# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1961111'
loop_
_audit_author_name
_audit_author_address
'Jiao Liu'
;Northwest University
China
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2020-01-24 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         ?
_chemical_formula_sum            'C22 H14 N4 O9 Pb2'
_chemical_formula_weight         892.75

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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   10.489(3)
_cell_length_b                   11.331(3)
_cell_length_c                   11.564(3)
_cell_angle_alpha                90.053(4)
_cell_angle_beta                 107.913(5)
_cell_angle_gamma                103.473(4)
_cell_volume                     1267.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3690
_cell_measurement_theta_min      2.725
_cell_measurement_theta_max      28.423

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.339
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    13.319
_shelx_estimated_absorpt_T_min   0.166
_shelx_estimated_absorpt_T_max   0.349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.136
_exptl_absorpt_correction_T_max  0.264
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ω
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6251
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.854
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4382
_reflns_number_gt                3570
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2680P)²+0.2195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4382
_refine_ls_number_parameters     310
_refine_ls_number_restraints     222
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2931
_refine_ls_wR_factor_gt          0.2570
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.952
_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 0.78054(6) 0.08563(6) -0.24840(5) 0.0139(3) Uani 1 1 d . U . . .
Pb2 Pb 1.37451(7) 0.18169(6) 0.56026(6) 0.0160(3) Uani 1 1 d . U . . .
O1 O 0.9360(14) 0.2196(13) -0.0869(13) 0.026(3) Uani 1 1 d . U . . .
O2 O 0.9451(13) 0.3243(12) -0.2435(12) 0.023(3) Uani 1 1 d . U . . .
O3 O 1.4921(14) 0.6536(12) 0.2934(13) 0.026(3) Uani 1 1 d . U . . .
O4 O 1.3938(14) 0.7997(12) 0.1977(12) 0.023(3) Uani 1 1 d . U . . .
O5 O 0.9853(18) -0.0700(15) 0.2521(16) 0.042(4) Uani 1 1 d . U . . .
O6 O 1.1334(19) 0.1019(18) 0.3307(18) 0.056(5) Uani 1 1 d . U . . .
O7 O 0.4500(14) 0.1244(13) 0.3524(12) 0.027(3) Uani 1 1 d . U . . .
O8 O 0.6035(16) 0.1945(14) 0.5347(14) 0.032(3) Uani 1 1 d . U . . .
O9 O 1.2138(19) 0.2513(16) 0.6809(16) 0.049(4) Uani 1 1 d . U . . .
H9A H 1.1571 0.1994 0.7005 0.059 Uiso 1 1 d R U . . .
H9B H 1.1308 0.2432 0.6468 0.059 Uiso 1 1 d R U . . .
N1 N 1.3458(16) 0.3538(14) 0.4472(14) 0.019(3) Uani 1 1 d . U . . .
N2 N 1.2797(15) 0.4534(13) 0.2883(13) 0.017(3) Uani 1 1 d . U . . .
N3 N 0.7590(16) -0.0179(14) -0.0636(14) 0.021(3) Uani 1 1 d . U . . .
N4 N 0.7455(16) -0.0043(14) 0.1198(14) 0.017(3) Uani 1 1 d . U . . .
C1 C 0.981(2) 0.3139(17) -0.1368(17) 0.021(4) Uani 1 1 d . U . . .
C2 C 1.0975(11) 0.4101(9) -0.0422(9) 0.014(3) Uani 1 1 d G U . . .
C3 C 1.1435(11) 0.3895(8) 0.0805(10) 0.020(4) Uani 1 1 d G U . . .
H3 H 1.1091 0.3148 0.1069 0.023 Uiso 1 1 calc R U . . .
C4 C 1.2408(11) 0.4804(9) 0.1636(7) 0.020(4) Uani 1 1 d G U . . .
C5 C 1.2922(10) 0.5919(8) 0.1241(9) 0.008(3) Uani 1 1 d G U . . .
