# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_ga220630a_0m
_database_code_depnum_ccdc_archive 'CCDC 2280046'
loop_
_audit_author_name
_audit_author_address
'Song Sun' 'Changzhou University'
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2022-06-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O4 S'
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.38
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   9.907(4)
_cell_length_b                   10.099(4)
_cell_length_c                   17.406(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.78(3)
_cell_angle_gamma                90
_cell_volume                     1683.8(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1352
_cell_measurement_temperature    128.00
_cell_measurement_theta_max      55.67
_cell_measurement_theta_min      4.43
_shelx_estimated_absorpt_T_max   0.790
_shelx_estimated_absorpt_T_min   0.708
_exptl_absorpt_coefficient_mu    1.239
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.4919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1531 before and 0.0922 after correction.
The Ratio of minimum to maximum transmission is 0.6542.
The λ/2 correction factor is Not present.
;
_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    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1688
_diffrn_reflns_av_unetI/netI     0.1287
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11571
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        52.968
_diffrn_reflns_theta_max         52.968
_diffrn_reflns_theta_min         4.442
_diffrn_ambient_temperature      128.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2494002
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1852
_reflns_number_total             2909
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.039(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0818
_refine_ls_restrained_S_all      0.998
_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)+(0.1603P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2078
_refine_ls_wR_factor_ref         0.2496
_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:
 C00A(H00A), C00D(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00B(H00B,H00C,H00D), C00M(H00G,H00M,H00N), C00O(H00O,H00P,H00Q)
;
_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 0.82264(9) 0.22284(10) 0.48553(5) 0.0558(5) Uani 1 1 d . . . . .
O3 O 0.7215(3) 0.5328(3) 0.75241(16) 0.0635(8) Uani 1 1 d . . . . .
O4 O 0.6321(3) 0.3294(3) 0.75042(16) 0.0682(8) Uani 1 1 d . . . . .
N1 N 0.8822(3) 0.2535(3) 0.58185(17) 0.0522(8) Uani 1 1 d . . . . .
O2 O 0.8372(3) 0.0853(3) 0.46961(16) 0.0726(8) Uani 1 1 d . . . . .
O1 O 0.8816(3) 0.3136(3) 0.43977(15) 0.0690(8) Uani 1 1 d . . . . .
C007 C 0.7840(3) 0.3102(3) 0.6179(2) 0.0473(9) Uani 1 1 d . . . . .
C008 C 0.9666(3) 0.4073(3) 0.73238(19) 0.0469(9) Uani 1 1 d . . . . .
C009 C 0.6525(3) 0.2656(4) 0.4848(2) 0.0504(9) Uani 1 1 d . . . . .
C00A C 1.1529(4) 0.4148(4) 0.8527(2) 0.0607(11) Uani 1 1 d . . . . .
H00A H 1.188138 0.392106 0.907108 0.073 Uiso 1 1 calc R U . . .
C00B C 1.0166(4) 0.1953(4) 0.6230(2) 0.0577(10) Uani 1 1 d . . . . .
H00B H 1.035360 0.117897 0.593384 0.087 Uiso 1 1 calc R U . . .
H00C H 1.013516 0.168023 0.676600 0.087 Uiso 1 1 calc R U . . .
H00D H 1.090813 0.260904 0.626676 0.087 Uiso 1 1 calc R U . . .
C00C C 0.6440(3) 0.3060(3) 0.56055(19) 0.0465(9) Uani 1 1 d . . . . .
C00D C 1.0208(4) 0.3731(4) 0.8117(2) 0.0534(9) Uani 1 1 d . . . . .
H00E H 0.966744 0.320614 0.838086 0.064 Uiso 1 1 calc R U . . .
C00E C 0.8208(3) 0.3689(3) 0.69000(19) 0.0474(9) Uani 1 1 d . . . . .
C00F C 1.1807(4) 0.5236(4) 0.7362(2) 0.0602(11) Uani 1 1 d . . . . .
H00F H 1.235926 0.574859 0.710050 0.072 Uiso 1 1 calc R U . . .
