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_7161108
_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         'C8 H12 I2 O'
_chemical_formula_sum            'C8 H12 I2 O'
_chemical_formula_weight         377.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 128.734(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1580(8)
_cell_length_b                   5.3842(2)
_cell_length_c                   13.0363(6)
_cell_measurement_reflns_used    3809
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.73
_cell_volume                     1048.95(10)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7025
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.978
_diffrn_reflns_theta_max         24.978
_diffrn_reflns_theta_min         2.726
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.946
_exptl_absorpt_correction_T_max  0.8277
_exptl_absorpt_correction_T_min  0.3537
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.393
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.598
_refine_diff_density_min         -1.336
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0088P)^2^+13.7636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                828
_reflns_number_total             924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00368k2.cif
_cod_data_source_block           v586
_cod_depositor_comments
'Adding full bibliography for 7161105--7161112.cif.'
_cod_original_cell_volume        1048.95(9)
_cod_database_code               7161108
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.717
_shelx_estimated_absorpt_t_min   0.368
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
;
_shelx_res_checksum              48651
_olex2_submission_special_instructions 'No special instructions were received'