# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

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

data_FA25_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1974621'
loop_
_audit_author_name
_audit_author_address
'Damir Safin'
;University of Tyumen
Russia
;
_audit_update_record             
;
2020-04-05 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            22-FG
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H28 Bi Cl3 N6'
_chemical_formula_sum            'C38 H28 Bi Cl3 N6'
_chemical_formula_weight         883.99

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.9808(14)
_cell_length_b                   19.684(3)
_cell_length_c                   21.185(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.110(2)
_cell_angle_gamma                90
_cell_volume                     3697.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.2896
_cell_measurement_theta_max      24.2182

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.020
_shelx_estimated_absorpt_T_min   0.540
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            137542
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.947
_diffrn_reflns_theta_max         29.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10106
_reflns_number_gt                7829
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 V2013.10.0 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 V2013.10.0 (Bruker, 2013)'
_computing_data_reduction        'APEX2 V2013.10.0 (Bruker, 2013)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0192P)²+3.0592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10106
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0576
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.37356(2) 0.79729(2) 0.38393(2) 0.02712(4) Uani 1 1 d . . . . .
Cl1 Cl 0.54198(9) 0.73363(4) 0.48065(4) 0.04126(18) Uani 1 1 d . . . . .
Cl2 Cl 0.30922(9) 0.88898(4) 0.46364(4) 0.04052(18) Uani 1 1 d . . . . .
Cl3 Cl 0.19173(10) 0.85840(5) 0.28900(4) 0.0512(2) Uani 1 1 d . . . . .
N1 N 0.1433(3) 0.73513(12) 0.40843(13) 0.0359(6) Uani 1 1 d . . . . .
N2 N 0.3490(3) 0.66046(11) 0.35596(12) 0.0293(5) Uani 1 1 d . . . . .
N3 N 0.4804(3) 0.62487(12) 0.34715(12) 0.0323(6) Uani 1 1 d . . . . .
N4 N 0.4379(3) 0.73884(12) 0.23438(12) 0.0320(6) Uani 1 1 d . . . . .
N5 N 0.5184(3) 0.77470(12) 0.28497(12) 0.0315(6) Uani 1 1 d . . . . .
N6 N 0.6108(3) 0.86960(12) 0.37376(12) 0.0324(6) Uani 1 1 d . . . . .
C1 C 0.0289(4) 0.77164(17) 0.42350(19) 0.0475(9) Uani 1 1 d . . . . .
H1 H 0.041066 0.818886 0.428296 0.057 Uiso 1 1 calc R U . . .
C2 C -0.1063(4) 0.74315(17) 0.43233(18) 0.0466(9) Uani 1 1 d . . . . .
H2 H -0.184518 0.770432 0.443061 0.056 Uiso 1 1 calc R U . . .
C3 C -0.1250(4) 0.67411(18) 0.42518(17) 0.0424(8) Uani 1 1 d . . . . .
H3 H -0.217069 0.653510 0.429813 0.051 Uiso 1 1 calc R U . . .
C4 C -0.0056(4) 0.63539(17) 0.41103(15) 0.0384(7) Uani 1 1 d . . . . .
H4 H -0.014930 0.587942 0.407219 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1276(3) 0.66712(15) 0.40252(14) 0.0298(6) Uani 1 1 d . . . . .
C6 C 0.2578(3) 0.62772(14) 0.38541(14) 0.0288(6) Uani 1 1 d . . . . .
C7 C 0.2733(3) 0.55482(15) 0.40328(15) 0.0333(7) Uani 1 1 d . . . . .
C8 C 0.2809(5) 0.53588(18) 0.46631(17) 0.0567(10) Uani 1 1 d . . . . .
H8 H 0.269949 0.568569 0.497595 0.068 Uiso 1 1 calc R U . . .
C9 C 0.3047(6) 0.4682(2) 0.4833(2) 0.0782(15) Uani 1 1 d . . . . .
H9 H 0.313541 0.455582 0.526490 0.094 Uiso 1 1 calc R U . . .
C10 C 0.3155(5) 0.4202(2) 0.4385(2) 0.0690(13) Uani 1 1 d . . . . .
H10 H 0.331038 0.374480 0.450681 0.083 Uiso 1 1 calc R U . . .
C11 C 0.3038(5) 0.43807(18) 0.3753(2) 0.0548(10) Uani 1 1 d . . . . .
H11 H 0.308251 0.404604 0.343977 0.066 Uiso 1 1 calc R U . . .
C12 C 0.2854(4) 0.50552(16) 0.35795(17) 0.0400(8) Uani 1 1 d . . . . .
H12 H 0.281010 0.518031 0.314879 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5211(3) 0.63322(14) 0.29240(14) 0.0296(6) Uani 1 1 d . . . . .
C14 C 0.6583(3) 0.59827(15) 0.27949(16) 0.0363(7) Uani 1 1 d . . . . .
C15 C 0.7121(4) 0.54103(17) 0.31497(18) 0.0457(8) Uani 1 1 d . . . . .
H15 H 0.661154 0.524713 0.347384 0.055 Uiso 1 1 calc R U . . .
C16 C 0.8409(4) 0.5084(2) 0.3022(2) 0.0604(11) Uani 1 1 d . . . . .
H16 H 0.877362 0.469975 0.326215 0.073 Uiso 1 1 calc R U . . .
C17 C 0.9159(4) 0.5319(2) 0.2546(3) 0.0713(14) Uani 1 1 d . . . . .
H17 H 1.002931 0.509431 0.246079 0.086 Uiso 1 1 calc R U . . .
C18 C 0.8639(5) 0.5872(2) 0.2201(3) 0.0746(14) Uani 1 1 d . . . . .
