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_1517970
_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         'C12 H10 Au Br2 N, H2 O'
_chemical_formula_sum            'C12 H12 Au Br2 N O'
_chemical_formula_weight         543.01
_chemical_name_systematic
;
 ?
;
_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   mixed
_atom_sites_solution_primary     direct
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Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                97.689(5)
_cell_angle_beta                 99.690(5)
_cell_angle_gamma                92.960(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0801(4)
_cell_length_b                   10.0993(7)
_cell_length_c                   10.1771(7)
_cell_measurement_reflns_used    2944
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6530
_cell_measurement_theta_min      3.6780
_cell_volume                     708.82(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2012 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
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_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      -0.0254678000
_diffrn_orient_matrix_UB_13      0.0610117000
_diffrn_orient_matrix_UB_21      0.0531774000
_diffrn_orient_matrix_UB_22      -0.0543723000
_diffrn_orient_matrix_UB_23      -0.0202895000
_diffrn_orient_matrix_UB_31      0.0867787000
_diffrn_orient_matrix_UB_32      0.0380350000
_diffrn_orient_matrix_UB_33      0.0311766000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
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_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5824
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.927
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    15.998
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.544
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
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_exptl_crystal_size_min          0.05
_refine_diff_density_max         6.486
_refine_diff_density_min         -1.947
_refine_diff_density_rms         0.442
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0658
_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^)+(0.1469P)^2^+0.4645P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.1941
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_reflns_number_gt                2596
_reflns_number_total             2890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc02070g2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1517970--1517972.cif.'
_cod_original_cell_volume        708.83(8)
_cod_database_code               1517970
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2br2au1
_shelx_estimated_absorpt_t_max   0.502
_shelx_estimated_absorpt_t_min   0.086
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              66878