# 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. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1967143'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2019-11-21 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H13 K O9 S'
_chemical_formula_weight         300.32

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'
K K 0.2009 0.2494 '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                   7.1850(14)
_cell_length_b                   10.000(2)
_cell_length_c                   15.059(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1082.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    1845
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      31.4

_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.721
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.710757
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10195
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         31.621
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3142
_reflns_number_gt                1838
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.846
_reflns_Friedel_fraction_full    0.999

_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       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1055P)²+0.4711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.069(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 555 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3142
_refine_ls_number_parameters     177
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.1829
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.041
_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
C2 C -0.0033(11) 0.3975(8) 0.3929(5) 0.0444(18) Uani 1 1 d . . . . .
H2 H -0.046335 0.305803 0.403109 0.053 Uiso 1 1 calc R U . A 1
C3 C 0.1820(10) 0.4153(7) 0.4376(5) 0.0380(16) Uani 1 1 d . . . . .
H3 H 0.220286 0.509140 0.433075 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3269(10) 0.3272(7) 0.3924(5) 0.0377(15) Uani 1 1 d . . . . .
H4 H 0.295822 0.232890 0.402200 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3297(11) 0.3564(7) 0.2928(5) 0.0389(16) Uani 1 1 d . . . . .
H5 H 0.366078 0.449703 0.283221 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4623(11) 0.2656(8) 0.2433(5) 0.0426(16) Uani 1 1 d . . . . .
H6A H 0.405000 0.178343 0.236441 0.051 Uiso 1 1 calc R U . . .
H6B H 0.574378 0.254155 0.278416 0.051 Uiso 1 1 calc R U . . .
C1 C 0.0116(12) 0.4206(8) 0.2936(5) 0.0491(19) Uani 0.697(18) 1 d . . P B 1
H1 H -0.108711 0.397921 0.266835 0.059 Uiso 0.697(18) 1 calc R U P B 1
O1 O 0.0470(11) 0.5487(6) 0.2758(5) 0.041(2) Uani 0.697(18) 1 d D . P B 1
C1A C 0.0116(12) 0.4206(8) 0.2936(5) 0.0491(19) Uani 0.303(18) 1 d D . P B 2
H1A H 0.066049 0.510082 0.288379 0.059 Uiso 0.303(18) 1 calc R U P B 2
O1B O -0.140(3) 0.430(3) 0.2565(13) 0.070(9) Uani 0.303(18) 1 d . . P B 2
O2 O -0.1338(9) 0.4875(6) 0.4312(4) 0.0547(15) Uani 1 1 d . . . . .
H2A H -0.144292 0.471554 0.484363 0.082 Uiso 1 1 calc R U . . .
O3 O 0.1743(8) 0.3778(5) 0.5289(3) 0.0410(12) Uani 1 1 d . . . . .
H3A H 0.100453 0.426302 0.555141 0.062 Uiso 1 1 calc R U . . .
O4 O 0.5067(7) 0.3548(5) 0.4289(3) 0.0414(12) Uani 1 1 d . . . . .
H4A H 0.561612 0.284299 0.438200 0.062 Uiso 1 1 calc R U . . .
O5 O 0.1477(8) 0.3349(6) 0.2566(3) 0.0438(12) Uani 1 1 d . . . . .
O6 O 0.3683(12) 0.3211(12) 0.0797(4) 0.103(3) Uani 1 1 d . . . . .
O7 O 0.5778(13) 0.4648(6) 0.1503(5) 0.082(3) Uani 1 1 d . . . . .
O8 O 0.6728(10) 0.2480(7) 0.1055(4) 0.0649(18) Uani 1 1 d . . . . .
O9 O -0.0556(12) 0.5139(7) 0.0961(5) 0.0624(18) Uani 1 1 d D . . . .
S1 S 0.5246(3) 0.3274(2) 0.13681(13) 0.0466(5) Uani 1 1 d . . . . .
K1 K 0.0299(3) 0.2475(2) 0.08783(14) 0.0581(6) Uani 1 1 d . . . . .
H9A H -0.05(3) 0.560(14) 0.051(6) 0.16(7) Uiso 1 1 d D . . . .
H9B H -0.06(4) 0.54(2) 0.149(5) 0.246 Uiso 1 1 d D U . . .
H1C H -0.043(2) 0.599(3) 0.267(9) 0.246 Uiso 0.697(18) 1 d D U P . .


_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
C2 O2 1.423(9) . ?
C2 C3 1.503(11) . ?
C2 C1 1.516(11) . ?
C2 C1A 1.516(11) . ?
C2 K1 3.518(8) 3 ?
C2 H2 0.9800 . ?
C3 O3 1.426(9) . ?
C3 C4 1.524(10) . ?
C3 H3 0.9800 . ?
C4 O4 1.431(9) . ?
C4 C5 1.528(11) . ?
C4 H4 0.9800 . ?
C5 O5 1.433(10) . ?
C5 C6 1.513(10) . ?
C5 H5 0.9800 . ?
C6 S1 1.776(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C1 O1 1.333(10) . ?
C1 O5 1.414(9) . ?
C1 H1 0.9800 . ?
O1 K1 2.911(8) 3 ?
O1 H1C 0.8300(14) . ?
C1A O1B 1.23(2) . ?
C1A O5 1.414(9) . ?
C1A H1A 0.9800 . ?
O1B K1 3.36(2) . ?
O2 H2A 0.8200 . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?
O5 K1 2.818(5) . ?
O6 S1 1.416(8) . ?
O6 K1 2.543(9) . ?
O6 K1 2.861(8) 4 ?
O7 S1 1.440(7) . ?
O8 S1 1.409(6) . ?
O8 K1 2.580(7) 1_655 ?
O8 K1 3.088(7) 4 ?
O9 K1 2.736(7) . ?
O9 H9A 0.823(14) . ?
O9 H9B 0.823(14) . ?
S1 K1 3.465(3) 4 ?
S1 K1 3.717(3) . ?
S1 K1 3.790(3) 1_655 ?

