# Electronic Supplementary Material (ESI) for ChemComm.
# 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/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_40708ta
_database_code_depnum_ccdc_archive 'CCDC 1047801'
_audit_update_record             
;
2015-02-05 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 O2 S'
_chemical_formula_sum            'C18 H20 O2 S'
_chemical_formula_weight         300.40
_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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.323(5)
_cell_length_b                   12.346(9)
_cell_length_c                   9.152(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.447(17)
_cell_angle_gamma                90.00
_cell_volume                     784.9(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7702
_exptl_absorpt_correction_T_max  0.9470
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10183
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         6.79
_diffrn_reflns_theta_max         68.28
_reflns_number_total             2650
_reflns_number_gt                2554
_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)+(0.0586P)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    constr
_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   -0.007(14)
_refine_ls_number_reflns         2650
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 1.02776(6) 0.44908(4) 1.03434(5) 0.02101(14) Uani 1 1 d . . .
O2 O 1.0887(2) 0.52522(14) 1.16021(15) 0.0311(4) Uani 1 1 d . . .
O3 O 1.14874(19) 0.35693(13) 1.03319(17) 0.0282(4) Uani 1 1 d . . .
C4 C 1.0371(3) 0.47397(17) 0.7398(2) 0.0220(5) Uani 1 1 d . . .
H1 H 1.0952 0.4043 0.7508 0.026 Uiso 1 1 calc R . .
C5 C 0.9082(3) 0.62350(18) 0.8468(2) 0.0193(4) Uani 1 1 d . . .
H2 H 0.8790 0.6552 0.9313 0.023 Uiso 1 1 calc R . .
C6 C 0.7076(3) 0.30807(17) 0.9226(2) 0.0190(4) Uani 1 1 d . . .
H3 H 0.8043 0.2482 0.9420 0.023 Uiso 1 1 calc R . .
C7 C 0.7964(3) 0.40118(18) 1.0331(2) 0.0208(4) Uani 1 1 d . . .
H4 H 0.8070 0.3776 1.1388 0.025 Uiso 1 1 calc R . .
H5 H 0.7057 0.4630 1.0075 0.025 Uiso 1 1 calc R . .
C8 C 0.9984(3) 0.53077(19) 0.6025(2) 0.0256(5) Uani 1 1 d . . .
H6 H 1.0309 0.4995 0.5191 0.031 Uiso 1 1 calc R . .
C9 C 0.5393(3) 0.42839(18) 0.6924(2) 0.0233(5) Uani 1 1 d . . .
H7 H 0.5042 0.4767 0.7598 0.028 Uiso 1 1 calc R . .
C10 C 0.4815(3) 0.4498(2) 0.5358(2) 0.0288(5) Uani 1 1 d . . .
H8 H 0.4073 0.5126 0.4966 0.035 Uiso 1 1 calc R . .
C11 C 0.8705(3) 0.67874(19) 0.7099(2) 0.0231(4) Uani 1 1 d . . .
H9 H 0.8150 0.7490 0.7003 0.028 Uiso 1 1 calc R . .
C12 C 0.9896(3) 0.52073(18) 0.8602(2) 0.0201(4) Uani 1 1 d . . .
C13 C 0.5315(3) 0.3797(2) 0.4356(2) 0.0294(5) Uani 1 1 d . . .
H10 H 0.4931 0.3948 0.3284 0.035 Uiso 1 1 calc R . .
C14 C 0.5346(3) 0.26696(19) 0.9643(2) 0.0218(4) Uani 1 1 d . . .
H11 H 0.4272 0.3201 0.9501 0.026 Uiso 1 1 calc R . .
C15 C 0.4749(3) 0.1512(2) 0.9326(2) 0.0274(5) Uani 1 1 d . . .
H12 H 0.5534 0.1043 0.8880 0.033 Uiso 1 1 calc R . .
H13 H 0.3354 0.1349 0.8974 0.033 Uiso 1 1 calc R . .
C16 C 0.6959(3) 0.26629(19) 0.6510(2) 0.0225(4) Uani 1 1 d . . .
H14 H 0.7686 0.2029 0.6898 0.027 Uiso 1 1 calc R . .
C17 C 0.9131(3) 0.6327(2) 0.5846(2) 0.0255(5) Uani 1 1 d . . .
C18 C 0.6485(3) 0.33668(17) 0.7523(2) 0.0193(4) Uani 1 1 d . . .
