Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes
Daniel Best; Szymon Kujawa; Hon Wai Lam; Journal of the American Chemical Society 134 (2012) 18193–18196; doi:10.1021/ja3083494

data_4118868
_publ_section_title
;
 Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of
 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18193
_journal_page_last               18196
_journal_paper_doi               10.1021/ja3083494
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H19 N3 O4'
_chemical_formula_sum            'C21 H19 N3 O4'
_chemical_formula_weight         377.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 91.7156(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.94049(7)
_cell_length_b                   31.6895(3)
_cell_length_c                   10.02062(7)
_cell_measurement_reflns_used    47286
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      77.0066
_cell_measurement_theta_min      4.1818
_cell_volume                     1885.55(3)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2011)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.3147
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            113692
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.214
_diffrn_reflns_theta_min         4.414
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 3398 quotients [(I+)-I(-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7920
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+1.4609P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1703
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                7623
_reflns_number_total             7920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja3083494_si_004.cif
_cod_data_source_block           hl2028
_cod_database_code               4118868
_shelx_estimated_absorpt_t_min   0.790
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2012-4
_shelx_res_checksum              62563