The [4+2] annulation of o-acylamino-aryl MBH carbonates with coumarins: facile access to tetrahydrochromeno[4,3-b]quinolin-6-ones
Xiang, Min; Liu, Gang-Yong; Liu, Hui-Mei; Zhou, Wen-Yi; Wang, Guang-Wei; Fei, Fei; Jia, Yun-Qing; Shen, Li-Wen; New Journal of Chemistry 49 (2025) 683–686; doi:10.1039/D4NJ04654D

data_7063576
_publ_section_title
;
 The [4+2] annulation of o-acylamino-aryl MBH carbonates with coumarins:
 facile access to tetrahydrochromeno[4,3-b]quinolin-6-ones
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              683
_journal_page_last               686
_journal_paper_doi               10.1039/D4NJ04654D
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C29 H30 Cl N O8'
_chemical_formula_sum            'C29 H30 Cl N O8'
_chemical_formula_weight         555.99
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-05 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                99.383(4)
_cell_angle_beta                 106.340(4)
_cell_angle_gamma                94.093(4)
_cell_formula_units_Z            4
_cell_length_a                   11.3573(5)
_cell_length_b                   15.0998(6)
_cell_length_c                   17.5183(8)
_cell_measurement_reflns_used    7465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5650
_cell_measurement_theta_min      3.6200
_cell_volume                     2822.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      5.00  33.00   1.00    1.50    --  -33.50  57.00 120.00   28
  2  \w    -94.00 -36.00   1.00    1.50    --  -33.50 -57.00 -30.00   58
  3  \w    -79.00 -15.00   1.00    1.50    --  -33.50 -37.00  30.00   64
  4  \w    -52.00 -24.00   1.00    1.50    --  -33.50  57.00 120.00   28
  5  \w    -94.00 -19.00   1.00    1.50    --  -33.50 -57.00-120.00   75
  6  \w      6.00  37.00   1.00    1.50    --   36.47  80.00 -45.74   31
  7  \w    -18.00  45.00   1.00    1.50    --   36.47 -77.00  30.00   63
  8  \w      0.00  25.00   1.00    1.50    --   36.47  92.00-171.56   25
  9  \w     61.00 107.00   1.00    1.50    --   36.47 178.00 -30.00   46
 10  \w     22.00  54.00   1.00    1.50    --   36.47  37.00   0.00   32
 11  \w     -1.00  24.00   1.00    1.50    --   36.47  94.00  12.14   25
 12  \w     79.00 107.00   1.00    1.50    --   36.47  37.00-120.00   28
 13  \w     14.00  43.00   1.00    1.50    --   36.47  37.00 -60.00   29
 14  \w      1.00  28.00   1.00    1.50    --   36.47  92.00  66.01   27
 15  \w     63.00  98.00   1.00    1.50    --   36.47 178.00 150.00   35
 16  \w    -33.00  49.00   1.00    1.50    --   36.47 -19.00 120.00   82
 17  \w     66.00  92.00   1.00    1.50    --   36.47  37.00 -60.00   26
 18  \w     66.00  98.00   1.00    1.50    --   36.47  37.00   0.00   32
 19  \w    -14.00  61.00   1.00    1.50    --   36.47 -73.00 119.00   75
 20  \w    127.00 166.00   1.00    8.00    --  108.00  61.00 150.00   39
 21  \w     92.00 132.00   1.00    8.00    --  108.00  61.00-150.00   40
 22  \w     39.00 106.00   1.00    8.00    --  108.00 -94.00  90.00   67
 23  \w     42.00 124.00   1.00    8.00    --  108.00 -61.00  90.00   82
 24  \w     42.00  80.00   1.00    8.00    --  108.00 -61.00 -60.00   38
 25  \w     74.00 108.00   1.00    8.00    --  108.00-111.00 -30.00   34
 26  \w    147.00 173.00   1.00    8.00    --  108.00  61.00-150.00   26
 27  \w    139.00 168.00   1.00    8.00    --  108.00  61.00-120.00   29
 28  \w     42.00 115.00   1.00    8.00    --  108.00 -77.00-150.00   73
 29  \w     40.00 125.00   1.00    8.00    --  108.00 -30.00  60.00   85
 30  \w     91.00 130.00   1.00    8.00    --  108.00  61.00-120.00   39
 31  \w     38.00  86.00   1.00    8.00    --  108.00 -94.00  30.00   48
 32  \w     62.00 108.00   1.00    8.00    --  108.00-111.00-150.00   46
 33  \w     45.00 110.00   1.00    8.00    --  108.00 -45.00-120.00   65
 34  \w    110.00 177.00   1.00    8.00    --  108.00  77.00  30.00   67