C6 C 1.2462(12) 0.6126(8) 0.0014(9) 0.025(4) Uani 1 1 d G U . . .
H6 H 1.2805 0.6872 -0.0250 0.030 Uiso 1 1 calc R U . . .
C7 C 1.1488(12) 0.5217(10) -0.0817(7) 0.031(5) Uani 1 1 d G U . . .
H7A H 1.1181 0.5355 -0.1638 0.038 Uiso 1 1 calc R U . . .
C8 C 1.4052(17) 0.6870(15) 0.2143(15) 0.012(3) Uani 1 1 d . U . . .
C9 C 1.317(2) 0.3497(18) 0.3310(17) 0.023(4) Uani 1 1 d . U . . .
H9 H 1.3200 0.2855 0.2827 0.028 Uiso 1 1 calc R U . . .
C10 C 1.268(2) 0.5187(19) 0.3835(18) 0.025(4) Uani 1 1 d . U . . .
H10 H 1.2335 0.5874 0.3806 0.031 Uiso 1 1 calc R U . . .
C11 C 1.3188(19) 0.4597(17) 0.4819(18) 0.023(4) Uani 1 1 d . U . . .
H11 H 1.3336 0.4867 0.5620 0.027 Uiso 1 1 calc R U . . .
C12 C 1.024(2) 0.0366(19) 0.2988(19) 0.026(4) Uani 1 1 d . U . . .
C13 C 0.8981(9) 0.0810(11) 0.3176(10) 0.014(3) Uani 1 1 d G U . . .
C14 C 0.9270(8) 0.1455(11) 0.4287(9) 0.026(4) Uani 1 1 d G U . . .
H14 H 1.0174 0.1688 0.4811 0.031 Uiso 1 1 calc R U . . .
C15 C 0.8208(11) 0.1751(10) 0.4616(8) 0.023(4) Uani 1 1 d G U . . .
H15 H 0.8402 0.2183 0.5359 0.027 Uiso 1 1 calc R U . . .
C16 C 0.6858(9) 0.1403(11) 0.3834(10) 0.018(4) Uani 1 1 d G U . . .
C17 C 0.6569(8) 0.0759(10) 0.2722(9) 0.012(3) Uani 1 1 d G U . . .
H17 H 0.5665 0.0526 0.2199 0.015 Uiso 1 1 calc R U . . .
C18 C 0.7630(10) 0.0462(10) 0.2394(8) 0.011(3) Uani 1 1 d G U . . .
C19 C 0.8029(19) 0.0478(17) 0.0435(17) 0.018(4) Uani 1 1 d . U . . .
H19 H 0.8675 0.1226 0.0608 0.022 Uiso 1 1 calc R U . . .
C20 C 0.6431(19) -0.1016(17) 0.0565(17) 0.017(4) Uani 1 1 d . U . . .
H20 H 0.5764 -0.1504 0.0849 0.020 Uiso 1 1 calc R U . . .
C21 C 0.657(2) -0.1136(18) -0.0539(18) 0.021(4) Uani 1 1 d . U . . .
H21 H 0.6053 -0.1762 -0.1138 0.025 Uiso 1 1 calc R U . . .
C22 C 0.575(2) 0.1453(19) 0.428(2) 0.032(5) Uani 1 1 d . U . . .


_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 2.327(14) . ?
Pb1 N3 2.484(15) . ?
Pb1 O5 2.517(17) 2_755 ?
Pb1 O4 2.672(13) 2_765 ?
Pb2 N1 2.375(15) . ?
Pb2 O3 2.371(14) 2_866 ?
Pb2 O8 2.481(15) 1_655 ?
Pb2 O9 2.734(17) . ?
O1 C1 1.28(2) . ?
O2 C1 1.19(2) . ?
O3 C8 1.21(2) . ?
O3 Pb2 2.371(14) 2_866 ?
O4 C8 1.32(2) . ?
