Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides.
Rezazadeh, Sina; Devannah, Vijayarajan; Watson, Donald A.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b04312

data_4126205
_publ_section_title
;
 Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl
 Iodides.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b04312
_journal_year                    2017
_chemical_formula_sum            'C14 H17 F N2 O3'
_chemical_formula_weight         280.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.174(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.0905(10)
_cell_length_b                   5.2366(2)
_cell_length_c                   18.6368(7)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.83
_cell_measurement_theta_min      4.75
_cell_volume                     2726.67(18)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_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  0.0548
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33803
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.141
_diffrn_reflns_theta_min         1.581
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.4344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.564
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0015(3)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5605
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0704
_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^)+(0.1416P)^2^+0.9947P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2013
_refine_ls_wR_factor_ref         0.2096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4946
_reflns_number_total             5605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b04312_si_005.cif
_cod_data_source_block           donw069a
_cod_database_code               4126205
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.634
_shelx_estimated_absorpt_t_max   0.944
_shelx_res_checksum              22376
_shelx_hkl_checksum              21389