# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_R1
_database_code_depnum_ccdc_archive 'CCDC 2024878'
loop_
_audit_author_name
_audit_author_address
'Kang Min Ok'
;Sogang University
South Korea
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C9 H13 N5 O6 Pb'
_chemical_formula_sum            'C9 H13 N5 O6 Pb'
_chemical_formula_weight         494.43
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   7.1661(18)
_cell_length_b                   9.589(3)
_cell_length_c                   22.282(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1531.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9191
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.4
_cell_measurement_wavelength     0.71076

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.058
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    11.051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.104
_shelx_estimated_absorpt_T_max   0.567

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'PHOTON II CPAD detector'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      -0.014316
_diffrn_orient_matrix_ub_12      0.029538
_diffrn_orient_matrix_ub_13      0.042824
_diffrn_orient_matrix_ub_21      -0.138784
_diffrn_orient_matrix_ub_22      -0.004875
_diffrn_orient_matrix_ub_23      -0.004171
_diffrn_orient_matrix_ub_31      0.002695
_diffrn_orient_matrix_ub_32      -0.099891
_diffrn_orient_matrix_ub_33      0.012759
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_number            31181
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.312
_diffrn_reflns_theta_max         28.421
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_coverage         0.733
_reflns_number_total             3853
_reflns_number_gt                3724
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.38A integration software'
_computing_data_reduction        'Bruker APEX3 software'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+0.3812P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3853
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.095
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_restrained_S_all      1.277
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.063(5)
_refine_diff_density_max         0.882
_refine_diff_density_min         -1.662
_refine_diff_density_rms         0.282

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.04997(4) 0.35383(4) 0.53011(2) 0.03248(12) Uani 1 1 d . . . . .
O1 O -0.0868(10) 0.1989(10) 0.4477(4) 0.050(2) Uani 1 1 d . . . . .
O2 O 0.2110(9) 0.1962(8) 0.4560(3) 0.0323(14) Uani 1 1 d . . . . .
O3 O -0.1051(12) 0.5068(13) 0.4473(4) 0.062(3) Uani 1 1 d . . . . .
O4 O 0.1993(11) 0.5186(11) 0.4384(4) 0.049(2) Uani 1 1 d . . . . .
O5 O 0.0491(11) 0.1131(9) 0.5835(4) 0.0464(17) Uani 1 1 d D . . . .
H5C H 0.15683 0.086999 0.588687 0.07 Uiso 1 1 calc R U . . .
O6 O 0.6438(13) 0.3045(8) 0.2188(4) 0.0464(19) Uani 1 1 d . . . . .
N1 N 0.2019(10) 0.3034(7) 0.3287(3) 0.0258(14) Uani 1 1 d . . . . .
N2 N 0.4238(12) 0.4219(8) 0.2705(3) 0.0294(15) Uani 1 1 d . . . . .
H2 H 0.466978 0.499919 0.257447 0.035 Uiso 1 1 calc R U . . .
N3 N 0.4523(12) 0.1798(7) 0.2802(4) 0.0304(15) Uani 1 1 d . . . . .
N4 N 0.2492(12) 0.0690(8) 0.3437(4) 0.0326(16) Uani 1 1 d . . . . .
H4 H 0.321024 -0.002621 0.341133 0.039 Uiso 1 1 calc R U . . .
N5 N 0.1830(11) 0.5413(7) 0.3166(4) 0.0315(16) Uani 1 1 d . . . . .
H5 H 0.231224 0.617206 0.303089 0.038 Uiso 1 1 calc R U . . .
C1 C 0.2691(12) 0.4216(9) 0.3057(4) 0.0264(15) Uani 1 1 d . . . . .
C2 C 0.5126(14) 0.3000(9) 0.2552(4) 0.0310(18) Uani 1 1 d . . . . .
C3 C 0.3025(12) 0.1894(8) 0.3162(4) 0.0255(16) Uani 1 1 d . . . . .
C4 C 0.0762(13) 0.0564(9) 0.3772(4) 0.0287(16) Uani 1 1 d . . . . .
H4A H 0.078139 -0.036643 0.395414 0.034 Uiso 1 1 calc R U . . .
C5 C 0.0093(12) 0.5487(10) 0.3506(5) 0.0330(18) Uani 1 1 d . . . . .
H5A H -0.073543 0.475222 0.335661 0.04 Uiso 1 1 calc R U . . .
C6 C -0.0978(16) 0.0614(13) 0.3383(5) 0.044(3) Uani 1 1 d . . . . .
H6A H -0.206502 0.05259 0.36322 0.067 Uiso 1 1 calc R U . . .
H6B H -0.102137 0.148655 0.317242 0.067 Uiso 1 1 calc R U . . .
H6C H -0.094697 -0.013844 0.309933 0.067 Uiso 1 1 calc R U . . .
C7 C -0.083(2) 0.6854(13) 0.3392(6) 0.056(3) Uani 1 1 d . . . . .
H7A H -0.197331 0.690337 0.361595 0.084 Uiso 1 1 calc R U . . .
H7B H -0.00169 0.759622 0.3515 0.084 Uiso 1 1 calc R U . . .
H7C H -0.1097 0.694323 0.297154 0.084 Uiso 1 1 calc R U . . .
C8 C 0.0670(12) 0.1598(9) 0.4295(3) 0.0245(14) Uani 1 1 d . . . . .
C9 C 0.0396(14) 0.5235(9) 0.4170(4) 0.0326(17) Uani 1 1 d . . . . .
H5D H -0.048(14) 0.056(11) 0.565(6) 0.05(4) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O2 2.495(7) 4_456 ?
Pb1 O2 2.518(7) . ?
Pb1 O1 2.558(8) . ?
Pb1 O5 2.597(8) . ?
Pb1 O3 2.606(10) . ?
Pb1 O1 2.697(8) 4_556 ?
Pb1 O4 2.795(10) . ?
O1 C8 1.233(11) . ?
O2 C8 1.239(10) . ?
O3 C9 1.248(13) . ?
O4 C9 1.241(13) . ?
O6 C2 1.242(12) . ?
N1 C1 1.334(11) . ?
N1 C3 1.339(10) . ?
N2 C1 1.359(11) . ?
N2 C2 1.373(12) . ?
N3 C3 1.343(10) . ?
N3 C2 1.352(11) . ?
N4 C3 1.363(11) . ?
N4 C4 1.453(11) . ?
N5 C1 1.325(11) . ?
N5 C5 1.460(11) . ?
C4 C6 1.520(14) . ?
C4 C8 1.531(11) . ?
C5 C7 1.491(14) . ?
C5 C9 1.513(13) . ?

