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_7230581
_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_absolute_configuration ad
_chemical_formula_moiety         'C15 H12 Br N O'
_chemical_formula_sum            'C15 H0 Br N O'
_chemical_formula_weight         290.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.29(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.72(4)
_cell_length_b                   5.675(7)
_cell_length_c                   7.425(9)
_cell_measurement_reflns_used    2326
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.75
_cell_volume                     1247(3)
_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      293.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0840
_diffrn_reflns_av_unetI/netI     0.1069
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4021
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.38
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.280
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10312
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.492
_refine_diff_density_min         -0.965
_refine_diff_density_rms         0.218
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0727
_refine_ls_shift/su_max          0.173
_refine_ls_shift/su_mean         0.034
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1440P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2171
_reflns_number_gt                1538
_reflns_number_total             2051
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8gc00630j2.cif
_cod_data_source_block           aaaa
_cod_depositor_comments
'Adding full bibliography for 7230581--7230582.cif.'
_cod_database_code               7230581
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.93(3)
 0.07(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C13(H13), C17(H17), C28(H28), C31(H31), C35(H35),
 C41(H41)
;
_olex2_submission_special_instructions 'No special instructions were received'