# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_AU2329_ClO4_c
_database_code_depnum_ccdc_archive 'CCDC 1590324'
_audit_update_record             
;
2017-12-11 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C24 H16 Cl O6 S12'
_chemical_formula_moiety         'C24 H16 Cl O6 S12'
_chemical_formula_weight         820.56
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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                   33.29(4)
_cell_length_b                   7.227(7)
_cell_length_c                   13.232(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.227(18)
_cell_angle_gamma                90.0000
_cell_volume                     3072(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2852
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1668.00
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_T_max  0.822

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

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            11375
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_theta_max         27.400
_diffrn_reflns_theta_min         3.109
_diffrn_reflns_theta_full        27.400
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3476
_reflns_number_gt                1365
_reflns_threshold_expression     F²>2.0σ(F²)

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1869
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.2367
_refine_ls_wR_factor_gt          0.1778
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3476
_refine_ls_number_parameters     196
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0800P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.00
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl7 Cl 0.5000 0.4771(5) 0.2500 0.0837(9) Uani 1 2 d S . .
S1 S 0.20987(5) 0.1202(2) 0.30739(13) 0.0530(5) Uani 1 1 d . . .
S2 S 0.24095(6) 0.1203(2) 0.11677(13) 0.0572(5) Uani 1 1 d . . .
S3 S 0.33462(5) 0.1208(2) 0.25498(13) 0.0544(5) Uani 1 1 d . . .
S4 S 0.30700(5) 0.1166(2) 0.44860(13) 0.0539(5) Uani 1 1 d . . .
S5 S 0.39171(6) 0.1159(3) 0.59117(15) 0.0703(6) Uani 1 1 d . . .
S6 S 0.42460(6) 0.1320(3) 0.35815(16) 0.0740(6) Uani 1 1 d . . .
O10 O 0.4652(2) 0.5867(10) 0.2523(6) 0.138(3) Uani 1 1 d . . .
O13 O 0.5104(2) 0.3662(11) 0.3422(6) 0.158(3) Uani 1 1 d . . .
O20 O 0.05890(17) 0.1361(7) 0.0700(5) 0.0989(19) Uani 1 1 d . . .
H20 H 0.0504 0.0354 0.0841 0.119 Uiso 1 1 calc R . .
C1 C 0.1859(2) 0.1216(8) 0.0965(5) 0.0473(15) Uani 1 1 d . . .
C2 C 0.36069(19) 0.1161(8) 0.4610(5) 0.0492(16) Uani 1 1 d . . .
C3 C 0.2529(2) 0.1191(8) 0.2529(5) 0.0458(15) Uani 1 1 d . . .
C4 C 0.37412(19) 0.1212(8) 0.3720(5) 0.0497(16) Uani 1 1 d . . .
C6 C 0.1716(2) 0.1201(7) 0.1877(5) 0.0465(15) Uani 1 1 d . . .
C8 C 0.2933(2) 0.1192(8) 0.3119(5) 0.0495(16) Uani 1 1 d . . .
C9 C 0.1153(2) 0.1269(9) -0.0115(6) 0.067(2) Uani 1 1 d . . .
H9 H 0.0963 0.1304 -0.0769 0.081 Uiso 1 1 calc R . .
C11 C 0.1019(2) 0.1254(9) 0.0799(6) 0.0585(18) Uani 1 1 d . . .
C12 C 0.4428(2) 0.0669(10) 0.5734(6) 0.079(2) Uani 1 1 d . . .
H12A H 0.4634 0.0872 0.6393 0.095 Uiso 1 1 calc R . .
H12B H 0.4440 -0.0627 0.5553 0.095 Uiso 1 1 calc R . .
C15 C 0.4540(2) 0.1828(10) 0.4899(5) 0.071(2) Uani 1 1 d . . .
H15A H 0.4834 0.1650 0.4946 0.085 Uiso 1 1 calc R . .
H15B H 0.4501 0.3122 0.5042 0.085 Uiso 1 1 calc R . .
C18 C 0.1285(2) 0.1219(7) 0.1786(5) 0.0507(16) Uani 1 1 d . . .
H18 H 0.1183 0.1207 0.2377 0.061 Uiso 1 1 calc R . .
C19 C 0.1572(2) 0.1229(8) -0.0026(5) 0.0523(17) Uani 1 1 d . . .
H19 H 0.1667 0.1210 -0.0627 0.063 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

