401(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(5) . ?
C6 C7 1.505(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.506(5) . ?
C9 C10 1.389(5) . ?
C9 C14 1.391(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.513(5) . ?
C16 C17 1.394(5) . ?
C16 C21 1.398(5) . ?
C17 C18 1.375(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(6) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Bi1 Cl1 154.57(8) . . ?
C1 Bi1 Cl1 90.84(10) . . ?
C1 Bi1 N1 72.27(12) . . ?
C14 Bi1 Cl1 90.94(10) . . ?
C14 Bi1 N1 73.78(12) . . ?
C14 Bi1 C1 99.23(13) . . ?
C7 N1 Bi1 103.5(2) . . ?
C7 N1 C8 111.2(3) . . ?
C7 N1 C15 112.6(3) . . ?
C8 N1 Bi1 105.0(2) . . ?
C8 N1 C15 112.4(3) . . ?
C15 N1 Bi1 111.6(2) . . ?
C2 C1 Bi1 124.9(3) . . ?
C2 C1 C6 119.5(4) . . ?
C6 C1 Bi1 115.6(3) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 120.8(3) . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 119.5(3) . . ?
N1 C7 C6 110.3(3) . . ?
N1 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 112.2(3) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 C14 119.5(4) . . ?
C14 C9 C8 119.9(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(4) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(4) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 Bi1 116.9(3) . . ?
C13 C14 Bi1 122.8(3) . . ?
C13 C14 C9 119.6(4) . . ?
N1 C15 H15A 108.4 . . ?
N1 C15 H15B 108.4 . . ?
N1 C15 C16 115.5(3) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
C17 C16 C15 123.8(3) . . ?
C17 C16 C21 116.7(4) . . ?
C21 C16 C15 119.5(3) . . ?
C16 C17 Cl2 120.6(3) . . ?
C18 C17 Cl2 117.5(3) . . ?
C18 C17 C16 121.9(4) . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.3(4) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.2 . . ?
C20 C21 C16 121.7(4) . . ?
C20 C21 H21 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C7 C6 43.4(3) . . . . ?
Bi1 N1 C8 C9 35.8(3) . . . . ?
Bi1 N1 C15 C16 176.5(2) . . . . ?
Bi1 C1 C2 C3 179.7(3) . . . . ?
Bi1 C1 C6 C5 -178.9(3) . . . . ?
Bi1 C1 C6 C7 2.3(4) . . . . ?
Cl2 C17 C18 C19 178.5(3) . . . . ?
N1 C8 C9 C10 148.6(3) . . . . ?
N1 C8 C9 C14 -38.4(5) . . . . ?
N1 C15 C16 C17 100.4(4) . . . . ?
N1 C15 C16 C21 -80.1(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C1 C6 C7 N1 -35.1(5) . . . . ?
C2 C1 C6 C5 2.7(5) . . . . ?
C2 C1 C6 C7 -176.1(3) . . . . ?
C2 C3 C4 C5 1.9(6) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 177.8(4) . . . . ?
C5 C6 C7 N1 146.1(3) . . . . ?
C6 C1 C2 C3 -2.2(6) . . . . ?
C7 N1 C8 C9 147.1(3) . . . . ?
C7 N1 C15 C16 60.5(4) . . . . ?
C8 N1 C7 C6 -68.8(4) . . . . ?
C8 N1 C15 C16 -65.9(4) . . . . ?
C8 C9 C10 C11 172.4(4) . . . . ?
C8 C9 C14 Bi1 16.5(5) . . . . ?
C8 C9 C14 C13 -172.7(4) . . . . ?
C9 C10 C11 C12 -0.2(6) . . . . ?
C10 C9 C14 Bi1 -170.4(3) . . . . ?
C10 C9 C14 C13 0.4(6) . . . . ?
C10 C11 C12 C13 1.3(6) . . . . ?
C11 C12 C13 C14 -1.6(6) . . . . ?
C12 C13 C14 Bi1 171.0(3) . . . . ?
C12 C13 C14 C9 0.8(6) . . . . ?
C14 C9 C10 C11 -0.6(6) . . . . ?
C15 N1 C7 C6 164.0(3) . . . . ?
C15 N1 C8 C9 -85.6(4) . . . . ?
C15 C16 C17 Cl2 2.7(5) . . . . ?
C15 C16 C17 C18 -178.1(3) . . . . ?
C15 C16 C21 C20 178.1(4) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
C17 C16 C21 C20 -2.3(6) . . . . ?
C17 C18 C19 C20 -1.1(6) . . . . ?
