# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1492164'
_audit_update_record             
;
2016-07-12 deposited with the CCDC.
2016-08-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            LiMM4411
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H28 Li N O9 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         377.40
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.4370(12)
_cell_length_b                   15.0453(12)
_cell_length_c                   9.4300(8)
_cell_angle_alpha                90
_cell_angle_beta                 122.2871(9)
_cell_angle_gamma                90
_cell_volume                     1731.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1677
_cell_measurement_theta_min      2.5671
_cell_measurement_theta_max      27.3282
_cell_measurement_temperature    173

_exptl_crystal_description       prismatic
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4912
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_theta_min         2.149
_diffrn_reflns_theta_max         27.580
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             2432
_reflns_number_gt                2252
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0672
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_number_reflns         2432
_refine_ls_number_parameters     234
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.1489P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.305
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 410 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(6)

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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6624(3) 0.1622(2) 0.6636(4) 0.0224(7) Uani d . . . 1 . .
H H1A 0.6119 0.121 0.6695 0.034 Uiso calc U . R 1 . .
H H1B 0.7207 0.1285 0.6643 0.034 Uiso calc U . R 1 . .
H H1C 0.6222 0.1972 0.5601 0.034 Uiso calc U . R 1 . .
C C2 0.7638(3) 0.1685(2) 0.9701(4) 0.0220(7) Uani d . . . 1 . .
H H2A 0.8178 0.1281 0.9724 0.033 Uiso calc U . R 1 . .
H H2B 0.7072 0.1339 0.9724 0.033 Uiso calc U . R 1 . .
H H2C 0.8003 0.2078 1.0682 0.033 Uiso calc U . R 1 . .
C C3 0.8021(3) 0.2787(2) 0.8192(4) 0.0174(7) Uani d . . . 1 . .
H H3A 0.8617 0.2384 0.8374 0.021 Uiso calc U . R 1 . .
H H3B 0.8326 0.3192 0.9169 0.021 Uiso calc U . R 1 . .
C C4 0.7656(3) 0.3338(2) 0.6626(4) 0.0245(8) Uani d . . . 1 . .
H H4A 0.7029 0.3717 0.6389 0.029 Uiso calc U . R 1 . .
H H4B 0.7411 0.2937 0.5655 0.029 Uiso calc U . R 1 . .
C C5 0.8598(3) 0.3923(2) 0.6860(4) 0.0214(7) Uani d . . . 1 . .
H H5A 0.9259 0.3552 0.7263 0.026 Uiso calc U . R 1 . .
H H5B 0.8396 0.4182 0.5766 0.026 Uiso calc U . R 1 . .
C C6 0.8857(3) 0.4669(2) 0.8111(4) 0.0189(7) Uani d . . . 1 . .
H H6A 0.9108 0.4407 0.9224 0.023 Uiso calc U . R 1 . .
H H6B 0.8179 0.501 0.775 0.023 Uiso calc U . R 1 . .
C C7 0.6206(3) 0.2810(2) 0.7986(4) 0.0183(7) Uani d . . . 1 . .
H H7A 0.5905 0.3186 0.6971 0.022 Uiso calc U . R 1 . .
H H7B 0.5609 0.2416 0.7831 0.022 Uiso calc U . R 1 . .
C C8 0.6550(3) 0.3406(2) 0.9482(4) 0.0238(7) Uani d . . . 1 . .
H H8A 0.7257 0.3693 0.9829 0.029 Uiso calc U . R 1 . .
H H8B 0.6654 0.3044 1.0434 0.029 Uiso calc U . R 1 . .
C C9 0.5679(3) 0.4124(2) 0.9050(5) 0.0250(8) Uani d . . . 1 . .
H H9A 0.4942 0.3853 0.8373 0.03 Uiso calc U . R 1 . .
H H9B 0.5766 0.4349 1.0101 0.03 Uiso calc U . R 1 . .
C C10 0.5754(3) 0.4901(2) 0.8081(4) 0.0178(7) Uani d . . . 1 . .
H H10A 0.5637 0.4679 0.7008 0.021 Uiso calc U . R 1 . .
