Three-Component Heterocyclization ofgem-Bromofluorocyclopropanes with NOBF4: Access to 4-Fluoropyrimidine N-Oxides
Kseniya N. Sedenkova; Elena B. Averina; Yuri K. Grishin; Andrei G. Kutateladze; Victor B. Rybakov; Tamara S. Kuznetsova; Nikolay S. Zefirov; Journal of Organic Chemistry 77 (2012) 9893–9899; doi:10.1021/jo301880m

data_4027681
_publ_section_title
;
 Three-Component Heterocyclization ofgem-Bromofluorocyclopropanes with
 NOBF4: Access to 4-Fluoropyrimidine N-Oxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9893
_journal_page_last               9899
_journal_paper_doi               10.1021/jo301880m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C15 H14 F N5 O8'
_chemical_formula_weight         411.31
_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                 104.283(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.4647(5)
_cell_length_b                   20.6943(6)
_cell_length_c                   17.0214(7)
_cell_measurement_temperature    295(2)
_cell_volume                     3913.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1165
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7307
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9763
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.710
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         7307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.710
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0257P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                2569
_reflns_number_total             7307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301880m_si_003.cif
_cod_data_source_block           aver15
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027681