Synthesis and Catalytic Activity of Gold Chiral Nitrogen Acyclic Carbenes and Gold Hydrogen Bonded Heterocyclic Carbenes in Cyclopropanation of Vinyl Arenes and in Intramolecular Hydroalkoxylation of Allenes
Camino Bartolomé; Domingo García-Cuadrado; Zoraida Ramiro; Pablo Espinet; Inorganic Chemistry 49 (2010) 9758–9764; doi:10.1021/ic101059c

data_4316918
_publ_contact_author
;
 Camino Bartolome
 IU CINQUIMA/Quimica Inorganica
 Facultad de Ciencias
 Universidad de Valladolid
 E47071
 Valladolid
 Spain
;
_publ_contact_author_email       caminob@qi.uva.es
_publ_contact_author_fax         '+34 983 186350'
_publ_contact_author_phone       '+34 983 186342'
_publ_section_title
;
 Synthesis and Catalytic Activity of Gold Chiral Nitrogen Acyclic Carbenes
 and Gold Hydrogen Bonded Heterocyclic Carbenes in Cyclopropanation of
 Vinyl Arenes and in Intramolecular Hydroalkoxylation of Allenes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9758
_journal_page_last               9764
_journal_paper_doi               10.1021/ic101059c
_journal_volume                  49
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H15 Au Cl N3'
_chemical_formula_weight         457.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.6832(2)
_cell_length_b                   16.2667(3)
_cell_length_c                   19.8061(4)
_cell_measurement_reflns_used    18583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4914
_cell_measurement_theta_min      2.9360
_cell_volume                     3119.73(11)
_computing_cell_refinement
; 
'Thu Nov 05 17:38:08 2009' 
;
_computing_data_collection
; 
'Thu Nov 05 17:38:08 2009' 
;
_computing_data_reduction
; 
'Thu Nov 05 17:38:08 2009' 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4757
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -59.00  -29.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -11.4741  128.0000  -98.0000 30

  2 omega  -53.00   27.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       12.4116  -37.0000  120.0000 80

  3 omega   31.00   91.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       12.4116   77.0000 -180.0000 60

  4 omega  -45.00   67.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -11.4741   77.0000 -120.0000 112

  5 omega  -32.00   27.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -11.4741  -90.0000   79.0000 59

  6 omega  -33.00   50.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       12.4116  -88.0000   42.0000 83

;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31001
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    9.592
_exptl_absorpt_correction_T_max  0.697
_exptl_absorpt_correction_T_min  0.262
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.949
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             1727
_exptl_crystal_size_max          0.3345
_exptl_crystal_size_mid          0.3196
_exptl_crystal_size_min          0.0834
_refine_diff_density_max         1.753
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                5561
_reflns_number_total             6368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101059c_si_001_1.cif
_cod_data_source_block           2
_cod_database_code               4316918
_cell_oxdiff_length_a            9.6825(2)
_cell_oxdiff_length_b            16.2659(3)
_cell_oxdiff_length_c            19.8085(5)
_cell_oxdiff_angle_alpha         90.000(2)
_cell_oxdiff_angle_beta          90.006(2)
_cell_oxdiff_angle_gamma         90.0391(19)
_cell_oxdiff_volume              3119.73(13)
_cell_oxdiff_measurement_reflns_used 18583