# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_jrn071_a1_a
_database_code_depnum_ccdc_archive 'CCDC 1945574'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;Colorado State University
United States of America
;
#Added by publCIF



_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'HELIOS optics'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Bi I5 N2 O'
_chemical_formula_weight         1043.72

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   8.8873(16)
_cell_length_b                   12.724(2)
_cell_length_c                   19.021(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.769(5)
_cell_angle_gamma                90
_cell_volume                     2125.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7880
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.39

_exptl_crystal_description       Fragment
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.261
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    15.556
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3567
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\ms microfocus tube'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14836
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         26.412
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4349
_reflns_number_gt                3487
_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       'APEX3 (Bruker-AXS, 2015)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Vesta (K. Momma and F. Izumi, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0373P)²+12.9448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4349
_refine_ls_number_parameters     197
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.500000 0.71572(4) 0.750000 0.02875(13) Uani 1 2 d S T P . .
Bi2 Bi 0.000000 0.33968(4) 0.750000 0.02972(13) Uani 1 2 d S T P . .
I1 I -0.07634(8) 0.34299(6) 0.58652(3) 0.04739(19) Uani 1 1 d . . . . .
I2 I 0.37890(9) 0.71449(6) 0.58970(3) 0.04663(19) Uani 1 1 d . . . . .
I3 I -0.22894(8) 0.18062(6) 0.76121(4) 0.0534(2) Uani 1 1 d . . . . .
I4 I 0.25724(8) 0.52978(6) 0.76379(5) 0.0589(2) Uani 1 1 d . . . . .
I5 I 0.71907(11) 0.87722(8) 0.72499(5) 0.0729(3) Uani 1 1 d . . . . .
N2 N 0.9093(9) 0.8490(6) 0.5733(4) 0.0399(19) Uani 1 1 d . . . . .
H2A H 0.940779 0.787550 0.587366 0.048 Uiso 1 1 calc R U . . .
N1 N 0.7570(9) 0.6640(6) 0.5085(5) 0.0396(19) Uani 1 1 d . . . . .
H1A H 0.829618 0.655946 0.543550 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5487(12) 0.8794(8) 0.4085(6) 0.049(3) Uani 1 1 d . . . . .
H5 H 0.468861 0.887723 0.371126 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5959(10) 0.7761(8) 0.4308(5) 0.037(2) Uani 1 1 d . . . . .
C11 C 0.7907(10) 0.8563(8) 0.5204(5) 0.038(2) Uani 1 1 d . . . . .
C12 C 0.7152(10) 0.7625(7) 0.4870(5) 0.0330(19) Uani 1 1 d . . . . .
C7 C 0.7376(10) 0.9537(7) 0.4970(5) 0.037(2) Uani 1 1 d . . . . .
C9 C 0.9277(14) 1.0316(10) 0.5866(6) 0.054(3) Uani 1 1 d . . . . .
H9 H 0.972520 1.089887 0.610898 0.065 Uiso 1 1 calc R U . . .
C3 C 0.5261(13) 0.6874(9) 0.3988(6) 0.051(3) Uani 1 1 d . . . . .
H3 H 0.445472 0.695152 0.361766 0.061 Uiso 1 1 calc R U . . .
C2 C 0.5734(13) 0.5876(9) 0.4205(7) 0.056(3) Uani 1 1 d . . . . .
H2 H 0.528719 0.528187 0.397658 0.067 Uiso 1 1 calc R U . . .
C6 C 0.6169(12) 0.9652(8) 0.4401(5) 0.043(2) Uani 1 1 d . . . . .
H6 H 0.584503 1.031920 0.424578 0.052 Uiso 1 1 calc R U . . .
C10 C 0.9790(12) 0.9311(10) 0.6042(6) 0.053(3) Uani 1 1 d . . . . .
H10 H 1.064288 0.921724 0.638606 0.063 Uiso 1 1 calc R U . . .
C1 C 0.6896(12) 0.5794(9) 0.4773(6) 0.050(3) Uani 1 1 d . . . . .
H1 H 0.721293 0.513098 0.494080 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8100(12) 1.0424(9) 0.5328(6) 0.047(2) Uani 1 1 d . . . . .
H8 H 0.775721 1.109437 0.519016 0.056 Uiso 1 1 calc R U . . .
O1 O 0.9928(11) 0.6522(8) 0.6221(6) 0.076(3) Uani 1 1 d D . . . .
H1B H 1.092(4) 0.652(12) 0.618(8) 0.091 Uiso 1 1 d D U . . .
H2B H 0.962(15) 0.621(11) 0.660(5) 0.091 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
Bi1 I5 2.9192(9) 2_656 ?
Bi1 I5 2.9193(9) . ?
Bi1 I2 3.0748(8) . ?
Bi1 I2 3.0749(8) 2_656 ?
Bi1 I4 3.2393(8) 2_656 ?
Bi1 I4 3.2393(8) . ?
Bi2 I3 2.9006(8) 2_556 ?
Bi2 I3 2.9006(8) . ?
Bi2 I1 3.0802(8) . ?
Bi2 I1 3.0802(8) 2_556 ?
Bi2 I4 3.3111(8) . ?
Bi2 I4 3.3111(8) 2_556 ?
N2 C10 1.308(14) . ?
N2 C11 1.344(12) . ?
N2 H2A 0.8600 . ?
N1 C1 1.328(13) . ?
N1 C12 1.353(12) . ?
N1 H1A 0.8600 . ?
C5 C6 1.346(14) . ?
C5 C4 1.425(14) . ?
C5 H5 0.9300 . ?
C4 C3 1.383(14) . ?
C4 C12 1.397(13) . ?
C11 C7 1.375(13) . ?
C11 C12 1.466(14) . ?
C7 C6 1.411(13) . ?
C7 C8 1.421(14) . ?
C9 C8 1.354(15) . ?
C9 C10 1.381(17) . ?
C9 H9 0.9300 . ?
C3 C2 1.381(16) . ?
C3 H3 0.9300 . ?
C2 C1 1.380(16) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C10 H10 0.9300 . ?
C1 H1 0.9300 . ?
C8 H8 0.9300 . ?
O1 H1B 0.900(10) . ?
O1 H2B 0.899(10) . ?

