# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_tx2668_pl
_database_code_depnum_ccdc_archive 'CCDC 2024060'
loop_
_audit_author_name
_audit_author_address
'Wubo Du'
;Qingdao University of science and technology
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-02-27 downloaded from the CCDC.
;
_audit_creation_date             2020-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 O3 S'
_chemical_formula_sum            'C17 H18 O3 S'
_chemical_formula_weight         302.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOS
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   15.40316(12)
_cell_length_b                   7.20606(3)
_cell_length_c                   15.43887(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.8711(9)
_cell_angle_gamma                90
_cell_volume                     1528.62(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20963
_cell_measurement_temperature    170.00(15)
_cell_measurement_theta_max      75.3900
_cell_measurement_theta_min      3.2040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.942
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23298
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.419
_diffrn_reflns_theta_min         3.364
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -84.00   0.50    0.05    --  -47.20 -38.00-151.00   50
  2  ω    -33.00  20.00   0.50    0.05    --  -47.20  38.00   3.00  106
  3  ω     48.00  78.00   0.50    0.05    --   47.20  38.00   3.00   60
  4  ω      4.00  46.00   0.50    0.05    --   47.20 -38.00-151.00   84
  5  ω   -127.00 -90.00   0.50    0.05    --  -99.00 -38.00-151.00   74
  6  ω     91.00 131.00   0.50    0.05    --  103.25  38.00   3.00   80
  7  ω   -119.00 -74.00   0.50    0.05    --  -47.20-125.00 -90.00   90
  8  ω   -120.00 -75.00   0.50    0.05    --  -47.20-125.00   0.00   90
  9  ω   -113.00 -74.00   0.50    0.05    --  -47.20-125.00 120.00   78
 10  ω     35.00  74.00   0.50    0.05    --   47.20  57.00  90.00   78
 11  ω     58.00  85.00   0.50    0.05    --   47.20  38.00  60.00   54
 12  ω     33.00 116.00   0.50    0.05    --   47.20  57.00 150.00  166
 13  ω    -22.00   8.00   0.50    0.05    --   47.20 -19.00  90.00   60
 14  ω     33.00  68.00   0.50    0.05    --   47.20  57.00 120.00   70
 15  ω   -108.00 -82.00   0.50    0.05    --  -99.00 -61.00 150.00   52
 16  ω   -110.00 -78.00   0.50    0.05    --  -99.00 -73.00-177.11   64
 17  ω   -115.00 -82.00   0.50    0.05    --  -99.00 -62.00  76.53   66
 18  ω   -150.00-124.00   0.50    0.05    --  -99.00 -77.00  90.00   52
 19  ω   -117.00 -86.00   0.50    0.05    --  -99.00 -52.00 101.66   62
 20  ω   -168.00-114.00   0.50    0.05    --  -99.00 -70.00 147.49  108
 21  ω   -105.00 -79.00   0.50    0.05    --  -99.00 -77.00-180.00   52
 22  ω   -153.00-126.00   0.50    0.05    --  -99.00 -66.00 129.05   54
 23  ω    -65.00 -31.00   0.50    0.05    --  -99.00  61.00 150.00   68
 24  ω   -159.00-121.00   0.50    0.05    --  -99.00 -45.00  30.00   76
 25  ω   -146.00 -86.00   0.50    0.05    --  -99.00 -45.00  60.00  120
 26  ω   -125.00 -81.00   0.50    0.05    --  -99.00 -66.00 129.05   88
 27  ω    -68.00 -35.00   0.50    0.05    --  -99.00  61.00  30.00   66
 28  ω   -165.00-121.00   0.50    0.05    --  -99.00 -73.00-177.11   88
