Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides.
Devannah, Vijayarajan; Sharma, Rajgopal; Watson, Donald A.; Journal of the American Chemical Society 141 (2019) 8436–8440; doi:10.1021/jacs.9b04175

data_4127279
_publ_section_title
;
 Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of
 Enantioenriched \b-Nitroamides.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8436
_journal_page_last               8440
_journal_paper_doi               10.1021/jacs.9b04175
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H34 N2 O3 S'
_chemical_formula_weight         490.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4430(4)
_cell_length_b                   14.6580(4)
_cell_length_c                   16.1254(5)
_cell_measurement_reflns_used    5047
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.75
_cell_measurement_theta_min      4.08
_cell_volume                     2704.74(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19478
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.482
_diffrn_reflns_theta_min         4.076
_exptl_absorpt_coefficient_mu    1.310
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
; 
 Flack x determined using 1539 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.018(19)
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5536
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0891P)^2^+0.4430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1775
_refine_ls_wR_factor_ref         0.1898
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                4532
_reflns_number_total             5536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04175_si_005.cif
_cod_data_source_block           donw073
_cod_depositor_comments
'Adding full bibliography for 4127279--4127281.cif.'
_cod_database_code               4127279
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.705
_shelx_estimated_absorpt_t_max   0.863
_shelx_res_checksum              15521
_shelx_hkl_checksum              11154