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_7161109
_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_formula_moiety         'C13 H22 N2 O3'
_chemical_formula_sum            'C13 H22 N2 O3'
_chemical_formula_weight         254.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 117.2665(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3355(3)
_cell_length_b                   11.1067(2)
_cell_length_c                   12.0599(3)
_cell_measurement_reflns_used    3955
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.56
_cell_measurement_theta_min      2.64
_cell_volume                     1349.63(6)
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20493
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.653
_diffrn_reflns_theta_min         2.021
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.3208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2122
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00368k2.cif
_cod_data_source_block           ivv2794
_cod_depositor_comments
'Adding full bibliography for 7161105--7161112.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7161109
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              64716