H18 H 0.916365 0.603422 0.188067 0.090 Uiso 1 1 calc R U . . .
C19 C 0.7339(4) 0.62057(19) 0.2313(2) 0.0566(10) Uani 1 1 d . . . . .
H19 H 0.697579 0.658213 0.206235 0.068 Uiso 1 1 calc R U . . .
C20 C 0.4312(3) 0.67360(15) 0.23930(14) 0.0291(6) Uani 1 1 d . . . . .
C21 C 0.3288(3) 0.63604(14) 0.18988(14) 0.0308(6) Uani 1 1 d . . . . .
C22 C 0.3248(4) 0.56551(15) 0.19010(15) 0.0354(7) Uani 1 1 d . . . . .
H22 H 0.390114 0.541232 0.221184 0.043 Uiso 1 1 calc R U . . .
C23 C 0.2249(4) 0.53064(17) 0.14464(16) 0.0435(8) Uani 1 1 d . . . . .
H23 H 0.222332 0.482905 0.145124 0.052 Uiso 1 1 calc R U . . .
C24 C 0.1298(4) 0.56592(18) 0.09902(17) 0.0484(9) Uani 1 1 d . . . . .
H24 H 0.062479 0.542186 0.068264 0.058 Uiso 1 1 calc R U . . .
C25 C 0.1324(4) 0.63592(19) 0.09800(18) 0.0520(10) Uani 1 1 d . . . . .
H25 H 0.066462 0.659801 0.066854 0.062 Uiso 1 1 calc R U . . .
C26 C 0.2323(4) 0.67103(17) 0.14287(17) 0.0458(8) Uani 1 1 d . . . . .
H26 H 0.235016 0.718745 0.141651 0.055 Uiso 1 1 calc R U . . .
C27 C 0.6252(3) 0.81406(14) 0.27288(14) 0.0291(6) Uani 1 1 d . . . . .
C28 C 0.6799(4) 0.81410(15) 0.21012(16) 0.0360(7) Uani 1 1 d . . . . .
C29 C 0.5807(4) 0.83122(19) 0.15504(17) 0.0492(9) Uani 1 1 d . . . . .
H29 H 0.481317 0.844276 0.157989 0.059 Uiso 1 1 calc R U . . .
C30 C 0.6279(6) 0.8291(3) 0.0959(2) 0.0762(14) Uani 1 1 d . . . . .
H30 H 0.561147 0.841369 0.058888 0.091 Uiso 1 1 calc R U . . .
C31 C 0.7709(7) 0.8091(3) 0.0913(3) 0.0872(17) Uani 1 1 d . . . . .
H31 H 0.801827 0.807400 0.050957 0.105 Uiso 1 1 calc R U . . .
C32 C 0.8698(6) 0.7916(2) 0.1443(3) 0.0728(14) Uani 1 1 d . . . . .
H32 H 0.967911 0.777662 0.140197 0.087 Uiso 1 1 calc R U . . .
C33 C 0.8263(4) 0.79435(18) 0.2050(2) 0.0510(9) Uani 1 1 d . . . . .
H33 H 0.895125 0.782995 0.241667 0.061 Uiso 1 1 calc R U . . .
C34 C 0.6876(3) 0.86277(14) 0.32429(14) 0.0298(6) Uani 1 1 d . . . . .
C35 C 0.8177(3) 0.90007(16) 0.32156(16) 0.0385(7) Uani 1 1 d . . . . .
H35 H 0.869496 0.895270 0.286582 0.046 Uiso 1 1 calc R U . . .
C36 C 0.8702(4) 0.94426(18) 0.37067(17) 0.0477(9) Uani 1 1 d . . . . .
H36 H 0.959610 0.968942 0.370046 0.057 Uiso 1 1 calc R U . . .
C37 C 0.7906(4) 0.95175(19) 0.42041(18) 0.0514(9) Uani 1 1 d . . . . .
H37 H 0.822715 0.982405 0.453808 0.062 Uiso 1 1 calc R U . . .
C38 C 0.6619(4) 0.91315(17) 0.42026(16) 0.0428(8) Uani 1 1 d . . . . .
H38 H 0.607990 0.917879 0.454581 0.051 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 N1 2.527(2) . ?
Bi1 Cl2 2.5985(8) . ?
Bi1 N6 2.600(2) . ?
Bi1 Cl1 2.6600(8) . ?
Bi1 Cl3 2.6679(9) . ?
Bi1 N5 2.674(2) . ?
Bi1 N2 2.759(2) . ?
N1 C1 1.333(4) . ?
N1 C5 1.350(4) . ?
N2 C6 1.280(3) . ?
N2 N3 1.410(3) . ?
N3 C13 1.281(4) . ?
N4 C20 1.291(4) . ?
N4 N5 1.387(3) . ?
N5 C27 1.290(4) . ?
N6 C38 1.331(4) . ?
N6 C34 1.349(4) . ?
C1 C2 1.377(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.375(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.495(4) . ?
C6 C7 1.485(4) . ?
C7 C8 1.378(4) . ?
C7 C12 1.382(4) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.355(6) . ?
C9 H9 0.9400 . ?
C10 C11 1.372(6) . ?
C10 H10 0.9400 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.474(4) . ?
C13 C20 1.504(4) . ?
C14 C19 1.384(5) . ?
C14 C15 1.398(5) . ?
C15 C16 1.387(5) . ?
C15 H15 0.9400 . ?
C16 C17 1.378(6) . ?
C16 H16 0.9400 . ?
C17 C18 1.354(6) . ?
C17 H17 0.9400 . ?
C18 C19 1.392(5) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C20 C21 1.478(4) . ?
C21 C22 1.389(4) . ?
