# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_tcd409
_database_code_depnum_ccdc_archive 'CCDC 1958067'
loop_
_audit_author_name
_audit_author_address
Brendan
;TCD
Republic of Ireland
;
_audit_update_record             
;
2019-10-08 deposited with the CCDC.	2020-01-24 downloaded from the CCDC.
;
_audit_creation_date             2016-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H28 Na O7 S, C H4 O'
_chemical_formula_sum            'C19 H32 Na O8 S'
_chemical_formula_weight         443.49
_chemical_melting_point          ?
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'
Na Na 0.1353 0.1239 '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'

_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                   4.8228(4)
_cell_length_b                   15.0261(16)
_cell_length_c                   15.5936(15)
_cell_angle_alpha                88.598(8)
_cell_angle_beta                 88.036(6)
_cell_angle_gamma                82.569(7)
_cell_volume                     1119.66(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4176
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0896 after correction.
The Ratio of minimum to maximum transmission is 0.7995.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             474
_exptl_crystal_recrystallization_method 'MeOH crystallization'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12214
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.288
_diffrn_reflns_theta_min         2.836
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'DUO Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3026
_reflns_number_total             4041
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX 3 (Bruker, 2015) '
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'XP (Bruker, 2008-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'

_refine_diff_density_max         0.893
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.1107
_refine_ls_restrained_S_all      1.093
_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)+(0.1122P)²+6.7122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2990
_refine_ls_wR_factor_ref         0.3125
_refine_special_details          
;MeOH solvent modelled over two positions with refined occupancy 
75:25%. Constraints (EADP) and restraints (ISOR, DFIX) used 
in this part of the model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O24-H24
 0.87 with sigma of 0.01
 C2S-O2S
 1.4 with sigma of 0.02
 C25-H24
 1.895249 with sigma of 0.02
 Na1-H24
 3.108011 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1S) \\sim Ueq, Uanis(C1S) \\sim Ueq, Uanis(C2S) \\sim Ueq, Uanis(O2S)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O2S) = Uanis(O1S)
Uanis(C2S) = Uanis(C1S)
4. Others
 Sof(O2S)=Sof(H2S)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=1-FVAR(1)
 Sof(O1S)=Sof(H1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=FVAR(1)
5.a Everything fixed:
 H1S, H2S
5.b Ternary CH refined with riding coordinates:
 C15(H15)
5.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5)
5.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C20(H20A,H20B,H20C), C25(H25A,H25B,H25C), C1S(H1SA,H1SB,
 H1SC), C2S(H2SA,H2SB,H2SC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.4249(14) 0.7151(5) 0.5864(5) 0.0420(16) Uani 1 1 d . . . . .
H1 H 0.3651 0.7683 0.5543 0.050 Uiso 1 1 calc R . . . .
C2 C 0.2837(14) 0.6973(5) 0.6611(4) 0.0399(15) Uani 1 1 d . . . . .
C3 C 0.3670(13) 0.6193(5) 0.7099(5) 0.0392(15) Uani 1 1 d . . . . .
C4 C 0.5974(14) 0.5623(5) 0.6815(5) 0.0415(16) Uani 1 1 d . . . . .
H4 H 0.6585 0.5099 0.7145 0.050 Uiso 1 1 calc R . . . .
C5 C 0.7405(14) 0.5798(5) 0.6064(5) 0.0426(16) Uani 1 1 d . . . . .
H5 H 0.8984 0.5394 0.5884 0.051 Uiso 1 1 calc R . . . .
C6 C 0.6561(14) 0.6566(5) 0.5561(5) 0.0426(16) Uani 1 1 d . . . . .
C8 C -0.0210(16) 0.8355(5) 0.6545(5) 0.0484(17) Uani 1 1 d . . . . .
H8A H 0.1371 0.8705 0.6511 0.073 Uiso 1 1 calc GR . . . .
H8B H -0.1779 0.8690 0.6863 0.073 Uiso 1 1 calc GR . . . .
