# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1820029'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 I6 N2 O0 Pb2'
_chemical_formula_weight         1418.13

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'
O O 0.0106 0.0060 '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'
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                   7.8674(6)
_cell_length_b                   17.7109(16)
_cell_length_c                   21.9456(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.763(2)
_cell_angle_gamma                90
_cell_volume                     3022.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5248
_cell_measurement_theta_min      3.043
_cell_measurement_theta_max      27.011

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.117
_exptl_crystal_F_000             2456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    17.261
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22797
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.043
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             5248
_reflns_number_gt                3756
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0435P)²] 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     SHELXL
_refine_ls_extinction_coef       0.00015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5248
_refine_ls_number_parameters     240
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.001

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 0.41836(5) 0.86364(2) 0.01159(2) 0.05669(15) Uani 1 1 d . . . . .
Pb2 Pb -0.04717(5) 0.95165(3) 0.10308(2) 0.05609(15) Uani 1 1 d . . . . .
I4 I 0.26570(8) 1.03646(4) 0.04175(3) 0.0553(2) Uani 1 1 d . . . . .
I3 I 0.63888(9) 0.87031(5) 0.14919(3) 0.0686(2) Uani 1 1 d . . . . .
I5 I 0.10008(9) 0.79055(4) 0.05466(4) 0.0644(2) Uani 1 1 d . . . . .
I2 I 0.21091(9) 0.88966(4) -0.12395(3) 0.0637(2) Uani 1 1 d . . . . .
I1 I 0.54968(11) 0.70944(5) -0.02131(4) 0.0777(3) Uani 1 1 d . . . . .
I6 I 0.15351(12) 0.95407(6) 0.23236(4) 0.0896(3) Uani 1 1 d . . . . .
N1 N -0.2117(14) 1.0829(7) 0.3308(5) 0.083(3) Uani 1 1 d . U . . .
N2 N -0.9139(13) 1.2680(6) 0.1654(5) 0.074(3) Uani 1 1 d . . . . .
C3 C -0.4965(15) 1.1520(7) 0.2666(5) 0.070(2) Uani 1 1 d . U . . .
C9 C -0.7472(17) 1.2403(8) 0.2590(6) 0.080(3) Uani 1 1 d . U . . .
H9 H -0.7246 1.2468 0.3015 0.095 Uiso 1 1 calc R U . . .
C5 C -0.2974(16) 1.0478(8) 0.2827(6) 0.077(3) Uani 1 1 d . U . . .
H5 H -0.2620 1.0006 0.2709 0.093 Uiso 1 1 calc R U . . .
C6 C -0.8190(16) 1.2194(8) 0.1368(6) 0.079(3) Uani 1 1 d . U . . .
H6 H -0.8463 1.2122 0.0944 0.095 Uiso 1 1 calc R U . . .
