# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1535557'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-03-09 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            'C12 H10 N6 O7 Pb'
_chemical_formula_weight         557.45

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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9846(2)
_cell_length_b                   17.4996(4)
_cell_length_c                   11.4514(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.0640(10)
_cell_angle_gamma                90
_cell_volume                     1597.79(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.31

_exptl_crystal_description       lozenge
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.317
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.601
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.298
_exptl_absorpt_coefficient_mu    10.612
_shelx_estimated_absorpt_T_min   0.061
_shelx_estimated_absorpt_T_max   0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3396
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22011
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.128
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3986
_reflns_number_gt                3502
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'


_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)+(0.0348P)²+1.4119P] 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         3986
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.36507(2) 0.53155(2) 0.18128(2) 0.01650(6) Uani 1 1 d . . . . .
C1 C 0.5806(6) 0.7764(2) 0.4238(4) 0.0277(9) Uani 1 1 d . . . . .
H1 H 0.4934 0.7822 0.3646 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6481(6) 0.8396(2) 0.4808(4) 0.0297(10) Uani 1 1 d . . . . .
H2 H 0.6061 0.8887 0.4591 0.036 Uiso 1 1 calc R U . . .
N3 N 0.7700(5) 0.83499(19) 0.5651(3) 0.0255(8) Uani 1 1 d . . . . .
C4 C 0.8278(6) 0.7656(2) 0.5934(4) 0.0270(9) Uani 1 1 d . . . . .
H4 H 0.9154 0.7616 0.6526 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7673(5) 0.6991(2) 0.5412(3) 0.0224(8) Uani 1 1 d . . . . .
H5 H 0.8112 0.6507 0.5650 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6414(5) 0.7046(2) 0.4537(3) 0.0182(8) Uani 1 1 d . . . . .
C7 C 0.5668(5) 0.6376(2) 0.3900(3) 0.0179(8) Uani 1 1 d . . . . .
O8 O 0.4354(4) 0.64236(15) 0.3296(3) 0.0251(6) Uani 1 1 d . . . . .
N9 N 0.6516(5) 0.57168(19) 0.4039(4) 0.0290(9) Uani 1 1 d . . . . .
N10 N 0.5860(5) 0.50837(19) 0.3458(3) 0.0214(7) Uani 1 1 d . . . . .
C11 C 0.6607(6) 0.4449(3) 0.3659(4) 0.0326(11) Uani 1 1 d . . . . .
H11 H 0.7580 0.4424 0.4173 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5935(6) 0.3760(2) 0.3082(4) 0.0235(9) Uani 1 1 d . . . . .
N13 N 0.4654(5) 0.38471(17) 0.2285(3) 0.0206(7) Uani 1 1 d . . . . .
C14 C 0.4048(6) 0.3228(2) 0.1751(4) 0.0271(9) Uani 1 1 d . . . . .
H14 H 0.3163 0.3284 0.1169 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4653(7) 0.2498(2) 0.2006(4) 0.0330(11) Uani 1 1 d . . . . .
H15 H 0.4173 0.2065 0.1615 0.040 Uiso 1 1 calc R U . . .
C16 C 0.5940(7) 0.2411(2) 0.2822(4) 0.0334(11) Uani 1 1 d . . . . .
H16 H 0.6367 0.1917 0.3011 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6618(6) 0.3050(3) 0.3372(4) 0.0323(10) Uani 1 1 d . . . . .
H17 H 0.7529 0.3006 0.3936 0.039 Uiso 1 1 calc R U . . .
N18 N 0.0794(5) 0.5416(2) 0.3587(4) 0.0330(9) Uani 1 1 d . . . . .
O19 O 0.0222(6) 0.5524(3) 0.2587(4) 0.0643(13) Uani 1 1 d . . . . .
O20 O 0.2081(4) 0.5004(2) 0.3741(3) 0.0379(8) Uani 1 1 d . . . . .
O21 O 0.0159(5) 0.5750(2) 0.4435(3) 0.0415(8) Uani 1 1 d . . . . .
N22 N 0.7016(5) 0.5561(2) 0.0664(3) 0.0239(7) Uani 1 1 d . . . . .
O23 O 0.8113(4) 0.5695(2) -0.0010(3) 0.0403(8) Uani 1 1 d . . . . .
O24 O 0.6448(4) 0.49007(19) 0.0759(3) 0.0346(8) Uani 1 1 d . . . . .
O25 O 0.6376(4) 0.60850(17) 0.1244(3) 0.0324(7) Uani 1 1 d . . . . .
H9 H 0.752(7) 0.572(3) 0.430(5) 0.036(15) Uiso 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 N10 2.544(3) . ?
Pb1 O8 2.619(3) . ?
Pb1 O20 2.653(3) . ?
Pb1 O25 2.669(3) . ?
Pb1 O24 2.694(3) . ?
Pb1 N13 2.737(3) . ?
Pb1 N3 2.774(3) 4_575 ?
C1 C2 1.379(6) . ?
C1 C6 1.384(6) . ?
C1 H1 0.9500 . ?
C2 N3 1.336(6) . ?
C2 H2 0.9500 . ?
N3 C4 1.333(5) . ?
N3 Pb1 2.774(3) 4_676 ?
C4 C5 1.383(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.489(5) . ?
C7 O8 1.229(5) . ?
C7 N9 1.342(5) . ?
N9 N10 1.381(5) . ?
N9 H9 0.84(6) . ?
N10 C11 1.276(6) . ?
C11 C12 1.464(6) . ?
C11 H11 0.9500 . ?
C12 N13 1.342(5) . ?
C12 C17 1.389(6) . ?
N13 C14 1.324(5) . ?
C14 C15 1.391(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.360(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N18 O19 1.225(6) . ?
N18 O20 1.259(5) . ?
N18 O21 1.263(5) . ?
N22 O23 1.220(5) . ?
N22 O24 1.248(5) . ?
N22 O25 1.257(5) . ?

