Transition-Metal-Free Addition Reaction for the Synthesis of 3-(Aminobenzylidene/aminoalkylidene)indolin-2-ones and Its Synthetic Applications.
Bisht, Girish Singh; Gnanaprakasam, Boopathy; The Journal of organic chemistry 84 (2019) 13516–13527; doi:10.1021/acs.joc.9b01771

data_4034536
_publ_section_title
;
 Transition-Metal-Free Addition Reaction for the Synthesis of
 3-(Aminobenzylidene/aminoalkylidene)indolin-2-ones and Its Synthetic
 Applications.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13516
_journal_page_last               13527
_journal_paper_doi               10.1021/acs.joc.9b01771
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C10 H10 N2 O'
_chemical_formula_weight         174.20
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 92.210(3)
_cell_angle_gamma                90
_cell_formula_units_Z            48
_cell_length_a                   45.984(3)
_cell_length_b                   14.1262(9)
_cell_length_c                   15.9483(10)
_cell_measurement_reflns_used    9667
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      65.33
_cell_measurement_theta_min      2.88
_cell_volume                     10352.0(11)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'fine focused sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            98429
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        65.322
_diffrn_reflns_theta_max         65.322
_diffrn_reflns_theta_min         2.885
_exptl_absorpt_coefficient_mu    0.721
_exptl_crystal_colour            coloured
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       needleshape
_exptl_crystal_F_000             4416
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1417
_refine_ls_number_reflns         17685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0465
_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^)+(0.1000P)^2^+0.5415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15233
_reflns_number_total             17685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01771_si_002.cif
_cod_data_source_block           TRY_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034536
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              80794
_shelx_hkl_checksum              90663