H8C H -0.0783 0.8243 0.5965 0.073 Uiso 1 1 calc GR . . . .
C10 C 0.8097(15) 0.6772(6) 0.4739(5) 0.0459(17) Uani 1 1 d . . . . .
H10A H 0.9986 0.6424 0.4738 0.055 Uiso 1 1 calc R . . . .
H10B H 0.8334 0.7417 0.4722 0.055 Uiso 1 1 calc R . . . .
C11 C 0.6630(14) 0.6557(5) 0.3927(5) 0.0413(16) Uani 1 1 d . . . . .
H11A H 0.6536 0.5904 0.3918 0.050 Uiso 1 1 calc R . . . .
H11B H 0.4687 0.6866 0.3950 0.050 Uiso 1 1 calc R . . . .
C12 C 0.8072(13) 0.6836(5) 0.3111(5) 0.0420(16) Uani 1 1 d . . . . .
C14 C 0.7178(13) 0.6462(5) 0.2296(5) 0.0380(15) Uani 1 1 d . . . . .
H14A H 0.5109 0.6545 0.2289 0.046 Uiso 1 1 calc R . . . .
H14B H 0.7818 0.5809 0.2290 0.046 Uiso 1 1 calc R . . . .
C15 C 0.8330(13) 0.6903(4) 0.1483(4) 0.0340(14) Uani 1 1 d . . . . .
H15 H 0.9913 0.7222 0.1656 0.041 Uiso 1 1 calc R . . . .
C16 C 0.6211(13) 0.7593(5) 0.1044(5) 0.0388(15) Uani 1 1 d . . . . .
H16A H 0.7142 0.7855 0.0539 0.047 Uiso 1 1 calc R . . . .
H16B H 0.4686 0.7283 0.0832 0.047 Uiso 1 1 calc R . . . .
C17 C 0.4955(13) 0.8341(5) 0.1615(4) 0.0375(15) Uani 1 1 d . . . . .
H17A H 0.6474 0.8651 0.1832 0.045 Uiso 1 1 calc R . . . .
H17B H 0.3996 0.8084 0.2116 0.045 Uiso 1 1 calc R . . . .
C18 C 0.2874(14) 0.9024(5) 0.1156(5) 0.0428(16) Uani 1 1 d . . . . .
H18A H 0.3854 0.9283 0.0660 0.051 Uiso 1 1 calc R . . . .
H18B H 0.1390 0.8707 0.0928 0.051 Uiso 1 1 calc R . . . .
C19 C 0.1521(15) 0.9778(5) 0.1703(5) 0.0457(17) Uani 1 1 d . . . . .
H19A H 0.2993 1.0105 0.1924 0.055 Uiso 1 1 calc R . . . .
H19B H 0.0546 0.9523 0.2202 0.055 Uiso 1 1 calc R . . . .
C20 C -0.0585(15) 1.0444(5) 0.1217(5) 0.0491(18) Uani 1 1 d . . . . .
H20A H 0.0380 1.0717 0.0735 0.074 Uiso 1 1 calc GR . . . .
H20B H -0.1420 1.0914 0.1607 0.074 Uiso 1 1 calc GR . . . .
H20C H -0.2059 1.0126 0.1000 0.074 Uiso 1 1 calc GR . . . .
C25 C 1.4003(15) 0.2348(5) 0.1392(5) 0.0457(17) Uani 1 1 d D . . . .
H25A H 1.5538 0.2286 0.0960 0.069 Uiso 1 1 calc GR . . . .
H25B H 1.2778 0.1888 0.1306 0.069 Uiso 1 1 calc GR . . . .
H25C H 1.4771 0.2274 0.1967 0.069 Uiso 1 1 calc GR . . . .
Na1 Na 1.5260(5) 0.43479(17) 0.08298(16) 0.0357(6) Uani 1 1 d D . . . .
