# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_test1
_database_code_depnum_ccdc_archive 'CCDC 1572814'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N O S2'
_chemical_formula_weight         286.38

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   10.834(4)
_cell_length_b                   10.782(4)
_cell_length_c                   11.696(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.39(3)
_cell_angle_gamma                90.00
_cell_volume                     1363.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_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            9778
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2391
_reflns_number_gt                1517
_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)+(0.1000P)²+0.9780P] 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         2391
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1987
_refine_ls_wR_factor_gt          0.1761
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_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
S1 S 0.97530(12) 0.20662(11) 0.36953(12) 0.0776(5) Uani 1 1 d . . .
S2 S 0.83592(12) 0.37170(12) 0.21107(11) 0.0782(5) Uani 1 1 d . . .
C11 C 1.0980(4) 0.2245(4) 0.4707(4) 0.0622(11) Uani 1 1 d . . .
C7 C 0.9572(4) 0.3520(4) 0.3161(4) 0.0625(11) Uani 1 1 d . . .
C9 C 1.1276(4) 0.4500(4) 0.4352(4) 0.0619(11) Uani 1 1 d . . .
C8 C 1.0289(4) 0.4497(4) 0.3499(4) 0.0658(12) Uani 1 1 d . . .
H8 H 1.0115 0.5247 0.3131 0.079 Uiso 1 1 calc R . .
C2 C 0.6670(4) 0.2005(4) 0.2634(4) 0.0621(11) Uani 1 1 d . . .
C10 C 1.1579(4) 0.3354(4) 0.4967(4) 0.0611(11) Uani 1 1 d . . .
C1 C 0.5942(5) 0.1013(4) 0.2239(4) 0.0735(13) Uani 1 1 d . . .
H1 H 0.6102 0.0629 0.1551 0.088 Uiso 1 1 calc R . .
C12 C 1.1335(4) 0.1183(5) 0.5298(5) 0.0816(14) Uani 1 1 d . . .
H12 H 1.0949 0.0433 0.5113 0.098 Uiso 1 1 calc R . .
C3 C 0.6390(5) 0.2555(5) 0.3638(4) 0.0770(14) Uani 1 1 d . . .
H3 H 0.6856 0.3226 0.3917 0.092 Uiso 1 1 calc R . .
C14 C 1.2832(5) 0.2323(5) 0.6442(5) 0.0879(15) Uani 1 1 d . . .
H14 H 1.3436 0.2355 0.7040 0.105 Uiso 1 1 calc R . .
C6 C 0.4981(5) 0.0596(5) 0.2867(6) 0.0861(16) Uani 1 1 d . . .
H6 H 0.4512 -0.0080 0.2605 0.103 Uiso 1 1 calc R . .
C15 C 1.2505(4) 0.3363(5) 0.5836(4) 0.0772(14) Uani 1 1 d . . .
H15 H 1.2917 0.4102 0.6011 0.093 Uiso 1 1 calc R . .
C13 C 1.2251(5) 0.1228(5) 0.6153(5) 0.0883(16) Uani 1 1 d . . .
H13 H 1.2484 0.0506 0.6544 0.106 Uiso 1 1 calc R . .
C5 C 0.4718(5) 0.1156(7) 0.3852(6) 0.1027(19) Uani 1 1 d . . .
H5 H 0.4060 0.0885 0.4263 0.123 Uiso 1 1 calc R . .
C4 C 0.5433(6) 0.2130(6) 0.4237(5) 0.0970(18) Uani 1 1 d . . .
H4 H 0.5264 0.2512 0.4923 0.116 Uiso 1 1 calc R . .
O1 O 1.1868(3) 0.5452(3) 0.4585(3) 0.0803(10) Uani 1 1 d . . .
N1 N 0.7674(4) 0.2350(4) 0.2016(4) 0.0742(11) Uani 1 1 d . . .
H1N H 0.796(4) 0.196(4) 0.145(4) 0.063(14) Uiso 1 1 d . . .


_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
S1 C7 1.694(4) . ?
S1 C11 1.738(4) . ?
S2 N1 1.652(4) . ?
S2 C7 1.758(5) . ?
C11 C12 1.380(6) . ?
C11 C10 1.386(6) . ?
C7 C8 1.354(6) . ?
C9 O1 1.232(5) . ?
C9 C8 1.419(6) . ?
C9 C10 1.457(6) . ?
C2 C3 1.366(6) . ?
C2 C1 1.392(6) . ?
C2 N1 1.391(6) . ?
C10 C15 1.386(6) . ?
C1 C6 1.384(7) . ?
C12 C13 1.369(7) . ?
C3 C4 1.363(7) . ?
C14 C15 1.362(7) . ?
C14 C13 1.371(7) . ?
C6 C5 1.346(8) . ?
C5 C4 1.366(9) . ?

