# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_n-FMDABCO_483K
_database_code_depnum_ccdc_archive 'CCDC 1923364'
loop_
_audit_author_name
_audit_author_address
'Zhong-Xia Wang'
;Nanchang University
China
;
_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 N2, 3(I Pb0.33)'
_chemical_formula_sum            'C7 H9 I3 N2 Pb'
_chemical_formula_weight         709.06

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'
F F 0.0171 0.0103 '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'

_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'

_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.
;

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                   10.6336(7)
_cell_length_b                   10.6336(7)
_cell_length_c                   8.1342(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     796.54(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    483(2)
_cell_measurement_reflns_used    735
_cell_measurement_theta_min      3.3450
_cell_measurement_theta_max      26.2790

_exptl_crystal_description       Block
_exptl_crystal_colour            Pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.956
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    16.375
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.028
_exptl_absorpt_correction_T_max  0.038
_exptl_absorpt_process_details   'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      483(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2029
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         28.930
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             436
_reflns_number_gt                222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+1.2851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         436
_refine_ls_number_parameters     25
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.048
_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_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 1.0000 1.0000 0.5000 0.1280(8) Uani 1 12 d S T P . .
I1 I 0.7275(2) 0.86375(10) 0.2500 0.1762(10) Uani 1 4 d S T P . .
C2 C 0.667(2) 0.333(2) 0.549(5) 0.54(6) Uani 0.0833 1 d D U P A -1
H2A H 0.7158 0.2842 0.5879 0.814 Uiso 0.0833 1 d R U P A -1
H2B H 0.7158 0.4317 0.5879 0.814 Uiso 0.0833 1 d R U P A -1
H2C H 0.5683 0.2842 0.5879 0.814 Uiso 0.0833 1 d R U P A -1
C1 C 0.5959(16) 0.4041(16) 0.324(4) 0.44(3) Uani 1 2 d DS TU P A .
H1A H 0.6443 0.5021 0.3638 0.529 Uiso 0.5 1 d R U P . .
N1 N 0.6667 0.3333 0.379(4) 0.46(3) Uani 1 6 d DS TU P . .

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 0.1475(10) 0.1475(10) 0.0889(8) 0.000 0.000 0.0738(5)
I1 0.1440(15) 0.2126(17) 0.1492(15) 0.000 0.000 0.0720(7)
C2 0.48(8) 0.48(8) 0.53(8) -0.01(7) 0.01(7) 0.15(8)
C1 0.42(3) 0.42(3) 0.56(8) -0.063(16) 0.063(16) 0.27(2)
N1 0.42(3) 0.42(3) 0.53(8) 0.000 0.000 0.209(17)

_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 3.2300(14) 13_776 ?
Pb1 I1 3.2300(14) 14_566 ?
Pb1 I1 3.2300(14) 2_765 ?
Pb1 I1 3.2300(14) 15_656 ?
Pb1 I1 3.2300(14) 3_675 ?
Pb1 I1 3.2300(14) . ?
I1 Pb1 3.2300(14) 4_774 ?
C2 N1 1.38(3) . ?
C2 H2A 0.9601 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 C1 1.20(6) 10_665 ?
C1 N1 1.38(3) . ?
C1 H1A 0.9602 . ?
N1 C1 1.38(3) 2_655 ?
N1 C1 1.38(3) 3_665 ?

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 84.57(3) 13_776 14_566 ?
I1 Pb1 I1 95.43(3) 13_776 2_765 ?
I1 Pb1 I1 180.0 14_566 2_765 ?
I1 Pb1 I1 84.57(3) 13_776 15_656 ?
I1 Pb1 I1 84.57(3) 14_566 15_656 ?
I1 Pb1 I1 95.43(3) 2_765 15_656 ?
I1 Pb1 I1 95.43(3) 13_776 3_675 ?
I1 Pb1 I1 95.43(3) 14_566 3_675 ?
I1 Pb1 I1 84.57(3) 2_765 3_675 ?
I1 Pb1 I1 180.0 15_656 3_675 ?
I1 Pb1 I1 180.00(5) 13_776 . ?
I1 Pb1 I1 95.43(3) 14_566 . ?
I1 Pb1 I1 84.57(3) 2_765 . ?
I1 Pb1 I1 95.43(3) 15_656 . ?
I1 Pb1 I1 84.57(3) 3_675 . ?
Pb1 I1 Pb1 78.04(4) . 4_774 ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C1 N1 109.0(7) 10_665 . ?
C1 C1 H1A 109.9 10_665 . ?
N1 C1 H1A 109.9 . . ?
C1 N1 C1 110.0(7) 2_655 3_665 ?
C1 N1 C1 110.0(7) 2_655 . ?
C1 N1 C1 110.0(7) 3_665 . ?
C1 N1 C2 109.0(11) 2_655 . ?
C1 N1 C2 109.0(11) 3_665 . ?
C1 N1 C2 108.9(11) . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.088