O7 O 0.0605(10) 0.7521(3) 0.6977(3) 0.0430(11) Uani 1 1 d . . . . .
O9 O 0.2335(9) 0.6002(3) 0.7851(3) 0.0381(11) Uani 1 1 d . . . . .
O13 O 0.9911(11) 0.7325(4) 0.3119(3) 0.0547(14) Uani 1 1 d . . . . .
O21 O 1.1724(8) 0.5446(3) 0.1240(3) 0.0365(10) Uani 1 1 d . . . . .
O22 O 0.7390(8) 0.5612(3) 0.0469(3) 0.0343(10) Uani 1 1 d . . . . .
O23 O 1.1049(8) 0.6511(3) 0.0031(3) 0.0353(10) Uani 1 1 d . . . . .
O24 O 1.2444(9) 0.3212(3) 0.1308(3) 0.0384(11) Uani 1 1 d D . . . .
H24 H 1.088(7) 0.3209(17) 0.161(4) 0.058 Uiso 1 1 d DR . . . .
S1 S 0.9736(3) 0.60456(11) 0.07524(10) 0.0324(4) Uani 1 1 d . . . . .
O1S O 0.265(4) 0.9587(11) 0.4844(10) 0.126(5) Uani 0.753(13) 1 d . U P A 1
H1S H 0.0958 0.9821 0.4883 0.188 Uiso 0.7532 1 d . . P A 1
C1S C 0.313(4) 0.9158(12) 0.4075(12) 0.099(5) Uani 0.753(13) 1 d . U P A 1
H1SA H 0.3433 0.9599 0.3619 0.149 Uiso 0.753(13) 1 calc GR . P A 1
H1SB H 0.1506 0.8860 0.3945 0.149 Uiso 0.753(13) 1 calc GR . P A 1
H1SC H 0.4791 0.8711 0.4112 0.149 Uiso 0.753(13) 1 calc GR . P A 1
O2S O 0.496(11) 0.923(3) 0.472(3) 0.126(5) Uani 0.247(13) 1 d D U P A 2
H2S H 0.5682 0.9521 0.5102 0.188 Uiso 0.2468 1 d . . P A 2
C2S C 0.643(12) 0.922(4) 0.392(3) 0.099(5) Uani 0.247(13) 1 d D U P A 2
H2SA H 0.6341 0.8646 0.3645 0.149 Uiso 0.247(13) 1 calc GR . P A 2
H2SB H 0.8394 0.9290 0.4014 0.149 Uiso 0.247(13) 1 calc GR . P A 2
H2SC H 0.5592 0.9713 0.3556 0.149 Uiso 0.247(13) 1 calc GR . P A 2


_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 H1 0.9500 . ?
C1 C2 1.367(10) . ?
C1 C6 1.404(11) . ?
C2 C3 1.404(10) . ?
C2 O7 1.383(9) . ?
C3 C4 1.380(10) . ?
C3 O9 1.361(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(11) . ?
C6 C10 1.504(10) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 O7 1.423(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.532(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.506(10) . ?
C12 C14 1.499(10) . ?
C12 O13 1.224(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.537(9) . ?
C15 H15 1.0000 . ?
C15 C16 1.526(9) . ?
C15 S1 1.792(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.504(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.523(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.501(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.536(10) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 O24 1.419(9) . ?
Na1 Na1 3.205(5) 2_865 ?
Na1 O9 2.410(5) 2_766 ?
Na1 O21 2.300(5) . ?
Na1 O22 2.426(5) 2_765 ?
Na1 O22 2.322(5) 1_655 ?
Na1 O23 2.442(5) 2_865 ?
Na1 O24 2.404(5) . ?
O9 Na1 2.410(5) 2_766 ?
O21 S1 1.450(5) . ?
O22 Na1 2.322(5) 1_455 ?
O22 Na1 2.426(5) 2_765 ?
O22 S1 1.463(4) . ?
O23 Na1 2.442(5) 2_865 ?
