# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_pyi_0m
_database_code_depnum_ccdc_archive 'CCDC 1886890'
loop_
_audit_author_name
_audit_author_address
'Jim Britten'
;McMaster University
Canada
;
_audit_update_record             
;
2018-12-21 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;
_audit_creation_date             2018-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(I3 Pb1), 1(C4 H10 N1)'
_chemical_formula_sum            'C4 H10 I3 N Pb'
_chemical_formula_weight         660.05
_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      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   9.3117(5)
_cell_length_b                   9.3117(5)
_cell_length_c                   8.1080(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     608.84(7)
_cell_formula_units_Z            1.99992
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    297
_cell_measurement_theta_max      23.57
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.566
_shelx_estimated_absorpt_T_min   0.047
_exptl_absorpt_coefficient_mu    21.405
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.2518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. 
wR2(int) was 0.1405 before and 0.0419 after correction. The Ratio of 
minimum to maximum transmission is 0.3375. The λ/2 correction factor 
is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    3.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6688
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.433
_diffrn_reflns_theta_min         2.526
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                316
_reflns_number_total             384
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     21
_refine_ls_number_reflns         384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.042
_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)+(0.0333P)²+0.0834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0589
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C4) = Uanis(N1) = Uanis(C1) = Uanis(C2)
3. Others
 Fixed Sof: I1(0.25) C1(0.08333) H1A(0.08333) H1B(0.08333) C2(0.08333)
 H2A(0.08333) H2B(0.08333) C3(0.08333) H3A(0.08333) H3B(0.08333) C4(0.08333)
 H4A(0.08333) H4B(0.08333) N1(0.08333) H1C(0.08333) H1D(0.08333)
4.a Free rotating group:
 C1(H1A,H1B,C2,H2A,H2B,C3,H3A,H3B,C4,H4A,H4B,N1,H1C,H1D)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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
Pb1 Pb 0.000000 0.000000 0.500000 0.04934(18) Uani 1 12 d S T P . .
I1 I 0.19699(9) 0.31142(9) 0.250000 0.0676(3) Uani 0.5 2 d S T P . .
C1 C 0.590(9) 0.159(4) 0.170(5) 0.083(6) Uani 0.0833 1 d . . . A -1
H1A H 0.474754 0.091701 0.136729 0.100 Uiso 0.0833 1 d G . . A -1
H1B H 0.649312 0.102146 0.138188 0.100 Uiso 0.0833 1 d G . . A -1
C2 C 0.603(7) 0.191(3) 0.352(4) 0.083(6) Uani 0.0833 1 d G . . A -1
H2A H 0.711955 0.218294 0.393098 0.100 Uiso 0.0833 1 d G . . A -1
H2B H 0.519374 0.095418 0.412028 0.100 Uiso 0.0833 1 d G . . A -1
C3 C 0.575(6) 0.338(5) 0.368(4) 0.083(6) Uani 0.0833 1 d G . . A -1
H3A H 0.458121 0.302023 0.361120 0.100 Uiso 0.0833 1 d G . . A -1
H3B H 0.619012 0.395359 0.471400 0.100 Uiso 0.0833 1 d G . . A -1
C4 C 0.669(6) 0.446(3) 0.223(4) 0.083(6) Uani 0.0833 1 d G . . A -1
H4A H 0.614714 0.505103 0.182281 0.100 Uiso 0.0833 1 d G . . A -1
H4B H 0.781823 0.526688 0.254240 0.100 Uiso 0.0833 1 d G . . A -1
N1 N 0.667(8) 0.329(6) 0.094(2) 0.083(6) Uani 0.0833 1 d G . . A -1
H1C H 0.610279 0.324191 0.013290 0.100 Uiso 0.0833 1 d G . . A -1
H1D H 0.767587 0.353556 0.051039 0.100 Uiso 0.0833 1 d G . . A -1


_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 3.2501(6) 14_556 ?
Pb1 I1 3.2501(6) 13_556 ?
Pb1 I1 3.2501(6) 3 ?
Pb1 I1 3.2501(6) 20 ?
Pb1 I1 3.2501(6) 8_556 ?
Pb1 I1 3.2501(6) 9_556 ?
Pb1 I1 3.2501(6) 21 ?
Pb1 I1 3.2501(6) 7_556 ?
Pb1 I1 3.2501(6) 15_556 ?
Pb1 I1 3.2501(6) . ?
Pb1 I1 3.2501(6) 19 ?
Pb1 I1 3.2501(6) 2 ?
I1 I1 0.7688(15) 20 ?
C1 C2 1.5005 . ?
C1 N1 1.5064 . ?
C2 C3 1.5178 . ?
C3 C4 1.5109 . ?
C4 N1 1.5087 . ?

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 I1 180.0 14_556 2 ?