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
N10 Pb1 O8 61.42(9) . . ?
N10 Pb1 O20 71.98(12) . . ?
O8 Pb1 O20 72.95(12) . . ?
N10 Pb1 O25 73.68(11) . . ?
O8 Pb1 O25 68.60(9) . . ?
O20 Pb1 O25 137.23(11) . . ?
N10 Pb1 O24 74.33(12) . . ?
O8 Pb1 O24 109.61(10) . . ?
O20 Pb1 O24 139.22(10) . . ?
O25 Pb1 O24 47.20(9) . . ?
N10 Pb1 N13 61.31(10) . . ?
O8 Pb1 N13 121.12(9) . . ?
O20 Pb1 N13 77.83(11) . . ?
O25 Pb1 N13 106.75(10) . . ?
O24 Pb1 N13 66.09(10) . . ?
N10 Pb1 N3 130.60(11) . 4_575 ?
O8 Pb1 N3 74.41(10) . 4_575 ?
O20 Pb1 N3 116.27(11) . 4_575 ?
O25 Pb1 N3 70.37(10) . 4_575 ?
O24 Pb1 N3 102.97(11) . 4_575 ?
N13 Pb1 N3 162.76(10) . 4_575 ?
C2 C1 C6 119.2(4) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
N3 C2 C1 123.0(4) . . ?
N3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C4 N3 C2 117.4(4) . . ?
C4 N3 Pb1 124.6(3) . 4_676 ?
C2 N3 Pb1 117.8(3) . 4_676 ?
N3 C4 C5 123.6(4) . . ?
N3 C4 H4 118.2 . . ?
C5 C4 H4 118.2 . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 118.3(4) . . ?
C1 C6 C7 117.9(4) . . ?
C5 C6 C7 123.8(3) . . ?
O8 C7 N9 122.4(4) . . ?
O8 C7 C6 122.0(3) . . ?
N9 C7 C6 115.6(3) . . ?
C7 O8 Pb1 117.5(2) . . ?
C7 N9 N10 117.1(4) . . ?
C7 N9 H9 121(4) . . ?
N10 N9 H9 120(4) . . ?
C11 N10 N9 116.7(4) . . ?
C11 N10 Pb1 124.9(3) . . ?
N9 N10 Pb1 117.3(3) . . ?
N10 C11 C12 118.6(4) . . ?
N10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
N13 C12 C17 122.6(4) . . ?
N13 C12 C11 117.4(4) . . ?
C17 C12 C11 119.9(4) . . ?
C14 N13 C12 117.8(4) . . ?
C14 N13 Pb1 125.6(3) . . ?
C12 N13 Pb1 116.5(2) . . ?
N13 C14 C15 122.7(4) . . ?
N13 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C16 C15 C14 119.2(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 118.4(4) . . ?
C16 C17 H17 120.8 . . ?
C12 C17 H17 120.8 . . ?
O19 N18 O20 118.7(4) . . ?
O19 N18 O21 120.2(4) . . ?
O20 N18 O21 121.0(4) . . ?
N18 O20 Pb1 100.6(3) . . ?
O23 N22 O24 120.7(4) . . ?
O23 N22 O25 121.3(4) . . ?
O24 N22 O25 118.0(4) . . ?
N22 O24 Pb1 95.9(2) . . ?
N22 O25 Pb1 96.9(2) . . ?