 29  ω   -116.00 -85.00   0.50    0.05    --  -99.00 -50.00  88.01   62
 30  ω   -148.00 -82.00   0.50    0.05    --  -99.00 -61.00  90.00  132
 31  ω   -108.00 -82.00   0.50    0.05    --  -99.00 -61.00 120.00   52
 32  ω   -102.00 -76.00   0.50    0.05    --  -99.00 -77.00  90.00   52
 33  ω   -100.00 -75.00   0.50    0.05    --  -99.00 -79.00 115.00   50
 34  ω   -156.00 -82.00   0.50    0.05    --  -99.00 -61.00  60.00  148
 35  ω   -166.00-141.00   0.50    0.05    --  -99.00 -79.00 115.00   50
 36  ω   -106.00 -80.00   0.50    0.05    --  -99.00 -70.00 147.49   52
 37  ω   -166.00-124.00   0.50    0.05    --  -99.00 -30.00 150.00   84
 38  ω   -121.00 -82.00   0.50    0.05    --  -99.00 -62.00 146.15   78
 39  ω   -103.00 -78.00   0.50    0.05    --  -99.00 -73.00 101.26   50
 40  ω   -103.00 -77.00   0.50    0.05    --  -99.00 -77.00 120.00   52
 41  ω   -121.00 -87.00   0.50    0.05    --  -99.00-125.00 -30.00   68
 42  ω   -152.00-127.00   0.50    0.05    --  -99.00 -72.00 143.58   50
 43  ω   -103.00 -78.00   0.50    0.05    --  -99.00 -72.00 143.58   50
 44  ω     81.00 126.00   0.50    0.05    --  103.25 125.00-120.00   90
 45  ω     37.00  74.00   0.50    0.05    --  103.25 -61.00 120.00   74
 46  ω     43.00  74.00   0.50    0.05    --  103.25 -61.00  60.00   62
 47  ω     31.00  75.00   0.50    0.05    --  103.25 -61.00-180.00   88
 48  ω     92.00 161.00   0.50    0.05    --  103.25  45.00  60.00  138
 49  ω     32.00  67.00   0.50    0.05    --  103.25 -61.00-150.00   70
 50  ω     81.00 169.00   0.50    0.05    --  103.25  77.00 150.00  176
 51  ω    127.00 152.00   0.50    0.05    --  103.25  77.00 120.00   50
 52  ω     82.00 109.00   0.50    0.05    --  103.25  77.00 120.00   54
 53  ω     41.00  75.00   0.50    0.05    --  103.25 -61.00   0.00   68
 54  ω     56.00 106.00   0.50    0.05    --  103.25 -94.00-120.00  100
 55  ω     45.00 109.00   0.50    0.05    --  103.25 -77.00  60.00  128
 56  ω     33.00  75.00   0.50    0.05    --  103.25 -61.00-120.00   84
 57  ω     32.00  89.00   0.50    0.05    --  103.25 -94.00 -30.00  114
 58  ω     31.00  69.00   0.50    0.05    --  103.25 -61.00  30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0452872000
_diffrn_orient_matrix_UB_12      -0.1945724000
_diffrn_orient_matrix_UB_13      -0.0296377000
_diffrn_orient_matrix_UB_21      -0.0530258000
_diffrn_orient_matrix_UB_22      0.0629201000
_diffrn_orient_matrix_UB_23      -0.1067828000
_diffrn_orient_matrix_UB_31      0.0878012000
_diffrn_orient_matrix_UB_32      -0.0623714000
_diffrn_orient_matrix_UB_33      -0.0152115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3014
_reflns_number_total             3042
_reflns_odcompleteness_completeness 98.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.6969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.69871(2) 0.45647(4) 0.46850(2) 0.02157(11) Uani 1 1 d . . . . .
O1 O 0.66884(7) 0.26527(13) 0.46291(7) 0.0289(2) Uani 1 1 d . . . . .
O2 O 0.76916(7) 0.52498(15) 0.56198(7) 0.0305(2) Uani 1 1 d . . . . .
O3 O 0.74495(8) 0.56349(16) 0.24064(7) 0.0345(2) Uani 1 1 d . . . . .
C1 C 0.59447(9) 0.59816(18) 0.42916(9) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.50273(10) 0.51829(19) 0.39403(9) 0.0253(3) Uani 1 1 d . . . . .
H2 H 0.495686 0.389947 0.391801 0.030 Uiso 1 1 calc R . . . .
