# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1012805'
#Added by publCIF



_audit_update_record             
;
2014-07-08 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;


_cell_special_details            ?
#Added by publCIF




_symmetry_space_group_name_hall  'C -2yc'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'I3 Pb, C4 H6 O2, C3 H10 N'
_chemical_formula_sum            'C7 H16 I3 N O2 Pb'
_chemical_formula_weight         734.10

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   17.7703(9)
_cell_length_b                   12.3805(8)
_cell_length_c                   8.0711(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.773(7)
_cell_angle_gamma                90.00
_cell_volume                     1585.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      6.6
_cell_measurement_theta_max      19.9

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.076
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288
_exptl_absorpt_coefficient_mu    16.468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.030
_exptl_absorpt_correction_T_max  0.061
_exptl_absorpt_process_details   SADABS

_exptl_special_details           ?

_diffrn_ambient_temperature      173(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  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20621
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.05
_diffrn_reflns_theta_max         30.01
_reflns_number_total             4472
_reflns_number_gt                4226
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Collect(Nonius)
_computing_cell_refinement       Dirax
_computing_data_reduction        EvalCCD
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  SHELXL-97
_computing_molecular_graphics    Diamond
_computing_publication_material  ?

_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)+(0.0110P)²+21.7695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   0.194(8)
_refine_ls_number_reflns         4472
_refine_ls_number_parameters     130
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2273(7) 0.1452(8) 0.2727(14) 0.044(2) Uani 1 1 d . . .
C2 C 0.2468(11) 0.1636(13) 0.4591(18) 0.066(5) Uani 1 1 d . . .
H2A H 0.2902 0.1124 0.5421 0.079 Uiso 1 1 calc R . .
H2B H 0.1961 0.1578 0.4797 0.079 Uiso 1 1 calc R . .
C3 C 0.2832(7) 0.2886(11) 0.4914(14) 0.047(3) Uani 1 1 d . . .
H3A H 0.2421 0.3410 0.4959 0.056 Uiso 1 1 calc R . .
H3B H 0.3375 0.2955 0.6046 0.056 Uiso 1 1 calc R . .
C4 C 0.2936(9) 0.2999(12) 0.313(2) 0.067(5) Uani 1 1 d . . .
H4A H 0.2727 0.3712 0.2553 0.080 Uiso 1 1 calc R . .
H4B H 0.3538 0.2935 0.3421 0.080 Uiso 1 1 calc R . .
C5 C 0.0521(5) 0.1365(7) 0.6794(13) 0.0323(18) Uani 1 1 d . . .
H5A H 0.0398 0.1393 0.5470 0.039 Uiso 1 1 calc R . .
H5B H 0.0320 0.2046 0.7102 0.039 Uiso 1 1 calc R . .
C6 C 0.0073(10) 0.0424(11) 0.7116(19) 0.064(3) Uani 1 1 d . . .
H6A H 0.0104 0.0460 0.8371 0.076 Uiso 1 1 calc R . .
H6B H 0.0325 -0.0266 0.6994 0.076 Uiso 1 1 calc R . .
C7 C -0.0877(8) 0.0519(11) 0.557(3) 0.082(6) Uani 1 1 d . . .
H7A H -0.0921 0.1091 0.4687 0.123 Uiso 1 1 calc R . .
H7B H -0.1241 0.0694 0.6150 0.123 Uiso 1 1 calc R . .
H7C H -0.1056 -0.0170 0.4903 0.123 Uiso 1 1 calc R . .
I1 I -0.11127(3) 0.60408(5) 0.00770(5) 0.02596(14) Uani 1 1 d . . .
I2 I 0.02638(6) 0.29529(3) 0.14575(16) 0.02936(9) Uani 1 1 d . . .
I3 I 0.16674(2) 0.41053(4) 0.78304(5) 0.02236(12) Uani 1 1 d . . .
N1 N 0.1443(5) 0.1254(7) 0.7970(18) 0.058(3) Uani 1 1 d . . .
H1A H 0.1692 0.1915 0.8139 0.087 Uiso 1 1 calc R . .
H1B H 0.1662 0.0808 0.7401 0.087 Uiso 1 1 calc R . .
H1C H 0.1542 0.0971 0.9089 0.087 Uiso 1 1 calc R . .
O1 O 0.2495(5) 0.2218(7) 0.2000(11) 0.0499(18) Uani 1 1 d . . .
O2 O 0.1860(6) 0.0651(7) 0.1792(11) 0.058(2) Uani 1 1 d . . .
Pb1 Pb 0.02364(4) 0.49982(2) 0.39451(10) 0.02042(6) 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
C1 O2 1.262(13) . ?
C1 O1 1.269(14) . ?
C1 C2 1.402(16) . ?
C2 C3 1.65(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.54(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.319(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.484(11) . ?
C5 C6 1.499(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.59(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
I1 Pb1 3.1951(8) 2_564 ?
I1 Pb1 3.2275(9) . ?
I2 Pb1 3.2340(9) 2_564 ?
I2 Pb1 3.2454(9) . ?
I3 Pb1 3.2152(8) . ?
I3 Pb1 3.2510(8) 2_565 ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
Pb1 I1 3.1951(8) 2_565 ?
Pb1 I2 3.2340(9) 2_565 ?
Pb1 I3 3.2510(8) 2_564 ?

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
O2 C1 O1 122.0(10) . . ?
O2 C1 C2 124.5(12) . . ?
O1 C1 C2 113.3(11) . . ?
C1 C2 C3 102.3(10) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C4 C3 C2 98.1(9) . . ?
C4 C3 H3A 112.1 . . ?
C2 C3 H3A 112.1 . . ?
C4 C3 H3B 112.1 . . ?
C2 C3 H3B 112.1 . . ?
H3A C3 H3B 109.8 . . ?
O1 C4 C3 107.3(12) . . ?
O1 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
O1 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
N1 C5 C6 109.7(9) . . ?
N1 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C7 105.4(10) . . ?
C5 C6 H6A 110.7 . . ?
C7 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
C7 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Pb1 I1 Pb1 77.852(17) 2_564 . ?
Pb1 I2 Pb1 77.044(9) 2_564 . ?
Pb1 I3 Pb1 77.229(17) . 2_565 ?
C5 N1 H1A 109.5 . . ?
C5 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C5 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O1 C4 116.0(11) . . ?
I1 Pb1 I3 87.04(2) 2_565 . ?
I1 Pb1 I1 96.40(2) 2_565 . ?
I3 Pb1 I1 175.87(2) . . ?
I1 Pb1 I2 86.43(2) 2_565 2_565 ?
I3 Pb1 I2 82.89(2) . 2_565 ?
I1 Pb1 I2 95.03(2) . 2_565 ?
I1 Pb1 I2 94.88(2) 2_565 . ?
I3 Pb1 I2 96.29(2) . . ?
I1 Pb1 I2 85.71(2) . . ?
I2 Pb1 I2 178.41(4) 2_565 . ?
I1 Pb1 I3 176.12(2) 2_565 2_564 ?
I3 Pb1 I3 90.78(2) . 2_564 ?
I1 Pb1 I3 85.90(2) . 2_564 ?
I2 Pb1 I3 96.49(2) 2_565 2_564 ?
I2 Pb1 I3 82.16(2) . 2_564 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A I3 0.91 2.72 3.560(9) 153.6 .
N1 H1B O2 0.91 1.94 2.765(13) 149.1 2
N1 H1C O2 0.91 2.03 2.926(16) 168.0 1_556

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.882
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.182


