# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2247661'
loop_
_audit_author_name
_audit_author_address
'Masaharu Takatsuki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-03-10 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H18 O4 S'
_chemical_formula_moiety         'C18 H18 O4 S'
_chemical_formula_weight         330.40
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.3144(3)
_cell_length_b                   9.8167(4)
_cell_length_c                   20.8013(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.087(7)
_cell_angle_gamma                90.0000
_cell_volume                     1676.48(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12976
_cell_measurement_theta_min      4.30
_cell_measurement_theta_max      68.26
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.00
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_T_max  0.756

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18018
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_theta_max         68.194
_diffrn_reflns_theta_min         4.305
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3027
_reflns_number_gt                2023
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1426
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3027
_refine_ls_number_parameters     208
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0725P)²+0.8960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.017
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.55444(10) -0.03775(8) 0.23107(4) 0.0503(3) Uani 1 1 d . . . . .
O1 O 0.6074(3) -0.1771(2) 0.23583(11) 0.0646(7) Uani 1 1 d . . . . .
O2 O 0.6198(3) 0.0499(3) 0.18627(11) 0.0667(7) Uani 1 1 d . . . . .
O3 O 0.8063(3) -0.0329(3) 0.54386(11) 0.0764(8) Uani 1 1 d . . . . .
O4 O 0.7874(4) -0.1188(3) 0.43950(14) 0.0972(10) Uani 1 1 d . . . . .
C1 C 0.3412(4) -0.0347(3) 0.21201(15) 0.0508(8) Uani 1 1 d . . . . .
C2 C 0.2681(5) 0.0640(4) 0.17041(18) 0.0670(10) Uani 1 1 d . . . . .
H2 H 0.331399 0.127869 0.152788 0.080 Uiso 1 1 calc R U . . .
C3 C 0.1020(6) 0.0681(5) 0.1550(2) 0.0901(14) Uani 1 1 d . . . . .
H3 H 0.052075 0.134794 0.127010 0.108 Uiso 1 1 calc R U . . .
C4 C 0.0089(5) -0.0271(6) 0.1812(3) 0.0962(16) Uani 1 1 d . . . . .
H4 H -0.103937 -0.024792 0.170525 0.115 Uiso 1 1 calc R U . . .
C5 C 0.0823(5) -0.1253(5) 0.2230(2) 0.0834(13) Uani 1 1 d . . . . .
H5 H 0.018591 -0.188073 0.241113 0.100 Uiso 1 1 calc R U . . .
C6 C 0.2497(4) -0.1313(4) 0.23823(18) 0.0627(10) Uani 1 1 d . . . . .
H6 H 0.299896 -0.198995 0.265589 0.075 Uiso 1 1 calc R U . . .
C7 C 0.5960(4) 0.0373(3) 0.30877(14) 0.0474(7) Uani 1 1 d . . . . .
H7 H 0.560769 0.132713 0.306750 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5364(4) -0.0353(4) 0.36583(15) 0.0579(9) Uani 1 1 d . . . . .
H8A H 0.514483 -0.131511 0.358382 0.069 Uiso 1 1 calc R U . . .
H8B H 0.445733 0.009776 0.381114 0.069 Uiso 1 1 calc R U . . .
C9 C 0.7725(4) 0.0257(4) 0.34477(15) 0.0596(9) Uani 1 1 d . . . . .
H9A H 0.833357 -0.049174 0.329890 0.071 Uiso 1 1 calc R U . . .
H9B H 0.833606 0.110074 0.346291 0.071 Uiso 1 1 calc R U . . .
C10 C 0.7033(4) -0.0053(3) 0.40751(15) 0.0576(9) Uani 1 1 d . . . . .
C11 C 0.7028(4) 0.1124(3) 0.45435(16) 0.0572(9) Uani 1 1 d . . . . .
C12 C 0.6497(5) 0.2422(4) 0.43443(18) 0.0714(11) Uani 1 1 d . . . . .
H12 H 0.611645 0.257803 0.390566 0.086 Uiso 1 1 calc R U . . .
