# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
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data_32088001_0m
_database_code_depnum_ccdc_archive 'CCDC 2218896'
loop_
_audit_author_name
_audit_author_address
'Laura Valencia Matarranz'
;Universidade de Vigo
Spain
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;
_audit_creation_date             2022-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 Bi N4 O8, 5(H2 O)'
_chemical_formula_sum            'C23 H33 Bi N4 O13'
_chemical_formula_weight         782.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0759(7)
_cell_length_b                   11.0409(7)
_cell_length_c                   12.3655(7)
_cell_angle_alpha                102.261(2)
_cell_angle_beta                 95.473(2)
_cell_angle_gamma                92.621(2)
_cell_volume                     1335.04(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9537
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.572
_shelx_estimated_absorpt_T_min   0.402
_exptl_absorpt_coefficient_mu    6.679
_exptl_absorpt_correction_T_max  0.4920
_exptl_absorpt_correction_T_min  0.3741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1198 before and 0.0510 after correction. The Ratio of minimum to maximum transmission is 0.7604. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            65778
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         2.035
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6562
_reflns_number_total             6647
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0122
_refine_ls_R_factor_gt           0.0119
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0016P)²+1.2462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0285
_refine_ls_wR_factor_ref         0.0286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5W(H5WA,H5WB), O4W(H4WA,H4WB), O2W(H2WA), O1W(H1WA,H1WB), O3W(H3WA,H3WB)
2.b Ternary CH refined with riding coordinates:
 C12(H12), C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C7(H7A,H7B), C11(H11A,H11B), C20(H20A,H20B), C10(H10A,H10B),
 C9(H9A,H9B), C22(H22A,H22B)
2.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C3(H3), C4(H4A), C5(H5)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.30923(2) 0.37521(2) 0.22519(2) 0.00831(2) Uani 1 1 d . . . . .
O3 O 0.55029(12) 0.32888(11) 0.14190(10) 0.0143(2) Uani 1 1 d . . . . .
O2 O 0.26901(12) 0.60414(11) 0.56803(10) 0.0162(2) Uani 1 1 d . . . . .
O5W O 0.55835(12) 0.64852(13) 0.10461(10) 0.0193(3) Uani 1 1 d . . . . .
H5WA H 0.478316 0.612011 0.092415 0.029 Uiso 1 1 d G . . . .
H5WB H 0.593304 0.640525 0.042024 0.029 Uiso 1 1 d G . . . .
O7 O 0.30783(11) 0.54233(11) 0.11093(10) 0.0153(2) Uani 1 1 d . . . . .
O8 O 0.18616(12) 0.67638(11) 0.03733(10) 0.0142(2) Uani 1 1 d . . . . .
O4 O 0.64969(12) 0.18006(11) 0.03096(10) 0.0170(2) Uani 1 1 d . . . . .
H4 H 0.692165 0.241173 0.016989 0.025 Uiso 1 1 calc GR . . . .
O5 O 0.25666(11) 0.26075(10) 0.04579(9) 0.0125(2) Uani 1 1 d . . . . .
O1 O 0.23652(12) 0.51178(11) 0.38719(9) 0.0144(2) Uani 1 1 d . . . . .
O6 O 0.13407(13) 0.10481(11) -0.07040(10) 0.0182(2) Uani 1 1 d . . . . .
N4 N 0.09293(13) 0.45248(12) 0.18731(11) 0.0097(2) Uani 1 1 d . . . . .
O4W O 0.65856(14) 0.88925(13) 0.20395(12) 0.0250(3) Uani 1 1 d . . . . .
H4WA H 0.728239 0.892564 0.167924 0.037 Uiso 1 1 d G . . . .
H4WB H 0.620341 0.815431 0.176323 0.037 Uiso 1 1 d G . . . .
O2W O 0.15278(16) 0.81423(15) 0.52827(15) 0.0337(3) Uani 1 1 d . . . . .
H2WA H 0.070397 0.802282 0.497895 0.051 Uiso 1 1 d G . . . .
O1W O -0.11205(15) 0.75808(14) 0.45076(12) 0.0278(3) Uani 1 1 d . . . . .
H1WA H -0.155433 0.822489 0.442679 0.042 Uiso 1 1 d G . . . .
