Electrochemical <i>N</i>-sulfonylation of <i>in situ</i> generated indole-based hydrazones and antimicrobial evaluation.
Kaur, Parmjeet; Kumar, Anuj; Palmo, Tashi; Singh, Kuljit; Tyagi, Vikas; Organic & biomolecular chemistry 23 (2025) 8948–8960; doi:10.1039/d5ob01107h

data_7160720
_publ_section_title
;
 Electrochemical <i>N</i>-sulfonylation of <i>in situ</i> generated
 indole-based hydrazones and antimicrobial evaluation.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8948
_journal_page_last               8960
_journal_paper_doi               10.1039/d5ob01107h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H21 N3 O4 S2'
_chemical_formula_sum            'C23 H21 N3 O4 S2'
_chemical_formula_weight         467.55
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-06
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-07-09 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                72.906(5)
_cell_angle_beta                 88.731(5)
_cell_angle_gamma                80.529(5)
_cell_formula_units_Z            2
_cell_length_a                   7.5075(5)
_cell_length_b                   10.2822(5)
_cell_length_c                   15.6878(9)
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5410
_cell_measurement_theta_min      3.6170
_cell_volume                     1141.28(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.914
_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    -41.00  -6.00   0.50   12.65    --   -9.32  99.00  91.00   70
  2  \w      0.00  41.00   0.50   12.65    --    9.60 -99.00 -14.00   82
  3  \w    -23.00  36.00   0.50   12.65    --   -9.32  77.00  30.00  118
  4  \w     14.00  39.00   0.50   12.65    --    9.60 -99.00  60.00   50
  5  \w      9.00  56.00   0.50   12.65    --    9.60-125.00-150.00   94
  6  \w    -54.00  23.00   0.50   12.65    --    9.60 -38.00-120.00  154
  7  \w    -18.00   7.00   0.50   12.65    --    9.60 107.00 -48.26   50
  8  \w    -41.00  32.00   0.50   12.65    --    9.60 -77.00   0.00  146
  9  \w     -5.00  23.00   0.50   12.65    --    9.60  88.00-140.35   56
 10  \w    -11.00  35.00   0.50   12.65    --    9.60 -99.00  90.00   92
 11  \w     16.00  51.00   0.50   12.65    --    9.60-125.00 -60.00   70
 12  \w    -32.00  -5.00   0.50   12.65    --    9.60 -57.00-180.00   54
 13  \w      0.00  25.00   0.50   12.65    --    9.60 -57.00-180.00   50
 14  \w    -33.00  -5.00   0.50   12.65    --    9.60 123.00 106.03   56
 15  \w    -56.00  22.00   0.50   12.65    --    9.60 -19.00  90.00  156
 16  \w    -31.00  -5.00   0.50   12.65    --    9.60 -77.00 -30.00   52
 17  \w    -33.00  -8.00   0.50   12.65    --    9.60 120.00  43.13   50
 18  \w    -54.00 -14.00   0.50   12.65    --    9.60 -57.00-150.00   80
;
_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      0.0654862000
_diffrn_orient_matrix_UB_12      -0.0316179000
_diffrn_orient_matrix_UB_13      0.0349872000
_diffrn_orient_matrix_UB_21      -0.0676370000
_diffrn_orient_matrix_UB_22      -0.0290969000
_diffrn_orient_matrix_UB_23      0.0279948000
_diffrn_orient_matrix_UB_31      0.0178466000
_diffrn_orient_matrix_UB_32      -0.0592359000
_diffrn_orient_matrix_UB_33      -0.0152160000
_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  0.1534
_diffrn_reflns_av_unetI/netI     0.1333
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14961
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.079
_diffrn_reflns_theta_min         3.233
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0676
_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/[\s^2^(Fo^2^)+(0.0713P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2338
_reflns_number_total             4595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01107h2.cif
_cod_data_source_block           ex-pm908
_cod_depositor_comments          'Adding full bibliography for 7160720.cif.'
_cod_database_code               7160720
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O S'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N007(H007), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00U(H00U)
2.b Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00E), C00W(H00F,H00J,H00L)
;
_shelx_res_checksum              45351
_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 4.070
_oxdiff_exptl_absorpt_empirical_full_min 0.161