Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines
Chung-Yang (Dennis) Huang; Abigail G. Doyle; Journal of the American Chemical Society 134 (2012) 9541–9544; doi:10.1021/ja3013825

data_4118045
_publ_section_title
;
 Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9541
_journal_page_last               9544
_journal_paper_doi               10.1021/ja3013825
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H25 N O2 S'
_chemical_formula_weight         331.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.000
_cell_angle_beta                 109.371(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   10.938(5)
_cell_length_b                   5.438(5)
_cell_length_c                   16.031(5)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.23
_cell_measurement_theta_min      4.29
_cell_volume                     899.6(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP3 (Farraguia, 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14726
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         66.29
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    1.662
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       rod
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.069(16)
_refine_ls_extinction_coef       0.0121(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.4531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                2817
_reflns_number_total             2822
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja3013825_si_003.cif
_cod_data_source_block           cyh2
_cod_database_code               4118045