# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_final_a
_database_code_depnum_ccdc_archive 'CCDC 2252252'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_final_a             
;
PROBLEM: Short Inter D...A Contact  O13      ..O81B     .       2.07 Ang.  
RESPONSE: O81B and O201 are the minor components of disordered lattice water 
molecules and the H atoms could not be located in the difference map and thus 
were left off.  There is likely hydrogen bonding between these atoms. 
;
_vrf_PLAT971_final_a             
;
PROBLEM: Check Calcd Resid. Dens.  1.08Ang From Bi1             4.94 eA-3  
RESPONSE: This is most likely caused by twinning in the crystal about the plane
that the bismuth metal centers lie leading to residual density from the twinned
bismuth ions.  All attempts to process the data/refine the structure as a twin 
were unsuccessful.
;
_vrf_PLAT417_final_a             
;
PROBLEM: Short Inter D-H..H-D       H22A     ..H71B     .       2.09 Ang.  
RESPONSE: These groups are involved in a hydrogen bonding network that likely 
holds the atoms closer than is typically observed.
;
_vrf_PLAT213_final_a             
;
PROBLEM: Atom O13             has ADP max/min Ratio .....        4.0 prolat
RESPONSE: This alert may be a result of the previous PLAT971 alert relating to 
resid. density from Bi1. That resid. density is in the vicinity of O13, which may
affect the ADP of O13 giving the appearance of potential disorder. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C28 H14 Bi2 N5 O19, C14 H13 N2, 3.837(H2 O), 0.163(O) 
;
_chemical_formula_sum            'C42 H34.67 Bi2 N7 O23'
_chemical_formula_weight         1423.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   9.3536(4)
_cell_length_b                   12.0494(6)
_cell_length_c                   21.2373(10)
_cell_angle_alpha                87.1920(10)
_cell_angle_beta                 84.0250(10)
_cell_angle_gamma                68.3220(10)
_cell_volume                     2212.04(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9799
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.42
_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.137
_exptl_crystal_F_000             1371
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    8.046
_shelx_estimated_absorpt_T_min   0.469
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63438
_exptl_absorpt_correction_T_max  0.90341
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52444
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         26.425
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9080
_reflns_number_gt                6995
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the un??ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The highest peaks in the final difference Fourier map 
were in the vicinity of the Bi atoms; the final map had no other significant 
features.  A final analysis of variance between observed and calculated 
structure factors showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0259P)²+24.1529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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         9080
_refine_ls_number_parameters     710
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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 0.64530(3) 0.60883(2) 0.31017(2) 0.01413(8) Uani 1 1 d . . . . .
Bi2 Bi 0.91210(3) 0.35409(2) 0.17732(2) 0.01592(8) Uani 1 1 d . . . . .
N11 N 0.3943(6) 0.6523(5) 0.2721(2) 0.0126(12) Uani 1 1 d . . . . .
O11 O 0.6500(5) 0.5092(4) 0.2077(2) 0.0154(10) Uani 1 1 d . . . . .
O12 O 0.5103(5) 0.4742(5) 0.1355(2) 0.0216(11) Uani 1 1 d . . . . .
O13 O 0.4437(5) 0.7222(4) 0.3811(2) 0.0151(10) Uani 1 1 d . . . . .
O14 O 0.2022(6) 0.8480(5) 0.3985(2) 0.0207(11) Uani 1 1 d . . . . .
C11 C 0.5231(8) 0.5223(6) 0.1833(3) 0.0147(15) Uani 1 1 d . . . . .
C12 C 0.3778(8) 0.6046(6) 0.2197(3) 0.0152(15) Uani 1 1 d . . . . .
C13 C 0.2311(8) 0.6275(6) 0.1996(3) 0.0183(15) Uani 1 1 d . . . . .
H13 H 0.220506 0.591848 0.162338 0.022 Uiso 1 1 calc R U . . .
C14 C 0.1027(8) 0.7027(7) 0.2350(3) 0.0205(16) Uani 1 1 d . . . . .
H14 H 0.002296 0.719926 0.222224 0.025 Uiso 1 1 calc R U . . .
C16 C 0.2705(8) 0.7242(6) 0.3068(3) 0.0142(14) Uani 1 1 d . . . . .
C15 C 0.1217(8) 0.7534(6) 0.2900(3) 0.0174(15) Uani 1 1 d . . . . .
H15 H 0.035225 0.806112 0.314953 0.021 Uiso 1 1 calc R U . . .
C17 C 0.3065(8) 0.7690(6) 0.3666(3) 0.0151(14) Uani 1 1 d . . . . .
N21 N 0.7099(6) 0.5379(5) 0.4180(2) 0.0136(12) Uani 1 1 d . . . . .
O21 O 0.7722(6) 0.7269(4) 0.3701(2) 0.0202(11) Uani 1 1 d . . . . .
O22 O 0.8642(6) 0.7469(5) 0.4603(2) 0.0227(12) Uani 1 1 d D . . . .
H22A H 0.867(8) 0.809(4) 0.442(3) 0.034 Uiso 1 1 d D U . . .
O23 O 0.5752(5) 0.4484(4) 0.3417(2) 0.0166(10) Uani 1 1 d . . . . .
O24 O 0.5794(6) 0.3007(4) 0.4093(2) 0.0209(11) Uani 1 1 d . . . . .
C21 C 0.8033(8) 0.6955(6) 0.4240(3) 0.0167(15) Uani 1 1 d . . . . .
C22 C 0.7722(8) 0.5920(6) 0.4546(3) 0.0152(14) Uani 1 1 d . . . . .
C23 C 0.8032(8) 0.5528(7) 0.5159(3) 0.0192(15) Uani 1 1 d . . . . .
H23 H 0.847312 0.591961 0.541474 0.023 Uiso 1 1 calc R U . . .
C24 C 0.7688(8) 0.4556(7) 0.5392(3) 0.0207(16) Uani 1 1 d . . . . .
H24 H 0.789591 0.426792 0.581008 0.025 Uiso 1 1 calc R U . . .
C25 C 0.7037(8) 0.4007(7) 0.5012(3) 0.0203(16) Uani 1 1 d . . . . .
H25 H 0.678609 0.334214 0.516667 0.024 Uiso 1 1 calc R U . . .
C26 C 0.6758(8) 0.4442(6) 0.4404(3) 0.0148(14) Uani 1 1 d . . . . .
C27 C 0.6043(7) 0.3929(6) 0.3944(3) 0.0141(14) Uani 1 1 d . . . . .
N31 N 1.1667(6) 0.3069(5) 0.2153(3) 0.0138(12) Uani 1 1 d . . . . .
O31 O 0.9073(5) 0.4361(4) 0.2838(2) 0.0174(10) Uani 1 1 d . . . . .
O32 O 1.0420(6) 0.4741(5) 0.3558(2) 0.0229(12) Uani 1 1 d . . . . .
O33 O 1.1136(5) 0.2352(4) 0.1080(2) 0.0176(10) Uani 1 1 d . . . . .
O34 O 1.3627(6) 0.1347(5) 0.0815(2) 0.0255(12) Uani 1 1 d . . . . .
C31 C 1.0350(8) 0.4286(7) 0.3068(3) 0.0176(15) Uani 1 1 d . . . . .
C32 C 1.1818(8) 0.3559(6) 0.2686(3) 0.0152(14) Uani 1 1 d . . . . .
C33 C 1.3263(8) 0.3407(6) 0.2859(3) 0.0157(15) Uani 1 1 d . . . . .
H33 H 1.336220 0.375010 0.323790 0.019 Uiso 1 1 calc R U . . .
C34 C 1.4560(8) 0.2750(7) 0.2478(3) 0.0202(16) Uani 1 1 d . . . . .
H34 H 1.555873 0.264577 0.259033 0.024 Uiso 1 1 calc R U . . .
C35 C 1.4401(8) 0.2243(7) 0.1928(3) 0.0209(16) Uani 1 1 d . . . . .
H35 H 1.528094 0.177973 0.166240 0.025 Uiso 1 1 calc R U . . .
C36 C 1.2920(8) 0.2433(6) 0.1779(3) 0.0167(15) Uani 1 1 d . . . . .
C37 C 1.2570(8) 0.1976(6) 0.1179(3) 0.0176(15) Uani 1 1 d . . . . .
N41 N 0.8302(6) 0.4366(5) 0.0755(3) 0.0165(12) Uani 1 1 d . . . . .
O41 O 0.7925(5) 0.2331(4) 0.1137(2) 0.0187(11) Uani 1 1 d . . . . .
O42 O 0.6758(6) 0.2326(5) 0.0268(2) 0.0230(12) Uani 1 1 d D . . . .
H42A H 0.685(9) 0.163(3) 0.040(4) 0.035 Uiso 1 1 d D U . . .
O43 O 0.9796(6) 0.5087(4) 0.1531(2) 0.0178(11) Uani 1 1 d . . . . .
O44 O 0.9707(6) 0.6647(5) 0.0914(2) 0.0249(12) Uani 1 1 d . . . . .
C41 C 0.7444(8) 0.2763(6) 0.0635(3) 0.0165(15) Uani 1 1 d . . . . .
C42 C 0.7553(8) 0.3930(7) 0.0393(3) 0.0185(15) Uani 1 1 d . . . . .
C43 C 0.6921(8) 0.4539(7) -0.0140(3) 0.0188(16) Uani 1 1 d . . . . .
H43 H 0.644165 0.419758 -0.040631 0.023 Uiso 1 1 calc R U . . .
C44 C 0.6991(8) 0.5649(7) -0.0281(3) 0.0215(16) Uani 1 1 d . . . . .
H44 H 0.652009 0.609830 -0.063397 0.026 Uiso 1 1 calc R U . . .
C45 C 0.7764(8) 0.6098(7) 0.0103(3) 0.0197(16) Uani 1 1 d . . . . .
H45 H 0.783347 0.685817 0.001550 0.024 Uiso 1 1 calc R U . . .
C46 C 0.8437(8) 0.5411(6) 0.0618(3) 0.0172(15) Uani 1 1 d . . . . .
C47 C 0.9353(8) 0.5777(6) 0.1044(3) 0.0167(15) Uani 1 1 d . . . . .
N51 N 0.2966(7) 1.0365(5) 0.3054(3) 0.0182(13) Uani 1 1 d . . . . .
H51A H 0.385(10) 0.989(7) 0.282(4) 0.027 Uiso 1 1 d . U . . .
N52 N 0.2911(7) 0.9467(5) 0.1916(3) 0.0197(13) Uani 1 1 d . . . . .
C51 C 0.3119(10) 1.0781(7) 0.3605(3) 0.0244(17) Uani 1 1 d . . . . .
C52 C 0.1769(10) 1.1456(7) 0.3970(4) 0.0292(19) Uani 1 1 d . . . . .
H52 H 0.184609 1.178087 0.435800 0.035 Uiso 1 1 calc R U . . .
C53 C 0.0362(10) 1.1655(7) 0.3783(4) 0.0260(18) Uani 1 1 d . . . . .
H53 H -0.053653 1.210683 0.404283 0.031 Uiso 1 1 calc R U . . .
C54 C 0.0210(9) 1.1200(6) 0.3206(3) 0.0227(16) Uani 1 1 d . . . . .
C55 C 0.1580(8) 1.0557(6) 0.2839(3) 0.0186(15) Uani 1 1 d . . . . .
C56 C -0.1240(8) 1.1326(7) 0.2980(4) 0.0256(17) Uani 1 1 d . . . . .
H56 H -0.217780 1.175528 0.322414 0.031 Uiso 1 1 calc R U . . .
C57 C -0.1288(9) 1.0848(7) 0.2430(4) 0.0244(17) Uani 1 1 d . . . . .
H57 H -0.225912 1.093295 0.229373 0.029 Uiso 1 1 calc R U . . .
C58 C 0.0104(9) 1.0209(7) 0.2042(4) 0.0224(16) Uani 1 1 d . . . . .
C59 C 0.1539(8) 1.0059(6) 0.2240(3) 0.0184(15) Uani 1 1 d . . . . .
C60 C 0.0114(9) 0.9707(7) 0.1450(4) 0.0244(17) Uani 1 1 d . . . . .
H60 H -0.082701 0.979002 0.128503 0.029 Uiso 1 1 calc R U . . .
C61 C 0.1497(10) 0.9106(7) 0.1123(4) 0.0276(18) Uani 1 1 d . . . . .
H61 H 0.152430 0.876019 0.072731 0.033 Uiso 1 1 calc R U . . .
C62 C 0.2891(9) 0.8991(7) 0.1368(3) 0.0227(16) Uani 1 1 d . . . . .
C63 C 0.4712(10) 1.0484(8) 0.3800(4) 0.034(2) Uani 1 1 d . . . . .
H63A H 0.482478 1.001444 0.419427 0.051 Uiso 1 1 calc R U . . .
H63B H 0.487999 1.122424 0.386645 0.051 Uiso 1 1 calc R U . . .
H63C H 0.547334 1.002001 0.346692 0.051 Uiso 1 1 calc R U . . .
C64 C 0.4439(9) 0.8321(8) 0.1010(4) 0.0299(19) Uani 1 1 d . . . . .
H64A H 0.452126 0.750322 0.093292 0.045 Uiso 1 1 calc R U . . .
H64B H 0.527021 0.829876 0.126181 0.045 Uiso 1 1 calc R U . . .
H64C H 0.452713 0.872616 0.060499 0.045 Uiso 1 1 calc R U . . .
N61 N 0.6531(8) 0.8390(6) 0.2343(3) 0.0280(15) Uani 1 1 d . . . . .
O61 O 0.5482(6) 0.8325(5) 0.2782(3) 0.0315(13) Uani 1 1 d . . . . .
O62 O 0.7456(7) 0.7419(6) 0.2129(3) 0.0391(15) Uani 1 1 d . . . . .
O63 O 0.6540(8) 0.9350(6) 0.2181(4) 0.0545(19) Uani 1 1 d . . . . .
O71 O 0.8913(6) 0.9307(4) 0.4147(2) 0.0211(11) Uani 1 1 d D . . . .
H71B H 0.989(3) 0.921(5) 0.416(4) 0.032 Uiso 1 1 d D U . . .
H71A H 0.824(7) 0.993(3) 0.436(3) 0.032 Uiso 1 1 d D U . . .
O81 O 0.7056(7) 1.1021(5) 0.4877(3) 0.0250(15) Uani 0.914(9) 1 d D . P A 1
H81A H 0.747(10) 1.125(8) 0.517(3) 0.037 Uiso 0.914(9) 1 d D U P A 1
H81B H 0.653(10) 1.166(5) 0.468(4) 0.037 Uiso 0.914(9) 1 d D U P A 1
O81B O 0.622(7) 1.137(5) 0.557(3) 0.0250(15) Uani 0.086(9) 1 d . . P A 2
O91 O 0.6771(7) 0.0375(5) 0.0635(3) 0.0304(13) Uani 1 1 d D . . . .
H91B H 0.582(4) 0.040(6) 0.072(4) 0.046 Uiso 1 1 d D U . . .
H91A H 0.729(9) -0.030(5) 0.044(4) 0.046 Uiso 1 1 d D U . . .
O101 O 0.9105(7) -0.1405(5) 0.0105(3) 0.0213(14) Uani 0.923(9) 1 d D . P B 1
H101 H 0.922(11) -0.187(7) -0.021(3) 0.032 Uiso 0.923(9) 1 d D U P B 1
H102 H 0.910(11) -0.200(5) 0.035(4) 0.032 Uiso 0.923(9) 1 d D U P B 1
O201 O 0.820(8) -0.098(6) -0.044(3) 0.0213(14) Uani 0.077(9) 1 d . . P B 2


