# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_e5055b_a
_database_code_depnum_ccdc_archive 'CCDC 2132416'
loop_
_audit_author_name
_audit_author_address
'Gruber Nathalie'
;University  of Strasbourg
France
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-06-17 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         'C10 H10 N O3 S'
_chemical_formula_sum            'C10 H10 N O3 S'
_chemical_formula_weight         224.25

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.4296(4)
_cell_length_b                   7.2645(4)
_cell_length_c                   11.6117(6)
_cell_angle_alpha                76.869(2)
_cell_angle_beta                 79.676(2)
_cell_angle_gamma                67.916(2)
_cell_volume                     486.77(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6112
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      28.34

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             234
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.317
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_T_max  0.7545
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12135
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.074
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             2279
_reflns_number_gt                2072
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0346P)²+0.3297P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2279
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_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 0.66110(6) 0.59483(6) 0.61777(3) 0.02666(13) Uani 1 1 d . . . . .
O1 O 0.6661(2) 0.40750(19) 0.59584(12) 0.0378(3) Uani 1 1 d . . . . .
O2 O 0.7503(2) 0.7165(2) 0.52273(12) 0.0442(3) Uani 1 1 d . . . . .
N1 N 0.7888(2) 0.5516(2) 0.73981(12) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.3998(2) 0.7335(2) 0.68453(13) 0.0235(3) Uani 1 1 d . . . . .
C2 C 0.2009(3) 0.8243(2) 0.63078(14) 0.0288(3) Uani 1 1 d . . . . .
H2 H 0.196155 0.816570 0.550762 0.035 Uiso 1 1 calc R U . . .
C3 C 0.0101(3) 0.9263(2) 0.69843(16) 0.0303(3) Uani 1 1 d . . . . .
H3 H -0.128845 0.991504 0.664359 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0189(3) 0.9348(2) 0.81580(16) 0.0300(3) Uani 1 1 d . . . . .
H4 H -0.114485 1.004765 0.861068 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2201(3) 0.8425(2) 0.86789(15) 0.0284(3) Uani 1 1 d . . . . .
H5 H 0.224834 0.849093 0.948106 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4134(2) 0.7408(2) 0.80109(14) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.6444(3) 0.6323(2) 0.84225(14) 0.0268(3) Uani 1 1 d . . . . .
H7A H 0.698598 0.726608 0.867178 0.032 Uiso 1 1 calc R U . . .
H7B H 0.642339 0.522014 0.910073 0.032 Uiso 1 1 calc R U . . .
C8 C 1.0109(2) 0.4323(2) 0.74296(14) 0.0258(3) Uani 1 1 d . . . . .
H8 H 1.088671 0.379284 0.673393 0.031 Uiso 1 1 calc R U . . .
C9 C 1.1271(3) 0.3844(2) 0.83704(15) 0.0268(3) Uani 1 1 d . . . . .
H9 H 1.054447 0.430915 0.909124 0.032 Uiso 1 1 calc R U . . .
C10 C 1.3627(3) 0.2622(3) 0.82791(16) 0.0315(4) Uani 1 1 d . . . . .
H10 H 1.425267 0.208408 0.756967 0.038 Uiso 1 1 calc R U . . .
O3 O 1.4880(2) 0.2224(2) 0.90428(13) 0.0438(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
S1 O1 1.4282(13) . ?
S1 O2 1.4279(13) . ?
S1 N1 1.6737(13) . ?
S1 C1 1.7474(16) . ?
N1 C8 1.3657(19) . ?
N1 C7 1.460(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.387(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.503(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.341(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.438(2) . ?
C9 H9 0.9500 . ?
C10 O3 1.218(2) . ?
C10 H10 0.9500 . ?

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
O1 S1 O2 117.08(9) . . ?
O1 S1 N1 109.04(7) . . ?
O2 S1 N1 110.05(8) . . ?
O1 S1 C1 112.80(8) . . ?
O2 S1 C1 112.50(8) . . ?
N1 S1 C1 92.58(7) . . ?
C8 N1 C7 123.61(13) . . ?
C8 N1 S1 120.11(11) . . ?
C7 N1 S1 116.04(10) . . ?
C6 C1 C2 123.09(15) . . ?
C6 C1 S1 111.29(11) . . ?
C2 C1 S1 125.62(13) . . ?
C3 C2 C1 117.23(15) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 120.80(14) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.99(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.99(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 118.91(14) . . ?
C5 C6 C7 126.42(14) . . ?
C1 C6 C7 114.67(13) . . ?
N1 C7 C6 105.38(12) . . ?
N1 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
N1 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 N1 124.79(15) . . ?
C9 C8 H8 117.6 . . ?
N1 C8 H8 117.6 . . ?
C8 C9 C10 119.44(15) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
O3 C10 C9 124.93(17) . . ?
O3 C10 H10 117.5 . . ?
C9 C10 H10 117.5 . . ?

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
O1 S1 N1 C8 61.22(14) . . . . ?
O2 S1 N1 C8 -68.47(14) . . . . ?
C1 S1 N1 C8 176.43(13) . . . . ?
O1 S1 N1 C7 -113.38(12) . . . . ?
O2 S1 N1 C7 116.93(12) . . . . ?
C1 S1 N1 C7 1.83(12) . . . . ?
O1 S1 C1 C6 110.57(12) . . . . ?
O2 S1 C1 C6 -114.30(12) . . . . ?
N1 S1 C1 C6 -1.34(12) . . . . ?
O1 S1 C1 C2 -68.71(16) . . . . ?
O2 S1 C1 C2 66.42(16) . . . . ?
N1 S1 C1 C2 179.38(14) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
S1 C1 C2 C3 179.42(12) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 C7 -179.89(15) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
S1 C1 C6 C5 -179.05(12) . . . . ?
C2 C1 C6 C7 179.87(14) . . . . ?
S1 C1 C6 C7 0.57(17) . . . . ?
C8 N1 C7 C6 -176.10(13) . . . . ?
S1 N1 C7 C6 -1.72(16) . . . . ?
C5 C6 C7 N1 -179.75(14) . . . . ?
C1 C6 C7 N1 0.65(18) . . . . ?
C7 N1 C8 C9 -4.2(2) . . . . ?
S1 N1 C8 C9 -178.34(13) . . . . ?
N1 C8 C9 C10 -178.09(14) . . . . ?
C8 C9 C10 O3 174.21(17) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.050

