# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zwd-1
_database_code_depnum_ccdc_archive 'CCDC 1988940'
loop_
_audit_author_name
_audit_author_address
'Jiangwei Zhang'
;Dalian Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-03-08 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_audit_creation_date             2019-08-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I4 Pb, C5 H16 N2'
_chemical_formula_sum            'C5 H16 I4 N2 Pb'
_chemical_formula_weight         818.99
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.435(2)
_cell_length_b                   8.6432(12)
_cell_length_c                   20.797(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3313.7(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    618
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.606
_exptl_absorpt_correction_T_max  0.172
_exptl_absorpt_correction_T_min  0.020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ad
_exptl_crystal_density_diffrn    3.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3988
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        27.739
_diffrn_reflns_theta_max         27.739
_diffrn_reflns_theta_min         2.781
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2309
_reflns_number_total             3815
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       0.00055(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0718
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-C1
 2.5 with sigma of 0.02
 N009-C3
 1.47 with sigma of 0.02
 C3-C20
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N006) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C20)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(N009) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C10) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 N006(H006)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C20(H20A,H20B)
4.c Idealised Me refined as rotating group:
 N009(H00A,H00B,H00C), C4(H4A,H4B,H4C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Pb01 Pb 0.37735(2) 0.62864(4) 0.72975(4) 0.0316(3) Uani 1 1 d . . . . .
I002 I 0.48921(4) 0.90851(8) 0.74410(6) 0.0500(5) Uani 1 1 d . . . . .
I003 I 0.23420(4) 0.84858(8) 0.71592(7) 0.0516(5) Uani 1 1 d . . . . .
I004 I 0.39930(5) 0.62297(9) 0.58039(7) 0.0497(6) Uani 1 1 d . . . . .
I005 I 0.34548(5) 0.66370(10) 0.88611(8) 0.0597(6) Uani 1 1 d . . . . .
N006 N 0.1224(5) 0.7905(12) 1.0504(9) 0.052(4) Uani 1 1 d . U . . .
H006 H 0.133431 0.685096 1.064777 0.062 Uiso 1 1 calc R . . . .
N009 N 0.1616(5) 0.5682(12) 0.8379(8) 0.062(5) Uani 1 1 d D U . . .
H00A H 0.149983 0.585287 0.796973 0.074 Uiso 1 1 calc GR . . . .
H00B H 0.156819 0.467892 0.846637 0.074 Uiso 1 1 calc GR . . . .
H00C H 0.207278 0.597007 0.844728 0.074 Uiso 1 1 calc GR . . . .
C1 C 0.0935(9) 0.7801(18) 0.9844(10) 0.074(6) Uani 1 1 d D U . . .
H1A H 0.091646 0.881982 0.964864 0.089 Uiso 1 1 calc R . . . .
H1B H 0.044805 0.737444 0.984941 0.089 Uiso 1 1 calc R . . . .
C3 C 0.1140(9) 0.656(2) 0.8790(10) 0.089(7) Uani 1 1 d D U . . .
H3A H 0.067323 0.604778 0.881250 0.107 Uiso 1 1 calc R . . . .
H3B H 0.106395 0.757662 0.860189 0.107 Uiso 1 1 calc R . . . .
C4 C 0.1912(8) 0.8800(16) 1.0515(13) 0.082(7) Uani 1 1 d . U . . .
H4A H 0.225621 0.832880 1.022896 0.123 Uiso 1 1 calc GR . . . .
H4B H 0.210508 0.880549 1.094381 0.123 Uiso 1 1 calc GR . . . .
H4C H 0.182005 0.984309 1.037952 0.123 Uiso 1 1 calc GR . . . .
C10 C 0.0725(9) 0.8579(16) 1.0965(12) 0.080(5) Uani 1 1 d . U . . .
H10A H 0.098895 0.891281 1.133787 0.120 Uiso 1 1 calc GR . . . .
H10B H 0.037119 0.782074 1.108815 0.120 Uiso 1 1 calc GR . . . .
H10C H 0.048516 0.945060 1.077322 0.120 Uiso 1 1 calc GR . . . .
C20 C 0.1438(10) 0.676(2) 0.9470(12) 0.099(7) Uani 1 1 d D U . . .
H20A H 0.147231 0.575840 0.967910 0.119 Uiso 1 1 calc R . . . .
H20B H 0.191932 0.720951 0.945297 0.119 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pb01 0.0278(3) 0.0241(2) 0.0430(8) 0.0001(2) -0.0014(3) -0.00061(15)
I002 0.0443(5) 0.0357(4) 0.0699(16) -0.0066(4) -0.0006(6) -0.0182(3)
I003 0.0472(5) 0.0358(4) 0.0717(18) -0.0029(5) -0.0082(6) 0.0196(3)
I004 0.0481(5) 0.0556(5) 0.0455(19) -0.0002(5) 0.0033(6) -0.0089(4)
I005 0.0552(6) 0.0738(6) 0.050(2) 0.0051(6) -0.0021(7) 0.0006(4)
N006 0.046(6) 0.056(5) 0.054(11) 0.005(6) 0.005(7) 0.003(4)
N009 0.063(7) 0.066(6) 0.055(16) -0.013(7) -0.023(9) -0.010(6)
C1 0.063(8) 0.083(7) 0.078(12) -0.011(8) -0.006(8) -0.004(6)
C3 0.077(8) 0.109(9) 0.082(12) -0.026(8) 0.003(9) 0.005(7)
C4 0.071(9) 0.108(10) 0.07(2) 0.020(10) -0.010(11) -0.045(8)
C10 0.080(5) 0.080(5) 0.080(6) -0.001(2) 0.001(2) 0.000(2)
C20 0.088(9) 0.116(9) 0.094(13) -0.001(9) 0.005(9) 0.011(7)

_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
Pb01 I002 3.1570(9) 3_646 ?
Pb01 I002 3.1927(8) . ?
Pb01 I003 3.2651(9) . ?
Pb01 I003 3.1892(8) 8_655 ?
Pb01 I004 3.1328(18) . ?
Pb01 I005 3.319(2) . ?
N006 C1 1.48(2) . ?
N006 C4 1.486(15) . ?
N006 C10 1.45(2) . ?
N009 C3 1.442(14) . ?
C1 C20 1.51(2) . ?
C3 C20 1.526(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I002 Pb01 I002 86.402(14) 3_646 . ?
I002 Pb01 I003 95.12(2) . . ?
I002 Pb01 I003 93.47(2) 3_646 8_655 ?
I002 Pb01 I003 174.76(4) 3_646 . ?
I002 Pb01 I005 87.34(3) . . ?
I002 Pb01 I005 91.38(3) 3_646 . ?
I003 Pb01 I002 179.79(4) 8_655 . ?
I003 Pb01 I003 84.996(14) 8_655 . ?
I003 Pb01 I005 83.69(3) . . ?
I003 Pb01 I005 92.49(3) 8_655 . ?
I004 Pb01 I002 91.21(3) . . ?
I004 Pb01 I002 93.49(3) . 3_646 ?
I004 Pb01 I003 88.97(3) . 8_655 ?
I004 Pb01 I003 91.50(3) . . ?
I004 Pb01 I005 174.82(2) . . ?
Pb01 I002 Pb01 167.42(3) 3_656 . ?
Pb01 I003 Pb01 162.77(4) 8_665 . ?
C1 N006 C4 110.8(16) . . ?
C10 N006 C1 114.2(12) . . ?
C10 N006 C4 108.8(14) . . ?
N006 C1 C20 107.1(14) . . ?
N009 C3 C20 112.9(15) . . ?
C1 C20 C3 108.8(13) . . ?
