# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc2bk2cc
_database_code_depnum_ccdc_archive 'CCDC 2161362'
loop_
_audit_author_name
_audit_author_address
'Canming Zhu'
;Shantou University
China
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2022-03-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.02.24 svn.r684696ac for OlexSys, GUI svn.r6476)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O S'
_chemical_formula_sum            'C16 H16 O S'
_chemical_formula_weight         256.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
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                   6.0752(3)
_cell_length_b                   9.8777(5)
_cell_length_c                   22.1887(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.536(5)
_cell_angle_gamma                90
_cell_volume                     1331.04(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0540
_cell_measurement_theta_min      4.9060
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5767
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.816
_diffrn_reflns_theta_min         3.986
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  80.00   0.50    1.50    --    0.00  57.00  60.00   74
  2  ω    -78.00 -24.00   0.50    1.50    --    0.00 -57.00  30.00  108
  3  ω    -21.00  18.00   0.50    1.50    --    0.00  57.00  60.00   78
  4  ω     58.00 108.00   0.50    6.00    --   89.30  82.00-180.00  100
  5  ω     62.00 135.00   0.50    6.00    --   89.30  82.00-150.00  146
  6  ω     57.00 164.00   0.50    6.00    --   89.30  82.00   0.00  214
  7  ω     80.00 111.00   0.50    6.00    --   89.30 -61.00  60.00   62
  8  ω      6.00  56.00   0.50    6.00    --   89.30 -61.00  60.00  100
  9  ω    130.00 179.00   0.50    6.00    --   89.30  82.00-180.00   98
 10  ω     65.00 127.00   0.50    6.00    --   89.30  61.00   0.00  124
 11  ω     50.00 122.00   0.50    6.00    --   89.30 -82.00  90.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0083343000
_diffrn_orient_matrix_UB_12      0.1437446000
_diffrn_orient_matrix_UB_13      -0.0269173000
_diffrn_orient_matrix_UB_21      -0.1900532000
_diffrn_orient_matrix_UB_22      -0.0431812000
_diffrn_orient_matrix_UB_23      -0.0430664000
_diffrn_orient_matrix_UB_31      -0.1678405000
_diffrn_orient_matrix_UB_32      0.0421372000
_diffrn_orient_matrix_UB_33      0.0474149000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2075
_reflns_number_total             2471
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.7043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C3(H3), C12(H12), C5(H5), C11(H11), C2(H2), C1(H1), C6(H6)
;
_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 0.13854(11) 0.56325(7) 0.61449(3) 0.0636(2) Uani 1 1 d . . . . .
C4 C 0.7605(4) 0.4805(2) 0.82917(10) 0.0493(5) Uani 1 1 d . . . . .
C7 C 0.6006(4) 0.4998(2) 0.77814(10) 0.0476(5) Uani 1 1 d . . . . .
O1 O -0.0204(4) 0.3086(2) 0.60977(12) 0.1035(9) Uani 1 1 d . . . . .
C10 C 0.3061(4) 0.5340(2) 0.67956(10) 0.0504(5) Uani 1 1 d . . . . .
C8 C 0.5807(4) 0.6233(2) 0.74853(11) 0.0534(6) Uani 1 1 d . . . . .
H8 H 0.667605 0.695722 0.761478 0.064 Uiso 1 1 calc R U . . .
C9 C 0.4354(4) 0.6410(3) 0.70047(11) 0.0548(6) Uani 1 1 d . . . . .
H9 H 0.423723 0.725162 0.681889 0.066 Uiso 1 1 calc R U . . .
C3 C 0.9653(4) 0.5449(3) 0.82913(11) 0.0570(6) Uani 1 1 d . . . . .
H3 H 1.001272 0.600296 0.796967 0.068 Uiso 1 1 calc R U . . .
C12 C 0.4663(4) 0.3943(2) 0.75764(11) 0.0525(6) Uani 1 1 d . . . . .
H12 H 0.473670 0.311144 0.777278 0.063 Uiso 1 1 calc R U . . .
C5 C 0.7134(4) 0.3975(3) 0.87771(11) 0.0579(6) Uani 1 1 d . . . . .
H5 H 0.578775 0.352809 0.878482 0.069 Uiso 1 1 calc R U . . .
C11 C 0.3227(4) 0.4099(2) 0.70890(11) 0.0546(6) Uani 1 1 d . . . . .
H11 H 0.236710 0.337320 0.695667 0.065 Uiso 1 1 calc R U . . .
C2 C 1.1148(4) 0.5270(3) 0.87647(13) 0.0656(7) Uani 1 1 d . . . . .
H2 H 1.250401 0.570635 0.875966 0.079 Uiso 1 1 calc R U . . .
C1 C 1.0651(5) 0.4455(3) 0.92410(13) 0.0691(8) Uani 1 1 d . . . . .
H1 H 1.166385 0.434020 0.955863 0.083 Uiso 1 1 calc R U . . .
C13 C -0.0838(4) 0.4443(3) 0.62005(12) 0.0642(7) Uani 1 1 d . . . . .