C13 C 0.6519(5) 0.3484(4) 0.4778(2) 0.0822(12) Uani 1 1 d . . . . .
H13 H 0.616326 0.434432 0.463188 0.099 Uiso 1 1 calc R U . . .
C14 C 0.7065(5) 0.3264(5) 0.5423(2) 0.0847(13) Uani 1 1 d . . . . .
H14 H 0.707004 0.397630 0.571812 0.102 Uiso 1 1 calc R U . . .
C15 C 0.7604(5) 0.2004(5) 0.56377(18) 0.0776(12) Uani 1 1 d . . . . .
H15 H 0.799311 0.186513 0.607699 0.093 Uiso 1 1 calc R U . . .
C16 C 0.7571(4) 0.0925(4) 0.51981(17) 0.0631(10) Uani 1 1 d . . . . .
C18 C 0.7646(7) -0.1400(4) 0.4996(2) 0.0930(14) Uani 1 1 d . . . . .
H18 H 0.646781 -0.151893 0.497196 0.112 Uiso 1 1 calc R U . . .
C19 C 0.8378(6) -0.2686(4) 0.5275(2) 0.0997(15) Uani 1 1 d . . . . .
H19A H 0.817147 -0.278297 0.571432 0.120 Uiso 1 1 calc R U . . .
H19B H 0.790619 -0.344090 0.501889 0.120 Uiso 1 1 calc R U . . .
H19C H 0.953241 -0.266910 0.527434 0.120 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.436(2) . ?
S1 O2 1.437(2) . ?
S1 C1 1.754(3) . ?
S1 C7 1.760(3) . ?
O3 C16 1.367(4) . ?
O3 C18 1.404(5) . ?
O4 C18 1.310(5) . ?
O4 C10 1.424(4) . ?
C1 C2 1.376(5) . ?
C1 C6 1.381(5) . ?
C2 C3 1.368(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.532(4) . ?
C7 C9 1.543(4) . ?
C7 H7 0.9800 . ?
C8 C10 1.544(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.537(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.512(4) . ?
C11 C16 1.379(4) . ?
C11 C12 1.390(5) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(5) . ?
C15 H15 0.9300 . ?
C18 C19 1.481(5) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 118.18(15) . . ?
O1 S1 C1 108.62(15) . . ?
O2 S1 C1 108.39(15) . . ?
O1 S1 C7 108.79(15) . . ?
O2 S1 C7 107.78(15) . . ?
C1 S1 C7 104.19(14) . . ?
C16 O3 C18 113.9(3) . . ?
C18 O4 C10 115.8(3) . . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 S1 119.0(3) . . ?
C6 C1 S1 120.0(3) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C8 C7 C9 89.3(2) . . ?
C8 C7 S1 118.4(2) . . ?
C9 C7 S1 116.6(2) . . ?
C8 C7 H7 110.3 . . ?
C9 C7 H7 110.3 . . ?
S1 C7 H7 110.3 . . ?
C7 C8 C10 88.5(2) . . ?
C7 C8 H8A 113.9 . . ?
C10 C8 H8A 113.9 . . ?
C7 C8 H8B 113.9 . . ?
C10 C8 H8B 113.9 . . ?
H8A C8 H8B 111.1 . . ?
C10 C9 C7 88.4(2) . . ?
C10 C9 H9A 113.9 . . ?
C7 C9 H9A 113.9 . . ?
C10 C9 H9B 113.9 . . ?
C7 C9 H9B 113.9 . . ?
H9A C9 H9B 111.1 . . ?
O4 C10 C11 110.4(3) . . ?
O4 C10 C9 109.2(3) . . ?
C11 C10 C9 115.8(3) . . ?
O4 C10 C8 116.4(3) . . ?
C11 C10 C8 114.5(3) . . ?
C9 C10 C8 89.1(2) . . ?
C16 C11 C12 117.6(3) . . ?
C16 C11 C10 119.6(3) . . ?
C12 C11 C10 122.8(3) . . ?
C13 C12 C11 121.9(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
O3 C16 C11 121.4(3) . . ?