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
C7 S1 C11 102.5(2) . . ?
N1 S2 C7 104.7(2) . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 S1 115.3(3) . . ?
C10 C11 S1 125.0(3) . . ?
C8 C7 S1 124.1(4) . . ?
C8 C7 S2 120.1(3) . . ?
S1 C7 S2 115.8(3) . . ?
O1 C9 C8 121.2(4) . . ?
O1 C9 C10 119.8(4) . . ?
C8 C9 C10 118.9(4) . . ?
C7 C8 C9 127.0(4) . . ?
C3 C2 C1 118.0(5) . . ?
C3 C2 N1 123.4(4) . . ?
C1 C2 N1 118.6(4) . . ?
C11 C10 C15 118.4(4) . . ?
C11 C10 C9 122.3(4) . . ?
C15 C10 C9 119.3(4) . . ?
C2 C1 C6 120.2(5) . . ?
C13 C12 C11 120.3(5) . . ?
C4 C3 C2 120.7(5) . . ?
C15 C14 C13 118.6(5) . . ?
C5 C6 C1 120.8(5) . . ?
C14 C15 C10 122.1(5) . . ?
C12 C13 C14 120.9(5) . . ?
C6 C5 C4 118.8(6) . . ?
C5 C4 C3 121.5(6) . . ?
C2 N1 S2 124.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.151
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_kmtbaso
_database_code_depnum_ccdc_archive 'CCDC 1583531'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        km-t-ba-so
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H13 N O3 S2'
_chemical_formula_sum            'C16 H13 N O3 S2'
_chemical_compound_source        synthesis
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         331.39

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'
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'
N N 0.0061 0.0033 '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'
_symmetry_int_tables_number      4
_chemical_absolute_configuration ?

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

_cell_length_a                   10.3912(7)
_cell_length_b                   5.6999(3)
_cell_length_c                   12.8081(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.459(7)
_cell_angle_gamma                90.00
_cell_volume                     740.75(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3207
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      24.99
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2827
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2197
_reflns_number_gt                1878
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Brucker SHELXTL'
_computing_publication_material  'Brucker SHELXTL'

