# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 2339688'
loop_
_audit_author_name
_audit_author_address
'Alfonso Castineiras'
;University of Santiago de Compostela
Spain
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 N9 O Pb'
_chemical_formula_sum            'C11 H9 N9 O Pb'
_chemical_formula_weight         490.46

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7307(3)
_cell_length_b                   16.6328(7)
_cell_length_c                   9.6082(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.1460(10)
_cell_angle_gamma                90
_cell_volume                     1373.45(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      30.48

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.372
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    12.302
_shelx_estimated_absorpt_T_min   0.439
_shelx_estimated_absorpt_T_max   0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41121
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4198
_reflns_number_gt                3849
_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       'APEX4 Software (Bruker, 2022)'
_computing_cell_refinement       'APEX4 Software (Bruker, 2022)'
_computing_data_reduction        'APEX4 Software (Bruker, 2022)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND, Brandenburg,K.(1999)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0106P)²+0.9808P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4198
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0175
_refine_ls_R_factor_gt           0.0144
_refine_ls_wR_factor_ref         0.0311
_refine_ls_wR_factor_gt          0.0303
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.003
_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 0.94020(2) -0.02741(2) 0.76163(2) 0.02086(3) Uani 1 1 d . . . . .
O1 O 0.77029(16) 0.05181(9) 0.59869(15) 0.0230(3) Uani 1 1 d . . . . .
N1 N 1.25421(19) -0.03028(10) 0.82356(18) 0.0217(3) Uani 1 1 d . . . . .
N2 N 1.07357(17) 0.06063(10) 0.62897(17) 0.0183(3) Uani 1 1 d . . . . .
N3 N 0.98634(18) 0.11457(10) 0.53589(18) 0.0202(3) Uani 1 1 d . . . . .
N4 N 1.5757(2) -0.03413(11) 0.8327(2) 0.0274(4) Uani 1 1 d . . . . .
N5 N 1.2837(2) 0.14241(11) 0.6026(2) 0.0233(3) Uani 1 1 d . . . . .
H5A H 1.225(3) 0.1710(16) 0.558(3) 0.028 Uiso 1 1 d . U . . .
H5B H 1.364(3) 0.1620(15) 0.646(3) 0.028 Uiso 1 1 d . U . . .
N6 N 0.5428(2) 0.27502(11) 0.2760(2) 0.0292(4) Uani 1 1 d . . . . .
N7 N 0.9642(2) 0.08245(12) 0.9237(2) 0.0311(4) Uani 1 1 d . . . . .
N8 N 1.0656(2) 0.13109(12) 0.92539(19) 0.0285(4) Uani 1 1 d . . . . .
N9 N 1.1620(3) 0.17903(14) 0.9308(3) 0.0459(5) Uani 1 1 d . . . . .
C1 C 1.3441(2) -0.08396(13) 0.9017(2) 0.0258(4) Uani 1 1 d . . . . .
H1 H 1.298614 -0.121454 0.955256 0.031 Uiso 1 1 calc R U . . .
C2 C 1.5047(2) -0.08572(13) 0.9056(2) 0.0278(4) Uani 1 1 d . . . . .
H2 H 1.564524 -0.124660 0.961742 0.033 Uiso 1 1 calc R U . . .
C3 C 1.4851(2) 0.02003(12) 0.7545(2) 0.0230(4) Uani 1 1 d . . . . .
H3 H 1.531265 0.057735 0.701835 0.028 Uiso 1 1 calc R U . . .
C4 C 1.3243(2) 0.02230(11) 0.7487(2) 0.0189(3) Uani 1 1 d . . . . .
C5 C 1.2214(2) 0.07896(11) 0.65732(19) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.8361(2) 0.10394(11) 0.52945(19) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.7351(2) 0.16211(11) 0.4373(2) 0.0189(3) Uani 1 1 d . . . . .
C8 C 0.7975(2) 0.22332(12) 0.3660(2) 0.0260(4) Uani 1 1 d . . . . .
H8 H 0.905719 0.227623 0.370905 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6977(3) 0.27779(13) 0.2878(2) 0.0297(5) Uani 1 1 d . . . . .
H9 H 0.741113 0.319019 0.240246 0.036 Uiso 1 1 calc R U . . .
C10 C 0.4839(2) 0.21582(13) 0.3434(2) 0.0280(4) Uani 1 1 d . . . . .
H10 H 0.375243 0.212696 0.335796 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5747(2) 0.15838(13) 0.4244(2) 0.0233(4) Uani 1 1 d . . . . .
H11 H 0.527886 0.117499 0.469949 0.028 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 O1 2.3600(14) . ?
Pb1 N2 2.3765(16) . ?
Pb1 N7 2.3862(19) . ?
Pb1 N1 2.7013(17) . ?
Pb1 N7 3.1280(19) 3_757 ?
Pb1 N3 3.3662(17) 3_756 ?
Pb1 N4 3.3724(19) 1_455 ?
O1 C6 1.288(2) . ?
N1 C1 1.330(3) . ?
N1 C4 1.346(2) . ?
N2 C5 1.307(2) . ?
N2 N3 1.395(2) . ?
N3 C6 1.314(2) . ?
N4 C2 1.328(3) . ?
N4 C3 1.339(3) . ?
N5 C5 1.337(3) . ?
N5 H5A 0.77(3) . ?
N5 H5B 0.82(3) . ?
N6 C10 1.330(3) . ?
N6 C9 1.338(3) . ?
N7 N8 1.198(3) . ?
N8 N9 1.153(3) . ?
C1 C2 1.396(3) . ?
C1 H1 0.9400 . ?
C2 H2 0.9400 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.480(3) . ?
C6 C7 1.491(3) . ?
C7 C11 1.386(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9400 . ?
C9 H9 0.9400 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?

