1,6-Carbene Transfer: Gold-Catalyzed Oxidative Diyne Cyclizations
Pascal Nösel; Laura Nunes dos Santos Comprido; Tobias Lauterbach; Matthias Rudolph; Frank Rominger; A. Stephen K. Hashmi; Journal of the American Chemical Society 135 (2013) 15662–15666; doi:10.1021/ja4085385

data_4120970
_publ_contact_author_address
;
        Organisch-Chemisches Institut
        Universit\"at Heidelberg
        Im Neuenheimer Feld 270
        D-69120 Heidelberg
        Germany
;
_publ_contact_author_email       hashmi@hashmi.de
_publ_contact_author_fax         '049 6221 54- 4205'
_publ_contact_author_name        'Hashmi, A. Stephen K.'
_publ_contact_author_phone       '049 6221 54- 8413'
_publ_section_title
;
 1,6-Carbene Transfer: Gold-Catalyzed Oxidative Diyne Cyclizations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15662
_journal_page_last               15666
_journal_paper_doi               10.1021/ja4085385
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C14 H13 I O'
_chemical_formula_weight         324.14
_chemical_name_common            '2a in manuscript'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.725(2)
_cell_angle_beta                 95.624(1)
_cell_angle_gamma                101.077(1)
_cell_formula_units_Z            2
_cell_length_a                   7.4148(2)
_cell_length_b                   8.0910(2)
_cell_length_c                   11.0119(3)
_cell_measurement_reflns_used    6291
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.61
_cell_volume                     633.18(3)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II Quazar'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'ImuS microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8072
_diffrn_reflns_theta_full        28.46
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    2.505
_exptl_absorpt_correction_T_max  0.7877
_exptl_absorpt_correction_T_min  0.5011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+0.5036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0613
_reflns_number_gt                2993
_reflns_number_total             3168
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4085385_si_002_1.cif
_cod_data_source_block           pno20
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