# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

data_111
_audit_creation_date               2021-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790;
Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984;
Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45,
 575-580.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C17 H17 N3 O4 S'
_chemical_formula_sum              'C17 H17 N3 O4 S'
_chemical_formula_weight           359.39
_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                     8.7875(5)
_cell_length_b                     8.8129(5)
_cell_length_c                     11.7354(6)
_cell_angle_alpha                  93.835(2)
_cell_angle_beta                   111.598(2)
_cell_angle_gamma                  96.227(2)
_cell_volume                       834.41(8)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9934
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        27.508
_cell_measurement_theta_min        3.167
_shelx_estimated_absorpt_T_max     0.967
_shelx_estimated_absorpt_T_min     0.932
_exptl_absorpt_coefficient_mu      0.222
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6900
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0494 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.9254.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colorless
_exptl_crystal_density_diffrn      1.430
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               376
_exptl_crystal_size_max            0.32
_exptl_crystal_size_mid            0.21
_exptl_crystal_size_min            0.15
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0228
_diffrn_reflns_av_unetI/netI       0.0208
_diffrn_reflns_Laue_measured_fraction_full  0.993
_diffrn_reflns_Laue_measured_fraction_max  0.994
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         15
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              17497
_diffrn_reflns_point_group_measured_fraction_full  0.993
_diffrn_reflns_point_group_measured_fraction_max  0.994
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.538
_diffrn_reflns_theta_min           3.167
_diffrn_ambient_temperature        293(2)
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.993
_diffrn_measured_fraction_theta_max  0.994
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator    'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3202
_reflns_number_total               3842
_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 V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max           0.235
_refine_diff_density_min           -0.345
_refine_diff_density_rms           0.039
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       228
_refine_ls_number_reflns           3842
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0481
_refine_ls_R_factor_gt             0.0388
_refine_ls_restrained_S_all        1.046
_refine_ls_shift/su_max            0.004
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0614P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1068
_refine_ls_wR_factor_ref           0.1133
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C14(H14), C13(H13), C4(H4), C6(H6), C3(H3), C7(H7)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_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 0.32291(5) 0.83090(4) 0.31410(3) 0.04545(14) Uani 1 1 d . . . . .
 O4 O 0.16821(14) 0.29000(11) -0.05570(10) 0.0446(3) Uani 1 1 d . . . . .
 N3 N 0.32338(14) 0.58409(12) -0.07180(10) 0.0328(2) Uani 1 1 d . . . . .
 O2 O 0.32679(17) 0.97473(13) 0.26692(12) 0.0579(3) Uani 1 1 d . . . . .
 O3 O 0.13010(15) 0.38476(13) 0.11352(10) 0.0493(3) Uani 1 1 d . . . . .
 O1 O 0.22347(18) 0.79441(17) 0.38350(12) 0.0639(4) Uani 1 1 d . . . . .
 N1 N 0.25236(17) 0.69541(15) 0.19713(12) 0.0448(3) Uani 1 1 d . . . . .
 H1 H 0.178148 0.624154 0.198427 0.054 Uiso 1 1 calc R . . . .
 N2 N 0.38136(16) 0.79729(13) 0.06343(11) 0.0401(3) Uani 1 1 d . . . . .
 C8 C 0.29864(17) 0.68254(16) 0.09636(12) 0.0353(3) Uani 1 1 d . . . . .
 C15 C 0.18009(17) 0.40214(16) 0.03036(13) 0.0377(3) Uani 1 1 d . . . . .
 C10 C 0.39513(17) 0.73657(15) -0.03973(13) 0.0347(3) Uani 1 1 d . . . . .
 C5 C 0.5261(2) 0.80098(17) 0.39993(13) 0.0435(3) Uani 1 1 d . . . . .
 C9 C 0.26019(17) 0.54743(16) 0.01743(12) 0.0349(3) Uani 1 1 d . . . . .
