# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_8z03-rk01-061
_database_code_depnum_ccdc_archive 'CCDC 2130644'
loop_
_audit_author_name
_audit_author_address
'Hatsumi Mori'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-12-23 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2MeS2EDOT_HSO4
_chemical_formula_moiety         'C14 H14 O4 S4, O4 S'
_chemical_formula_sum            'C14 H14 O8 S5'
_chemical_formula_weight         470.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8176(7)
_cell_length_b                   22.839(2)
_cell_length_c                   4.0259(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.428(7)
_cell_angle_gamma                90
_cell_volume                     981.21(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3167
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.5270
_cell_measurement_theta_min      2.5960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic bluish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_preparation       'Electrochemical oxidation'
_exptl_crystal_recrystallization_method 
'Electrochemical oxidation in CH3CN with NBu4HSO4 as an electrolyte'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8326
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.600
_diffrn_reflns_theta_min         1.908
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   50.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50   50.00    --  -20.00  45.00  90.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0646917000
_diffrn_orient_matrix_UB_12      -0.0063975000
_diffrn_orient_matrix_UB_13      -0.0105093000
_diffrn_orient_matrix_UB_21      -0.0143564000
_diffrn_orient_matrix_UB_22      0.0301771000
_diffrn_orient_matrix_UB_23      -0.0231819000
_diffrn_orient_matrix_UB_31      -0.0052293000
_diffrn_orient_matrix_UB_32      -0.0035734000
_diffrn_orient_matrix_UB_33      -0.1767557000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1432
_reflns_number_total             2687
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.1380
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0716P)²+0.8864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1834
_refine_special_details          'Solvent mask was used'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S3-O3 \\sim S3-O4 \\sim S3-O5 \\sim S3-O6
 with sigma of 0.02
 O3-O5 \\sim O4-O6 \\sim O3-O6 \\sim O4-O5 \\sim O3-O4 \\sim O5-O6
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
S3 \\sim O3 \\sim O4 \\sim O5 \\sim O6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 S3, O3, O4, O5, O6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: S3(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
6.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.07192(8) 0.42248(5) 0.7642(2) 0.0518(3) Uani 1 1 d . . . . .
S2 S 0.31214(9) 0.39504(6) 0.4844(3) 0.0658(4) Uani 1 1 d . . . . .
O1 O 0.1679(2) 0.58194(14) 1.0139(7) 0.0620(8) Uani 1 1 d . . . . .
O2 O 0.3571(2) 0.52307(14) 0.7042(7) 0.0629(8) Uani 1 1 d . . . . .
C2 C 0.1582(3) 0.52646(18) 0.9037(9) 0.0478(9) Uani 1 1 d . . . . .
C1 C 0.0534(3) 0.49196(18) 0.9328(8) 0.0471(9) Uani 1 1 d . . . . .
C3 C 0.2470(3) 0.4981(2) 0.7533(9) 0.0532(10) Uani 1 1 d . . . . .
C4 C 0.2165(3) 0.4409(2) 0.6634(9) 0.0526(10) Uani 1 1 d . . . . .
C5 C 0.2669(4) 0.6130(2) 0.8819(12) 0.0703(13) Uani 1 1 d . . . . .
H5A H 0.287365 0.648685 1.009758 0.084 Uiso 1 1 calc R U . . .
H5B H 0.237710 0.623742 0.649167 0.084 Uiso 1 1 calc R U . . .
C6 C 0.3825(4) 0.5754(2) 0.9027(12) 0.0745(14) Uani 1 1 d . . . . .
H6A H 0.448290 0.597576 0.822631 0.089 Uiso 1 1 calc R U . . .
H6B H 0.411837 0.564880 1.135639 0.089 Uiso 1 1 calc R U . . .
C7 C 0.2310(5) 0.3268(2) 0.4773(14) 0.0880(15) Uani 1 1 d . . . . .
H7A H 0.148100 0.331030 0.351396 0.132 Uiso 1 1 calc R U . . .
H7B H 0.225651 0.315062 0.703597 0.132 Uiso 1 1 calc R U . . .
H7C H 0.275624 0.297496 0.373239 0.132 Uiso 1 1 calc R U . . .
S3 S -0.4534(4) 0.2520(2) -0.191(4) 0.204(4) Uani 0.5 1 d D U P A -1
O3 O -0.3396(13) 0.2350(7) 0.020(6) 0.238(7) Uani 0.5 1 d D U P A -1
O4 O -0.518(3) 0.2034(10) -0.355(6) 0.240(10) Uani 0.5 1 d D U P A -1
O5 O -0.531(2) 0.2810(11) 0.023(6) 0.260(9) Uani 0.5 1 d D U P A -1
O6 O -0.4341(16) 0.2984(5) -0.424(5) 0.237(7) Uani 0.5 1 d D U P A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.750(4) . ?