C18 C19 C20 C21 1.1(6) . . . . ?
C19 C20 C21 C16 0.6(6) . . . . ?
C21 C16 C17 Cl2 -176.9(3) . . . . ?
C21 C16 C17 C18 2.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.788
_oxdiff_exptl_absorpt_empirical_full_min 0.686
####################################################################### 
# 
# 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_AzabismocineCl2-Compound7a
_database_code_depnum_ccdc_archive 'CCDC 2144023'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2022-01-24 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2021-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 Bi Cl2 N'
_chemical_formula_sum            'C24 H26 Bi Cl2 N'
_chemical_formula_weight         608.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H26Bi1Cl2N1
_chemical_oxdiff_usercomment     tBuAzabismocine-Cl2Ph
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.3838(4)
_cell_length_b                   8.4575(2)
_cell_length_c                   17.0618(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.724(2)
_cell_angle_gamma                90
_cell_volume                     2218.88(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11413
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.7680
_cell_measurement_theta_min      1.8100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1176
_exptl_crystal_recrystallization_method 'Recrystallized from ether'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12692
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.728
_diffrn_reflns_theta_min         2.388
_diffrn_ambient_temperature      153(2)
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

 # Type Start End Width tₑₓₚ ω θ κ φ Frames
#--------------------------------------------------------------------------
 1 ω 2.33 183.94 0.30 4.99 -- 28.00 73.57 -25.67 606
 2 ω 2.33 132.69 0.30 4.99 -- 28.00 73.57 64.33 435
 3 ω 2.33 71.26 0.30 4.99 -- 28.00 73.57 154.33 230
 4 ω 2.33 17.31 0.30 4.99 -- 28.00 73.57 -25.67 50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0315635000
_diffrn_orient_matrix_UB_12      -0.0606345000
_diffrn_orient_matrix_UB_13      0.0030945000
_diffrn_orient_matrix_UB_21      -0.0031356000
_diffrn_orient_matrix_UB_22      -0.0055489000
_diffrn_orient_matrix_UB_23      -0.0414821000
_diffrn_orient_matrix_UB_31      0.0334903000
_diffrn_orient_matrix_UB_32      -0.0576382000
_diffrn_orient_matrix_UB_33      0.0007535000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4392
_reflns_number_total             4717
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0154P)²+5.3824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0445
_refine_ls_wR_factor_ref         0.0454
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Bi1 Bi 0.24710(2) 0.41553(2) 0.66803(2) 0.01458(4) Uani 1 1 d . . . . .
Cl1 Cl 0.14714(5) 0.22592(10) 0.58322(5) 0.02154(17) Uani 1 1 d . . . . .
Cl2 Cl 0.34838(6) 0.60101(10) 0.74854(5) 0.02472(18) Uani 1 1 d . . . . .
N1 N 0.26481(17) 0.1544(3) 0.77177(15) 0.0156(6) Uani 1 1 d . . . . .
C1 C 0.1444(2) 0.4257(4) 0.75487(18) 0.0170(7) Uani 1 1 d . . . . .
C2 C 0.1008(2) 0.5683(4) 0.7612(2) 0.0212(7) Uani 1 1 d . . . . .
H2 H 0.116022 0.655526 0.731422 0.025 Uiso 1 1 calc R U . . .
C3 C 0.0335(2) 0.5764(5) 0.8137(2) 0.0248(8) Uani 1 1 d . . . . .
H3 H 0.003102 0.670438 0.819691 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0120(2) 0.4455(5) 0.8569(2) 0.0272(8) Uani 1 1 d . . . . .
H4 H -0.033520 0.451452 0.891462 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0572(2) 0.3051(4) 0.8495(2) 0.0229(8) Uani 1 1 d . . . . .
H5 H 0.042027 0.218121 0.879465 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1255(2) 0.2923(4) 0.79725(19) 0.0177(7) Uani 1 1 d . . . . .
C7 C 0.1711(2) 0.1359(4) 0.7859(2) 0.0193(7) Uani 1 1 d . . . . .
H7A H 0.164094 0.071161 0.832208 0.023 Uiso 1 1 calc R U . . .
H7B H 0.143799 0.081020 0.741755 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2960(2) 0.0433(4) 0.71202(19) 0.0173(7) Uani 1 1 d . . . . .
H8A H 0.247090 0.009018 0.679049 0.021 Uiso 1 1 calc R U . . .
H8B H 0.320471 -0.049273 0.737961 0.021 Uiso 1 1 calc R U . . .
