Synthesis of <i>N</i>-substituted 3-(2-aryl-2-oxoethyl)-3-hydroxyindolin-2-ones and their conversion to <i>N</i>-substituted (<i>E</i>)-3-(2-aryl-2-oxoethylidene)indolin-2-ones: synthetic sequence, spectroscopic characterization and structures of four 3-hydroxy compounds and five oxoethylidene products
Becerra, Diana; Castillo, Juan; Insuasty, Braulio; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 76 (2020) 433–445; doi:10.1107/S2053229620004143

data_2022153
_publ_section_title
;
 Synthesis of <i>N</i>-substituted
 3-(2-aryl-2-oxoethyl)-3-hydroxyindolin-2-ones and their conversion to
 <i>N</i>-substituted (<i>E</i>)-3-(2-aryl-2-oxoethylidene)indolin-2-ones:
 synthetic sequence, spectroscopic characterization and structures of four
 3-hydroxy compounds and five oxoethylidene products
;
_journal_coeditor_code           SK3748
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              433
_journal_page_last               445
_journal_paper_doi               10.1107/S2053229620004143
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C23 H16 F N O2'
_chemical_formula_moiety         'C23 H16 F N O2'
_chemical_formula_sum            'C23 H16 F N O2'
_chemical_formula_weight         357.37
_chemical_name_systematic
;
(<i>E</i>)-1-Benzyl-3-[2-(4-fluorophenyl)-2-oxoethylidene]indolin-2-one
;
_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
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 96.986(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6021(6)
_cell_length_b                   20.4880(13)
_cell_length_c                   10.9319(7)
_cell_measurement_reflns_used    3896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.627
_cell_measurement_theta_min      2.124
_cell_volume                     1690.0(2)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_min         2.124
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0606P)^2^+0.9100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1340
_reflns_number_gt                2995
_reflns_number_total             3896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3748sup1.cif
_cod_data_source_block           IIa
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022153
_cod_database_fobs_code          2022153
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.990
_shelx_hkl_checksum              83076
_shelx_res_checksum              28059
_shelxl_version_number           2.014