Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines
Bhandari, Sonal; Sana, Sravani; Lahoti, Vandana; Tokala, Ramya; Shankaraiah, Nagula; RSC Advances 10 (2020) 16101–16109; doi:10.1039/D0RA00684J

data_7240402
_publ_section_title
;
 Ring-opening cyclization of activated spiro-aziridine oxindoles with
 heteroarenes: a facile synthetic approach to spiro-oxindole-fused
 pyrroloindolines
;
_journal_issue                   27
_journal_name_full               'RSC Advances'
_journal_page_first              16101
_journal_page_last               16109
_journal_paper_doi               10.1039/D0RA00684J
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H28 Cl N3 O3 S'
_chemical_formula_sum            'C24 H28 Cl N3 O3 S'
_chemical_formula_weight         474.00
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-12-06 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.53409(9)
_cell_length_b                   7.53409(9)
_cell_length_c                   42.4001(5)
_cell_measurement_reflns_used    8968
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      2.87
_cell_measurement_theta_min      2.70
_cell_volume                     2406.74(5)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1111
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            18924
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_min         2.704
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1158 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         18924
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0689
_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^)+1.0826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                13231
_reflns_number_total             18924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra00684j2.cif
_cod_data_source_block           KA778_TWIN
_cod_depositor_comments          'Adding full bibliography for 7240402.cif.'
_cod_original_cell_volume        2406.74(6)
_cod_database_code               7240402
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              29726