# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_a21060801aqlq1
_database_code_depnum_ccdc_archive 'CCDC 2308239'
loop_
_audit_author_name
_audit_author_address
'Qin Shengxiang'
;Sun Yat Sen University
China
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 S'
_chemical_formula_sum            'C17 H14 S'
_chemical_formula_weight         250.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHS
_chemical_oxdiff_usercomment     210608
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2038(9)
_cell_length_b                   8.2643(9)
_cell_length_c                   10.5638(10)
_cell_angle_alpha                105.060(9)
_cell_angle_beta                 106.146(9)
_cell_angle_gamma                103.841(10)
_cell_volume                     625.75(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1608
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.4410
_cell_measurement_theta_min      4.6180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3942
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.014
_diffrn_reflns_theta_min         4.652
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -16.00   1.00    1.00    --  -40.77 -57.00 120.00   94
  2  ω    -63.00  28.00   1.00    1.00    --  -40.77  57.00 -90.00   91
  3  ω     57.00  99.00   1.00    1.00    --   40.77-133.00  90.00   42
  4  ω    -32.00  63.00   1.00    1.00    --   40.77 -38.00 -30.00   95
  5  ω     89.00 170.00   1.00    1.02    --  105.29  45.00  30.00   81
  6  ω     27.00  97.00   1.00    1.02    --  105.29 -94.00  60.00   70
  7  ω     36.00  91.00   1.00    1.02    --  105.29 -45.00  30.00   55
  8  ω     38.00  81.00   1.00    1.02    --  105.29-125.00   0.00   43
  9  ω     77.00 123.00   1.00    1.02    --  105.29  30.00-150.00   46
 10  ω     82.00 112.00   1.00    1.02    --  105.29-125.00   0.00   30
 11  ω     29.00  71.00   1.00    1.02    --  105.29 -94.00-180.00   42
 12  ω     83.00 109.00   1.00    1.02    --  105.29-125.00 -90.00   26
 13  ω     42.00 112.00   1.00    1.02    --  105.29-125.00-180.00   70
 14  ω     82.00 177.00   1.00    1.02    --  105.29  30.00 -60.00   95
 15  ω     35.00 124.00   1.00    1.02    --  105.29 -61.00-180.00   89
 16  ω    126.00 153.00   1.00    1.02    --  105.29  77.00-150.00   27
 17  ω     97.00 166.00   1.00    1.02    --  105.29 125.00 120.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0657536000
_diffrn_orient_matrix_UB_12      -0.1055590000
_diffrn_orient_matrix_UB_13      0.0921117000
_diffrn_orient_matrix_UB_21      -0.0431029000
_diffrn_orient_matrix_UB_22      -0.1589295000
_diffrn_orient_matrix_UB_23      -0.1333326000
_diffrn_orient_matrix_UB_31      0.1920804000
_diffrn_orient_matrix_UB_32      0.0748356000
_diffrn_orient_matrix_UB_33      0.0020920000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2101
_reflns_number_total             2387
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.275
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      0.986
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1400
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_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
C1 C 0.3883(2) 0.6526(3) 0.3457(2) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.2788(2) 0.7522(2) 0.40275(19) 0.0233(4) Uani 1 1 d . . . . .
H2 H 0.3586 0.8588 0.4840 0.028 Uiso 1 1 calc R . . . .
C3 C 0.1714(3) 0.6132(3) 0.4529(2) 0.0255(4) Uani 1 1 d . . . . .
H3A H 0.2208 0.6494 0.5546 0.031 Uiso 1 1 calc R . . . .
H3B H 0.0457 0.6050 0.4243 0.031 Uiso 1 1 calc R . . . .
C4 C 0.1883(3) 0.4314(3) 0.3845(2) 0.0260(4) Uani 1 1 d . . . . .
H4A H 0.2178 0.3740 0.4528 0.031 Uiso 1 1 calc R . . . .
H4B H 0.0777 0.3530 0.3073 0.031 Uiso 1 1 calc R . . . .
C5 C 0.3394(2) 0.4807(3) 0.3328(2) 0.0232(4) Uani 1 1 d . . . . .
C6 C 0.4378(2) 0.3848(3) 0.26908(19) 0.0235(4) Uani 1 1 d . . . . .
