Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones.
Chen, Xiaoyu; Day, David Philip; Teo, Wan Teng; Chan, Philip Wai Hong; Organic letters 18 (2016) 5936–; doi:10.1021/acs.orglett.6b03049

data_1544394
_publ_section_title
;
 Gold- and Br\/onsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl
 Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5936
_journal_paper_doi               10.1021/acs.orglett.6b03049
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C23 H22 O'
_chemical_formula_weight         314.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                116.215(2)
_cell_angle_beta                 94.594(3)
_cell_angle_gamma                107.174(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6465(7)
_cell_length_b                   11.1436(11)
_cell_length_c                   11.8808(9)
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      27.5473
_cell_measurement_theta_min      2.1925
_cell_volume                     841.15(13)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11521
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.415
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0802P)^2^+0.1138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                3166
_reflns_number_total             4144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03049_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1544394.cif.'
_cod_database_code               1544394
_shelx_res_checksum              16868
_shelx_hkl_checksum              48342