An Enantioselective Oxidative C-H/C-H Cross-Coupling Reaction: Highly Efficient Method To Prepare Planar Chiral Ferrocenes.
Gao, De-Wei; Gu, Qing; You, Shu-Li; Journal of the American Chemical Society 138 (2016) 2544–2547; doi:10.1021/jacs.6b00127

data_4130095
_publ_section_title
;
 An Enantioselective Oxidative C-H/C-H Cross-Coupling Reaction: Highly
 Efficient Method To Prepare Planar Chiral Ferrocenes.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2544
_journal_page_last               2547
_journal_paper_doi               10.1021/jacs.6b00127
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H22 Fe N2 O'
_chemical_formula_sum            'C19 H22 Fe N2 O'
_chemical_formula_weight         350.23
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-29
_audit_creation_method
; 
Olex2 1.2 
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4957(7)
_cell_length_b                   13.2816(10)
_cell_length_c                   14.4218(11)
_cell_measurement_reflns_used    7053
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.268
_cell_measurement_theta_min      2.78
_cell_volume                     1627.3(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.710
_diffrn_reflns_theta_min         2.085
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0683 before and 0.0478 after correction. 
The Ratio of minimum to maximum transmission is 0.7909. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
; 
 Flack x determined using 1875 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         5003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0269
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0363P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0646
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4592
_reflns_number_total             5003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b00127_si_002.cif
_cod_data_source_block           dm15443
_cod_database_code               4130095
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.800
_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 Secondary CH2 refined with riding coordinates: 
 C11(H11A,H11B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), 
 C16(H16), C18(H18) 
2.c Idealised Me refined as rotating group: 
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C19(H19A,H19B,H19C) 
;
_shelx_res_checksum              28113
_shelx_hkl_checksum              69350
_olex2_submission_special_instructions 'No special instructions were received'