# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mm

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 O2 S2'
_chemical_formula_weight         400.49

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   14.959(5)
_cell_length_b                   4.722(5)
_cell_length_c                   26.639(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1882(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(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    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_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            12806
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         26.90
_reflns_number_total             3684
_reflns_number_gt                3349
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0548P)²+0.0197P] 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   0.02(6)
_refine_ls_number_reflns         3684
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
S1 S 1.11475(4) 0.20156(13) 0.30010(2) 0.04346(17) Uani 1 1 d . . .
S2 S 0.83194(4) 0.30679(12) 0.11006(2) 0.03968(16) Uani 1 1 d . . .
O3 O 1.16631(10) 0.5977(4) 0.21538(7) 0.0434(4) Uani 1 1 d . . .
H3 H 1.1767 0.7078 0.1923 0.065 Uiso 1 1 calc R . .
C4 C 0.74156(15) 0.1073(5) 0.08849(9) 0.0339(5) Uani 1 1 d . . .
O5 O 0.71187(11) -0.1011(4) 0.16773(6) 0.0430(4) Uani 1 1 d . . .
H5 H 0.7535 0.0055 0.1743 0.064 Uiso 1 1 calc R . .
C6 C 0.69124(14) -0.0798(5) 0.11727(9) 0.0354(5) Uani 1 1 d . . .
C7 C 0.72254(15) 0.1488(5) 0.03783(9) 0.0352(5) Uani 1 1 d . . .
C8 C 1.04597(15) 0.4110(5) 0.26235(9) 0.0351(5) Uani 1 1 d . . .
C9 C 0.78414(15) 0.3521(5) 0.01561(9) 0.0350(5) Uani 1 1 d . . .
C10 C 1.07507(15) 0.5914(5) 0.22465(8) 0.0358(5) Uani 1 1 d . . .
C11 C 0.84544(15) 0.4558(5) 0.05043(9) 0.0376(5) Uani 1 1 d . . .
C12 C 1.01381(17) 0.7491(5) 0.19854(10) 0.0427(6) Uani 1 1 d . . .
H12 H 1.0327 0.8734 0.1736 0.051 Uiso 1 1 calc R . .
C13 C 0.92290(18) 0.7223(6) 0.20950(11) 0.0472(6) Uani 1 1 d . . .
H13 H 0.8816 0.8286 0.1914 0.057 Uiso 1 1 calc R . .
C14 C 0.94083(17) 0.1793(5) 0.31309(9) 0.0433(6) Uani 1 1 d . . .
C15 C 0.95524(16) 0.3826(5) 0.27301(9) 0.0385(5) Uani 1 1 d . . .
C16 C 0.90981(17) 0.6569(5) 0.03704(11) 0.0452(6) Uani 1 1 d . . .
H16 H 0.9500 0.7277 0.0605 0.054 Uiso 1 1 calc R . .
C17 C 1.02068(18) 0.0637(5) 0.33108(9) 0.0437(6) Uani 1 1 d . . .
C18 C 0.78820(17) 0.4465(6) -0.03429(9) 0.0448(6) Uani 1 1 d . . .
H18 H 0.7481 0.3785 -0.0581 0.054 Uiso 1 1 calc R . .
C19 C 0.89330(16) 0.5426(6) 0.24632(10) 0.0448(6) Uani 1 1 d . . .
H19 H 0.8326 0.5278 0.2534 0.054 Uiso 1 1 calc R . .
C20 C 0.60330(18) -0.1882(6) 0.04476(11) 0.0495(7) Uani 1 1 d . . .
H20 H 0.5573 -0.2915 0.0301 0.059 Uiso 1 1 calc R . .
C21 C 0.85228(19) 0.6408(6) -0.04735(11) 0.0532(7) Uani 1 1 d . . .
H21 H 0.8560 0.7027 -0.0804 0.064 Uiso 1 1 calc R . .
C22 C 0.65293(16) 0.0018(6) 0.01562(10) 0.0446(6) Uani 1 1 d . . .
H22 H 0.6394 0.0289 -0.0181 0.054 Uiso 1 1 calc R . .
C23 C 0.62219(17) -0.2238(6) 0.09530(11) 0.0446(6) Uani 1 1 d . . .
H23 H 0.5876 -0.3468 0.1145 0.054 Uiso 1 1 calc R . .
C24 C 1.0221(2) -0.1389(6) 0.36911(10) 0.0571(8) Uani 1 1 d . . .
H24 H 1.0758 -0.2149 0.3805 0.069 Uiso 1 1 calc R . .
C25 C 0.8602(2) 0.0885(7) 0.33460(12) 0.0594(8) Uani 1 1 d . . .
H25 H 0.8061 0.1642 0.3239 0.071 Uiso 1 1 calc R . .
C26 C 0.9420(3) -0.2226(7) 0.38911(12) 0.0683(9) Uani 1 1 d . . .
