# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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 1059556'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N7 O Pb'
_chemical_formula_sum            'C13 H11 N7 O Pb'
_chemical_formula_weight         488.48

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4765(3)
_cell_length_b                   9.8748(5)
_cell_length_c                   10.3866(9)
_cell_angle_alpha                85.982(6)
_cell_angle_beta                 77.230(7)
_cell_angle_gamma                71.633(6)
_cell_volume                     709.77(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.286
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    11.899
_shelx_estimated_absorpt_T_min   0.077
_shelx_estimated_absorpt_T_max   0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0415
_exptl_absorpt_correction_T_max  0.1812
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            14106
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.069
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4097
_reflns_number_gt                3831
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0337P)²+0.2700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4097
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0619
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.30508(2) 0.41962(2) 0.48598(2) 0.02890(5) Uani 1 1 d . . . . .
N1A N 0.8082(5) -0.2221(3) 0.3279(3) 0.0360(7) Uani 1 1 d . . . . .
C2A C 0.7155(5) -0.0832(3) 0.3510(3) 0.0336(7) Uani 1 1 d . . . . .
H2A H 0.6492 -0.0557 0.4367 0.040 Uiso 1 1 calc R U . . .
C3A C 0.7120(5) 0.0222(3) 0.2555(3) 0.0288(6) Uani 1 1 d . . . . .
C4A C 0.8103(5) -0.0197(4) 0.1278(4) 0.0341(7) Uani 1 1 d . . . . .
H4A H 0.8105 0.0473 0.0603 0.041 Uiso 1 1 calc R U . . .
C5A C 0.9083(6) -0.1635(4) 0.1023(4) 0.0395(8) Uani 1 1 d . . . . .
H5A H 0.9753 -0.1939 0.0175 0.047 Uiso 1 1 calc R U . . .
C6A C 0.9049(6) -0.2598(4) 0.2039(4) 0.0383(8) Uani 1 1 d . . . . .
H6A H 0.9726 -0.3555 0.1861 0.046 Uiso 1 1 calc R U . . .
C7A C 0.6003(5) 0.1724(3) 0.2938(3) 0.0299(6) Uani 1 1 d . . . . .
O7A O 0.4780(4) 0.1914(3) 0.4020(3) 0.0463(7) Uani 1 1 d . . . . .
N8A N 0.6395(4) 0.2708(3) 0.2099(3) 0.0329(6) Uani 1 1 d . . . . .
N9A N 0.5263(4) 0.4058(3) 0.2562(3) 0.0325(6) Uani 1 1 d . . . . .
C10A C 0.5568(5) 0.5118(3) 0.1846(4) 0.0308(6) Uani 1 1 d . . . . .
C101 C 0.7091(6) 0.4920(4) 0.0621(4) 0.0448(9) Uani 1 1 d . . . . .
H10A H 0.6938 0.4259 0.0049 0.067 Uiso 1 1 calc R U . . .
H10B H 0.8336 0.4552 0.0842 0.067 Uiso 1 1 calc R U . . .
H10C H 0.6982 0.5820 0.0179 0.067 Uiso 1 1 calc R U . . .
C11A C 0.4344(5) 0.6569(3) 0.2316(4) 0.0315(7) Uani 1 1 d . . . . .
N12A N 0.3192(5) 0.6667(3) 0.3525(3) 0.0392(7) Uani 1 1 d . . . . .
C13A C 0.2114(6) 0.7963(4) 0.3993(4) 0.0473(9) Uani 1 1 d . . . . .
H13A H 0.1320 0.8031 0.4828 0.057 Uiso 1 1 calc R U . . .
C14A C 0.2124(7) 0.9195(4) 0.3302(5) 0.0489(10) Uani 1 1 d . . . . .
H14A H 0.1376 1.0078 0.3672 0.059 Uiso 1 1 calc R U . . .
C15A C 0.3251(7) 0.9108(4) 0.2059(5) 0.0478(10) Uani 1 1 d . . . . .
H15A H 0.3252 0.9926 0.1559 0.057 Uiso 1 1 calc R U . . .
C16A C 0.4392(6) 0.7773(4) 0.1563(4) 0.0412(8) Uani 1 1 d . . . . .
H16A H 0.5185 0.7689 0.0726 0.049 Uiso 1 1 calc R U . . .
N1B N 0.0697(4) 0.4100(4) 0.3770(3) 0.0447(8) Uani 1 1 d . . . . .
N2B N 0.1194(5) 0.3378(3) 0.2807(3) 0.0368(6) Uani 1 1 d . . . . .
N3B N 0.1625(8) 0.2705(5) 0.1871(5) 0.0670(13) 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 N1B 2.321(3) . ?
Pb1 O7A 2.335(2) . ?
Pb1 N9A 2.571(3) . ?
Pb1 N12A 2.741(3) . ?
N1A C2A 1.339(4) . ?
N1A C6A 1.344(5) . ?
C2A C3A 1.384(5) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.387(5) . ?
C3A C7A 1.487(4) . ?
C4A C5A 1.391(5) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.371(6) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A O7A 1.266(4) . ?
C7A N8A 1.318(4) . ?
N8A N9A 1.386(4) . ?
N9A C10A 1.292(4) . ?
C10A C11A 1.484(4) . ?
C10A C101 1.485(5) . ?
C101 H10A 0.9600 . ?
C101 H10B 0.9600 . ?
C101 H10C 0.9600 . ?
C11A N12A 1.346(5) . ?
C11A C16A 1.383(5) . ?
N12A C13A 1.337(4) . ?
C13A C14A 1.370(6) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.368(7) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.387(5) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
N1B N2B 1.190(4) . ?
N2B N3B 1.143(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
N1B Pb1 O7A 86.44(11) . . ?
N1B Pb1 N9A 86.43(11) . . ?
O7A Pb1 N9A 63.47(9) . . ?
N1B Pb1 N12A 88.88(12) . . ?
O7A Pb1 N12A 124.03(9) . . ?
N9A Pb1 N12A 60.58(9) . . ?
C2A N1A C6A 117.1(3) . . ?
N1A C2A C3A 124.2(3) . . ?
N1A C2A H2A 117.9 . . ?
C3A C2A H2A 117.9 . . ?
C2A C3A C4A 117.6(3) . . ?
C2A C3A C7A 118.8(3) . . ?
C4A C3A C7A 123.6(3) . . ?
C3A C4A C5A 119.0(3) . . ?
C3A C4A H4A 120.5 . . ?
C5A C4A H4A 120.5 . . ?
C6A C5A C4A 119.2(3) . . ?
C6A C5A H5A 120.4 . . ?
C4A C5A H5A 120.4 . . ?
N1A C6A C5A 123.0(3) . . ?
N1A C6A H6A 118.5 . . ?
C5A C6A H6A 118.5 . . ?
O7A C7A N8A 127.5(3) . . ?
O7A C7A C3A 116.7(3) . . ?
N8A C7A C3A 115.9(3) . . ?
C7A O7A Pb1 121.6(2) . . ?
C7A N8A N9A 110.4(3) . . ?
C10A N9A N8A 116.2(3) . . ?
C10A N9A Pb1 126.7(2) . . ?
N8A N9A Pb1 116.7(2) . . ?
N9A C10A C11A 116.8(3) . . ?
N9A C10A C101 122.4(3) . . ?
C11A C10A C101 120.8(3) . . ?
C10A C101 H10A 109.5 . . ?
C10A C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C10A C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
N12A C11A C16A 121.1(3) . . ?
N12A C11A C10A 117.0(3) . . ?
C16A C11A C10A 121.9(3) . . ?
C13A N12A C11A 118.4(3) . . ?
C13A N12A Pb1 123.1(3) . . ?
C11A N12A Pb1 118.4(2) . . ?
N12A C13A C14A 123.1(4) . . ?
N12A C13A H13A 118.4 . . ?
C14A C13A H13A 118.4 . . ?
C15A C14A C13A 119.0(4) . . ?
C15A C14A H14A 120.5 . . ?
C13A C14A H14A 120.5 . . ?
C14A C15A C16A 118.6(4) . . ?
C14A C15A H15A 120.7 . . ?
C16A C15A H15A 120.7 . . ?
C11A C16A C15A 119.7(4) . . ?
C11A C16A H16A 120.1 . . ?
C15A C16A H16A 120.1 . . ?
N2B N1B Pb1 117.8(2) . . ?
N3B N2B N1B 178.1(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
C6A N1A C2A C3A 0.7(6) . . . . ?
N1A C2A C3A C4A 0.4(6) . . . . ?
N1A C2A C3A C7A 178.8(3) . . . . ?
C2A C3A C4A C5A -0.8(5) . . . . ?
C7A C3A C4A C5A -179.1(3) . . . . ?
C3A C4A C5A C6A 0.1(6) . . . . ?
C2A N1A C6A C5A -1.4(6) . . . . ?
C4A C5A C6A N1A 1.0(6) . . . . ?
C2A C3A C7A O7A -16.7(5) . . . . ?
C4A C3A C7A O7A 161.7(4) . . . . ?
C2A C3A C7A N8A 163.8(3) . . . . ?
C4A C3A C7A N8A -17.8(5) . . . . ?
N8A C7A O7A Pb1 -5.1(5) . . . . ?
C3A C7A O7A Pb1 175.5(2) . . . . ?
O7A C7A N8A N9A 0.4(5) . . . . ?
C3A C7A N8A N9A 179.8(3) . . . . ?
C7A N8A N9A C10A 177.5(3) . . . . ?
C7A N8A N9A Pb1 3.9(4) . . . . ?
N8A N9A C10A C11A 179.0(3) . . . . ?
Pb1 N9A C10A C11A -8.1(5) . . . . ?
N8A N9A C10A C101 -2.2(5) . . . . ?
Pb1 N9A C10A C101 170.7(3) . . . . ?
N9A C10A C11A N12A 8.0(5) . . . . ?
C101 C10A C11A N12A -170.8(4) . . . . ?
N9A C10A C11A C16A -172.8(3) . . . . ?
C101 C10A C11A C16A 8.4(5) . . . . ?
C16A C11A N12A C13A -1.2(6) . . . . ?
C10A C11A N12A C13A 178.0(3) . . . . ?
C16A C11A N12A Pb1 176.2(3) . . . . ?
C10A C11A N12A Pb1 -4.6(4) . . . . ?
C11A N12A C13A C14A 0.1(6) . . . . ?
Pb1 N12A C13A C14A -177.1(3) . . . . ?
N12A C13A C14A C15A 1.6(7) . . . . ?
C13A C14A C15A C16A -2.1(7) . . . . ?
N12A C11A C16A C15A 0.6(6) . . . . ?
C10A C11A C16A C15A -178.6(4) . . . . ?
C14A C15A C16A C11A 1.0(7) . . . . ?

