Au-Catalyzed Biaryl Coupling To Generate 5- to 9-Membered Rings: Turnover-Limiting Reductive Elimination versus π-Complexation.
Corrie, Tom J. A.; Ball, Liam T.; Russell, Christopher A.; Lloyd-Jones, Guy C; Journal of the American Chemical Society 139 (2017) 245–254; doi:10.1021/jacs.6b10018

data_4125622
_publ_section_title
;
 Au-Catalyzed Biaryl Coupling To Generate 5- to 9-Membered Rings:
 Turnover-Limiting Reductive Elimination versus \p-Complexation.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              245
_journal_page_last               254
_journal_paper_doi               10.1021/jacs.6b10018
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H16 O'
_chemical_formula_sum            'C16 H16 O'
_chemical_formula_weight         224.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.4854(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.92506(15)
_cell_length_b                   7.62053(8)
_cell_length_c                   22.4351(2)
_cell_measurement_reflns_used    34216
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      76.1350
_cell_measurement_theta_min      3.9210
_cell_volume                     2380.65(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_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_environment      air
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega    7.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   87.0000 -122.6502 27

  2 omega -113.00  -16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.9186  -57.0000  -30.0000 97

  3 omega  -50.00   30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.9186   38.0000  150.0000 80

  4 omega -116.00  -20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.9186  -38.0000  150.0000 96

  5 omega -113.00  -16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.9186  -57.0000   60.0000 97

  6 omega  -74.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.9186   77.0000 -150.0000 105

  7 omega   23.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.9186 -125.0000   30.0000 75

  8 omega   14.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   78.0000  144.6859 35

  9 omega   13.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000  -12.5670 32

 10 omega   18.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  -54.6125 31

 11 omega   18.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000   55.4635 28

 12 omega   22.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -167.2683 27

 13 omega   22.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   40.9721 27

 14 omega   27.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  138.8699 105

 15 omega   35.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000   55.1306 104

 16 omega   35.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -82.8675 105

 17 omega   39.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   76.0000 -165.3028 104

 18 omega   39.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000  161.1425 104

 19 omega   39.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   82.0351 105

 20 omega   43.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000 -145.1387 105

 21 omega   43.00  147.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   76.0000 -117.4125 104

 22 omega   43.00  147.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   75.0000   63.3076 104

 23 omega   43.00  147.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   76.0000  -68.6949 104

 24 omega   43.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  -13.3706 105

 25 omega   43.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  -53.6018 105

 26 omega   53.00  153.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   67.0000  109.4192 100

 27 omega   52.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   73.0000  -78.3851 102

 28 omega   58.00  156.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   63.0000   29.6474 98

 29 omega   61.00  161.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   69.0000 -149.4920 100

 30 omega   62.00  160.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   63.0000  178.5846 98

 31 omega   60.00  162.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   73.0000   -9.7743 102

 32 omega   64.00  166.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   70.0000  138.3756 102

 33 omega   68.00  164.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   56.0000  -97.1791 96

 34 omega   67.00  172.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   77.0000  -47.7025 105

 35 omega   67.00  171.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   76.0000   49.3939 104

 36 omega   72.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   70.0000   97.7343 102

 37 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  120.0000 98

 38 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -180.0000 98

 39 omega   85.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   53.0000 -126.2537 93

 40 omega   83.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -60.0000 95

 41 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -90.0000 98

 42 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   60.0000 98

 43 omega   83.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -150.0000 95

 44 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -60.0000 82

 45 omega   40.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  120.0000 59

 46 omega   83.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  150.0000 95

 47 omega   36.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   60.0000 55

 48 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000    0.0000 98

 49 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -120.0000 98

 50 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -180.0000 82

 51 omega   66.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000   30.0000 112

 52 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -30.0000 98

 53 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   90.0000 91

 54 omega   83.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -180.0000 95

 55 omega   37.00  142.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000   60.0000 105

 56 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -150.0000 79

 57 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   60.0000 82

 58 omega   40.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   30.0000 59

 59 omega   83.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -120.0000 95

 60 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -60.0000 79

 61 omega   83.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   30.0000 95

 62 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   60.0000 79

 63 omega   41.00  139.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -120.0000 98

 64 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  150.0000 79

 65 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -30.0000 79

 66 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  150.0000 98

 67 omega   83.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -90.0000 95

 68 omega   37.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -32.0000  167.8442 54

 69 omega   83.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -30.0000 95

 70 omega   82.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   67.0000  112.1114 96

 71 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   60.0000 91

 72 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000    0.0000 79

 73 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  120.0000 82

 74 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -90.0000 82

 75 omega    0.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   94.0000 -137.0306 26

 76 omega   18.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  136.3802 29

 77 omega   18.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000 -117.8413 29

 78 omega   22.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000    0.0004 27

 79 omega   31.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000 -178.1366 105

 80 omega   31.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000  -62.8358 104

 81 omega   38.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   61.0000  157.6945 98

 82 omega   35.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000 -101.9146 104

 83 omega   36.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   70.0000   39.1865 102

 84 omega  137.00  163.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   50.0000  104.0000 26

 85 omega   71.00   97.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 26

 86 omega   63.00  101.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -69.0000  133.7830 38

 87 omega  125.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000  -30.0000 49

 88 omega   40.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000    0.0000 26

 89 omega   96.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000    0.0000 25

 90 omega   98.00  124.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -90.0000 26

 91 omega   56.00   82.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000    0.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0938135000
_diffrn_orient_matrix_UB_12      0.0198697000
_diffrn_orient_matrix_UB_13      -0.0362688000
_diffrn_orient_matrix_UB_21      0.0095143000
_diffrn_orient_matrix_UB_22      -0.1908699000
_diffrn_orient_matrix_UB_23      -0.0218007000
_diffrn_orient_matrix_UB_31      -0.0577409000
_diffrn_orient_matrix_UB_32      -0.0637384000
_diffrn_orient_matrix_UB_33      0.0541142000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            55336
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.555
_diffrn_reflns_theta_min         3.941
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0872 after correction.
The Ratio of minimum to maximum transmission is 0.8720.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method
'The material was recrystallised from methanol by slow cooling'
_exptl_crystal_size_max          0.2118
_exptl_crystal_size_mid          0.1184
_exptl_crystal_size_min          0.0688
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2283 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4857
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0566P)^2^+0.9509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                4802
_reflns_number_total             4857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b10018_si_003.cif
_cod_data_source_block           gl15002
_cod_database_code               4125622
_chemical_oxdiff_formula         'C16 H16 O'
_chemical_oxdiff_usercomment     '@ 120 K TC252'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C57(H57A,H57B),
 C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C52(H52), C53(H53), C54(H54), C55(H55), C63(H63), C64(H64), C65(H65), C66(H66)
;
_shelx_res_checksum              95589
_shelx_hkl_checksum              15390
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-22
_olex2_date_sample_submission    2015-11-19
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id TC252
_olex2_submission_special_instructions 'No special instructions were received'