# Supplementary Information (SI) for Journal of Materials Chemistry B.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2431873'
_audit_update_record             
;
2025-03-17 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   25.83
_cell_length_b                   7.69
_cell_length_c                   19.44
_cell_angle_alpha                90
_cell_angle_beta                 104.31
_cell_angle_gamma                90
_cell_volume                     3741.95

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Bi -4.1077 10.2566 33.3689 0.7040 12.9510 2.9238 16.5877 8.7937 6.4692 48.0093
13.5782 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C6.75 H10.50 Bi0.25 Cl0.50 N1 O2.50 
# Dc =      0.77 Fooo =    858.00 Mu =     24.53 M =    215.63
# Found Formula = C14 H21 Bi0.50 Cl3.50 N2 O2.50 
# Dc =      1.72 FOOO =   1920.00 Mu =     52.52 M =    485.91

_chemical_formula_sum            'C14 H21 Bi0.50 Cl3.50 N2 O2.50'
_chemical_formula_moiety         'C14 H21 Bi0.50 Cl3.50 N2 O2.50'
_chemical_compound_source        .
_chemical_formula_weight         485.91


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    293

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_max          ?

_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    5.252

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   none
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            22381
_diffrn_reflns_av_unetI/netI     0.072
_reflns_number_total             4471
_diffrn_reflns_av_R_equivalents  0.051
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4471 
# Theoretical number of reflections is about 8948 


_diffrn_reflns_theta_min         1.627
_diffrn_reflns_theta_max         27.902
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        27.902
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -34
_reflns_limit_h_max              32
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   2.07
_oxford_diffrn_Wilson_scale      16.66

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.59
_refine_diff_density_max         0.84


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_restraints     24
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3006
_oxford_refine_ls_R_factor_ref   0.0266
_refine_ls_wR_factor_ref         0.0288
_refine_ls_goodness_of_fit_ref   1.0442
_refine_ls_shift/su_max          0.0011911
_refine_ls_shift/su_mean         0.0000605


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3006
_refine_ls_R_factor_all          0.0266
_refine_ls_wR_factor_all         0.0288

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3006
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_gt          0.0288