H H10B 0.6501 0.5157 0.8738 0.021 Uiso calc U . R 1 . .
H H23 1.213(4) 0.726(3) 1.300(6) 0.042(13) Uiso d . . . 1 . .
H H24 1.107(4) 0.764(3) 1.261(6) 0.058(14) Uiso d . . . 1 . .
H H22 1.308(4) 0.542(3) 1.403(6) 0.042(13) Uiso d . . . 1 . .
H H21 1.295(3) 0.530(2) 1.251(5) 0.031(12) Uiso d . . . 1 . .
H H25 0.908(4) 0.291(3) 0.406(6) 0.055(17) Uiso d . . . 1 . .
H H26 0.896(4) 0.218(3) 0.452(6) 0.031(12) Uiso d . . . 1 . .
Li Li1 1.1226(4) 0.5877(3) 1.2231(7) 0.0184(12) Uani d . . . 1 . .
N N1 0.7119(2) 0.22364(15) 0.8124(3) 0.0143(5) Uani d . . . 1 . .
O O1 1.02080(18) 0.59363(13) 0.9799(3) 0.0201(5) Uani d . . . 1 . .
O O2 0.93815(19) 0.59458(15) 0.6801(3) 0.0237(6) Uani d . . . 1 . .
O O3 1.07620(18) 0.48451(15) 0.8500(3) 0.0232(5) Uani d . . . 1 . .
O O4 0.49117(19) 0.60090(15) 0.9238(3) 0.0250(5) Uani d . . . 1 . .
O O5 0.37055(17) 0.53557(14) 0.6496(3) 0.0220(5) Uani d . . . 1 . .
O O6 0.50240(19) 0.64705(13) 0.6855(3) 0.0249(5) Uani d . . . 1 . .
O O7 1.2674(2) 0.54847(16) 1.2992(4) 0.0249(6) Uani d . . . 1 . .
O O8 1.1507(2) 0.71180(17) 1.2876(3) 0.0254(6) Uani d . . . 1 . .
O O9 0.8668(2) 0.2543(2) 0.3869(4) 0.0346(7) Uani d . . . 1 . .
S S1 0.98734(6) 0.53997(5) 0.82974(9) 0.01391(16) Uani d . . . 1 . .
S S2 0.47792(6) 0.57519(5) 0.76510(9) 0.01566(17) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.504(4) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 N1 . 1.507(4) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 N1 . 1.516(4) ?
C3 C4 . 1.520(5) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.533(4) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.523(4) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 S1 . 1.766(3) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.514(4) ?
C7 N1 . 1.522(4) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.538(4) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.523(4) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 S2 . 1.782(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
Li1 O7 . 1.906(6) ?
Li1 O8 . 1.938(6) ?
Li1 O1 . 1.956(6) ?
Li1 O3 2_565 1.980(6) ?
O1 S1 . 1.469(2) ?
O2 S1 . 1.449(2) ?
O3 S1 . 1.455(2) ?
O3 Li1 2_564 1.979(6) ?
O4 S2 . 1.456(2) ?
O5 S2 . 1.463(2) ?
O6 S2 . 1.463(2) ?
O7 H22 . 0.83(5) ?
O7 H21 . 0.80(4) ?
O8 H23 . 0.87(4) ?
O8 H24 . 0.95(5) ?
O9 H25 . 0.76(5) ?
O9 H26 . 0.76(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
N1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
N1 C3 C4 . . 114.3(3) ?
N1 C3 H3A . . 108.7 ?
C4 C3 H3A . . 108.7 ?
N1 C3 H3B . . 108.7 ?
C4 C3 H3B . . 108.7 ?
H3A C3 H3B . . 107.6 ?
C3 C4 C5 . . 110.6(3) ?
C3 C4 H4A . . 109.5 ?
C5 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
C5 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
C6 C5 C4 . . 111.5(3) ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5B . . 109.3 ?
C4 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
C5 C6 S1 . . 112.5(2) ?
C5 C6 H6A . . 109.1 ?
S1 C6 H6A . . 109.1 ?
C5 C6 H6B . . 109.1 ?
S1 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.8 ?