_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)+(0.0192P)²+0.1528P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(11)
_refine_ls_number_reflns         2197
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_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
S2 S 0.16061(12) 0.97975(18) 0.11571(9) 0.0417(3) Uani 1 1 d . . .
S1 S 0.03749(11) 0.6117(2) 0.21997(10) 0.0436(3) Uani 1 1 d . . .
O2 O 0.0238(3) 1.0431(5) 0.0891(3) 0.0543(10) Uani 1 1 d . . .
O3 O 0.2610(3) 1.1523(5) 0.1474(3) 0.0574(10) Uani 1 1 d . . .
O1 O 0.4355(3) 0.5569(6) 0.4301(3) 0.0649(11) Uani 1 1 d . . .
N1 N 0.1894(3) 0.8399(6) 0.0150(3) 0.0421(10) Uani 1 1 d . . .
H1 H 0.1305 0.8343 -0.0435 0.051 Uiso 1 1 calc R . .
C2 C 0.2210(4) 0.3999(8) 0.3839(4) 0.0399(11) Uani 1 1 d . . .
C8 C 0.2955(4) 0.7457(8) 0.2886(3) 0.0386(11) Uani 1 1 d . . .
H8 H 0.3629 0.8477 0.2814 0.046 Uiso 1 1 calc R . .
C7 C 0.3246(4) 0.5672(9) 0.3725(4) 0.0441(12) Uani 1 1 d . . .
C6 C -0.0013(5) 0.2447(7) 0.3371(4) 0.0447(12) Uani 1 1 d . . .
H6 H -0.0864 0.2509 0.2954 0.054 Uiso 1 1 calc R . .
C11 C 0.3383(4) 0.6692(9) -0.0876(4) 0.0435(12) Uani 1 1 d . . .
C4 C 0.1586(5) 0.0607(8) 0.4757(4) 0.0485(13) Uani 1 1 d . . .
H4 H 0.1801 -0.0569 0.5268 0.058 Uiso 1 1 calc R . .
C1 C 0.0930(4) 0.4077(7) 0.3215(3) 0.0355(11) Uani 1 1 d . . .
C3 C 0.2524(5) 0.2199(8) 0.4611(4) 0.0458(12) Uani 1 1 d . . .
H3 H 0.3376 0.2091 0.5024 0.055 Uiso 1 1 calc R . .
C9 C 0.1787(4) 0.7717(7) 0.2217(3) 0.0359(10) Uani 1 1 d . . .
C14 C 0.3737(6) 0.5792(13) -0.2926(4) 0.0736(19) Uani 1 1 d . . .
H14 H 0.3862 0.5486 -0.3610 0.088 Uiso 1 1 calc R . .
C15 C 0.4153(6) 0.7846(12) -0.2430(5) 0.0722(18) Uani 1 1 d . . .
H15 H 0.4567 0.8959 -0.2775 0.087 Uiso 1 1 calc R . .
C16 C 0.3963(5) 0.8285(10) -0.1417(4) 0.0584(15) Uani 1 1 d . . .
H16 H 0.4240 0.9712 -0.1094 0.070 Uiso 1 1 calc R . .
C13 C 0.3136(6) 0.4191(10) -0.2407(5) 0.0722(18) Uani 1 1 d . . .
H13 H 0.2838 0.2789 -0.2746 0.087 Uiso 1 1 calc R . .
C12 C 0.2958(5) 0.4605(9) -0.1387(4) 0.0580(14) Uani 1 1 d . . .
H12 H 0.2552 0.3480 -0.1042 0.070 Uiso 1 1 calc R . .
C10 C 0.3174(4) 0.7201(9) 0.0226(4) 0.0507(13) Uani 1 1 d . . .
H10A H 0.3184 0.5746 0.0621 0.061 Uiso 1 1 calc R . .
H10B H 0.3881 0.8189 0.0607 0.061 Uiso 1 1 calc R . .
C5 C 0.0320(5) 0.0762(9) 0.4140(4) 0.0534(13) Uani 1 1 d . . .
H5 H -0.0315 -0.0303 0.4250 0.064 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
S2 O3 1.427(3) . ?
S2 O2 1.435(3) . ?
S2 N1 1.598(4) . ?
S2 C9 1.782(4) . ?
S1 C9 1.724(4) . ?
S1 C1 1.747(4) . ?
O1 C7 1.228(5) . ?
N1 C10 1.479(5) . ?
C2 C1 1.397(5) . ?
C2 C3 1.413(6) . ?
C2 C7 1.468(6) . ?
C8 C9 1.335(5) . ?
C8 C7 1.463(6) . ?
C6 C5 1.366(6) . ?
C6 C1 1.396(6) . ?
C11 C16 1.360(7) . ?
C11 C12 1.383(7) . ?
C11 C10 1.502(6) . ?
C4 C3 1.374(6) . ?
C4 C5 1.384(6) . ?
C14 C15 1.357(8) . ?
C14 C13 1.358(8) . ?
C15 C16 1.376(7) . ?
C13 C12 1.378(7) . ?

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
O3 S2 O2 121.3(2) . . ?
O3 S2 N1 108.7(2) . . ?
O2 S2 N1 106.4(2) . . ?
O3 S2 C9 107.0(2) . . ?
O2 S2 C9 106.5(2) . . ?
N1 S2 C9 105.99(19) . . ?
C9 S1 C1 101.5(2) . . ?
C10 N1 S2 120.0(3) . . ?
C1 C2 C3 118.1(4) . . ?
C1 C2 C7 123.4(4) . . ?
C3 C2 C7 118.5(4) . . ?
C9 C8 C7 124.3(4) . . ?
O1 C7 C8 119.5(4) . . ?
O1 C7 C2 121.5(4) . . ?
C8 C7 C2 119.0(4) . . ?
C5 C6 C1 119.7(4) . . ?
C16 C11 C12 117.7(5) . . ?
C16 C11 C10 121.4(5) . . ?
C12 C11 C10 121.0(5) . . ?
C3 C4 C5 119.7(4) . . ?
C6 C1 C2 120.5(4) . . ?
C6 C1 S1 114.9(3) . . ?
C2 C1 S1 124.6(3) . . ?
C4 C3 C2 120.7(4) . . ?
C8 C9 S1 127.1(4) . . ?
C8 C9 S2 119.7(3) . . ?
S1 C9 S2 113.1(2) . . ?
C15 C14 C13 118.9(5) . . ?
C14 C15 C16 120.1(6) . . ?
C11 C16 C15 121.9(5) . . ?
C14 C13 C12 121.3(5) . . ?
C13 C12 C11 120.1(5) . . ?
N1 C10 C11 109.7(4) . . ?
C6 C5 C4 121.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_km_t_am_ax_a
_database_code_depnum_ccdc_archive 'CCDC 1583530'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        km-t-ant
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 N O S2, H2 O'
_chemical_formula_sum            'C23 H17 N O2 S2'
_chemical_formula_weight         403.50

