Preparation of α,β,γ,γ-tetrasubstituted α,β-unsaturated γ-lactams <i>via</i> a tandem or one-pot oxidative Ritter reaction/Knoevenagel condensation.
Chen, Yu-Ting; Hu, Yue-Hong; Gan, Zhang-Yan; Yu, Chun-Yu; Mo, Juxin; Chen, Meng-En; Zhang, Xiao-Ming; Zhang, Fu-Min; Organic & biomolecular chemistry 23 (2025) 9570–9575; doi:10.1039/d5ob01300c

data_7160760
_publ_section_title
;
 Preparation of &#x3b1;,&#x3b2;,&#x3b3;,&#x3b3;-tetrasubstituted
 &#x3b1;,&#x3b2;-unsaturated &#x3b3;-lactams <i>via</i> a tandem or
 one-pot oxidative Ritter reaction/Knoevenagel condensation.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9570
_journal_page_last               9575
_journal_paper_doi               10.1039/d5ob01300c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_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     dual
_audit_creation_date             2024-12-13
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-07-06 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.611(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5269(2)
_cell_length_b                   6.68550(10)
_cell_length_c                   24.6306(3)
_cell_measurement_reflns_used    25385
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.0420
_cell_measurement_theta_min      2.3500
_cell_volume                     3073.06(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (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      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.953
_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    -61.00  27.00   0.50    0.05    --  -44.63  57.00 -60.00  176
  2  \w    -70.00 -26.00   0.50    0.05    -- -100.00  61.00   0.00   88
  3  \w    -53.00 -27.00   0.50    0.05    -- -100.00  45.00   0.00   52
  4  \w    -53.00 -27.00   0.50    0.05    -- -100.00  45.00 150.00   52
  5  \w   -175.00 -77.00   0.50    0.05    -- -100.00  -9.00  40.00  196
  6  \w   -106.00 -81.00   0.50    0.05    --  -44.63-141.00 167.00   50
  7  \w    -33.00  11.00   0.50    0.05    --   44.63 -19.00 -30.00   88
  8  \w     -3.00  22.00   0.50    0.05    --   44.63 -19.00-150.00   50
  9  \w     40.00  66.00   0.50    0.05    --  108.93 -61.00 -60.00   52
 10  \w     38.00  72.00   0.50    0.05    --  108.93-129.00 -20.00   68
 11  \w     79.00 114.00   0.50    0.05    --  108.93-129.00 -20.00   70
 12  \w     99.00 125.00   0.50    0.05    --  108.93-153.00  85.00   52
 13  \w     54.00  93.00   0.50    0.05    --  108.93-153.00  85.00   78
 14  \w     64.00 118.00   0.50    0.05    --   44.63 153.00 126.00  108
 15  \w    -90.00 -56.00   0.50    0.05    --  -44.63 179.00-180.00   68
 16  \w   -116.00 -48.00   0.50    0.05    --  -44.63-179.00  30.00  136
 17  \w    -28.00  34.00   0.50    0.05    --  -44.63  19.00-180.00  124
 18  \w    -28.00  32.00   0.50    0.05    --  -44.63  19.00-120.00  120
 19  \w    -33.00  -8.00   0.50    0.05    --   44.63 -19.00  60.00   50
 20  \w      5.00  38.00   0.50    0.05    --   44.63 -37.00 150.00   66
 21  \w     -3.00  23.00   0.50    0.05    --   44.63 -19.00-150.00   52
 22  \w    -93.00 -63.00   0.50    0.05    -- -100.00 125.00-150.00   60
 23  \w    -75.00 -49.00   0.50    0.05    -- -100.00 141.00 128.06   52
 24  \w    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 -90.00   50
 25  \w    -51.00 -25.00   0.50    0.05    -- -100.00  45.00 -60.00   52
 26  \w   -123.00 -92.00   0.50    0.05    -- -100.00 141.00 128.06   62
