# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_exp_248
_database_code_depnum_ccdc_archive 'CCDC 1838957'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 O3 S'
_chemical_formula_weight         360.41

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.1358(3)
_cell_length_b                   18.8753(7)
_cell_length_c                   20.9542(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3613.4(2)
_cell_formula_units_Z            8
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50439
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.629
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3548
_reflns_number_gt                3135
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+1.5170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3548
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.58894(7) 0.58805(4) 0.62195(3) 0.0587(2) Uani 1 1 d . . . . .
O1 O 0.5877(2) 0.52840(10) 0.66416(9) 0.0761(6) Uani 1 1 d . . . . .
O2 O 0.46596(19) 0.60036(13) 0.58115(9) 0.0807(6) Uani 1 1 d . . . . .
O3 O 0.9941(2) 0.62702(10) 0.45528(8) 0.0660(5) Uani 1 1 d . . . . .
C1 C 0.7713(2) 0.61212(12) 0.51743(10) 0.0474(5) Uani 1 1 d . . . . .
C2 C 0.7497(2) 0.58252(12) 0.57514(10) 0.0473(5) Uani 1 1 d . . . . .
C3 C 0.8891(2) 0.55323(12) 0.60136(11) 0.0484(5) Uani 1 1 d . . . . .
C4 C 0.9217(3) 0.52063(14) 0.65842(12) 0.0613(7) Uani 1 1 d . . . . .
H4 H 0.849070 0.511442 0.688372 0.074 Uiso 1 1 calc R U . . .
C5 C 1.0662(3) 0.50191(15) 0.66988(14) 0.0694(8) Uani 1 1 d . . . . .
H5 H 1.090141 0.480172 0.708315 0.083 Uiso 1 1 calc R U . . .
C6 C 1.1749(3) 0.51459(14) 0.62605(14) 0.0674(7) Uani 1 1 d . . . . .
H6 H 1.270625 0.501117 0.634953 0.081 Uiso 1 1 calc R U . . .
C7 C 1.1422(3) 0.54746(13) 0.56847(13) 0.0583(6) Uani 1 1 d . . . . .
H7 H 1.214914 0.556358 0.538453 0.070 Uiso 1 1 calc R U . . .
C8 C 0.9991(2) 0.56647(12) 0.55714(11) 0.0474(5) Uani 1 1 d . . . . .
C9 C 0.9338(3) 0.60453(12) 0.50221(11) 0.0484(5) Uani 1 1 d . . . . .
C10 C 0.6716(3) 0.65027(13) 0.47406(10) 0.0510(6) Uani 1 1 d . . . . .
C11 C 0.7047(3) 0.71958(14) 0.45741(12) 0.0636(7) Uani 1 1 d . . . . .
H11 H 0.789058 0.741027 0.473036 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6114(4) 0.75668(17) 0.41735(15) 0.0857(10) Uani 1 1 d . . . . .
H12 H 0.632737 0.803338 0.406520 0.103 Uiso 1 1 calc R U . . .
C13 C 0.4884(4) 0.7251(2) 0.39370(17) 0.0970(12) Uani 1 1 d . . . . .
H13 H 0.426148 0.750450 0.367026 0.116 Uiso 1 1 calc R U . . .
C14 C 0.4562(4) 0.6565(2) 0.40899(15) 0.0899(10) Uani 1 1 d . . . . .
H14 H 0.372573 0.635180 0.392517 0.108 Uiso 1 1 calc R U . . .
C15 C 0.5477(3) 0.61880(16) 0.44881(12) 0.0664(7) Uani 1 1 d . . . . .
H15 H 0.525968 0.571954 0.458767 0.080 Uiso 1 1 calc R U . . .
C20 C 0.6214(2) 0.66529(14) 0.66606(11) 0.0502(6) Uani 1 1 d . . . . .
C21 C 0.5797(3) 0.73026(15) 0.64103(12) 0.0607(7) Uani 1 1 d . . . . .
H21 H 0.531962 0.732635 0.601881 0.073 Uiso 1 1 calc R U . . .
C22 C 0.6094(3) 0.79103(16) 0.67465(13) 0.0645(7) Uani 1 1 d . . . . .
H22 H 0.580168 0.834505 0.658103 0.077 Uiso 1 1 calc R U . . .
C23 C 0.6816(3) 0.78902(14) 0.73230(12) 0.0626(7) Uani 1 1 d . . . . .
C24 C 0.7230(3) 0.72377(15) 0.75627(12) 0.0671(7) Uani 1 1 d . . . . .
H24 H 0.772188 0.721686 0.795080 0.081 Uiso 1 1 calc R U . . .
C25 C 0.6932(3) 0.66189(14) 0.72417(11) 0.0597(6) Uani 1 1 d . . . . .
H25 H 0.720833 0.618415 0.741238 0.072 Uiso 1 1 calc R U . . .
C26 C 0.7178(4) 0.85601(17) 0.76758(16) 0.0949(11) Uani 1 1 d . . . . .
H26A H 0.755229 0.844456 0.809100 0.142 Uiso 1 1 calc R U . . .
H26B H 0.631012 0.884273 0.771981 0.142 Uiso 1 1 calc R U . . .
H26C H 0.790283 0.882139 0.744205 0.142 Uiso 1 1 calc R U . . .


