Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization
Niemeyer, Zachary L.; Pindi, Suresh; Khrakovsky, Dimitri A.; Kuzniewski, Christian N.; Hong, Cynthia M.; Joyce, Leo A.; Sigman, Matthew S.; Toste, F. Dean; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b08791

data_4126373
_publ_section_title
;
 Parameterization of Acyclic Diaminocarbene Ligands Applied to a
 Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b08791
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C70 H68 Au2 Cl2 F12 N6 O2'
_chemical_formula_weight         1718.13
_chemical_name_common            cmh_sp_1027
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                99.429(3)
_cell_angle_beta                 103.897(2)
_cell_angle_gamma                101.439(2)
_cell_formula_units_Z            1
_cell_length_a                   11.2332(15)
_cell_length_b                   13.4974(18)
_cell_length_c                   13.5685(18)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      2.47
_cell_volume                     1908.4(4)
_computing_cell_refinement       'Bruker SAINT V8.34A'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT V8.34a'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13583
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.375
_diffrn_reflns_theta_min         1.579
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    3.983
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             846
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         2.007
_refine_diff_density_min         -4.438
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details
;
 Flack x determined using 5984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     824
_refine_ls_number_reflns         13583
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          3.870
_refine_ls_shift/su_mean         0.164
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+4.4589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.981
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                13005
_reflns_number_total             13583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08791_si_001.cif
_cod_data_source_block           shelx
_cod_database_code               4126373
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.692
_shelx_estimated_absorpt_t_max   0.692
_shelx_res_checksum              14629
_shelx_hkl_checksum              5357
_shelx_fab_checksum              32297