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_7160270
_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         'C28 H18 N2 O3, 0.5[C3H6O]'
_chemical_formula_sum            'C29.5 H21 N2 O3.5'
_chemical_formula_weight         459.48
_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     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                 100.514(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2834(7)
_cell_length_b                   9.2034(5)
_cell_length_c                   20.3095(13)
_cell_measurement_reflns_used    7690
_cell_measurement_temperature    219.7(6)
_cell_measurement_theta_max      32.4460
_cell_measurement_theta_min      2.1510
_cell_volume                     2257.4(2)
_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      219.7(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_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    -20.00  43.00   0.50    5.00    --    8.20  80.00 -98.00  126
  2  \w      6.00  34.00   0.50    5.00    --    8.20 -80.00 137.00   56
  3  \w    -15.00  43.00   0.50    5.00    --   -9.45  80.00 -98.00  116
  4  \w      3.00  45.00   0.50    5.00    --    8.20 -99.00   0.00   84
  5  \w     14.00  44.00   0.50    5.00    --    8.20 -99.00 -90.00   60
  6  \w     43.00  82.00   0.50    5.00    --    8.20  57.00  90.00   78
  7  \w    -11.00  39.00   0.50    5.00    --    8.20  57.00  90.00  100
  8  \w      1.00  44.00   0.50    5.00    --    8.20 -99.00 -30.00   86
  9  \w    -41.00  -2.00   0.50    5.00    --   -9.45 -57.00 120.00   78
 10  \w    -69.00 -44.00   0.50    5.00    --   -9.45 -57.00 120.00   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      -0.0206230000
_diffrn_orient_matrix_UB_12      -0.0618153000
_diffrn_orient_matrix_UB_13      0.0146052000
_diffrn_orient_matrix_UB_21      -0.0276705000
_diffrn_orient_matrix_UB_22      -0.0227879000
_diffrn_orient_matrix_UB_23      -0.0320666000
_diffrn_orient_matrix_UB_31      0.0475159000
_diffrn_orient_matrix_UB_32      -0.0400695000
_diffrn_orient_matrix_UB_33      -0.0043458000
_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  0.0508
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26341
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.124
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45317
_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    1.352
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0569P)^2^+0.2788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3868
_reflns_number_total             5558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01719f2.cif
_cod_data_source_block           swg24jc01
_cod_depositor_comments
'Adding full bibliography for 7160265--7160271.cif.'
_cod_original_formula_sum        'C29.50 H21 N2 O3.50'
_cod_database_code               7160270
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C28H17N2O3
_chemical_oxdiff_usercomment     MeIsatin
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.916
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C28(H28), C27(H27), C7(H7), C16(H16), C5(H5), C25(H25), C19(H19),
 C6(H6), C26(H26), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 68 electrons were 
found in a volume of 310\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[C3H6O] per Asymmetric Unit 
which account for 64 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              36179
_shelx_fab_checksum              33355
_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.382