# Supplementary Information (SI) for Nanoscale.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_Bi3C8H16NO11
_database_code_depnum_ccdc_archive 'CCDC 2516205'
loop_
_audit_author_name
_audit_author_address
'Abdeljalil Assoud'
;University of Waterloo
Canada
;
_audit_update_record             
;
2025-12-16 deposited with the CCDC.	2026-04-01 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         ?
_chemical_formula_sum            'C8 H16 Bi3 N O11'
_chemical_formula_weight         929.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.4599(4)
_cell_length_b                   15.1984(9)
_cell_length_c                   13.7746(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.8916(16)
_cell_angle_gamma                90
_cell_volume                     1559.76(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    511
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      30.0

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.957
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    33.820
_shelx_estimated_absorpt_T_min   0.283
_shelx_estimated_absorpt_T_max   0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4199
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER kappa APEX II'
_diffrn_measurement_method       'Omega and phi scan'
_diffrn_standards_number         3
_diffrn_standards_interval_time  0.5
_diffrn_standards_decay_%        0
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19027
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.680
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4545
_reflns_number_gt                3589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker kappa APEX II'
_computing_cell_refinement       "SMART, 'Bruker APEX II"
_computing_data_reduction        "SAINT, 'Bruker APEX II"
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Mercury
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0185P)²+0.5621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   FMap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.000075(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4545
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0507
_refine_ls_wR_factor_gt          0.0471
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.71793(3) 0.20099(2) 0.19733(2) 0.01440(6) Uani 1 1 d . . . . .
Bi2 Bi 0.96671(3) 0.23989(2) 0.45131(2) 0.01475(6) Uani 1 1 d . . . . .
Bi3 Bi 0.21730(3) 0.28724(2) 0.20554(2) 0.01391(6) Uani 1 1 d . . . . .
O1 O 0.8018(6) 0.3391(3) 0.5113(3) 0.0219(9) Uani 1 1 d . . . . .
O2 O 0.7585(5) 0.2818(3) 0.3265(3) 0.0181(9) Uani 1 1 d . . . . .
O3 O 0.0418(5) 0.1856(3) 0.2693(3) 0.0174(8) Uani 1 1 d . . . . .
O4 O 0.4055(5) 0.1849(3) 0.2558(3) 0.0186(9) Uani 1 1 d . . . . .
O5 O 0.1743(5) 0.2103(3) 0.0699(3) 0.0209(9) Uani 1 1 d . . . . .
O6 O 0.1344(6) 0.1668(3) -0.1185(2) 0.0217(9) Uani 1 1 d . . . . .
O7 O 0.8919(5) 0.3028(3) 0.1321(3) 0.0170(8) Uani 1 1 d . . . . .
O8 O 0.5296(5) 0.3002(3) 0.1441(3) 0.0194(9) Uani 1 1 d . . . . .
C1 C 0.7169(9) 0.3954(4) 0.4409(4) 0.0208(13) Uani 1 1 d . . . . .
H1A H 0.804997 0.434894 0.415299 0.025 Uiso 1 1 calc R U . . .
H1B H 0.626848 0.430637 0.471175 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6294(8) 0.3424(4) 0.3590(4) 0.0209(13) Uani 1 1 d . . . . .
H2A H 0.526104 0.311073 0.381412 0.025 Uiso 1 1 calc R U . . .
H2B H 0.589331 0.381026 0.306139 0.025 Uiso 1 1 calc R U . . .
C3 C 0.1325(8) 0.1032(4) 0.2762(5) 0.0265(14) Uani 1 1 d . . . . .
H3A H 0.127798 0.074637 0.213140 0.032 Uiso 1 1 calc R U . . .
H3B H 0.073885 0.065256 0.321489 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3278(9) 0.1178(4) 0.3111(5) 0.0294(15) Uani 1 1 d . . . . .
H4A H 0.333316 0.134342 0.379194 0.035 Uiso 1 1 calc R U . . .
H4B H 0.394812 0.063641 0.304631 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2975(8) 0.1487(4) 0.0350(4) 0.0214(13) Uani 1 1 d . . . . .
H5A H 0.329352 0.105859 0.085175 0.026 Uiso 1 1 calc R U . . .
H5B H 0.406017 0.178403 0.017100 0.026 Uiso 1 1 calc R U . . .
C6 C 0.2096(8) 0.1032(4) -0.0527(4) 0.0187(12) Uani 1 1 d . . . . .