_refine_diff_density_max         1.680
_refine_diff_density_min         -1.888
_refine_diff_density_rms         0.145

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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 1059557'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N6 O4 Pb S'
_chemical_formula_sum            'C14 H12 N6 O4 Pb S'
_chemical_formula_weight         567.56

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/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                   9.60250(10)
_cell_length_b                   14.5202(2)
_cell_length_c                   12.4996(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.7659(7)
_cell_angle_gamma                90
_cell_volume                     1712.15(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.202
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    10.010
_shelx_estimated_absorpt_T_min   0.099
_shelx_estimated_absorpt_T_max   0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0621
_exptl_absorpt_correction_T_max  0.1974
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            20335
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.172
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4989
_reflns_number_gt                4166
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0111P)²+0.7208P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4989
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0535
_refine_ls_wR_factor_gt          0.0514
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.22656(2) 0.21829(2) 0.43685(2) 0.02802(4) Uani 1 1 d . . . . .
N1A N 0.0039(3) -0.20405(17) 0.4549(2) 0.0369(6) Uani 1 1 d . . . . .
C2A C 0.0626(4) -0.1216(2) 0.4469(3) 0.0382(8) Uani 1 1 d . . . . .
H2A H 0.0146 -0.0699 0.4648 0.046 Uiso 1 1 calc R U . . .
C3A C 0.1910(3) -0.10848(19) 0.4134(2) 0.0271(6) Uani 1 1 d . . . . .
C4A C 0.2606(3) -0.1851(2) 0.3853(3) 0.0329(7) Uani 1 1 d . . . . .
H4A H 0.3471 -0.1793 0.3627 0.039 Uiso 1 1 calc R U . . .
C5A C 0.2005(4) -0.2705(2) 0.3913(3) 0.0362(7) Uani 1 1 d . . . . .
H5A H 0.2447 -0.3231 0.3715 0.043 Uiso 1 1 calc R U . . .
C6A C 0.0740(4) -0.27677(19) 0.4270(3) 0.0352(7) Uani 1 1 d . . . . .
H6A H 0.0351 -0.3349 0.4320 0.042 Uiso 1 1 calc R U . . .
C7A C 0.2465(3) -0.01304(19) 0.4177(2) 0.0276(6) Uani 1 1 d . . . . .
O7A O 0.1997(2) 0.04647(14) 0.47222(19) 0.0364(5) Uani 1 1 d . . . . .
N8A N 0.3527(3) 0.00582(16) 0.3639(2) 0.0316(6) Uani 1 1 d . . . . .
H8A H 0.3892 -0.0366 0.3271 0.038 Uiso 1 1 calc R U . . .
N9A N 0.4010(3) 0.09623(16) 0.3701(2) 0.0304(5) Uani 1 1 d . . . . .
C10A C 0.5180(3) 0.1152(2) 0.3391(2) 0.0297(6) Uani 1 1 d . . . . .
C101 C 0.6124(4) 0.0472(2) 0.2979(3) 0.0409(8) Uani 1 1 d . . . . .
H10A H 0.5874 -0.0140 0.3164 0.061 Uiso 1 1 calc R U . . .
H10B H 0.7093 0.0593 0.3306 0.061 Uiso 1 1 calc R U . . .
H10C H 0.6011 0.0526 0.2202 0.061 Uiso 1 1 calc R U . . .
C11A C 0.5592(3) 0.2142(2) 0.3481(2) 0.0297(6) Uani 1 1 d . . . . .
N12A N 0.4716(3) 0.27229(16) 0.3869(2) 0.0358(6) Uani 1 1 d . . . . .
C13A C 0.5081(4) 0.3613(2) 0.3969(3) 0.0449(8) Uani 1 1 d . . . . .
H13A H 0.4480 0.4018 0.4237 0.054 Uiso 1 1 calc R U . . .
C14A C 0.6306(4) 0.3959(2) 0.3695(3) 0.0463(9) Uani 1 1 d . . . . .
H14A H 0.6530 0.4581 0.3784 0.056 Uiso 1 1 calc R U . . .
C15A C 0.7175(4) 0.3368(3) 0.3290(3) 0.0506(9) Uani 1 1 d . . . . .
H15A H 0.8000 0.3583 0.3087 0.061 Uiso 1 1 calc R U . . .
C16A C 0.6822(4) 0.2446(3) 0.3184(3) 0.0427(8) Uani 1 1 d . . . . .
H16A H 0.7412 0.2034 0.2914 0.051 Uiso 1 1 calc R U . . .
N1B N 0.3827(4) 0.2230(2) 0.6168(3) 0.0485(8) Uani 1 1 d . . . . .
C2B C 0.4349(4) 0.2863(2) 0.6662(3) 0.0390(8) Uani 1 1 d . . . . .
S3B S 0.50824(11) 0.37288(7) 0.73763(9) 0.0546(3) Uani 1 1 d . . . . .
N1C N 0.1577(3) 0.43378(18) 0.4085(3) 0.0414(7) Uani 1 1 d . . . . .
O1C O 0.1530(4) 0.51703(18) 0.4007(3) 0.0960(13) Uani 1 1 d . . . . .
O2C O 0.1280(3) 0.38604(16) 0.3245(2) 0.0573(8) Uani 1 1 d . . . . .
O3C O 0.1971(3) 0.39705(17) 0.5003(2) 0.0535(7) 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 N1B 2.460(3) . ?
Pb1 O7A 2.555(2) . ?
Pb1 N12A 2.662(3) . ?
Pb1 N9A 2.677(2) . ?
Pb1 O3C 2.744(3) . ?
N1A C6A 1.333(4) . ?
N1A C2A 1.335(4) . ?
C2A C3A 1.387(4) . ?
C3A C4A 1.377(4) . ?
C3A C7A 1.482(4) . ?
C4A C5A 1.375(4) . ?
C5A C6A 1.373(5) . ?
C7A O7A 1.237(4) . ?
C7A N8A 1.350(4) . ?
N8A N9A 1.390(3) . ?
N9A C10A 1.285(4) . ?
C10A C11A 1.490(4) . ?
C10A C101 1.495(4) . ?
C11A N12A 1.345(4) . ?
C11A C16A 1.375(5) . ?
N12A C13A 1.339(4) . ?
C13A C14A 1.380(5) . ?
C14A C15A 1.358(5) . ?
C15A C16A 1.381(5) . ?
N1B C2B 1.166(4) . ?
C2B S3B 1.625(4) . ?
N1C O1C 1.213(4) . ?
N1C O2C 1.246(4) . ?
N1C O3C 1.257(4) . ?

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
N1B Pb1 O7A 86.16(9) . . ?
N1B Pb1 N12A 77.99(10) . . ?
O7A Pb1 N12A 116.77(7) . . ?
N1B Pb1 N9A 89.63(9) . . ?
O7A Pb1 N9A 59.79(7) . . ?
N12A Pb1 N9A 59.34(7) . . ?
N1B Pb1 O3C 77.74(9) . . ?
O7A Pb1 O3C 148.69(8) . . ?
N12A Pb1 O3C 86.13(8) . . ?
N9A Pb1 O3C 145.15(8) . . ?
C6A N1A C2A 116.8(3) . . ?
N1A C2A C3A 123.8(3) . . ?
C4A C3A C2A 117.9(3) . . ?
C4A C3A C7A 125.2(3) . . ?
C2A C3A C7A 116.8(3) . . ?
C5A C4A C3A 119.0(3) . . ?
C6A C5A C4A 118.9(3) . . ?
N1A C6A C5A 123.5(3) . . ?
O7A C7A N8A 121.3(3) . . ?
O7A C7A C3A 120.5(3) . . ?
N8A C7A C3A 118.2(3) . . ?
C7A O7A Pb1 121.9(2) . . ?
C7A N8A N9A 116.0(2) . . ?
C10A N9A N8A 119.1(3) . . ?
C10A N9A Pb1 125.84(19) . . ?
N8A N9A Pb1 114.91(18) . . ?
N9A C10A C11A 114.8(3) . . ?
N9A C10A C101 125.6(3) . . ?
C11A C10A C101 119.6(3) . . ?
N12A C11A C16A 121.5(3) . . ?
N12A C11A C10A 117.2(3) . . ?
C16A C11A C10A 121.3(3) . . ?
C13A N12A C11A 117.9(3) . . ?
C13A N12A Pb1 119.4(2) . . ?
C11A N12A Pb1 122.69(19) . . ?
N12A C13A C14A 123.3(4) . . ?
C15A C14A C13A 118.3(3) . . ?
C14A C15A C16A 119.4(3) . . ?
C11A C16A C15A 119.6(4) . . ?
C2B N1B Pb1 129.3(3) . . ?
N1B C2B S3B 178.6(3) . . ?
O1C N1C O2C 119.1(3) . . ?
O1C N1C O3C 119.8(3) . . ?
O2C N1C O3C 121.0(3) . . ?
N1C O3C Pb1 99.65(19) . . ?

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
C6A N1A C2A C3A -1.0(5) . . . . ?
N1A C2A C3A C4A 0.9(5) . . . . ?
N1A C2A C3A C7A -175.2(3) . . . . ?
C2A C3A C4A C5A 0.2(5) . . . . ?
C7A C3A C4A C5A 176.0(3) . . . . ?
C3A C4A C5A C6A -1.2(5) . . . . ?
C2A N1A C6A C5A -0.1(5) . . . . ?
C4A C5A C6A N1A 1.2(5) . . . . ?
C4A C3A C7A O7A -158.8(3) . . . . ?
C2A C3A C7A O7A 16.9(4) . . . . ?
C4A C3A C7A N8A 18.7(5) . . . . ?
C2A C3A C7A N8A -165.5(3) . . . . ?
N8A C7A O7A Pb1 22.9(4) . . . . ?
C3A C7A O7A Pb1 -159.6(2) . . . . ?
O7A C7A N8A N9A -2.6(4) . . . . ?
C3A C7A N8A N9A 179.9(2) . . . . ?
C7A N8A N9A C10A 166.9(3) . . . . ?
C7A N8A N9A Pb1 -16.7(3) . . . . ?
N8A N9A C10A C11A 179.4(2) . . . . ?
Pb1 N9A C10A C11A 3.3(4) . . . . ?
N8A N9A C10A C101 -1.5(5) . . . . ?
Pb1 N9A C10A C101 -177.5(2) . . . . ?
N9A C10A C11A N12A 0.0(4) . . . . ?
C101 C10A C11A N12A -179.2(3) . . . . ?
N9A C10A C11A C16A 179.7(3) . . . . ?
C101 C10A C11A C16A 0.5(5) . . . . ?
C16A C11A N12A C13A -0.6(5) . . . . ?
C10A C11A N12A C13A 179.1(3) . . . . ?
C16A C11A N12A Pb1 177.1(2) . . . . ?
C10A C11A N12A Pb1 -3.2(4) . . . . ?
C11A N12A C13A C14A 0.0(5) . . . . ?
Pb1 N12A C13A C14A -177.8(3) . . . . ?
N12A C13A C14A C15A 0.8(6) . . . . ?
C13A C14A C15A C16A -1.1(6) . . . . ?
N12A C11A C16A C15A 0.3(5) . . . . ?
C10A C11A C16A C15A -179.3(3) . . . . ?
C14A C15A C16A C11A 0.5(6) . . . . ?
O1C N1C O3C Pb1 -169.2(3) . . . . ?
O2C N1C O3C Pb1 8.2(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
C2A H2A O7A 0.93 2.36 3.083(4) 134.3 3_556
C5A H5A O1C 0.93 2.53 3.124(4) 121.7 1_545
C6A H6A O1C 0.93 2.49 3.121(4) 124.9 1_545
N8A H8A O2C 0.88 2.18 2.961(4) 147.3 2_545

