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_4125623
_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_formula_moiety         'C15 H14 O'
_chemical_formula_sum            'C15 H14 O'
_chemical_formula_weight         210.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-23
_audit_creation_method
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Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_formula_units_Z            8
_cell_length_a                   7.69025(7)
_cell_length_b                   13.54657(17)
_cell_length_c                   20.9417(2)
_cell_measurement_reflns_used    11490
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.9380
_cell_measurement_theta_min      4.1950
_cell_volume                     2181.63(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
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_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega -113.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -57.0000  120.0000 96

  2 omega  -70.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   57.0000  -90.0000 97

  3 omega   24.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1686 -126.0000  -31.0000 75

  4 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1686 -125.0000 -180.0000 75

  5 omega   39.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  150.0000 82

  6 omega   87.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  150.0000 91

  7 omega   94.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000   30.0000 84

  8 omega   41.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000  -60.0000 98

  9 omega   39.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000    0.0000 82

 10 omega   87.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -120.0000 91

 11 omega   40.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -120.0000 59

 12 omega   39.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -120.0000 82

 13 omega   30.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  120.0000 79

 14 omega   94.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000  150.0000 84

 15 omega   36.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000    0.0000 55

 16 omega -117.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000  -30.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0009722000
_diffrn_orient_matrix_UB_12      -0.1126329000
_diffrn_orient_matrix_UB_13      -0.0103454000
_diffrn_orient_matrix_UB_21      -0.0954524000
_diffrn_orient_matrix_UB_22      -0.0138045000
_diffrn_orient_matrix_UB_23      0.0640285000
_diffrn_orient_matrix_UB_31      -0.1760839000
_diffrn_orient_matrix_UB_32      0.0081720000
_diffrn_orient_matrix_UB_33      -0.0346760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17154
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.161
_diffrn_reflns_theta_min         4.222
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_recrystallization_method
'The material was recrystallised from methanol by slow cooling'
_exptl_crystal_size_max          0.3937
_exptl_crystal_size_mid          0.3069
_exptl_crystal_size_min          0.0702
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0085(15)
_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   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0904P)^2^+0.7282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2132
_reflns_number_total             2265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b10018_si_002.cif
_cod_data_source_block           gl15001
_cod_database_code               4125623
_chemical_oxdiff_formula         'C15 H14 O'
_chemical_oxdiff_usercomment     '@ 120 K TC91'
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              54099
_shelx_hkl_checksum              65130
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    2015-07-21
_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 TC91
_olex2_submission_special_instructions 'No special instructions were received'