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 Pb1 O2 114.31(15) 4_456 . ?
O2 Pb1 O1 66.7(2) 4_456 . ?
O2 Pb1 O1 49.9(2) . . ?
O2 Pb1 O5 76.7(2) 4_456 . ?
O2 Pb1 O5 76.6(2) . . ?
O1 Pb1 O5 79.2(3) . . ?
O2 Pb1 O3 77.3(2) 4_456 . ?
O2 Pb1 O3 94.0(3) . . ?
O1 Pb1 O3 69.8(3) . . ?
O5 Pb1 O3 145.5(3) . . ?
O2 Pb1 O1 151.7(3) 4_456 4_556 ?
O2 Pb1 O1 64.3(2) . 4_556 ?
O1 Pb1 O1 113.13(19) . 4_556 ?
O5 Pb1 O1 75.6(3) . 4_556 ?
O3 Pb1 O1 130.3(3) . 4_556 ?
O2 Pb1 O4 124.9(2) 4_456 . ?
O2 Pb1 O4 71.6(2) . . ?
O1 Pb1 O4 87.1(3) . . ?
O5 Pb1 O4 147.0(3) . . ?
O3 Pb1 O4 47.7(2) . . ?
O1 Pb1 O4 82.6(3) 4_556 . ?
C8 O1 Pb1 94.0(5) . . ?
C8 O1 Pb1 150.0(7) . 4_456 ?
Pb1 O1 Pb1 110.3(3) . 4_456 ?
C8 O2 Pb1 144.6(6) . 4_556 ?
C8 O2 Pb1 95.8(5) . . ?
Pb1 O2 Pb1 118.7(3) 4_556 . ?
C9 O3 Pb1 95.8(7) . . ?
C9 O4 Pb1 87.1(6) . . ?
C1 N1 C3 114.8(7) . . ?
C1 N2 C2 121.3(7) . . ?
C3 N3 C2 116.3(7) . . ?
C3 N4 C4 122.8(7) . . ?
C1 N5 C5 122.3(7) . . ?
N5 C1 N1 119.9(8) . . ?
N5 C1 N2 118.9(8) . . ?
N1 C1 N2 121.2(8) . . ?
O6 C2 N3 122.7(8) . . ?
O6 C2 N2 118.9(8) . . ?
N3 C2 N2 118.4(8) . . ?
N1 C3 N3 127.7(7) . . ?
N1 C3 N4 116.5(7) . . ?
N3 C3 N4 115.8(7) . . ?
N4 C4 C6 113.8(8) . . ?
N4 C4 C8 112.0(7) . . ?
C6 C4 C8 112.2(8) . . ?
N5 C5 C7 109.4(9) . . ?
N5 C5 C9 112.2(8) . . ?
C7 C5 C9 111.8(9) . . ?
O1 C8 O2 120.2(7) . . ?
O1 C8 C4 119.0(8) . . ?
O2 C8 C4 120.6(7) . . ?
O4 C9 O3 123.5(9) . . ?
O4 C9 C5 121.0(9) . . ?
O3 C9 C5 115.5(9) . . ?