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 C2 C3 109.1(6) . . ?
O2 C2 C1 110.5(6) . . ?
C3 C2 C1 111.2(7) . . ?
O2 C2 C1A 110.5(6) . . ?
C3 C2 C1A 111.2(7) . . ?
O2 C2 K1 45.6(4) . 3 ?
C3 C2 K1 83.9(4) . 3 ?
C1 C2 K1 86.2(4) . 3 ?
O2 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
K1 C2 H2 154.3 3 . ?
O3 C3 C2 111.5(6) . . ?
O3 C3 C4 107.7(6) . . ?
C2 C3 C4 109.6(6) . . ?
O3 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
O4 C4 C3 109.5(6) . . ?
O4 C4 C5 109.1(6) . . ?
C3 C4 C5 109.7(6) . . ?
O4 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
O5 C5 C6 107.3(6) . . ?
O5 C5 C4 109.4(6) . . ?
C6 C5 C4 112.2(6) . . ?
O5 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C5 C6 S1 113.2(5) . . ?
C5 C6 H6A 108.9 . . ?
S1 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
S1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O1 C1 O5 111.8(7) . . ?
O1 C1 C2 110.9(7) . . ?
O5 C1 C2 110.1(6) . . ?
O1 C1 H1 107.9 . . ?
O5 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
C1 O1 K1 118.6(6) . 3 ?
C1 O1 H1C 117.8(10) . . ?
K1 O1 H1C 63(9) 3 . ?
O1B C1A O5 118.8(13) . . ?
O1B C1A C2 113.5(12) . . ?
O5 C1A C2 110.1(6) . . ?
O1B C1A H1A 104.2 . . ?
O5 C1A H1A 104.2 . . ?
C2 C1A H1A 104.2 . . ?
C1A O1B K1 88.8(12) . . ?
C2 O2 H2A 109.5 . . ?
C3 O3 H3A 109.5 . . ?
C4 O4 H4A 109.5 . . ?
C1A O5 C5 113.0(6) . . ?
C1 O5 C5 113.0(6) . . ?
C1A O5 K1 109.6(4) . . ?
C1 O5 K1 109.6(4) . . ?
C5 O5 K1 131.6(4) . . ?
S1 O6 K1 137.9(4) . . ?
S1 O6 K1 103.0(4) . 4 ?
K1 O6 K1 111.1(3) . 4 ?
S1 O8 K1 141.9(4) . 1_655 ?
S1 O8 K1 93.2(3) . 4 ?
K1 O8 K1 103.48(19) 1_655 4 ?
K1 O9 H9A 120(10) . . ?
K1 O9 H9B 109(10) . . ?
H9A O9 H9B 130(10) . . ?
O8 S1 O6 111.8(5) . . ?
O8 S1 O7 112.6(4) . . ?
O6 S1 O7 109.8(6) . . ?
O8 S1 C6 107.2(4) . . ?
O6 S1 C6 109.5(4) . . ?
O7 S1 C6 105.8(4) . . ?
O8 S1 K1 62.8(3) . 4 ?
O6 S1 K1 53.6(3) . 4 ?
O7 S1 K1 109.9(3) . 4 ?
C6 S1 K1 144.0(3) . 4 ?
O8 S1 K1 122.3(3) . . ?
O6 S1 K1 27.3(3) . . ?
O7 S1 K1 119.1(4) . . ?
C6 S1 K1 82.1(3) . . ?
K1 S1 K1 76.72(6) 4 . ?
O8 S1 K1 24.8(3) . 1_655 ?
O6 S1 K1 129.2(4) . 1_655 ?
O7 S1 K1 88.5(3) . 1_655 ?
C6 S1 K1 110.1(3) . 1_655 ?
K1 S1 K1 75.75(5) 4 1_655 ?
K1 S1 K1 146.31(8) . 1_655 ?
O6 K1 O8 162.8(3) . 1_455 ?
O6 K1 O2 90.5(3) . 3_545 ?
O8 K1 O2 106.6(2) 1_455 3_545 ?
O6 K1 O9 86.3(3) . . ?
O8 K1 O9 76.7(2) 1_455 . ?
O2 K1 O9 175.4(2) 3_545 . ?
O6 K1 O5 70.5(2) . . ?
O8 K1 O5 101.8(2) 1_455 . ?
O2 K1 O5 107.99(19) 3_545 . ?
O9 K1 O5 74.0(2) . . ?
O6 K1 O6 114.5(2) . 4_455 ?
O8 K1 O6 71.8(2) 1_455 4_455 ?
O2 K1 O6 77.8(3) 3_545 4_455 ?
O9 K1 O6 100.5(3) . 4_455 ?
O5 K1 O6 172.6(2) . 4_455 ?
O6 K1 O1 114.4(3) . 3_545 ?
O8 K1 O1 74.9(2) 1_455 3_545 ?
O2 K1 O1 58.23(19) 3_545 3_545 ?
O9 K1 O1 126.2(2) . 3_545 ?
O5 K1 O1 68.43(18) . 3_545 ?
O6 K1 O1 112.4(3) 4_455 3_545 ?
O6 K1 O8 68.46(19) . 4_455 ?
O8 K1 O8 115.3(2) 1_455 4_455 ?
O2 K1 O8 79.82(18) 3_545 4_455 ?
O9 K1 O8 95.9(2) . 4_455 ?
O5 K1 O8 138.28(17) . 4_455 ?
O6 K1 O8 46.1(2) 4_455 4_455 ?
O1 K1 O8 137.56(19) 3_545 4_455 ?
O6 K1 O1B 103.1(4) . . ?
O8 K1 O1B 63.9(4) 1_455 . ?
O2 K1 O1B 134.4(5) 3_545 . ?
O9 K1 O1B 49.8(5) . . ?
O5 K1 O1B 42.1(3) . . ?
O6 K1 O1B 130.6(4) 4_455 . ?
O8 K1 O1B 145.7(5) 4_455 . ?
O6 K1 S1 91.51(18) . 4_455 ?
O8 K1 S1 95.19(16) 1_455 4_455 ?
O2 K1 S1 72.15(14) 3_545 4_455 ?
O9 K1 S1 104.63(17) . 4_455 ?
O5 K1 S1 161.99(14) . 4_455 ?
O6 K1 S1 23.46(17) 4_455 4_455 ?
O1 K1 S1 122.60(15) 3_545 4_455 ?
O8 K1 S1 23.95(12) 4_455 4_455 ?
O6 K1 C2 110.1(3) . 3_545 ?
O8 K1 C2 86.5(2) 1_455 3_545 ?
O2 K1 C2 21.96(17) 3_545 3_545 ?
O9 K1 C2 162.3(2) . 3_545 ?
O5 K1 C2 104.49(18) . 3_545 ?
O6 K1 C2 79.2(3) 4_455 3_545 ?
O1 K1 C2 41.55(18) 3_545 3_545 ?
O8 K1 C2 96.34(17) 4_455 3_545 ?
S1 K1 C2 82.24(14) 4_455 3_545 ?
O6 K1 S1 14.79(15) . . ?
O8 K1 S1 158.46(17) 1_455 . ?
O2 K1 S1 87.93(14) 3_545 . ?
O9 K1 S1 89.79(19) . . ?
O5 K1 S1 57.80(12) . . ?
O6 K1 S1 127.93(18) 4_455 . ?
O1 K1 S1 100.85(17) 3_545 . ?
O8 K1 S1 82.31(12) 4_455 . ?
O1B K1 S1 94.6(3) . . ?
S1 K1 S1 104.52(7) 4_455 . ?
C2 K1 S1 104.45(14) 3_545 . ?