C00G C 0.3960(3) 0.3433(3) 0.5033(2) 0.0529(10) Uani 1 1 d . . . . .
C00H C 0.5396(4) 0.2672(4) 0.4186(2) 0.0576(10) Uani 1 1 d . . . . .
H00H H 0.549642 0.241905 0.367764 0.069 Uiso 1 1 calc R U . . .
C00I C 0.4118(4) 0.3068(4) 0.4289(2) 0.0581(10) Uani 1 1 d . . . . .
H00I H 0.333076 0.309262 0.384307 0.070 Uiso 1 1 calc R U . . .
C00J C 0.5123(3) 0.3445(3) 0.5683(2) 0.0496(9) Uani 1 1 d . . . . .
H00J H 0.502027 0.371845 0.618744 0.060 Uiso 1 1 calc R U . . .
C00K C 1.0479(4) 0.4840(4) 0.6949(2) 0.0538(9) Uani 1 1 d . . . . .
H00K H 1.012239 0.509238 0.640983 0.065 Uiso 1 1 calc R U . . .
C00L C 1.2332(4) 0.4892(4) 0.8149(2) 0.0620(11) Uani 1 1 d . . . . .
H00L H 1.324234 0.516576 0.842783 0.074 Uiso 1 1 calc R U . . .
C00M C 0.2539(4) 0.3796(5) 0.5131(2) 0.0688(12) Uani 1 1 d . . . . .
H00G H 0.204917 0.434386 0.468115 0.103 Uiso 1 1 calc R U . . .
H00M H 0.264171 0.429241 0.562636 0.103 Uiso 1 1 calc R U . . .
H00N H 0.199987 0.298786 0.514892 0.103 Uiso 1 1 calc R U . . .
C00N C 0.7141(4) 0.4047(4) 0.73291(18) 0.0504(9) Uani 1 1 d . . . . .
C00O C 0.6263(4) 0.5785(5) 0.7971(3) 0.0811(13) Uani 1 1 d . . . . .
H00O H 0.531191 0.550585 0.770399 0.122 Uiso 1 1 calc R U . . .
H00P H 0.630036 0.675375 0.800620 0.122 Uiso 1 1 calc R U . . .
H00Q H 0.653075 0.540698 0.850724 0.122 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 N1 1.658(3) . ?
S1 O2 1.431(3) . ?
S1 O1 1.433(3) . ?
S1 C009 1.737(4) . ?
O3 C00N 1.335(4) . ?
O3 C00O 1.443(5) . ?
O4 C00N 1.208(4) . ?
N1 C007 1.408(4) . ?
N1 C00B 1.464(4) . ?
C007 C00C 1.488(4) . ?
C007 C00E 1.351(5) . ?
C008 C00D 1.392(4) . ?
C008 C00E 1.495(4) . ?
C008 C00K 1.393(5) . ?
C009 C00C 1.404(5) . ?
C009 C00H 1.386(5) . ?
C00A H00A 0.9500 . ?
C00A C00D 1.387(5) . ?
C00A C00L 1.378(6) . ?
C00B H00B 0.9800 . ?
C00B H00C 0.9800 . ?
C00B H00D 0.9800 . ?
C00C C00J 1.401(5) . ?
C00D H00E 0.9500 . ?
C00E C00N 1.486(5) . ?
C00F H00F 0.9500 . ?
C00F C00K 1.387(5) . ?
C00F C00L 1.379(6) . ?
C00G C00I 1.393(5) . ?
C00G C00J 1.393(5) . ?
C00G C00M 1.507(5) . ?
C00H H00H 0.9500 . ?
C00H C00I 1.382(5) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00M H00G 0.9800 . ?
C00M H00M 0.9800 . ?
C00M H00N 0.9800 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00O H00Q 0.9800 . ?

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
N1 S1 C009 93.19(16) . . ?
O2 S1 N1 110.45(16) . . ?
O2 S1 O1 115.95(19) . . ?
O2 S1 C009 112.70(17) . . ?
O1 S1 N1 110.61(16) . . ?
