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_4024063
_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            'C12 H10 F4 N2 O'
_chemical_formula_weight         274.22
_chemical_name_systematic
; 
 ? 
;
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.790(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1074(14)
_cell_length_b                   17.390(5)
_cell_length_c                   12.980(3)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.34
_cell_volume                     1132.5(5)
_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 0.924
_diffrn_measured_fraction_theta_max 0.924
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6710
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0865P)^2^+0.3845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                2136
_reflns_number_total             2600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070564msi20070514_030908.cif
_cod_data_source_block           r20i
_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/c'
_cod_database_code               4024063