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 N2 67.06(5) . . ?
O1 Pb1 N7 88.75(6) . . ?
N2 Pb1 N7 83.30(6) . . ?
O1 Pb1 N1 130.61(5) . . ?
N2 Pb1 N1 63.57(5) . . ?
N7 Pb1 N1 84.31(6) . . ?
O1 Pb1 N7 146.52(5) . 3_757 ?
N2 Pb1 N7 128.76(5) . 3_757 ?
N7 Pb1 N7 67.39(7) . 3_757 ?
N1 Pb1 N7 72.19(5) . 3_757 ?
O1 Pb1 N3 82.45(5) . 3_756 ?
N2 Pb1 N3 67.99(5) . 3_756 ?
N7 Pb1 N3 151.19(5) . 3_756 ?
N1 Pb1 N3 80.89(4) . 3_756 ?
N7 Pb1 N3 129.52(4) 3_757 3_756 ?
O1 Pb1 N4 69.36(5) . 1_455 ?
N2 Pb1 N4 134.27(5) . 1_455 ?
N7 Pb1 N4 82.56(6) . 1_455 ?
N1 Pb1 N4 155.80(5) . 1_455 ?
N7 Pb1 N4 84.00(5) 3_757 1_455 ?
N3 Pb1 N4 119.04(4) 3_756 1_455 ?
C6 O1 Pb1 115.66(11) . . ?
C1 N1 C4 117.31(17) . . ?
C1 N1 Pb1 127.68(14) . . ?
C4 N1 Pb1 114.23(12) . . ?
C5 N2 N3 113.03(15) . . ?
C5 N2 Pb1 126.22(13) . . ?
N3 N2 Pb1 118.46(11) . . ?
C6 N3 N2 111.81(15) . . ?
C2 N4 C3 116.52(18) . . ?
C5 N5 H5A 115.3(19) . . ?
C5 N5 H5B 119.3(18) . . ?
H5A N5 H5B 118(3) . . ?
C10 N6 C9 117.12(18) . . ?
N8 N7 Pb1 120.36(15) . . ?
N9 N8 N7 177.8(2) . . ?
N1 C1 C2 121.3(2) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
N4 C2 C1 122.12(19) . . ?
N4 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
N4 C3 C4 122.1(2) . . ?
N4 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
N1 C4 C3 120.68(18) . . ?
N1 C4 C5 116.41(16) . . ?
C3 C4 C5 122.85(18) . . ?
N2 C5 N5 123.90(17) . . ?
N2 C5 C4 116.71(17) . . ?
N5 C5 C4 119.29(16) . . ?
O1 C6 N3 126.77(17) . . ?
O1 C6 C7 118.20(16) . . ?
N3 C6 C7 114.94(16) . . ?
C11 C7 C8 117.80(18) . . ?
C11 C7 C6 120.46(17) . . ?
C8 C7 C6 121.70(17) . . ?
C9 C8 C7 118.87(19) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
N6 C9 C8 123.6(2) . . ?
N6 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
N6 C10 C11 123.40(19) . . ?
N6 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C7 C11 C10 119.17(19) . . ?
C7 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 N3 C6 -168.21(17) . . . . ?
Pb1 N2 N3 C6 -4.3(2) . . . . ?
C4 N1 C1 C2 -0.1(3) . . . . ?
Pb1 N1 C1 C2 169.14(15) . . . . ?
C3 N4 C2 C1 0.0(3) . . . . ?
N1 C1 C2 N4 0.3(3) . . . . ?
C2 N4 C3 C4 -0.4(3) . . . . ?
C1 N1 C4 C3 -0.3(3) . . . . ?
Pb1 N1 C4 C3 -170.95(15) . . . . ?
C1 N1 C4 C5 177.18(18) . . . . ?
Pb1 N1 C4 C5 6.5(2) . . . . ?
N4 C3 C4 N1 0.5(3) . . . . ?
N4 C3 C4 C5 -176.76(19) . . . . ?
N3 N2 C5 N5 -0.4(3) . . . . ?
Pb1 N2 C5 N5 -162.81(15) . . . . ?
N3 N2 C5 C4 -176.54(16) . . . . ?
Pb1 N2 C5 C4 21.1(2) . . . . ?
N1 C4 C5 N2 -16.9(3) . . . . ?
C3 C4 C5 N2 160.49(18) . . . . ?
N1 C4 C5 N5 166.77(18) . . . . ?
C3 C4 C5 N5 -15.8(3) . . . . ?
Pb1 O1 C6 N3 3.4(3) . . . . ?
Pb1 O1 C6 C7 -173.08(13) . . . . ?
N2 N3 C6 O1 0.6(3) . . . . ?
N2 N3 C6 C7 177.14(16) . . . . ?
O1 C6 C7 C11 -1.6(3) . . . . ?
N3 C6 C7 C11 -178.46(18) . . . . ?
O1 C6 C7 C8 175.97(19) . . . . ?
N3 C6 C7 C8 -0.9(3) . . . . ?
C11 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C9 -176.8(2) . . . . ?
C10 N6 C9 C8 -0.5(3) . . . . ?
C7 C8 C9 N6 -0.2(4) . . . . ?
C9 N6 C10 C11 0.5(3) . . . . ?
C8 C7 C11 C10 -0.8(3) . . . . ?
C6 C7 C11 C10 176.83(19) . . . . ?
N6 C10 C11 C7 0.2(3) . . . . ?

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
N5 H5B N6 0.82(3) 2.10(3) 2.907(2) 169(2) 4_666 yes
C2 H2 N9 0.94 2.59 3.426(3) 148.1 3_857 yes
C3 H3 O1 0.94 2.46 3.168(3) 131.6 1_655 yes
C9 H9 O1 0.94 2.58 3.485(3) 161.7 4_565 yes

_refine_diff_density_max         0.703
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2339690'
loop_
_audit_author_name
_audit_author_address
'Alfonso Castineiras'
;University of Santiago de Compostela
Spain
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 N7 O3 Pb'
_chemical_formula_sum            'C11 H9 N7 O3 Pb'
_chemical_formula_weight         494.44

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1869(3)
_cell_length_b                   18.1539(7)
_cell_length_c                   10.3088(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.142(2)
_cell_angle_gamma                90
_cell_volume                     1334.56(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7986
_cell_measurement_theta_min      2.855
_cell_measurement_theta_max      28.285

