Electroreductive coupling of phthalimides with alpha,beta-unsaturated esters: unusual rearrangement of resulting silyl ketene acetals.
Kise, Naoki; Isemoto, Shinsaku; Sakurai, Toshihiko; Organic letters 11 (2009) 4902–4905; doi:10.1021/ol902016a

data_1504239
_publ_section_title
;
 Electroreductive coupling of phthalimides with alpha,beta-unsaturated
 esters: unusual rearrangement of resulting silyl ketene acetals.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4902
_journal_page_last               4905
_journal_paper_doi               10.1021/ol902016a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.24
_chemical_melting_point          423.0(10)
_chemical_name_systematic
; 
 ethyl 1-hydroxy-4-(methylamino)-2-naphthoate 
;
_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                 87.67(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.578(4)
_cell_length_b                   17.794(10)
_cell_length_c                   8.169(5)
_cell_measurement_temperature    298(2)
_cell_volume                     1100.6(11)
_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 0.951
_diffrn_measured_fraction_theta_max 0.951
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9675
_diffrn_reflns_theta_full        27.34
_diffrn_reflns_theta_max         27.34
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9612
_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    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0685P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                1502
_reflns_number_total             2367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902016a_si_005.cif
_cod_data_source_block           nk081220
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '422-424' was changed to '423.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1100.6(10)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               1504239