# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Bz-Pb-I
_database_code_depnum_ccdc_archive 'CCDC 1534632'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Bz-Pb-I
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C6H9I3NOPb
_chemical_formula_sum            'C6 H9 I3 N O Pb'
_chemical_formula_weight         699.03

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'
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'
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           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                   4.481(3)
_cell_length_b                   13.193(9)
_cell_length_c                   22.544(15)
_cell_angle_alpha                90
_cell_angle_beta                 89.879(13)
_cell_angle_gamma                90
_cell_volume                     1332.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8369
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.25

_exptl_crystal_description       needle
_exptl_crystal_colour            'yellow coloured'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.484
_exptl_crystal_F_000             1204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    19.573
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4076
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS;Universitat Gottingen,1997'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17207
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.111
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2353
_reflns_number_gt                2277
_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.

 Here we were unable to obtain single crystals with reasonable 
 size to have good quality x-ray diffraction data. Unfortunately 
 sufficiently sized crystals were all twinned. This resulted in 
 strong spurious diffraction spots adjacent to the metal and 
 some of the other atoms. The correlations between these spurious 
 reflections, created problems in locating or fixing the hydrogens 
 on the solvent atom. 

 We tried different absorption correction models (spherical,
 numerical) considering the material to be weak to strong 
 absorber, yet we obtained no appreciable difference in the 
 refined data.  
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+205.0542P] 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         2353
_refine_ls_number_parameters     81
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1798
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.387
_refine_ls_restrained_S_all      1.367
_refine_ls_shift/su_max          0.046
_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 0.7446(2) 0.47471(8) 0.40866(4) 0.0203(3) Uani 1 1 d . . . . .
I2 I 0.7491(4) 0.58549(13) 0.28816(8) 0.0217(4) Uani 1 1 d . . . . .
I1 I 1.2435(4) 0.62980(13) 0.45663(8) 0.0234(4) Uani 1 1 d . . . . .
I3 I 1.2396(5) 0.31485(14) 0.36720(9) 0.0269(5) Uani 1 1 d . . . . .
N1A N 0.69(2) 0.916(7) 0.297(3) 0.04(3) Uiso 0.30(3) 1 d D U P A 1
H1A1 H 0.5219 0.8759 0.2987 0.058 Uiso 0.30(3) 1 calc R U P A 1
H1A2 H 0.8338 0.8837 0.2767 0.058 Uiso 0.30(3) 1 calc R U P A 1
H1A3 H 0.6388 0.9748 0.2774 0.058 Uiso 0.30(3) 1 calc R U P A 1
C1A C 0.786(14) 0.940(5) 0.356(2) 0.024(14) Uiso 0.30(3) 1 d DG U P A 1
C2A C 0.858(18) 1.039(4) 0.371(3) 0.049(17) Uiso 0.30(3) 1 d DG U P A 1
H2A H 0.8402 1.0916 0.3419 0.059 Uiso 0.30(3) 1 calc R U P A 1
C3A C 0.96(2) 1.062(5) 0.428(3) 0.054(19) Uiso 0.30(3) 1 d DG U P A 1
H3A H 1.0042 1.1301 0.4378 0.064 Uiso 0.30(3) 1 calc R U P A 1
C4A C 0.981(18) 0.986(6) 0.470(2) 0.05(2) Uiso 0.30(3) 1 d DG U P A 1
C5A C 0.91(2) 0.887(5) 0.455(3) 0.055(19) Uiso 0.30(3) 1 d DG U P A 1
H5A H 0.9265 0.8343 0.4837 0.066 Uiso 0.30(3) 1 calc R U P A 1
C6A C 0.812(19) 0.864(4) 0.398(3) 0.048(17) Uiso 0.30(3) 1 d DG U P A 1
H6A H 0.7625 0.7958 0.3879 0.058 Uiso 0.30(3) 1 calc R U P A 1
N1B N 0.762(10) 0.911(3) 0.2928(14) 0.028(11) Uiso 0.70(3) 1 d D U P A 2
H1B1 H 0.9617 0.9127 0.2858 0.043 Uiso 0.70(3) 1 calc R U P A 2
H1B2 H 0.6690 0.9560 0.2681 0.043 Uiso 0.70(3) 1 calc R U P A 2
H1B3 H 0.6906 0.8479 0.2860 0.043 Uiso 0.70(3) 1 calc R U P A 2
C1B C 0.704(7) 0.939(2) 0.3534(11) 0.036(10) Uiso 0.70(3) 1 d DG U P A 2
C2B C 0.682(9) 0.864(2) 0.3964(14) 0.054(12) Uiso 0.70(3) 1 d DG U P A 2
H2B H 0.7122 0.7954 0.3860 0.065 Uiso 0.70(3) 1 calc R U P A 2
C3B C 0.615(10) 0.890(3) 0.4548(13) 0.070(14) Uiso 0.70(3) 1 d DG U P A 2
H3B H 0.5999 0.8389 0.4842 0.084 Uiso 0.70(3) 1 calc R U P A 2
C4B C 0.571(9) 0.991(3) 0.4700(12) 0.056(13) Uiso 0.70(3) 1 d DG U P A 2
C5B C 0.593(10) 1.066(2) 0.4270(15) 0.071(14) Uiso 0.70(3) 1 d DG U P A 2
H5B H 0.5625 1.1352 0.4375 0.085 Uiso 0.70(3) 1 calc R U P A 2
C6B C 0.660(9) 1.040(2) 0.3687(13) 0.047(11) Uiso 0.70(3) 1 d DG U P A 2
H6B H 0.6748 1.0917 0.3393 0.056 Uiso 0.70(3) 1 calc R U P A 2
O1S O 0.255(5) 0.7963(15) 0.2638(10) 0.033(5) 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 I2 3.085(3) . ?
Pb1 I3 3.199(3) . ?
Pb1 I1 3.219(3) . ?
Pb1 I1 3.223(2) 1_455 ?
Pb1 I3 3.233(3) 1_455 ?
Pb1 I1 3.336(3) 3_766 ?
I1 Pb1 3.223(3) 1_655 ?
I1 Pb1 3.336(3) 3_766 ?
I3 Pb1 3.233(3) 1_655 ?
N1A C1A 1.44(4) . ?
N1A H1A1 0.9101 . ?
N1A H1A2 0.9101 . ?
N1A H1A3 0.9101 . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900(13) . ?
C4A C4A 1.42(10) 3_776 ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N1B C1B 1.44(3) . ?
N1B H1B1 0.9100 . ?
N1B H1B2 0.9100 . ?
N1B H1B3 0.9100 . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C2B C3B 1.3900 . ?
C2B H2B 0.9500 . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3900 . ?
C4B C4B 1.51(5) 3_676 ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?