 C11 C 0.46806(19) 0.80612(17) -0.11481(14) 0.0404(3) Uani 1 1 d . . . . .
 H11 H 0.516080 0.908623 -0.095436 0.049 Uiso 1 1 calc R . . . .
 C12 C 0.4677(2) 0.72179(18) -0.21636(14) 0.0442(3) Uani 1 1 d . . . . .
 H12 H 0.516308 0.766685 -0.266516 0.053 Uiso 1 1 calc R . . . .
 C14 C 0.32304(19) 0.49964(16) -0.17450(13) 0.0406(3) Uani 1 1 d . . . . .
 H14 H 0.274407 0.397336 -0.194618 0.049 Uiso 1 1 calc R . . . .
 C16 C 0.1002(2) 0.13716(16) -0.04354(15) 0.0450(4) Uani 1 1 d . . . . .
 H16A H -0.013272 0.135183 -0.050012 0.054 Uiso 1 1 calc R . . . .
 H16B H 0.164460 0.106080 0.035771 0.054 Uiso 1 1 calc R . . . .
 C13 C 0.3943(2) 0.56721(18) -0.24580(14) 0.0453(4) Uani 1 1 d . . . . .
 H13 H 0.394831 0.510705 -0.315447 0.054 Uiso 1 1 calc R . . . .
 C4 C 0.5544(3) 0.7141(2) 0.49728(15) 0.0565(4) Uani 1 1 d . . . . .
 H4 H 0.467323 0.674231 0.518525 0.068 Uiso 1 1 calc R . . . .
 C6 C 0.6554(2) 0.8607(2) 0.36835(16) 0.0554(4) Uani 1 1 d . . . . .
 H6 H 0.636680 0.921259 0.303900 0.066 Uiso 1 1 calc R . . . .
 C17 C 0.1079(3) 0.0317(2) -0.14619(18) 0.0576(4) Uani 1 1 d . . . . .
 H17A H 0.042951 0.063161 -0.224025 0.086 Uiso 1 1 calc GR . . . .
 H17B H 0.065004 -0.071518 -0.141157 0.086 Uiso 1 1 calc GR . . . .
 H17C H 0.220643 0.035728 -0.139176 0.086 Uiso 1 1 calc GR . . . .
 C3 C 0.7131(3) 0.6872(3) 0.56271(17) 0.0674(5) Uani 1 1 d . . . . .
 H3 H 0.732615 0.630312 0.629355 0.081 Uiso 1 1 calc R . . . .
 C7 C 0.8124(2) 0.8295(2) 0.43362(18) 0.0632(5) Uani 1 1 d . . . . .
 H7 H 0.899069 0.867524 0.411267 0.076 Uiso 1 1 calc R . . . .
 C2 C 0.8439(3) 0.7431(2) 0.53127(16) 0.0613(5) Uani 1 1 d . . . . .
 C1 C 1.0172(3) 0.7102(3) 0.6013(2) 0.0932(8) Uani 1 1 d . . . . .
 H1A H 1.014883 0.639543 0.659657 0.140 Uiso 1 1 calc GR . . . .
 H1B H 1.086726 0.804242 0.644316 0.140 Uiso 1 1 calc GR . . . .
 H1C H 1.060163 0.665995 0.544479 0.140 Uiso 1 1 calc GR . . . .


_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 O2 1.4188(13) . ?
 S1 O1 1.4243(13) . ?
 S1 N1 1.6394(13) . ?
 S1 C5 1.7569(17) . ?
 O4 C15 1.3319(18) . ?
 O4 C16 1.4510(17) . ?
 N3 C10 1.3852(17) . ?
 N3 C9 1.3940(17) . ?
 N3 C14 1.3724(18) . ?
 O3 C15 1.2207(18) . ?
 N1 H1 0.8600 . ?
 N1 C8 1.3866(18) . ?
 N2 C8 1.3418(18) . ?
 N2 C10 1.3423(18) . ?
 C8 C9 1.3874(19) . ?
