# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1579314'
loop_
_audit_author_name
_audit_author_address
'Tuncer Hokelek'
;Hacettepe University Department of Physics Beytepe Ankara
Turkey
;
_audit_update_record             
;
2019-02-22 deposited with the CCDC.	2019-03-05 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         'C22 H16 O3 S'
_chemical_formula_sum            'C22 H16 O3 S'
_chemical_formula_weight         360.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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                   9.9226(2)
_cell_length_b                   15.7155(3)
_cell_length_c                   11.5782(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.572(3)
_cell_angle_gamma                90.00
_cell_volume                     1711.47(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8525
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   ?
_exptl_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9263
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16080
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.165
_diffrn_reflns_theta_max         28.420
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4292
_reflns_number_gt                3770
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)'
_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)+(0.0370P)²+0.8190P] 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         4292
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.07785(3) 0.14552(2) 0.14261(3) 0.02069(8) Uani 1 1 d . . . . .
O1 O 0.15945(9) -0.15144(5) 0.47638(8) 0.01979(18) Uani 1 1 d . . . . .
O2 O 0.28268(9) 0.06110(5) 0.33645(7) 0.01846(17) Uani 1 1 d . . . . .
O3 O 0.14355(9) -0.22249(5) 0.30692(8) 0.02135(18) Uani 1 1 d . . . . .
C1 C 0.23820(11) -0.00652(7) 0.38507(10) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.20891(11) -0.00043(7) 0.49813(10) 0.0169(2) Uani 1 1 d . . . . .
C3 C 0.21286(12) 0.07454(8) 0.56445(11) 0.0199(2) Uani 1 1 d . . . . .
H3 H 0.2361 0.1260 0.5360 0.024 Uiso 1 1 calc R U . . .
C4 C 0.18200(13) 0.07143(8) 0.67239(12) 0.0234(3) Uani 1 1 d . . . . .
H4 H 0.1834 0.1211 0.7164 0.028 Uiso 1 1 calc R U . . .
C5 C 0.14869(13) -0.00590(9) 0.71581(11) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.1296 -0.0072 0.7894 0.029 Uiso 1 1 calc R U . . .
C6 C 0.14349(12) -0.08076(8) 0.65141(11) 0.0223(2) Uani 1 1 d . . . . .
H6 H 0.1219 -0.1322 0.6811 0.027 Uiso 1 1 calc R U . . .
C7 C 0.17141(12) -0.07698(7) 0.54120(11) 0.0179(2) Uani 1 1 d . . . . .
C8 C 0.17209(11) -0.15539(7) 0.35975(11) 0.0172(2) Uani 1 1 d . . . . .
C9 C 0.22065(11) -0.07867(7) 0.31879(10) 0.0159(2) Uani 1 1 d . . . . .
C10 C 0.24793(11) -0.06188(7) 0.20040(10) 0.0151(2) Uani 1 1 d . . . . .
H10 H 0.1565 -0.0614 0.1348 0.018 Uiso 1 1 calc R U . . .
C11 C 0.34582(12) -0.12394(7) 0.16672(11) 0.0166(2) Uani 1 1 d . . . . .
C12 C 0.45164(12) -0.16766(7) 0.25512(11) 0.0198(2) Uani 1 1 d . . . . .
H12 H 0.4619 -0.1597 0.3371 0.024 Uiso 1 1 calc R U . . .
C13 C 0.54216(13) -0.22303(8) 0.22195(13) 0.0247(3) Uani 1 1 d . . . . .
H13 H 0.6124 -0.2521 0.2817 0.030 Uiso 1 1 calc R U . . .
C14 C 0.52798(14) -0.23503(8) 0.09997(14) 0.0285(3) Uani 1 1 d . . . . .
H14 H 0.5886 -0.2720 0.0778 0.034 Uiso 1 1 calc R U . . .
C15 C 0.42328(14) -0.19177(9) 0.01140(13) 0.0277(3) Uani 1 1 d . . . . .
H15 H 0.4139 -0.1995 -0.0704 0.033 Uiso 1 1 calc R U . . .
C16 C 0.33214(13) -0.13674(8) 0.04445(12) 0.0215(2) Uani 1 1 d . . . . .
H16 H 0.2615 -0.1082 -0.0156 0.026 Uiso 1 1 calc R U . . .
C17 C 0.30684(12) 0.03307(7) 0.22176(10) 0.0157(2) Uani 1 1 d . . . . .
