Potassiumtert-Butoxide Promoted Annulation of 2-Alkynylphenyl Propargyl Ethers: Selective Synthesis of Benzofuran and 12H-Benzoannulene Derivatives
Tamiris B. Grimaldi; Davi F. Back; Gilson Zeni; Journal of Organic Chemistry 78 (2013) 11017–11031; doi:10.1021/jo4020062

data_4028737
_publ_section_title
;
 Potassiumtert-Butoxide Promoted Annulation of 2-Alkynylphenyl Propargyl
 Ethers: Selective Synthesis of Benzofuran and 12H-Benzoannulene
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11017
_journal_page_last               11031
_journal_paper_doi               10.1021/jo4020062
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C23 H16 O'
_chemical_formula_weight         308.36
_chemical_melting_point          398
_chemical_name_common            12H-benzo-7-phenyl[7]annulen-6-benzo[b]furan
_chemical_name_systematic
;
 12H-benzo-7-phenyl[7]annulen-6-benzo[b]furan
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2013-07-19T12:18:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.719(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.9774(10)
_cell_length_b                   8.8710(4)
_cell_length_c                   17.3971(9)
_cell_measurement_reflns_used    3731
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.1425
_cell_measurement_theta_min      2.493
_cell_volume                     3236.0(3)
_computing_cell_refinement       'BRUKER SANT'
_computing_data_collection       'BRUKER APEX-II'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'X8 APEX II'
_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  0.0781
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            50699
_diffrn_reflns_theta_full        27.2
_diffrn_reflns_theta_max         27.2
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0044(6)
_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   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         7162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                3202
_reflns_number_total             7162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4020062_si_003.cif
_cod_data_source_block           teste1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_database_code               4028737