H1WB H -0.116077 0.705640 0.386942 0.042 Uiso 1 1 d G . . . .
O3W O 0.26523(16) 1.04814(14) 0.56952(13) 0.0310(3) Uani 1 1 d . . . . .
H3WA H 0.288469 1.071279 0.640818 0.046 Uiso 1 1 d G . . . .
H3WB H 0.220834 0.976066 0.554978 0.046 Uiso 1 1 d G . . . .
C18 C 0.07914(15) 0.55087(14) 0.14039(12) 0.0105(3) Uani 1 1 d . . . . .
N2 N 0.40865(13) 0.15250(12) 0.22450(11) 0.0104(2) Uani 1 1 d . . . . .
C15 C -0.13089(16) 0.46048(15) 0.23247(13) 0.0133(3) Uani 1 1 d . . . . .
H15 H -0.202827 0.427080 0.263896 0.016 Uiso 1 1 calc R . . . .
C16 C -0.14634(16) 0.56276(16) 0.18447(14) 0.0148(3) Uani 1 1 d . . . . .
H16 H -0.228966 0.600868 0.183505 0.018 Uiso 1 1 calc R . . . .
N1 N 0.39442(13) 0.33341(12) 0.41815(11) 0.0109(2) Uani 1 1 d . . . . .
C19 C 0.20086(16) 0.59389(14) 0.09177(13) 0.0116(3) Uani 1 1 d . . . . .
C14 C -0.00817(15) 0.40821(14) 0.23350(12) 0.0107(3) Uani 1 1 d . . . . .
C17 C -0.03977(16) 0.60877(15) 0.13788(13) 0.0130(3) Uani 1 1 d . . . . .
H17 H -0.048434 0.678685 0.104930 0.016 Uiso 1 1 calc R . . . .
N3 N 0.12169(13) 0.22585(12) 0.22497(11) 0.0098(2) Uani 1 1 d . . . . .
C21 C 0.56324(15) 0.21969(15) 0.10118(13) 0.0119(3) Uani 1 1 d . . . . .
C3 C 0.41643(16) 0.40367(16) 0.61600(13) 0.0140(3) Uani 1 1 d . . . . .
H3 H 0.397878 0.462680 0.679788 0.017 Uiso 1 1 calc R . . . .
C1 C 0.28429(16) 0.51897(15) 0.48773(13) 0.0128(3) Uani 1 1 d . . . . .
C13 C 0.01994(15) 0.29833(14) 0.28555(13) 0.0114(3) Uani 1 1 d . . . . .
H13A H 0.053737 0.327745 0.365135 0.014 Uiso 1 1 calc R . . . .
H13B H -0.063251 0.245194 0.280470 0.014 Uiso 1 1 calc R . . . .
C6 C 0.47010(15) 0.23954(15) 0.42846(13) 0.0117(3) Uani 1 1 d . . . . .
C7 C 0.50938(16) 0.16214(15) 0.32265(13) 0.0121(3) Uani 1 1 d . . . . .
H7A H 0.595019 0.198392 0.306478 0.015 Uiso 1 1 calc R . . . .
H7B H 0.524445 0.077513 0.333973 0.015 Uiso 1 1 calc R . . . .
C4 C 0.49282(17) 0.30424(16) 0.62676(14) 0.0160(3) Uani 1 1 d . . . . .
H4A H 0.526142 0.293621 0.698415 0.019 Uiso 1 1 calc R . . . .
C5 C 0.51989(16) 0.22076(16) 0.53198(14) 0.0147(3) Uani 1 1 d . . . . .
H5 H 0.571465 0.152038 0.537672 0.018 Uiso 1 1 calc R . . . .
C2 C 0.36786(15) 0.41465(15) 0.50965(13) 0.0116(3) Uani 1 1 d . . . . .
C23 C 0.15918(16) 0.17698(15) 0.02099(13) 0.0119(3) Uani 1 1 d . . . . .
C11 C 0.07907(16) 0.02254(14) 0.29569(13) 0.0130(3) Uani 1 1 d . . . . .
H11A H 0.055462 0.034088 0.372962 0.016 Uiso 1 1 calc R . . . .
H11B H -0.003900 0.017395 0.244665 0.016 Uiso 1 1 calc R . . . .
C20 C 0.47855(16) 0.11292(14) 0.12424(13) 0.0117(3) Uani 1 1 d . . . . .