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.461
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    12.668
_shelx_estimated_absorpt_T_min   0.197
_shelx_estimated_absorpt_T_max   0.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28327
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.244
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3308
_reflns_number_gt                3013
_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       'APEX4 Software (Bruker, 2022)'
_computing_cell_refinement       'APEX4 Software (Bruker, 2022)'
_computing_data_reduction        'APEX4 Software (Bruker, 2022)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND, Brandenburg,K.(1999)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0183P)²+3.4691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3308
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0473
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.96774(2) -0.03438(2) 0.72673(2) 0.01141(5) Uani 1 1 d . . . . .
O3 O 0.8050(5) -0.0216(2) 0.9627(3) 0.0420(9) Uani 1 1 d . . . . .
N1 N 0.9121(4) 0.11321(16) 0.7464(3) 0.0131(5) Uani 1 1 d . . . . .
N2 N 0.7979(4) 0.02362(14) 0.5438(3) 0.0098(5) Uani 1 1 d . . . . .
N3 N 0.7234(4) -0.01915(15) 0.4376(3) 0.0099(5) Uani 1 1 d . . . . .
N4 N 0.8943(4) 0.26620(16) 0.7158(3) 0.0151(6) Uani 1 1 d . . . . .
N5 N 0.6407(4) 0.11970(16) 0.4274(3) 0.0120(6) Uani 1 1 d . . . . .
H15A H 0.600(6) 0.095(2) 0.379(4) 0.014 Uiso 1 1 d . U . . .
H15B H 0.603(6) 0.162(2) 0.429(4) 0.014 Uiso 1 1 d . U . . .
N6 N 0.5082(4) -0.23426(16) 0.1552(3) 0.0130(6) Uani 1 1 d . . . . .
N7 N 0.6591(5) -0.04523(18) 0.9002(4) 0.0286(8) Uani 1 1 d . . . . .
O1 O 0.8424(3) -0.11915(13) 0.5635(2) 0.0134(5) Uani 1 1 d . . . . .
O2 O 0.6559(4) -0.05261(15) 0.7841(3) 0.0249(6) Uani 1 1 d . . . . .
C1 C 0.9851(5) 0.15820(19) 0.8407(3) 0.0138(6) Uani 1 1 d . . . . .
H1 H 1.044216 0.138115 0.920467 0.017 Uiso 1 1 d R U . . .
C2 C 0.9764(5) 0.23454(19) 0.8247(3) 0.0143(7) Uani 1 1 d . . . . .
H2 H 1.030947 0.265041 0.894146 0.017 Uiso 1 1 d R U . . .
C3 C 0.8179(4) 0.22045(18) 0.6227(3) 0.0124(6) Uani 1 1 d . . . . .
H3 H 0.754315 0.240763 0.544484 0.015 Uiso 1 1 d R U . . .
C4 C 0.8275(4) 0.14400(18) 0.6356(3) 0.0102(6) Uani 1 1 d . . . . .
C5 C 0.7503(4) 0.09347(17) 0.5307(3) 0.0092(6) Uani 1 1 d . . . . .
C6 C 0.7539(4) -0.08956(17) 0.4602(3) 0.0102(6) Uani 1 1 d . . . . .
C7 C 0.6710(4) -0.13935(18) 0.3527(3) 0.0109(6) Uani 1 1 d . . . . .
C8 C 0.5883(5) -0.11197(19) 0.2325(3) 0.0134(6) Uani 1 1 d . . . . .
H8 H 0.585539 -0.060477 0.215954 0.016 Uiso 1 1 d R U . . .
C9 C 0.5102(5) -0.16090(19) 0.1377(3) 0.0142(7) Uani 1 1 d . . . . .
H9 H 0.455206 -0.141580 0.056231 0.017 Uiso 1 1 d R U . . .
C10 C 0.5896(5) -0.25972(18) 0.2699(3) 0.0142(6) Uani 1 1 d . . . . .
H10 H 0.591736 -0.311493 0.283413 0.017 Uiso 1 1 d R U . . .
C11 C 0.6710(5) -0.21524(18) 0.3706(3) 0.0121(6) Uani 1 1 d . . . . .
H11 H 0.725969 -0.236303 0.450618 0.014 Uiso 1 1 d 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 N2 2.363(3) . ?
Pb1 O1 2.374(2) . ?
Pb1 O2 2.411(3) . ?
Pb1 N1 2.720(3) . ?
Pb1 O3 2.837(4) . ?
Pb1 N3 3.111(3) 3_756 ?
Pb1 N2 3.437(3) 3_756 ?
Pb1 O3 3.557(3) 3_757 ?
O3 N7 1.237(5) . ?
N1 C1 1.327(4) . ?
N1 C4 1.347(4) . ?
N2 C5 1.316(4) . ?
N2 N3 1.393(4) . ?
N3 C6 1.313(4) . ?
N4 C2 1.332(5) . ?
N4 C3 1.335(4) . ?
N5 C5 1.332(4) . ?
N5 H15A 0.71(5) . ?
N5 H15B 0.82(4) . ?
N6 C10 1.335(4) . ?
N6 C9 1.344(4) . ?
N7 O2 1.202(5) . ?
O1 C6 1.288(4) . ?
C1 C2 1.396(5) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.473(4) . ?
C6 C7 1.495(4) . ?
C7 C11 1.390(4) . ?
C7 C8 1.397(5) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?

