Gold-catalyzed cycloisomerization of 1,6-diyne esters to 1H-cyclopenta[b]naphthalenes, cis-cyclopenten-2-yl δ-diketones, and bicyclo[3.2.0]hepta-1,5-dienes.
Li, Dan; Rao, Weidong; Tay, Guan Liang; Ayers, Benjamin James; Chan, Philip Wai Hong; The Journal of organic chemistry 79 (2014) 11301–11315; doi:10.1021/jo5020195

data_4030060
_publ_section_title
;
 Gold-catalyzed cycloisomerization of 1,6-diyne esters to
 1H-cyclopenta[b]naphthalenes, cis-cyclopenten-2-yl \d-diketones, and
 bicyclo[3.2.0]hepta-1,5-dienes.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11301
_journal_page_last               11315
_journal_paper_doi               10.1021/jo5020195
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C27 H21 F O2, 0.15(H2 O)'
_chemical_formula_sum            'C27 H21.3 F O2.15'
_chemical_formula_weight         396.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 100.506(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4017(6)
_cell_length_b                   9.8934(5)
_cell_length_c                   20.6445(12)
_cell_measurement_reflns_used    8377
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      30.9808
_cell_measurement_theta_min      2.2901
_cell_volume                     2088.9(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            35570
_diffrn_reflns_theta_full        31.15
_diffrn_reflns_theta_max         31.15
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             833
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         6711
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.6269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                5272
_reflns_number_total             6711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5020195_si_009.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4030057--4030064.cif.'
_cod_original_formula_sum        'C27 H21.30 F O2.15'
_cod_database_code               4030060
_shelx_res_checksum              43266
_shelx_hkl_checksum              57712