# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2348187'
loop_
_audit_author_name
_audit_author_address
'Damir Safin'
;Tyumen State University
Russia
;
_audit_update_record             
;
2024-04-14 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N12 O5 Pb2, 2(C2 H3 N), 2(C H4 O)'
_chemical_formula_sum            'C29 H32 N14 O7 Pb2'
_chemical_formula_weight         1103.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   26.8255(16)
_cell_length_b                   9.3424(6)
_cell_length_c                   13.8939(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.608(2)
_cell_angle_gamma                90
_cell_volume                     3475.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9744
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.54

_exptl_crystal_description       plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    9.744
_shelx_estimated_absorpt_T_min   0.246
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6452
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_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            101368
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.309
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5310
_reflns_number_gt                4975
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0143P)²+6.7731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5310
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0164
_refine_ls_R_factor_gt           0.0143
_refine_ls_wR_factor_ref         0.0353
_refine_ls_wR_factor_gt          0.0344
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 -0.02468(2) 0.84198(2) 0.40851(2) 0.01430(2) Uani 1 1 d . . . . .
O11 O 0.000000 0.88701(19) 0.250000 0.0155(3) Uani 1 2 d S T P . .
O12 O -0.01113(6) 1.09170(14) 0.32701(10) 0.0221(3) Uani 1 1 d . . . . .
O17 O 0.05984(5) 0.84893(13) 0.45669(10) 0.0174(3) Uani 1 1 d . . . . .
N11 N -0.07937(6) 0.63466(16) 0.31883(12) 0.0158(3) Uani 1 1 d . . . . .
N12 N 0.01470(6) 0.61688(16) 0.39205(11) 0.0133(3) Uani 1 1 d . . . . .
N13 N 0.06374(6) 0.60232(16) 0.42911(11) 0.0148(3) Uani 1 1 d . . . . .
N14 N 0.22781(6) 0.70361(19) 0.60529(12) 0.0199(3) Uani 1 1 d . . . . .
N15 N -0.13344(6) 0.39271(18) 0.25651(11) 0.0178(3) Uani 1 1 d . . . . .
N16 N 0.01599(6) 0.36818(15) 0.37989(11) 0.0149(3) Uani 1 1 d . . . . .
H16A H 0.046812 0.369820 0.404014 0.018 Uiso 1 1 d R U . . .
H16B H 0.002112 0.284720 0.358214 0.018 Uiso 1 1 d R U . . .
C10 C 0.000000 1.0296(3) 0.250000 0.0162(5) Uani 1 2 d S T P . .
C11 C -0.12604(7) 0.6450(2) 0.28082(14) 0.0186(3) Uani 1 1 d . . . . .
H11 H -0.141403 0.736497 0.275185 0.022 Uiso 1 1 calc R U . . .
C12 C -0.15283(7) 0.5240(2) 0.24910(13) 0.0186(3) Uani 1 1 d . . . . .
H12 H -0.185879 0.535556 0.221403 0.022 Uiso 1 1 calc R U . . .
C14 C -0.08690(7) 0.38289(19) 0.29622(13) 0.0155(3) Uani 1 1 d . . . . .
H14 H -0.072082 0.290928 0.304051 0.019 Uiso 1 1 calc R U . . .
C15 C -0.05925(7) 0.50325(17) 0.32665(12) 0.0128(3) Uani 1 1 d . . . . .
C16 C -0.00724(6) 0.49487(17) 0.36817(12) 0.0122(3) Uani 1 1 d . . . . .
C17 C 0.08223(7) 0.72586(19) 0.45930(12) 0.0144(3) Uani 1 1 d . . . . .
C18 C 0.13411(7) 0.71983(19) 0.50418(12) 0.0152(3) Uani 1 1 d . . . . .
C19 C 0.16272(7) 0.5948(2) 0.50270(13) 0.0173(3) Uani 1 1 d . . . . .
H19 H 0.150726 0.513083 0.467788 0.021 Uiso 1 1 calc R U . . .
C110 C 0.20887(7) 0.5927(2) 0.55315(14) 0.0194(3) Uani 1 1 d . . . . .
H110 H 0.228325 0.507917 0.550834 0.023 Uiso 1 1 calc R U . . .
C112 C 0.20054(8) 0.8238(2) 0.60416(14) 0.0202(4) Uani 1 1 d . . . . .
H112 H 0.213586 0.904230 0.639233 0.024 Uiso 1 1 calc R U . . .
C113 C 0.15418(8) 0.83718(19) 0.55438(14) 0.0178(3) Uani 1 1 d . . . . .
H113 H 0.136481 0.925229 0.554682 0.021 Uiso 1 1 calc R U . . .
O2 O 0.27952(6) 0.36945(16) 0.27828(11) 0.0241(3) Uani 1 1 d . . . . .