S1 C4 1.731(4) . ?
S2 C4 1.712(4) . ?
S2 C7 1.788(5) . ?
O1 C2 1.341(5) . ?
O1 C5 1.456(5) . ?
O2 C3 1.364(4) . ?
O2 C6 1.440(5) . ?
C2 C1 1.401(5) . ?
C2 C3 1.379(5) . ?
C1 C1 1.403(6) 3_567 ?
C3 C4 1.380(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.507(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
S3 O3 1.429(15) . ?
S3 O4 1.418(17) . ?
S3 O5 1.459(15) . ?
S3 O6 1.450(14) . ?

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
C4 S1 C1 92.04(18) . . ?
C4 S2 C7 102.2(2) . . ?
C2 O1 C5 111.2(3) . . ?
C3 O2 C6 111.1(3) . . ?
O1 C2 C1 121.6(3) . . ?
O1 C2 C3 124.6(3) . . ?
C3 C2 C1 113.8(4) . . ?
C2 C1 S1 109.4(3) . . ?
C2 C1 C1 127.9(5) . 3_567 ?
C1 C1 S1 122.7(4) 3_567 . ?
O2 C3 C2 123.7(4) . . ?
O2 C3 C4 122.3(3) . . ?
C2 C3 C4 113.9(3) . . ?
S2 C4 S1 125.6(3) . . ?
C3 C4 S1 110.8(3) . . ?
C3 C4 S2 123.6(3) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
O1 C5 C6 110.8(4) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O2 C6 C5 111.1(4) . . ?
O2 C6 H6A 109.4 . . ?
O2 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
S2 C7 H7A 109.5 . . ?
S2 C7 H7B 109.5 . . ?
S2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 S3 O5 107.2(14) . . ?
O3 S3 O6 112.3(12) . . ?
O4 S3 O3 112.1(12) . . ?
O4 S3 O5 109.9(9) . . ?
O4 S3 O6 112.7(14) . . ?
O6 S3 O5 102.0(12) . . ?

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
O1 C2 C1 S1 180.0(3) . . . . ?
O1 C2 C1 C1 1.1(7) . . . 3_567 ?
O1 C2 C3 O2 1.2(6) . . . . ?
O1 C2 C3 C4 179.5(3) . . . . ?
O1 C5 C6 O2 61.5(5) . . . . ?
O2 C3 C4 S1 179.2(3) . . . . ?
O2 C3 C4 S2 0.4(5) . . . . ?
C2 O1 C5 C6 -43.8(5) . . . . ?
C2 C3 C4 S1 0.8(4) . . . . ?
C2 C3 C4 S2 -177.9(3) . . . . ?
C1 S1 C4 S2 178.1(3) . . . . ?
C1 S1 C4 C3 -0.6(3) . . . . ?
C1 C2 C3 O2 -179.0(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C3 O2 C6 C5 -44.6(5) . . . . ?
C3 C2 C1 S1 0.1(4) . . . . ?
C3 C2 C1 C1 -178.8(4) . . . 3_567 ?
C4 S1 C1 C2 0.3(3) . . . . ?
C4 S1 C1 C1 179.3(4) . . . 3_567 ?
C5 O1 C2 C1 -165.5(4) . . . . ?
C5 O1 C2 C3 14.3(5) . . . . ?
C6 O2 C3 C2 15.0(5) . . . . ?
C6 O2 C3 C4 -163.2(4) . . . . ?
C7 S2 C4 S1 -5.4(3) . . . . ?
C7 S2 C4 C3 173.2(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.048 0.250 -0.299 62.5 25.4 ?
2 0.048 0.750 -0.565 62.5 25.4 ?

