Trans-stereoselectivity in the reaction between homophthalic anhydride and imines.
Vara, Yosu; Bello, Tamara; Aldaba, Eneko; Arrieta, Ana; Pizarro, José L; Arriortua, María I; Lopez, Xabier; Cossío, Fernando P; Organic letters 10 (2008) 4759–4762; doi:10.1021/ol801757r

data_1504893
_publ_section_title
;
 Trans-stereoselectivity in the reaction between homophthalic anhydride
 and imines.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4759
_journal_page_last               4762
_journal_paper_doi               10.1021/ol801757r
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H27 N1 O6'
_chemical_formula_sum            'C24 H27 N O6'
_chemical_formula_weight         425.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-02-28T13:37:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.291(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0148(4)
_cell_length_b                   15.6616(7)
_cell_length_c                   13.2742(5)
_cell_measurement_reflns_used    15637
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      1.85
_cell_measurement_wavelength     0.71073
_cell_volume                     2289.34(16)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
    Reference Run
      Phi                  : 90.0
      Omega range          : 0.0 - 20.0
      Omega increment      : 20.0
      Exposure time [min]  : 2.0
      Frames               : 1
      Interval [h]         : 1.00

    Run #1
      Phi                  : 0.0
      Omega range          : 0.0 - 180.0
      Omega increment      : 1.0
      Exposure time [min]  : 3.0
      Frames               : 180

    Run #2
      Phi                  : 90.0
      Omega range          : 0.0 - 180.0
      Omega increment      : 1.0
      Exposure time [min]  : 3.0
      Frames               : 180

    Measured runs                        : 2 (out of 2)
    Measured frames                      : 360 (out of 360)
    Remeasured frames with filter        : 0
    Measured reference runs              : 27
    Statistics over all measured frames
      Mean minimum pixel intensity       : 1.0
      Mean average pixel intensity       : 11.5
      Mean maximum pixel intensity       : 15778.4
      Total number of overflow pixels    : 8
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.8 mm diameter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31000
_diffrn_reflns_theta_full        25.58
_diffrn_reflns_theta_max         25.58
_diffrn_reflns_theta_min         1.85
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     572
_refine_ls_number_reflns         4464
_refine_ls_number_restraints     604
_refine_ls_restrained_S_all      0.836
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                3124
_reflns_number_total             4464
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol801757r_si_002.cif
_cod_data_source_block           yhist01
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1504893