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
N2 Pb1 O1 67.06(8) . . ?
N2 Pb1 O2 81.57(10) . . ?
O1 Pb1 O2 78.60(9) . . ?
N2 Pb1 N1 63.54(9) . . ?
O1 Pb1 N1 130.17(8) . . ?
O2 Pb1 N1 88.13(9) . . ?
N2 Pb1 O3 114.91(10) . . ?
O1 Pb1 O3 120.01(9) . . ?
O2 Pb1 O3 46.04(10) . . ?
N1 Pb1 O3 77.05(10) . . ?
N2 Pb1 N3 76.04(9) . 3_756 ?
O1 Pb1 N3 92.87(8) . 3_756 ?
O2 Pb1 N3 157.60(9) . 3_756 ?
N1 Pb1 N3 81.62(8) . 3_756 ?
O3 Pb1 N3 147.12(9) . 3_756 ?
N2 Pb1 N2 65.39(10) . 3_756 ?
O1 Pb1 N2 69.08(7) . 3_756 ?
O2 Pb1 N2 140.43(9) . 3_756 ?
N1 Pb1 N2 95.49(8) . 3_756 ?
O3 Pb1 N2 170.68(9) . 3_756 ?
N3 Pb1 N2 23.90(6) 3_756 3_756 ?
N2 Pb1 O3 136.46(9) . 3_757 ?
O1 Pb1 O3 156.17(8) . 3_757 ?
O2 Pb1 O3 98.94(9) . 3_757 ?
N1 Pb1 O3 72.94(9) . 3_757 ?
O3 Pb1 O3 52.92(12) . 3_757 ?
N3 Pb1 O3 97.00(8) 3_756 3_757 ?
N2 Pb1 O3 119.82(7) 3_756 3_757 ?
N7 O3 Pb1 86.4(3) . . ?
C1 N1 C4 117.5(3) . . ?
C1 N1 Pb1 127.8(2) . . ?
C4 N1 Pb1 113.6(2) . . ?
C5 N2 N3 112.8(3) . . ?
C5 N2 Pb1 127.8(2) . . ?
N3 N2 Pb1 119.24(19) . . ?
C6 N3 N2 111.3(3) . . ?
C2 N4 C3 115.9(3) . . ?
C5 N5 H15A 119(3) . . ?
C5 N5 H15B 119(3) . . ?
H15A N5 H15B 120(4) . . ?
C10 N6 C9 116.8(3) . . ?
O2 N7 O3 117.9(4) . . ?
C6 O1 Pb1 114.9(2) . . ?
N7 O2 Pb1 109.0(2) . . ?
N1 C1 C2 121.1(3) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
N4 C2 C1 122.4(3) . . ?
N4 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
N4 C3 C4 122.6(3) . . ?
N4 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
N1 C4 C3 120.4(3) . . ?
N1 C4 C5 117.0(3) . . ?
C3 C4 C5 122.7(3) . . ?
N2 C5 N5 123.1(3) . . ?
N2 C5 C4 117.1(3) . . ?
N5 C5 C4 119.7(3) . . ?
O1 C6 N3 127.4(3) . . ?
O1 C6 C7 118.1(3) . . ?
N3 C6 C7 114.5(3) . . ?
C11 C7 C8 117.6(3) . . ?
C11 C7 C6 120.5(3) . . ?
C8 C7 C6 121.9(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N6 C9 C8 123.4(3) . . ?
N6 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N6 C10 C11 124.0(3) . . ?
N6 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C7 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C7 C11 H11 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 N3 C6 -172.3(3) . . . . ?
Pb1 N2 N3 C6 3.1(3) . . . . ?
Pb1 O3 N7 O2 -7.2(3) . . . . ?
O3 N7 O2 Pb1 8.9(4) . . . . ?
C4 N1 C1 C2 -0.8(5) . . . . ?
Pb1 N1 C1 C2 166.2(2) . . . . ?
C3 N4 C2 C1 1.0(5) . . . . ?
N1 C1 C2 N4 0.5(5) . . . . ?
C2 N4 C3 C4 -2.0(5) . . . . ?
C1 N1 C4 C3 -0.2(5) . . . . ?
Pb1 N1 C4 C3 -169.1(2) . . . . ?
C1 N1 C4 C5 178.9(3) . . . . ?
Pb1 N1 C4 C5 10.0(4) . . . . ?
N4 C3 C4 N1 1.8(5) . . . . ?
N4 C3 C4 C5 -177.3(3) . . . . ?
N3 N2 C5 N5 0.7(5) . . . . ?
Pb1 N2 C5 N5 -174.2(2) . . . . ?
N3 N2 C5 C4 -177.8(3) . . . . ?
Pb1 N2 C5 C4 7.2(4) . . . . ?
N1 C4 C5 N2 -11.6(4) . . . . ?
C3 C4 C5 N2 167.5(3) . . . . ?
N1 C4 C5 N5 169.8(3) . . . . ?
C3 C4 C5 N5 -11.1(5) . . . . ?
Pb1 O1 C6 N3 -1.5(4) . . . . ?
Pb1 O1 C6 C7 179.9(2) . . . . ?
N2 N3 C6 O1 -1.1(5) . . . . ?
N2 N3 C6 C7 177.6(3) . . . . ?
O1 C6 C7 C11 7.4(5) . . . . ?
N3 C6 C7 C11 -171.5(3) . . . . ?
O1 C6 C7 C8 -173.8(3) . . . . ?
N3 C6 C7 C8 7.3(5) . . . . ?
C11 C7 C8 C9 0.2(5) . . . . ?
C6 C7 C8 C9 -178.6(3) . . . . ?
C10 N6 C9 C8 -1.1(5) . . . . ?
C7 C8 C9 N6 0.4(5) . . . . ?
C9 N6 C10 C11 1.2(5) . . . . ?
N6 C10 C11 C7 -0.6(5) . . . . ?
C8 C7 C11 C10 -0.2(5) . . . . ?
C6 C7 C11 C10 178.7(3) . . . . ?

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
N5 H15A O2 0.71(5) 2.45(4) 3.102(4) 153(4) 3_656 yes
N5 H15B N6 0.82(4) 2.18(4) 2.945(4) 156(4) 2_655 yes
C1 H1 O3 0.95 2.60 3.430(5) 145.9 3_757 yes
C2 H2 O1 0.95 2.31 3.115(4) 142.1 2_756 yes
C3 H3 N6 0.95 2.65 3.564(4) 160.9 2_655 yes
C10 H10 O2 0.95 2.51 3.441(4) 166.6 4 yes

_refine_diff_density_max         0.735
_refine_diff_density_min         -1.333
_refine_diff_density_rms         0.146

####################################################################### 
# 
# 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 2339689'
loop_
_audit_author_name
_audit_author_address
'Alfonso Castineiras'
;University of Santiago de Compostela
Spain
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N7 O Pb S'
_chemical_formula_sum            'C12 H9 N7 O Pb S'
_chemical_formula_weight         506.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4135(7)
_cell_length_b                   16.6666(12)
_cell_length_c                   10.1721(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.905(2)
_cell_angle_gamma                90
_cell_volume                     1418.81(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8805
_cell_measurement_theta_min      2.355
_cell_measurement_theta_max      28.285