_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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Six frame series 
were integrated and filtered for statistical outliers using SAINT 
(Bruker, 2016) then corrected for absorption by integration using SAINT/SADABS 
v2014/2 (Bruker, 2016) to sort, merge, and scale the combined data.  No decay 
correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0140
0.00 0.00 -1.00 0.0230
1.00 0.00 0.00 0.0490
-1.00 0.00 0.00 0.0160
0.00 -1.00 1.00 0.0100
0.00 1.00 -1.00 0.0070
0.00 1.00 0.00 0.0040
0.00 -1.00 0.00 0.0120

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 O23 2.310(5) . ?
Bi1 O13 2.324(4) . ?
Bi1 N11 2.426(5) . ?
Bi1 N21 2.461(5) . ?
Bi1 O11 2.524(4) . ?
Bi1 O61 2.587(6) . ?
Bi1 O31 2.591(5) . ?
Bi1 O21 2.607(5) . ?
Bi2 O43 2.200(5) . ?
Bi2 O33 2.325(5) . ?
Bi2 N41 2.414(6) . ?
Bi2 N31 2.449(5) . ?
Bi2 O31 2.502(4) . ?
Bi2 O11 2.515(5) . ?
Bi2 O41 2.630(5) . ?
N11 C12 1.324(8) . ?
N11 C16 1.334(8) . ?
O11 C11 1.298(8) . ?
O12 C11 1.233(8) . ?
O13 C17 1.261(8) . ?
O14 C17 1.247(8) . ?
C11 C12 1.513(10) . ?
C12 C13 1.405(9) . ?
C13 C14 1.380(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.400(10) . ?
C14 H14 0.9500 . ?
C16 C15 1.385(9) . ?
C16 C17 1.519(9) . ?
C15 H15 0.9500 . ?
N21 C26 1.335(9) . ?
N21 C22 1.339(8) . ?
O21 C21 1.218(8) . ?
O22 C21 1.304(8) . ?
O22 H22A 0.836(19) . ?
O23 C27 1.276(8) . ?
O24 C27 1.236(8) . ?
C21 C22 1.487(10) . ?
C22 C23 1.386(9) . ?
C23 C24 1.381(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(10) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.511(9) . ?
N31 C36 1.340(9) . ?
N31 C32 1.346(9) . ?
O31 C31 1.308(8) . ?
O32 C31 1.219(8) . ?
O33 C37 1.285(8) . ?
O34 C37 1.223(8) . ?
C31 C32 1.503(10) . ?
C32 C33 1.382(9) . ?
C33 C34 1.379(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(10) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(10) . ?
C35 H35 0.9500 . ?
C36 C37 1.523(10) . ?
N41 C46 1.325(9) . ?
N41 C42 1.335(9) . ?
O41 C41 1.217(8) . ?
O42 C41 1.299(8) . ?
O42 H42A 0.85(2) . ?
O43 C47 1.298(8) . ?
O44 C47 1.223(8) . ?
C41 C42 1.509(10) . ?
C42 C43 1.380(9) . ?
C43 C44 1.380(10) . ?
C43 H43 0.9500 . ?
C44 C45 1.390(10) . ?
C44 H44 0.9500 . ?
C45 C46 1.396(10) . ?
C45 H45 0.9500 . ?
C46 C47 1.493(9) . ?
N51 C51 1.338(9) . ?
N51 C55 1.354(9) . ?
N51 H51A 0.92(8) . ?
N52 C62 1.328(9) . ?
N52 C59 1.349(9) . ?
C51 C52 1.398(11) . ?
C51 C63 1.496(11) . ?
C52 C53 1.347(11) . ?
C52 H52 0.9500 . ?
C53 C54 1.409(10) . ?
C53 H53 0.9500 . ?
C54 C55 1.402(10) . ?
C54 C56 1.438(11) . ?
C55 C59 1.443(10) . ?
C56 C57 1.339(11) . ?
C56 H56 0.9500 . ?
C57 C58 1.437(10) . ?
C57 H57 0.9500 . ?
C58 C59 1.393(10) . ?
C58 C60 1.420(10) . ?
C60 C61 1.360(11) . ?
C60 H60 0.9500 . ?
C61 C62 1.411(11) . ?
C61 H61 0.9500 . ?
C62 C64 1.514(10) . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
N61 O63 1.193(9) . ?
N61 O62 1.243(8) . ?
N61 O61 1.304(8) . ?
O71 H71B 0.88(2) . ?
O71 H71A 0.88(2) . ?
O81 H81A 0.87(2) . ?
O81 H81B 0.87(2) . ?
O91 H91B 0.88(2) . ?
O91 H91A 0.88(2) . ?
O101 H101 0.86(2) . ?
O101 H102 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O23 Bi1 O13 86.92(17) . . ?
O23 Bi1 N11 74.25(17) . . ?
O13 Bi1 N11 67.60(17) . . ?
O23 Bi1 N21 67.14(17) . . ?
O13 Bi1 N21 71.86(17) . . ?
N11 Bi1 N21 124.45(18) . . ?
O23 Bi1 O11 76.00(15) . . ?
O13 Bi1 O11 132.25(15) . . ?
N11 Bi1 O11 64.91(16) . . ?
N21 Bi1 O11 134.86(17) . . ?
O23 Bi1 O61 145.75(17) . . ?
O13 Bi1 O61 68.71(17) . . ?
N11 Bi1 O61 74.32(18) . . ?
N21 Bi1 O61 122.77(18) . . ?
O11 Bi1 O61 102.36(16) . . ?
O23 Bi1 O31 80.47(16) . . ?
O13 Bi1 O31 152.06(15) . . ?
N11 Bi1 O31 130.87(16) . . ?
N21 Bi1 O31 80.26(16) . . ?
O11 Bi1 O31 68.46(14) . . ?
O61 Bi1 O31 131.54(16) . . ?
O23 Bi1 O21 130.95(15) . . ?
O13 Bi1 O21 77.03(15) . . ?
N11 Bi1 O21 135.51(17) . . ?
N21 Bi1 O21 63.83(17) . . ?
O11 Bi1 O21 145.42(15) . . ?
O61 Bi1 O21 68.10(16) . . ?
O31 Bi1 O21 92.58(15) . . ?
O43 Bi2 O33 90.63(17) . . ?
O43 Bi2 N41 69.47(18) . . ?
O33 Bi2 N41 77.78(18) . . ?
O43 Bi2 N31 73.27(18) . . ?
O33 Bi2 N31 66.87(17) . . ?
N41 Bi2 N31 127.48(18) . . ?
O43 Bi2 O31 77.60(16) . . ?
O33 Bi2 O31 132.08(15) . . ?
N41 Bi2 O31 135.90(18) . . ?
N31 Bi2 O31 65.25(17) . . ?
O43 Bi2 O11 84.41(17) . . ?
O33 Bi2 O11 155.67(15) . . ?
N41 Bi2 O11 78.18(17) . . ?
N31 Bi2 O11 133.11(17) . . ?
O31 Bi2 O11 70.00(15) . . ?
O43 Bi2 O41 133.10(15) . . ?
O33 Bi2 O41 74.30(15) . . ?
N41 Bi2 O41 64.03(17) . . ?
N31 Bi2 O41 133.35(17) . . ?
O31 Bi2 O41 143.88(15) . . ?
O11 Bi2 O41 91.82(15) . . ?
C12 N11 C16 120.3(6) . . ?
C12 N11 Bi1 122.1(5) . . ?
C16 N11 Bi1 117.6(4) . . ?
C11 O11 Bi2 126.0(4) . . ?
C11 O11 Bi1 121.2(4) . . ?
Bi2 O11 Bi1 111.43(16) . . ?
C17 O13 Bi1 122.3(4) . . ?
O12 C11 O11 127.1(6) . . ?
O12 C11 C12 118.4(6) . . ?
O11 C11 C12 114.5(6) . . ?
N11 C12 C13 121.3(7) . . ?
N11 C12 C11 117.3(6) . . ?
C13 C12 C11 121.4(6) . . ?
C14 C13 C12 118.8(6) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 119.4(6) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N11 C16 C15 122.4(6) . . ?
N11 C16 C17 114.4(6) . . ?
C15 C16 C17 123.2(6) . . ?
C16 C15 C14 117.9(7) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
O14 C17 O13 123.6(6) . . ?
O14 C17 C16 119.8(6) . . ?
O13 C17 C16 116.6(6) . . ?
C26 N21 C22 120.2(6) . . ?
C26 N21 Bi1 117.5(4) . . ?
C22 N21 Bi1 122.4(4) . . ?
C21 O21 Bi1 117.9(4) . . ?
C21 O22 H22A 108(5) . . ?
C27 O23 Bi1 124.0(4) . . ?
O21 C21 O22 125.1(7) . . ?
O21 C21 C22 121.3(6) . . ?
O22 C21 C22 113.7(6) . . ?
N21 C22 C23 121.4(6) . . ?
N21 C22 C21 114.6(6) . . ?
C23 C22 C21 124.0(6) . . ?
C24 C23 C22 118.7(6) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 119.5(7) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 119.0(7) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
N21 C26 C25 121.3(6) . . ?
N21 C26 C27 114.6(6) . . ?
C25 C26 C27 124.1(6) . . ?
O24 C27 O23 124.3(6) . . ?
O24 C27 C26 119.0(6) . . ?
O23 C27 C26 116.7(6) . . ?
C36 N31 C32 120.3(6) . . ?
C36 N31 Bi2 118.4(4) . . ?
C32 N31 Bi2 120.8(4) . . ?
C31 O31 Bi2 121.1(4) . . ?
C31 O31 Bi1 123.1(4) . . ?
Bi2 O31 Bi1 109.67(17) . . ?
C37 O33 Bi2 124.5(4) . . ?
O32 C31 O31 125.2(7) . . ?
O32 C31 C32 119.5(6) . . ?
O31 C31 C32 115.4(6) . . ?
N31 C32 C33 120.7(6) . . ?
N31 C32 C31 116.8(6) . . ?
C33 C32 C31 122.5(6) . . ?
C34 C33 C32 119.3(6) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C33 C34 C35 119.8(6) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 118.1(7) . . ?
C36 C35 H35 121.0 . . ?
C34 C35 H35 121.0 . . ?
N31 C36 C35 121.8(6) . . ?
N31 C36 C37 114.4(6) . . ?
C35 C36 C37 123.8(7) . . ?
O34 C37 O33 124.4(6) . . ?
O34 C37 C36 120.1(6) . . ?
O33 C37 C36 115.4(6) . . ?
C46 N41 C42 120.8(6) . . ?
C46 N41 Bi2 114.4(4) . . ?
C42 N41 Bi2 124.0(5) . . ?
C41 O41 Bi2 116.8(4) . . ?
C41 O42 H42A 109(6) . . ?
C47 O43 Bi2 123.3(4) . . ?
O41 C41 O42 125.7(7) . . ?
O41 C41 C42 121.0(6) . . ?
O42 C41 C42 113.2(6) . . ?
N41 C42 C43 121.2(7) . . ?
N41 C42 C41 113.7(6) . . ?
C43 C42 C41 125.1(6) . . ?
C42 C43 C44 119.3(6) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 H43 120.3 . . ?
C43 C44 C45 118.8(6) . . ?
C43 C44 H44 120.6 . . ?
C45 C44 H44 120.6 . . ?
C44 C45 C46 118.8(7) . . ?
C44 C45 H45 120.6 . . ?
C46 C45 H45 120.6 . . ?
N41 C46 C45 121.0(6) . . ?
N41 C46 C47 115.6(6) . . ?
C45 C46 C47 123.5(7) . . ?
O44 C47 O43 123.4(6) . . ?
O44 C47 C46 120.6(6) . . ?
O43 C47 C46 115.9(6) . . ?
C51 N51 C55 123.2(7) . . ?
C51 N51 H51A 118(5) . . ?
C55 N51 H51A 119(5) . . ?
C62 N52 C59 117.4(6) . . ?
N51 C51 C52 117.6(7) . . ?
N51 C51 C63 118.4(7) . . ?
C52 C51 C63 123.9(7) . . ?
C53 C52 C51 121.4(7) . . ?
C53 C52 H52 119.3 . . ?
C51 C52 H52 119.3 . . ?
C52 C53 C54 120.6(7) . . ?
C52 C53 H53 119.7 . . ?
C54 C53 H53 119.7 . . ?
C55 C54 C53 116.9(7) . . ?
C55 C54 C56 118.6(7) . . ?
C53 C54 C56 124.5(7) . . ?
N51 C55 C54 120.2(6) . . ?
N51 C55 C59 119.0(6) . . ?
C54 C55 C59 120.8(7) . . ?
C57 C56 C54 121.0(7) . . ?
C57 C56 H56 119.5 . . ?
C54 C56 H56 119.5 . . ?
C56 C57 C58 121.2(7) . . ?
C56 C57 H57 119.4 . . ?
C58 C57 H57 119.4 . . ?
C59 C58 C60 116.6(7) . . ?
C59 C58 C57 120.1(7) . . ?
C60 C58 C57 123.3(7) . . ?
N52 C59 C58 124.9(7) . . ?
N52 C59 C55 116.8(6) . . ?
C58 C59 C55 118.3(7) . . ?
C61 C60 C58 118.7(7) . . ?
C61 C60 H60 120.7 . . ?
C58 C60 H60 120.7 . . ?
C60 C61 C62 120.5(7) . . ?
C60 C61 H61 119.8 . . ?
C62 C61 H61 119.8 . . ?
N52 C62 C61 122.0(7) . . ?
N52 C62 C64 117.0(7) . . ?
C61 C62 C64 121.0(7) . . ?
C51 C63 H63A 109.5 . . ?
C51 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C51 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C62 C64 H64A 109.5 . . ?
C62 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C62 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
O63 N61 O62 125.5(7) . . ?
O63 N61 O61 118.8(7) . . ?
O62 N61 O61 115.7(7) . . ?
N61 O61 Bi1 103.7(4) . . ?
H71B O71 H71A 115(7) . . ?
H81A O81 H81B 106(9) . . ?
H91B O91 H91A 106(8) . . ?
H101 O101 H102 86(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15 O71 0.95 2.60 3.491(9) 155.6 1_455 yes
O22 H22A O71 0.836(19) 1.63(2) 2.462(7) 171(8) . yes
C23 H23 O32 0.95 2.48 3.163(8) 128.7 2_766 yes
C25 H25 O13 0.95 2.53 3.281(9) 136.2 2_666 yes
O42 H42A O91 0.85(2) 1.59(2) 2.437(8) 172(8) . yes
C43 H43 O12 0.95 2.60 3.252(8) 126.1 2_665 yes
N51 H51A N61 0.92(8) 2.63(9) 3.536(9) 171(7) . yes
N51 H51A O61 0.92(8) 1.94(8) 2.737(9) 145(7) . yes
N51 H51A O63 0.92(8) 2.61(8) 3.467(9) 156(7) . yes
C52 H52 O22 0.95 2.36 3.283(9) 163.8 2_676 yes
C61 H61 O42 0.95 2.60 3.433(9) 146.2 2_665 yes
C63 H63C O61 0.98 2.56 3.286(10) 130.8 . yes
O71 H71B O14 0.88(2) 1.86(4) 2.693(7) 157(7) 1_655 yes
O71 H71A O81^a 0.88(2) 1.73(3) 2.606(8) 171(8) . yes
O81^a H81A^a O14 0.87(2) 1.98(4) 2.812(7) 160(9) 2_676 yes
O81^a H81B^a O24 0.87(2) 1.95(3) 2.798(7) 167(9) 1_565 yes
O91 H91B O34 0.88(2) 1.94(4) 2.726(8) 149(6) 1_455 yes
O91 H91A O101^a 0.88(2) 1.82(5) 2.627(8) 151(9) . yes
O101^a H102^a O44 0.87(2) 1.92(3) 2.759(8) 163(9) 1_545 yes
O101^a H101^a O33 0.86(2) 2.06(4) 2.876(7) 157(9) 2_755 yes
O91 H91A O201^b 0.88(2) 2.04(9) 2.79(6) 142(9) . yes