 C15 C9 1.4377(19) . ?
 C10 C11 1.4020(19) . ?
 C5 C4 1.379(2) . ?
 C5 C6 1.383(2) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.360(2) . ?
 C12 H12 0.9300 . ?
 C12 C13 1.405(2) . ?
 C14 H14 0.9300 . ?
 C14 C13 1.348(2) . ?
 C16 H16A 0.9700 . ?
 C16 H16B 0.9700 . ?
 C16 C17 1.498(2) . ?
 C13 H13 0.9300 . ?
 C4 H4 0.9300 . ?
 C4 C3 1.378(3) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.378(3) . ?
 C17 H17A 0.9600 . ?
 C17 H17B 0.9600 . ?
 C17 H17C 0.9600 . ?
 C3 H3 0.9300 . ?
 C3 C2 1.383(3) . ?
 C7 H7 0.9300 . ?
 C7 C2 1.378(3) . ?
 C2 C1 1.512(3) . ?
 C1 H1A 0.9600 . ?
 C1 H1B 0.9600 . ?
 C1 H1C 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
 O2 S1 O1 120.85(8) . . ?
 O2 S1 N1 108.08(7) . . ?
 O2 S1 C5 109.20(8) . . ?
 O1 S1 N1 103.55(8) . . ?
 O1 S1 C5 108.49(8) . . ?
 N1 S1 C5 105.57(7) . . ?
 C15 O4 C16 116.82(11) . . ?
 C10 N3 C9 106.21(11) . . ?
 C14 N3 C10 121.63(12) . . ?
 C14 N3 C9 132.15(12) . . ?
 S1 N1 H1 116.3 . . ?
 C8 N1 S1 127.45(11) . . ?
 C8 N1 H1 116.3 . . ?
 C8 N2 C10 104.56(12) . . ?
 N1 C8 C9 122.44(13) . . ?
 N2 C8 N1 124.49(13) . . ?
 N2 C8 C9 113.06(12) . . ?
 O4 C15 C9 113.50(12) . . ?
 O3 C15 O4 123.99(13) . . ?
 O3 C15 C9 122.51(13) . . ?
 N3 C10 C11 118.96(13) . . ?
 N2 C10 N3 111.89(12) . . ?
 N2 C10 C11 129.15(13) . . ?
 C4 C5 S1 119.14(14) . . ?
 C4 C5 C6 120.49(17) . . ?
 C6 C5 S1 120.35(13) . . ?
 N3 C9 C15 128.83(13) . . ?
 C8 C9 N3 104.28(11) . . ?
 C8 C9 C15 126.83(13) . . ?
 C10 C11 H11 120.4 . . ?
 C12 C11 C10 119.17(13) . . ?
 C12 C11 H11 120.4 . . ?
 C11 C12 H12 119.8 . . ?
 C11 C12 C13 120.31(14) . . ?
 C13 C12 H12 119.8 . . ?
 N3 C14 H14 120.5 . . ?
 C13 C14 N3 119.01(13) . . ?
 C13 C14 H14 120.5 . . ?
 O4 C16 H16A 110.4 . . ?
 O4 C16 H16B 110.4 . . ?
 O4 C16 C17 106.62(13) . . ?
 H16A C16 H16B 108.6 . . ?
 C17 C16 H16A 110.4 . . ?
 C17 C16 H16B 110.4 . . ?
 C12 C13 H13 119.5 . . ?
 C14 C13 C12 120.92(14) . . ?
 C14 C13 H13 119.5 . . ?
 C5 C4 H4 120.4 . . ?
 C3 C4 C5 119.24(18) . . ?
 C3 C4 H4 120.4 . . ?
 C5 C6 H6 120.4 . . ?
 C7 C6 C5 119.13(17) . . ?
 C7 C6 H6 120.4 . . ?
 C16 C17 H17A 109.5 . . ?
 C16 C17 H17B 109.5 . . ?
 C16 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 C4 C3 H3 119.3 . . ?
