Synthesis of imidazolidin-2-one-4-carboxylate and of (tetrahydro)pyrimidin-2-one-5-carboxylate via an efficient modification of the Hofmann rearrangement
Angelici, Gaetano; Contaldi, Simone; Lynn Green, Sarah; Tomasini, Claudia; Organic & Biomolecular Chemistry 6 (2008) 1849–1852; doi:10.1039/b801909f

data_7150896
_publ_section_title
;
 Synthesis of imidazolidin-2-one-4-carboxylate and of
 (tetrahydro)pyrimidin-2-one-5-carboxylate via an efficient
 modification of the Hofmann rearrangement
;
_journal_issue                   10
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              1849
_journal_page_last               1852
_journal_paper_doi               10.1039/b801909f
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration 'syn R'
_chemical_formula_sum            'C13 H14 N2 O5'
_chemical_formula_weight         278.26
_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                 118.0930(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6240(11)
_cell_length_b                   7.9566(9)
_cell_length_c                   9.8099(11)
_cell_measurement_temperature    296(2)
_cell_volume                     662.68(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'SCHAKAL-99 (Keller, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Giacovazzo, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_method       'phi and omega scans'
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5616
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1655
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                1433
_reflns_number_total             1655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b801909f.txt
_cod_data_source_block           compd2a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7150896