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_4133730
_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         'C18 H16 F10 N2 Ni O3 S, C H2 Cl2'
_chemical_formula_sum            'C19 H18 Cl2 F10 N2 Ni O3 S'
_chemical_formula_weight         674.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 103.8290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.38320(10)
_cell_length_b                   20.3013(3)
_cell_length_c                   13.4142(2)
_cell_measurement_reflns_used    28373
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      69.0970
_cell_measurement_theta_min      3.3840
_cell_volume                     2481.22(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_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  0.0389
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37101
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.425
_diffrn_reflns_theta_min         4.032
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    4.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61284
_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    1.804
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.0114(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     324
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0770P)^2^+2.1746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4477
_reflns_number_total             4619
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11999_si_003.cif
_cod_data_source_block           ccrni4otf
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4133730
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.388
_shelx_estimated_absorpt_t_max   0.510
_shelx_res_checksum              7125
_shelx_hkl_checksum              90430