# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1457404'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 S3'
_chemical_formula_weight         296.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   15.042(5)
_cell_length_b                   11.404(4)
_cell_length_c                   32.856(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.094(5)
_cell_angle_gamma                90.00
_cell_volume                     5614(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3653
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.83

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2432
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8791
_exptl_absorpt_correction_T_max  0.9185
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13829
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4882
_reflns_number_gt                3386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0020P)²+45.0000P] 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       0.00086(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4882
_refine_ls_number_parameters     352
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0881
_refine_ls_wR_factor_ref         0.2094
_refine_ls_wR_factor_gt          0.1980
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.071
_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 0.59215(19) 0.2447(3) 0.32247(10) 0.1447(13) Uani 1 1 d . . .
S2 S 0.38239(9) 0.56544(13) 0.21740(4) 0.0503(4) Uani 1 1 d . . .
S3' S 0.18910(18) 0.9766(2) 0.10933(8) 0.0655(7) Uani 0.50 1 d P . .
C14' C 0.18910(18) 0.9766(2) 0.10933(8) 0.0655(7) Uani 0.50 1 d P . .
H14B H 0.1419 0.9945 0.1247 0.079 Uiso 0.50 1 calc PR . .
S4 S -0.03596(18) 0.3592(2) -0.02112(9) 0.1150(9) Uani 1 1 d . . .
S5 S 0.28056(10) 0.53214(14) 0.08976(5) 0.0629(5) Uani 1 1 d . . .
S6 S 0.64770(16) 0.7876(3) 0.14632(9) 0.1182(9) Uani 1 1 d . . .
C1 C 0.5976(6) 0.1345(9) 0.3527(3) 0.107(3) Uani 1 1 d U . .
H1 H 0.6508 0.0951 0.3598 0.129 Uiso 1 1 calc R . .
C2 C 0.5210(7) 0.1025(8) 0.3670(3) 0.112(3) Uani 1 1 d . . .
H2 H 0.5169 0.0375 0.3838 0.135 Uiso 1 1 calc R . .
C3 C 0.4431(4) 0.1768(5) 0.35437(17) 0.0528(15) Uani 1 1 d . . .
H3 H 0.3854 0.1738 0.3624 0.063 Uiso 1 1 calc R . .
C4 C 0.4835(4) 0.2608(6) 0.32420(18) 0.0601(15) Uani 1 1 d . . .
C5 C 0.4362(4) 0.3501(5) 0.30232(17) 0.0518(14) Uani 1 1 d . . .
C6 C 0.3955(3) 0.4245(5) 0.28402(17) 0.0483(13) Uani 1 1 d . . .
C7 C 0.3471(3) 0.5135(5) 0.26230(15) 0.0448(12) Uani 1 1 d . . .
C8 C 0.2710(4) 0.5674(6) 0.27113(18) 0.0643(17) Uani 1 1 d . . .
H8 H 0.2413 0.5500 0.2940 0.077 Uiso 1 1 calc R . .
C9 C 0.2417(4) 0.6517(6) 0.24219(18) 0.0638(17) Uani 1 1 d . . .
H9 H 0.1903 0.6961 0.2440 0.077 Uiso 1 1 calc R . .
C10 C 0.2947(3) 0.6631(4) 0.21148(15) 0.0427(12) Uani 1 1 d . . .
C11 C 0.2852(3) 0.7374(5) 0.17771(17) 0.0462(12) Uani 1 1 d . . .
C12 C 0.2764(3) 0.8021(5) 0.14880(16) 0.0450(12) Uani 1 1 d . . .
C13 C 0.2661(3) 0.8787(5) 0.11529(16) 0.0454(12) Uani 1 1 d . . .
S3 S 0.33269(18) 0.8756(2) 0.07934(8) 0.0654(7) Uani 0.50 1 d P . .
C14 C 0.33269(18) 0.8756(2) 0.07934(8) 0.0654(7) Uani 0.50 1 d P . .
H14A H 0.3807 0.8277 0.0746 0.078 Uiso 0.50 1 calc PR . .
C15 C 0.2874(7) 0.9831(7) 0.0549(2) 0.079(2) Uani 1 1 d . . .
C16 C 0.2186(6) 1.0302(6) 0.0703(3) 0.080(2) Uani 1 1 d D . .
