Axially Chiral Triazoloisoquinolin-3-ylidene Ligands in Gold(I)-Catalyzed Asymmetric Intermolecular (4 + 2) Cycloadditions of Allenamides and Dienes
Javier Francos; Francisca Grande-Carmona; Hélio Faustino; Javier Iglesias-Sigüenza; Elena Díez; Isaac Alonso; Rosario Fernández; José M. Lassaletta; Fernando López; José L. Mascareñas; Journal of the American Chemical Society 134 (2012) 14322–14325; doi:10.1021/ja3065446

data_4118579
_publ_section_title
;
 Axially Chiral Triazoloisoquinolin-3-ylidene Ligands in Gold(I)-Catalyzed
 Asymmetric Intermolecular (4 + 2) Cycloadditions of Allenamides and
 Dienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14322
_journal_page_last               14325
_journal_paper_doi               10.1021/ja3065446
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C36 H37 Au Cl N3'
_chemical_formula_sum            'C36 H37 Au Cl N3'
_chemical_formula_weight         744.11
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           21
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      21
_symmetry_space_group_name_Hall  'C 2 2'
_symmetry_space_group_name_H-M   'C 2 2 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-05-24T13:44:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.428(4)
_cell_length_b                   27.216(4)
_cell_length_c                   12.0685(18)
_cell_measurement_reflns_used    1973
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.24
_cell_measurement_wavelength     0.71073
_cell_volume                     8024(2)
_computing_cell_refinement       'BRUKER Smart'
_computing_data_collection       'BRUKER Smart'
_computing_data_reduction        'BRUKER Saint'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'DIRDIF99 ( Beurskens et al, 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46289
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    3.756
_exptl_absorpt_correction_T_max  0.6880
_exptl_absorpt_correction_T_min  0.5200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       prism
_exptl_crystal_F_000             2960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
;
_refine_diff_density_max         0.807
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.022(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         7921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+15.2951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.069
_reflns_number_gt                7200
_reflns_number_total             7921
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja3065446_si_002.cif
_cod_data_source_block           JF116
_cod_database_code               4118579