O3 C16 C15 118.0(3) . . ?
C11 C16 C15 120.6(4) . . ?
O4 C18 O3 116.7(4) . . ?
O4 C18 C19 113.4(4) . . ?
O3 C18 C19 109.7(4) . . ?
O4 C18 H18 105.3 . . ?
O3 C18 H18 105.3 . . ?
C19 C18 H18 105.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 -142.8(3) . . . . ?
O2 S1 C1 C2 -13.2(3) . . . . ?
C7 S1 C1 C2 101.4(3) . . . . ?
O1 S1 C1 C6 36.6(3) . . . . ?
O2 S1 C1 C6 166.2(3) . . . . ?
C7 S1 C1 C6 -79.2(3) . . . . ?
C6 C1 C2 C3 0.6(5) . . . . ?
S1 C1 C2 C3 -179.9(3) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 -1.2(7) . . . . ?
C4 C5 C6 C1 1.7(6) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
S1 C1 C6 C5 179.2(3) . . . . ?
O1 S1 C7 C8 -51.6(3) . . . . ?
O2 S1 C7 C8 179.1(2) . . . . ?
C1 S1 C7 C8 64.1(3) . . . . ?
O1 S1 C7 C9 53.3(3) . . . . ?
O2 S1 C7 C9 -76.0(3) . . . . ?
C1 S1 C7 C9 169.0(2) . . . . ?
C9 C7 C8 C10 16.1(2) . . . . ?
S1 C7 C8 C10 136.4(2) . . . . ?
C8 C7 C9 C10 -16.2(2) . . . . ?
S1 C7 C9 C10 -138.0(2) . . . . ?
C18 O4 C10 C11 38.4(5) . . . . ?
C18 O4 C10 C9 166.9(4) . . . . ?
C18 O4 C10 C8 -94.2(4) . . . . ?
C7 C9 C10 O4 133.8(3) . . . . ?
C7 C9 C10 C11 -100.8(3) . . . . ?
C7 C9 C10 C8 16.1(3) . . . . ?
C7 C8 C10 O4 -127.3(3) . . . . ?
C7 C8 C10 C11 101.9(3) . . . . ?
C7 C8 C10 C9 -16.2(3) . . . . ?
O4 C10 C11 C16 -9.2(5) . . . . ?
C9 C10 C11 C16 -133.9(3) . . . . ?
C8 C10 C11 C16 124.5(3) . . . . ?
O4 C10 C11 C12 170.7(4) . . . . ?
C9 C10 C11 C12 46.0(5) . . . . ?
C8 C10 C11 C12 -55.6(5) . . . . ?
C16 C11 C12 C13 0.6(6) . . . . ?
C10 C11 C12 C13 -179.3(4) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
C12 C13 C14 C15 0.7(7) . . . . ?
C13 C14 C15 C16 -1.2(6) . . . . ?
C18 O3 C16 C11 -12.6(5) . . . . ?
C18 O3 C16 C15 166.2(4) . . . . ?
C12 C11 C16 O3 177.7(3) . . . . ?
C10 C11 C16 O3 -2.3(5) . . . . ?
C12 C11 C16 C15 -1.0(5) . . . . ?
C10 C11 C16 C15 178.9(3) . . . . ?
C14 C15 C16 O3 -177.5(3) . . . . ?
C14 C15 C16 C11 1.3(6) . . . . ?
C10 O4 C18 O3 -58.2(6) . . . . ?
C10 O4 C18 C19 172.7(4) . . . . ?
C16 O3 C18 O4 43.3(6) . . . . ?