O1 S1 C009 111.68(17) . . ?
C00N O3 C00O 116.5(3) . . ?
C007 N1 S1 114.7(2) . . ?
C007 N1 C00B 126.2(3) . . ?
C00B N1 S1 117.7(2) . . ?
N1 C007 C00C 108.7(3) . . ?
C00E C007 N1 122.6(3) . . ?
C00E C007 C00C 128.4(3) . . ?
C00D C008 C00E 120.3(3) . . ?
C00D C008 C00K 118.7(3) . . ?
C00K C008 C00E 120.9(3) . . ?
C00C C009 S1 110.9(3) . . ?
C00H C009 S1 125.8(3) . . ?
C00H C009 C00C 123.3(3) . . ?
C00D C00A H00A 119.9 . . ?
C00L C00A H00A 119.9 . . ?
C00L C00A C00D 120.3(3) . . ?
N1 C00B H00B 109.5 . . ?
N1 C00B H00C 109.5 . . ?
N1 C00B H00D 109.5 . . ?
H00B C00B H00C 109.5 . . ?
H00B C00B H00D 109.5 . . ?
H00C C00B H00D 109.5 . . ?
C009 C00C C007 111.7(3) . . ?
C00J C00C C007 131.2(3) . . ?
C00J C00C C009 116.9(3) . . ?
C008 C00D H00E 119.7 . . ?
C00A C00D C008 120.6(4) . . ?
C00A C00D H00E 119.7 . . ?
C007 C00E C008 124.8(3) . . ?
C007 C00E C00N 121.0(3) . . ?
C00N C00E C008 114.2(3) . . ?
C00K C00F H00F 119.7 . . ?
C00L C00F H00F 119.7 . . ?
C00L C00F C00K 120.6(4) . . ?
C00I C00G C00J 119.5(3) . . ?
C00I C00G C00M 120.0(3) . . ?
C00J C00G C00M 120.6(3) . . ?
C009 C00H H00H 121.1 . . ?
C00I C00H C009 117.8(4) . . ?
C00I C00H H00H 121.1 . . ?
C00G C00I H00I 119.3 . . ?
C00H C00I C00G 121.4(3) . . ?
C00H C00I H00I 119.3 . . ?
C00C C00J H00J 119.5 . . ?
C00G C00J C00C 121.1(3) . . ?
C00G C00J H00J 119.5 . . ?
C008 C00K H00K 119.9 . . ?
C00F C00K C008 120.2(3) . . ?
C00F C00K H00K 119.9 . . ?
C00A C00L C00F 119.6(3) . . ?
C00A C00L H00L 120.2 . . ?
C00F C00L H00L 120.2 . . ?
C00G C00M H00G 109.5 . . ?
C00G C00M H00M 109.5 . . ?
C00G C00M H00N 109.5 . . ?
H00G C00M H00M 109.5 . . ?
H00G C00M H00N 109.5 . . ?
H00M C00M H00N 109.5 . . ?
O3 C00N C00E 111.3(3) . . ?
O4 C00N O3 122.9(3) . . ?
O4 C00N C00E 125.8(4) . . ?
O3 C00O H00O 109.5 . . ?
O3 C00O H00P 109.5 . . ?
O3 C00O H00Q 109.5 . . ?
H00O C00O H00P 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 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
S1 N1 C007 C00C 9.5(4) . . . . ?
S1 N1 C007 C00E -164.5(3) . . . . ?
S1 C009 C00C C007 4.3(4) . . . . ?
S1 C009 C00C C00J 179.5(3) . . . . ?
S1 C009 C00H C00I -178.6(3) . . . . ?
N1 S1 C009 C00C 0.9(3) . . . . ?
N1 S1 C009 C00H 177.8(3) . . . . ?
N1 C007 C00C C009 -8.5(4) . . . . ?
N1 C007 C00C C00J 177.1(3) . . . . ?
N1 C007 C00E C008 13.7(5) . . . . ?
N1 C007 C00E C00N -168.2(3) . . . . ?
O2 S1 N1 C007 -122.0(3) . . . . ?
