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_4119815
_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            'C28 H24 N O4.5'
_chemical_formula_weight         446.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 94.2700(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6947(2)
_cell_length_b                   6.93150(10)
_cell_length_c                   31.4287(6)
_cell_measurement_reflns_used    7303
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.39
_cell_volume                     2323.35(7)
_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      153(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.940
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            20306
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6664
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0800P)^2^+0.5798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1521
_reflns_number_gt                5151
_reflns_number_total             6664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4032727_si_002.cif
_cod_data_source_block           chan212s
_cod_original_formula_sum        'C28 H24 N O4.50'
_cod_database_code               4119815