_refine_diff_density_max         5.602
_refine_diff_density_min         -1.530
_refine_diff_density_rms         0.194



####################################################################### 
# 
# 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_final_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2252254'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2023-09-22 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         'C28 H14 Bi2 N6 O22, 2(C12 H8 Cl N2), 6(H2 O)'
_chemical_formula_sum            'C52 H42 Bi2 Cl2 N10 O28'
_chemical_formula_weight         1743.81

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                   9.2038(10)
_cell_length_b                   11.4928(13)
_cell_length_c                   14.7710(17)
_cell_angle_alpha                72.918(4)
_cell_angle_beta                 78.693(3)
_cell_angle_gamma                71.408(3)
_cell_volume                     1406.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.35

_exptl_crystal_description       Plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    6.448
_shelx_estimated_absorpt_T_min   0.524
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73869
_exptl_absorpt_correction_T_max  0.90094
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18666
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         25.446
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5174
_reflns_number_gt                4748
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'


_refine_special_details          
;
Structure was phased by Intrinsic methods (Sheldrick, 
2015).  Systematic conditions suggested the ambiguous space group.  
The space group choice was confirmed by successful convergence of the 
full-matrix least-squares refinement on F².  A final analysis of 
variance between observed and calculated structure factors showed little 
dependence on amplitude and resolution. 

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0104P)²+1.1648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Intrinsic
_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         5174
_refine_ls_number_parameters     447
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0398
_refine_ls_wR_factor_gt          0.0386
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.52926(2) 0.66681(2) 0.39785(2) 0.00980(4) Uani 1 1 d . . . . .
N11 N 0.3723(3) 0.8566(2) 0.45162(17) 0.0108(6) Uani 1 1 d . . . . .
O11 O 0.2913(2) 0.8238(2) 0.29776(15) 0.0156(5) Uani 1 1 d . . . . .
O12 O 0.1221(3) 1.0173(2) 0.27532(16) 0.0197(5) Uani 1 1 d D . . . .
H12 H 0.115(3) 1.0031(16) 0.2233(16) 0.030 Uiso 1 1 calc DR U . . .
O13 O 0.6145(2) 0.67811(19) 0.52434(14) 0.0129(5) Uani 1 1 d . . . . .
O14 O 0.5908(2) 0.7677(2) 0.64278(15) 0.0189(5) Uani 1 1 d . . . . .
C11 C 0.2235(3) 0.9227(3) 0.3212(2) 0.0136(7) Uani 1 1 d . . . . .
C12 C 0.2540(3) 0.9453(3) 0.4095(2) 0.0118(7) Uani 1 1 d . . . . .
C13 C 0.1675(4) 1.0463(3) 0.4467(2) 0.0159(7) Uani 1 1 d . . . . .
H13 H 0.083431 1.107723 0.416200 0.019 Uiso 1 1 calc R U . . .
C14 C 0.2058(4) 1.0561(3) 0.5296(2) 0.0181(7) Uani 1 1 d . . . . .
H14 H 0.146999 1.124153 0.557281 0.022 Uiso 1 1 calc R U . . .
C15 C 0.3301(4) 0.9666(3) 0.5719(2) 0.0143(7) Uani 1 1 d . . . . .
H15 H 0.359654 0.973028 0.628002 0.017 Uiso 1 1 calc R U . . .
C16 C 0.4108(3) 0.8669(3) 0.5304(2) 0.0125(7) Uani 1 1 d . . . . .
C17 C 0.5480(3) 0.7646(3) 0.5711(2) 0.0142(7) Uani 1 1 d . . . . .
N21 N 0.8088(3) 0.5989(2) 0.36813(17) 0.0097(5) Uani 1 1 d . . . . .
O21 O 0.6529(2) 0.43558(19) 0.47217(15) 0.0138(5) Uani 1 1 d . . . . .
O22 O 0.8705(2) 0.2755(2) 0.48552(17) 0.0226(6) Uani 1 1 d . . . . .
O23 O 0.6320(2) 0.83416(18) 0.31384(14) 0.0122(5) Uani 1 1 d . . . . .
O24 O 0.8329(2) 0.90391(19) 0.23860(15) 0.0170(5) Uani 1 1 d . . . . .
C21 C 0.7999(3) 0.3871(3) 0.4582(2) 0.0128(7) Uani 1 1 d . . . . .
C22 C 0.8905(3) 0.4789(3) 0.4030(2) 0.0105(6) Uani 1 1 d . . . . .
C23 C 1.0504(3) 0.4445(3) 0.3909(2) 0.0134(7) Uani 1 1 d . . . . .
H23 H 1.107307 0.359158 0.414882 0.016 Uiso 1 1 calc R U . . .
C24 C 1.1261(4) 0.5349(3) 0.3439(2) 0.0154(7) Uani 1 1 d . . . . .
H24 H 1.235689 0.512678 0.335828 0.018 Uiso 1 1 calc R U . . .
C25 C 1.0412(3) 0.6589(3) 0.3085(2) 0.0140(7) Uani 1 1 d . . . . .
H25 H 1.091202 0.722742 0.275999 0.017 Uiso 1 1 calc R U . . .
C26 C 0.8810(3) 0.6873(3) 0.3217(2) 0.0113(7) Uani 1 1 d . . . . .
C27 C 0.7767(4) 0.8193(3) 0.2874(2) 0.0127(7) Uani 1 1 d . . . . .
N31 N 0.5053(3) 0.6192(2) 0.19496(19) 0.0155(6) Uani 1 1 d . . . . .
O31 O 0.5766(2) 0.6907(2) 0.20399(15) 0.0184(5) Uani 1 1 d . . . . .
O32 O 0.4852(3) 0.5288(2) 0.26285(15) 0.0200(5) Uani 1 1 d . . . . .
O33 O 0.4545(3) 0.6396(2) 0.11660(16) 0.0206(5) Uani 1 1 d . . . . .
N41 N 0.3234(3) 0.4698(3) 0.08531(19) 0.0157(6) Uani 1 1 d . . . . .
H41 H 0.351(4) 0.531(3) 0.086(2) 0.024 Uiso 1 1 d . U . . .
N42 N 0.2942(3) 0.6762(2) -0.06542(19) 0.0191(6) Uani 1 1 d . . . . .
Cl41 Cl 0.06843(10) 0.24934(8) -0.06286(6) 0.02355(19) Uani 1 1 d . . . . .
C41 C 0.3456(4) 0.3726(3) 0.1616(2) 0.0187(7) Uani 1 1 d . . . . .
H41A H 0.392715 0.375723 0.212248 0.022 Uiso 1 1 calc R U . . .
C42 C 0.3001(4) 0.2672(3) 0.1670(2) 0.0186(8) Uani 1 1 d . . . . .
H42 H 0.316142 0.197150 0.221179 0.022 Uiso 1 1 calc R U . . .
C43 C 0.2317(4) 0.2644(3) 0.0936(2) 0.0168(7) Uani 1 1 d . . . . .
H43 H 0.201051 0.191685 0.096671 0.020 Uiso 1 1 calc R U . . .
C44 C 0.2065(3) 0.3681(3) 0.0140(2) 0.0143(7) Uani 1 1 d . . . . .
C45 C 0.2562(3) 0.4726(3) 0.0109(2) 0.0131(7) Uani 1 1 d . . . . .
C46 C 0.1303(4) 0.3770(3) -0.0647(2) 0.0166(7) Uani 1 1 d . . . . .
C47 C 0.1065(4) 0.4806(3) -0.1386(2) 0.0161(7) Uani 1 1 d . . . . .
H47 H 0.053686 0.483630 -0.188759 0.019 Uiso 1 1 calc R U . . .
C48 C 0.1601(3) 0.5858(3) -0.1421(2) 0.0142(7) Uani 1 1 d . . . . .
C49 C 0.2372(3) 0.5824(3) -0.0680(2) 0.0143(7) Uani 1 1 d . . . . .
C50 C 0.1385(4) 0.6959(3) -0.2172(2) 0.0182(7) Uani 1 1 d . . . . .
H50 H 0.086859 0.703475 -0.269230 0.022 Uiso 1 1 calc R U . . .
C51 C 0.1929(4) 0.7916(3) -0.2142(2) 0.0188(8) Uani 1 1 d . . . . .
H51 H 0.178155 0.867322 -0.263785 0.023 Uiso 1 1 calc R U . . .
H51A H 0.846(3) 0.047(3) 0.908(2) 0.028 Uiso 1 1 d D U . . .
C52 C 0.2709(4) 0.7778(3) -0.1374(2) 0.0202(8) Uani 1 1 d . . . . .
H52 H 0.308968 0.845417 -0.137152 0.024 Uiso 1 1 calc R U . . .
O51 O 0.9300(3) 0.0101(2) 0.87552(17) 0.0219(5) Uani 1 1 d D . . . .
H51B H 0.993(4) 0.058(3) 0.860(3) 0.033 Uiso 1 1 d D U . . .
O61 O 0.6505(3) 0.0989(2) 0.96339(17) 0.0251(6) Uani 1 1 d D . . . .
H61B H 0.606(4) 0.1812(19) 0.948(3) 0.038 Uiso 1 1 d D U . . .
H61A H 0.611(4) 0.075(3) 1.0221(16) 0.038 Uiso 1 1 d D U . . .
O71 O 0.5019(3) -0.0006(2) 1.13608(17) 0.0249(6) Uani 1 1 d D . . . .
H71A H 0.457(4) -0.040(3) 1.113(3) 0.037 Uiso 1 1 d D U . . .
H71B H 0.555(4) -0.053(3) 1.183(2) 0.037 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O13 2.215(2) . ?
Bi1 O23 2.330(2) . ?
Bi1 N21 2.429(2) . ?
Bi1 N11 2.457(2) . ?
Bi1 O21 2.532(2) . ?
Bi1 O21 2.559(2) 2_666 ?
Bi1 O11 2.724(2) . ?
Bi1 O31 2.755(2) . ?
N11 C16 1.328(4) . ?
N11 C12 1.340(4) . ?
O11 C11 1.222(4) . ?
O12 C11 1.296(4) . ?
O12 H12 0.851(18) . ?
O13 C17 1.300(4) . ?
O14 C17 1.213(4) . ?
C11 C12 1.495(4) . ?
C12 C13 1.378(4) . ?
C13 C14 1.382(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.508(4) . ?
N21 C26 1.337(4) . ?
N21 C22 1.344(4) . ?
O21 C21 1.289(3) . ?
O22 C21 1.224(4) . ?
O23 C27 1.283(4) . ?
O24 C27 1.223(4) . ?
C21 C22 1.504(4) . ?
C22 C23 1.386(4) . ?
C23 C24 1.377(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.513(4) . ?
N31 O32 1.247(3) . ?
N31 O31 1.252(3) . ?
N31 O33 1.263(3) . ?
N41 C41 1.327(4) . ?
N41 C45 1.351(4) . ?
N41 H41 0.83(4) . ?
N42 C52 1.319(4) . ?
N42 C49 1.353(4) . ?
Cl41 C46 1.726(3) . ?
C41 C42 1.380(5) . ?
C41 H41A 0.9500 . ?
C42 C43 1.369(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.401(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.401(4) . ?
C44 C46 1.435(5) . ?
C45 C49 1.435(4) . ?
C46 C47 1.349(4) . ?
C47 C48 1.428(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.402(4) . ?
C48 C50 1.405(4) . ?
C50 C51 1.360(5) . ?
C50 H50 0.9500 . ?
C51 C52 1.403(5) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
O51 H51A 0.882(18) . ?
O51 H51B 0.877(19) . ?
O61 H61B 0.882(19) . ?
O61 H61A 0.873(19) . ?
O71 H71A 0.869(19) . ?
O71 H71B 0.889(19) . ?