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.371
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    12.051
_shelx_estimated_absorpt_T_min   0.486
_shelx_estimated_absorpt_T_max   0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7405
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24267
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.355
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3231
_reflns_number_gt                2807
_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       'APEX4 Software (Bruker, 2022)'
_computing_cell_refinement       'APEX4 Software (Bruker, 2022)'
_computing_data_reduction        'APEX4 Software (Bruker, 2022)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND, Brandenburg,K.(1999)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0083P)²+3.2879P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3231
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0445
_refine_ls_wR_factor_gt          0.0422
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_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 -0.11215(2) -0.03951(2) 0.71351(2) 0.01081(5) Uani 1 1 d . . . . .
S1 S 0.13839(14) 0.15850(6) 1.01596(11) 0.0225(2) Uani 1 1 d . . . . .
O1 O -0.2712(3) 0.04908(15) 0.5774(2) 0.0132(6) Uani 1 1 d . . . . .
N1 N 0.2056(4) -0.03660(19) 0.7955(3) 0.0114(6) Uani 1 1 d . . . . .
N2 N 0.0407(4) 0.05865(18) 0.6132(3) 0.0093(6) Uani 1 1 d . . . . .
N3 N -0.0403(4) 0.11616(19) 0.5304(3) 0.0113(6) Uani 1 1 d . . . . .
N4 N 0.5394(4) -0.0287(2) 0.8250(3) 0.0160(7) Uani 1 1 d . . . . .
N5 N 0.2529(4) 0.1481(2) 0.6220(4) 0.0142(7) Uani 1 1 d . . . . .
H15A H 0.192(6) 0.179(3) 0.582(4) 0.017 Uiso 1 1 d . U . . .
H15B H 0.325(6) 0.162(3) 0.656(4) 0.017 Uiso 1 1 d . U . . .
N6 N -0.4844(4) 0.2728(2) 0.2816(3) 0.0151(7) Uani 1 1 d . . . . .
N7 N -0.0935(4) 0.0630(2) 0.8763(3) 0.0159(7) Uani 1 1 d . . . . .
C1 C 0.2938(5) -0.0892(2) 0.8705(4) 0.0138(8) Uani 1 1 d . . . . .
H1 H 0.242412 -0.130701 0.914294 0.017 Uiso 1 1 d R U . . .
C2 C 0.4601(5) -0.0842(2) 0.8853(4) 0.0155(8) Uani 1 1 d . . . . .
H2 H 0.518996 -0.122041 0.940773 0.019 Uiso 1 1 d R U . . .
C3 C 0.4499(5) 0.0248(2) 0.7521(4) 0.0139(8) Uani 1 1 d . . . . .
H3 H 0.501413 0.066274 0.708561 0.017 Uiso 1 1 d R U . . .
C4 C 0.2846(5) 0.0214(2) 0.7383(3) 0.0101(8) Uani 1 1 d . . . . .
C5 C 0.1869(5) 0.0803(2) 0.6533(3) 0.0111(8) Uani 1 1 d . . . . .
C6 C -0.1964(4) 0.1044(2) 0.5199(3) 0.0096(7) Uani 1 1 d . . . . .
C7 C -0.2940(5) 0.1635(2) 0.4359(3) 0.0098(8) Uani 1 1 d . . . . .
C8 C -0.2259(5) 0.2259(2) 0.3703(4) 0.0145(8) Uani 1 1 d . . . . .
H8 H -0.113180 0.232483 0.377161 0.017 Uiso 1 1 d R U . . .
C9 C -0.3252(5) 0.2781(2) 0.2948(4) 0.0172(9) Uani 1 1 d . . . . .
H9 H -0.277354 0.320240 0.249634 0.021 Uiso 1 1 d R U . . .
C10 C -0.5485(5) 0.2128(2) 0.3456(4) 0.0154(8) Uani 1 1 d . . . . .
H10 H -0.661641 0.208062 0.337537 0.018 Uiso 1 1 d R U . . .
C11 C -0.4593(5) 0.1572(2) 0.4229(4) 0.0149(8) Uani 1 1 d . . . . .
H11 H -0.510484 0.115423 0.466133 0.018 Uiso 1 1 d R U . . .
C12 C 0.0057(5) 0.1023(2) 0.9337(4) 0.0152(8) Uani 1 1 d . . . . .


_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 2.346(3) . ?
Pb1 N7 2.374(3) . ?
Pb1 N2 2.375(3) . ?
Pb1 N1 2.717(3) . ?
Pb1 N3 3.176(3) 3_556 ?
Pb1 N4 3.255(3) 1_455 ?
Pb1 S1 3.4175(11) 3_557 ?
Pb1 N2 3.452(3) 3_556 ?
S1 C12 1.623(4) . ?
O1 C6 1.289(4) . ?
N1 C1 1.337(5) . ?
N1 C4 1.340(5) . ?
N2 C5 1.306(5) . ?
N2 N3 1.406(4) . ?
N3 C6 1.321(5) . ?
N4 C2 1.328(5) . ?
N4 C3 1.340(5) . ?
N5 C5 1.312(5) . ?
N5 H15A 0.80(5) . ?
N5 H15B 0.71(5) . ?
N6 C9 1.336(5) . ?
N6 C10 1.336(5) . ?
N7 C12 1.168(5) . ?
C1 C2 1.395(6) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.497(5) . ?
C6 C7 1.493(5) . ?
C7 C11 1.388(5) . ?
C7 C8 1.391(5) . ?
C8 C9 1.384(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?

