Aromatic Cyanoalkylation through Double C-H Activation Mediated by Ni(III).
Zhou, Wen; Zheng, Shuai; Schultz, Jason W.; Rath, Nigam P.; Mirica, Liviu M.; Journal of the American Chemical Society 138 (2016) 5777–5780; doi:10.1021/jacs.6b02405

data_4130339
_publ_section_title
;
 Aromatic Cyanoalkylation through Double C-H Activation Mediated by
 Ni(III).
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5777
_journal_page_last               5780
_journal_paper_doi               10.1021/jacs.6b02405
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C23 H33 Br2 N3 Ni, 2(C4 H8 O)'
_chemical_formula_sum            'C31 H49 Br2 N3 Ni O2'
_chemical_formula_weight         714.26
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.342(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2127(10)
_cell_length_b                   14.1765(11)
_cell_length_c                   16.9635(12)
_cell_measurement_reflns_used    9229
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.45
_cell_volume                     3115.4(4)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            51071
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.509
_diffrn_reflns_theta_min         1.888
_exptl_absorpt_coefficient_mu    3.220
_exptl_absorpt_correction_T_max  0.5624
_exptl_absorpt_correction_T_min  0.3957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2012/1'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6436
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0233P)^2^+5.6569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0745
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5176
_reflns_number_total             6436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02405_si_002.cif
_cod_data_source_block           l17013
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4130339
_shelx_estimated_absorpt_t_min   0.386
_shelx_estimated_absorpt_t_max   0.813
_shelxl_version_number           2013-4
_shelx_res_checksum              52019
_shelx_hkl_checksum              96136