# Supplementary Information (SI) for Organic & Biomolecular 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_Thioester_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2339403'
_audit_update_record             
;
2024-03-11 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.85 H2.67 I0.30 O0.30 S0.30'
_chemical_formula_weight         100.79

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'
I I -0.4742 1.8119 '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      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                   18.834(3)
_cell_length_b                   7.9364(13)
_cell_length_c                   17.557(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.605(6)
_cell_angle_gamma                90
_cell_volume                     2550.7(7)
_cell_formula_units_Z            27
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    57729
_cell_measurement_theta_min      2.225
_cell_measurement_theta_max      24.854

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.650
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57729
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         24.854
_diffrn_reflns_theta_full        24.854
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4423
_reflns_number_gt                3404
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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] 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         4423
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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
I1 I 0.29993(3) 0.56962(7) 0.36875(3) 0.0628(2) Uani 1 1 d . . . . .
I2 I 0.19421(3) 0.84425(7) 0.14025(3) 0.0746(2) Uani 1 1 d . . . . .
S1 S 0.56454(11) 0.5477(2) 0.42244(12) 0.0640(5) Uani 1 1 d . . . . .
S2 S 0.13666(14) 0.8105(3) 0.39353(11) 0.0760(7) Uani 1 1 d . . . . .
O1 O 0.4504(3) 0.6940(6) 0.3304(3) 0.0712(15) Uani 1 1 d . . . . .
O2 O 0.0923(3) 0.9579(6) 0.2563(3) 0.0697(15) Uani 1 1 d . . . . .
C1 C 0.5946(3) 0.7607(8) 0.4259(3) 0.0432(15) Uani 1 1 d . . . . .
C2 C 0.5807(4) 0.8675(9) 0.4821(4) 0.0580(18) Uani 1 1 d . . . . .
H2 H 0.554048 0.829586 0.517084 0.070 Uiso 1 1 calc R U . . .
C3 C 0.6062(4) 1.0308(9) 0.4868(4) 0.0596(18) Uani 1 1 d . . . . .
H3 H 0.596929 1.102539 0.525266 0.071 Uiso 1 1 calc R U . . .
C4 C 0.6450(4) 1.0880(9) 0.4353(5) 0.0613(19) Uani 1 1 d . . . . .
H4 H 0.662569 1.197972 0.438910 0.074 Uiso 1 1 calc R U . . .
C5 C 0.6580(4) 0.9822(10) 0.3781(4) 0.066(2) Uani 1 1 d . . . . .
H5 H 0.683272 1.021703 0.342201 0.079 Uiso 1 1 calc R U . . .
C6 C 0.6337(4) 0.8176(10) 0.3738(4) 0.0628(19) Uani 1 1 d . . . . .
H6 H 0.643653 0.745476 0.335841 0.075 Uiso 1 1 calc R U . . .
C7 C 0.4763(4) 0.5635(7) 0.3580(4) 0.0461(15) Uani 1 1 d . . . . .
C8 C 0.4391(4) 0.3960(7) 0.3418(4) 0.0448(14) Uani 1 1 d . . . . .
C9 C 0.3648(4) 0.3772(8) 0.3400(4) 0.0479(16) Uani 1 1 d . . . . .
C10 C 0.3323(4) 0.2185(9) 0.3245(4) 0.0583(19) Uani 1 1 d . . . . .
H10 H 0.283095 0.204425 0.323861 0.070 Uiso 1 1 calc R U . . .
C11 C 0.3733(5) 0.0817(9) 0.3101(4) 0.063(2) Uani 1 1 d . . . . .
H11 H 0.351282 -0.023122 0.298619 0.076 Uiso 1 1 calc R U . . .
C12 C 0.4458(5) 0.1006(8) 0.3126(4) 0.061(2) Uani 1 1 d . . . . .
H12 H 0.473416 0.007871 0.304797 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4781(4) 0.2566(8) 0.3267(4) 0.0493(16) Uani 1 1 d . . . . .
H13 H 0.527026 0.268857 0.326063 0.059 Uiso 1 1 calc R U . . .
C14 C 0.1220(4) 1.0166(9) 0.4231(4) 0.0548(17) Uani 1 1 d . . . . .
C15 C 0.0533(5) 1.0693(10) 0.4239(5) 0.075(2) Uani 1 1 d . . . . .
H15 H 0.013894 0.996794 0.407292 0.090 Uiso 1 1 calc R U . . .
C16 C 0.0418(6) 1.2297(12) 0.4491(6) 0.092(3) Uani 1 1 d . . . . .
H16 H -0.005491 1.264128 0.448764 0.111 Uiso 1 1 calc R U . . .
C17 C 0.0972(6) 1.3362(10) 0.4740(5) 0.080(3) Uani 1 1 d . . . . .
H17 H 0.088507 1.442446 0.492204 0.096 Uiso 1 1 calc R U . . .
C18 C 0.1660(6) 1.2900(12) 0.4729(5) 0.086(3) Uani 1 1 d . . . . .
H18 H 0.204177 1.366061 0.488488 0.103 Uiso 1 1 calc R U . . .
C19 C 0.1800(5) 1.1276(11) 0.4482(5) 0.071(2) Uani 1 1 d . . . . .
H19 H 0.227435 1.094698 0.448596 0.086 Uiso 1 1 calc R U . . .
C20 C 0.1100(4) 0.8275(7) 0.2891(4) 0.0471(15) Uani 1 1 d . . . . .
C21 C 0.1133(3) 0.6620(8) 0.2506(4) 0.0470(15) Uani 1 1 d . . . . .
C22 C 0.0861(4) 0.5198(9) 0.2788(4) 0.0586(18) Uani 1 1 d . . . . .
H22 H 0.064274 0.529607 0.320896 0.070 Uiso 1 1 calc R U . . .
C23 C 0.0905(4) 0.3657(9) 0.2466(5) 0.067(2) Uani 1 1 d . . . . .
H23 H 0.071765 0.272337 0.267214 0.080 Uiso 1 1 calc R U . . .
C24 C 0.1214(5) 0.3453(9) 0.1852(5) 0.069(2) Uani 1 1 d . . . . .
H24 H 0.123961 0.238989 0.163779 0.083 Uiso 1 1 calc R U . . .
C25 C 0.1494(4) 0.4857(10) 0.1542(4) 0.0633(19) Uani 1 1 d . . . . .
H25 H 0.170885 0.473212 0.111887 0.076 Uiso 1 1 calc R U . . .
C26 C 0.1451(4) 0.6449(8) 0.1869(4) 0.0468(15) 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
I1 C9 2.090(7) . ?
I2 C26 2.094(7) . ?
S1 C1 1.779(6) . ?
S1 C7 1.781(7) . ?
S2 C14 1.757(7) . ?
S2 C20 1.789(7) . ?
O1 C7 1.197(7) . ?
O2 C20 1.193(7) . ?
C1 C2 1.372(9) . ?
C1 C6 1.379(9) . ?
C2 C3 1.378(9) . ?
C3 C4 1.368(10) . ?
C4 C5 1.373(11) . ?
C5 C6 1.380(10) . ?
C7 C8 1.499(8) . ?
C8 C13 1.387(9) . ?
C8 C9 1.400(9) . ?
C9 C10 1.400(9) . ?
C10 C11 1.391(11) . ?
C11 C12 1.363(11) . ?
C12 C13 1.376(9) . ?
C14 C15 1.363(11) . ?
C14 C19 1.392(11) . ?
C15 C16 1.382(11) . ?
C16 C17 1.334(13) . ?
C17 C18 1.350(13) . ?
C18 C19 1.404(12) . ?
C20 C21 1.484(8) . ?
C21 C22 1.379(9) . ?
C21 C26 1.395(9) . ?
C22 C23 1.358(9) . ?
C23 C24 1.349(11) . ?
C24 C25 1.397(11) . ?
C25 C26 1.398(9) . ?