_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 1.4307(19) . ?
S1 O1 1.432(2) . ?
S1 C20 1.752(3) . ?
S1 C2 1.769(2) . ?
O3 C9 1.205(3) . ?
C1 C2 1.347(3) . ?
C1 C10 1.475(3) . ?
C1 C9 1.525(3) . ?
C2 C3 1.494(3) . ?
C3 C4 1.377(3) . ?
C3 C8 1.389(3) . ?
C4 C5 1.387(4) . ?
C5 C6 1.373(4) . ?
C6 C7 1.389(4) . ?
C7 C8 1.376(3) . ?
C8 C9 1.482(3) . ?
C10 C15 1.383(4) . ?
C10 C11 1.387(3) . ?
C11 C12 1.386(4) . ?
C12 C13 1.365(5) . ?
C13 C14 1.366(5) . ?
C14 C15 1.379(4) . ?
C20 C25 1.384(3) . ?
C20 C21 1.387(4) . ?
C21 C22 1.373(4) . ?
C22 C23 1.377(4) . ?
C23 C24 1.383(4) . ?
C23 C26 1.502(4) . ?
C24 C25 1.375(4) . ?

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 O1 119.39(12) . . ?
O2 S1 C20 108.25(13) . . ?
O1 S1 C20 109.27(11) . . ?
O2 S1 C2 109.27(11) . . ?
O1 S1 C2 107.61(12) . . ?
C20 S1 C2 101.60(10) . . ?
C2 C1 C10 131.7(2) . . ?
C2 C1 C9 107.0(2) . . ?
C10 C1 C9 121.2(2) . . ?
C1 C2 C3 111.0(2) . . ?
C1 C2 S1 126.54(19) . . ?
C3 C2 S1 121.73(16) . . ?
C4 C3 C8 120.2(2) . . ?
C4 C3 C2 132.0(2) . . ?
C8 C3 C2 107.76(19) . . ?
C3 C4 C5 118.0(3) . . ?
C6 C5 C4 121.8(3) . . ?
C5 C6 C7 120.2(3) . . ?
C8 C7 C6 118.0(3) . . ?
C7 C8 C3 121.7(2) . . ?
C7 C8 C9 130.0(2) . . ?
C3 C8 C9 108.3(2) . . ?
O3 C9 C8 128.3(2) . . ?
O3 C9 C1 125.7(2) . . ?
C8 C9 C1 105.97(19) . . ?
C15 C10 C11 119.1(2) . . ?
C15 C10 C1 122.1(2) . . ?
C11 C10 C1 118.7(2) . . ?
C12 C11 C10 119.6(3) . . ?
C13 C12 C11 120.4(3) . . ?
C12 C13 C14 120.4(3) . . ?
C13 C14 C15 120.0(3) . . ?
C14 C15 C10 120.4(3) . . ?
C25 C20 C21 120.3(2) . . ?
C25 C20 S1 120.4(2) . . ?
C21 C20 S1 119.32(19) . . ?
C22 C21 C20 119.3(2) . . ?
C21 C22 C23 121.5(3) . . ?
C22 C23 C24 118.3(3) . . ?
C22 C23 C26 120.9(3) . . ?
C24 C23 C26 120.7(3) . . ?
C25 C24 C23 121.7(2) . . ?
C24 C25 C20 119.0(2) . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.035