_refine_diff_density_max         1.008
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.109

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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 1059558'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N4 O3 Pb'
_chemical_formula_sum            'C15 H14 N4 O3 Pb'
_chemical_formula_weight         505.49

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                   8.70720(10)
_cell_length_b                   20.7055(3)
_cell_length_c                   8.96340(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.0686(6)
_cell_angle_gamma                90
_cell_volume                     1574.13(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.133
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    10.738
_shelx_estimated_absorpt_T_min   0.073
_shelx_estimated_absorpt_T_max   0.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0736
_exptl_absorpt_correction_T_max  0.2537
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            30250
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.967
_diffrn_reflns_theta_max         29.994
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4587
_reflns_number_gt                3818
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0642P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0112(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4587
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.12511(2) 0.58730(2) 0.64523(2) 0.03367(8) Uani 1 1 d . . . . .
N1A N -0.0087(5) 0.35948(18) 1.0854(4) 0.0482(10) Uani 1 1 d . . . . .
C2A C 0.0444(7) 0.4047(2) 1.0022(5) 0.0438(11) Uani 1 1 d . . . . .
H2A H 0.0442 0.4476 1.0333 0.053 Uiso 1 1 calc R U . . .
C3A C 0.0997(5) 0.3909(2) 0.8723(4) 0.0345(8) Uani 1 1 d . . . . .
C4A C 0.1109(6) 0.32669(19) 0.8329(5) 0.0420(10) Uani 1 1 d . . . . .
H4A H 0.1536 0.3151 0.7505 0.050 Uiso 1 1 calc R U . . .
C5A C 0.0573(7) 0.2804(2) 0.9190(5) 0.0507(12) Uani 1 1 d . . . . .
H5A H 0.0620 0.2369 0.8941 0.061 Uiso 1 1 calc R U . . .
C6A C -0.0029(6) 0.2983(2) 1.0412(5) 0.0486(11) Uani 1 1 d . . . . .
H6A H -0.0416 0.2664 1.0958 0.058 Uiso 1 1 calc R U . . .
C7A C 0.1417(5) 0.44521(18) 0.7795(4) 0.0340(8) Uani 1 1 d . . . . .
O7A O 0.1274(5) 0.50245(14) 0.8254(4) 0.0546(10) Uani 1 1 d . . . . .
N8A N 0.1908(5) 0.42751(16) 0.6568(4) 0.0370(8) Uani 1 1 d . . . . .
N9A N 0.2194(4) 0.48062(15) 0.5739(3) 0.0330(7) Uani 1 1 d . . . . .
C10A C 0.2812(5) 0.47050(17) 0.4574(4) 0.0318(7) Uani 1 1 d . . . . .
C101 C 0.3268(6) 0.4045(2) 0.4139(5) 0.0417(10) Uani 1 1 d . . . . .
H10A H 0.3411 0.3764 0.5011 0.063 Uiso 1 1 calc R U . . .
H10B H 0.4235 0.4071 0.3797 0.063 Uiso 1 1 calc R U . . .
H10C H 0.2450 0.3876 0.3329 0.063 Uiso 1 1 calc R U . . .
C11A C 0.3052(5) 0.52712(19) 0.3662(4) 0.0337(8) Uani 1 1 d . . . . .
N12A N 0.2634(5) 0.58531(14) 0.4152(4) 0.0355(8) Uani 1 1 d . . . . .
C13A C 0.2847(6) 0.6376(2) 0.3358(5) 0.0432(10) Uani 1 1 d . . . . .
H13A H 0.2581 0.6775 0.3700 0.052 Uiso 1 1 calc R U . . .
C14A C 0.3439(7) 0.6359(2) 0.2062(5) 0.0503(12) Uani 1 1 d . . . . .
H14A H 0.3545 0.6736 0.1531 0.060 Uiso 1 1 calc R U . . .
C15A C 0.3876(8) 0.5766(3) 0.1564(6) 0.0559(14) Uani 1 1 d . . . . .
H15A H 0.4293 0.5738 0.0698 0.067 Uiso 1 1 calc R U . . .
C16A C 0.3676(6) 0.5221(2) 0.2382(5) 0.0440(10) Uani 1 1 d . . . . .
H16A H 0.3962 0.4819 0.2071 0.053 Uiso 1 1 calc R U . . .
C1B C 0.3857(6) 0.6702(2) 0.7732(5) 0.0426(9) Uani 1 1 d . . . . .
O1B O 0.3733(4) 0.60937(15) 0.7876(3) 0.0413(6) Uani 1 1 d . . . . .
O2B O 0.2855(5) 0.70283(16) 0.6882(5) 0.0706(12) Uani 1 1 d . . . . .
C2B C 0.5334(7) 0.7012(3) 0.8674(7) 0.0683(16) Uani 1 1 d . . . . .
H2B1 H 0.5123 0.7455 0.8869 0.102 Uiso 1 1 calc R U . . .
H2B2 H 0.6158 0.6991 0.8123 0.102 Uiso 1 1 calc R U . . .
H2B3 H 0.5659 0.6786 0.9629 0.102 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 O1B 2.294(3) . ?
Pb1 O7A 2.383(3) . ?
Pb1 N9A 2.490(3) . ?
Pb1 N12A 2.613(4) . ?
Pb1 O2B 2.753(4) . ?
Pb1 C1B 2.869(4) . ?
N1A C6A 1.331(6) . ?
N1A C2A 1.343(6) . ?
C2A C3A 1.387(6) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.384(6) . ?
C3A C7A 1.493(5) . ?
C4A C5A 1.377(6) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.368(7) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A O7A 1.270(5) . ?
C7A N8A 1.319(5) . ?
N8A N9A 1.381(5) . ?
N9A C10A 1.296(5) . ?
C10A C11A 1.471(5) . ?
C10A C101 1.500(5) . ?
C101 H10A 0.9600 . ?
C101 H10B 0.9600 . ?
C101 H10C 0.9600 . ?
C11A N12A 1.360(5) . ?
C11A C16A 1.380(6) . ?
N12A C13A 1.331(5) . ?
C13A C14A 1.373(7) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.389(7) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.379(7) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C1B O2B 1.223(5) . ?
C1B O1B 1.273(5) . ?
C1B C2B 1.513(7) . ?
C2B H2B1 0.9600 . ?
C2B H2B2 0.9600 . ?
C2B H2B3 0.9600 . ?

