Cyclooctadiene-Derived Cage-Divergent Synthesis of Heteroadamantanes and Alternative Polycyclic Systems
Lysenko, Vladyslav; Popov, Ioann O.; Slobodyanyuk, Evgeniy Y.; Rusanov, Eduard; Pashenko, Olexandr Ye.; Volochnyuk, Dmitriy M.; Ryabukhin, Serhiy V.; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00368K

data_7161106
_publ_section_title
;
 Cyclooctadiene-derived cage-divergent synthesis of heteroadamantanes and
 alternative polycyclic systems.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3643
_journal_page_last               3648
_journal_paper_doi               10.1039/d6ob00368k
_journal_volume                  24
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H14 N O, Br'
_chemical_formula_sum            'C8 H14 Br N O'
_chemical_formula_weight         220.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7405(2)
_cell_length_b                   7.1349(2)
_cell_length_c                   17.6338(5)
_cell_measurement_reflns_used    1930
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.31
_cell_volume                     848.06(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7211
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.914
_diffrn_reflns_theta_min         2.310
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    4.789
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       prizm
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 529 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0130P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0525
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                1457
_reflns_number_total             1630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00368k2.cif
_cod_data_source_block           xr284
_cod_depositor_comments
'Adding full bibliography for 7161105--7161112.cif.'
_cod_database_code               7161106
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.369
_shelx_estimated_absorpt_t_max   0.497
_shelx_res_checksum              97900