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
I5 Bi1 I5 90.52(5) 2_656 . ?
I5 Bi1 I2 91.37(2) 2_656 . ?
I5 Bi1 I2 89.04(2) . . ?
I5 Bi1 I2 89.04(2) 2_656 2_656 ?
I5 Bi1 I2 91.37(2) . 2_656 ?
I2 Bi1 I2 179.42(3) . 2_656 ?
I5 Bi1 I4 175.05(2) 2_656 2_656 ?
I5 Bi1 I4 91.83(3) . 2_656 ?
I2 Bi1 I4 93.02(2) . 2_656 ?
I2 Bi1 I4 86.55(2) 2_656 2_656 ?
I5 Bi1 I4 91.83(3) 2_656 . ?
I5 Bi1 I4 175.05(2) . . ?
I2 Bi1 I4 86.55(2) . . ?
I2 Bi1 I4 93.02(2) 2_656 . ?
I4 Bi1 I4 86.17(3) 2_656 . ?
I3 Bi2 I3 91.51(4) 2_556 . ?
I3 Bi2 I1 89.11(2) 2_556 . ?
I3 Bi2 I1 91.99(2) . . ?
I3 Bi2 I1 91.99(2) 2_556 2_556 ?
I3 Bi2 I1 89.11(2) . 2_556 ?
I1 Bi2 I1 178.43(3) . 2_556 ?
I3 Bi2 I4 91.83(3) 2_556 . ?
I3 Bi2 I4 170.93(2) . . ?
I1 Bi2 I4 96.50(2) . . ?
I1 Bi2 I4 82.35(2) 2_556 . ?
I3 Bi2 I4 170.93(2) 2_556 2_556 ?
I3 Bi2 I4 91.83(3) . 2_556 ?
I1 Bi2 I4 82.35(2) . 2_556 ?
I1 Bi2 I4 96.50(2) 2_556 2_556 ?
I4 Bi2 I4 86.14(3) . 2_556 ?
Bi1 I4 Bi2 170.92(3) . . ?
C10 N2 C11 123.1(9) . . ?
C10 N2 H2A 118.5 . . ?
C11 N2 H2A 118.5 . . ?
C1 N1 C12 122.1(9) . . ?
C1 N1 H1A 119.0 . . ?
C12 N1 H1A 119.0 . . ?
C6 C5 C4 121.5(9) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C3 C4 C12 118.2(10) . . ?
C3 C4 C5 122.0(9) . . ?
C12 C4 C5 119.8(9) . . ?
N2 C11 C7 119.7(9) . . ?
N2 C11 C12 121.6(9) . . ?
C7 C11 C12 118.8(9) . . ?
N1 C12 C4 119.2(9) . . ?
N1 C12 C11 122.4(9) . . ?
C4 C12 C11 118.3(9) . . ?
C11 C7 C6 121.7(9) . . ?
C11 C7 C8 116.9(9) . . ?
C6 C7 C8 121.4(9) . . ?
C8 C9 C10 117.7(11) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C2 C3 C4 121.5(11) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C1 C2 C3 117.5(10) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C5 C6 C7 119.8(10) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N2 C10 C9 120.9(10) . . ?
N2 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
N1 C1 C2 121.4(10) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C9 C8 C7 121.5(10) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
H1B O1 H2B 120(10) . . ?

_refine_diff_density_max         1.482
_refine_diff_density_min         -1.474
_refine_diff_density_rms         0.233




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_jrn070_a2_a
_database_code_depnum_ccdc_archive 'CCDC 1945577'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;Colorado State University
United States of America
;
#Added by publCIF



_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'HELIOS optics'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 I10 N4 O2 Pb3'
_chemical_formula_weight         2291.04

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'
I I -0.4742 1.8119 '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'
Pb Pb -3.3944 10.1111 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5780(5)
_cell_length_b                   14.1272(9)
_cell_length_c                   18.0628(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.434(2)
_cell_angle_gamma                90
_cell_volume                     2185.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7603
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.45

_exptl_crystal_description       fragment
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.482
_exptl_crystal_F_000             1976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    18.621
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\ms microfocus tube'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12858
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.680
_diffrn_reflns_theta_max         26.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4458
_reflns_number_gt                3762
_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       'APEX3 (Bruker-AXS, 2015)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Vesta (K. Momma and F. Izumi, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0276P)²+3.2348P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.00081(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4458
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Pb1 Pb 0.39548(3) 0.65516(2) 0.55077(2) 0.03377(9) Uani 1 1 d . . . . .
Pb2 Pb 0.000000 0.500000 0.500000 0.03677(11) Uani 1 2 d S . P . .
I1 I 0.41918(6) 0.87036(3) 0.54441(3) 0.04281(14) Uani 1 1 d . . . . .
I2 I 0.32710(6) 0.41678(3) 0.56505(3) 0.04477(14) Uani 1 1 d . . . . .
I3 I 0.57536(7) 0.64950(4) 0.70231(3) 0.04915(15) Uani 1 1 d . . . . .
I4 I 0.18245(6) 0.63098(4) 0.38597(3) 0.04802(14) Uani 1 1 d . . . . .
I5 I 0.06379(7) 0.67440(4) 0.61182(3) 0.05097(15) Uani 1 1 d . . . . .
O1 O 0.1665(9) 0.3217(5) 0.7243(5) 0.0522(17) Uani 1 1 d . . . . .
H1B H 0.116(9) 0.285(5) 0.749(4) 0.03(2) Uiso 1 1 d . . . . .
H2B H 0.147(14) 0.332(7) 0.692(6) 0.06(4) Uiso 1 1 d . . . . .
N1 N 0.1298(7) 0.5030(4) 0.7812(4) 0.0387(14) Uani 1 1 d . . . . .
H1A H 0.143512 0.454118 0.754046 0.046 Uiso 1 1 calc R U . . .
N2 N 0.4305(7) 0.4119(4) 0.7879(3) 0.0360(13) Uani 1 1 d . . . . .
H2A H 0.357769 0.391089 0.757282 0.043 Uiso 1 1 calc R U . . .
C1 C -0.0081(10) 0.5460(6) 0.7758(5) 0.049(2) Uani 1 1 d . . . . .
H1 H -0.086840 0.522767 0.743113 0.059 Uiso 1 1 calc R U . . .
C2 C -0.0356(10) 0.6254(5) 0.8183(5) 0.0454(18) Uani 1 1 d . . . . .
H2 H -0.132042 0.655600 0.814659 0.054 Uiso 1 1 calc R U . . .
C3 C 0.0820(10) 0.6579(5) 0.8656(5) 0.0424(18) Uani 1 1 d . . . . .
H3 H 0.065122 0.711156 0.894274 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2296(9) 0.6125(4) 0.8720(4) 0.0378(16) Uani 1 1 d . . . . .
C5 C 0.3508(10) 0.6437(5) 0.9228(5) 0.0447(19) Uani 1 1 d . . . . .
H5 H 0.334695 0.696218 0.952431 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4887(10) 0.5986(5) 0.9289(5) 0.0484(19) Uani 1 1 d . . . . .
H6 H 0.566775 0.619254 0.963070 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5148(9) 0.5189(5) 0.8828(4) 0.0400(17) Uani 1 1 d . . . . .
C8 C 0.6631(9) 0.4721(5) 0.8868(5) 0.0462(19) Uani 1 1 d . . . . .
H8 H 0.742051 0.491538 0.920970 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6872(10) 0.3983(6) 0.8396(5) 0.051(2) Uani 1 1 d . . . . .
H9 H 0.783197 0.367602 0.840928 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5672(10) 0.3701(5) 0.7899(5) 0.0470(19) Uani 1 1 d . . . . .
H10 H 0.583688 0.320539 0.757397 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3985(8) 0.4863(4) 0.8317(4) 0.0306(14) Uani 1 1 d . . . . .
C12 C 0.2502(8) 0.5328(4) 0.8279(4) 0.0314(14) 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
Pb1 I1 3.0496(5) . ?
Pb1 I3 3.0616(6) . ?
Pb1 I5 3.1243(6) . ?
Pb1 I4 3.4155(6) . ?
Pb1 I2 3.4160(6) 3_666 ?
Pb2 I2 3.2001(5) . ?
Pb2 I2 3.2001(5) 3_566 ?
Pb2 I5 3.2119(5) 3_566 ?
Pb2 I5 3.2120(5) . ?
Pb2 I4 3.2406(6) 3_566 ?
Pb2 I4 3.2406(6) . ?
O1 H1B 0.83(8) . ?
O1 H2B 0.61(11) . ?
N1 C1 1.328(10) . ?
N1 C12 1.360(9) . ?
N1 H1A 0.8600 . ?
N2 C10 1.311(10) . ?
N2 C11 1.354(9) . ?
N2 H2A 0.8600 . ?
C1 C2 1.387(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.418(11) . ?
C3 H3 0.9300 . ?
C4 C12 1.397(9) . ?
C4 C5 1.415(10) . ?
C5 C6 1.341(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.426(11) . ?
C6 H6 0.9300 . ?
C7 C11 1.396(10) . ?
C7 C8 1.432(11) . ?
C8 C9 1.370(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(11) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.430(10) . ?