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
O1B Pb1 O7A 84.69(13) . . ?
O1B Pb1 N9A 89.75(11) . . ?
O7A Pb1 N9A 64.36(10) . . ?
O1B Pb1 N12A 84.14(12) . . ?
O7A Pb1 N12A 126.05(10) . . ?
N9A Pb1 N12A 62.99(10) . . ?
O1B Pb1 O2B 50.55(11) . . ?
O7A Pb1 O2B 128.28(12) . . ?
N9A Pb1 O2B 128.36(13) . . ?
N12A Pb1 O2B 79.31(12) . . ?
O1B Pb1 C1B 25.57(12) . . ?
O7A Pb1 C1B 106.59(14) . . ?
N9A Pb1 C1B 110.88(12) . . ?
N12A Pb1 C1B 82.01(12) . . ?
O2B Pb1 C1B 25.03(11) . . ?
C6A N1A C2A 117.2(4) . . ?
N1A C2A C3A 123.4(4) . . ?
N1A C2A H2A 118.3 . . ?
C3A C2A H2A 118.3 . . ?
C4A C3A C2A 118.0(4) . . ?
C4A C3A C7A 122.8(4) . . ?
C2A C3A C7A 119.1(4) . . ?
C5A C4A C3A 118.3(4) . . ?
C5A C4A H4A 120.9 . . ?
C3A C4A H4A 120.9 . . ?
C6A C5A C4A 120.0(4) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
N1A C6A C5A 122.9(4) . . ?
N1A C6A H6A 118.5 . . ?
C5A C6A H6A 118.5 . . ?
O7A C7A N8A 127.1(4) . . ?
O7A C7A C3A 118.0(4) . . ?
N8A C7A C3A 114.9(3) . . ?
C7A O7A Pb1 117.1(3) . . ?
C7A N8A N9A 111.0(3) . . ?
C10A N9A N8A 117.6(3) . . ?
C10A N9A Pb1 124.9(2) . . ?
N8A N9A Pb1 117.3(2) . . ?
N9A C10A C11A 117.2(3) . . ?
N9A C10A C101 122.7(4) . . ?
C11A C10A C101 120.2(3) . . ?
C10A C101 H10A 109.5 . . ?
C10A C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C10A C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
N12A C11A C16A 121.3(4) . . ?
N12A C11A C10A 116.4(3) . . ?
C16A C11A C10A 122.3(4) . . ?
C13A N12A C11A 117.9(4) . . ?
C13A N12A Pb1 123.7(3) . . ?
C11A N12A Pb1 118.3(3) . . ?
N12A C13A C14A 123.8(4) . . ?
N12A C13A H13A 118.1 . . ?
C14A C13A H13A 118.1 . . ?
C13A C14A C15A 118.5(4) . . ?
C13A C14A H14A 120.8 . . ?
C15A C14A H14A 120.8 . . ?
C16A C15A C14A 118.4(5) . . ?
C16A C15A H15A 120.8 . . ?
C14A C15A H15A 120.8 . . ?
C15A C16A C11A 120.1(4) . . ?
C15A C16A H16A 120.0 . . ?
C11A C16A H16A 120.0 . . ?
O2B C1B O1B 123.1(4) . . ?
O2B C1B C2B 120.6(4) . . ?
O1B C1B C2B 116.3(4) . . ?
O2B C1B Pb1 72.2(3) . . ?
O1B C1B Pb1 51.1(2) . . ?
C2B C1B Pb1 166.6(4) . . ?
C1B O1B Pb1 103.3(3) . . ?
C1B O2B Pb1 82.8(3) . . ?
C1B C2B H2B1 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 109.5 . . ?
C1B C2B H2B3 109.5 . . ?
H2B1 C2B H2B3 109.5 . . ?
H2B2 C2B H2B3 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
C6A N1A C2A C3A 1.9(8) . . . . ?
N1A C2A C3A C4A -4.7(8) . . . . ?
N1A C2A C3A C7A 174.2(5) . . . . ?
C2A C3A C4A C5A 4.1(7) . . . . ?
C7A C3A C4A C5A -174.8(4) . . . . ?
C3A C4A C5A C6A -1.0(8) . . . . ?
C2A N1A C6A C5A 1.6(8) . . . . ?
C4A C5A C6A N1A -2.0(8) . . . . ?
C4A C3A C7A O7A -180.0(5) . . . . ?
C2A C3A C7A O7A 1.2(7) . . . . ?
C4A C3A C7A N8A -0.1(6) . . . . ?
C2A C3A C7A N8A -179.0(5) . . . . ?
N8A C7A O7A Pb1 16.7(7) . . . . ?
C3A C7A O7A Pb1 -163.5(3) . . . . ?
O7A C7A N8A N9A -3.2(7) . . . . ?
C3A C7A N8A N9A 177.0(4) . . . . ?
C7A N8A N9A C10A 174.2(4) . . . . ?
C7A N8A N9A Pb1 -11.4(5) . . . . ?
N8A N9A C10A C11A 177.6(4) . . . . ?
Pb1 N9A C10A C11A 3.6(5) . . . . ?
N8A N9A C10A C101 -2.1(6) . . . . ?
Pb1 N9A C10A C101 -176.1(3) . . . . ?
N9A C10A C11A N12A 1.5(6) . . . . ?
C101 C10A C11A N12A -178.8(4) . . . . ?
N9A C10A C11A C16A -178.9(4) . . . . ?
C101 C10A C11A C16A 0.8(6) . . . . ?
C16A C11A N12A C13A -0.1(7) . . . . ?
C10A C11A N12A C13A 179.5(4) . . . . ?
C16A C11A N12A Pb1 175.0(3) . . . . ?
C10A C11A N12A Pb1 -5.4(5) . . . . ?
C11A N12A C13A C14A 1.2(8) . . . . ?
Pb1 N12A C13A C14A -173.7(4) . . . . ?
N12A C13A C14A C15A -1.5(8) . . . . ?
C13A C14A C15A C16A 0.8(9) . . . . ?
C14A C15A C16A C11A 0.1(9) . . . . ?
N12A C11A C16A C15A -0.5(8) . . . . ?
C10A C11A C16A C15A 179.9(5) . . . . ?
O2B C1B O1B Pb1 -5.7(6) . . . . ?
C2B C1B O1B Pb1 174.5(4) . . . . ?
O1B C1B O2B Pb1 4.7(5) . . . . ?
C2B C1B O2B Pb1 -175.5(5) . . . . ?

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
C2A H2A O7A 0.93 2.40 3.060(6) 127.9 3_567
C101 H10B O1B 0.96 2.59 3.506(6) 160.2 3_666

_refine_diff_density_max         3.122
_refine_diff_density_min         -2.668
_refine_diff_density_rms         0.200

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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 1059559'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N4 O Pb, Cl O4, O'
_chemical_formula_sum            'C13 H11 Cl N4 O6 Pb'
_chemical_formula_weight         561.90

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      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                   10.0724(8)
_cell_length_b                   13.9283(11)
_cell_length_c                   13.2362(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.0650(10)
_cell_angle_gamma                90
_cell_volume                     1720.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    9.996
_shelx_estimated_absorpt_T_min   0.115
_shelx_estimated_absorpt_T_max   0.240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1154
_exptl_absorpt_correction_T_max  0.2397
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            9073
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.190
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3042
_reflns_number_gt                2737
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_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)+(0.0500P)²+3.3183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3042
_refine_ls_number_parameters     273
_refine_ls_number_restraints     130
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      1.042
_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 0.29045(2) 0.59875(2) 0.37139(2) 0.01724(9) Uani 1 1 d . . . . .
N1A N 0.8437(4) 0.7933(3) 0.7398(3) 0.0196(9) Uani 1 1 d . . . . .
C2A C 0.7334(5) 0.7477(3) 0.6654(4) 0.0170(10) Uani 1 1 d . . . . .
H2A H 0.6393 0.7637 0.6602 0.020 Uiso 1 1 calc R U . . .
C3A C 0.7488(5) 0.6781(3) 0.5953(4) 0.0164(10) Uani 1 1 d . . . . .
C4A C 0.8872(6) 0.6558(4) 0.6015(4) 0.0239(11) Uani 1 1 d . . . . .
H4A H 0.9024 0.6092 0.5545 0.029 Uiso 1 1 calc R U . . .
C5A C 1.0007(6) 0.7034(4) 0.6781(5) 0.0294(12) Uani 1 1 d . . . . .
H5A H 1.0959 0.6892 0.6846 0.035 Uiso 1 1 calc R U . . .
C6A C 0.9773(5) 0.7714(4) 0.7451(4) 0.0255(12) Uani 1 1 d . . . . .
H6A H 1.0571 0.8040 0.7964 0.031 Uiso 1 1 calc R U . . .
C7A C 0.6176(5) 0.6340(3) 0.5140(4) 0.0158(10) Uani 1 1 d . . . . .
O7A O 0.4989(4) 0.6754(2) 0.4963(3) 0.0209(7) Uani 1 1 d . . . . .
N8A N 0.6391(4) 0.5550(3) 0.4653(3) 0.0169(8) Uani 1 1 d . . . . .
N9A N 0.5123(4) 0.5265(3) 0.3816(3) 0.0162(8) Uani 1 1 d . . . . .
C10A C 0.5218(5) 0.4596(3) 0.3164(4) 0.0176(10) Uani 1 1 d . . . . .
C101 C 0.6559(6) 0.4098(3) 0.3275(5) 0.0247(12) Uani 1 1 d . . . . .
H10A H 0.7349 0.4352 0.3909 0.037 Uiso 1 1 calc R U . . .
H10B H 0.6766 0.4202 0.2616 0.037 Uiso 1 1 calc R U . . .
H10C H 0.6454 0.3408 0.3373 0.037 Uiso 1 1 calc R U . . .
C11A C 0.3851(6) 0.4342(3) 0.2254(4) 0.0198(10) Uani 1 1 d . . . . .
N12A N 0.2655(5) 0.4768(3) 0.2254(3) 0.0213(9) Uani 1 1 d . . . . .
C13A C 0.1406(6) 0.4548(4) 0.1470(5) 0.0297(13) Uani 1 1 d . . . . .
H13A H 0.0563 0.4842 0.1485 0.036 Uiso 1 1 calc R U . . .
C14A C 0.1275(7) 0.3914(4) 0.0638(5) 0.0330(14) Uani 1 1 d . . . . .
H14A H 0.0364 0.3768 0.0097 0.040 Uiso 1 1 calc R U . . .
C15A C 0.2514(6) 0.3495(4) 0.0611(5) 0.0306(13) Uani 1 1 d . . . . .
H15A H 0.2467 0.3075 0.0033 0.037 Uiso 1 1 calc R U . . .
C16A C 0.3825(6) 0.3696(4) 0.1442(4) 0.0269(12) Uani 1 1 d . . . . .
H16A H 0.4681 0.3400 0.1455 0.032 Uiso 1 1 calc R U . . .
Cl1B Cl 0.89237(16) 0.62213(11) 0.27814(14) 0.0389(4) Uani 1 1 d D U . . .
O1B O 0.9725(5) 0.6602(3) 0.2172(4) 0.0455(11) Uani 1 1 d D U . . .
O2B O 0.7471(8) 0.5988(8) 0.2071(9) 0.059(3) Uani 0.581(13) 1 d D U P A 1
O3B O 0.9581(9) 0.5524(8) 0.3556(9) 0.066(3) Uani 0.581(13) 1 d D U P A 1
O4B O 0.8642(13) 0.7042(6) 0.3412(9) 0.073(4) Uani 0.581(13) 1 d D U P A 1
O2'B O 0.7496(9) 0.6454(12) 0.2342(13) 0.068(4) Uani 0.419(13) 1 d D U P A 2
O3'B O 0.9202(19) 0.5199(6) 0.2794(18) 0.085(5) Uani 0.419(13) 1 d D U P A 2
O4'B O 0.9675(16) 0.6587(13) 0.3882(7) 0.084(5) Uani 0.419(13) 1 d D U P A 2
O1W1 O 0.152(2) 0.0940(9) 0.5059(15) 0.091(6) Uani 0.4 1 d . U P B 1
O1W2 O 0.250(3) 0.1071(17) 0.567(2) 0.083(7) Uani 0.3 1 d . U P C 2
O1W3 O 0.087(2) 0.0089(17) 0.5548(17) 0.085(6) Uani 0.3 1 d . U P D 3


_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 O7A 2.382(3) . ?
Pb1 N9A 2.408(4) . ?
Pb1 N1A 2.506(4) 4_575 ?
Pb1 N12A 2.513(4) . ?
N1A C2A 1.337(6) . ?
N1A C6A 1.356(7) . ?
N1A Pb1 2.506(4) 4_676 ?
C2A C3A 1.391(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.400(7) . ?
C3A C7A 1.487(7) . ?
C4A C5A 1.380(8) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.377(7) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O7A 1.268(6) . ?
C7A N8A 1.333(6) . ?
N8A N9A 1.398(6) . ?
N9A C10A 1.298(6) . ?
C10A C101 1.477(7) . ?
C10A C11A 1.492(7) . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C11A N12A 1.343(7) . ?
C11A C16A 1.395(8) . ?
N12A C13A 1.331(7) . ?
C13A C14A 1.379(8) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.390(9) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.393(8) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
Cl1B O2'B 1.372(7) . ?
Cl1B O3B 1.387(6) . ?
Cl1B O1B 1.440(4) . ?
Cl1B O2B 1.448(7) . ?
Cl1B O3'B 1.450(8) . ?
Cl1B O4'B 1.458(8) . ?
Cl1B O4B 1.504(7) . ?

