Efficient Synthesis of N-Alkylated α,β-Unsaturated Ketonitrones via Cu-Catalyzed Rearrangement.
Nakamura, Itaru; Onuma, Toshiki; Kanazawa, Ryo; Nishigai, Yuki; Terada, Masahiro; Organic letters 16 (2014) 4198–4200; doi:10.1021/ol501889g

data_1517217
_publ_section_title
;
 Efficient Synthesis of N-Alkylated \a,\b-Unsaturated Ketonitrones via
 Cu-Catalyzed Rearrangement.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4198
_journal_page_last               4200
_journal_paper_doi               10.1021/ol501889g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C22 H18 N2 O3'
_chemical_formula_sum            'C22 H18 N2 O3'
_chemical_formula_weight         358.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.499(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.0236(14)
_cell_length_b                   6.7864(7)
_cell_length_c                   19.674(2)
_cell_measurement_reflns_used    17484
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      3.00
_cell_volume                     1812.7(3)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 6.827
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19527
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.210
_refine_ls_extinction_coef       0.0011(7)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.5326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                3542
_reflns_number_total             4149
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol501889g_si_001.cif
_cod_data_source_block           01
_cod_depositor_comments          'Adding full bibliography for 1517217.cif.'
_cod_original_cell_volume        1812.7(4)
_cod_database_code               1517217