Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5' linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindoles.
Babu, K. Naresh; Kinthada, Lakshmana K.; Ghosh, Santanu; Bisai, Alakesh; Organic & biomolecular chemistry 13 (2015) 10641–10655; doi:10.1039/c5ob01670c

data_7154664
_publ_section_title
;
 Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5'
 linkage via Friedel-Crafts alkylations of 2-oxindoles with
 3-hydroxy-2-oxindoles.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10641
_journal_page_last               10655
_journal_paper_doi               10.1039/c5ob01670c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C24 H20 Cl2 N2 O2'
_chemical_formula_weight         438.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-03-26 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.661(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.2646(12)
_cell_length_b                   9.4866(4)
_cell_length_c                   15.7986(7)
_cell_measurement_temperature    140(2)
_cell_volume                     4262.0(3)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0719
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23016
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         1.432
_exptl_absorpt_coefficient_mu    0.333
_exptl_crystal_colour            PINK
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1856
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.489
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.455
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.455
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0749
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3355
_reflns_number_total             4358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01670c2.cif
_cod_data_source_block           TRYA2_final
_cod_depositor_comments
'Adding full bibliography for 7154664--7154665.cif.'
_cod_database_code               7154664
_shelxl_version_number           2014/6
_shelx_res_checksum              5563