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_4027680
_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_moiety         'C18 H22 Cl2 Cu F2 N4 O2'
_chemical_formula_sum            'C18 H22 Cl2 Cu F2 N4 O2'
_chemical_formula_weight         498.84
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.773(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.0434(3)
_cell_length_b                   15.9831(7)
_cell_length_c                   9.6404(4)
_cell_measurement_reflns_used    3352
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      3.13
_cell_volume                     1021.28(8)
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_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  0.0920
_diffrn_reflns_av_sigmaI/netI    0.1406
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3352
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    1.371
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.775
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.775
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0475P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                1056
_reflns_number_total             1911
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo301880m_si_002.cif
_cod_data_source_block           aver14
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027680