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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1552829'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O7 Pb S2'
_chemical_formula_weight         705.70

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      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                   10.7014(3)
_cell_length_b                   11.1489(4)
_cell_length_c                   11.3358(6)
_cell_angle_alpha                84.683(2)
_cell_angle_beta                 65.943(2)
_cell_angle_gamma                63.957(2)
_cell_volume                     1103.44(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    41554
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.68

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.124
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    7.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_T_max  0.532
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_special_details           'crystal-to-detector distance 32 mm'
_diffrn_ambient_temperature      150(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  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'1 φ and 11 ω scans with 2° steps (515 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            41554
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4194
_reflns_number_gt                3685
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by intrinsic phasing and subsequent difference Fourier
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms bound to O7 were found on a 
 difference Fourier map and all the others were introduced at calculated
 positions; all were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom (1.5 for CH₃, with
 optimized geometry). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.1866P] 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         4194
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0790
_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 0.54720(2) 0.64838(2) 0.82027(2) 0.03378(10) Uani 1 1 d . . . . .
S2 S 0.36946(17) 0.45434(15) 0.89941(14) 0.0353(3) Uani 1 1 d . . . . .
S1 S 0.79137(17) 0.80069(15) 0.58986(14) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.6889(5) 0.7845(4) 0.7180(4) 0.0377(10) Uani 1 1 d . . . . .
O2 O 0.9159(5) 0.6722(4) 0.5220(4) 0.0430(10) Uani 1 1 d . . . . .
O3 O 0.8399(5) 0.9000(4) 0.5999(4) 0.0430(10) Uani 1 1 d . . . . .
O4 O 0.3365(5) 0.5659(4) 0.9859(4) 0.0438(11) Uani 1 1 d . . . . .
O5 O 0.4736(5) 0.4532(4) 0.7674(4) 0.0416(10) Uani 1 1 d . . . . .
O6 O 0.4173(5) 0.3258(4) 0.9524(4) 0.0413(10) Uani 1 1 d . . . . .
O7 O 0.7631(5) 0.5090(4) 0.5853(4) 0.0495(12) Uani 1 1 d . . . . .
H7A H 0.7866 0.5749 0.5400 0.059 Uiso 1 1 d R U . . .
H7B H 0.8441 0.4370 0.5875 0.059 Uiso 1 1 d R U . . .
N1 N 0.3804(6) 0.7607(5) 0.7035(5) 0.0398(13) Uani 1 1 d . . . . .
N2 N 0.3474(6) 0.8827(5) 0.9178(5) 0.0355(11) Uani 1 1 d . . . . .
C1 C 0.6819(7) 0.8586(6) 0.4955(5) 0.0315(13) Uani 1 1 d . . . . .
C2 C 0.7309(7) 0.7829(6) 0.3841(5) 0.0359(14) Uani 1 1 d . . . . .
H2 H 0.8235 0.7026 0.3571 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6456(7) 0.8227(6) 0.3091(6) 0.0372(14) Uani 1 1 d . . . . .
H3 H 0.6819 0.7692 0.2311 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5126(7) 0.9359(6) 0.3454(6) 0.0356(14) Uani 1 1 d . . . . .
H4 H 0.4552 0.9609 0.2941 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4584(7) 1.0184(5) 0.4632(5) 0.0314(13) Uani 1 1 d . . . . .
C6 C 0.1923(7) 0.4903(6) 0.8942(6) 0.0327(13) Uani 1 1 d . . . . .
C7 C 0.1799(7) 0.5228(6) 0.7786(6) 0.0341(13) Uani 1 1 d . . . . .
H7 H 0.2631 0.5267 0.7059 0.041 Uiso 1 1 calc R U . . .
C8 C 0.0443(7) 0.5502(6) 0.7680(6) 0.0376(14) Uani 1 1 d . . . . .
H8 H 0.0362 0.5717 0.6876 0.045 Uiso 1 1 calc R U . . .
C9 C -0.0770(7) 0.5462(6) 0.8728(5) 0.0366(14) Uani 1 1 d . . . . .
H9 H -0.1686 0.5659 0.8643 0.044 Uiso 1 1 calc R U . . .
C10 C -0.0672(6) 0.5132(5) 0.9934(5) 0.0285(12) Uani 1 1 d . . . . .