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
O2 C2 C3 O3 65.1(8) . . . . ?
C1 C2 C3 O3 -172.8(6) . . . . ?
C1A C2 C3 O3 -172.8(6) . . . . ?
K1 C2 C3 O3 103.7(5) 3 . . . ?
O2 C2 C3 C4 -175.7(6) . . . . ?
C1 C2 C3 C4 -53.5(8) . . . . ?
C1A C2 C3 C4 -53.5(8) . . . . ?
K1 C2 C3 C4 -137.0(5) 3 . . . ?
O3 C3 C4 O4 -64.6(7) . . . . ?
C2 C3 C4 O4 173.9(6) . . . . ?
O3 C3 C4 C5 175.7(6) . . . . ?
C2 C3 C4 C5 54.2(8) . . . . ?
O4 C4 C5 O5 -177.3(5) . . . . ?
C3 C4 C5 O5 -57.4(8) . . . . ?
O4 C4 C5 C6 63.7(8) . . . . ?
C3 C4 C5 C6 -176.4(6) . . . . ?
O5 C5 C6 S1 78.2(7) . . . . ?
C4 C5 C6 S1 -161.5(5) . . . . ?
O2 C2 C1 O1 53.0(9) . . . . ?
C3 C2 C1 O1 -68.3(9) . . . . ?
K1 C2 C1 O1 13.6(7) 3 . . . ?
O2 C2 C1 O5 177.4(6) . . . . ?
C3 C2 C1 O5 56.1(9) . . . . ?
K1 C2 C1 O5 138.0(6) 3 . . . ?
O5 C1 O1 K1 -142.3(5) . . . 3 ?
C2 C1 O1 K1 -18.9(9) . . . 3 ?
O2 C2 C1A O1B -46.7(18) . . . . ?
C3 C2 C1A O1B -168.0(17) . . . . ?
K1 C2 C1A O1B -86.1(17) 3 . . . ?
O2 C2 C1A O5 177.4(6) . . . . ?
C3 C2 C1A O5 56.1(9) . . . . ?
K1 C2 C1A O5 138.0(6) 3 . . . ?
O5 C1A O1B K1 -7.6(14) . . . . ?
C2 C1A O1B K1 -139.4(7) . . . . ?
O1B C1A O5 C5 165.9(16) . . . . ?
C2 C1A O5 C5 -60.7(8) . . . . ?
O1B C1A O5 K1 9.6(17) . . . . ?
C2 C1A O5 K1 142.9(5) . . . . ?
O1 C1 O5 C5 63.1(8) . . . . ?
C2 C1 O5 C5 -60.7(8) . . . . ?
O1 C1 O5 K1 -93.3(7) . . . . ?
C2 C1 O5 K1 142.9(5) . . . . ?
C6 C5 O5 C1A -176.2(6) . . . . ?
C4 C5 O5 C1A 61.9(8) . . . . ?
C6 C5 O5 C1 -176.2(6) . . . . ?
C4 C5 O5 C1 61.9(8) . . . . ?
C6 C5 O5 K1 -26.5(8) . . . . ?
C4 C5 O5 K1 -148.5(4) . . . . ?
K1 O8 S1 O6 139.3(7) 1_655 . . . ?
K1 O8 S1 O6 22.5(5) 4 . . . ?
K1 O8 S1 O7 15.1(9) 1_655 . . . ?
K1 O8 S1 O7 -101.6(4) 4 . . . ?
K1 O8 S1 C6 -100.8(7) 1_655 . . . ?
K1 O8 S1 C6 142.4(3) 4 . . . ?
K1 O8 S1 K1 116.8(7) 1_655 . . 4 ?
K1 O8 S1 K1 167.7(5) 1_655 . . . ?
K1 O8 S1 K1 50.9(3) 4 . . . ?
K1 O8 S1 K1 -116.8(7) 4 . . 1_655 ?
K1 O6 S1 O8 118.8(9) . . . . ?
K1 O6 S1 O8 -25.0(6) 4 . . . ?
K1 O6 S1 O7 -115.6(10) . . . . ?
K1 O6 S1 O7 100.6(5) 4 . . . ?
K1 O6 S1 C6 0.2(12) . . . . ?
K1 O6 S1 C6 -143.7(3) 4 . . . ?
K1 O6 S1 K1 143.8(13) . . . 4 ?
K1 O6 S1 K1 -143.8(13) 4 . . . ?
K1 O6 S1 K1 139.5(7) . . . 1_655 ?
K1 O6 S1 K1 -4.3(7) 4 . . 1_655 ?
C5 C6 S1 O8 169.2(6) . . . . ?
C5 C6 S1 O6 -69.4(8) . . . . ?
C5 C6 S1 O7 48.8(7) . . . . ?
C5 C6 S1 K1 -123.6(5) . . . 4 ?
C5 C6 S1 K1 -69.3(5) . . . . ?
C5 C6 S1 K1 143.1(5) . . . 1_655 ?

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
C3 H3 O8 0.98 2.58 3.547(10) 170.9 3_655
O2 H2A O7 0.82 2.62 3.358(9) 150.0 2_565
O3 H3A O6 0.82 2.56 3.121(13) 126.6 2_565
O3 H3A O7 0.82 2.21 3.016(10) 168.2 2_565
O3 H3A S1 0.82 2.90 3.657(6) 155.3 2_565
O4 H4A O3 0.82 1.88 2.695(7) 173.9 4_556
O9 H9A O4 0.823(14) 2.05(4) 2.861(8) 170(17) 2_564
O9 H9B O1 0.823(14) 2.06(12) 2.826(11) 155(28) .
O9 H9B O1B 0.823(14) 2.0(2) 2.63(2) 129(24) .
C3 H3 O8 0.98 2.58 3.547(10) 170.9 3_655
O2 H2A O7 0.82 2.62 3.358(9) 150.0 2_565
O3 H3A O6 0.82 2.56 3.121(13) 126.6 2_565
O3 H3A O7 0.82 2.21 3.016(10) 168.2 2_565
O3 H3A S1 0.82 2.90 3.657(6) 155.3 2_565
O4 H4A O3 0.82 1.88 2.695(7) 173.9 4_556
O9 H9A O4 0.823(14) 2.05(4) 2.861(8) 170(17) 2_564
O9 H9B O1 0.823(14) 2.06(12) 2.826(11) 155(28) .
O9 H9B O1B 0.823(14) 2.0(2) 2.63(2) 129(24) .