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 I3 91.638(15) . . ?
I1 Pb1 I5 89.473(16) . . ?
I3 Pb1 I5 96.176(18) . . ?
I1 Pb1 I4 95.756(15) . . ?
I3 Pb1 I4 172.420(16) . . ?
I5 Pb1 I4 82.261(17) . . ?
I1 Pb1 I2 102.889(15) . 3_666 ?
I3 Pb1 I2 101.974(17) . 3_666 ?
I5 Pb1 I2 157.607(16) . 3_666 ?
I4 Pb1 I2 78.021(15) . 3_666 ?
I2 Pb2 I2 180.0 . 3_566 ?
I2 Pb2 I5 93.536(15) . 3_566 ?
I2 Pb2 I5 86.463(15) 3_566 3_566 ?
I2 Pb2 I5 86.464(15) . . ?
I2 Pb2 I5 93.537(15) 3_566 . ?
I5 Pb2 I5 180.0 3_566 . ?
I2 Pb2 I4 90.177(14) . 3_566 ?
I2 Pb2 I4 89.823(14) 3_566 3_566 ?
I5 Pb2 I4 83.752(15) 3_566 3_566 ?
I5 Pb2 I4 96.248(15) . 3_566 ?
I2 Pb2 I4 89.824(14) . . ?
I2 Pb2 I4 90.176(13) 3_566 . ?
I5 Pb2 I4 96.248(15) 3_566 . ?
I5 Pb2 I4 83.752(15) . . ?
I4 Pb2 I4 180.0 3_566 . ?
Pb2 I2 Pb1 120.805(18) . 3_666 ?
Pb2 I4 Pb1 75.919(13) . . ?
Pb1 I5 Pb2 80.548(13) . . ?
H1B O1 H2B 123(10) . . ?
C1 N1 C12 123.0(7) . . ?
C1 N1 H1A 118.5 . . ?
C12 N1 H1A 118.5 . . ?
C10 N2 C11 123.0(6) . . ?
C10 N2 H2A 118.5 . . ?
C11 N2 H2A 118.5 . . ?
N1 C1 C2 120.6(7) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 118.4(8) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.5(7) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C12 C4 C5 120.5(7) . . ?
C12 C4 C3 117.4(7) . . ?
C5 C4 C3 122.0(7) . . ?
C6 C5 C4 121.0(7) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.7(7) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C11 C7 C6 121.0(7) . . ?
C11 C7 C8 118.6(7) . . ?
C6 C7 C8 120.4(7) . . ?
C9 C8 C7 119.1(7) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 119.3(8) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 121.2(8) . . ?
N2 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
N2 C11 C7 118.7(7) . . ?
N2 C11 C12 122.6(6) . . ?
C7 C11 C12 118.7(6) . . ?
N1 C12 C4 119.0(7) . . ?
N1 C12 C11 121.9(6) . . ?
C4 C12 C11 119.0(6) . . ?

_refine_diff_density_max         1.092
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.217




_publcif_funding_html            
;
;
# start Validation Reply Form
_vrf_PLAT417_jrn070_a2_a         
;
PROBLEM: Short Inter D-H..H-D       H1A      ..H2B      .       2.06 Ang.  
RESPONSE: Short distance is due to disordered nature and difficulty in
finding accurate location of H2B atom located on the water molecule.
;
_vrf_PLAT420_jrn070_a2_a         
;
PROBLEM: D-H Without Acceptor       O1       --H2B      .     Please Check 
RESPONSE: H2B atom does not have a nearest neighbor to act as an acceptor,
as the H-atoms on the N atoms of the phen molecule rigidifies the H2O 
molecule, thereby stabilizing it without the need for signifigant D-H
interactions.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_jrn089_a2_C2c_a
_database_code_depnum_ccdc_archive 'CCDC 1945576'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;Colorado State University
United States of America
;
#Added by publCIF



_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'HELIOS optics'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 I10 N4 Pb3'
_chemical_formula_weight         2206.97

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.0581(9)
_cell_length_b                   9.6584(4)
_cell_length_c                   20.2649(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.4910(10)
_cell_angle_gamma                90
_cell_volume                     4073.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.48

