# 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_20140
_database_code_depnum_ccdc_archive 'CCDC 2171923'
loop_
_audit_author_name
_audit_author_address
'Maren Pink' 'Indiana University'
_audit_update_record             
;
2022-05-10 deposited with the CCDC.	2022-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'0.98 (C13H6N2O5), 0.98 SO(CH3)2, 0.02 PtClC13H4N2O5'
_chemical_formula_sum            'C14.96 H11.84 Cl0.02 N2 O5.98 Pt0.02 S0.98'
_chemical_formula_weight         351.40

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt -1.7033 8.3905 '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                   14.2283(5)
_cell_length_b                   12.4939(4)
_cell_length_c                   8.2937(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.4225(12)
_cell_angle_gamma                90
_cell_volume                     1458.44(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9780
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.192
_exptl_absorpt_coefficient_mu    0.455
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6887
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
; 
L. Krause, R. Herbst-Irmer, G.M. Sheldrick, D. Stalke, 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. (2015), 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'0.50 degree frames measured for 1 and 1.5 seconds each'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            78401
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         27.520
_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             3356
_reflns_number_gt                2861
_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       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'
_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)+(0.0419P)²+1.0894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3356
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
O1 O 0.89139(9) 0.55194(9) 0.28242(16) 0.0311(3) Uani 1 1 d . . . . .
O2 O 0.90224(10) 1.05217(10) 0.38748(16) 0.0347(3) Uani 1 1 d . . . . .
O3 O 0.73656(12) 1.10416(10) 0.4926(2) 0.0493(4) Uani 1 1 d . . . . .
O4 O 0.48380(9) 0.67535(10) 0.77676(16) 0.0332(3) Uani 1 1 d . . . . .
O5 O 0.57882(10) 0.56800(10) 0.66426(16) 0.0320(3) Uani 1 1 d . . . . .
H5O H 0.626(2) 0.565(2) 0.609(3) 0.059(8) Uiso 0.9795(2) 1 d . . P A 1
N1 N 0.81787(10) 0.68634(11) 0.39987(16) 0.0216(3) Uani 1 1 d . . . . .
H1N H 0.7808(15) 0.6370(18) 0.439(3) 0.034(6) Uiso 0.9795(2) 1 d . . P A 1
N2 N 0.67416(10) 0.73596(10) 0.56533(16) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.88864(12) 0.64818(13) 0.3145(2) 0.0245(3) Uani 1 1 d . . . . .
C2 C 0.95169(12) 0.72953(14) 0.2676(2) 0.0264(4) Uani 1 1 d . . . . .
H2 H 1.002171 0.708946 0.210828 0.032 Uiso 1 1 calc R U . . .
C3 C 0.94067(12) 0.83417(14) 0.3024(2) 0.0263(4) Uani 1 1 d . . . . .
H3 H 0.983969 0.885617 0.271818 0.032 Uiso 1 1 calc R U . . .
C4 C 0.86453(12) 0.86766(13) 0.38450(19) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.84951(13) 0.98103(13) 0.41767(19) 0.0251(3) Uani 1 1 d . . . . .
C6 C 0.75921(13) 1.01122(13) 0.4878(2) 0.0284(4) Uani 1 1 d . . . . .
C7 C 0.69998(12) 0.92463(12) 0.5425(2) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.62149(13) 0.94682(13) 0.6184(2) 0.0258(3) Uani 1 1 d . . . . .
H8 H 0.602992 1.018643 0.634393 0.031 Uiso 1 1 calc R U . . .
C9 C 0.57069(12) 0.86223(13) 0.6702(2) 0.0248(3) Uani 1 1 d . . . . .
H9 H 0.516996 0.874546 0.723585 0.030 Uiso 1 1 calc R U . . .
C10 C 0.60039(12) 0.75861(13) 0.64205(19) 0.0223(3) Uani 1 1 d . . . . .
C11 C 0.72350(11) 0.81773(12) 0.51688(18) 0.0199(3) Uani 1 1 d . . . . .
C12 C 0.80455(11) 0.79121(12) 0.43174(18) 0.0203(3) Uani 1 1 d . . . . .
C13 C 0.54895(12) 0.66401(13) 0.7002(2) 0.0252(3) Uani 1 1 d . . . . .
S1 S 0.72374(4) 0.40323(4) 0.45354(6) 0.02606(13) Uani 0.9795(2) 1 d . . P A 1
O6 O 0.72782(10) 0.51457(10) 0.52848(18) 0.0346(3) Uani 0.9795(2) 1 d . . P A 1
C14 C 0.65933(16) 0.32782(14) 0.5810(3) 0.0383(5) Uani 0.9795(2) 1 d . . P A 1
H14A H 0.654212 0.253485 0.543001 0.057 Uiso 0.9795(2) 1 calc R U P A 1
H14B H 0.595579 0.358275 0.577382 0.057 Uiso 0.9795(2) 1 calc R U P A 1
H14C H 0.692497 0.329931 0.693154 0.057 Uiso 0.9795(2) 1 calc R U P A 1
C15 C 0.83900(14) 0.34828(15) 0.5110(3) 0.0376(5) Uani 0.9795(2) 1 d . . P A 1
H15A H 0.838643 0.272584 0.479927 0.056 Uiso 0.9795(2) 1 calc R U P A 1
H15B H 0.857124 0.354792 0.629182 0.056 Uiso 0.9795(2) 1 calc R U P A 1
H15C H 0.884784 0.387175 0.455441 0.056 Uiso 0.9795(2) 1 calc R U P A 1
Pt1 Pt 0.7159(3) 0.5918(3) 0.5129(5) 0.0346(3) Uani 0.0205(2) 1 d . . P A 2
Cl1 Cl 0.7607(19) 0.393(2) 0.458(3) 0.02606(13) Uani 0.0205(2) 1 d . . P A 2


