# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_2

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 N13 O12 Pb2'
_chemical_formula_weight         977.73

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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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                   9.4199(3)
_cell_length_b                   12.6344(4)
_cell_length_c                   20.5258(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2442.87(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9808
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.52

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.658
_exptl_crystal_F_000             1800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    13.856
_shelx_estimated_absorpt_T_min   0.287
_shelx_estimated_absorpt_T_max   0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.364
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33703
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.557
_diffrn_reflns_theta_max         30.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3694
_reflns_number_gt                3250
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_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)+(0.0393P)²+3.9429P] 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         3694
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb -0.06934(2) 0.38760(2) 0.27590(2) 0.01988(6) Uani 1 1 d . . . . .
O1 O 0.1491(3) 0.5135(2) 0.24243(16) 0.0332(6) Uani 1 1 d . . . . .
O2 O -0.0489(3) 0.5794(3) 0.2089(2) 0.0417(8) Uani 1 1 d . . . . .
O3 O 0.1384(3) 0.6772(2) 0.2143(2) 0.0500(10) Uani 1 1 d . . . . .
O4 O -0.0408(4) 0.5493(3) 0.35645(17) 0.0515(9) Uani 1 1 d . . . . .
O5 O -0.1676(5) 0.4265(3) 0.39923(18) 0.0621(11) Uani 1 1 d . . . . .
O6 O -0.1021(6) 0.5626(4) 0.45643(19) 0.0814(15) Uani 1 1 d . . . . .
N1 N 0.1353(3) 0.2871(2) 0.21015(13) 0.0182(5) Uani 1 1 d . . . . .
N2 N 0.2500 0.2500 0.11055(19) 0.0244(8) Uani 1 2 d S T P . .
N3 N -0.0963(4) 0.3551(3) 0.14644(17) 0.0322(7) Uani 1 1 d . . . . .
N4 N 0.0176(4) 0.3251(4) 0.04547(17) 0.0463(10) Uani 1 1 d . . . . .
N5 N 0.1484(3) 0.3057(2) 0.34302(13) 0.0212(5) Uani 1 1 d . . . . .
N6 N 0.0775(3) 0.5906(3) 0.22109(17) 0.0278(7) Uani 1 1 d . . . . .
N7 N -0.1057(4) 0.5141(3) 0.40466(18) 0.0371(8) Uani 1 1 d . . . . .
C1 C 0.1400(3) 0.2844(3) 0.14548(15) 0.0191(6) Uani 1 1 d . . . . .
C2 C 0.0126(4) 0.3241(3) 0.10971(17) 0.0250(7) Uani 1 1 d . . . . .
C3 C -0.0987(6) 0.3619(5) 0.0160(2) 0.0590(16) Uani 1 1 d . . . . .
H3A H -0.0993 0.3654 -0.0302 0.071 Uiso 1 1 calc R U . . .
C4 C -0.2176(6) 0.3950(5) 0.0492(3) 0.0563(16) Uani 1 1 d . . . . .
H4A H -0.3000 0.4193 0.0271 0.068 Uiso 1 1 calc R U . . .
C5 C -0.2106(5) 0.3911(4) 0.1159(2) 0.0505(13) Uani 1 1 d . . . . .
H5A H -0.2895 0.4146 0.1408 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2500 0.2500 0.2410(2) 0.0147(7) Uani 1 2 d S T P . .
C7 C 0.2500 0.2500 0.3134(2) 0.0166(8) Uani 1 2 d S T P . .
C8 C 0.1493(4) 0.3048(3) 0.40817(17) 0.0297(8) Uani 1 1 d . . . . .
H8A H 0.0782 0.3431 0.4310 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2500 0.2500 0.4433(3) 0.0346(12) Uani 1 2 d S T P . .
H9A H 0.2500 0.2500 0.4896 0.042 Uiso 1 2 calc R U P . .


