# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_kobayashi_y202001g_113k1_0m
_database_code_depnum_ccdc_archive 'CCDC 1992525'
loop_
_audit_author_name
_audit_author_address
'Yoshitaka Matsushita'
;NIMS
Japan
;
_audit_update_record             
;
2020-04-29 deposited with the CCDC.	2020-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H2.50 O4 S8'
_chemical_formula_weight         467.12

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   3.7464(2)
_cell_length_b                   11.8946(6)
_cell_length_c                   20.2094(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.506(2)
_cell_angle_gamma                90
_cell_volume                     898.88(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    9455
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      39.44

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             469
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.017
_exptl_absorpt_coefficient_mu    1.007
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7764
_exptl_absorpt_correction_T_max  0.9283
_exptl_absorpt_process_details   
;
CrystalClear (Rigaku, 1997--2002)
;
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Rigaku AFC11 Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_number            11520
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.426
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1922
_reflns_number_gt                1728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrystalClear (Rigaku, 1997--2002)'
_computing_cell_refinement       'CrystalClear (Rigaku, 1997--2002)'
_computing_data_reduction        'CrystalClear (Rigaku, 1997--2002)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0619P)²+5.3024P] 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_number_reflns         1922
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1595
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_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 -0.3961(11) 0.6938(4) 0.7641(2) 0.0170(8) Uani 1 1 d . . . . .
H1 H -0.473362 0.652383 0.800763 0.020 Uiso 1 1 calc R U . . .
C2 C -0.1580(14) 0.750000 0.6520(3) 0.0110(10) Uani 1 2 d S T P . .
C3 C -0.0208(14) 0.750000 0.5909(3) 0.0104(10) Uani 1 2 d S T P . .
C4 C 0.2157(9) 0.6935(3) 0.47994(17) 0.0098(7) Uani 1 1 d . . . . .
C5 C 0.4546(14) 0.750000 0.3688(3) 0.0110(10) Uani 1 2 d S T P . .
C6 C 0.5916(14) 0.750000 0.3088(3) 0.0112(10) Uani 1 2 d S T P . .
C7 C 0.8426(10) 0.6931(3) 0.19732(19) 0.0145(8) Uani 1 1 d . . . . .
C8 C 0.9500(13) 0.6102(4) 0.1460(2) 0.0240(10) Uani 1 1 d . . . . .
O1 O 0.9086(10) 0.5099(3) 0.15819(17) 0.0309(8) Uani 1 1 d . . . . .
O2 O 1.0850(10) 0.6483(3) 0.09319(18) 0.0360(9) Uani 1 1 d . . . . .
H1O H 1.02(5) 0.750000 0.082(10) 0.054 Uiso 0.5 2 d S U P . .
S1 S -0.2491(3) 0.62625(8) 0.69431(5) 0.0126(3) Uani 1 1 d . . . . .
S2 S 0.0846(2) 0.62424(7) 0.55032(5) 0.0100(3) Uani 1 1 d . . . . .
S3 S 0.3547(2) 0.62399(7) 0.41031(5) 0.0104(3) Uani 1 1 d . . . . .
S4 S 0.6895(3) 0.62556(8) 0.26684(5) 0.0129(3) Uani 1 1 d . . . . .


_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 C1 1.336(8) 4_575 ?
C1 S1 1.741(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.365(8) . ?
C2 S1 1.747(3) 4_575 ?
C2 S1 1.747(3) . ?
C3 S2 1.763(3) . ?
C3 S2 1.763(3) 4_575 ?
C4 C4 1.343(8) 4_575 ?
C4 S3 1.739(4) . ?
C4 S2 1.740(4) . ?
C5 C6 1.345(8) . ?
C5 S3 1.769(3) . ?
C5 S3 1.769(3) 4_575 ?
C6 S4 1.755(3) . ?
C6 S4 1.755(3) 4_575 ?
C7 C7 1.354(8) 4_575 ?
C7 C8 1.503(6) . ?
C7 S4 1.745(4) . ?
C8 O1 1.230(6) . ?
C8 O2 1.292(6) . ?
O2 H1O 1.25(5) . ?

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
C1 C1 S1 117.49(14) 4_575 . ?
C1 C1 H1 121.3 4_575 . ?
S1 C1 H1 121.3 . . ?
C3 C2 S1 122.58(15) . 4_575 ?
C3 C2 S1 122.58(15) . . ?
S1 C2 S1 114.8(3) 4_575 . ?
C2 C3 S2 121.88(15) . . ?
C2 C3 S2 121.88(15) . 4_575 ?
S2 C3 S2 116.1(3) . 4_575 ?
C4 C4 S3 118.40(13) 4_575 . ?
C4 C4 S2 118.26(13) 4_575 . ?
S3 C4 S2 123.3(2) . . ?
C6 C5 S3 122.09(15) . . ?
C6 C5 S3 122.09(15) . 4_575 ?
S3 C5 S3 115.8(3) . 4_575 ?
C5 C6 S4 122.52(15) . . ?
C5 C6 S4 122.52(15) . 4_575 ?
S4 C6 S4 115.0(3) . 4_575 ?
C7 C7 C8 131.0(2) 4_575 . ?
C7 C7 S4 117.39(14) 4_575 . ?
C8 C7 S4 111.6(3) . . ?
O1 C8 O2 124.5(4) . . ?
O1 C8 C7 117.1(4) . . ?
O2 C8 C7 118.3(4) . . ?
C8 O2 H1O 114(9) . . ?
C1 S1 C2 95.1(2) . . ?
C4 S2 C3 93.5(2) . . ?
C4 S3 C5 93.6(2) . . ?
C7 S4 C6 95.1(2) . . ?

_refine_diff_density_max         1.538
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.198