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

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl7 O10 1.410(6) . ?
Cl7 O10 1.410(6) 2_655 ?
Cl7 O13 1.424(6) 2_655 ?
Cl7 O13 1.424(6) . ?
S1 C6 1.752(7) . ?
S1 C3 1.766(6) . ?
S2 C3 1.740(6) . ?
S2 C1 1.781(7) . ?
S3 C8 1.733(6) . ?
S3 C4 1.749(7) . ?
S4 C8 1.746(7) . ?
S4 C2 1.752(7) . ?
S5 C2 1.761(7) . ?
S5 C12 1.812(7) . ?
S6 C4 1.740(6) . ?
S6 C15 1.799(7) . ?
O20 C11 1.406(8) . ?
O20 H20 0.8200 . ?
C1 C19 1.406(8) . ?
C1 C6 1.410(8) . ?
C2 C4 1.365(8) . ?
C3 C8 1.365(9) . ?
C6 C18 1.410(8) . ?
C9 C19 1.367(9) . ?
C9 C11 1.394(10) . ?
C9 H9 0.9300 . ?
C11 C18 1.371(9) . ?
C12 C15 1.510(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O10 Cl7 O10 111.7(7) . 2_655 ?
O10 Cl7 O13 108.6(4) . 2_655 ?
O10 Cl7 O13 108.2(4) 2_655 2_655 ?
O10 Cl7 O13 108.2(4) . . ?
O10 Cl7 O13 108.6(4) 2_655 . ?
O13 Cl7 O13 111.5(7) 2_655 . ?
C6 S1 C3 96.1(3) . . ?
C3 S2 C1 95.9(3) . . ?
C8 S3 C4 96.5(3) . . ?
C8 S4 C2 94.6(3) . . ?
C2 S5 C12 101.7(3) . . ?
C4 S6 C15 101.7(3) . . ?
C11 O20 H20 109.5 . . ?
C19 C1 C6 119.9(6) . . ?
C19 C1 S2 124.2(5) . . ?
C6 C1 S2 115.9(5) . . ?
C4 C2 S4 118.5(5) . . ?
C4 C2 S5 127.1(5) . . ?
S4 C2 S5 114.4(3) . . ?
C8 C3 S2 121.0(5) . . ?
C8 C3 S1 123.3(5) . . ?
S2 C3 S1 115.6(4) . . ?
C2 C4 S6 129.5(5) . . ?
C2 C4 S3 115.0(5) . . ?
S6 C4 S3 115.4(4) . . ?
C18 C6 C1 119.5(6) . . ?
C18 C6 S1 124.1(5) . . ?
C1 C6 S1 116.4(5) . . ?
C3 C8 S3 121.7(5) . . ?
C3 C8 S4 122.9(5) . . ?
S3 C8 S4 115.4(4) . . ?
C19 C9 C11 118.5(7) . . ?
C19 C9 H9 120.8 . . ?
C11 C9 H9 120.8 . . ?
C18 C11 C9 123.6(7) . . ?
C18 C11 O20 118.4(7) . . ?
C9 C11 O20 118.0(7) . . ?
C15 C12 S5 114.1(5) . . ?
C15 C12 H12A 108.7 . . ?
S5 C12 H12A 108.7 . . ?
C15 C12 H12B 108.7 . . ?
S5 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C15 S6 114.8(5) . . ?
C12 C15 H15A 108.6 . . ?
S6 C15 H15A 108.6 . . ?
C12 C15 H15B 108.6 . . ?
S6 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C11 C18 C6 117.9(6) . . ?
C11 C18 H18 121.0 . . ?
C6 C18 H18 121.0 . . ?
C9 C19 C1 120.6(6) . . ?
C9 C19 H19 119.7 . . ?
C1 C19 H19 119.7 . . ?

