# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

 
data_x
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             none
_chemical_melting_point           'not measured'
_chemical_formula_moiety          'C6 H8 Cl2 N2 O2 Pb'
_chemical_formula_sum
 'C6 H8 Cl2 N2 O2 Pb' 
_chemical_formula_weight          418.23

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/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                    8.0984(6)
_cell_length_b                    17.9704(10)
_cell_length_c                    7.8257(6)
_cell_angle_alpha                 90
_cell_angle_beta                  112.445(9)
_cell_angle_gamma                 90
_cell_volume                      1052.61(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     295(2)
_cell_measurement_reflns_used     1888
_cell_measurement_theta_min       3.8160
_cell_measurement_theta_max       27.7540
 
_exptl_crystal_description        block
_exptl_crystal_colour             white
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     2.639          
_exptl_crystal_F_000              760
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.180
_exptl_crystal_size_min           0.150
_exptl_absorpt_coefficient_mu     16.505
_shelx_estimated_absorpt_T_min    0.137
_shelx_estimated_absorpt_T_max    0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min   0.54426
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       295(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type   'multiwire proportional'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  16.2083
_diffrn_reflns_number             5633
_diffrn_reflns_av_unetI/netI      0.0336
_diffrn_reflns_av_R_equivalents   0.0261
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        23
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.543
_diffrn_reflns_theta_max          28.132
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.849
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.849
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.849
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              2193
_reflns_number_gt                 1604
_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 FRAMBO'
_computing_cell_refinement        'Bruker FRAMBO'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_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)+(0.0450P)²+4.0000P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef        0.0006(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2193
_refine_ls_number_parameters      120
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0507
_refine_ls_R_factor_gt            0.0326
_refine_ls_wR_factor_ref          0.0917
_refine_ls_wR_factor_gt           0.0819
_refine_ls_goodness_of_fit_ref    0.999
_refine_ls_restrained_S_all       0.999
_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 0.29600(4) 0.25172(2) 0.50957(4) 0.03035(15) Uani 1 1 d . . . . .
Cl1 Cl 0.0473(3) 0.32289(12) 0.6217(3) 0.0422(5) Uani 1 1 d . . . . .
Cl2 Cl 0.3109(4) 0.36683(13) 0.2808(3) 0.0599(8) Uani 1 1 d . . . . .
O1 O 0.6331(10) 0.2623(3) 0.6808(10) 0.0507(17) Uani 1 1 d . . . . .
O2 O 0.4738(7) 0.3296(3) 0.7952(7) 0.0375(13) Uani 1 1 d . . . . .
N1 N 0.7741(8) 0.4016(3) 1.0396(8) 0.0312(14) Uani 1 1 d . . . . .