O4 Pb1 2.672(13) 2_765 ?
O5 C12 1.25(3) . ?
O5 Pb1 2.517(17) 2_755 ?
O6 C12 1.16(3) . ?
O7 C22 1.30(3) . ?
O8 C22 1.27(3) . ?
O8 Pb2 2.481(15) 1_455 ?
O9 H9A 0.8199 . ?
O9 H9B 0.8200 . ?
N1 C9 1.28(2) . ?
N1 C11 1.38(2) . ?
N2 C9 1.37(2) . ?
N2 C10 1.38(2) . ?
N2 C4 1.426(16) . ?
N3 C19 1.34(2) . ?
N3 C21 1.37(2) . ?
N4 C19 1.29(2) . ?
N4 C20 1.37(3) . ?
N4 C18 1.437(17) . ?
C1 C2 1.56(2) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C8 1.515(18) . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.35(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.60(2) . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C16 C22 1.42(2) . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.34(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
O1 Pb1 N3 75.7(5) . . ?
O1 Pb1 O5 75.5(5) . 2_755 ?
N3 Pb1 O5 102.9(5) . 2_755 ?
O1 Pb1 O4 80.8(4) . 2_765 ?
N3 Pb1 O4 81.7(5) . 2_765 ?
O5 Pb1 O4 153.8(5) 2_755 2_765 ?
N1 Pb2 O3 77.5(5) . 2_866 ?
N1 Pb2 O8 91.9(5) . 1_655 ?
O3 Pb2 O8 81.0(5) 2_866 1_655 ?
N1 Pb2 O9 85.6(5) . . ?
O3 Pb2 O9 69.9(5) 2_866 . ?
O8 Pb2 O9 150.7(5) 1_655 . ?
C1 O1 Pb1 104.8(12) . . ?
C8 O3 Pb2 109.9(11) . 2_866 ?
C8 O4 Pb1 129.8(11) . 2_765 ?
C12 O5 Pb1 95.6(13) . 2_755 ?
C22 O8 Pb2 104.3(13) . 1_455 ?
Pb2 O9 H9A 119.6 . . ?
Pb2 O9 H9B 120.5 . . ?
H9A O9 H9B 59.8 . . ?
C9 N1 C11 106.5(16) . . ?
C9 N1 Pb2 122.8(13) . . ?
C11 N1 Pb2 128.4(12) . . ?
C9 N2 C10 108.1(15) . . ?
C9 N2 C4 125.6(14) . . ?
C10 N2 C4 125.8(14) . . ?
C19 N3 C21 104.7(15) . . ?
C19 N3 Pb1 119.2(12) . . ?
C21 N3 Pb1 128.6(12) . . ?
C19 N4 C20 106.7(17) . . ?
C19 N4 C18 125.9(15) . . ?
C20 N4 C18 125.9(16) . . ?
O2 C1 O1 124.3(18) . . ?
O2 C1 C2 123.7(16) . . ?
O1 C1 C2 111.9(15) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 121.5(10) . . ?
C7 C2 C1 118.3(10) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 N2 116.6(9) . . ?
C5 C4 N2 123.4(9) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 120.5(9) . . ?
C4 C5 C8 119.3(9) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C2 C7 H7A 120.0 . . ?
O3 C8 O4 127.2(16) . . ?
O3 C8 C5 118.6(15) . . ?
O4 C8 C5 114.2(14) . . ?
N1 C9 N2 110.1(17) . . ?
N1 C9 H9 125.0 . . ?
N2 C9 H9 125.0 . . ?
C11 C10 N2 103.9(17) . . ?
C11 C10 H10 128.0 . . ?
N2 C10 H10 128.0 . . ?
C10 C11 N1 110.6(18) . . ?
C10 C11 H11 124.7 . . ?
N1 C11 H11 124.7 . . ?
O6 C12 O5 130(2) . . ?
O6 C12 C13 119.0(18) . . ?