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.155



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1967144'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2019-11-21 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H13 Na O9 S'
_chemical_formula_weight         284.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0047 0.0022 '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 0.0150 0.0081 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0466 0.0330 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1523 0.1592 '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 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.9360(14)
_cell_length_b                   15.065(3)
_cell_length_c                   9.817(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.38(3)
_cell_angle_gamma                90
_cell_volume                     1025.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    2108
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      31.9

_exptl_crystal_description       prism
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.542
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.799895
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12133
_diffrn_reflns_av_unetI/netI     0.1140
_diffrn_reflns_av_R_equivalents  0.1237
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         31.972
_diffrn_reflns_theta_full        28.680
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             4037
_reflns_number_gt                3847
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.797
_reflns_Friedel_fraction_full    0.929

_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       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0144P)²+3.2395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1576 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4037
_refine_ls_number_parameters     353
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.2562(11) 0.4595(6) 0.9245(10) 0.0289(19) Uani 1 1 d D . . . .
H1 H 0.130813 0.486603 0.904169 0.035 Uiso 1 1 calc R U . . .
C2 C 0.2358(10) 0.3597(5) 0.9085(9) 0.0242(17) Uani 1 1 d D . . . .
H2 H 0.179762 0.346880 0.818684 0.029 Uiso 1 1 calc R U . . .
C3 C 0.4312(10) 0.3130(5) 0.9204(9) 0.0217(16) Uani 1 1 d . . . . .
H3 H 0.478120 0.317811 1.014490 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5756(10) 0.3561(5) 0.8262(9) 0.0218(16) Uani 1 1 d . . . . .
H4 H 0.539729 0.344738 0.731097 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5825(10) 0.4562(5) 0.8527(9) 0.0212(16) Uani 1 1 d . . . . .
H5 H 0.623418 0.467322 0.946948 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7161(10) 0.5031(5) 0.7566(9) 0.0230(16) Uani 1 1 d . . . . .
H6A H 0.653426 0.507139 0.668245 0.028 Uiso 1 1 calc R U . . .
H6B H 0.830959 0.467080 0.745800 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2359(12) 0.5440(6) 0.4452(11) 0.033(2) Uani 1 1 d . . . . .
C8 C 0.2560(11) 0.6434(5) 0.4166(10) 0.0244(17) Uani 1 1 d D . . . .
H8 H 0.313578 0.652757 0.326828 0.029 Uiso 1 1 calc R U . . .
C9 C 0.0610(10) 0.6888(5) 0.4234(9) 0.0233(16) Uani 1 1 d D . . . .
H9 H 0.013301 0.686296 0.517050 0.028 Uiso 1 1 calc R U . . .
C10 C -0.0813(11) 0.6421(5) 0.3292(9) 0.0228(16) Uani 1 1 d . . . . .
H10 H -0.048119 0.653484 0.233875 0.027 Uiso 1 1 calc R U . . .
C11 C -0.0821(11) 0.5421(5) 0.3572(9) 0.0232(16) Uani 1 1 d . . . . .
H11 H -0.125446 0.531367 0.450531 0.028 Uiso 1 1 calc R U . . .
C12 C -0.2117(11) 0.4926(5) 0.2590(9) 0.0235(16) Uani 1 1 d . . . . .
H12A H -0.152241 0.491823 0.169806 0.028 Uiso 1 1 calc R U . . .
H12B H -0.333443 0.523860 0.250817 0.028 Uiso 1 1 calc R U . . .
O1 O 0.3931(7) 0.4939(4) 0.8298(7) 0.0251(12) Uani 1 1 d . . . . .
O2 O 0.3021(9) 0.4782(5) 1.0567(7) 0.0342(15) Uani 1 1 d D . . . .