C9 C 0.3639(2) 0.1169(4) 0.66123(18) 0.0164(7) Uani 1 1 d . . . . .
C10 C 0.4358(2) 0.0285(4) 0.6380(2) 0.0228(7) Uani 1 1 d . . . . .
H10 H 0.441724 -0.075814 0.654441 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4979(2) 0.0940(5) 0.5908(2) 0.0242(8) Uani 1 1 d . . . . .
H11 H 0.544975 0.033159 0.575876 0.029 Uiso 1 1 calc R U . . .
C12 C 0.4909(2) 0.2483(5) 0.5659(2) 0.0249(8) Uani 1 1 d . . . . .
H12 H 0.532881 0.291251 0.534143 0.030 Uiso 1 1 calc R U . . .
C13 C 0.4211(2) 0.3398(4) 0.58822(19) 0.0215(7) Uani 1 1 d . . . . .
H13 H 0.416003 0.444725 0.572496 0.026 Uiso 1 1 calc R U . . .
C14 C 0.35901(19) 0.2710(4) 0.63449(18) 0.0168(7) Uani 1 1 d . . . . .
C15 C 0.3200(2) 0.1527(4) 0.84708(19) 0.0185(7) Uani 1 1 d . . . . .
C16 C 0.2894(2) 0.2837(4) 0.90110(19) 0.0228(8) Uani 1 1 d . . . . .
H16A H 0.289625 0.382743 0.873612 0.034 Uiso 1 1 calc R U . . .
H16B H 0.327877 0.290065 0.946366 0.034 Uiso 1 1 calc R U . . .
H16C H 0.231562 0.260838 0.917341 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3145(2) -0.0062(4) 0.8894(2) 0.0266(8) Uani 1 1 d . . . . .
H17A H 0.256085 -0.023176 0.905691 0.040 Uiso 1 1 calc R U . . .
H17B H 0.353342 -0.005756 0.934498 0.040 Uiso 1 1 calc R U . . .
H17C H 0.330747 -0.089511 0.854487 0.040 Uiso 1 1 calc R U . . .
C18 C 0.4150(2) 0.1854(5) 0.8283(2) 0.0232(8) Uani 1 1 d . . . . .
H18A H 0.437526 0.098710 0.798782 0.035 Uiso 1 1 calc R U . . .
H18B H 0.448614 0.197212 0.876274 0.035 Uiso 1 1 calc R U . . .
H18C H 0.418490 0.280809 0.798074 0.035 Uiso 1 1 calc R U . . .
C19 C 0.2183(2) 0.6095(4) 0.58228(19) 0.0181(7) Uani 1 1 d . . . . .
C20 C 0.2787(2) 0.7269(4) 0.57078(19) 0.0226(7) Uani 1 1 d . . . . .
H20 H 0.331619 0.726258 0.598582 0.027 Uiso 1 1 calc R U . . .
C21 C 0.2594(3) 0.8463(4) 0.5172(2) 0.0261(8) Uani 1 1 d . . . . .
H21 H 0.300242 0.924675 0.507851 0.031 Uiso 1 1 calc R U . . .
C22 C 0.1796(3) 0.8487(5) 0.4775(2) 0.0288(8) Uani 1 1 d . . . . .
H22 H 0.166803 0.929343 0.441896 0.035 Uiso 1 1 calc R U . . .
C23 C 0.1190(2) 0.7326(5) 0.4904(2) 0.0308(9) Uani 1 1 d . . . . .
H23 H 0.065181 0.735798 0.464143 0.037 Uiso 1 1 calc R U . . .
C24 C 0.1382(2) 0.6098(4) 0.5430(2) 0.0251(8) Uani 1 1 d . . . . .
H24 H 0.098014 0.529944 0.551382 0.030 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
Bi1 Cl1 2.6261(8) . ?
Bi1 Cl2 2.5781(8) . ?
Bi1 N1 2.838(3) . ?
Bi1 C1 2.199(3) . ?
Bi1 C14 2.201(3) . ?
Bi1 C19 2.234(3) . ?
N1 C7 1.477(4) . ?
N1 C8 1.477(4) . ?
N1 C15 1.519(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.376(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(4) . ?
C6 C7 1.512(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.512(4) . ?
C9 C10 1.401(5) . ?
C9 C14 1.382(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(5) . ?
C15 C16 1.525(5) . ?
C15 C17 1.529(5) . ?
C15 C18 1.531(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.378(5) . ?
C19 C24 1.385(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.398(5) . ?
C24 H24 0.9300 . ?