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
C6 C1 C2 N3 -0.5(8) . . . . ?
C1 C2 N3 C4 0.5(7) . . . . ?
C1 C2 N3 Pb1 -174.4(4) . . . 4_676 ?
C2 N3 C4 C5 -0.7(7) . . . . ?
Pb1 N3 C4 C5 173.8(3) 4_676 . . . ?
N3 C4 C5 C6 0.9(7) . . . . ?
C2 C1 C6 C5 0.7(7) . . . . ?
C2 C1 C6 C7 -179.6(4) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
C1 C6 C7 O8 -14.0(6) . . . . ?
C5 C6 C7 O8 165.7(4) . . . . ?
C1 C6 C7 N9 166.6(4) . . . . ?
C5 C6 C7 N9 -13.6(6) . . . . ?
N9 C7 O8 Pb1 -16.7(5) . . . . ?
C6 C7 O8 Pb1 163.9(3) . . . . ?
O8 C7 N9 N10 0.8(6) . . . . ?
C6 C7 N9 N10 -179.9(4) . . . . ?
C7 N9 N10 C11 -175.2(4) . . . . ?
C7 N9 N10 Pb1 16.1(5) . . . . ?
N9 N10 C11 C12 178.7(4) . . . . ?
Pb1 N10 C11 C12 -13.5(7) . . . . ?
N10 C11 C12 N13 6.1(7) . . . . ?
N10 C11 C12 C17 -173.6(5) . . . . ?
C17 C12 N13 C14 -1.0(6) . . . . ?
C11 C12 N13 C14 179.4(4) . . . . ?
C17 C12 N13 Pb1 -177.3(3) . . . . ?
C11 C12 N13 Pb1 3.1(5) . . . . ?
C12 N13 C14 C15 1.8(7) . . . . ?
Pb1 N13 C14 C15 177.8(3) . . . . ?
N13 C14 C15 C16 -1.2(7) . . . . ?
C14 C15 C16 C17 -0.3(7) . . . . ?
C15 C16 C17 C12 1.1(7) . . . . ?
N13 C12 C17 C16 -0.4(7) . . . . ?
C11 C12 C17 C16 179.2(5) . . . . ?
O19 N18 O20 Pb1 32.3(5) . . . . ?
O21 N18 O20 Pb1 -143.6(4) . . . . ?
O23 N22 O24 Pb1 -163.0(3) . . . . ?
O25 N22 O24 Pb1 14.1(4) . . . . ?
O23 N22 O25 Pb1 162.9(3) . . . . ?
O24 N22 O25 Pb1 -14.2(4) . . . . ?

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
C2 H2 O23 0.95 2.53 3.141(6) 122.2 4_576
C5 H5 O21 0.95 2.57 3.185(5) 122.7 1_655
C11 H11 O20 0.95 2.59 3.247(6) 126.6 3_666
C11 H11 O21 0.95 2.36 3.309(6) 173.5 3_666
C4 H4 O8 0.95 2.63 3.225(5) 121.0 4_676
C14 H14 O23 0.95 2.42 3.184(6) 137.5 3_665
N9 H9 O20 0.84(6) 2.57(5) 3.001(5) 113(4) 3_666
N9 H9 O21 0.84(6) 2.10(6) 2.920(5) 163(5) 1_655
C2 H2 O23 0.95 2.53 3.141(6) 122.2 4_576
C5 H5 O21 0.95 2.57 3.185(5) 122.7 1_655
C11 H11 O20 0.95 2.59 3.247(6) 126.6 3_666
C11 H11 O21 0.95 2.36 3.309(6) 173.5 3_666
C4 H4 O8 0.95 2.63 3.225(5) 121.0 4_676
C14 H14 O23 0.95 2.42 3.184(6) 137.5 3_665
N9 H9 O20 0.84(6) 2.57(5) 3.001(5) 113(4) 3_666
N9 H9 O21 0.84(6) 2.10(6) 2.920(5) 163(5) 1_655

_refine_diff_density_max         0.934
_refine_diff_density_min         -1.753
_refine_diff_density_rms         0.194




# start Validation Reply Form

_vrf_PLAT972_shelx               
;
PROBLEM: Check Calcd Residual Density  0.72A From     Pb1      -1.80 eA-3  
RESPONSE: Diffraction patterns and Twinrotmat routine of Platon 
didn't show any non-merohedral or merohedral twinning.
The compound was counted as "strong absorber" for the absorption
correction.
;

_vrf_PLAT974_shelx               
;
PROBLEM: Check Calcd Negative Residual Density on     Pb1      -1.45 eA-3  
RESPONSE: Diffraction patterns and Twinrotmat routine of Platon 
didn't show any non-merohedral or merohedral twinning.
The compound was counted as "strong absorber" for the absorption
correction.
;