O3 O 0.1172(8) 0.3225(4) 1.0092(7) 0.0305(14) Uani 1 1 d D . . . .
O4 O 0.4163(7) 0.2215(4) 0.8846(6) 0.0231(12) Uani 1 1 d D . . . .
O5 O 0.7624(8) 0.3191(4) 0.8549(7) 0.0261(13) Uani 1 1 d D . . . .
O6 O 0.8148(8) 0.6095(4) 0.9558(6) 0.0276(12) Uani 1 1 d . . . . .
O7 O 0.9680(8) 0.6284(4) 0.7380(7) 0.0296(13) Uani 1 1 d . . . . .
O8 O 0.6362(9) 0.6733(4) 0.7667(8) 0.0360(16) Uani 1 1 d . . . . .
O9 O 0.1095(7) 0.5081(4) 0.3417(7) 0.0272(13) Uani 1 1 d . . . . .
O10 O 0.4071(12) 0.5070(6) 0.4424(11) 0.0294(19) Uani 0.659(12) 1 d D . P A 1
O10A O 0.216(2) 0.5208(12) 0.555(2) 0.0294(19) Uani 0.341(12) 1 d . . P A 2
O11 O 0.3765(8) 0.6823(4) 0.5211(7) 0.0311(14) Uani 1 1 d D . . . .
O12 O 0.0718(7) 0.7788(4) 0.3808(6) 0.0218(11) Uani 1 1 d D . . . .
O13 O -0.2709(7) 0.6773(4) 0.3584(7) 0.0251(13) Uani 1 1 d D . . . .
O14 O -0.0910(8) 0.3272(4) 0.2774(7) 0.0314(14) Uani 1 1 d . . . . .
O15 O -0.2850(8) 0.3855(4) 0.4579(7) 0.0287(13) Uani 1 1 d . . . . .
O16 O -0.4292(8) 0.3531(4) 0.2393(7) 0.0304(13) Uani 1 1 d . . . . .
O17 O 0.3137(8) 0.3375(5) 0.4853(7) 0.0345(15) Uani 1 1 d D . . . .
O18 O 0.2073(9) 0.6559(4) 0.9993(7) 0.0302(14) Uani 1 1 d D . . . .
Na2 Na 0.2323(5) 0.3567(3) 0.2418(4) 0.0407(10) Uani 1 1 d D . . . .
Na1 Na 0.2959(5) 0.6716(4) 0.7642(5) 0.0519(13) Uani 1 1 d D . . . .
S1 S -0.2567(2) 0.38082(12) 0.3120(2) 0.0225(4) Uani 1 1 d . . . . .
S2 S 0.7878(2) 0.61200(12) 0.8081(2) 0.0229(4) Uani 1 1 d . . . . .
H12 H 0.145(12) 0.807(2) 0.431(6) 0.034 Uiso 1 1 d D U . . .
H13 H -0.320(12) 0.678(7) 0.282(4) 0.02(2) Uiso 1 1 d D . . . .
H3A H 0.004(2) 0.323(6) 0.985(5) 0.02(2) Uiso 1 1 d D . . . .
H18B H 0.242(15) 0.694(5) 1.054(4) 0.06(4) Uiso 1 1 d D . . . .
H4A H 0.361(12) 0.200(6) 0.951(6) 0.01(2) Uiso 1 1 d D . . . .
H5A H 0.840(12) 0.311(8) 0.793(8) 0.03(3) Uiso 1 1 d D . . . .
H18A H 0.094(4) 0.652(9) 1.020(4) 0.10(7) Uiso 1 1 d D . . . .
H17A H 0.25(2) 0.370(10) 0.537(4) 0.153 Uiso 1 1 d D U . . .
H17B H 0.424(10) 0.353(13) 0.505(5) 0.153 Uiso 1 1 d D U . . .
H2A H 0.25(4) 0.524(12) 1.088(11) 0.153 Uiso 0.659(12) 1 d D U P . .
H10A H 0.41(3) 0.456(6) 0.41(3) 0.153 Uiso 1 1 d D U . . .
H11A H 0.4896(19) 0.674(16) 0.500(14) 0.153 Uiso 1 1 d D 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
C1 O2 1.364(12) . ?
C1 O1 1.431(10) . ?
C1 C2 1.519(12) . ?
C1 H1 0.9800 . ?
C2 O3 1.407(11) . ?
C2 C3 1.531(10) . ?
C2 H2 0.9800 . ?
C3 O4 1.425(9) . ?
C3 C4 1.514(11) . ?
C3 H3 0.9800 . ?
C4 O5 1.436(9) . ?
C4 C5 1.531(10) . ?
C4 H4 0.9800 . ?
C5 O1 1.447(9) . ?
C5 C6 1.502(11) . ?
C5 H5 0.9800 . ?
C6 S2 1.787(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O10A 1.14(2) . ?
C7 O10 1.312(12) . ?
C7 O9 1.443(11) . ?
C7 C8 1.530(12) . ?
C8 O11 1.443(10) . ?
C8 C9 1.517(10) . ?
C8 H8 0.9800 . ?
C9 O12 1.422(9) . ?
C9 C10 1.521(11) . ?
C9 H9 0.9800 . ?
C10 O13 1.449(9) . ?
C10 C11 1.532(11) . ?
C10 H10 0.9800 . ?
C11 O9 1.433(9) . ?
C11 C12 1.510(11) . ?
C11 H11 0.9800 . ?
C12 S1 1.790(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O1 Na1 2.833(7) . ?
O2 Na2 2.627(8) 1_556 ?
O2 H2A 0.821(15) . ?
O3 Na2 2.468(8) 1_556 ?
O3 H3A 0.821(15) . ?
O4 H4A 0.820(15) . ?
O5 H5A 0.823(15) . ?
O6 S2 1.461(7) . ?
O7 S2 1.452(6) . ?
O7 Na1 2.377(7) 1_655 ?
O8 S2 1.455(6) . ?
O8 Na1 2.360(7) . ?
O8 Na2 2.910(8) 2_656 ?
O9 Na2 2.627(7) . ?
O10 H10A 0.821(15) . ?
O11 Na1 2.460(9) . ?
O11 H11A 0.821(15) . ?
O12 H12 0.823(13) . ?
O13 H13 0.821(15) . ?
O14 S1 1.447(6) . ?
O14 Na2 2.314(7) . ?
O14 Na1 2.771(8) 2_546 ?
O15 S1 1.449(7) . ?
O16 S1 1.451(6) . ?
O16 Na2 2.349(6) 1_455 ?
O16 Na1 2.887(9) 2_546 ?
O17 Na2 2.469(8) . ?
O17 H17A 0.817(15) . ?
O17 H17B 0.819(15) . ?
O18 Na1 2.404(8) . ?
O18 H18B 0.820(15) . ?
O18 H18A 0.818(15) . ?
Na2 H10A 2.57(16) . ?
Na1 S1 3.251(6) 2_556 ?