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.598
_exptl_crystal_F_000             3776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    19.964
_shelx_estimated_absorpt_T_min   0.340
_shelx_estimated_absorpt_T_max   0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4966
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\ms microfocus tube'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27016
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.754
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4203
_reflns_number_gt                3436
_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       'APEX3 (Bruker-AXS, 2015)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Vesta (K. Momma and F. Izumi, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0326P)²+17.4976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4203
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Pb1 Pb 0.35414(2) 0.73440(3) 0.55324(2) 0.03809(9) Uani 1 1 d . . . . .
Pb2 Pb 0.500000 0.72704(4) 0.750000 0.04067(11) Uani 1 2 d S T P . .
I1 I 0.24478(2) 0.50023(5) 0.49378(2) 0.03932(12) Uani 1 1 d . . . . .
I2 I 0.46307(2) 0.96512(5) 0.62693(3) 0.04497(13) Uani 1 1 d . . . . .
I3 I 0.34868(3) 0.69645(6) 0.71471(3) 0.04736(13) Uani 1 1 d . . . . .
I4 I 0.46668(2) 0.50470(5) 0.62091(3) 0.04738(13) Uani 1 1 d . . . . .
I5 I 0.35964(3) 0.72084(5) 0.40329(3) 0.04879(14) Uani 1 1 d . . . . .
N1 N 0.1956(3) 0.1828(7) 0.3353(4) 0.066(2) Uani 1 1 d . . . . .
H1A H 0.211071 0.108885 0.360414 0.079 Uiso 1 1 calc R U . . .
N2 N 0.3451(3) 0.3628(6) 0.4013(3) 0.0429(14) Uani 1 1 d . . . . .
H2A H 0.328379 0.444268 0.393051 0.051 Uiso 1 1 calc R U . . .
C1 C 0.1325(5) 0.1930(10) 0.2985(6) 0.078(3) Uani 1 1 d . . . . .
H1 H 0.106510 0.119972 0.299387 0.094 Uiso 1 1 calc R U . . .
C2 C 0.1051(4) 0.3085(9) 0.2595(5) 0.055(2) Uani 1 1 d . . . . .
H2 H 0.060768 0.316610 0.233651 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1446(4) 0.4107(8) 0.2597(4) 0.055(2) Uani 1 1 d . . . . .
H3 H 0.127285 0.491669 0.233873 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2103(4) 0.3977(7) 0.2976(4) 0.053(2) Uani 1 1 d . . . . .
H4 H 0.236717 0.469985 0.296962 0.063 Uiso 1 1 calc R U . . .
C5 C 0.2370(4) 0.2814(7) 0.3356(4) 0.0345(15) Uani 1 1 d . . . . .
C6 C 0.3055(4) 0.2526(7) 0.3761(4) 0.0374(16) Uani 1 1 d . . . . .
C7 C 0.3329(4) 0.1238(7) 0.3899(4) 0.0434(17) Uani 1 1 d . . . . .
H7 H 0.306999 0.045849 0.372904 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3981(4) 0.1084(8) 0.4284(4) 0.0499(19) Uani 1 1 d . . . . .
H8 H 0.416151 0.020279 0.438099 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4368(4) 0.2233(9) 0.4526(5) 0.055(2) Uani 1 1 d . . . . .
H9 H 0.481157 0.214692 0.478153 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4079(4) 0.3518(9) 0.4377(4) 0.0498(19) Uani 1 1 d . . . . .
H10 H 0.432891 0.431175 0.453529 0.060 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
Pb1 I5 3.0984(6) . ?
Pb1 I2 3.2056(5) . ?
Pb1 I1 3.2109(5) . ?
Pb1 I4 3.2363(6) . ?
Pb1 I1 3.2877(5) 7_566 ?
Pb1 I3 3.3485(6) . ?
Pb2 I4 3.2118(6) 2_656 ?
Pb2 I4 3.2118(6) . ?
Pb2 I2 3.2257(6) . ?
Pb2 I2 3.2257(6) 2_656 ?
Pb2 I3 3.2596(5) . ?
Pb2 I3 3.2597(5) 2_656 ?
N1 C1 1.323(11) . ?
N1 C5 1.346(9) . ?
N1 H1A 0.8600 . ?
N2 C10 1.316(9) . ?
N2 C6 1.350(9) . ?
N2 H2A 0.8600 . ?
C1 C2 1.356(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.341(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.351(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.461(11) . ?
C6 C7 1.368(9) . ?
C7 C8 1.372(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(11) . ?
C9 H9 0.9300 . ?
C10 H10 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
I5 Pb1 I2 97.563(15) . . ?
I5 Pb1 I1 87.662(14) . . ?
I2 Pb1 I1 174.740(15) . . ?
I5 Pb1 I4 91.303(15) . . ?
I2 Pb1 I4 87.394(15) . . ?
I1 Pb1 I4 91.897(15) . . ?
I5 Pb1 I1 93.717(14) . 7_566 ?
I2 Pb1 I1 84.252(14) . 7_566 ?
I1 Pb1 I1 96.059(14) . 7_566 ?
I4 Pb1 I1 170.752(15) . 7_566 ?
I5 Pb1 I3 171.291(16) . . ?
I2 Pb1 I3 88.415(14) . . ?
I1 Pb1 I3 86.325(14) . . ?
I4 Pb1 I3 82.612(14) . . ?
I1 Pb1 I3 93.177(14) 7_566 . ?
I4 Pb2 I4 96.08(2) 2_656 . ?
I4 Pb2 I2 175.884(15) 2_656 . ?
I4 Pb2 I2 87.470(14) . . ?
I4 Pb2 I2 87.469(14) 2_656 2_656 ?
I4 Pb2 I2 175.885(15) . 2_656 ?
I2 Pb2 I2 89.06(2) . 2_656 ?
I4 Pb2 I3 88.642(14) 2_656 . ?
I4 Pb2 I3 84.402(14) . . ?
I2 Pb2 I3 89.629(14) . . ?
I2 Pb2 I3 97.800(14) 2_656 . ?
I4 Pb2 I3 84.403(14) 2_656 2_656 ?
I4 Pb2 I3 88.644(14) . 2_656 ?
I2 Pb2 I3 97.800(14) . 2_656 ?
I2 Pb2 I3 89.628(14) 2_656 2_656 ?
I3 Pb2 I3 169.60(2) . 2_656 ?
Pb1 I1 Pb1 83.942(14) . 7_566 ?
Pb1 I2 Pb2 75.985(13) . . ?
Pb2 I3 Pb1 73.596(12) . . ?
Pb2 I4 Pb1 75.751(12) . . ?
C1 N1 C5 123.8(7) . . ?
C1 N1 H1A 118.1 . . ?
C5 N1 H1A 118.1 . . ?
C10 N2 C6 123.3(7) . . ?
C10 N2 H2A 118.4 . . ?
C6 N2 H2A 118.4 . . ?
N1 C1 C2 120.8(9) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 117.3(9) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.1(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.9(7) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N1 C5 C4 116.0(7) . . ?
N1 C5 C6 117.5(6) . . ?
C4 C5 C6 126.5(7) . . ?
N2 C6 C7 117.6(7) . . ?
N2 C6 C5 117.0(6) . . ?
C7 C6 C5 125.5(7) . . ?
C6 C7 C8 120.7(7) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 119.9(8) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 118.0(8) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
N2 C10 C9 120.5(7) . . ?
N2 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?

