# 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_114
_database_code_depnum_ccdc_archive 'CCDC 917236'
_audit_update_record             
;
2012-12-27 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
#TrackingRef '114.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H30 N2, 2(I3 Pb)'
_chemical_formula_sum            'C10 H15 I3 N Pb'
_chemical_formula_weight         737.12

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4 21 c'
_symmetry_space_group_name_hall  'P -4 2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   22.156(8)
_cell_length_b                   22.156(8)
_cell_length_c                   8.111(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3982(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6749
_cell_measurement_theta_min      2.0553
_cell_measurement_theta_max      27.4584

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2584
_exptl_absorpt_coefficient_mu    13.107
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.2013
_exptl_absorpt_correction_T_max  0.5602
_exptl_absorpt_process_details   'Sphere (Rigaku CrystalClear)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Ultrax-Saturn 70'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26296
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3699
_reflns_number_gt                2306
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'Siemens SHELXTLTM 5'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0829P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         3699
_refine_ls_number_parameters     88
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1507
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.008

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.24095(2) 0.73861(2) 0.18603(5) 0.06287(12) Uani 1 1 d . . .
I1 I 0.15785(4) 0.81984(4) -0.04000(10) 0.0993(3) Uani 1 1 d . . .
I2 I 0.21440(4) 0.62902(4) -0.08014(10) 0.0889(3) Uani 1 1 d . . .
I3 I 0.34782(4) 0.77503(4) -0.08025(9) 0.0873(3) Uani 1 1 d . . .
C1 C 0.4899(3) 0.8402(2) -0.4788(5) 0.105(2) Uani 1 1 d GDU . .
C2 C 0.5429(3) 0.8674(3) -0.5326(9) 0.105(2) Uani 1 1 d GU . .
H2A H 0.5752 0.8437 -0.5664 0.126 Uiso 1 1 calc R . .
C3 C 0.5475(4) 0.9299(3) -0.5357(10) 0.105(2) Uani 1 1 d GU . .
H3A H 0.5830 0.9481 -0.5717 0.126 Uiso 1 1 calc R . .
C4 C 0.4991(5) 0.9653(2) -0.4851(9) 0.105(2) Uani 1 1 d GU . .
C5 C 0.4461(4) 0.9382(3) -0.4314(10) 0.105(2) Uani 1 1 d GU . .
H5A H 0.4137 0.9618 -0.3975 0.126 Uiso 1 1 calc R . .
C6 C 0.4415(3) 0.8756(3) -0.4282(9) 0.105(2) Uani 1 1 d GU . .
H6A H 0.4060 0.8574 -0.3923 0.126 Uiso 1 1 calc R . .
C7 C 0.5003(5) 0.7489(4) -0.6093(10) 0.209(4) Uani 1 1 d DU . .
H7A H 0.5353 0.7720 -0.6432 0.251 Uiso 1 1 calc R . .
H7B H 0.5123 0.7069 -0.5992 0.251 Uiso 1 1 calc R . .
C8 C 0.4557(6) 0.7540(10) -0.7266(17) 0.225(2) Uani 1 1 d D . .
H8A H 0.4700 0.7380 -0.8295 0.337 Uiso 1 1 calc R . .
H8B H 0.4452 0.7957 -0.7404 0.337 Uiso 1 1 calc R . .
H8C H 0.4207 0.7318 -0.6918 0.337 Uiso 1 1 calc R . .
C9 C 0.5069(7) 0.7711(4) -0.2914(12) 0.203(8) Uani 1 1 d DU . .
H9A H 0.5500 0.7787 -0.2922 0.244 Uiso 1 1 calc R . .
H9B H 0.4865 0.7981 -0.2157 0.244 Uiso 1 1 calc R . .
N1 N 0.4798(6) 0.7699(6) -0.4571(9) 0.164(4) Uani 1 1 d DU . .
H11A H 0.4396 0.7623 -0.4481 0.196 Uiso 1 1 calc R . .
C10 C 0.4922(9) 0.7100(5) -0.267(2) 0.225(2) Uani 1 1 d DU . .
H10A H 0.5068 0.6971 -0.1617 0.337 Uiso 1 1 calc R . .
H10B H 0.5105 0.6861 -0.3524 0.337 Uiso 1 1 calc R . .
H10C H 0.4491 0.7052 -0.2716 0.337 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
Pb1 0.0722(2) 0.0767(3) 0.03972(18) -0.00013(19) 0.00116(19) -0.0055(2)
I1 0.1150(6) 0.1151(7) 0.0677(5) 0.0002(5) -0.0065(5) 0.0433(5)
I2 0.1260(6) 0.0734(5) 0.0672(4) -0.0023(4) 0.0156(5) -0.0271(4)
I3 0.0861(5) 0.1166(6) 0.0590(4) -0.0084(5) 0.0028(4) -0.0319(5)
C1 0.088(4) 0.105(4) 0.121(4) -0.008(3) -0.022(3) 0.000(3)
C2 0.088(4) 0.105(4) 0.121(4) -0.008(3) -0.022(3) 0.000(3)
C3 0.088(4) 0.105(4) 0.121(4) -0.008(3) -0.022(3) 0.000(3)
C4 0.088(4) 0.105(4) 0.121(4) -0.008(3) -0.022(3) 0.000(3)
C5 0.088(4) 0.105(4) 0.121(4) -0.008(3) -0.022(3) 0.000(3)
C6 0.088(4) 0.105(4) 0.121(4) -0.008(3) -0.022(3) 0.000(3)
C7 0.207(6) 0.210(6) 0.210(6) 0.008(5) 0.002(5) 0.006(5)
C8 0.223(3) 0.227(3) 0.224(3) 0.000(2) 0.001(2) -0.001(2)
C9 0.143(13) 0.193(16) 0.272(15) 0.061(13) 0.093(12) 0.066(11)
N1 0.160(6) 0.163(6) 0.168(5) -0.003(5) -0.028(5) -0.002(5)
C10 0.223(3) 0.227(3) 0.224(3) 0.000(2) 0.001(2) -0.001(2)