H20A H 0.411874 0.079971 0.059251 0.014 Uiso 1 1 calc R . . . .
H20B H 0.536303 0.045299 0.134862 0.014 Uiso 1 1 calc R . . . .
C10 C 0.15607(18) -0.09564(15) 0.26450(15) 0.0176(3) Uani 1 1 d . . . . .
H10A H 0.144186 -0.150618 0.317010 0.021 Uiso 1 1 calc R . . . .
H10B H 0.124280 -0.142255 0.188127 0.021 Uiso 1 1 calc R . . . .
C9 C 0.30324(17) -0.04868(15) 0.27210(14) 0.0155(3) Uani 1 1 d . . . . .
H9A H 0.344973 -0.027242 0.350116 0.019 Uiso 1 1 calc R . . . .
H9B H 0.355676 -0.110463 0.227262 0.019 Uiso 1 1 calc R . . . .
C22 C 0.06417(16) 0.17034(15) 0.10845(13) 0.0116(3) Uani 1 1 d . . . . .
H22A H -0.016515 0.213567 0.091144 0.014 Uiso 1 1 calc R . . . .
H22B H 0.035623 0.082125 0.103343 0.014 Uiso 1 1 calc R . . . .
C12 C 0.17667(15) 0.13062(14) 0.28395(13) 0.0104(3) Uani 1 1 d . . . . .
H12 H 0.215696 0.174594 0.360369 0.012 Uiso 1 1 calc R . . . .
C8 C 0.28941(15) 0.06675(14) 0.22317(13) 0.0107(3) Uani 1 1 d . . . . .
H8 H 0.252688 0.036825 0.143395 0.013 Uiso 1 1 calc R . . . .
H2WB H 0.192(3) 0.746(3) 0.531(3) 0.056(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O3 2.7549(12) . ?
Bi1 O7 2.5510(12) . ?
Bi1 O5 2.3071(11) . ?
Bi1 O1 2.4334(11) . ?
Bi1 N4 2.4171(13) . ?
Bi1 N2 2.6959(13) . ?
Bi1 N1 2.5993(13) . ?
Bi1 N3 2.4499(13) . ?
O3 C21 1.222(2) . ?
O2 C1 1.241(2) . ?
O5W H5WA 0.8699 . ?
O5W H5WB 0.8698 . ?
O7 C19 1.2675(19) . ?
O8 C19 1.2484(19) . ?
O4 H4 0.8400 . ?
O4 C21 1.312(2) . ?
O5 C23 1.2858(19) . ?
O1 C1 1.2744(19) . ?
O6 C23 1.2331(19) . ?
N4 C18 1.342(2) . ?
N4 C14 1.337(2) . ?
O4W H4WA 0.8701 . ?
O4W H4WB 0.8702 . ?
O2W H2WA 0.8700 . ?
O2W H2WB 0.87(3) . ?
O1W H1WA 0.8701 . ?
O1W H1WB 0.8702 . ?
O3W H3WA 0.8700 . ?
O3W H3WB 0.8700 . ?
C18 C19 1.516(2) . ?
C18 C17 1.384(2) . ?
N2 C7 1.4882(19) . ?
N2 C20 1.4794(19) . ?
N2 C8 1.4919(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(2) . ?
C15 C14 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(2) . ?
N1 C6 1.335(2) . ?
N1 C2 1.344(2) . ?
C14 C13 1.515(2) . ?
C17 H17 0.9500 . ?
N3 C13 1.490(2) . ?
N3 C22 1.4902(19) . ?
N3 C12 1.4988(19) . ?
C21 C20 1.515(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C3 C2 1.391(2) . ?
C1 C2 1.512(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C6 C7 1.501(2) . ?
C6 C5 1.390(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C4 H4A 0.9500 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9500 . ?
C23 C22 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.546(2) . ?
C11 C12 1.551(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.536(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.529(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C8 1.537(2) . ?
C8 H8 1.0000 . ?

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
O7 Bi1 O3 83.07(4) . . ?
O7 Bi1 N2 139.44(4) . . ?
O7 Bi1 N1 142.52(4) . . ?
O5 Bi1 O3 74.32(4) . . ?
O5 Bi1 O7 77.54(4) . . ?
