# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_khc1016b
_database_code_depnum_ccdc_archive 'CCDC 1568889'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2018-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          501
_chemical_formula_moiety         'C16 H12 N2 O Pt S'
_chemical_formula_sum            'C16 H12 N2 O Pt S'
_chemical_formula_weight         475.42

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'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   8.6392(17)
_cell_length_b                   8.6163(17)
_cell_length_c                   20.066(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.80(3)
_cell_angle_gamma                90.00
_cell_volume                     1490.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2624
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    9.553
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2511
_exptl_absorpt_correction_T_max  0.4486
_exptl_absorpt_process_details   'shape of crystal determined optically'

_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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7906
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_sigmaI/netI    0.1221
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2624
_reflns_number_gt                1605
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0172P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2624
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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
Pt1 Pt 0.56573(7) 0.91651(6) 0.60302(2) 0.04896(18) Uani 1 1 d . . .
S1 S 0.3386(5) 0.7992(4) 0.57841(19) 0.0656(11) Uani 1 1 d . . .
O1 O 0.6355(12) 0.8107(10) 0.5163(4) 0.060(3) Uani 1 1 d . . .
N1 N 0.7676(13) 1.0307(10) 0.6258(5) 0.047(3) Uani 1 1 d . . .
N2 N 0.5222(19) 0.7284(13) 0.4819(5) 0.064(4) Uani 1 1 d . . .
C1 C 0.5098(16) 1.0201(14) 0.6864(6) 0.050(3) Uani 1 1 d . . .
C2 C 0.3784(17) 1.0170(14) 0.7187(6) 0.051(3) Uani 1 1 d . . .
H2 H 0.2966 0.9572 0.7003 0.062 Uiso 1 1 calc R . .
C3 C 0.3557(19) 1.097(2) 0.7774(7) 0.079(4) Uani 1 1 d . . .
H3 H 0.2621 1.0907 0.7977 0.094 Uiso 1 1 calc R . .
C4 C 0.482(2) 1.1878(17) 0.8055(7) 0.068(5) Uani 1 1 d . . .
H4 H 0.4705 1.2439 0.8444 0.082 Uiso 1 1 calc R . .
C5 C 0.621(2) 1.1937(16) 0.7756(7) 0.062(4) Uani 1 1 d . . .
H5 H 0.7036 1.2515 0.7945 0.074 Uiso 1 1 calc R . .
C6 C 0.6356(16) 1.1102(15) 0.7160(6) 0.048(3) Uani 1 1 d . . .
C7 C 0.7766(18) 1.1163(13) 0.6818(6) 0.052(4) Uani 1 1 d . . .
C8 C 0.912(2) 1.1950(17) 0.6991(7) 0.066(5) Uani 1 1 d . . .
H8 H 0.9195 1.2512 0.7387 0.079 Uiso 1 1 calc R . .
C9 C 1.0345(19) 1.1932(16) 0.6599(8) 0.068(4) Uani 1 1 d . . .
H9 H 1.1231 1.2510 0.6717 0.082 Uiso 1 1 calc R . .
C10 C 1.0257(16) 1.1050(17) 0.6030(7) 0.071(4) Uani 1 1 d . . .
H10 H 1.1090 1.0993 0.5761 0.085 Uiso 1 1 calc R . .
C11 C 0.885(2) 1.0216(15) 0.5859(7) 0.070(5) Uani 1 1 d . . .
H11 H 0.8752 0.9617 0.5473 0.084 Uiso 1 1 calc R . .
C12 C 0.383(2) 0.7095(14) 0.5054(7) 0.060(4) Uani 1 1 d . . .
C13 C 0.273(2) 0.6180(15) 0.4666(7) 0.072(5) Uani 1 1 d . . .
H13 H 0.1726 0.6054 0.4798 0.086 Uiso 1 1 calc R . .
C14 C 0.318(2) 0.5492(17) 0.4096(9) 0.081(6) Uani 1 1 d . . .
H14 H 0.2487 0.4841 0.3855 0.097 Uiso 1 1 calc R . .
C15 C 0.458(2) 0.573(2) 0.3878(8) 0.080(6) Uani 1 1 d . . .
H15 H 0.4840 0.5274 0.3482 0.096 Uiso 1 1 calc R . .
C16 C 0.564(2) 0.6645(17) 0.4225(7) 0.078(5) Uani 1 1 d . . .
H16 H 0.6611 0.6831 0.4067 0.094 Uiso 1 1 calc R . .