C16 O3 C18 C19 174.1(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_C18H17S1O4
_database_code_depnum_ccdc_archive 'CCDC 2247662'
loop_
_audit_author_name
_audit_author_address
'Masaharu Takatsuki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-03-10 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H18 O4 S'
_chemical_formula_moiety         'C18 H18 O4 S'
_chemical_formula_weight         330.40
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.154(2)
_cell_length_b                   8.1794(13)
_cell_length_c                   17.502(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.951(4)
_cell_angle_gamma                90.0000
_cell_volume                     1585.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3206
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.00
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.344
_exptl_absorpt_correction_T_max  0.978

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            15152
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_min         3.096
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3639
_reflns_number_gt                2734
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.1891
_refine_ls_wR_factor_gt          0.1827
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3639
_refine_ls_number_parameters     218
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1279P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         1.40
_refine_diff_density_min         -0.78
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.39729(6) 0.62217(7) 0.69751(3) 0.0223(2) Uani 1 1 d . . . . .
O1 O 0.68620(17) 0.9121(2) 1.01715(10) 0.0269(4) Uani 1 1 d . . . . .
O2A O 0.6247(2) 0.7021(2) 0.93235(11) 0.0238(8) Uani 0.864(8) 1 d D U P A 1
O2B O 0.5436(13) 0.7348(16) 0.9396(5) 0.020(5) Uani 0.136(8) 1 d D U P A 2
O3 O 0.27324(18) 0.6048(2) 0.71107(12) 0.0327(5) Uani 1 1 d . . . . .
O4 O 0.43144(19) 0.7556(2) 0.65069(10) 0.0322(5) Uani 1 1 d . . . . .
C1 C 0.6322(3) 0.6553(4) 1.06605(16) 0.0378(7) Uani 1 1 d . . . . .
H1A H 0.681532 0.705690 1.108360 0.045 Uiso 1 1 calc R U . . .
H1B H 0.557255 0.620694 1.082531 0.045 Uiso 1 1 calc R U . . .
H1C H 0.673732 0.562334 1.048512 0.045 Uiso 1 1 calc R U . . .
C2 C 0.6077(3) 0.7757(4) 1.00187(16) 0.0367(7) Uani 1 1 d D . . . .
H2 H 0.523815 0.813020 0.999363 0.044 Uiso 1 1 calc R U . A 1
C3 C 0.6804(2) 1.0197(3) 0.95654(14) 0.0235(5) Uani 1 1 d . . . . .
C4 C 0.7290(2) 1.1761(3) 0.97194(16) 0.0274(6) Uani 1 1 d . . . . .
H4 H 0.764744 1.203129 1.021083 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7229(2) 1.2897(3) 0.91295(17) 0.0306(6) Uani 1 1 d . . . . .
H5 H 0.753856 1.394141 0.922806 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6712(3) 1.2494(3) 0.83944(17) 0.0316(6) Uani 1 1 d . . . . .
H6 H 0.667369 1.326586 0.800191 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6251(2) 1.0933(3) 0.82449(16) 0.0272(6) Uani 1 1 d . . . . .
H7 H 0.590754 1.066427 0.775004 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6296(2) 0.9765(3) 0.88281(14) 0.0232(5) Uani 1 1 d . . . . .
C9 C 0.5815(3) 0.8050(3) 0.86788(14) 0.0268(6) Uani 1 1 d D . . . .
C10 C 0.6120(2) 0.7087(3) 0.79697(15) 0.0299(6) Uani 1 1 d . . . . .
H10A H 0.675474 0.628255 0.808443 0.036 Uiso 1 1 calc R U . . .
H10B H 0.627090 0.777206 0.753921 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4461(3) 0.7804(3) 0.83937(16) 0.0305(6) Uani 1 1 d . . . . .
H11A H 0.409392 0.871335 0.809586 0.037 Uiso 1 1 calc R U . . .
H11B H 0.397965 0.748321 0.879458 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4829(3) 0.6364(3) 0.78991(14) 0.0261(6) Uani 1 1 d . . . . .
H12 H 0.481774 0.532735 0.817872 0.031 Uiso 1 1 calc R U . . .
C13 C 0.4427(2) 0.4369(3) 0.65786(13) 0.0207(5) Uani 1 1 d . . . . .
C14 C 0.3920(2) 0.2920(3) 0.68013(14) 0.0232(5) Uani 1 1 d . . . . .
H14 H 0.337167 0.293336 0.716154 0.028 Uiso 1 1 calc R U . . .
