Nickel-Catalyzed Formation of Fluorine-Containing Ketones via the Selective Cross-Trimerization Reaction of Tetrafluoroethylene, Ethylene, and Aldehydes.
Ohashi, Masato; Shirataki, Hiroshi; Kikushima, Kotaro; Ogoshi, Sensuke; Journal of the American Chemical Society 137 (2015) 6496–6499; doi:10.1021/jacs.5b03587

data_4123619
_publ_section_title
;
 Nickel-Catalyzed Formation of Fluorine-Containing Ketones via the
 Selective Cross-Trimerization Reaction of Tetrafluoroethylene, Ethylene,
 and Aldehydes.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6496
_journal_page_last               6499
_journal_paper_doi               10.1021/jacs.5b03587
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C66 H80 F16 N4 Ni2'
_chemical_formula_sum            'C66 H80 F16 N4 Ni2'
_chemical_formula_weight         1350.76
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.001(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3010(5)
_cell_length_b                   19.2677(8)
_cell_length_c                   16.8297(7)
_cell_measurement_reflns_used    19083
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.02
_cell_volume                     3289.5(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_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  0.0933
_diffrn_reflns_av_unetI/netI     0.1463
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32381
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.026
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.359
_exptl_crystal_size_min          0.184
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 2746 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.015(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     882
_refine_ls_number_reflns         14936
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0261P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.926
_reflns_friedel_fraction_full    0.993
_reflns_friedel_fraction_max     0.981
_reflns_number_gt                7908
_reflns_number_total             14936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b03587_si_001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4123619.cif.'
_cod_original_cell_volume        3289.6(3)
_cod_database_code               4123619
_shelx_estimated_absorpt_t_min   0.775
_shelx_estimated_absorpt_t_max   0.888
_shelxl_version_number           2013-4
_shelx_res_checksum              27103
_shelx_hkl_checksum              51262