Bi(III)-Catalyzed Intermolecular Reactions of (Z)-Pent-2-en-4-yl Acetates with Ethynylarenes for the Construction of Multisubstituted Fluorene Skeletons through a Cascade Electrophilic Addition/Cycloisomerization Sequence
Xiang-Chuan Wang; Ru-Long Yan; Mei-Jin Zhong; Yong-Min Liang; Journal of Organic Chemistry 77 (2012) 2064–2068; doi:10.1021/jo202607z

data_4026992
_publ_section_title
;
 Bi(III)-Catalyzed Intermolecular Reactions of (Z)-Pent-2-en-4-yl Acetates
 with Ethynylarenes for the Construction of Multisubstituted Fluorene
 Skeletons through a Cascade Electrophilic Addition/Cycloisomerization
 Sequence
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2064
_journal_page_last               2068
_journal_paper_doi               10.1021/jo202607z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C34 H25 N O'
_chemical_formula_weight         463.55
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 97.721(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.739(8)
_cell_length_b                   15.319(10)
_cell_length_c                   28.17(2)
_cell_measurement_reflns_used    1270
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.32
_cell_measurement_theta_min      2.24
_cell_volume                     5020(6)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0822
_diffrn_reflns_av_sigmaI/netI    0.1142
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10759
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00039(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.2166
_refine_ls_R_factor_gt           0.0815
_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^)+(0.0668P)^2^+10.9041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.2483
_reflns_number_gt                1750
_reflns_number_total             4617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202607z_si_002.cif
_cod_data_source_block           c2c
_cod_original_cell_volume        5021(6)
_cod_database_code               4026992