# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_151024g
_database_code_depnum_ccdc_archive 'CCDC 1524687'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H28 Bi2 I9 N5'
_chemical_formula_weight         1874.51

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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   16.7661(15)
_cell_length_b                   22.860(2)
_cell_length_c                   11.4060(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4371.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3950
_cell_measurement_theta_min      2.316
_cell_measurement_theta_max      26.810

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    2.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3256
_exptl_absorpt_coefficient_mu    14.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.008
_exptl_absorpt_correction_T_max  0.202
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3950
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1549
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3950
_reflns_number_gt                1754
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1426P)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_number_reflns         3950
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2059
_refine_ls_R_factor_gt           0.0859
_refine_ls_wR_factor_ref         0.2904
_refine_ls_wR_factor_gt          0.2283
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_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
Bi1 Bi 0.14588(7) 0.15705(6) -0.00206(10) 0.0513(5) Uani 1 1 d . . .
I1 I 0.15562(17) 0.2500 -0.2177(2) 0.0566(9) Uani 1 2 d S . .
I2 I 0.26304(19) 0.2500 0.1326(3) 0.0690(10) Uani 1 2 d S . .
I3 I 0.00951(17) 0.2500 0.0870(3) 0.0594(9) Uani 1 2 d S . .
I4 I 0.13384(14) 0.08451(12) 0.2113(2) 0.0745(8) Uani 1 1 d . . .
I5 I 0.02948(15) 0.08718(12) -0.1346(2) 0.0820(9) Uani 1 1 d . . .
I6 I 0.28232(14) 0.09006(12) -0.0927(2) 0.0802(9) Uani 1 1 d . . .
N1 N 0.340(2) 0.100(2) 0.423(3) 0.099(11) Uani 1 1 d . . .
N2 N 0.457(4) 0.2500 0.916(6) 0.14(2) Uani 1 2 d S . .
N3 N 0.540(3) 0.2807(17) 1.061(3) 0.144(19) Uani 1 1 d . . .
H3 H 0.5669 0.3029 1.1084 0.173 Uiso 0.50 1 calc PR . .
C1 C 0.305(3) 0.148(2) 0.425(4) 0.100(15) Uani 1 1 d . . .
H1 H 0.3194 0.1777 0.3742 0.121 Uiso 1 1 calc R . .
C2 C 0.241(3) 0.155(2) 0.504(4) 0.099(14) Uani 1 1 d . . .
H2A H 0.2095 0.1884 0.5004 0.119 Uiso 1 1 calc R . .
C3 C 0.228(3) 0.116(2) 0.582(4) 0.100(14) Uani 1 1 d . . .
H3A H 0.1924 0.1235 0.6425 0.120 Uiso 1 1 calc R . .
C4 C 0.266(3) 0.065(2) 0.573(4) 0.101(14) Uani 1 1 d . . .
H4 H 0.2523 0.0346 0.6239 0.121 Uiso 1 1 calc R . .
C5 C 0.324(3) 0.055(2) 0.495(4) 0.100(14) Uani 1 1 d . . .
H5 H 0.3506 0.0200 0.4901 0.119 Uiso 1 1 calc R . .
C6 C 0.409(3) 0.088(2) 0.350(4) 0.102(14) Uani 1 1 d . . .
H6A H 0.4339 0.0509 0.3715 0.122 Uiso 1 1 calc R . .
H6B H 0.4482 0.1187 0.3540 0.122 Uiso 1 1 calc R . .
C7 C 0.372(3) 0.0839(19) 0.228(4) 0.112(16) Uani 1 1 d . . .
H7A H 0.4126 0.0754 0.1713 0.168 Uiso 1 1 calc R . .
H7B H 0.3472 0.1207 0.2089 0.168 Uiso 1 1 calc R . .
H7C H 0.3324 0.0535 0.2267 0.168 Uiso 1 1 calc R . .
C8 C 0.489(4) 0.300(3) 0.971(4) 0.14(2) Uani 1 1 d . . .
H8 H 0.4790 0.3382 0.9505 0.169 Uiso 1 1 calc R . .
C9 C 0.395(5) 0.2500 0.831(7) 0.14(3) Uani 1 2 d S . .
H9A H 0.3627 0.2160 0.8473 0.173 Uiso 0.50 1 calc PR . .
H9B H 0.3627 0.2840 0.8473 0.173 Uiso 0.50 1 calc PR . .
C10 C 0.408(4) 0.2500 0.719(6) 0.14(3) Uani 1 2 d S . .
H10A H 0.3573 0.2500 0.6789 0.211 Uiso 1 2 calc SR . .
H10B H 0.4373 0.2157 0.6976 0.211 Uiso 0.50 1 calc PR . .
H10C H 0.4373 0.2843 0.6976 0.211 Uiso 0.50 1 calc PR . .

