Experimental and Theoretical Studies on Ru(II)-Catalyzed Oxidative C–H/C–H Coupling of Phenols with Aromatic Amides Using Air as Oxidant: Scope, Synthetic Applications, and Mechanistic Insights
Zhang, Luoqiang; Zhu, Lei; Zhang, Yuming; Yang, Yudong; Wu, Yimin; Ma, Weixin; Lan, Yu; You, Jingsong; ACS Catalysis 8 (2018) 8324–; doi:10.1021/acscatal.8b02816

data_4515726
_publ_section_title
;
 Experimental and Theoretical Studies on Ru(II)-Catalyzed Oxidative
 C--H/C--H Coupling of Phenols with Aromatic Amides Using Air as Oxidant:
 Scope, Synthetic Applications, and Mechanistic Insights
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8324
_journal_paper_doi               10.1021/acscatal.8b02816
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C23 H24 N2 O2'
_chemical_formula_sum            'C23 H24 N2 O2'
_chemical_formula_weight         360.44
_chemical_name_systematic        yjs-zlq-1
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.50(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.295(7)
_cell_length_b                   11.086(10)
_cell_length_c                   21.615(16)
_cell_measurement_reflns_used    6125
_cell_measurement_temperature    295.28(11)
_cell_measurement_theta_max      72.4650
_cell_measurement_theta_min      4.4440
_cell_volume                     1984(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.28(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -120.0000 95

  2 omega    7.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   19.0000 -180.0000 100

  3 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000   90.0000 66

  4 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  150.0000 66

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -150.0000 84

  6 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -30.0000 84

  7 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

  8 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

  9 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 10 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 85

 11 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 12 omega  100.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 78

 13 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 14 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 15 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 16 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 17 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   60.0000 95

 18 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000   90.0000 88

 19 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000    0.0000 84

 20 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  -30.0000 66

 21 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -60.0000 95

 22 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000    0.0000 88

 23 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -180.0000 95

 24 omega   70.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 108

 25 omega   70.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 108

 26 omega   81.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 27 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0949798000
_diffrn_orient_matrix_UB_12      -0.0591835000
_diffrn_orient_matrix_UB_13      0.0555109000
_diffrn_orient_matrix_UB_21      -0.1406268000
_diffrn_orient_matrix_UB_22      0.0264629000
_diffrn_orient_matrix_UB_23      0.0412741000
_diffrn_orient_matrix_UB_31      -0.0762607000
_diffrn_orient_matrix_UB_32      -0.1228721000
_diffrn_orient_matrix_UB_33      -0.0178585000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17090
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         5.343
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42879
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       irregular
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.1036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1685P)^2^+0.0730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2167
_refine_ls_wR_factor_ref         0.2530
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2586
_reflns_number_total             3534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b02816_si_002.cif
_cod_data_source_block           yjs-zlq-1
_cod_database_code               4515726
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.89
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N004(H004), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F),
 C00H(H00H), C00I(H00I), C00L(H00L), C00N(H00O), C00O(H00P), C00Q(H00T)
2.b Idealised Me refined as rotating group:
 C00K(H00C,H00G,H00J), C00M(H00K,H00M,H00N), C00P(H00Q,H00R,H00S), C00R(H00U,
 H00V,H00W)
;
_olex2_date_sample_data_collection 2016-07-30
_olex2_submission_special_instructions 'No special instructions were received'