C18 C 0.22257(11) 0.09304(7) 0.12478(10) 0.0148(2) Uani 1 1 d . . . . .
C19 C 0.24095(13) 0.11304(8) 0.01648(11) 0.0199(2) Uani 1 1 d . . . . .
H19 H 0.3141 0.0914 -0.0090 0.024 Uiso 1 1 calc R U . . .
C20 C 0.13576(13) 0.17089(8) -0.05390(11) 0.0217(2) Uani 1 1 d . . . . .
H20 H 0.1329 0.1912 -0.1301 0.026 Uiso 1 1 calc R U . . .
C21 C 0.04032(13) 0.19293(8) 0.00282(11) 0.0208(2) Uani 1 1 d . . . . .
H21 H -0.0361 0.2294 -0.0303 0.025 Uiso 1 1 calc R U . . .
C22 C 0.46536(12) 0.04068(7) 0.24330(12) 0.0212(2) Uani 1 1 d . . . . .
H22A H 0.4862 0.0232 0.1714 0.032 Uiso 1 1 calc R U . . .
H22B H 0.4944 0.0987 0.2618 0.032 Uiso 1 1 calc R U . . .
H22C H 0.5158 0.0050 0.3104 0.032 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 C18 1.7245(12) . ?
S1 C21 1.7116(13) . ?
O1 C7 1.3747(14) . ?
O1 C8 1.3968(15) . ?
O2 C1 1.3414(14) . ?
O2 C17 1.4892(14) . ?
O3 C8 1.2067(14) . ?
C2 C1 1.4316(16) . ?
C2 C3 1.4000(17) . ?
C2 C7 1.3974(16) . ?
C3 H3 0.9300 . ?
C4 C3 1.3791(18) . ?
C4 C5 1.3945(19) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C5 1.3850(18) . ?
C6 H6 0.9300 . ?
C7 C6 1.3906(17) . ?
C9 C1 1.3490(16) . ?
C9 C8 1.4340(16) . ?
C10 C9 1.5027(16) . ?
C10 C11 1.5126(16) . ?
C10 C17 1.5929(16) . ?
C10 H10 0.9800 . ?
C11 C12 1.3920(17) . ?
C11 C16 1.3931(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(2) . ?
C13 C12 1.3897(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C15 1.390(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.5001(16) . ?
C17 C22 1.5168(18) . ?
C18 C19 1.3602(17) . ?
C19 C20 1.4277(18) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C20 1.3580(19) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 91.93(6) . . ?
C7 O1 C8 123.15(9) . . ?
C1 O2 C17 107.93(8) . . ?
O2 C1 C2 121.37(10) . . ?
O2 C1 C9 115.30(10) . . ?
C9 C1 C2 123.32(10) . . ?
C3 C2 C1 125.41(10) . . ?
C7 C2 C1 115.05(10) . . ?
C7 C2 C3 119.53(11) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.45(11) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.27(12) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.24(12) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 118.27(11) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
O1 C7 C6 117.18(10) . . ?
O1 C7 C2 121.63(11) . . ?
C6 C7 C2 121.18(11) . . ?
O1 C8 C9 115.18(10) . . ?
O3 C8 O1 116.75(10) . . ?
O3 C8 C9 128.06(11) . . ?
C1 C9 C8 120.98(10) . . ?
C1 C9 C10 110.07(10) . . ?
C8 C9 C10 128.79(10) . . ?
C9 C10 C11 116.04(9) . . ?
C9 C10 C17 100.76(9) . . ?
C9 C10 H10 108.5 . . ?
C11 C10 C17 114.21(9) . . ?
C11 C10 H10 108.5 . . ?
C17 C10 H10 108.5 . . ?
C12 C11 C10 121.64(11) . . ?
C12 C11 C16 118.85(11) . . ?
C16 C11 C10 119.50(11) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.56(12) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.11(12) . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.78(13) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.16(13) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.54(12) . . ?
C15 C16 H16 119.7 . . ?
O2 C17 C10 105.08(9) . . ?
O2 C17 C18 105.78(9) . . ?
O2 C17 C22 106.44(9) . . ?
C18 C17 C10 112.51(9) . . ?
C18 C17 C22 112.04(10) . . ?
C22 C17 C10 114.17(9) . . ?
C17 C18 S1 119.85(8) . . ?
C19 C18 S1 111.17(9) . . ?
C19 C18 C17 128.96(11) . . ?
C18 C19 C20 112.65(11) . . ?
C18 C19 H19 123.7 . . ?
C20 C19 H19 123.7 . . ?