C19 C 0.6381(3) 0.2877(2) 0.4941(2) 0.0284(5) Uani 1 1 d . . .
H15 H 0.6718 0.2390 0.4264 0.034 Uiso 1 1 calc R . .
C20 C 0.5640(3) 0.18915(18) 1.0960(2) 0.0249(5) Uani 1 1 d . . .
H16 H 0.6973 0.1657 1.1515 0.030 Uiso 1 1 calc R . .
H17 H 0.4792 0.1963 1.1609 0.030 Uiso 1 1 calc R . .
C21 C 0.8634(3) 0.6932(2) 0.4350(3) 0.0360(6) Uani 1 1 d . . .
H18 H 0.7231 0.6987 0.3905 0.054 Uiso 1 1 calc R . .
H19 H 0.9153 0.6544 0.3634 0.054 Uiso 1 1 calc R . .
H20 H 0.9193 0.7660 0.4533 0.054 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 O2 1.4438(17) . ?
S1 O3 1.4441(17) . ?
S1 C12 1.766(2) . ?
S1 C7 1.791(2) . ?
C4 C12 1.383(3) . ?
C4 C8 1.387(3) . ?
C4 H1 0.9500 . ?
C5 C11 1.375(3) . ?
C5 C12 1.391(3) . ?
C5 H2 0.9500 . ?
C6 C14 1.521(3) . ?
C6 C18 1.522(3) . ?
C6 C7 1.533(3) . ?
C6 H3 1.0000 . ?
C7 H4 0.9900 . ?
C7 H5 0.9900 . ?
C8 C17 1.392(3) . ?
C8 H6 0.9500 . ?
C9 C10 1.386(3) . ?
C9 C18 1.394(3) . ?
C9 H7 0.9500 . ?
C10 C13 1.391(3) . ?
C10 H8 0.9500 . ?
C11 C17 1.401(3) . ?
C11 H9 0.9500 . ?
C13 C19 1.387(4) . ?
C13 H10 0.9500 . ?
C14 C15 1.496(4) . ?
C14 C20 1.502(3) . ?
C14 H11 1.0000 . ?
C15 C20 1.504(3) . ?
C15 H12 0.9900 . ?
C15 H13 0.9900 . ?
C16 C19 1.388(3) . ?
C16 C18 1.392(3) . ?
C16 H14 0.9500 . ?
C17 C21 1.500(3) . ?
C19 H15 0.9500 . ?
C20 H16 0.9900 . ?
C20 H17 0.9900 . ?
C21 H18 0.9800 . ?
C21 H19 0.9800 . ?
C21 H20 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
O2 S1 O3 118.91(10) . . ?
O2 S1 C12 108.34(11) . . ?
O3 S1 C12 108.08(10) . . ?
O2 S1 C7 105.84(9) . . ?
O3 S1 C7 108.72(11) . . ?
C12 S1 C7 106.27(9) . . ?
C12 C4 C8 118.68(19) . . ?
C12 C4 H1 120.7 . . ?
C8 C4 H1 120.7 . . ?
C11 C5 C12 119.34(19) . . ?
C11 C5 H2 120.3 . . ?
C12 C5 H2 120.3 . . ?
C14 C6 C18 110.20(14) . . ?
C14 C6 C7 107.34(15) . . ?
C18 C6 C7 115.16(18) . . ?
C14 C6 H3 108.0 . . ?
C18 C6 H3 108.0 . . ?
C7 C6 H3 108.0 . . ?
C6 C7 S1 117.08(14) . . ?
C6 C7 H4 108.0 . . ?
S1 C7 H4 108.0 . . ?
C6 C7 H5 108.0 . . ?
S1 C7 H5 108.0 . . ?
H4 C7 H5 107.3 . . ?
C4 C8 C17 121.29(19) . . ?
C4 C8 H6 119.4 . . ?
C17 C8 H6 119.4 . . ?
C10 C9 C18 120.7(2) . . ?
C10 C9 H7 119.6 . . ?
C18 C9 H7 119.6 . . ?
C9 C10 C13 120.3(2) . . ?
C9 C10 H8 119.8 . . ?
C13 C10 H8 119.8 . . ?
C5 C11 C17 120.8(2) . . ?
C5 C11 H9 119.6 . . ?
C17 C11 H9 119.6 . . ?
C4 C12 C5 121.29(18) . . ?
C4 C12 S1 120.15(17) . . ?
