An umpolung approach toward N-aryl nitrone construction: a phosphine-mediated addition of 1,2-dicarbonyls to nitroso electrophiles
Aditi P. Chavannavar; Allen G. Oliver; Brandon L. Ashfeld; Chem.Commun. 50 (2014) 10853–; doi:10.1039/C4cc05044D

data_7115611
_publ_section_title
;
 An umpolung approach toward N-aryl nitrone construction: a
 phosphine-mediated addition of 1,2-dicarbonyls to nitroso electrophiles
;
_journal_name_full               Chem.Commun.
_journal_page_first              10853
_journal_paper_doi               10.1039/C4cc05044D
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C15 H12 F N O3'
_chemical_formula_sum            'C15 H12 F N O3'
_chemical_formula_weight         273.26
_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     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90.7253(19)
_cell_angle_beta                 108.2012(17)
_cell_angle_gamma                106.1890(19)
_cell_formula_units_Z            4
_cell_length_a                   10.1802(5)
_cell_length_b                   10.4053(5)
_cell_length_c                   13.1475(6)
_cell_measurement_reflns_used    7933
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.20
_cell_volume                     1262.93(11)
_computing_cell_refinement       'Bruker SAINT v8.32B'
_computing_data_collection       'Bruker APEX-II v2013-10.0'
_computing_data_reduction        'Bruker SAINT v8.32B'
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_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of \w and \f-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  0.0199
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.712
_diffrn_reflns_theta_min         1.640
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.0000
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_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 20080'
_exptl_crystal_colour            colorless
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_exptl_crystal_description       plate
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_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.4513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                4389
_reflns_number_total             5348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc05044d2.cif
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_cod_database_code               7115611
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2014-3
_shelx_res_checksum              30683