C8 C7 N1 . . 114.7(3) ?
C8 C7 H7A . . 108.6 ?
N1 C7 H7A . . 108.6 ?
C8 C7 H7B . . 108.6 ?
N1 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
C7 C8 C9 . . 110.7(3) ?
C7 C8 H8A . . 109.5 ?
C9 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
C10 C9 C8 . . 112.8(3) ?
C10 C9 H9A . . 109.0 ?
C8 C9 H9A . . 109.0 ?
C10 C9 H9B . . 109.0 ?
C8 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C9 C10 S2 . . 112.8(2) ?
C9 C10 H10A . . 109.0 ?
S2 C10 H10A . . 109.0 ?
C9 C10 H10B . . 109.0 ?
S2 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
O7 Li1 O8 . . 100.2(3) ?
O7 Li1 O1 . . 116.2(3) ?
O8 Li1 O1 . . 103.0(3) ?
O7 Li1 O3 . 2_565 105.0(3) ?
O8 Li1 O3 . 2_565 114.9(3) ?
O1 Li1 O3 . 2_565 116.7(3) ?
C1 N1 C2 . . 108.7(2) ?
C1 N1 C3 . . 110.2(2) ?
C2 N1 C3 . . 107.2(2) ?
C1 N1 C7 . . 108.1(2) ?
C2 N1 C7 . . 110.4(2) ?
C3 N1 C7 . . 112.3(2) ?
S1 O1 Li1 . . 139.4(2) ?
S1 O3 Li1 . 2_564 142.6(2) ?
Li1 O7 H22 . . 116.(3) ?
Li1 O7 H21 . . 132.(3) ?
H22 O7 H21 . . 112.(4) ?
Li1 O8 H23 . . 108.(3) ?
Li1 O8 H24 . . 136.(3) ?
H23 O8 H24 . . 108.(4) ?
H25 O9 H26 . . 108.(5) ?
O2 S1 O3 . . 113.09(14) ?
O2 S1 O1 . . 111.38(12) ?
O3 S1 O1 . . 112.06(14) ?
O2 S1 C6 . . 107.89(16) ?
O3 S1 C6 . . 106.48(13) ?
O1 S1 C6 . . 105.41(14) ?
O4 S2 O6 . . 113.33(14) ?
O4 S2 O5 . . 112.27(13) ?
O6 S2 O5 . . 111.66(14) ?
O4 S2 C10 . . 107.63(15) ?
O6 S2 C10 . . 105.64(14) ?
O5 S2 C10 . . 105.71(14) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1492165'
_audit_update_record             
;
2016-07-12 deposited with the CCDC.
2016-08-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            NaMM4411
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H22 N Na O7 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         355.39

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.6781(16)
_cell_length_b                   10.9086(6)
_cell_length_c                   9.8067(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.1423(6)
_cell_angle_gamma                90
_cell_volume                     3078.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3446
_cell_measurement_theta_min      2.7991
_cell_measurement_theta_max      27.5728
_cell_measurement_temperature    173

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504

_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8673
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_theta_min         1.415
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             3515
_reflns_number_gt                2969
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1398
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_number_reflns         3515
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2205P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.379
_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 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'
N N 0.0061 0.0033 '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'
Na Na 0.0362 0.0249 '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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.44837(7) 0.40586(19) 0.3638(2) 0.0162(4) Uani d . . . 1 . .
H H1A 0.4502 0.4937 0.3853 0.024 Uiso calc U . R 1 . .
H H1B 0.4367 0.3941 0.2623 0.024 Uiso calc U . R 1 . .
H H1C 0.4794 0.3693 0.3947 0.024 Uiso calc U . R 1 . .
C C2 0.43876(8) 0.3426(2) 0.5938(2) 0.0213(5) Uani d . . . 1 . .
H H2A 0.468 0.2968 0.6098 0.032 Uiso calc U . R 1 . .
H H2B 0.418 0.3027 0.644 0.032 Uiso calc U . R 1 . .
H H2C 0.4451 0.4267 0.6285 0.032 Uiso calc U . R 1 . .