_olex2_exptl_crystal_mounting_method 'Mitegen Microloop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.095
_oxdiff_exptl_absorpt_empirical_full_min 0.588
_chemical_properties_physical    Efflorescent
####################################################################### 
# 
# 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_8z03-rk01-065
_database_code_depnum_ccdc_archive 'CCDC 2130652'
loop_
_audit_author_name
_audit_author_address
'Hatsumi Mori'
;The Institute for Solid State Physics, The University of Tokyo
Japan
;
_audit_update_record             
;
2021-12-23 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2MeS2EDOT_HSO4
_chemical_formula_moiety         'C14 H14 O4 S4, O4 S'
_chemical_formula_sum            'C14 H14 O8 S5'
_chemical_formula_weight         470.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6718(6)
_cell_length_b                   22.7325(12)
_cell_length_c                   3.9848(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.355(6)
_cell_angle_gamma                90
_cell_volume                     950.95(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4007
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      29.8420
_cell_measurement_theta_min      2.6320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic bluish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_preparation       'electrochemical oxidation'
_exptl_crystal_recrystallization_method 
'electrochemical oxidation in CH3CN with NBu4HSO4 as an electrolyte'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8016
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.489
_diffrn_reflns_theta_min         3.316
_diffrn_ambient_temperature      150.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   50.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50   50.00    --  -20.00  45.00  90.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0634470000
_diffrn_orient_matrix_UB_12      0.0097602000
_diffrn_orient_matrix_UB_13      0.0050479000
_diffrn_orient_matrix_UB_21      0.0220418000
_diffrn_orient_matrix_UB_22      -0.0293822000
_diffrn_orient_matrix_UB_23      0.0253468000
_diffrn_orient_matrix_UB_31      -0.0073298000
_diffrn_orient_matrix_UB_32      -0.0038816000
_diffrn_orient_matrix_UB_33      -0.1790648000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1742
_reflns_number_total             2616
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0939P)²+2.1783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1918
_refine_ls_wR_factor_ref         0.2117
_refine_special_details          'Solvent mask was used.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S2-O3 \\sim S2-O4 \\sim S2-O5 \\sim S2-O6
 with sigma of 0.02
 O3-O5 \\sim O4-O6 \\sim O3-O6 \\sim O4-O5 \\sim O3-O4 \\sim O5-O6
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
S2 \\sim O3 \\sim O4 \\sim O5 \\sim O6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 S2, O3, O4, O5, O6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: S2(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00A(H00C,H00D)
6.b Idealised Me refined as rotating group:
 C00B(H00E,H00F,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.93187(10) 0.42092(5) 0.2372(3) 0.0276(3) Uani 1 1 d . . . . .
S002 S 0.69106(10) 0.39109(5) 0.5200(3) 0.0353(3) Uani 1 1 d . . . . .
O003 O 0.8274(3) 0.58141(14) -0.0120(8) 0.0355(7) Uani 1 1 d . . . . .
O004 O 0.6398(3) 0.52044(15) 0.3047(8) 0.0364(7) Uani 1 1 d . . . . .
C005 C 0.8394(4) 0.52546(18) 0.0982(10) 0.0265(8) Uani 1 1 d . . . . .
C006 C 0.7509(4) 0.4960(2) 0.2510(11) 0.0295(9) Uani 1 1 d . . . . .
C007 C 0.9464(4) 0.49124(19) 0.0671(10) 0.0286(9) Uani 1 1 d . . . . .
C008 C 0.7265(5) 0.6122(2) 0.1221(13) 0.0402(11) Uani 1 1 d . . . . .
H00A H 0.703601 0.648668 -0.010366 0.048 Uiso 1 1 calc R U . . .
H00B H 0.757899 0.623342 0.362664 0.048 Uiso 1 1 calc R U . . .
C009 C 0.7849(4) 0.4390(2) 0.3393(10) 0.0296(9) Uani 1 1 d . . . . .
C00A C 0.6119(5) 0.5745(2) 0.1020(13) 0.0418(12) Uani 1 1 d . . . . .
H00C H 0.544200 0.596870 0.186408 0.050 Uiso 1 1 calc R U . . .
H00D H 0.579804 0.563955 -0.139157 0.050 Uiso 1 1 calc R U . . .
C00B C 0.7762(6) 0.3239(2) 0.5214(14) 0.0493(13) Uani 1 1 d . . . . .
H00E H 0.783062 0.313336 0.286950 0.074 Uiso 1 1 calc R U . . .
H00F H 0.730847 0.292728 0.620347 0.074 Uiso 1 1 calc R U . . .
H00G H 0.861704 0.328560 0.657708 0.074 Uiso 1 1 calc R U . . .
S2 S 0.5408(5) 0.7473(2) 0.320(2) 0.123(2) Uani 0.5 1 d D U P A -1
O3 O 0.5766(19) 0.7941(6) 0.078(5) 0.160(7) Uani 0.5 1 d D U P A -1
O4 O 0.4728(15) 0.7832(7) 0.558(5) 0.133(6) Uani 0.5 1 d D U P A -1
O5 O 0.6683(15) 0.7294(8) 0.535(5) 0.158(7) Uani 0.5 1 d D U P A -1
O6 O 0.467(2) 0.6992(8) 0.152(6) 0.154(8) Uani 0.5 1 d D U P A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C007 1.754(4) . ?
S001 C009 1.738(4) . ?
S002 C009 1.722(4) . ?
S002 C00B 1.777(6) . ?