C21 C26 1.394(4) . ?
C22 C23 1.390(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.372(5) . ?
C23 H23 0.9400 . ?
C24 C25 1.378(5) . ?
C24 H24 0.9400 . ?
C25 C26 1.384(5) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 C28 1.488(4) . ?
C27 C34 1.492(4) . ?
C28 C33 1.392(5) . ?
C28 C29 1.393(5) . ?
C29 C30 1.386(6) . ?
C29 H29 0.9400 . ?
C30 C31 1.361(7) . ?
C30 H30 0.9400 . ?
C31 C32 1.361(7) . ?
C31 H31 0.9400 . ?
C32 C33 1.403(6) . ?
C32 H32 0.9400 . ?
C33 H33 0.9400 . ?
C34 C35 1.389(4) . ?
C35 C36 1.381(5) . ?
C35 H35 0.9400 . ?
C36 C37 1.372(5) . ?
C36 H36 0.9400 . ?
C37 C38 1.382(5) . ?
C37 H37 0.9400 . ?
C38 H38 0.9400 . ?

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 Cl2 85.95(6) . . ?
N1 Bi1 N6 172.10(8) . . ?
Cl2 Bi1 N6 86.74(6) . . ?
N1 Bi1 Cl1 89.87(6) . . ?
Cl2 Bi1 Cl1 89.11(3) . . ?
N6 Bi1 Cl1 87.03(6) . . ?
N1 Bi1 Cl3 87.13(6) . . ?
Cl2 Bi1 Cl3 90.24(3) . . ?
N6 Bi1 Cl3 95.89(6) . . ?
Cl1 Bi1 Cl3 176.97(3) . . ?
N1 Bi1 N5 126.61(8) . . ?
Cl2 Bi1 N5 144.19(5) . . ?
N6 Bi1 N5 61.25(8) . . ?
Cl1 Bi1 N5 103.75(6) . . ?
Cl3 Bi1 N5 78.45(6) . . ?
N1 Bi1 N2 62.04(8) . . ?
Cl2 Bi1 N2 143.04(5) . . ?
N6 Bi1 N2 123.74(7) . . ?
Cl1 Bi1 N2 73.86(6) . . ?
Cl3 Bi1 N2 105.05(6) . . ?
N5 Bi1 N2 72.64(7) . . ?
C1 N1 C5 118.9(3) . . ?
C1 N1 Bi1 118.4(2) . . ?
C5 N1 Bi1 122.54(19) . . ?
C6 N2 N3 115.3(2) . . ?
C6 N2 Bi1 115.00(19) . . ?
N3 N2 Bi1 118.25(16) . . ?
C13 N3 N2 114.9(2) . . ?
C20 N4 N5 118.0(3) . . ?
C27 N5 N4 117.7(2) . . ?
C27 N5 Bi1 121.68(19) . . ?
N4 N5 Bi1 115.57(17) . . ?
C38 N6 C34 118.7(3) . . ?
C38 N6 Bi1 118.8(2) . . ?
C34 N6 Bi1 122.42(19) . . ?
N1 C1 C2 122.9(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 120.9(3) . . ?
N1 C5 C6 117.6(2) . . ?
C4 C5 C6 121.5(3) . . ?
N2 C6 C7 124.7(3) . . ?
N2 C6 C5 116.3(2) . . ?
C7 C6 C5 119.0(2) . . ?
C8 C7 C12 119.1(3) . . ?
C8 C7 C6 119.8(3) . . ?
C12 C7 C6 121.1(3) . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N3 C13 C14 118.4(3) . . ?
N3 C13 C20 123.3(3) . . ?
C14 C13 C20 118.3(3) . . ?
C19 C14 C15 118.9(3) . . ?
C19 C14 C13 120.7(3) . . ?
C15 C14 C13 120.3(3) . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 120.0(4) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N4 C20 C21 118.2(3) . . ?
N4 C20 C13 124.0(3) . . ?
C21 C20 C13 117.8(2) . . ?
C22 C21 C26 118.9(3) . . ?
C22 C21 C20 120.7(3) . . ?
C26 C21 C20 120.4(3) . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
N5 C27 C28 122.6(3) . . ?
N5 C27 C34 116.5(3) . . ?
C28 C27 C34 120.9(2) . . ?
C33 C28 C29 119.3(3) . . ?
C33 C28 C27 121.3(3) . . ?
C29 C28 C27 119.4(3) . . ?
C30 C29 C28 120.2(4) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 120.1(5) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C32 C31 C30 120.9(4) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 120.4(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C28 C33 C32 119.1(4) . . ?
C28 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
N6 C34 C35 121.1(3) . . ?
N6 C34 C27 116.9(2) . . ?
C35 C34 C27 122.0(3) . . ?
C36 C35 C34 119.4(3) . . ?
C36 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
C37 C36 C35 119.3(3) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C36 C37 C38 118.5(3) . . ?
C36 C37 H37 120.8 . . ?
C38 C37 H37 120.8 . . ?
N6 C38 C37 123.1(3) . . ?
N6 C38 H38 118.5 . . ?
C37 C38 H38 118.5 . . ?

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
C6 N2 N3 C13 139.4(3) . . . . ?
Bi1 N2 N3 C13 -78.8(3) . . . . ?
C20 N4 N5 C27 124.4(3) . . . . ?
C20 N4 N5 Bi1 -80.2(3) . . . . ?
C5 N1 C1 C2 -1.1(5) . . . . ?
Bi1 N1 C1 C2 174.3(3) . . . . ?
N1 C1 C2 C3 -0.2(6) . . . . ?
C1 C2 C3 C4 1.7(5) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C1 N1 C5 C4 0.9(5) . . . . ?
