Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles.
Mo, Dong-Liang; Wink, Donald A.; Anderson, Laura L.; Organic letters 14 (2012) 5180–5183; doi:10.1021/ol3022885

data_1508669
_publ_section_title
;
 Preparation and rearrangement of N-vinyl nitrones: synthesis of
 spiroisoxazolines and fluorene-tethered isoxazoles.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5180
_journal_page_last               5183
_journal_paper_doi               10.1021/ol3022885
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C25 H22 N2 O3'
_chemical_formula_sum            'C25 H22 N2 O3'
_chemical_formula_weight         398.45
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.697(3)
_cell_angle_beta                 97.648(3)
_cell_angle_gamma                96.324(3)
_cell_formula_units_Z            4
_cell_length_a                   12.4131(19)
_cell_length_b                   12.868(2)
_cell_length_c                   13.645(2)
_cell_measurement_temperature    298(2)
_cell_volume                     2136.7(6)
_computing_cell_refinement       'SAINT (Bruker)'
_computing_data_collection       'SMART (Bruker)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.910
_diffrn_measured_fraction_theta_max 0.910
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19969
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9798
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         9610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1686
_refine_ls_R_factor_gt           0.0745
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1501P)^2^+0.2728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2274
_refine_ls_wR_factor_ref         0.3084
_reflns_number_gt                4018
_reflns_number_total             9610
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3022885_si_002.cif
_cod_data_source_block           Compound8m
_cod_original_cell_volume        2136.6(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508669