O2 S1 N1 C00B 45.5(3) . . . . ?
O2 S1 C009 C00C 114.7(3) . . . . ?
O2 S1 C009 C00H -68.4(3) . . . . ?
O1 S1 N1 C007 108.3(3) . . . . ?
O1 S1 N1 C00B -84.2(3) . . . . ?
O1 S1 C009 C00C -112.7(3) . . . . ?
O1 S1 C009 C00H 64.2(4) . . . . ?
C007 C00C C00J C00G 173.6(3) . . . . ?
C007 C00E C00N O3 -125.0(4) . . . . ?
C007 C00E C00N O4 56.6(5) . . . . ?
C008 C00E C00N O3 53.2(4) . . . . ?
C008 C00E C00N O4 -125.2(4) . . . . ?
C009 S1 N1 C007 -6.3(3) . . . . ?
C009 S1 N1 C00B 161.2(3) . . . . ?
C009 C00C C00J C00G -0.5(5) . . . . ?
C009 C00H C00I C00G -0.4(5) . . . . ?
C00B N1 C007 C00C -156.8(3) . . . . ?
C00B N1 C007 C00E 29.2(5) . . . . ?
C00C C007 C00E C008 -159.1(3) . . . . ?
C00C C007 C00E C00N 19.0(6) . . . . ?
C00C C009 C00H C00I -2.1(5) . . . . ?
C00D C008 C00E C007 -131.4(4) . . . . ?
C00D C008 C00E C00N 50.4(5) . . . . ?
C00D C008 C00K C00F 0.8(5) . . . . ?
C00D C00A C00L C00F 1.0(6) . . . . ?
C00E C007 C00C C009 165.1(4) . . . . ?
C00E C007 C00C C00J -9.3(6) . . . . ?
C00E C008 C00D C00A -176.3(3) . . . . ?
C00E C008 C00K C00F 177.2(3) . . . . ?
C00H C009 C00C C007 -172.7(3) . . . . ?
C00H C009 C00C C00J 2.5(5) . . . . ?
C00I C00G C00J C00C -1.8(5) . . . . ?
C00J C00G C00I C00H 2.3(6) . . . . ?
C00K C008 C00D C00A 0.2(5) . . . . ?
C00K C008 C00E C007 52.2(5) . . . . ?
C00K C008 C00E C00N -126.0(4) . . . . ?
C00K C00F C00L C00A 0.0(6) . . . . ?
C00L C00A C00D C008 -1.0(6) . . . . ?
C00L C00F C00K C008 -0.8(6) . . . . ?
C00M C00G C00I C00H -177.0(3) . . . . ?
C00M C00G C00J C00C 177.5(3) . . . . ?
C00O O3 C00N O4 0.7(5) . . . . ?
C00O O3 C00N C00E -177.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_b230920a_0m
_database_code_depnum_ccdc_archive 'CCDC 2348034'
loop_
_audit_author_name
_audit_author_address
'Song Sun'
;Changzhou University
China
;
_audit_update_record             
;
2024-04-13 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2023-09-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O6 S'
_chemical_formula_sum            'C14 H15 N O6 S'
_chemical_formula_weight         325.33
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9471(6)
_cell_length_b                   7.9767(6)
_cell_length_c                   12.2761(10)
_cell_angle_alpha                74.518(2)
_cell_angle_beta                 88.476(3)
_cell_angle_gamma                84.620(2)
_cell_volume                     746.66(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6916
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1334 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.7158.
The λ/2 correction factor is Not present.
;
_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    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14032
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2767
_reflns_number_total             3395
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.079
_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)+(0.0366P)²+1.1225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1375
_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:
 C00D(H00D), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00C), C00I(H00E,H00F,H00G), C00L(H00H,H00I,H00L), C00M(H00M,
 H00N,H00O)
;
_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 0.10411(8) 0.74560(9) 0.16222(6) 0.02654(18) Uani 1 1 d . . . . .
O4 O 0.5131(2) 0.2601(2) 0.51317(15) 0.0266(4) Uani 1 1 d . . . . .
