Copper-Catalyzed Tandem [2,3]-Rearrangement and 6π-3-Azatriene Electrocyclization in (E)-O-Propargylic α,β-Unsaturated Oximes
Itaru Nakamura; Dong Zhang; Masahiro Terada; Journal of the American Chemical Society 132 (2010) 7884–7886; doi:10.1021/ja102436z

data_4102523
_publ_contact_author_email       itaru-n@m.tains.tohoku.ac.jp
_publ_contact_author_fax         +81-22-795-6602
_publ_contact_author_name        'Itaru Nakamura'
_publ_contact_author_phone       +81-22-795-6754
_publ_section_title
;
 Copper-Catalyzed Tandem [2,3]-Rearrangement and 6\p-3-Azatriene
 Electrocyclization in (E)-O-Propargylic \a,\b-Unsaturated Oximes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7884
_journal_page_last               7886
_journal_paper_doi               10.1021/ja102436z
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C24 H19 N O '
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_date             2009-07-07
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.846(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   13.331(4)
_cell_length_b                   13.030(4)
_cell_length_c                   22.476(7)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     3756(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR2004
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            54225
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424.00
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8593
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0001Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                6049
_reflns_number_total             8593
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja102436z_si_002.cif
_cod_data_source_block           '__a'
_cod_original_cell_volume        3755.5(19)
_cod_original_formula_sum        'C24 H19 N O '
_cod_database_code               4102523