Bi1 N1 C5 C4 -174.4(2) . . . . ?
C1 N1 C5 C6 179.8(3) . . . . ?
Bi1 N1 C5 C6 4.6(4) . . . . ?
C3 C4 C5 N1 0.6(5) . . . . ?
C3 C4 C5 C6 -178.3(3) . . . . ?
N3 N2 C6 C7 -7.2(4) . . . . ?
Bi1 N2 C6 C7 -150.2(2) . . . . ?
N3 N2 C6 C5 172.6(2) . . . . ?
Bi1 N2 C6 C5 29.6(3) . . . . ?
N1 C5 C6 N2 -24.3(4) . . . . ?
C4 C5 C6 N2 154.7(3) . . . . ?
N1 C5 C6 C7 155.6(3) . . . . ?
C4 C5 C6 C7 -25.5(4) . . . . ?
N2 C6 C7 C8 123.0(4) . . . . ?
C5 C6 C7 C8 -56.8(4) . . . . ?
N2 C6 C7 C12 -54.8(4) . . . . ?
C5 C6 C7 C12 125.3(3) . . . . ?
C12 C7 C8 C9 1.8(6) . . . . ?
C6 C7 C8 C9 -176.0(4) . . . . ?
C7 C8 C9 C10 -2.3(8) . . . . ?
C8 C9 C10 C11 0.4(8) . . . . ?
C9 C10 C11 C12 1.9(7) . . . . ?
C10 C11 C12 C7 -2.3(6) . . . . ?
C8 C7 C12 C11 0.4(5) . . . . ?
C6 C7 C12 C11 178.3(3) . . . . ?
N2 N3 C13 C14 179.4(2) . . . . ?
N2 N3 C13 C20 -4.2(4) . . . . ?
N3 C13 C14 C19 -159.7(3) . . . . ?
C20 C13 C14 C19 23.7(4) . . . . ?
N3 C13 C14 C15 21.6(4) . . . . ?
C20 C13 C14 C15 -154.9(3) . . . . ?
C19 C14 C15 C16 1.1(5) . . . . ?
C13 C14 C15 C16 179.7(3) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C15 C16 C17 C18 0.2(6) . . . . ?
C16 C17 C18 C19 -0.9(7) . . . . ?
C15 C14 C19 C18 -1.8(6) . . . . ?
C13 C14 C19 C18 179.6(3) . . . . ?
C17 C18 C19 C14 1.8(7) . . . . ?
N5 N4 C20 C21 171.7(2) . . . . ?
N5 N4 C20 C13 -8.2(4) . . . . ?
N3 C13 C20 N4 83.2(4) . . . . ?
C14 C13 C20 N4 -100.5(3) . . . . ?
N3 C13 C20 C21 -96.7(3) . . . . ?
C14 C13 C20 C21 79.6(3) . . . . ?
N4 C20 C21 C22 175.3(3) . . . . ?
C13 C20 C21 C22 -4.8(4) . . . . ?
N4 C20 C21 C26 -5.9(4) . . . . ?
C13 C20 C21 C26 174.0(3) . . . . ?
C26 C21 C22 C23 -0.8(5) . . . . ?
C20 C21 C22 C23 178.0(3) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C23 C24 C25 -0.1(6) . . . . ?
C23 C24 C25 C26 0.5(6) . . . . ?
C24 C25 C26 C21 -1.1(6) . . . . ?
C22 C21 C26 C25 1.2(5) . . . . ?
C20 C21 C26 C25 -177.6(3) . . . . ?
N4 N5 C27 C28 -9.7(4) . . . . ?
Bi1 N5 C27 C28 -163.5(2) . . . . ?
N4 N5 C27 C34 167.3(2) . . . . ?
Bi1 N5 C27 C34 13.5(3) . . . . ?
N5 C27 C28 C33 -115.5(4) . . . . ?
C34 C27 C28 C33 67.6(4) . . . . ?
N5 C27 C28 C29 61.5(4) . . . . ?
C34 C27 C28 C29 -115.4(3) . . . . ?
C33 C28 C29 C30 -0.5(5) . . . . ?
C27 C28 C29 C30 -177.6(3) . . . . ?
C28 C29 C30 C31 1.1(7) . . . . ?
C29 C30 C31 C32 -0.6(8) . . . . ?
C30 C31 C32 C33 -0.5(8) . . . . ?
C29 C28 C33 C32 -0.5(5) . . . . ?
C27 C28 C33 C32 176.5(3) . . . . ?
C31 C32 C33 C28 1.0(6) . . . . ?
C38 N6 C34 C35 0.2(4) . . . . ?
Bi1 N6 C34 C35 -177.2(2) . . . . ?
C38 N6 C34 C27 -179.3(3) . . . . ?
Bi1 N6 C34 C27 3.3(3) . . . . ?
N5 C27 C34 N6 -11.0(4) . . . . ?
C28 C27 C34 N6 166.1(3) . . . . ?
N5 C27 C34 C35 169.6(3) . . . . ?
C28 C27 C34 C35 -13.4(4) . . . . ?
N6 C34 C35 C36 0.8(5) . . . . ?
C27 C34 C35 C36 -179.8(3) . . . . ?
C34 C35 C36 C37 -1.7(5) . . . . ?
C35 C36 C37 C38 1.7(6) . . . . ?
C34 N6 C38 C37 -0.2(5) . . . . ?
Bi1 N6 C38 C37 177.3(3) . . . . ?
C36 C37 C38 N6 -0.7(6) . . . . ?