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
Cl1 Bi1 N1 84.96(6) . . ?
Cl2 Bi1 Cl1 178.48(3) . . ?
Cl2 Bi1 N1 95.51(6) . . ?
C1 Bi1 Cl1 88.54(9) . . ?
C1 Bi1 Cl2 92.98(9) . . ?
C1 Bi1 N1 70.59(10) . . ?
C1 Bi1 C14 141.25(12) . . ?
C1 Bi1 C19 106.28(12) . . ?
C14 Bi1 Cl1 88.12(8) . . ?
C14 Bi1 Cl2 90.67(9) . . ?
C14 Bi1 N1 70.66(10) . . ?
C14 Bi1 C19 112.26(12) . . ?
C19 Bi1 Cl1 89.21(9) . . ?
C19 Bi1 Cl2 90.39(9) . . ?
C19 Bi1 N1 173.42(10) . . ?
C7 N1 Bi1 96.22(18) . . ?
C7 N1 C8 112.6(3) . . ?
C7 N1 C15 112.6(2) . . ?
C8 N1 Bi1 95.25(17) . . ?
C8 N1 C15 113.1(2) . . ?
C15 N1 Bi1 125.17(19) . . ?
C2 C1 Bi1 116.5(2) . . ?
C6 C1 Bi1 119.3(2) . . ?
C6 C1 C2 124.2(3) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.7(3) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 116.4(3) . . ?
C1 C6 C7 122.9(3) . . ?
C5 C6 C7 120.6(3) . . ?
N1 C7 C6 112.8(3) . . ?
N1 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 112.2(3) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C10 C9 C8 120.5(3) . . ?
C14 C9 C8 123.1(3) . . ?
C14 C9 C10 116.4(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.4(3) . . ?
C14 C13 H13 120.8 . . ?
C9 C14 Bi1 118.3(2) . . ?
C9 C14 C13 123.5(3) . . ?
C13 C14 Bi1 118.2(3) . . ?
N1 C15 C16 109.3(3) . . ?
N1 C15 C17 111.8(3) . . ?
N1 C15 C18 109.5(3) . . ?
C16 C15 C17 109.4(3) . . ?
C16 C15 C18 108.0(3) . . ?
C17 C15 C18 108.9(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 Bi1 120.1(2) . . ?
C20 C19 C24 121.6(3) . . ?
C24 C19 Bi1 118.3(2) . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.1(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 118.7(3) . . ?
C19 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C1 C2 C3 177.8(2) . . . . ?
Bi1 C1 C6 C5 -177.6(2) . . . . ?
Bi1 C1 C6 C7 -1.2(4) . . . . ?
Bi1 C19 C20 C21 180.0(3) . . . . ?
Bi1 C19 C24 C23 178.7(3) . . . . ?
N1 C8 C9 C10 140.8(3) . . . . ?
N1 C8 C9 C14 -40.0(4) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C6 C7 N1 38.4(4) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C2 C1 C6 C7 176.7(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C4 C5 C6 C7 -176.4(3) . . . . ?
C5 C6 C7 N1 -145.3(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C7 N1 C8 C9 143.5(3) . . . . ?
C7 N1 C15 C16 -57.5(4) . . . . ?
C7 N1 C15 C17 63.7(3) . . . . ?
C7 N1 C15 C18 -175.6(3) . . . . ?
C8 N1 C7 C6 -140.6(3) . . . . ?
C8 N1 C15 C16 173.4(3) . . . . ?
C8 N1 C15 C17 -65.4(3) . . . . ?
C8 N1 C15 C18 55.4(4) . . . . ?
C8 C9 C10 C11 179.4(3) . . . . ?
C8 C9 C14 Bi1 0.2(4) . . . . ?
C8 C9 C14 C13 179.7(3) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C9 C14 Bi1 179.4(2) . . . . ?
C10 C9 C14 C13 -1.1(5) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C12 C13 C14 Bi1 -179.0(2) . . . . ?
C12 C13 C14 C9 1.6(5) . . . . ?
C14 C9 C10 C11 0.1(5) . . . . ?
C15 N1 C7 C6 90.1(3) . . . . ?
C15 N1 C8 C9 -87.4(3) . . . . ?
C19 C20 C21 C22 1.7(5) . . . . ?
C20 C19 C24 C23 0.2(5) . . . . ?
C20 C21 C22 C23 -0.5(6) . . . . ?
C21 C22 C23 C24 -0.9(6) . . . . ?
C22 C23 C24 C19 1.1(6) . . . . ?
C24 C19 C20 C21 -1.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.844
