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_7160759
_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         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_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             2025-06-18
_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                 106.410(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1025(2)
_cell_length_b                   7.40740(10)
_cell_length_c                   19.1639(3)
_cell_measurement_reflns_used    5523
_cell_measurement_temperature    300.96(10)
_cell_measurement_theta_max      75.3680
_cell_measurement_theta_min      4.1380
_cell_volume                     1511.85(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 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      air
_diffrn_ambient_temperature      300.96(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.947
_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    -53.00 -28.00   0.50    0.05    -- -100.00  61.00 -30.00   50
  2  \w    -74.00 -35.00   0.50    0.05    -- -100.00  61.00 -60.00   78
  3  \w    -74.00 -45.00   0.50    0.05    -- -100.00  61.00 -90.00   58
  4  \w    -73.00 -36.00   0.50    0.05    -- -100.00  61.00-120.00   74
  5  \w    -54.00 -25.00   0.50    0.05    -- -100.00  45.00-150.00   58
  6  \w    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 -90.00   50
  7  \w    -52.00 -27.00   0.50    0.05    -- -100.00  45.00 -30.00   50
  8  \w    -33.00  24.00   0.50    0.05    --   44.66 -19.00-150.00  114
  9  \w     -5.00  21.00   0.50    0.05    --   44.66 -19.00-180.00   52
 10  \w    -33.00  -8.00   0.50    0.05    --  -44.66  41.00 136.00   50
 11  \w    -14.00  35.00   0.50    0.05    --   44.66 -41.00 -16.00   98
 12  \w     43.00  83.00   0.50    0.05    --  108.90 -94.00  60.00   80
 13  \w     47.00 106.00   0.50    0.05    --  108.90 -94.00 -30.00  118
 14  \w     37.00  65.00   0.50    0.05    --  108.90 -61.00   0.00   56
 15  \w     38.00  63.00   0.50    0.05    --  108.90 -61.00 -30.00   50
 16  \w     38.00  65.00   0.50    0.05    --  108.90 -61.00  30.00   54
 17  \w     38.00  68.00   0.50    0.05    --  108.90 -61.00  60.00   60
 18  \w     50.00 102.00   0.50    0.05    --  108.90 -77.00 120.00  104
 19  \w     26.00 113.00   0.50    0.05    --   44.66  41.00 136.00  174
 20  \w     91.00 151.00   0.50    0.05    --  108.90  41.00 136.00  120
 21  \w    117.00 172.00   0.50    0.05    --  108.90  45.00-120.00  110
 22  \w   -119.00 -25.00   0.50    0.05    --  -44.66 -41.00 -16.00  188
 23  \w   -137.00 -80.00   0.50    0.05    -- -100.00 -41.00 -16.00  114
;
_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      0.0773045000
_diffrn_orient_matrix_UB_12      -0.0532282000
_diffrn_orient_matrix_UB_13      0.0774202000
_diffrn_orient_matrix_UB_21      0.0973314000
_diffrn_orient_matrix_UB_22      -0.0932984000
_diffrn_orient_matrix_UB_23      -0.0313719000
_diffrn_orient_matrix_UB_31      0.0740633000
_diffrn_orient_matrix_UB_32      0.1780317000
_diffrn_orient_matrix_UB_33      0.0066726000
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9096
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.736
_diffrn_reflns_theta_min         4.151
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63967
_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    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0628P)^2^+0.2159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2533
_reflns_number_total             2976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01300c3.cif
_cod_data_source_block           chenyuting-zhfm_0618_auto
_cod_depositor_comments
'Adding full bibliography for 7160759--7160760.cif.'
_cod_database_code               7160759
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C11(H11A,H11B), C14(H14A,H14B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C9(H9), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_shelx_res_checksum              51484
_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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.786