Metal-free quinoline synthesis <i>via</i> Brønsted acid-promoted cyclization of ene-ynamides.
Wang, Yijie; Li, Yu; Zhang, Lisha; Chang, Junbiao; Wang, Xiao-Na; Organic & biomolecular chemistry 24 (2026) 899–904; doi:10.1039/d5ob01680k

data_7161019
_publ_section_title
;
 Metal-free quinoline synthesis <i>via</i> Br&#xf8;nsted acid-promoted
 cyclization of ene-ynamides.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              899
_journal_page_last               904
_journal_paper_doi               10.1039/d5ob01680k
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C27 H25 N O2 S'
_chemical_formula_sum            'C27 H25 N O2 S'
_chemical_formula_weight         427.54
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2025-04-07
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-10-09 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.910(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3321(3)
_cell_length_b                   13.1747(4)
_cell_length_c                   17.9409(4)
_cell_measurement_reflns_used    2522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3410
_cell_measurement_theta_min      4.1580
_cell_volume                     2202.95(11)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (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     -7.00  24.00   1.00    1.00    --    0.00  77.00 120.00   31
  2  \w   -104.00 -65.00   1.00    1.00    --  -33.50 178.00 -30.00   39
  3  \w     23.00  75.00   1.00    1.00    --   36.47  37.00 150.00   52
  4  \w    -22.00   4.00   1.00    1.00    --   36.47 -57.00 150.00   26
  5  \w    -18.00  64.00   1.00    1.00    --   36.47 -77.00 150.00   82
  6  \w     72.00 104.00   1.00    1.00    --   36.47 178.00   0.00   32
  7  \w     29.00 103.00   1.00    1.00    --   36.47  57.00-120.00   74
  8  \w     76.00 109.00   1.00    1.00    --   36.47 178.00  90.00   33
  9  \w     30.00  55.00   1.00    1.00    --   36.47 -57.00 150.00   25
 10  \w     39.00  90.00   1.00    3.00    --  108.00 -94.00  30.00   51
 11  \w    153.00 178.00   1.00    3.00    --  108.00  45.00 150.00   25
 12  \w     89.00 117.00   1.00    3.00    --  108.00  45.00 150.00   28
 13  \w     50.00  91.00   1.00    3.00    --  108.00 -94.00  90.00   41
 14  \w     38.00  63.00   1.00    3.00    --  108.00 -45.00 150.00   25
 15  \w     66.00 102.00   1.00    3.00    --  108.00 -94.00 -60.00   36
 16  \w     48.00 127.00   1.00    3.00    --  108.00 -45.00  60.00   79
 17  \w    104.00 173.00   1.00    3.00    --  108.00  77.00-180.00   69
 18  \w     89.00 177.00   1.00    3.00    --  108.00  45.00-120.00   88
 19  \w    101.00 127.00   1.00    3.00    --  108.00 -45.00 150.00   26
 20  \w    121.00 147.00   1.00    3.00    --  108.00 111.00-120.00   26
 21  \w     57.00 105.00   1.00    3.00    --  108.00-111.00-180.00   48
;
_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      0.1078238000
_diffrn_orient_matrix_UB_12      -0.0340289000
_diffrn_orient_matrix_UB_13      -0.0572488000
_diffrn_orient_matrix_UB_21      0.1227474000
_diffrn_orient_matrix_UB_22      0.0071342000
_diffrn_orient_matrix_UB_23      0.0605124000
_diffrn_orient_matrix_UB_31      -0.0249492000
_diffrn_orient_matrix_UB_32      -0.1116369000
_diffrn_orient_matrix_UB_33      0.0213571000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8449
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.165
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93399
_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    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0579
_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^)+(0.1059P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2999
_reflns_number_total             3932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01680k2.cif
_cod_data_source_block           20250496_auto
_cod_original_cell_volume        2202.96(11)
_cod_database_code               7161019
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C21H17O6N2S1
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.776
_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. Uiso/Uaniso restraints and constraints
Uanis(C15A) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C18A) \\sim Ueq,
Uanis(C19A) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C20)
\\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C15) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C15A)=Sof(C20A)=Sof(H20A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=1-FVAR(1)
 Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C20A(H20A), C19A(H19A), C18A(H18A), C17A(H17A), C16A(H16A), C22(H22),
  C23(H23), C25(H25), C26(H26)
4.c Fitted hexagon refined as free rotating group:
 C15(C16,C17,C18,C19,C20), C15A(C20A,C19A,C18A,C17A,C16A)
4.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              37152
_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 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.878