_refine_diff_density_max         1.244
_refine_diff_density_min         -1.070
_refine_diff_density_rms         0.190




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_jrn102_a1_a
_database_code_depnum_ccdc_archive 'CCDC 1945575'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;Colorado State University
United States of America
;
#Added by publCIF



_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'HELIOS optics'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Bi Br2 I4 N2 O'
_chemical_formula_weight         1049.59

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'
I I -0.4742 1.8119 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.8894(12)
_cell_length_b                   16.2437(11)
_cell_length_c                   7.7193(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.266(2)
_cell_angle_gamma                90
_cell_volume                     2011.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6078
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.53

_exptl_crystal_description       Fragment
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.467
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    18.878
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4617
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\ms microfocus tube'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10201
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.508
_diffrn_reflns_theta_max         26.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2095
_reflns_number_gt                1887
_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       'APEX3 (Bruker-AXS, 2015)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Vesta (K. Momma and F. Izumi, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0265P)²+8.0203P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2095
_refine_ls_number_parameters     98
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.500000 0.91986(2) 0.750000 0.03140(10) Uani 1 2 d S T P . .
I1 I 0.60717(2) 0.93344(2) 0.49435(5) 0.03774(11) Uani 1 1 d . . . . .
I2 I 0.38325(3) 0.79661(2) 0.52703(6) 0.04507(12) Uani 1 1 d . . . . .
Br1 Br 0.31099(5) 0.56428(4) 0.43143(10) 0.05210(18) Uani 1 1 d . . . . .
N1 N 0.4272(3) 0.4506(3) 0.6211(7) 0.0357(10) Uani 1 1 d . . . . .
H1 H 0.453176 0.494432 0.670659 0.043 Uiso 0.5 1 calc R U P . .
C1 C 0.3547(4) 0.4571(4) 0.4895(8) 0.0386(13) Uani 1 1 d . . . . .
C2 C 0.3102(4) 0.3894(5) 0.4018(9) 0.0498(16) Uani 1 1 d . . . . .
H2 H 0.259475 0.395277 0.310000 0.060 Uiso 1 1 calc R U . . .
C3 C 0.3444(5) 0.3127(5) 0.4567(10) 0.0591(19) Uani 1 1 d . . . . .
H3 H 0.317121 0.265692 0.399241 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4188(5) 0.3056(4) 0.5962(10) 0.0517(17) Uani 1 1 d . . . . .
H4 H 0.440964 0.253969 0.635590 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4603(4) 0.3768(3) 0.6774(8) 0.0360(12) Uani 1 1 d . . . . .
O1 O 0.500000 0.6065(4) 0.750000 0.080(3) Uani 1 2 d DS T P . .
H5 H 0.537(4) 0.653(3) 0.770(13) 0.097 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
Bi1 I2 2.9549(4) . ?
Bi1 I2 2.9549(4) 2_656 ?
Bi1 I1 3.0754(4) 2_656 ?
Bi1 I1 3.0755(4) . ?
Bi1 I1 3.2206(4) 6_576 ?
Bi1 I1 3.2206(4) 5_676 ?
Br1 C1 1.890(7) . ?
N1 C1 1.328(8) . ?
N1 C5 1.337(7) . ?
N1 H1 0.8600 . ?
C1 C2 1.382(9) . ?
C2 C3 1.383(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(8) . ?
C4 H4 0.9300 . ?
C5 C5 1.453(12) 2_656 ?
O1 H5 0.955(10) . ?

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
I2 Bi1 I2 94.698(19) . 2_656 ?
I2 Bi1 I1 90.163(12) . 2_656 ?
I2 Bi1 I1 95.414(13) 2_656 2_656 ?
I2 Bi1 I1 95.413(13) . . ?
I2 Bi1 I1 90.161(12) 2_656 . ?
I1 Bi1 I1 171.775(17) 2_656 . ?
I2 Bi1 I1 172.932(12) . 6_576 ?
I2 Bi1 I1 90.584(12) 2_656 6_576 ?
I1 Bi1 I1 84.658(11) 2_656 6_576 ?
I1 Bi1 I1 89.254(11) . 6_576 ?
I2 Bi1 I1 90.585(12) . 5_676 ?
I2 Bi1 I1 172.931(12) 2_656 5_676 ?
I1 Bi1 I1 89.254(11) 2_656 5_676 ?
I1 Bi1 I1 84.658(11) . 5_676 ?
I1 Bi1 I1 84.555(16) 6_576 5_676 ?
Bi1 I1 Bi1 95.341(11) . 5_676 ?
C1 N1 C5 120.7(5) . . ?
C1 N1 H1 119.6 . . ?
C5 N1 H1 119.6 . . ?
N1 C1 C2 122.8(6) . . ?
N1 C1 Br1 116.9(4) . . ?
C2 C1 Br1 120.3(5) . . ?
C1 C2 C3 117.1(7) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 120.4(6) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.2(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 119.8(6) . . ?
N1 C5 C5 116.2(3) . 2_656 ?
C4 C5 C5 124.0(4) . 2_656 ?

_refine_diff_density_max         1.358
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.160




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_jrn075_P-1_a
_database_code_depnum_ccdc_archive 'CCDC 1945579'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;Colorado State University
United States of America
;
#Added by publCIF



_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'HELIOS optics'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Bi2 I10 N4'
_chemical_formula_weight         2003.36

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'
I I -0.4742 1.8119 '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'

_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                   9.9732(4)
_cell_length_b                   10.5908(5)
_cell_length_c                   19.3664(9)
_cell_angle_alpha                80.227(2)
_cell_angle_beta                 88.320(2)
_cell_angle_gamma                88.114(2)
_cell_volume                     2014.20(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9640
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.47