O23 S1 1.477(5) . ?
O24 H24 0.875(10) . ?
O1S H1S 0.8459 . ?
O1S C1S 1.37(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
O2S H2S 0.8567 . ?
O2S C2S 1.41(2) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?

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 H1 119.3 . . ?
C2 C1 C6 121.5(7) . . ?
C6 C1 H1 119.3 . . ?
C1 C2 C3 120.6(7) . . ?
C1 C2 O7 125.8(7) . . ?
O7 C2 C3 113.6(6) . . ?
C4 C3 C2 118.4(7) . . ?
O9 C3 C2 122.1(6) . . ?
O9 C3 C4 119.5(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(7) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(7) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C10 120.9(7) . . ?
C5 C6 C1 117.4(7) . . ?
C5 C6 C10 121.7(7) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
C6 C10 H10A 108.7 . . ?
C6 C10 H10B 108.7 . . ?
C6 C10 C11 114.0(6) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.4(6) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C14 C12 C11 116.3(6) . . ?
O13 C12 C11 121.4(7) . . ?
O13 C12 C14 122.3(7) . . ?
C12 C14 H14A 108.9 . . ?
C12 C14 H14B 108.9 . . ?
C12 C14 C15 113.3(6) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15 107.4 . . ?
C14 C15 S1 109.2(5) . . ?
C16 C15 C14 114.3(5) . . ?
C16 C15 H15 107.4 . . ?
C16 C15 S1 110.8(5) . . ?
S1 C15 H15 107.4 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.9(6) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C16 C17 C18 112.7(6) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.5 . . ?
C19 C18 C17 114.8(6) . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C18 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C18 C19 C20 113.1(6) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
O9 Na1 Na1 144.94(18) 2_766 2_865 ?
O9 Na1 O22 168.28(19) 2_766 2_765 ?
O9 Na1 O23 93.01(17) 2_766 2_865 ?
O21 Na1 Na1 77.52(15) . 2_865 ?
O21 Na1 O9 102.35(19) . 2_766 ?
O21 Na1 O22 82.72(17) . 2_765 ?
O21 Na1 O22 80.46(17) . 1_655 ?
O21 Na1 O23 161.2(2) . 2_865 ?
O21 Na1 O24 90.06(18) . . ?
O22 Na1 Na1 46.20(12) 2_765 2_865 ?
O22 Na1 Na1 48.94(13) 1_655 2_865 ?
O22 Na1 O9 96.12(18) 1_655 2_766 ?
O22 Na1 O22 95.14(16) 1_655 2_765 ?
O22 Na1 O23 87.25(17) 1_655 2_865 ?
O22 Na1 O23 84.29(16) 2_765 2_865 ?
O22 Na1 O24 170.5(2) 1_655 . ?
O23 Na1 Na1 83.68(15) 2_865 2_865 ?
O24 Na1 Na1 130.12(16) . 2_865 ?
O24 Na1 O9 84.75(17) . 2_766 ?
O24 Na1 O22 84.68(17) . 2_765 ?
O24 Na1 O23 102.22(18) . 2_865 ?
C2 O7 C8 116.4(6) . . ?
C3 O9 Na1 123.0(4) . 2_766 ?
S1 O21 Na1 132.2(3) . . ?
Na1 O22 Na1 84.86(16) 1_455 2_765 ?
S1 O22 Na1 135.5(3) . 2_765 ?
S1 O22 Na1 137.9(3) . 1_455 ?
S1 O23 Na1 118.2(3) . 2_865 ?
C25 O24 Na1 113.1(4) . . ?
C25 O24 H24 107.8(18) . . ?
Na1 O24 H24 135(2) . . ?
O21 S1 C15 105.4(3) . . ?
O21 S1 O22 113.0(3) . . ?
O21 S1 O23 113.3(3) . . ?
O22 S1 C15 107.2(3) . . ?
O22 S1 O23 111.3(3) . . ?