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 C1 O1 113.1(7) . . ?
O2 C1 C2 108.9(8) . . ?
O1 C1 C2 110.7(7) . . ?
O2 C1 H1 108.0 . . ?
O1 C1 H1 108.0 . . ?
C2 C1 H1 108.0 . . ?
O3 C2 C1 112.1(7) . . ?
O3 C2 C3 106.5(7) . . ?
C1 C2 C3 111.4(6) . . ?
O3 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
O4 C3 C4 108.1(6) . . ?
O4 C3 C2 111.3(6) . . ?
C4 C3 C2 110.2(7) . . ?
O4 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
O5 C4 C3 108.3(6) . . ?
O5 C4 C5 108.8(6) . . ?
C3 C4 C5 109.8(6) . . ?
O5 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
C5 C4 H4 110.0 . . ?
O1 C5 C6 106.3(6) . . ?
O1 C5 C4 109.4(5) . . ?
C6 C5 C4 112.0(7) . . ?
O1 C5 H5 109.7 . . ?
C6 C5 H5 109.7 . . ?
C4 C5 H5 109.7 . . ?
C5 C6 S2 115.2(6) . . ?
C5 C6 H6A 108.5 . . ?
S2 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
S2 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
O10A C7 O9 118.2(12) . . ?
O10 C7 O9 111.8(9) . . ?
O10A C7 C8 119.0(13) . . ?
O10 C7 C8 109.2(8) . . ?
O9 C7 C8 107.1(7) . . ?
O11 C8 C9 107.4(7) . . ?
O11 C8 C7 108.6(7) . . ?
C9 C8 C7 110.5(7) . . ?
O11 C8 H8 110.1 . . ?
C9 C8 H8 110.1 . . ?
C7 C8 H8 110.1 . . ?
O12 C9 C8 111.6(6) . . ?
O12 C9 C10 107.3(6) . . ?
C8 C9 C10 109.9(7) . . ?
O12 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
O13 C10 C9 107.3(7) . . ?
O13 C10 C11 108.7(6) . . ?
C9 C10 C11 110.4(7) . . ?
O13 C10 H10 110.1 . . ?
C9 C10 H10 110.1 . . ?
C11 C10 H10 110.1 . . ?
O9 C11 C12 107.7(6) . . ?
O9 C11 C10 109.2(6) . . ?
C12 C11 C10 112.0(7) . . ?
O9 C11 H11 109.3 . . ?
C12 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C11 C12 S1 112.5(6) . . ?
C11 C12 H12A 109.1 . . ?
S1 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
S1 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C1 O1 C5 111.3(6) . . ?
C1 O1 Na1 109.4(4) . . ?
C5 O1 Na1 128.3(4) . . ?
C1 O2 Na2 118.1(5) . 1_556 ?
C1 O2 H2A 115(2) . . ?
Na2 O2 H2A 104(10) 1_556 . ?
C2 O3 Na2 112.4(5) . 1_556 ?
C2 O3 H3A 111(2) . . ?
Na2 O3 H3A 124(5) 1_556 . ?
C3 O4 H4A 102(7) . . ?
C4 O5 H5A 120(8) . . ?
S2 O7 Na1 145.2(4) . 1_655 ?
S2 O8 Na1 135.8(4) . . ?
S2 O8 Na2 112.6(3) . 2_656 ?
Na1 O8 Na2 108.9(3) . 2_656 ?
C11 O9 C7 110.5(6) . . ?
C11 O9 Na2 130.8(4) . . ?
C7 O9 Na2 113.1(5) . . ?
C7 O10 H10A 117(10) . . ?
C8 O11 Na1 121.9(5) . . ?
C8 O11 H11A 108.1(19) . . ?
Na1 O11 H11A 117(10) . . ?
C9 O12 H12 110.1(19) . . ?
C10 O13 H13 101(6) . . ?
S1 O14 Na2 134.5(4) . . ?
S1 O14 Na1 95.7(3) . 2_546 ?
Na2 O14 Na1 129.5(3) . 2_546 ?
S1 O16 Na2 144.0(4) . 1_455 ?
S1 O16 Na1 90.9(3) . 2_546 ?
Na2 O16 Na1 110.0(2) 1_455 2_546 ?
Na2 O17 H17A 115(3) . . ?
Na2 O17 H17B 114(3) . . ?
H17A O17 H17B 100(2) . . ?
Na1 O18 H18B 119(3) . . ?
Na1 O18 H18A 120(3) . . ?
H18B O18 H18A 99(2) . . ?
O14 Na2 O16 165.2(3) . 1_655 ?
O14 Na2 O3 78.0(2) . 1_554 ?
O16 Na2 O3 107.6(3) 1_655 1_554 ?
O14 Na2 O17 92.7(3) . . ?
O16 Na2 O17 77.6(2) 1_655 . ?
O3 Na2 O17 160.3(3) 1_554 . ?
O14 Na2 O9 78.1(2) . . ?
O16 Na2 O9 110.5(2) 1_655 . ?
O3 Na2 O9 115.0(3) 1_554 . ?
O17 Na2 O9 79.2(2) . . ?
O14 Na2 O2 114.9(3) . 1_554 ?
O16 Na2 O2 79.6(2) 1_655 1_554 ?
O3 Na2 O2 64.2(2) 1_554 1_554 ?
O17 Na2 O2 135.1(3) . 1_554 ?
O9 Na2 O2 73.4(2) . 1_554 ?
O14 Na2 O8 97.3(3) . 2_646 ?
O16 Na2 O8 70.4(2) 1_655 2_646 ?
O3 Na2 O8 82.8(2) 1_554 2_646 ?
O17 Na2 O8 81.2(3) . 2_646 ?
O9 Na2 O8 159.6(3) . 2_646 ?
O2 Na2 O8 125.6(2) 1_554 2_646 ?
O14 Na2 H10A 119(5) . . ?
O16 Na2 H10A 62(5) 1_655 . ?
O3 Na2 H10A 152(6) 1_554 . ?
O17 Na2 H10A 48(6) . . ?
O9 Na2 H10A 54(4) . . ?
O2 Na2 H10A 87(6) 1_554 . ?
O8 Na2 H10A 115(4) 2_646 . ?
O8 Na1 O7 163.7(4) . 1_455 ?
O8 Na1 O18 104.7(3) . . ?
O7 Na1 O18 80.0(2) 1_455 . ?
O8 Na1 O11 77.0(3) . . ?
O7 Na1 O11 97.8(3) 1_455 . ?
O18 Na1 O11 177.4(3) . . ?
O8 Na1 O14 120.3(3) . 2_556 ?
O7 Na1 O14 74.1(2) 1_455 2_556 ?
O18 Na1 O14 95.2(3) . 2_556 ?
O11 Na1 O14 85.5(2) . 2_556 ?
O8 Na1 O1 76.8(2) . . ?
O7 Na1 O1 89.6(2) 1_455 . ?
O18 Na1 O1 75.6(2) . . ?
O11 Na1 O1 103.1(3) . . ?
O14 Na1 O1 162.6(2) 2_556 . ?
O8 Na1 O16 70.7(2) . 2_556 ?
O7 Na1 O16 124.3(3) 1_455 2_556 ?
O18 Na1 O16 100.8(3) . 2_556 ?
O11 Na1 O16 81.5(2) . 2_556 ?
O14 Na1 O16 50.26(19) 2_556 2_556 ?
O1 Na1 O16 145.3(2) . 2_556 ?
O8 Na1 S1 94.2(2) . 2_556 ?
O7 Na1 S1 99.3(2) 1_455 2_556 ?
O18 Na1 S1 107.1(2) . 2_556 ?
O11 Na1 S1 74.49(19) . 2_556 ?
O14 Na1 S1 26.29(13) 2_556 2_556 ?
O1 Na1 S1 171.03(17) . 2_556 ?
O16 Na1 S1 26.50(12) 2_556 2_556 ?
O14 S1 O15 111.9(4) . . ?
O14 S1 O16 112.2(4) . . ?
O15 S1 O16 112.6(3) . . ?
O14 S1 C12 108.4(4) . . ?
O15 S1 C12 105.5(4) . . ?
O16 S1 C12 105.8(4) . . ?
O14 S1 Na1 58.0(3) . 2_546 ?
O15 S1 Na1 105.2(3) . 2_546 ?
O16 S1 Na1 62.6(3) . 2_546 ?
C12 S1 Na1 149.3(3) . 2_546 ?
O7 S2 O8 112.5(4) . . ?
O7 S2 O6 111.7(3) . . ?
O8 S2 O6 112.4(4) . . ?
O7 S2 C6 105.1(4) . . ?
O8 S2 C6 107.7(4) . . ?
O6 S2 C6 106.9(4) . . ?

