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_4133732
_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 H17 F7 N2 Ni'
_chemical_formula_sum            'C17 H17 F7 N2 Ni'
_chemical_formula_weight         441.03
_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-2016/6
_cell_angle_alpha                98.804(2)
_cell_angle_beta                 99.219(2)
_cell_angle_gamma                91.664(2)
_cell_formula_units_Z            4
_cell_length_a                   10.0599(3)
_cell_length_b                   10.1627(3)
_cell_length_c                   17.7842(4)
_cell_measurement_reflns_used    15120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.0040
_cell_measurement_theta_min      4.4030
_cell_volume                     1770.87(9)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.967
_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  0.0479
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26755
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.245
_diffrn_reflns_theta_min         4.409
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    2.288
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74980
_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    1.654
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.0104(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         6398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0593
_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^)+(0.1010P)^2^+0.7339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6014
_reflns_number_total             6398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11999_si_004.cif
_cod_data_source_block           ec315
_cod_database_code               4133732
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.633
_shelx_estimated_absorpt_t_max   0.914
_shelx_res_checksum              14465
_shelx_hkl_checksum              5222