# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_zhw0925
_database_code_depnum_ccdc_archive 'CCDC 1050464'
_audit_update_record             
;
2015-02-19 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2 S'
_chemical_formula_sum            'C18 H16 O2 S'
_chemical_formula_weight         296.37

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   8.3022(3)
_cell_length_b                   11.1608(4)
_cell_length_c                   16.3992(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.2720(10)
_cell_angle_gamma                90.00
_cell_volume                     1515.32(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    11794
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.4

_exptl_crystal_description       chunk
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8910
_exptl_absorpt_correction_T_max  0.9502
_exptl_absorpt_process_details   'Higashi,T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14547
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.44
_reflns_number_total             3450
_reflns_number_gt                2944
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0652P)²+0.3969P] 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     SHELXL
_refine_ls_extinction_coef       0.062(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3450
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C1 C 0.24430(17) 0.46644(12) 0.17860(9) 0.0374(3) Uani 1 1 d . . .
C2 C 0.1037(2) 0.42689(14) 0.13557(11) 0.0494(4) Uani 1 1 d . . .
H2 H 0.1096 0.3807 0.0887 0.059 Uiso 1 1 calc R . .
C3 C -0.0443(2) 0.45644(18) 0.16271(13) 0.0607(5) Uani 1 1 d . . .
H3 H -0.1388 0.4287 0.1350 0.073 Uiso 1 1 calc R . .
C4 C -0.0515(2) 0.52733(18) 0.23106(12) 0.0585(5) Uani 1 1 d . . .
H4 H -0.1516 0.5483 0.2488 0.070 Uiso 1 1 calc R . .
C5 C 0.08693(19) 0.56752(15) 0.27344(11) 0.0468(4) Uani 1 1 d . . .
H5 H 0.0788 0.6145 0.3198 0.056 Uiso 1 1 calc R . .
C6 C 0.24078(17) 0.53920(12) 0.24832(9) 0.0353(3) Uani 1 1 d . . .
C7 C 0.38476(17) 0.58772(12) 0.29576(9) 0.0365(3) Uani 1 1 d . . .
C8 C 0.51497(18) 0.63388(13) 0.26293(9) 0.0416(3) Uani 1 1 d . . .
H8 H 0.5941 0.6642 0.3005 0.050 Uiso 1 1 calc R . .
C9 C 0.55106(18) 0.64358(14) 0.17728(10) 0.0428(3) Uani 1 1 d . . .
C10 C 0.51822(18) 0.55899(14) 0.12084(10) 0.0433(3) Uani 1 1 d . . .
H10 H 0.5433 0.5738 0.0674 0.052 Uiso 1 1 calc R . .
C11 C 0.6340(3) 0.75710(17) 0.15313(12) 0.0635(5) Uani 1 1 d . . .
H11A H 0.6722 0.7474 0.0997 0.095 Uiso 1 1 calc R . .
H11B H 0.7236 0.7736 0.1919 0.095 Uiso 1 1 calc R . .
H11C H 0.5588 0.8225 0.1524 0.095 Uiso 1 1 calc R . .
C12 C 0.3755(2) 0.59217(13) 0.38806(9) 0.0431(4) Uani 1 1 d . . .
H12A H 0.4785 0.6196 0.4131 0.052 Uiso 1 1 calc R . .
H12B H 0.2940 0.6501 0.4008 0.052 Uiso 1 1 calc R . .
C13 C 0.33526(18) 0.47242(14) 0.42483(9) 0.0414(3) Uani 1 1 d . . .
C14 C 0.2245(2) 0.4644(2) 0.48413(11) 0.0604(5) Uani 1 1 d . . .
H14 H 0.1746 0.5335 0.5016 0.072 Uiso 1 1 calc R . .
C15 C 0.1876(3) 0.3542(3) 0.51764(14) 0.0774(7) Uani 1 1 d . . .
H15 H 0.1136 0.3500 0.5574 0.093 Uiso 1 1 calc R . .
C16 C 0.2595(3) 0.2524(2) 0.49243(13) 0.0752(7) Uani 1 1 d . . .
H16 H 0.2339 0.1787 0.5146 0.090 Uiso 1 1 calc R . .
C17 C 0.3689(3) 0.25874(18) 0.43454(12) 0.0712(6) Uani 1 1 d . . .
H17 H 0.4181 0.1892 0.4174 0.085 Uiso 1 1 calc R . .
C18 C 0.4073(3) 0.36824(15) 0.40105(10) 0.0553(4) Uani 1 1 d . . .
H18 H 0.4827 0.3714 0.3619 0.066 Uiso 1 1 calc R . .
O1 O 0.39685(17) 0.35927(11) 0.06668(8) 0.0605(4) Uani 1 1 d . . .
O2 O 0.52600(15) 0.36114(10) 0.20656(8) 0.0539(3) Uani 1 1 d . . .
S1 S 0.43069(5) 0.42251(3) 0.14283(2) 0.04137(15) Uani 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
C1 C2 1.390(2) . ?
C1 C6 1.404(2) . ?
C1 S1 1.7647(14) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.479(2) . ?
C7 C8 1.346(2) . ?
C7 C12 1.522(2) . ?
C8 C9 1.462(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.336(2) . ?
C9 C11 1.509(2) . ?
C10 S1 1.7371(16) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.514(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.377(2) . ?
C13 C14 1.390(2) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O1 S1 1.4437(12) . ?
O2 S1 1.4369(12) . ?

