# 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_vbchem224_a
_database_code_depnum_ccdc_archive 'CCDC 1539031'
_audit_update_record             
;
2017-03-20 deposited with the CCDC.
2017-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 O3 S'
_chemical_formula_weight         358.39

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.1926(11)
_cell_length_b                   16.181(2)
_cell_length_c                   13.1852(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.684(7)
_cell_angle_gamma                90
_cell_volume                     1690.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(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    0.704
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      296(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            54311
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.570
_diffrn_reflns_theta_max         28.590
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4275
_reflns_number_gt                3124
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+1.0126P] 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         4275
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0808
_refine_ls_wR_factor_ref         0.2619
_refine_ls_wR_factor_gt          0.2299
_refine_ls_goodness_of_fit_ref   1.482
_refine_ls_restrained_S_all      1.482
_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
S1 S 1.01244(12) 0.24499(6) 0.36955(9) 0.0602(3) Uani 1 1 d . . . . .
O3 O 0.5938(2) 0.36594(13) 0.36548(15) 0.0374(5) Uani 1 1 d . . . . .
O1 O 0.2403(3) 0.42167(13) 0.52750(18) 0.0428(5) Uani 1 1 d . . . . .
O2 O 0.3191(4) 0.31669(16) 0.6343(2) 0.0557(7) Uani 1 1 d . . . . .
C19 C 0.8444(3) 0.3712(2) 0.2605(2) 0.0398(7) Uani 1 1 d . . . . .
H19 H 0.7676 0.4136 0.2369 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4781(3) 0.37938(17) 0.4215(2) 0.0297(5) Uani 1 1 d . . . . .
C12 C 0.7168(3) 0.30555(17) 0.4031(2) 0.0326(6) Uani 1 1 d . . . . .
C8 C 0.4604(3) 0.33047(17) 0.5003(2) 0.0310(5) Uani 1 1 d . . . . .
C6 C 0.3747(3) 0.45166(16) 0.3891(2) 0.0296(5) Uani 1 1 d . . . . .
C1 C 0.3872(4) 0.50325(19) 0.3070(2) 0.0387(6) Uani 1 1 d . . . . .
H1 H 0.4686 0.4931 0.2705 0.046 Uiso 1 1 calc R U . . .
C18 C 0.8458(3) 0.31009(17) 0.3449(2) 0.0341(6) Uani 1 1 d . . . . .
C5 C 0.2549(3) 0.46896(18) 0.4444(2) 0.0344(6) Uani 1 1 d . . . . .
C9 C 0.3402(4) 0.35249(18) 0.5593(2) 0.0378(6) Uani 1 1 d . . . . .
C13 C 0.4529(4) 0.17507(18) 0.4968(2) 0.0372(6) Uani 1 1 d . . . . .
C10 C 0.5628(4) 0.25212(17) 0.5299(2) 0.0367(6) Uani 1 1 d . . . . .
H10 H 0.6080 0.2511 0.6062 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4090(4) 0.15001(19) 0.3929(2) 0.0413(7) Uani 1 1 d . . . . .
H14 H 0.4521 0.1783 0.3440 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7078(4) 0.25492(19) 0.4795(2) 0.0389(7) Uani 1 1 d . . . . .
H11 H 0.7970 0.2185 0.5039 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1480(4) 0.5365(2) 0.4178(3) 0.0451(7) Uani 1 1 d . . . . .
H4 H 0.0689 0.5480 0.4555 0.054 Uiso 1 1 calc R U . . .
C2 C 0.2781(4) 0.5698(2) 0.2796(3) 0.0454(7) Uani 1 1 d . . . . .
H2 H 0.2843 0.6035 0.2235 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1598(4) 0.5860(2) 0.3359(3) 0.0502(8) Uani 1 1 d . . . . .
H3 H 0.0877 0.6310 0.3178 0.060 Uiso 1 1 calc R U . . .
C21 C 1.0870(4) 0.2854(2) 0.2729(3) 0.0508(8) Uani 1 1 d . . . . .
H21 H 1.1836 0.2658 0.2561 0.061 Uiso 1 1 calc R U . . .
C00M C 0.3888(5) 0.1314(2) 0.5691(3) 0.0507(8) Uani 1 1 d . . . . .
H00M H 0.4165 0.1475 0.6391 0.061 Uiso 1 1 calc R U . . .
C15 C 0.3026(5) 0.0838(2) 0.3608(3) 0.0522(8) Uani 1 1 d . . . . .
H15 H 0.2723 0.0683 0.2906 0.063 Uiso 1 1 calc R U . . .
C20 C 0.9958(4) 0.3483(2) 0.2223(3) 0.0526(9) Uani 1 1 d . . . . .
H20 H 1.0243 0.3758 0.1673 0.063 Uiso 1 1 calc R U . . .
C17 C 0.2839(6) 0.0641(2) 0.5371(3) 0.0597(10) Uani 1 1 d . . . . .
H17 H 0.2423 0.0347 0.5858 0.072 Uiso 1 1 calc R U . . .
C16 C 0.2411(6) 0.0407(2) 0.4334(3) 0.0618(10) Uani 1 1 d . . . . .
H16 H 0.1705 -0.0045 0.4122 0.074 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 C21 1.679(4) . ?
S1 C18 1.689(3) . ?
O3 C7 1.359(3) . ?
O3 C12 1.401(3) . ?
O1 C5 1.367(4) . ?
O1 C9 1.387(4) . ?
O2 C9 1.197(4) . ?
C19 C18 1.486(4) . ?
C19 C20 1.499(4) . ?
C19 H19 0.9300 . ?
C7 C8 1.343(4) . ?
C7 C6 1.444(4) . ?
C12 C11 1.316(4) . ?
C12 C18 1.457(4) . ?
C8 C9 1.445(4) . ?
C8 C10 1.516(4) . ?
C6 C1 1.391(4) . ?
C6 C5 1.391(4) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9300 . ?
C5 C4 1.389(4) . ?
C13 C14 1.387(4) . ?
C13 C00M 1.392(4) . ?
C13 C10 1.535(4) . ?
C10 C11 1.502(4) . ?
C10 H10 0.9800 . ?
C14 C15 1.378(5) . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C4 C3 1.366(5) . ?
C4 H4 0.9300 . ?
C2 C3 1.388(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C21 C20 1.336(5) . ?
C21 H21 0.9300 . ?
C00M C17 1.386(5) . ?
C00M H00M 0.9300 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C20 H20 0.9300 . ?
C17 C16 1.376(6) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?

