Thiazolidine-2,4-dione framework containing spiropyrrolidine-oxindole and 1,2,3-triazole scaffold: synthesis, in vitro α-amylase inhibition and in silico studies
Duhan, Meenakshi; Singh, Rahul; Devi, Meena; Sindhu, Jayant; Kumar, Parvin; Kumar, Sudhir; Kataria, Ramesh; Kumar, Ashwani; Lal, Sohan; Singh, Devender; New Journal of Chemistry 47 (2023) 5399–5412; doi:10.1039/D2NJ05059E

data_7062274
_publ_section_title
;
 Thiazolidine-2,4-dione framework containing spiropyrrolidine-oxindole and
 1,2,3-triazole scaffold: synthesis, in vitro \a-amylase inhibition and in
 silico studies
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5399
_journal_page_last               5412
_journal_paper_doi               10.1039/D2NJ05059E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C31 H28 N6 O4 S, H2 O'
_chemical_formula_sum            'C31 H30 N6 O5 S'
_chemical_formula_weight         598.68
_chemical_name_systematic        spirooxindole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc250h7y
_audit_creation_date             2020-04-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-03-23 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                94.876(2)
_cell_angle_beta                 91.993(2)
_cell_angle_gamma                96.337(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5926(2)
_cell_length_b                   11.2880(2)
_cell_length_c                   13.4778(3)
_cell_measurement_reflns_used    11544
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6540
_cell_measurement_theta_min      3.3880
_cell_volume                     1594.30(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -16.00  52.00   0.50    5.19    --   -9.95  56.00-104.00  136
  2  \w    -40.00  -1.00   0.50    5.19    --   -9.95 -56.00 113.00   78
  3  \w    -53.00 -15.00   0.50    5.19    --   10.22 -56.00 113.00   76
  4  \w     -1.00  35.00   0.50    5.19    --   10.22  56.00-104.00   72
  5  \w     -8.00  18.00   0.50    5.19    --   -9.95  57.00  30.00   52
  6  \w    -57.00  -4.00   0.50    5.19    --   -9.95 125.00 -30.00  106
  7  \w    -51.00 -17.00   0.50    5.19    --   -9.95 125.00-150.00   68
  8  \w    -34.00  52.00   0.50    5.19    --   -9.95  77.00 120.00  172
  9  \w    -12.00  60.00   0.50    5.19    --   -9.95  19.00-150.00  144
 10  \w    -53.00 -12.00   0.50    5.19    --   10.22 -57.00-120.00   82
 11  \w     46.00  73.00   0.50    5.19    --   10.22  38.00  60.00   54
 12  \w    -18.00  36.00   0.50    5.19    --   10.22 -99.00  90.00  108
 13  \w    -34.00   0.00   0.50    5.19    --   10.22 122.00 142.34   68
 14  \w    -32.00  -7.00   0.50    5.19    --   10.22 122.00 -91.20   50
 15  \w    -19.00  41.00   0.50    5.19    --   10.22 -99.00 -30.00  120
 16  \w     -3.00  26.00   0.50    5.19    --   10.22  38.00  60.00   58
 17  \w    -34.00  -7.00   0.50    5.19    --   10.22 131.00 -44.19   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0349264000
_diffrn_orient_matrix_UB_12      -0.0281786000
_diffrn_orient_matrix_UB_13      0.0352432000
_diffrn_orient_matrix_UB_21      0.0486552000
_diffrn_orient_matrix_UB_22      0.0488288000
_diffrn_orient_matrix_UB_23      0.0030070000
_diffrn_orient_matrix_UB_31      -0.0310009000
_diffrn_orient_matrix_UB_32      0.0291731000
_diffrn_orient_matrix_UB_33      0.0392967000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22342
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.391
_diffrn_reflns_theta_min         3.308
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       needle
_exptl_crystal_F_000             628
_exptl_crystal_preparation       'Multicomponent reaction'
_exptl_crystal_recrystallization_method 'Solvent diffusion method'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         6778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.0437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4909
_reflns_number_total             6778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05059e2.cif
_cod_data_source_block           rk-j1
_cod_depositor_comments
;
          Adding full bibliography for 7062274.cif.

2025-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         52.06
_cod_original_formula_moiety         '0.087(C31 H28 N6 O4 S), 0.087(H2 O)'
_cod_original_formula_units_Z            23
_cod_original_formula_sum        'C2.70 H2.61 N0.52 O0.43 S0.09'
_cod_database_code               7062274
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B)
2.b Ternary CH refined with riding coordinates:
 C24(H24)
2.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C27(H27A,H27B)
2.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C9(H9), C15(H15), C16(H16), C19(H19), C20(H20), C28(H28), C2(H2A),
 C4(H4), C32(H32), C5(H5), C30(H30), C7(H7), C31(H31)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C33(H33A,H33B,H33C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              39782
_shelx_fab_checksum              66843
_olex2_submission_original_sample_id RK-ji
_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 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.784