# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 1580069'
_audit_update_record             
;
2017-10-15 deposited with the CCDC.
2017-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H13 Cl4 N3 Pb'
_chemical_formula_weight         476.18

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.7639(2)
_cell_length_b                   8.7962(4)
_cell_length_c                   26.1501(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.237(2)
_cell_angle_gamma                90.00
_cell_volume                     1320.29(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6703
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.39

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    13.557
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15449
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3027
_reflns_number_gt                2512
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0330P)²+1.3036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3027
_refine_ls_number_parameters     128
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.02150(3) 0.35797(2) 0.327584(8) 0.03201(8) Uani 1 1 d . . .
Cl2 Cl 0.0449(3) 0.5223(2) 0.41563(7) 0.0568(4) Uani 1 1 d . . .
Cl4 Cl 0.5192(3) 0.3478(3) 0.32710(8) 0.0649(6) Uani 1 1 d . . .
Cl3 Cl 0.0594(4) 0.0940(2) 0.38572(9) 0.0806(6) Uani 1 1 d . . .
Cl1 Cl 0.0275(5) 0.6258(2) 0.25966(9) 0.0859(7) Uani 1 1 d . . .
N5 N 0.4880(11) 0.2083(8) 0.5395(2) 0.0583(15) Uani 1 1 d . . .
C2 C 0.4831(16) 0.3164(9) 0.4671(3) 0.062(2) Uani 1 1 d U . .
H2 H 0.4377 0.3755 0.4385 0.074 Uiso 1 1 calc R . .
N3 N 0.6752(15) 0.2294(9) 0.4734(3) 0.084(2) Uani 1 1 d U . .
H3 H 0.7770 0.2192 0.4515 0.101 Uiso 1 1 calc R . .
C4 C 0.6815(13) 0.1624(8) 0.5185(3) 0.0552(18) Uani 1 1 d . . .
H4 H 0.7960 0.0969 0.5330 0.066 Uiso 1 1 calc R . .
C1 C 0.3736(15) 0.3041(10) 0.5071(3) 0.070(2) Uani 1 1 d . . .
H1 H 0.2360 0.3542 0.5127 0.084 Uiso 1 1 calc R . .
N9 N 0.4940(17) 0.0200(10) 0.6969(4) 0.117(3) Uani 1 1 d D . .
H9A H 0.4738 -0.0419 0.6699 0.176 Uiso 1 1 calc R . .
H9B H 0.4098 -0.0131 0.7215 0.176 Uiso 1 1 calc R . .
H9C H 0.6440 0.0214 0.7086 0.176 Uiso 1 1 calc R . .
C7 C 0.5176(15) 0.2246(9) 0.6325(3) 0.073(2) Uani 1 1 d D . .
H7A H 0.4924 0.3333 0.6288 0.088 Uiso 1 1 calc R . .
H7B H 0.6841 0.2062 0.6347 0.088 Uiso 1 1 calc R . .
C6 C 0.4062(17) 0.1469(11) 0.5878(3) 0.084(3) Uani 1 1 d . . .
H6A H 0.2386 0.1591 0.5869 0.101 Uiso 1 1 calc R . .
H6B H 0.4410 0.0392 0.5903 0.101 Uiso 1 1 calc R . .
C8 C 0.421(2) 0.1700(12) 0.6819(3) 0.112(4) Uani 1 1 d D . .
H8A H 0.4703 0.2399 0.7095 0.134 Uiso 1 1 calc R . .
H8B H 0.2521 0.1725 0.6772 0.134 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pb1 0.02555(12) 0.03629(12) 0.03465(14) -0.00125(9) 0.00520(8) 0.00000(9)
Cl2 0.0704(11) 0.0581(10) 0.0433(10) -0.0129(8) 0.0133(8) -0.0043(9)
Cl4 0.0256(7) 0.0967(16) 0.0728(14) -0.0171(11) 0.0073(8) -0.0004(8)
Cl3 0.1070(17) 0.0549(11) 0.0810(15) 0.0234(11) 0.0136(13) 0.0050(11)
Cl1 0.1138(19) 0.0829(15) 0.0648(14) 0.0349(11) 0.0294(13) 0.0310(13)
N5 0.062(4) 0.074(4) 0.040(3) 0.009(3) 0.015(3) 0.004(3)
C2 0.095(6) 0.056(4) 0.031(4) 0.007(3) -0.009(4) -0.015(4)
N3 0.110(6) 0.083(5) 0.063(5) -0.015(4) 0.021(4) -0.029(4)
C4 0.059(4) 0.062(5) 0.047(4) 0.004(3) 0.017(3) 0.002(3)
C1 0.066(5) 0.070(5) 0.074(6) 0.002(5) -0.003(5) 0.010(4)
N9 0.158(9) 0.092(7) 0.107(7) 0.003(6) 0.046(6) 0.026(6)
C7 0.091(6) 0.055(5) 0.073(6) -0.009(4) 0.003(5) -0.017(4)
C6 0.085(6) 0.106(8) 0.063(6) -0.002(5) 0.015(5) -0.034(5)
C8 0.148(11) 0.146(11) 0.041(5) -0.008(6) 0.015(6) 0.048(9)

