2,2,3,3-Tetrafluoronickelacyclopentanes Generated via the Oxidative Cyclization of Tetrafluoroethylene and Simple Alkenes: A Key Intermediate in Nickel-Catalyzed C‒C Bond-Forming Reactions
Ohashi, Masato; Kawashima, Takuya; Taniguchi, Tomoaki; Kikushima, Kotaro; Ogoshi, Sensuke; Organometallics 34 (2015) 1604–; doi:10.1021/acs.organomet.5b00218

data_4087521
_publ_section_title
;
 2,2,3,3-Tetrafluoronickelacyclopentanes Generated via the Oxidative
 Cyclization of Tetrafluoroethylene and Simple Alkenes: A Key Intermediate
 in Nickel-Catalyzed C--C Bond-Forming Reactions
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              1604
_journal_paper_doi               10.1021/acs.organomet.5b00218
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C40 H34 F4 Ni P2'
_chemical_formula_weight         711.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5320(3)
_cell_length_b                   36.1812(11)
_cell_length_c                   9.6015(4)
_cell_measurement_reflns_used    17766
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      3.07
_cell_volume                     3311.4(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalMaker for Windows ver. 2.7.6'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013) and modified'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Sir2011 (Murla, et al., 2012)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21005
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.299
_diffrn_reflns_theta_min         3.064
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6019
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0320P)^2^+0.1299P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0619
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5547
_reflns_number_total             6019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00218_si_002.cif
_cod_data_source_block           Complex1
_cod_database_code               4087521
_shelxl_version_number           2013-4
_shelx_res_checksum              50694
_shelx_hkl_checksum              93446