_refine_diff_density_max         0.731
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1974622'
loop_
_audit_author_name
_audit_author_address
'Damir Safin'
;University of Tyumen
Russia
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C13 H12 N3 O2), Bi Cl5, 0.5(C2 H6 O), 0.5(C2 H6 O)'
_chemical_formula_sum            'C28 H30 Bi Cl5 N6 O5'
_chemical_formula_weight         916.81

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.5632(4)
_cell_length_b                   11.7963(5)
_cell_length_c                   19.9471(9)
_cell_angle_alpha                74.681(2)
_cell_angle_beta                 79.486(3)
_cell_angle_gamma                86.386(3)
_cell_volume                     1687.38(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      24.85

_exptl_crystal_description       dentrite
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    5.667
_shelx_estimated_absorpt_T_min   0.630
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6892
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.790
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6892
_reflns_number_gt                6033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 V2013.10.0 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 V2013.10.0 (Bruker, 2013)'
_computing_data_reduction        'APEX2 V2013.10.0 (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+2.1710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6892
_refine_ls_number_parameters     441
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 1.30221(3) 0.38686(2) 0.43337(2) 0.02038(6) Uani 1 1 d . . . . .
Cl1 Cl 1.000000 0.500000 0.500000 0.0573(9) Uani 1 2 d S . P . .
Cl2 Cl 1.500000 0.500000 0.500000 0.0536(7) Uani 1 2 d S . P . .
Cl3 Cl 1.5905(2) 0.28999(13) 0.37845(8) 0.0305(3) Uani 1 1 d . . . . .
Cl4 Cl 1.10524(19) 0.27569(12) 0.37296(8) 0.0272(3) Uani 1 1 d . . . . .
Cl5 Cl 1.2540(2) 0.19745(11) 0.54718(7) 0.0350(3) Uani 1 1 d . . . . .
Cl6 Cl 1.3268(3) 0.56626(11) 0.31995(8) 0.0445(4) Uani 1 1 d . . . . .
O1 O 0.2268(7) -0.6396(4) 1.0442(2) 0.0546(13) Uani 1 1 d . . . . .
H1 H 0.152788 -0.607963 1.070039 0.082 Uiso 1 1 calc R U . . .
O2 O 0.4035(6) 0.0318(4) 0.7304(3) 0.0524(14) Uani 1 1 d . . . . .
N1 N 0.4649(7) -0.2035(4) 0.7810(2) 0.0317(11) Uani 1 1 d . . . . .
N2 N 0.5559(6) -0.1354(4) 0.7178(2) 0.0290(12) Uani 1 1 d . . . . .
H2 H 0.643(8) -0.169(5) 0.693(3) 0.035 Uiso 1 1 d . U . . .
N3 N 0.8127(7) 0.1718(4) 0.5062(3) 0.0396(14) Uani 1 1 d . . . . .
H3 H 0.889(9) 0.218(5) 0.467(3) 0.048 Uiso 1 1 d . U . . .
C1 C 0.2938(9) -0.5572(5) 0.9841(3) 0.0370(15) Uani 1 1 d . . . . .
C2 C 0.2349(9) -0.4404(6) 0.9710(4) 0.0447(17) Uani 1 1 d . . . . .
H2A H 0.147264 -0.415843 1.004451 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3049(9) -0.3613(6) 0.9094(3) 0.0390(16) Uani 1 1 d . . . . .
H3A H 0.262456 -0.283076 0.900559 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4370(8) -0.3945(5) 0.8598(3) 0.0317(13) Uani 1 1 d . . . . .
C28 C 0.4924(9) -0.5121(5) 0.8735(3) 0.0411(16) Uani 1 1 d . . . . .
H28 H 0.580885 -0.536811 0.840481 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4198(10) -0.5934(5) 0.9349(3) 0.0437(16) Uani 1 1 d . . . . .
H6 H 0.456647 -0.672743 0.942815 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5169(8) -0.3111(5) 0.7953(3) 0.0317(14) Uani 1 1 d . . . . .
H7 H 0.608302 -0.336624 0.763652 0.038 Uiso 1 1 calc R U . . .
C8 C 0.5168(8) -0.0209(5) 0.6968(3) 0.0317(14) Uani 1 1 d . . . . .
C9 C 0.6224(8) 0.0448(4) 0.6281(3) 0.0266(12) Uani 1 1 d . . . . .
C10 C 0.6714(8) 0.1584(5) 0.6211(3) 0.0350(16) Uani 1 1 d . . . . .
H10 H 0.637272 0.192744 0.659059 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7690(9) 0.2216(5) 0.5595(3) 0.0394(15) Uani 1 1 d . . . . .
H11 H 0.804448 0.298605 0.554933 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7642(8) 0.0626(5) 0.5089(3) 0.0346(15) Uani 1 1 d . . . . .
H12 H 0.795173 0.032138 0.469160 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6691(9) -0.0029(4) 0.5702(3) 0.0300(12) Uani 1 1 d . . . . .
H13 H 0.635357 -0.079713 0.573493 0.036 Uiso 1 1 calc R U . . .
O3 O -0.3627(13) 1.2139(7) 0.8380(5) 0.165(4) Uani 1 1 d . U . . .
H3B H -0.341980 1.279897 0.810625 0.248 Uiso 1 1 calc R U . . .
O4 O -0.0567(7) 0.4993(4) 0.8672(2) 0.0521(12) Uani 1 1 d . . . . .
N4 N -0.0164(7) 0.7276(4) 0.7988(3) 0.0344(12) Uani 1 1 d . . . . .
N5 N 0.0737(7) 0.6383(4) 0.7727(2) 0.0299(11) Uani 1 1 d . . . . .
H5 H 0.155(8) 0.655(5) 0.733(3) 0.036 Uiso 1 1 d . U . . .
