Photooxygenation of 5-Dialkylamino-4-pyrrolin-3-ones. Synthesis of Highly Functionalized Ureas, 2-Oxazolidinones, and 2-Oxazolinones
Ihsan Erden; Galip Özer; Christophe Hoarau; Weiguo Cao; Jiangao Song; Christian Gärtner; Journal of Organic Chemistry 73 (2008) 6943–6945; doi:10.1021/jo801192z

data_4023659
_publ_section_title
;
 Photooxygenation of 5-Dialkylamino-4-pyrrolin-3-ones. Synthesis of
 Highly Functionalized Ureas, 2-Oxazolidinones, and 2-Oxazolinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6943
_journal_page_last               6945
_journal_paper_doi               10.1021/jo801192z
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C17 H20 N2 O5'
_chemical_formula_weight         332.35
_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                 90.46(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.800(4)
_cell_length_b                   35.181(14)
_cell_length_c                   10.149(7)
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.91
_cell_measurement_theta_min      2.21
_cell_volume                     3499(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       psi-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  0.1157
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            39775
_diffrn_reflns_theta_full        24.21
_diffrn_reflns_theta_max         24.21
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         5575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0799
_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^)+(0.1056P)^2^+2.2158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2261
_reflns_number_gt                3083
_reflns_number_total             5575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801192z_si_002.cif
_cod_data_source_block           sort
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023659