O5 C12 C13 110.6(16) . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C12 115.0(10) . . ?
C18 C13 C12 124.4(10) . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 C22 118.9(11) . . ?
C15 C16 C22 119.5(11) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 N4 123.4(9) . . ?
C13 C18 N4 116.0(9) . . ?
N4 C19 N3 112.1(17) . . ?
N4 C19 H19 123.9 . . ?
N3 C19 H19 123.9 . . ?
C21 C20 N4 107.3(18) . . ?
C21 C20 H20 126.3 . . ?
N4 C20 H20 126.3 . . ?
C20 C21 N3 108.3(17) . . ?
C20 C21 H21 125.9 . . ?
N3 C21 H21 125.9 . . ?
O8 C22 O7 120.2(19) . . ?
O8 C22 C16 118.5(18) . . ?
O7 C22 C16 119.7(18) . . ?

_refine_diff_density_max         4.491
_refine_diff_density_min         -6.146
_refine_diff_density_rms         0.963


# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.098 0.500 0.402 162.7 84.4
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1961112'
loop_
_audit_author_name
_audit_author_address
'Jiao Liu'
;Northwest University
China
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2020-01-24 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         ?
_chemical_formula_sum            'C22 H14 N4 O9 Pb Zn'
_chemical_formula_weight         750.93

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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   10.1986(4)
_cell_length_b                   12.0740(5)
_cell_length_c                   13.1106(6)
_cell_angle_alpha                112.5250(10)
_cell_angle_beta                 91.2160(10)
_cell_angle_gamma                95.0110(10)
_cell_volume                     1482.93(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.543
_cell_measurement_theta_max      25.452

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.527
_shelx_estimated_absorpt_T_min   0.341
_shelx_estimated_absorpt_T_max   0.561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.321
_exptl_absorpt_correction_T_max  0.521
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ω
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33680
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5217
_reflns_number_gt                4986
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0489P)²+0.3503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5217
_refine_ls_number_parameters     334
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.065
_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 0.05396(2) 0.63465(2) 0.16306(2) 0.03147(7) Uani 1 1 d . . . . .
Zn1 Zn 0.26639(4) 0.96803(4) 0.39760(3) 0.03063(10) Uani 1 1 d . . . . .
O1 O 0.3954(2) 0.9025(2) 0.2905(2) 0.0374(6) Uani 1 1 d . . . . .
O2 O 0.2526(2) 0.8030(2) 0.1454(2) 0.0414(6) Uani 1 1 d . . . . .
O3 O 0.8605(3) 0.5131(3) 0.0093(2) 0.0524(8) Uani 1 1 d . . . . .
O4 O 0.7493(3) 0.4737(3) -0.1471(2) 0.0502(7) Uani 1 1 d . . . . .
O5 O 0.2167(3) 0.8831(2) 0.4979(2) 0.0452(7) Uani 1 1 d . . . . .
O6 O 0.1882(3) 0.7249(3) 0.3424(2) 0.0492(7) Uani 1 1 d . . . . .
O7 O 0.1236(3) 0.3650(2) 0.6597(2) 0.0488(7) Uani 1 1 d . . . . .
O8 O 0.0275(3) 0.5162(2) 0.7804(2) 0.0486(7) Uani 1 1 d . . . . .
O9 O 0.0713(8) 0.7518(7) 0.9592(6) 0.196(3) Uani 1 1 d . U . . .
H9A H 0.1300 0.7634 1.0069 0.236 Uiso 1 1 d R U . . .
H9B H 0.0627 0.6880 0.9050 0.236 Uiso 1 1 d R U . . .
N1 N 0.5860(3) 0.7645(3) 0.3079(2) 0.0307(6) Uani 1 1 d . . . . .
N2 N 0.6418(3) 0.8842(3) 0.4797(2) 0.0353(7) Uani 1 1 d . . . . .
