# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_j00222_b
_database_code_depnum_ccdc_archive 'CCDC 2432056'
loop_
_audit_author_name
_audit_author_address
'Vojtech Jancik'
;Instituto de Quimica, Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2025-03-17 deposited with the CCDC.	2025-07-21 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         'I4 Pb, 2(C12 H12 N)'
_chemical_formula_sum            'C24 H24 I4 N2 Pb'
_chemical_formula_weight         1055.24

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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   19.2091(6)
_cell_length_b                   8.9415(3)
_cell_length_c                   8.2849(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.1220(10)
_cell_angle_gamma                90
_cell_volume                     1419.32(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.51

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.469
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.169
_exptl_absorpt_coefficient_mu    10.308
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0148
_exptl_absorpt_correction_T_max  0.0371
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec IuS with mirrors'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            35589
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.514
_diffrn_reflns_theta_max         27.511
_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             3273
_reflns_number_gt                3248
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0080P)²+1.9290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     151
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0133
_refine_ls_R_factor_gt           0.0131
_refine_ls_wR_factor_ref         0.0303
_refine_ls_wR_factor_gt          0.0302
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_restrained_S_all      1.205
_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
Pb1 Pb 1.000000 0.500000 1.000000 0.01476(3) Uani 1 2 d S . P . .
I1 I 0.96624(2) 0.70175(2) 0.68893(2) 0.01877(4) Uani 1 1 d . . . . .
I2 I 0.83868(2) 0.41859(2) 0.98641(2) 0.01898(4) Uani 1 1 d . . . . .
C1 C 0.79565(13) 0.5127(3) 0.4718(3) 0.0210(5) Uani 1 1 d . . . . .
H1A H 0.799208 0.519976 0.591372 0.025 Uiso 1 1 calc R U . . .
H1B H 0.759790 0.436820 0.439641 0.025 Uiso 1 1 calc R U . . .
C2 C 0.77386(13) 0.6639(3) 0.3990(3) 0.0226(5) Uani 1 1 d . . . . .
H2A H 0.808623 0.740982 0.434617 0.027 Uiso 1 1 calc R U . . .
H2B H 0.771762 0.657991 0.279425 0.027 Uiso 1 1 calc R U . . .
C3 C 0.70507(13) 0.7049(3) 0.4519(3) 0.0235(5) Uani 1 1 d . . . . .
C4 C 0.64797(13) 0.7249(3) 0.4957(3) 0.0230(5) Uani 1 1 d . . . . .
C5 C 0.58164(13) 0.7404(3) 0.5470(3) 0.0234(5) Uani 1 1 d . . . . .
C6 C 0.52361(13) 0.7476(3) 0.5931(3) 0.0231(5) Uani 1 1 d . . . . .
C7 C 0.45573(12) 0.7523(3) 0.6546(3) 0.0210(5) Uani 1 1 d . . . . .
C8 C 0.42438(13) 0.6195(3) 0.7021(3) 0.0237(5) Uani 1 1 d . . . . .
H8 H 0.446919 0.526345 0.688116 0.028 Uiso 1 1 calc R U . . .
C9 C 0.36033(13) 0.6242(3) 0.7696(3) 0.0253(5) Uani 1 1 d . . . . .
H9 H 0.339622 0.534447 0.804454 0.030 Uiso 1 1 calc R U . . .
C10 C 0.32656(13) 0.7598(3) 0.7864(3) 0.0251(5) Uani 1 1 d . . . . .
H10 H 0.282609 0.762560 0.832035 0.030 Uiso 1 1 calc R U . . .
C11 C 0.35678(13) 0.8919(3) 0.7365(3) 0.0252(5) Uani 1 1 d . . . . .
H11 H 0.333286 0.984440 0.747430 0.030 Uiso 1 1 calc R U . . .
C12 C 0.42129(13) 0.8884(3) 0.6708(3) 0.0234(5) Uani 1 1 d . . . . .
H12 H 0.441956 0.978578 0.636911 0.028 Uiso 1 1 calc R U . . .
N1 N 0.86441(11) 0.4655(2) 0.4149(3) 0.0213(4) Uani 1 1 d D . . . .
H1 H 0.8768(15) 0.373(2) 0.451(3) 0.032 Uiso 1 1 d D U . . .
H2 H 0.8969(14) 0.531(3) 0.455(3) 0.032 Uiso 1 1 d D U . . .
H3 H 0.8635(17) 0.466(3) 0.306(2) 0.032 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
Pb1 I1 3.17432(15) 3_767 ?
Pb1 I1 3.17432(15) . ?
Pb1 I2 3.17731(19) . ?
Pb1 I2 3.17734(17) 3_767 ?
Pb1 I1 3.18251(17) 2_746 ?
Pb1 I1 3.18251(16) 4_576 ?
C1 N1 1.495(3) . ?
C1 C2 1.526(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.468(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.193(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.206(4) . ?
C6 C7 1.434(3) . ?
C7 C12 1.396(3) . ?
C7 C8 1.400(4) . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N1 H1 0.905(18) . ?
N1 H2 0.903(18) . ?
N1 H3 0.904(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
I1 Pb1 I1 180.0 3_767 . ?
I1 Pb1 I2 92.315(4) 3_767 . ?
I1 Pb1 I2 87.685(4) . . ?
I1 Pb1 I2 87.685(4) 3_767 3_767 ?
I1 Pb1 I2 92.316(4) . 3_767 ?
I2 Pb1 I2 180.0 . 3_767 ?
I1 Pb1 I1 83.463(2) 3_767 2_746 ?
I1 Pb1 I1 96.537(3) . 2_746 ?
I2 Pb1 I1 91.334(4) . 2_746 ?
I2 Pb1 I1 88.666(4) 3_767 2_746 ?
I1 Pb1 I1 96.537(3) 3_767 4_576 ?
I1 Pb1 I1 83.463(3) . 4_576 ?
I2 Pb1 I1 88.666(4) . 4_576 ?
I2 Pb1 I1 91.334(4) 3_767 4_576 ?
I1 Pb1 I1 180.0 2_746 4_576 ?
Pb1 I1 Pb1 146.987(5) . 2_756 ?
N1 C1 C2 110.4(2) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C1 109.3(2) . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C2 174.1(3) . . ?
C3 C4 C5 177.1(3) . . ?
C6 C5 C4 177.2(3) . . ?
C5 C6 C7 177.3(3) . . ?
C12 C7 C8 119.7(2) . . ?
C12 C7 C6 120.6(2) . . ?
C8 C7 C6 119.7(2) . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C1 N1 H1 112(2) . . ?
C1 N1 H2 108(2) . . ?
H1 N1 H2 108.5(15) . . ?
C1 N1 H3 111(2) . . ?
H1 N1 H3 108.7(15) . . ?
H2 N1 H3 109.1(15) . . ?

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 H2A I2 0.99 3.12 3.986(3) 146.5 4_575 yes
N1 H1 I2 0.905(18) 2.73(2) 3.526(2) 147(2) 4_565 yes
N1 H2 I1 0.903(18) 2.74(2) 3.578(2) 156(2) . yes
N1 H3 I2 0.904(18) 2.688(19) 3.574(2) 167(2) 1_554 yes

_refine_diff_density_max         0.596
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.086



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile-HI'
