# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_9250
_database_code_depnum_ccdc_archive 'CCDC 2062315'
loop_
_audit_author_name
_audit_author_address
'Dr. Patrick J. Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-03-04 downloaded from the CCDC.
;

#Crystallographer: Michael R. Gau

_audit_creation_date             2020-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C18 H24 O7 S'
_chemical_formula_sum            'C18 H24 O7 S'
_chemical_formula_weight         384.43
_chemical_absolute_configuration ad

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.1341(2)
_cell_length_b                   5.53710(10)
_cell_length_c                   15.0402(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.768(2)
_cell_angle_gamma                90
_cell_volume                     1001.03(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12851
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.2720
_cell_measurement_theta_min      3.1490
_exptl_absorpt_coefficient_mu    1.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       bar
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16678
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.497
_diffrn_reflns_theta_min         3.211
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 120.00   0.50    0.05    --   47.20  77.00  90.00  190
  2  ω     91.00 178.00   0.50    0.10    --  107.75  61.00  90.00  174
  3  ω     95.00 178.00   0.50    0.10    --  107.75  45.00  60.00  166
  4  ω     95.00 178.00   0.50    0.10    --  107.75  30.00  30.00  166
  5  ω     95.00 178.00   0.50    0.10    --  107.75  30.00   0.00  166
  6  ω     94.00 178.00   0.50    0.10    --  107.75  15.00 -30.00  168
  7  ω     95.00 178.00   0.50    0.10    --  107.75  30.00-150.00  166
  8  ω     35.00 106.00   0.50    0.10    --  107.75 -94.00   0.00  142
  9  ω     35.00 112.00   0.50    0.10    --  107.75-125.00 120.00  154
 10  ω     35.00 112.00   0.50    0.10    --  107.75-125.00 150.00  154
 11  ω     35.00 112.00   0.50    0.10    --  107.75-125.00  90.00  154
 12  ω     34.00  95.00   0.50    0.05    --   47.20-125.00  30.00  122
 13  ω     35.00 112.00   0.50    0.10    --  107.75-125.00-120.00  154
 14  ω     35.00 112.00   0.50    0.10    --  107.75-125.00-180.00  154
 15  ω     35.00 107.00   0.50    0.10    --  107.75-108.00-178.39  144
 16  ω     35.00 107.00   0.50    0.10    --  107.75-104.00 -68.06  144
 17  ω     35.00 106.00   0.50    0.10    --  107.75 -94.00 -30.00  142
 18  ω     35.00 106.00   0.50    0.10    --  107.75 -94.00 -60.00  142
 19  ω    -26.00  39.00   0.50    0.05    --   47.20 -37.00 -30.00  130
 20  ω     35.00 103.00   0.50    0.10    --  107.75 -77.00 120.00  136
 21  ω     35.00 103.00   0.50    0.10    --  107.75 -77.00   0.00  136
 22  ω     35.00 103.00   0.50    0.10    --  107.75 -77.00-150.00  136
 23  ω     35.00 103.00   0.50    0.10    --  107.75 -77.00-180.00  136
 24  ω     35.00  68.00   0.50    0.10    --  107.75 -61.00-150.00   66
 25  ω     35.00  68.00   0.50    0.10    --  107.75 -61.00-120.00   66
 26  ω     35.00  68.00   0.50    0.10    --  107.75 -61.00-180.00   66
 27  ω     35.00  68.00   0.50    0.10    --  107.75 -61.00 -30.00   66
 28  ω     35.00  68.00   0.50    0.10    --  107.75 -61.00  30.00   66
 29  ω     35.00  68.00   0.50    0.10    --  107.75 -61.00  90.00   66
 30  ω     35.00  68.00   0.50    0.10    --  107.75 -61.00 150.00   66
 31  ω    -29.00  28.00   0.50    0.05    --  -47.20  19.00-180.00  114
 32  ω    -86.00 -13.00   0.50    0.05    --  -47.20 125.00-180.00  146
 33  ω    -38.00 -11.00   0.50    0.10    --  -86.25  30.00 -60.00   54
 34  ω   -159.00 -83.00   0.50    0.10    --  -86.25 -94.00  90.00  152
 35  ω   -120.00 -73.00   0.50    0.05    --  -47.20-125.00 -90.00   94
 36  ω   -120.00 -73.00   0.50    0.05    --  -47.20-125.00-120.00   94
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0112477000
_diffrn_orient_matrix_UB_12      -0.1240576000
_diffrn_orient_matrix_UB_13      -0.0951984000
_diffrn_orient_matrix_UB_21      -0.0109798000
_diffrn_orient_matrix_UB_22      -0.2469883000
_diffrn_orient_matrix_UB_23      0.0425800000
_diffrn_orient_matrix_UB_31      -0.1271362000
_diffrn_orient_matrix_UB_32      0.0322197000
_diffrn_orient_matrix_UB_33      -0.0406011000
_diffrn_oxdiff_digest_frames     
;
01cb3c8603cc30ddc3b5af28768638f0e00459217ad
;
_diffrn_oxdiff_digest_hkl        
;
019d9026f2b584f1f95d1952b6f175c4b76617
;
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                3923
_reflns_number_total             3995
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3995
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.1843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0704
_refine_special_details          
;
The data were corrected for the presence of disordered solvent using
the program SQUEEZE.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual

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 0.16085(3) 0.31441(9) 0.09277(3) 0.02334(12) Uani 1 1 d . . . . .
O1 O 0.67026(10) 0.7869(3) 0.29088(10) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.62767(10) 0.5682(3) 0.45493(10) 0.0222(3) Uani 1 1 d . . . . .
O3 O 0.78219(11) 0.8023(3) 0.51346(11) 0.0277(3) Uani 1 1 d . . . . .
O4 O 0.90168(11) 0.5048(3) 0.36468(10) 0.0230(3) Uani 1 1 d . . . . .
O5 O 0.81365(10) 0.7583(3) 0.23828(10) 0.0228(3) Uani 1 1 d . . . . .
O6 O 0.10102(12) 0.4190(4) 0.14457(12) 0.0346(4) Uani 1 1 d . . . . .
O7 O 0.15139(12) 0.0583(3) 0.07414(15) 0.0425(5) Uani 1 1 d . . . . .
C1 C 0.65134(14) 0.5365(3) 0.30366(14) 0.0185(4) Uani 1 1 d . . . . .
H1 H 0.690532 0.439102 0.272957 0.022 Uiso 1 1 calc R . . . .
C2 C 0.69851(14) 0.4755(4) 0.41199(14) 0.0188(4) Uani 1 1 d . . . . .
H2 H 0.707104 0.300378 0.421532 0.023 Uiso 1 1 calc R . . . .
C3 C 0.68882(15) 0.7280(4) 0.53276(15) 0.0234(4) Uani 1 1 d . . . . .
C4 C 0.81061(16) 0.6040(4) 0.46796(14) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.862142 0.495639 0.517054 0.027 Uiso 1 1 calc R . . . .
C5 C 0.86462(15) 0.7047(4) 0.40413(14) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.927293 0.809685 0.441795 0.025 Uiso 1 1 calc R . . . .
C6 C 0.90418(15) 0.5892(4) 0.27568(15) 0.0213(4) Uani 1 1 d . . . . .
C7 C 0.78333(14) 0.8370(4) 0.31361(14) 0.0210(4) Uani 1 1 d . . . . .
H7 H 0.795868 1.011435 0.322640 0.025 Uiso 1 1 calc R . . . .
C8 C 0.6182(2) 0.9445(4) 0.5276(2) 0.0368(6) Uani 1 1 d . . . . .
H8a H 0.594348 1.016763 0.464393 0.055 Uiso 1 1 calc GR . . . .
H8b H 0.660765 1.059593 0.576076 0.055 Uiso 1 1 calc GR . . . .
H8c H 0.554362 0.895874 0.538989 0.055 Uiso 1 1 calc GR . . . .
C9 C 0.72689(18) 0.5945(5) 0.62913(16) 0.0309(5) Uani 1 1 d . . . . .
H9a H 0.663094 0.540266 0.639473 0.046 Uiso 1 1 calc GR . . . .
H9b H 0.770323 0.701124 0.680864 0.046 Uiso 1 1 calc GR . . . .
H9c H 0.771285 0.457872 0.627874 0.046 Uiso 1 1 calc GR . . . .
C10 C 1.01337(15) 0.7176(4) 0.29485(15) 0.0247(4) Uani 1 1 d . . . . .
H10a H 1.015597 0.764352 0.234194 0.037 Uiso 1 1 calc GR . . . .
H10b H 1.074316 0.610869 0.328815 0.037 Uiso 1 1 calc GR . . . .
H10c H 1.019142 0.858795 0.333663 0.037 Uiso 1 1 calc GR . . . .
C11 C 0.8825(2) 0.3825(4) 0.20581(18) 0.0315(5) Uani 1 1 d . . . . .
H11a H 0.812480 0.308913 0.195753 0.047 Uiso 1 1 calc GR . . . .
H11b H 0.940851 0.265158 0.232031 0.047 Uiso 1 1 calc GR . . . .
H11c H 0.880190 0.441093 0.144965 0.047 Uiso 1 1 calc GR . . . .
C12 C 0.52820(14) 0.4847(4) 0.25296(14) 0.0189(4) Uani 1 1 d . . . . .
C13 C 0.44858(16) 0.6501(4) 0.25354(15) 0.0230(4) Uani 1 1 d . . . . .
H13 H 0.470988 0.795408 0.286703 0.028 Uiso 1 1 calc R . . . .
C14 C 0.33596(16) 0.5995(4) 0.20498(15) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.282787 0.710638 0.204829 0.028 Uiso 1 1 calc R . . . .
C15 C 0.30412(15) 0.3815(4) 0.15685(14) 0.0214(4) Uani 1 1 d . . . . .
C16 C 0.38174(16) 0.2119(4) 0.15755(16) 0.0275(4) Uani 1 1 d . . . . .
H16 H 0.359091 0.064864 0.125759 0.033 Uiso 1 1 calc R . . . .
C17 C 0.49423(16) 0.2648(4) 0.20660(16) 0.0265(4) Uani 1 1 d . . . . .
H17 H 0.547177 0.151329 0.208282 0.032 Uiso 1 1 calc R . . . .
C18 C 0.12218(17) 0.4673(5) -0.01841(16) 0.0307(5) Uani 1 1 d . . . . .
H18a H 0.044884 0.438392 -0.057658 0.046 Uiso 1 1 calc GR . . . .
H18b H 0.166177 0.409631 -0.051785 0.046 Uiso 1 1 calc GR . . . .
H18c H 0.134340 0.637408 -0.006555 0.046 Uiso 1 1 calc GR . . . .