# end Validation Reply Form
####################################################################### 
# 
# 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 1535558'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-03-09 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            'C16 H15 N6 O2 Pb S2'
_chemical_formula_weight         594.65

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'
S S 0.1246 0.1234 '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                   12.964(4)
_cell_length_b                   8.401(3)
_cell_length_c                   18.917(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.216(3)
_cell_angle_gamma                90
_cell_volume                     1987.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9871
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.23

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_F_000             1132
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.972
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    8.721
_shelx_estimated_absorpt_T_min   0.043
_shelx_estimated_absorpt_T_max   0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3479
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22625
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.628
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4871
_reflns_number_gt                4278
_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       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'


_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)+(0.0398P)²] 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         4871
_refine_ls_number_parameters     249
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.09032(2) 0.56575(2) 0.29651(2) 0.02654(6) Uani 1 1 d . . . . .
S1 S 0.02137(7) 0.86499(11) 0.35844(5) 0.02926(19) Uani 1 1 d . . . . .
S2 S 0.19413(8) 0.25333(11) 0.28863(6) 0.0403(2) Uani 1 1 d . . . . .
C1 C 0.4715(3) 0.7672(5) 0.4194(2) 0.0454(10) Uani 1 1 d . . . . .
H1 H 0.4468 0.7735 0.3676 0.055 Uiso 1 1 calc R U . . .
C2 C 0.5697(3) 0.8286(6) 0.4553(3) 0.0544(12) Uani 1 1 d . . . . .
H2 H 0.6135 0.8751 0.4278 0.065 Uiso 1 1 calc R U . . .
N3 N 0.6038(3) 0.8237(4) 0.5275(2) 0.0444(9) Uani 1 1 d . . . . .
C4 C 0.5452(3) 0.7573(6) 0.5685(3) 0.0500(11) Uani 1 1 d . . . . .
H4 H 0.5716 0.7549 0.6203 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4461(3) 0.6921(5) 0.5352(2) 0.0420(10) Uani 1 1 d . . . . .
H5 H 0.4042 0.6450 0.5639 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4092(3) 0.6963(4) 0.4597(2) 0.0308(8) Uani 1 1 d . . . . .
C7 C 0.3015(3) 0.6299(4) 0.4200(2) 0.0284(7) Uani 1 1 d . . . . .
O8 O 0.26785(19) 0.6602(3) 0.35242(14) 0.0347(6) Uani 1 1 d . . . . .
N9 N 0.2563(2) 0.5456(3) 0.46259(17) 0.0274(6) Uani 1 1 d . . . . .
N10 N 0.1560(2) 0.4923(3) 0.42386(15) 0.0243(6) Uani 1 1 d . . . . .
C11 C 0.1062(3) 0.3963(4) 0.45758(18) 0.0237(7) Uani 1 1 d . . . . .
C12 C 0.1520(3) 0.3380(4) 0.53413(19) 0.0315(8) Uani 1 1 d . . . . .
H12A H 0.2182 0.3959 0.5564 0.047 Uiso 1 1 calc R U . . .
H12B H 0.1674 0.2239 0.5332 0.047 Uiso 1 1 calc R U . . .
H12C H 0.1003 0.3559 0.5630 0.047 Uiso 1 1 calc R U . . .
C13 C -0.0018(3) 0.3453(4) 0.41648(18) 0.0238(7) Uani 1 1 d . . . . .
C14 C -0.0636(3) 0.2431(4) 0.4452(2) 0.0321(8) Uani 1 1 d . . . . .
H14 H -0.0360 0.1998 0.4928 0.038 Uiso 1 1 calc R U . . .
C15 C -0.1660(3) 0.2033(5) 0.4048(2) 0.0392(9) Uani 1 1 d . . . . .
H15 H -0.2087 0.1322 0.4241 0.047 Uiso 1 1 calc R U . . .
C16 C -0.2046(3) 0.2683(4) 0.3365(2) 0.0318(8) Uani 1 1 d . . . . .
H16 H -0.2748 0.2443 0.3081 0.038 Uiso 1 1 calc R U . . .
C17 C -0.1393(3) 0.3699(4) 0.3096(2) 0.0293(7) Uani 1 1 d . . . . .
H17 H -0.1658 0.4142 0.2621 0.035 Uiso 1 1 calc R U . . .
N18 N -0.0404(2) 0.4073(3) 0.34842(17) 0.0255(6) Uani 1 1 d . . . . .
C19 C 0.1338(3) 0.9454(4) 0.4058(2) 0.0293(8) Uani 1 1 d . . . . .
N20 N 0.2125(3) 1.0042(5) 0.4398(2) 0.0467(9) Uani 1 1 d . . . . .
C21 C 0.2523(3) 0.3247(5) 0.2272(2) 0.0388(9) Uani 1 1 d . . . . .
N22 N 0.2931(3) 0.3751(5) 0.1847(2) 0.0579(10) Uani 1 1 d . . . . .
C24 C 0.5455(7) 0.5149(10) 0.2625(5) 0.110(3) Uani 1 1 d . . . . .
H24A H 0.5811 0.6018 0.2942 0.165 Uiso 1 1 calc R U . . .
H24B H 0.5989 0.4522 0.2463 0.165 Uiso 1 1 calc R U . . .
H24C H 0.5083 0.4464 0.2897 0.165 Uiso 1 1 calc R U . . .
O23 O 0.4718(5) 0.5779(5) 0.2015(4) 0.1065(19) Uani 1 1 d D . . . .
H23 H 0.426(6) 0.508(9) 0.195(5) 0.160 Uiso 1 1 d 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 O8 2.401(2) . ?
Pb1 N10 2.415(3) . ?
Pb1 N18 2.546(3) . ?
Pb1 S2 2.9710(13) . ?
Pb1 S1 3.0068(12) . ?
S1 C19 1.643(4) . ?
S2 C21 1.655(5) . ?
C1 C2 1.376(5) . ?
C1 C6 1.383(5) . ?
C1 H1 0.9500 . ?
C2 N3 1.321(6) . ?
C2 H2 0.9500 . ?
N3 C4 1.341(6) . ?
C4 C5 1.387(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.508(4) . ?
C7 O8 1.263(4) . ?
C7 N9 1.320(5) . ?
N9 N10 1.389(4) . ?
N10 C11 1.299(4) . ?
C11 C13 1.476(4) . ?
C11 C12 1.496(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N18 1.357(4) . ?
C13 C14 1.379(5) . ?
C14 C15 1.388(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.370(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(5) . ?
C16 H16 0.9500 . ?
C17 N18 1.337(4) . ?
C17 H17 0.9500 . ?
C19 N20 1.164(5) . ?
C21 N22 1.152(6) . ?
C24 O23 1.394(9) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O23 H23 0.83(2) . ?