 C4 C3 C2 121.33(18) . . ?
 C2 C3 H3 119.3 . . ?
 C6 C7 H7 119.3 . . ?
 C6 C7 C2 121.49(19) . . ?
 C2 C7 H7 119.3 . . ?
 C3 C2 C1 121.2(2) . . ?
 C7 C2 C3 118.30(18) . . ?
 C7 C2 C1 120.5(2) . . ?
 C2 C1 H1A 109.5 . . ?
 C2 C1 H1B 109.5 . . ?
 C2 C1 H1C 109.5 . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 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 C8 N2 -16.2(2) . . . . ?
 S1 N1 C8 C9 164.94(12) . . . . ?
 S1 C5 C4 C3 178.33(14) . . . . ?
 S1 C5 C6 C7 -176.98(14) . . . . ?
 O4 C15 C9 N3 0.6(2) . . . . ?
 O4 C15 C9 C8 -176.15(13) . . . . ?
 N3 C10 C11 C12 -0.6(2) . . . . ?
 N3 C14 C13 C12 -0.2(2) . . . . ?
 O2 S1 N1 C8 45.84(15) . . . . ?
 O2 S1 C5 C4 150.24(13) . . . . ?
 O2 S1 C5 C6 -31.27(16) . . . . ?
 O3 C15 C9 N3 179.86(14) . . . . ?
 O3 C15 C9 C8 3.1(2) . . . . ?
 O1 S1 N1 C8 175.15(13) . . . . ?
 O1 S1 C5 C4 16.70(16) . . . . ?
 O1 S1 C5 C6 -164.82(14) . . . . ?
 N1 S1 C5 C4 -93.77(14) . . . . ?
 N1 S1 C5 C6 84.72(14) . . . . ?
 N1 C8 C9 N3 178.22(12) . . . . ?
 N1 C8 C9 C15 -4.4(2) . . . . ?
 N2 C8 C9 N3 -0.74(16) . . . . ?
 N2 C8 C9 C15 176.65(13) . . . . ?
 N2 C10 C11 C12 -179.89(15) . . . . ?
 C8 N2 C10 N3 -0.58(16) . . . . ?
 C8 N2 C10 C11 178.77(15) . . . . ?
 C15 O4 C16 C17 -177.14(13) . . . . ?
 C10 N3 C9 C8 0.34(14) . . . . ?
 C10 N3 C9 C15 -176.98(14) . . . . ?
 C10 N3 C14 C13 -0.1(2) . . . . ?
 C10 N2 C8 N1 -178.11(13) . . . . ?
 C10 N2 C8 C9 0.83(16) . . . . ?
 C10 C11 C12 C13 0.4(2) . . . . ?
 C5 S1 N1 C8 -70.91(14) . . . . ?
 C5 C4 C3 C2 -1.2(3) . . . . ?
 C5 C6 C7 C2 -1.5(3) . . . . ?
 C9 N3 C10 N2 0.15(15) . . . . ?
 C9 N3 C10 C11 -179.28(12) . . . . ?
 C9 N3 C14 C13 179.57(14) . . . . ?
 C11 C12 C13 C14 0.0(3) . . . . ?
 C14 N3 C10 N2 179.87(12) . . . . ?
 C14 N3 C10 C11 0.4(2) . . . . ?
 C14 N3 C9 C8 -179.34(14) . . . . ?
 C14 N3 C9 C15 3.3(2) . . . . ?
 C16 O4 C15 O3 -3.8(2) . . . . ?
 C16 O4 C15 C9 175.44(12) . . . . ?
 C4 C5 C6 C7 1.5(3) . . . . ?
 C4 C3 C2 C7 1.2(3) . . . . ?
 C4 C3 C2 C1 -178.54(19) . . . . ?
 C6 C5 C4 C3 -0.2(3) . . . . ?
 C6 C7 C2 C3 0.2(3) . . . . ?
 C6 C7 C2 C1 179.93(19) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