C15 C 0.4236(3) 0.1458(3) 0.64832(16) 0.0298(6) Uani 1 1 d . . . . .
H15 H 0.390143 0.048132 0.662847 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5049(3) 0.1454(3) 0.59503(19) 0.0370(7) Uani 1 1 d . . . . .
H16 H 0.526118 0.046911 0.573736 0.044 Uiso 1 1 calc R U . . .
C17 C 0.5556(3) 0.2897(4) 0.57275(19) 0.0432(8) Uani 1 1 d . . . . .
H17 H 0.609996 0.287908 0.536477 0.052 Uiso 1 1 calc R U . . .
C18 C 0.5250(3) 0.4374(3) 0.60467(16) 0.0325(6) Uani 1 1 d . . . . .
H18 H 0.559192 0.534868 0.590519 0.039 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       DTREK
_computing_cell_refinement       DTREK
_computing_data_reduction        DTREK
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O3 1.439(2) . ?
S1 O4 1.4436(18) . ?
S1 C13 1.766(2) . ?
S1 C12 1.780(3) . ?
O1 C3 1.374(3) . ?
O1 C2 1.424(3) . ?
O2A C2 1.391(3) . ?
O2A C9 1.442(3) . ?
O2B C2 1.274(10) . ?
O2B C9 1.487(10) . ?
C1 C2 1.494(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2 0.9800 . ?
C3 C8 1.390(4) . ?
C3 C4 1.403(3) . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.514(3) . ?
C9 C10 1.542(4) . ?
C9 C11 1.545(4) . ?
C10 C12 1.547(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.546(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C13 C18 1.384(4) . ?
C13 C14 1.389(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(4) . ?
C17 H17 0.9300 . ?
C18 H18 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
O3 S1 O4 119.55(12) . . ?
O3 S1 C13 107.91(11) . . ?
O4 S1 C13 108.52(11) . . ?
O3 S1 C12 106.13(13) . . ?
O4 S1 C12 108.48(12) . . ?
C13 S1 C12 105.38(12) . . ?
C3 O1 C2 112.7(2) . . ?
C2 O2A C9 111.4(2) . . ?
C2 O2B C9 115.7(8) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2B C2 O1 129.4(5) . . ?
O2A C2 O1 110.9(2) . . ?
O2B C2 C1 120.3(6) . . ?
O2A C2 C1 109.9(2) . . ?
O1 C2 C1 108.8(2) . . ?
O2A C2 H2 109.0 . . ?
O1 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
O1 C3 C8 122.0(2) . . ?
O1 C3 C4 117.1(2) . . ?
C8 C3 C4 121.0(2) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 118.7(2) . . ?
C3 C8 C9 119.4(2) . . ?
C7 C8 C9 121.9(2) . . ?
O2A C9 C8 109.1(2) . . ?
O2B C9 C8 110.1(5) . . ?
O2A C9 C10 104.3(2) . . ?
O2B C9 C10 126.5(5) . . ?
C8 C9 C10 120.3(2) . . ?
O2A C9 C11 113.4(2) . . ?
O2B C9 C11 81.7(5) . . ?
C8 C9 C11 119.2(2) . . ?
C10 C9 C11 88.60(19) . . ?
C9 C10 C12 88.1(2) . . ?
C9 C10 H10A 114.0 . . ?
C12 C10 H10A 114.0 . . ?
C9 C10 H10B 114.0 . . ?
C12 C10 H10B 114.0 . . ?
H10A C10 H10B 111.2 . . ?
C9 C11 C12 87.96(19) . . ?
C9 C11 H11A 114.0 . . ?
C12 C11 H11A 114.0 . . ?
C9 C11 H11B 114.0 . . ?
C12 C11 H11B 114.0 . . ?
H11A C11 H11B 111.2 . . ?
C11 C12 C10 88.37(19) . . ?
C11 C12 S1 114.13(19) . . ?
C10 C12 S1 119.31(19) . . ?
C11 C12 H12 111.0 . . ?
C10 C12 H12 111.0 . . ?