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 N10 66.36(9) . . ?
O8 Pb1 N18 131.36(9) . . ?
N10 Pb1 N18 65.01(9) . . ?
O8 Pb1 S2 85.39(7) . . ?
N10 Pb1 S2 77.21(7) . . ?
N18 Pb1 S2 85.04(7) . . ?
O8 Pb1 S1 84.30(7) . . ?
N10 Pb1 S1 83.57(7) . . ?
N18 Pb1 S1 89.47(7) . . ?
S2 Pb1 S1 160.56(3) . . ?
C19 S1 Pb1 104.14(13) . . ?
C21 S2 Pb1 90.62(14) . . ?
C2 C1 C6 119.2(4) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
N3 C2 C1 121.0(4) . . ?
N3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 N3 C4 121.6(4) . . ?
N3 C4 C5 119.9(4) . . ?
N3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 122.0(3) . . ?
C1 C6 C7 118.9(3) . . ?
O8 C7 N9 129.4(3) . . ?
O8 C7 C6 117.3(3) . . ?
N9 C7 C6 113.3(3) . . ?
C7 O8 Pb1 114.6(2) . . ?
C7 N9 N10 110.8(3) . . ?
C11 N10 N9 117.2(3) . . ?
C11 N10 Pb1 123.9(2) . . ?
N9 N10 Pb1 118.7(2) . . ?
N10 C11 C13 116.5(3) . . ?
N10 C11 C12 123.8(3) . . ?
C13 C11 C12 119.7(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N18 C13 C14 120.4(3) . . ?
N18 C13 C11 116.8(3) . . ?
C14 C13 C11 122.8(3) . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 118.9(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
N18 C17 C16 122.2(3) . . ?
N18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 N18 C13 119.5(3) . . ?
C17 N18 Pb1 123.4(2) . . ?
C13 N18 Pb1 116.7(2) . . ?
N20 C19 S1 178.8(4) . . ?
N22 C21 S2 179.6(4) . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C24 O23 H23 99(7) . . ?