C10 C -0.8748(18) 1.2786(8) 0.2269(6) 0.085(3) Uani 1 1 d . U . . .
H10 H -0.9377 1.3129 0.2467 0.101 Uiso 1 1 calc R U . . .
C4 C -0.4387(16) 1.0818(7) 0.2505(6) 0.074(3) Uani 1 1 d . U . . .
H4 H -0.4985 1.0570 0.2164 0.089 Uiso 1 1 calc R U . . .
C7 C -0.6851(16) 1.1811(8) 0.1686(6) 0.076(3) Uani 1 1 d . U . . .
H7 H -0.6206 1.1486 0.1479 0.092 Uiso 1 1 calc R U . . .
C8 C -0.6446(15) 1.1901(7) 0.2311(5) 0.070(2) Uani 1 1 d . U . . .
C2 C -0.4009(16) 1.1862(8) 0.3180(6) 0.081(3) Uani 1 1 d . U . . .
H2 H -0.4334 1.2336 0.3303 0.098 Uiso 1 1 calc R U . . .
C1 C -0.2604(18) 1.1515(9) 0.3506(6) 0.090(4) Uani 1 1 d . U . . .
H1 H -0.1994 1.1742 0.3855 0.108 Uiso 1 1 calc R U . . .
C14 C -1.050(2) 1.3111(10) 0.1272(7) 0.102(4) Uani 1 1 d . U . . .
H14 H -1.0995 1.2783 0.0931 0.123 Uiso 1 1 calc R U . . .
C15 C -0.983(2) 1.3791(10) 0.0997(8) 0.135(6) Uani 1 1 d . U . . .
H15A H -0.8970 1.3645 0.0752 0.202 Uiso 1 1 calc R U . . .
H15B H -0.9323 1.4124 0.1320 0.202 Uiso 1 1 calc R U . . .
H15C H -1.0752 1.4045 0.0742 0.202 Uiso 1 1 calc R U . . .
C11 C -0.055(2) 1.0461(11) 0.3653(9) 0.125(5) Uani 1 1 d . U . . .
H11 H -0.0328 1.0024 0.3401 0.150 Uiso 1 1 calc R U . . .
C16 C -1.199(2) 1.3304(11) 0.1666(8) 0.142(6) Uani 1 1 d . U . . .
H16A H -1.1610 1.3701 0.1953 0.214 Uiso 1 1 calc R U . . .
H16B H -1.2252 1.2863 0.1888 0.214 Uiso 1 1 calc R U . . .
H16C H -1.2997 1.3465 0.1395 0.214 Uiso 1 1 calc R U . . .
C12 C 0.102(2) 1.0965(10) 0.3661(8) 0.123(5) Uani 1 1 d . U . . .
H12A H 0.1268 1.1023 0.3249 0.185 Uiso 1 1 calc R U . . .
H12B H 0.1989 1.0740 0.3915 0.185 Uiso 1 1 calc R U . . .
H12C H 0.0789 1.1451 0.3824 0.185 Uiso 1 1 calc R U . . .
C13 C -0.086(3) 1.0143(14) 0.4239(9) 0.174(7) Uani 1 1 d . U . . .
H13A H -0.1261 1.0533 0.4486 0.260 Uiso 1 1 calc R U . . .
H13B H 0.0186 0.9932 0.4453 0.260 Uiso 1 1 calc R U . . .
H13C H -0.1717 0.9753 0.4163 0.260 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 I1 3.0454(10) . ?
Pb1 I5 3.0920(8) . ?
Pb1 I2 3.2008(8) . ?
Pb1 I3 3.2475(8) . ?
Pb1 I4 3.3897(9) . ?
Pb1 I4 3.4010(8) 3_675 ?
Pb2 I6 3.0297(9) . ?
Pb2 I2 3.1540(9) 3_575 ?
Pb2 I3 3.1562(8) 1_455 ?
Pb2 I5 3.3147(9) . ?
Pb2 I4 3.3370(8) . ?
Pb2 I4 3.3820(8) 3_575 ?
I4 Pb2 3.3820(8) 3_575 ?
I4 Pb1 3.4009(8) 3_675 ?
I3 Pb2 3.1562(8) 1_655 ?
I2 Pb2 3.1540(9) 3_575 ?
N1 C5 1.318(14) . ?
N1 C1 1.366(16) . ?
N1 C11 1.497(19) . ?
N2 C6 1.355(15) . ?
N2 C10 1.352(14) . ?
N2 C14 1.467(17) . ?
C3 C4 1.390(17) . ?
C3 C2 1.394(15) . ?
C3 C8 1.464(17) . ?
C9 C10 1.323(17) . ?
C9 C8 1.402(16) . ?
C5 C4 1.363(17) . ?
C6 C7 1.354(17) . ?
C7 C8 1.370(15) . ?
C2 C1 1.368(17) . ?
C14 C15 1.48(2) . ?
C14 C16 1.60(2) . ?
C11 C13 1.46(2) . ?
C11 C12 1.52(2) . ?