_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 O4 2.642(3) . ?
Pb1 N1 2.674(3) . ?
Pb1 N5 2.679(3) . ?
Pb1 O1 2.690(3) . ?
Pb1 N3 2.701(3) . ?
Pb1 O5 2.740(4) . ?
Pb1 O3 2.744(3) 3_545 ?
O1 N6 1.263(5) . ?
O2 N6 1.225(4) . ?
O3 N6 1.244(4) . ?
O3 Pb1 2.744(3) 3 ?
O4 N7 1.245(5) . ?
O5 N7 1.256(5) . ?
O6 N7 1.227(5) . ?
N1 C1 1.329(4) . ?
N1 C6 1.337(3) . ?
N2 C1 1.333(4) 2 ?
N2 C1 1.333(4) . ?
N3 C5 1.326(5) . ?
N3 C2 1.332(5) . ?
N4 C2 1.319(5) . ?
N4 C3 1.335(6) . ?
N5 C7 1.334(3) . ?
N5 C8 1.337(4) . ?
C1 C2 1.494(5) . ?
C3 C4 1.376(7) . ?
C4 C5 1.372(7) . ?
C6 N1 1.337(3) 2 ?
C6 C7 1.486(6) . ?
C7 N5 1.334(3) 2 ?
C8 C9 1.378(5) . ?
C9 C8 1.378(5) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Pb1 N1 127.57(10) . . ?
O4 Pb1 N5 84.21(11) . . ?
N1 Pb1 N5 61.58(8) . . ?
O4 Pb1 O1 67.96(10) . . ?
N1 Pb1 O1 66.44(9) . . ?
N5 Pb1 O1 76.95(9) . . ?
O4 Pb1 N3 138.00(12) . . ?
N1 Pb1 N3 59.93(9) . . ?
N5 Pb1 N3 121.27(9) . . ?
O1 Pb1 N3 84.87(11) . . ?
O4 Pb1 O5 46.96(11) . . ?
N1 Pb1 O5 142.66(12) . . ?
N5 Pb1 O5 81.53(12) . . ?
O1 Pb1 O5 112.86(11) . . ?
N3 Pb1 O5 154.77(12) . . ?
O4 Pb1 O3 136.66(12) . 3_545 ?
N1 Pb1 O3 75.41(9) . 3_545 ?
N5 Pb1 O3 76.68(10) . 3_545 ?
O1 Pb1 O3 140.62(9) . 3_545 ?
N3 Pb1 O3 84.40(12) . 3_545 ?
O5 Pb1 O3 91.47(12) . 3_545 ?
N6 O1 Pb1 97.8(2) . . ?
N6 O3 Pb1 137.3(3) . 3 ?
N7 O4 Pb1 99.9(2) . . ?
N7 O5 Pb1 94.8(2) . . ?
C1 N1 C6 115.9(3) . . ?
C1 N1 Pb1 122.7(2) . . ?
C6 N1 Pb1 120.7(2) . . ?
C1 N2 C1 114.9(4) 2 . ?
C5 N3 C2 117.3(4) . . ?
C5 N3 Pb1 119.3(3) . . ?
C2 N3 Pb1 122.0(2) . . ?
C2 N4 C3 115.3(4) . . ?
C7 N5 C8 116.5(3) . . ?
C7 N5 Pb1 121.2(2) . . ?
C8 N5 Pb1 121.5(2) . . ?
O2 N6 O3 121.8(4) . . ?
O2 N6 O1 120.1(4) . . ?
O3 N6 O1 118.1(3) . . ?
O6 N7 O4 119.8(4) . . ?
O6 N7 O5 122.0(4) . . ?
O4 N7 O5 118.1(4) . . ?
N2 C1 N1 124.9(3) . . ?
N2 C1 C2 118.0(3) . . ?
N1 C1 C2 117.1(3) . . ?
N4 C2 N3 126.2(3) . . ?
N4 C2 C1 117.8(3) . . ?
N3 C2 C1 116.1(3) . . ?
N4 C3 C4 123.3(5) . . ?
C3 C4 C5 116.3(4) . . ?
N3 C5 C4 121.6(5) . . ?
N1 C6 N1 123.5(4) 2 . ?
N1 C6 C7 118.3(2) 2 . ?
N1 C6 C7 118.3(2) . . ?
N5 C7 N5 125.8(4) . 2 ?
N5 C7 C6 117.1(2) . . ?
N5 C7 C6 117.1(2) 2 . ?
N5 C8 C9 122.2(4) . . ?
C8 C9 C8 116.8(5) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pb1 O3 N6 O2 31.5(7) 3 . . . ?
Pb1 O3 N6 O1 -147.1(3) 3 . . . ?
Pb1 O1 N6 O2 -15.1(4) . . . . ?
Pb1 O1 N6 O3 163.5(3) . . . . ?
Pb1 O4 N7 O6 171.4(4) . . . . ?
Pb1 O4 N7 O5 -5.1(5) . . . . ?
Pb1 O5 N7 O6 -171.6(4) . . . . ?
Pb1 O5 N7 O4 4.8(5) . . . . ?
C1 N2 C1 N1 0.8(2) 2 . . . ?
C1 N2 C1 C2 -179.9(3) 2 . . . ?
C6 N1 C1 N2 -1.5(4) . . . . ?
Pb1 N1 C1 N2 169.08(19) . . . . ?
C6 N1 C1 C2 179.2(3) . . . . ?
Pb1 N1 C1 C2 -10.2(4) . . . . ?
C3 N4 C2 N3 0.6(8) . . . . ?
C3 N4 C2 C1 -179.6(5) . . . . ?
C5 N3 C2 N4 -0.4(7) . . . . ?
Pb1 N3 C2 N4 -166.5(4) . . . . ?
C5 N3 C2 C1 179.8(4) . . . . ?
Pb1 N3 C2 C1 13.7(5) . . . . ?
N2 C1 C2 N4 -1.5(5) . . . . ?
N1 C1 C2 N4 177.8(4) . . . . ?
N2 C1 C2 N3 178.3(3) . . . . ?
N1 C1 C2 N3 -2.4(5) . . . . ?
C2 N4 C3 C4 -1.1(9) . . . . ?
N4 C3 C4 C5 1.6(10) . . . . ?
C2 N3 C5 C4 0.9(8) . . . . ?
Pb1 N3 C5 C4 167.3(5) . . . . ?
C3 C4 C5 N3 -1.4(9) . . . . ?
C1 N1 C6 N1 0.7(2) . . . 2 ?
Pb1 N1 C6 N1 -170.1(2) . . . 2 ?
C1 N1 C6 C7 -179.3(2) . . . . ?
Pb1 N1 C6 C7 9.9(2) . . . . ?
C8 N5 C7 N5 -0.2(2) . . . 2 ?
Pb1 N5 C7 N5 -170.4(2) . . . 2 ?
C8 N5 C7 C6 179.8(2) . . . . ?
Pb1 N5 C7 C6 9.6(2) . . . . ?
N1 C6 C7 N5 167.16(19) 2 . . . ?
N1 C6 C7 N5 -12.84(19) . . . . ?
N1 C6 C7 N5 -12.84(19) 2 . . 2 ?
N1 C6 C7 N5 167.16(19) . . . 2 ?
C7 N5 C8 C9 0.4(5) . . . . ?
Pb1 N5 C8 C9 170.6(2) . . . . ?
N5 C8 C9 C8 -0.2(3) . . . 2 ?

_refine_diff_density_max         1.303
_refine_diff_density_min         -1.965
_refine_diff_density_rms         0.164

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 966468'
