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_7160266
_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[CH2Cl2]'
_chemical_formula_sum            'C28.5 H19 Cl N2 O3'
_chemical_formula_weight         472.91
_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
;
2024-11-07 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.858(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3461(7)
_cell_length_b                   9.1978(5)
_cell_length_c                   20.5495(11)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      60.541
_cell_measurement_theta_min      3.841
_cell_volume                     2275.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  BrukerD8
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1493
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            104411
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.790
_diffrn_reflns_theta_min         3.840
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1783 before and 0.1097 after correction.
The Ratio of minimum to maximum transmission is 0.8502.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       plate
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.0094(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1157P)^2^+0.1729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.1982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2720
_reflns_number_total             4170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01719f2.cif
_cod_data_source_block           cu_dwg24jc02
_cod_depositor_comments
'Adding full bibliography for 7160265--7160271.cif.'
_cod_original_formula_sum        'C28.50 H19 Cl N2 O3'
_cod_database_code               7160266
_shelx_shelxl_version_number     2019/1
_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:
 C6(H6a,H6b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1a), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              68307
_shelx_fab_checksum              57500
_olex2_submission_special_instructions 'No special instructions were received'