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
O7A Pb1 N9A 65.86(12) . . ?
O7A Pb1 N1A 81.40(13) . 4_575 ?
N9A Pb1 N1A 81.57(13) . 4_575 ?
O7A Pb1 N12A 130.11(12) . . ?
N9A Pb1 N12A 65.38(13) . . ?
N1A Pb1 N12A 81.80(13) 4_575 . ?
C2A N1A C6A 117.7(4) . . ?
C2A N1A Pb1 117.5(3) . 4_676 ?
C6A N1A Pb1 124.5(3) . 4_676 ?
N1A C2A C3A 123.5(4) . . ?
N1A C2A H2A 118.2 . . ?
C3A C2A H2A 118.2 . . ?
C2A C3A C4A 118.3(5) . . ?
C2A C3A C7A 118.6(4) . . ?
C4A C3A C7A 123.0(4) . . ?
C5A C4A C3A 117.9(5) . . ?
C5A C4A H4A 121.0 . . ?
C3A C4A H4A 121.0 . . ?
C6A C5A C4A 120.6(5) . . ?
C6A C5A H5A 119.7 . . ?
C4A C5A H5A 119.7 . . ?
N1A C6A C5A 121.9(5) . . ?
N1A C6A H6A 119.1 . . ?
C5A C6A H6A 119.1 . . ?
O7A C7A N8A 126.8(4) . . ?
O7A C7A C3A 117.8(4) . . ?
N8A C7A C3A 115.4(4) . . ?
C7A O7A Pb1 116.7(3) . . ?
C7A N8A N9A 110.6(4) . . ?
C10A N9A N8A 117.3(4) . . ?
C10A N9A Pb1 124.2(3) . . ?
N8A N9A Pb1 118.5(3) . . ?
N9A C10A C101 124.4(5) . . ?
N9A C10A C11A 115.5(4) . . ?
C101 C10A C11A 120.1(4) . . ?
C10A C101 H10A 109.5 . . ?
C10A C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C10A C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
N12A C11A C16A 121.9(5) . . ?
N12A C11A C10A 116.8(4) . . ?
C16A C11A C10A 121.3(5) . . ?
C13A N12A C11A 118.9(5) . . ?
C13A N12A Pb1 123.2(4) . . ?
C11A N12A Pb1 117.9(3) . . ?
N12A C13A C14A 123.3(6) . . ?
N12A C13A H13A 118.4 . . ?
C14A C13A H13A 118.4 . . ?
C13A C14A C15A 118.2(6) . . ?
C13A C14A H14A 120.9 . . ?
C15A C14A H14A 120.9 . . ?
C16A C15A C14A 119.3(5) . . ?
C16A C15A H15A 120.4 . . ?
C14A C15A H15A 120.4 . . ?
C15A C16A C11A 118.4(5) . . ?
C15A C16A H16A 120.8 . . ?
C11A C16A H16A 120.8 . . ?
O2'B Cl1B O1B 113.3(6) . . ?
O3B Cl1B O1B 117.4(4) . . ?
O3B Cl1B O2B 114.1(6) . . ?
O1B Cl1B O2B 111.2(5) . . ?
O2'B Cl1B O3'B 113.8(9) . . ?
O1B Cl1B O3'B 102.8(6) . . ?
O2'B Cl1B O4'B 114.1(8) . . ?
O1B Cl1B O4'B 104.0(6) . . ?
O3'B Cl1B O4'B 107.8(9) . . ?
O3B Cl1B O4B 105.0(6) . . ?
O1B Cl1B O4B 107.1(4) . . ?
O2B Cl1B O4B 100.1(6) . . ?

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
C6A N1A C2A C3A 1.4(7) . . . . ?
Pb1 N1A C2A C3A -172.9(4) 4_676 . . . ?
N1A C2A C3A C4A -1.2(7) . . . . ?
N1A C2A C3A C7A -178.6(4) . . . . ?
C2A C3A C4A C5A 0.8(7) . . . . ?
C7A C3A C4A C5A 178.0(5) . . . . ?
C3A C4A C5A C6A -0.7(8) . . . . ?
C2A N1A C6A C5A -1.3(8) . . . . ?
Pb1 N1A C6A C5A 172.6(4) 4_676 . . . ?
C4A C5A C6A N1A 0.9(9) . . . . ?
C2A C3A C7A O7A 14.8(6) . . . . ?
C4A C3A C7A O7A -162.5(5) . . . . ?
C2A C3A C7A N8A -166.6(4) . . . . ?
C4A C3A C7A N8A 16.1(7) . . . . ?
N8A C7A O7A Pb1 4.2(6) . . . . ?
C3A C7A O7A Pb1 -177.4(3) . . . . ?
O7A C7A N8A N9A 5.7(7) . . . . ?
C3A C7A N8A N9A -172.7(4) . . . . ?
C7A N8A N9A C10A 169.7(4) . . . . ?
C7A N8A N9A Pb1 -12.8(5) . . . . ?
N8A N9A C10A C101 2.4(7) . . . . ?
Pb1 N9A C10A C101 -175.0(3) . . . . ?
N8A N9A C10A C11A -177.5(4) . . . . ?
Pb1 N9A C10A C11A 5.1(6) . . . . ?
N9A C10A C11A N12A -5.3(6) . . . . ?
C101 C10A C11A N12A 174.7(4) . . . . ?
N9A C10A C11A C16A 174.4(5) . . . . ?
C101 C10A C11A C16A -5.6(7) . . . . ?
C16A C11A N12A C13A 1.6(7) . . . . ?
C10A C11A N12A C13A -178.7(4) . . . . ?
C16A C11A N12A Pb1 -176.4(4) . . . . ?
C10A C11A N12A Pb1 3.3(5) . . . . ?
C11A N12A C13A C14A -1.3(8) . . . . ?
Pb1 N12A C13A C14A 176.7(4) . . . . ?
N12A C13A C14A C15A -0.8(9) . . . . ?
C13A C14A C15A C16A 2.6(8) . . . . ?
C14A C15A C16A C11A -2.2(8) . . . . ?
N12A C11A C16A C15A 0.1(8) . . . . ?
C10A C11A C16A C15A -179.6(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
C2A H2A O1B 0.95 2.34 3.220(6) 154.2 4_576
C6A H6A O2'B 0.95 2.48 3.029(11) 117.1 4_676
C16A H16A O4B 0.95 2.50 3.388(11) 156.2 2_645

_refine_diff_density_max         1.367
_refine_diff_density_min         -1.171
_refine_diff_density_rms         0.143

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1059560'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N5 O3 Pb'
_chemical_formula_sum            'C13 H11 N5 O3 Pb'
_chemical_formula_weight         492.46

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                   15.4332(16)
_cell_length_b                   9.3720(10)
_cell_length_c                   10.1192(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.149(2)
_cell_angle_gamma                90
_cell_volume                     1430.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.286
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    11.812
_shelx_estimated_absorpt_T_min   0.072
_shelx_estimated_absorpt_T_max   0.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0720
_exptl_absorpt_correction_T_max  0.6494
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            10487
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         25.032
_diffrn_reflns_theta_full        25.000
_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             2521
_reflns_number_gt                2276
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2521
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.27358(2) 0.70284(2) 0.76428(2) 0.01712(12) Uani 1 1 d . . . . .
N1A N 0.6290(3) 0.9744(5) 0.6146(4) 0.0193(10) Uani 1 1 d . . . . .
C2A C 0.5562(4) 0.9156(6) 0.6430(5) 0.0200(12) Uani 1 1 d . . . . .
H2A H 0.5350 0.9516 0.7181 0.024 Uiso 1 1 calc R U . . .
C3A C 0.5095(4) 0.8040(5) 0.5684(6) 0.0186(13) Uani 1 1 d . . . . .
C4A C 0.5423(4) 0.7513(7) 0.4595(5) 0.0208(12) Uani 1 1 d . . . . .
H4A H 0.5144 0.6726 0.4085 0.025 Uiso 1 1 calc R U . . .
C5A C 0.6158(5) 0.8150(6) 0.4267(6) 0.0244(14) Uani 1 1 d . . . . .
H5A H 0.6378 0.7834 0.3509 0.029 Uiso 1 1 calc R U . . .
C6A C 0.6566(4) 0.9255(6) 0.5065(5) 0.0229(12) Uani 1 1 d . . . . .
H6A H 0.7069 0.9690 0.4833 0.028 Uiso 1 1 calc R U . . .
C7A C 0.4290(4) 0.7455(6) 0.6052(5) 0.0198(12) Uani 1 1 d . . . . .
O7A O 0.4010(3) 0.8037(4) 0.7019(4) 0.0230(9) Uani 1 1 d . . . . .
N8A N 0.3906(3) 0.6374(5) 0.5284(4) 0.0182(10) Uani 1 1 d . . . . .
N9A N 0.3175(3) 0.5859(4) 0.5717(4) 0.0180(9) Uani 1 1 d . . . . .
C10A C 0.2682(4) 0.4921(5) 0.4969(5) 0.0187(11) Uani 1 1 d . . . . .
C101 C 0.2841(4) 0.4405(6) 0.3624(5) 0.0228(12) Uani 1 1 d . . . . .
H10C H 0.3392 0.4823 0.3462 0.034 Uiso 1 1 calc R U . . .
H10B H 0.2345 0.4695 0.2901 0.034 Uiso 1 1 calc R U . . .
H10A H 0.2890 0.3362 0.3638 0.034 Uiso 1 1 calc R U . . .
C11A C 0.1915(4) 0.4375(6) 0.5464(5) 0.0224(12) Uani 1 1 d . . . . .
N12A N 0.1722(3) 0.5039(5) 0.6545(4) 0.0228(10) Uani 1 1 d . . . . .
C13A C 0.1022(4) 0.4597(7) 0.7016(6) 0.0313(14) Uani 1 1 d . . . . .
H13A H 0.0879 0.5092 0.7761 0.038 Uiso 1 1 calc R U . . .
C14A C 0.0496(5) 0.3457(8) 0.6478(7) 0.0414(17) Uani 1 1 d . . . . .
H14A H -0.0001 0.3177 0.6832 0.050 Uiso 1 1 calc R U . . .
C15A C 0.0723(6) 0.2732(9) 0.5395(8) 0.045(2) Uani 1 1 d . . . . .
H15A H 0.0403 0.1906 0.5028 0.055 Uiso 1 1 calc R U . . .
C16A C 0.1414(5) 0.3226(7) 0.4867(7) 0.0373(17) Uani 1 1 d . . . . .
H16A H 0.1550 0.2783 0.4091 0.045 Uiso 1 1 calc R U . . .
N1B N 0.1271(3) 0.8797(6) 0.5578(5) 0.0360(13) Uani 1 1 d . . . . .
O11B O 0.1101(3) 0.8601(7) 0.6701(5) 0.0506(13) Uani 1 1 d . . . . .
O12B O 0.2007(3) 0.8299(5) 0.5468(4) 0.0303(10) 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 O7A 2.384(4) . ?
Pb1 N9A 2.452(4) . ?
Pb1 N12A 2.535(5) . ?
Pb1 O12B 2.547(4) . ?
Pb1 N1A 2.752(4) 2_646 ?
N1A C2A 1.335(7) . ?
N1A C6A 1.336(7) . ?
N1A Pb1 2.752(4) 2_656 ?
C2A C3A 1.398(8) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.396(8) . ?
C3A C7A 1.476(9) . ?
C4A C5A 1.383(9) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.380(8) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O7A 1.273(7) . ?
C7A N8A 1.337(7) . ?
N8A N9A 1.380(6) . ?
N9A C10A 1.298(7) . ?
C10A C11A 1.471(8) . ?
C10A C101 1.512(7) . ?
C101 H10C 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10A 0.9800 . ?
C11A N12A 1.345(7) . ?
C11A C16A 1.388(9) . ?
N12A C13A 1.335(8) . ?
C13A C14A 1.383(9) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.396(10) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.370(11) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
N1B O11B 1.233(7) . ?
N1B O12B 1.254(7) . ?