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
_geom_hbond_publ_flag
O5 H5C O3 0.82 2.09 2.818(12) 147.9 4_556 yes
N2 H2 N3 0.86 2 2.859(10) 173.8 3_655 yes
N4 H4 O6 0.86 2.29 2.993(10) 138.4 3_645 yes
N5 H5 O6 0.86 2.07 2.921(10) 173.1 3_655 yes
C6 H6B N1 0.96 2.65 3.169(14) 114.5 . yes
O5 H5D O4 0.98(3) 1.95(8) 2.849(12) 152(12) 4_456 yes
####################################################################### 
# 
# 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_S1
_database_code_depnum_ccdc_archive 'CCDC 2024879'
loop_
_audit_author_name
_audit_author_address
'Kang Min Ok'
;Sogang University
South Korea
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C9 H13 N5 O6 Pb'
_chemical_formula_sum            'C9 H13 N5 O6 Pb'
_chemical_formula_weight         494.44
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   7.218(5)
_cell_length_b                   9.690(9)
_cell_length_c                   22.366(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1564(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4645
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.22
_cell_measurement_wavelength     0.71076

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.063
_exptl_crystal_density_diffrn    2.1
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    10.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.438
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.243
_shelx_estimated_absorpt_T_max   0.549

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'PHOTON II CPAD detector'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      0.016118
_diffrn_orient_matrix_ub_12      0.049137
_diffrn_orient_matrix_ub_13      0.038937
_diffrn_orient_matrix_ub_21      -0.136103
_diffrn_orient_matrix_ub_22      0.018633
_diffrn_orient_matrix_ub_23      0.001364
_diffrn_orient_matrix_ub_31      -0.020326
_diffrn_orient_matrix_ub_32      -0.088822
_diffrn_orient_matrix_ub_33      0.021936
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_number            23321
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.781
_diffrn_reflns_theta_max         28.261
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_coverage         0.732
_reflns_number_total             3866
_reflns_number_gt                3608
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.38A integration software'
_computing_data_reduction        'Bruker APEX3 software'
_computing_structure_solution    'SHELXS-2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+5.1779P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3866
_refine_ls_number_parameters     198
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.16
_refine_ls_restrained_S_all      1.16
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1331 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(7)
_refine_diff_density_max         1.704
_refine_diff_density_min         -2.392
_refine_diff_density_rms         0.174

