# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

 
data_bjr-340
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H24 O3 S4'
_chemical_formula_weight          488.70
 
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            triclinic
_symmetry_space_group_name_H-M    'P -1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.0622(3)
_cell_length_b                    8.0832(5)
_cell_length_c                    19.3119(11)
_cell_angle_alpha                 96.786(5)
_cell_angle_beta                  92.066(4)
_cell_angle_gamma                 103.632(4)
_cell_volume                      1211.84(11)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     2388
_cell_measurement_theta_min       3.1875
_cell_measurement_theta_max       28.8358
 
_exptl_crystal_description        triclinic
_exptl_crystal_colour             Yellow
_exptl_crystal_size_max           0.3
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.1
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.339
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              464
_exptl_absorpt_coefficient_mu      0.415
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.83647
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(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   'Xcalibur, Eos'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  16.0938
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             9169
_diffrn_reflns_av_R_equivalents   0.0188
_diffrn_reflns_av_sigmaI/netI     0.0435
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        26
_diffrn_reflns_theta_min          3.19
_diffrn_reflns_theta_max          28.90
_reflns_number_total              5500
_reflns_number_gt                 3790
_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)+(0.1082P)²+0.4851P] 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          5500
_refine_ls_number_parameters      280
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0797
_refine_ls_R_factor_gt            0.0494
_refine_ls_wR_factor_ref          0.1714
_refine_ls_wR_factor_gt           0.1407
_refine_ls_goodness_of_fit_ref    0.874
_refine_ls_restrained_S_all       0.874
_refine_ls_shift/su_max           0.064
_refine_ls_shift/su_mean          0.019
 