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
Bi1 0.0422(7) 0.0586(9) 0.0531(7) -0.0013(7) 0.0013(6) 0.0009(6)
I1 0.0510(17) 0.072(2) 0.0466(16) 0.000 0.0048(13) 0.000
I2 0.0568(19) 0.075(3) 0.075(2) 0.000 -0.0195(16) 0.000
I3 0.0424(16) 0.073(2) 0.0630(19) 0.000 0.0127(14) 0.000
I4 0.0702(16) 0.087(2) 0.0658(15) 0.0152(15) 0.0054(11) 0.0025(13)
I5 0.0690(16) 0.089(2) 0.0883(18) -0.0172(15) -0.0126(14) -0.0141(13)
I6 0.0619(15) 0.095(2) 0.0837(17) -0.0015(17) 0.0095(12) 0.0214(13)
N1 0.10(3) 0.10(3) 0.10(3) 0.00(3) 0.02(2) 0.02(2)
N2 0.13(6) 0.17(8) 0.11(5) 0.000 -0.01(4) 0.000
N3 0.15(4) 0.17(5) 0.12(3) -0.03(3) 0.00(3) -0.02(3)
C1 0.10(4) 0.10(4) 0.10(3) 0.01(3) 0.02(3) 0.01(3)
C2 0.10(3) 0.10(4) 0.10(3) 0.01(3) 0.03(3) 0.01(3)
C3 0.11(4) 0.10(4) 0.10(3) 0.01(3) 0.03(3) 0.01(3)
C4 0.11(4) 0.10(4) 0.10(3) 0.01(3) 0.03(3) 0.01(3)
C5 0.11(3) 0.10(4) 0.10(3) 0.01(3) 0.03(3) 0.01(3)
C6 0.10(3) 0.10(4) 0.10(3) 0.01(3) 0.02(3) 0.01(3)
C7 0.12(4) 0.10(4) 0.11(4) -0.01(3) 0.03(3) 0.02(3)
C8 0.14(5) 0.16(6) 0.12(4) 0.00(4) 0.00(4) 0.00(5)
C9 0.14(7) 0.17(8) 0.12(7) 0.000 -0.01(6) 0.000
C10 0.14(7) 0.17(8) 0.11(6) 0.000 0.00(5) 0.000

