Synthesis of 2-furanyl quinolines <i>via</i> zinc-catalyzed cascade cyclization of enynones with anthranils.
Feng, Yadong; Wang, Pu; Wang, Chaoyu; Wang, Tian; Cui, Xiuling; Organic & biomolecular chemistry 24 (2026) 1666–1671; doi:10.1039/d5ob01994j

data_7160951
_publ_section_title
;
 Synthesis of 2-furanyl quinolines <i>via</i> zinc-catalyzed cascade
 cyclization of enynones with anthranils.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1666
_journal_page_last               1671
_journal_paper_doi               10.1039/d5ob01994j
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-08 deposited with the CCDC.	2026-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.167(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2466(3)
_cell_length_b                   21.5948(6)
_cell_length_c                   9.1672(2)
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9300
_cell_measurement_theta_min      5.3640
_cell_volume                     1582.88(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -103.00 -60.00   1.00    2.00    --  -33.50 -77.00-150.00   43
  2  \w    -53.00  28.00   1.00    2.00    --  -33.50  37.00-180.00   81
  3  \w      9.00  73.00   1.00    2.00    --   36.47  77.00-150.00   64
  4  \w     76.00 110.00   1.00    2.00    --   36.47 178.00 -30.00   34
  5  \w     60.00 110.00   1.00    2.00    --   36.47 178.00-150.00   50
  6  \w     14.00  39.00   1.00    2.00    --   36.47  19.00 -90.00   25
  7  \w     61.00 107.00   1.00    2.00    --   36.47  19.00 -90.00   46
  8  \w     79.00 109.00   1.00    2.00    --   36.47 178.00-180.00   30
  9  \w     61.00  98.00   1.00   10.00    --  108.00-111.00 -90.00   37
 10  \w     39.00 114.00   1.00   10.00    --  108.00 -45.00 150.00   75
 11  \w     41.00  67.00   1.00   10.00    --  108.00 -15.00  90.00   26
 12  \w     46.00 134.00   1.00   10.00    --  108.00 -30.00   0.00   88
 13  \w    146.00 172.00   1.00   10.00    --  108.00  61.00  90.00   26
 14  \w     88.00 176.00   1.00   10.00    --  108.00  45.00-180.00   88
 15  \w     42.00  67.00   1.00   10.00    --  108.00 -94.00-180.00   25
 16  \w     97.00 142.00   1.00   10.00    --  108.00 -15.00  90.00   45
 17  \w     40.00 129.00   1.00   10.00    --  108.00 -77.00  90.00   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      0.1741919000
_diffrn_orient_matrix_UB_12      -0.0087874000
_diffrn_orient_matrix_UB_13      -0.0304928000
_diffrn_orient_matrix_UB_21      -0.0824048000
_diffrn_orient_matrix_UB_22      -0.0194487000
_diffrn_orient_matrix_UB_23      -0.1629744000
_diffrn_orient_matrix_UB_31      -0.0010764000
_diffrn_orient_matrix_UB_32      0.0680694000
_diffrn_orient_matrix_UB_33      -0.0504259000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5824
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         5.382
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1008P)^2^+0.1478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.2086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1823
_reflns_number_total             2823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01994j2.cif
_cod_data_source_block           20210488
_cod_depositor_comments          'Adding full bibliography for 7160951.cif.'
_cod_original_cell_volume        1582.87(8)
_cod_database_code               7160951
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O5N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.889
_reflns_odcompleteness_completeness 99.93
_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
 C17A-C18A
 1.55 with sigma of 0.02
 C18A-C19A
 1.53 with sigma of 0.02
 C17A-C8
 1.53 with sigma of 0.02
 C17-C18
 1.55 with sigma of 0.02
 C8-C17
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
4. Others
 Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C19A)=
 Sof(H19A)=Sof(H19B)=Sof(H19C)=1-FVAR(1)
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19D)=
 Sof(H19E)=Sof(H19F)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C17A(H17C,H17D), C18(H18A,H18B), C18A(H18C,H18D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C11(H11)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C19A(H19A,H19B,H19C), C19(H19D,H19E,
 H19F)
;
_shelx_res_checksum              46543
_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 2.040
_oxdiff_exptl_absorpt_empirical_full_min 0.800