O6 O 0.7122(2) 0.2678(2) 0.30495(17) 0.0289(4) Uani 1 1 d . . . . .
O5 O 0.7470(2) 0.5273(2) 0.33443(16) 0.0291(4) Uani 1 1 d . . . . .
O3 O 0.2648(2) 0.2511(3) 0.43221(18) 0.0365(5) Uani 1 1 d . . . . .
O1 O -0.0152(2) 0.6572(3) 0.11821(17) 0.0396(5) Uani 1 1 d . . . . .
O2 O 0.0416(3) 0.9041(3) 0.18825(18) 0.0407(5) Uani 1 1 d . . . . .
N1 N 0.2032(2) 0.6129(3) 0.27484(17) 0.0233(4) Uani 1 1 d . . . . .
C009 C 0.4216(3) 0.6578(3) 0.1397(2) 0.0194(5) Uani 1 1 d . . . . .
C00A C 0.3712(3) 0.5619(3) 0.2555(2) 0.0209(5) Uani 1 1 d . . . . .
C00B C 0.6569(3) 0.4205(3) 0.3230(2) 0.0216(5) Uani 1 1 d . . . . .
C00C C 0.3990(3) 0.3105(3) 0.4292(2) 0.0226(5) Uani 1 1 d . . . . .
C00D C 0.5734(3) 0.6432(3) 0.0827(2) 0.0228(5) Uani 1 1 d . . . . .
H00D H 0.667045 0.569991 0.120509 0.027 Uiso 1 1 calc R U . . .
C00E C 0.4679(3) 0.4393(3) 0.3315(2) 0.0206(5) Uani 1 1 d . . . . .
C00F C 0.5880(3) 0.7368(3) -0.0306(2) 0.0242(5) Uani 1 1 d . . . . .
C00G C 0.2865(3) 0.7637(3) 0.0808(2) 0.0244(5) Uani 1 1 d . . . . .
C00H C 0.1268(3) 0.6062(4) 0.3854(2) 0.0292(6) Uani 1 1 d . . . . .
H00A H 0.043547 0.707115 0.378914 0.044 Uiso 1 1 calc R U . . .
H00B H 0.214868 0.608645 0.439199 0.044 Uiso 1 1 calc R U . . .
H00C H 0.070663 0.498328 0.412301 0.044 Uiso 1 1 calc R U . . .
C00I C 0.7505(3) 0.7227(4) -0.0945(2) 0.0317(6) Uani 1 1 d . . . . .
H00E H 0.816863 0.819350 -0.092609 0.048 Uiso 1 1 calc R U . . .
H00F H 0.725198 0.728021 -0.173141 0.048 Uiso 1 1 calc R U . . .
H00G H 0.815259 0.611378 -0.059443 0.048 Uiso 1 1 calc R U . . .
C00J C 0.2957(3) 0.8573(4) -0.0314(2) 0.0318(6) Uani 1 1 d . . . . .
H00J H 0.200997 0.928239 -0.069441 0.038 Uiso 1 1 calc R U . . .
C00K C 0.4484(3) 0.8429(4) -0.0852(2) 0.0300(6) Uani 1 1 d . . . . .
H00K H 0.459288 0.907100 -0.161934 0.036 Uiso 1 1 calc R U . . .
C00L C 0.4665(4) 0.1270(3) 0.6112(2) 0.0340(6) Uani 1 1 d . . . . .
H00H H 0.423491 0.031464 0.587134 0.051 Uiso 1 1 calc R U . . .
H00I H 0.378573 0.177189 0.653733 0.051 Uiso 1 1 calc R U . . .
H00L H 0.565847 0.082062 0.659443 0.051 Uiso 1 1 calc R U . . .
C00M C 0.8952(3) 0.2300(4) 0.3066(3) 0.0441(8) Uani 1 1 d . . . . .
H00M H 0.946153 0.321617 0.249188 0.066 Uiso 1 1 calc R U . . .
H00N H 0.924107 0.116900 0.290378 0.066 Uiso 1 1 calc R U . . .