_shelx_res_file                  
;

    dai.res created by SHELXL-2014/7


TITL dai in P6(3)/mmc
CELL 0.71073  10.6336  10.6336   8.1342  90.000  90.000 120.000
ZERR    7.00   0.0007   0.0007   0.0005   0.000   0.000   0.000
LATT 1
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SYMM -X, -Y, 0.5+Z
SYMM Y, -X+Y, 0.5+Z
SYMM X-Y, X, 0.5+Z
SYMM Y, X, -Z
SYMM X-Y, -Y, -Z
SYMM -X, -X+Y, -Z
SYMM -Y, -X, 0.5-Z
SYMM -X+Y, Y, 0.5-Z
SYMM X, X-Y, 0.5-Z
SFAC C  H  N  F  I  Pb
UNIT 14 30 4 2 6 2
L.S. 20
ACTA
BOND $H
FMAP 2
PLAN 50
LIST 4
Eqiv $1 1-x+y, 1-x, +z
EQIV $2 1-y, +x-y, +z
EQIV $3 1-y, 1-x, 1/2-z
DFIX 1.5 0.1 C1 C1_$3
SIMU C2 > N1
DELU C2 > N1
SADI N1 C1 N1 C2 N1 C1_$1 C1_$2 N1
SADI C2 C1 C2 C1_$1 C2 C1_$2 C1 C1_$1 C1_$2 C1
TEMP 210.0
WGHT    0.067900    1.285100
FVAR       0.21405
PB1   6    1.000000    1.000000    0.500000    10.08333    0.14754    0.14754 =
         0.08889    0.00000    0.00000    0.07377
I1    5    0.727491    0.863745    0.250000    10.25000    0.14399    0.21265 =
         0.14921    0.00000    0.00000    0.07199
PART  -1
C2    1    0.666633    0.333368    0.548550    10.08333    0.48367    0.48367 =
         0.53350   -0.00875    0.00875    0.14593
AFIX   3
H2A   2    0.715773    0.284228    0.587940    10.08333   -1.50000
H2B   2    0.715773    0.431658    0.587870    10.08333   -1.50000
H2C   2    0.568343    0.284228    0.587860    10.08333   -1.50000
AFIX   0
PART   0
C1    1    0.595921    0.404079    0.323575    10.50000    0.42129    0.42129 =
         0.55648   -0.06259    0.06259    0.26715
AFIX   3
H1A   2    0.644271    0.502120    0.363755    10.50000   -1.20000
AFIX   0
N1    3    0.666667    0.333333    0.378586    10.16667    0.41778    0.41778 =
         0.53381    0.00000    0.00000    0.20889

HKLF 4

REM  dai in P6(3)/mmc
REM R1 =  0.0406 for     222 Fo > 4sig(Fo)  and  0.0690 for all     384 data
REM     25 parameters refined using     32 restraints