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 N7 87.21(10) . . ?
O1 Pb1 N2 67.30(10) . . ?
N7 Pb1 N2 78.70(11) . . ?
O1 Pb1 N1 130.76(9) . . ?
N7 Pb1 N1 77.34(11) . . ?
N2 Pb1 N1 63.93(10) . . ?
O1 Pb1 N3 92.52(8) . 3_556 ?
N7 Pb1 N3 146.26(10) . 3_556 ?
N2 Pb1 N3 70.21(9) . 3_556 ?
N1 Pb1 N3 77.47(8) . 3_556 ?
O1 Pb1 N4 72.03(9) . 1_455 ?
N7 Pb1 N4 73.39(10) . 1_455 ?
N2 Pb1 N4 131.17(9) . 1_455 ?
N1 Pb1 N4 141.70(8) . 1_455 ?
N3 Pb1 N4 138.17(8) 3_556 1_455 ?
O1 Pb1 S1 139.48(7) . 3_557 ?
N7 Pb1 S1 82.01(8) . 3_557 ?
N2 Pb1 S1 145.92(8) . 3_557 ?
N1 Pb1 S1 84.62(7) . 3_557 ?
N3 Pb1 S1 117.40(6) 3_556 3_557 ?
N4 Pb1 S1 67.45(6) 1_455 3_557 ?
O1 Pb1 N2 68.61(8) . 3_556 ?
N7 Pb1 N2 137.11(9) . 3_556 ?
N2 Pb1 N2 59.64(11) . 3_556 ?
N1 Pb1 N2 91.93(8) . 3_556 ?
N3 Pb1 N2 24.02(7) 3_556 3_556 ?
N4 Pb1 N2 126.35(8) 1_455 3_556 ?
S1 Pb1 N2 138.90(5) 3_557 3_556 ?
C6 O1 Pb1 116.2(2) . . ?
C1 N1 C4 116.8(3) . . ?
C1 N1 Pb1 129.4(3) . . ?
C4 N1 Pb1 113.3(2) . . ?
C5 N2 N3 112.4(3) . . ?
C5 N2 Pb1 126.2(2) . . ?
N3 N2 Pb1 118.5(2) . . ?
C6 N3 N2 111.3(3) . . ?
C2 N4 C3 116.0(3) . . ?
C5 N5 H15A 114(3) . . ?
C5 N5 H15B 122(4) . . ?
H15A N5 H15B 120(5) . . ?
C9 N6 C10 116.9(3) . . ?
C12 N7 Pb1 138.1(3) . . ?
N1 C1 C2 121.0(4) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
N4 C2 C1 122.5(4) . . ?
N4 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
N4 C3 C4 122.1(4) . . ?
N4 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
N1 C4 C3 121.6(3) . . ?
N1 C4 C5 117.2(3) . . ?
C3 C4 C5 121.2(3) . . ?
N2 C5 N5 124.8(4) . . ?
N2 C5 C4 116.3(3) . . ?
N5 C5 C4 118.9(3) . . ?
O1 C6 N3 126.7(3) . . ?
O1 C6 C7 117.7(3) . . ?
N3 C6 C7 115.5(3) . . ?
C11 C7 C8 117.9(3) . . ?
C11 C7 C6 119.5(3) . . ?
C8 C7 C6 122.6(3) . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
N6 C9 C8 123.7(4) . . ?
N6 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
N6 C10 C11 123.7(4) . . ?
N6 C10 H10 118.1 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C7 118.9(4) . . ?
C10 C11 H11 120.5 . . ?
C7 C11 H11 120.6 . . ?
N7 C12 S1 177.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 N3 C6 -163.1(3) . . . . ?
Pb1 N2 N3 C6 -1.1(4) . . . . ?
C4 N1 C1 C2 -1.3(5) . . . . ?
Pb1 N1 C1 C2 169.8(3) . . . . ?
C3 N4 C2 C1 2.4(6) . . . . ?
N1 C1 C2 N4 -1.2(6) . . . . ?
C2 N4 C3 C4 -1.2(6) . . . . ?
C1 N1 C4 C3 2.5(5) . . . . ?
Pb1 N1 C4 C3 -170.1(3) . . . . ?
C1 N1 C4 C5 179.5(3) . . . . ?
Pb1 N1 C4 C5 7.0(4) . . . . ?
N4 C3 C4 N1 -1.2(6) . . . . ?
N4 C3 C4 C5 -178.2(3) . . . . ?
N3 N2 C5 N5 0.6(5) . . . . ?
Pb1 N2 C5 N5 -159.7(3) . . . . ?
N3 N2 C5 C4 -177.9(3) . . . . ?
Pb1 N2 C5 C4 21.8(4) . . . . ?
N1 C4 C5 N2 -17.8(5) . . . . ?
C3 C4 C5 N2 159.3(3) . . . . ?
N1 C4 C5 N5 163.6(3) . . . . ?
C3 C4 C5 N5 -19.3(5) . . . . ?
Pb1 O1 C6 N3 -0.3(5) . . . . ?
Pb1 O1 C6 C7 -178.1(2) . . . . ?
N2 N3 C6 O1 0.9(5) . . . . ?
N2 N3 C6 C7 178.8(3) . . . . ?
O1 C6 C7 C11 0.1(5) . . . . ?
N3 C6 C7 C11 -178.0(3) . . . . ?
O1 C6 C7 C8 179.5(3) . . . . ?
N3 C6 C7 C8 1.4(5) . . . . ?
C11 C7 C8 C9 -0.4(5) . . . . ?
C6 C7 C8 C9 -179.8(3) . . . . ?
C10 N6 C9 C8 -0.3(6) . . . . ?
C7 C8 C9 N6 0.6(6) . . . . ?
C9 N6 C10 C11 -0.1(6) . . . . ?
N6 C10 C11 C7 0.2(6) . . . . ?
C8 C7 C11 C10 0.0(6) . . . . ?
C6 C7 C11 C10 179.4(3) . . . . ?

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
N5 H15A S1 0.80(5) 2.82(5) 3.503(4) 145(4) 4_565 yes
N5 H15B N6 0.71(5) 2.22(5) 2.919(5) 167(5) 4_666 yes
C2 H2 S1 0.95 2.93 3.640(4) 132.1 3_657 yes
C3 H3 O1 0.95 2.46 3.113(5) 125.9 1_655 yes
C8 H8 S1 0.95 3.03 3.791(4) 138.5 4_565 yes

_refine_diff_density_max         0.762
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.145

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2339691'
loop_
_audit_author_name
_audit_author_address
'Alfonso Castineiras'
;University of Santiago de Compostela
Spain
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 N7 O4 Pb'
_chemical_formula_sum            'C11 H9 N7 O4 Pb'
_chemical_formula_weight         510.44

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1282(3)
_cell_length_b                   16.9244(6)
_cell_length_c                   12.1283(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.3430(10)
_cell_angle_gamma                90
_cell_volume                     1417.56(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    8032
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      29.77

