Regioselective House–Meinwald Rearrangement in Oxindoles: Access to Substituted Quinolinones
Mohan, B.; Sandhya, K. S.; Thushara, Ramakrishnan; Santhoshkumar, Athira Chithralekha; K, Liyo Vincent; Suresh, Cherumuttathu Hariharan; Purushothaman, Jayamurthy; Sasidhar, B. S.; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00128A

data_7160936
_publ_section_title
;
 Regioselective House-Meinwald rearrangement in oxindoles: access to
 substituted quinolinones.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2028
_journal_page_last               2033
_journal_paper_doi               10.1039/d6ob00128a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C15 H11 N O3, H2 O '
_chemical_formula_sum            'C15 H13 N O4'
_chemical_formula_weight         271.26
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-22 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                68.4130(10)
_cell_angle_beta                 86.8380(10)
_cell_angle_gamma                67.7030(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2227(3)
_cell_length_b                   9.2625(4)
_cell_length_c                   11.1958(4)
_cell_measurement_reflns_used    9134
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.45
_cell_measurement_theta_min      3.06
_cell_volume                     641.28(5)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27762
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         3.338
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0622P)^2^+0.2108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2658
_reflns_number_total             3099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00128a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7160936.cif.'
_cod_database_code               7160936
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              77216