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_7112035
_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            'C17 H30 N2 O3 Si'
_chemical_formula_weight         338.52
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   24.0386(14)
_cell_length_b                   17.4493(11)
_cell_length_c                   18.3975(13)
_cell_measurement_reflns_used    1577
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.12
_cell_measurement_theta_min      3.13
_cell_volume                     7717.0(9)
_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 0.944
_diffrn_measured_fraction_theta_max 0.918
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.2104
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13438
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         69.89
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  0.9209
_exptl_absorpt_correction_T_min  0.628481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2944
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     862
_refine_ls_number_reflns         13438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1642
_refine_ls_R_factor_gt           0.0912
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1072P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2155
_refine_ls_wR_factor_ref         0.2779
_reflns_number_gt                7400
_reflns_number_total             13438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48932a.txt
_cod_data_source_block           s3814pat5
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7112035