C3 C 0.42201(10) 0.6325(2) 0.36243(9) 0.0290(3) Uani 1 1 d . . . . .
H3 H 0.360477 0.579734 0.339424 0.035 Uiso 1 1 calc R . . . .
C4 C 0.43102(10) 0.8248(2) 0.36435(10) 0.0304(3) Uani 1 1 d . . . . .
C5 C 0.52417(11) 0.9016(2) 0.40234(11) 0.0325(3) Uani 1 1 d . . . . .
H5 H 0.531447 1.029895 0.405666 0.039 Uiso 1 1 calc R . . . .
C6 C 0.60573(10) 0.78981(19) 0.43507(10) 0.0278(3) Uani 1 1 d . . . . .
H6 H 0.667526 0.842270 0.460800 0.033 Uiso 1 1 calc R . . . .
C7 C 0.34216(13) 0.9470(3) 0.32505(13) 0.0452(4) Uani 1 1 d . . . . .
H7A H 0.323197 0.974475 0.258045 0.068 Uiso 1 1 calc GR . . . .
H7B H 0.356690 1.060448 0.361533 0.068 Uiso 1 1 calc GR . . . .
H7C H 0.289943 0.884021 0.330526 0.068 Uiso 1 1 calc GR . . . .
C8 C 0.75156(9) 0.49487(18) 0.38901(9) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.86113(10) 0.5076(2) 0.43876(10) 0.0293(3) Uani 1 1 d . . . . .
H9A H 0.880706 0.621858 0.474409 0.044 Uiso 1 1 calc GR . . . .
H9B H 0.884803 0.504105 0.390954 0.044 Uiso 1 1 calc GR . . . .
H9C H 0.887621 0.404978 0.482577 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.69704(9) 0.50950(18) 0.29255(9) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.70566(12) 0.5098(2) 0.14068(10) 0.0317(3) Uani 1 1 d . . . . .
H11A H 0.641058 0.558892 0.105611 0.048 Uiso 1 1 calc GR . . . .
H11B H 0.703484 0.376861 0.136036 0.048 Uiso 1 1 calc GR . . . .
H11C H 0.746129 0.557628 0.113416 0.048 Uiso 1 1 calc GR . . . .
C12 C 0.59033(9) 0.48158(19) 0.23768(9) 0.0236(3) Uani 1 1 d . . . . .
C13 C 0.55119(10) 0.3043(2) 0.22752(10) 0.0281(3) Uani 1 1 d . . . . .
H13 H 0.591806 0.203605 0.256499 0.034 Uiso 1 1 calc R . . . .
C14 C 0.45154(11) 0.2774(2) 0.17413(11) 0.0365(3) Uani 1 1 d . . . . .
H14 H 0.425467 0.158756 0.167155 0.044 Uiso 1 1 calc R . . . .
C15 C 0.39124(11) 0.4270(3) 0.13145(11) 0.0415(4) Uani 1 1 d . . . . .
H15 H 0.324548 0.408746 0.095649 0.050 Uiso 1 1 calc R . . . .
C16 C 0.42953(11) 0.6040(3) 0.14167(11) 0.0411(4) Uani 1 1 d . . . . .
H16 H 0.388478 0.704541 0.113573 0.049 Uiso 1 1 calc R . . . .
C17 C 0.52900(11) 0.6315(2) 0.19375(10) 0.0320(3) Uani 1 1 d . . . . .
H17 H 0.554837 0.750068 0.199385 0.038 Uiso 1 1 calc R . . . .


_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 O1 1.4427(10) . ?
S1 O2 1.4452(10) . ?
S1 C1 1.7630(13) . ?
S1 C8 1.7744(13) . ?
O3 C10 1.3685(16) . ?
O3 C11 1.4330(16) . ?
C1 C2 1.3890(18) . ?
C1 C6 1.3898(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C4 C5 1.396(2) . ?
C4 C7 1.505(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.5082(18) . ?
C8 C10 1.3431(18) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.4836(18) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.3910(19) . ?
C12 C17 1.3928(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.3890(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(2) . ?
C17 H17 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
O1 S1 O2 117.47(6) . . ?