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
O13 Bi1 O23 86.04(7) . . ?
O13 Bi1 N21 74.50(8) . . ?
O23 Bi1 N21 67.70(7) . . ?
O13 Bi1 N11 69.10(8) . . ?
O23 Bi1 N11 72.00(7) . . ?
N21 Bi1 N11 126.59(8) . . ?
O13 Bi1 O21 78.16(7) . . ?
O23 Bi1 O21 132.49(7) . . ?
N21 Bi1 O21 64.95(7) . . ?
N11 Bi1 O21 137.75(7) . . ?
O13 Bi1 O21 81.23(7) . 2_666 ?
O23 Bi1 O21 153.48(7) . 2_666 ?
N21 Bi1 O21 129.59(7) . 2_666 ?
N11 Bi1 O21 81.72(7) . 2_666 ?
O21 Bi1 O21 67.21(7) . 2_666 ?
O13 Bi1 O11 131.29(7) . . ?
O23 Bi1 O11 79.10(7) . . ?
N21 Bi1 O11 136.76(7) . . ?
N11 Bi1 O11 62.19(7) . . ?
O21 Bi1 O11 142.41(7) . . ?
O21 Bi1 O11 91.98(6) 2_666 . ?
O13 Bi1 O31 147.13(7) . . ?
O23 Bi1 O31 67.18(7) . . ?
N21 Bi1 O31 77.74(7) . . ?
N11 Bi1 O31 116.50(7) . . ?
O21 Bi1 O31 105.54(6) . . ?
O21 Bi1 O31 130.85(7) 2_666 . ?
O11 Bi1 O31 63.92(6) . . ?
C16 N11 C12 119.7(3) . . ?
C16 N11 Bi1 114.68(19) . . ?
C12 N11 Bi1 125.6(2) . . ?
C11 O11 Bi1 116.3(2) . . ?
C11 O12 H12 109.5 . . ?
C17 O13 Bi1 124.19(19) . . ?
O11 C11 O12 126.1(3) . . ?
O11 C11 C12 121.0(3) . . ?
O12 C11 C12 112.9(3) . . ?
N11 C12 C13 121.9(3) . . ?
N11 C12 C11 114.2(3) . . ?
C13 C12 C11 123.8(3) . . ?
C12 C13 C14 118.5(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 118.3(3) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
N11 C16 C15 121.8(3) . . ?
N11 C16 C17 115.8(3) . . ?
C15 C16 C17 122.4(3) . . ?
O14 C17 O13 124.2(3) . . ?
O14 C17 C16 119.7(3) . . ?
O13 C17 C16 116.0(3) . . ?
C26 N21 C22 120.2(3) . . ?
C26 N21 Bi1 117.71(19) . . ?
C22 N21 Bi1 121.86(19) . . ?
C21 O21 Bi1 120.84(18) . . ?
C21 O21 Bi1 124.82(18) . 2_666 ?
Bi1 O21 Bi1 112.79(7) . 2_666 ?
C27 O23 Bi1 122.95(18) . . ?
O22 C21 O21 126.3(3) . . ?
O22 C21 C22 118.2(3) . . ?
O21 C21 C22 115.5(3) . . ?
N21 C22 C23 120.8(3) . . ?
N21 C22 C21 116.7(3) . . ?
C23 C22 C21 122.5(3) . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 119.5(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 118.4(3) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
N21 C26 C25 121.6(3) . . ?
N21 C26 C27 115.4(3) . . ?
C25 C26 C27 123.0(3) . . ?
O24 C27 O23 124.4(3) . . ?
O24 C27 C26 119.6(3) . . ?
O23 C27 C26 116.0(3) . . ?
O32 N31 O31 120.0(3) . . ?
O32 N31 O33 120.7(3) . . ?
O31 N31 O33 119.3(3) . . ?
N31 O31 Bi1 102.32(17) . . ?
C41 N41 C45 123.4(3) . . ?
C41 N41 H41 116(2) . . ?
C45 N41 H41 121(2) . . ?
C52 N42 C49 116.4(3) . . ?
N41 C41 C42 119.8(3) . . ?
N41 C41 H41A 120.1 . . ?
C42 C41 H41A 120.1 . . ?
C43 C42 C41 119.4(3) . . ?
C43 C42 H42 120.3 . . ?
C41 C42 H42 120.3 . . ?
C42 C43 C44 120.4(3) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C45 C44 C43 118.3(3) . . ?
C45 C44 C46 116.8(3) . . ?
C43 C44 C46 124.9(3) . . ?
N41 C45 C44 118.6(3) . . ?
N41 C45 C49 119.0(3) . . ?
C44 C45 C49 122.4(3) . . ?
C47 C46 C44 122.2(3) . . ?
C47 C46 Cl41 120.0(3) . . ?
C44 C46 Cl41 117.8(2) . . ?
C46 C47 C48 120.6(3) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C49 C48 C50 116.9(3) . . ?
C49 C48 C47 120.0(3) . . ?
C50 C48 C47 123.0(3) . . ?
N42 C49 C48 124.5(3) . . ?
N42 C49 C45 117.6(3) . . ?
C48 C49 C45 117.9(3) . . ?
C51 C50 C48 118.9(3) . . ?
C51 C50 H50 120.6 . . ?
C48 C50 H50 120.6 . . ?
C50 C51 C52 119.7(3) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 H51 120.2 . . ?
N42 C52 C51 123.6(3) . . ?
N42 C52 H52 118.2 . . ?
C51 C52 H52 118.2 . . ?
H51A O51 H51B 109(3) . . ?
H61B O61 H61A 103(3) . . ?
H71A O71 H71B 112(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O12 H12 O51 0.85 1.65 2.495(3) 170.4 2_666 yes
C25 H25 O11 0.95 2.58 3.373(4) 141.1 1_655 yes
N41 H41 O33 0.83(4) 1.98(4) 2.780(4) 163(3) . yes
C41 H41A O14 0.95 2.28 2.936(4) 125.1 2_666 yes
C41 H41A O32 0.95 2.52 3.304(4) 139.7 . yes
C42 H42 O14 0.95 2.51 3.041(4) 115.4 2_666 yes
O51 H51A O61 0.882(18) 1.81(2) 2.672(3) 165(3) . yes
O51 H51B O24 0.877(19) 2.01(3) 2.744(3) 141(3) 2_766 yes
O61 H61B O33 0.882(19) 1.94(2) 2.806(3) 165(4) 2_666 yes
O61 H61A O71 0.873(19) 1.90(2) 2.757(3) 166(4) . yes
O71 H71A O61 0.869(19) 2.01(2) 2.863(4) 168(4) 2_657 yes
O71 H71B O23 0.889(19) 2.09(2) 2.964(3) 167(3) 1_546 yes

_refine_diff_density_max         1.115
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.106



####################################################################### 
# 
# 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_p1_a
_database_code_depnum_ccdc_archive 'CCDC 2252255'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_PLAT417_p1_a                
;
PROBLEM: Short Inter D-H..H-D       H12      ..H41B     .       2.03 Ang.  
RESPONSE: These alerts involve lattice waters with hydrogens that are 
difficult and unreliable to determine the location of through x-ray diffraction.
There is likely hydrogen bonding that results in the close D-H..H-D contacts
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H14 Bi2 Cl2 N4 O16, 2(C12 H9 N2), 8(H2 O)'
_chemical_formula_sum            'C52 H48 Bi2 Cl2 N8 O24'
_chemical_formula_weight         1657.84

