Novel Synthesis of 7-Fluoro-8-(trifluoromethyl)-1H-1,6-naphthyridin-4-one Derivatives: Intermolecular Cyclization of an N-Silyl-1-azaallyl Anion with Perfluoroalkene and Subsequent Intramolecular Skeletal Transformation of the Resulting Pentasubstituted Pyridines
Hiroyuki Suzuki; Norio Sakai; Ryohei Iwahara; Takayuki Fujiwaka; Mitsunobu Satoh; Akikazu Kakehi; Takeo Konakahara; Journal of Organic Chemistry 72 (2007) 5878–5881; doi:10.1021/jo070564m

data_4024062
_publ_section_title
;
 Novel Synthesis of 7-Fluoro-8-(trifluoromethyl)-1H-1,6-naphthyridin-4-one
 Derivatives: Intermolecular Cyclization of an N-Silyl-1-azaallyl
 Anion with Perfluoroalkene and Subsequent Intramolecular Skeletal
 Transformation of the Resulting Pentasubstituted Pyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5878
_journal_page_last               5881
_journal_paper_doi               10.1021/jo070564m
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H9 F9 N2 O'
_chemical_formula_weight         392.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.986(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.563(4)
_cell_length_b                   9.543(4)
_cell_length_c                   15.602(6)
_cell_measurement_reflns_used    1702
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.98
_cell_measurement_theta_min      2.53
_cell_volume                     1504.2(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8879
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  -183
_exptl_absorpt_correction_T_min  -183
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.221
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.1017
_refine_ls_shift/su_max          0.175
_refine_ls_shift/su_mean         0.033
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1848P)^2^+4.7989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2729
_refine_ls_wR_factor_ref         0.3046
_reflns_number_gt                2448
_reflns_number_total             3401
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070564msi20070514_030735.cif
_cod_data_source_block           r10i
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024062