Enantioselective formal [2+2+2] cycloaddition of 1,3,5-triazinanes to construct tetrahydropyrimidin-4-one derivatives
Ruan, Peiran; Tang, Qiong; Yang, Zun; Liu, Xiaohua; Feng, Xiaoming; Chemical Communications  (2021) –; doi:10.1039/D1CC06549A

data_7129372
_publ_section_title
;
 Enantioselective formal [2+2+2] cycloaddition of 1,3,5-triazinanes to
 construct tetrahydropyrimidin-4-one derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06549A
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H29 N3 O3'
_chemical_formula_sum            'C31 H29 N3 O3'
_chemical_formula_weight         491.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-14 deposited with the CCDC.	2021-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0721(3)
_cell_length_b                   12.0638(4)
_cell_length_c                   20.9044(6)
_cell_measurement_reflns_used    5921
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      4.23
_cell_volume                     2540.05(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      172(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10611
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.129
_diffrn_reflns_theta_min         4.230
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       flake
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
; 
 Flack x determined using 1559 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.06(16)
_refine_ls_extinction_coef       0.0027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                4014
_reflns_number_total             4449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06549a2.cif
_cod_data_source_block           rpr010
_cod_database_code               7129372
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.753
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              26525
_shelx_hkl_checksum              91634