_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
O1 C1 1.233(2) . ?
O2 C5 1.213(2) . ?
O3 C6 1.207(2) . ?
O4 C13 1.206(2) . ?
O5 C13 1.321(2) . ?
O5 Pt1 2.488(4) . ?
O5 H5O 0.87(3) . ?
N1 C12 1.355(2) . ?
N1 C1 1.397(2) . ?
N1 Pt1 2.185(4) . ?
N1 H1N 0.90(2) . ?
N2 C11 1.334(2) . ?
N2 C10 1.335(2) . ?
N2 Pt1 1.966(4) . ?
C1 C2 1.446(2) . ?
C2 C3 1.353(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(2) . ?
C3 H3 0.9500 . ?
C4 C12 1.375(2) . ?
C4 C5 1.465(2) . ?
C5 C6 1.533(2) . ?
C6 C7 1.483(2) . ?
C7 C8 1.388(2) . ?
C7 C11 1.401(2) . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C13 1.506(2) . ?
C11 C12 1.475(2) . ?
S1 O6 1.5213(13) . ?
S1 C14 1.7688(19) . ?
S1 C15 1.777(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
Pt1 Cl1 2.62(3) . ?

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
C13 O5 Pt1 107.92(13) . . ?
C13 O5 H5O 117.5(19) . . ?
C12 N1 C1 124.09(14) . . ?
C12 N1 Pt1 108.57(14) . . ?
C1 N1 Pt1 127.28(14) . . ?
C12 N1 H1N 118.9(14) . . ?
C1 N1 H1N 117.0(14) . . ?
C11 N2 C10 117.79(13) . . ?
C11 N2 Pt1 116.45(15) . . ?
C10 N2 Pt1 125.74(15) . . ?
O1 C1 N1 119.35(16) . . ?
O1 C1 C2 125.91(16) . . ?
N1 C1 C2 114.72(14) . . ?
C3 C2 C1 121.73(16) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 120.39(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C12 C4 C3 118.64(15) . . ?
C12 C4 C5 120.30(15) . . ?
C3 C4 C5 121.07(15) . . ?
O2 C5 C4 123.95(16) . . ?
O2 C5 C6 118.44(15) . . ?
C4 C5 C6 117.56(14) . . ?
O3 C6 C7 121.70(17) . . ?
O3 C6 C5 119.44(16) . . ?
C7 C6 C5 118.82(14) . . ?
C8 C7 C11 119.04(15) . . ?
C8 C7 C6 121.61(15) . . ?
C11 C7 C6 119.35(15) . . ?
C9 C8 C7 118.68(15) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 118.23(15) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
N2 C10 C9 123.79(15) . . ?
N2 C10 C13 116.06(14) . . ?
C9 C10 C13 120.15(15) . . ?
N2 C11 C7 122.43(15) . . ?
N2 C11 C12 117.05(13) . . ?
C7 C11 C12 120.51(14) . . ?
N1 C12 C4 120.36(15) . . ?
N1 C12 C11 116.86(14) . . ?
C4 C12 C11 122.78(14) . . ?
O4 C13 O5 121.53(15) . . ?
O4 C13 C10 121.57(15) . . ?
O5 C13 C10 116.90(15) . . ?
O6 S1 C14 103.59(8) . . ?
O6 S1 C15 105.38(9) . . ?
C14 S1 C15 99.94(11) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 Pt1 N1 80.83(13) . . ?
N2 Pt1 O5 73.30(13) . . ?
N1 Pt1 O5 154.13(17) . . ?
N2 Pt1 Cl1 175.0(6) . . ?
N1 Pt1 Cl1 104.2(6) . . ?
O5 Pt1 Cl1 101.7(6) . . ?

