Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to alpha-hydroxy-N-acyl-carbamides
Michal Szostak; Brice Sautier; David J. Procter; Chem.Commun. 50 (2014) 2518–; doi:10.1039/c3cc48932a

data_7112036
_publ_section_title
;
 Structural analysis and reactivity of unusual tetrahedral intermediates
 enabled by SmI2-mediated reduction of barbituric acids: vinylogous
 N-acyliminium additions to alpha-hydroxy-N-acyl-carbamides
;
_journal_name_full               Chem.Commun.
_journal_page_first              2518
_journal_paper_doi               10.1039/c3cc48932a
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C12 H18 N2 O3'
_chemical_formula_weight         238.28
_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                 93.726(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3649(4)
_cell_length_b                   6.9926(4)
_cell_length_c                   19.9506(10)
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.92
_cell_measurement_theta_min      5.30
_cell_volume                     1164.49(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7587
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         72.96
_diffrn_reflns_theta_min         5.30
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_correction_T_min  0.660645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.520
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.1005
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1622P)^2^+2.6929P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2615
_refine_ls_wR_factor_ref         0.2736
_reflns_number_gt                1897
_reflns_number_total             2266
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48932a.txt
_cod_data_source_block           s3799ma
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7112036