H13 H -0.147670 0.451484 0.660016 0.077 Uiso 1 1 calc R U . . .
C6 C 0.8642(5) 0.3804(3) 0.92484(12) 0.0679(7) Uani 1 1 d . . . . .
H6 H 0.830127 0.324956 0.957153 0.082 Uiso 1 1 calc R U . . .
C14 C -0.2592(4) 0.4793(3) 0.57188(13) 0.0692(7) Uani 1 1 d . . . . .
H14A H -0.379867 0.529288 0.589034 0.083 Uiso 1 1 calc R U . . .
H14B H -0.197327 0.532162 0.539634 0.083 Uiso 1 1 calc R U . . .
C15 C -0.3339(6) 0.3433(4) 0.54970(15) 0.0842(10) Uani 1 1 d . . . . .
H15A H -0.383460 0.347082 0.507811 0.101 Uiso 1 1 calc R U . . .
H15B H -0.451307 0.307708 0.573868 0.101 Uiso 1 1 calc R U . . .
C16 C -0.1281(6) 0.2607(3) 0.55723(15) 0.0874(10) Uani 1 1 d . . . . .
H16A H -0.163879 0.165440 0.561303 0.105 Uiso 1 1 calc R U . . .
H16B H -0.035349 0.271821 0.522670 0.105 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 C10 1.768(2) . ?
S1 C13 1.797(3) . ?
C4 C7 1.484(3) . ?
C4 C3 1.397(3) . ?
C4 C5 1.390(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.392(3) . ?
O1 C13 1.414(4) . ?
O1 C16 1.404(3) . ?
C10 C9 1.389(3) . ?
C10 C11 1.390(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(3) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.381(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.380(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C11 H11 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.369(4) . ?
C1 H1 0.9300 . ?
C1 C6 1.380(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.528(4) . ?
C6 H6 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.496(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.499(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C10 S1 C13 104.74(12) . . ?
C3 C4 C7 120.4(2) . . ?
C5 C4 C7 121.5(2) . . ?
C5 C4 C3 118.1(2) . . ?
C8 C7 C4 121.3(2) . . ?
C8 C7 C12 117.4(2) . . ?
C12 C7 C4 121.3(2) . . ?
C16 O1 C13 109.3(2) . . ?
C9 C10 S1 117.15(18) . . ?
C9 C10 C11 118.8(2) . . ?
C11 C10 S1 124.02(19) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.8 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.7(2) . . ?
C11 C12 H12 119.2 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C3 C2 H2 119.7 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.7 . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.8(2) . . ?
C6 C1 H1 120.1 . . ?
S1 C13 H13 109.3 . . ?
O1 C13 S1 113.6(2) . . ?
O1 C13 H13 109.3 . . ?
O1 C13 C14 106.8(2) . . ?
C14 C13 S1 108.4(2) . . ?
C14 C13 H13 109.3 . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 H6 119.9 . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 C13 103.1(3) . . ?
C15 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C14 C15 H15A 111.4 . . ?
C14 C15 H15B 111.4 . . ?
C14 C15 C16 102.0(2) . . ?
H15A C15 H15B 109.2 . . ?
C16 C15 H15A 111.4 . . ?
C16 C15 H15B 111.4 . . ?
O1 C16 C15 106.1(3) . . ?
O1 C16 H16A 110.5 . . ?
O1 C16 H16B 110.5 . . ?
C15 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?

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 C10 C9 C8 -175.77(19) . . . . ?
S1 C10 C11 C12 176.65(19) . . . . ?
S1 C13 C14 C15 140.6(2) . . . . ?
C4 C7 C8 C9 178.8(2) . . . . ?
C4 C7 C12 C11 -177.7(2) . . . . ?
C4 C3 C2 C1 0.2(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C7 C4 C3 C2 -179.8(2) . . . . ?
C7 C4 C5 C6 179.9(2) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C7 C12 C11 C10 -1.2(4) . . . . ?
O1 C13 C14 C15 17.9(3) . . . . ?
C10 S1 C13 O1 -71.7(2) . . . . ?
C10 S1 C13 C14 169.78(18) . . . . ?
C8 C7 C12 C11 1.6(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C3 C4 C7 C8 -35.9(3) . . . . ?
C3 C4 C7 C12 143.4(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C2 C1 C6 0.1(4) . . . . ?
C12 C7 C8 C9 -0.5(4) . . . . ?
C5 C4 C7 C8 144.9(2) . . . . ?
C5 C4 C7 C12 -35.8(3) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?
C11 C10 C9 C8 1.5(4) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C13 S1 C10 C9 -154.7(2) . . . . ?
C13 S1 C10 C11 28.3(2) . . . . ?
C13 O1 C16 C15 -25.3(4) . . . . ?
C13 C14 C15 C16 -31.5(3) . . . . ?
C14 C15 C16 O1 35.6(3) . . . . ?
C16 O1 C13 S1 -115.0(3) . . . . ?
C16 O1 C13 C14 4.4(3) . . . . ?

_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 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.774
