# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2143103'
loop_
_audit_author_name
_audit_author_address
'Wei Xu'
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-06-07 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 O2 Pb1 S2'
_chemical_formula_weight         457.52
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   15.1207
_cell_length_b                   5.2004
_cell_length_c                   7.6325
_cell_angle_alpha                90
_cell_angle_beta                 95.5358
_cell_angle_gamma                90
_cell_volume                     597.367


_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    2.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             424

_pd_spec_size_axial              ?
_pd_spec_size_equat              ?
_pd_spec_size_thick              ?
_pd_spec_mounting                ?
_pd_spec_mount_mode              ?
_pd_spec_shape                   ?
_pd_char_particle_morphology     ?
_pd_char_colour                  brown
_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

_exptl_absorpt_coefficient_mu    30.612
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?
_pd_instr_location               
; ?
;
_pd_calibration_special_details  
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   ?
_diffrn_source_target            ?
_diffrn_source_type              ?
_diffrn_radiation_type           CuK\a1
_diffrn_radiation_wavelength     1.54059
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       CuKα1
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_type            ?

_pd_meas_scan_method             ?
_pd_meas_special_details         
; ?
;
_pd_meas_number_of_points        11601
_pd_meas_2theta_range_min        4.000
_pd_meas_2theta_range_max        120.000
_pd_meas_2theta_range_inc        0.01

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_pd_proc_ls_special_details      
; ?
;
_pd_proc_ls_profile_function     Pseudo-Voigt
_pd_proc_ls_background_function  ?
_pd_proc_ls_pref_orient_corr     none
_pd_proc_ls_prof_R_factor        0.0685
_pd_proc_ls_prof_wR_factor       0.0952
_pd_proc_ls_prof_wR_expected     0.0952

_refine_special_details          
; ?
;

_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_gt          0.0627
_refine_ls_R_factor_all          0.0598
_refine_ls_wR_factor_all         0.0637
_refine_ls_goodness_of_fit_all   1.00
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_parameters     26
_refine_ls_number_restraints     20
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0289
_refine_ls_shift/su_mean         0.0073
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?

_pd_proc_2theta_range_min        4
_pd_proc_2theta_range_max        120
_pd_proc_2theta_range_inc        0.01
_pd_proc_wavelength              ?

_pd_block_diffractogram_id       ?

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0191 0.0096 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0516 0.0335 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Pb -4.0837 8.6878 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
S 0.3357 0.5642 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?


#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1205(10) 0.591(4) 0.241(4) Uiso 0.038 4 1 d . . .
C2 C 0.1834(11) 0.782(4) 0.290(4) Uiso 0.038 4 1 d . . .
C3 C 0.2717(10) 0.751(4) 0.253(3) Uiso 0.038 4 1 d . . .
C4 C 0.2969(10) 0.529(4) 0.166(4) Uiso 0.038 4 1 d . . .
C5 C 0.2339(11) 0.339(4) 0.116(4) Uiso 0.038 4 1 d . . .
C6 C 0.1457(10) 0.370(4) 0.154(4) Uiso 0.038 4 1 d . . .
O1 O 0.031(3) 0.635(5) 0.238(5) Uiso 0.038 4 1 d . . .
S1 S 0.4220(8) 0.454(3) 0.1242(16) Uiso 0.011 4 1 d . . .
Pb1 Pb 0.5 0.5 0.5 Uiso 0.011 2 1 d . . .
H1c2 H 0.166151 0.93351 0.350056 Uiso 0.0456 4 1 d . . .
H1c3 H 0.314821 0.881456 0.28664 Uiso 0.0456 4 1 d . . .
H1c5 H 0.251225 0.187088 0.056903 Uiso 0.0456 4 1 d . . .
H1c6 H 0.102547 0.239277 0.120151 Uiso 0.0456 4 1 d . . .
H1 H 0.014149 0.767 0.288418 Uiso 0.0456 4 1 d . . .