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
C12 N1 C1 O1 -175.39(15) . . . . ?
Pt1 N1 C1 O1 7.6(3) . . . . ?
C12 N1 C1 C2 2.9(2) . . . . ?
Pt1 N1 C1 C2 -174.04(18) . . . . ?
O1 C1 C2 C3 177.09(17) . . . . ?
N1 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C12 1.9(2) . . . . ?
C2 C3 C4 C5 -177.71(16) . . . . ?
C12 C4 C5 O2 175.94(16) . . . . ?
C3 C4 C5 O2 -4.4(3) . . . . ?
C12 C4 C5 C6 -6.9(2) . . . . ?
C3 C4 C5 C6 172.78(15) . . . . ?
O2 C5 C6 O3 9.1(3) . . . . ?
C4 C5 C6 O3 -168.27(18) . . . . ?
O2 C5 C6 C7 -173.18(16) . . . . ?
C4 C5 C6 C7 9.5(2) . . . . ?
O3 C6 C7 C8 -7.3(3) . . . . ?
C5 C6 C7 C8 175.04(15) . . . . ?
O3 C6 C7 C11 172.57(18) . . . . ?
C5 C6 C7 C11 -5.1(2) . . . . ?
C11 C7 C8 C9 1.8(2) . . . . ?
C6 C7 C8 C9 -178.35(16) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C11 N2 C10 C9 1.8(2) . . . . ?
Pt1 N2 C10 C9 -177.0(2) . . . . ?
C11 N2 C10 C13 -177.77(14) . . . . ?
Pt1 N2 C10 C13 3.4(3) . . . . ?
C8 C9 C10 N2 -1.2(3) . . . . ?
C8 C9 C10 C13 178.36(15) . . . . ?
C10 N2 C11 C7 -0.6(2) . . . . ?
Pt1 N2 C11 C7 178.34(19) . . . . ?
C10 N2 C11 C12 -179.77(14) . . . . ?
Pt1 N2 C11 C12 -0.9(2) . . . . ?
C8 C7 C11 N2 -1.2(2) . . . . ?
C6 C7 C11 N2 178.92(15) . . . . ?
C8 C7 C11 C12 177.95(15) . . . . ?
C6 C7 C11 C12 -1.9(2) . . . . ?
C1 N1 C12 C4 -2.3(2) . . . . ?
Pt1 N1 C12 C4 175.13(17) . . . . ?
C1 N1 C12 C11 177.24(14) . . . . ?
Pt1 N1 C12 C11 -5.3(2) . . . . ?
C3 C4 C12 N1 -0.2(2) . . . . ?
C5 C4 C12 N1 179.43(14) . . . . ?
C3 C4 C12 C11 -179.77(14) . . . . ?
C5 C4 C12 C11 -0.1(2) . . . . ?
N2 C11 C12 N1 4.5(2) . . . . ?
C7 C11 C12 N1 -174.71(14) . . . . ?
N2 C11 C12 C4 -175.93(15) . . . . ?
C7 C11 C12 C4 4.9(2) . . . . ?
Pt1 O5 C13 O4 -178.58(17) . . . . ?
Pt1 O5 C13 C10 1.1(2) . . . . ?
N2 C10 C13 O4 176.92(16) . . . . ?
C9 C10 C13 O4 -2.7(3) . . . . ?
N2 C10 C13 O5 -2.8(2) . . . . ?
C9 C10 C13 O5 177.65(15) . . . . ?

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
_geom_hbond_publ_flag
O5 H5O^a S1^a 0.87(3) 2.86(3) 3.5497(14) 137(2) . yes
O5 H5O^a O6^a 0.87(3) 1.80(3) 2.6282(19) 161(3) . yes
N1 H1N^a S1^a 0.90(2) 3.04(2) 3.8311(15) 147.5(17) . yes
N1 H1N^a O6^a 0.90(2) 1.90(2) 2.7902(19) 167(2) . yes
C2 H2 O2 0.95 2.58 3.416(2) 146.4 2_745 yes
C14^a H14A^a O3 0.98 2.27 3.129(2) 145.1 1_545 yes
C14^a H14C^a O3 0.98 2.60 3.533(3) 158.3 4_576 yes
C15^a H15A^a O3 0.98 2.57 3.374(2) 139.6 1_545 yes
C15^a H15B^a O2 0.98 2.44 3.359(3) 156.2 4_576 yes
C15^a H15C^a O1 0.98 2.52 3.322(2) 139.1 . yes

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.051