_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
Bi1 I5 2.940(3) . ?
Bi1 I6 2.941(3) . ?
Bi1 I4 2.952(3) . ?
Bi1 I1 3.255(2) . ?
Bi1 I2 3.276(3) . ?
Bi1 I3 3.282(2) . ?
I1 Bi1 3.255(2) 8_565 ?
I2 Bi1 3.276(3) 8_565 ?
I3 Bi1 3.282(2) 8_565 ?
N1 C1 1.24(5) . ?
N1 C5 1.34(5) . ?
N1 C6 1.45(5) . ?
N2 C8 1.40(6) 8_565 ?
N2 C8 1.40(6) . ?
N2 C9 1.41(9) . ?
N3 N3 1.40(8) 8_565 ?
N3 C8 1.41(6) . ?
N3 H3 0.8600 . ?
C1 C2 1.41(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.27(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.35(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.33(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.52(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C9 C10 1.29(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
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
I5 Bi1 I6 93.02(8) . . ?
I5 Bi1 I4 94.21(8) . . ?
I6 Bi1 I4 92.89(8) . . ?
I5 Bi1 I1 89.96(7) . . ?
I6 Bi1 I1 92.02(7) . . ?
I4 Bi1 I1 173.38(7) . . ?
I5 Bi1 I2 172.47(8) . . ?
I6 Bi1 I2 92.07(8) . . ?
I4 Bi1 I2 91.08(8) . . ?
I1 Bi1 I2 84.31(7) . . ?
I5 Bi1 I3 92.78(8) . . ?
I6 Bi1 I3 171.04(7) . . ?
I4 Bi1 I3 93.49(7) . . ?
I1 Bi1 I3 81.16(6) . . ?
I2 Bi1 I3 81.53(7) . . ?
Bi1 I1 Bi1 81.51(8) 8_565 . ?
Bi1 I2 Bi1 80.87(8) . 8_565 ?
Bi1 I3 Bi1 80.68(7) . 8_565 ?
C1 N1 C5 124(4) . . ?
C1 N1 C6 124(5) . . ?
C5 N1 C6 112(4) . . ?
C8 N2 C8 108(7) 8_565 . ?
C8 N2 C9 126(4) 8_565 . ?
C8 N2 C9 126(4) . . ?
N3 N3 C8 108(3) 8_565 . ?
N3 N3 H3 126.1 8_565 . ?
C8 N3 H3 126.1 . . ?
N1 C1 C2 119(5) . . ?
N1 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 120(5) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 118(5) . . ?
C2 C3 H3A 120.8 . . ?
C4 C3 H3A 120.8 . . ?
C5 C4 C3 122(5) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 N1 116(5) . . ?
C4 C5 H5 121.9 . . ?
N1 C5 H5 121.9 . . ?
N1 C6 C7 102(4) . . ?
N1 C6 H6A 111.4 . . ?
C7 C6 H6A 111.4 . . ?
N1 C6 H6B 111.4 . . ?
C7 C6 H6B 111.4 . . ?
H6A C6 H6B 109.2 . . ?
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 . . ?
N2 C8 N3 108(6) . . ?
N2 C8 H8 125.8 . . ?
N3 C8 H8 125.8 . . ?
C10 C9 N2 124(8) . . ?
C10 C9 H9A 106.2 . . ?
N2 C9 H9A 106.2 . . ?
C10 C9 H9B 106.2 . . ?
N2 C9 H9B 106.2 . . ?
H9A C9 H9B 106.4 . . ?
C9 C10 H10A 109.5 . . ?
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        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         3.747
_refine_diff_density_min         -4.736
_refine_diff_density_rms         0.580
####################################################################### 
# 
# 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_151002d
_database_code_depnum_ccdc_archive 'CCDC 1524688'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H10 I3 N Pb'
_chemical_formula_weight         696.05

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           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   18.36(2)
_cell_length_b                   7.910(10)
_cell_length_c                   19.67(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2857(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13836
_cell_measurement_theta_min      2.337
_cell_measurement_theta_max      27.138

