# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_b250109c_a
_database_code_depnum_ccdc_archive 'CCDC 2417131'
loop_
_audit_author_name
_audit_author_address
'Propargyl sulfoxide'
;soochou university
China
;
_audit_update_record             
;
2025-01-15 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H32 O2 S'
_chemical_formula_weight         396.56

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.6368(2)
_cell_length_b                   11.6180(3)
_cell_length_c                   22.8872(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2296.56(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.6698
_cell_measurement_theta_max      27.4626

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(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            24205
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.966
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5215
_reflns_number_gt                4694
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.995

_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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+0.3131P] 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_abs_structure_details 
;
 Flack x determined using 1811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5215
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_restrained_S_all      0.878
_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 0.31314(7) 0.31985(5) 0.39444(2) 0.03367(17) Uani 1 1 d . . . . .
O1 O 0.3304(3) 0.19756(15) 0.38821(9) 0.0491(5) Uani 1 1 d . . . . .
O2 O 0.2118(2) 0.35877(18) 0.43977(8) 0.0480(5) Uani 1 1 d . . . . .
C1 C 0.5032(3) 0.3777(2) 0.41108(10) 0.0343(5) Uani 1 1 d . . . . .
H1 H 0.574537 0.356793 0.378934 0.041 Uiso 1 1 calc R U . . .
C2 C 0.4986(3) 0.5031(2) 0.41567(10) 0.0344(5) Uani 1 1 d . . . . .
C3 C 0.5048(3) 0.6040(2) 0.42308(11) 0.0370(5) Uani 1 1 d . . . . .
C4 C 0.5195(3) 0.7243(2) 0.43520(10) 0.0344(5) Uani 1 1 d . . . . .
C5 C 0.4092(3) 0.8038(2) 0.41770(13) 0.0438(6) Uani 1 1 d . . . . .
H5 H 0.322076 0.778948 0.396557 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4258(4) 0.9188(2) 0.43094(14) 0.0504(7) Uani 1 1 d . . . . .
H6 H 0.350440 0.971834 0.418547 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5513(4) 0.9561(3) 0.46205(14) 0.0530(7) Uani 1 1 d . . . . .
H7 H 0.560987 1.034460 0.471701 0.064 Uiso 1 1 calc R U . . .
C8 C 0.6638(4) 0.8790(3) 0.47927(13) 0.0541(8) Uani 1 1 d . . . . .
H8 H 0.750781 0.905092 0.500107 0.065 Uiso 1 1 calc R U . . .
C9 C 0.6491(3) 0.7639(3) 0.46605(12) 0.0462(6) Uani 1 1 d . . . . .
H9 H 0.726274 0.711701 0.477747 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5619(4) 0.3216(3) 0.46748(14) 0.0575(8) Uani 1 1 d . . . . .
H10A H 0.665729 0.348720 0.475837 0.086 Uiso 1 1 calc R U . . .
H10B H 0.563275 0.238615 0.462750 0.086 Uiso 1 1 calc R U . . .
H10C H 0.493675 0.341846 0.499548 0.086 Uiso 1 1 calc R U . . .
C11 C 0.2612(3) 0.3796(2) 0.32484(10) 0.0309(5) Uani 1 1 d . . . . .
C12 C 0.1441(3) 0.4642(2) 0.31943(11) 0.0346(5) Uani 1 1 d . . . . .
C13 C 0.1013(3) 0.4962(2) 0.26317(12) 0.0418(6) Uani 1 1 d . . . . .
H13 H 0.021409 0.550442 0.258746 0.050 Uiso 1 1 calc R U . . .
C14 C 0.1700(3) 0.4522(2) 0.21339(11) 0.0407(6) Uani 1 1 d . . . . .
C15 C 0.2887(3) 0.3740(2) 0.22045(11) 0.0396(6) Uani 1 1 d . . . . .
H15 H 0.338396 0.345444 0.186923 0.047 Uiso 1 1 calc R U . . .
C16 C 0.3382(3) 0.3354(2) 0.27485(10) 0.0335(5) Uani 1 1 d . . . . .
C17 C 0.0585(3) 0.5218(3) 0.37000(13) 0.0420(6) Uani 1 1 d . . . . .
H17 H 0.126783 0.519176 0.404727 0.050 Uiso 1 1 calc R U . . .
C18 C 0.0209(5) 0.6487(3) 0.35741(16) 0.0625(9) Uani 1 1 d . . . . .
H18A H 0.111481 0.686268 0.341172 0.094 Uiso 1 1 calc R U . . .
H18B H -0.008741 0.686689 0.393438 0.094 Uiso 1 1 calc R U . . .
H18C H -0.063771 0.653088 0.329659 0.094 Uiso 1 1 calc R U . . .
C19 C -0.0895(4) 0.4551(4) 0.38452(17) 0.0640(9) Uani 1 1 d . . . . .
H19A H -0.155284 0.451806 0.350219 0.096 Uiso 1 1 calc R U . . .
H19B H -0.144107 0.493602 0.415960 0.096 Uiso 1 1 calc R U . . .
H19C H -0.062723 0.377543 0.396573 0.096 Uiso 1 1 calc R U . . .
C20 C 0.1230(4) 0.4900(3) 0.15257(13) 0.0510(7) Uani 1 1 d . . . . .
H20 H 0.172456 0.435574 0.124984 0.061 Uiso 1 1 calc R U . . .
C21 C 0.1858(7) 0.6062(4) 0.13870(18) 0.0956(17) Uani 1 1 d . . . . .
H21A H 0.173747 0.621312 0.097264 0.143 Uiso 1 1 calc R U . . .
H21B H 0.294765 0.609105 0.148897 0.143 Uiso 1 1 calc R U . . .
H21C H 0.129856 0.663888 0.160892 0.143 Uiso 1 1 calc R U . . .
C22 C -0.0490(5) 0.4827(4) 0.14191(19) 0.0787(12) Uani 1 1 d . . . . .
H22A H -0.086658 0.407970 0.154352 0.118 Uiso 1 1 calc R U . . .
H22B H -0.069747 0.492887 0.100583 0.118 Uiso 1 1 calc R U . . .
H22C H -0.101117 0.542568 0.163938 0.118 Uiso 1 1 calc R U . . .
C23 C 0.4734(3) 0.2513(2) 0.27459(11) 0.0416(6) Uani 1 1 d . . . . .
H23 H 0.498268 0.232355 0.315695 0.050 Uiso 1 1 calc R U . . .
C24 C 0.6166(4) 0.3071(3) 0.24736(14) 0.0586(8) Uani 1 1 d . . . . .
H24A H 0.592838 0.331720 0.207863 0.088 Uiso 1 1 calc R U . . .
H24B H 0.700663 0.251789 0.246437 0.088 Uiso 1 1 calc R U . . .
H24C H 0.647168 0.373272 0.270510 0.088 Uiso 1 1 calc R U . . .
C25 C 0.4301(5) 0.1394(3) 0.24352(17) 0.0679(10) Uani 1 1 d . . . . .
H25A H 0.341850 0.104649 0.262920 0.102 Uiso 1 1 calc R U . . .
H25B H 0.517172 0.086756 0.244746 0.102 Uiso 1 1 calc R U . . .
H25C H 0.403727 0.155799 0.203166 0.102 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 O2 1.4309(19) . ?
S1 O1 1.4356(18) . ?
S1 C11 1.795(2) . ?
S1 C1 1.815(3) . ?
C1 C2 1.461(3) . ?
C1 C10 1.532(4) . ?
C2 C3 1.185(4) . ?
C3 C4 1.431(4) . ?
C4 C5 1.386(4) . ?
C4 C9 1.401(4) . ?
C5 C6 1.377(4) . ?
C6 C7 1.368(5) . ?
C7 C8 1.379(5) . ?
C8 C9 1.377(4) . ?
C11 C12 1.416(3) . ?
C11 C16 1.419(3) . ?
C12 C13 1.390(4) . ?
C12 C17 1.528(3) . ?
C13 C14 1.383(4) . ?
C14 C15 1.379(4) . ?
C14 C20 1.515(4) . ?
C15 C16 1.391(3) . ?
C16 C23 1.523(3) . ?
C17 C19 1.532(4) . ?
C17 C18 1.536(4) . ?
C20 C21 1.489(5) . ?
C20 C22 1.508(5) . ?
C23 C25 1.528(4) . ?
C23 C24 1.529(4) . ?