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
O7A Pb1 N9A 65.51(13) . . ?
O7A Pb1 N12A 130.02(13) . . ?
N9A Pb1 N12A 64.62(14) . . ?
O7A Pb1 O12B 79.92(14) . . ?
N9A Pb1 O12B 70.63(14) . . ?
N12A Pb1 O12B 81.11(14) . . ?
O7A Pb1 N1A 91.28(14) . 2_646 ?
N9A Pb1 N1A 77.83(13) . 2_646 ?
N12A Pb1 N1A 81.49(15) . 2_646 ?
O12B Pb1 N1A 148.14(13) . 2_646 ?
C2A N1A C6A 117.5(5) . . ?
C2A N1A Pb1 129.1(3) . 2_656 ?
C6A N1A Pb1 113.1(4) . 2_656 ?
N1A C2A C3A 123.7(5) . . ?
N1A C2A H2A 118.2 . . ?
C3A C2A H2A 118.2 . . ?
C4A C3A C2A 117.4(6) . . ?
C4A C3A C7A 122.1(5) . . ?
C2A C3A C7A 120.5(5) . . ?
C5A C4A C3A 119.2(5) . . ?
C5A C4A H4A 120.4 . . ?
C3A C4A H4A 120.4 . . ?
C6A C5A C4A 118.7(5) . . ?
C6A C5A H5A 120.7 . . ?
C4A C5A H5A 120.7 . . ?
N1A C6A C5A 123.5(5) . . ?
N1A C6A H6A 118.3 . . ?
C5A C6A H6A 118.3 . . ?
O7A C7A N8A 126.3(5) . . ?
O7A C7A C3A 118.3(5) . . ?
N8A C7A C3A 115.4(5) . . ?
C7A O7A Pb1 117.7(3) . . ?
C7A N8A N9A 111.8(4) . . ?
C10A N9A N8A 118.0(4) . . ?
C10A N9A Pb1 122.7(3) . . ?
N8A N9A Pb1 118.5(3) . . ?
N9A C10A C11A 116.8(4) . . ?
N9A C10A C101 123.8(5) . . ?
C11A C10A C101 119.4(5) . . ?
C10A C101 H10C 109.5 . . ?
C10A C101 H10B 109.5 . . ?
H10C C101 H10B 109.5 . . ?
C10A C101 H10A 109.5 . . ?
H10C C101 H10A 109.5 . . ?
H10B C101 H10A 109.5 . . ?
N12A C11A C16A 120.9(6) . . ?
N12A C11A C10A 116.7(5) . . ?
C16A C11A C10A 122.4(5) . . ?
C13A N12A C11A 118.8(5) . . ?
C13A N12A Pb1 122.9(4) . . ?
C11A N12A Pb1 118.3(4) . . ?
N12A C13A C14A 123.5(6) . . ?
N12A C13A H13A 118.3 . . ?
C14A C13A H13A 118.3 . . ?
C13A C14A C15A 117.5(6) . . ?
C13A C14A H14A 121.3 . . ?
C15A C14A H14A 121.3 . . ?
C16A C15A C14A 119.1(7) . . ?
C16A C15A H15A 120.4 . . ?
C14A C15A H15A 120.4 . . ?
C15A C16A C11A 120.0(6) . . ?
C15A C16A H16A 120.0 . . ?
C11A C16A H16A 120.0 . . ?
O11B N1B O12B 113.5(5) . . ?
N1B O12B Pb1 109.9(3) . . ?

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
C6A N1A C2A C3A 1.9(8) . . . . ?
Pb1 N1A C2A C3A 176.1(4) 2_656 . . . ?
N1A C2A C3A C4A 0.8(8) . . . . ?
N1A C2A C3A C7A -179.4(5) . . . . ?
C2A C3A C4A C5A -3.0(8) . . . . ?
C7A C3A C4A C5A 177.2(5) . . . . ?
C3A C4A C5A C6A 2.5(9) . . . . ?
C2A N1A C6A C5A -2.4(8) . . . . ?
Pb1 N1A C6A C5A -177.6(5) 2_656 . . . ?
C4A C5A C6A N1A 0.2(9) . . . . ?
C4A C3A C7A O7A -176.8(5) . . . . ?
C2A C3A C7A O7A 3.4(8) . . . . ?
C4A C3A C7A N8A 1.0(8) . . . . ?
C2A C3A C7A N8A -178.8(5) . . . . ?
N8A C7A O7A Pb1 4.4(7) . . . . ?
C3A C7A O7A Pb1 -178.1(4) . . . . ?
O7A C7A N8A N9A -4.3(8) . . . . ?
C3A C7A N8A N9A 178.1(4) . . . . ?
C7A N8A N9A C10A 172.1(5) . . . . ?
C7A N8A N9A Pb1 2.0(5) . . . . ?
N8A N9A C10A C11A 179.1(4) . . . . ?
Pb1 N9A C10A C11A -11.2(6) . . . . ?
N8A N9A C10A C101 -2.5(7) . . . . ?
Pb1 N9A C10A C101 167.2(4) . . . . ?
N9A C10A C11A N12A 9.1(7) . . . . ?
C101 C10A C11A N12A -169.3(5) . . . . ?
N9A C10A C11A C16A -170.4(6) . . . . ?
C101 C10A C11A C16A 11.2(8) . . . . ?
C16A C11A N12A C13A -1.7(9) . . . . ?
C10A C11A N12A C13A 178.9(5) . . . . ?
C16A C11A N12A Pb1 176.4(5) . . . . ?
C10A C11A N12A Pb1 -3.1(6) . . . . ?
C11A N12A C13A C14A 2.1(9) . . . . ?
Pb1 N12A C13A C14A -175.9(5) . . . . ?
N12A C13A C14A C15A 0.7(11) . . . . ?
C13A C14A C15A C16A -3.9(12) . . . . ?
C14A C15A C16A C11A 4.3(12) . . . . ?
N12A C11A C16A C15A -1.5(11) . . . . ?
C10A C11A C16A C15A 177.9(7) . . . . ?
O11B N1B O12B Pb1 2.5(6) . . . . ?

_refine_diff_density_max         1.480
_refine_diff_density_min         -2.465
_refine_diff_density_rms         0.238

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1059561'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N4 O3 Pb, Cl O4'
_chemical_formula_sum            'C15 H15 Cl N4 O7 Pb'
_chemical_formula_weight         605.95