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.693 -0.124 0.166 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Bi1 Bi 0.5000 0.5000 0.5000 0.0262 1.0000 Uani S . . . . .
Cl2 Cl 0.44705(5) 0.74897(18) 0.41234(8) 0.0430 1.0000 Uani . . . . . .
Cl4 Cl 0.44135(5) 0.55728(18) 0.59484(8) 0.0429 1.0000 Uani . . . . . .
Cl9 Cl 0.56309(5) 0.75930(17) 0.56659(7) 0.0371 1.0000 Uani . . . . . .
Cl10 Cl 0.5000 0.0800(2) 0.2500 0.0397 1.0000 Uani S T . . . .
O11 O 0.76340(15) -0.1328(5) 0.4195(2) 0.0481 1.0000 Uani . . . . . .
C12 C 0.7130(2) -0.0941(6) 0.4259(3) 0.0335 1.0000 Uani . . . . . .
C13 C 0.70204(18) 0.0037(8) 0.4799(2) 0.0355 1.0000 Uani . . . . . .
C14 C 0.6495(2) 0.0396(6) 0.4801(3) 0.0331 1.0000 Uani . . . . . .
C15 C 0.60895(18) -0.0256(6) 0.4275(3) 0.0295 1.0000 Uani D . . . . .
N16 N 0.55295(15) 0.0169(6) 0.4266(3) 0.0415 1.0000 Uani D . . . . .
C17 C 0.6193(2) -0.1280(7) 0.3736(3) 0.0408 1.0000 Uani . . . . . .
C18 C 0.6719(2) -0.1620(7) 0.3738(3) 0.0423 1.0000 Uani . . . . . .
C19 C 0.8075(2) -0.0501(8) 0.4671(4) 0.0563 1.0000 Uani . . . . . .
O20 O 0.71065(13) 0.0918(5) 0.65705(18) 0.0359 1.0000 Uani . . . . . .
C21 C 0.76361(18) 0.0825(6) 0.6902(2) 0.0269 1.0000 Uani . . . . . .
C22 C 0.78533(17) -0.0133(7) 0.7512(2) 0.0285 1.0000 Uani . . . . . .
C23 C 0.84020(16) -0.0090(8) 0.7807(2) 0.0302 1.0000 Uani . . . . . .
C24 C 0.87201(17) 0.0895(6) 0.7482(3) 0.0289 1.0000 Uani D . . . . .
N25 N 0.93031(16) 0.0950(6) 0.7801(3) 0.0417 1.0000 Uani D . . . . .
C26 C 0.8512(2) 0.1828(6) 0.6879(3) 0.0335 1.0000 Uani . . . . . .
C27 C 0.7971(2) 0.1785(7) 0.6585(3) 0.0344 1.0000 Uani . . . . . .
C28 C 0.67531(19) -0.0184(8) 0.6831(3) 0.0449 1.0000 Uani . . . . . .
O6 O 1.0000 0.1650(8) 0.2500 0.0895 1.0000 Uani S T . . . .
H131 H 0.7295 0.0455 0.5162 0.0429 1.0000 Uiso . . . . . .
H141 H 0.6423 0.1077 0.5162 0.0399 1.0000 Uiso . . . . . .
H171 H 0.5913 -0.1723 0.3379 0.0489 1.0000 Uiso . . . . . .
H181 H 0.6793 -0.2305 0.3383 0.0511 1.0000 Uiso . . . . . .
H192 H 0.8396 -0.0891 0.4558 0.0837 1.0000 Uiso . . . . . .
H191 H 0.8083 -0.0803 0.5154 0.0838 1.0000 Uiso . . . . . .
H193 H 0.8051 0.0737 0.4612 0.0838 1.0000 Uiso . . . . . .
H221 H 0.7634 -0.0789 0.7724 0.0340 1.0000 Uiso . . . . . .
H231 H 0.8554 -0.0723 0.8213 0.0364 1.0000 Uiso . . . . . .
H261 H 0.8732 0.2472 0.6666 0.0399 1.0000 Uiso . . . . . .
H271 H 0.7825 0.2391 0.6168 0.0409 1.0000 Uiso . . . . . .
H282 H 0.6397 -0.0023 0.6535 0.0671 1.0000 Uiso . . . . . .
H283 H 0.6767 0.0132 0.7318 0.0667 1.0000 Uiso . . . . . .
H281 H 0.6858 -0.1375 0.6807 0.0668 1.0000 Uiso . . . . . .
H253 H 0.9455(10) -0.001(3) 0.770(2) 0.059(2) 1.0000 Uiso D . . . . .
H252 H 0.9444(10) 0.188(4) 0.763(2) 0.059(2) 1.0000 Uiso D . . . . .
H251 H 0.9361(10) 0.105(6) 0.8273(11) 0.059(2) 1.0000 Uiso D . . . . .
H163 H 0.5356(10) -0.080(3) 0.433(2) 0.060(2) 1.0000 Uiso D . . . . .
H161 H 0.5370(10) 0.063(5) 0.3850(13) 0.060(2) 1.0000 Uiso D . . . . .
H162 H 0.5521(10) 0.092(5) 0.4607(17) 0.060(2) 1.0000 Uiso D . . . . .
H62 H 1.0008 0.2256 0.2151 0.1302 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.17738(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Bi1 . Cl2 2_666 2.6997(13) yes
Bi1 . Cl4 2_666 2.6964(12) yes
Bi1 . Cl9 2_666 2.6952(12) yes
Bi1 . Cl2 . 2.6997(13) yes
Bi1 . Cl4 . 2.6964(12) yes
Bi1 . Cl9 . 2.6952(12) yes
O11 . C12 . 1.371(6) yes
O11 . C19 . 1.427(8) yes
C12 . C13 . 1.377(7) yes
C12 . C18 . 1.377(7) yes
