Copper-Catalyzed Aerobic Oxidation of Hydroxamic Acids Leads to a Mild and Versatile Acylnitroso Ene Reaction
Charles P. Frazier; Jarred R. Engelking; Javier Read de Alaniz; Journal of the American Chemical Society 133 (2011) 10430–10433; doi:10.1021/ja204603u

data_4106397
_publ_section_title
;
 Copper-Catalyzed Aerobic Oxidation of Hydroxamic Acids Leads to a Mild
 and Versatile Acylnitroso Ene Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10430
_journal_page_last               10433
_journal_paper_doi               10.1021/ja204603u
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 97.069(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2292(4)
_cell_length_b                   13.0040(8)
_cell_length_c                   15.5592(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1250.79(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10680
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0047(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.515
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.515
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.1662
_reflns_number_gt                3736
_reflns_number_total             3817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja204603u_si_002.cif
_cod_data_source_block           j03032011_0m
_cod_original_cell_volume        1250.78(14)
_cod_database_code               4106397