Intramolecular Direct C-H Arylation via a Metallocenic Radical Pathway: Stereospecific Approach to Planar-Chiral Ferrocenes.
Liu, Yang; Xu, Jiancong; Zhang, Jinling; Xu, Xiaohua; Jin, Zhong; Organic letters 19 (2017) 5709–5712; doi:10.1021/acs.orglett.7b02995

data_1547601
_publ_section_title
;
 Intramolecular Direct C-H Arylation via a Metallocenic Radical Pathway:
 Stereospecific Approach to Planar-Chiral Ferrocenes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5709
_journal_page_last               5712
_journal_paper_doi               10.1021/acs.orglett.7b02995
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C19 H17 Fe N O'
_chemical_formula_weight         331.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-08-10 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.165(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.945(4)
_cell_length_b                   8.3402(18)
_cell_length_c                   17.264(4)
_cell_measurement_reflns_used    8276
_cell_measurement_temperature    128(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2871.2(11)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      128(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30398
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_T_max  0.8843
_exptl_absorpt_correction_T_min  0.8174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'colorless prism'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    CONNSTR
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+0.7222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0691
_reflns_number_gt                5802
_reflns_number_total             6595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b02995_si_002.cif
_cod_data_source_block           m20170426a1
_cod_depositor_comments
'Adding full bibliography for 1547599--1547601.cif.'
_cod_original_cell_volume        2871.1(10)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1547601