Palladium-catalyzed direct C-H arylation of ferrocenecarboxamides with aryl halides
Qiao, Huijie; Sun, Suyan; Yang, Fan; Zhu, Yu; Zhu, Weiguo; Wu, Yusheng; Wu, Yangjie; RSC Adv.  (2016) –; doi:10.1039/C6RA11972G

data_7225513
_publ_section_title
;
 Palladium-catalyzed direct C-H arylation of ferrocenecarboxamides with
 aryl halides
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA11972G
_journal_year                    2016
_chemical_formula_moiety         'C32 H24 Fe N2 O'
_chemical_formula_sum            'C32 H24 Fe N2 O'
_chemical_formula_weight         508.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     heavy
_audit_creation_date             2015-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-01-10 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.980(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3423(6)
_cell_length_b                   14.2822(4)
_cell_length_c                   16.0589(7)
_cell_measurement_reflns_used    3017
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.9060
_cell_measurement_theta_min      4.2240
_cell_volume                     2474.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_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  -65.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 28

  2 omega  -27.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000  150.0000 25

  3 omega   -1.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000  150.0000 44

  4 omega  -72.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000  150.0000 25

  5 omega   -5.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   60.0000 75

  6 omega   26.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   30.0000 79

  7 omega   37.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -180.0000 38

  8 omega   31.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  -30.0000 91

  9 omega   44.00   91.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 47

 10 omega   63.00   88.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 25

 11 omega   42.00   96.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 54

 12 omega   48.00  109.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 61

 13 omega   50.00   90.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 40

 14 omega   44.00   98.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 54

 15 omega   63.00   98.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 35

 16 omega   46.00   72.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 26

 17 omega   91.00  156.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 65

 18 omega   49.00  107.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  120.0000 58

 19 omega   68.00   94.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 26

 20 omega  105.00  131.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 26

 21 omega  -69.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0175559000
_diffrn_orient_matrix_UB_12      -0.1036218000
_diffrn_orient_matrix_UB_13      0.0199288000
_diffrn_orient_matrix_UB_21      -0.1411932000
_diffrn_orient_matrix_UB_22      0.0104793000
_diffrn_orient_matrix_UB_23      -0.0416186000
_diffrn_orient_matrix_UB_31      0.0118707000
_diffrn_orient_matrix_UB_32      -0.0278333000
_diffrn_orient_matrix_UB_33      -0.0898362000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9066
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         4.098
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4408
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.3722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3578
_reflns_number_total             4408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra11972g2.cif
_cod_data_source_block           201506168
_cod_database_code               7225513
_chemical_oxdiff_formula         C20H20N4O4Fe1
_shelx_estimated_absorpt_t_max   0.496
_shelx_estimated_absorpt_t_min   0.429
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 C3, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C25(H25), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), N1(H1A)
;
_shelx_res_checksum              95056
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'