END

WGHT      0.0619      1.3112

REM Highest difference peak  0.441,  deepest hole -0.406,  1-sigma level  0.088
Q1    1   1.0000  1.0000  0.6030  10.16667  0.05    0.44
Q2    1   0.7877  0.9588  0.2500  10.50000  0.05    0.37
Q3    1   0.6700  0.8350  0.1675  10.50000  0.05    0.34
Q4    1   0.9539  0.9077  0.4988  10.50000  0.05    0.31
Q5    1   0.7620  0.5240  0.3189  10.50000  0.05    0.31
Q6    1   0.5919  0.4081  0.4830  10.50000  0.05    0.27
Q7    1   1.0000  1.0000  0.2500  10.08333  0.05    0.27
Q8    1   0.6121  0.3879  0.5487  10.50000  0.05    0.23
Q9    1   0.5360  0.4640  0.4413  10.50000  0.05    0.18
Q10   1   0.7292  0.7292  0.5000  10.50000  0.05    0.10
Q11   1   0.8480  0.6960  0.4295  10.50000  0.05    0.09
Q12   1   0.7986  0.8993  0.6129  10.50000  0.05    0.08
Q13   1   0.8382  0.6764  0.3291  10.50000  0.05    0.08
Q14   1   0.6001  0.5224  0.3615  11.00000  0.05    0.08
Q15   1   0.7690  0.8845  0.0034  10.50000  0.05    0.07
Q16   1   0.6202  0.5782  0.3392  11.00000  0.05    0.06
Q17   1   0.8089  0.6178  0.4910  10.50000  0.05    0.06
Q18   1   0.5182  0.4818  0.2500  10.25000  0.05    0.06
Q19   1   0.6600  0.6626  0.3417  11.00000  0.05    0.06
Q20   1   0.7264  0.6620  0.2500  10.50000  0.05    0.05
Q21   1   0.7981  0.7888  0.1153  11.00000  0.05    0.05
Q22   1   1.0565  0.9435  0.6931  10.50000  0.05    0.04
Q23   1   0.4811  0.5189  0.3764  10.50000  0.05    0.03
Q24   1   0.6139  0.5771  0.5421  11.00000  0.05    0.02
Q25   1   0.5916  0.9145  0.2500  10.50000  0.05    0.00
;
_shelx_res_checksum              10343
_vrf_PLAT260_n-FMDABCO_483K      
;
PROBLEM: Large Average Ueq of Residue Including        N1      0.478 Check 
RESPONSE: The alert is due to the highly disordered cation
;
_vrf_PLAT342_n-FMDABCO_483K      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............       0.05 Ang.  
RESPONSE: The alert is due to the highly disordered cation
;

####################################################################### 
# 
# 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_n-FMDABCO_293K
_database_code_depnum_ccdc_archive 'CCDC 1923365'
loop_
_audit_author_name
_audit_author_address
'Zhong-Xia Wang'
;Nanchang University
China
;
_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'I3 Pb, C7 H14 F N2'
_chemical_formula_sum            'C7 H14 F I3 N2 Pb'
_chemical_formula_weight         733.10

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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'

_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.
;

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                   17.4558(5)
_cell_length_b                   8.0494(2)
_cell_length_c                   21.4892(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3019.42(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9372
_cell_measurement_theta_min      2.8500
_cell_measurement_theta_max      30.2450

