Diverse reactivity of isatin-based N,N′-cyclic azomethine imine dipoles with arynes: synthesis of 1′-methyl-2′-oxospiro [indene-1,3′-indolines] and 3-aryl-3-pyrazol-2-oxindoles
Meerakrishna, Ramakrishnan Suseela; Smile, Suresh Snoxma; Athira, Mohanakumaran; Choutipalli, Venkata Surya Kumar; Shanmugam, Ponnusamy; New Journal of Chemistry 44 (2020) 11593–11601; doi:10.1039/D0NJ01684E

data_7059694
_publ_section_title
;
 Diverse reactivity of isatin-based N,N&#x2032;-cyclic azomethine imine
 dipoles with arynes: synthesis of 1&#x2032;-methyl-2&#x2032;-oxospiro
 [indene-1,3&#x2032;-indolines] and 3-aryl-3-pyrazol-2-oxindoles
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11593
_journal_page_last               11601
_journal_paper_doi               10.1039/D0NJ01684E
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C24 H19 N3 O2'
_chemical_formula_sum            'C24 H19 N3 O2'
_chemical_formula_weight         381.42
_chemical_name_systematic        'MKII-249 F3'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-23 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.326(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1075(9)
_cell_length_b                   15.3568(12)
_cell_length_c                   10.8188(7)
_cell_measurement_reflns_used    3366
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.53
_cell_measurement_theta_min      2.35
_cell_volume                     1949.0(2)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_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  0.0763
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28245
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.185
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.7021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc/Hexane'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0049(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0417P)^2^+0.5235P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1876
_reflns_number_total             3438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01684e2.cif
_cod_data_source_block           249
_cod_depositor_comments
;Adding full bibliography for 7059694--7059695.cif.

 Adding full bibliography for 7059694--7059695.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7059694
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              30094