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
O2 C1 C2 O3 49.0(9) . . . . ?
O1 C1 C2 O3 173.9(6) . . . . ?
O2 C1 C2 C3 -70.3(9) . . . . ?
O1 C1 C2 C3 54.6(10) . . . . ?
O3 C2 C3 O4 66.5(9) . . . . ?
C1 C2 C3 O4 -171.0(7) . . . . ?
O3 C2 C3 C4 -173.6(7) . . . . ?
C1 C2 C3 C4 -51.0(10) . . . . ?
O4 C3 C4 O5 -66.4(8) . . . . ?
C2 C3 C4 O5 171.8(6) . . . . ?
O4 C3 C4 C5 174.9(6) . . . . ?
C2 C3 C4 C5 53.1(9) . . . . ?
O5 C4 C5 O1 -177.6(7) . . . . ?
C3 C4 C5 O1 -59.3(9) . . . . ?
O5 C4 C5 C6 64.7(9) . . . . ?
C3 C4 C5 C6 -176.9(7) . . . . ?
O1 C5 C6 S2 77.7(7) . . . . ?
C4 C5 C6 S2 -162.8(5) . . . . ?
O10A C7 C8 O11 40.7(14) . . . . ?
O10 C7 C8 O11 -60.7(11) . . . . ?
O9 C7 C8 O11 178.1(7) . . . . ?
O10A C7 C8 C9 -76.9(13) . . . . ?
O10 C7 C8 C9 -178.3(9) . . . . ?
O9 C7 C8 C9 60.5(10) . . . . ?
O11 C8 C9 O12 68.9(9) . . . . ?
C7 C8 C9 O12 -172.8(7) . . . . ?
O11 C8 C9 C10 -172.1(7) . . . . ?
C7 C8 C9 C10 -53.8(10) . . . . ?
O12 C9 C10 O13 -68.8(8) . . . . ?
C8 C9 C10 O13 169.7(7) . . . . ?
O12 C9 C10 C11 172.9(6) . . . . ?
C8 C9 C10 C11 51.4(9) . . . . ?
O13 C10 C11 O9 -174.3(7) . . . . ?
C9 C10 C11 O9 -56.9(9) . . . . ?
O13 C10 C11 C12 66.5(9) . . . . ?
C9 C10 C11 C12 -176.1(7) . . . . ?
O9 C11 C12 S1 73.0(7) . . . . ?
C10 C11 C12 S1 -167.0(5) . . . . ?
O2 C1 O1 C5 61.0(9) . . . . ?
C2 C1 O1 C5 -61.5(9) . . . . ?
O2 C1 O1 Na1 -86.4(7) . . . . ?
C2 C1 O1 Na1 151.1(6) . . . . ?
C6 C5 O1 C1 -175.0(7) . . . . ?
C4 C5 O1 C1 63.9(9) . . . . ?
C6 C5 O1 Na1 -35.4(9) . . . . ?
C4 C5 O1 Na1 -156.5(5) . . . . ?
O1 C1 O2 Na2 -142.5(5) . . . 1_556 ?
C2 C1 O2 Na2 -19.0(8) . . . 1_556 ?
C1 C2 O3 Na2 -56.3(8) . . . 1_556 ?
C3 C2 O3 Na2 65.8(7) . . . 1_556 ?
C12 C11 O9 C7 -172.3(7) . . . . ?
C10 C11 O9 C7 65.9(9) . . . . ?
C12 C11 O9 Na2 -21.2(9) . . . . ?
C10 C11 O9 Na2 -143.0(6) . . . . ?
O10A C7 O9 C11 70.7(13) . . . . ?
O10 C7 O9 C11 173.3(8) . . . . ?
C8 C7 O9 C11 -67.2(9) . . . . ?
O10A C7 O9 Na2 -85.9(13) . . . . ?
O10 C7 O9 Na2 16.8(10) . . . . ?
C8 C7 O9 Na2 136.3(6) . . . . ?
C9 C8 O11 Na1 62.1(8) . . . . ?
C7 C8 O11 Na1 -57.5(8) . . . . ?
Na2 O14 S1 O15 -91.5(6) . . . . ?
Na1 O14 S1 O15 94.8(3) 2_546 . . . ?
Na2 O14 S1 O16 140.9(5) . . . . ?
Na1 O14 S1 O16 -32.8(4) 2_546 . . . ?
Na2 O14 S1 C12 24.4(7) . . . . ?
Na1 O14 S1 C12 -149.3(3) 2_546 . . . ?
Na2 O14 S1 Na1 173.7(7) . . . 2_546 ?
Na2 O16 S1 O14 158.3(6) 1_455 . . . ?
Na1 O16 S1 O14 31.2(4) 2_546 . . . ?
Na2 O16 S1 O15 31.1(8) 1_455 . . . ?
Na1 O16 S1 O15 -96.0(3) 2_546 . . . ?
Na2 O16 S1 C12 -83.6(7) 1_455 . . . ?
Na1 O16 S1 C12 149.2(3) 2_546 . . . ?
Na2 O16 S1 Na1 127.1(7) 1_455 . . 2_546 ?
C11 C12 S1 O14 -79.1(7) . . . . ?
C11 C12 S1 O15 40.9(6) . . . . ?
C11 C12 S1 O16 160.4(6) . . . . ?
C11 C12 S1 Na1 -136.9(5) . . . 2_546 ?
Na1 O7 S2 O8 116.1(7) 1_655 . . . ?
Na1 O7 S2 O6 -11.4(8) 1_655 . . . ?
Na1 O7 S2 C6 -127.0(7) 1_655 . . . ?
Na1 O8 S2 O7 155.6(6) . . . . ?
Na2 O8 S2 O7 -46.0(5) 2_656 . . . ?
Na1 O8 S2 O6 -77.3(7) . . . . ?
Na2 O8 S2 O6 81.1(4) 2_656 . . . ?
Na1 O8 S2 C6 40.2(8) . . . . ?
Na2 O8 S2 C6 -161.4(4) 2_656 . . . ?
C5 C6 S2 O7 156.8(6) . . . . ?
C5 C6 S2 O8 -83.1(7) . . . . ?
C5 C6 S2 O6 37.9(7) . . . . ?

