Electroreductive Intermolecular Coupling of Uracils with Aromatic Ketones: Synthesis of 6-Substituted and cis-5,6-Disubstituted 5,6-Dihydro-1,3-dimethyluracils and Their Transformation to 6-Substituted 1,3-Dimethyluracils, trans-5,6-Disubstituted 5,6-Dihydro-1,3-dimethyluracils, and 4,5,5-Trisubstituted 3-Methyloxazolizin-2-ones.
Kise, Naoki; Hamada, Yusuke; Sakurai, Toshihiko; The Journal of organic chemistry 81 (2016) 5101–5119; doi:10.1021/acs.joc.6b00670

data_4036839
_publ_section_title
;
 Electroreductive Intermolecular Coupling of Uracils with Aromatic
 Ketones: Synthesis of 6-Substituted and cis-5,6-Disubstituted
 5,6-Dihydro-1,3-dimethyluracils and Their Transformation to 6-Substituted
 1,3-Dimethyluracils, trans-5,6-Disubstituted
 5,6-Dihydro-1,3-dimethyluracils, and 4,5,5-Trisubstituted
 3-Methyloxazolizin-2-ones.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5101
_journal_page_last               5119
_journal_paper_doi               10.1021/acs.joc.6b00670
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C20 H20 F2 N2 O3'
_chemical_formula_sum            'C20 H20 F2 N2 O3'
_chemical_formula_weight         374.38
_chemical_melting_point          497.0(10)
_chemical_name_systematic
; 
(5R*,6R*)-6-(bis(4-fluorophenyl)(hydroxy)methyl)-1,3,5-trimethyldihydropyrimidine-2,4(1H,3H)-dione
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 19.1869(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.813(2)
_cell_length_b                   10.0379(12)
_cell_length_c                   23.641(2)
_cell_measurement_reflns_used    5869
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      3.3
_cell_volume                     1857.2(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_publication_material  yadokari-XG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16220
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0026(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0558P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                2477
_reflns_number_total             4051
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00670_si_009.cif
_cod_data_source_block           cis-11i
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '496-498' was changed to
'497.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4036839