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_1504891
_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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H15 N1 O3, H2 O1'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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             2008-05-02T12:39:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                96.026(8)
_cell_angle_beta                 90.191(8)
_cell_angle_gamma                111.306(7)
_cell_formula_units_Z            2
_cell_length_a                   7.0418(7)
_cell_length_b                   8.4665(8)
_cell_length_c                   13.3322(13)
_cell_measurement_reflns_used    8034
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.62
_cell_measurement_theta_min      2.6
_cell_measurement_wavelength     0.71073
_cell_volume                     735.70(13)
_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      150(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
    Reference Run
      Phi                  : 160.0
      Omega range          : 40.0 - 60.0
      Omega increment      : 20.0
      Exposure time [min]  : 1.5
      Frames               : 1
      Interval [h]         : 1.00

    Run #1
      Phi                  : 160.0
      Omega range          : 0.0 - 160.0
      Omega increment      : 1.0
      Exposure time [min]  : 1.5
      Frames               : 160

    Run #2
      Phi                  : 50.0
      Omega range          : 40.0 - 132.0
      Omega increment      : 1.0
      Exposure time [min]  : 1.5
      Frames               : 92

    Measured runs                        : 2 (out of 2)
    Measured frames                      : 252 (out of 252)
    Remeasured frames with filter        : 0
    Measured reference runs              : 14
    Statistics over all measured frames
      Mean minimum pixel intensity       : 1.0
      Mean average pixel intensity       : 10.1
      Mean maximum pixel intensity       : 12198.4
      Total number of overflow pixels    : 0

;
_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10262
_diffrn_reflns_theta_full        30
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_min         2.6
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9879
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.88
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.88
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                2779
_reflns_number_total             4265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801757r_si_002.cif
_cod_data_source_block           tb75_150
_cod_original_cell_volume        735.70(12)
_cod_database_code               1504891