Reductive Coupling of Phthalimides with Ketones and Aldehydes by Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones
Naoki Kise; Yusuke Kawano; Toshihiko Sakurai; Journal of Organic Chemistry 78 (2013) 12453–12459; doi:10.1021/jo402125u

data_4028867
_publ_section_title
;
 Reductive Coupling of Phthalimides with Ketones and Aldehydes by
 Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12453
_journal_page_last               12459
_journal_paper_doi               10.1021/jo402125u
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C16 H12 F N O'
_chemical_formula_sum            'C16 H12 F N O'
_chemical_formula_weight         253.27
_chemical_melting_point          429(1)
_chemical_name_systematic
; 
(E)-3-(4-fluorobenzylidene)-2-methylisoindolin-1-one 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.012(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5792(7)
_cell_length_b                   11.4148(9)
_cell_length_c                   11.4639(7)
_cell_measurement_temperature    298(2)
_cell_volume                     1251.78(15)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_publication_material  yadokari-XG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11797
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_correction_T_min  0.9544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.0644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2222
_reflns_number_total             2838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402125u_si_008.cif
_cod_data_source_block           E-7j
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028867