#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . . 1.40(3) ?
C1 C6 . . 1.40(3) ?
C1 O1 . . 1.36(4) ?
C2 C3 . . 1.40(3) ?
C2 H1c2 . . 0.96 ?
C3 C4 . . 1.40(3) ?
C3 H1c3 . . 0.96 ?
C4 C5 . . 1.40(3) ?
C4 S1 . . 1.99(2) ?
C5 C6 . . 1.40(3) ?
C5 H1c5 . . 0.96 ?
C6 H1c6 . . 0.96 ?
O1 H1 . . 0.84(3) ?
S1 Pb1 . . 3.003(12) ?
S1 Pb1 . 2_645 2.844(14) ?
S1 Pb1 . 2_655 3.250(14) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . . 120.0(17) ?
C2 C1 O1 . . . 122(2) ?
C6 C1 O1 . . . 116(2) ?
C1 C2 C3 . . . 120(2) ?
C1 C2 H1c2 . . . 120 ?
C3 C2 H1c2 . . . 120 ?
C2 C3 C4 . . . 120.0(17) ?
C2 C3 H1c3 . . . 120 ?
C4 C3 H1c3 . . . 120 ?
C3 C4 C5 . . . 120.0(17) ?
C3 C4 S1 . . . 123.0(13) ?
C5 C4 S1 . . . 116.8(16) ?
C4 C5 C6 . . . 120(2) ?
C4 C5 H1c5 . . . 120 ?
C6 C5 H1c5 . . . 120 ?
C1 C6 C5 . . . 120.0(17) ?
C1 C6 H1c6 . . . 120 ?
C5 C6 H1c6 . . . 120 ?
C1 O1 H1 . . . 119(3) ?
C4 S1 Pb1 . . . 97.1(9) ?
C4 S1 Pb1 . . 2_645 130.4(9) ?
C4 S1 Pb1 . . 2_655 104.7(8) ?
Pb1 S1 Pb1 . . 2_645 104.3(4) ?
Pb1 S1 Pb1 . . 2_655 95.1(4) ?
Pb1 S1 Pb1 2_645 . 2_655 117.0(4) ?
S1 Pb1 S1 . . 2_645 76.9(3) ?
S1 Pb1 S1 . . 2_655 83.4(4) ?
S1 Pb1 S1 . . 3_666 180 ?
S1 Pb1 S1 . . 4_555 96.6(4) ?
S1 Pb1 S1 . . 4_565 103.1(3) ?
S1 Pb1 S1 2_645 . 2_655 117.0(4) ?
S1 Pb1 S1 2_645 . 3_666 103.1(3) ?
S1 Pb1 S1 2_645 . 4_555 63.0(4) ?
S1 Pb1 S1 2_645 . 4_565 180 ?
S1 Pb1 S1 2_655 . 3_666 96.6(4) ?
S1 Pb1 S1 2_655 . 4_555 180 ?
S1 Pb1 S1 2_655 . 4_565 63.0(4) ?
S1 Pb1 S1 3_666 . 4_555 83.4(4) ?
S1 Pb1 S1 3_666 . 4_565 76.9(3) ?
S1 Pb1 S1 4_555 . 4_565 117.0(4) ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H1c2 C5 . . 4_565 0.96 2.49 3.21(4) 132.02 ?
C6 H1c6 O1 . . 2_545 0.96 2.45 3.12(4) 127.40 ?
O1 H1 O1 . . 2_555 0.84(3) 2.04(3) 2.78(4) 147(3) ?
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2143104'
loop_
_audit_author_name
_audit_author_address
'Wei Xu'
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-06-07 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C6 H4 Pb1 S2'
_chemical_formula_weight         347.41
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   7.4789(7)
_cell_length_b                   5.2068(5)
_cell_length_c                   17.4623(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.3828(19)
_cell_angle_gamma                90
_cell_volume                     678.83(11)


_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    3.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_pd_spec_size_axial              ?
_pd_spec_size_equat              ?
_pd_spec_size_thick              ?
_pd_spec_mounting                ?
_pd_spec_mount_mode              ?
_pd_spec_shape                   ?
_pd_char_particle_morphology     ?
_pd_char_colour                  yellow
_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

_exptl_absorpt_coefficient_mu    53.2
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?
_pd_instr_location               
; ?
;
_pd_calibration_special_details  
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   ?
_diffrn_source_target            ?
_diffrn_source_type              ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54059
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       CuKα
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_type            ?

_pd_meas_scan_method             ?
_pd_meas_special_details         
; ?
;
_pd_meas_number_of_points        11501
_pd_meas_2theta_range_min        5.000
_pd_meas_2theta_range_max        120.000
_pd_meas_2theta_range_inc        0.01

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_pd_proc_ls_special_details      
; ?
;
_pd_proc_ls_profile_function     Pseudo-Voigt
_pd_proc_ls_background_function  '25 Legendre polynoms'
_pd_proc_ls_pref_orient_corr     none
_pd_proc_ls_prof_R_factor        0.0269
_pd_proc_ls_prof_wR_factor       0.0358
_pd_proc_ls_prof_wR_expected     0.0405

_refine_special_details          
; ?
;

_refine_ls_R_factor_gt           0.0179
_refine_ls_wR_factor_gt          0.0217
_refine_ls_R_factor_all          0.0180
_refine_ls_wR_factor_all         0.0218
_refine_ls_goodness_of_fit_all   0.88
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_parameters     68
_refine_ls_number_restraints     12
_refine_ls_number_constraints    2
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0220
_refine_ls_shift/su_mean         0.0027
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        120
_pd_proc_2theta_range_inc        0.01
_pd_proc_wavelength              ?

