TfOH-triggered denitrogenative union of diazo carbonyl compounds and indolin-2-thiones toward functionalized indole derivatives and their preliminary anticancer assessment.
Sable, Sakshi Haridas; Ambadipudi, S. S. S. S. Sudha; Andugulapati, Sai Balaji; Balasubramani, Alagesan; Organic & biomolecular chemistry 24 (2026) 1697–1702; doi:10.1039/d5ob01227a

data_7160927
_publ_section_title
;
 TfOH-triggered denitrogenative union of diazo carbonyl compounds and
 indolin-2-thiones toward functionalized indole derivatives and their
 preliminary anticancer assessment.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1697
_journal_page_last               1702
_journal_paper_doi               10.1039/d5ob01227a
_journal_volume                  24
_journal_year                    2026
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H10 Cl N S'
_chemical_formula_sum            'C16 H10 Cl N S'
_chemical_formula_weight         283.783
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_audit_creation_date             2025-04-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-11-17 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6596(4)
_cell_length_b                   10.8313(5)
_cell_length_c                   16.1412(7)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.26
_cell_volume                     1339.13(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20879
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9991
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1350 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.9245.
The \l/2 correction factor is Not present.
;
_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    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             585.270
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.3549
_refine_diff_density_min         -0.3064
_refine_diff_density_rms         0.0877
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.35(7)
_refine_ls_d_res_high            0.7598
_refine_ls_d_res_low             8.9940
_refine_ls_goodness_of_fit_ref   0.9986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9986
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0619P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2571
_reflns_number_total             3201
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01227a2.cif
_cod_data_source_block           5c
_cod_depositor_comments          'Adding full bibliography for 7160927.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7160927
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00D(H00D), C00C(H00C), C00G(H00G), C00J(H00J),
 C00I(H00I), C00H(H00H), C009(H009), C00E(H00E)
;
_olex2_submission_special_instructions 'No special instructions were received'