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'
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'
H H 0.0000 0.0000 '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/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                   16.5683(9)
_cell_length_b                   13.2261(7)
_cell_length_c                   8.5713(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.047(3)
_cell_angle_gamma                90.00
_cell_volume                     1870.98(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5287
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.73

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9261
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3307
_reflns_number_gt                2550
_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)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3307
_refine_ls_number_parameters     269
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          1.027
_refine_ls_shift/su_mean         0.033

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
S2 S 0.28436(4) 0.42166(4) 0.86218(7) 0.0337(2) Uani 1 1 d . . .
S1 S 0.20923(4) 0.58697(5) 0.66835(8) 0.0443(2) Uani 1 1 d . . .
O1 O 0.09476(13) 0.33104(15) 0.3996(2) 0.0596(6) Uani 1 1 d . . .
N1 N 0.20544(15) 0.5521(2) 1.0922(3) 0.0490(6) Uani 1 1 d . . .
C21 C 0.39932(14) 0.57400(16) 0.9054(3) 0.0282(5) Uani 1 1 d . . .
C2A C 0.32207(14) 0.53669(17) 0.9438(3) 0.0295(5) Uani 1 1 d . . .
C19 C 0.52190(14) 0.56509(18) 0.7675(3) 0.0314(6) Uani 1 1 d . . .
C20 C 0.44627(13) 0.52688(17) 0.7998(3) 0.0303(5) Uani 1 1 d . . .
H20 H 0.4269 0.4684 0.7492 0.036 Uiso 1 1 calc R . .
C12 C 0.43026(14) 0.66533(17) 0.9806(3) 0.0317(6) Uani 1 1 d . . .
C14 C 0.55215(14) 0.65599(18) 0.8428(3) 0.0322(6) Uani 1 1 d . . .
C1A C 0.21810(13) 0.45934(18) 0.7026(3) 0.0308(5) Uani 1 1 d . . .
C1 C 0.17896(15) 0.38705(19) 0.6126(3) 0.0363(6) Uani 1 1 d . . .
H1 H 0.1888 0.3201 0.6417 0.044 Uiso 1 1 calc R . .
C9 C 0.27920(15) 0.58413(17) 1.0540(3) 0.0334(6) Uani 1 1 d . . .
C13 C 0.50515(15) 0.70312(18) 0.9482(3) 0.0361(6) Uani 1 1 d . . .
H13 H 0.5245 0.7617 0.9984 0.043 Uiso 1 1 calc R . .
C11 C 0.38280(16) 0.71268(19) 1.0913(3) 0.0391(6) Uani 1 1 d . . .
H11 H 0.4018 0.7719 1.1402 0.047 Uiso 1 1 calc R . .
C10 C 0.31189(16) 0.67441(19) 1.1267(3) 0.0402(6) Uani 1 1 d . . .
H10 H 0.2832 0.7072 1.2003 0.048 Uiso 1 1 calc R . .
C3 C 0.10261(14) 0.5083(2) 0.4302(3) 0.0372(6) Uani 1 1 d . . .
C18 C 0.57119(15) 0.5162(2) 0.6618(3) 0.0395(6) Uani 1 1 d . . .
H18 H 0.5532 0.4566 0.6129 0.047 Uiso 1 1 calc R . .
C8 C 0.13838(16) 0.59213(19) 0.5047(3) 0.0378(6) Uani 1 1 d . . .
C15 C 0.62889(15) 0.6935(2) 0.8081(3) 0.0443(7) Uani 1 1 d . . .
H15 H 0.6492 0.7522 0.8567 0.053 Uiso 1 1 calc R . .
C2 C 0.12404(16) 0.4043(2) 0.4772(3) 0.0386(6) Uani 1 1 d . . .
C16 C 0.67285(16) 0.6449(2) 0.7052(3) 0.0482(7) Uani 1 1 d . . .
H16 H 0.7227 0.6710 0.6828 0.058 Uiso 1 1 calc R . .
C4 C 0.04400(16) 0.5249(2) 0.3041(3) 0.0497(7) Uani 1 1 d . . .
H4 H 0.0182 0.4699 0.2540 0.060 Uiso 1 1 calc R . .
C7 C 0.11870(18) 0.6904(2) 0.4508(3) 0.0510(7) Uani 1 1 d . . .
H7 H 0.1439 0.7461 0.4999 0.061 Uiso 1 1 calc R . .
C17 C 0.64366(16) 0.5551(2) 0.6318(3) 0.0491(7) Uani 1 1 d . . .
H17 H 0.6746 0.5223 0.5619 0.059 Uiso 1 1 calc R . .
C6 C 0.06232(18) 0.7035(3) 0.3260(4) 0.0573(8) Uani 1 1 d . . .
H6 H 0.0496 0.7683 0.2897 0.069 Uiso 1 1 calc R . .
C5 C 0.02420(17) 0.6211(3) 0.2536(4) 0.0580(9) Uani 1 1 d . . .
H5 H -0.0150 0.6307 0.1704 0.070 Uiso 1 1 calc R . .
O2 O 0.88813(16) 0.64500(19) 0.9325(3) 0.0706(7) Uani 1 1 d D . .
H1A H 0.1831(18) 0.491(3) 1.062(4) 0.067(10) Uiso 1 1 d . . .
H1B H 0.188(2) 0.581(2) 1.175(4) 0.071(11) Uiso 1 1 d . . .
H2A H 0.893(4) 0.658(4) 0.832(3) 0.18(3) Uiso 1 1 d D . .
H2B H 0.875(6) 0.692(5) 0.999(9) 0.35(5) Uiso 1 1 d D . .


