Iron(iii)-catalyzed selective N–O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from N-vinyl-α,β-unsaturated ketonitrones
Chen, Chun-Hua; Wu, Qing-Yan; Wei, Cui; Liang, Cui; Su, Gui-Fa; Mo, Dong-Liang; Green Chemistry 20 (2018) 2722–; doi:10.1039/C8GC00630J

data_7230582
_publ_section_title
;
 Iron(iii)-catalyzed selective N--O bond cleavage to prepare
 tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from
 N-vinyl-\a,\b-unsaturated ketonitrones
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              2722
_journal_paper_doi               10.1039/C8GC00630J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C20 H16 F3 N'
_chemical_formula_sum            'C20 H16 F3 N'
_chemical_formula_weight         327.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2017-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-01-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                91.079(3)
_cell_angle_beta                 103.819(3)
_cell_angle_gamma                90.728(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5850(15)
_cell_length_b                   9.8690(17)
_cell_length_c                   10.0994(17)
_cell_measurement_reflns_used    4409
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.80
_cell_volume                     830.6(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9632
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.06
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.414
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.928
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.1156
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3948
_refine_ls_wR_factor_ref         0.4283
_reflns_number_gt                2663
_reflns_number_total             3406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8gc00630j2.cif
_cod_data_source_block           aaaa_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7230581--7230582.cif.'
_cod_database_code               7230582
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C19(H19), C15(H15), C17(H17), C16(H16), C18(H18), C11(H11), C8(H8),
 C7(H7), C10(H10)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'