Direct Catalytic Asymmetric Vinylogous Mannich-Type and Michael Reactions of an α,β-Unsaturated γ-Butyrolactam under Dinuclear Nickel Catalysis
Nicholas E. Shepherd; Hirooki Tanabe; Yingjie Xu; Shigeki Matsunaga; Masakatsu Shibasaki; Journal of the American Chemical Society 132 (2010) 3666–3667; doi:10.1021/ja1002636

data_4102094
_publ_section_title
;
 Direct Catalytic Asymmetric Vinylogous Mannich-Type and Michael Reactions
 of an \a,\b-Unsaturated \g-Butyrolactam under Dinuclear Nickel Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3666
_journal_page_last               3667
_journal_paper_doi               10.1021/ja1002636
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 Br N2 O5 '
_chemical_formula_sum            'C17 H19 Br N2 O5'
_chemical_formula_weight         411.25
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.5750(17)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.7145(3)
_cell_length_b                   7.1225(3)
_cell_length_c                   12.4937(3)
_cell_measurement_reflns_used    5260
_cell_measurement_temperature    103.1
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      3.8
_cell_volume                     898.34(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla, 2003)'
_diffrn_ambient_temperature      103.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.077
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9153
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_exptl_absorpt_coefficient_mu    3.389
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.396
_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    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420.00
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.48
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1355 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.039(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3134
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                2620
_reflns_number_total             3134
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja1002636_si_003.cif
_cod_data_source_block           '_091221'
_cod_original_cell_volume        898.35(5)
_cod_original_formula_sum        'C17 H19 Br N2 O5 '
_cod_database_code               4102094