C11 C 0.4027(7) 0.7033(7) 0.5939(5) 0.0384(14) Uani 1 1 d . . . . .
H11 H 0.4922 0.6223 0.5535 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2975(9) 0.7592(7) 0.5361(6) 0.0501(18) Uani 1 1 d . . . . .
H12 H 0.3157 0.7155 0.4587 0.060 Uiso 1 1 calc R U . . .
C13 C 0.1676(8) 0.8780(7) 0.5933(6) 0.0426(15) Uani 1 1 d . . . . .
H13 H 0.0948 0.9150 0.5565 0.051 Uiso 1 1 calc R U . . .
C14 C 0.1434(8) 0.9448(7) 0.7072(6) 0.0409(15) Uani 1 1 d . . . . .
C15 C 0.2540(7) 0.8808(6) 0.7568(6) 0.0372(14) Uani 1 1 d . . . . .
C16 C 0.2409(7) 0.9449(6) 0.8702(5) 0.0337(13) Uani 1 1 d . . . . .
C17 C 0.1184(7) 1.0745(6) 0.9220(6) 0.0415(15) Uani 1 1 d . . . . .
C18 C 0.0054(7) 1.1330(6) 0.8709(6) 0.0432(15) Uani 1 1 d . . . . .
H18 H -0.0801 1.2165 0.9113 0.052 Uiso 1 1 calc R U . . .
C19 C 0.0166(7) 1.0736(7) 0.7678(6) 0.0427(16) Uani 1 1 d . . . . .
C20 C 0.1161(8) 1.1376(7) 1.0253(6) 0.0450(16) Uani 1 1 d . . . . .
H20 H 0.0362 1.2240 1.0643 0.054 Uiso 1 1 calc R U . . .
C21 C 0.2261(8) 1.0767(6) 1.0694(6) 0.0437(15) Uani 1 1 d . . . . .
H21 H 0.2262 1.1209 1.1370 0.052 Uiso 1 1 calc R U . . .
C22 C 0.3399(7) 0.9477(6) 1.0146(6) 0.0387(14) Uani 1 1 d . . . . .
H22 H 0.4153 0.9046 1.0482 0.046 Uiso 1 1 calc R U . . .
C23 C -0.1060(8) 1.1417(7) 0.7158(7) 0.0512(17) Uani 1 1 d . . . . .
H23A H -0.1888 1.2221 0.7742 0.077 Uiso 1 1 calc R U . . .
H23B H -0.1463 1.0795 0.7107 0.077 Uiso 1 1 calc R U . . .
H23C H -0.0619 1.1674 0.6291 0.077 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 N1 2.482(5) . ?
Pb1 O1 2.491(4) . ?
Pb1 N2 2.515(5) . ?
Pb1 O7 2.729(4) . ?
Pb1 O4 2.740(4) . ?
Pb1 O6 2.811(4) 2_667 ?
S2 O5 1.454(4) . ?
S2 O6 1.457(4) . ?
S2 O4 1.480(4) . ?
S2 C6 1.783(6) . ?
S1 O3 1.444(4) . ?
S1 O2 1.454(4) . ?
S1 O1 1.474(4) . ?
S1 C1 1.779(6) . ?
O7 H7A 0.9242 . ?
O7 H7B 0.8934 . ?
N1 C11 1.335(7) . ?
N1 C15 1.371(8) . ?
N2 C22 1.326(7) . ?
N2 C16 1.345(8) . ?
C1 C2 1.360(8) . ?
C1 C5 1.446(8) 2_676 ?
C2 C3 1.400(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.352(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.447(8) . ?
C4 H4 0.9500 . ?
C5 C5 1.371(12) 2_676 ?
C5 C1 1.446(8) 2_676 ?
C6 C7 1.370(8) . ?
C6 C10 1.436(8) 2_567 ?
C7 C8 1.400(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(8) . ?
C9 H9 0.9500 . ?
C10 C10 1.404(11) 2_567 ?
C10 C6 1.436(8) 2_567 ?
C11 C12 1.412(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.422(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(9) . ?
C14 C19 1.445(9) . ?
C15 C16 1.456(9) . ?
C16 C17 1.420(9) . ?
C17 C20 1.408(9) . ?
C17 C18 1.426(9) . ?
C18 C19 1.334(9) . ?
C18 H18 0.9500 . ?
C19 C23 1.522(10) . ?
