Catalytic Au(I)/Au(III) Arylation with the Hemilabile MeDalphos Ligand: Unusual Selectivity for Electron-Rich Iodoarenes and Efficient Application to Indoles
Rodriguez, Jessica; Zeineddine, Abdallah; Sosa Carrizo, E. Daiann; Miqueu, Karinne; Saffon, Nathalie; Amgoune, Abderrahmane; Bourissou, Didier; Chemical Science  (2019) –; doi:10.1039/C9SC01954E

data_1551495
_publ_section_title
;
 Catalytic Au(I)/Au(III) Arylation with the Hemilabile MeDalphos Ligand:
 Unusual Selectivity for Electron-Rich Iodoarenes and Efficient
 Application to Indoles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01954E
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H12 Br N'
_chemical_formula_weight         286.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-01-31 deposited with the CCDC.    2019-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0113(7)
_cell_length_b                   10.6464(12)
_cell_length_c                   16.842(2)
_cell_measurement_reflns_used    9198
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      3.08
_cell_volume                     1257.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8-Venture CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29152
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.373
_diffrn_reflns_theta_min         3.084
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.245
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
; 
 Flack x determined using 914 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.014(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0299P)^2^+0.3751P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2490
_reflns_number_total             3131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01954e3.cif
_cod_data_source_block           JRV380B_a
_cod_database_code               1551495
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.357
_shelx_estimated_absorpt_t_max   0.938
_shelx_res_checksum              63423