# Supplementary Information (SI) for RSC Advances.
# 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_shs_558_mobo_auto
_database_code_depnum_ccdc_archive 'CCDC 2387887'
#Added by publCIF



_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2026-02-04 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  mirror
# publcif _publ_body_element loop end
_audit_creation_date             2024-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br4, 2(H2 O), C10 H13 N4'
_chemical_formula_sum            'C10 H17 Bi Br4 N4 O2'
_chemical_formula_weight         753.89
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.2869(2)
_cell_length_b                   7.3842(2)
_cell_length_c                   24.8911(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.917(2)
_cell_angle_gamma                90
_cell_volume                     1880.67(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9401
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.1250
_cell_measurement_theta_min      2.8500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.107a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    2.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.820
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15853
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.181
_diffrn_reflns_theta_min         2.879
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.820
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4099
_reflns_number_total             4581
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.135
_refine_diff_density_min         -1.344
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.00045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         4581
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0230
_refine_ls_restrained_S_all      1.052
_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)+(0.0182P)²+4.5747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6)
2.d X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 0.60523(2) 0.23970(2) 0.52392(2) 0.01007(5) Uani 1 1 d . . . . .
Br1 Br 0.83185(4) 0.08032(5) 0.50732(2) 0.01950(9) Uani 1 1 d . . . . .
Br2 Br 0.66286(4) 0.55640(5) 0.46466(2) 0.01417(8) Uani 1 1 d . . . . .
Br3 Br 0.71889(4) 0.38417(5) 0.61753(2) 0.01712(9) Uani 1 1 d . . . . .
Br4 Br 0.48995(4) 0.06482(5) 0.42005(2) 0.01421(8) Uani 1 1 d . . . . .
O1 O 0.9938(3) -0.1036(4) 0.18190(11) 0.0206(6) Uani 1 1 d G . . . .
H1A H 1.035740 -0.068735 0.156067 0.031 Uiso 1 1 d G U . . .
H1B H 1.004972 -0.019186 0.205138 0.031 Uiso 1 1 d G U . . .
O2 O 1.0417(3) 0.3752(5) 0.45279(12) 0.0276(7) Uani 1 1 d G . . . .
H2A H 1.117601 0.400347 0.467745 0.041 Uiso 1 1 d G U . . .
H2B H 1.004221 0.322001 0.477237 0.041 Uiso 1 1 d G U . . .
N1 N 0.8689(3) 0.2191(4) 0.27603(12) 0.0123(6) Uani 1 1 d . . . . .
N2 N 0.9953(3) 0.1606(4) 0.26752(13) 0.0137(6) Uani 1 1 d . . . . .
N3 N 0.9874(3) 0.2431(4) 0.35235(13) 0.0141(7) Uani 1 1 d . . . . .
H3 H 1.013460 0.263570 0.385741 0.017 Uiso 1 1 calc R U . . .
N4 N 0.7669(3) 0.3337(5) 0.35177(13) 0.0177(7) Uani 1 1 d . . . . .
H4A H 0.776883 0.360242 0.385587 0.021 Uiso 1 1 calc R U . . .
H4B H 0.692021 0.348029 0.333483 0.021 Uiso 1 1 calc R U . . .
C1 C 0.7714(4) 0.2373(5) 0.23134(14) 0.0113(7) Uani 1 1 d . . . . .
C2 C 0.8076(4) 0.3042(5) 0.18256(15) 0.0131(7) Uani 1 1 d . . . . .
H2 H 0.894112 0.334650 0.179191 0.016 Uiso 1 1 calc R U . . .
C3 C 0.7127(4) 0.3246(5) 0.13926(15) 0.0163(8) Uani 1 1 d . . . . .
H3A H 0.735547 0.370479 0.106722 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5840(4) 0.2772(5) 0.14408(16) 0.0177(8) Uani 1 1 d . . . . .
H4 H 0.521184 0.290888 0.114724 0.021 Uiso 1 1 calc R U . . .
C5 C 0.5486(4) 0.2095(5) 0.19238(16) 0.0162(8) Uani 1 1 d . . . . .
H5 H 0.462091 0.178307 0.195387 0.019 Uiso 1 1 calc R U . . .
C6 C 0.6425(4) 0.1881(5) 0.23650(15) 0.0138(8) Uani 1 1 d . . . . .
H6 H 0.619330 0.141701 0.268922 0.017 Uiso 1 1 calc R U . . .
C7 C 0.8659(4) 0.2713(5) 0.32809(16) 0.0147(8) Uani 1 1 d . . . . .
C8 C 1.0626(4) 0.1755(5) 0.31414(15) 0.0141(8) Uani 1 1 d . . . . .
C9 C 1.2024(4) 0.1245(6) 0.32752(17) 0.0205(9) Uani 1 1 d . . . . .
H9A H 1.209585 0.045315 0.358767 0.025 Uiso 1 1 calc R U . . .
H9B H 1.252594 0.233044 0.337201 0.025 Uiso 1 1 calc R U . . .
