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_7225514
_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         '2(C31 H28 Fe N2 O), C Cl2'
_chemical_formula_sum            'C63 H58 Cl2 Fe2 N4 O2'
_chemical_formula_weight         1085.73
_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   mixed
_atom_sites_solution_primary     direct
_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                 95.6050(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.7314(2)
_cell_length_b                   10.30632(19)
_cell_length_c                   17.8542(4)
_cell_measurement_reflns_used    3674
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.9760
_cell_measurement_theta_min      4.2790
_cell_volume                     2697.78(9)
_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
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_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  -61.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 28

  2 omega  -26.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   90.0000 45

  3 omega  -69.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 25

  4 omega   20.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   90.0000 52

  5 omega   61.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -180.0000 46

  6 omega   -3.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   90.0000 69

  7 omega   68.00  125.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 57

  8 omega   93.00  122.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   60.0000 29

  9 omega   -4.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -150.0000 77

 10 omega   46.00   96.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 50

 11 omega   93.00  118.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 25

 12 omega   46.00  107.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 61

 13 omega  121.00  176.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 55

 14 omega   44.00   98.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 54

 15 omega   55.00   88.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 33

 16 omega   43.00   93.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 50

 17 omega   59.00   85.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  150.0000 26

 18 omega   66.00   92.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 26

 19 omega   93.00  164.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  120.0000 71

 20 omega  -21.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 90

 21 omega  -73.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000   60.0000 117
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0669309000
_diffrn_orient_matrix_UB_12      -0.0441186000
_diffrn_orient_matrix_UB_13      0.0560583000
_diffrn_orient_matrix_UB_21      -0.0796749000
_diffrn_orient_matrix_UB_22      0.0110537000
_diffrn_orient_matrix_UB_23      -0.0623008000
_diffrn_orient_matrix_UB_31      0.0145855000
_diffrn_orient_matrix_UB_32      -0.1424059000
_diffrn_orient_matrix_UB_33      -0.0221800000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9723
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.014
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40527
_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    1.337
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4818
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0497
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3885
_reflns_number_total             4818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra11972g2.cif
_cod_data_source_block           201506167
_cod_database_code               7225514
_chemical_oxdiff_formula         C20H20N4O4Fe1
_shelx_estimated_absorpt_t_max   0.450
_shelx_estimated_absorpt_t_min   0.372
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C32-Cl1
 1.7 with sigma of 0.02
 C32_$1-Cl1_$1
 1.7 with sigma of 0.02
 C32_$1-C32
 2.2 with sigma of 0.02
 Cl1-C32
 1.76 with sigma of 0.02
3. Others
 Fixed Sof: C32(0.5)
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),
  C28(H28), C29(H29), C30(H30), C31(H31)
4.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              74468
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'