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
S4AA S 0.08700(9) 0.72686(9) 0.13159(4) 0.0483(2) Uani 1 1 d . . .
S0AA S -0.41039(9) 0.60835(12) 0.26005(4) 0.0573(2) Uani 1 1 d . . .
S1AA S 0.27811(10) 1.09244(11) 0.18304(5) 0.0633(3) Uani 1 1 d . . .
S2AA S -0.14303(11) 0.61938(16) 0.37232(4) 0.0779(3) Uani 1 1 d . . .
C7CA C -0.0792(3) 0.7026(3) 0.24146(12) 0.0394(6) Uani 1 1 d . . .
C0AA C -0.0640(3) 0.6079(3) 0.17941(13) 0.0408(6) Uani 1 1 d . . .
C1AA C -0.1474(3) 0.4295(3) 0.15063(12) 0.0393(5) Uani 1 1 d . . .
C2AA C 0.1927(3) 1.0672(4) 0.35978(13) 0.0441(6) Uani 1 1 d . . .
O O -0.3790(3) -0.0704(3) 0.06424(11) 0.0640(6) Uani 1 1 d . . .
O0AA O -0.0976(3) 1.0462(3) 0.32497(12) 0.0726(7) Uani 1 1 d . . .
C5AA C 0.0340(3) 0.8711(3) 0.25109(13) 0.0421(6) Uani 1 1 d . . .
C6AA C -0.1948(4) 0.3845(4) 0.07960(13) 0.0471(6) Uani 1 1 d . . .
H6AA H -0.1744 0.4686 0.0499 0.057 Uiso 1 1 calc R . .
O30 O 0.6175(3) 1.2744(4) 0.49670(11) 0.0750(7) Uani 1 1 d . . .
C8AA C -0.1780(3) 0.2999(4) 0.19317(13) 0.0451(6) Uani 1 1 d . . .
H8AA H -0.1463 0.3271 0.2407 0.054 Uiso 1 1 calc R . .
C9AA C -0.3021(3) 0.0903(3) 0.09637(14) 0.0452(6) Uani 1 1 d . . .
C0BA C -0.2538(3) 0.1325(4) 0.16684(14) 0.0478(6) Uani 1 1 d . . .
H0BA H -0.2725 0.0479 0.1964 0.057 Uiso 1 1 calc R . .
C1BA C 0.4838(4) 1.2008(4) 0.44954(14) 0.0528(7) Uani 1 1 d . . .
C2BA C -0.2712(4) 0.2179(4) 0.05284(14) 0.0512(7) Uani 1 1 d . . .
H2BA H -0.3024 0.1902 0.0053 0.061 Uiso 1 1 calc R . .
C3BA C 0.0339(3) 1.0009(4) 0.31360(14) 0.0490(7) Uani 1 1 d . . .
C4BA C 0.3418(4) 1.0142(4) 0.34900(14) 0.0490(6) Uani 1 1 d . . .
H4BA H 0.3442 0.9328 0.3110 0.059 Uiso 1 1 calc R . .
C5BA C 0.4873(4) 1.0791(4) 0.39324(15) 0.0518(7) Uani 1 1 d . . .
H5BA H 0.5862 1.0414 0.3852 0.062 Uiso 1 1 calc R . .
C6BA C -0.2044(3) 0.6422(4) 0.29376(13) 0.0450(6) Uani 1 1 d . . .
C7BA C 0.1283(3) 0.9043(4) 0.19468(14) 0.0456(6) Uani 1 1 d . . .
C8BA C 0.3352(4) 1.2554(5) 0.46112(15) 0.0639(9) Uani 1 1 d . . .
H8BA H 0.3330 1.3372 0.4990 0.077 Uiso 1 1 calc R . .
C9BA C 0.1921(4) 1.1897(4) 0.41717(15) 0.0570(8) Uani 1 1 d . . .
H9BA H 0.0932 1.2270 0.4256 0.068 Uiso 1 1 calc R . .
C0CA C -0.5412(4) 0.5359(5) 0.32883(17) 0.0660(9) Uani 1 1 d . . .
H0C1 H -0.5246 0.4260 0.3390 0.079 Uiso 1 1 calc R . .
H0C2 H -0.5092 0.6176 0.3709 0.079 Uiso 1 1 calc R . .
C1CA C -0.7256(4) 0.5184(5) 0.3062(2) 0.0718(10) Uani 1 1 d . . .
H1C1 H -0.7965 0.4801 0.3429 0.108 Uiso 1 1 calc R . .
H1C2 H -0.7568 0.4364 0.2649 0.108 Uiso 1 1 calc R . .
H1C3 H -0.7412 0.6277 0.2964 0.108 Uiso 1 1 calc R . .
C2CA C -0.4105(5) -0.2057(4) 0.1060(2) 0.0705(9) Uani 1 1 d . . .
H2C1 H -0.4648 -0.3114 0.0774 0.106 Uiso 1 1 calc R . .
H2C2 H -0.4838 -0.1817 0.1420 0.106 Uiso 1 1 calc R . .
H2C3 H -0.3041 -0.2157 0.1270 0.106 Uiso 1 1 calc R . .
C3CA C 0.7754(4) 1.2300(6) 0.4859(2) 0.0859(12) Uani 1 1 d . . .
H3C1 H 0.8583 1.2904 0.5228 0.129 Uiso 1 1 calc R . .
H3C2 H 0.8147 1.2611 0.4418 0.129 Uiso 1 1 calc R . .
H3C3 H 0.7600 1.1086 0.4859 0.129 Uiso 1 1 calc R . .
C4CA C 0.2897(6) 1.3188(5) 0.0897(2) 0.0911(13) Uani 1 1 d . . .
H4C1 H 0.2446 1.3459 0.0469 0.137 Uiso 1 1 calc R . .
H4C2 H 0.4088 1.3215 0.0864 0.137 Uiso 1 1 calc R . .
H4C3 H 0.2766 1.4015 0.1278 0.137 Uiso 1 1 calc R . .
C5CA C 0.1952(6) 1.1442(5) 0.10217(19) 0.0807(11) Uani 1 1 d . . .
H5C1 H 0.2078 1.0603 0.0637 0.097 Uiso 1 1 calc R . .
H5C2 H 0.0744 1.1404 0.1047 0.097 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
S4AA C0AA 1.732(2) . ?
S4AA C7BA 1.728(3) . ?
S0AA C6BA 1.710(3) . ?
S0AA C0CA 1.793(3) . ?
S1AA C7BA 1.748(3) . ?
S1AA C5CA 1.809(4) . ?
S2AA C6BA 1.623(3) . ?
C7CA C0AA 1.369(3) . ?
C7CA C5AA 1.437(4) . ?
C7CA C6BA 1.495(3) . ?
C0AA C1AA 1.472(4) . ?
C1AA C8AA 1.389(4) . ?
C1AA C6AA 1.393(3) . ?
C2AA C4BA 1.382(4) . ?
C2AA C9BA 1.397(4) . ?
C2AA C3BA 1.484(4) . ?
O C9AA 1.364(3) . ?
O C2CA 1.415(4) . ?
O0AA C3BA 1.220(3) . ?
C5AA C7BA 1.367(4) . ?
C5AA C3BA 1.503(4) . ?
C6AA C2BA 1.371(4) . ?
O30 C1BA 1.358(3) . ?
O30 C3CA 1.417(4) . ?
C8AA C0BA 1.374(4) . ?
C9AA C0BA 1.382(4) . ?
C9AA C2BA 1.390(4) . ?
C1BA C5BA 1.383(4) . ?
C1BA C8BA 1.388(4) . ?
C4BA C5BA 1.383(4) . ?
C8BA C9BA 1.367(4) . ?
C0CA C1CA 1.503(4) . ?
C4CA C5CA 1.489(5) . ?
 