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
C1 S1 C7 101.3(3) . . ?
C14 S2 C20 101.9(3) . . ?
C2 C1 C6 119.8(6) . . ?
C2 C1 S1 119.9(5) . . ?
C6 C1 S1 120.3(5) . . ?
C1 C2 C3 120.1(7) . . ?
C4 C3 C2 120.3(7) . . ?
C3 C4 C5 119.7(7) . . ?
C4 C5 C6 120.4(7) . . ?
C1 C6 C5 119.7(7) . . ?
O1 C7 C8 124.2(6) . . ?
O1 C7 S1 123.2(5) . . ?
C8 C7 S1 112.5(4) . . ?
C13 C8 C9 118.8(6) . . ?
C13 C8 C7 119.9(6) . . ?
C9 C8 C7 121.2(6) . . ?
C8 C9 C10 119.3(6) . . ?
C8 C9 I1 123.7(5) . . ?
C10 C9 I1 116.8(5) . . ?
C11 C10 C9 120.1(7) . . ?
C12 C11 C10 120.2(7) . . ?
C11 C12 C13 120.1(7) . . ?
C12 C13 C8 121.3(7) . . ?
C15 C14 C19 118.6(7) . . ?
C15 C14 S2 120.3(6) . . ?
C19 C14 S2 121.1(6) . . ?
C14 C15 C16 120.5(8) . . ?
C17 C16 C15 121.2(10) . . ?
C16 C17 C18 120.2(9) . . ?
C17 C18 C19 120.3(8) . . ?
C14 C19 C18 119.2(8) . . ?
O2 C20 C21 125.8(6) . . ?
O2 C20 S2 122.6(5) . . ?
C21 C20 S2 111.6(4) . . ?
C22 C21 C26 118.3(6) . . ?
C22 C21 C20 120.1(6) . . ?
C26 C21 C20 121.5(6) . . ?
C23 C22 C21 121.6(7) . . ?
C24 C23 C22 121.3(8) . . ?
C23 C24 C25 119.3(7) . . ?
C24 C25 C26 119.8(7) . . ?
C21 C26 C25 119.7(6) . . ?
C21 C26 I2 123.5(5) . . ?
C25 C26 I2 116.7(5) . . ?

_refine_diff_density_max         0.590
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.153

