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_7160269
_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         'C27 H16 N2 O3, H2 O, 1[C1H4O]'
_chemical_formula_sum            'C28 H22 N2 O5'
_chemical_formula_weight         466.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                 110.155(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.0157(11)
_cell_length_b                   7.5409(3)
_cell_length_c                   27.2889(15)
_cell_measurement_reflns_used    2630
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.7000
_cell_measurement_theta_min      2.8790
_cell_volume                     4446.2(4)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0434
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -50.00  33.00   1.00   75.00    --   19.52 -38.00-120.00   83
  2  \w     -8.00  83.00   1.00   75.00    --   19.52  19.00-120.00   91
  3  \w    -12.00  15.00   1.00   75.00    --   19.52 -77.00  30.00   27
  4  \w    -79.00 -40.00   1.00   75.00    --  -20.77-178.00   0.00   39
  5  \w    -91.00 -45.00   1.00   75.00    --  -20.77-178.00-120.00   46
;
_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      0.0124247000
_diffrn_orient_matrix_UB_12      -0.0679455000
_diffrn_orient_matrix_UB_13      -0.0114241000
_diffrn_orient_matrix_UB_21      -0.0139157000
_diffrn_orient_matrix_UB_22      0.0395306000
_diffrn_orient_matrix_UB_23      -0.0248888000
_diffrn_orient_matrix_UB_31      0.0270219000
_diffrn_orient_matrix_UB_32      0.0516439000
_diffrn_orient_matrix_UB_33      0.0040048000
_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  0.0421
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10491
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.122
_diffrn_reflns_theta_max         25.122
_diffrn_reflns_theta_min         2.816
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52233
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       prism
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0508P)^2^+0.2033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2850
_reflns_number_total             3941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01719f2.cif
_cod_data_source_block           gwg23jc03_auto
_cod_depositor_comments
'Adding full bibliography for 7160265--7160271.cif.'
_cod_database_code               7160269
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H15 N O5'
_chemical_oxdiff_usercomment     SD2
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.85
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O4-H4B
 0.87 with sigma of 0.02
3.a Free rotating group:
 O4(H4A)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C14(H14), C17(H17), C5(H5), C27(H27), C8(H8), C16(H16),
 C15(H15), C26(H26), C24(H24), C6(H6), C25(H25), C7(H7)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 120 electrons were 
found in a volume of 476\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
MeOH per formula unit.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              78338
_shelx_fab_checksum              27503
_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 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.766