Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)‒H arylation
Wu, Qian; Du, Chenglong; Huang, Yumin; Liu, Xingyan; Long, Zhen; Song, Feijie; You, Jingsong; Chem. Sci. 6 (2015) 288–; doi:10.1039/C4SC02070G

data_1517972
_publ_section_title
;
 Stoichiometric to catalytic reactivity of the aryl cycloaurated species
 with arylboronic acids: insight into the mechanism of gold-catalyzed
 oxidative C(sp2)--H arylation
;
_journal_issue                   1
_journal_name_full               'Chem. Sci.'
_journal_page_first              288
_journal_paper_doi               10.1039/C4SC02070G
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C18 H16 Au Cl2 N'
_chemical_formula_sum            'C18 H16 Au Cl2 N'
_chemical_formula_weight         514.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
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_cell_angle_gamma                113.776(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8572(3)
_cell_length_b                   8.2744(4)
_cell_length_c                   15.3789(5)
_cell_measurement_reflns_used    8880
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.6200
_cell_measurement_theta_min      5.8800
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
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;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293
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_diffrn_detector_type            EosS2
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_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000    0.0000 94

  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000   90.0000 84

  3 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  120.0000 94

  4 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000 -120.0000 88

  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -120.0000 67

  6 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -150.0000 84

  7 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  -60.0000 74

  8 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -19.0000  -30.0000 101

  9 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 10 omega   38.00  116.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

 11 omega   39.00  109.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 12 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 13 omega  100.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 78

 14 omega   37.00  146.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 109

 15 omega   91.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 16 omega   57.00  150.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 93

 17 omega   40.00   98.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 18 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 19 omega   39.00  109.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 20 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 21 omega  100.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

 22 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 23 omega   41.00  126.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 85

 24 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -180.0000 67

 25 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -150.0000 94

 26 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -120.0000 94

 27 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000   90.0000 88

 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -60.0000 94

 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000    0.0000 94

 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -30.0000 94

 31 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 32 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 95

 33 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 34 omega   70.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 108

 35 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

 36 omega   70.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108

 37 omega   91.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

 38 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 39 omega   87.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

 40 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 41 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 42 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 43 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 44 omega   70.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      0.0433268000
_diffrn_orient_matrix_UB_13      -0.0966985000
_diffrn_orient_matrix_UB_21      0.2180616000
_diffrn_orient_matrix_UB_22      0.1262539000
_diffrn_orient_matrix_UB_23      0.0296890000
_diffrn_orient_matrix_UB_31      0.0456066000
_diffrn_orient_matrix_UB_32      -0.1575804000
_diffrn_orient_matrix_UB_33      -0.0263147000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.985
_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       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15399
_diffrn_reflns_point_group_measured_fraction_full 0.985
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.076
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_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'yellowish yellow'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.797
_refine_diff_density_min         -1.132
_refine_diff_density_rms         0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0760P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2978
_reflns_number_total             3132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc02070g2.cif
_cod_data_source_block           wq6
_cod_depositor_comments
'Adding full bibliography for 1517970--1517972.cif.'
_cod_original_cell_volume        876.94(6)
_cod_database_code               1517972
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              46838
_olex2_submission_special_instructions 'No special instructions were received'