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.303
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    16.406
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3823
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\ms microfocus tube'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64662
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         26.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8392
_reflns_number_gt                6482
_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       'APEX3 (Bruker-AXS, 2015)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Vesta (K. Momma and F. Izumi, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0326P)²+15.2371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8392
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.84182(4) 0.89613(3) 0.78618(2) 0.04403(10) Uani 1 1 d . . . . .
Bi2 Bi 0.81019(4) 1.23816(3) 0.63546(2) 0.04626(10) Uani 1 1 d . . . . .
I1 I 1.05312(7) 1.12386(6) 0.74055(4) 0.05246(17) Uani 1 1 d . . . . .
I2 I 0.58133(8) 1.31398(8) 0.54417(4) 0.0668(2) Uani 1 1 d . . . . .
I3 I 0.37961(8) 0.40309(8) 0.89835(5) 0.0728(2) Uani 1 1 d . . . . .
I4 I 0.62408(9) 0.71195(8) 0.81399(5) 0.0759(2) Uani 1 1 d . . . . .
I5 I 0.82469(10) 1.48609(8) 0.67677(5) 0.0826(3) Uani 1 1 d . . . . .
I6 I 0.87260(10) 0.91509(10) 0.93567(4) 0.0821(3) Uani 1 1 d . . . . .
I7 I 0.61998(7) 1.12940(7) 0.77021(4) 0.05882(18) Uani 1 1 d . . . . .
I8 I 0.81569(7) 0.92277(6) 0.62017(3) 0.05373(17) Uani 1 1 d . . . . .
I9 I 1.05784(7) 0.69711(6) 0.79158(4) 0.06069(19) Uani 1 1 d . . . . .
I10 I 1.00867(7) 1.29120(7) 0.51846(3) 0.05360(17) Uani 1 1 d . . . . .
N1 N 0.3920(11) 0.0644(11) 0.9306(6) 0.0830(15) Uani 1 1 d . . . . .
H1A H 0.405955 0.143088 0.933310 0.100 Uiso 1 1 calc R U . . .
N2 N 0.0401(12) 0.3958(11) 0.9380(6) 0.0889(16) Uani 1 1 d . . . . .
H2A H 0.125271 0.393495 0.944094 0.107 Uiso 1 1 calc R U . . .
N3 N 0.4209(9) 0.5823(9) 0.6894(6) 0.0690(9) Uani 1 1 d . . . . .
H3A H 0.483428 0.627962 0.701164 0.083 Uiso 1 1 calc R U . . .
N4 N 0.2055(9) 0.8444(9) 0.6074(5) 0.0690(9) Uani 1 1 d . . . . .
H4A H 0.132620 0.802876 0.608312 0.083 Uiso 1 1 calc R U . . .
C1 C 0.3103(14) 0.0439(14) 0.8837(7) 0.0830(15) Uani 1 1 d . . . . .
H1 H 0.270291 0.111643 0.853699 0.100 Uiso 1 1 calc R U . . .
C2 C 0.2853(14) -0.0747(14) 0.8796(7) 0.0830(15) Uani 1 1 d . . . . .
H2 H 0.221107 -0.088795 0.848114 0.100 Uiso 1 1 calc R U . . .
C3 C 0.3441(13) -0.1759(14) 0.9169(7) 0.0830(15) Uani 1 1 d . . . . .
H3 H 0.327053 -0.258379 0.909595 0.100 Uiso 1 1 calc R U . . .
C4 C 0.4452(13) -0.1512(14) 0.9746(7) 0.0830(15) Uani 1 1 d . . . . .
H4 H 0.490427 -0.216150 1.004192 0.100 Uiso 1 1 calc R U . . .
C5 C 0.4580(14) -0.0257(15) 0.9758(7) 0.0830(15) Uani 1 1 d . . . . .
C6 C -0.0030(14) 0.3293(14) 0.8926(8) 0.0889(16) Uani 1 1 d . . . . .
H6 H 0.056796 0.283152 0.868065 0.107 Uiso 1 1 calc R U . . .
C7 C -0.1338(14) 0.3290(14) 0.8823(8) 0.0889(16) Uani 1 1 d . . . . .
H7 H -0.167738 0.274951 0.854293 0.107 Uiso 1 1 calc R U . . .
C8 C -0.2165(15) 0.4062(14) 0.9122(8) 0.0889(16) Uani 1 1 d . . . . .
H8 H -0.307644 0.410877 0.902861 0.107 Uiso 1 1 calc R U . . .
C9 C -0.1633(14) 0.4822(14) 0.9590(8) 0.0889(16) Uani 1 1 d . . . . .
H9 H -0.218146 0.541598 0.977467 0.107 Uiso 1 1 calc R U . . .
C10 C -0.0347(15) 0.4669(14) 0.9759(8) 0.0889(16) Uani 1 1 d . . . . .
C11 C 0.4274(12) 0.4545(10) 0.7101(7) 0.0690(9) Uani 1 1 d . . . . .
H11 H 0.500141 0.417801 0.735931 0.083 Uiso 1 1 calc R U . . .
C12 C 0.3332(11) 0.3798(11) 0.6947(7) 0.0690(9) Uani 1 1 d . . . . .
H12 H 0.338096 0.291594 0.709598 0.083 Uiso 1 1 calc R U . . .
C13 C 0.2281(12) 0.4366(11) 0.6560(7) 0.0690(9) Uani 1 1 d . . . . .
H13 H 0.159761 0.386565 0.644578 0.083 Uiso 1 1 calc R U . . .
C14 C 0.2228(12) 0.5676(10) 0.6337(7) 0.0690(9) Uani 1 1 d . . . . .
H14 H 0.151702 0.604734 0.606612 0.083 Uiso 1 1 calc R U . . .
C15 C 0.3180(12) 0.6416(11) 0.6504(7) 0.0690(9) Uani 1 1 d . . . . .
C16 C 0.3182(12) 0.7791(11) 0.6298(7) 0.0690(9) Uani 1 1 d . . . . .
C17 C 0.4298(12) 0.8500(11) 0.6273(7) 0.0690(9) Uani 1 1 d . . . . .
H17 H 0.510791 0.809221 0.641579 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4267(12) 0.9800(10) 0.6043(7) 0.0690(9) Uani 1 1 d . . . . .