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

_cell_length_a                   12.8619(4)
_cell_length_b                   15.9903(5)
_cell_length_c                   18.1591(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3734.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    9.225
_shelx_estimated_absorpt_T_min   0.236
_shelx_estimated_absorpt_T_max   0.459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2383
_exptl_absorpt_correction_T_max  0.4471
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            14736
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.321
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_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             3288
_reflns_number_gt                2240
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3288
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 0.74134(2) 0.60111(2) 0.56881(2) 0.03594(13) Uani 1 1 d . . . . .
N1A N 0.2603(5) 0.7517(4) 0.5089(4) 0.0430(17) Uani 1 1 d . . . . .
C2A C 0.3543(6) 0.7166(5) 0.5163(5) 0.037(2) Uani 1 1 d . . . . .
H2A H 0.4097 0.7385 0.4896 0.044 Uiso 1 1 calc R U . . .
C3A C 0.3717(5) 0.6494(4) 0.5619(4) 0.0277(18) Uani 1 1 d . . . . .
C4A C 0.2915(6) 0.6209(5) 0.6044(5) 0.0372(19) Uani 1 1 d . . . . .
H4A H 0.3018 0.5775 0.6377 0.045 Uiso 1 1 calc R U . . .
C5A C 0.1948(7) 0.6578(6) 0.5972(5) 0.049(2) Uani 1 1 d . . . . .
H5A H 0.1387 0.6394 0.6251 0.058 Uiso 1 1 calc R U . . .
C6A C 0.1837(7) 0.7217(5) 0.5481(5) 0.050(3) Uani 1 1 d . . . . .
H6A H 0.1181 0.7451 0.5422 0.061 Uiso 1 1 calc R U . . .
C7A C 0.4781(5) 0.6142(5) 0.5660(4) 0.0325(18) Uani 1 1 d . . . . .
O7A O 0.5555(4) 0.6559(3) 0.5488(3) 0.0488(16) Uani 1 1 d . . . . .
N8A N 0.4857(4) 0.5327(3) 0.5888(4) 0.0343(16) Uani 1 1 d . . . . .
H8A H 0.4302 0.5026 0.5988 0.041 Uiso 1 1 calc R U . . .
N9A N 0.5839(4) 0.5003(4) 0.5953(3) 0.0311(15) Uani 1 1 d . . . . .
C10A C 0.5955(6) 0.4291(5) 0.6277(4) 0.0315(19) Uani 1 1 d . . . . .
C101 C 0.5095(6) 0.3802(5) 0.6598(5) 0.051(2) Uani 1 1 d . . . . .
H10C H 0.4577 0.3701 0.6228 0.076 Uiso 1 1 calc R U . . .
H10B H 0.4792 0.4108 0.6999 0.076 Uiso 1 1 calc R U . . .
H10A H 0.5358 0.3277 0.6776 0.076 Uiso 1 1 calc R U . . .
C11A C 0.7061(6) 0.3982(4) 0.6312(4) 0.0289(17) Uani 1 1 d . . . . .
N12A N 0.7768(5) 0.4433(4) 0.5961(4) 0.0406(17) Uani 1 1 d . . . . .
C13A C 0.8772(6) 0.4173(5) 0.5949(5) 0.051(2) Uani 1 1 d . . . . .
H13A H 0.9264 0.4487 0.5695 0.061 Uiso 1 1 calc R U . . .
C14A C 0.9080(7) 0.3447(6) 0.6311(5) 0.050(3) Uani 1 1 d . . . . .
H14A H 0.9766 0.3266 0.6291 0.060 Uiso 1 1 calc R U . . .
C15A C 0.8353(6) 0.3009(5) 0.6695(5) 0.048(2) Uani 1 1 d . . . . .
H15A H 0.8548 0.2537 0.6960 0.057 Uiso 1 1 calc R U . . .
C16A C 0.7325(6) 0.3265(5) 0.6690(5) 0.043(2) Uani 1 1 d . . . . .
H16A H 0.6821 0.2958 0.6938 0.051 Uiso 1 1 calc R U . . .
C1B C 0.7943(7) 0.5706(5) 0.4218(5) 0.044(2) Uani 1 1 d . . . . .
O11B O 0.7001(4) 0.5651(3) 0.4455(3) 0.0415(14) Uani 1 1 d . . . . .
O12B O 0.8677(4) 0.5763(4) 0.4654(4) 0.0513(16) Uani 1 1 d . . . . .
C2B C 0.8115(8) 0.5737(7) 0.3373(6) 0.077(3) Uani 1 1 d . . . . .
H2B3 H 0.8774 0.5489 0.3255 0.116 Uiso 1 1 calc R U . . .
H2B2 H 0.8106 0.6308 0.3210 0.116 Uiso 1 1 calc R U . . .
H2B1 H 0.7570 0.5432 0.3131 0.116 Uiso 1 1 calc R U . . .
Cl1C Cl 0.94073(18) 0.62269(16) 0.71811(15) 0.0562(6) Uani 1 1 d . . . . .
O1C O 0.8568(9) 0.5742(7) 0.7299(5) 0.166(6) Uani 1 1 d . . . . .
O2C O 0.9369(8) 0.6919(5) 0.7645(4) 0.103(3) Uani 1 1 d . . . . .
O3C O 1.0348(10) 0.5815(9) 0.7395(6) 0.177(6) Uani 1 1 d . . . . .
O4C O 0.9464(5) 0.6455(5) 0.6432(4) 0.075(2) 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 O11B 2.373(5) . ?
Pb1 O12B 2.516(6) . ?
Pb1 O7A 2.572(5) . ?
Pb1 N12A 2.612(7) . ?
Pb1 N9A 2.632(6) . ?
Pb1 N1A 2.755(7) 2_566 ?
Pb1 C1B 2.798(9) . ?
N1A C6A 1.307(10) . ?
N1A C2A 1.339(9) . ?
N1A Pb1 2.754(7) 2_466 ?
C2A C3A 1.375(10) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.368(11) . ?
C3A C7A 1.482(9) . ?
C4A C5A 1.382(11) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.364(11) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A O7A 1.239(8) . ?
C7A N8A 1.371(9) . ?
N8A N9A 1.371(7) . ?
N8A H8A 0.8800 . ?
N9A C10A 1.290(9) . ?
C10A C101 1.475(10) . ?
C10A C11A 1.508(10) . ?
C101 H10C 0.9600 . ?
C101 H10B 0.9600 . ?
C101 H10A 0.9600 . ?
C11A N12A 1.324(10) . ?
C11A C16A 1.380(10) . ?
N12A C13A 1.357(10) . ?
C13A C14A 1.391(12) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.359(12) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.384(10) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C1B O12B 1.235(10) . ?
C1B O11B 1.288(11) . ?
C1B C2B 1.551(12) . ?
C2B H2B3 0.9600 . ?
C2B H2B2 0.9600 . ?
C2B H2B1 0.9600 . ?
Cl1C O1C 1.346(8) . ?
Cl1C O2C 1.392(8) . ?
Cl1C O4C 1.409(6) . ?
Cl1C O3C 1.432(10) . ?

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
O11B Pb1 O12B 53.22(19) . . ?
O11B Pb1 O7A 75.0(2) . . ?
O12B Pb1 O7A 123.3(2) . . ?
O11B Pb1 N12A 89.0(2) . . ?
O12B Pb1 N12A 82.9(2) . . ?
O7A Pb1 N12A 121.23(17) . . ?
O11B Pb1 N9A 81.49(19) . . ?
O12B Pb1 N9A 122.48(19) . . ?
O7A Pb1 N9A 61.31(17) . . ?
N12A Pb1 N9A 60.52(18) . . ?
O11B Pb1 N1A 75.1(2) . 2_566 ?
O12B Pb1 N1A 72.24(19) . 2_566 ?
O7A Pb1 N1A 73.65(17) . 2_566 ?
N12A Pb1 N1A 155.1(2) . 2_566 ?
N9A Pb1 N1A 133.23(18) . 2_566 ?
O11B Pb1 C1B 27.3(2) . . ?
O12B Pb1 C1B 26.2(2) . . ?
O7A Pb1 C1B 98.7(2) . . ?
N12A Pb1 C1B 88.3(2) . . ?
N9A Pb1 C1B 104.8(2) . . ?
N1A Pb1 C1B 68.8(2) 2_566 . ?
C6A N1A C2A 118.1(7) . . ?
C6A N1A Pb1 121.8(5) . 2_466 ?
C2A N1A Pb1 119.3(5) . 2_466 ?
N1A C2A C3A 122.4(7) . . ?
N1A C2A H2A 118.8 . . ?
C3A C2A H2A 118.8 . . ?
C4A C3A C2A 118.6(7) . . ?
C4A C3A C7A 122.8(7) . . ?
C2A C3A C7A 118.6(7) . . ?
C3A C4A C5A 118.9(8) . . ?
C3A C4A H4A 120.6 . . ?
C5A C4A H4A 120.6 . . ?
C6A C5A C4A 118.4(8) . . ?
C6A C5A H5A 120.8 . . ?
C4A C5A H5A 120.8 . . ?
N1A C6A C5A 123.6(8) . . ?
N1A C6A H6A 118.2 . . ?
C5A C6A H6A 118.2 . . ?
O7A C7A N8A 122.1(7) . . ?
O7A C7A C3A 121.6(7) . . ?
N8A C7A C3A 116.3(6) . . ?
C7A O7A Pb1 121.8(5) . . ?
N9A N8A C7A 116.8(6) . . ?
N9A N8A H8A 121.6 . . ?
C7A N8A H8A 121.6 . . ?
C10A N9A N8A 118.6(6) . . ?
C10A N9A Pb1 122.4(5) . . ?
N8A N9A Pb1 117.5(4) . . ?
N9A C10A C101 124.2(7) . . ?
N9A C10A C11A 114.6(6) . . ?
C101 C10A C11A 121.2(7) . . ?
C10A C101 H10C 109.5 . . ?
C10A C101 H10B 109.5 . . ?
H10C C101 H10B 109.5 . . ?
C10A C101 H10A 109.5 . . ?
H10C C101 H10A 109.5 . . ?
H10B C101 H10A 109.5 . . ?
N12A C11A C16A 121.6(7) . . ?
N12A C11A C10A 116.7(7) . . ?
C16A C11A C10A 121.7(7) . . ?
C11A N12A C13A 119.6(7) . . ?
C11A N12A Pb1 119.8(5) . . ?
C13A N12A Pb1 117.3(6) . . ?
N12A C13A C14A 121.2(8) . . ?
N12A C13A H13A 119.4 . . ?
C14A C13A H13A 119.4 . . ?
C15A C14A C13A 118.5(8) . . ?
C15A C14A H14A 120.8 . . ?
C13A C14A H14A 120.8 . . ?
C14A C15A C16A 120.1(8) . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C11A C16A C15A 118.9(8) . . ?
C11A C16A H16A 120.5 . . ?
C15A C16A H16A 120.5 . . ?
O12B C1B O11B 120.7(8) . . ?
O12B C1B C2B 121.5(9) . . ?
O11B C1B C2B 117.8(8) . . ?
O12B C1B Pb1 64.1(5) . . ?
O11B C1B Pb1 57.7(4) . . ?
C2B C1B Pb1 166.7(7) . . ?
C1B O11B Pb1 95.0(5) . . ?
C1B O12B Pb1 89.7(5) . . ?
C1B C2B H2B3 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B3 C2B H2B2 109.5 . . ?
C1B C2B H2B1 109.5 . . ?
H2B3 C2B H2B1 109.5 . . ?
H2B2 C2B H2B1 109.5 . . ?
O1C Cl1C O2C 109.4(6) . . ?
O1C Cl1C O4C 110.1(5) . . ?
O2C Cl1C O4C 112.3(5) . . ?
O1C Cl1C O3C 111.7(9) . . ?
O2C Cl1C O3C 103.4(7) . . ?
O4C Cl1C O3C 109.8(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
C6A N1A C2A C3A 1.7(12) . . . . ?
Pb1 N1A C2A C3A 171.5(6) 2_466 . . . ?
N1A C2A C3A C4A -4.1(12) . . . . ?
N1A C2A C3A C7A 179.4(7) . . . . ?
C2A C3A C4A C5A 3.4(12) . . . . ?
C7A C3A C4A C5A 179.7(7) . . . . ?
C3A C4A C5A C6A -0.5(13) . . . . ?
C2A N1A C6A C5A 1.5(13) . . . . ?
Pb1 N1A C6A C5A -168.1(7) 2_466 . . . ?
C4A C5A C6A N1A -2.1(14) . . . . ?
C4A C3A C7A O7A -154.3(8) . . . . ?
C2A C3A C7A O7A 22.1(12) . . . . ?
C4A C3A C7A N8A 26.7(11) . . . . ?
C2A C3A C7A N8A -157.0(7) . . . . ?
N8A C7A O7A Pb1 -7.7(11) . . . . ?
C3A C7A O7A Pb1 173.3(5) . . . . ?
O7A C7A N8A N9A 3.2(11) . . . . ?
C3A C7A N8A N9A -177.8(6) . . . . ?
C7A N8A N9A C10A 168.9(7) . . . . ?
C7A N8A N9A Pb1 2.6(8) . . . . ?
N8A N9A C10A C101 -1.1(12) . . . . ?
Pb1 N9A C10A C101 164.5(6) . . . . ?
N8A N9A C10A C11A 179.2(6) . . . . ?
Pb1 N9A C10A C11A -15.2(9) . . . . ?
N9A C10A C11A N12A -5.3(10) . . . . ?
C101 C10A C11A N12A 175.0(8) . . . . ?
N9A C10A C11A C16A 174.8(7) . . . . ?
C101 C10A C11A C16A -4.8(11) . . . . ?
C16A C11A N12A C13A 2.1(12) . . . . ?
C10A C11A N12A C13A -177.8(8) . . . . ?
C16A C11A N12A Pb1 -157.0(6) . . . . ?
C10A C11A N12A Pb1 23.1(8) . . . . ?
C11A N12A C13A C14A -1.1(13) . . . . ?
Pb1 N12A C13A C14A 158.6(7) . . . . ?
N12A C13A C14A C15A -1.6(14) . . . . ?
C13A C14A C15A C16A 3.1(13) . . . . ?
N12A C11A C16A C15A -0.6(12) . . . . ?
C10A C11A C16A C15A 179.3(7) . . . . ?
C14A C15A C16A C11A -2.1(13) . . . . ?
O12B C1B O11B Pb1 12.0(8) . . . . ?
C2B C1B O11B Pb1 -165.6(7) . . . . ?
O11B C1B O12B Pb1 -11.2(7) . . . . ?
C2B C1B O12B Pb1 166.2(8) . . . . ?

