Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes
Ma, Teng; Chen, Yate; Li, Yuxiu; Ping, Yuanyuan; Kong, Wangqing; ACS Catalysis 9 (2019) 9127–; doi:10.1021/acscatal.9b03172

data_4514631
_publ_section_title
;
 Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of
 Alkenes
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9127
_journal_paper_doi               10.1021/acscatal.9b03172
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H22 F N O'
_chemical_formula_sum            'C25 H22 F N O'
_chemical_formula_weight         371.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-30
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9609(2)
_cell_length_b                   9.0105(2)
_cell_length_c                   32.0299(7)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.23
_cell_measurement_theta_min      5.10
_cell_volume                     2008.95(9)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13095
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        64.974
_diffrn_reflns_theta_max         64.974
_diffrn_reflns_theta_min         5.099
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4491
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
; 
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       0.0266(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0710P)^2^+0.1012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3258
_reflns_number_total             3302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03172_si_002.cif
_cod_data_source_block           cu_190529c_0m
_cod_database_code               4514631
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.882
_shelx_estimated_absorpt_t_min   0.830
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C11(H11A,H11B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C15(H15), C16(H16), C18(H18), 
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25) 
2.c Idealised Me refined as rotating group: 
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C) 
;
_shelx_res_checksum              89865
_shelx_hkl_checksum              1801
_olex2_submission_special_instructions 'No special instructions were received'