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_4127280
_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            'C21 H24 N2 O5'
_chemical_formula_weight         384.42
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_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'
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_cell_angle_gamma                90
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_cell_length_a                   9.7516(3)
_cell_length_b                   13.2713(4)
_cell_length_c                   15.4202(5)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.96
_cell_measurement_theta_min      3.33
_cell_volume                     1995.63(11)
_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'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_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  0.0949
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.955
_diffrn_reflns_theta_min         4.395
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
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_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 1697 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_coef       0.0212(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+0.2160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3993
_reflns_number_total             4057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04175_si_003.cif
_cod_data_source_block           donw063
_cod_depositor_comments
'Adding full bibliography for 4127279--4127281.cif.'
_cod_database_code               4127280
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.740
_shelx_estimated_absorpt_t_max   0.862
_shelx_res_checksum              41123
_shelx_hkl_checksum              30088