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      3.237
_exptl_crystal_density_diffrn    3.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2400
_exptl_absorpt_coefficient_mu    18.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.050
_exptl_absorpt_correction_T_max  0.110
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13836
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2718
_reflns_number_gt                1767
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0388P)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     SHELXL
_refine_ls_extinction_coef       0.00063(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2718
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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
Pb1 Pb 0.74923(2) 0.99854(5) 0.64693(2) 0.03585(18) Uani 1 1 d . . .
I1 I 0.86481(6) 1.2500 0.57798(5) 0.0410(3) Uani 1 2 d S . .
I2 I 0.63530(6) 0.7500 0.72691(5) 0.0426(3) Uani 1 2 d S . .
I3 I 0.75775(6) 1.2500 0.77825(5) 0.0455(3) Uani 1 2 d S . .
I4 I 0.71933(7) 0.7500 0.51906(6) 0.0458(3) Uani 1 2 d S . .
I5 I 0.62733(6) 1.2500 0.58673(5) 0.0389(3) Uani 1 2 d S . .
I6 I 0.88455(6) 0.7500 0.68693(6) 0.0500(4) Uani 1 2 d S . .
N1 N 0.6392(10) 0.2500 0.3842(9) 0.081(6) Uani 1 2 d S . .
N2 N 0.0545(9) 0.2500 0.6630(9) 0.072(5) Uani 1 2 d S . .
C1 C 0.6056(10) 0.098(3) 0.3938(8) 0.094(6) Uani 1 1 d . . .
H1 H 0.6311 -0.0029 0.3888 0.113 Uiso 1 1 calc R . .
C2 C 0.5328(11) 0.098(3) 0.4112(8) 0.106(7) Uani 1 1 d . . .
H2 H 0.5084 -0.0030 0.4196 0.127 Uiso 1 1 calc R . .
C3 C 0.4972(15) 0.2500 0.4157(12) 0.096(9) Uani 1 2 d S . .
H3 H 0.4470 0.2500 0.4221 0.115 Uiso 1 2 calc SR . .
C4 C 0.7159(13) 0.2500 0.3614(13) 0.101(9) Uani 1 2 d S . .
H4 H 0.7247 0.1510 0.3335 0.122 Uiso 1 1 d R . .
C5 C 0.7630(13) 0.2500 0.4135(12) 0.114(11) Uani 1 2 d S . .
H5A H 0.8119 0.2500 0.3960 0.171 Uiso 1 2 d SR . .
H5B H 0.7556 0.3491 0.4408 0.171 Uiso 1 1 d R . .
C6 C 0.0614(8) 0.103(2) 0.6300(8) 0.089(6) Uani 1 1 d . . .
H6 H 0.0584 0.0015 0.6536 0.106 Uiso 1 1 calc R . .
C7 C 0.0732(9) 0.104(3) 0.5607(9) 0.100(6) Uani 1 1 d . . .
H7 H 0.0748 0.0033 0.5362 0.120 Uiso 1 1 calc R . .
C8 C 0.0822(14) 0.2500 0.5303(14) 0.094(9) Uani 1 2 d S . .
H8 H 0.0957 0.2500 0.4848 0.113 Uiso 1 2 calc SR . .
C9 C 0.0459(13) 0.2500 0.7366(11) 0.098(8) Uani 1 2 d S . .
H9 H 0.0696 0.1511 0.7556 0.117 Uiso 1 1 d R . .
C10 C -0.0269(12) 0.2500 0.7576(10) 0.095(8) Uani 1 2 d S . .
H10A H -0.0295 0.2500 0.8063 0.143 Uiso 1 2 d SR . .
H10B H -0.0507 0.3491 0.7402 0.143 Uiso 1 1 d 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 0.0391(3) 0.0275(3) 0.0409(3) 0.0010(2) 0.0001(2) 0.0002(2)
I1 0.0353(6) 0.0445(7) 0.0431(7) 0.000 0.0066(5) 0.000
I2 0.0405(7) 0.0441(8) 0.0432(7) 0.000 0.0065(5) 0.000
I3 0.0539(8) 0.0476(7) 0.0350(7) 0.000 -0.0014(5) 0.000
I4 0.0554(8) 0.0448(7) 0.0373(7) 0.000 0.0005(6) 0.000
I5 0.0341(7) 0.0408(7) 0.0420(7) 0.000 -0.0061(5) 0.000
I6 0.0430(7) 0.0420(8) 0.0651(8) 0.000 -0.0119(6) 0.000
N1 0.057(13) 0.13(2) 0.058(12) 0.000 0.013(9) 0.000
N2 0.061(12) 0.115(18) 0.041(12) 0.000 0.005(9) 0.000
C1 0.070(13) 0.135(19) 0.078(12) -0.013(12) 0.009(10) -0.014(12)
C2 0.087(16) 0.15(2) 0.083(13) -0.009(14) -0.002(11) -0.030(14)
C3 0.057(18) 0.15(3) 0.075(18) 0.000 -0.005(13) 0.000
C4 0.075(18) 0.15(3) 0.082(19) 0.000 0.013(16) 0.000
C5 0.08(2) 0.19(3) 0.074(19) 0.000 -0.010(15) 0.000
C6 0.078(12) 0.128(18) 0.060(12) 0.007(11) 0.006(9) 0.022(12)
C7 0.083(13) 0.14(2) 0.082(15) -0.029(13) 0.010(11) 0.024(14)
C8 0.068(17) 0.15(3) 0.063(19) 0.000 0.015(14) 0.000
C9 0.09(2) 0.13(2) 0.072(18) 0.000 -0.003(14) 0.000
C10 0.084(18) 0.15(3) 0.049(14) 0.000 0.014(13) 0.000

