One-Pot Synthesis of Ferrocenyl Ketones Containing Biaryls and 6-Aryl-2-ferrocenylquinolines via Ir/Pd-Cocatalyzed α-Alkylation/Suzuki Reaction
Chen Xu; Xin-Qi Hao; Zhi-Qiang Xiao; Zhi-Qiang Wang; Xiao-Er Yuan; Wei-Jun Fu; Bao-Ming Ji; Mao-Ping Song; Journal of Organic Chemistry 78 (2013) 8730–8738; doi:10.1021/jo401421b

data_4028565
_publ_contact_author_name
;
;
_publ_section_title
;
 One-Pot Synthesis of Ferrocenyl Ketones Containing Biaryls and
 6-Aryl-2-ferrocenylquinolines via Ir/Pd-Cocatalyzed \a-Alkylation/Suzuki
 Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8730
_journal_page_last               8738
_journal_paper_doi               10.1021/jo401421b
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C27 H21 Fe N O2'
_chemical_formula_sum            'C27 H21 Fe N O2'
_chemical_formula_weight         447.30
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.952(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1180(3)
_cell_length_b                   11.4661(4)
_cell_length_c                   29.4764(10)
_cell_measurement_reflns_used    3148
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.1530
_cell_measurement_theta_min      3.2860
_cell_volume                     2066.56(14)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
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SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -85.00  -56.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2885  141.0000  110.0000 58

  2 omega  -73.00  -48.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2885  128.0000  -60.0000 50

  3 omega    2.00   59.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885 -128.0000 -134.0000 114

  4 omega    7.00   52.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885 -141.0000   53.0000 90

  5 omega    0.00   25.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2885  -99.0000   60.0000 50

  6 omega   36.00   96.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  178.0000  -60.0000 120

  7 omega  -49.00   40.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -57.0000   60.0000 178
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0897743000
_diffrn_orient_matrix_UB_12      -0.0385609000
_diffrn_orient_matrix_UB_13      0.0034436000
_diffrn_orient_matrix_UB_21      -0.0030456000
_diffrn_orient_matrix_UB_22      0.0094782000
_diffrn_orient_matrix_UB_23      0.0237421000
_diffrn_orient_matrix_UB_31      -0.0734800000
_diffrn_orient_matrix_UB_32      -0.0474311000
_diffrn_orient_matrix_UB_33      0.0019312000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12476
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'Enhance (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description
;
;
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0455P)^2^+0.4471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                3233
_reflns_number_total             4222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401421b_si_001_5.cif
_cod_data_source_block           29
_cod_original_cell_volume        2066.55(13)
_cod_database_code               4028565
_chemical_oxdiff_formula         C20H20N2O3Fe1
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9),
 C12(H12), C13(H13), C16(H16), C17(H17), C19(H19), C21(H21), C23(H23), C24(H24),
  C25(H25)
;