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
O2 S1 O1 116.63(12) . . ?
O2 S1 C11 111.61(12) . . ?
O1 S1 C11 108.71(11) . . ?
O2 S1 C1 106.51(12) . . ?
O1 S1 C1 107.09(12) . . ?
C11 S1 C1 105.62(11) . . ?
C2 C1 C10 111.9(2) . . ?
C2 C1 S1 111.09(18) . . ?
C10 C1 S1 108.5(2) . . ?
C3 C2 C1 174.1(3) . . ?
C2 C3 C4 176.1(3) . . ?
C5 C4 C9 118.5(2) . . ?
C5 C4 C3 122.3(2) . . ?
C9 C4 C3 119.3(2) . . ?
C6 C5 C4 120.7(3) . . ?
C7 C6 C5 120.3(3) . . ?
C6 C7 C8 120.1(3) . . ?
C9 C8 C7 120.2(3) . . ?
C8 C9 C4 120.2(3) . . ?
C12 C11 C16 121.0(2) . . ?
C12 C11 S1 121.66(18) . . ?
C16 C11 S1 117.28(18) . . ?
C13 C12 C11 117.2(2) . . ?
C13 C12 C17 117.1(2) . . ?
C11 C12 C17 125.7(2) . . ?
C14 C13 C12 123.4(2) . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 C20 119.8(2) . . ?
C13 C14 C20 122.4(2) . . ?
C14 C15 C16 123.1(2) . . ?
C15 C16 C11 117.5(2) . . ?
C15 C16 C23 116.0(2) . . ?
C11 C16 C23 126.5(2) . . ?
C12 C17 C19 110.2(2) . . ?
C12 C17 C18 112.4(2) . . ?
C19 C17 C18 110.5(3) . . ?
C21 C20 C22 112.0(4) . . ?
C21 C20 C14 111.1(3) . . ?
C22 C20 C14 113.4(3) . . ?
C16 C23 C25 111.1(2) . . ?
C16 C23 C24 110.5(2) . . ?
C25 C23 C24 111.6(3) . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.034