H26 H 0.9414 -0.3553 0.4149 0.082 Uiso 1 1 calc R . .
C27 C 0.91164(19) 0.7464(6) -0.01199(12) 0.0519(7) Uani 1 1 d . . .
H27 H 0.9536 0.8809 -0.0217 0.062 Uiso 1 1 calc R . .
C28 C 0.8621(3) -0.1136(8) 0.37166(13) 0.0721(10) Uani 1 1 d . . .
H28 H 0.8086 -0.1783 0.3853 0.087 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
S1 C8 1.746(2) . ?
S1 C17 1.756(3) . ?
S2 C4 1.745(2) . ?
S2 C11 1.749(2) . ?
O3 C10 1.387(3) . ?
O3 H3 0.8200 . ?
C4 C6 1.391(3) . ?
C4 C7 1.393(3) . ?
O5 C6 1.383(3) . ?
O5 H5 0.8200 . ?
C6 C23 1.368(4) . ?
C7 C22 1.384(3) . ?
C7 C9 1.456(3) . ?
C8 C10 1.387(3) . ?
C8 C15 1.393(3) . ?
C9 C11 1.393(3) . ?
C9 C18 1.403(3) . ?
C10 C12 1.370(3) . ?
C11 C16 1.399(3) . ?
C12 C13 1.397(4) . ?
C12 H12 0.9300 . ?
C13 C19 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C17 1.398(4) . ?
C14 C25 1.402(4) . ?
C14 C15 1.452(4) . ?
C15 C19 1.391(4) . ?
C16 C27 1.373(4) . ?
C16 H16 0.9300 . ?
C17 C24 1.394(4) . ?
C18 C21 1.372(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C23 1.386(4) . ?
C20 C22 1.400(4) . ?
C20 H20 0.9300 . ?
C21 C27 1.387(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C26 1.370(5) . ?
C24 H24 0.9300 . ?
C25 C28 1.373(5) . ?
C25 H25 0.9300 . ?
C26 C28 1.382(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28 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
C8 S1 C17 90.48(12) . . ?
C4 S2 C11 90.44(12) . . ?
C10 O3 H3 109.5 . . ?
C6 C4 C7 120.9(2) . . ?
C6 C4 S2 125.50(18) . . ?
C7 C4 S2 113.65(18) . . ?
C6 O5 H5 109.5 . . ?
C23 C6 O5 123.2(2) . . ?
C23 C6 C4 119.2(2) . . ?
O5 C6 C4 117.46(19) . . ?
C22 C7 C4 119.8(2) . . ?
C22 C7 C9 129.3(2) . . ?
C4 C7 C9 110.9(2) . . ?
C10 C8 C15 120.8(2) . . ?
C10 C8 S1 125.45(18) . . ?
C15 C8 S1 113.72(19) . . ?
C11 C9 C18 119.4(2) . . ?
C11 C9 C7 112.2(2) . . ?
C18 C9 C7 128.4(2) . . ?
C12 C10 C8 119.4(2) . . ?
C12 C10 O3 123.8(2) . . ?
C8 C10 O3 116.8(2) . . ?
C9 C11 C16 121.5(2) . . ?
C9 C11 S2 112.78(18) . . ?
C16 C11 S2 125.7(2) . . ?
C10 C12 C13 119.7(2) . . ?
C10 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C19 C13 C12 121.4(2) . . ?
C19 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C17 C14 C25 118.4(3) . . ?
C17 C14 C15 112.5(2) . . ?
C25 C14 C15 129.1(3) . . ?
C19 C15 C8 119.5(2) . . ?
C19 C15 C14 129.5(2) . . ?
C8 C15 C14 111.0(2) . . ?
C27 C16 C11 117.7(3) . . ?
C27 C16 H16 121.1 . . ?
C11 C16 H16 121.1 . . ?
C24 C17 C14 122.0(3) . . ?
C24 C17 S1 125.7(2) . . ?
C14 C17 S1 112.27(19) . . ?
C21 C18 C9 118.9(3) . . ?
C21 C18 H18 120.6 . . ?
C9 C18 H18 120.6 . . ?
C13 C19 C15 119.1(2) . . ?
C13 C19 H19 120.4 . . ?
C15 C19 H19 120.4 . . ?
C23 C20 C22 120.6(2) . . ?
C23 C20 H20 119.7 . . ?
C22 C20 H20 119.7 . . ?
C18 C21 C27 121.0(3) . . ?
C18 C21 H21 119.5 . . ?
C27 C21 H21 119.5 . . ?
C7 C22 C20 118.9(2) . . ?
C7 C22 H22 120.5 . . ?
C20 C22 H22 120.5 . . ?
C6 C23 C20 120.6(2) . . ?
C6 C23 H23 119.7 . . ?
C20 C23 H23 119.7 . . ?
C26 C24 C17 117.8(3) . . ?