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 I5 90.97(3) . . ?
I1 Pb1 I2 92.99(2) . . ?
I5 Pb1 I2 91.28(2) . . ?
I1 Pb1 I3 95.77(2) . . ?
I5 Pb1 I3 94.23(2) . . ?
I2 Pb1 I3 169.56(3) . . ?
I1 Pb1 I4 177.55(2) . . ?
I5 Pb1 I4 89.47(2) . . ?
I2 Pb1 I4 84.60(2) . . ?
I3 Pb1 I4 86.59(2) . . ?
I1 Pb1 I4 95.32(2) . 3_675 ?
I5 Pb1 I4 172.50(2) . 3_675 ?
I2 Pb1 I4 84.32(2) . 3_675 ?
I3 Pb1 I4 89.21(2) . 3_675 ?
I4 Pb1 I4 84.07(2) . 3_675 ?
I6 Pb2 I2 91.01(3) . 3_575 ?
I6 Pb2 I3 91.59(3) . 1_455 ?
I2 Pb2 I3 90.19(2) 3_575 1_455 ?
I6 Pb2 I5 98.90(3) . . ?
I2 Pb2 I5 169.74(2) 3_575 . ?
I3 Pb2 I5 92.22(2) 1_455 . ?
I6 Pb2 I4 93.45(3) . . ?
I2 Pb2 I4 90.01(2) 3_575 . ?
I3 Pb2 I4 174.95(2) 1_455 . ?
I5 Pb2 I4 86.72(2) . . ?
I6 Pb2 I4 175.55(3) . 3_575 ?
I2 Pb2 I4 85.44(2) 3_575 3_575 ?
I3 Pb2 I4 91.10(2) 1_455 3_575 ?
I5 Pb2 I4 84.54(2) . 3_575 ?
I4 Pb2 I4 83.889(19) . 3_575 ?
Pb2 I4 Pb2 96.110(19) . 3_575 ?
Pb2 I4 Pb1 88.71(2) . . ?
Pb2 I4 Pb1 90.988(19) 3_575 . ?
Pb2 I4 Pb1 174.69(3) . 3_675 ?
Pb2 I4 Pb1 86.425(19) 3_575 3_675 ?
Pb1 I4 Pb1 95.93(2) . 3_675 ?
Pb2 I3 Pb1 92.97(2) 1_655 . ?
Pb1 I5 Pb2 94.39(2) . . ?
Pb2 I2 Pb1 98.92(2) 3_575 . ?
C5 N1 C1 122.7(12) . . ?
C5 N1 C11 118.9(13) . . ?
C1 N1 C11 118.5(12) . . ?
C6 N2 C10 119.6(12) . . ?
C6 N2 C14 118.1(11) . . ?
C10 N2 C14 122.2(12) . . ?
C4 C3 C2 116.0(12) . . ?
C4 C3 C8 122.8(10) . . ?
C2 C3 C8 121.2(12) . . ?
C10 C9 C8 122.3(12) . . ?
N1 C5 C4 119.1(13) . . ?
N2 C6 C7 121.3(12) . . ?
C9 C10 N2 119.9(13) . . ?
C5 C4 C3 122.3(11) . . ?
C8 C7 C6 120.2(12) . . ?
C7 C8 C9 116.7(12) . . ?
C7 C8 C3 121.7(11) . . ?
C9 C8 C3 121.6(11) . . ?
C1 C2 C3 121.4(13) . . ?
C2 C1 N1 118.5(12) . . ?
N2 C14 C15 112.5(13) . . ?
N2 C14 C16 109.4(13) . . ?
C15 C14 C16 112.5(15) . . ?
C13 C11 N1 112.0(16) . . ?
C13 C11 C12 117.6(17) . . ?
N1 C11 C12 110.8(15) . . ?

_refine_diff_density_max         1.297
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.193

_shelxl_version_number           2014-1