N2 N 0.7408(10) 0.4658(4) 1.2556(9) 0.0449(18) Uani 1 1 d . . . . .
C1 C 0.6184(10) 0.3091(4) 0.7932(10) 0.0286(16) Uani 1 1 d . . . . .
C2 C 0.7957(10) 0.3386(4) 0.9334(11) 0.0336(18) Uani 1 1 d . . . . .
H2A H 0.856250 0.298835 1.017861 0.040 Uiso 1 1 calc R U . . .
H2B H 0.871041 0.353450 0.868263 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7567(15) 0.4744(5) 0.9856(13) 0.054(3) Uani 1 1 d . . . . .
H3A H 0.758321 0.492667 0.875069 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7371(15) 0.5141(5) 1.1186(13) 0.058(3) Uani 1 1 d . . . . .
H4A H 0.723277 0.565443 1.119151 0.069 Uiso 1 1 calc R U . . .
C5 C 0.7619(11) 0.3982(4) 1.2021(11) 0.0361(19) Uani 1 1 d . . . . .
H5A H 0.767339 0.354816 1.268910 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7262(17) 0.4860(6) 1.4284(14) 0.069(3) Uani 1 1 d . . . . .
H6A H 0.826327 0.466172 1.529576 0.104 Uiso 1 1 calc R U . . .
H6B H 0.617510 0.465949 1.431588 0.104 Uiso 1 1 calc R U . . .
H6C H 0.724980 0.539206 1.438475 0.104 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 O1 2.548(8) . ?
Pb1 O2 2.563(5) . ?
Pb1 Cl2 2.768(2) . ?
Pb1 Cl1 2.795(2) . ?
Pb1 Cl2 2.977(2) 4_566 ?
O1 C1 1.255(9) . ?
O2 C1 1.233(8) . ?
N1 C5 1.314(9) . ?
N1 C3 1.366(11) . ?
N1 C2 1.453(9) . ?
N2 C5 1.318(10) . ?
N2 C4 1.370(11) . ?
N2 C6 1.447(11) . ?
C1 C2 1.532(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.321(13) . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
O1 Pb1 O2 50.82(18) . . ?
O1 Pb1 Cl2 88.98(17) . . ?
O2 Pb1 Cl2 90.43(13) . . ?
O1 Pb1 Cl1 123.83(15) . . ?
O2 Pb1 Cl1 73.06(12) . . ?
Cl2 Pb1 Cl1 94.34(7) . . ?
O1 Pb1 Cl2 86.24(17) . 4_566 ?
O2 Pb1 Cl2 84.97(13) . 4_566 ?
Cl2 Pb1 Cl2 174.81(11) . 4_566 ?
Cl1 Pb1 Cl2 86.65(7) . 4_566 ?
Pb1 Cl2 Pb1 85.78(6) . 4_565 ?
C1 O1 Pb1 92.8(5) . . ?
C1 O2 Pb1 92.6(5) . . ?
C5 N1 C3 107.9(7) . . ?
C5 N1 C2 126.0(7) . . ?
C3 N1 C2 126.1(7) . . ?
C5 N2 C4 107.6(7) . . ?
C5 N2 C6 126.5(8) . . ?
C4 N2 C6 126.0(8) . . ?
O2 C1 O1 123.6(8) . . ?
O2 C1 C2 121.5(7) . . ?
O1 C1 C2 114.9(7) . . ?
N1 C2 C1 113.3(6) . . ?
N1 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 N1 107.6(8) . . ?
C4 C3 H3A 126.2 . . ?
N1 C3 H3A 126.2 . . ?
C3 C4 N2 107.5(8) . . ?
C3 C4 H4A 126.2 . . ?
N2 C4 H4A 126.2 . . ?
N1 C5 N2 109.4(7) . . ?
N1 C5 H5A 125.3 . . ?
N2 C5 H5A 125.3 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
Pb1 O2 C1 O1 -3.5(8) . . . . ?
Pb1 O2 C1 C2 177.8(6) . . . . ?
Pb1 O1 C1 O2 3.6(8) . . . . ?
Pb1 O1 C1 C2 -177.7(6) . . . . ?
C5 N1 C2 C1 93.8(9) . . . . ?
C3 N1 C2 C1 -83.8(10) . . . . ?
O2 C1 C2 N1 -11.3(11) . . . . ?
O1 C1 C2 N1 170.0(7) . . . . ?
C5 N1 C3 C4 1.0(12) . . . . ?
C2 N1 C3 C4 179.0(8) . . . . ?
N1 C3 C4 N2 -0.5(13) . . . . ?
C5 N2 C4 C3 -0.2(12) . . . . ?
C6 N2 C4 C3 179.1(11) . . . . ?
C3 N1 C5 N2 -1.1(10) . . . . ?
C2 N1 C5 N2 -179.1(7) . . . . ?
C4 N2 C5 N1 0.8(10) . . . . ?
C6 N2 C5 N1 -178.5(9) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
C2 H2A Cl1  0.97 2.62 3.529(8) 155.6 4_666
C2 H2B Cl1  0.97 2.86 3.739(8) 151.5 1_655
C3 H3A Cl2  0.93 2.77 3.452(9) 131.3 3_666
C4 H4A Cl1  0.93 2.95 3.613(9) 129.3 3_667
C5 H5A Cl1  0.93 2.88 3.487(8) 123.8 1_656
C5 H5A O1  0.93 2.35 3.049(10) 132.0 4_566
 
_refine_diff_density_max    1.943
_refine_diff_density_min   -1.373
_refine_diff_density_rms    0.163