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 Pb1 I3 92.98(6) . . ?
I2 Pb1 I1 89.51(6) . . ?
I3 Pb1 I1 92.04(7) . . ?
I2 Pb1 I1 89.88(6) . 1_455 ?
I3 Pb1 I1 177.14(6) . 1_455 ?
I1 Pb1 I1 88.14(7) . 1_455 ?
I2 Pb1 I3 93.32(6) . 1_455 ?
I3 Pb1 I3 88.32(7) . 1_455 ?
I1 Pb1 I3 177.13(6) . 1_455 ?
I1 Pb1 I3 91.35(7) 1_455 1_455 ?
I2 Pb1 I1 175.92(6) . 3_766 ?
I3 Pb1 I1 88.91(6) . 3_766 ?
I1 Pb1 I1 86.81(6) . 3_766 ?
I1 Pb1 I1 88.24(6) 1_455 3_766 ?
I3 Pb1 I1 90.35(6) 1_455 3_766 ?
Pb1 I1 Pb1 88.14(7) . 1_655 ?
Pb1 I1 Pb1 93.19(6) . 3_766 ?
Pb1 I1 Pb1 91.76(6) 1_655 3_766 ?
Pb1 I3 Pb1 88.33(7) . 1_655 ?
C1A N1A H1A1 109.5 . . ?
C1A N1A H1A2 109.5 . . ?
H1A1 N1A H1A2 109.5 . . ?
C1A N1A H1A3 109.5 . . ?
H1A1 N1A H1A3 109.5 . . ?
H1A2 N1A H1A3 109.5 . . ?
C2A C1A C6A 120.0 . . ?
C2A C1A N1A 119.9(16) . . ?
C6A C1A N1A 120.1(16) . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C4A C3A C2A 120.00(8) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A C4A 118(10) . 3_776 ?
C5A C4A C4A 120(10) . 3_776 ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C1A 120.00(7) . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C1B N1B H1B1 109.5 . . ?
C1B N1B H1B2 109.5 . . ?
H1B1 N1B H1B2 109.5 . . ?
C1B N1B H1B3 109.5 . . ?
H1B1 N1B H1B3 109.5 . . ?
H1B2 N1B H1B3 109.5 . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B N1B 119.5(14) . . ?
C6B C1B N1B 120.5(14) . . ?
C3B C2B C1B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B C4B 115(5) . 3_676 ?
C5B C4B C4B 123(5) . 3_676 ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?

_refine_diff_density_max         2.536
_refine_diff_density_min         -4.152
_refine_diff_density_rms         0.465

