# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_1
_audit_block_doi                 10.5517/cc13ctx6
_database_code_depnum_ccdc_archive 'CCDC 1024268'
_audit_update_record             
;
2014-09-15 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 N2 O S3'
_chemical_formula_sum            'C17 H20 N2 O S3'
_chemical_formula_weight         364.53
_chemical_absolute_configuration ad

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           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   8.2731(4)
_cell_length_b                   10.7452(5)
_cell_length_c                   20.7803(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1847.29(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5733
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.51

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8512
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_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_reflns_number            12666
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.58
_reflns_number_total             4266
_reflns_number_gt                3894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0587P)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     SHELXL
_refine_ls_extinction_coef       0.044(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_number_reflns         4266
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.046
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1597(2) 0.62643(16) 0.77679(8) 0.0378(3) Uani 1 1 d . . .
C2 C 0.2034(2) 0.69911(18) 0.87438(8) 0.0432(4) Uani 1 1 d . . .
C3 C 0.1346(2) 0.58538(17) 0.89147(8) 0.0426(4) Uani 1 1 d . . .
C4 C 0.1189(2) 0.5492(2) 0.95574(9) 0.0536(5) Uani 1 1 d . . .
H4 H 0.0735 0.4730 0.9669 0.064 Uiso 1 1 calc R . .
C5 C 0.1733(3) 0.6311(3) 1.00196(9) 0.0631(6) Uani 1 1 d . . .
H5 H 0.1649 0.6094 1.0452 0.076 Uiso 1 1 calc R . .
C6 C 0.2397(3) 0.7440(2) 0.98563(10) 0.0682(6) Uani 1 1 d . . .
H6 H 0.2741 0.7972 1.0182 0.082 Uiso 1 1 calc R . .
C7 C 0.2569(3) 0.7809(2) 0.92218(9) 0.0584(5) Uani 1 1 d . . .
H7 H 0.3025 0.8574 0.9117 0.070 Uiso 1 1 calc R . .
C8 C 0.15011(19) 0.61859(17) 0.70346(8) 0.0379(3) Uani 1 1 d . . .
C9 C 0.4323(2) 0.84116(18) 0.59158(9) 0.0482(4) Uani 1 1 d . . .
C10 C 0.5781(3) 0.7611(3) 0.60655(14) 0.0803(7) Uani 1 1 d . . .
H10A H 0.6749 0.8059 0.5960 0.120 Uiso 1 1 calc R . .
H10B H 0.5732 0.6860 0.5816 0.120 Uiso 1 1 calc R . .
H10C H 0.5786 0.7407 0.6515 0.120 Uiso 1 1 calc R . .
C11 C 0.4197(3) 0.9561(2) 0.63383(12) 0.0705(6) Uani 1 1 d . . .
H11A H 0.4993 1.0159 0.6207 0.106 Uiso 1 1 calc R . .
H11B H 0.4380 0.9333 0.6779 0.106 Uiso 1 1 calc R . .
H11C H 0.3138 0.9916 0.6296 0.106 Uiso 1 1 calc R . .
C12 C 0.4325(4) 0.8805(3) 0.52022(10) 0.0720(7) Uani 1 1 d . . .
H12A H 0.3412 0.9332 0.5119 0.108 Uiso 1 1 calc R . .
H12B H 0.4263 0.8078 0.4935 0.108 Uiso 1 1 calc R . .
H12C H 0.5303 0.9250 0.5108 0.108 Uiso 1 1 calc R . .
C13 C 0.21306(18) 0.49206(16) 0.68370(7) 0.0375(3) Uani 1 1 d . . .
C14 C 0.1274(2) 0.38730(18) 0.66982(9) 0.0496(4) Uani 1 1 d . . .
H14 H 0.0161 0.3869 0.6635 0.059 Uiso 1 1 calc R . .
C15 C 0.2239(3) 0.27957(18) 0.66604(11) 0.0598(5) Uani 1 1 d . . .
H15 H 0.1833 0.2008 0.6569 0.072 Uiso 1 1 calc R . .
C16 C 0.3801(3) 0.3028(2) 0.67699(10) 0.0597(5) Uani 1 1 d . . .
H16 H 0.4602 0.2420 0.6771 0.072 Uiso 1 1 calc R . .
C17 C -0.0282(2) 0.6351(2) 0.68368(9) 0.0490(4) Uani 1 1 d . . .