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'
Cl Cl 0.1484 0.1585 '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                   10.0241(4)
_cell_length_b                   11.9736(5)
_cell_length_c                   13.5032(6)
_cell_angle_alpha                112.4310(10)
_cell_angle_beta                 111.6370(10)
_cell_angle_gamma                91.0590(10)
_cell_volume                     1368.43(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.012
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.216
_exptl_absorpt_coefficient_mu    6.615
_shelx_estimated_absorpt_T_min   0.158
_shelx_estimated_absorpt_T_max   0.329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.17791
_exptl_absorpt_correction_T_max  0.34881
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35661
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.676
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5598
_reflns_number_gt                5509
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0154P)²+1.3361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Intrinsic
_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         5598
_refine_ls_number_parameters     427
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0141
_refine_ls_R_factor_gt           0.0137
_refine_ls_wR_factor_ref         0.0354
_refine_ls_wR_factor_gt          0.0352
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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 0.36434(2) 0.31723(2) 0.90270(2) 0.00656(3) Uani 1 1 d . . . . .
Cl1 Cl 0.12767(6) 0.37047(5) 0.74397(5) 0.01432(10) Uani 1 1 d . . . . .
O11 O 0.35795(16) 0.16858(13) 0.70226(13) 0.0106(3) Uani 1 1 d . . . . .
O12 O 0.45140(17) 0.02137(14) 0.60196(13) 0.0131(3) Uani 1 1 d D . . . .
H12 H 0.382(2) 0.0248(19) 0.5419(12) 0.020 Uiso 1 1 calc DR U . . .
O13 O 0.48418(17) 0.31354(14) 1.08654(13) 0.0136(3) Uani 1 1 d . . . . .
O14 O 0.63695(19) 0.24379(15) 1.20687(14) 0.0188(4) Uani 1 1 d . . . . .
N11 N 0.52592(19) 0.15944(16) 0.90361(15) 0.0088(3) Uani 1 1 d . . . . .
C11 C 0.4409(2) 0.09451(19) 0.69692(18) 0.0098(4) Uani 1 1 d . . . . .
C12 C 0.5370(2) 0.08177(19) 0.80614(18) 0.0100(4) Uani 1 1 d . . . . .
C13 C 0.6241(2) -0.0069(2) 0.80687(19) 0.0136(4) Uani 1 1 d . . . . .
H13 H 0.630888 -0.061266 0.736832 0.016 Uiso 1 1 calc R U . . .
C14 C 0.7011(3) -0.0138(2) 0.9128(2) 0.0159(5) Uani 1 1 d . . . . .
H14 H 0.761518 -0.073652 0.916094 0.019 Uiso 1 1 calc R U . . .
C15 C 0.6894(2) 0.0669(2) 1.01393(19) 0.0135(4) Uani 1 1 d . . . . .
H15 H 0.741523 0.063572 1.087144 0.016 Uiso 1 1 calc R U . . .
C16 C 0.5994(2) 0.15289(19) 1.00541(18) 0.0097(4) Uani 1 1 d . . . . .
C17 C 0.5733(2) 0.24267(19) 1.10841(18) 0.0110(4) Uani 1 1 d . . . . .
O21 O 0.39093(16) 0.53545(14) 1.04453(13) 0.0121(3) Uani 1 1 d . . . . .
O22 O 0.31911(17) 0.66569(14) 1.17662(14) 0.0149(3) Uani 1 1 d . . . . .
O23 O 0.21719(16) 0.13543(13) 0.84599(13) 0.0115(3) Uani 1 1 d . . . . .
O24 O 0.03742(17) 0.03374(14) 0.85574(14) 0.0147(3) Uani 1 1 d . . . . .
N21 N 0.19554(18) 0.34763(16) 0.99503(15) 0.0079(3) Uani 1 1 d . . . . .
C21 C 0.3102(2) 0.56333(19) 1.10152(18) 0.0096(4) Uani 1 1 d . . . . .
C22 C 0.1942(2) 0.45833(19) 1.07180(18) 0.0085(4) Uani 1 1 d . . . . .
C23 C 0.0908(2) 0.47367(19) 1.11900(18) 0.0102(4) Uani 1 1 d . . . . .
H23 H 0.091256 0.552167 1.174269 0.012 Uiso 1 1 calc R U . . .
C24 C -0.0135(2) 0.3731(2) 1.08470(19) 0.0120(4) Uani 1 1 d . . . . .
H24 H -0.087125 0.382731 1.114234 0.014 Uiso 1 1 calc R U . . .
C25 C -0.0092(2) 0.2587(2) 1.00699(19) 0.0109(4) Uani 1 1 d . . . . .
H25 H -0.078218 0.188313 0.983506 0.013 Uiso 1 1 calc R U . . .
C26 C 0.0988(2) 0.24947(19) 0.96425(18) 0.0089(4) Uani 1 1 d . . . . .
C27 C 0.1144(2) 0.12856(19) 0.88119(18) 0.0101(4) Uani 1 1 d . . . . .
N31 N 0.5004(2) 0.54040(18) 0.67273(16) 0.0113(4) Uani 1 1 d . . . . .
H31A H 0.516(3) 0.615(3) 0.714(3) 0.023(8) Uiso 1 1 d . . . . .
N32 N 0.7335(2) 0.69692(17) 0.70887(16) 0.0119(4) Uani 1 1 d . . . . .
C31 C 0.3821(2) 0.4711(2) 0.65601(19) 0.0135(4) Uani 1 1 d . . . . .
H31 H 0.316775 0.507929 0.689359 0.016 Uiso 1 1 calc R U . . .
C32 C 0.3541(2) 0.3452(2) 0.58999(19) 0.0135(4) Uani 1 1 d . . . . .
H32 H 0.268490 0.295559 0.576186 0.016 Uiso 1 1 calc R U . . .
C33 C 0.4514(2) 0.2930(2) 0.54472(19) 0.0126(4) Uani 1 1 d . . . . .
H33 H 0.433697 0.206553 0.500548 0.015 Uiso 1 1 calc R U . . .
C34 C 0.5766(2) 0.3659(2) 0.56304(18) 0.0107(4) Uani 1 1 d . . . . .
C35 C 0.5989(2) 0.49356(19) 0.62827(18) 0.0093(4) Uani 1 1 d . . . . .
C36 C 0.6827(2) 0.3162(2) 0.51949(19) 0.0131(4) Uani 1 1 d . . . . .
H36 H 0.668435 0.230176 0.474599 0.016 Uiso 1 1 calc R U . . .
C37 C 0.8031(2) 0.3906(2) 0.54172(19) 0.0124(4) Uani 1 1 d . . . . .
H37 H 0.873524 0.355773 0.513747 0.015 Uiso 1 1 calc R U . . .
C38 C 0.8263(2) 0.5214(2) 0.60693(18) 0.0112(4) Uani 1 1 d . . . . .
C39 C 0.7232(2) 0.57441(19) 0.64952(18) 0.0098(4) Uani 1 1 d . . . . .
C40 C 0.9498(2) 0.6025(2) 0.63182(19) 0.0146(4) Uani 1 1 d . . . . .
H40 H 1.024693 0.571628 0.607829 0.018 Uiso 1 1 calc R U . . .
C41 C 0.9605(2) 0.7261(2) 0.6909(2) 0.0158(5) Uani 1 1 d . . . . .
H41 H 1.042194 0.782216 0.707482 0.019 Uiso 1 1 calc R U . . .
C42 C 0.8496(2) 0.7693(2) 0.7270(2) 0.0145(4) Uani 1 1 d . . . . .
H42 H 0.858195 0.855594 0.766687 0.017 Uiso 1 1 calc R U . . .
O41 O 0.25117(17) 0.02996(15) 0.43128(14) 0.0139(3) Uani 1 1 d D . . . .
H41B H 0.218(3) -0.0446(18) 0.379(2) 0.021 Uiso 1 1 d D U . . .
H41A H 0.184(3) 0.065(2) 0.446(2) 0.021 Uiso 1 1 d D U . . .
O51 O 0.0429(2) 0.1325(2) 0.49114(18) 0.0391(6) Uani 1 1 d D . . . .
H51B H -0.043(3) 0.105(4) 0.437(3) 0.059 Uiso 1 1 d D U . . .
H51A H 0.049(4) 0.172(3) 0.562(2) 0.059 Uiso 1 1 d D U . . .
O61 O -0.14833(19) 0.20060(15) 0.72072(15) 0.0179(3) Uani 1 1 d D . . . .
H61B H -0.197(3) 0.247(2) 0.755(3) 0.027 Uiso 1 1 d D U . . .
H61A H -0.078(3) 0.243(3) 0.723(3) 0.027 Uiso 1 1 d D U . . .
O71 O 0.76842(18) 0.09305(15) 1.31876(14) 0.0166(3) Uani 1 1 d D . . . .
H71B H 0.770(3) 0.022(2) 1.263(2) 0.025 Uiso 1 1 d D U . . .
H71A H 0.726(3) 0.136(3) 1.279(2) 0.025 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O23 2.2972(14) . ?
Bi1 O13 2.3438(15) . ?
Bi1 N21 2.4046(17) . ?
Bi1 N11 2.5118(17) . ?
Bi1 O21 2.5190(15) . ?
Bi1 O11 2.5863(15) . ?
Bi1 O21 2.6888(15) 2_667 ?
Bi1 Cl1 2.8245(5) . ?
O11 C11 1.227(3) . ?
O12 C11 1.292(3) . ?
O12 H12 0.867(17) . ?
O13 C17 1.277(3) . ?
O14 C17 1.239(3) . ?
N11 C16 1.333(3) . ?
N11 C12 1.337(3) . ?
C11 C12 1.502(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.515(3) . ?
O21 C21 1.277(3) . ?
O22 C21 1.232(3) . ?
O23 C27 1.297(3) . ?
O24 C27 1.215(3) . ?
N21 C26 1.335(3) . ?
N21 C22 1.339(3) . ?
C21 C22 1.520(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.509(3) . ?
N31 C31 1.330(3) . ?
N31 C35 1.360(3) . ?
N31 H31A 0.83(3) . ?
N32 C42 1.325(3) . ?
N32 C39 1.357(3) . ?
C31 C32 1.386(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.374(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.401(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.406(3) . ?
C34 C36 1.432(3) . ?
C35 C39 1.433(3) . ?
C36 C37 1.353(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.437(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.409(3) . ?
C38 C40 1.410(3) . ?
C40 C41 1.367(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.403(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
O41 H41B 0.860(17) . ?
O41 H41A 0.842(17) . ?
O51 H51B 0.853(19) . ?
O51 H51A 0.868(19) . ?
O61 H61B 0.865(18) . ?
O61 H61A 0.847(18) . ?
O71 H71B 0.896(18) . ?
O71 H71A 0.891(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O23 Bi1 O13 87.78(5) . . ?
O23 Bi1 N21 68.41(5) . . ?
O13 Bi1 N21 72.34(5) . . ?
O23 Bi1 N11 73.39(5) . . ?
O13 Bi1 N11 65.89(5) . . ?
N21 Bi1 N11 123.38(6) . . ?
O23 Bi1 O21 133.65(5) . . ?
O13 Bi1 O21 76.62(5) . . ?
N21 Bi1 O21 65.30(5) . . ?
N11 Bi1 O21 133.15(5) . . ?
O23 Bi1 O11 73.05(5) . . ?
O13 Bi1 O11 128.58(5) . . ?
N21 Bi1 O11 135.11(5) . . ?
N11 Bi1 O11 62.99(5) . . ?
O21 Bi1 O11 148.07(5) . . ?
O23 Bi1 O21 156.63(5) . 2_667 ?
O13 Bi1 O21 86.54(5) . 2_667 ?
N21 Bi1 O21 130.55(5) . 2_667 ?
N11 Bi1 O21 83.61(5) . 2_667 ?
O21 Bi1 O21 66.52(5) . 2_667 ?
O11 Bi1 O21 93.06(5) . 2_667 ?
O23 Bi1 Cl1 87.83(4) . . ?
O13 Bi1 Cl1 150.01(4) . . ?
N21 Bi1 Cl1 78.47(4) . . ?
N11 Bi1 Cl1 139.97(4) . . ?
O21 Bi1 Cl1 85.18(4) . . ?
O11 Bi1 Cl1 77.94(3) . . ?
O21 Bi1 Cl1 107.97(4) 2_667 . ?
C11 O11 Bi1 120.48(13) . . ?
C11 O12 H12 109.5 . . ?
C17 O13 Bi1 125.16(13) . . ?
C16 N11 C12 120.05(18) . . ?
C16 N11 Bi1 117.65(13) . . ?
C12 N11 Bi1 122.28(14) . . ?
O11 C11 O12 125.0(2) . . ?
O11 C11 C12 119.83(19) . . ?
O12 C11 C12 115.11(18) . . ?
N11 C12 C13 122.0(2) . . ?
N11 C12 C11 114.15(18) . . ?
C13 C12 C11 123.79(19) . . ?
C12 C13 C14 118.2(2) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 118.4(2) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
N11 C16 C15 121.69(19) . . ?
N11 C16 C17 114.97(18) . . ?
C15 C16 C17 123.32(19) . . ?
O14 C17 O13 123.9(2) . . ?
O14 C17 C16 119.79(19) . . ?
O13 C17 C16 116.31(18) . . ?
C21 O21 Bi1 120.90(13) . . ?
C21 O21 Bi1 124.18(13) . 2_667 ?
Bi1 O21 Bi1 113.48(5) . 2_667 ?
C27 O23 Bi1 123.16(13) . . ?
C26 N21 C22 120.54(18) . . ?
C26 N21 Bi1 117.20(13) . . ?
C22 N21 Bi1 122.23(13) . . ?
O22 C21 O21 125.9(2) . . ?
O22 C21 C22 118.76(19) . . ?
O21 C21 C22 115.35(18) . . ?
N21 C22 C23 120.73(19) . . ?
N21 C22 C21 116.10(18) . . ?
C23 C22 C21 123.17(19) . . ?
C22 C23 C24 119.3(2) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 119.4(2) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 118.3(2) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
N21 C26 C25 121.68(19) . . ?
N21 C26 C27 116.05(18) . . ?
C25 C26 C27 122.27(19) . . ?
O24 C27 O23 124.9(2) . . ?
O24 C27 C26 119.99(19) . . ?
O23 C27 C26 115.03(18) . . ?
C31 N31 C35 123.0(2) . . ?
C31 N31 H31A 118(2) . . ?
C35 N31 H31A 119(2) . . ?
C42 N32 C39 116.39(19) . . ?
N31 C31 C32 120.0(2) . . ?
N31 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 119.3(2) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 120.7(2) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C35 118.1(2) . . ?
C33 C34 C36 123.0(2) . . ?
C35 C34 C36 118.9(2) . . ?
N31 C35 C34 118.88(19) . . ?
N31 C35 C39 119.68(19) . . ?
C34 C35 C39 121.44(19) . . ?
C37 C36 C34 120.6(2) . . ?
C37 C36 H36 119.7 . . ?
C34 C36 H36 119.7 . . ?
C36 C37 C38 121.2(2) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 H37 119.4 . . ?
C39 C38 C40 116.8(2) . . ?
C39 C38 C37 120.1(2) . . ?
C40 C38 C37 123.1(2) . . ?
N32 C39 C38 124.37(19) . . ?
N32 C39 C35 117.82(19) . . ?
C38 C39 C35 117.82(19) . . ?
C41 C40 C38 119.1(2) . . ?
C41 C40 H40 120.4 . . ?
C38 C40 H40 120.4 . . ?
C40 C41 C42 119.4(2) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
N32 C42 C41 123.9(2) . . ?
N32 C42 H42 118.0 . . ?
C41 C42 H42 118.0 . . ?
H41B O41 H41A 112(3) . . ?
H51B O51 H51A 117(4) . . ?
H61B O61 H61A 111(3) . . ?
H71B O71 H71A 103(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O12 H12 O41 0.87 1.61 2.475(2) 178.5 . yes
C15 H15 O24 0.95 2.53 3.200(3) 128.0 2_657 yes
N31 H31A O13 0.83(3) 2.50(3) 2.988(2) 119(2) 2_667 yes
N31 H31A O14 0.83(3) 2.51(3) 3.129(2) 133(3) 2_667 yes
O41 H41B O61 0.860(17) 1.770(18) 2.628(2) 176(3) 2_556 yes
O41 H41A O51 0.842(17) 1.827(18) 2.665(3) 173(3) . yes
O51 H51B O71 0.853(19) 1.93(2) 2.757(3) 162(4) 1_454 yes
O51 H51A Cl1 0.868(19) 2.52(3) 3.293(2) 149(3) . yes
O61 H61B O22 0.865(18) 1.890(18) 2.752(2) 174(3) 2_567 yes
O61 H61A Cl1 0.847(18) 2.403(18) 3.2487(18) 176(3) . yes
O71 H71B O23 0.896(18) 1.946(18) 2.839(2) 175(3) 2_657 yes
O71 H71A O14 0.891(18) 1.937(18) 2.824(2) 174(3) . yes

_refine_diff_density_max         0.635
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.087