O5 Bi1 O1 148.23(4) . . ?
O5 Bi1 N4 81.74(4) . . ?
O5 Bi1 N2 74.67(4) . . ?
O5 Bi1 N1 137.22(4) . . ?
O5 Bi1 N3 71.81(4) . . ?
O1 Bi1 O3 135.57(4) . . ?
O1 Bi1 O7 93.73(4) . . ?
O1 Bi1 N2 124.90(4) . . ?
O1 Bi1 N1 63.57(4) . . ?
O1 Bi1 N3 89.71(4) . . ?
N4 Bi1 O3 143.65(4) . . ?
N4 Bi1 O7 65.10(4) . . ?
N4 Bi1 O1 67.04(4) . . ?
N4 Bi1 N2 136.95(4) . . ?
N4 Bi1 N1 122.82(4) . . ?
N4 Bi1 N3 66.37(4) . . ?
N2 Bi1 O3 61.38(4) . . ?
N1 Bi1 O3 93.01(4) . . ?
N1 Bi1 N2 63.65(4) . . ?
N3 Bi1 O3 127.95(4) . . ?
N3 Bi1 O7 125.20(4) . . ?
N3 Bi1 N2 72.20(4) . . ?
N3 Bi1 N1 86.19(4) . . ?
C21 O3 Bi1 114.58(10) . . ?
H5WA O5W H5WB 109.5 . . ?
C19 O7 Bi1 119.85(10) . . ?
C21 O4 H4 109.5 . . ?
C23 O5 Bi1 121.48(10) . . ?
C1 O1 Bi1 125.26(10) . . ?
C18 N4 Bi1 121.62(10) . . ?
C14 N4 Bi1 116.62(10) . . ?
C14 N4 C18 120.63(13) . . ?
H4WA O4W H4WB 104.5 . . ?
H2WA O2W H2WB 114.2 . . ?
H1WA O1W H1WB 109.4 . . ?
H3WA O3W H3WB 109.5 . . ?
N4 C18 C19 116.04(13) . . ?
N4 C18 C17 121.16(15) . . ?
C17 C18 C19 122.80(14) . . ?
C7 N2 Bi1 110.01(9) . . ?
C7 N2 C8 114.06(12) . . ?
C20 N2 Bi1 109.95(9) . . ?
C20 N2 C7 106.91(12) . . ?
C20 N2 C8 111.18(12) . . ?
C8 N2 Bi1 104.74(9) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.63(15) . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.43(15) . . ?
C17 C16 H16 120.3 . . ?
C6 N1 Bi1 122.17(10) . . ?
C6 N1 C2 119.67(14) . . ?
C2 N1 Bi1 118.01(10) . . ?
O7 C19 C18 116.42(14) . . ?
O8 C19 O7 126.49(15) . . ?
O8 C19 C18 117.09(14) . . ?
N4 C14 C15 121.30(14) . . ?
N4 C14 C13 115.85(13) . . ?
C15 C14 C13 122.84(14) . . ?
C18 C17 C16 118.83(15) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C13 N3 Bi1 105.98(9) . . ?
C13 N3 C22 109.48(12) . . ?
C13 N3 C12 112.58(12) . . ?
C22 N3 Bi1 110.00(9) . . ?
C22 N3 C12 112.38(12) . . ?
C12 N3 Bi1 106.16(9) . . ?
O3 C21 O4 124.69(15) . . ?
O3 C21 C20 123.75(14) . . ?
O4 C21 C20 111.55(13) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.42(15) . . ?
O2 C1 O1 125.69(15) . . ?
O2 C1 C2 117.79(14) . . ?
O1 C1 C2 116.52(14) . . ?
C14 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
N3 C13 C14 108.60(12) . . ?
N3 C13 H13A 110.0 . . ?
N3 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N1 C6 C7 116.53(13) . . ?
N1 C6 C5 121.87(15) . . ?
C5 C6 C7 121.37(14) . . ?
N2 C7 C6 114.00(13) . . ?
N2 C7 H7A 108.8 . . ?
N2 C7 H7B 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.6 . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 C3 119.42(15) . . ?
C5 C4 H4A 120.3 . . ?
C6 C5 H5 120.6 . . ?
C4 C5 C6 118.74(15) . . ?
C4 C5 H5 120.6 . . ?