_exptl_crystal_description       Block
_exptl_crystal_colour            Pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.225
_exptl_crystal_F_000             2560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    17.293
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.022
_exptl_absorpt_correction_T_max  0.031
_exptl_absorpt_process_details   'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16409
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.944
_diffrn_reflns_theta_max         30.688
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3862
_reflns_number_gt                3182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+4.2605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00085(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3862
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0647
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_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 0.25002(2) 0.41051(2) 0.40412(2) 0.03466(8) Uani 1 1 d . . . . .
I1 I 0.19420(2) 0.16387(4) 0.29791(2) 0.04350(10) Uani 1 1 d . . . . .
I2 I 0.10388(2) 0.64341(4) 0.41323(2) 0.04099(10) Uani 1 1 d . . . . .
I3 I 0.16861(2) 0.15972(4) 0.50210(2) 0.04725(11) Uani 1 1 d . . . . .
N1 N 0.9025(2) 0.3018(4) 0.36674(17) 0.0317(8) Uani 1 1 d . . . . .
F1 F 0.8283(2) 0.5377(5) 0.36698(18) 0.0787(12) Uani 1 1 d . . . . .
N2 N 0.9471(3) 0.0443(6) 0.3088(2) 0.0586(13) Uani 1 1 d . . . . .
C4 C 0.9422(4) 0.3505(6) 0.3081(2) 0.0515(14) Uani 1 1 d . . . . .
H4A H 0.9875 0.4153 0.3176 0.062 Uiso 1 1 calc R U . . .
H4B H 0.9084 0.4177 0.2826 0.062 Uiso 1 1 calc R U . . .
C1 C 0.8782(3) 0.4521(7) 0.4024(2) 0.0514(14) Uani 1 1 d . . . . .
H1A H 0.8540 0.4193 0.4411 0.062 Uiso 1 1 calc R U . . .
H1B H 0.9223 0.5205 0.4121 0.062 Uiso 1 1 calc R U . . .
C6 C 0.9578(3) 0.2061(7) 0.4065(2) 0.0474(12) Uani 1 1 d . . . . .
H6A H 0.9329 0.1707 0.4446 0.057 Uiso 1 1 calc R U . . .
H6B H 1.0012 0.2756 0.4174 0.057 Uiso 1 1 calc R U . . .
C2 C 0.8354(3) 0.1927(7) 0.3522(3) 0.0556(15) Uani 1 1 d . . . . .
H2A H 0.7999 0.2512 0.3253 0.067 Uiso 1 1 calc R U . . .
H2B H 0.8088 0.1639 0.3903 0.067 Uiso 1 1 calc R U . . .
C7 C 0.9851(3) 0.0538(7) 0.3694(3) 0.0520(14) Uani 1 1 d . . . . .
H7A H 1.0401 0.0605 0.3633 0.062 Uiso 1 1 calc R U . . .
H7B H 0.9743 -0.0463 0.3929 0.062 Uiso 1 1 calc R U . . .
C5 C 0.9645(4) 0.1929(8) 0.2733(3) 0.0616(16) Uani 1 1 d . . . . .
H5A H 0.9372 0.1890 0.2340 0.074 Uiso 1 1 calc R U . . .
H5B H 1.0189 0.1957 0.2643 0.074 Uiso 1 1 calc R U . . .
C3 C 0.8636(4) 0.0363(8) 0.3203(4) 0.0698(18) Uani 1 1 d . . . . .
H3A H 0.8521 -0.0593 0.3461 0.084 Uiso 1 1 calc R U . . .
H3B H 0.8369 0.0227 0.2810 0.084 Uiso 1 1 calc R U . . .

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 0.04084(13) 0.02600(11) 0.03714(11) -0.00037(7) -0.00054(8) -0.00001(6)
I1 0.0532(2) 0.04127(18) 0.03606(17) 0.00024(13) -0.00955(14) -0.00214(14)
I2 0.03410(18) 0.03930(17) 0.0496(2) 0.00048(14) -0.00236(14) 0.00154(12)
I3 0.0617(2) 0.03743(18) 0.04267(19) 0.00038(14) 0.01625(16) 0.00059(14)
N1 0.032(2) 0.0319(18) 0.0314(19) -0.0021(16) -0.0014(15) 0.0037(15)
F1 0.095(3) 0.071(2) 0.070(2) -0.012(2) -0.011(2) 0.050(2)
N2 0.063(3) 0.049(3) 0.064(3) -0.012(2) 0.000(3) 0.017(2)
C4 0.061(4) 0.053(3) 0.040(3) 0.017(2) 0.012(3) 0.010(3)
C1 0.061(4) 0.050(3) 0.043(3) -0.009(2) -0.002(2) 0.018(3)
C6 0.047(3) 0.055(3) 0.039(3) 0.008(2) -0.014(2) 0.005(2)
C2 0.031(3) 0.067(4) 0.068(4) -0.019(3) -0.003(3) -0.010(2)
C7 0.050(3) 0.047(3) 0.059(3) 0.010(3) 0.004(3) 0.019(2)
C5 0.069(4) 0.079(4) 0.037(3) -0.001(3) 0.009(3) 0.023(3)
C3 0.064(4) 0.056(3) 0.090(5) -0.022(4) -0.014(4) -0.009(3)

_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 I2 3.1718(4) . ?
Pb1 I1 3.1780(4) . ?
Pb1 I1 3.2120(4) 8_665 ?
Pb1 I3 3.2365(4) 8_665 ?
Pb1 I3 3.2447(4) . ?
Pb1 I2 3.3414(4) 8_655 ?
I1 Pb1 3.2120(4) 8_655 ?
I2 Pb1 3.3414(4) 8_665 ?
I3 Pb1 3.2366(4) 8_655 ?
N1 C4 1.490(6) . ?
N1 C1 1.494(6) . ?
N1 C2 1.497(6) . ?
N1 C6 1.502(6) . ?
F1 C1 1.346(6) . ?
N2 C5 1.451(8) . ?
N2 C7 1.463(7) . ?
N2 C3 1.481(8) . ?
C4 C5 1.523(7) . ?
C6 C7 1.538(8) . ?
C2 C3 1.516(8) . ?