C17 C -0.1111(5) 0.2545(9) -0.0255(3) 0.099(3) Uani 1 1 d . . .
H17 H -0.1626 0.2582 -0.0434 0.118 Uiso 1 1 calc R . .
C18 C -0.0916(5) 0.1671(9) -0.0018(3) 0.090(2) Uani 1 1 d . . .
H18 H -0.1286 0.1019 -0.0010 0.108 Uiso 1 1 calc R . .
C19 C -0.0084(3) 0.1767(5) 0.02348(14) 0.0446(13) Uani 1 1 d . . .
H19 H 0.0164 0.1223 0.0423 0.054 Uiso 1 1 calc R . .
C20 C 0.0285(4) 0.2910(6) 0.01311(18) 0.0576(15) Uani 1 1 d . . .
C21 C 0.1123(4) 0.3349(5) 0.03082(17) 0.0556(14) Uani 1 1 d . . .
C22 C 0.1827(4) 0.3678(5) 0.04513(17) 0.0525(14) Uani 1 1 d . . .
C23 C 0.2675(4) 0.4048(5) 0.06245(16) 0.0495(13) Uani 1 1 d . . .
C24 C 0.3461(4) 0.3507(6) 0.0606(2) 0.0723(19) Uani 1 1 d . . .
H24 H 0.3523 0.2798 0.0472 0.087 Uiso 1 1 calc R . .
C25 C 0.4178(4) 0.4106(6) 0.0807(2) 0.0714(19) Uani 1 1 d . . .
H25 H 0.4763 0.3835 0.0821 0.086 Uiso 1 1 calc R . .
C26 C 0.3940(3) 0.5117(5) 0.09788(16) 0.0485(13) Uani 1 1 d . . .
C27 C 0.4486(4) 0.5948(5) 0.11955(17) 0.0503(13) Uani 1 1 d . . .
C28 C 0.4950(4) 0.6655(5) 0.13735(17) 0.0536(14) Uani 1 1 d . . .
C29 C 0.5488(4) 0.7494(5) 0.15869(18) 0.0567(15) Uani 1 1 d . . .
C30 C 0.5246(4) 0.8156(6) 0.19638(16) 0.066(2) Uani 1 1 d . . .
H30 H 0.4727 0.8098 0.2097 0.080 Uiso 1 1 calc R . .
C31 C 0.6022(7) 0.8904(8) 0.2066(3) 0.110(3) Uani 1 1 d . . .
H31 H 0.6061 0.9409 0.2289 0.132 Uiso 1 1 calc R . .
C32 C 0.6653(5) 0.8816(7) 0.1823(3) 0.089(2) Uani 1 1 d . . .
H32 H 0.7170 0.9266 0.1856 0.107 Uiso 1 1 calc R . .
H16A H 0.184(4) 1.098(4) 0.062(2) 0.10(2) Uiso 1 1 d D . .
H15A H 0.313(5) 1.000(7) 0.033(2) 0.09(2) 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 C1 1.599(9) . ?
S1 C4 1.651(6) . ?
S2 C7 1.717(5) . ?
S2 C10 1.723(5) . ?
S3' C16 1.521(9) . ?
S3' C13 1.608(6) . ?
S4 C20 1.617(7) . ?
S4 C17 1.642(10) . ?
S5 C23 1.709(6) . ?
S5 C26 1.719(5) . ?
S6 C32 1.600(9) . ?
S6 C29 1.636(6) . ?
C1 C2 1.334(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.475(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.542(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(8) . ?
C5 C6 1.179(7) . ?
C6 C7 1.407(7) . ?
C7 C8 1.353(8) . ?
C8 C9 1.396(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.347(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.393(7) . ?
C11 C12 1.201(7) . ?
C12 C13 1.404(7) . ?
C13 S3 1.615(6) . ?
S3 C15 1.586(9) . ?
C15 C16 1.308(12) . ?
C15 H15A 0.87(7) . ?
C16 H16A 0.95(2) . ?
C17 C18 1.282(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.444(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.469(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.431(8) . ?
C21 C22 1.180(7) . ?
C22 C23 1.414(8) . ?
C23 C24 1.341(8) . ?
C24 C25 1.392(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.346(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.405(8) . ?
