Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1H-fluorenes
Weidong Rao; Ming Joo Koh; Dan Li; Hajime Hirao; Philip Wai Hong Chan; Journal of the American Chemical Society 135 (2013) 7926–7932; doi:10.1021/ja4032727

data_4119818
_publ_section_title
;
 Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to
 2,4a-Dihydro-1H-fluorenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7926
_journal_page_last               7932
_journal_paper_doi               10.1021/ja4032727
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C35.5 H57 Au Cl F6 N P Sb'
_chemical_formula_weight         996.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.1340(10)
_cell_angle_beta                 84.9200(10)
_cell_angle_gamma                84.2460(10)
_cell_formula_units_Z            4
_cell_length_a                   8.7642(2)
_cell_length_b                   19.0150(4)
_cell_length_c                   23.7599(5)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      30.91
_cell_measurement_theta_min      2.34
_cell_volume                     3923.07(15)
_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      103(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            76174
_diffrn_reflns_theta_full        31.01
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    4.586
_exptl_absorpt_correction_T_max  0.6570
_exptl_absorpt_correction_T_min  0.2613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_description       prism
_exptl_crystal_F_000             1972
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.389
_refine_diff_density_min         -1.726
_refine_diff_density_rms         0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1046
_refine_ls_number_reflns         24949
_refine_ls_number_restraints     696
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+0.3148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                19736
_reflns_number_total             24949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4032727_si_005.cif
_cod_data_source_block           chan192s
_cod_original_formula_sum        'C35.50 H57 Au Cl F6 N P Sb'
_cod_database_code               4119818