S1 C12 H12 111.0 . . ?
C18 C13 C14 121.1(2) . . ?
C18 C13 S1 120.45(18) . . ?
C14 C13 S1 118.40(18) . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 118.8(2) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?

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
C9 O2B C2 O1 20.8(17) . . . . ?
C9 O2B C2 C1 -143.5(7) . . . . ?
C9 O2A C2 O1 -69.8(3) . . . . ?
C9 O2A C2 C1 169.8(2) . . . . ?
C3 O1 C2 O2B 6.7(10) . . . . ?
C3 O1 C2 O2A 51.4(3) . . . . ?
C3 O1 C2 C1 172.4(2) . . . . ?
C2 O1 C3 C8 -16.4(3) . . . . ?
C2 O1 C3 C4 164.0(2) . . . . ?
O1 C3 C4 C5 -178.7(2) . . . . ?
C8 C3 C4 C5 1.8(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
O1 C3 C8 C7 178.9(2) . . . . ?
C4 C3 C8 C7 -1.6(4) . . . . ?
O1 C3 C8 C9 -1.3(4) . . . . ?
C4 C3 C8 C9 178.2(2) . . . . ?
C6 C7 C8 C3 0.6(4) . . . . ?
C6 C7 C8 C9 -179.2(2) . . . . ?
C2 O2A C9 C8 48.1(3) . . . . ?
C2 O2A C9 C10 177.8(2) . . . . ?
C2 O2A C9 C11 -87.5(3) . . . . ?
C2 O2B C9 C8 -35.4(13) . . . . ?
C2 O2B C9 C10 124.4(9) . . . . ?
C2 O2B C9 C11 -153.5(12) . . . . ?
C3 C8 C9 O2A -13.9(3) . . . . ?
C7 C8 C9 O2A 165.9(2) . . . . ?
C3 C8 C9 O2B 27.0(7) . . . . ?
C7 C8 C9 O2B -153.2(7) . . . . ?
C3 C8 C9 C10 -134.2(2) . . . . ?
C7 C8 C9 C10 45.6(4) . . . . ?
C3 C8 C9 C11 118.7(3) . . . . ?
C7 C8 C9 C11 -61.6(3) . . . . ?
O2A C9 C10 C12 94.0(2) . . . . ?
O2B C9 C10 C12 58.7(7) . . . . ?
C8 C9 C10 C12 -143.3(2) . . . . ?
C11 C9 C10 C12 -19.85(19) . . . . ?
O2A C9 C11 C12 -85.1(2) . . . . ?
O2B C9 C11 C12 -107.4(6) . . . . ?
C8 C9 C11 C12 144.2(2) . . . . ?
C10 C9 C11 C12 19.86(19) . . . . ?
C9 C11 C12 C10 -19.80(19) . . . . ?
C9 C11 C12 S1 -141.39(18) . . . . ?
C9 C10 C12 C11 19.84(19) . . . . ?
C9 C10 C12 S1 136.78(18) . . . . ?
O3 S1 C12 C11 -58.6(2) . . . . ?
O4 S1 C12 C11 71.0(2) . . . . ?
C13 S1 C12 C11 -172.92(18) . . . . ?
O3 S1 C12 C10 -161.08(19) . . . . ?
O4 S1 C12 C10 -31.4(2) . . . . ?
C13 S1 C12 C10 84.6(2) . . . . ?
O3 S1 C13 C18 146.5(2) . . . . ?
O4 S1 C13 C18 15.6(3) . . . . ?
C12 S1 C13 C18 -100.4(2) . . . . ?
O3 S1 C13 C14 -32.1(2) . . . . ?
O4 S1 C13 C14 -163.00(19) . . . . ?
C12 S1 C13 C14 81.0(2) . . . . ?
C18 C13 C14 C15 -0.4(4) . . . . ?
S1 C13 C14 C15 178.25(19) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C14 C13 C18 C17 0.7(4) . . . . ?
S1 C13 C18 C17 -177.9(2) . . . . ?
C16 C17 C18 C13 -0.7(5) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