C10 C 1.2612(4) 0.0301(6) 0.28160(17) 0.0211(9) Uani 1 1 d . . . . .
H10A H 1.254319 0.107484 0.250440 0.032 Uiso 1 1 calc R U . . .
H10B H 1.214883 -0.080727 0.272974 0.032 Uiso 1 1 calc R U . . .
H10C H 1.351525 0.003800 0.292314 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br1 2.6812(4) . ?
Bi1 Br2 3.1803(4) 3_666 ?
Bi1 Br2 2.8596(4) . ?
Bi1 Br3 2.7151(4) . ?
Bi1 Br4 3.0211(4) . ?
Bi1 Br4 2.8708(4) 3_656 ?
O1 H1A 0.8502 . ?
O1 H1B 0.8503 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8496 . ?
N1 N2 1.407(4) . ?
N1 C1 1.426(5) . ?
N1 C7 1.355(5) . ?
N2 C8 1.293(5) . ?
N3 H3 0.8600 . ?
N3 C7 1.347(5) . ?
N3 C8 1.380(5) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C7 1.312(5) . ?
C1 C2 1.397(5) . ?
C1 C6 1.394(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.386(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.490(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.517(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
Br1 Bi1 Br2 175.782(12) . 3_666 ?
Br1 Bi1 Br2 92.848(12) . . ?
Br1 Bi1 Br3 90.024(12) . . ?
Br1 Bi1 Br4 87.208(12) . . ?
Br1 Bi1 Br4 94.392(12) . 3_656 ?
Br2 Bi1 Br2 83.496(11) . 3_666 ?
Br2 Bi1 Br4 89.542(11) . . ?
Br2 Bi1 Br4 172.061(12) . 3_656 ?
Br3 Bi1 Br2 91.580(12) . . ?
Br3 Bi1 Br2 92.175(11) . 3_666 ?
Br3 Bi1 Br4 91.672(12) . 3_656 ?
Br3 Bi1 Br4 177.061(12) . . ?
Br4 Bi1 Br2 90.650(11) . 3_666 ?
Br4 Bi1 Br2 89.144(11) 3_656 3_666 ?
Br4 Bi1 Br4 87.562(10) 3_656 . ?
Bi1 Br2 Bi1 96.503(11) . 3_666 ?
Bi1 Br4 Bi1 92.437(10) 3_656 . ?
H1A O1 H1B 104.4 . . ?
H2A O2 H2B 104.6 . . ?
N2 N1 C1 119.9(3) . . ?
C7 N1 N2 110.1(3) . . ?
C7 N1 C1 129.5(3) . . ?
C8 N2 N1 104.8(3) . . ?
C7 N3 H3 126.1 . . ?
C7 N3 C8 107.9(3) . . ?
C8 N3 H3 126.1 . . ?
H4A N4 H4B 120.0 . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
C2 C1 N1 118.8(3) . . ?
C6 C1 N1 120.2(3) . . ?
C6 C1 C2 120.9(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3A 119.8 . . ?
C2 C3 C4 120.5(4) . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N3 C7 N1 105.9(3) . . ?
N4 C7 N1 128.7(4) . . ?
N4 C7 N3 125.5(4) . . ?
N2 C8 N3 111.3(3) . . ?
N2 C8 C9 126.4(4) . . ?
N3 C8 C9 122.3(3) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C10 113.5(3) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
O1 H1A Br3 0.85 2.59 3.364(3) 152.3 4_665 yes
O1 H1B N2 0.85 2.05 2.888(4) 167.2 . yes
O2 H2B Br1 0.85 2.68 3.442(3) 150.6 . yes
N3 H3 O2 0.86 1.86 2.688(4) 162.0 . yes
N4 H4B O1 0.86 1.94 2.765(4) 159.4 2_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C8 N3 -0.9(4) . . . . ?
N1 N2 C8 C9 177.8(4) . . . . ?
N1 C1 C2 C3 -179.1(3) . . . . ?
N1 C1 C6 C5 179.2(3) . . . . ?
N2 N1 C1 C2 -38.3(5) . . . . ?
N2 N1 C1 C6 141.5(3) . . . . ?
N2 N1 C7 N3 -1.1(4) . . . . ?
N2 N1 C7 N4 -180.0(4) . . . . ?
N2 C8 C9 C10 -6.3(6) . . . . ?
N3 C8 C9 C10 172.2(3) . . . . ?
C1 N1 N2 C8 173.8(3) . . . . ?
C1 N1 C7 N3 -172.8(3) . . . . ?
C1 N1 C7 N4 8.4(7) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C7 N1 N2 C8 1.3(4) . . . . ?
C7 N1 C1 C2 132.7(4) . . . . ?
C7 N1 C1 C6 -47.6(5) . . . . ?
C7 N3 C8 N2 0.2(4) . . . . ?
C7 N3 C8 C9 -178.5(4) . . . . ?
C8 N3 C7 N1 0.6(4) . . . . ?
C8 N3 C7 N4 179.5(4) . . . . ?




_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
;
;