O23 S1 C15 106.0(3) . . ?
C1S O1S H1S 109.4 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S O2S H2S 113.3 . . ?
O2S C2S H2SA 109.5 . . ?
O2S C2S H2SB 109.5 . . ?
O2S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O24 H24 O9 0.875(10) 2.001(19) 2.755(6) 144(2) 2_666
O1S H1S O1S 0.85 1.89 2.73(4) 170 2_576
O2S H2S O2S 0.86 1.89 2.50(9) 127 2_676

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
C1 C2 C3 C4 1.3(10) . . . . ?
C1 C2 C3 O9 179.1(6) . . . . ?
C1 C2 O7 C8 -2.3(10) . . . . ?
C1 C6 C10 C11 -78.7(9) . . . . ?
C2 C1 C6 C5 -1.2(10) . . . . ?
C2 C1 C6 C10 -179.9(6) . . . . ?
C2 C3 C4 C5 -1.3(10) . . . . ?
C2 C3 O9 Na1 -127.3(5) . . . 2_766 ?
C3 C2 O7 C8 175.5(6) . . . . ?
C3 C4 C5 C6 0.0(10) . . . . ?
C4 C3 O9 Na1 50.6(8) . . . 2_766 ?
C4 C5 C6 C1 1.2(10) . . . . ?
C4 C5 C6 C10 179.9(6) . . . . ?
C5 C6 C10 C11 102.7(8) . . . . ?
C6 C1 C2 C3 0.0(10) . . . . ?
C6 C1 C2 O7 177.7(6) . . . . ?
C6 C10 C11 C12 175.3(7) . . . . ?
C10 C11 C12 C14 166.2(6) . . . . ?
C10 C11 C12 O13 -12.4(10) . . . . ?
C11 C12 C14 C15 169.5(6) . . . . ?
C12 C14 C15 C16 -102.2(6) . . . . ?
C12 C14 C15 S1 133.2(5) . . . . ?
C14 C15 C16 C17 56.8(8) . . . . ?
C14 C15 S1 O21 -54.0(5) . . . . ?
C14 C15 S1 O22 66.6(5) . . . . ?
C14 C15 S1 O23 -174.4(4) . . . . ?
C15 C16 C17 C18 179.4(5) . . . . ?
C16 C15 S1 O21 179.3(4) . . . . ?
C16 C15 S1 O22 -60.1(5) . . . . ?
C16 C15 S1 O23 58.9(5) . . . . ?
C16 C17 C18 C19 179.0(6) . . . . ?
C17 C18 C19 C20 -179.3(6) . . . . ?
Na1 O21 S1 C15 -164.3(3) . . . . ?
Na1 O21 S1 O22 79.0(4) . . . . ?
Na1 O21 S1 O23 -48.8(4) . . . . ?
Na1 O22 S1 C15 -96.3(4) 1_455 . . . ?
Na1 O22 S1 C15 104.5(4) 2_765 . . . ?
Na1 O22 S1 O21 -139.9(4) 2_765 . . . ?
Na1 O22 S1 O21 19.3(5) 1_455 . . . ?
Na1 O22 S1 O23 148.2(4) 1_455 . . . ?
Na1 O22 S1 O23 -11.0(5) 2_765 . . . ?
Na1 O23 S1 C15 156.4(3) 2_865 . . . ?
Na1 O23 S1 O21 41.3(4) 2_865 . . . ?
Na1 O23 S1 O22 -87.4(3) 2_865 . . . ?
O7 C2 C3 C4 -176.7(6) . . . . ?
O7 C2 C3 O9 1.2(9) . . . . ?
O9 C3 C4 C5 -179.2(6) . . . . ?
O13 C12 C14 C15 -12.0(10) . . . . ?
S1 C15 C16 C17 -179.4(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mitegen loop'
_olex2_submission_original_sample_id AR82
_olex2_submission_special_instructions 'No special instructions were received'