N1 C2 C3 121.86(15) . . ?
N1 C2 C1 115.02(13) . . ?
C3 C2 C1 123.11(15) . . ?
O5 C23 C22 117.83(14) . . ?
O6 C23 O5 124.51(15) . . ?
O6 C23 C22 117.59(14) . . ?
H11A C11 H11B 108.8 . . ?
C10 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
C10 C11 C12 104.92(13) . . ?
C12 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
N2 C20 C21 111.52(13) . . ?
N2 C20 H20A 109.3 . . ?
N2 C20 H20B 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C9 C10 C11 105.24(13) . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C10 C9 H9A 111.6 . . ?
C10 C9 H9B 111.6 . . ?
H9A C9 H9B 109.4 . . ?
C8 C9 C10 100.85(13) . . ?
C8 C9 H9A 111.6 . . ?
C8 C9 H9B 111.6 . . ?
N3 C22 C23 114.50(13) . . ?
N3 C22 H22A 108.6 . . ?
N3 C22 H22B 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
N3 C12 C11 117.59(12) . . ?
N3 C12 H12 107.9 . . ?
N3 C12 C8 110.24(12) . . ?
C11 C12 H12 107.9 . . ?
C8 C12 C11 104.81(12) . . ?
C8 C12 H12 107.9 . . ?
N2 C8 C9 120.34(13) . . ?
N2 C8 C12 113.44(12) . . ?
N2 C8 H8 106.6 . . ?
C9 C8 C12 102.40(12) . . ?
C9 C8 H8 106.6 . . ?
C12 C8 H8 106.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_32078801_0m
_database_code_depnum_ccdc_archive 'CCDC 2218897'
loop_
_audit_author_name
_audit_author_address
'Laura Valencia Matarranz'
;Universidade de Vigo
Spain
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;
_audit_creation_date             2022-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H25 Bi N4 O8, H2 O'
_chemical_formula_sum            'C24 H27 Bi N4 O9'
_chemical_formula_weight         724.47
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.9617(3)
_cell_length_b                   13.5542(5)
_cell_length_c                   20.2007(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2453.75(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.347
_exptl_absorpt_coefficient_mu    7.248
_exptl_absorpt_correction_T_max  0.0962
_exptl_absorpt_correction_T_min  0.0629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1513 before and 0.0524 after correction. The Ratio of minimum to maximum transmission is 0.6538. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.017
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.324
_diffrn_reflns_theta_min         2.016
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5907
_reflns_number_total             6097
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         2.357
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Flack x determined using 2489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+5.8350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0529
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C14(H14A,H14B), C21(H21A,H21B), C23(H23A,H23B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.36412(2) 0.33291(2) 0.31938(2) 0.01355(5) Uani 1 1 d . . . . .
C1 C 0.0571(7) 0.3494(4) 0.4406(3) 0.0188(12) Uani 1 1 d . . . . .
C2 C 0.1940(7) 0.3735(4) 0.4807(3) 0.0168(11) Uani 1 1 d . . . . .
C3 C 0.1834(7) 0.3905(5) 0.5482(3) 0.0218(13) Uani 1 1 d . . . . .
H3 H 0.089306 0.390948 0.569874 0.026 Uiso 1 1 calc R . . . .
C4 C 0.3136(8) 0.4068(5) 0.5831(3) 0.0258(14) Uani 1 1 d . . . . .
H4 H 0.309226 0.418811 0.629442 0.031 Uiso 1 1 calc R . . . .
C5 C 0.4500(7) 0.4059(5) 0.5513(3) 0.0193(12) Uani 1 1 d . . . . .
H5 H 0.540524 0.414934 0.575090 0.023 Uiso 1 1 calc R . . . .
C6 C 0.4497(6) 0.3913(4) 0.4834(3) 0.0145(11) Uani 1 1 d . . . . .
C7 C 0.5930(7) 0.3874(4) 0.4454(3) 0.0181(12) Uani 1 1 d . . . . .
H7A H 0.671725 0.421223 0.471271 0.022 Uiso 1 1 calc R . . . .
H7B H 0.623255 0.317631 0.440033 0.022 Uiso 1 1 calc R . . . .
C8 C 0.5529(7) 0.5441(4) 0.3797(3) 0.0166(11) Uani 1 1 d . . . . .
