Enantioselective Organocatalytic Michael Additions of N,N'-Dialkylbarbituric Acids to Enones
Liu, Ying; Zhang, Yongna; Duan, Hui-Xin; Wanyan, Dong-Yan; Wang, You-Qing; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02116J

data_7155903
_publ_section_title
;
 Enantioselective Organocatalytic Michael Additions of
 N,N'-Dialkylbarbituric Acids to Enones
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02116J
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source
1,3-di-tert-butylpyrimidine-2,4,6(1H,3H,5H)-trione/3-(4-chlorophenyl)-1-(p-tolyl)propan-1-one
_chemical_formula_sum            'C28 H33 Cl N2 O4'
_chemical_formula_weight         497.01
_chemical_melting_point          140.6
_chemical_name_common
1,3-di-tert-butyl-5-(1-(4-chlorophenyl)-3-oxo-3-(p-tolyl)propyl)pyrimidine-2,4,6(1H,3H,5H)-trione
_chemical_name_systematic
1,3-di-tert-butyl-5-(1-(4-chlorophenyl)-3-oxo-3-(p-tolyl)propyl)pyrimidine-2,4,6(1H,3H,5H)-trione
_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
_audit_update_record
;
2017-01-18 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.324(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.660(4)
_cell_length_b                   9.536(4)
_cell_length_c                   13.873(5)
_cell_measurement_reflns_used    2340
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      18.517
_cell_measurement_theta_min      2.632
_cell_volume                     1346.3(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD area detector'
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13894
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9279
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0249P)^2^+1.0523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                3422
_reflns_number_total             4455
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02116j2.cif
_cod_data_source_block           mpt9849_0m
_cod_original_cell_volume        1346.2(8)
_cod_original_sg_symbol_H-M      P21
_cod_original_formula_moiety     497.03
_cod_database_code               7155903