N3 N 0.0313(3) 0.8421(3) 0.6422(2) 0.0337(7) Uani 1 1 d . . . . .
N4 N -0.1098(3) 0.9707(3) 0.6483(2) 0.0351(7) Uani 1 1 d . . . . .
C1 C 0.3630(3) 0.8224(3) 0.1933(3) 0.0329(8) Uani 1 1 d . . . . .
C2 C 0.4700(3) 0.7474(3) 0.1345(3) 0.0310(7) Uani 1 1 d . . . . .
C3 C 0.5740(3) 0.7212(3) 0.1895(3) 0.0316(7) Uani 1 1 d . . . . .
C4 C 0.6683(3) 0.6499(3) 0.1321(3) 0.0340(8) Uani 1 1 d . . . . .
H4 H 0.7363 0.6327 0.1703 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6615(3) 0.6040(3) 0.0174(3) 0.0340(8) Uani 1 1 d . . . . .
C6 C 0.5585(4) 0.6283(4) -0.0385(3) 0.0390(9) Uani 1 1 d . . . . .
H6 H 0.5527 0.5972 -0.1154 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4640(4) 0.6989(4) 0.0199(3) 0.0398(9) Uani 1 1 d . . . . .
H7 H 0.3949 0.7141 -0.0186 0.048 Uiso 1 1 calc R U . . .
C8 C 0.7640(3) 0.5259(3) -0.0443(3) 0.0368(8) Uani 1 1 d . . . . .
C9 C 0.6553(4) 0.8660(3) 0.3753(3) 0.0369(8) Uani 1 1 d . . . . .
H9 H 0.7069 0.9177 0.3514 0.044 Uiso 1 1 calc R U . . .
C10 C 0.5220(5) 0.7151(4) 0.3738(4) 0.0542(12) Uani 1 1 d . . . . .
H10 H 0.4652 0.6444 0.3507 0.065 Uiso 1 1 calc R U . . .
C11 C 0.5580(5) 0.7898(4) 0.4782(3) 0.0562(12) Uani 1 1 d . . . . .
H11 H 0.5296 0.7784 0.5407 0.067 Uiso 1 1 calc R U . . .
C12 C 0.1884(3) 0.7729(3) 0.4441(3) 0.0331(8) Uani 1 1 d . . . . .
C13 C 0.1606(3) 0.6944(3) 0.5080(3) 0.0311(7) Uani 1 1 d . . . . .
C14 C 0.0911(4) 0.7304(3) 0.6039(3) 0.0335(8) Uani 1 1 d . . . . .
C15 C 0.0717(4) 0.6593(3) 0.6639(3) 0.0355(8) Uani 1 1 d . . . . .
H15 H 0.0256 0.6861 0.7279 0.043 Uiso 1 1 calc R U . . .
C16 C 0.1205(3) 0.5473(3) 0.6295(3) 0.0348(8) Uani 1 1 d . . . . .
C17 C 0.1880(4) 0.5094(3) 0.5327(3) 0.0399(9) Uani 1 1 d . . . . .
H17 H 0.2215 0.4349 0.5085 0.048 Uiso 1 1 calc R U . . .
C18 C 0.2058(4) 0.5803(3) 0.4729(3) 0.0396(9) Uani 1 1 d . . . . .
H18 H 0.2488 0.5519 0.4074 0.047 Uiso 1 1 calc R U . . .
C19 C 0.0906(4) 0.4691(4) 0.6931(3) 0.0401(9) Uani 1 1 d . . . . .
C20 C -0.0653(4) 0.8675(3) 0.5871(3) 0.0351(8) Uani 1 1 d . . . . .
H20 H -0.0972 0.8192 0.5153 0.042 Uiso 1 1 calc R U . . .
C21 C -0.0341(4) 1.0134(4) 0.7486(3) 0.0480(10) Uani 1 1 d . . . . .
H21 H -0.0421 1.0850 0.8084 0.058 Uiso 1 1 calc R U . . .