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.04928(5) 0.64652(5) 0.53025(2) 0.03307(11) Uani 1 1 d . . . . .
O1 O 0.2100(9) 0.8031(9) 0.4559(3) 0.0351(19) Uani 1 1 d . . . . .
O2 O -0.0877(10) 0.8016(11) 0.4479(4) 0.053(3) Uani 1 1 d . . . . .
O3 O 0.2000(12) 0.4846(11) 0.4403(4) 0.048(2) Uani 1 1 d . . . . .
O4 O -0.1046(12) 0.4938(13) 0.4475(4) 0.062(3) Uani 1 1 d . . . . .
O5 O 0.0478(12) 0.8844(9) 0.5839(4) 0.047(2) Uani 1 1 d D . . . .
O6 O 0.6440(13) 0.6934(8) 0.2189(4) 0.047(2) Uani 1 1 d . . . . .
N1 N 0.2014(11) 0.6937(9) 0.3281(4) 0.0282(19) Uani 1 1 d . . . . .
N2 N 0.4230(12) 0.5759(9) 0.2703(4) 0.0303(19) Uani 1 1 d . . . . .
H2 H 0.465672 0.498592 0.257336 0.036 Uiso 1 1 calc R U . . .
N3 N 0.4519(13) 0.8173(8) 0.2798(3) 0.0314(18) Uani 1 1 d . . . . .
N4 N 0.2469(13) 0.9293(10) 0.3428(4) 0.035(2) Uani 1 1 d . . . . .
H4 H 0.316803 1.000663 0.339078 0.042 Uiso 1 1 calc R U . . .
N5 N 0.1862(12) 0.4577(10) 0.3173(4) 0.036(2) Uani 1 1 d . . . . .
H5 H 0.236539 0.38269 0.304698 0.043 Uiso 1 1 calc R U . . .
C1 C 0.2687(13) 0.5771(11) 0.3058(4) 0.027(2) Uani 1 1 d . . . . .
C2 C 0.5114(15) 0.6980(11) 0.2549(5) 0.033(2) Uani 1 1 d . . . . .
C3 C 0.3005(14) 0.8078(11) 0.3159(4) 0.028(2) Uani 1 1 d . . . . .
C4 C 0.0762(14) 0.9417(11) 0.3775(4) 0.030(2) Uani 1 1 d . . . . .
H4A H 0.078192 1.034141 0.395291 0.037 Uiso 1 1 calc R U . . .
C5 C 0.0129(14) 0.4498(12) 0.3505(5) 0.038(3) Uani 1 1 d . . . . .
H5A H -0.069273 0.521936 0.334986 0.045 Uiso 1 1 calc R U . . .
C6 C -0.0983(18) 0.9364(17) 0.3372(6) 0.054(4) Uani 1 1 d . . . . .
H6A H -0.203673 0.968706 0.35932 0.08 Uiso 1 1 calc R U . . .
H6B H -0.11946 0.843138 0.324463 0.08 Uiso 1 1 calc R U . . .
H6C H -0.079719 0.994151 0.302827 0.08 Uiso 1 1 calc R U . . .
C7 C -0.080(2) 0.3129(15) 0.3398(7) 0.070(5) Uani 1 1 d . . . . .
H7A H -0.20276 0.31458 0.356613 0.105 Uiso 1 1 calc R U . . .
H7B H -0.009518 0.240822 0.358372 0.105 Uiso 1 1 calc R U . . .
H7C H -0.088346 0.295952 0.297582 0.105 Uiso 1 1 calc R U . . .
C8 C 0.0657(14) 0.8411(11) 0.4293(4) 0.0267(19) Uani 1 1 d . . . . .
C9 C 0.0412(19) 0.4778(11) 0.4183(5) 0.036(2) Uani 1 1 d . . . . .
H5C H -0.057(12) 0.940(12) 0.570(5) 0.054 Uiso 1 1 d D U . . .
H5D H 0.119(16) 0.967(8) 0.593(6) 0.054 Uiso 1 1 d D U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 2.516(7) 4_466 ?
Pb1 O1 2.532(8) . ?
Pb1 O2 2.575(8) . ?
Pb1 O5 2.599(9) . ?
Pb1 O4 2.617(11) . ?
Pb1 O2 2.713(8) 4_566 ?
Pb1 O3 2.774(10) . ?
O1 C8 1.255(12) . ?
O2 C8 1.242(12) . ?
O3 C9 1.249(15) . ?
O4 C9 1.249(14) . ?
O5 H5C 0.98(3) . ?
O5 H5D 0.98(3) . ?
O6 C2 1.250(13) . ?
N1 C1 1.328(13) . ?
N1 C3 1.344(13) . ?
N2 C1 1.368(12) . ?
N2 C2 1.388(13) . ?
N2 H2 0.86 . ?
N3 C2 1.353(13) . ?
N3 C3 1.361(12) . ?
N4 C3 1.378(13) . ?
N4 C4 1.461(12) . ?
N4 H4 0.86 . ?
N5 C1 1.326(13) . ?
N5 C5 1.457(13) . ?
N5 H5 0.86 . ?
C4 C8 1.516(13) . ?
C4 C6 1.549(15) . ?
C4 H4A 0.98 . ?
C5 C7 1.507(17) . ?
C5 C9 1.553(15) . ?
C5 H5A 0.98 . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?