O1 S1 C1 108.44(6) . . ?
O1 S1 C8 109.95(6) . . ?
O2 S1 C1 107.58(6) . . ?
O2 S1 C8 105.39(6) . . ?
C1 S1 C8 107.61(6) . . ?
C10 O3 C11 118.48(11) . . ?
C2 C1 S1 120.13(10) . . ?
C2 C1 C6 120.81(12) . . ?
C6 C1 S1 119.06(10) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.00(13) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.34(13) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.50(13) . . ?
C3 C4 C7 120.68(14) . . ?
C5 C4 C7 120.81(15) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.98(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.31(13) . . ?
C5 C6 H6 120.3 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 114.51(9) . . ?
C10 C8 S1 121.79(10) . . ?
C10 C8 C9 123.70(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 C12 117.11(11) . . ?
C8 C10 O3 116.06(12) . . ?
C8 C10 C12 126.77(12) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 120.05(12) . . ?
C13 C12 C17 119.56(13) . . ?
C17 C12 C10 120.36(13) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.09(14) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.93(15) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.34(14) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.02(15) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.04(15) . . ?
C16 C17 H17 120.0 . . ?

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
S1 C1 C2 C3 -179.15(10) . . . . ?
S1 C1 C6 C5 178.56(10) . . . . ?
S1 C8 C10 O3 171.58(9) . . . . ?
S1 C8 C10 C12 -5.4(2) . . . . ?
O1 S1 C1 C2 -4.03(12) . . . . ?
O1 S1 C1 C6 175.14(10) . . . . ?
O1 S1 C8 C9 -103.54(11) . . . . ?
O1 S1 C8 C10 75.96(13) . . . . ?
O2 S1 C1 C2 -132.03(10) . . . . ?
O2 S1 C1 C6 47.14(12) . . . . ?
O2 S1 C8 C9 23.96(12) . . . . ?
O2 S1 C8 C10 -156.54(11) . . . . ?
O3 C10 C12 C13 111.93(14) . . . . ?
O3 C10 C12 C17 -66.25(17) . . . . ?
C1 S1 C8 C9 138.54(10) . . . . ?
C1 S1 C8 C10 -41.96(13) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C1 C6 C5 -2.3(2) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
C2 C3 C4 C7 176.92(13) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C6 C1 C2 C3 1.69(19) . . . . ?
C7 C4 C5 C6 -177.52(14) . . . . ?
C8 S1 C1 C2 114.85(11) . . . . ?
C8 S1 C1 C6 -65.98(12) . . . . ?
C8 C10 C12 C13 -71.08(19) . . . . ?
C8 C10 C12 C17 110.74(16) . . . . ?
C9 C8 C10 O3 -9.0(2) . . . . ?
C9 C8 C10 C12 174.01(13) . . . . ?
C10 C12 C13 C14 -178.41(12) . . . . ?
C10 C12 C17 C16 179.24(12) . . . . ?
C11 O3 C10 C8 154.32(13) . . . . ?
C11 O3 C10 C12 -28.37(18) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C12 C17 C16 1.1(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C12 -1.4(2) . . . . ?
C17 C12 C13 C14 -0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.828
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether / ethyl acetate'
####################################################################### 
# 
# 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_200903b
_database_code_depnum_ccdc_archive 'CCDC 2032053'
loop_
_audit_author_name
_audit_author_address
'Wu-Bo du'
;Qingdao University of science and technology
China
;
_audit_update_record             
;
2020-10-26 deposited with the CCDC.	2021-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_weight         270.33

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.5976(8)
_cell_length_b                   10.8141(9)
_cell_length_c                   15.2294(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1416.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2213
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      23.592

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9161
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6668
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_sigmaI/netI    0.1064
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2477
_reflns_number_gt                1784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0351P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(12)
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O1 O 0.6641(3) 0.4705(3) 0.75274(15) 0.0643(8) Uani 1 1 d . . .
O2 O 0.9199(4) 0.5537(3) 0.70302(14) 0.0641(9) Uani 1 1 d . . .