C27 C28 1.186(7) . ?
C28 C29 1.400(8) . ?
C29 C30 1.522(8) . ?
C30 C31 1.462(9) . ?
C30 H30 0.9300 . ?
C31 C32 1.296(12) . ?
C31 H31 0.9300 . ?
C32 H32 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 S1 C4 93.6(4) . . ?
C7 S2 C10 91.6(3) . . ?
C16 S3' C13 96.9(4) . . ?
C20 S4 C17 94.4(4) . . ?
C23 S5 C26 91.9(3) . . ?
C32 S6 C29 95.1(4) . . ?
C2 C1 S1 115.8(6) . . ?
C2 C1 H1 122.1 . . ?
S1 C1 H1 122.1 . . ?
C1 C2 C3 115.7(8) . . ?
C1 C2 H2 122.2 . . ?
C3 C2 H2 122.2 . . ?
C2 C3 C4 100.9(6) . . ?
C2 C3 H3 129.5 . . ?
C4 C3 H3 129.5 . . ?
C5 C4 C3 124.7(5) . . ?
C5 C4 S1 121.5(5) . . ?
C3 C4 S1 113.6(4) . . ?
C6 C5 C4 179.3(7) . . ?
C5 C6 C7 179.8(7) . . ?
C8 C7 C6 129.0(5) . . ?
C8 C7 S2 111.1(4) . . ?
C6 C7 S2 119.9(4) . . ?
C7 C8 C9 112.9(5) . . ?
C7 C8 H8 123.6 . . ?
C9 C8 H8 123.6 . . ?
C10 C9 C8 113.9(5) . . ?
C10 C9 H9 123.1 . . ?
C8 C9 H9 123.1 . . ?
C9 C10 C11 129.0(5) . . ?
C9 C10 S2 110.6(4) . . ?
C11 C10 S2 120.4(4) . . ?
C12 C11 C10 179.3(6) . . ?
C11 C12 C13 179.4(6) . . ?
C12 C13 S3' 123.7(4) . . ?
C12 C13 S3 121.9(4) . . ?
S3' C13 S3 114.4(3) . . ?
C15 S3 C13 95.0(4) . . ?
C16 C15 S3 116.1(6) . . ?
C16 C15 H15A 131(5) . . ?
S3 C15 H15A 113(5) . . ?
C15 C16 S3' 117.5(6) . . ?
C15 C16 H16A 131(5) . . ?
S3' C16 H16A 111(5) . . ?
C18 C17 S4 113.2(6) . . ?
C18 C17 H17 123.4 . . ?
S4 C17 H17 123.4 . . ?
C17 C18 C19 115.5(7) . . ?
C17 C18 H18 122.3 . . ?
C19 C18 H18 122.3 . . ?
C18 C19 C20 105.1(6) . . ?
C18 C19 H19 127.5 . . ?
C20 C19 H19 127.5 . . ?
C21 C20 C19 123.6(5) . . ?
C21 C20 S4 124.5(5) . . ?
C19 C20 S4 111.9(4) . . ?
C22 C21 C20 177.9(7) . . ?
C21 C22 C23 178.8(7) . . ?
C24 C23 C22 127.8(6) . . ?
C24 C23 S5 110.7(4) . . ?
C22 C23 S5 121.5(5) . . ?
C23 C24 C25 113.7(6) . . ?
C23 C24 H24 123.1 . . ?
C25 C24 H24 123.1 . . ?
C26 C25 C24 113.3(6) . . ?
C26 C25 H25 123.3 . . ?
C24 C25 H25 123.3 . . ?
C25 C26 C27 128.6(5) . . ?
C25 C26 S5 110.4(4) . . ?
C27 C26 S5 121.0(4) . . ?
C28 C27 C26 179.1(6) . . ?
C27 C28 C29 179.2(7) . . ?
C28 C29 C30 125.3(5) . . ?
C28 C29 S6 123.7(5) . . ?
C30 C29 S6 111.0(4) . . ?
C31 C30 C29 103.4(6) . . ?
C31 C30 H30 128.3 . . ?
C29 C30 H30 128.3 . . ?
C32 C31 C30 115.3(7) . . ?
C32 C31 H31 122.3 . . ?
C30 C31 H31 122.3 . . ?