_pd_block_diffractogram_id       ?

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0191 0.0096 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Pb -4.0837 8.6878 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
S 0.3357 0.5642 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'



#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.2531(10) -0.3248(3) 0.2501(8) Uiso 0.0119 4 1 d . . .
S1 S 0.095(4) 0.107(7) 0.178(2) Uiso 0.0143 4 1 d . . .
S2 S 0.388(4) 0.115(7) 0.326(2) Uiso 0.0143 4 1 d . . .
C1 C 0.447(4) 0.039(7) 0.4236(8) Uiso 0.0171 4 1 d . . .
C4 C 0.042(4) 0.037(7) 0.0774(6) Uiso 0.0171 4 1 d . . .
C2 C 0.401(3) 0.216(4) 0.478(2) Uiso 0.0171 4 1 d . . .
C3 C 0.454(3) 0.177(5) 0.5547(16) Uiso 0.0171 4 1 d . . .
C5 C -0.061(4) 0.217(4) 0.036(2) Uiso 0.0171 4 1 d . . .
C6 C -0.103(3) 0.180(5) -0.0411(19) Uiso 0.0171 4 1 d . . .
H1c2 H 0.331614 0.364746 0.463447 Uiso 0.0206 4 1 d . . .
H1c3 H 0.421487 0.298722 0.59276 Uiso 0.0206 4 1 d . . .
H1c5 H -0.103538 0.36695 0.061488 Uiso 0.0206 4 1 d . . .
H1c6 H -0.174834 0.304769 -0.069544 Uiso 0.0206 4 1 d . . .



#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pb1 S1 . . 2.81(4) ?
Pb1 S1 . 2_545 2.98(3) ?
Pb1 S2 . . 2.80(4) ?
Pb1 S2 . 2_645 3.08(3) ?
S1 C4 . . 1.81(4) ?
S2 C1 . . 1.79(4) ?
C1 C2 . . 1.38(4) ?
C1 C3 . 3_656 1.39(4) ?
C4 C5 . . 1.39(4) ?
C4 C6 . 3_555 1.39(4) ?
C2 C3 . . 1.38(5) ?
C2 H1c2 . . 0.96 ?
C3 H1c3 . . 0.96 ?
C5 C6 . . 1.38(5) ?
C5 H1c5 . . 0.96 ?
C6 H1c6 . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
S1 Pb1 S1 . . 2_545 86.0(10) ?
S1 Pb1 S2 . . . 71.8(10) ?
S1 Pb1 S2 . . 2_645 104.0(10) ?
S1 Pb1 S2 2_545 . . 101.4(10) ?
S1 Pb1 S2 2_545 . 2_645 167.4(10) ?
S2 Pb1 S2 . . 2_645 89.2(9) ?
Pb1 S1 Pb1 . . 2_555 105.1(12) ?
Pb1 S1 C4 . . . 110(2) ?
Pb1 S1 C4 2_555 . . 106.7(16) ?
Pb1 S2 Pb1 . . 2_655 100.4(11) ?
Pb1 S2 C1 . . . 109(2) ?
Pb1 S2 C1 2_655 . . 105.2(15) ?
S2 C1 C2 . . . 117(3) ?
S2 C1 C3 . . 3_656 123(2) ?
C2 C1 C3 . . 3_656 120(2) ?
S1 C4 C5 . . . 117(3) ?
S1 C4 C6 . . 3_555 123(2) ?
C5 C4 C6 . . 3_555 120(2) ?
C1 C2 C3 . . . 120(2) ?
C1 C2 H1c2 . . . 120 ?
C3 C2 H1c2 . . . 120 ?
C1 C3 C2 3_656 . . 120(2) ?
C1 C3 H1c3 3_656 . . 120 ?
C2 C3 H1c3 . . . 120 ?
C4 C5 C6 . . . 120(2) ?
C4 C5 H1c5 . . . 119.95 ?
C6 C5 H1c5 . . . 119.94 ?
C4 C6 C5 3_555 . . 120(2) ?
C4 C6 H1c6 3_555 . . 120.09 ?
C5 C6 H1c6 . . . 120.08 ?