C C3 0.37138(7) 0.41929(19) 0.4221(2) 0.0144(4) Uani d . . . 1 . .
H H3A 0.3498 0.3721 0.4645 0.017 Uiso calc U . R 1 . .
H H3B 0.3789 0.4961 0.4766 0.017 Uiso calc U . R 1 . .
C C4 0.34608(7) 0.45255(19) 0.2724(2) 0.0158(4) Uani d . . . 1 . .
H H4A 0.3375 0.3773 0.2156 0.019 Uiso calc U . R 1 . .
H H4B 0.3664 0.5031 0.2284 0.019 Uiso calc U . R 1 . .
C C5 0.30224(7) 0.52465(19) 0.2785(2) 0.0145(4) Uani d . . . 1 . .
H H5A 0.2836 0.4762 0.3302 0.017 Uiso calc U . R 1 . .
H H5B 0.3113 0.6022 0.3304 0.017 Uiso calc U . R 1 . .
C C6 0.27287(7) 0.55322(19) 0.1312(2) 0.0158(4) Uani d . . . 1 . .
H H6A 0.2655 0.4756 0.0782 0.019 Uiso calc U . R 1 . .
H H6B 0.2913 0.6046 0.0816 0.019 Uiso calc U . R 1 . .
C C7 0.40393(7) 0.21546(18) 0.3872(2) 0.0154(4) Uani d . . . 1 . .
H H7A 0.3826 0.2194 0.2924 0.019 Uiso calc U . R 1 . .
H H7B 0.3871 0.175 0.4504 0.019 Uiso calc U . R 1 . .
C C8 0.44566(7) 0.13635(18) 0.3796(2) 0.0170(4) Uani d . . . 1 . .
H H8A 0.4692 0.1403 0.4706 0.02 Uiso calc U . R 1 . .
H H8B 0.46 0.1688 0.3058 0.02 Uiso calc U . R 1 . .
C C9 0.43123(7) 0.00246(19) 0.3463(2) 0.0174(4) Uani d . . . 1 . .
H H9A 0.4036 0.0006 0.2657 0.021 Uiso calc U . R 1 . .
H H9B 0.4567 -0.041 0.3176 0.021 Uiso calc U . R 1 . .
C C10 0.41993(7) -0.06559(19) 0.4697(2) 0.0169(4) Uani d . . . 1 . .
H H10A 0.3911 -0.0312 0.4883 0.02 Uiso calc U . R 1 . .
H H10B 0.4454 -0.0527 0.5548 0.02 Uiso calc U . R 1 . .
N N1 0.41604(5) 0.34530(16) 0.43929(17) 0.0117(3) Uani d . . . 1 . .
Na Na1 0.19709(3) 0.35041(8) 0.24870(9) 0.0206(2) Uani d . . . 1 . .
O O1 0.23276(5) 0.75079(14) 0.19290(18) 0.0240(4) Uani d . . . 1 . .
O O2 0.19337(5) 0.63672(17) -0.01431(16) 0.0268(4) Uani d . . . 1 . .
O O3 0.19666(5) 0.55770(14) 0.21893(16) 0.0194(3) Uani d . . . 1 . .
O O4 0.39958(7) -0.27767(16) 0.55923(18) 0.0340(5) Uani d . . . 1 . .
O O5 0.45608(5) -0.27324(15) 0.41869(19) 0.0267(4) Uani d . . . 1 . .
O O6 0.37522(5) -0.23672(14) 0.30897(15) 0.0182(3) Uani d . . . 1 . .
O O7 0.20406(9) 0.3136(2) -0.0033(2) 0.0510(6) Uani d . . . 1 . .
S S1 0.22003(2) 0.63060(5) 0.13140(5) 0.01327(16) Uani d . . . 1 . .
S S2 0.41238(2) -0.22596(5) 0.43669(5) 0.01441(16) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.501(3) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 N1 . 1.501(2) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 C4 . 1.520(3) ?
C3 N1 . 1.525(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.534(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.526(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 S1 . 1.7814(19) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 N1 . 1.519(3) ?
C7 C8 . 1.526(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.535(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.525(3) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 S2 . 1.783(2) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
Na1 O3 . 2.2796(18) ?
