Versatile and Enantioselective Preparation of Planar-Chiral Metallocene-Fused 4-Dialkylaminopyridines and Their Application in Asymmetric Organocatalysis
Yoshida, Kazuhiro; Liu, Qiang; Yasue, Risa; Wada, Shiro; Kimura, Ryosuke; Konishi, Takuma; Ogasawara, Masamichi; ACS Catalysis  (2019) 292–; doi:10.1021/acscatal.9b04438

data_4517163
_publ_section_title
;
 Versatile and Enantioselective Preparation of Planar-Chiral
 Metallocene-Fused 4-Dialkylaminopyridines and Their Application in
 Asymmetric Organocatalysis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              292
_journal_paper_doi               10.1021/acscatal.9b04438
_journal_year                    2019
_chemical_formula_sum            'C50 H46 Fe N2'
_chemical_formula_weight         730.74
_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'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9661(8)
_cell_length_b                   17.5243(12)
_cell_length_c                   19.8084(14)
_cell_measurement_reflns_used    4310
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.8983
_cell_measurement_theta_min      2.3244
_cell_volume                     3806.6(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19243
_diffrn_reflns_theta_full        25.53
_diffrn_reflns_theta_max         25.53
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.252
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.024(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         7079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                5816
_reflns_number_total             7079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04438_si_002.cif
_cod_data_source_block           I
_cod_database_code               4517163
_shelx_res_checksum              55705
_shelx_hkl_checksum              13020