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.392
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    11.936
_shelx_estimated_absorpt_T_min   0.236
_shelx_estimated_absorpt_T_max   0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27636
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.407
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2895
_reflns_number_gt                2500
_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       'APEX4 Software (Bruker, 2022)'
_computing_cell_refinement       'APEX4 Software (Bruker, 2022)'
_computing_data_reduction        'APEX4 Software (Bruker, 2022)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND, Brandenburg,K.(1999)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0300P)²+7.7050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2895
_refine_ls_number_parameters     214
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_restrained_S_all      1.239
_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 1.00564(4) 0.06221(2) 0.18386(2) 0.02918(11) Uani 1 1 d . . . . .
O1 O 0.8290(8) 0.1291(3) 0.0227(4) 0.0319(12) Uani 1 1 d . . . . .
N1 N 0.9673(10) -0.0943(4) 0.2448(5) 0.0288(14) Uani 1 1 d . . . . .
N2 N 0.8097(9) -0.0239(3) 0.0469(5) 0.0264(13) Uani 1 1 d . . . . .
N3 N 0.7116(9) 0.0092(3) -0.0578(5) 0.0285(14) Uani 1 1 d . . . . .
N4 N 0.9685(11) -0.2575(4) 0.2668(6) 0.0411(17) Uani 1 1 d . . . . .
N5 N 0.6579(11) -0.1385(4) -0.0316(6) 0.0333(16) Uani 1 1 d . . . . .
H5A H 0.602(13) -0.110(5) -0.086(8) 0.040 Uiso 1 1 d . U . . .
H5B H 0.642(13) -0.184(6) -0.032(7) 0.040 Uiso 1 1 d . U . . .
N6 N 0.4371(11) 0.2033(4) -0.3671(6) 0.0415(17) Uani 1 1 d . . . . .
N7 N 0.7482(12) 0.0840(4) 0.3426(6) 0.0419(16) Uani 1 1 d . U . . .
O2 O 0.7047(9) 0.0778(3) 0.2351(5) 0.0447(15) Uani 1 1 d . . . . .
O3 O 0.9188(14) 0.0813(6) 0.3958(7) 0.090(3) Uani 1 1 d . U . . .
O4 O 0.6171(14) 0.0949(5) 0.3929(7) 0.076(2) Uani 1 1 d . . . . .
C1 C 1.0540(12) -0.1295(5) 0.3413(7) 0.0352(18) Uani 1 1 d . . . . .
H1 H 1.118327 -0.098819 0.403872 0.042 Uiso 1 1 d R U . . .
C2 C 1.0505(13) -0.2102(5) 0.3521(7) 0.041(2) Uani 1 1 d . . . . .
H2 H 1.109323 -0.232955 0.422960 0.049 Uiso 1 1 d R U . . .
C3 C 0.8818(13) -0.2228(4) 0.1687(7) 0.0357(19) Uani 1 1 d . . . . .
H3 H 0.822426 -0.254008 0.105571 0.043 Uiso 1 1 d R U . . .
C4 C 0.8776(11) -0.1404(4) 0.1584(6) 0.0273(16) Uani 1 1 d . . . . .
C5 C 0.7765(11) -0.0991(4) 0.0530(6) 0.0266(15) Uani 1 1 d . . . . .
C6 C 0.7299(10) 0.0858(4) -0.0588(6) 0.0247(15) Uani 1 1 d . . . . .
C7 C 0.6278(11) 0.1259(4) -0.1654(6) 0.0264(15) Uani 1 1 d . . . . .
C8 C 0.5383(12) 0.0840(4) -0.2630(7) 0.0341(18) Uani 1 1 d . . . . .
H8 H 0.539617 0.028467 -0.262863 0.041 Uiso 1 1 d R U . . .
C9 C 0.4480(12) 0.1254(5) -0.3605(7) 0.0345(18) Uani 1 1 d . . . . .
H9 H 0.390732 0.096155 -0.426123 0.041 Uiso 1 1 d R U . . .
C10 C 0.5192(16) 0.2427(5) -0.2715(8) 0.055(3) Uani 1 1 d . . . . .
H10 H 0.512162 0.298117 -0.273556 0.066 Uiso 1 1 d R U . . .
C11 C 0.6129(14) 0.2075(5) -0.1707(7) 0.041(2) Uani 1 1 d . . . . .
H11 H 0.666124 0.238382 -0.106111 0.050 Uiso 1 1 d 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 O1 2.338(5) . ?
Pb1 N2 2.384(6) . ?
Pb1 O2 2.391(6) . ?
Pb1 N1 2.782(6) . ?
Pb1 O3 2.808(9) . ?
Pb1 N3 3.064(6) 3_755 ?
Pb1 N4 3.106(6) 2_755 ?
Pb1 N2 3.437(6) 3_755 ?
Pb1 Pb1 4.9145(5) 3_755 ?
O1 C6 1.291(8) . ?
N1 C1 1.323(9) . ?
N1 C4 1.335(9) . ?
N2 C5 1.300(9) . ?
N2 N3 1.405(8) . ?
N3 C6 1.304(9) . ?
N4 C2 1.324(11) . ?
N4 C3 1.333(10) . ?
N5 C5 1.336(9) . ?
N5 H5A 0.84(9) . ?
N5 H5B 0.78(9) . ?
N6 C9 1.322(10) . ?
N6 C10 1.339(11) . ?
N7 O3 1.228(11) . ?
N7 O4 1.250(10) . ?
N7 O2 1.268(9) . ?
C1 C2 1.373(11) . ?
C1 H1 0.9400 . ?
C2 H2 0.9400 . ?
C3 C4 1.399(10) . ?
C3 H3 0.9400 . ?
C4 C5 1.479(9) . ?
C6 C7 1.481(9) . ?
C7 C11 1.386(10) . ?
C7 C8 1.391(10) . ?
C8 C9 1.388(11) . ?
C8 H8 0.9400 . ?
C9 H9 0.9400 . ?
C10 C11 1.375(11) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?