H8 H 0.611809 0.572751 0.342261 0.020 Uiso 1 1 calc R . . . .
C9 C 0.6063(7) 0.5965(4) 0.4428(3) 0.0182(12) Uani 1 1 d . . . . .
H9A H 0.551284 0.570069 0.481374 0.022 Uiso 1 1 calc R . . . .
H9B H 0.713778 0.582954 0.449511 0.022 Uiso 1 1 calc R . . . .
C10 C 0.5819(7) 0.7075(5) 0.4384(3) 0.0225(13) Uani 1 1 d . . . . .
H10A H 0.612728 0.738512 0.480664 0.027 Uiso 1 1 calc R . . . .
H10B H 0.645287 0.734920 0.402772 0.027 Uiso 1 1 calc R . . . .
C11 C 0.4199(8) 0.7330(5) 0.4246(3) 0.0249(14) Uani 1 1 d . . . . .
H11A H 0.408905 0.805291 0.419536 0.030 Uiso 1 1 calc R . . . .
H11B H 0.356674 0.711504 0.462104 0.030 Uiso 1 1 calc R . . . .
C12 C 0.3700(8) 0.6812(4) 0.3612(3) 0.0221(12) Uani 1 1 d . . . . .
H12A H 0.429814 0.706148 0.323510 0.027 Uiso 1 1 calc R . . . .
H12B H 0.264046 0.697296 0.352429 0.027 Uiso 1 1 calc R . . . .
C13 C 0.3877(7) 0.5689(4) 0.3657(3) 0.0156(11) Uani 1 1 d . . . . .
H13 H 0.326975 0.545106 0.404014 0.019 Uiso 1 1 calc R . . . .
C14 C 0.1713(6) 0.5362(4) 0.2951(3) 0.0161(12) Uani 1 1 d . . . . .
H14A H 0.157860 0.604590 0.278906 0.019 Uiso 1 1 calc R . . . .
H14B H 0.119715 0.530461 0.338231 0.019 Uiso 1 1 calc R . . . .
C15 C 0.1014(6) 0.4659(4) 0.2467(3) 0.0158(11) Uani 1 1 d . . . . .
C16 C -0.0249(6) 0.4904(5) 0.2095(3) 0.0182(12) Uani 1 1 d . . . . .
H16 H -0.070926 0.553227 0.213749 0.022 Uiso 1 1 calc R . . . .
C17 C -0.0808(7) 0.4203(4) 0.1662(3) 0.0195(12) Uani 1 1 d . . . . .
H17 H -0.165895 0.435048 0.139929 0.023 Uiso 1 1 calc R . . . .
C18 C -0.0129(6) 0.3286(5) 0.1611(3) 0.0184(11) Uani 1 1 d . . . . .
H18 H -0.048630 0.280922 0.130458 0.022 Uiso 1 1 calc R . . . .
C19 C 0.1074(6) 0.3082(4) 0.2014(3) 0.0151(11) Uani 1 1 d . . . . .
C20 C 0.1809(7) 0.2070(4) 0.2046(3) 0.0170(12) Uani 1 1 d . . . . .
C21 C 0.7234(6) 0.4125(4) 0.3443(3) 0.0136(11) Uani 1 1 d . . . . .
H21A H 0.808501 0.431355 0.372872 0.016 Uiso 1 1 calc R . . . .
H21B H 0.729059 0.452231 0.303218 0.016 Uiso 1 1 calc R . . . .
C22 C 0.7349(6) 0.3036(4) 0.3270(3) 0.0152(11) Uani 1 1 d . . . . .
C23 C 0.4171(7) 0.5451(4) 0.2441(3) 0.0177(11) Uani 1 1 d . . . . .
H23A H 0.495259 0.592943 0.257148 0.021 Uiso 1 1 calc R . . . .
H23B H 0.346975 0.580227 0.214438 0.021 Uiso 1 1 calc R . . . .
C24 C 0.4914(7) 0.4633(4) 0.2043(3) 0.0173(12) Uani 1 1 d . . . . .
N1 N 0.3257(5) 0.3754(4) 0.4489(2) 0.0164(10) Uani 1 1 d . . . . .
N2 N 0.5823(5) 0.4342(3) 0.3789(2) 0.0140(9) Uani 1 1 d . . . . .