C22 C 0.0518(4) 0.9344(4) 0.7442(3) 0.0479(10) Uani 1 1 d . . . . .
H22 H 0.1136 0.9409 0.7998 0.058 Uiso 1 1 calc R U . . .


_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 O8 2.314(3) 2_566 ?
Pb1 O4 2.459(3) 2_665 ?
Pb1 O6 2.496(3) . ?
Pb1 O3 2.514(3) 2_665 ?
Pb1 O3 2.677(3) 1_455 ?
Pb1 C8 2.841(3) 2_665 ?
Zn1 O1 1.934(2) . ?
Zn1 N4 1.992(3) 2_576 ?
Zn1 O5 2.001(3) . ?
Zn1 N2 2.023(3) 2_676 ?
O1 C1 1.285(4) . ?
O2 C1 1.235(4) . ?
O3 C8 1.253(5) . ?
O3 Pb1 2.514(3) 2_665 ?
O3 Pb1 2.677(3) 1_655 ?
O4 C8 1.249(5) . ?
O4 Pb1 2.459(3) 2_665 ?
O5 C12 1.248(4) . ?
O6 C12 1.233(4) . ?
O7 C19 1.242(5) . ?
O8 C19 1.282(5) . ?
O8 Pb1 2.313(3) 2_566 ?
O9 H9B 0.8200 . ?
O9 H9A 0.8199 . ?
O9 H9B 0.8200 . ?
N1 C9 1.332(5) . ?
N1 C10 1.371(5) . ?
N1 C3 1.434(4) . ?
N2 C9 1.313(5) . ?
N2 C11 1.357(5) . ?
N2 Zn1 2.023(3) 2_676 ?
N3 C20 1.335(5) . ?
N3 C22 1.372(5) . ?
N3 C14 1.442(4) . ?
N4 C20 1.323(4) . ?
N4 C21 1.399(5) . ?
N4 Zn1 1.992(3) 2_576 ?
C1 C2 1.509(4) . ?
C2 C7 1.386(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.383(5) . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C5 C8 1.503(5) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 Pb1 2.841(3) 2_665 ?
C9 H9 0.9300 . ?
C10 C11 1.341(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.501(5) . ?
C13 C14 1.394(5) . ?
C13 C18 1.399(5) . ?
C14 C15 1.376(5) . ?
C15 C16 1.392(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(5) . ?
C16 C19 1.498(5) . ?
C17 C18 1.370(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.336(5) . ?
C21 H21 0.9300 . ?
C22 H22 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
O8 Pb1 O4 80.13(11) 2_566 2_665 ?
O8 Pb1 O6 87.32(10) 2_566 . ?
O4 Pb1 O6 71.32(10) 2_665 . ?
O8 Pb1 O3 92.62(11) 2_566 2_665 ?
O4 Pb1 O3 52.13(9) 2_665 2_665 ?
O6 Pb1 O3 122.40(10) . 2_665 ?
O8 Pb1 O3 76.92(11) 2_566 1_455 ?
O4 Pb1 O3 113.59(9) 2_665 1_455 ?
O6 Pb1 O3 162.02(10) . 1_455 ?
O3 Pb1 O3 67.71(10) 2_665 1_455 ?
O8 Pb1 C8 86.54(10) 2_566 2_665 ?
O4 Pb1 C8 25.99(10) 2_665 2_665 ?
O6 Pb1 C8 96.69(11) . 2_665 ?
O3 Pb1 C8 26.16(10) 2_665 2_665 ?
O3 Pb1 C8 91.01(10) 1_455 2_665 ?
O1 Zn1 N4 118.75(12) . 2_576 ?
O1 Zn1 O5 118.11(11) . . ?
N4 Zn1 O5 110.91(13) 2_576 . ?
O1 Zn1 N2 107.07(11) . 2_676 ?
N4 Zn1 N2 103.38(12) 2_576 2_676 ?