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
C6 C1 C2 N3 -1.5(7) . . . . ?
C1 C2 N3 C4 0.9(7) . . . . ?
C2 N3 C4 C5 -0.2(6) . . . . ?
N3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 -0.7(6) . . . . ?
C4 C5 C6 C7 -179.0(4) . . . . ?
C2 C1 C6 C5 1.4(6) . . . . ?
C2 C1 C6 C7 179.7(4) . . . . ?
C5 C6 C7 O8 169.7(4) . . . . ?
C1 C6 C7 O8 -8.6(5) . . . . ?
C5 C6 C7 N9 -10.9(5) . . . . ?
C1 C6 C7 N9 170.8(4) . . . . ?
N9 C7 O8 Pb1 5.0(5) . . . . ?
C6 C7 O8 Pb1 -175.6(2) . . . . ?
O8 C7 N9 N10 -2.7(5) . . . . ?
C6 C7 N9 N10 177.9(3) . . . . ?
C7 N9 N10 C11 174.3(3) . . . . ?
C7 N9 N10 Pb1 -1.1(4) . . . . ?
N9 N10 C11 C13 177.9(3) . . . . ?
Pb1 N10 C11 C13 -6.9(4) . . . . ?
N9 N10 C11 C12 -1.6(5) . . . . ?
Pb1 N10 C11 C12 173.6(2) . . . . ?
N10 C11 C13 N18 -2.1(4) . . . . ?
C12 C11 C13 N18 177.5(3) . . . . ?
N10 C11 C13 C14 179.7(3) . . . . ?
C12 C11 C13 C14 -0.8(5) . . . . ?
N18 C13 C14 C15 -0.2(5) . . . . ?
C11 C13 C14 C15 178.0(3) . . . . ?
C13 C14 C15 C16 -0.6(6) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 N18 -0.6(6) . . . . ?
C16 C17 N18 C13 -0.3(5) . . . . ?
C16 C17 N18 Pb1 172.5(3) . . . . ?
C14 C13 N18 C17 0.7(5) . . . . ?
C11 C13 N18 C17 -177.6(3) . . . . ?
C14 C13 N18 Pb1 -172.6(3) . . . . ?
C11 C13 N18 Pb1 9.1(4) . . . . ?

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
C4 H4 O23 0.95 2.65 3.227(7) 119.2 4_576
C14 H14 S1 0.95 2.82 3.722(4) 158.3 3_566
C17 H17 S2 0.95 3.00 3.694(4) 131.2 2
O23 H23 N22 0.83(2) 2.01(3) 2.826(7) 167(11) .

_refine_diff_density_max         0.950
_refine_diff_density_min         -1.310
_refine_diff_density_rms         0.179

####################################################################### 
# 
# 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 1535556'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-03-09 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            'C12 H10 Cl2 N4 O Pb'
_chemical_formula_weight         504.33