H00O H 0.938477 0.225946 0.381357 0.066 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 O1 1.430(2) . ?
S1 O2 1.428(2) . ?
S1 N1 1.665(2) . ?
S1 C00G 1.734(3) . ?
O4 C00C 1.344(3) . ?
O4 C00L 1.443(3) . ?
O6 C00B 1.329(3) . ?
O6 C00M 1.457(3) . ?
O5 C00B 1.200(3) . ?
O3 C00C 1.203(3) . ?
N1 C00A 1.392(3) . ?
N1 C00H 1.462(3) . ?
C009 C00A 1.488(3) . ?
C009 C00D 1.390(3) . ?
C009 C00G 1.391(3) . ?
C00A C00E 1.352(3) . ?
C00B C00E 1.499(3) . ?
C00C C00E 1.486(3) . ?
C00D H00D 0.9500 . ?
C00D C00F 1.400(3) . ?
C00F C00I 1.504(4) . ?
C00F C00K 1.399(4) . ?
C00G C00J 1.384(4) . ?
C00H H00A 0.9800 . ?
C00H H00B 0.9800 . ?
C00H H00C 0.9800 . ?
C00I H00E 0.9800 . ?
C00I H00F 0.9800 . ?
C00I H00G 0.9800 . ?
C00J H00J 0.9500 . ?
C00J C00K 1.376(4) . ?
C00K H00K 0.9500 . ?
C00L H00H 0.9800 . ?
C00L H00I 0.9800 . ?
C00L H00L 0.9800 . ?
C00M H00M 0.9800 . ?
C00M H00N 0.9800 . ?
C00M H00O 0.9800 . ?

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 N1 111.13(12) . . ?
O1 S1 C00G 110.62(12) . . ?
O2 S1 O1 116.69(13) . . ?
O2 S1 N1 109.17(12) . . ?
O2 S1 C00G 113.61(13) . . ?
N1 S1 C00G 93.16(11) . . ?
C00C O4 C00L 116.1(2) . . ?
C00B O6 C00M 115.3(2) . . ?
C00A N1 S1 114.26(17) . . ?
C00A N1 C00H 125.7(2) . . ?
C00H N1 S1 117.25(16) . . ?
C00D C009 C00A 129.7(2) . . ?
C00D C009 C00G 118.4(2) . . ?
C00G C009 C00A 111.7(2) . . ?
N1 C00A C009 109.6(2) . . ?
C00E C00A N1 123.5(2) . . ?
C00E C00A C009 126.8(2) . . ?
O6 C00B C00E 111.2(2) . . ?
O5 C00B O6 124.3(2) . . ?
O5 C00B C00E 124.5(2) . . ?
O4 C00C C00E 110.16(19) . . ?
O3 C00C O4 123.9(2) . . ?
O3 C00C C00E 125.8(2) . . ?
C009 C00D H00D 120.1 . . ?
C009 C00D C00F 119.8(2) . . ?
C00F C00D H00D 120.1 . . ?
C00A C00E C00B 122.2(2) . . ?
C00A C00E C00C 123.9(2) . . ?
C00C C00E C00B 113.9(2) . . ?
C00D C00F C00I 120.9(2) . . ?
C00K C00F C00D 119.3(2) . . ?
C00K C00F C00I 119.8(2) . . ?
C009 C00G S1 110.99(18) . . ?
C00J C00G S1 125.3(2) . . ?
C00J C00G C009 123.5(2) . . ?
N1 C00H H00A 109.5 . . ?
N1 C00H H00B 109.5 . . ?
N1 C00H H00C 109.5 . . ?
H00A C00H H00B 109.5 . . ?
H00A C00H H00C 109.5 . . ?
H00B C00H H00C 109.5 . . ?
C00F C00I H00E 109.5 . . ?
C00F C00I H00F 109.5 . . ?
C00F C00I H00G 109.5 . . ?
H00E C00I H00F 109.5 . . ?
H00E C00I H00G 109.5 . . ?
H00F C00I H00G 109.5 . . ?
