Nickel-Catalyzed Formation of 1,3-Dienes via a Highly Selective Cross-Tetramerization of Tetrafluoroethylene, Styrenes, Alkynes, and Ethylene.
Kawashima, Takuya; Ohashi, Masato; Ogoshi, Sensuke; Journal of the American Chemical Society 139 (2017) 17795–17798; doi:10.1021/jacs.7b12007

data_4131882
_publ_section_title
;
 Nickel-Catalyzed Formation of 1,3-Dienes via a Highly Selective
 Cross-Tetramerization of Tetrafluoroethylene, Styrenes, Alkynes, and
 Ethylene.
;
_journal_issue                   49
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17795
_journal_page_last               17798
_journal_paper_doi               10.1021/jacs.7b12007
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C50 H39 F4 Ni P'
_chemical_formula_sum            'C50 H39 F4 Ni P'
_chemical_formula_weight         805.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.961(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.8594(11)
_cell_length_b                   19.4976(16)
_cell_length_c                   37.261(3)
_cell_measurement_reflns_used    12820
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.04
_cell_volume                     7831.2(12)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Crystal Structure'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013) and modified'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'PATTY (Bueskens, et al., 1994)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.968
_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  0.1121
_diffrn_reflns_av_unetI/netI     0.1581
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            29027
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.036
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             3344
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 2936 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.032(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1009
_refine_ls_number_reflns         13474
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0733
_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^)+(0.0238P)^2^+0.0196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.960
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                8844
_reflns_number_total             13474
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b12007_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        7831.1(12)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4131882
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.932
_shelxl_version_number           2013-4
_shelx_res_checksum              97260
_shelx_hkl_checksum              10264