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

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#
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#                                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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_3y19har

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 O3 S'
_chemical_formula_weight         380.48
_chemical_absolute_configuration S

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           Orthorhombic
_symmetry_space_group_name_H-M   p_21_21_21

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                   6.5465(17)
_cell_length_b                   7.844(2)
_cell_length_c                   38.945(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1999.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8682
_exptl_absorpt_correction_T_max  0.9475
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(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 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12232
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.3355
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         29.14
_reflns_number_total             5092
_reflns_number_gt                1597
_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)+(0.0191P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_number_reflns         5092
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0426
_refine_ls_wR_factor_gt          0.0420
_refine_ls_goodness_of_fit_ref   0.662
_refine_ls_restrained_S_all      0.662
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.004

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 0.57291(8) 1.01013(7) 0.861929(13) 0.02633(12) Uani 1 1 d . . .
O3 O 1.1222(2) 1.27133(15) 0.96996(3) 0.0222(3) Uani 1 1 d . . .
O1 O 0.6269(2) 0.77745(16) 0.90959(3) 0.0279(3) Uani 1 1 d . . .
C17 C 1.0985(3) 0.9886(2) 0.89979(4) 0.0195(4) Uani 1 1 d . . .
H17 H 1.1120 1.0673 0.8814 0.023 Uiso 1 1 calc R . .
C18 C 1.1065(3) 1.0511(2) 0.93113(5) 0.0230(4) Uani 1 1 d . . .
H18 H 1.1024 0.9766 0.9503 0.028 Uiso 1 1 calc R . .
O2 O 1.1304(2) 1.33823(16) 0.91350(3) 0.0294(3) Uani 1 1 d . . .
C5 C 1.0793(4) 0.9950(3) 0.78412(4) 0.0268(4) Uani 1 1 d . . .
H5 H 1.1901 0.9904 0.7684 0.032 Uiso 1 1 calc R . .
C10 C 0.6766(3) 0.5455(2) 0.83682(4) 0.0176(4) Uani 1 1 d . . .
C16 C 1.0700(4) 0.8054(2) 0.89049(4) 0.0191(4) Uani 1 1 d . . .
H16A H 1.0459 0.7380 0.9116 0.023 Uiso 1 1 calc R . .
H16B H 1.1960 0.7620 0.8795 0.023 Uiso 1 1 calc R . .
C2 C 0.8876(3) 0.78253(19) 0.86571(4) 0.0179(4) Uani 1 1 d . . .
C4 C 1.0724(4) 0.8834(2) 0.81148(4) 0.0231(4) Uani 1 1 d . . .
H4 H 1.1775 0.8012 0.8145 0.028 Uiso 1 1 calc R . .
C8 C 0.7614(3) 1.0142(3) 0.82966(4) 0.0186(4) Uani 1 1 d . . .
C14 C 0.4867(3) 0.5381(3) 0.78400(5) 0.0237(5) Uani 1 1 d . . .
H14 H 0.4745 0.5677 0.7604 0.028 Uiso 1 1 calc R . .
C13 C 0.3322(3) 0.4473(2) 0.80029(6) 0.0269(5) Uani 1 1 d . . .
H13 H 0.2147 0.4129 0.7878 0.032 Uiso 1 1 calc R . .
C15 C 0.6568(3) 0.5845(2) 0.80227(5) 0.0207(4) Uani 1 1 d . . .
H15 H 0.7634 0.6446 0.7910 0.025 Uiso 1 1 calc R . .
C19 C 1.1218(3) 1.2363(2) 0.93641(4) 0.0208(4) Uani 1 1 d . . .
C20 C 1.1146(4) 1.4495(2) 0.98191(5) 0.0251(5) Uani 1 1 d . . .
C9 C 0.8674(3) 0.5916(2) 0.85663(5) 0.0210(4) Uani 1 1 d . . .
H9A H 0.9879 0.5573 0.8429 0.025 Uiso 1 1 calc R . .
H9B H 0.8697 0.5247 0.8782 0.025 Uiso 1 1 calc R . .
C22 C 0.9150(4) 1.5262(3) 0.97077(5) 0.0305(5) Uani 1 1 d . . .
H22A H 0.9067 1.5252 0.9456 0.046 Uiso 1 1 calc R . .
H22B H 0.9063 1.6440 0.9791 0.046 Uiso 1 1 calc R . .
H22C H 0.8019 1.4596 0.9803 0.046 Uiso 1 1 calc R . .
C12 C 0.3497(3) 0.4075(2) 0.83453(5) 0.0257(5) Uani 1 1 d . . .
H12 H 0.2440 0.3455 0.8457 0.031 Uiso 1 1 calc R . .
