Synthesis of Ferrocene-Based Pyridinones through Rh(III)-Catalyzed Direct C‒H Functionalization Reaction
Wang, Shao-Bo; Zheng, Jun; You, Shu-Li; Organometallics 35 (2016) 1420–; doi:10.1021/acs.organomet.6b00020

data_4088358
_publ_section_title
;
 Synthesis of Ferrocene-Based Pyridinones through Rh(III)-Catalyzed Direct
 C--H Functionalization Reaction
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              1420
_journal_paper_doi               10.1021/acs.organomet.6b00020
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C20 H17 Fe N O'
_chemical_formula_sum            'C20 H17 Fe N O'
_chemical_formula_weight         343.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.591(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2332(14)
_cell_length_b                   9.8643(11)
_cell_length_c                   13.7723(16)
_cell_measurement_reflns_used    2207
_cell_measurement_temperature    130
_cell_measurement_theta_max      25.797
_cell_measurement_theta_min      2.62
_cell_volume                     1523.0(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0548
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15048
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.573
_diffrn_reflns_theta_min         1.886
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0566 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.8938.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.0284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3334
_reflns_number_total             4669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00020_si_002.cif
_cod_data_source_block           mo_dm15372_0m
_cod_database_code               4088358
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.907
_shelx_estimated_absorpt_t_min   0.789
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              26576
_shelx_hkl_checksum              46291
_olex2_submission_special_instructions 'No special instructions were received'