H6A H 0.297956 0.068286 -0.084803 0.022 Uiso 1 1 calc R U . . .
H6B H 0.116075 0.064019 -0.032212 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7971(8) 0.3848(4) 0.1234(4) 0.0213(13) Uani 1 1 d . . . . .
H7A H 0.855749 0.423149 0.078490 0.026 Uiso 1 1 calc R U . . .
H7B H 0.797766 0.413716 0.186154 0.026 Uiso 1 1 calc R U . . .
C8 C 0.6060(8) 0.3674(4) 0.0866(4) 0.0245(14) Uani 1 1 d . . . . .
H8A H 0.535792 0.420934 0.090467 0.029 Uiso 1 1 calc R U . . .
H8B H 0.604164 0.348995 0.019182 0.029 Uiso 1 1 calc R U . . .
N1 N 0.2499(7) 0.5091(4) 0.1506(4) 0.0276(12) Uani 1 1 d . . . . .
O9 O 0.2929(9) 0.4837(4) 0.2343(3) 0.0565(17) Uani 1 1 d . . . . .
O10 O 0.2576(7) 0.5895(3) 0.1318(3) 0.0356(12) Uani 1 1 d . . . . .
O11 O 0.2017(7) 0.4547(4) 0.0870(4) 0.0438(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O8 2.164(4) . ?
Bi1 O2 2.171(4) . ?
Bi1 O7 2.237(4) . ?
Bi1 O4 2.516(4) . ?
Bi1 O3 2.576(4) 1_655 ?
Bi1 O1 2.737(4) 4_565 ?
Bi2 O1 2.139(4) . ?
Bi2 O6 2.150(4) 4_666 ?
Bi2 O5 2.320(4) 4_666 ?
Bi2 O2 2.346(4) . ?
Bi2 O7 2.659(4) 4_566 ?
Bi2 O3 2.725(4) 1_655 ?
Bi3 O4 2.184(4) . ?
Bi3 O5 2.214(4) . ?
Bi3 O3 2.233(4) . ?
Bi3 O8 2.526(4) . ?
Bi3 O7 2.594(4) 1_455 ?
Bi3 O6 2.626(4) 4_566 ?
O1 C1 1.418(7) . ?
O2 C2 1.421(7) . ?
O3 C3 1.424(7) . ?
O4 C4 1.415(7) . ?
O5 C5 1.413(7) . ?
O6 C6 1.421(6) . ?
O7 C7 1.434(7) . ?
O8 C8 1.428(7) . ?
C1 C2 1.507(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.527(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.513(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.512(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N1 O9 1.242(7) . ?
N1 O11 1.244(7) . ?
N1 O10 1.250(7) . ?

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
O8 Bi1 O2 86.81(15) . . ?
O8 Bi1 O7 76.20(14) . . ?
O2 Bi1 O7 82.99(14) . . ?
O8 Bi1 O4 65.15(13) . . ?
O2 Bi1 O4 83.44(14) . . ?
O7 Bi1 O4 139.56(14) . . ?
O8 Bi1 O3 140.73(14) . 1_655 ?
O2 Bi1 O3 69.32(13) . 1_655 ?
O7 Bi1 O3 70.47(13) . 1_655 ?
O4 Bi1 O3 137.25(11) . 1_655 ?
O8 Bi1 O1 90.77(13) . 4_565 ?
O2 Bi1 O1 149.81(14) . 4_565 ?
O7 Bi1 O1 67.25(13) . 4_565 ?
O4 Bi1 O1 122.51(12) . 4_565 ?
O3 Bi1 O1 94.90(12) 1_655 4_565 ?
O1 Bi2 O6 93.83(16) . 4_666 ?
O1 Bi2 O5 82.79(15) . 4_666 ?
O6 Bi2 O5 73.57(13) 4_666 4_666 ?
O1 Bi2 O2 73.69(13) . . ?
O6 Bi2 O2 82.62(14) 4_666 . ?
O5 Bi2 O2 145.18(14) 4_666 . ?
O1 Bi2 O7 70.03(13) . 4_566 ?
O6 Bi2 O7 137.25(13) 4_666 4_566 ?
O5 Bi2 O7 65.46(12) 4_666 4_566 ?
O2 Bi2 O7 126.15(13) . 4_566 ?
O1 Bi2 O3 135.91(13) . 1_655 ?
O6 Bi2 O3 68.70(13) 4_666 1_655 ?
O5 Bi2 O3 125.85(13) 4_666 1_655 ?
O2 Bi2 O3 64.35(12) . 1_655 ?