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
C0AA S4AA C7BA 92.83(13) . . ?
C6BA S0AA C0CA 105.19(14) . . ?
C7BA S1AA C5CA 101.95(16) . . ?
C0AA C7CA C5AA 113.4(2) . . ?
C0AA C7CA C6BA 124.3(2) . . ?
C5AA C7CA C6BA 122.3(2) . . ?
C7CA C0AA C1AA 131.2(2) . . ?
C7CA C0AA S4AA 110.25(19) . . ?
C1AA C0AA S4AA 118.53(18) . . ?
C8AA C1AA C6AA 117.8(2) . . ?
C8AA C1AA C0AA 121.1(2) . . ?
C6AA C1AA C0AA 121.1(2) . . ?
C4BA C2AA C9BA 118.1(2) . . ?
C4BA C2AA C3BA 123.4(2) . . ?
C9BA C2AA C3BA 118.5(2) . . ?
C9AA O C2CA 117.7(2) . . ?
C7BA C5AA C7CA 112.6(2) . . ?
C7BA C5AA C3BA 124.3(2) . . ?
C7CA C5AA C3BA 122.8(2) . . ?
C2BA C6AA C1AA 121.0(2) . . ?
C1BA O30 C3CA 117.9(3) . . ?
C0BA C8AA C1AA 121.7(2) . . ?
O C9AA C0BA 125.2(3) . . ?
O C9AA C2BA 115.4(2) . . ?
C0BA C9AA C2BA 119.4(2) . . ?
C8AA C0BA C9AA 119.8(3) . . ?
O30 C1BA C5BA 124.9(3) . . ?
O30 C1BA C8BA 115.2(3) . . ?
C5BA C1BA C8BA 119.9(3) . . ?
C6AA C2BA C9AA 120.4(2) . . ?
O0AA C3BA C2AA 122.4(2) . . ?
O0AA C3BA C5AA 118.6(2) . . ?
C2AA C3BA C5AA 119.0(2) . . ?
C2AA C4BA C5BA 121.7(3) . . ?
C1BA C5BA C4BA 119.1(3) . . ?
C7CA C6BA S2AA 121.92(19) . . ?
C7CA C6BA S0AA 111.28(18) . . ?
S2AA C6BA S0AA 126.77(16) . . ?
C5AA C7BA S4AA 110.9(2) . . ?
C5AA C7BA S1AA 128.2(2) . . ?
S4AA C7BA S1AA 120.89(15) . . ?
C9BA C8BA C1BA 120.4(3) . . ?
C8BA C9BA C2AA 120.8(3) . . ?
C1CA C0CA S0AA 109.0(2) . . ?
C4CA C5CA S1AA 109.8(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.865
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.243
_refine_diff_density_min   -0.347
_refine_diff_density_rms    0.048
