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_4028870
_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         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_chemical_melting_point          486(1)
_chemical_name_systematic
; 
(Z)-3-benzylidene-4,5-dimethoxyisoindolin-1-one 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 97.549(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.896(2)
_cell_length_b                   15.281(4)
_cell_length_c                   10.5883(18)
_cell_measurement_temperature    298(2)
_cell_volume                     1426.9(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13608
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9563
_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    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0545P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                1847
_reflns_number_total             3224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402125u_si_011.cif
_cod_data_source_block           Z-8a
_cod_original_cell_volume        1426.8(6)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4028870