# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_1905
_database_code_depnum_ccdc_archive 'CCDC 2105227'
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;
_audit_creation_date             2021-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N O4 S3'
_chemical_formula_sum            'C10 H13 N O4 S3'
_chemical_formula_weight         307.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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                   12.8766(3)
_cell_length_b                   6.30850(10)
_cell_length_c                   16.9497(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1376.86(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4967
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.2380
_cell_measurement_theta_min      5.2350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.999
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11537
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.029
_diffrn_reflns_theta_max         67.029
_diffrn_reflns_theta_min         5.219
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  89.00   1.00    1.00    --    0.00  19.00-120.00   45
  2  ω    -25.00  41.00   1.00    1.00    --    0.00  77.00 -30.00   66
  3  ω    -83.00 -26.00   1.00    1.00    --    0.00 -19.00 -90.00   57
  4  ω    -22.00   8.00   1.00    1.00    --    0.00  19.00-120.00   30
  5  ω     48.00  84.00   1.00    1.00    --    0.00  77.00 -30.00   36
  6  ω     -8.00  24.00   1.00    1.00    --    0.00 -19.00 -90.00   32
  7  ω     78.00 104.00   1.00    2.00    --   95.80 -82.00  30.00   26
  8  ω    104.00 182.00   1.00    2.00    --   95.80  15.00-180.00   78
  9  ω     24.00 116.00   1.00    2.00    --   95.80 -45.00 -30.00   92
 10  ω     30.00 120.00   1.00    2.00    --   95.80 -61.00  90.00   90
 11  ω     81.00 185.00   1.00    2.00    --   95.80  30.00 120.00  104
 12  ω    101.00 151.00   1.00    2.00    --   95.80  30.00-150.00   50
 13  ω     51.00 120.00   1.00    2.00    --   95.80 -82.00  90.00   69
 14  ω     70.00 103.00   1.00    2.00    --   95.80 -82.00-180.00   33
 15  ω      9.00 121.00   1.00    2.00    --   95.80 -82.00-120.00  112
 16  ω     27.00  98.00   1.00    2.00    --   95.80 -82.00   0.00   71
 17  ω     93.00 124.00   1.00    2.00    --   95.80 -77.00 -60.00   31
 18  ω     30.00  56.00   1.00    2.00    --   95.80 -77.00 -60.00   26
 19  ω     12.00 107.00   1.00    2.00    --   95.80 -61.00-120.00   95
 20  ω     85.00 183.00   1.00    2.00    --   95.80  30.00  90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0106104000
_diffrn_orient_matrix_UB_12      0.1949283000
_diffrn_orient_matrix_UB_13      -0.0541049000
_diffrn_orient_matrix_UB_21      -0.1192083000
_diffrn_orient_matrix_UB_22      -0.0162355000
_diffrn_orient_matrix_UB_23      0.0053229000
_diffrn_orient_matrix_UB_31      0.0008465000
_diffrn_orient_matrix_UB_32      0.1462841000
_diffrn_orient_matrix_UB_33      0.0727745000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                2244
_reflns_number_total             2332
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.049
_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)+(0.0235P)²+0.3313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0696
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_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
C1 C 0.1987(3) 0.6992(6) 0.3491(2) 0.0267(8) Uani 1 1 d . . . . .
C2 C 0.2902(3) 0.8052(6) 0.3621(2) 0.0265(8) Uani 1 1 d . . . . .
H2 H 0.300032 0.941816 0.342882 0.032 Uiso 1 1 calc R . . . .
C3 C 0.3675(3) 0.7039(6) 0.4045(2) 0.0241(8) Uani 1 1 d . . . . .
H3 H 0.430240 0.771975 0.414495 0.029 Uiso 1 1 calc R . . . .
C4 C 0.3506(3) 0.5020(6) 0.4317(2) 0.0226(8) Uani 1 1 d . . . . .
C5 C 0.2559(3) 0.3980(6) 0.4214(2) 0.0263(8) Uani 1 1 d . . . . .
H5 H 0.244759 0.264229 0.442854 0.032 Uiso 1 1 calc R . . . .
C6 C 0.1787(3) 0.4992(7) 0.3784(2) 0.0301(9) Uani 1 1 d . . . . .
H6 H 0.115000 0.433762 0.369487 0.036 Uiso 1 1 calc R . . . .
