Friedel-Crafts-type cyclization of 2,2-difluorovinyl ketones via alpha-fluorocarbocations and its application in domino cyclizations.
Ichikawa, Junji; Kaneko, Mikio; Yokota, Misaki; Itonaga, Masaaki; Yokoyama, Takaharu; Organic letters 8 (2006) 3167–3170; doi:10.1021/ol060912r

data_1506030
_publ_section_title
;
 Friedel-Crafts-type cyclization of 2,2-difluorovinyl ketones via
 alpha-fluorocarbocations and its application in domino cyclizations.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3167
_journal_page_last               3170
_journal_paper_doi               10.1021/ol060912r
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C24 H20 N2'
_chemical_formula_weight         336.42
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 102.500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.314(2)
_cell_length_b                   20.0240(10)
_cell_length_c                   10.9690(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1782.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2858
_diffrn_reflns_theta_full        60.06
_diffrn_reflns_theta_max         60.06
_diffrn_reflns_theta_min         4.13
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  0.8954
_exptl_absorpt_correction_T_min  0.8489
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.1593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                1994
_reflns_number_total             2651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060912rsi20060414_101733.cif
_cod_data_source_block           cif
_cod_database_code               1506030