####################################################################### 
# 
# 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_final2_a
_database_code_depnum_ccdc_archive 'CCDC 2252256'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT417_final2_a            
;
PROBLEM: Short Inter D-H..H-D       H22A     ..H61B     .       2.03 Ang.  
RESPONSE: These alerts involve lattice waters with hydrogens that are 
difficult and unreliable to determine the location of through x-ray diffraction.
There is likely hydrogen bonding that results in the close D-H..H-D contacts.
;
_vrf_PLAT420_final2_a            
;
PROBLEM: D-H Bond Without Acceptor  O51      --H51A     .     Please Check 
RESPONSE: H51B is involved in a strong hydrogen bond with both N52 and Cl52. This
causes H51A to be rotated slightly away from the potential acceptor Cl51. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H16 Bi2 N4 O17, C12 H6 Cl2 N2, 4(H2 O)'
_chemical_formula_sum            'C40 H30 Bi2 Cl2 N6 O21'
_chemical_formula_weight         1419.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   9.121(2)
_cell_length_b                   12.323(3)
_cell_length_c                   21.183(5)
_cell_angle_alpha                85.845(3)
_cell_angle_beta                 83.706(3)
_cell_angle_gamma                68.570(3)
_cell_volume                     2201.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8965
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.141
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    8.198
_shelx_estimated_absorpt_T_min   0.361
_shelx_estimated_absorpt_T_max   0.635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55603
_exptl_absorpt_correction_T_max  0.81481
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29870
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         26.385
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9031
_reflns_number_gt                7002
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by Intrinsic methods (Sheldrick, 
2015).  Systematic conditions suggested the ambiguous space group.  
The space group choice was confirmed by successful convergence of the 
full-matrix least-squares refinement on F².  A final analysis of 
variance between observed and calculated structure factors showed little 
dependence on amplitude and resolution.  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Intrinsic
_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         9031
_refine_ls_number_parameters     674
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.64852(2) 0.60795(2) 0.30937(2) 0.01415(6) Uani 1 1 d . . . . .
Bi2 Bi 0.90523(2) 0.35344(2) 0.18005(2) 0.01389(6) Uani 1 1 d . . . . .
N11 N 0.3878(4) 0.6557(3) 0.27196(17) 0.0143(9) Uani 1 1 d . . . . .
O11 O 0.6463(4) 0.5140(3) 0.20645(14) 0.0176(7) Uani 1 1 d . . . . .
O12 O 0.4985(4) 0.4719(3) 0.14050(15) 0.0226(8) Uani 1 1 d . . . . .
O13 O 0.4486(4) 0.7276(3) 0.37670(14) 0.0168(7) Uani 1 1 d . . . . .
O14 O 0.1994(4) 0.8449(3) 0.39740(15) 0.0202(8) Uani 1 1 d . . . . .
C11 C 0.5133(6) 0.5231(4) 0.1854(2) 0.0169(11) Uani 1 1 d . . . . .
C12 C 0.3660(6) 0.6061(4) 0.2204(2) 0.0160(11) Uani 1 1 d . . . . .
C13 C 0.2146(5) 0.6291(4) 0.2027(2) 0.0180(11) Uani 1 1 d . . . . .
H13 H 0.200633 0.594305 0.167416 0.022 Uiso 1 1 calc R U . . .
C15 C 0.1097(6) 0.7541(4) 0.2910(2) 0.0175(11) Uani 1 1 d . . . . .
H15 H 0.024557 0.804004 0.315729 0.021 Uiso 1 1 calc R U . . .
C14 C 0.0853(6) 0.7041(4) 0.2379(2) 0.0210(11) Uani 1 1 d . . . . .
H14 H -0.016453 0.720935 0.226472 0.025 Uiso 1 1 calc R U . . .
C16 C 0.2635(6) 0.7279(4) 0.3062(2) 0.0148(10) Uani 1 1 d . . . . .
C17 C 0.3035(6) 0.7722(4) 0.3645(2) 0.0153(10) Uani 1 1 d . . . . .
N21 N 0.7087(4) 0.5415(3) 0.41777(16) 0.0139(8) Uani 1 1 d . . . . .
O21 O 0.7739(4) 0.7284(3) 0.36828(14) 0.0181(8) Uani 1 1 d . . . . .
O22 O 0.8513(5) 0.7528(3) 0.46170(15) 0.0269(9) Uani 1 1 d D . . . .
H22A H 0.864(7) 0.813(3) 0.4418(10) 0.040 Uiso 1 1 calc DR U . . .
O23 O 0.5702(4) 0.4563(3) 0.34115(14) 0.0177(7) Uani 1 1 d . . . . .
O24 O 0.5854(4) 0.3054(3) 0.40786(16) 0.0264(9) Uani 1 1 d . . . . .
C21 C 0.7976(5) 0.7005(4) 0.4245(2) 0.0177(11) Uani 1 1 d . . . . .
C22 C 0.7693(5) 0.5960(4) 0.4548(2) 0.0162(10) Uani 1 1 d . . . . .
C23 C 0.7998(6) 0.5564(4) 0.5169(2) 0.0191(11) Uani 1 1 d . . . . .
H23 H 0.838881 0.595708 0.542595 0.023 Uiso 1 1 calc R U . . .
C24 C 0.7705(6) 0.4568(5) 0.5398(2) 0.0221(12) Uani 1 1 d . . . . .
H24 H 0.792472 0.427481 0.580786 0.027 Uiso 1 1 calc R U . . .
C25 C 0.7088(6) 0.4017(5) 0.5012(2) 0.0195(11) Uani 1 1 d . . . . .
H25 H 0.687818 0.335365 0.515846 0.023 Uiso 1 1 calc R U . . .
C26 C 0.6784(5) 0.4478(4) 0.4398(2) 0.0151(10) Uani 1 1 d . . . . .
C27 C 0.6070(6) 0.3961(4) 0.3939(2) 0.0175(11) Uani 1 1 d . . . . .
N31 N 1.1670(5) 0.3065(4) 0.21699(17) 0.0159(9) Uani 1 1 d . . . . .
O31 O 0.9041(4) 0.4317(3) 0.28595(14) 0.0195(8) Uani 1 1 d . . . . .
O32 O 1.0451(4) 0.4751(3) 0.35398(15) 0.0245(8) Uani 1 1 d . . . . .
O33 O 1.1077(4) 0.2410(3) 0.10947(14) 0.0194(8) Uani 1 1 d . . . . .
O34 O 1.3604(4) 0.1324(3) 0.08618(16) 0.0252(8) Uani 1 1 d . . . . .
C31 C 1.0349(6) 0.4267(5) 0.3076(2) 0.0185(11) Uani 1 1 d . . . . .
C32 C 1.1847(6) 0.3515(4) 0.2701(2) 0.0167(11) Uani 1 1 d . . . . .
C33 C 1.3346(6) 0.3331(5) 0.2878(2) 0.0223(12) Uani 1 1 d . . . . .
H33 H 1.346614 0.365571 0.324317 0.027 Uiso 1 1 calc R U . . .
C34 C 1.4650(6) 0.2659(5) 0.2503(2) 0.0259(13) Uani 1 1 d . . . . .
H34 H 1.566127 0.252795 0.261365 0.031 Uiso 1 1 calc R U . . .
C35 C 1.4454(6) 0.2177(5) 0.1960(2) 0.0217(12) Uani 1 1 d . . . . .
H35 H 1.532424 0.170865 0.170812 0.026 Uiso 1 1 calc R U . . .
C36 C 1.2935(6) 0.2409(4) 0.1804(2) 0.0154(10) Uani 1 1 d . . . . .
C37 C 1.2553(6) 0.2000(4) 0.1210(2) 0.0173(11) Uani 1 1 d . . . . .
N41 N 0.8244(4) 0.4345(3) 0.07682(17) 0.0135(8) Uani 1 1 d . . . . .
O41 O 0.7868(4) 0.2332(3) 0.11563(15) 0.0185(7) Uani 1 1 d . . . . .
O42 O 0.6774(4) 0.2303(3) 0.02622(15) 0.0225(8) Uani 1 1 d D . . . .
H42A H 0.673(6) 0.167(3) 0.0426(13) 0.034 Uiso 1 1 calc DR U . . .
O43 O 0.9694(4) 0.5084(3) 0.15561(14) 0.0178(7) Uani 1 1 d . . . . .
O44 O 0.9437(4) 0.6697(3) 0.09653(15) 0.0236(8) Uani 1 1 d . . . . .
C41 C 0.7415(5) 0.2753(4) 0.0637(2) 0.0170(11) Uani 1 1 d . . . . .
C42 C 0.7540(5) 0.3876(4) 0.0394(2) 0.0162(10) Uani 1 1 d . . . . .
C43 C 0.6950(5) 0.4454(5) -0.0169(2) 0.0187(11) Uani 1 1 d . . . . .
H43 H 0.649508 0.412122 -0.043410 0.022 Uiso 1 1 calc R U . . .
C44 C 0.7061(6) 0.5531(5) -0.0320(2) 0.0191(11) Uani 1 1 d . . . . .
H44 H 0.666229 0.593543 -0.068934 0.023 Uiso 1 1 calc R U . . .
C45 C 0.7756(6) 0.6011(5) 0.0070(2) 0.0180(11) Uani 1 1 d . . . . .
H45 H 0.782021 0.674137 -0.002839 0.022 Uiso 1 1 calc R U . . .
C46 C 0.8365(5) 0.5373(4) 0.0619(2) 0.0151(10) Uani 1 1 d . . . . .
C47 C 0.9209(5) 0.5782(4) 0.1073(2) 0.0152(10) Uani 1 1 d . . . . .
O51 O 0.6166(5) 0.8149(4) 0.25238(17) 0.0322(9) Uani 1 1 d D . . . .
H51B H 0.565(6) 0.854(5) 0.2186(19) 0.048 Uiso 1 1 d D U . . .
H51A H 0.625(7) 0.871(4) 0.275(2) 0.048 Uiso 1 1 d D U . . .
N51 N 0.3367(6) 1.0201(4) 0.3043(2) 0.0311(11) Uani 1 1 d . . . . .
N52 N 0.3200(6) 0.9278(4) 0.19343(19) 0.0272(11) Uani 1 1 d . . . . .
Cl51 Cl 0.5287(2) 1.03316(15) 0.38143(8) 0.0486(4) Uani 1 1 d . . . . .
Cl52 Cl 0.48647(18) 0.80030(15) 0.10032(7) 0.0439(4) Uani 1 1 d . . . . .
C51 C 0.3393(8) 1.0633(5) 0.3583(3) 0.0353(14) Uani 1 1 d . . . . .
C52 C 0.2075(8) 1.1306(5) 0.3981(3) 0.0357(15) Uani 1 1 d . . . . .
H52 H 0.220449 1.158950 0.435757 0.043 Uiso 1 1 calc R U . . .
C53 C 0.0614(8) 1.1525(5) 0.3796(3) 0.0339(14) Uani 1 1 d . . . . .
H53 H -0.028768 1.195299 0.404750 0.041 Uiso 1 1 calc R U . . .
C54 C 0.0490(7) 1.1081(5) 0.3206(3) 0.0304(13) Uani 1 1 d . . . . .
C55 C 0.1897(7) 1.0433(5) 0.2850(2) 0.0263(13) Uani 1 1 d . . . . .
C56 C -0.0996(7) 1.1257(5) 0.2978(3) 0.0337(14) Uani 1 1 d . . . . .
H56 H -0.192536 1.167356 0.321795 0.040 Uiso 1 1 calc R U . . .
C57 C -0.1077(7) 1.0829(5) 0.2419(2) 0.0338(14) Uani 1 1 d . . . . .
H57 H -0.206017 1.096417 0.227719 0.041 Uiso 1 1 calc R U . . .
C58 C 0.0326(7) 1.0170(5) 0.2041(2) 0.0304(13) Uani 1 1 d . . . . .
C59 C 0.1816(7) 0.9953(5) 0.2257(2) 0.0269(13) Uani 1 1 d . . . . .
C60 C 0.0284(6) 0.9700(5) 0.1442(2) 0.0289(13) Uani 1 1 d . . . . .
H60 H -0.067675 0.983690 0.127932 0.035 Uiso 1 1 calc R U . . .
C61 C 0.1660(7) 0.9058(5) 0.1119(3) 0.0329(14) Uani 1 1 d . . . . .
H61 H 0.166957 0.874820 0.073062 0.039 Uiso 1 1 calc R U . . .
C62 C 0.3076(7) 0.8875(5) 0.1392(2) 0.0309(13) Uani 1 1 d . . . . .
O61 O 0.8848(4) 0.9314(3) 0.41571(16) 0.0214(8) Uani 1 1 d D . . . .
H61B H 0.986(3) 0.916(5) 0.407(2) 0.032 Uiso 1 1 d D U . . .
H61A H 0.834(6) 0.991(3) 0.439(2) 0.032 Uiso 1 1 d D U . . .
O71 O 0.7328(6) 1.1102(4) 0.48390(19) 0.0486(13) Uani 1 1 d D . . . .
H71B H 0.662(7) 1.171(4) 0.466(3) 0.073 Uiso 1 1 d D U . . .
H71A H 0.729(9) 1.130(6) 0.5230(15) 0.073 Uiso 1 1 d D U . . .
O81 O 0.6810(4) 0.0348(3) 0.06663(18) 0.0269(9) Uani 1 1 d D . . . .
H81B H 0.582(3) 0.043(5) 0.071(3) 0.040 Uiso 1 1 d D U . . .
