Nickel-Catalyzed Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates.
Huang, David; Olivieri, Diego; Sun, Yang; Zhang, Pengpeng; Newhouse, Timothy R.; Journal of the American Chemical Society 141 (2019) 16249–16254; doi:10.1021/jacs.9b09245

data_4127696
_publ_section_title
;
 Nickel-Catalyzed Difunctionalization of Unactivated Alkenes Initiated by
 Unstabilized Enolates.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16249
_journal_page_last               16254
_journal_paper_doi               10.1021/jacs.9b09245
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C22 H27 F3 O'
_chemical_formula_sum            'C22 H27 F3 O'
_chemical_formula_weight         364.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.314(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.1927(9)
_cell_length_b                   6.0161(2)
_cell_length_c                   27.2923(9)
_cell_measurement_reflns_used    16123
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.4260
_cell_measurement_theta_min      3.2690
_cell_volume                     3746.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            65974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.815
_diffrn_reflns_theta_max         66.815
_diffrn_reflns_theta_min         3.292
_diffrn_source                   'microfocus rotating anode'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.251
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0535P)^2^+2.8071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2649
_reflns_number_total             3332
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09245_si_003.cif
_cod_data_source_block           007a-19042
_cod_database_code               4127696
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              22113
_shelx_hkl_checksum              26879