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 N2 67.19(18) . . ?
O1 Pb1 O2 80.3(2) . . ?
N2 Pb1 O2 80.8(2) . . ?
O1 Pb1 N1 127.95(17) . . ?
N2 Pb1 N1 61.57(18) . . ?
O2 Pb1 N1 83.26(19) . . ?
O1 Pb1 O3 121.0(2) . . ?
N2 Pb1 O3 118.9(3) . . ?
O2 Pb1 O3 48.2(2) . . ?
N1 Pb1 O3 78.9(2) . . ?
O1 Pb1 N3 93.36(17) . 3_755 ?
N2 Pb1 N3 75.85(19) . 3_755 ?
O2 Pb1 N3 156.43(19) . 3_755 ?
N1 Pb1 N3 82.93(17) . 3_755 ?
O3 Pb1 N3 145.5(2) . 3_755 ?
O1 Pb1 N4 71.30(17) . 2_755 ?
N2 Pb1 N4 136.98(19) . 2_755 ?
O2 Pb1 N4 81.7(2) . 2_755 ?
N1 Pb1 N4 152.79(19) . 2_755 ?
O3 Pb1 N4 74.1(3) . 2_755 ?
N3 Pb1 N4 117.96(18) 3_755 2_755 ?
O1 Pb1 N2 69.29(17) . 3_755 ?
N2 Pb1 N2 66.0(2) . 3_755 ?
O2 Pb1 N2 141.41(19) . 3_755 ?
N1 Pb1 N2 96.84(16) . 3_755 ?
O3 Pb1 N2 169.4(2) . 3_755 ?
N3 Pb1 N2 24.10(14) 3_755 3_755 ?
N4 Pb1 N2 109.03(17) 2_755 3_755 ?
O1 Pb1 Pb1 64.19(12) . 3_755 ?
N2 Pb1 Pb1 39.72(15) . 3_755 ?
O2 Pb1 Pb1 117.97(15) . 3_755 ?
N1 Pb1 Pb1 81.51(12) . 3_755 ?
O3 Pb1 Pb1 157.3(2) . 3_755 ?
N3 Pb1 Pb1 40.80(11) 3_755 3_755 ?
N4 Pb1 Pb1 125.64(13) 2_755 3_755 ?
N2 Pb1 Pb1 26.31(10) 3_755 3_755 ?
C6 O1 Pb1 116.4(4) . . ?
C1 N1 C4 117.3(6) . . ?
C1 N1 Pb1 127.5(5) . . ?
C4 N1 Pb1 114.1(4) . . ?
C5 N2 N3 112.6(6) . . ?
C5 N2 Pb1 129.9(5) . . ?
N3 N2 Pb1 117.4(4) . . ?
C6 N3 N2 112.1(5) . . ?
C2 N4 C3 116.7(7) . . ?
C5 N5 H5A 114(6) . . ?
C5 N5 H5B 125(7) . . ?
H5A N5 H5B 122(9) . . ?
C9 N6 C10 115.9(7) . . ?
O3 N7 O4 120.8(8) . . ?
O3 N7 O2 119.7(8) . . ?
O4 N7 O2 119.5(8) . . ?
N7 O2 Pb1 105.6(5) . . ?
N7 O3 Pb1 86.4(5) . . ?
N1 C1 C2 121.1(8) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.3 . . ?
N4 C2 C1 122.8(8) . . ?
N4 C2 H2 118.5 . . ?
C1 C2 H2 118.7 . . ?
N4 C3 C4 120.9(7) . . ?
N4 C3 H3 119.6 . . ?
C4 C3 H3 119.5 . . ?
N1 C4 C3 121.2(7) . . ?
N1 C4 C5 116.0(6) . . ?
C3 C4 C5 122.9(7) . . ?
N2 C5 N5 122.3(6) . . ?
N2 C5 C4 117.1(6) . . ?
N5 C5 C4 120.5(6) . . ?
O1 C6 N3 126.4(6) . . ?
O1 C6 C7 117.8(6) . . ?
N3 C6 C7 115.7(6) . . ?
C11 C7 C8 117.0(7) . . ?
C11 C7 C6 120.8(7) . . ?
C8 C7 C6 122.2(6) . . ?
C7 C8 C9 119.1(7) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.5 . . ?
N6 C9 C8 124.2(7) . . ?
N6 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
N6 C10 C11 124.5(8) . . ?
N6 C10 H10 117.7 . . ?
C11 C10 H10 117.8 . . ?
C10 C11 C7 119.2(8) . . ?
C10 C11 H11 120.5 . . ?
C7 C11 H11 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 N3 C6 173.5(7) . . . . ?
Pb1 N2 N3 C6 -6.3(8) . . . . ?
O3 N7 O2 Pb1 0.0(10) . . . . ?
O4 N7 O2 Pb1 178.2(6) . . . . ?
O4 N7 O3 Pb1 -178.2(8) . . . . ?
O2 N7 O3 Pb1 0.0(8) . . . . ?
C4 N1 C1 C2 -0.4(12) . . . . ?
Pb1 N1 C1 C2 -167.6(6) . . . . ?
C3 N4 C2 C1 -2.2(14) . . . . ?
N1 C1 C2 N4 2.9(15) . . . . ?
C2 N4 C3 C4 -0.6(13) . . . . ?
C1 N1 C4 C3 -2.4(12) . . . . ?
Pb1 N1 C4 C3 166.6(6) . . . . ?
C1 N1 C4 C5 178.0(7) . . . . ?
Pb1 N1 C4 C5 -13.1(8) . . . . ?
N4 C3 C4 N1 3.0(13) . . . . ?
N4 C3 C4 C5 -177.4(8) . . . . ?
N3 N2 C5 N5 -1.4(11) . . . . ?
Pb1 N2 C5 N5 178.4(6) . . . . ?
N3 N2 C5 C4 178.2(6) . . . . ?
Pb1 N2 C5 C4 -2.0(10) . . . . ?
N1 C4 C5 N2 11.0(11) . . . . ?
C3 C4 C5 N2 -168.7(8) . . . . ?
N1 C4 C5 N5 -169.4(7) . . . . ?
C3 C4 C5 N5 10.9(12) . . . . ?
Pb1 O1 C6 N3 3.5(10) . . . . ?
Pb1 O1 C6 C7 -175.7(5) . . . . ?
N2 N3 C6 O1 1.9(11) . . . . ?
N2 N3 C6 C7 -178.9(6) . . . . ?
O1 C6 C7 C11 -10.3(12) . . . . ?
N3 C6 C7 C11 170.4(8) . . . . ?
O1 C6 C7 C8 171.5(7) . . . . ?
N3 C6 C7 C8 -7.8(11) . . . . ?
C11 C7 C8 C9 2.9(12) . . . . ?
C6 C7 C8 C9 -178.9(8) . . . . ?
C10 N6 C9 C8 -0.4(14) . . . . ?
C7 C8 C9 N6 -1.4(14) . . . . ?
C9 N6 C10 C11 0.7(16) . . . . ?
N6 C10 C11 C7 0.8(17) . . . . ?
C8 C7 C11 C10 -2.6(13) . . . . ?
C6 C7 C11 C10 179.1(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
N5 H5A O2 0.84(9) 2.52(9) 3.265(9) 148(8) 3_655 yes
N5 H5B N6 0.78(9) 2.26(9) 2.953(9) 149(8) 2_644 yes
C1 H1 O3 0.94 2.53 3.250(12) 134.0 3_756 yes
C2 H2 O1 0.94 2.44 3.129(9) 130.5 2_745 yes
C8 H8 O2 0.94 2.58 3.302(10) 133.6 3_655 yes
C10 H10 N5 0.94 2.60 3.138(10) 116.4 2_654 yes
C10 H10 O2 0.94 2.50 3.307(11) 144.4 4_565 yes

_refine_diff_density_max         2.266
_refine_diff_density_min         -1.212
_refine_diff_density_rms         0.178

