N–S bond cleavage of tosyl hydrazones by dual reactive arynes: synthesis of diaryl sulfones, spiro[indazole-3,3′-indolin]-2′-one, and N-phenyl sulfonohydrazides
Smile, Suresh Snoxma; Shanmugam, Ponnusamy; New Journal of Chemistry 47 (2023) 3856–3863; doi:10.1039/D3NJ00050H

data_7062229
_publ_section_title
;
 N--S bond cleavage of tosyl hydrazones by dual reactive arynes: synthesis
 of diaryl sulfones, spiro[indazole-3,3&#x2032;-indolin]-2&#x2032;-one,
 and N-phenyl sulfonohydrazides
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3856
_journal_page_last               3863
_journal_paper_doi               10.1039/D3NJ00050H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C22 H19 N3 O3 S'
_chemical_formula_sum            'C22 H19 N3 O3 S'
_chemical_formula_weight         405.46
_chemical_name_common            SS2-89F3
_chemical_name_systematic
(E)-4-methyl-N'-(1-methyl-2-oxoindolin-3-ylidene)-N-phenylbenzenesulfonohydrazide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
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_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-16 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;
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_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
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_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_min         3.128
_exptl_absorpt_coefficient_mu    0.195
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            orange
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_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0470P)^2^+0.3956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2773
_reflns_number_total             4015
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_depositor_comments
'Adding full bibliography for 7062229--7062232.cif.'
_cod_database_code               7062229
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              44378