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
C3 S2 C1 C19 180.0(5) . . . . ?
C3 S2 C1 C6 -0.4(5) . . . . ?
C8 S4 C2 C4 1.2(5) . . . . ?
C8 S4 C2 S5 179.4(3) . . . . ?
C12 S5 C2 C4 -13.4(7) . . . . ?
C12 S5 C2 S4 168.6(3) . . . . ?
C1 S2 C3 C8 -179.5(5) . . . . ?
C1 S2 C3 S1 -0.2(4) . . . . ?
C6 S1 C3 C8 179.9(5) . . . . ?
C6 S1 C3 S2 0.5(4) . . . . ?
S4 C2 C4 S6 177.0(3) . . . . ?
S5 C2 C4 S6 -1.0(9) . . . . ?
S4 C2 C4 S3 -1.8(7) . . . . ?
S5 C2 C4 S3 -179.7(3) . . . . ?
C15 S6 C4 C2 -11.4(7) . . . . ?
C15 S6 C4 S3 167.4(4) . . . . ?
C8 S3 C4 C2 1.3(5) . . . . ?
C8 S3 C4 S6 -177.6(3) . . . . ?
C19 C1 C6 C18 -0.7(8) . . . . ?
S2 C1 C6 C18 179.7(4) . . . . ?
C19 C1 C6 S1 -179.6(4) . . . . ?
S2 C1 C6 S1 0.8(6) . . . . ?
C3 S1 C6 C18 -179.6(5) . . . . ?
C3 S1 C6 C1 -0.8(5) . . . . ?
S2 C3 C8 S3 0.1(7) . . . . ?
S1 C3 C8 S3 -179.2(3) . . . . ?
S2 C3 C8 S4 -179.6(3) . . . . ?
S1 C3 C8 S4 1.1(8) . . . . ?
C4 S3 C8 C3 179.7(5) . . . . ?
C4 S3 C8 S4 -0.5(4) . . . . ?
C2 S4 C8 C3 179.5(5) . . . . ?
C2 S4 C8 S3 -0.2(4) . . . . ?
C19 C9 C11 C18 0.6(10) . . . . ?
C19 C9 C11 O20 177.8(5) . . . . ?
C2 S5 C12 C15 47.4(6) . . . . ?
S5 C12 C15 S6 -69.0(7) . . . . ?
C4 S6 C15 C12 45.8(6) . . . . ?
C9 C11 C18 C6 0.2(10) . . . . ?
O20 C11 C18 C6 -177.0(5) . . . . ?
C1 C6 C18 C11 -0.1(8) . . . . ?
S1 C6 C18 C11 178.7(5) . . . . ?
C11 C9 C19 C1 -1.4(9) . . . . ?
C6 C1 C19 C9 1.5(9) . . . . ?
S2 C1 C19 C9 -178.9(5) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O20 H20 O10 . . 4_545 2.700(11) 0.820 2.385 103.8 no

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

#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method electrocrystallization
####################################################################### 
# 
# 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_AU3527_0deg
_database_code_depnum_ccdc_archive 'CCDC 1590325'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C12 H8 O S6'
_chemical_formula_moiety         'C12 H8 O S6'
_chemical_formula_weight         360.55
_chemical_melting_point          387-388

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.369(5)
_cell_length_b                   11.196(4)
_cell_length_c                   10.011(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.537(5)
_cell_angle_gamma                90.0000
_cell_volume                     1385.1(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2329
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.46
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736.00
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            10347
_diffrn_reflns_av_R_equivalents  0.1460
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_full        27.470
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3146
_reflns_number_gt                1601
_reflns_threshold_expression     F²>2.0σ(F²)