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.0154(6)
_cell_length_b                   12.5288(5)
_cell_length_c                   16.4104(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2881.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2619
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      24.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.325
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    12.080
_shelx_estimated_absorpt_T_min   0.060
_shelx_estimated_absorpt_T_max   0.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5485
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20923
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.482
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3590
_reflns_number_gt                2226
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0335P)²] 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         3590
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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 0.59465(2) 0.36502(3) 0.51936(2) 0.02199(13) Uani 1 1 d . . . . .
Cl1 Cl 0.41666(18) 0.4010(2) 0.44218(16) 0.0359(7) Uani 1 1 d . . . . .
Cl2 Cl 0.57238(18) 0.1441(2) 0.50425(16) 0.0377(7) Uani 1 1 d . . . . .
C1 C 0.8349(7) 0.3497(9) 0.7792(6) 0.029(3) Uani 1 1 d . . . . .
H1 H 0.7675 0.3451 0.7843 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8908(7) 0.3493(9) 0.8482(6) 0.030(3) Uani 1 1 d . . . . .
H2 H 0.8609 0.3440 0.9000 0.036 Uiso 1 1 calc R U . . .
N3 N 0.9849(6) 0.3562(7) 0.8445(5) 0.028(2) Uani 1 1 d . . . . .
C4 C 1.0249(7) 0.3624(8) 0.7711(6) 0.030(3) Uani 1 1 d . . . . .
H4 H 1.0925 0.3668 0.7678 0.036 Uiso 1 1 calc R U . . .
C5 C 0.9735(6) 0.3629(9) 0.6996(6) 0.027(2) Uani 1 1 d . . . . .
H5 H 1.0051 0.3675 0.6485 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8748(6) 0.3564(9) 0.7035(6) 0.024(2) Uani 1 1 d . . . . .
C7 C 0.8095(6) 0.3601(8) 0.6306(6) 0.019(2) Uani 1 1 d . . . . .
O8 O 0.7238(5) 0.3481(6) 0.6400(4) 0.0287(18) Uani 1 1 d . . . . .
N9 N 0.8489(5) 0.3780(7) 0.5580(5) 0.024(2) Uani 1 1 d D . . . .
N10 N 0.7886(6) 0.3804(6) 0.4916(5) 0.024(2) Uani 1 1 d . . . . .
C11 C 0.8234(7) 0.4007(8) 0.4228(6) 0.024(3) Uani 1 1 d . . . . .
H11 H 0.8893 0.4170 0.4174 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7607(7) 0.3990(8) 0.3504(6) 0.022(2) Uani 1 1 d . . . . .
N13 N 0.6660(5) 0.3851(6) 0.3646(4) 0.021(2) Uani 1 1 d . . . . .
C14 C 0.6093(7) 0.3793(8) 0.2998(6) 0.024(2) Uani 1 1 d . . . . .
H14 H 0.5428 0.3711 0.3090 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6396(7) 0.3843(8) 0.2214(6) 0.025(3) Uani 1 1 d . . . . .
H15 H 0.5959 0.3777 0.1774 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7362(8) 0.3994(8) 0.2073(6) 0.029(3) Uani 1 1 d . . . . .
H16 H 0.7602 0.4030 0.1533 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7968(7) 0.4089(8) 0.2727(6) 0.028(3) Uani 1 1 d . . . . .
H17 H 0.8628 0.4222 0.2644 0.034 Uiso 1 1 calc R U . . .
H9 H 0.908(3) 0.399(7) 0.555(6) 0.034 Uiso 1 1 d 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 O8 2.690(6) . ?
Pb1 N3 2.714(8) 6_557 ?
Pb1 N13 2.741(7) . ?
Pb1 N10 2.763(8) . ?
Pb1 Cl2 2.796(3) . ?
Pb1 Cl1 2.834(2) . ?
Pb1 Cl1 3.003(3) 5_666 ?
Cl1 Pb1 3.003(3) 5_666 ?
C1 C6 1.364(14) . ?
C1 C2 1.378(13) . ?
C1 H1 0.9500 . ?
C2 N3 1.323(12) . ?
C2 H2 0.9500 . ?
N3 C4 1.331(12) . ?
N3 Pb1 2.714(8) 6_657 ?
C4 C5 1.376(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.507(13) . ?
C7 O8 1.221(10) . ?
C7 N9 1.332(12) . ?
N9 N10 1.379(10) . ?
N9 H9 0.87(2) . ?
N10 C11 1.256(11) . ?
C11 C12 1.478(13) . ?
C11 H11 0.9500 . ?
C12 N13 1.359(11) . ?
C12 C17 1.377(13) . ?
N13 C14 1.329(11) . ?
C14 C15 1.355(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(13) . ?
C16 H16 0.9500 . ?
C17 H17 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
O8 Pb1 N3 76.8(2) . 6_557 ?
O8 Pb1 N13 116.3(2) . . ?
N3 Pb1 N13 166.6(2) 6_557 . ?
O8 Pb1 N10 57.6(2) . . ?
N3 Pb1 N10 134.1(2) 6_557 . ?
N13 Pb1 N10 58.8(2) . . ?
O8 Pb1 Cl2 93.57(16) . . ?
