Nickel(II/IV) Manifold Enables Room-Temperature C(sp3)‒H Functionalization
Roberts, Courtney C.; Chong, Eugene; Kampf, Jeff W.; Canty, Allan J.; Ariafard, Alireza; Sanford, Melanie S.; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b11999

data_4133733
_publ_section_title
;
 Nickel(II/IV) Manifold Enables Room-Temperature C(sp3)--H
 Functionalization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b11999
_journal_year                    2019
_chemical_formula_sum            'C17 H16 F8 N2 Ni'
_chemical_formula_weight         459.03
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                103.369(3)
_cell_angle_beta                 90.992(2)
_cell_angle_gamma                111.482(3)
_cell_formula_units_Z            4
_cell_length_a                   10.1598(4)
_cell_length_b                   12.5223(5)
_cell_length_c                   14.8714(4)
_cell_measurement_reflns_used    13162
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      69.0790
_cell_measurement_theta_min      3.0330
_cell_volume                     1701.95(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      225(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26180
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.534
_diffrn_reflns_theta_min         3.074
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    2.498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         12678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0664
_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^)+(0.1368P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9698
_reflns_number_total             12678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11999_si_006.cif
_cod_data_source_block           ni4f
_cod_original_cell_volume        1701.95(11)
_cod_database_code               4133733
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.721
_shelx_estimated_absorpt_t_max   0.788
_shelx_res_checksum              16455
_shelx_hkl_checksum              96705