Gold-Catalyzed Simultaneous Formation of C-C, C=O, and C-F bonds in the Presence of Selectfluor: A Synthesis of Fluoroindenes from Allene Esters
Yunkui Liu; Jie Zhu; Jianqiang Qian; Zhenyuan Xu; Journal of Organic Chemistry 77 (2012) 5411–5417; doi:10.1021/jo3006528

data_4027242
_publ_section_title
;
 Gold-Catalyzed Simultaneous Formation of C-C, C=O, and C-F bonds in the
 Presence of Selectfluor: A Synthesis of Fluoroindenes from Allene Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5411
_journal_page_last               5417
_journal_paper_doi               10.1021/jo3006528
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C14 H12 Cl F O3'
_chemical_formula_sum            'C14 H12 Cl F O3'
_chemical_formula_weight         282.69
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.555(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1890(6)
_cell_length_b                   7.1850(5)
_cell_length_c                   11.2590(7)
_cell_measurement_reflns_used    3934
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     661.18(8)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rolling anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6553
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_correction_T_min  0.8764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       chunk
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, Friedel pairs  1270'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0405P)^2^+0.6556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                1454
_reflns_number_total             2906
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3006528_si_002.cif
_cod_data_source_block           zj178
_cod_database_code               4027242