Cobalt-Catalyzed Oxidative C-H/N-H Cross-Coupling: Selective and Facile Access to Triarylamines
Du, Cong; Li, Peng-Xiang; Zhu, Xinju; Han, Jiao-Na; Niu, Jun-Long; Song, Mao-Ping; ACS Catalysis  (2017) –; doi:10.1021/acscatal.7b00262

data_4514073
_publ_section_title
;
 Cobalt-Catalyzed Oxidative C-H/N-H Cross-Coupling: Selective and Facile
 Access to Triarylamines
;
_journal_name_full               'ACS Catalysis'
_journal_paper_doi               10.1021/acscatal.7b00262
_journal_year                    2017
_chemical_formula_moiety         'C38 H27 N5 O2'
_chemical_formula_sum            'C38 H27 N5 O2'
_chemical_formula_weight         585.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1283(11)
_cell_length_b                   9.2992(4)
_cell_length_c                   18.9173(5)
_cell_measurement_reflns_used    2679
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6700
_cell_measurement_theta_min      4.6660
_cell_volume                     3013.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -72.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   30.0000 44

  2 omega  -48.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000 -120.0000 32

  3 omega   82.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 28

  4 omega   61.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 31

  5 omega  -32.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 66

  6 omega   69.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 26

  7 omega   14.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 55

  8 omega   41.00  105.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 64

  9 omega  100.00  163.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 63

 10 omega   37.00   73.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 36

 11 omega   59.00  125.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 66

 12 omega   41.00   84.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 43

 13 omega   95.00  158.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0842038000
_diffrn_orient_matrix_UB_12      -0.0385595000
_diffrn_orient_matrix_UB_13      -0.0216901000
_diffrn_orient_matrix_UB_21      0.0252013000
_diffrn_orient_matrix_UB_22      -0.1569279000
_diffrn_orient_matrix_UB_23      -0.0126891000
_diffrn_orient_matrix_UB_31      -0.0194027000
_diffrn_orient_matrix_UB_32      -0.0363864000
_diffrn_orient_matrix_UB_33      0.0774379000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0208
_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       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.098
_diffrn_reflns_theta_max         67.098
_diffrn_reflns_theta_min         4.675
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.00115(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0525P)^2^+0.5599P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2219
_reflns_number_total             2694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00262_si_002.cif
_cod_data_source_block           201608111
_cod_database_code               4514073
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              91364
_shelx_hkl_checksum              70893
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'