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_4517162
_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            'C53 H44 Cl Fe N O3 S'
_chemical_formula_weight         866.25
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                75.2715(7)
_cell_angle_beta                 69.3507(7)
_cell_angle_gamma                63.0204(6)
_cell_formula_units_Z            2
_cell_length_a                   12.2076(7)
_cell_length_b                   12.7468(7)
_cell_length_c                   16.7154(9)
_cell_measurement_reflns_used    5448
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.2917
_cell_measurement_theta_min      2.3469
_cell_volume                     2155.2(2)
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0158
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11587
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.06
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.660
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.000(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1086
_refine_ls_number_reflns         9817
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0736P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                8846
_reflns_number_total             9817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04438_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2020-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C106 H88 Cl2 Fe2 N2 O6 S2'
_cod_original_formula_weight         1732.50
_cod_original_formula_units_Z            1
_cod_database_code               4517162
_shelx_res_checksum              81413
_shelx_hkl_checksum              27446