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
C3 H3 O16 0.98 2.35 3.326(11) 170.6 1_656
C9 H9 O7 0.98 2.36 3.287(11) 157.5 1_455
C12 H12B O10 0.97 2.62 3.216(12) 119.7 1_455
O12 H12 O15 0.823(13) 1.876(12) 2.692(8) 171(6) 2_556
O12 H12 S1 0.823(13) 2.86(4) 3.613(6) 153(8) 2_556
O13 H13 O4 0.821(15) 1.88(4) 2.669(9) 161(10) 2_556
O3 H3A O5 0.821(15) 2.10(3) 2.882(9) 159(5) 1_455
O18 H18B O4 0.820(15) 2.48(9) 3.009(8) 123(9) 2_657
O18 H18B O5 0.820(15) 2.09(6) 2.852(9) 155(11) 2_657
O4 H4A O6 0.820(15) 2.06(5) 2.812(8) 153(9) 2_647
O4 H4A S2 0.820(15) 2.91(2) 3.726(6) 172(8) 2_647
O5 H5A O12 0.823(15) 1.88(4) 2.660(9) 158(11) 2_646
O18 H18A O6 0.818(15) 2.13(4) 2.840(8) 146(6) 1_455
O18 H18A S2 0.818(15) 3.02(4) 3.515(7) 121(4) 1_455
O17 H17A O10A 0.817(15) 2.30(13) 2.924(18) 134(16) .
O17 H17B O15 0.819(15) 2.13(4) 2.889(8) 154(7) 1_655
O17 H17B S1 0.819(15) 2.95(6) 3.502(6) 126(6) 1_655
C3 H3 O16 0.98 2.35 3.326(11) 170.6 1_656
C9 H9 O7 0.98 2.36 3.287(11) 157.5 1_455
C12 H12B O10 0.97 2.62 3.216(12) 119.7 1_455
O12 H12 O15 0.823(13) 1.876(12) 2.692(8) 171(6) 2_556
O12 H12 S1 0.823(13) 2.86(4) 3.613(6) 153(8) 2_556
O13 H13 O4 0.821(15) 1.88(4) 2.669(9) 161(10) 2_556
O3 H3A O5 0.821(15) 2.10(3) 2.882(9) 159(5) 1_455
O18 H18B O4 0.820(15) 2.48(9) 3.009(8) 123(9) 2_657
O18 H18B O5 0.820(15) 2.09(6) 2.852(9) 155(11) 2_657
O4 H4A O6 0.820(15) 2.06(5) 2.812(8) 153(9) 2_647
O4 H4A S2 0.820(15) 2.91(2) 3.726(6) 172(8) 2_647
O5 H5A O12 0.823(15) 1.88(4) 2.660(9) 158(11) 2_646
O18 H18A O6 0.818(15) 2.13(4) 2.840(8) 146(6) 1_455
O18 H18A S2 0.818(15) 3.02(4) 3.515(7) 121(4) 1_455
O17 H17A O10A 0.817(15) 2.30(13) 2.924(18) 134(16) .
O17 H17B O15 0.819(15) 2.13(4) 2.889(8) 154(7) 1_655
O17 H17B S1 0.819(15) 2.95(6) 3.502(6) 126(6) 1_655
O2 H2A O18 0.821(15) 2.20(17) 2.812(9) 132(20) .
O10 H10A O15 0.821(15) 2.4(2) 2.816(10) 113(19) 1_655
O10 H10A O16 0.821(15) 2.56(15) 3.267(12) 145(23) 1_655
O10 H10A O17 0.821(15) 2.04(19) 2.669(12) 133(24) .
O10 H10A S1 0.821(15) 2.7(2) 3.276(9) 124(20) 1_655
C3 H3 O16 0.98 2.35 3.326(11) 170.6 1_656
C9 H9 O7 0.98 2.36 3.287(11) 157.5 1_455
C12 H12B O10 0.97 2.62 3.216(12) 119.7 1_455
O12 H12 O15 0.823(13) 1.876(12) 2.692(8) 171(6) 2_556
O12 H12 S1 0.823(13) 2.86(4) 3.613(6) 153(8) 2_556
O13 H13 O4 0.821(15) 1.88(4) 2.669(9) 161(10) 2_556
O3 H3A O5 0.821(15) 2.10(3) 2.882(9) 159(5) 1_455
O18 H18B O4 0.820(15) 2.48(9) 3.009(8) 123(9) 2_657
O18 H18B O5 0.820(15) 2.09(6) 2.852(9) 155(11) 2_657
O4 H4A O6 0.820(15) 2.06(5) 2.812(8) 153(9) 2_647
O4 H4A S2 0.820(15) 2.91(2) 3.726(6) 172(8) 2_647
O5 H5A O12 0.823(15) 1.88(4) 2.660(9) 158(11) 2_646
O18 H18A O6 0.818(15) 2.13(4) 2.840(8) 146(6) 1_455
O18 H18A S2 0.818(15) 3.02(4) 3.515(7) 121(4) 1_455
O17 H17A O10A 0.817(15) 2.30(13) 2.924(18) 134(16) .
O17 H17B O15 0.819(15) 2.13(4) 2.889(8) 154(7) 1_655
O17 H17B S1 0.819(15) 2.95(6) 3.502(6) 126(6) 1_655
O2 H2A O18 0.821(15) 2.20(17) 2.812(9) 132(20) .
O10 H10A O15 0.821(15) 2.4(2) 2.816(10) 113(19) 1_655
O10 H10A O16 0.821(15) 2.56(15) 3.267(12) 145(23) 1_655
O10 H10A O17 0.821(15) 2.04(19) 2.669(12) 133(24) .
O10 H10A S1 0.821(15) 2.7(2) 3.276(9) 124(20) 1_655
O11 H11A O13 0.821(15) 2.17(9) 2.931(9) 153(19) 1_655
C3 H3 O16 0.98 2.35 3.326(11) 170.6 1_656
C9 H9 O7 0.98 2.36 3.287(11) 157.5 1_455
C12 H12B O10 0.97 2.62 3.216(12) 119.7 1_455
O12 H12 O15 0.823(13) 1.876(12) 2.692(8) 171(6) 2_556
O12 H12 S1 0.823(13) 2.86(4) 3.613(6) 153(8) 2_556
O13 H13 O4 0.821(15) 1.88(4) 2.669(9) 161(10) 2_556
O3 H3A O5 0.821(15) 2.10(3) 2.882(9) 159(5) 1_455
O18 H18B O4 0.820(15) 2.48(9) 3.009(8) 123(9) 2_657
O18 H18B O5 0.820(15) 2.09(6) 2.852(9) 155(11) 2_657
O4 H4A O6 0.820(15) 2.06(5) 2.812(8) 153(9) 2_647
O4 H4A S2 0.820(15) 2.91(2) 3.726(6) 172(8) 2_647
O5 H5A O12 0.823(15) 1.88(4) 2.660(9) 158(11) 2_646
O18 H18A O6 0.818(15) 2.13(4) 2.840(8) 146(6) 1_455
O18 H18A S2 0.818(15) 3.02(4) 3.515(7) 121(4) 1_455
O17 H17A O10A 0.817(15) 2.30(13) 2.924(18) 134(16) .
O17 H17B O15 0.819(15) 2.13(4) 2.889(8) 154(7) 1_655
O17 H17B S1 0.819(15) 2.95(6) 3.502(6) 126(6) 1_655
O2 H2A O18 0.821(15) 2.20(17) 2.812(9) 132(20) .
O10 H10A O15 0.821(15) 2.4(2) 2.816(10) 113(19) 1_655
O10 H10A O16 0.821(15) 2.56(15) 3.267(12) 145(23) 1_655
O10 H10A O17 0.821(15) 2.04(19) 2.669(12) 133(24) .
O10 H10A S1 0.821(15) 2.7(2) 3.276(9) 124(20) 1_655
O11 H11A O13 0.821(15) 2.17(9) 2.931(9) 153(19) 1_655

_refine_diff_density_max         0.709
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.113