_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
S2 C1A 1.750(2) . ?
S2 C2A 1.766(2) . ?
S1 C1A 1.717(2) . ?
S1 C8 1.749(3) . ?
O1 C2 1.249(3) . ?
N1 C9 1.361(3) . ?
N1 H1A 0.92(3) . ?
N1 H1B 0.88(4) . ?
C21 C20 1.392(3) . ?
C21 C2A 1.437(3) . ?
C21 C12 1.442(3) . ?
C2A C9 1.381(3) . ?
C19 C20 1.401(3) . ?
C19 C18 1.427(3) . ?
C19 C14 1.434(3) . ?
C20 H20 0.9300 . ?
C12 C13 1.388(3) . ?
C12 C11 1.429(3) . ?
C14 C13 1.391(3) . ?
C14 C15 1.421(3) . ?
C1A C1 1.357(3) . ?
C1 C2 1.428(3) . ?
C1 H1 0.9300 . ?
C9 C10 1.431(3) . ?
C13 H13 0.9300 . ?
C11 C10 1.339(4) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C3 C8 1.386(4) . ?
C3 C4 1.405(4) . ?
C3 C2 1.469(4) . ?
C18 C17 1.352(4) . ?
C18 H18 0.9300 . ?
C8 C7 1.408(4) . ?
C15 C16 1.354(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.410(4) . ?
C16 H16 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C7 C6 1.368(4) . ?
C7 H7 0.9300 . ?
C17 H17 0.9300 . ?
C6 C5 1.379(5) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
O2 H2A 0.886(14) . ?
O2 H2B 0.879(15) . ?

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
C1A S2 C2A 103.89(11) . . ?
C1A S1 C8 102.51(11) . . ?
C9 N1 H1A 124(2) . . ?
C9 N1 H1B 115(2) . . ?
H1A N1 H1B 117(3) . . ?
C20 C21 C2A 123.7(2) . . ?
C20 C21 C12 118.0(2) . . ?
C2A C21 C12 118.3(2) . . ?
C9 C2A C21 121.5(2) . . ?
C9 C2A S2 118.49(18) . . ?
C21 C2A S2 119.78(17) . . ?
C20 C19 C18 122.3(2) . . ?
C20 C19 C14 119.8(2) . . ?
C18 C19 C14 118.0(2) . . ?
C21 C20 C19 121.9(2) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 C21 120.1(2) . . ?
C11 C12 C21 118.0(2) . . ?
C13 C14 C15 122.8(2) . . ?
C13 C14 C19 118.3(2) . . ?
C15 C14 C19 118.8(2) . . ?
C1 C1A S1 124.47(19) . . ?
C1 C1A S2 118.64(19) . . ?
S1 C1A S2 116.87(13) . . ?
C1A C1 C2 126.0(2) . . ?
C1A C1 H1 117.0 . . ?
C2 C1 H1 117.0 . . ?
N1 C9 C2A 123.4(2) . . ?
N1 C9 C10 117.9(2) . . ?
C2A C9 C10 118.6(2) . . ?
C12 C13 C14 122.0(2) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C10 C11 C12 122.0(2) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C8 C3 C4 117.9(2) . . ?
C8 C3 C2 122.7(2) . . ?
C4 C3 C2 119.4(2) . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C3 C8 C7 120.7(2) . . ?
C3 C8 S1 124.60(19) . . ?
C7 C8 S1 114.8(2) . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O1 C2 C1 119.9(2) . . ?
O1 C2 C3 120.5(2) . . ?
C1 C2 C3 119.6(2) . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
H2A O2 H2B 122(7) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.064