 27  \w   -174.00-149.00   0.50    0.05    -- -100.00 -94.00 150.00   50
 28  \w   -124.00 -87.00   0.50    0.05    -- -100.00 -94.00 150.00   74
 29  \w   -109.00 -80.00   0.50    0.05    -- -100.00 115.00-107.38   58
 30  \w    -85.00 -34.00   0.50    0.05    -- -100.00 142.00 -19.89  102
 31  \w    -52.00 -26.00   0.50    0.05    -- -100.00  45.00 120.00   52
 32  \w    -68.00 -36.00   0.50    0.05    -- -100.00  61.00-120.00   64
 33  \w   -168.00-108.00   0.50    0.05    -- -100.00-120.00-116.00  120
 34  \w   -124.00 -98.00   0.50    0.05    -- -100.00 142.00 -19.89   52
 35  \w    -60.00 -35.00   0.50    0.05    -- -100.00 151.00  85.51   50
 36  \w   -101.00 -75.00   0.50    0.05    -- -100.00 151.00  85.51   52
 37  \w    -58.00 -33.00   0.50    0.05    -- -100.00 125.00-150.00   50
 38  \w    -53.00 -27.00   0.50    0.05    -- -100.00  45.00  90.00   52
 39  \w    -84.00 -50.00   0.50    0.05    -- -100.00  77.00-120.00   68
 40  \w    -62.00 -35.00   0.50    0.05    -- -100.00  61.00 -30.00   54
 41  \w   -112.00 -29.00   0.50    0.05    -- -100.00 125.00 150.00  166
 42  \w   -122.00 -97.00   0.50    0.05    -- -100.00 139.00  56.01   50
 43  \w    -84.00 -34.00   0.50    0.05    -- -100.00 139.00  56.01  100
 44  \w     81.00 107.00   0.50    0.05    --  108.93-125.00   0.00   52
 45  \w     40.00  66.00   0.50    0.05    --  108.93-125.00   0.00   52
 46  \w    138.00 170.00   0.50    0.05    --  108.93  61.00-150.00   64
 47  \w    100.00 154.00   0.50    0.05    --  108.93  45.00-120.00  108
 48  \w     98.00 134.00   0.50    0.05    --  108.93  61.00-150.00   72
 49  \w     65.00  90.00   0.50    0.05    --  108.93 -77.00  30.00   50
 50  \w     40.00 103.00   0.50    0.05    --  108.93 -77.00  60.00  126
 51  \w     35.00  60.00   0.50    0.05    --  108.93 -61.00  30.00   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      0.0627086000
_diffrn_orient_matrix_UB_12      -0.0170566000
_diffrn_orient_matrix_UB_13      -0.0186668000
_diffrn_orient_matrix_UB_21      0.0536901000
_diffrn_orient_matrix_UB_22      0.0221113000
_diffrn_orient_matrix_UB_23      0.0657438000
_diffrn_orient_matrix_UB_31      0.0005239000
_diffrn_orient_matrix_UB_32      -0.2287475000
_diffrn_orient_matrix_UB_33      0.0077464000
_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  0.0501
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            36404
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.171
_diffrn_reflns_theta_min         2.368
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.8054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5430
_reflns_number_total             6133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01300c3.cif
_cod_data_source_block           chenyut2_1209_autored
_cod_depositor_comments
'Adding full bibliography for 7160759--7160760.cif.'
_cod_database_code               7160760
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C56(H56)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C18(H18A,H18B), C21(H21A,H21B), C23(H23A,
 H23B), C24(H24A,H24B), C35(H35A,H35B), C44(H44A,H44B), C54(H54A,H54B),
 C57(H57A,H57B), C63(H63A,H63B), C64(H64A,H64B), C67(H67A,H67B), C76(H76A,H76B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C14(H14), C15(H15), C26(H26), C28(H28), C39(H39), N47(H47), C58(H58),
 C59(H59), C69(H69), C71(H71), C82(H82)
;
_shelx_res_checksum              30648
_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 1.888
_oxdiff_exptl_absorpt_empirical_full_min 0.322