S1 S 0.81086(13) 0.53095(9) 0.77556(5) 0.0436(3) Uani 1 1 d . . .
C1 C 0.7756(4) 0.6694(3) 0.8370(2) 0.0368(10) Uani 1 1 d . . .
C2 C 0.8305(5) 0.6588(3) 0.9206(2) 0.0326(8) Uani 1 1 d . . .
C3 C 0.9047(4) 0.5349(3) 0.93945(19) 0.0327(8) Uani 1 1 d . . .
C4 C 0.9057(4) 0.4569(4) 0.8657(2) 0.0379(9) Uani 1 1 d . . .
C5 C 0.9748(5) 0.3413(4) 0.8663(2) 0.0464(11) Uani 1 1 d . . .
H5 H 0.9745 0.2908 0.8169 0.056 Uiso 1 1 calc R . .
C6 C 1.0462(5) 0.3038(4) 0.9461(3) 0.0516(12) Uani 1 1 d . . .
H6 H 1.0956 0.2273 0.9481 0.062 Uiso 1 1 calc R . .
C7 C 1.0452(5) 0.3772(4) 1.0219(2) 0.0449(10) Uani 1 1 d . . .
C8 C 0.9752(4) 0.4948(3) 1.0180(2) 0.0381(9) Uani 1 1 d . . .
H8 H 0.9755 0.5460 1.0671 0.046 Uiso 1 1 calc R . .
C9 C 0.8266(4) 0.7581(3) 0.9895(2) 0.0334(8) Uani 1 1 d . . .
C10 C 0.8879(5) 0.8753(3) 0.9718(2) 0.0440(10) Uani 1 1 d . . .
H10 H 0.9274 0.8933 0.9164 0.053 Uiso 1 1 calc R . .
C11 C 0.8895(5) 0.9663(4) 1.0384(3) 0.0608(12) Uani 1 1 d . . .
H11 H 0.9305 1.0440 1.0262 0.073 Uiso 1 1 calc R . .
C12 C 0.8306(6) 0.9418(4) 1.1219(3) 0.0641(14) Uani 1 1 d . . .
H12 H 0.8343 1.0020 1.1654 0.077 Uiso 1 1 calc R . .
C13 C 0.7662(5) 0.8261(5) 1.1396(2) 0.0562(13) Uani 1 1 d . . .
H13 H 0.7228 0.8098 1.1943 0.067 Uiso 1 1 calc R . .
C14 C 0.7671(4) 0.7353(4) 1.0750(2) 0.0410(10) Uani 1 1 d . . .
H14 H 0.7277 0.6574 1.0881 0.049 Uiso 1 1 calc R . .
C15 C 0.6869(5) 0.7728(4) 0.7920(2) 0.0510(11) Uani 1 1 d . . .
H15A H 0.5772 0.7576 0.7968 0.076 Uiso 1 1 calc R . .
H15B H 0.7158 0.7762 0.7312 0.076 Uiso 1 1 calc R . .
H15C H 0.7115 0.8502 0.8196 0.076 Uiso 1 1 calc R . .
C16 C 1.1242(6) 0.3358(5) 1.1092(2) 0.0768(16) Uani 1 1 d . . .
H16A H 1.1125 0.2481 1.1162 0.115 Uiso 1 1 calc R . .
H16B H 1.0761 0.3776 1.1577 0.115 Uiso 1 1 calc R . .
H16C H 1.2328 0.3563 1.1073 0.115 Uiso 1 1 calc R . .


_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 S1 1.463(3) . ?
O2 S1 1.470(3) . ?
S1 C4 1.786(4) . ?
S1 C1 1.792(4) . ?
C1 C2 1.363(5) . ?
C1 C15 1.517(5) . ?
C2 C9 1.502(5) . ?
C2 C3 1.511(5) . ?
C3 C4 1.405(4) . ?
C3 C8 1.409(4) . ?
C4 C5 1.384(5) . ?
C5 C6 1.422(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.408(5) . ?
C7 C16 1.558(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.399(5) . ?
C9 C14 1.420(5) . ?