H18 H 0.504436 1.026332 0.603674 0.083 Uiso 1 1 calc R U . . .
C19 C 0.3077(11) 1.0414(11) 0.5822(7) 0.0690(9) Uani 1 1 d . . . . .
H19 H 0.302471 1.129516 0.566816 0.083 Uiso 1 1 calc R U . . .
C20 C 0.2008(12) 0.9693(11) 0.5838(7) 0.0690(9) Uani 1 1 d . . . . .
H20 H 0.119788 1.007969 0.567923 0.083 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 I4 2.9435(8) . ?
Bi1 I9 2.9554(8) . ?
Bi1 I6 2.9614(8) . ?
Bi1 I8 3.1969(7) . ?
Bi1 I7 3.2428(8) . ?
Bi1 I1 3.2467(7) . ?
Bi2 I5 2.8810(8) . ?
Bi2 I2 2.9349(8) . ?
Bi2 I10 2.9573(8) . ?
Bi2 I7 3.2510(8) . ?
Bi2 I1 3.2768(7) . ?
Bi2 I8 3.4016(8) . ?
N1 C1 1.287(16) . ?
N1 C5 1.349(17) . ?
N1 H1A 0.8600 . ?
N2 C6 1.306(15) . ?
N2 C10 1.334(17) . ?
N2 H2A 0.8600 . ?
N3 C11 1.344(13) . ?
N3 C15 1.364(14) . ?
N3 H3A 0.8600 . ?
N4 C20 1.324(14) . ?
N4 C16 1.344(14) . ?
N4 H4A 0.8600 . ?
C1 C2 1.305(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.316(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.587(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.343(19) . ?
C4 H4 0.9300 . ?
C5 C5 1.46(3) 2_657 ?
C6 C7 1.326(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.332(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.433(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.331(18) . ?
C9 H9 0.9300 . ?
C10 C10 1.46(3) 2_567 ?
C11 C12 1.321(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.332(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.443(15) . ?
C16 C17 1.358(15) . ?
C17 C18 1.373(15) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(15) . ?
C18 H18 0.9300 . ?
C19 C20 1.328(15) . ?
C19 H19 0.9300 . ?
C20 H20 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
I4 Bi1 I9 94.60(3) . . ?
I4 Bi1 I6 94.29(3) . . ?
I9 Bi1 I6 92.06(3) . . ?
I4 Bi1 I8 92.61(2) . . ?
I9 Bi1 I8 93.05(2) . . ?
I6 Bi1 I8 171.05(3) . . ?
I4 Bi1 I7 89.41(3) . . ?
I9 Bi1 I7 175.16(2) . . ?
I6 Bi1 I7 90.33(3) . . ?
I8 Bi1 I7 84.05(2) . . ?
I4 Bi1 I1 171.93(3) . . ?
I9 Bi1 I1 91.80(2) . . ?
I6 Bi1 I1 90.37(2) . . ?
I8 Bi1 I1 82.134(19) . . ?
I7 Bi1 I1 83.97(2) . . ?
I5 Bi2 I2 93.86(3) . . ?
I5 Bi2 I10 95.22(2) . . ?
I2 Bi2 I10 93.17(2) . . ?
I5 Bi2 I7 92.49(2) . . ?
I2 Bi2 I7 93.29(2) . . ?
I10 Bi2 I7 169.59(2) . . ?
I5 Bi2 I1 91.14(3) . . ?
I2 Bi2 I1 174.10(2) . . ?
I10 Bi2 I1 89.48(2) . . ?
I7 Bi2 I1 83.36(2) . . ?
I5 Bi2 I8 168.29(3) . . ?
I2 Bi2 I8 96.05(2) . . ?
I10 Bi2 I8 90.44(2) . . ?
I7 Bi2 I8 80.755(19) . . ?
I1 Bi2 I8 78.646(18) . . ?
Bi1 I1 Bi2 81.494(17) . . ?
Bi1 I7 Bi2 81.948(18) . . ?
Bi1 I8 Bi2 80.312(16) . . ?
C1 N1 C5 126.2(13) . . ?
C1 N1 H1A 116.9 . . ?
C5 N1 H1A 116.9 . . ?
C6 N2 C10 126.6(13) . . ?
C6 N2 H2A 116.7 . . ?
C10 N2 H2A 116.7 . . ?
C11 N3 C15 121.9(10) . . ?
C11 N3 H3A 119.1 . . ?
C15 N3 H3A 119.1 . . ?
C20 N4 C16 123.5(10) . . ?
C20 N4 H4A 118.3 . . ?
C16 N4 H4A 118.3 . . ?
N1 C1 C2 118.0(15) . . ?
N1 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
C1 C2 C3 124.9(14) . . ?
C1 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
C2 C3 C4 117.2(13) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C5 C4 C3 112.2(13) . . ?
C5 C4 H4 123.9 . . ?
C3 C4 H4 123.9 . . ?
C4 C5 N1 121.3(13) . . ?
C4 C5 C5 124.5(17) . 2_657 ?
N1 C5 C5 114.2(17) . 2_657 ?
N2 C6 C7 118.7(14) . . ?
N2 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C8 119.7(13) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 119.2(13) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 119.4(13) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 N2 115.4(12) . . ?
C9 C10 C10 126.6(17) . 2_567 ?
N2 C10 C10 117.4(16) . 2_567 ?
C12 C11 N3 121.8(11) . . ?
C12 C11 H11 119.1 . . ?
N3 C11 H11 119.1 . . ?
C11 C12 C13 117.8(11) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C12 C13 C14 120.4(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.9(11) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 N3 117.2(10) . . ?
C14 C15 C16 124.0(11) . . ?
N3 C15 C16 118.8(10) . . ?
N4 C16 C17 115.5(10) . . ?
N4 C16 C15 120.5(10) . . ?
C17 C16 C15 123.9(11) . . ?
C16 C17 C18 122.0(11) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C19 119.6(11) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 117.1(11) . . ?
C20 C19 H19 121.5 . . ?
C18 C19 H19 121.5 . . ?
N4 C20 C19 122.3(11) . . ?
N4 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?