C7 C 0.6175(3) 0.7467(6) 0.6407(2) 0.0273(8) Uani 1 1 d . . . . .
C8 C 0.6420(3) 0.9838(7) 0.6386(3) 0.0390(10) Uani 1 1 d . . . . .
H8A H 0.709963 1.007747 0.660151 0.059 Uiso 1 1 calc GR . . . .
H8B H 0.591492 1.059391 0.669346 0.059 Uiso 1 1 calc GR . . . .
H8C H 0.639959 1.033072 0.585069 0.059 Uiso 1 1 calc GR . . . .
C9 C 0.6897(3) 0.6225(7) 0.5869(3) 0.0394(11) Uani 1 1 d . . . . .
H9A H 0.682840 0.673550 0.533789 0.059 Uiso 1 1 calc GR . . . .
H9B H 0.671741 0.474851 0.588689 0.059 Uiso 1 1 calc GR . . . .
H9C H 0.760156 0.640544 0.604169 0.059 Uiso 1 1 calc GR . . . .
C10 C 0.6204(4) 0.6637(8) 0.7254(3) 0.0452(11) Uani 1 1 d . . . . .
H10A H 0.689392 0.678086 0.746080 0.068 Uiso 1 1 calc GR . . . .
H10B H 0.600605 0.516926 0.725910 0.068 Uiso 1 1 calc GR . . . .
H10C H 0.572904 0.743743 0.757294 0.068 Uiso 1 1 calc GR . . . .
N1 N 0.1195(3) 0.8034(6) 0.29925(19) 0.0357(9) Uani 1 1 d . . . . .
O1 O 0.1364(3) 0.9827(6) 0.2762(2) 0.0474(9) Uani 1 1 d . . . . .
O2 O 0.0415(3) 0.7003(6) 0.28309(19) 0.0496(9) Uani 1 1 d . . . . .
O3 O 0.5487(2) 0.4480(5) 0.44579(17) 0.0363(7) Uani 1 1 d . . . . .
O4 O 0.4333(2) 0.1426(4) 0.4734(2) 0.0450(8) Uani 1 1 d . . . . .
S1 S 0.45419(7) 0.36462(14) 0.47808(6) 0.0276(2) Uani 1 1 d . . . . .
S2 S 0.44074(7) 0.43276(14) 0.59871(6) 0.0294(2) Uani 1 1 d . . . . .
S3 S 0.48127(7) 0.74190(13) 0.60448(7) 0.0273(2) 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 C2 1.373(6) . ?
C1 C6 1.380(5) . ?
C1 N1 1.478(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(5) . ?
C4 C5 1.395(6) . ?
C4 S1 1.775(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.529(5) . ?
C7 C9 1.521(6) . ?
C7 C10 1.527(6) . ?
C7 S3 1.859(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 O1 1.216(5) . ?
N1 O2 1.228(5) . ?
O3 S1 1.434(3) . ?
O4 S1 1.429(3) . ?
S1 S2 2.0965(15) . ?
S2 S3 2.0212(13) . ?

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
C2 C1 C6 123.2(4) . . ?
C2 C1 N1 117.9(4) . . ?
C6 C1 N1 118.9(4) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 122.3(4) . . ?
C3 C4 S1 118.8(3) . . ?
C5 C4 S1 118.9(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.4(4) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 118.4(4) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C8 C7 S3 101.7(3) . . ?
C9 C7 C8 111.3(3) . . ?
C9 C7 C10 111.8(4) . . ?
C9 C7 S3 111.7(3) . . ?
C10 C7 C8 110.6(4) . . ?
C10 C7 S3 109.1(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 N1 C1 118.3(4) . . ?
O1 N1 O2 124.6(4) . . ?
O2 N1 C1 117.2(4) . . ?
C4 S1 S2 105.65(13) . . ?
O3 S1 C4 106.86(19) . . ?
O3 S1 S2 111.53(13) . . ?
O4 S1 C4 108.20(18) . . ?
O4 S1 O3 119.86(19) . . ?
O4 S1 S2 103.89(17) . . ?
S3 S2 S1 102.93(6) . . ?
C7 S3 S2 105.98(13) . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.462
_oxdiff_exptl_absorpt_empirical_full_min 0.437
