Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.
Poremba, Kelsey E.; Kadunce, Nathaniel T.; Suzuki, Naoyuki; Cherney, Alan H.; Reisman, Sarah E.; Journal of the American Chemical Society 139 (2017) 5684–5687; doi:10.1021/jacs.7b01705

data_4131247
_publ_section_title
;
 Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access
 1,1-Diarylalkanes.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5684
_journal_page_last               5687
_journal_paper_doi               10.1021/jacs.7b01705
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 F3 N O'
_chemical_formula_sum            'C17 H16 F3 N O'
_chemical_formula_weight         307.30
_chemical_name_common            KEP-2-091
_chemical_name_systematic        KEP-2-091
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5921(3)
_cell_length_b                   5.30640(10)
_cell_length_c                   22.4242(5)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    200
_cell_measurement_theta_max      78.67
_cell_measurement_theta_min      3.79
_cell_volume                     1479.90(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (She ldrick, 2013)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20749
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.473
_diffrn_reflns_theta_min         3.554
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_coef       0.0007(2)
_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   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6253
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0488
_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^)+(0.0252P)^2^+0.3460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                5418
_reflns_number_total             6253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b01705_si_001.cif
_cod_data_source_block           p16163_jlh_a
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H16 F3 N O)'
_cod_original_formula_sum        'C34 H32 F6 N2 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     614.61
_cod_database_code               4131247
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.827
_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 Ternary CH refined with riding coordinates:
 C7B(H7B), C7A(H7A)
2.b Secondary CH2 refined with riding coordinates:
 C8B(H8BA,H8BB), C8A(H8AA,H8AB)
2.c Aromatic/amide H refined with riding coordinates:
 C15B(H15B), C12B(H12B), C14B(H14B), C11B(H11B), C14A(H14A), C11A(H11A),
 C12A(H12A), C15A(H15A), C6B(H6B), C2B(H2B), C3B(H3B), C6A(H6A), C2A(H2A),
 C5B(H5B), C4B(H4B), C5A(H5A), C3A(H3A), C4A(H4A)
2.d Idealised Me refined as rotating group:
 C9B(H9BA,H9BB,H9BC), C9A(H9AA,H9AB,H9AC)
;
_shelx_res_checksum              11527
_shelx_hkl_checksum              4182
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'