# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_BN0854
_database_code_depnum_ccdc_archive 'CCDC 1571217'
_audit_update_record             
;
2017-08-28 deposited with the CCDC.
2017-12-13 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         'C20 H20 O2 S'
_chemical_formula_sum            'C20 H20 O2 S'
_chemical_formula_weight         324.42

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   6.2278(6)
_cell_length_b                   37.440(4)
_cell_length_c                   7.3546(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1714.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    657
_cell_measurement_theta_min      14.9
_cell_measurement_theta_max      71.8

_exptl_crystal_description       'large thin plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.724
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.641
_exptl_special_details           
;
 Reqab (Higashi, Rigaku, 1998)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku Rotating Anode'
_diffrn_radiation_monochromator  'Osmic Confocal CMF mirrors'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid2 curved IP'
_diffrn_measurement_device       
;
Crystal Goniometer Chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku mm007HF microfocus
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            12953
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.989
_diffrn_reflns_theta_max         68.206
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1591
_reflns_number_gt                831
_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_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)+(0.1209P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_number_reflns         1591
_refine_ls_number_parameters     116
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.2021
_refine_ls_wR_factor_gt          0.1663
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.928
_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_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
O1 O 0.5067(3) 0.07817(5) -0.0071(3) 0.0836(7) Uani 1 1 d . . . . .
C1 C 0.3004(7) 0.250000 0.0272(5) 0.0692(10) Uani 1 2 d DS T P A .
H1 H 0.442475 0.250000 0.066046 0.083 Uiso 1 2 calc R U P . .
C2 C 0.1758(5) 0.21860(7) -0.0068(3) 0.0673(7) Uani 1 1 d D . . . .
C3 C -0.044(3) 0.2237(6) -0.045(3) 0.093(6) Uani 0.5 1 d D . P A 1
H31 H -0.153763 0.207358 -0.064181 0.112 Uiso 0.5 1 calc R U P A 1
S1 S -0.0774(6) 0.22938(18) -0.0664(10) 0.0822(9) Uani 0.5 1 d . . P A 2
C4 C 0.2576(5) 0.18184(7) -0.0007(3) 0.0645(8) Uani 1 1 d D . . . .
C7 C 0.4319(5) 0.11275(7) 0.0024(4) 0.0687(8) Uani 1 1 d . . . . .
C6 C 0.5349(5) 0.14002(7) 0.0942(3) 0.0734(8) Uani 1 1 d . . . . .
H6 H 0.661791 0.135481 0.156791 0.088 Uiso 1 1 calc R U . . .
C5 C 0.4489(4) 0.17403(7) 0.0928(3) 0.0697(8) Uani 1 1 d . . . . .
H5 H 0.519184 0.192207 0.155143 0.084 Uiso 1 1 calc R U . . .
C9 C 0.1588(5) 0.15378(7) -0.0891(3) 0.0709(8) Uani 1 1 d . . . . .
H9 H 0.031802 0.158048 -0.152006 0.085 Uiso 1 1 calc R U . . .
C8 C 0.2415(5) 0.11973(7) -0.0874(3) 0.0721(8) Uani 1 1 d . . . . .
H8 H 0.169314 0.101379 -0.146785 0.087 Uiso 1 1 calc R U . . .
C11 C 0.7708(7) 0.03344(9) 0.0212(7) 0.1546(17) Uani 1 1 d D . . . .
H11A H 0.788367 0.032031 -0.108284 0.232 Uiso 1 1 calc R U . . .
H11B H 0.659272 0.017363 0.058777 0.232 Uiso 1 1 calc R U . . .
H11C H 0.903026 0.026971 0.079718 0.232 Uiso 1 1 calc R U . . .
C10 C 0.7116(5) 0.07067(8) 0.0731(5) 0.0974(11) Uani 1 1 d D . . . .
H10A H 0.703418 0.072844 0.204321 0.117 Uiso 1 1 calc R U . . .
H10B H 0.818500 0.087362 0.028593 0.117 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
O1 C7 1.378(3) . ?
O1 C10 1.433(3) . ?
C1 C2 1.430(4) . ?
C1 C2 1.431(4) 8_565 ?
C2 C3 1.408(15) . ?
C2 C4 1.468(3) . ?
C2 S1 1.686(5) . ?
C3 S1 1.777(5) 8_565 ?
C4 C9 1.380(3) . ?
C4 C5 1.406(4) . ?
C7 C6 1.382(4) . ?
C7 C8 1.382(4) . ?
C6 C5 1.382(4) . ?
C9 C8 1.375(3) . ?
C11 C10 1.491(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
C7 O1 C10 117.7(2) . . ?
C2 C1 C2 110.5(4) . 8_565 ?
C3 C2 C1 116.7(10) . . ?
C3 C2 C4 118.0(10) . . ?
C1 C2 C4 125.3(3) . . ?
C1 C2 S1 110.8(3) . . ?
C4 C2 S1 123.8(3) . . ?
C2 C3 C3 97.8(10) . 8_565 ?
S1 S1 C2 103.9(2) 8_565 . ?
C9 C4 C5 116.7(3) . . ?
C9 C4 C2 123.0(3) . . ?
C5 C4 C2 120.2(2) . . ?
O1 C7 C6 124.2(3) . . ?
O1 C7 C8 116.3(2) . . ?
C6 C7 C8 119.5(3) . . ?
C7 C6 C5 119.8(3) . . ?
C6 C5 C4 121.6(3) . . ?
C8 C9 C4 122.3(3) . . ?
C9 C8 C7 120.1(3) . . ?
O1 C10 C11 107.3(3) . . ?

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
C2 C1 C2 C3 -6.9(13) 8_565 . . . ?
C2 C1 C2 C4 174.56(15) 8_565 . . . ?
C2 C1 C2 S1 -2.4(4) 8_565 . . . ?
C1 C2 C3 C3 4.0(7) . . . 8_565 ?
C4 C2 C3 C3 -177.4(5) . . . 8_565 ?
C1 C2 S1 S1 1.4(3) . . . 8_565 ?
C4 C2 S1 S1 -175.6(2) . . . 8_565 ?
C3 C2 C4 C9 23.5(13) . . . . ?
C1 C2 C4 C9 -158.1(3) . . . . ?
S1 C2 C4 C9 18.6(5) . . . . ?
C3 C2 C4 C5 -158.9(12) . . . . ?
C1 C2 C4 C5 19.6(4) . . . . ?
S1 C2 C4 C5 -163.8(4) . . . . ?
C10 O1 C7 C6 -4.4(4) . . . . ?
C10 O1 C7 C8 175.5(2) . . . . ?
O1 C7 C6 C5 178.8(2) . . . . ?
C8 C7 C6 C5 -1.1(4) . . . . ?
C7 C6 C5 C4 -0.1(4) . . . . ?
C9 C4 C5 C6 0.7(4) . . . . ?
C2 C4 C5 C6 -177.1(2) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C2 C4 C9 C8 177.6(2) . . . . ?
C4 C9 C8 C7 -1.1(4) . . . . ?
O1 C7 C8 C9 -178.2(2) . . . . ?
C6 C7 C8 C9 1.7(4) . . . . ?
C7 O1 C10 C11 -171.6(3) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.053



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
