Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines.
Kokuev, Aleksandr O.; Antonova, Yulia A.; Dorokhov, Valentin S.; Golovanov, Ivan S.; Nelyubina, Yulia V.; Tabolin, Andrey A.; Sukhorukov, Alexey Yu; Ioffe, Sema L.; The Journal of organic chemistry 83 (2018) 11057–11066; doi:10.1021/acs.joc.8b01652

data_4035657
_publ_section_title
;
 Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ
 Generated N-Acyloxy, N-oxyenamines.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11057
_journal_page_last               11066
_journal_paper_doi               10.1021/acs.joc.8b01652
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H21 N O4'
_chemical_formula_sum            'C16 H21 N O4'
_chemical_formula_weight         291.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 109.329(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.614(6)
_cell_length_b                   10.485(4)
_cell_length_c                   11.854(5)
_cell_measurement_reflns_used    1854
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1596.7(12)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX2 DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36584
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_min         2.507
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.4425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2302
_reflns_number_total             3482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01652_si_003.cif
_cod_data_source_block           ka104
_cod_original_cell_volume        1596.7(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035657
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2014/6
_shelx_res_checksum              20218
_shelx_hkl_checksum              69743