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
O1 Pb1 O1 114.23(16) 4_466 . ?
O1 Pb1 O2 66.5(2) 4_466 . ?
O1 Pb1 O2 49.9(2) . . ?
O1 Pb1 O5 76.5(3) 4_466 . ?
O1 Pb1 O5 76.9(3) . . ?
O2 Pb1 O5 79.1(3) . . ?
O1 Pb1 O4 77.5(3) 4_466 . ?
O1 Pb1 O4 94.0(3) . . ?
O2 Pb1 O4 70.2(3) . . ?
O5 Pb1 O4 145.7(3) . . ?
O1 Pb1 O2 151.9(3) 4_466 4_566 ?
O1 Pb1 O2 64.2(2) . 4_566 ?
O2 Pb1 O2 113.07(19) . 4_566 ?
O5 Pb1 O2 75.9(3) . 4_566 ?
O4 Pb1 O2 130.0(3) . 4_566 ?
O1 Pb1 O3 125.5(2) 4_466 . ?
O1 Pb1 O3 71.5(3) . . ?
O2 Pb1 O3 87.8(3) . . ?
O5 Pb1 O3 147.0(3) . . ?
O4 Pb1 O3 48.2(2) . . ?
O2 Pb1 O3 81.8(3) 4_566 . ?
C8 O1 Pb1 144.0(7) . 4_566 ?
C8 O1 Pb1 96.1(6) . . ?
Pb1 O1 Pb1 118.8(3) 4_566 . ?
C8 O2 Pb1 94.4(6) . . ?
C8 O2 Pb1 149.8(8) . 4_466 ?
Pb1 O2 Pb1 110.5(3) . 4_466 ?
C9 O3 Pb1 87.5(7) . . ?
C9 O4 Pb1 94.8(7) . . ?
Pb1 O5 H5C 110(8) . . ?
Pb1 O5 H5D 146(8) . . ?
H5C O5 H5D 91(10) . . ?
C1 N1 C3 115.4(8) . . ?
C1 N2 C2 120.7(9) . . ?
C1 N2 H2 119.6 . . ?
C2 N2 H2 119.6 . . ?
C2 N3 C3 116.2(9) . . ?
C3 N4 C4 122.6(9) . . ?
C3 N4 H4 118.7 . . ?
C4 N4 H4 118.7 . . ?
C1 N5 C5 122.0(9) . . ?
C1 N5 H5 119 . . ?
C5 N5 H5 119 . . ?
N5 C1 N1 120.4(9) . . ?
N5 C1 N2 118.1(9) . . ?
N1 C1 N2 121.5(9) . . ?
O6 C2 N3 122.6(10) . . ?
O6 C2 N2 118.7(10) . . ?
N3 C2 N2 118.7(9) . . ?
N1 C3 N3 127.1(9) . . ?
N1 C3 N4 117.7(8) . . ?
N3 C3 N4 115.2(9) . . ?
N4 C4 C8 113.2(8) . . ?
N4 C4 C6 111.9(9) . . ?
C8 C4 C6 112.5(10) . . ?
N4 C4 H4A 106.2 . . ?
C8 C4 H4A 106.2 . . ?
C6 C4 H4A 106.2 . . ?
N5 C5 C7 110.4(10) . . ?
N5 C5 C9 112.1(9) . . ?
C7 C5 C9 111.6(10) . . ?
N5 C5 H5A 107.5 . . ?
C7 C5 H5A 107.5 . . ?
C9 C5 H5A 107.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 O1 119.4(8) . . ?
O2 C8 C4 119.8(9) . . ?
O1 C8 C4 120.6(9) . . ?
O4 C9 O3 124.1(10) . . ?
O4 C9 C5 115.0(11) . . ?
O3 C9 C5 120.9(11) . . ?

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
_geom_hbond_publ_flag
N2 H2 N3 0.86 2.03 2.890(12) 174.4 3_645 yes
N4 H4 O6 0.86 2.29 3.013(12) 141.5 3_655 yes
N5 H5 O6 0.86 2.09 2.952(13) 175.4 3_645 yes
O5 H5C O3 0.98(3) 1.92(5) 2.864(13) 163(12) 4_466 yes
O5 H5D O4 0.98(3) 2.22(11) 2.860(13) 122(10) 4_566 yes
