Highly Stereoselective Nickel-Catalyzed Difluoroalkylation of Aryl Ketones to Tetrasubstituted Monofluoroalkenes and Quaternary Alkyl Difluorides
Li, Chao; Cao, Yi-Xuan; Jin, Ruoxing; Bian, Kang-Jie; Qin, Zi-Yang; Lan, Quan; Wang, Xi-Sheng; Chemical Science  (2019) –; doi:10.1039/C9SC02806D

data_1552250
_publ_section_title
;
 Highly Stereoselective Nickel-Catalyzed Difluoroalkylation of Aryl
 Ketones to Tetrasubstituted Monofluoroalkenes and Quaternary Alkyl
 Difluorides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02806D
_journal_year                    2019
_chemical_formula_sum            'C30 H24 Cl N O2'
_chemical_formula_weight         465.95
_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
_audit_block_doi                 10.5517/ccdc.csd.cc214bbw
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-11-24 deposited with the CCDC.    2019-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.894(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.3331(3)
_cell_length_b                   14.0402(2)
_cell_length_c                   20.1069(3)
_cell_measurement_reflns_used    5999
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.1720
_cell_measurement_theta_min      4.0250
_cell_volume                     4925.17(14)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9721
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.352
_diffrn_reflns_theta_min         3.905
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00074(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0876P)^2^+2.9235P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4009
_reflns_number_total             4666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02806d2.cif
_cod_data_source_block           shelxl
_cod_database_code               1552250
_shelx_estimated_absorpt_t_min   0.666
_shelx_estimated_absorpt_t_max   0.722
_shelxl_version_number           2013-4
_shelx_res_checksum              72440