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_7160265
_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 H15 N O5'
_chemical_formula_sum            'C26 H15 N O5'
_chemical_formula_weight         421.39
_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             2024-10-11
_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                 116.173(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.885(2)
_cell_length_b                   9.4476(11)
_cell_length_c                   15.911(2)
_cell_measurement_reflns_used    1973
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      24.8650
_cell_measurement_theta_min      2.9110
_cell_volume                     2008.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0217
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -30.00  35.00   1.00    5.00    --   19.52 -57.00-150.00   65
  2  \w     17.00  46.00   1.00    5.00    --   19.52 -77.00 120.00   29
  3  \w     12.00  38.00   1.00    5.00    --   19.52  77.00-180.00   26
  4  \w    -84.00  -4.00   1.00    5.00    --  -20.93 -57.00 -60.00   80
  5  \w    -32.00  31.00   1.00    5.00    --  -20.93  57.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0117680000
_diffrn_orient_matrix_UB_12      0.0366033000
_diffrn_orient_matrix_UB_13      0.0328649000
_diffrn_orient_matrix_UB_21      0.0442077000
_diffrn_orient_matrix_UB_22      0.0409811000
_diffrn_orient_matrix_UB_23      0.0139388000
_diffrn_orient_matrix_UB_31      -0.0269552000
_diffrn_orient_matrix_UB_32      0.0511567000
_diffrn_orient_matrix_UB_33      -0.0344817000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.121
_diffrn_reflns_theta_max         25.121
_diffrn_reflns_theta_min         2.641
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0562P)^2^+0.6480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2538
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01719f2.cif
_cod_data_source_block           gwg23jc01_auto
_cod_depositor_comments
'Adding full bibliography for 7160265--7160271.cif.'
_cod_original_cell_volume        2008.0(6)
_cod_database_code               7160265
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H15 N O5'
_chemical_oxdiff_usercomment     'oidb - dark crystal'
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.953
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C17 \\sim C12 \\sim C11 \\sim C14 \\sim C15 \\sim C16: within 2A with sigma of
0.02 and sigma for terminal atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C18(H18), C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C4(H4), C7(H7), C23(H23), C26(H26), C24(H24),
 C25(H25), C14(H14), C15(H15), C17(H17), C16(H16)
;
_shelx_res_checksum              93139
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.799