_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 3.209(3) . ?
Pb1 I5 3.220(3) . ?
Pb1 I4 3.240(3) . ?
Pb1 I6 3.264(3) . ?
Pb1 I3 3.264(3) . ?
Pb1 I2 3.273(3) . ?
I1 Pb1 3.209(3) 7_585 ?
I2 Pb1 3.273(3) 7_575 ?
I3 Pb1 3.264(3) 7_585 ?
I4 Pb1 3.240(3) 7_575 ?
I5 Pb1 3.220(3) 7_585 ?
I6 Pb1 3.264(3) 7_575 ?
N1 C1 1.37(2) . ?
N1 C1 1.365(19) 7_565 ?
N1 C4 1.48(3) . ?
N2 C6 1.336(17) . ?
N2 C6 1.336(17) 7_565 ?
N2 C9 1.46(2) . ?
C1 C2 1.38(2) . ?
C2 C3 1.37(2) . ?
C3 C2 1.37(2) 7_565 ?
C4 C5 1.34(3) . ?
C6 C7 1.38(2) . ?
C7 C8 1.31(2) . ?
C8 C7 1.31(2) 7_565 ?
C9 C10 1.40(3) . ?

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 I4 99.20(8) . . ?
I5 Pb1 I4 88.37(7) . . ?
I5 Pb1 I6 171.75(3) . . ?
I4 Pb1 I6 87.17(7) . . ?
I1 Pb1 I3 85.71(7) . . ?
I5 Pb1 I3 87.02(7) . . ?
I4 Pb1 I3 172.98(3) . . ?
I6 Pb1 I3 98.03(6) . . ?
I1 Pb1 I2 176.28(3) . . ?
I4 Pb1 I2 84.29(8) . . ?
I3 Pb1 I2 90.93(8) . . ?
Pb1 I1 Pb1 76.61(9) . 7_585 ?
Pb1 I2 Pb1 73.83(9) . 7_575 ?
Pb1 I3 Pb1 75.09(10) . 7_585 ?
Pb1 I4 Pb1 74.72(10) . 7_575 ?
Pb1 I5 Pb1 76.31(9) 7_585 . ?
Pb1 I6 Pb1 74.07(9) 7_575 . ?
C1 N1 C1 124(2) . 7_565 ?
C1 N1 C4 118.2(11) . . ?
C1 N1 C4 118.2(11) 7_565 . ?
C6 N2 C6 121(2) . 7_565 ?
C6 N2 C9 119.5(10) . . ?
C6 N2 C9 119.5(10) 7_565 . ?
N1 C1 C2 118(2) . . ?
C3 C2 C1 118(2) . . ?
C2 C3 C2 123(3) 7_565 . ?
C5 C4 N1 113(2) . . ?
N2 C6 C7 119.4(19) . . ?
C8 C7 C6 118(2) . . ?
C7 C8 C7 124(3) 7_565 . ?
C10 C9 N2 113(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.267
_refine_diff_density_min         -1.449
_refine_diff_density_rms         0.343
####################################################################### 
# 
# 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_151005b
_database_code_depnum_ccdc_archive 'CCDC 1524689'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 I3 N Pb'
_chemical_formula_weight         668.00

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           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   14.9571(12)
_cell_length_b                   8.0960(8)
_cell_length_c                   9.8979(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1198.56(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5862
_cell_measurement_theta_min      2.460
_cell_measurement_theta_max      27.817

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      3.702
_exptl_crystal_density_diffrn    3.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    21.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.052
_exptl_absorpt_correction_T_max  0.170
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5862
_diffrn_reflns_av_R_equivalents  0.1676
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1142
_reflns_number_gt                933
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1339P)²+12.8303P] 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     SHELXL
_refine_ls_extinction_coef       0.0020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1142
_refine_ls_number_parameters     53
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0900
_refine_ls_wR_factor_ref         0.2263
_refine_ls_wR_factor_gt          0.2185
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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
Pb1 Pb 0.0000 0.0000 0.5000 0.0402(6) Uani 1 2 d S . .
I1 I -0.06121(15) 0.2500 0.7410(2) 0.0519(7) Uani 1 2 d S . .
I2 I 0.10944(16) -0.2500 0.6920(2) 0.0553(8) Uani 1 2 d S . .
I3 I 0.16574(13) 0.2500 0.4656(2) 0.0548(7) Uani 1 2 d S . .
N1 N 0.8518(19) 0.916(3) 0.023(2) 0.071(7) Uani 0.50 1 d P A 1
H1 H 0.8539 1.0218 0.0227 0.085 Uiso 0.50 1 calc PR A 1
C1 C 0.8518(19) 0.916(3) 0.023(2) 0.071(7) Uani 0.50 1 d P A 2
H1A H 0.8541 1.0305 0.0227 0.085 Uiso 0.50 1 calc PR A 2
C2 C 0.892(2) 0.831(3) -0.075(2) 0.084(9) Uani 1 1 d . . .
H2 H 0.9212 0.8873 -0.1440 0.101 Uiso 1 1 calc R A 1
C3 C 0.8092(17) 0.839(4) 0.118(3) 0.078(8) Uani 1 1 d . . .
H3 H 0.7793 0.8979 0.1847 0.093 Uiso 1 1 calc R A 1