C19 C20 H20 123.8 . . ?
C21 C20 C19 112.46(11) . . ?
C21 C20 H20 123.8 . . ?
S1 C21 H21 124.1 . . ?
C20 C21 S1 111.78(10) . . ?
C20 C21 H21 124.1 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C21 S1 C18 C17 -177.7(4) . . . . ?
C21 S1 C18 C19 1.01(10) . . . . ?
C18 S1 C21 C20 -1.13(10) . . . . ?
C8 O1 C7 C2 -5.34(18) . . . . ?
C8 O1 C7 C6 174.17(11) . . . . ?
C7 O1 C8 O3 -171.81(11) . . . . ?
C7 O1 C8 C9 9.39(16) . . . . ?
C17 O2 C1 C2 178.54(10) . . . . ?
C17 O2 C1 C9 -2.86(13) . . . . ?
C1 O2 C17 C10 7.60(11) . . . . ?
C1 O2 C17 C18 126.82(10) . . . . ?
C1 O2 C17 C22 -113.85(10) . . . . ?
C3 C2 C1 O2 4.70(18) . . . . ?
C3 C2 C1 C9 -173.79(12) . . . . ?
C7 C2 C1 O2 -176.45(11) . . . . ?
C7 C2 C1 C9 5.06(17) . . . . ?
C1 C2 C7 O1 -2.1(5) . . . . ?
C1 C2 C7 C6 178.43(11) . . . . ?
C3 C2 C7 O1 176.84(11) . . . . ?
C3 C2 C7 C6 -2.6(6) . . . . ?
C1 C2 C3 C4 179.90(11) . . . . ?
C7 C2 C3 C4 1.09(18) . . . . ?
C5 C4 C3 C2 0.71(19) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C7 C6 C5 C4 -0.47(19) . . . . ?
O1 C7 C6 C5 -177.20(11) . . . . ?
C2 C7 C6 C5 2.3(6) . . . . ?
C8 C9 C1 O2 -179.34(10) . . . . ?
C8 C9 C1 C2 -0.77(18) . . . . ?
C10 C9 C1 O2 -3.63(14) . . . . ?
C10 C9 C1 C2 174.95(10) . . . . ?
C1 C9 C8 O1 -6.30(16) . . . . ?
C1 C9 C8 O3 175.06(12) . . . . ?
C10 C9 C8 O1 178.86(11) . . . . ?
C10 C9 C8 O3 0.2(2) . . . . ?
C11 C10 C9 C1 131.65(11) . . . . ?
C11 C10 C9 C8 -53.07(16) . . . . ?
C17 C10 C9 C1 7.78(12) . . . . ?
C17 C10 C9 C8 -176.94(11) . . . . ?
C9 C10 C11 C12 -28.09(16) . . . . ?
C9 C10 C11 C16 153.18(11) . . . . ?
C17 C10 C11 C12 88.49(13) . . . . ?
C17 C10 C11 C16 -90.24(13) . . . . ?
C9 C10 C17 O2 -8.98(11) . . . . ?
C9 C10 C17 C18 -123.60(10) . . . . ?
C9 C10 C17 C22 107.27(11) . . . . ?
C11 C10 C17 O2 -134.10(10) . . . . ?
C11 C10 C17 C18 111.28(11) . . . . ?
C11 C10 C17 C22 -17.85(14) . . . . ?
C10 C11 C12 C13 -178.66(11) . . . . ?
C16 C11 C12 C13 0.07(17) . . . . ?
C10 C11 C16 C15 178.3(3) . . . . ?
C12 C11 C16 C15 -0.45(19) . . . . ?
C14 C13 C12 C11 0.20(18) . . . . ?
C12 C13 C14 C15 -0.09(19) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C11 C16 C15 C14 0.6(2) . . . . ?
O2 C17 C18 S1 -24.36(12) . . . . ?
O2 C17 C18 C19 157.17(12) . . . . ?
C10 C17 C18 S1 89.83(11) . . . . ?
C10 C17 C18 C19 -88.64(15) . . . . ?
C22 C17 C18 S1 -139.94(9) . . . . ?
C22 C17 C18 C19 41.59(16) . . . . ?
S1 C18 C19 C20 -0.65(14) . . . . ?
C17 C18 C19 C20 177.92(11) . . . . ?
C18 C19 C20 C21 -0.19(16) . . . . ?
S1 C21 C20 C19 0.96(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H21 O1 0.93 2.43 3.2052(16) 141.4 2

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.045

