Access to Planar Chiral Ferrocenes via N-Heterocyclic Carbene-Catalyzed Enantioselective Desymmetrization Reactions
Lv, Xiaokang; Xu, Jun; Sun, Cuiyun; Su, Fen; Cai, Yuanlin; Jin, Zhichao; Chi, Yonggui Robin; ACS Catalysis 12 (2022) 2706–2713; doi:10.1021/acscatal.2c00001

data_4519341
_publ_section_title
;
 Access to Planar Chiral Ferrocenes via N-Heterocyclic Carbene-Catalyzed
 Enantioselective Desymmetrization Reactions
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2706
_journal_page_last               2713
_journal_paper_doi               10.1021/acscatal.2c00001
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C21 H19 Fe N O6'
_chemical_formula_sum            'C21 H19 Fe N O6'
_chemical_formula_weight         437.22
_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   geom
_audit_creation_date             2021-05-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.481(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6105(6)
_cell_length_b                   8.0429(7)
_cell_length_c                   15.2788(13)
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.149
_cell_measurement_theta_min      2.721
_cell_volume                     916.51(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4427
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.721
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  0.7817
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1080 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0348P)^2^+0.2311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.879
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                2743
_reflns_number_total             3043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs2c00001_si_002.cif
_cod_data_source_block           210513e
_cod_database_code               4519341
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.782
_shelx_estimated_absorpt_t_min   0.697
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              63369
_shelx_hkl_checksum              41112
_olex2_submission_special_instructions 'No special instructions were received'