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_4130338
_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         'C25 H37 Br2 N3 Ni'
_chemical_formula_sum            'C25 H37 Br2 N3 Ni'
_chemical_formula_weight         598.10
_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-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 118.951(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2268(6)
_cell_length_b                   14.1760(6)
_cell_length_c                   14.3580(6)
_cell_measurement_reflns_used    9659
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.87
_cell_volume                     2533.84(19)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0581
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33080
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.463
_diffrn_reflns_theta_min         1.636
_exptl_absorpt_coefficient_mu    3.937
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2014/4'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0557
_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^)+(0.0369P)^2^+3.1153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3999
_reflns_number_total             5206
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02405_si_002.cif
_cod_data_source_block           l12015
_cod_original_cell_volume        2533.85(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4130338
_shelx_estimated_absorpt_t_min   0.383
_shelx_estimated_absorpt_t_max   0.852
_shelxl_version_number           2014/6
_shelx_res_checksum              73701
_shelx_hkl_checksum              65953