O003 C005 1.344(5) . ?
O003 C008 1.463(5) . ?
O004 C006 1.360(5) . ?
O004 C00A 1.472(6) . ?
C005 C006 1.385(6) . ?
C005 C007 1.406(6) . ?
C006 C009 1.376(6) . ?
C007 C007 1.404(8) 3_765 ?
C008 H00A 0.9900 . ?
C008 H00B 0.9900 . ?
C008 C00A 1.483(7) . ?
C00A H00C 0.9900 . ?
C00A H00D 0.9900 . ?
C00B H00E 0.9800 . ?
C00B H00F 0.9800 . ?
C00B H00G 0.9800 . ?
S2 O3 1.531(14) . ?
S2 O4 1.529(15) . ?
S2 O5 1.527(15) . ?
S2 O6 1.444(16) . ?

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
C009 S001 C007 91.2(2) . . ?
C009 S002 C00B 102.1(2) . . ?
C005 O003 C008 111.5(3) . . ?
C006 O004 C00A 110.6(3) . . ?
O003 C005 C006 124.6(4) . . ?
O003 C005 C007 121.8(4) . . ?
C006 C005 C007 113.6(4) . . ?
O004 C006 C005 123.7(4) . . ?
O004 C006 C009 122.8(4) . . ?
C009 C006 C005 113.5(4) . . ?
C005 C007 S001 109.9(3) . . ?
C007 C007 S001 122.7(4) 3_765 . ?
C007 C007 C005 127.3(5) 3_765 . ?
O003 C008 H00A 109.4 . . ?
O003 C008 H00B 109.4 . . ?
O003 C008 C00A 111.0(4) . . ?
H00A C008 H00B 108.0 . . ?
C00A C008 H00A 109.4 . . ?
C00A C008 H00B 109.4 . . ?
S002 C009 S001 124.5(3) . . ?
C006 C009 S001 111.8(3) . . ?
C006 C009 S002 123.8(3) . . ?
O004 C00A C008 111.6(4) . . ?
O004 C00A H00C 109.3 . . ?
O004 C00A H00D 109.3 . . ?
C008 C00A H00C 109.3 . . ?
C008 C00A H00D 109.3 . . ?
H00C C00A H00D 108.0 . . ?
S002 C00B H00E 109.5 . . ?
S002 C00B H00F 109.5 . . ?
S002 C00B H00G 109.5 . . ?
H00E C00B H00F 109.5 . . ?
H00E C00B H00G 109.5 . . ?
H00F C00B H00G 109.5 . . ?
O4 S2 O3 102.7(10) . . ?
O5 S2 O3 103.9(11) . . ?
O5 S2 O4 105.6(10) . . ?
O6 S2 O3 114.3(11) . . ?
O6 S2 O4 114.2(8) . . ?
O6 S2 O5 114.7(11) . . ?

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
O003 C005 C006 O004 0.7(7) . . . . ?
O003 C005 C006 C009 179.7(4) . . . . ?
O003 C005 C007 S001 179.7(3) . . . . ?
O003 C005 C007 C007 1.7(8) . . . 3_765 ?
O003 C008 C00A O004 61.0(5) . . . . ?
O004 C006 C009 S001 179.9(3) . . . . ?
O004 C006 C009 S002 1.3(6) . . . . ?
C005 O003 C008 C00A -43.5(5) . . . . ?
C005 C006 C009 S001 0.9(5) . . . . ?
C005 C006 C009 S002 -177.7(3) . . . . ?
C006 O004 C00A C008 -44.7(5) . . . . ?
C006 C005 C007 S001 -0.1(5) . . . . ?
C006 C005 C007 C007 -178.2(5) . . . 3_765 ?
C007 S001 C009 S002 177.8(3) . . . . ?
C007 S001 C009 C006 -0.8(3) . . . . ?
C007 C005 C006 O004 -179.5(4) . . . . ?
C007 C005 C006 C009 -0.5(5) . . . . ?
C008 O003 C005 C006 14.1(6) . . . . ?
C008 O003 C005 C007 -165.7(4) . . . . ?
C009 S001 C007 C005 0.5(3) . . . . ?
C009 S001 C007 C007 178.7(5) . . . 3_765 ?
C00A O004 C006 C005 15.0(6) . . . . ?
C00A O004 C006 C009 -163.9(4) . . . . ?
C00B S002 C009 S001 -5.5(4) . . . . ?
C00B S002 C009 C006 172.9(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.051 0.250 -0.150 54.5 26.7 ?
2 -0.051 0.750 -0.176 54.5 26.7 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'Mitegen Microloop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.721
_chemical_properties_physical    Efflorescent