C7 C 0.5642(3) 0.4986(3) 0.2344(2) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.6745(3) 0.4367(3) 0.1696(2) 0.0290(4) Uani 1 1 d . . . . .
H8 H 0.7566 0.5124 0.1472 0.035 Uiso 1 1 calc R . . . .
C9 C 0.6586(3) 0.2592(3) 0.1395(2) 0.0316(5) Uani 1 1 d . . . . .
H9 H 0.7309 0.2152 0.0959 0.038 Uiso 1 1 calc R . . . .
C10 C 0.5356(3) 0.1438(3) 0.1734(2) 0.0301(5) Uani 1 1 d . . . . .
H10 H 0.5279 0.0251 0.1526 0.036 Uiso 1 1 calc R . . . .
C11 C 0.4257(3) 0.2063(3) 0.2377(2) 0.0268(4) Uani 1 1 d . . . . .
H11 H 0.3442 0.1297 0.2599 0.032 Uiso 1 1 calc R . . . .
C12 C 0.1530(2) 0.8029(2) 0.2963(2) 0.0225(4) Uani 1 1 d . . . . .
C13 C 0.1064(3) 0.7262(3) 0.1518(2) 0.0265(4) Uani 1 1 d . . . . .
H13 H 0.1602 0.6466 0.1172 0.032 Uiso 1 1 calc R . . . .
C14 C -0.0197(3) 0.7674(3) 0.0586(2) 0.0312(5) Uani 1 1 d . . . . .
H14 H -0.0497 0.7156 -0.0379 0.037 Uiso 1 1 calc R . . . .
C15 C -0.1008(3) 0.8855(3) 0.1092(2) 0.0322(5) Uani 1 1 d . . . . .
H15 H -0.1863 0.9120 0.0468 0.039 Uiso 1 1 calc R . . . .
C16 C -0.0545(3) 0.9642(3) 0.2531(2) 0.0296(5) Uani 1 1 d . . . . .
H16 H -0.1090 1.0433 0.2874 0.036 Uiso 1 1 calc R . . . .
C17 C 0.0734(3) 0.9246(3) 0.3456(2) 0.0255(4) Uani 1 1 d . . . . .
H17 H 0.1065 0.9801 0.4420 0.031 Uiso 1 1 calc R . . . .
S1 S 0.55782(6) 0.71589(6) 0.28197(5) 0.0282(2) Uani 1 1 d . . . . .


_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
C1 C2 1.498(3) . ?
C1 C5 1.340(3) . ?
C1 S1 1.7371(19) . ?
C2 H2 0.9800 . ?
C2 C3 1.570(2) . ?
C2 C12 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.546(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.500(3) . ?
C5 C6 1.436(3) . ?
C6 C7 1.421(3) . ?
C6 C11 1.397(3) . ?
C7 C8 1.390(3) . ?
C7 S1 1.752(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.404(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(3) . ?
C12 C17 1.393(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
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
C2 C1 S1 131.54(14) . . ?
C5 C1 C2 114.54(17) . . ?
C5 C1 S1 113.76(16) . . ?
C1 C2 H2 109.8 . . ?
C1 C2 C3 100.75(15) . . ?
C1 C2 C12 114.77(16) . . ?
C3 C2 H2 109.8 . . ?
C12 C2 H2 109.8 . . ?
C12 C2 C3 111.60(14) . . ?
C2 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 C2 107.63(15) . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 C3 102.98(15) . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C1 C5 C4 111.61(18) . . ?
C1 C5 C6 113.66(17) . . ?
C6 C5 C4 134.68(17) . . ?
C7 C6 C5 110.61(17) . . ?
C11 C6 C5 130.64(17) . . ?
C11 C6 C7 118.75(18) . . ?
C6 C7 S1 111.56(15) . . ?
C8 C7 C6 121.75(18) . . ?
C8 C7 S1 126.69(15) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 118.01(19) . . ?
C9 C8 H8 121.0 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.22(19) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 120.1 . . ?
C10 C11 C6 119.77(18) . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C2 122.99(18) . . ?
C13 C12 C17 118.55(18) . . ?
C17 C12 C2 118.37(17) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.72(19) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.94(19) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.75(19) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.99(19) . . ?
C16 C17 H17 119.5 . . ?
C1 S1 C7 90.41(9) . . ?


_olex2_date_sample_data_collection 2021-06-08
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.721