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
I2 Pb1 I1 99.613(10) . . ?
I2 Pb1 I1 84.976(10) . 8_665 ?
I1 Pb1 I1 88.813(11) . 8_665 ?
I2 Pb1 I3 86.930(10) . 8_665 ?
I1 Pb1 I3 171.476(12) . 8_665 ?
I1 Pb1 I3 86.311(10) 8_665 8_665 ?
I2 Pb1 I3 88.594(10) . . ?
I1 Pb1 I3 86.740(10) . . ?
I1 Pb1 I3 171.471(12) 8_665 . ?
I3 Pb1 I3 98.954(13) 8_665 . ?
I2 Pb1 I2 172.117(13) . 8_655 ?
I1 Pb1 I2 82.772(9) . 8_655 ?
I1 Pb1 I2 102.636(10) 8_665 8_655 ?
I3 Pb1 I2 91.472(10) 8_665 8_655 ?
I3 Pb1 I2 84.026(9) . 8_655 ?
Pb1 I1 Pb1 78.075(8) . 8_655 ?
Pb1 I2 Pb1 76.279(7) . 8_665 ?
Pb1 I3 Pb1 76.776(8) 8_655 . ?
C4 N1 C1 110.7(4) . . ?
C4 N1 C2 110.0(4) . . ?
C1 N1 C2 111.0(4) . . ?
C4 N1 C6 108.5(4) . . ?
C1 N1 C6 107.9(4) . . ?
C2 N1 C6 108.7(4) . . ?
C5 N2 C7 109.3(5) . . ?
C5 N2 C3 109.2(5) . . ?
C7 N2 C3 107.5(5) . . ?
N1 C4 C5 108.3(4) . . ?
F1 C1 N1 108.0(4) . . ?
N1 C6 C7 108.3(4) . . ?
N1 C2 C3 109.1(4) . . ?
N2 C7 C6 111.3(4) . . ?
N2 C5 C4 112.0(4) . . ?
N2 C3 C2 111.0(5) . . ?

_refine_diff_density_max         1.047
_refine_diff_density_min         -0.873
_refine_diff_density_rms         0.165

_shelx_res_file                  
;