H17A H -0.0641 0.7169 0.6954 0.073 Uiso 1 1 calc R . .
H17B H -0.0933 0.5740 0.7053 0.073 Uiso 1 1 calc R . .
H17C H -0.0383 0.6245 0.6380 0.073 Uiso 1 1 calc R . .
N1 N 0.21525(17) 0.72047(14) 0.80784(7) 0.0430(3) Uani 1 1 d . . .
N2 N 0.25823(19) 0.71701(13) 0.67824(7) 0.0410(3) Uani 1 1 d D . .
H2 H 0.255(3) 0.7792(16) 0.6998(10) 0.049 Uiso 1 1 d D . .
O1 O 0.11219(18) 0.82997(15) 0.58393(6) 0.0598(4) Uani 1 1 d . . .
S1 S 0.08502(6) 0.50280(4) 0.822406(19) 0.04625(12) Uani 1 1 d . . .
S2 S 0.24848(5) 0.74518(4) 0.599071(18) 0.04123(12) Uani 1 1 d . . .
S3 S 0.41573(6) 0.45771(5) 0.69088(2) 0.05414(14) Uani 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
C1 N1 1.284(2) . ?
C1 C8 1.528(2) . ?
C1 S1 1.7450(18) . ?
C2 C3 1.394(3) . ?
C2 C7 1.399(3) . ?
C2 N1 1.405(2) . ?
C3 C4 1.397(2) . ?
C3 S1 1.7366(17) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.481(2) . ?
C8 C13 1.513(2) . ?
C8 C17 1.542(2) . ?
C9 C10 1.514(3) . ?
C9 C11 1.519(3) . ?
C9 C12 1.542(3) . ?
C9 S2 1.8441(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.361(3) . ?
C13 S3 1.7234(16) . ?
C14 C15 1.408(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.336(3) . ?
C15 H15 0.9300 . ?
C16 S3 1.715(2) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N2 S2 1.6748(15) . ?
N2 H2 0.804(15) . ?
O1 S2 1.4833(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
N1 C1 C8 124.26(16) . . ?
N1 C1 S1 116.93(12) . . ?
C8 C1 S1 118.77(13) . . ?
C3 C2 C7 119.97(18) . . ?
C3 C2 N1 115.00(15) . . ?
C7 C2 N1 125.02(18) . . ?
C2 C3 C4 121.71(17) . . ?
C2 C3 S1 109.50(12) . . ?
C4 C3 S1 128.74(16) . . ?
C5 C4 C3 117.3(2) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C6 C5 C4 121.48(19) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.93(19) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C2 117.6(2) . . ?
C6 C7 H7 121.2 . . ?
C2 C7 H7 121.2 . . ?
N2 C8 C13 109.75(13) . . ?
N2 C8 C1 106.39(13) . . ?
C13 C8 C1 107.60(14) . . ?
N2 C8 C17 113.68(15) . . ?
C13 C8 C17 111.12(15) . . ?
C1 C8 C17 108.01(13) . . ?
C10 C9 C11 113.4(2) . . ?
C10 C9 C12 110.64(19) . . ?
C11 C9 C12 109.46(19) . . ?
C10 C9 S2 108.79(15) . . ?
C11 C9 S2 110.44(14) . . ?
C12 C9 S2 103.62(14) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C8 128.44(15) . . ?
C14 C13 S3 110.35(13) . . ?
C8 C13 S3 120.26(12) . . ?
C13 C14 C15 113.36(17) . . ?
C13 C14 H14 123.3 . . ?
C15 C14 H14 123.3 . . ?
C16 C15 C14 112.69(19) . . ?
C16 C15 H15 123.7 . . ?
C14 C15 H15 123.7 . . ?
C15 C16 S3 112.08(16) . . ?
C15 C16 H16 124.0 . . ?
S3 C16 H16 124.0 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 C2 109.93(15) . . ?
C8 N2 S2 116.59(11) . . ?
C8 N2 H2 112.2(16) . . ?
S2 N2 H2 113.3(15) . . ?
C3 S1 C1 88.64(9) . . ?
O1 S2 N2 110.85(8) . . ?
O1 S2 C9 105.40(9) . . ?
N2 S2 C9 98.30(8) . . ?
C16 S3 C13 91.51(10) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.034
