Electrophilic α-oxygenation reaction of β-ketoesters using N-hydroxycarbamates: control of the ambident reactivity of nitrosoformate intermediates
Frazier, Charles P.; Sandoval, David; Palmer, Leoni I.; Read de Alaniz, Javier; Chemical Science 4 (2013) 3857–; doi:10.1039/c3sc51658j

data_1514534
_publ_section_title
;
 Electrophilic \a-oxygenation reaction of \b-ketoesters using
 N-hydroxycarbamates: control of the ambident reactivity of nitrosoformate
 intermediates
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              3857
_journal_paper_doi               10.1039/c3sc51658j
_journal_volume                  4
_journal_year                    2013
_chemical_formula_sum            'C16 H25 N O6'
_chemical_formula_weight         327.37
_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                 92.813(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8524(4)
_cell_length_b                   15.9675(5)
_cell_length_c                   10.5673(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1660.43(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa Apex'
_diffrn_measurement_method       'omega scan'
_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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13745
_diffrn_reflns_theta_full        27.17
_diffrn_reflns_theta_max         27.17
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.8586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                3345
_reflns_number_total             3678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc51658j.txt
_cod_data_source_block           l10192012_0m
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1514534