# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_mo_ValerieC_1_orth_0m
_audit_block_doi                 10.5517/ccdc.csd.cc25q367
_database_code_depnum_ccdc_archive 'CCDC 2017238'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0SC05172A 2021
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2023-07-26 deposited with the CCDC.	2023-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H13 N O4 S2'
_chemical_formula_sum            'C8 H13 N O4 S2'
_chemical_formula_weight         251.31

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0194(4)
_cell_length_b                   7.1500(6)
_cell_length_c                   27.3932(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1178.97(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    16371
_cell_measurement_theta_min      2.944
_cell_measurement_theta_max      25.002

_exptl_crystal_description       paralelipiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.446
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8728
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.944
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_full        25.002
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2080
_reflns_number_gt                1949
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0267P)²+2.0062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2080
_refine_ls_number_parameters     145
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.190
_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
S1 S 0.9912(2) 0.6943(3) 0.62813(5) 0.0571(5) Uani 1 1 d . U . . .
O1 O 0.4067(8) 0.8846(8) 0.73529(19) 0.0743(17) Uani 1 1 d . U . . .
N1 N 0.5852(7) 0.6547(6) 0.66878(13) 0.0296(9) Uani 1 1 d D . . . .
H1 H 0.515(8) 0.749(5) 0.6563(17) 0.035 Uiso 1 1 d D U . . .
C1 C 0.9170(9) 0.8441(10) 0.6779(2) 0.0486(14) Uani 1 1 d . U . . .
H1A H 1.043684 0.865923 0.699030 0.058 Uiso 1 1 calc R U . . .
H1B H 0.862842 0.963435 0.666009 0.058 Uiso 1 1 calc R U . . .
S2 S 0.5070(5) 0.2243(3) 0.62702(8) 0.0844(7) Uani 1 1 d D . . . .
H2 H 0.490(13) 0.237(11) 0.5833(10) 0.127 Uiso 1 1 d D U . . .
O2 O 0.7232(7) 0.9428(7) 0.77278(15) 0.0573(13) Uani 1 1 d . . . . .
H2A H 0.637(8) 1.008(11) 0.792(3) 0.086 Uiso 1 1 calc R U . . .
C2 C 0.7354(8) 0.7399(7) 0.70498(17) 0.0319(11) Uani 1 1 d . . . . .
H2B H 0.803925 0.639774 0.724212 0.038 Uiso 1 1 calc R U . . .
O3 O 0.6884(7) 0.5200(6) 0.54455(13) 0.0522(11) Uani 1 1 d . . . . .
C3 C 0.6002(10) 0.8623(9) 0.73895(19) 0.0396(13) Uani 1 1 d . . . . .
C4 C 0.7156(8) 0.5741(7) 0.62913(18) 0.0350(11) Uani 1 1 d . U . . .
O4 O 0.4717(7) 0.7457(6) 0.57625(13) 0.0487(10) Uani 1 1 d . . . . .
C7 C 0.5976(14) 0.5573(11) 0.4960(2) 0.0645(19) Uani 1 1 d . U . . .
H7A H 0.709596 0.531050 0.471453 0.077 Uiso 1 1 calc R U . . .
H7B H 0.557315 0.688280 0.493430 0.077 Uiso 1 1 calc R U . . .
C6 C 0.6068(9) 0.6240(8) 0.58050(18) 0.0357(12) Uani 1 1 d . . . . .
C5 C 0.7522(12) 0.3657(9) 0.6360(2) 0.0563(17) Uani 1 1 d D . . . .
H5A H 0.807583 0.344417 0.668829 0.068 Uiso 1 1 calc R U . . .
H5B H 0.865968 0.324660 0.613382 0.068 Uiso 1 1 calc R U . . .
C8 C 0.4013(19) 0.4409(14) 0.4870(3) 0.105(3) Uani 1 1 d . U . . .
H8A H 0.352697 0.457525 0.453914 0.157 Uiso 1 1 calc R U . . .
H8B H 0.284368 0.477080 0.508902 0.157 Uiso 1 1 calc R U . . .
H8C H 0.438173 0.311895 0.492352 0.157 Uiso 1 1 calc R U . . .