H81A H 0.748(6) -0.027(3) 0.045(2) 0.040 Uiso 1 1 d D U . . .
O91 O 0.9127(5) -0.1423(4) 0.00979(17) 0.0340(10) Uani 1 1 d D . . . .
H91B H 0.915(8) -0.194(4) 0.041(2) 0.051 Uiso 1 1 d D U . . .
H91A H 0.888(7) -0.160(5) -0.0257(17) 0.051 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O23 2.268(3) . ?
Bi1 O13 2.303(3) . ?
Bi1 N21 2.433(3) . ?
Bi1 N11 2.440(4) . ?
Bi1 O11 2.547(3) . ?
Bi1 O31 2.570(3) . ?
Bi1 O21 2.625(3) . ?
Bi1 O51 2.671(4) . ?
Bi2 O43 2.205(3) . ?
Bi2 O33 2.322(3) . ?
Bi2 N41 2.413(4) . ?
Bi2 N31 2.446(4) . ?
Bi2 O31 2.502(3) . ?
Bi2 O11 2.502(3) . ?
Bi2 O41 2.648(3) . ?
N11 C16 1.334(6) . ?
N11 C12 1.355(6) . ?
O11 C11 1.302(5) . ?
O12 C11 1.224(5) . ?
O13 C17 1.281(6) . ?
O14 C17 1.230(6) . ?
C11 C12 1.513(7) . ?
C12 C13 1.393(6) . ?
C13 C14 1.383(7) . ?
C13 H13 0.9300 . ?
C15 C16 1.388(6) . ?
C15 C14 1.395(6) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C16 C17 1.517(6) . ?
N21 C26 1.324(6) . ?
N21 C22 1.347(6) . ?
O21 C21 1.235(5) . ?
O22 C21 1.291(5) . ?
O22 H22A 0.86(2) . ?
O23 C27 1.301(5) . ?
O24 C27 1.215(6) . ?
C21 C22 1.491(7) . ?
C22 C23 1.391(6) . ?
C23 C24 1.393(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.397(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.517(6) . ?
N31 C32 1.339(6) . ?
N31 C36 1.341(6) . ?
O31 C31 1.304(5) . ?
O32 C31 1.214(5) . ?
O33 C37 1.297(6) . ?
O34 C37 1.228(6) . ?
C31 C32 1.517(7) . ?
C32 C33 1.392(6) . ?
C33 C34 1.378(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.389(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.508(6) . ?
N41 C46 1.324(6) . ?
N41 C42 1.351(6) . ?
O41 C41 1.228(5) . ?
O42 C41 1.298(5) . ?
O42 H42A 0.84(2) . ?
O43 C47 1.295(5) . ?
O44 C47 1.221(6) . ?
C41 C42 1.480(7) . ?
C42 C43 1.398(6) . ?
C43 C44 1.379(7) . ?
C43 H43 0.9300 . ?
C44 C45 1.377(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.405(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.512(6) . ?
O51 H51B 0.91(2) . ?
O51 H51A 0.89(2) . ?
N51 C51 1.303(7) . ?
N51 C55 1.367(7) . ?
N52 C62 1.316(7) . ?
N52 C59 1.370(7) . ?
Cl51 C51 1.747(6) . ?
Cl52 C62 1.746(6) . ?
C51 C52 1.412(8) . ?
C52 C53 1.355(8) . ?
C52 H52 0.9300 . ?
C53 C54 1.432(8) . ?
C53 H53 0.9300 . ?
C54 C55 1.406(8) . ?
C54 C56 1.426(8) . ?
C55 C59 1.447(7) . ?
C56 C57 1.351(8) . ?
C56 H56 0.9300 . ?
C57 C58 1.431(8) . ?
C57 H57 0.9300 . ?
C58 C59 1.408(7) . ?
C58 C60 1.442(7) . ?
C60 C61 1.354(8) . ?
C60 H60 0.9300 . ?
C61 C62 1.408(7) . ?
C61 H61 0.9300 . ?
O61 H61B 0.87(2) . ?
O61 H61A 0.86(2) . ?
O71 H71B 0.88(2) . ?
O71 H71A 0.88(2) . ?
O81 H81B 0.87(2) . ?
O81 H81A 0.90(2) . ?
O91 H91B 0.89(2) . ?
O91 H91A 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O23 Bi1 O13 89.99(12) . . ?
O23 Bi1 N21 68.38(12) . . ?
O13 Bi1 N21 72.40(12) . . ?
O23 Bi1 N11 73.64(12) . . ?
O13 Bi1 N11 67.35(12) . . ?
N21 Bi1 N11 123.53(12) . . ?
O23 Bi1 O11 75.64(11) . . ?
O13 Bi1 O11 132.19(10) . . ?
N21 Bi1 O11 136.50(12) . . ?
N11 Bi1 O11 64.86(11) . . ?
O23 Bi1 O31 78.04(11) . . ?
O13 Bi1 O31 153.01(10) . . ?
N21 Bi1 O31 80.68(11) . . ?
N11 Bi1 O31 129.76(11) . . ?
O11 Bi1 O31 68.41(10) . . ?
O23 Bi1 O21 132.60(10) . . ?
O13 Bi1 O21 73.41(10) . . ?
N21 Bi1 O21 64.32(11) . . ?
N11 Bi1 O21 132.60(12) . . ?
O11 Bi1 O21 146.45(10) . . ?
O31 Bi1 O21 96.94(10) . . ?
O23 Bi1 O51 154.69(12) . . ?
O13 Bi1 O51 80.23(12) . . ?
N21 Bi1 O51 128.80(12) . . ?
N11 Bi1 O51 81.05(12) . . ?
O11 Bi1 O51 93.69(11) . . ?
O31 Bi1 O51 119.81(11) . . ?
O21 Bi1 O51 66.78(11) . . ?
O43 Bi2 O33 91.73(12) . . ?
O43 Bi2 N41 69.43(12) . . ?
O33 Bi2 N41 75.94(12) . . ?
O43 Bi2 N31 74.15(12) . . ?
O33 Bi2 N31 67.28(12) . . ?
N41 Bi2 N31 126.48(12) . . ?
O43 Bi2 O31 76.47(11) . . ?
O33 Bi2 O31 132.51(11) . . ?
N41 Bi2 O31 136.33(12) . . ?
N31 Bi2 O31 65.24(12) . . ?
O43 Bi2 O11 78.96(11) . . ?
O33 Bi2 O11 153.04(10) . . ?
N41 Bi2 O11 77.10(11) . . ?
N31 Bi2 O11 131.91(12) . . ?
O31 Bi2 O11 70.16(10) . . ?
O43 Bi2 O41 133.03(10) . . ?
O33 Bi2 O41 72.55(11) . . ?
N41 Bi2 O41 63.90(12) . . ?
N31 Bi2 O41 131.96(12) . . ?
O31 Bi2 O41 145.40(10) . . ?
O11 Bi2 O41 95.33(10) . . ?
C16 N11 C12 120.0(4) . . ?
C16 N11 Bi1 117.8(3) . . ?
C12 N11 Bi1 122.1(3) . . ?
C11 O11 Bi2 124.5(3) . . ?
C11 O11 Bi1 120.6(3) . . ?
Bi2 O11 Bi1 110.90(11) . . ?
C17 O13 Bi1 124.0(3) . . ?
O12 C11 O11 126.0(5) . . ?
O12 C11 C12 118.6(4) . . ?
O11 C11 C12 115.4(4) . . ?
N11 C12 C13 120.8(4) . . ?
N11 C12 C11 116.4(4) . . ?
C13 C12 C11 122.8(4) . . ?
C14 C13 C12 119.4(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C16 C15 C14 118.8(5) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N11 C16 C15 121.9(4) . . ?
N11 C16 C17 114.6(4) . . ?
C15 C16 C17 123.3(4) . . ?
O14 C17 O13 124.0(4) . . ?
O14 C17 C16 120.3(4) . . ?
O13 C17 C16 115.7(4) . . ?
C26 N21 C22 120.4(4) . . ?
C26 N21 Bi1 116.8(3) . . ?
C22 N21 Bi1 122.8(3) . . ?
C21 O21 Bi1 116.9(3) . . ?
C21 O22 H22A 109.5 . . ?
C27 O23 Bi1 123.2(3) . . ?
O21 C21 O22 125.7(5) . . ?
O21 C21 C22 120.6(4) . . ?
O22 C21 C22 113.6(4) . . ?
N21 C22 C23 121.1(4) . . ?
N21 C22 C21 115.1(4) . . ?
C23 C22 C21 123.8(4) . . ?
C22 C23 C24 118.6(4) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 119.6(4) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 118.6(5) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
N21 C26 C25 121.7(4) . . ?
N21 C26 C27 115.3(4) . . ?
C25 C26 C27 123.0(4) . . ?
O24 C27 O23 124.3(4) . . ?
O24 C27 C26 120.3(4) . . ?
O23 C27 C26 115.4(4) . . ?
C32 N31 C36 120.7(4) . . ?
C32 N31 Bi2 121.0(3) . . ?
C36 N31 Bi2 118.2(3) . . ?
C31 O31 Bi2 121.3(3) . . ?
C31 O31 Bi1 119.9(3) . . ?
Bi2 O31 Bi1 110.15(11) . . ?
C37 O33 Bi2 123.4(3) . . ?
O32 C31 O31 126.0(5) . . ?
O32 C31 C32 119.4(4) . . ?
O31 C31 C32 114.6(4) . . ?
N31 C32 C33 120.8(5) . . ?
N31 C32 C31 116.9(4) . . ?
C33 C32 C31 122.3(4) . . ?
C34 C33 C32 118.8(4) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C33 C34 C35 120.0(5) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 118.4(5) . . ?
C36 C35 H35 120.8 . . ?
C34 C35 H35 120.8 . . ?
N31 C36 C35 121.4(4) . . ?
N31 C36 C37 114.6(4) . . ?
C35 C36 C37 124.0(5) . . ?
O34 C37 O33 123.3(4) . . ?
O34 C37 C36 120.6(4) . . ?
O33 C37 C36 116.2(4) . . ?
C46 N41 C42 120.9(4) . . ?
C46 N41 Bi2 115.0(3) . . ?
C42 N41 Bi2 123.6(3) . . ?
C41 O41 Bi2 116.5(3) . . ?
C41 O42 H42A 109.5 . . ?
C47 O43 Bi2 123.5(3) . . ?
O41 C41 O42 125.2(5) . . ?
O41 C41 C42 120.9(4) . . ?
O42 C41 C42 113.9(4) . . ?
N41 C42 C43 120.7(5) . . ?
N41 C42 C41 114.9(4) . . ?
C43 C42 C41 124.3(4) . . ?
C44 C43 C42 118.3(4) . . ?
C44 C43 H43 120.9 . . ?
C42 C43 H43 120.9 . . ?
C45 C44 C43 120.6(4) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C44 C45 C46 118.4(5) . . ?
C44 C45 H45 120.8 . . ?
C46 C45 H45 120.8 . . ?
N41 C46 C45 121.0(4) . . ?
N41 C46 C47 115.4(4) . . ?
C45 C46 C47 123.6(4) . . ?
O44 C47 O43 124.0(4) . . ?
O44 C47 C46 120.5(4) . . ?
O43 C47 C46 115.4(4) . . ?
Bi1 O51 H51B 133(4) . . ?
Bi1 O51 H51A 119(4) . . ?
H51B O51 H51A 104(5) . . ?
C51 N51 C55 115.5(5) . . ?
C62 N52 C59 116.5(5) . . ?
N51 C51 C52 126.8(6) . . ?
N51 C51 Cl51 114.5(5) . . ?
C52 C51 Cl51 118.7(4) . . ?
C53 C52 C51 117.9(5) . . ?
C53 C52 H52 121.0 . . ?
C51 C52 H52 121.0 . . ?
C52 C53 C54 118.4(6) . . ?
C52 C53 H53 120.8 . . ?
C54 C53 H53 120.8 . . ?
C55 C54 C56 119.6(5) . . ?
C55 C54 C53 118.0(5) . . ?
C56 C54 C53 122.3(5) . . ?
N51 C55 C54 123.3(5) . . ?
N51 C55 C59 117.2(5) . . ?
C54 C55 C59 119.6(5) . . ?
C57 C56 C54 121.0(5) . . ?
C57 C56 H56 119.5 . . ?
C54 C56 H56 119.5 . . ?
C56 C57 C58 121.1(5) . . ?
C56 C57 H57 119.4 . . ?
C58 C57 H57 119.4 . . ?
C59 C58 C57 119.6(5) . . ?
C59 C58 C60 117.8(5) . . ?
C57 C58 C60 122.6(5) . . ?
N52 C59 C58 122.5(5) . . ?
N52 C59 C55 118.5(5) . . ?
C58 C59 C55 119.1(5) . . ?
C61 C60 C58 119.2(5) . . ?
C61 C60 H60 120.4 . . ?
C58 C60 H60 120.4 . . ?
C60 C61 C62 117.8(5) . . ?
C60 C61 H61 121.1 . . ?
C62 C61 H61 121.1 . . ?
N52 C62 C61 126.2(5) . . ?
N52 C62 Cl52 114.9(4) . . ?
C61 C62 Cl52 118.9(4) . . ?
H61B O61 H61A 117(5) . . ?
H71B O71 H71A 104(6) . . ?
H81B O81 H81A 117(5) . . ?
H91B O91 H91A 114(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15 O61 0.93 2.65 3.512(6) 155.2 1_455 yes
O22 H22A O61 0.86 1.59 2.450(5) 171.1 . yes
C23 H23 O32 0.93 2.50 3.151(5) 127.5 2_766 yes
O42 H42A O81 0.84 1.65 2.487(5) 172.3 . yes
C43 H43 O12 0.93 2.62 3.213(5) 122.1 2_665 yes
O51 H51B N52 0.91(2) 2.19(4) 2.924(6) 137(5) . yes
O51 H51B Cl52 0.91(2) 2.86(4) 3.591(4) 138(5) . yes
O51 H51A Cl51 0.89(2) 2.97(3) 3.789(4) 153(5) . yes
C52 H52 O22 0.93 2.42 3.299(6) 158.4 2_676 yes
C61 H61 O42 0.93 2.55 3.385(6) 149.3 2_665 yes
O61 H61B O14 0.87(2) 1.81(2) 2.664(5) 164(5) 1_655 yes
O61 H61A O71 0.86(2) 1.72(2) 2.579(5) 179(6) . yes
O71 H71B O24 0.88(2) 1.95(3) 2.782(5) 157(7) 1_565 yes
O71 H71A O14 0.88(2) 1.95(3) 2.794(5) 160(7) 2_676 yes
O81 H81B O34 0.87(2) 1.92(3) 2.721(5) 153(6) 1_455 yes
O81 H81A O91 0.90(2) 1.78(2) 2.671(6) 168(6) . yes
O91 H91B O44 0.89(2) 1.93(2) 2.800(5) 168(6) 1_545 yes
O91 H91A O33 0.87(2) 2.09(3) 2.934(5) 164(6) 2_755 yes
O91 H91A O34 0.87(2) 2.63(4) 3.347(5) 140(5) 2_755 yes

