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_1514533
_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_absolute_configuration ad
_chemical_formula_sum            'C27 H23 Br2 N O6'
_chemical_formula_weight         617.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.939(4)
_cell_length_b                   18.900(9)
_cell_length_c                   19.529(11)
_cell_measurement_temperature    100(2)
_cell_volume                     2561(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.2219
_diffrn_reflns_av_sigmaI/netI    0.3125
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12302
_diffrn_reflns_theta_full        24.11
_diffrn_reflns_theta_max         24.11
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    3.208
_exptl_absorpt_correction_T_max  0.9386
_exptl_absorpt_correction_T_min  0.4462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.806
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.168
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0041(10)
_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   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.2205
_refine_ls_R_factor_gt           0.0951
_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^)+(0.0894P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1869
_refine_ls_wR_factor_ref         0.2325
_reflns_number_gt                1863
_reflns_number_total             4039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc51658j.txt
_cod_data_source_block           d02282013_0m
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1514533