DABCO-promoted highly diastereo- and regioselective construction of C-3 functionalized spirooxindoles via [3 + 2] cycloaddition of 2-aryl/heteroarylidene-1H-indene-1,3(2H)-diones with N-2,2,2-trifluoroethylisatin ketimines at ambient conditions
Prasad, Madavi S.; Bharani, Sankar; Sharief, Syed Mastan; Ravi, Mudavath; Sivaprakash, Murugesan; Borah, Biplob; Chowhan, L. Raju; RSC Advances 12 (2022) 34941–34945; doi:10.1039/D2RA07141J

data_7245975
_publ_section_title
;
 DABCO-promoted highly diastereo- and regioselective construction of C-3
 functionalized spirooxindoles via [3 + 2] cycloaddition of
 2-aryl/heteroarylidene-1H-indene-1,3(2H)-diones with
 N-2,2,2-trifluoroethylisatin ketimines at ambient conditions
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              34941
_journal_page_last               34945
_journal_paper_doi               10.1039/D2RA07141J
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C27 H19 F3 N2 O3'
_chemical_formula_sum            'C27 H19 F3 N2 O3'
_chemical_formula_weight         476.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-22 deposited with the CCDC.	2022-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0771(4)
_cell_length_b                   19.0403(7)
_cell_length_c                   20.1521(8)
_cell_measurement_reflns_used    8424
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.68
_cell_measurement_theta_min      2.23
_cell_volume                     4634.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0962
_diffrn_reflns_av_unetI/netI     0.0450
_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       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            69301
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.672
_diffrn_reflns_theta_min         2.139
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0010(2)
_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   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0521P)^2^+1.8133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2399
_reflns_number_total             4398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra07141j2.cif
_cod_data_source_block           ME
_cod_database_code               7245975
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              5477