One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction to access 5-quaternary-4-amidocyclopent-2-enones and 2-quaternary-3-amidoindanones.
Hu, Yue-Hong; Chen, Yu-Ting; He, Zhi-Juan; Gan, Zhang-Yan; Zhang, Ling-Hui; Xi, Wen-Jie; Li, Baosheng; Zhang, Fu-Min; Chemical communications (Cambridge, England) 61 (2025) 3720–3723; doi:10.1039/d4cc06597b

data_1573799
_publ_section_title
;
 One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter
 reaction to access 5-quaternary-4-amidocyclopent-2-enones and
 2-quaternary-3-amidoindanones.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3720
_journal_page_last               3723
_journal_paper_doi               10.1039/d4cc06597b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C18 H16 F N O2'
_chemical_formula_sum            'C18 H16 F N O2'
_chemical_formula_weight         297.32
_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             2024-11-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-12-10 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.5299(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.35635(9)
_cell_length_b                   20.16774(19)
_cell_length_c                   9.47069(10)
_cell_measurement_reflns_used    15574
_cell_measurement_temperature    271.7(3)
_cell_measurement_theta_max      77.3290
_cell_measurement_theta_min      2.1510
_cell_volume                     1484.72(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      271.7(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.970
_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    100.00 175.00   0.50    0.05    --  112.00  61.00-180.00  150
  2  \w    143.00 173.00   0.50    0.05    --  112.00  45.00 -90.00   60
  3  \w    101.00 127.00   0.50    0.05    --  112.00  45.00 -90.00   52
  4  \w     92.00 175.00   0.50    0.05    --  112.00  61.00   0.00  166
  5  \w     99.00 171.00   0.50    0.05    --  112.00  77.00  60.00  144
  6  \w    -25.00  20.00   0.50    0.05    --   44.32 -19.00   0.00   90
  7  \w    -25.00  16.00   0.50    0.05    --   44.32 -19.00 120.00   82
  8  \w     74.00 115.00   0.50    0.05    --   44.32-159.00  41.00   82
  9  \w     91.00 134.00   0.50    0.05    --  112.00-159.00  41.00   86
 10  \w     82.00 112.00   0.50    0.05    --  112.00-125.00 120.00   60
 11  \w     43.00  77.00   0.50    0.05    --  112.00-125.00 120.00   68
 12  \w     44.00  78.00   0.50    0.05    --  112.00-159.00  41.00   68
 13  \w     40.00  98.00   0.50    0.05    --  112.00 -94.00   0.00  116
 14  \w    -29.00  -4.00   0.50    0.05    --   44.32 -19.00-180.00   50
 15  \w     29.00  54.00   0.50    0.05    --   44.32-118.00-165.00   50
 16  \w     44.00  79.00   0.50    0.05    --  112.00-125.00-150.00   70
 17  \w     50.00  75.00   0.50    0.05    --  112.00-118.00-165.00   50
 18  \w     42.00  67.00   0.50    0.05    --  112.00 -61.00-180.00   50
 19  \w     41.00  89.00   0.50    0.05    --  112.00 -77.00-180.00   96
 20  \w     39.00  91.00   0.50    0.05    --  112.00 -77.00 -60.00  104
 21  \w     65.00 100.00   0.50    0.05    --  112.00 -77.00   0.00   70
 22  \w     39.00  99.00   0.50    0.05    --  112.00 -77.00  60.00  120
 23  \w     43.00  68.00   0.50    0.05    --  112.00 -61.00  90.00   50
 24  \w     40.00  65.00   0.50    0.05    --  112.00 -61.00-150.00   50
 25  \w     81.00 136.00   0.50    0.05    --  112.00 118.00 -78.00  110
 26  \w     82.00 107.00   0.50    0.05    --  112.00 159.00  73.00   50
 27  \w     53.00  80.00   0.50    0.05    --   44.32 159.00  73.00   54
 28  \w    -22.00  28.00   0.50    0.05    --  -44.32  19.00  30.00  100
 29  \w    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 -90.00   50
 30  \w     -3.00  35.00   0.50    0.05    --  -44.32  19.00  60.00   76
 31  \w    -54.00 -25.00   0.50    0.05    -- -100.00  45.00 150.00   58
 32  \w    -54.00 -25.00   0.50    0.05    -- -100.00  45.00  90.00   58
 33  \w    -70.00 -26.00   0.50    0.05    -- -100.00  61.00  30.00   88
 34  \w    -68.00 -43.00   0.50    0.05    -- -100.00 118.00 -78.00   50
 35  \w   -126.00 -55.00   0.50    0.05    -- -100.00 146.00-158.55  142
 36  \w    -96.00 -71.00   0.50    0.05    --  -44.32 159.00  73.00   50
 37  \w   -121.00 -87.00   0.50    0.05    -- -100.00 148.00 125.80   68
 38  \w    -65.00 -36.00   0.50    0.05    -- -100.00 148.00 125.80   58
 39  \w   -126.00 -33.00   0.50    0.05    -- -100.00 144.00  97.24  186
 40  \w   -111.00 -86.00   0.50    0.05    -- -100.00 159.00  73.00   50
 41  \w    -58.00 -32.00   0.50    0.05    -- -100.00 125.00 -30.00   52
 42  \w   -108.00 -80.00   0.50    0.05    -- -100.00 125.00 -30.00   56
 43  \w    -92.00 -19.00   0.50    0.05    --  -44.32 118.00 -78.00  146
 44  \w    -55.00 -28.00   0.50    0.05    -- -100.00 125.00-150.00   54
 45  \w   -112.00 -59.00   0.50    0.05    -- -100.00 125.00-150.00  106
 46  \w   -177.00-101.00   0.50    0.05    -- -100.00 -30.00  90.00  152
 47  \w   -118.00 -29.00   0.50    0.05    --  -44.32 -57.00  90.00  178
 48  \w    -88.00 -59.00   0.50    0.05    --  -44.32-159.00  41.00   58
 49  \w   -125.00 -99.00   0.50    0.05    -- -100.00-159.00  41.00   52
 50  \w   -130.00 -97.00   0.50    0.05    -- -100.00-118.00-165.00   66
 51  \w   -172.00-147.00   0.50    0.05    -- -100.00-118.00-165.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1248558000
_diffrn_orient_matrix_UB_12      -0.0401845000
_diffrn_orient_matrix_UB_13      0.0524996000
_diffrn_orient_matrix_UB_21      0.0542760000
_diffrn_orient_matrix_UB_22      -0.0640771000
_diffrn_orient_matrix_UB_23      -0.0589483000
_diffrn_orient_matrix_UB_31      0.1440402000
_diffrn_orient_matrix_UB_32      -0.0106704000
_diffrn_orient_matrix_UB_33      0.1560396000
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19065
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.494
_diffrn_reflns_theta_min         6.054
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0683P)^2^+0.2604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2882
_reflns_number_total             3061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06597b3.cif
_cod_data_source_block           huyuehong2-zhfm_0426_auto
_cod_depositor_comments
'Adding full bibliography for 1573796--1573800.cif.'
_cod_database_code               1573799
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              76972
_shelx_hkl_checksum              94046
_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 1.905
_oxdiff_exptl_absorpt_empirical_full_min 0.618