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_4133731
_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_moiety         'C17 H16 Cl F7 N2 Ni'
_chemical_formula_sum            'C17 H16 Cl F7 N2 Ni'
_chemical_formula_weight         475.48
_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
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 115.122(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.5124(3)
_cell_length_b                   12.35978(12)
_cell_length_c                   16.5380(2)
_cell_measurement_reflns_used    31182
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.9080
_cell_measurement_theta_min      2.6370
_cell_volume                     3426.10(10)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_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  0.0453
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            50875
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.397
_diffrn_reflns_theta_min         2.636
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    3.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91624
_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    1.844
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         6311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0698P)^2^+2.4900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6217
_reflns_number_total             6311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11999_si_005.cif
_cod_data_source_block           ec318
_cod_original_cell_volume        3426.11(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4133731
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.546
_shelx_estimated_absorpt_t_max   0.657
_shelx_res_checksum              93056
_shelx_hkl_checksum              41897