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 0.0437(8) 0.0289(8) 0.0480(9) 0.0012(4) 0.0015(4) -0.0006(4)
I1 0.0580(13) 0.0464(12) 0.0514(12) 0.000 0.0065(10) 0.000
I2 0.0618(14) 0.0457(13) 0.0584(13) 0.000 -0.0207(10) 0.000
I3 0.0373(11) 0.0433(13) 0.0837(15) 0.000 0.0110(10) 0.000
N1 0.076(17) 0.038(13) 0.098(18) 0.002(11) -0.002(14) 0.007(12)
C1 0.076(17) 0.038(13) 0.098(18) 0.002(11) -0.002(14) 0.007(12)
C2 0.13(3) 0.069(16) 0.053(14) 0.022(12) 0.026(16) 0.011(18)
C3 0.063(15) 0.10(2) 0.066(15) -0.003(15) 0.021(13) 0.009(15)

_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 I3 3.2184(15) . ?
Pb1 I3 3.2184(15) 5_556 ?
Pb1 I2 3.2228(16) . ?
Pb1 I2 3.2228(16) 5_556 ?
Pb1 I1 3.2595(16) 5_556 ?
Pb1 I1 3.2595(16) . ?
I1 Pb1 3.2595(16) 4_556 ?
I2 Pb1 3.2228(16) 4_546 ?
I3 Pb1 3.2184(15) 4_556 ?
N1 C3 1.29(3) . ?
N1 C2 1.33(4) . ?
N1 H1 0.8600 . ?
C2 C2 1.31(5) 8_575 ?
C2 H2 0.9300 . ?
C3 C3 1.45(6) 8_575 ?
C3 H3 0.9300 . ?

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
I3 Pb1 I3 180.00(4) . 5_556 ?
I3 Pb1 I2 93.79(5) . . ?
I3 Pb1 I2 86.21(5) 5_556 . ?
I3 Pb1 I2 86.21(5) . 5_556 ?
I3 Pb1 I2 93.79(5) 5_556 5_556 ?
I2 Pb1 I2 180.0 . 5_556 ?
I3 Pb1 I1 95.56(5) . 5_556 ?
I3 Pb1 I1 84.44(5) 5_556 5_556 ?
I2 Pb1 I1 84.19(4) . 5_556 ?
I2 Pb1 I1 95.81(4) 5_556 5_556 ?
I3 Pb1 I1 84.44(5) . . ?
I3 Pb1 I1 95.56(5) 5_556 . ?
I2 Pb1 I1 95.81(4) . . ?
I2 Pb1 I1 84.19(4) 5_556 . ?
I1 Pb1 I1 180.00(9) 5_556 . ?
Pb1 I1 Pb1 76.77(4) . 4_556 ?
Pb1 I2 Pb1 77.81(4) 4_546 . ?
Pb1 I3 Pb1 77.94(4) . 4_556 ?
C3 N1 C2 120(3) . . ?
C3 N1 H1 119.8 . . ?
C2 N1 H1 119.8 . . ?
C2 C2 N1 121.1(16) 8_575 . ?
C2 C2 H2 119.5 8_575 . ?
N1 C2 H2 119.5 . . ?
N1 C3 C3 118.6(17) . 8_575 ?
N1 C3 H3 120.7 . . ?
C3 C3 H3 120.7 8_575 . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         5.374
_refine_diff_density_min         -2.225
_refine_diff_density_rms         0.757

#===END  