N6 N 0.2701(8) 0.2534(5) 0.7224(4) 0.065(2) Uani 1 1 d . . . . .
H6A H 0.317055 0.195800 0.705007 0.078 Uiso 1 1 calc R U . . .
C14 C -0.2494(16) 1.1292(9) 0.8122(7) 0.088(3) Uani 1 1 d . U . . .
C15 C -0.1318(13) 1.1412(8) 0.7571(6) 0.076(3) Uani 1 1 d . U . . .
H15 H -0.105744 1.216363 0.727011 0.092 Uiso 1 1 calc R U . . .
C16 C -0.0425(11) 1.0444(6) 0.7414(5) 0.060(2) Uani 1 1 d . . . . .
H16 H 0.044128 1.055337 0.700084 0.072 Uiso 1 1 calc R U . . .
C17 C -0.0735(10) 0.9310(6) 0.7835(4) 0.0457(17) Uani 1 1 d . . . . .
C18 C -0.2021(13) 0.9145(8) 0.8429(5) 0.076(3) Uani 1 1 d . . . . .
H18 H -0.225519 0.838272 0.871980 0.091 Uiso 1 1 calc R U . . .
C19 C -0.3026(15) 1.0141(11) 0.8613(6) 0.113(4) Uani 1 1 d . . . . .
H19 H -0.393858 1.006104 0.901073 0.136 Uiso 1 1 calc R U . . .
C20 C 0.0216(8) 0.8320(5) 0.7634(3) 0.0366(15) Uani 1 1 d . . . . .
H20 H 0.113113 0.845013 0.723541 0.044 Uiso 1 1 calc R U . . .
C21 C 0.0402(8) 0.5272(5) 0.8102(3) 0.0316(15) Uani 1 1 d . . . . .
C22 C 0.1276(9) 0.4332(4) 0.7762(3) 0.0323(12) Uani 1 1 d . . . . .
C23 C 0.1590(10) 0.4463(5) 0.7048(3) 0.0388(14) Uani 1 1 d . . . . .
H23 H 0.131511 0.517951 0.674163 0.047 Uiso 1 1 calc R U . . .
C24 C 0.2308(10) 0.3542(6) 0.6784(4) 0.058(2) Uani 1 1 d . . . . .
H24 H 0.252216 0.362144 0.629430 0.070 Uiso 1 1 calc R U . . .
C25 C 0.2401(11) 0.2377(6) 0.7918(6) 0.066(2) Uani 1 1 d . . . . .
H25 H 0.267799 0.164788 0.821231 0.080 Uiso 1 1 calc R U . . .
C26 C 0.1697(10) 0.3264(5) 0.8209(4) 0.052(2) Uani 1 1 d . . . . .
H26 H 0.149752 0.315774 0.870033 0.062 Uiso 1 1 calc R U . . .
O7 O 0.246(3) -0.0577(19) 0.8817(13) 0.193(9) Uani 0.5 1 d G U P A 2
H7A H 0.316990 -0.026170 0.845491 0.289 Uiso 0.5 1 calc R U P A 2
C1C C 0.317(5) -0.0530(17) 0.9424(17) 0.259(18) Uani 0.5 1 d G U P A 2
H1CA H 0.445343 -0.073701 0.936437 0.310 Uiso 0.5 1 calc R U P A 2
H1CB H 0.254560 -0.108686 0.984409 0.310 Uiso 0.5 1 calc R U P A 2
C1D C 0.289(2) 0.0709(16) 0.9503(10) 0.088(6) Uani 0.5 1 d G U P A 2
H1DA H 0.335861 0.076999 0.991275 0.132 Uiso 0.5 1 calc R U P A 2
H1DB H 0.351337 0.125103 0.908426 0.132 Uiso 0.5 1 calc R U P A 2
H1DC H 0.161364 0.090267 0.956193 0.132 Uiso 0.5 1 calc R U P A 2
O5 O -0.025(2) -0.1895(12) 0.9930(9) 0.124(5) Uani 0.5 1 d G U P B 1
H5A H -0.113992 -0.144940 0.996857 0.186 Uiso 0.5 1 calc R U P B 1
C5 C 0.130(2) -0.1344(16) 0.9997(10) 0.107(7) Uani 0.5 1 d G U P B 1
H5B H 0.233351 -0.189256 1.000306 0.128 Uiso 0.5 1 calc R U P B 1
H5C H 0.109660 -0.109580 1.043682 0.128 Uiso 0.5 1 calc R U P B 1
C1E C 0.168(3) -0.0290(19) 0.9370(13) 0.153(11) Uani 0.5 1 d G U P B 1
H1EA H 0.273341 0.010643 0.940024 0.229 Uiso 0.5 1 calc R U P B 1
H1EB H 0.188206 -0.054611 0.893848 0.229 Uiso 0.5 1 calc R U P B 1
H1EC H 0.065042 0.024725 0.937039 0.229 Uiso 0.5 1 calc R U P B 1


_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 Cl3 2.5954(15) . ?
Bi1 Cl6 2.6453(14) . ?
Bi1 Cl4 2.6697(14) . ?
Bi1 Cl5 2.7202(13) . ?
Bi1 Cl2 2.7749(2) . ?
Bi1 Cl1 2.8664(2) . ?
O1 C1 1.365(7) . ?
O1 H1 0.8300 . ?
O2 C8 1.231(7) . ?
N1 C7 1.278(7) . ?
N1 N2 1.389(6) . ?
N2 C8 1.335(7) . ?
N2 H2 0.88(6) . ?
N3 C11 1.326(8) . ?
N3 C12 1.347(7) . ?
N3 H3 0.94(6) . ?
C1 C6 1.371(9) . ?
C1 C2 1.393(9) . ?