_refine_diff_density_max         1.924
_refine_diff_density_min         -1.439
_refine_diff_density_rms         0.184




_publcif_funding_html            
;
;
# start Validation Reply Form
_vrf_PLAT369_jrn075_P-1_a        
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C3       - C4       .       1.59 Ang.  
RESPONSE: Slight disorder exists in the bpy molecule resulting in the 
slight elongation of the bond.
;
_vrf_PLAT414_jrn075_P-1_a        
;
PROBLEM: Short Intra D-H..H-X       H1A      ..H4               1.89 Ang.  
RESPONSE: Short contact exists due to the protonation of the bpy 
molecule.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_jrn111_P21c_a
_database_code_depnum_ccdc_archive 'CCDC 1945578'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;Colorado State University
United States of America
;
#Added by publCIF



_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'HELIOS optics'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 Br2 I3 N2 Pb'
_chemical_formula_weight         902.89

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'
Br Br -0.2901 2.4595 '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'
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'

_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                   13.655(2)
_cell_length_b                   17.038(3)
_cell_length_c                   8.0837(12)
_cell_angle_alpha                90
_cell_angle_beta                 104.528(3)
_cell_angle_gamma                90
_cell_volume                     1820.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.43

_exptl_crystal_description       Fragment
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.294
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .08
_exptl_crystal_size_mid          .06
_exptl_crystal_size_min          .01
_exptl_absorpt_coefficient_mu    18.730
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3682
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\ms microfocus tube'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27395
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.845
_diffrn_reflns_theta_max         28.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4565
_reflns_number_gt                3655
_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       'APEX3 (Bruker-AXS, 2015)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Vesta (K. Momma and F. Izumi, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0912P)²+248.7615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4565
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2785
_refine_ls_wR_factor_gt          0.2685
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
Pb1 Pb 0.22266(8) 0.25069(6) 0.33834(12) 0.0347(3) Uani 1 1 d . . . . .
I2 I 0.20877(15) 0.39957(10) 0.0823(2) 0.0401(4) Uani 1 1 d . . . . .
I3 I 0.05798(14) 0.33051(12) 0.5093(2) 0.0450(5) Uani 1 1 d . . . . .
I4 I 0.38969(15) 0.31497(12) 0.6463(2) 0.0447(5) Uani 1 1 d . . . . .
Br1 Br 0.53127(19) 0.56166(16) 0.7415(3) 0.0369(6) Uani 1 1 d . . . . .
Br2 Br 0.3804(3) 0.7090(2) -0.0485(4) 0.0526(8) Uani 1 1 d . . . . .
N1 N 0.3405(19) 0.5769(14) 0.488(3) 0.039(5) Uani 1 1 d . . . . .
H1 H 0.379965 0.597213 0.431935 0.047 Uiso 1 1 calc R U . . .
N2 N 0.2867(17) 0.6350(13) 0.182(3) 0.038(5) Uani 1 1 d . . . . .
C1 C 0.382(2) 0.5509(16) 0.643(4) 0.042(6) Uani 1 1 d . . . . .
C2 C 0.320(2) 0.518(2) 0.737(4) 0.047(7) Uani 1 1 d . . . . .
H2 H 0.346666 0.500203 0.847243 0.057 Uiso 1 1 calc R U . . .
C3 C 0.220(3) 0.513(2) 0.664(4) 0.060(9) Uani 1 1 d . . . . .
H3 H 0.177686 0.489887 0.724053 0.072 Uiso 1 1 calc R U . . .
C4 C 0.180(2) 0.5415(17) 0.501(4) 0.046(7) Uani 1 1 d . . . . .
H4 H 0.110074 0.538183 0.454582 0.055 Uiso 1 1 calc R U . . .
C5 C 0.238(2) 0.5740(16) 0.409(4) 0.045(7) Uani 1 1 d . . . . .
C6 C 0.213(2) 0.6059(17) 0.237(4) 0.043(6) Uani 1 1 d . . . . .
C7 C 0.113(3) 0.612(2) 0.143(4) 0.064(10) Uani 1 1 d . . . . .
H7 H 0.061357 0.594575 0.188374 0.077 Uiso 1 1 calc R U . . .
C8 C 0.092(2) 0.643(3) -0.014(4) 0.063(10) Uani 1 1 d . . . . .
H8 H 0.025827 0.645762 -0.080463 0.076 Uiso 1 1 calc R U . . .
C9 C 0.171(3) 0.672(2) -0.073(4) 0.060(9) Uani 1 1 d . . . . .
H9 H 0.158382 0.695975 -0.179888 0.073 Uiso 1 1 calc R U . . .
C10 C 0.264(2) 0.6658(18) 0.020(4) 0.045(7) 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
Pb1 I4 3.123(2) . ?
Pb1 I3 3.221(2) . ?
Pb1 I2 3.249(2) . ?
Pb1 I4 3.262(2) 4_565 ?
Pb1 I2 3.266(2) 4_566 ?
Pb1 I3 3.323(2) 4_565 ?
Br1 C1 2.01(3) . ?
Br2 C10 1.95(3) . ?
N1 C1 1.31(3) . ?
N1 C5 1.39(4) . ?
N1 H1 0.8600 . ?
N2 C6 1.30(4) . ?
N2 C10 1.37(4) . ?
C1 C2 1.39(4) . ?
C2 C3 1.34(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.38(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.34(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.45(4) . ?
C6 C7 1.39(4) . ?
C7 C8 1.33(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.38(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.31(5) . ?
C9 H9 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
I4 Pb1 I3 87.64(6) . . ?
I4 Pb1 I2 98.53(6) . . ?
I3 Pb1 I2 90.47(5) . . ?
I4 Pb1 I4 92.39(6) . 4_565 ?
I3 Pb1 I4 174.71(6) . 4_565 ?
I2 Pb1 I4 84.30(5) . 4_565 ?
I4 Pb1 I2 86.27(5) . 4_566 ?
I3 Pb1 I2 85.37(5) . 4_566 ?
I2 Pb1 I2 173.53(8) . 4_566 ?
I4 Pb1 I2 99.90(6) 4_565 4_566 ?
I4 Pb1 I3 175.11(6) . 4_565 ?
I3 Pb1 I3 96.55(7) . 4_565 ?
I2 Pb1 I3 84.00(5) . 4_565 ?
I4 Pb1 I3 83.67(5) 4_565 4_565 ?
I2 Pb1 I3 91.54(5) 4_566 4_565 ?
Pb1 I2 Pb1 76.69(4) . 4_565 ?
Pb1 I3 Pb1 76.27(4) . 4_566 ?
Pb1 I4 Pb1 78.53(5) . 4_566 ?
C1 N1 C5 125(3) . . ?
C1 N1 H1 117.6 . . ?
C5 N1 H1 117.6 . . ?
C6 N2 C10 118(2) . . ?
N1 C1 C2 119(3) . . ?
N1 C1 Br1 120(2) . . ?
C2 C1 Br1 121(2) . . ?
C3 C2 C1 119(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 N1 116(3) . . ?
C4 C5 C6 131(3) . . ?
N1 C5 C6 113(3) . . ?
N2 C6 C7 121(3) . . ?
N2 C6 C5 117(3) . . ?
C7 C6 C5 121(3) . . ?
C8 C7 C6 120(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 118(3) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C10 C9 C8 120(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 N2 122(3) . . ?
C9 C10 Br2 123(3) . . ?
N2 C10 Br2 114(2) . . ?

_refine_diff_density_max         10.396
_refine_diff_density_min         -4.586
_refine_diff_density_rms         0.573


_publcif_funding_html            
;
;

# start Validation Reply Form
_vrf_PLAT097_jrn111_P21c_a       
;
PROBLEM: Large Reported Max.  (Positive) Residual Density      10.40 eA-3  
RESPONSE: Large residual density exists due to this structure being an
average structure: The Pb-I chains can occupy one of two possible
positions in 50% occupancy, where the large residual density resides.
Attempts at refining the average structure completely were not
successful, therefore the average structure was reported.
;
_vrf_PLAT342_jrn111_P21c_a       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04556 Ang.  
RESPONSE: The difficulty in growing large single crystals limited the 
specimens available to collect data on. Additionally, the large
difference in scattering between the inorganic and organic units further
increases difficulty in resolving the organic components. Nonetheless,
we note that bonds in the organic cations are chemically reasonable
with little constraints needed.
;
_vrf_PLAT930_jrn111_P21c_a       
;
PROBLEM: FCF-based   Twin Law ( 1 0 0)[ 5 0 2] Est.d BASF       0.20 Check 
RESPONSE: The predicted twin domain appears due to the split-site 
disorder of the Pb-I chains. Attempts at deconvoluting the two positions
were unsuccessful, thus the structure reported is the average structure.
;
# end Validation Reply Form