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
C2 C1 C6 121.95(14) . . ?
C2 C1 S1 117.83(12) . . ?
C6 C1 S1 120.22(11) . . ?
C3 C2 C1 119.70(16) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.61(16) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.94(16) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.49(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 116.28(13) . . ?
C1 C6 C7 125.08(12) . . ?
C5 C6 C7 118.65(13) . . ?
C8 C7 C6 124.85(13) . . ?
C8 C7 C12 119.13(13) . . ?
C6 C7 C12 115.87(12) . . ?
C7 C8 C9 129.87(14) . . ?
C7 C8 H8 115.1 . . ?
C9 C8 H8 115.1 . . ?
C10 C9 C8 124.57(14) . . ?
C10 C9 C11 119.03(15) . . ?
C8 C9 C11 116.39(15) . . ?
C9 C10 S1 122.88(12) . . ?
C9 C10 H10 118.6 . . ?
S1 C10 H10 118.6 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C7 113.34(12) . . ?
C13 C12 H12A 108.9 . . ?
C7 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C7 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 117.87(16) . . ?
C18 C13 C12 121.28(14) . . ?
C14 C13 C12 120.85(15) . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.83(19) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.99(18) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O2 S1 O1 117.21(8) . . ?
O2 S1 C10 110.66(8) . . ?
O1 S1 C10 107.85(8) . . ?
O2 S1 C1 109.86(7) . . ?
O1 S1 C1 107.72(8) . . ?
C10 S1 C1 102.48(7) . . ?

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
C6 C1 C2 C3 -1.9(2) . . . . ?
S1 C1 C2 C3 178.25(14) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
S1 C1 C6 C5 -178.61(11) . . . . ?
C2 C1 C6 C7 -178.06(14) . . . . ?
S1 C1 C6 C7 1.8(2) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C5 C6 C7 178.65(15) . . . . ?
C1 C6 C7 C8 42.0(2) . . . . ?
C5 C6 C7 C8 -137.52(16) . . . . ?
C1 C6 C7 C12 -142.39(14) . . . . ?
C5 C6 C7 C12 38.06(18) . . . . ?
C6 C7 C8 C9 -2.8(2) . . . . ?
C12 C7 C8 C9 -178.24(15) . . . . ?
C7 C8 C9 C10 -39.8(3) . . . . ?
C7 C8 C9 C11 141.41(17) . . . . ?
C8 C9 C10 S1 -1.5(2) . . . . ?
C11 C9 C10 S1 177.31(13) . . . . ?
C8 C7 C12 C13 -129.71(15) . . . . ?
C6 C7 C12 C13 54.44(17) . . . . ?
C7 C12 C13 C18 43.4(2) . . . . ?
C7 C12 C13 C14 -136.88(16) . . . . ?
C18 C13 C14 C15 -0.4(3) . . . . ?
C12 C13 C14 C15 179.88(17) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
C12 C13 C18 C17 -179.52(17) . . . . ?
C16 C17 C18 C13 -0.5(3) . . . . ?
C9 C10 S1 O2 -56.70(15) . . . . ?
C9 C10 S1 O1 173.89(13) . . . . ?
C9 C10 S1 C1 60.38(15) . . . . ?
C2 C1 S1 O2 -123.20(13) . . . . ?
C6 C1 S1 O2 56.91(13) . . . . ?
C2 C1 S1 O1 5.55(14) . . . . ?
C6 C1 S1 O1 -174.34(11) . . . . ?
C2 C1 S1 C10 119.15(13) . . . . ?
C6 C1 S1 C10 -60.74(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.065