I1 Pb1 I1 94.787(12) 8_556 21 ?
I1 Pb1 I1 93.49(2) 14_556 9_556 ?
I1 Pb1 I1 93.49(2) 2 21 ?
I1 Pb1 I1 85.213(12) 20 21 ?
I1 Pb1 I1 86.51(2) 7_556 . ?
I1 Pb1 I1 166.42(3) 3 9_556 ?
I1 Pb1 I1 180.0 3 15_556 ?
I1 Pb1 I1 93.49(2) 7_556 13_556 ?
I1 Pb1 I1 85.214(12) 2 . ?
I1 Pb1 I1 85.213(13) 19 21 ?
I1 Pb1 I1 13.58(3) 3 21 ?
I1 Pb1 I1 94.787(13) 14_556 3 ?
I1 Pb1 I1 93.49(2) 20 3 ?
I1 Pb1 I1 104.82(2) 14_556 20 ?
I1 Pb1 I1 85.213(12) 13_556 15_556 ?
I1 Pb1 I1 86.51(2) 19 13_556 ?
I1 Pb1 I1 75.18(2) 7_556 15_556 ?
I1 Pb1 I1 94.786(12) 14_556 . ?
I1 Pb1 I1 86.51(2) 14_556 21 ?
I1 Pb1 I1 166.42(3) 2 7_556 ?
I1 Pb1 I1 75.18(2) 2 20 ?
I1 Pb1 I1 104.82(2) 13_556 21 ?
I1 Pb1 I1 94.786(13) 20 7_556 ?
I1 Pb1 I1 85.214(13) 8_556 7_556 ?
I1 Pb1 I1 94.787(12) 20 9_556 ?
I1 Pb1 I1 85.213(13) 2 3 ?
I1 Pb1 I1 75.18(2) 13_556 9_556 ?
I1 Pb1 I1 85.214(13) 14_556 13_556 ?
I1 Pb1 I1 75.18(2) 14_556 8_556 ?
I1 Pb1 I1 85.213(13) 14_556 15_556 ?
I1 Pb1 I1 104.82(2) 19 15_556 ?
I1 Pb1 I1 13.58(3) 8_556 13_556 ?
I1 Pb1 I1 93.49(2) 8_556 15_556 ?
I1 Pb1 I1 94.786(13) 8_556 19 ?
I1 Pb1 I1 104.82(2) 2 8_556 ?
I1 Pb1 I1 75.18(2) . 21 ?
I1 Pb1 I1 94.787(13) . 15_556 ?
I1 Pb1 I1 166.42(3) 15_556 21 ?
I1 Pb1 I1 13.58(3) 14_556 7_556 ?
I1 Pb1 I1 86.51(2) 2 9_556 ?
I1 Pb1 I1 13.58(3) 20 . ?
I1 Pb1 I1 85.213(12) 8_556 9_556 ?
I1 Pb1 I1 180.0 20 8_556 ?
I1 Pb1 I1 85.213(13) 7_556 9_556 ?
I1 Pb1 I1 166.42(3) 8_556 . ?
I1 Pb1 I1 104.82(2) . 9_556 ?
I1 Pb1 I1 93.49(2) 19 . ?
I1 Pb1 I1 13.58(3) 15_556 9_556 ?
I1 Pb1 I1 180.0 13_556 . ?
I1 Pb1 I1 75.18(2) 19 3 ?
I1 Pb1 I1 166.42(3) 14_556 19 ?
I1 Pb1 I1 104.82(2) 7_556 3 ?
I1 Pb1 I1 94.787(13) 19 9_556 ?
I1 Pb1 I1 94.786(13) 2 13_556 ?
I1 Pb1 I1 180.0 19 7_556 ?
I1 Pb1 I1 94.787(12) 13_556 3 ?
I1 Pb1 I1 86.51(2) 8_556 3 ?
I1 Pb1 I1 85.213(13) . 3 ?
I1 Pb1 I1 13.58(3) 2 19 ?
I1 Pb1 I1 166.42(3) 20 13_556 ?
I1 Pb1 I1 180.0 21 9_556 ?
I1 Pb1 I1 85.214(13) 20 19 ?
I1 Pb1 I1 86.51(2) 20 15_556 ?
I1 Pb1 I1 94.787(13) 2 15_556 ?
I1 Pb1 I1 94.787(13) 7_556 21 ?
Pb1 I1 Pb1 77.169(17) 4_554 . ?
I1 I1 Pb1 83.206(13) 20 . ?
I1 I1 Pb1 83.206(13) 20 4_554 ?
C2 C1 N1 104.1 . . ?
C1 C2 C3 103.2 . . ?
C4 C3 C2 103.7 . . ?
N1 C4 C3 105.1 . . ?
C1 N1 C4 107.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