_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 1.791(7) . ?
S1 C4 1.868(6) . ?
O1 C3 1.180(6) . ?
N1 C4 1.459(6) . ?
N1 C2 1.474(6) . ?
N1 H1 0.865(13) . ?
C1 C2 1.516(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
S2 C5 1.806(8) . ?
S2 H2 1.20(3) . ?
O2 C3 1.319(7) . ?
O2 H2A 0.88(8) . ?
C2 C3 1.515(7) . ?
C2 H2B 0.9800 . ?
O3 C6 1.328(7) . ?
O3 C7 1.463(7) . ?
C4 C5 1.518(8) . ?
C4 C6 1.527(7) . ?
O4 C6 1.197(6) . ?
C7 C8 1.466(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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 S1 C4 92.4(3) . . ?
C4 N1 C2 109.5(4) . . ?
C4 N1 H1 106(4) . . ?
C2 N1 H1 104(4) . . ?
C2 C1 S1 105.0(4) . . ?
C2 C1 H1A 110.7 . . ?
S1 C1 H1A 110.7 . . ?
C2 C1 H1B 110.7 . . ?
S1 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C5 S2 H2 99(3) . . ?
C3 O2 H2A 109.5 . . ?
N1 C2 C3 108.8(4) . . ?
N1 C2 C1 108.4(4) . . ?
C3 C2 C1 113.8(5) . . ?
N1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C6 O3 C7 115.7(5) . . ?
O1 C3 O2 123.7(6) . . ?
O1 C3 C2 123.8(6) . . ?
O2 C3 C2 112.5(5) . . ?
N1 C4 C5 111.9(5) . . ?
N1 C4 C6 109.1(4) . . ?
C5 C4 C6 113.6(5) . . ?
N1 C4 S1 107.9(4) . . ?
C5 C4 S1 108.9(4) . . ?
C6 C4 S1 105.1(3) . . ?
O3 C7 C8 110.5(6) . . ?
O3 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
O3 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O4 C6 O3 125.9(5) . . ?
O4 C6 C4 123.1(5) . . ?
O3 C6 C4 110.9(5) . . ?
C4 C5 S2 114.5(4) . . ?
C4 C5 H5A 108.6 . . ?
S2 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
S2 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C4 S1 C1 C2 23.7(4) . . . . ?
C4 N1 C2 C3 166.4(4) . . . . ?
C4 N1 C2 C1 42.1(6) . . . . ?
S1 C1 C2 N1 -41.3(5) . . . . ?
S1 C1 C2 C3 -162.6(4) . . . . ?
N1 C2 C3 O1 -1.2(9) . . . . ?
C1 C2 C3 O1 119.9(8) . . . . ?
N1 C2 C3 O2 179.5(5) . . . . ?
C1 C2 C3 O2 -59.4(6) . . . . ?
C2 N1 C4 C5 97.1(5) . . . . ?
C2 N1 C4 C6 -136.4(4) . . . . ?
C2 N1 C4 S1 -22.7(5) . . . . ?
C1 S1 C4 N1 -1.3(4) . . . . ?
C1 S1 C4 C5 -123.0(4) . . . . ?
C1 S1 C4 C6 114.9(4) . . . . ?
C6 O3 C7 C8 -89.5(8) . . . . ?
C7 O3 C6 O4 -1.7(8) . . . . ?
C7 O3 C6 C4 -179.4(5) . . . . ?
N1 C4 C6 O4 16.6(7) . . . . ?
C5 C4 C6 O4 142.1(6) . . . . ?
S1 C4 C6 O4 -98.9(5) . . . . ?
N1 C4 C6 O3 -165.7(4) . . . . ?
C5 C4 C6 O3 -40.2(6) . . . . ?
S1 C4 C6 O3 78.8(5) . . . . ?
N1 C4 C5 S2 71.3(5) . . . . ?
C6 C4 C5 S2 -52.7(6) . . . . ?
S1 C4 C5 S2 -169.5(3) . . . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.061