C00G C00J H00J 121.5 . . ?
C00K C00J C00G 116.9(2) . . ?
C00K C00J H00J 121.5 . . ?
C00F C00K H00K 119.0 . . ?
C00J C00K C00F 122.1(2) . . ?
C00J C00K H00K 119.0 . . ?
O4 C00L H00H 109.5 . . ?
O4 C00L H00I 109.5 . . ?
O4 C00L H00L 109.5 . . ?
H00H C00L H00I 109.5 . . ?
H00H C00L H00L 109.5 . . ?
H00I C00L H00L 109.5 . . ?
O6 C00M H00M 109.5 . . ?
O6 C00M H00N 109.5 . . ?
O6 C00M H00O 109.5 . . ?
H00M C00M H00N 109.5 . . ?
H00M C00M H00O 109.5 . . ?
H00N C00M H00O 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
S1 N1 C00A C009 6.1(3) . . . . ?
S1 N1 C00A C00E -172.08(19) . . . . ?
S1 C00G C00J C00K -173.9(2) . . . . ?
O4 C00C C00E C00A -153.3(2) . . . . ?
O4 C00C C00E C00B 27.4(3) . . . . ?
O6 C00B C00E C00A -115.4(3) . . . . ?
O6 C00B C00E C00C 63.8(3) . . . . ?
O5 C00B C00E C00A 66.7(4) . . . . ?
O5 C00B C00E C00C -114.1(3) . . . . ?
O3 C00C C00E C00A 30.5(4) . . . . ?
O3 C00C C00E C00B -148.8(3) . . . . ?
O1 S1 N1 C00A 107.83(19) . . . . ?
O1 S1 N1 C00H -90.1(2) . . . . ?
O1 S1 C00G C009 -110.4(2) . . . . ?
O1 S1 C00G C00J 63.9(3) . . . . ?
O2 S1 N1 C00A -122.07(19) . . . . ?
O2 S1 N1 C00H 40.0(2) . . . . ?
O2 S1 C00G C009 116.09(19) . . . . ?
O2 S1 C00G C00J -69.5(3) . . . . ?
N1 S1 C00G C009 3.57(19) . . . . ?
N1 S1 C00G C00J 177.9(2) . . . . ?
N1 C00A C00E C00B -163.1(2) . . . . ?
N1 C00A C00E C00C 17.7(4) . . . . ?
C009 C00A C00E C00B 19.0(4) . . . . ?
C009 C00A C00E C00C -160.2(2) . . . . ?
C009 C00D C00F C00I -179.7(2) . . . . ?
C009 C00D C00F C00K -0.5(4) . . . . ?
C009 C00G C00J C00K -0.3(4) . . . . ?
C00A C009 C00D C00F 174.4(2) . . . . ?
C00A C009 C00G S1 -0.7(3) . . . . ?
C00A C009 C00G C00J -175.2(2) . . . . ?
C00D C009 C00A N1 -176.8(2) . . . . ?
C00D C009 C00A C00E 1.3(4) . . . . ?
C00D C009 C00G S1 173.62(18) . . . . ?
C00D C009 C00G C00J -0.9(4) . . . . ?
C00D C00F C00K C00J -0.6(4) . . . . ?
C00G S1 N1 C00A -5.72(19) . . . . ?
C00G S1 N1 C00H 156.3(2) . . . . ?
C00G C009 C00A N1 -3.3(3) . . . . ?
C00G C009 C00A C00E 174.8(2) . . . . ?
C00G C009 C00D C00F 1.2(3) . . . . ?
C00G C00J C00K C00F 1.0(4) . . . . ?
C00H N1 C00A C009 -154.2(2) . . . . ?
C00H N1 C00A C00E 27.6(4) . . . . ?
C00I C00F C00K C00J 178.5(3) . . . . ?
C00L O4 C00C O3 -0.2(4) . . . . ?
C00L O4 C00C C00E -176.5(2) . . . . ?
C00M O6 C00B O5 3.8(4) . . . . ?
C00M O6 C00B C00E -174.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