C10 C11 1.413(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O1 S1 O2 116.51(16) . . ?
O1 S1 C4 112.08(17) . . ?
O2 S1 C4 111.19(17) . . ?
O1 S1 C1 110.58(18) . . ?
O2 S1 C1 111.13(17) . . ?
C4 S1 C1 92.92(16) . . ?
C2 C1 C15 131.2(3) . . ?
C2 C1 S1 111.0(3) . . ?
C15 C1 S1 117.8(2) . . ?
C1 C2 C9 125.8(3) . . ?
C1 C2 C3 113.5(3) . . ?
C9 C2 C3 120.7(3) . . ?
C4 C3 C8 119.4(3) . . ?
C4 C3 C2 112.6(3) . . ?
C8 C3 C2 128.0(3) . . ?
C5 C4 C3 122.7(3) . . ?
C5 C4 S1 127.3(3) . . ?
C3 C4 S1 110.0(3) . . ?
C4 C5 C6 116.7(4) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
C7 C6 C5 122.7(4) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C8 118.6(3) . . ?
C6 C7 C16 122.5(4) . . ?
C8 C7 C16 118.9(4) . . ?
C7 C8 C3 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C3 C8 H8 120.1 . . ?
C10 C9 C14 118.0(3) . . ?
C10 C9 C2 120.4(3) . . ?
C14 C9 C2 121.6(3) . . ?
C9 C10 C11 119.8(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C9 121.9(4) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O1 S1 C1 C2 114.1(3) . . . . ?
O2 S1 C1 C2 -114.9(3) . . . . ?
C4 S1 C1 C2 -0.8(3) . . . . ?
O1 S1 C1 C15 -63.1(3) . . . . ?
O2 S1 C1 C15 67.9(3) . . . . ?
C4 S1 C1 C15 -178.0(3) . . . . ?
C15 C1 C2 C9 -5.8(7) . . . . ?
S1 C1 C2 C9 177.6(3) . . . . ?
C15 C1 C2 C3 176.4(4) . . . . ?
S1 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 1.7(5) . . . . ?
C9 C2 C3 C4 -176.3(3) . . . . ?
C1 C2 C3 C8 178.6(4) . . . . ?
C9 C2 C3 C8 0.6(6) . . . . ?
C8 C3 C4 C5 -0.6(5) . . . . ?
C2 C3 C4 C5 176.6(3) . . . . ?
C8 C3 C4 S1 -179.4(3) . . . . ?
C2 C3 C4 S1 -2.2(4) . . . . ?
O1 S1 C4 C5 69.4(4) . . . . ?
O2 S1 C4 C5 -63.0(4) . . . . ?
C1 S1 C4 C5 -177.0(4) . . . . ?
O1 S1 C4 C3 -111.9(3) . . . . ?
O2 S1 C4 C3 115.8(3) . . . . ?
C1 S1 C4 C3 1.7(3) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
S1 C4 C5 C6 178.6(3) . . . . ?
C4 C5 C6 C7 1.4(6) . . . . ?
C5 C6 C7 C8 -2.2(6) . . . . ?
C5 C6 C7 C16 -179.7(4) . . . . ?
C6 C7 C8 C3 1.6(6) . . . . ?
C16 C7 C8 C3 179.2(3) . . . . ?
C4 C3 C8 C7 -0.3(5) . . . . ?
C2 C3 C8 C7 -177.0(4) . . . . ?
C1 C2 C9 C10 -53.0(6) . . . . ?
C3 C2 C9 C10 124.7(4) . . . . ?
C1 C2 C9 C14 129.6(4) . . . . ?
C3 C2 C9 C14 -52.7(5) . . . . ?
C14 C9 C10 C11 0.2(5) . . . . ?
C2 C9 C10 C11 -177.3(3) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C10 C11 C12 C13 -1.3(6) . . . . ?
C11 C12 C13 C14 2.6(7) . . . . ?
C12 C13 C14 C9 -2.6(6) . . . . ?
C10 C9 C14 C13 1.1(6) . . . . ?
C2 C9 C14 C13 178.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.052