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 O6 1.4331(17) . ?
S1 O7 1.4414(19) . ?
S1 C15 1.7736(18) . ?
S1 C18 1.757(2) . ?
O1 C1 1.435(2) . ?
O1 C7 1.411(2) . ?
O2 C2 1.425(2) . ?
O2 C3 1.428(2) . ?
O3 C3 1.430(2) . ?
O3 C4 1.421(3) . ?
O4 C5 1.431(2) . ?
O4 C6 1.431(2) . ?
O5 C6 1.438(2) . ?
O5 C7 1.413(2) . ?
C1 C2 1.529(3) . ?
C1 C12 1.512(2) . ?
C2 C4 1.544(3) . ?
C3 C8 1.498(3) . ?
C3 C9 1.521(3) . ?
C4 C5 1.512(3) . ?
C5 C7 1.536(3) . ?
C6 C10 1.521(3) . ?
C6 C11 1.502(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.385(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.383(3) . ?
C16 C17 1.391(3) . ?

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
O6 S1 O7 118.70(12) . . ?
O6 S1 C15 108.30(10) . . ?
O6 S1 C18 108.13(11) . . ?
O7 S1 C15 107.53(9) . . ?
O7 S1 C18 108.66(13) . . ?
C18 S1 C15 104.64(10) . . ?
C7 O1 C1 112.32(15) . . ?
C2 O2 C3 109.90(13) . . ?
C4 O3 C3 106.77(16) . . ?
C6 O4 C5 105.98(15) . . ?
C7 O5 C6 110.06(14) . . ?
O1 C1 C2 109.78(16) . . ?
O1 C1 C12 108.87(15) . . ?
C12 C1 C2 112.78(15) . . ?
O2 C2 C1 110.19(15) . . ?
O2 C2 C4 103.89(15) . . ?
C1 C2 C4 111.53(16) . . ?
O2 C3 O3 104.89(15) . . ?
O2 C3 C8 108.74(18) . . ?
O2 C3 C9 109.89(17) . . ?
O3 C3 C8 108.82(18) . . ?
O3 C3 C9 110.72(16) . . ?
C8 C3 C9 113.41(19) . . ?
O3 C4 C2 103.94(15) . . ?
O3 C4 C5 107.59(18) . . ?
C5 C4 C2 114.34(16) . . ?
O4 C5 C4 107.64(17) . . ?
O4 C5 C7 103.44(15) . . ?
C4 C5 C7 113.74(15) . . ?
O4 C6 O5 104.57(14) . . ?
O4 C6 C10 110.54(16) . . ?
O4 C6 C11 109.65(18) . . ?
O5 C6 C10 109.74(17) . . ?
O5 C6 C11 109.20(17) . . ?
C11 C6 C10 112.82(16) . . ?
O1 C7 O5 110.76(15) . . ?
O1 C7 C5 114.13(16) . . ?
O5 C7 C5 104.12(15) . . ?
C13 C12 C1 121.72(18) . . ?
C17 C12 C1 118.87(17) . . ?
C17 C12 C13 119.40(17) . . ?
C14 C13 C12 120.51(19) . . ?
C15 C14 C13 118.97(19) . . ?
C14 C15 S1 119.88(15) . . ?
C14 C15 C16 121.49(17) . . ?
C16 C15 S1 118.63(16) . . ?
C15 C16 C17 118.9(2) . . ?
C12 C17 C16 120.69(19) . . ?

# SQUEEZE RESULTS (Version = 101019)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 -0.051 1.000 121 34 ' '
_platon_squeeze_void_probe_radius 1.20
