Oxidation of oximes to nitrile oxides with hypervalent iodine reagents.
Mendelsohn, Brian A.; Lee, Shelley; Kim, Simon; Teyssier, Florian; Aulakh, Virender S.; Ciufolini, Marco A.; Organic letters 11 (2009) 1539–1542; doi:10.1021/ol900194v

data_1503824
_publ_section_title
;
 Oxidation of oximes to nitrile oxides with hypervalent iodine reagents.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1539
_journal_page_last               1542
_journal_paper_doi               10.1021/ol900194v
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C11 H12 N2 O3'
_chemical_formula_weight         220.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.696(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4372(4)
_cell_length_b                   7.6194(3)
_cell_length_c                   18.2141(9)
_cell_measurement_reflns_used    6401
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.74
_cell_volume                     1031.00(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_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    0.0244
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12044
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.3215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                2132
_reflns_number_total             2466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900194v_si_001.cif
_cod_data_source_block           mc017
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503824