_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
Pt1 C1 1.984(13) . ?
Pt1 N1 2.028(11) . ?
Pt1 O1 2.089(9) . ?
Pt1 S1 2.233(4) . ?
S1 C12 1.723(15) . ?
O1 N2 1.359(14) . ?
N1 C11 1.333(18) . ?
N1 C7 1.342(14) . ?
N2 C12 1.327(18) . ?
N2 C16 1.382(18) . ?
C1 C2 1.344(18) . ?
C1 C6 1.432(17) . ?
C2 C3 1.388(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.43(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.38(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(16) . ?
C5 H5 0.9300 . ?
C6 C7 1.438(19) . ?
C7 C8 1.374(19) . ?
C8 C9 1.36(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(18) . ?
C9 H9 0.9300 . ?
C10 C11 1.436(19) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.429(18) . ?
C13 C14 1.37(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.33(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.36(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C1 Pt1 N1 81.1(5) . . ?
C1 Pt1 O1 177.3(5) . . ?
N1 Pt1 O1 96.2(4) . . ?
C1 Pt1 S1 97.5(4) . . ?
N1 Pt1 S1 177.8(3) . . ?
O1 Pt1 S1 85.2(3) . . ?
C12 S1 Pt1 98.5(6) . . ?
N2 O1 Pt1 114.4(9) . . ?
C11 N1 C7 122.0(12) . . ?
C11 N1 Pt1 120.8(9) . . ?
C7 N1 Pt1 117.2(10) . . ?
C12 N2 O1 121.3(12) . . ?
C12 N2 C16 123.4(14) . . ?
O1 N2 C16 115.2(15) . . ?
C2 C1 C6 116.9(12) . . ?
C2 C1 Pt1 131.2(10) . . ?
C6 C1 Pt1 111.9(10) . . ?
C1 C2 C3 124.8(13) . . ?
C1 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
C2 C3 C4 117.3(14) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C5 C4 C3 120.9(14) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.7(14) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 121.4(13) . . ?
C5 C6 C7 120.8(13) . . ?
C1 C6 C7 117.8(12) . . ?
N1 C7 C8 118.9(15) . . ?
N1 C7 C6 112.0(12) . . ?
C8 C7 C6 129.1(13) . . ?
C9 C8 C7 122.0(14) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 119.0(14) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C11 118.5(14) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
N1 C11 C10 119.5(13) . . ?
N1 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
N2 C12 C13 117.4(15) . . ?
N2 C12 S1 120.4(11) . . ?
C13 C12 S1 122.1(15) . . ?
C14 C13 C12 118.7(17) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 121.3(15) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 121.3(17) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 N2 117.7(18) . . ?
C15 C16 H16 121.1 . . ?
N2 C16 H16 121.1 . . ?

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
C1 Pt1 S1 C12 179.4(5) . . . . ?
N1 Pt1 S1 C12 130(8) . . . . ?
O1 Pt1 S1 C12 -1.0(5) . . . . ?
C1 Pt1 O1 N2 175(9) . . . . ?
N1 Pt1 O1 N2 -175.3(7) . . . . ?
S1 Pt1 O1 N2 3.0(7) . . . . ?
C1 Pt1 N1 C11 -178.4(10) . . . . ?
O1 Pt1 N1 C11 2.1(10) . . . . ?
S1 Pt1 N1 C11 -128(8) . . . . ?
C1 Pt1 N1 C7 0.8(8) . . . . ?
O1 Pt1 N1 C7 -178.8(8) . . . . ?
S1 Pt1 N1 C7 51(9) . . . . ?
Pt1 O1 N2 C12 -4.7(14) . . . . ?
Pt1 O1 N2 C16 176.7(8) . . . . ?
N1 Pt1 C1 C2 180.0(13) . . . . ?
O1 Pt1 C1 C2 -170(8) . . . . ?
S1 Pt1 C1 C2 1.6(12) . . . . ?
N1 Pt1 C1 C6 -1.2(8) . . . . ?
O1 Pt1 C1 C6 9(9) . . . . ?
S1 Pt1 C1 C6 -179.6(8) . . . . ?
C6 C1 C2 C3 1.2(19) . . . . ?
Pt1 C1 C2 C3 180.0(10) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C4 C5 C6 C1 -0.2(19) . . . . ?
C4 C5 C6 C7 178.2(12) . . . . ?
C2 C1 C6 C5 -1.0(17) . . . . ?
Pt1 C1 C6 C5 -180.0(9) . . . . ?
C2 C1 C6 C7 -179.4(11) . . . . ?
Pt1 C1 C6 C7 1.6(14) . . . . ?
C11 N1 C7 C8 -1.1(17) . . . . ?
Pt1 N1 C7 C8 179.8(9) . . . . ?
C11 N1 C7 C6 179.0(11) . . . . ?
Pt1 N1 C7 C6 -0.1(12) . . . . ?
C5 C6 C7 N1 -179.4(10) . . . . ?
C1 C6 C7 N1 -1.0(15) . . . . ?
C5 C6 C7 C8 1(2) . . . . ?
C1 C6 C7 C8 179.1(12) . . . . ?
N1 C7 C8 C9 2(2) . . . . ?
C6 C7 C8 C9 -177.7(13) . . . . ?
C7 C8 C9 C10 -3(2) . . . . ?
C8 C9 C10 C11 2(2) . . . . ?
C7 N1 C11 C10 0.3(18) . . . . ?
Pt1 N1 C11 C10 179.4(8) . . . . ?
C9 C10 C11 N1 -0.7(18) . . . . ?
O1 N2 C12 C13 -178.5(10) . . . . ?
C16 N2 C12 C13 0.0(19) . . . . ?
O1 N2 C12 S1 3.9(17) . . . . ?
C16 N2 C12 S1 -177.6(9) . . . . ?
Pt1 S1 C12 N2 -1.1(11) . . . . ?
Pt1 S1 C12 C13 -178.6(10) . . . . ?
N2 C12 C13 C14 3.1(18) . . . . ?
S1 C12 C13 C14 -179.3(11) . . . . ?
C12 C13 C14 C15 -4(2) . . . . ?
C13 C14 C15 C16 2(3) . . . . ?
C14 C15 C16 N2 1(2) . . . . ?
C12 N2 C16 C15 -2(2) . . . . ?
O1 N2 C16 C15 176.3(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.156