Na1 O6 4 2.2883(16) ?
Na1 O1 4_545 2.2936(17) ?
Na1 O2 6_566 2.3576(18) ?
Na1 O7 . 2.562(2) ?
O1 S1 . 1.4540(16) ?
O1 Na1 4 2.2934(17) ?
O2 S1 . 1.4559(16) ?
O2 Na1 6_565 2.3577(18) ?
O3 S1 . 1.4633(15) ?
O4 S2 . 1.4592(17) ?
O5 S2 . 1.4459(16) ?
O6 S2 . 1.4574(14) ?
O6 Na1 4_545 2.2883(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
N1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 N1 . . 116.35(16) ?
C4 C3 H3A . . 108.2 ?
N1 C3 H3A . . 108.2 ?
C4 C3 H3B . . 108.2 ?
N1 C3 H3B . . 108.2 ?
H3A C3 H3B . . 107.4 ?
C3 C4 C5 . . 107.94(16) ?
C3 C4 H4A . . 110.1 ?
C5 C4 H4A . . 110.1 ?
C3 C4 H4B . . 110.1 ?
C5 C4 H4B . . 110.1 ?
H4A C4 H4B . . 108.4 ?
C6 C5 C4 . . 111.18(16) ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5A . . 109.4 ?
C6 C5 H5B . . 109.4 ?
C4 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C5 C6 S1 . . 113.26(14) ?
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 ?
N1 C7 C8 . . 114.55(16) ?
N1 C7 H7A . . 108.6 ?
C8 C7 H7A . . 108.6 ?
N1 C7 H7B . . 108.6 ?
C8 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
C7 C8 C9 . . 111.16(17) ?
C7 C8 H8A . . 109.4 ?
C9 C8 H8A . . 109.4 ?
C7 C8 H8B . . 109.4 ?
C9 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
C10 C9 C8 . . 113.47(17) ?
C10 C9 H9A . . 108.9 ?
C8 C9 H9A . . 108.9 ?
C10 C9 H9B . . 108.9 ?
C8 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
C9 C10 S2 . . 112.08(14) ?
C9 C10 H10A . . 109.2 ?
S2 C10 H10A . . 109.2 ?
C9 C10 H10B . . 109.2 ?
S2 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
C1 N1 C2 . . 108.83(16) ?
C1 N1 C7 . . 111.85(15) ?
C2 N1 C7 . . 109.40(16) ?
C1 N1 C3 . . 110.83(15) ?
C2 N1 C3 . . 106.60(15) ?
C7 N1 C3 . . 109.18(15) ?
O3 Na1 O6 . 4 113.88(6) ?
O3 Na1 O1 . 4_545 118.58(6) ?
O6 Na1 O1 4 4_545 127.17(7) ?
O3 Na1 O2 . 6_566 93.85(7) ?
O6 Na1 O2 4 6_566 90.08(6) ?
O1 Na1 O2 4_545 6_566 92.31(7) ?
O3 Na1 O7 . . 91.78(7) ?
O6 Na1 O7 4 . 89.34(7) ?
O1 Na1 O7 4_545 . 83.36(8) ?
O2 Na1 O7 6_566 . 174.08(8) ?
S1 O1 Na1 . 4 131.21(9) ?
S1 O2 Na1 . 6_565 145.59(10) ?
S1 O3 Na1 . . 128.73(9) ?
S2 O6 Na1 . 4_545 130.25(9) ?
O1 S1 O2 . . 112.93(10) ?
O1 S1 O3 . . 111.04(10) ?
O2 S1 O3 . . 112.26(10) ?
O1 S1 C6 . . 106.75(9) ?
O2 S1 C6 . . 106.74(10) ?
O3 S1 C6 . . 106.66(9) ?
O5 S2 O6 . . 112.29(9) ?
O5 S2 O4 . . 112.60(11) ?
O6 S2 O4 . . 112.46(10) ?
O5 S2 C10 . . 107.17(10) ?
O6 S2 C10 . . 105.67(9) ?
O4 S2 C10 . . 106.04(10) ?

