Pd-Catalyzed Highly Enantioselective Synthesis of Planar Chiral Ferrocenylpyridine Derivatives
Gao, De-Wei; Zheng, Chao; Gu, Qing; You, Shu-Li; Organometallics 34 (2015) 4618–; doi:10.1021/acs.organomet.5b00730

data_4086237
_publ_section_title
;
 Pd-Catalyzed Highly Enantioselective Synthesis of Planar Chiral
 Ferrocenylpyridine Derivatives
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              4618
_journal_paper_doi               10.1021/acs.organomet.5b00730
_journal_volume                  34
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H20 F Fe N O'
_chemical_formula_sum            'C21 H20 F Fe N O'
_chemical_formula_weight         377.23
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.043(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7804(9)
_cell_length_b                   13.8228(15)
_cell_length_c                   16.0974(17)
_cell_measurement_reflns_used    4680
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.51
_cell_measurement_theta_min      2.53
_cell_volume                     1730.1(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16863
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.406
_diffrn_reflns_theta_min         1.266
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0735 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.8176.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         8808
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.2990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.639
_reflns_friedel_fraction_full    0.785
_reflns_friedel_fraction_max     0.684
_reflns_number_gt                7090
_reflns_number_total             8808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00730_si_002.cif
_cod_data_source_block           mo_dm14524_0m
_cod_depositor_comments          'Adding full bibliography for 4086237.cif.'
_cod_database_code               4086237
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.822
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C23(H23), C24(H24), C25(H25),
 C30(H30), C31(H31)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,
 H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              88879
_shelx_hkl_checksum              71005
_olex2_submission_special_instructions 'No special instructions were received'