_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 Cl2 2.7116(17) . ?
Pb1 Cl3 2.773(2) . ?
Pb1 Cl4 2.8712(15) . ?
Pb1 Cl4 2.8955(15) 1_455 ?
Pb1 Cl1 2.9525(19) . ?
Pb1 Cl1 3.0559(19) 2_545 ?
Cl4 Pb1 2.8955(15) 1_655 ?
Cl1 Pb1 3.0559(19) 2 ?
N5 C1 1.327(10) . ?
N5 C4 1.350(9) . ?
N5 C6 1.488(10) . ?
C2 C1 1.274(11) . ?
C2 N3 1.344(11) . ?
C2 H2 0.9300 . ?
N3 C4 1.317(10) . ?
N3 H3 0.8600 . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
N9 C8 1.429(8) . ?
N9 H9A 0.8900 . ?
N9 H9B 0.8900 . ?
N9 H9C 0.8900 . ?
C7 C6 1.453(11) . ?
C7 C8 1.531(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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
Cl2 Pb1 Cl3 89.18(6) . . ?
Cl2 Pb1 Cl4 92.75(5) . . ?
Cl3 Pb1 Cl4 86.99(7) . . ?
Cl2 Pb1 Cl4 89.57(5) . 1_455 ?
Cl3 Pb1 Cl4 90.30(7) . 1_455 ?
Cl4 Pb1 Cl4 176.41(9) . 1_455 ?
Cl2 Pb1 Cl1 94.77(6) . . ?
Cl3 Pb1 Cl1 173.34(7) . . ?
Cl4 Pb1 Cl1 87.45(7) . . ?
Cl4 Pb1 Cl1 95.09(7) 1_455 . ?
Cl2 Pb1 Cl1 169.83(6) . 2_545 ?
Cl3 Pb1 Cl1 81.19(7) . 2_545 ?
Cl4 Pb1 Cl1 90.01(6) . 2_545 ?
Cl4 Pb1 Cl1 87.23(6) 1_455 2_545 ?
Cl1 Pb1 Cl1 95.134(11) . 2_545 ?
Pb1 Cl4 Pb1 176.41(9) . 1_655 ?
Pb1 Cl1 Pb1 167.70(11) . 2 ?
C1 N5 C4 108.1(7) . . ?
C1 N5 C6 126.5(8) . . ?
C4 N5 C6 125.0(7) . . ?
C1 C2 N3 108.5(7) . . ?
C1 C2 H2 125.8 . . ?
N3 C2 H2 125.8 . . ?
C4 N3 C2 108.6(7) . . ?
C4 N3 H3 125.7 . . ?
C2 N3 H3 125.7 . . ?
N3 C4 N5 105.9(7) . . ?
N3 C4 H4 127.0 . . ?
N5 C4 H4 127.0 . . ?
C2 C1 N5 108.9(8) . . ?
C2 C1 H1 125.6 . . ?
N5 C1 H1 125.6 . . ?
C8 N9 H9A 109.5 . . ?
C8 N9 H9B 109.5 . . ?
H9A N9 H9B 109.5 . . ?
C8 N9 H9C 109.5 . . ?
H9A N9 H9C 109.5 . . ?
H9B N9 H9C 109.5 . . ?
C6 C7 C8 111.4(7) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C6 N5 111.2(7) . . ?
C7 C6 H6A 109.4 . . ?
N5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N9 C8 C7 113.6(8) . . ?
N9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
N9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.133
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.148