N3 N 0.3343(5) 0.5163(3) 0.3045(2) 0.0141(10) Uani 1 1 d . . . . .
N4 N 0.1621(5) 0.3768(3) 0.2427(2) 0.0142(10) Uani 1 1 d . . . . .
O3 O 0.6220(4) 0.2516(3) 0.3212(2) 0.0189(8) Uani 1 1 d . . . . .
O4 O 0.8673(5) 0.2683(3) 0.3173(2) 0.0189(7) Uani 1 1 d . . . . .
O7 O 0.2866(5) 0.1978(3) 0.2463(2) 0.0196(9) Uani 1 1 d . . . . .
O8 O 0.1318(5) 0.1415(3) 0.16784(19) 0.0201(8) Uani 1 1 d . . . . .
O1 O 0.0809(4) 0.3438(3) 0.37702(19) 0.0187(8) Uani 1 1 d . . . . .
H1 H 0.013591 0.309673 0.359318 0.028 Uiso 1 1 calc GR . . . .
O2 O -0.0631(4) 0.3379(4) 0.46766(19) 0.0210(8) Uani 1 1 d . . . . .
O5 O 0.4902(5) 0.3757(3) 0.2279(2) 0.0182(9) Uani 1 1 d . . . . .
O6 O 0.5552(5) 0.4858(3) 0.1524(2) 0.0228(10) Uani 1 1 d . . . . .
O1W O 0.3162(5) 0.1607(4) 0.3982(2) 0.0216(9) Uani 1 1 d . . . . .
H1WA H 0.370373 0.114791 0.380005 0.032 Uiso 1 1 d G . . . .
H1WB H 0.343886 0.161121 0.439484 0.032 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N1 2.701(5) . ?
Bi1 N2 2.674(5) . ?
Bi1 N3 2.518(5) . ?
Bi1 N4 2.455(5) . ?
Bi1 O3 2.561(4) . ?
Bi1 O7 2.453(4) . ?
Bi1 O5 2.243(4) . ?
C1 C2 1.507(8) . ?
C1 O1 1.304(7) . ?
C1 O2 1.217(7) . ?
C2 C3 1.387(9) . ?
C2 N1 1.344(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(8) . ?
C6 C7 1.497(8) . ?
C6 N1 1.329(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N2 1.489(7) . ?
C8 H8 1.0000 . ?
C8 C9 1.536(8) . ?
C8 C13 1.544(8) . ?
C8 N2 1.513(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.518(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.528(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.533(7) . ?
C13 H13 1.0000 . ?
C13 N3 1.505(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.501(8) . ?
C14 N3 1.498(7) . ?
C15 C16 1.399(8) . ?
C15 N4 1.327(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(8) . ?
C19 C20 1.523(8) . ?
C19 N4 1.343(7) . ?
C20 O7 1.273(7) . ?
C20 O8 1.238(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.521(8) . ?
C21 N2 1.475(7) . ?
C22 O3 1.238(7) . ?
C22 O4 1.295(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.523(8) . ?
C23 N3 1.480(7) . ?
C24 O5 1.280(7) . ?
C24 O6 1.233(7) . ?
O1 H1 0.8400 . ?
O1W H1WA 0.8706 . ?
O1W H1WB 0.8699 . ?

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
N2 Bi1 N1 63.14(15) . . ?
N3 Bi1 N1 83.76(14) . . ?
N3 Bi1 N2 67.94(14) . . ?
N3 Bi1 O3 121.50(13) . . ?
N4 Bi1 N1 117.71(15) . . ?
N4 Bi1 N2 134.28(15) . . ?
N4 Bi1 N3 66.89(15) . . ?
N4 Bi1 O3 141.17(15) . . ?
O3 Bi1 N1 101.11(14) . . ?
O3 Bi1 N2 63.56(13) . . ?
O7 Bi1 N1 134.95(15) . . ?
O7 Bi1 N2 149.42(14) . . ?
O7 Bi1 N3 129.43(14) . . ?
O7 Bi1 N4 65.94(15) . . ?
O7 Bi1 O3 86.74(13) . . ?
O5 Bi1 N1 143.83(15) . . ?
O5 Bi1 N2 82.49(15) . . ?
O5 Bi1 N3 72.54(15) . . ?