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2098
_refine_ls_wR_factor_gt          0.1724
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3146
_refine_ls_number_parameters     184
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0787P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44788(14) 0.50143(14) 0.71901(17) 0.0372(5) Uani 1 1 d . . .
S2 S 0.53714(15) 0.28907(14) 0.58469(19) 0.0406(5) Uani 1 1 d . . .
S3 S 0.24372(13) 0.49957(14) 0.49360(17) 0.0372(5) Uani 1 1 d . . .
S4 S 0.33696(15) 0.28451(14) 0.37328(19) 0.0417(5) Uani 1 1 d . . .
S5 S 0.02710(16) 0.46172(19) 0.3483(2) 0.0553(6) Uani 1 1 d . . .
S6 S 0.1340(2) 0.21148(17) 0.2299(3) 0.0714(8) Uani 1 1 d . . .
O1 O 0.7671(5) 0.4709(6) 1.0700(7) 0.050(2) Uani 0.743(10) 1 d P A 1
H1A H 0.7571 0.5430 1.0775 0.060 Uiso 0.743(10) 1 calc PR A 1
O2 O 0.8444(19) 0.2865(19) 0.949(3) 0.075(9) Uani 0.257(10) 1 d P A 2
H2A H 0.8948 0.3311 0.9326 0.090 Uiso 0.257(10) 1 calc PR A 2
C1 C 0.5654(5) 0.4367(5) 0.7944(7) 0.0325(15) Uani 1 1 d . . .
C2 C 0.6187(5) 0.4848(5) 0.9074(6) 0.0344(15) Uani 1 1 d . A .
H1 H 0.5919 0.5524 0.9486 0.041 Uiso 1 1 calc R . .
C3 C 0.7122(6) 0.4300(6) 0.9572(7) 0.0425(18) Uani 1 1 d . . .
H3 H 0.7479 0.4604 1.0335 0.051 Uiso 0.257(10) 1 calc PR A 2
C4 C 0.7529(6) 0.3312(6) 0.8953(7) 0.0429(18) Uani 1 1 d . A .
H4 H 0.8163 0.2963 0.9301 0.051 Uiso 0.743(10) 1 calc PR A 1
C5 C 0.7023(6) 0.2832(6) 0.7839(7) 0.0421(18) Uani 1 1 d . . .
H2 H 0.7310 0.2167 0.7424 0.050 Uiso 1 1 calc R A .
C6 C 0.6060(5) 0.3361(5) 0.7330(6) 0.0298(14) Uani 1 1 d . A .
C7 C 0.4296(5) 0.3928(5) 0.5930(6) 0.0324(15) Uani 1 1 d . . .
C8 C 0.3488(5) 0.3908(5) 0.5032(7) 0.0331(15) Uani 1 1 d . . .
C9 C 0.1565(5) 0.4099(6) 0.3922(7) 0.0385(17) Uani 1 1 d . . .
C10 C 0.2003(6) 0.3120(6) 0.3380(7) 0.0409(18) Uani 1 1 d . . .
C11 C 0.0274(6) 0.4263(7) 0.1721(8) 0.055(2) Uani 1 1 d . . .
H11A H -0.0382 0.4580 0.1287 0.066 Uiso 1 1 calc R . .
H11B H 0.0882 0.4665 0.1338 0.066 Uiso 1 1 calc R . .
C12 C 0.0342(8) 0.2987(7) 0.1418(10) 0.073(3) Uani 1 1 d . . .
H12A H 0.0461 0.2909 0.0471 0.088 Uiso 1 1 calc R . .
H12B H -0.0358 0.2636 0.1572 0.088 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

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

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.760(6) . ?
S1 C1 1.764(6) . ?
S2 C6 1.760(6) . ?
S2 C7 1.770(6) . ?
S3 C9 1.762(7) . ?
S3 C8 1.781(6) . ?
S4 C10 1.739(7) . ?
S4 C8 1.764(6) . ?
S5 C9 1.741(7) . ?
S5 C11 1.808(8) . ?
S6 C10 1.741(7) . ?
S6 C12 1.778(8) . ?
O1 C3 1.370(9) . ?
O1 H1A 0.8200 . ?
O2 C4 1.33(2) . ?
O2 H2A 0.8200 . ?
C1 C6 1.387(9) . ?
C1 C2 1.392(8) . ?
C2 C3 1.382(9) . ?
C2 H1 0.9300 . ?
C3 C4 1.375(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(9) . ?
C5 H2 0.9300 . ?
C7 C8 1.315(9) . ?
C9 C10 1.348(9) . ?
C11 C12 1.464(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C7 S1 C1 95.7(3) . . ?
C6 S2 C7 95.8(3) . . ?
C9 S3 C8 93.9(3) . . ?
C10 S4 C8 94.5(3) . . ?
C9 S5 C11 97.6(3) . . ?
C10 S6 C12 104.5(3) . . ?
C3 O1 H1A 109.5 . . ?
C4 O2 H2A 109.5 . . ?
C6 C1 C2 120.4(6) . . ?
C6 C1 S1 116.8(5) . . ?
C2 C1 S1 122.7(5) . . ?
C3 C2 C1 118.7(6) . . ?
C3 C2 H1 120.7 . . ?
C1 C2 H1 120.7 . . ?
O1 C3 C4 117.5(6) . . ?
O1 C3 C2 121.7(7) . . ?
C4 C3 C2 120.8(6) . . ?
O1 C3 H3 2.1 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
O2 C4 C5 122.1(14) . . ?
O2 C4 C3 116.4(14) . . ?
C5 C4 C3 121.5(7) . . ?
O2 C4 H4 3.0 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.7(6) . . ?
C4 C5 H2 120.7 . . ?
C6 C5 H2 120.7 . . ?
C1 C6 C5 120.0(6) . . ?
C1 C6 S2 116.5(5) . . ?
C5 C6 S2 123.4(5) . . ?
C8 C7 S1 124.8(5) . . ?
C8 C7 S2 120.4(5) . . ?
S1 C7 S2 114.5(3) . . ?
C7 C8 S4 123.5(5) . . ?
C7 C8 S3 123.8(5) . . ?
S4 C8 S3 112.6(4) . . ?
C10 C9 S5 123.4(5) . . ?
C10 C9 S3 116.7(5) . . ?
S5 C9 S3 119.3(4) . . ?
C9 C10 S4 117.8(5) . . ?
C9 C10 S6 126.1(5) . . ?
S4 C10 S6 116.1(4) . . ?
C12 C11 S5 114.7(6) . . ?
C12 C11 H11A 108.6 . . ?
S5 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
S5 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 S6 118.6(6) . . ?
C11 C12 H12A 107.7 . . ?
S6 C12 H12A 107.7 . . ?
C11 C12 H12B 107.7 . . ?
S6 C12 H12B 107.7 . . ?
H12A C12 H12B 107.1 . . ?