H2 H 0.267128 0.343377 0.226218 0.036 Uiso 1 1 d R U . . .
C3 C 0.25702(9) 0.2907(3) 0.35140(16) 0.0279(4) Uani 1 1 d . . . . .
H3A H 0.279482 0.289128 0.409818 0.042 Uiso 1 1 calc R U . . .
H3B H 0.250661 0.192410 0.329158 0.042 Uiso 1 1 calc R U . . .
H3C H 0.225391 0.336031 0.365711 0.042 Uiso 1 1 calc R U . . .
N1 N 0.12381(8) 0.2269(2) 0.46812(15) 0.0323(4) Uani 1 1 d . . . . .
C1 C 0.12799(8) 0.1477(2) 0.40663(16) 0.0236(4) Uani 1 1 d . . . . .
C2 C 0.13252(9) 0.0468(2) 0.32789(16) 0.0273(4) Uani 1 1 d . . . . .
H2A H 0.103665 -0.017777 0.324350 0.041 Uiso 1 1 calc R U . . .
H2B H 0.163231 -0.009171 0.339274 0.041 Uiso 1 1 calc R U . . .
H2C H 0.133718 0.099265 0.267012 0.041 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 O17 2.3241(14) . y
Pb1 N12 2.3708(15) . y
Pb1 O11 2.3767(3) . y
Pb1 O12 2.6285(14) . y
Pb1 N11 2.6881(16) . y
Pb1 N1 3.316(2) 5_566 y
O11 C10 1.332(3) . ?
O12 C10 1.2691(18) . ?
O17 C17 1.297(2) . ?
N11 C11 1.331(2) . ?
N11 C15 1.343(2) . ?
N12 C16 1.316(2) . ?
N12 N13 1.389(2) . ?
N13 C17 1.314(2) . ?
N14 C112 1.340(3) . ?
N14 C110 1.346(3) . ?
N15 C12 1.334(3) . ?
N15 C14 1.336(2) . ?
N16 C16 1.343(2) . ?
N16 H16A 0.8725 . ?
N16 H16B 0.9073 . ?
C11 C12 1.396(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.398(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.478(2) . ?
C17 C18 1.490(2) . ?
C18 C113 1.390(2) . ?
C18 C19 1.398(3) . ?
C19 C110 1.384(3) . ?
C19 H19 0.9500 . ?
C110 H110 0.9500 . ?
C112 C113 1.390(3) . ?
C112 H112 0.9500 . ?
C113 H113 0.9500 . ?
O2 C3 1.420(3) . ?
O2 H2 0.8141 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N1 C1 1.141(3) . ?
C1 C2 1.455(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?

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
O17 Pb1 N12 67.67(5) . . y
O17 Pb1 O11 86.47(4) . . y
N12 Pb1 O11 85.17(5) . . y
O17 Pb1 O12 86.59(5) . . y
N12 Pb1 O12 132.16(5) . . y
O11 Pb1 O12 52.38(5) . . y
O17 Pb1 N11 130.37(4) . . y
N12 Pb1 N11 63.24(5) . . y
O11 Pb1 N11 82.75(5) . . y
O12 Pb1 N11 121.74(5) . . y
O17 Pb1 N1 130.99(5) . 5_566 y
N12 Pb1 N1 104.73(5) . 5_566 y
O11 Pb1 N1 142.41(4) . 5_566 y
O12 Pb1 N1 122.14(5) . 5_566 y
N11 Pb1 N1 70.59(5) . 5_566 y
C10 O11 Pb1 100.20(4) . 2 ?
C10 O11 Pb1 100.20(4) . . ?
Pb1 O11 Pb1 159.61(8) 2 . ?
C10 O12 Pb1 90.22(12) . . ?
C17 O17 Pb1 115.15(11) . . ?
C11 N11 C15 117.50(16) . . ?
C11 N11 Pb1 127.14(12) . . ?
C15 N11 Pb1 114.61(12) . . ?
C16 N12 N13 114.01(15) . . ?
C16 N12 Pb1 126.70(12) . . ?
N13 N12 Pb1 117.94(10) . . ?
C17 N13 N12 111.22(15) . . ?
C112 N14 C110 116.87(17) . . ?
C12 N15 C14 116.41(16) . . ?
C16 N16 H16A 116.9 . . ?
C16 N16 H16B 122.7 . . ?
H16A N16 H16B 120.1 . . ?
O12 C10 O12 125.6(2) . 2 ?
O12 C10 O11 117.19(12) . . ?
O12 C10 O11 117.19(12) 2 . ?
N11 C11 C12 121.28(17) . . ?
N11 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N15 C12 C11 121.99(17) . . ?
N15 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
N15 C14 C15 122.28(17) . . ?