C2 C3 1.372(9) . ?
C2 H2A 0.9400 . ?
C3 C4 1.387(8) . ?
C3 H3A 0.9400 . ?
C4 C28 1.394(8) . ?
C4 C7 1.452(8) . ?
C28 C6 1.386(8) . ?
C28 H28 0.9400 . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.495(8) . ?
C9 C10 1.376(7) . ?
C9 C13 1.393(7) . ?
C10 C11 1.365(8) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C13 1.364(7) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
O3 C14 1.415(11) . ?
O3 H3B 0.8300 . ?
O4 C21 1.212(7) . ?
N4 C20 1.268(7) . ?
N4 N5 1.383(6) . ?
N5 C21 1.340(7) . ?
N5 H5 0.89(6) . ?
N6 C25 1.327(10) . ?
N6 C24 1.331(9) . ?
N6 H6A 0.8700 . ?
C14 C15 1.262(14) . ?
C14 C19 1.479(16) . ?
C15 C16 1.368(11) . ?
C15 H15 0.9400 . ?
C16 C17 1.387(10) . ?
C16 H16 0.9400 . ?
C17 C18 1.367(11) . ?
C17 C20 1.442(9) . ?
C18 C19 1.451(12) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
C21 C22 1.505(7) . ?
C22 C23 1.369(7) . ?
C22 C26 1.394(8) . ?
C23 C24 1.370(8) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C26 1.360(10) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
O7 C1C 1.4257 . ?
O7 H7A 0.8300 . ?
C1C C1D 1.5094 . ?
C1C H1CA 0.9800 . ?
C1C H1CB 0.9800 . ?
C1D H1DA 0.9700 . ?
C1D H1DB 0.9700 . ?
C1D H1DC 0.9700 . ?
O5 C5 1.4251 . ?
O5 H5A 0.8300 . ?
C5 C1E 1.5100 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C1E H1EA 0.9700 . ?
C1E H1EB 0.9700 . ?
C1E H1EC 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
Cl3 Bi1 Cl6 91.04(5) . . ?
Cl3 Bi1 Cl4 89.52(4) . . ?
Cl6 Bi1 Cl4 88.83(5) . . ?
Cl3 Bi1 Cl5 90.59(5) . . ?
Cl6 Bi1 Cl5 175.62(5) . . ?
Cl4 Bi1 Cl5 87.12(5) . . ?
Cl3 Bi1 Cl2 91.60(4) . . ?
Cl6 Bi1 Cl2 92.47(4) . . ?
Cl4 Bi1 Cl2 178.27(3) . . ?
Cl5 Bi1 Cl2 91.55(3) . . ?
Cl3 Bi1 Cl1 175.73(4) . . ?
Cl6 Bi1 Cl1 89.71(4) . . ?
Cl4 Bi1 Cl1 94.70(3) . . ?
Cl5 Bi1 Cl1 88.97(3) . . ?
Cl2 Bi1 Cl1 84.170(6) . . ?
Bi1 Cl1 Bi1 180.0 2_766 . ?
Bi1 Cl2 Bi1 180.0 . 2_866 ?
C1 O1 H1 109.5 . . ?
C7 N1 N2 113.8(5) . . ?
C8 N2 N1 120.1(5) . . ?
C8 N2 H2 121(4) . . ?
N1 N2 H2 118(4) . . ?
C11 N3 C12 123.8(5) . . ?
C11 N3 H3 113(4) . . ?
C12 N3 H3 123(4) . . ?
O1 C1 C6 117.8(6) . . ?
O1 C1 C2 122.1(6) . . ?
C6 C1 C2 120.1(6) . . ?
C3 C2 C1 119.9(6) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 121.4(6) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C28 117.8(6) . . ?
C3 C4 C7 122.1(5) . . ?
C28 C4 C7 120.2(5) . . ?
C6 C28 C4 121.4(6) . . ?
C6 C28 H28 119.3 . . ?
C4 C28 H28 119.3 . . ?
C1 C6 C28 119.5(6) . . ?
C1 C6 H6 120.3 . . ?
C28 C6 H6 120.3 . . ?
N1 C7 C4 121.1(5) . . ?
N1 C7 H7 119.5 . . ?
C4 C7 H7 119.5 . . ?
O2 C8 N2 124.4(5) . . ?
O2 C8 C9 119.5(5) . . ?
N2 C8 C9 116.1(5) . . ?
C10 C9 C13 118.6(5) . . ?
C10 C9 C8 118.6(5) . . ?
C13 C9 C8 122.7(5) . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N3 C11 C10 118.5(5) . . ?
N3 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
N3 C12 C13 118.7(5) . . ?
N3 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C9 119.6(5) . . ?
C12 C13 H13 120.2 . . ?
C9 C13 H13 120.2 . . ?
C14 O3 H3B 109.5 . . ?
C20 N4 N5 116.7(5) . . ?
C21 N5 N4 117.9(5) . . ?
C21 N5 H5 122(4) . . ?
N4 N5 H5 120(4) . . ?
C25 N6 C24 122.3(6) . . ?
C25 N6 H6A 118.9 . . ?
C24 N6 H6A 118.9 . . ?
C15 C14 O3 130.2(11) . . ?
C15 C14 C19 123.7(9) . . ?
O3 C14 C19 106.0(11) . . ?
C14 C15 C16 119.8(10) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 123.2(9) . . ?
C15 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C18 C17 C16 118.6(7) . . ?
C18 C17 C20 120.6(7) . . ?
C16 C17 C20 120.8(7) . . ?
C17 C18 C19 120.3(9) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 114.3(10) . . ?
C18 C19 H19 122.8 . . ?
C14 C19 H19 122.8 . . ?
