# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_PhVPI
_database_code_depnum_ccdc_archive 'CCDC 1945001'
loop_
_audit_author_name
_audit_author_address
'Alberto Cassetta'
;CNR  Istituto di Cristallografia
Italy
;

_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;
_publcif_datablock.id            {f35dce63-f7ec-4bda-98a8-2145862da967}

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'phenyl viologen lead (II) iodide'
_chemical_name_common            ?
_chemical_melting_point          605
_chemical_formula_moiety         'C11 H9 I3 N Pb'
_chemical_formula_sum            'C11 H9 I3 N Pb'
_chemical_formula_weight         743.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4630 1.7726 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.0345 9.9071 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.530(1)
_cell_length_b                   12.610(3)
_cell_length_c                   14.680(3)
_cell_angle_alpha                107.85(3)
_cell_angle_beta                 93.47(3)
_cell_angle_gamma                98.10(3)
_cell_volume                     785.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    57
_cell_measurement_theta_min      1.444
_cell_measurement_theta_max      31.748

_exptl_crystal_description       'Thick rods'
_exptl_crystal_colour            Black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.142
_exptl_crystal_F_000             646
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    15.828
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.700

_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5038
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.444
_diffrn_reflns_theta_max         31.748
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             5038
_reflns_number_gt                4580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq. Anisotropic thermal motion modeling has been applied 
to all atoms. Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1424P)²+20.0298P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5038
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0915
_refine_ls_wR_factor_ref         0.2697
_refine_ls_wR_factor_gt          0.2671
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_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
Pb Pb 0.66808(14) 0.88600(6) 0.34469(5) 0.0484(2) Uani 1 1 d . . . . .
I2 I 1.1650(3) 0.97100(11) 0.23153(10) 0.0521(3) Uani 1 1 d . . . . .
I3 I 1.1667(3) 0.84220(10) 0.49321(9) 0.0498(3) Uani 1 1 d . . . . .
I1 I 0.6119(4) 0.64790(13) 0.21094(13) 0.0709(4) Uani 1 1 d . . . . .
N N 0.068(3) 0.3644(9) 0.2746(7) 0.052(3) Uani 1 1 d G . . . .
C1 C 0.189(3) 0.3004(6) 0.3245(8) 0.051(4) Uani 1 1 d G . . . .
H1 H 0.157056 0.222026 0.298696 0.062 Uiso 1 1 calc R U . . .
C2 C 0.360(3) 0.3535(8) 0.4131(8) 0.054(4) Uani 1 1 d G . . . .
H2 H 0.441033 0.310721 0.446493 0.064 Uiso 1 1 calc R U . . .
C3 C 0.408(3) 0.4707(8) 0.4517(7) 0.048(4) Uani 1 1 d G . . . .
C4 C 0.286(4) 0.5347(6) 0.4018(9) 0.074(7) Uani 1 1 d G . . . .
H4 H 0.318320 0.613081 0.427672 0.089 Uiso 1 1 calc R U . . .
C5 C 0.116(4) 0.4816(9) 0.3133(9) 0.078(8) Uani 1 1 d G . . . .
H5 H 0.034342 0.524388 0.279875 0.094 Uiso 1 1 calc R U . . .
C6 C -0.096(3) 0.3092(10) 0.1834(8) 0.048(4) Uani 1 1 d G . . . .
C7 C -0.304(3) 0.2116(11) 0.1689(10) 0.058(4) Uani 1 1 d G . . . .
H7 H -0.325890 0.180133 0.218162 0.070 Uiso 1 1 calc R U . . .
C8 C -0.478(3) 0.1611(12) 0.0807(12) 0.079(7) Uani 1 1 d G . . . .
H8 H -0.616476 0.095823 0.071024 0.095 Uiso 1 1 calc R U . . .
C9 C -0.444(4) 0.2082(15) 0.0071(9) 0.083(8) Uani 1 1 d G . . . .
H9 H -0.560803 0.174401 -0.051901 0.099 Uiso 1 1 calc R U . . .
C10 C -0.237(4) 0.3058(15) 0.0216(9) 0.080(7) Uani 1 1 d G . . . .
H10 H -0.214544 0.337290 -0.027689 0.096 Uiso 1 1 calc R U . . .
C11 C -0.063(3) 0.3563(11) 0.1097(10) 0.057(4) Uani 1 1 d G . . . .
H11 H 0.076046 0.421601 0.119449 0.069 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
Pb I1 3.008(2) . ?
Pb I2 3.1369(17) . ?
Pb I2 3.2285(16) 1_455 ?
Pb I3 3.2640(16) . ?
Pb I3 3.3469(17) 1_455 ?
N C1 1.3900 . ?
N C5 1.3900 . ?
N C6 1.411(13) . ?
C1 C2 1.3900 . ?
C1 H1 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 C3 1.514(17) 2_666 ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.3900 . ?
C6 C11 1.3900 . ?
C7 C8 1.3900 . ?
C7 H7 0.9300 . ?
C8 C9 1.3900 . ?
C8 H8 0.9300 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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 Pb I2 91.09(6) . . ?
I1 Pb I2 98.78(5) . 1_455 ?
I2 Pb I2 90.73(4) . 1_455 ?
I1 Pb I3 91.67(5) . . ?
I2 Pb I3 92.03(4) . . ?
I2 Pb I3 169.14(4) 1_455 . ?
I1 Pb I3 99.08(6) . 1_455 ?
I2 Pb I3 169.76(4) . 1_455 ?
I2 Pb I3 88.92(4) 1_455 1_455 ?
I3 Pb I3 86.50(4) . 1_455 ?
Pb I2 Pb 90.73(4) . 1_655 ?
Pb I3 Pb 86.50(4) . 1_655 ?
C1 N C5 120.0 . . ?
C1 N C6 119.2(9) . . ?
C5 N C6 120.8(9) . . ?
N C1 C2 120.0 . . ?
N C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 C3 120.4(13) . 2_666 ?
C4 C3 C3 119.6(13) . 2_666 ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 N 120.0 . . ?
C4 C5 H5 120.0 . . ?
N C5 H5 120.0 . . ?
C7 C6 C11 120.0 . . ?
C7 C6 N 120.0(9) . . ?
C11 C6 N 119.9(9) . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 120.0 . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?

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
C5 N C1 C2 0.0 . . . . ?
C6 N C1 C2 177.9(13) . . . . ?
N C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C3 180(2) . . . 2_666 ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C3 C4 C5 -180(2) 2_666 . . . ?
C3 C4 C5 N 0.0 . . . . ?
C1 N C5 C4 0.0 . . . . ?
C6 N C5 C4 -177.9(13) . . . . ?
C1 N C6 C7 44.0(15) . . . . ?
C5 N C6 C7 -138.2(10) . . . . ?
C1 N C6 C11 -139.9(10) . . . . ?
C5 N C6 C11 38.0(15) . . . . ?
C11 C6 C7 C8 0.0 . . . . ?
N C6 C7 C8 176.1(14) . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C6 0.0 . . . . ?
C7 C6 C11 C10 0.0 . . . . ?
N C6 C11 C10 -176.1(14) . . . . ?

_refine_diff_density_max         6.629
_refine_diff_density_min         -2.365
_refine_diff_density_rms         0.948


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_exptl_crystal_preparation       'low band gap semiconductor'