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
C5A H5A O4C 0.93 2.50 3.309(10) 145.9 1_455
C6A H6A O7A 0.93 2.42 3.106(10) 130.0 2_466
N8A H8A O11B 0.88 2.15 2.923(8) 146.1 5_666
C101 H10C O11B 0.96 2.59 3.419(10) 144.2 5_666
C16A H16A O2C 0.93 2.60 3.519(13) 171.0 6_755

_refine_diff_density_max         2.935
_refine_diff_density_min         -1.605
_refine_diff_density_rms         0.208

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 1059562'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N4 O, Cl O4'
_chemical_formula_sum            'C13 H13 Cl N4 O5'
_chemical_formula_weight         340.72

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'

_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                   8.151(3)
_cell_length_b                   8.049(3)
_cell_length_c                   21.772(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.501(6)
_cell_angle_gamma                90
_cell_volume                     1424.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.302
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            8470
_diffrn_reflns_av_unetI/netI     0.1386
_diffrn_reflns_av_R_equivalents  0.1511
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         23.322
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.811
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.811
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.811
_reflns_number_total             2046
_reflns_number_gt                1086
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0911P)²+2.8435P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2046
_refine_ls_number_parameters     209
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.1672
_refine_ls_R_factor_gt           0.0825
_refine_ls_wR_factor_ref         0.2144
_refine_ls_wR_factor_gt          0.1769
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_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
N1A N 0.8759(7) 0.0236(8) 0.2826(3) 0.0241(16) Uani 1 1 d . U . . .
C2A C 0.7314(9) 0.1045(9) 0.2771(3) 0.0232(19) Uani 1 1 d . U . . .
H2A H 0.6934 0.1483 0.2380 0.028 Uiso 1 1 calc R U . . .
C3A C 0.6349(9) 0.1266(9) 0.3269(3) 0.0221(19) Uani 1 1 d . U . . .
C4A C 0.6914(10) 0.0658(9) 0.3838(4) 0.029(2) Uani 1 1 d . U . . .
H4A H 0.6294 0.0808 0.4185 0.035 Uiso 1 1 calc R U . . .
C5A C 0.8431(10) -0.0192(10) 0.3894(4) 0.033(2) Uani 1 1 d . U . . .
H5Q H 0.8850 -0.0643 0.4278 0.040 Uiso 1 1 calc R U . . .
C6A C 0.9277(10) -0.0349(10) 0.3383(4) 0.029(2) Uani 1 1 d . U . . .
H6A H 1.0304 -0.0911 0.3424 0.035 Uiso 1 1 calc R U . . .
C7A C 0.4796(9) 0.2259(10) 0.3130(4) 0.0228(18) Uani 1 1 d . U . . .
O7A O 0.4561(6) 0.3047(7) 0.2664(3) 0.0288(14) Uani 1 1 d . . . . .
N8A N 0.3701(7) 0.2169(8) 0.3574(3) 0.0252(16) Uani 1 1 d . U . . .
H8A H 0.3976 0.1957 0.3985 0.030 Uiso 1 1 d R U . . .
N9A N 0.2241(7) 0.3059(8) 0.3467(3) 0.0259(16) Uani 1 1 d . U . . .
C10A C 0.1360(9) 0.3242(10) 0.3916(4) 0.027(2) Uani 1 1 d . U . . .
C101 C 0.1783(9) 0.2643(12) 0.4566(3) 0.039(2) Uani 1 1 d . U . . .
H10A H 0.1523 0.1458 0.4593 0.059 Uiso 1 1 calc R U . . .
H10B H 0.1141 0.3268 0.4850 0.059 Uiso 1 1 calc R U . . .
H10C H 0.2960 0.2813 0.4677 0.059 Uiso 1 1 calc R U . . .
C11A C -0.0204(9) 0.4172(9) 0.3767(3) 0.0229(19) Uani 1 1 d . U . . .
N12A N -0.0448(7) 0.4879(8) 0.3212(3) 0.0256(16) Uani 1 1 d . U . . .
H12A H 0.0377 0.4880 0.2911 0.031 Uiso 1 1 d R U . . .
C13A C -0.1806(10) 0.5739(10) 0.3033(4) 0.031(2) Uani 1 1 d . U . . .
H13A H -0.1921 0.6235 0.2636 0.038 Uiso 1 1 calc R U . . .
C14A C -0.3045(9) 0.5903(9) 0.3430(3) 0.0243(19) Uani 1 1 d . U . . .
H14A H -0.4011 0.6515 0.3307 0.029 Uiso 1 1 calc R U . . .
C15A C -0.2873(9) 0.5192(9) 0.3992(4) 0.027(2) Uani 1 1 d . U . . .
H15A H -0.3718 0.5304 0.4265 0.033 Uiso 1 1 calc R U . . .
C16A C -0.1450(9) 0.4288(10) 0.4172(4) 0.028(2) Uani 1 1 d . U . . .
H16A H -0.1333 0.3760 0.4563 0.034 Uiso 1 1 calc R U . . .
Cl1B Cl 0.3039(2) 0.7672(2) 0.43415(9) 0.0255(6) Uani 1 1 d . . . . .
O1B O 0.3112(10) 0.7416(10) 0.3708(3) 0.076(2) Uani 1 1 d . U . . .
O2B O 0.1389(7) 0.7682(9) 0.4497(3) 0.0594(19) Uani 1 1 d . U . . .
O3B O 0.3720(11) 0.9230(10) 0.4484(4) 0.090(3) Uani 1 1 d . U . . .
O4B O 0.3909(9) 0.6459(9) 0.4704(3) 0.071(2) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C6A 1.337(9) . ?
N1A C2A 1.343(9) . ?
C2A C3A 1.400(10) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.377(10) . ?
C3A C7A 1.507(10) . ?
C4A C5A 1.410(11) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.361(11) . ?
C5A H5Q 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O7A 1.200(9) . ?
C7A N8A 1.369(9) . ?
N8A N9A 1.393(8) . ?
N8A H8A 0.9208 . ?
N9A C10A 1.267(9) . ?
C10A C11A 1.492(10) . ?
C10A C101 1.508(10) . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C11A N12A 1.338(9) . ?
C11A C16A 1.399(10) . ?
N12A C13A 1.337(9) . ?
N12A H12A 0.9737 . ?
C13A C14A 1.386(11) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.348(10) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.399(11) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
Cl1B O3B 1.397(8) . ?
Cl1B O1B 1.401(7) . ?
Cl1B O4B 1.411(6) . ?
Cl1B O2B 1.412(6) . ?

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
C6A N1A C2A 117.6(7) . . ?
N1A C2A C3A 122.3(7) . . ?
N1A C2A H2A 118.8 . . ?
C3A C2A H2A 118.8 . . ?
C4A C3A C2A 118.9(7) . . ?
C4A C3A C7A 125.8(7) . . ?
C2A C3A C7A 115.3(7) . . ?
C3A C4A C5A 118.7(7) . . ?
C3A C4A H4A 120.7 . . ?
C5A C4A H4A 120.7 . . ?
C6A C5A C4A 118.1(7) . . ?
C6A C5A H5Q 121.0 . . ?
C4A C5A H5Q 121.0 . . ?
N1A C6A C5A 124.4(7) . . ?
N1A C6A H6A 117.8 . . ?
C5A C6A H6A 117.8 . . ?
O7A C7A N8A 123.8(7) . . ?
O7A C7A C3A 121.7(6) . . ?
N8A C7A C3A 114.5(7) . . ?
C7A N8A N9A 116.8(6) . . ?
C7A N8A H8A 125.0 . . ?
N9A N8A H8A 113.5 . . ?
C10A N9A N8A 117.3(6) . . ?
N9A C10A C11A 114.7(7) . . ?
N9A C10A C101 125.8(7) . . ?
C11A C10A C101 119.5(7) . . ?
C10A C101 H10A 109.5 . . ?
C10A C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C10A C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
N12A C11A C16A 118.5(7) . . ?
N12A C11A C10A 118.3(6) . . ?
C16A C11A C10A 123.2(7) . . ?
C13A N12A C11A 123.0(7) . . ?
C13A N12A H12A 113.9 . . ?
C11A N12A H12A 123.1 . . ?
N12A C13A C14A 119.7(7) . . ?
N12A C13A H13A 120.1 . . ?
C14A C13A H13A 120.1 . . ?
C15A C14A C13A 119.7(8) . . ?
C15A C14A H14A 120.1 . . ?
C13A C14A H14A 120.1 . . ?
C14A C15A C16A 120.0(8) . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A C11A 119.0(8) . . ?
C15A C16A H16A 120.5 . . ?
C11A C16A H16A 120.5 . . ?
O3B Cl1B O1B 107.7(5) . . ?
O3B Cl1B O4B 108.9(5) . . ?
O1B Cl1B O4B 113.0(4) . . ?
O3B Cl1B O2B 108.1(5) . . ?
O1B Cl1B O2B 110.6(4) . . ?
O4B Cl1B O2B 108.5(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
C2A H2A O1B 0.95 2.48 3.394(10) 161.1 2_645
C5A H5Q O2B 0.95 2.48 3.157(10) 127.8 1_645
N8A H8A O3B 0.92 2.46 3.084(10) 124.8 1_545
C101 H10A O3B 0.98 2.56 3.180(13) 121.4 1_545
N12A H12A N1A 0.97 1.83 2.751(9) 157.6 2_655
C14A H14A O7A 0.95 2.46 3.117(10) 126.5 2
C16A H16A O2B 0.95 2.36 3.301(10) 172.5 3_566

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.105

_shelxl_version_number           2013-2