N4 C20 C17 121.0(6) . . ?
N4 C20 H20 119.5 . . ?
C17 C20 H20 119.5 . . ?
O4 C21 N5 124.6(5) . . ?
O4 C21 C22 119.6(5) . . ?
N5 C21 C22 115.9(5) . . ?
C23 C22 C26 119.4(5) . . ?
C23 C22 C21 123.2(5) . . ?
C26 C22 C21 117.3(5) . . ?
C22 C23 C24 119.6(6) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
N6 C24 C23 119.6(7) . . ?
N6 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
N6 C25 C26 120.6(7) . . ?
N6 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C22 118.6(7) . . ?
C25 C26 H26 120.7 . . ?
C22 C26 H26 120.7 . . ?
C1C O7 H7A 109.5 . . ?
O7 C1C C1D 107.4 . . ?
O7 C1C H1CA 110.2 . . ?
C1D C1C H1CA 110.2 . . ?
O7 C1C H1CB 110.2 . . ?
C1D C1C H1CB 110.2 . . ?
H1CA C1C H1CB 108.5 . . ?
C1C C1D H1DA 109.5 . . ?
C1C C1D H1DB 109.5 . . ?
H1DA C1D H1DB 109.5 . . ?
C1C C1D H1DC 109.5 . . ?
H1DA C1D H1DC 109.5 . . ?
H1DB C1D H1DC 109.5 . . ?
C5 O5 H5A 109.5 . . ?
O5 C5 C1E 107.4 . . ?
O5 C5 H5B 110.2 . . ?
C1E C5 H5B 110.2 . . ?
O5 C5 H5C 110.2 . . ?
C1E C5 H5C 110.2 . . ?
H5B C5 H5C 108.5 . . ?
C5 C1E H1EA 109.5 . . ?
C5 C1E H1EB 109.5 . . ?
H1EA C1E H1EB 109.5 . . ?
C5 C1E H1EC 109.5 . . ?
H1EA C1E H1EC 109.5 . . ?
H1EB C1E H1EC 109.5 . . ?

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
C7 N1 N2 C8 -179.0(5) . . . . ?
O1 C1 C2 C3 -179.2(6) . . . . ?
C6 C1 C2 C3 -0.9(10) . . . . ?
C1 C2 C3 C4 -1.4(11) . . . . ?
C2 C3 C4 C28 2.1(10) . . . . ?
C2 C3 C4 C7 -177.9(6) . . . . ?
C3 C4 C28 C6 -0.7(10) . . . . ?
C7 C4 C28 C6 179.4(6) . . . . ?
O1 C1 C6 C28 -179.3(6) . . . . ?
C2 C1 C6 C28 2.3(10) . . . . ?
C4 C28 C6 C1 -1.5(10) . . . . ?
N2 N1 C7 C4 179.5(5) . . . . ?
C3 C4 C7 N1 -1.6(9) . . . . ?
C28 C4 C7 N1 178.3(6) . . . . ?
N1 N2 C8 O2 0.7(9) . . . . ?
N1 N2 C8 C9 179.8(5) . . . . ?
O2 C8 C9 C10 36.1(9) . . . . ?
N2 C8 C9 C10 -143.1(6) . . . . ?
O2 C8 C9 C13 -142.1(7) . . . . ?
N2 C8 C9 C13 38.7(8) . . . . ?
C13 C9 C10 C11 -2.2(9) . . . . ?
C8 C9 C10 C11 179.5(6) . . . . ?
C12 N3 C11 C10 1.0(10) . . . . ?
C9 C10 C11 N3 1.2(10) . . . . ?
C11 N3 C12 C13 -2.1(10) . . . . ?
N3 C12 C13 C9 0.9(9) . . . . ?
C10 C9 C13 C12 1.1(9) . . . . ?
C8 C9 C13 C12 179.3(6) . . . . ?
C20 N4 N5 C21 178.0(5) . . . . ?
O3 C14 C15 C16 -177.4(9) . . . . ?
C19 C14 C15 C16 -1.9(17) . . . . ?
C14 C15 C16 C17 -0.3(14) . . . . ?
C15 C16 C17 C18 1.4(12) . . . . ?
C15 C16 C17 C20 178.4(7) . . . . ?
C16 C17 C18 C19 -0.4(13) . . . . ?
C20 C17 C18 C19 -177.4(8) . . . . ?
C17 C18 C19 C14 -1.5(14) . . . . ?
C15 C14 C19 C18 2.7(16) . . . . ?
O3 C14 C19 C18 179.2(9) . . . . ?
N5 N4 C20 C17 175.8(6) . . . . ?
C18 C17 C20 N4 2.6(11) . . . . ?
C16 C17 C20 N4 -174.4(6) . . . . ?
N4 N5 C21 O4 -4.0(9) . . . . ?
N4 N5 C21 C22 174.3(5) . . . . ?
O4 C21 C22 C23 145.9(7) . . . . ?
N5 C21 C22 C23 -32.5(9) . . . . ?
O4 C21 C22 C26 -31.0(9) . . . . ?
N5 C21 C22 C26 150.7(6) . . . . ?
C26 C22 C23 C24 0.2(10) . . . . ?
C21 C22 C23 C24 -176.6(6) . . . . ?
C25 N6 C24 C23 0.9(11) . . . . ?
C22 C23 C24 N6 -0.4(11) . . . . ?
C24 N6 C25 C26 -1.1(12) . . . . ?
N6 C25 C26 C22 0.8(12) . . . . ?
C23 C22 C26 C25 -0.4(10) . . . . ?
C21 C22 C26 C25 176.6(7) . . . . ?

_refine_diff_density_max         1.119
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.138