C31 C32 S6 115.1(6) . . ?
C31 C32 H32 122.4 . . ?
S6 C32 H32 122.4 . . ?

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
C4 S1 C1 C2 -1.3(10) . . . . ?
S1 C1 C2 C3 -2.7(13) . . . . ?
C1 C2 C3 C4 5.5(11) . . . . ?
C2 C3 C4 C5 178.8(7) . . . . ?
C2 C3 C4 S1 -6.3(7) . . . . ?
C1 S1 C4 C5 179.9(6) . . . . ?
C1 S1 C4 C3 4.7(6) . . . . ?
C3 C4 C5 C6 -18(52) . . . . ?
S1 C4 C5 C6 167(100) . . . . ?
C4 C5 C6 C7 102(100) . . . . ?
C5 C6 C7 C8 -62(100) . . . . ?
C5 C6 C7 S2 120(100) . . . . ?
C10 S2 C7 C8 1.4(5) . . . . ?
C10 S2 C7 C6 -179.8(5) . . . . ?
C6 C7 C8 C9 -179.6(6) . . . . ?
S2 C7 C8 C9 -1.0(7) . . . . ?
C7 C8 C9 C10 -0.2(9) . . . . ?
C8 C9 C10 C11 179.5(6) . . . . ?
C8 C9 C10 S2 1.3(7) . . . . ?
C7 S2 C10 C9 -1.5(5) . . . . ?
C7 S2 C10 C11 -179.9(4) . . . . ?
C9 C10 C11 C12 13(61) . . . . ?
S2 C10 C11 C12 -169(100) . . . . ?
C10 C11 C12 C13 53(93) . . . . ?
C11 C12 C13 S3' -61(52) . . . . ?
C11 C12 C13 S3 119(52) . . . . ?
C16 S3' C13 C12 176.9(5) . . . . ?
C16 S3' C13 S3 -2.6(4) . . . . ?
C12 C13 S3 C15 -177.3(5) . . . . ?
S3' C13 S3 C15 2.3(4) . . . . ?
C13 S3 C15 C16 -1.0(7) . . . . ?
S3 C15 C16 S3' -0.6(9) . . . . ?
C13 S3' C16 C15 2.0(7) . . . . ?
C20 S4 C17 C18 0.6(8) . . . . ?
S4 C17 C18 C19 -0.5(10) . . . . ?
C17 C18 C19 C20 0.2(9) . . . . ?
C18 C19 C20 C21 -178.7(6) . . . . ?
C18 C19 C20 S4 0.2(6) . . . . ?
C17 S4 C20 C21 178.5(6) . . . . ?
C17 S4 C20 C19 -0.4(5) . . . . ?
C19 C20 C21 C22 51(19) . . . . ?
S4 C20 C21 C22 -128(19) . . . . ?
C20 C21 C22 C23 -28(44) . . . . ?
C21 C22 C23 C24 36(30) . . . . ?
C21 C22 C23 S5 -144(30) . . . . ?
C26 S5 C23 C24 0.8(5) . . . . ?
C26 S5 C23 C22 -179.2(5) . . . . ?
C22 C23 C24 C25 179.6(6) . . . . ?
S5 C23 C24 C25 -0.4(8) . . . . ?
C23 C24 C25 C26 -0.4(10) . . . . ?
C24 C25 C26 C27 -178.5(6) . . . . ?
C24 C25 C26 S5 1.0(8) . . . . ?
C23 S5 C26 C25 -1.1(5) . . . . ?
C23 S5 C26 C27 178.5(5) . . . . ?
C25 C26 C27 C28 81(44) . . . . ?
S5 C26 C27 C28 -98(44) . . . . ?
C26 C27 C28 C29 129(57) . . . . ?
C27 C28 C29 C30 9(56) . . . . ?
C27 C28 C29 S6 -172(100) . . . . ?
C32 S6 C29 C28 179.6(6) . . . . ?
C32 S6 C29 C30 -1.2(6) . . . . ?
C28 C29 C30 C31 179.7(7) . . . . ?
S6 C29 C30 C31 0.5(7) . . . . ?
C29 C30 C31 C32 0.7(11) . . . . ?
C30 C31 C32 S6 -1.6(12) . . . . ?
C29 S6 C32 C31 1.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.084