N15 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
N11 C15 C14 120.54(16) . . ?
N11 C15 C16 116.41(15) . . ?
C14 C15 C16 123.05(15) . . ?
N12 C16 N16 122.42(16) . . ?
N12 C16 C15 116.68(15) . . ?
N16 C16 C15 120.91(15) . . ?
O17 C17 N13 127.22(17) . . ?
O17 C17 C18 117.65(15) . . ?
N13 C17 C18 115.10(16) . . ?
C113 C18 C19 118.06(17) . . ?
C113 C18 C17 120.17(17) . . ?
C19 C18 C17 121.64(16) . . ?
C110 C19 C18 118.63(17) . . ?
C110 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
N14 C110 C19 123.84(18) . . ?
N14 C110 H110 118.1 . . ?
C19 C110 H110 118.1 . . ?
N14 C112 C113 123.48(17) . . ?
N14 C112 H112 118.3 . . ?
C113 C112 H112 118.3 . . ?
C18 C113 C112 119.04(18) . . ?
C18 C113 H113 120.5 . . ?
C112 C113 H113 120.5 . . ?
C3 O2 H2 108.2 . . ?
O2 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C1 C2 179.2(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

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
C16 N12 N13 C17 -174.53(15) . . . . ?
Pb1 N12 N13 C17 -6.86(18) . . . . ?
Pb1 O12 C10 O12 179.02(7) . . . 2 ?
Pb1 O12 C10 O11 -0.98(7) . . . . ?
Pb1 O11 C10 O12 -178.90(8) 2 . . . ?
Pb1 O11 C10 O12 1.10(8) . . . . ?
Pb1 O11 C10 O12 1.10(8) 2 . . 2 ?
Pb1 O11 C10 O12 -178.90(8) . . . 2 ?
C15 N11 C11 C12 -0.8(3) . . . . ?
Pb1 N11 C11 C12 -170.24(13) . . . . ?
C14 N15 C12 C11 0.2(3) . . . . ?
N11 C11 C12 N15 1.0(3) . . . . ?
C12 N15 C14 C15 -1.4(3) . . . . ?
C11 N11 C15 C14 -0.4(3) . . . . ?
Pb1 N11 C15 C14 170.34(13) . . . . ?
C11 N11 C15 C16 179.42(16) . . . . ?
Pb1 N11 C15 C16 -9.86(18) . . . . ?
N15 C14 C15 N11 1.6(3) . . . . ?
N15 C14 C15 C16 -178.21(16) . . . . ?
N13 N12 C16 N16 0.6(2) . . . . ?
Pb1 N12 C16 N16 -165.75(12) . . . . ?
N13 N12 C16 C15 -178.96(14) . . . . ?
Pb1 N12 C16 C15 14.7(2) . . . . ?
N11 C15 C16 N12 -1.1(2) . . . . ?
C14 C15 C16 N12 178.70(16) . . . . ?
N11 C15 C16 N16 179.30(16) . . . . ?
C14 C15 C16 N16 -0.9(3) . . . . ?
Pb1 O17 C17 N13 7.2(2) . . . . ?
Pb1 O17 C17 C18 -170.54(11) . . . . ?
N12 N13 C17 O17 -0.2(2) . . . . ?
N12 N13 C17 C18 177.54(14) . . . . ?
O17 C17 C18 C113 9.9(2) . . . . ?
N13 C17 C18 C113 -168.15(16) . . . . ?
O17 C17 C18 C19 -174.30(16) . . . . ?
N13 C17 C18 C19 7.7(2) . . . . ?
C113 C18 C19 C110 1.7(3) . . . . ?
C17 C18 C19 C110 -174.25(16) . . . . ?
C112 N14 C110 C19 -2.7(3) . . . . ?
C18 C19 C110 N14 1.1(3) . . . . ?
C110 N14 C112 C113 1.5(3) . . . . ?
C19 C18 C113 C112 -2.7(3) . . . . ?
C17 C18 C113 C112 173.25(17) . . . . ?
N14 C112 C113 C18 1.2(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
N16 H16A N1 0.87 2.57 3.341(3) 147.7 . yes
N16 H16B O12 0.91 1.88 2.7701(19) 165.2 1_545 yes
C11 H11 O2 0.95 2.46 3.287(2) 145.4 3_455 yes
C14 H14 O12 0.95 2.48 3.407(2) 163.6 1_545 yes
C112 H112 O2 0.95 2.41 3.325(2) 162.5 7_566 yes
O2 H2 N14 0.81 1.98 2.783(2) 171.2 6_565 yes
C2 H2A O17 0.98 2.57 3.295(3) 131.2 1_545 yes
C2 H2B O2 0.98 2.57 3.305(3) 131.4 4_545 yes

_refine_diff_density_max         0.674
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.088