C20 C21 1.345(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(9) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Pb1 O1 89.26(14) . . ?
N1 Pb1 N2 65.81(17) . . ?
O1 Pb1 N2 77.79(14) . . ?
N1 Pb1 O7 85.63(16) . . ?
O1 Pb1 O7 74.72(13) . . ?
N2 Pb1 O7 140.29(14) . . ?
N1 Pb1 O4 89.58(14) . . ?
O1 Pb1 O4 162.72(13) . . ?
N2 Pb1 O4 86.02(14) . . ?
O7 Pb1 O4 122.37(12) . . ?
N1 Pb1 O6 142.85(15) . 2_667 ?
O1 Pb1 O6 88.26(12) . 2_667 ?
N2 Pb1 O6 77.46(14) . 2_667 ?
O7 Pb1 O6 129.03(13) . 2_667 ?
O4 Pb1 O6 82.30(12) . 2_667 ?
O5 S2 O6 113.8(3) . . ?
O5 S2 O4 111.2(2) . . ?
O6 S2 O4 112.2(3) . . ?
O5 S2 C6 106.8(3) . . ?
O6 S2 C6 106.6(3) . . ?
O4 S2 C6 105.5(3) . . ?
O3 S1 O2 114.1(3) . . ?
O3 S1 O1 111.4(2) . . ?
O2 S1 O1 111.4(2) . . ?
O3 S1 C1 108.7(3) . . ?
O2 S1 C1 104.9(3) . . ?
O1 S1 C1 105.8(3) . . ?
S1 O1 Pb1 140.5(2) . . ?
S2 O4 Pb1 99.0(2) . . ?
Pb1 O7 H7A 101.8 . . ?
Pb1 O7 H7B 115.6 . . ?
H7A O7 H7B 113.7 . . ?
C11 N1 C15 117.9(6) . . ?
C11 N1 Pb1 122.1(4) . . ?
C15 N1 Pb1 119.9(4) . . ?
C22 N2 C16 118.2(5) . . ?
C22 N2 Pb1 123.8(4) . . ?
C16 N2 Pb1 118.0(4) . . ?
C2 C1 C5 120.1(6) . 2_676 ?
C2 C1 S1 118.6(5) . . ?
C5 C1 S1 121.3(4) 2_676 . ?
C1 C2 C3 120.4(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.3(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C5 C5 C1 118.8(6) 2_676 2_676 ?
C5 C5 C4 120.0(7) 2_676 . ?
C1 C5 C4 121.2(5) 2_676 . ?
C7 C6 C10 121.3(5) . 2_567 ?
C7 C6 S2 117.1(4) . . ?
C10 C6 S2 121.6(4) 2_567 . ?
C6 C7 C8 119.8(5) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.6(6) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.8(6) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C10 C10 C9 119.6(6) 2_567 . ?
C10 C10 C6 118.0(6) 2_567 2_567 ?
C9 C10 C6 122.4(5) . 2_567 ?
N1 C11 C12 122.1(6) . . ?
N1 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 119.4(6) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 119.9(6) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 116.1(6) . . ?
C15 C14 C19 120.4(6) . . ?
C13 C14 C19 123.4(6) . . ?
N1 C15 C14 124.5(6) . . ?
N1 C15 C16 115.9(5) . . ?
C14 C15 C16 119.6(6) . . ?
N2 C16 C17 122.9(5) . . ?
N2 C16 C15 119.3(5) . . ?
C17 C16 C15 117.7(6) . . ?
C20 C17 C16 116.1(6) . . ?
C20 C17 C18 123.6(6) . . ?
C16 C17 C18 120.4(6) . . ?
C19 C18 C17 121.7(6) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C14 120.0(6) . . ?
C18 C19 C23 119.5(6) . . ?
C14 C19 C23 120.5(6) . . ?
C21 C20 C17 120.6(6) . . ?
C21 C20 H20 119.7 . . ?
C17 C20 H20 119.7 . . ?
C20 C21 C22 119.2(6) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N2 C22 C21 122.9(6) . . ?
N2 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
O7 H7A O2 0.92 2.04 2.813(6) 139.7 .
O7 H7B O2 0.89 2.13 2.884(6) 141.0 2_766

_refine_diff_density_max         0.797
_refine_diff_density_min         -2.642
_refine_diff_density_rms         0.273

_shelxl_version_number           2014-3