O5 Zn1 N2 94.27(12) . 2_676 ?
C1 O1 Zn1 122.3(2) . . ?
C8 O3 Pb1 91.7(2) . 2_665 ?
C8 O3 Pb1 143.2(3) . 1_655 ?
Pb1 O3 Pb1 112.29(10) 2_665 1_655 ?
C8 O4 Pb1 94.3(2) . 2_665 ?
C12 O5 Zn1 111.0(2) . . ?
C12 O6 Pb1 147.0(3) . . ?
C19 O8 Pb1 108.8(2) . 2_566 ?
H9B O9 H9A 119.5 . . ?
H9B O9 H9B 0.0 . . ?
H9A O9 H9B 119.5 . . ?
C9 N1 C10 106.8(3) . . ?
C9 N1 C3 126.0(3) . . ?
C10 N1 C3 127.1(3) . . ?
C9 N2 C11 105.2(3) . . ?
C9 N2 Zn1 121.2(3) . 2_676 ?
C11 N2 Zn1 133.6(3) . 2_676 ?
C20 N3 C22 107.7(3) . . ?
C20 N3 C14 124.9(3) . . ?
C22 N3 C14 127.1(3) . . ?
C20 N4 C21 105.6(3) . . ?
C20 N4 Zn1 123.3(3) . 2_576 ?
C21 N4 Zn1 130.8(2) . 2_576 ?
O2 C1 O1 125.2(3) . . ?
O2 C1 C2 118.5(3) . . ?
O1 C1 C2 116.3(3) . . ?
C7 C2 C3 117.6(3) . . ?
C7 C2 C1 118.9(3) . . ?
C3 C2 C1 123.5(3) . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 N1 117.1(3) . . ?
C2 C3 N1 121.5(3) . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 C8 121.0(3) . . ?
C4 C5 C8 119.5(3) . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 121.5(4) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
O4 C8 O3 121.8(3) . . ?
O4 C8 C5 119.3(3) . . ?
O3 C8 C5 118.8(3) . . ?
O4 C8 Pb1 59.67(18) . 2_665 ?
O3 C8 Pb1 62.18(18) . 2_665 ?
C5 C8 Pb1 176.4(3) . 2_665 ?
N2 C9 N1 111.8(3) . . ?
N2 C9 H9 124.1 . . ?
N1 C9 H9 124.1 . . ?
C11 C10 N1 105.8(4) . . ?
C11 C10 H10 127.1 . . ?
N1 C10 H10 127.1 . . ?
C10 C11 N2 110.5(4) . . ?
C10 C11 H11 124.8 . . ?
N2 C11 H11 124.8 . . ?
O6 C12 O5 123.6(4) . . ?
O6 C12 C13 118.7(3) . . ?
O5 C12 C13 117.6(3) . . ?
C14 C13 C18 117.1(3) . . ?
C14 C13 C12 122.7(3) . . ?
C18 C13 C12 120.2(3) . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 N3 116.8(3) . . ?
C13 C14 N3 121.4(3) . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 118.3(3) . . ?
C15 C16 C19 119.0(3) . . ?
C17 C16 C19 122.5(3) . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 121.5(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
O7 C19 O8 123.9(4) . . ?
O7 C19 C16 120.6(4) . . ?
O8 C19 C16 115.5(3) . . ?
N4 C20 N3 110.9(3) . . ?
N4 C20 H20 124.6 . . ?
N3 C20 H20 124.6 . . ?
C22 C21 N4 108.8(3) . . ?
C22 C21 H21 125.6 . . ?
N4 C21 H21 125.6 . . ?
C21 C22 N3 107.0(3) . . ?
C21 C22 H22 126.5 . . ?
N3 C22 H22 126.5 . . ?

_refine_diff_density_max         0.834
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.118


# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.050 -0.005 -0.005 424.5 31.2
_platon_squeeze_details          
;
;