N3 Pb1 Cl2 88.2(2) 6_557 . ?
N13 Pb1 Cl2 92.82(18) . . ?
N10 Pb1 Cl2 99.45(16) . . ?
O8 Pb1 Cl1 158.99(15) . . ?
N3 Pb1 Cl1 82.85(19) 6_557 . ?
N13 Pb1 Cl1 83.81(17) . . ?
N10 Pb1 Cl1 141.39(17) . . ?
Cl2 Pb1 Cl1 91.13(8) . . ?
O8 Pb1 Cl1 87.59(16) . 5_666 ?
N3 Pb1 Cl1 80.6(2) 6_557 5_666 ?
N13 Pb1 Cl1 97.16(18) . 5_666 ?
N10 Pb1 Cl1 91.07(16) . 5_666 ?
Cl2 Pb1 Cl1 168.24(8) . 5_666 ?
Cl1 Pb1 Cl1 83.80(8) . 5_666 ?
Pb1 Cl1 Pb1 96.20(8) . 5_666 ?
C6 C1 C2 121.0(10) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
N3 C2 C1 121.9(10) . . ?
N3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 N3 C4 117.7(9) . . ?
C2 N3 Pb1 122.0(6) . 6_657 ?
C4 N3 Pb1 120.3(7) . 6_657 ?
N3 C4 C5 123.4(10) . . ?
N3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C6 118.9(9) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 117.1(9) . . ?
C1 C6 C7 118.3(9) . . ?
C5 C6 C7 124.6(9) . . ?
O8 C7 N9 122.7(9) . . ?
O8 C7 C6 119.6(9) . . ?
N9 C7 C6 117.7(8) . . ?
C7 O8 Pb1 124.1(6) . . ?
C7 N9 N10 117.2(8) . . ?
C7 N9 H9 120(7) . . ?
N10 N9 H9 122(7) . . ?
C11 N10 N9 118.5(8) . . ?
C11 N10 Pb1 123.0(6) . . ?
N9 N10 Pb1 118.1(5) . . ?
N10 C11 C12 119.3(9) . . ?
N10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N13 C12 C17 121.9(9) . . ?
N13 C12 C11 116.5(8) . . ?
C17 C12 C11 121.7(9) . . ?
C14 N13 C12 117.0(8) . . ?
C14 N13 Pb1 121.3(6) . . ?
C12 N13 Pb1 121.7(6) . . ?
N13 C14 C15 124.8(9) . . ?
N13 C14 H14 117.6 . . ?
C15 C14 H14 117.6 . . ?
C14 C15 C16 118.0(9) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 119.0(9) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C12 119.3(10) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 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
C6 C1 C2 N3 0.5(18) . . . . ?
C1 C2 N3 C4 -0.7(16) . . . . ?
C1 C2 N3 Pb1 177.0(8) . . . 6_657 ?
C2 N3 C4 C5 0.5(16) . . . . ?
Pb1 N3 C4 C5 -177.3(9) 6_657 . . . ?
N3 C4 C5 C6 0.0(18) . . . . ?
C2 C1 C6 C5 0.0(19) . . . . ?
C2 C1 C6 C7 -178.0(9) . . . . ?
C4 C5 C6 C1 -0.2(18) . . . . ?
C4 C5 C6 C7 177.6(10) . . . . ?
C1 C6 C7 O8 -6.1(16) . . . . ?
C5 C6 C7 O8 176.1(12) . . . . ?
C1 C6 C7 N9 173.1(11) . . . . ?
C5 C6 C7 N9 -4.7(17) . . . . ?
N9 C7 O8 Pb1 -3.4(15) . . . . ?
C6 C7 O8 Pb1 175.7(7) . . . . ?
O8 C7 N9 N10 -1.4(16) . . . . ?
C6 C7 N9 N10 179.5(9) . . . . ?
C7 N9 N10 C11 177.6(9) . . . . ?
C7 N9 N10 Pb1 5.1(11) . . . . ?
N9 N10 C11 C12 177.3(8) . . . . ?
Pb1 N10 C11 C12 -10.5(13) . . . . ?
N10 C11 C12 N13 6.1(14) . . . . ?
N10 C11 C12 C17 -172.7(9) . . . . ?
C17 C12 N13 C14 1.3(15) . . . . ?
C11 C12 N13 C14 -177.5(8) . . . . ?
C17 C12 N13 Pb1 179.9(7) . . . . ?
C11 C12 N13 Pb1 1.1(12) . . . . ?
C12 N13 C14 C15 1.3(15) . . . . ?
Pb1 N13 C14 C15 -177.3(8) . . . . ?
N13 C14 C15 C16 -1.8(16) . . . . ?
C14 C15 C16 C17 -0.2(15) . . . . ?
C15 C16 C17 C12 2.6(16) . . . . ?
N13 C12 C17 C16 -3.3(16) . . . . ?
C11 C12 C17 C16 175.5(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 Cl1 0.95 2.80 3.518(11) 133.4 6_657
C4 H4 O8 0.95 2.39 3.151(12) 136.5 6_657
C5 H5 Cl2 0.95 2.68 3.623(10) 170.2 4_556
N9 H9 Cl2 0.87(2) 2.55(6) 3.307(8) 145(8) 4_556
C11 H11 Cl2 0.95 2.97 3.731(10) 138.0 4_556
C14 H14 Cl1 0.95 2.84 3.582(10) 136.1 .
C15 H15 Cl2 0.95 2.87 3.703(10) 146.4 7_565
C2 H2 Cl1 0.95 2.80 3.518(11) 133.4 6_657
C4 H4 O8 0.95 2.39 3.151(12) 136.5 6_657
C5 H5 Cl2 0.95 2.68 3.623(10) 170.2 4_556
C11 H11 Cl2 0.95 2.97 3.731(10) 138.0 4_556
C14 H14 Cl1 0.95 2.84 3.582(10) 136.1 .
C15 H15 Cl2 0.95 2.87 3.703(10) 146.4 7_565
N9 H9 Cl2 0.87(2) 2.55(6) 3.307(8) 145(8) 4_556

_refine_diff_density_max         2.533
_refine_diff_density_min         -1.818
_refine_diff_density_rms         0.250






# start Validation Reply Form

_vrf_PLAT973_shelx               
;
PROBLEM: Check Calcd Positive Residual Density on     Pb1       1.85 eA-3  
RESPONSE: Diffraction patterns and Twinrotmat routine of Platon 
didn't show any non-merohedral or merohedral twinning.
The compound was counted as "strong absorber" for the absorption
correction.
;

# end Validation Reply Form