C5 C12 S1 118.55(15) . . ?
C19 C13 C10 119.3(2) . . ?
C19 C13 H10 120.4 . . ?
C10 C13 H10 120.4 . . ?
C15 C14 C20 60.23(14) . . ?
C15 C14 C6 119.05(19) . . ?
C20 C14 C6 119.67(17) . . ?
C15 C14 H11 115.6 . . ?
C20 C14 H11 115.6 . . ?
C6 C14 H11 115.6 . . ?
C14 C15 C20 60.09(14) . . ?
C14 C15 H12 117.8 . . ?
C20 C15 H12 117.8 . . ?
C14 C15 H13 117.8 . . ?
C20 C15 H13 117.8 . . ?
H12 C15 H13 114.9 . . ?
C19 C16 C18 120.8(2) . . ?
C19 C16 H14 119.6 . . ?
C18 C16 H14 119.6 . . ?
C8 C17 C11 118.58(19) . . ?
C8 C17 C21 121.9(2) . . ?
C11 C17 C21 119.5(2) . . ?
C16 C18 C9 118.58(18) . . ?
C16 C18 C6 119.15(19) . . ?
C9 C18 C6 122.17(18) . . ?
C16 C19 C13 120.3(2) . . ?
C16 C19 H15 119.8 . . ?
C13 C19 H15 119.8 . . ?
C15 C20 C14 59.68(15) . . ?
C15 C20 H16 117.8 . . ?
C14 C20 H16 117.8 . . ?
C15 C20 H17 117.8 . . ?
C14 C20 H17 117.8 . . ?
H16 C20 H17 114.9 . . ?
C17 C21 H18 109.5 . . ?
C17 C21 H19 109.5 . . ?
H18 C21 H19 109.5 . . ?
C17 C21 H20 109.5 . . ?
H18 C21 H20 109.5 . . ?
H19 C21 H20 109.5 . . ?

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
C14 C6 C7 S1 168.89(14) . . . . ?
C18 C6 C7 S1 -68.00(19) . . . . ?
O2 S1 C7 C6 -172.64(14) . . . . ?
O3 S1 C7 C6 -43.82(17) . . . . ?
C12 S1 C7 C6 72.30(18) . . . . ?
C12 C4 C8 C17 -0.2(3) . . . . ?
C18 C9 C10 C13 0.1(3) . . . . ?
C12 C5 C11 C17 0.0(3) . . . . ?
C8 C4 C12 C5 -1.3(3) . . . . ?
C8 C4 C12 S1 177.55(14) . . . . ?
C11 C5 C12 C4 1.4(3) . . . . ?
C11 C5 C12 S1 -177.49(14) . . . . ?
O2 S1 C12 C4 143.24(16) . . . . ?
O3 S1 C12 C4 13.14(18) . . . . ?
C7 S1 C12 C4 -103.41(16) . . . . ?
O2 S1 C12 C5 -37.84(17) . . . . ?
O3 S1 C12 C5 -167.94(14) . . . . ?
C7 S1 C12 C5 75.51(18) . . . . ?
C9 C10 C13 C19 0.7(3) . . . . ?
C18 C6 C14 C15 81.9(2) . . . . ?
C7 C6 C14 C15 -151.97(17) . . . . ?
C18 C6 C14 C20 152.20(18) . . . . ?
C7 C6 C14 C20 -81.7(2) . . . . ?
C6 C14 C15 C20 109.55(19) . . . . ?
C4 C8 C17 C11 1.5(3) . . . . ?
C4 C8 C17 C21 -177.59(19) . . . . ?
C5 C11 C17 C8 -1.5(3) . . . . ?
C5 C11 C17 C21 177.69(19) . . . . ?
C19 C16 C18 C9 0.9(3) . . . . ?
C19 C16 C18 C6 177.54(18) . . . . ?
C10 C9 C18 C16 -0.9(3) . . . . ?
C10 C9 C18 C6 -177.41(18) . . . . ?
C14 C6 C18 C16 -103.6(2) . . . . ?
C7 C6 C18 C16 134.8(2) . . . . ?
C14 C6 C18 C9 72.9(2) . . . . ?
C7 C6 C18 C9 -48.7(2) . . . . ?
C18 C16 C19 C13 -0.2(3) . . . . ?
C10 C13 C19 C16 -0.7(3) . . . . ?
C6 C14 C20 C15 -108.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        68.28
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