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
C7 S1 C1 C6 3.5(6) . . . . ?
C7 S1 C1 C2 -178.7(6) . . . . ?
C6 C1 C2 C3 -0.3(10) . . . . ?
S1 C1 C2 C3 -178.1(5) . . . . ?
C1 C2 C3 O1 -178.4(7) . . . . ?
C1 C2 C3 C4 1.1(11) . . . . ?
O1 C3 C4 O2 -2.1(16) . . . . ?
C2 C3 C4 O2 178.4(13) . . . . ?
O1 C3 C4 C5 178.8(7) . . . . ?
C2 C3 C4 C5 -0.6(12) . . . . ?
O2 C4 C5 C6 -179.6(14) . . . . ?
C3 C4 C5 C6 -0.6(11) . . . . ?
C2 C1 C6 C5 -0.9(10) . . . . ?
S1 C1 C6 C5 177.0(5) . . . . ?
C2 C1 C6 S2 -175.9(5) . . . . ?
S1 C1 C6 S2 2.0(7) . . . . ?
C4 C5 C6 C1 1.4(10) . . . . ?
C4 C5 C6 S2 176.0(5) . . . . ?
C7 S2 C6 C1 -6.3(6) . . . . ?
C7 S2 C6 C5 178.9(6) . . . . ?
C1 S1 C7 C8 177.8(6) . . . . ?
C1 S1 C7 S2 -7.7(4) . . . . ?
C6 S2 C7 C8 -176.6(6) . . . . ?
C6 S2 C7 S1 8.5(4) . . . . ?
S1 C7 C8 S4 176.7(3) . . . . ?
S2 C7 C8 S4 2.4(8) . . . . ?
S1 C7 C8 S3 0.4(9) . . . . ?
S2 C7 C8 S3 -173.9(3) . . . . ?
C10 S4 C8 C7 163.0(6) . . . . ?
C10 S4 C8 S3 -20.3(4) . . . . ?
C9 S3 C8 C7 -163.1(6) . . . . ?
C9 S3 C8 S4 20.2(4) . . . . ?
C11 S5 C9 C10 -36.8(7) . . . . ?
C11 S5 C9 S3 133.4(4) . . . . ?
C8 S3 C9 C10 -12.4(6) . . . . ?
C8 S3 C9 S5 176.7(4) . . . . ?
S5 C9 C10 S4 170.5(4) . . . . ?
S3 C9 C10 S4 0.0(8) . . . . ?
S5 C9 C10 S6 -7.2(10) . . . . ?
S3 C9 C10 S6 -177.6(4) . . . . ?
C8 S4 C10 C9 12.5(7) . . . . ?
C8 S4 C10 S6 -169.6(4) . . . . ?
C12 S6 C10 C9 29.9(9) . . . . ?
C12 S6 C10 S4 -147.7(5) . . . . ?
C9 S5 C11 C12 64.4(7) . . . . ?
S5 C11 C12 S6 -48.1(10) . . . . ?
C10 S6 C12 C11 0.6(10) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H3 O2 . . . 2.60(2) 0.442 2.455 104.3 no
O2 H4 O1 . . . 2.60(2) 0.402 2.496 100.6 no

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

#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
