Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1 H)-ones through Organocatalytic Transfer Hydrogenation of 2-Hydroxypyrimidines.
Meng, Fan-Jie; Shi, Lei; Feng, Guang-Shou; Sun, Lei; Zhou, Yong-Gui; The Journal of organic chemistry 84 (2019) 4435–4442; doi:10.1021/acs.joc.8b03128

data_4034278
_publ_section_title
;
 Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1 H)-ones through
 Organocatalytic Transfer Hydrogenation of 2-Hydroxypyrimidines.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4435
_journal_page_last               4442
_journal_paper_doi               10.1021/acs.joc.8b03128
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 102.7850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7922(2)
_cell_length_b                   14.2337(3)
_cell_length_c                   21.0488(4)
_cell_measurement_reflns_used    9781
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      139.649
_cell_measurement_theta_min      7.558
_cell_volume                     3445.38(11)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      270(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            72687
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.173
_diffrn_reflns_theta_min         3.779
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
; 
 Flack x determined using 4192 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.12(8)
_refine_ls_extinction_coef       0.0032(3)
_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   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     902
_refine_ls_number_reflns         12966
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.5962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                10348
_reflns_number_total             12966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03128_si_002.cif
_cod_data_source_block           cu_d8v18168_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034278
_shelx_estimated_absorpt_t_min   0.874
_shelx_estimated_absorpt_t_max   0.915
_shelxl_version_number           2013-4
_shelx_res_checksum              15953
_shelx_hkl_checksum              25293