One-pot synthesis of azepine spiro[4.6]-γ-lactams by a Hantzsch-type reaction.
Hopkins, Scarlet L.; Clarke, Kristen T.; Clegg, Jack K.; Gee, William J.; Organic & biomolecular chemistry 23 (2025) 614–618; doi:10.1039/d4ob01719f

data_7160271
_publ_section_title
;
 One-pot synthesis of azepine spiro[4.6]-&#x3b3;-lactams by a
 Hantzsch-type reaction.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              614
_journal_page_last               618
_journal_paper_doi               10.1039/d4ob01719f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C26 H13 N3 O5, 1[C3H6O]'
_chemical_formula_sum            'C29 H19 N3 O6'
_chemical_formula_weight         505.47
_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             2024-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.853(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8568(8)
_cell_length_b                   20.5209(17)
_cell_length_c                   11.6657(7)
_cell_measurement_reflns_used    4725
_cell_measurement_temperature    150
_cell_measurement_theta_max      32.6210
_cell_measurement_theta_min      3.0520
_cell_volume                     2246.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_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    -29.00  11.00   0.50   20.00    --    8.20 101.00 176.00   80
  2  \w    -27.00   0.00   0.50   20.00    --   -9.45 101.00 176.00   54
  3  \w      0.00  44.00   0.50   20.00    --    8.20 -99.00-180.00   88
  4  \w    -11.00  28.00   0.50   20.00    --    8.20  57.00   0.00   78
  5  \w     -2.00  45.00   0.50   20.00    --    8.20 -99.00  30.00   94
  6  \w     18.00  44.00   0.50   20.00    --    8.20 -99.00-120.00   52
  7  \w     38.00  82.00   0.50   20.00    --    8.20  57.00   0.00   88
  8  \w     -1.00  34.00   0.50   20.00    --    8.20 -99.00 120.00   70
  9  \w      0.00  36.00   0.50   20.00    --    8.20 -99.00-150.00   72
 10  \w    -29.00   6.00   0.50   20.00    --   -9.45 -37.00-150.00   70
 11  \w    -88.00 -34.00   0.50   20.00    --   -9.45 -37.00-150.00  108
 12  \w     32.00  57.00   0.50   20.00    --   -9.45  57.00 -90.00   50
 13  \w    -23.00   2.00   0.50   20.00    --   -9.45  57.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0575297000
_diffrn_orient_matrix_UB_12      -0.0186016000
_diffrn_orient_matrix_UB_13      0.0071783000
_diffrn_orient_matrix_UB_21      -0.0458232000
_diffrn_orient_matrix_UB_22      0.0272505000
_diffrn_orient_matrix_UB_23      -0.0181308000
_diffrn_orient_matrix_UB_31      -0.0174631000
_diffrn_orient_matrix_UB_32      -0.0103103000
_diffrn_orient_matrix_UB_33      -0.0608316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25280
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.122
_diffrn_reflns_theta_max         25.122
_diffrn_reflns_theta_min         1.985
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.5892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3034
_reflns_number_total             4003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01719f2.cif
_cod_data_source_block           swg24jc02
_cod_depositor_comments
'Adding full bibliography for 7160265--7160271.cif.'
_cod_database_code               7160271
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C27H25N3O5
_chemical_oxdiff_usercomment     MeIsatin
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C8(H8), C14(H14), C23(H23), C17(H17), C26(H26), C16(H16),
 C15(H15), C5(H5), C6(H6), C24(H24), C25(H25)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              32360
_shelx_fab_checksum              86829
_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 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.913