C26 C24 H24 121.1 . . ?
C17 C24 H24 121.1 . . ?
C28 C25 C14 119.3(3) . . ?
C28 C25 H25 120.4 . . ?
C14 C25 H25 120.4 . . ?
C24 C26 C28 121.2(3) . . ?
C24 C26 H26 119.4 . . ?
C28 C26 H26 119.4 . . ?
C16 C27 C21 121.5(3) . . ?
C16 C27 H27 119.3 . . ?
C21 C27 H27 119.3 . . ?
C25 C28 C26 121.2(3) . . ?
C25 C28 H28 119.4 . . ?
C26 C28 H28 119.4 . . ?

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
C11 S2 C4 C6 -179.8(2) . . . . ?
C11 S2 C4 C7 0.62(18) . . . . ?
C7 C4 C6 C23 -0.1(3) . . . . ?
S2 C4 C6 C23 -179.70(18) . . . . ?
C7 C4 C6 O5 -177.5(2) . . . . ?
S2 C4 C6 O5 2.9(3) . . . . ?
C6 C4 C7 C22 -0.2(3) . . . . ?
S2 C4 C7 C22 179.42(18) . . . . ?
C6 C4 C7 C9 -179.71(19) . . . . ?
S2 C4 C7 C9 -0.1(2) . . . . ?
C17 S1 C8 C10 -178.8(2) . . . . ?
C17 S1 C8 C15 0.92(19) . . . . ?
C22 C7 C9 C11 179.9(2) . . . . ?
C4 C7 C9 C11 -0.7(3) . . . . ?
C22 C7 C9 C18 -0.7(4) . . . . ?
C4 C7 C9 C18 178.8(2) . . . . ?
C15 C8 C10 C12 1.7(3) . . . . ?
S1 C8 C10 C12 -178.51(19) . . . . ?
C15 C8 C10 O3 -177.6(2) . . . . ?
S1 C8 C10 O3 2.2(3) . . . . ?
C18 C9 C11 C16 1.4(4) . . . . ?
C7 C9 C11 C16 -179.0(2) . . . . ?
C18 C9 C11 S2 -178.33(18) . . . . ?
C7 C9 C11 S2 1.2(3) . . . . ?
C4 S2 C11 C9 -1.04(18) . . . . ?
C4 S2 C11 C16 179.2(2) . . . . ?
C8 C10 C12 C13 -1.2(3) . . . . ?
O3 C10 C12 C13 178.0(2) . . . . ?
C10 C12 C13 C19 0.6(4) . . . . ?
C10 C8 C15 C19 -1.6(3) . . . . ?
S1 C8 C15 C19 178.63(18) . . . . ?
C10 C8 C15 C14 179.0(2) . . . . ?
S1 C8 C15 C14 -0.8(3) . . . . ?
C17 C14 C15 C19 -179.2(2) . . . . ?
C25 C14 C15 C19 1.2(4) . . . . ?
C17 C14 C15 C8 0.2(3) . . . . ?
C25 C14 C15 C8 -179.4(3) . . . . ?
C9 C11 C16 C27 -1.0(4) . . . . ?
S2 C11 C16 C27 178.7(2) . . . . ?
C25 C14 C17 C24 0.6(4) . . . . ?
C15 C14 C17 C24 -179.1(2) . . . . ?
C25 C14 C17 S1 -179.9(2) . . . . ?
C15 C14 C17 S1 0.5(3) . . . . ?
C8 S1 C17 C24 178.8(2) . . . . ?
C8 S1 C17 C14 -0.79(19) . . . . ?
C11 C9 C18 C21 -0.5(4) . . . . ?
C7 C9 C18 C21 -179.9(2) . . . . ?
C12 C13 C19 C15 -0.4(4) . . . . ?
C8 C15 C19 C13 0.9(4) . . . . ?
C14 C15 C19 C13 -179.8(2) . . . . ?
C9 C18 C21 C27 -0.8(4) . . . . ?
C4 C7 C22 C20 -0.5(4) . . . . ?
C9 C7 C22 C20 178.9(2) . . . . ?
C23 C20 C22 C7 1.5(4) . . . . ?
O5 C6 C23 C20 178.3(2) . . . . ?
C4 C6 C23 C20 1.1(4) . . . . ?
C22 C20 C23 C6 -1.8(4) . . . . ?
C14 C17 C24 C26 -0.4(4) . . . . ?
S1 C17 C24 C26 -180.0(2) . . . . ?
C17 C14 C25 C28 -1.3(4) . . . . ?
C15 C14 C25 C28 178.3(3) . . . . ?
C17 C24 C26 C28 1.1(5) . . . . ?
C11 C16 C27 C21 -0.4(4) . . . . ?
C18 C21 C27 C16 1.3(4) . . . . ?
C14 C25 C28 C26 1.9(5) . . . . ?
C24 C26 C28 C25 -1.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 996231'