_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 3.1609(14) . ?
Pb1 I3 3.1654(13) 8_455 ?
Pb1 I2 3.1679(13) 8_455 ?
Pb1 I2 3.3019(13) . ?
Pb1 I3 3.3051(13) . ?
Pb1 I1 3.3459(14) 8_455 ?
I1 Pb1 3.3459(14) 8_454 ?
I2 Pb1 3.1679(13) 8_454 ?
I3 Pb1 3.1654(13) 8_454 ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 N1 1.584(14) . ?
C2 C3 1.3900 . ?
C2 H2A 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3A 0.9300 . ?
C4 C5 1.3900 . ?
C4 C4 1.537(11) 2_675 ?
C5 C6 1.3900 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.377(13) . ?
C7 N1 1.396(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.405(13) . ?
C9 N1 1.473(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N1 H11A 0.9100 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 92.92(3) . 8_455 ?
I1 Pb1 I2 89.29(4) . 8_455 ?
I3 Pb1 I2 87.57(3) 8_455 8_455 ?
I1 Pb1 I2 86.32(4) . . ?
I3 Pb1 I2 175.03(3) 8_455 . ?
I2 Pb1 I2 97.32(4) 8_455 . ?
I1 Pb1 I3 84.22(3) . . ?
I3 Pb1 I3 91.93(4) 8_455 . ?
I2 Pb1 I3 173.46(3) 8_455 . ?
I2 Pb1 I3 83.10(4) . . ?
I1 Pb1 I1 173.75(3) . 8_455 ?
I3 Pb1 I1 83.48(3) 8_455 8_455 ?
I2 Pb1 I1 85.46(4) 8_455 8_455 ?
I2 Pb1 I1 97.70(4) . 8_455 ?
I3 Pb1 I1 100.97(4) . 8_455 ?
Pb1 I1 Pb1 77.07(4) . 8_454 ?
Pb1 I2 Pb1 77.62(4) 8_454 . ?
Pb1 I3 Pb1 77.61(4) 8_454 . ?
C2 C1 C6 120.0 . . ?
C2 C1 N1 125.5(5) . . ?
C6 C1 N1 114.4(5) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C4 117.0(11) . 2_675 ?
C3 C4 C4 123.0(11) . 2_675 ?
C4 C5 C6 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
C8 C7 N1 110.5(11) . . ?
C8 C7 H7A 109.6 . . ?
N1 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 90.9(12) . . ?
C10 C9 H9A 113.5 . . ?
N1 C9 H9A 113.5 . . ?
C10 C9 H9B 113.5 . . ?
N1 C9 H9B 113.5 . . ?
H9A C9 H9B 110.8 . . ?
C7 N1 C9 132.9(11) . . ?
C7 N1 C1 100.6(8) . . ?
C9 N1 C1 91.5(8) . . ?
C7 N1 H11A 109.2 . . ?
C9 N1 H11A 109.2 . . ?
C1 N1 H11A 109.2 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.292
_refine_diff_density_min         -1.172
_refine_diff_density_rms         0.200