O7 Bi2 O3 148.23(12) 4_566 1_655 ?
O4 Bi3 O5 87.43(14) . . ?
O4 Bi3 O3 76.29(14) . . ?
O5 Bi3 O3 84.46(14) . . ?
O4 Bi3 O8 64.70(13) . . ?
O5 Bi3 O8 81.69(14) . . ?
O3 Bi3 O8 138.97(14) . . ?
O4 Bi3 O7 139.72(14) . 1_455 ?
O5 Bi3 O7 68.03(13) . 1_455 ?
O3 Bi3 O7 70.18(13) . 1_455 ?
O8 Bi3 O7 136.31(11) . 1_455 ?
O4 Bi3 O6 94.26(14) . 4_566 ?
O5 Bi3 O6 152.70(14) . 4_566 ?
O3 Bi3 O6 69.59(13) . 4_566 ?
O8 Bi3 O6 123.53(12) . 4_566 ?
O7 Bi3 O6 94.39(12) 1_455 4_566 ?
C1 O1 Bi2 114.0(3) . . ?
C1 O1 Bi1 131.2(3) . 4_566 ?
Bi2 O1 Bi1 111.58(16) . 4_566 ?
C2 O2 Bi1 123.8(3) . . ?
C2 O2 Bi2 112.3(3) . . ?
Bi1 O2 Bi2 120.44(17) . . ?
C3 O3 Bi3 110.4(3) . . ?
C3 O3 Bi1 122.6(3) . 1_455 ?
Bi3 O3 Bi1 110.06(15) . 1_455 ?
C3 O3 Bi2 108.9(3) . 1_455 ?
Bi3 O3 Bi2 107.69(15) . 1_455 ?
Bi1 O3 Bi2 95.39(12) 1_455 1_455 ?
C4 O4 Bi3 114.2(3) . . ?
C4 O4 Bi1 130.8(3) . . ?
Bi3 O4 Bi1 114.88(15) . . ?
C5 O5 Bi3 124.6(3) . . ?
C5 O5 Bi2 113.5(3) . 4_465 ?
Bi3 O5 Bi2 119.03(17) . 4_465 ?
C6 O6 Bi2 112.5(3) . 4_465 ?
C6 O6 Bi3 131.7(3) . 4_565 ?
Bi2 O6 Bi3 114.03(17) 4_465 4_565 ?
C7 O7 Bi1 109.9(3) . . ?
C7 O7 Bi3 124.0(3) . 1_655 ?
Bi1 O7 Bi3 109.29(15) . 1_655 ?
C7 O7 Bi2 105.1(3) . 4_565 ?
Bi1 O7 Bi2 111.14(15) . 4_565 ?
Bi3 O7 Bi2 96.11(12) 1_655 4_565 ?
C8 O8 Bi1 114.6(3) . . ?
C8 O8 Bi3 129.9(3) . . ?
Bi1 O8 Bi3 115.23(16) . . ?
O1 C1 C2 110.6(5) . . ?
O1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O2 C2 C1 107.9(5) . . ?
O2 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
O2 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
O3 C3 C4 109.6(5) . . ?
O3 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
O3 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O4 C4 C3 110.2(5) . . ?
O4 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
O4 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
O5 C5 C6 108.2(5) . . ?
O5 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
O5 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
O6 C6 C5 109.9(5) . . ?
O6 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
O6 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
O7 C7 C8 109.2(5) . . ?
O7 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
O7 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O8 C8 C7 109.6(5) . . ?
O8 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
O8 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O9 N1 O11 119.9(6) . . ?
O9 N1 O10 118.9(6) . . ?
O11 N1 O10 121.2(5) . . ?

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
C2 H2B O8 0.97 2.57 3.082(6) 113.3 . yes
C3 H3B N1 0.97 2.61 3.390(8) 137.8 2_545 yes
C3 H3B O10 0.97 2.61 3.239(8) 122.5 2_545 yes
C6 H6A O9 0.97 2.61 3.305(7) 128.5 4_565 yes
C7 H7A O11 0.97 2.62 3.263(8) 123.8 1_655 yes
C8 H8A N1 0.97 2.68 3.564(8) 151.0 . yes
C8 H8A O11 0.97 2.54 3.295(8) 134.4 . yes
C8 H8B O10 0.97 2.55 3.291(7) 133.6 3_665 yes

_refine_diff_density_max         1.956
_refine_diff_density_min         -1.418
_refine_diff_density_rms         0.267