O5 Bi1 N4 77.83(16) . . ?
O5 Bi1 O3 70.65(15) . . ?
O5 Bi1 O7 80.77(15) . . ?
O1 C1 C2 114.1(5) . . ?
O2 C1 C2 120.4(5) . . ?
O2 C1 O1 125.5(5) . . ?
C3 C2 C1 120.6(5) . . ?
N1 C2 C1 117.5(5) . . ?
N1 C2 C3 121.8(6) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.1(6) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(6) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.4(6) . . ?
C6 C5 H5 121.3 . . ?
C5 C6 C7 120.7(5) . . ?
N1 C6 C5 122.9(5) . . ?
N1 C6 C7 116.3(5) . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N2 C7 C6 113.1(5) . . ?
N2 C7 H7A 109.0 . . ?
N2 C7 H7B 109.0 . . ?
C9 C8 H8 106.4 . . ?
C9 C8 C13 110.5(5) . . ?
C13 C8 H8 106.4 . . ?
N2 C8 H8 106.4 . . ?
N2 C8 C9 114.2(5) . . ?
N2 C8 C13 112.3(4) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.4(5) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 111.9(5) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C10 C11 C12 109.3(5) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C11 C12 C13 112.1(5) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C8 C13 H13 108.1 . . ?
C12 C13 C8 109.1(5) . . ?
C12 C13 H13 108.1 . . ?
N3 C13 C8 110.6(4) . . ?
N3 C13 C12 112.9(5) . . ?
N3 C13 H13 108.1 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
N3 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
N3 C14 C15 112.1(5) . . ?
C16 C15 C14 122.5(5) . . ?
N4 C15 C14 116.5(5) . . ?
N4 C15 C16 121.0(5) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.0(6) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(6) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.6(6) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C20 123.0(5) . . ?
N4 C19 C18 120.9(5) . . ?
N4 C19 C20 116.0(5) . . ?
O7 C20 C19 116.0(5) . . ?
O8 C20 C19 117.8(5) . . ?
O8 C20 O7 126.2(6) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
N2 C21 H21A 109.4 . . ?
N2 C21 H21B 109.4 . . ?
N2 C21 C22 111.1(5) . . ?
O3 C22 C21 121.3(5) . . ?
O3 C22 O4 121.6(5) . . ?
O4 C22 C21 117.1(5) . . ?
H23A C23 H23B 107.2 . . ?
C24 C23 H23A 107.9 . . ?
C24 C23 H23B 107.9 . . ?
N3 C23 H23A 107.9 . . ?
N3 C23 H23B 107.9 . . ?
N3 C23 C24 117.5(5) . . ?
O5 C24 C23 118.4(5) . . ?
O6 C24 C23 118.1(5) . . ?
O6 C24 O5 123.4(6) . . ?
C2 N1 Bi1 124.8(4) . . ?
C6 N1 Bi1 115.8(4) . . ?
C6 N1 C2 119.1(5) . . ?
C7 N2 Bi1 103.6(3) . . ?
C7 N2 C8 114.9(5) . . ?
C8 N2 Bi1 112.5(3) . . ?
C21 N2 Bi1 108.2(3) . . ?
C21 N2 C7 106.7(4) . . ?
C21 N2 C8 110.5(4) . . ?
C13 N3 Bi1 109.6(3) . . ?
C14 N3 Bi1 107.2(3) . . ?
C14 N3 C13 109.2(4) . . ?
C23 N3 Bi1 107.8(3) . . ?
C23 N3 C13 113.1(4) . . ?
C23 N3 C14 109.6(4) . . ?
C15 N4 Bi1 119.0(4) . . ?
C15 N4 C19 121.2(5) . . ?
C19 N4 Bi1 119.6(4) . . ?
C22 O3 Bi1 119.6(3) . . ?
C20 O7 Bi1 122.4(4) . . ?
C1 O1 H1 109.5 . . ?
C24 O5 Bi1 123.4(4) . . ?
H1WA O1W H1WB 104.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.077 0.093 0.007 42.3 9.0 ?
2 0.077 0.593 0.493 42.3 8.9 ?
3 0.423 0.407 -0.007 42.3 8.9 ?
4 0.577 0.907 0.507 42.3 9.1 ?

_olex2_submission_special_instructions 'No special instructions were received'
