Rongalite-promoted self-dimerization of 3-acylidene-2-oxindoles: a diastereoselective route to synthesis of bispirooxindoles.
Chaudhari, Suryakant S.; Nichinde, Chandrakant B.; Patil, Baliram R.; Girase, Amardipsing S.; Kaulage, Sandeep H.; Kinage, Anil K.; Organic & biomolecular chemistry 23 (2025) 8687–8694; doi:10.1039/d5ob01069a

data_7160715
_publ_section_title
;
 Rongalite-promoted self-dimerization of 3-acylidene-2-oxindoles: a
 diastereoselective route to synthesis of bispirooxindoles.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8687
_journal_page_last               8694
_journal_paper_doi               10.1039/d5ob01069a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration S
_chemical_formula_sum            'C72 H66 F6 N6 O12'
_chemical_formula_weight         1321.30
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-04-30 deposited with the CCDC.	2025-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            1
_cell_length_a                   11.106(3)
_cell_length_b                   11.106(3)
_cell_length_c                   14.374(6)
_cell_measurement_reflns_used    9749
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.55
_cell_volume                     1535.4(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37274
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_min         2.117
_exptl_absorpt_coefficient_mu    0.110
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             690
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6391
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.338
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_refine_ls_abs_structure_details
;
 Flack x determined using 1518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5101
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0560
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3926
_reflns_number_total             5101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01069a2.cif
_cod_data_source_block           A4_a
_cod_depositor_comments
'Adding full bibliography for 7160714--7160715.cif.'
_cod_original_cell_volume        1535.5(10)
_cod_database_code               7160715
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              32867