Gold-Catalyzed Formal [3 + 3] and [4 + 2] Cycloaddition Reactions of Nitrosobenzenes with Alkenylgold Carbenoids
Vinayak Vishnu Pagar; Appaso Mahadev Jadhav; Rai-Shung Liu; Journal of the American Chemical Society 133 (2011) 20728–20731; doi:10.1021/ja209980d

data_4107267
_publ_section_title
;
 Gold-Catalyzed Formal [3 + 3] and [4 + 2] Cycloaddition Reactions of
 Nitrosobenzenes with Alkenylgold Carbenoids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20728
_journal_page_last               20731
_journal_paper_doi               10.1021/ja209980d
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C24 H22 N2 O3'
_chemical_formula_weight         386.44
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 99.2420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.1039(10)
_cell_length_b                   10.4762(6)
_cell_length_c                   22.3799(12)
_cell_measurement_reflns_used    3347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.6799
_cell_measurement_theta_min      2.2535
_cell_volume                     4189.5(4)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3666
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13237
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+1.4653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                3161
_reflns_number_total             4287
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja209980d_si_002.cif
_cod_data_source_block           110650m
_cod_database_code               4107267