 35  \w    112.00 174.00   1.00    8.00    --  108.00  77.00-180.00   62
 36  \w     76.00 109.00   1.00    8.00    --  108.00-111.00  30.00   33
 37  \w     60.00 149.00   1.00    8.00    --  108.00 -15.00-180.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0217119000
_diffrn_orient_matrix_UB_12      -0.0299562000
_diffrn_orient_matrix_UB_13      0.0754071000
_diffrn_orient_matrix_UB_21      0.1081669000
_diffrn_orient_matrix_UB_22      -0.0572171000
_diffrn_orient_matrix_UB_23      0.0061422000
_diffrn_orient_matrix_UB_31      0.0901740000
_diffrn_orient_matrix_UB_32      0.0817899000
_diffrn_orient_matrix_UB_33      0.0547094000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21101
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.058
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         3.613
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     753
_refine_ls_number_reflns         10075
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0949P)^2^+0.4173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7499
_reflns_number_total             10075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj04654d2.cif
_cod_data_source_block           202405182_auto
_cod_depositor_comments          'Adding full bibliography for 7063576.cif.'
_cod_database_code               7063576
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N3O1Cl1
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.804
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-C24
 1.54 with sigma of 0.02
 C18-C19
 1.64 with sigma of 0.02
 C23A-O6A
 1.45 with sigma of 0.02
 C23A-C24A
 1.64 with sigma of 0.02
 O4'-C18'
 1.4 with sigma of 0.02
 C18'-C19'
 1.64 with sigma of 0.02
 C23'-C24'
 1.54 with sigma of 0.02
 C23B-C24B
 1.64 with sigma of 0.02
 C19-C18
 1.64 with sigma of 0.02
 C18A-C19A
 1.64 with sigma of 0.02
 C19B-C18B
 1.62 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23') \\sim Ueq, Uanis(C23B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O4'A) \\sim Ueq, Uanis(O4') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(O4) = Uanis(O4A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(O6) = Uanis(O6A)
Uanis(C18') = Uanis(C18B)
Uanis(C19') = Uanis(C19B)
Uanis(O4') = Uanis(O4'A)
Uanis(C23') = Uanis(C23B)
Uanis(C24') = Uanis(C24B)
4. Others
 Sof(O4A)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=1-FVAR(1)
 Sof(O4)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=
 FVAR(1)
 Sof(O6A)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=
 Sof(H24F)=1-FVAR(2)
 Sof(O6)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=
 FVAR(2)
 Sof(O4'A)=Sof(C18B)=Sof(H18G)=Sof(H18H)=Sof(C19B)=Sof(H19J)=Sof(H19K)=
 Sof(H19L)=1-FVAR(3)
 Sof(O4')=Sof(C18')=Sof(H18E)=Sof(H18F)=Sof(C19')=Sof(H19G)=Sof(H19H)=
 Sof(H19I)=FVAR(3)
 Sof(C23B)=Sof(H23G)=Sof(H23H)=Sof(C24B)=Sof(H24J)=Sof(H24K)=Sof(H24L)=1-FVAR(4)
 Sof(C23')=Sof(H23E)=Sof(H23F)=Sof(C24')=Sof(H24G)=Sof(H24H)=Sof(H24I)=FVAR(4)
5.a Riding coordinates:
 C19'(H19G,H19H,H19I)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C7'(H7'), C9'(H9')
5.c Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D), C23(H23A,H23B), C23A(H23C,H23D), C18'(H18E,
 H18F), C18B(H18G,H18H), C23'(H23E,H23F), C23B(H23G,H23H)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15), C1'(H1'),
 C3'(H3'), C4'(H4'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15')
5.e X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C21'(H21C,H21D)
5.f Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F), C24(H24A,H24B,H24C), C24A(H24D,
 H24E,H24F), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C),
 C19B(H19J,H19K,H19L), C24'(H24G,H24H,H24I), C24B(H24J,H24K,H24L), C27'(H27D,
 H27E,H27F), C28'(H28D,H28E,H28F), C29'(H29D,H29E,H29F)
;
_shelx_res_checksum              58632
_shelx_hkl_checksum              72253
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.893