Five-to-Six Membered Ring-Rearrangements in the Reaction of 5-Perfluoroalkyl-1,2,4-oxadiazoles with Hydrazine and Methylhydrazine
Silvestre Buscemi; Andrea Pace; Antonio Palumbo Piccionello; Ivana Pibiri; Nicoló Vivona; Gianluca Giorgi; Andrea Mazzanti; Domenico Spinelli; Journal of Organic Chemistry 71 (2006) 8106–8113; doi:10.1021/jo061251e

data_4022012
_publ_contact_author_address
;     Dipartimento di Chimica Organica "E. Patern\`o"
    Universit\`a degli Studi di Palermo, 
    Viale delle Scienze - Parco d'Orleans II
      I-90128 Palermo
      Italy 
;
_publ_contact_author_email       sbuscemi@unipa.it
_publ_contact_author_name        'Silvestre Buscemi'
_publ_section_title
;
 Five-to-Six Membered Ring-Rearrangements in the Reaction of
 5-Perfluoroalkyl-1,2,4-oxadiazoles with Hydrazine and Methylhydrazine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8106
_journal_page_last               8113
_journal_paper_doi               10.1021/jo061251e
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C11 H4 F15 N4 O2, C2 H6 O'
_chemical_formula_sum            'C13 H10 F15 N4 O3'
_chemical_formula_weight         555.26
_chemical_name_systematic
;
1-N-methyl-5-hydroxylamino-3-pentadecafluoroheptyl-1,2,4-triazin-6-one
;
_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                 102.160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.267(2)
_cell_length_b                   40.867(8)
_cell_length_c                   9.623(2)
_cell_measurement_reflns_used    42
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.5
_cell_measurement_theta_min      3.0
_cell_volume                     2024.8(10)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.808
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w 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  0.1180
_diffrn_reflns_av_sigmaI/netI    0.2493
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4215
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.99
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    geom
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.3206
_refine_ls_R_factor_gt           0.1088
_refine_ls_shift/su_max          0.877
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1007P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2149
_refine_ls_wR_factor_ref         0.3066
_reflns_number_gt                832
_reflns_number_total             2878
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061251esi_2.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022012