_refine_diff_density_max         0.951
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.141



####################################################################### 
# 
# 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_final2_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2252253'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT417_final2_a            
;
PROBLEM: Short Inter D-H..H-D       H12      ..H51B     .       2.08 Ang.  
RESPONSE: These alerts involve lattice waters with hydrogens that are 
difficult and unreliable to determine the location of through x-ray diffraction.
There is likely hydrogen bonding that results in the close D-H..H-D contacts.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H14 Bi2 N6 O22, 2(C13 H11 N2), 6(H2 O)'
_chemical_formula_sum            'C54 H48 Bi2 N10 O28'
_chemical_formula_weight         1702.98

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'

_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                   9.1883(7)
_cell_length_b                   11.5124(13)
_cell_length_c                   14.9478(17)
_cell_angle_alpha                72.800(3)
_cell_angle_beta                 78.455(3)
_cell_angle_gamma                71.506(3)
_cell_volume                     1422.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9738
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.40

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    6.281
_shelx_estimated_absorpt_T_min   0.480
_shelx_estimated_absorpt_T_max   0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55603
_exptl_absorpt_correction_T_max  0.81481
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22010
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.598
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5824
_reflns_number_gt                5499
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by Intrinsic methods (Sheldrick, 
2015).  Systematic conditions suggested the ambiguous space group.  
The space group choice was confirmed by successful convergence of the 
full-matrix least-squares refinement on F².  A final analysis of 
variance between observed and calculated structure factors showed little 
dependence on amplitude and resolution.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0110P)²+0.9378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Intrinsic
_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         5824
_refine_ls_number_parameters     451
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0163
_refine_ls_wR_factor_ref         0.0352
_refine_ls_wR_factor_gt          0.0344
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.47055(2) 0.33290(2) 0.10127(2) 0.00943(3) Uani 1 1 d . . . . .
O11 O 0.70861(18) 0.17438(15) 0.20123(11) 0.0150(4) Uani 1 1 d . . . . .
O12 O 0.87898(19) -0.01834(16) 0.22272(12) 0.0183(4) Uani 1 1 d D . . . .
H12 H 0.887(2) -0.0036(13) 0.2729(14) 0.027 Uiso 1 1 calc DR U . . .
O13 O 0.38597(18) 0.32144(15) -0.02397(11) 0.0133(3) Uani 1 1 d . . . . .
O14 O 0.40952(19) 0.23176(16) -0.14129(12) 0.0191(4) Uani 1 1 d . . . . .
N11 N 0.6282(2) 0.14276(17) 0.04767(13) 0.0109(4) Uani 1 1 d . . . . .
C11 C 0.7763(3) 0.0762(2) 0.17714(17) 0.0134(5) Uani 1 1 d . . . . .
C12 C 0.7466(3) 0.0545(2) 0.08955(17) 0.0120(5) Uani 1 1 d . . . . .
C13 C 0.8338(3) -0.0465(2) 0.05235(17) 0.0145(5) Uani 1 1 d . . . . .
H13 H 0.917522 -0.108027 0.082613 0.017 Uiso 1 1 calc R U . . .
C14 C 0.7961(3) -0.0558(2) -0.03016(18) 0.0162(5) Uani 1 1 d . . . . .
H14 H 0.855297 -0.123335 -0.057795 0.019 Uiso 1 1 calc R U . . .
C15 C 0.6717(3) 0.0338(2) -0.07205(17) 0.0144(5) Uani 1 1 d . . . . .
H15 H 0.642464 0.027695 -0.127617 0.017 Uiso 1 1 calc R U . . .
C16 C 0.5907(3) 0.1330(2) -0.03046(16) 0.0122(5) Uani 1 1 d . . . . .
C17 C 0.4528(3) 0.2355(2) -0.07058(16) 0.0127(5) Uani 1 1 d . . . . .
O21 O 0.34738(17) 0.56340(14) 0.02778(11) 0.0137(3) Uani 1 1 d . . . . .
O22 O 0.12942(19) 0.72352(16) 0.01271(14) 0.0236(4) Uani 1 1 d . . . . .
O23 O 0.36626(17) 0.16494(14) 0.18458(11) 0.0122(3) Uani 1 1 d . . . . .
O24 O 0.16409(19) 0.09739(15) 0.26390(12) 0.0174(4) Uani 1 1 d . . . . .
N21 N 0.1900(2) 0.40068(17) 0.13086(13) 0.0102(4) Uani 1 1 d . . . . .
C21 C 0.1999(3) 0.6125(2) 0.04112(17) 0.0137(5) Uani 1 1 d . . . . .
C22 C 0.1084(3) 0.5202(2) 0.09680(16) 0.0114(5) Uani 1 1 d . . . . .
C23 C -0.0519(3) 0.5556(2) 0.10908(17) 0.0142(5) Uani 1 1 d . . . . .
H23 H -0.108465 0.640945 0.085657 0.017 Uiso 1 1 calc R U . . .
C24 C -0.1281(3) 0.4645(2) 0.15607(17) 0.0156(5) Uani 1 1 d . . . . .
H24 H -0.237859 0.486510 0.164217 0.019 Uiso 1 1 calc R U . . .
C25 C -0.0433(3) 0.3408(2) 0.19121(17) 0.0144(5) Uani 1 1 d . . . . .
H25 H -0.093673 0.277150 0.223780 0.017 Uiso 1 1 calc R U . . .
C26 C 0.1176(3) 0.3123(2) 0.17756(16) 0.0115(5) Uani 1 1 d . . . . .
C27 C 0.2215(3) 0.1807(2) 0.21265(16) 0.0115(5) Uani 1 1 d . . . . .
N31 N 0.4923(2) 0.37898(18) 0.30225(14) 0.0150(4) Uani 1 1 d . . . . .
O31 O 0.42366(19) 0.30571(16) 0.29402(12) 0.0175(4) Uani 1 1 d . . . . .
O32 O 0.5100(2) 0.47057(16) 0.23461(12) 0.0200(4) Uani 1 1 d . . . . .
O33 O 0.5443(2) 0.36025(16) 0.37935(12) 0.0209(4) Uani 1 1 d . . . . .
N41 N 0.6741(2) 0.53097(18) 0.41200(14) 0.0146(4) Uani 1 1 d . . . . .
H41 H 0.644427 0.464342 0.414680 0.018 Uiso 1 1 calc R U . . .
N42 N 0.7081(2) 0.32372(19) 0.56153(15) 0.0182(5) Uani 1 1 d . . . . .
C41 C 0.6505(3) 0.6277(2) 0.33620(17) 0.0172(5) Uani 1 1 d . . . . .
H41A H 0.604250 0.623426 0.286253 0.021 Uiso 1 1 calc R U . . .
C42 C 0.6938(3) 0.7349(2) 0.33055(18) 0.0185(5) Uani 1 1 d . . . . .
H42 H 0.676900 0.804825 0.277016 0.022 Uiso 1 1 calc R U . . .
C43 C 0.7616(3) 0.7386(2) 0.40337(17) 0.0165(5) Uani 1 1 d . . . . .
H43 H 0.789918 0.812387 0.400116 0.020 Uiso 1 1 calc R U . . .
C44 C 0.7900(3) 0.6349(2) 0.48283(17) 0.0137(5) Uani 1 1 d . . . . .
C45 C 0.7414(3) 0.5295(2) 0.48542(17) 0.0140(5) Uani 1 1 d . . . . .
C46 C 0.8660(3) 0.6317(2) 0.55974(17) 0.0155(5) Uani 1 1 d . . . . .
C47 C 0.8905(3) 0.5255(2) 0.63185(17) 0.0160(5) Uani 1 1 d . . . . .
H47 H 0.943760 0.522239 0.681233 0.019 Uiso 1 1 calc R U . . .
C48 C 0.8392(3) 0.4185(2) 0.63638(17) 0.0145(5) Uani 1 1 d . . . . .
C49 C 0.7628(3) 0.4197(2) 0.56388(17) 0.0142(5) Uani 1 1 d . . . . .
C50 C 0.8608(3) 0.3089(2) 0.71163(18) 0.0182(5) Uani 1 1 d . . . . .
H50 H 0.912001 0.302654 0.762824 0.022 Uiso 1 1 calc R U . . .
C51 C 0.8071(3) 0.2115(2) 0.70995(18) 0.0190(5) Uani 1 1 d . . . . .
H51 H 0.821061 0.136688 0.759816 0.023 Uiso 1 1 calc R U . . .
C52 C 0.7312(3) 0.2234(2) 0.63391(18) 0.0206(6) Uani 1 1 d . . . . .
H52 H 0.693950 0.155066 0.634378 0.025 Uiso 1 1 calc R U . . .
C53 C 0.9127(3) 0.7456(2) 0.55930(18) 0.0206(6) Uani 1 1 d . . . . .
H53A H 0.968436 0.774975 0.497739 0.031 Uiso 1 1 calc R U . . .
H53B H 0.979864 0.723119 0.608662 0.031 Uiso 1 1 calc R U . . .
H53C H 0.820215 0.813192 0.571198 0.031 Uiso 1 1 calc R U . . .
O51 O 0.9255(2) 0.00900(17) 0.37463(13) 0.0190(4) Uani 1 1 d D . . . .
H51B H 0.992(3) 0.053(2) 0.357(2) 0.025(8) Uiso 1 1 d D . . . .
H51A H 0.838(3) 0.046(3) 0.403(2) 0.047(10) Uiso 1 1 d D . . . .
O61 O 0.6454(2) 0.10116(18) 0.46189(14) 0.0235(4) Uani 1 1 d D . . . .
H61B H 0.601(4) 0.1840(18) 0.447(2) 0.050(11) Uiso 1 1 d D . . . .
H61A H 0.603(4) 0.078(4) 0.5206(16) 0.069(13) Uiso 1 1 d D . . . .
O71 O 0.5083(2) -0.00339(17) 0.63574(14) 0.0234(4) Uani 1 1 d D . . . .
H71B H 0.552(4) -0.052(3) 0.6847(18) 0.051(11) Uiso 1 1 d D . . . .
H71A H 0.467(4) -0.051(3) 0.620(2) 0.054(12) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O13 2.2179(16) . ?
Bi1 O23 2.3413(15) . ?
Bi1 N21 2.4334(18) . ?
Bi1 N11 2.4685(19) . ?
Bi1 O21 2.5293(15) . ?
Bi1 O21 2.5609(15) 2_665 ?
Bi1 O11 2.7406(16) . ?
O11 C11 1.225(3) . ?
O12 C11 1.306(3) . ?
O12 H12 0.837(17) . ?
O13 C17 1.301(3) . ?
O14 C17 1.218(3) . ?
N11 C16 1.326(3) . ?
N11 C12 1.343(3) . ?
C11 C12 1.493(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.514(3) . ?
O21 C21 1.292(3) . ?
O22 C21 1.224(3) . ?
O23 C27 1.284(3) . ?
O24 C27 1.229(3) . ?
N21 C26 1.338(3) . ?
N21 C22 1.341(3) . ?
C21 C22 1.513(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.514(3) . ?
N31 O31 1.247(3) . ?
N31 O32 1.254(3) . ?
N31 O33 1.269(3) . ?
N41 C41 1.330(3) . ?
N41 C45 1.357(3) . ?
N41 H41 0.8800 . ?
N42 C52 1.322(3) . ?
N42 C49 1.363(3) . ?
C41 C42 1.387(4) . ?
C41 H41A 0.9500 . ?
C42 C43 1.375(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.411(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.408(3) . ?
C44 C46 1.446(3) . ?
C45 C49 1.439(3) . ?
C46 C47 1.360(3) . ?
C46 C53 1.502(3) . ?
C47 C48 1.432(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.398(3) . ?
C48 C50 1.410(3) . ?
C50 C51 1.369(4) . ?
C50 H50 0.9500 . ?
C51 C52 1.400(4) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
O51 H51B 0.861(17) . ?
O51 H51A 0.876(18) . ?
O61 H61B 0.888(18) . ?
O61 H61A 0.885(19) . ?
O71 H71B 0.863(18) . ?
O71 H71A 0.862(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13 Bi1 O23 85.89(6) . . ?
O13 Bi1 N21 74.57(6) . . ?
O23 Bi1 N21 67.69(6) . . ?
O13 Bi1 N11 68.95(6) . . ?
O23 Bi1 N11 71.95(6) . . ?
N21 Bi1 N11 126.56(6) . . ?
O13 Bi1 O21 78.20(5) . . ?
O23 Bi1 O21 132.40(5) . . ?
N21 Bi1 O21 64.88(5) . . ?
N11 Bi1 O21 137.70(6) . . ?
O13 Bi1 O21 81.12(6) . 2_665 ?
O23 Bi1 O21 153.66(5) . 2_665 ?
N21 Bi1 O21 129.24(6) . 2_665 ?
N11 Bi1 O21 81.99(5) . 2_665 ?
O21 Bi1 O21 66.90(6) . 2_665 ?
O13 Bi1 O11 131.13(5) . . ?
O23 Bi1 O11 78.87(5) . . ?
N21 Bi1 O11 136.52(6) . . ?
N11 Bi1 O11 62.18(6) . . ?
O21 Bi1 O11 142.74(5) . . ?
O21 Bi1 O11 92.60(5) 2_665 . ?
C11 O11 Bi1 115.86(15) . . ?
C11 O12 H12 109.5 . . ?
C17 O13 Bi1 124.36(14) . . ?
C16 N11 C12 119.9(2) . . ?
C16 N11 Bi1 114.71(14) . . ?
C12 N11 Bi1 125.38(15) . . ?
O11 C11 O12 125.3(2) . . ?
O11 C11 C12 121.4(2) . . ?
O12 C11 C12 113.3(2) . . ?
N11 C12 C13 121.7(2) . . ?
N11 C12 C11 114.54(19) . . ?
C13 C12 C11 123.8(2) . . ?
C12 C13 C14 118.5(2) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 118.2(2) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
N11 C16 C15 122.0(2) . . ?
N11 C16 C17 115.7(2) . . ?
C15 C16 C17 122.3(2) . . ?
O14 C17 O13 124.4(2) . . ?
O14 C17 C16 119.6(2) . . ?
O13 C17 C16 116.0(2) . . ?
C21 O21 Bi1 121.27(14) . . ?
C21 O21 Bi1 124.07(14) . 2_665 ?
Bi1 O21 Bi1 113.09(6) . 2_665 ?
C27 O23 Bi1 122.66(14) . . ?
C26 N21 C22 120.32(19) . . ?
C26 N21 Bi1 117.54(14) . . ?
C22 N21 Bi1 122.00(15) . . ?
O22 C21 O21 126.6(2) . . ?
O22 C21 C22 118.3(2) . . ?
O21 C21 C22 115.1(2) . . ?
N21 C22 C23 121.3(2) . . ?
N21 C22 C21 116.63(19) . . ?
C23 C22 C21 122.0(2) . . ?
C24 C23 C22 118.9(2) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 119.6(2) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 118.4(2) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
N21 C26 C25 121.4(2) . . ?
N21 C26 C27 115.69(19) . . ?
C25 C26 C27 122.9(2) . . ?
O24 C27 O23 124.7(2) . . ?
O24 C27 C26 119.4(2) . . ?
O23 C27 C26 115.92(19) . . ?
O31 N31 O32 120.1(2) . . ?
O31 N31 O33 119.6(2) . . ?
O32 N31 O33 120.2(2) . . ?
C41 N41 C45 123.5(2) . . ?
C41 N41 H41 118.2 . . ?
C45 N41 H41 118.2 . . ?
C52 N42 C49 116.0(2) . . ?
N41 C41 C42 119.6(2) . . ?
N41 C41 H41A 120.2 . . ?
C42 C41 H41A 120.2 . . ?
C43 C42 C41 119.2(2) . . ?
C43 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
C42 C43 C44 121.3(2) . . ?
C42 C43 H43 119.4 . . ?
C44 C43 H43 119.4 . . ?
C45 C44 C43 117.0(2) . . ?
C45 C44 C46 119.3(2) . . ?
C43 C44 C46 123.7(2) . . ?
N41 C45 C44 119.3(2) . . ?
N41 C45 C49 119.2(2) . . ?
C44 C45 C49 121.4(2) . . ?
C47 C46 C44 118.7(2) . . ?
C47 C46 C53 121.7(2) . . ?
C44 C46 C53 119.6(2) . . ?
C46 C47 C48 122.7(2) . . ?
C46 C47 H47 118.7 . . ?
C48 C47 H47 118.7 . . ?
C49 C48 C50 116.7(2) . . ?
C49 C48 C47 119.9(2) . . ?
C50 C48 C47 123.4(2) . . ?
N42 C49 C48 124.8(2) . . ?
N42 C49 C45 117.3(2) . . ?
C48 C49 C45 117.9(2) . . ?
C51 C50 C48 119.1(2) . . ?
C51 C50 H50 120.4 . . ?
C48 C50 H50 120.4 . . ?
C50 C51 C52 119.3(2) . . ?
C50 C51 H51 120.4 . . ?
C52 C51 H51 120.4 . . ?
N42 C52 C51 124.1(2) . . ?
N42 C52 H52 117.9 . . ?
C51 C52 H52 117.9 . . ?
C46 C53 H53A 109.5 . . ?
C46 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C46 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
H51B O51 H51A 114(3) . . ?
H61B O61 H61A 102(3) . . ?
H71B O71 H71A 104(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O12 H12 O51 0.84 1.69 2.517(2) 171.9 . yes
C25 H25 O11 0.95 2.58 3.370(3) 140.7 1_455 yes
N41 H41 O33 0.88 1.96 2.795(3) 158.6 . yes
C41 H41A O14 0.95 2.31 2.950(3) 124.2 2_665 yes
C41 H41A O32 0.95 2.55 3.337(3) 140.9 . yes
C42 H42 O14 0.95 2.51 3.042(3) 115.7 2_665 yes
O51 H51B O24 0.861(17) 1.98(2) 2.747(2) 147(3) 1_655 yes
O51 H51A O61 0.876(18) 1.815(19) 2.682(3) 170(3) . yes
O61 H61B O33 0.888(18) 1.93(2) 2.794(3) 162(3) . yes
O61 H61A O71 0.885(19) 1.89(2) 2.755(3) 166(4) . yes
O71 H71B O23 0.863(18) 2.129(19) 2.988(2) 173(3) 2_656 yes
O71 H71A O61 0.862(18) 2.05(2) 2.863(3) 157(3) 2_656 yes

_refine_diff_density_max         0.795
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.090



