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_4514074
_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         'C44 H31 Co N6 O2, C1 H2 Cl2'
_chemical_formula_sum            'C45 H33 Cl2 Co N6 O2'
_chemical_formula_weight         819.60
_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     heavy
_audit_creation_date             2016-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.838(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2327(4)
_cell_length_b                   13.1901(4)
_cell_length_c                   24.1763(8)
_cell_measurement_reflns_used    5277
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1060
_cell_measurement_theta_min      3.8070
_cell_volume                     3787.6(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 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_details
;
  1 omega  -30.00   -0.80   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3317   40.0000  -60.0000 73

  2 omega    0.00   85.20   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   40.0000  -60.0000 213

  3 omega   24.00   52.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3317   40.0000  -60.0000 70

  4 omega  -21.00   18.20   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3317  -99.0000  -60.0000 98

  5 omega   40.00   71.20   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  178.0000    0.0000 78

  6 omega  -16.00   54.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -99.0000   60.0000 175

  7 omega   36.00   62.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  178.0000   90.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0423464000
_diffrn_orient_matrix_UB_12      -0.0361743000
_diffrn_orient_matrix_UB_13      0.0113379000
_diffrn_orient_matrix_UB_21      0.0383766000
_diffrn_orient_matrix_UB_22      0.0397851000
_diffrn_orient_matrix_UB_23      0.0105268000
_diffrn_orient_matrix_UB_31      -0.0173789000
_diffrn_orient_matrix_UB_32      -0.0003453000
_diffrn_orient_matrix_UB_33      0.0259555000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22876
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         3.430
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87521
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       prism
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7740
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0853P)^2^+2.9089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5888
_reflns_number_total             7740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00262_si_002.cif
_cod_data_source_block           201612189
_cod_original_cell_volume        3787.7(2)
_cod_database_code               4514074
_chemical_oxdiff_formula         C30H30O2N2P2Co1
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 Cl1A-C45A
 1.76 with sigma of 0.02
 C45-Cl2
 1.7 with sigma of 0.02
 Cl2-Cl1
 2.8 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C45) \\sim Ueq, Uanis(C45A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O1) = Uanis(O1A)
Uanis(Cl2) = Uanis(Cl2A)
Uanis(Cl1) = Uanis(Cl1A)
Uanis(C45) = Uanis(C45A)
4. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
 Sof(C45A)=Sof(H45C)=Sof(H45D)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(2)
 Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(Cl1)=Sof(Cl2)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C45A(H45C,H45D)
5.b 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), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25), C29(H29), C30(H30), C31(H31), C35(H35), C36(H36), C37(H37),
 C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), N6(H6)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'