C1 C 0.6937(3) 0.8377(2) 0.88386(5) 0.0194(5) Uani 1 1 d . . .
C23 C 1.1238(4) 1.4301(3) 1.02032(5) 0.0344(6) Uani 1 1 d . . .
H23A H 1.0113 1.3570 1.0280 0.052 Uiso 1 1 calc R . .
H23B H 1.1117 1.5424 1.0311 0.052 Uiso 1 1 calc R . .
H23C H 1.2544 1.3782 1.0268 0.052 Uiso 1 1 calc R . .
C6 C 0.9247(4) 1.1139(2) 0.77952(4) 0.0252(4) Uani 1 1 d . . .
H6 H 0.9284 1.1882 0.7603 0.030 Uiso 1 1 calc R . .
C7 C 0.7660(3) 1.1249(3) 0.80264(5) 0.0245(5) Uani 1 1 d . . .
H7 H 0.6618 1.2079 0.7998 0.029 Uiso 1 1 calc R . .
C3 C 0.9127(3) 0.89145(19) 0.83447(4) 0.0169(4) Uani 1 1 d . . .
C11 C 0.5193(3) 0.4569(2) 0.85273(5) 0.0242(5) Uani 1 1 d . . .
H11 H 0.5291 0.4302 0.8765 0.029 Uiso 1 1 calc R . .
C21 C 1.3009(4) 1.5458(3) 0.96892(7) 0.0353(5) Uani 1 1 d . . .
H21A H 1.4252 1.4864 0.9762 0.053 Uiso 1 1 calc R . .
H21B H 1.3006 1.6615 0.9784 0.053 Uiso 1 1 calc R . .
H21C H 1.2969 1.5516 0.9438 0.053 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 1.7614(17) . ?
S1 C1 1.7847(19) . ?
O3 C19 1.3352(19) . ?
O3 C20 1.473(2) . ?
O1 C1 1.191(2) . ?
C17 C18 1.316(2) . ?
C17 C16 1.494(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.470(3) . ?
C18 H18 0.9500 . ?
O2 C19 1.200(2) . ?
C5 C4 1.380(2) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C10 C15 1.386(3) . ?
C10 C11 1.388(3) . ?
C10 C9 1.512(3) . ?
C16 C2 1.546(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C2 C3 1.496(2) . ?
C2 C1 1.515(3) . ?
C2 C9 1.545(2) . ?
C4 C3 1.378(3) . ?
C4 H4 0.9500 . ?
C8 C7 1.365(3) . ?
C8 C3 1.394(3) . ?
C14 C15 1.370(2) . ?
C14 C13 1.390(3) . ?
C14 H14 0.9500 . ?
C13 C12 1.375(3) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C20 C22 1.503(3) . ?
C20 C23 1.505(2) . ?
C20 C21 1.521(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C12 C11 1.373(3) . ?
C12 H12 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C6 C7 1.378(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C11 H11 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 C1 92.55(11) . . ?
C19 O3 C20 120.27(14) . . ?
C18 C17 C16 126.04(18) . . ?
C18 C17 H17 117.0 . . ?
C16 C17 H17 117.0 . . ?
C17 C18 C19 120.03(18) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C15 C10 C11 118.32(19) . . ?
C15 C10 C9 121.32(18) . . ?
C11 C10 C9 120.31(15) . . ?
C17 C16 C2 111.05(16) . . ?
C17 C16 H16A 109.4 . . ?
C2 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C2 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C3 C2 C1 107.96(14) . . ?
C3 C2 C9 112.16(13) . . ?
C1 C2 C9 108.17(15) . . ?
C3 C2 C16 110.89(15) . . ?
C1 C2 C16 108.83(15) . . ?
C9 C2 C16 108.75(14) . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C7 C8 C3 121.81(16) . . ?
C7 C8 S1 125.26(16) . . ?
C3 C8 S1 112.93(13) . . ?
C15 C14 C13 119.36(17) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C14 C15 C10 121.42(19) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
O2 C19 O3 126.20(17) . . ?
O2 C19 C18 123.89(17) . . ?
O3 C19 C18 109.90(16) . . ?
O3 C20 C22 108.56(17) . . ?
O3 C20 C23 102.52(15) . . ?
C22 C20 C23 111.23(19) . . ?
O3 C20 C21 109.82(16) . . ?
C22 C20 C21 113.71(17) . . ?
C23 C20 C21 110.4(2) . . ?
C10 C9 C2 114.79(15) . . ?
C10 C9 H9A 108.6 . . ?
C2 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C2 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C12 C13 120.24(19) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O1 C1 C2 125.93(17) . . ?
O1 C1 S1 122.71(16) . . ?
C2 C1 S1 111.36(13) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 C6 C5 120.50(18) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 118.76(19) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C4 C3 C8 118.93(15) . . ?
C4 C3 C2 125.84(17) . . ?
C8 C3 C2 115.19(16) . . ?
C12 C11 C10 120.72(18) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.948
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 995705'