    pbca.res created by SHELXL-2014/7

TITL pbca in Pbca
CELL 0.71073  17.4558   8.0494  21.4892  90.000  90.000  90.000
ZERR    1.00   0.0005   0.0002   0.0005   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C  H  N  F  I  Pb
UNIT 34 34 34 34 34 34
L.S. 20
ACTA
BOND
FMAP 2
PLAN 20
WGHT    0.028600    4.260500
EXTI    0.000849
FVAR       0.04714
MOLE 1
PB1   6    0.250015    0.410507    0.404115    11.00000    0.04084    0.02600 =
         0.03714   -0.00037   -0.00054   -0.00001
I1    5    0.194196    0.163870    0.297905    11.00000    0.05316    0.04127 =
         0.03606    0.00024   -0.00955   -0.00214
I2    5    0.103876    0.643415    0.413227    11.00000    0.03410    0.03930 =
         0.04958    0.00048   -0.00236    0.00154
I3    5    0.168613    0.159721    0.502101    11.00000    0.06166    0.03743 =
         0.04267    0.00038    0.01625    0.00059
N1    3    0.902543    0.301822    0.366740    11.00000    0.03192    0.03185 =
         0.03143   -0.00206   -0.00135    0.00368
F1    4    0.828346    0.537669    0.366977    11.00000    0.09488    0.07135 =
         0.06993   -0.01207   -0.01138    0.04972
N2    3    0.947115    0.044274    0.308817    11.00000    0.06257    0.04907 =
         0.06406   -0.01173    0.00021    0.01661
C4    1    0.942164    0.350518    0.308102    11.00000    0.06144    0.05337 =
         0.03974    0.01722    0.01152    0.00984
AFIX  23
H4A   2    0.987526    0.415338    0.317601    11.00000   -1.20000
H4B   2    0.908378    0.417703    0.282588    11.00000   -1.20000
AFIX   0
C1    1    0.878152    0.452075    0.402412    11.00000    0.06140    0.04968 =
         0.04305   -0.00927   -0.00198    0.01755
AFIX  23
H1A   2    0.853965    0.419250    0.441146    11.00000   -1.20000
H1B   2    0.922294    0.520549    0.412106    11.00000   -1.20000
AFIX   0
C6    1    0.957842    0.206072    0.406500    11.00000    0.04743    0.05533 =
         0.03938    0.00806   -0.01365    0.00505
AFIX  23
H6A   2    0.932933    0.170728    0.444616    11.00000   -1.20000
H6B   2    1.001219    0.275570    0.417375    11.00000   -1.20000
AFIX   0
C2    1    0.835428    0.192719    0.352232    11.00000    0.03129    0.06745 =
         0.06795   -0.01871   -0.00285   -0.01016
AFIX  23
H2A   2    0.799930    0.251198    0.325283    11.00000   -1.20000
H2B   2    0.808777    0.163943    0.390346    11.00000   -1.20000
AFIX   0
C7    1    0.985125    0.053819    0.369410    11.00000    0.05015    0.04692 =
         0.05881    0.00981    0.00373    0.01886
AFIX  23
H7A   2    1.040102    0.060526    0.363339    11.00000   -1.20000
H7B   2    0.974303   -0.046312    0.392936    11.00000   -1.20000
AFIX   0
C5    1    0.964490    0.192880    0.273307    11.00000    0.06858    0.07885 =
         0.03726   -0.00148    0.00931    0.02254
AFIX  23
H5A   2    0.937246    0.188987    0.233992    11.00000   -1.20000
H5B   2    1.018927    0.195702    0.264306    11.00000   -1.20000
AFIX   0
C3    1    0.863562    0.036325    0.320280    11.00000    0.06411    0.05554 =
         0.08971   -0.02166   -0.01404   -0.00921
AFIX  23
H3A   2    0.852103   -0.059286    0.346130    11.00000   -1.20000
H3B   2    0.836905    0.022686    0.281005    11.00000   -1.20000
AFIX   0
HKLF 4

REM  pbca in Pbca
REM R1 =  0.0286 for    3182 Fo > 4sig(Fo)  and  0.0391 for all    3862 data
REM    128 parameters refined using      0 restraints

END

WGHT      0.0281      4.4487

REM Highest difference peak  1.047,  deepest hole -0.873,  1-sigma level  0.165
Q1    1   0.2050  0.2938  0.4022  11.00000  0.05    1.05
Q2    1   0.2472  0.4163  0.4445  11.00000  0.05    0.88
Q3    1   0.2607  0.4177  0.3640  11.00000  0.05    0.81
Q4    1   0.2421  0.0319  0.2988  11.00000  0.05    0.80
Q5    1   0.2428  0.2997  0.2999  11.00000  0.05    0.80
Q6    1   0.1806  0.1594  0.5418  11.00000  0.05    0.80
Q7    1   0.1458  0.7531  0.4203  11.00000  0.05    0.78
Q8    1   0.2980  0.5247  0.4002  11.00000  0.05    0.78
Q9    1   0.2500  0.3396  0.4022  11.00000  0.05    0.78
Q10   1   0.2963  0.3004  0.4040  11.00000  0.05    0.76
Q11   1   0.1713  0.1837  0.3291  11.00000  0.05    0.72
Q12   1   0.1885  0.0784  0.2996  11.00000  0.05    0.70
Q13   1   0.2492  0.5114  0.4682  11.00000  0.05    0.68
Q14   1   0.1852  0.0748  0.5155  11.00000  0.05    0.67
Q15   1   0.0946  0.6644  0.3776  11.00000  0.05    0.66
Q16   1   0.1647  0.2485  0.4303  11.00000  0.05    0.66
Q17   1   0.2508  0.5274  0.4056  11.00000  0.05    0.63
Q18   1   0.1255  0.0988  0.5325  11.00000  0.05    0.60
Q19   1   0.1684  0.1656  0.4569  11.00000  0.05    0.60
Q20   1   0.2006  0.3786  0.3381  11.00000  0.05    0.59
;
_shelx_res_checksum              77007