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
C21 S1 C18 92.46(16) . . ?
C7 O3 C12 117.2(2) . . ?
C5 O1 C9 121.9(2) . . ?
C18 C19 C20 103.7(3) . . ?
C18 C19 H19 128.1 . . ?
C20 C19 H19 128.1 . . ?
C8 C7 O3 123.6(2) . . ?
C8 C7 C6 122.4(2) . . ?
O3 C7 C6 114.0(2) . . ?
C11 C12 O3 122.0(2) . . ?
C11 C12 C18 128.6(3) . . ?
O3 C12 C18 109.4(2) . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 C10 122.1(2) . . ?
C9 C8 C10 118.4(2) . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 124.3(2) . . ?
C5 C6 C7 116.5(2) . . ?
C2 C1 C6 120.0(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C12 C18 C19 124.0(2) . . ?
C12 C18 S1 121.7(2) . . ?
C19 C18 S1 114.3(2) . . ?
O1 C5 C4 117.7(3) . . ?
O1 C5 C6 121.6(3) . . ?
C4 C5 C6 120.6(3) . . ?
O2 C9 O1 116.2(3) . . ?
O2 C9 C8 125.9(3) . . ?
O1 C9 C8 117.8(2) . . ?
C14 C13 C00M 118.7(3) . . ?
C14 C13 C10 120.3(3) . . ?
C00M C13 C10 120.9(3) . . ?
C11 C10 C8 108.0(2) . . ?
C11 C10 C13 111.8(2) . . ?
C8 C10 C13 111.1(2) . . ?
C11 C10 H10 108.6 . . ?
C8 C10 H10 108.6 . . ?
C13 C10 H10 108.6 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C12 C11 C10 124.2(3) . . ?
C12 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C20 C21 S1 114.2(3) . . ?
C20 C21 H21 122.9 . . ?
S1 C21 H21 122.9 . . ?
C17 C00M C13 120.2(3) . . ?
C17 C00M H00M 119.9 . . ?
C13 C00M H00M 119.9 . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C21 C20 C19 115.2(3) . . ?
C21 C20 H20 122.4 . . ?
C19 C20 H20 122.4 . . ?
C16 C17 C00M 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C00M C17 H17 120.0 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?

_refine_diff_density_max         1.017
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.101

