Visible-light-induced annulation of 4-aminocoumarins to tetrahydropyrimidine-fused coumarins and evaluation of their antitumor activities
Li, Ning-Bo; Liu, Yun-Chang; Liu, Lun-Hang; Wei, Wan-Yu; Zhang, Di; He, Wei-Min; Jia, Hong-Yan; Bian, Wei; Green Chemistry 28 (2026) 1601–1606; doi:10.1039/D5GC05261K

data_7251701
_publ_section_title
;
 Visible-light-induced annulation of 4-aminocoumarins to
 tetrahydropyrimidine-fused coumarins and evaluation of their antitumor
 activities
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1601
_journal_page_last               1606
_journal_paper_doi               10.1039/D5GC05261K
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C21 H20 N2 O2'
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-02
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-03 deposited with the CCDC.	2025-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.666(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7577(2)
_cell_length_b                   9.9027(3)
_cell_length_c                   21.2760(5)
_cell_measurement_reflns_used    4279
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      71.2470
_cell_measurement_theta_min      4.2220
_cell_volume                     1631.12(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    100.00 132.00   0.50    0.50    --   42.10  77.00 120.00   64
  2  \w     80.00 130.00   0.50    0.50    --   42.10  77.00-120.00  100
  3  \w    -15.00  72.00   0.50    0.50    --   42.10 -57.00-180.00  174
  4  \w    -33.00  83.00   0.50    0.50    --   42.10 -82.00 150.00  232
  5  \w     40.00  84.00   0.50    0.50    --   42.10 -82.00-150.00   88
  6  \w     92.00 189.00   0.50    0.50    --  102.30  38.00   0.00  194
  7  \w    112.00 146.00   0.50    0.50    --  102.30 -38.00 -60.00   68
  8  \w     13.00  38.00   0.50    0.50    --  102.30 -82.00-180.00   50
  9  \w     19.00  48.00   0.50    0.50    --  102.30 -82.00  60.00   58
 10  \w     13.00  72.00   0.50    0.50    --  102.30 -38.00 -60.00  118
 11  \w     67.00 100.00   0.50    0.50    --  102.30 -82.00  60.00   66
 12  \w    112.00 137.00   0.50    0.50    --  102.30 -82.00  60.00   50
 13  \w     48.00  91.00   0.50    0.50    --  102.30 -82.00-120.00   86
 14  \w     15.00 120.00   0.50    0.50    --  102.30 -82.00  90.00  210
 15  \w     94.00 159.00   0.50    0.50    --  102.30  82.00  90.00  130
 16  \w     89.00 139.00   0.50    0.50    --  102.30  82.00 -90.00  100
 17  \w     52.00 145.00   0.50    0.50    --  102.30 -82.00-180.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0045179000
_diffrn_orient_matrix_UB_12      -0.1440062000
_diffrn_orient_matrix_UB_13      -0.0272370000
_diffrn_orient_matrix_UB_21      -0.0001355000
_diffrn_orient_matrix_UB_22      -0.0588199000
_diffrn_orient_matrix_UB_23      0.0670443000
_diffrn_orient_matrix_UB_31      -0.1989133000
_diffrn_orient_matrix_UB_32      -0.0030867000
_diffrn_orient_matrix_UB_33      -0.0053094000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_av_unetI/netI     0.1035
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7708
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         4.164
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.225
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.225
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0846
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.2437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2570
_reflns_number_total             2834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc05261k2.cif
_cod_data_source_block           bottle
_cod_database_code               7251701
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.908
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_shelx_res_checksum              96004
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.635