Multi-component cascade reaction of 3-formylchromones: highly selective synthesis of 4,5-dihydro-[4,5'-bipyrimidin]-6(1H)-one derivatives.
Chen, Li; Huang, Rong; Yun, Xing-Han; Hao, Tian-Hui; Yan, Sheng-Jiao; Chemical communications (Cambridge, England) 57 (2021) 7657–7660; doi:10.1039/d1cc02437j

data_7128587
_publ_section_title
;
 Multi-component cascade reaction of 3-formylchromones: highly selective
 synthesis of 4,5-dihydro-[4,5'-bipyrimidin]-6(1H)-one derivatives.
;
_journal_issue                   62
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7657
_journal_page_last               7660
_journal_paper_doi               10.1039/d1cc02437j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C27 H30 F N5 O2, 0.5(O)'
_chemical_formula_sum            'C27 H30 F N5 O2.5'
_chemical_formula_weight         483.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2021-04-07 deposited with the CCDC.	2021-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                92.075(2)
_cell_angle_beta                 114.267(2)
_cell_angle_gamma                104.496(2)
_cell_formula_units_Z            2
_cell_length_a                   11.2453(13)
_cell_length_b                   11.7271(13)
_cell_length_c                   12.9429(16)
_cell_measurement_reflns_used    2002
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.76
_cell_measurement_theta_min      2.33
_cell_volume                     1487.7(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9078
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.645
_diffrn_reflns_theta_min         2.327
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0412 before and 0.0297 after correction.
The Ratio of minimum to maximum transmission is 0.8947.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6522
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1587
_refine_ls_R_factor_gt           0.0884
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1830P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2421
_refine_ls_wR_factor_ref         0.3077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3257
_reflns_number_total             6522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02437j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7128586--7128587.cif.'
_cod_original_formula_sum        'C27 H30 F N5 O2.50'
_cod_database_code               7128587
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3) \\sim Ueq, Uanis(O3A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C27) \\sim Ueq, Uanis(C25A) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C26A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C26A, C25, C25A, C27, C19, C26, C27A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=Sof(C27A)=Sof(H27D)=Sof(H27E)=
 Sof(H27F)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
 Fixed Sof: O3(0.25) O3A(0.25)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C20(H20),
 C23(H23)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C25A(H25D,H25E,H25F),
 C27A(H27D,H27E,H27F), C26A(H26D,H26E,H26F)
5.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              13204
_shelx_hkl_checksum              6875
_olex2_submission_special_instructions 'No special instructions were received'