C13 . C14 . 1.387(6) yes
C13 . H131 . 0.925 no
C14 . C15 . 1.365(7) yes
C14 . H141 . 0.930 no
C15 . N16 . 1.479(6) yes
C15 . C17 . 1.389(7) yes
N16 . H163 . 0.892(19) no
N16 . H161 . 0.887(19) no
N16 . H162 . 0.883(19) no
C17 . C18 . 1.381(7) yes
C17 . H171 . 0.935 no
C18 . H181 . 0.925 no
C19 . H192 . 0.956 no
C19 . H191 . 0.961 no
C19 . H193 . 0.959 no
O20 . C21 . 1.363(5) yes
O20 . C28 . 1.427(6) yes
C21 . C22 . 1.390(7) yes
C21 . C27 . 1.392(6) yes
C22 . C23 . 1.392(6) yes
C22 . H221 . 0.929 no
C23 . C24 . 1.380(6) yes
C23 . H231 . 0.929 no
C24 . N25 . 1.481(6) yes
C24 . C26 . 1.365(7) yes
N25 . H253 . 0.883(19) no
N25 . H252 . 0.899(19) no
N25 . H251 . 0.895(19) no
C26 . C27 . 1.373(7) yes
C26 . H261 . 0.927 no
C27 . H271 . 0.930 no
C28 . H282 . 0.965 no
C28 . H283 . 0.969 no
C28 . H281 . 0.959 no
O6 . H62 6_755 0.827 no
O6 . H62 . 0.827 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl2 2_666 Bi1 . Cl4 2_666 91.91(4) yes
Cl2 2_666 Bi1 . Cl9 2_666 86.03(4) yes
Cl4 2_666 Bi1 . Cl9 2_666 85.75(4) yes
Cl2 2_666 Bi1 . Cl2 . 180.00 yes
Cl4 2_666 Bi1 . Cl2 . 88.09(4) yes
Cl9 2_666 Bi1 . Cl2 . 93.97(4) yes
Cl2 2_666 Bi1 . Cl4 . 88.09(4) yes
Cl4 2_666 Bi1 . Cl4 . 180.00 yes
Cl9 2_666 Bi1 . Cl4 . 94.25(4) yes
Cl2 . Bi1 . Cl4 . 91.91(4) yes
Cl2 2_666 Bi1 . Cl9 . 93.97(4) yes
Cl4 2_666 Bi1 . Cl9 . 94.25(4) yes
Cl9 2_666 Bi1 . Cl9 . 180.00 yes
Cl2 . Bi1 . Cl9 . 86.03(4) yes
Cl4 . Bi1 . Cl9 . 85.75(4) yes
C12 . O11 . C19 . 117.9(4) yes
O11 . C12 . C13 . 124.5(5) yes
O11 . C12 . C18 . 115.4(5) yes
C13 . C12 . C18 . 120.1(5) yes
C12 . C13 . C14 . 119.8(4) yes
C12 . C13 . H131 . 120.5 no
C14 . C13 . H131 . 119.7 no
C13 . C14 . C15 . 119.6(4) yes
C13 . C14 . H141 . 119.6 no
C15 . C14 . H141 . 120.8 no
C14 . C15 . N16 . 119.6(4) yes
C14 . C15 . C17 . 121.2(4) yes
N16 . C15 . C17 . 119.2(5) yes
C15 . N16 . H163 . 109.6(17) no
C15 . N16 . H161 . 109.4(17) no
H163 . N16 . H161 . 108.7(17) no
C15 . N16 . H162 . 110.0(17) no
H163 . N16 . H162 . 109.8(17) no
H161 . N16 . H162 . 109.3(17) no
C15 . C17 . C18 . 118.6(5) yes
C15 . C17 . H171 . 120.6 no
C18 . C17 . H171 . 120.8 no
C17 . C18 . C12 . 120.6(5) yes
C17 . C18 . H181 . 119.5 no
C12 . C18 . H181 . 119.9 no
O11 . C19 . H192 . 108.0 no
O11 . C19 . H191 . 110.3 no
H192 . C19 . H191 . 109.7 no
O11 . C19 . H193 . 110.3 no
H192 . C19 . H193 . 108.5 no
H191 . C19 . H193 . 110.0 no
C21 . O20 . C28 . 117.1(4) yes
O20 . C21 . C22 . 125.3(4) yes
O20 . C21 . C27 . 115.0(4) yes
C22 . C21 . C27 . 119.7(4) yes
C21 . C22 . C23 . 119.6(4) yes
C21 . C22 . H221 . 120.3 no
C23 . C22 . H221 . 120.0 no
C22 . C23 . C24 . 119.0(4) yes
C22 . C23 . H231 . 120.7 no
C24 . C23 . H231 . 120.3 no
C23 . C24 . N25 . 118.8(4) yes
C23 . C24 . C26 . 121.8(4) yes
N25 . C24 . C26 . 119.3(4) yes
C24 . N25 . H253 . 110.0(16) no
C24 . N25 . H252 . 109.2(17) no
H253 . N25 . H252 . 109.7(17) no
C24 . N25 . H251 . 109.2(16) no
H253 . N25 . H251 . 109.6(17) no
H252 . N25 . H251 . 109.1(17) no
C24 . C26 . C27 . 119.4(4) yes
C24 . C26 . H261 . 120.6 no
C27 . C26 . H261 . 120.0 no
C21 . C27 . C26 . 120.4(5) yes
C21 . C27 . H271 . 119.5 no
C26 . C27 . H271 . 120.1 no
O20 . C28 . H282 . 108.1 no
O20 . C28 . H283 . 109.0 no
H282 . C28 . H283 . 110.5 no
O20 . C28 . H281 . 109.7 no
H282 . C28 . H281 . 109.4 no
H283 . C28 . H281 . 110.1 no
H62 6_755 O6 . H62 . 111.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N25 . H253 . O6 2_756 161(3) 0.883 1.996 2.847(7) yes


