Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate.
Bakanas, Ian; Tang, Jess C.; Sarpong, Richmond; Chemical communications (Cambridge, England) 59 (2023) 3858–3861; doi:10.1039/d3cc00945a

data_7131392
_publ_section_title
;
 Skeletal diversification by C-C cleavage to access bicyclic frameworks
 from a common tricyclooctane intermediate.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3858
_journal_page_last               3861
_journal_paper_doi               10.1039/d3cc00945a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C11 H18 O2'
_chemical_formula_sum            'C11 H18 O2'
_chemical_formula_weight         182.25
_space_group_crystal_system      tetragonal
_space_group_IT_number           102
_space_group_name_Hall           'P 4n -2n'
_space_group_name_H-M_alt        'P 42 n m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-03 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   23.5301(3)
_cell_length_b                   23.5301(3)
_cell_length_c                   5.98071(11)
_cell_measurement_reflns_used    17157
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      74.4970
_cell_measurement_theta_min      3.7280
_cell_volume                     3311.31(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_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    -74.00  14.00   0.50    3.00    --    0.00 -53.00 -71.00  176
  2  \w    -14.00  74.00   0.50    3.00    --    0.00  53.00  73.00  176
  3  \w    -63.00 -26.00   0.50   13.00    -- -100.00  53.00  73.00   74
  4  \w   -174.00 -86.00   0.50   13.00    -- -100.00 -53.00 -71.00  176
  5  \w     26.00  57.00   0.50   13.00    --  100.18 -53.00 -71.00   62
  6  \w     86.00 174.00   0.50   13.00    --  100.18  53.00  73.00  176
  7  \w    -23.00  45.00   0.50    3.00    --    0.00  77.00 120.00  136
  8  \w    -23.00  45.00   0.50    3.00    --    0.00  77.00   0.00  136
  9  \w    -23.00  45.00   0.50    3.00    --    0.00  77.00-150.00  136
 10  \w    -54.00 -24.00   0.50   13.00    -- -100.00  45.00  30.00   60
 11  \w    -54.00 -24.00   0.50   13.00    -- -100.00  45.00 150.00   60
 12  \w    -74.00 -29.00   0.50   13.00    -- -100.00  61.00  90.00   90
 13  \w    -54.00 -24.00   0.50   13.00    -- -100.00  45.00   0.00   60
 14  \w    -54.00 -24.00   0.50   13.00    -- -100.00  45.00  60.00   60
 15  \w   -178.00 -86.00   0.50   13.00    -- -100.00 -30.00-120.00  184
 16  \w    -54.00 -24.00   0.50   13.00    -- -100.00  45.00 120.00   60
 17  \w   -178.00 -88.00   0.50   13.00    -- -100.00 -15.00 -30.00  180
 18  \w    -54.00 -24.00   0.50   13.00    -- -100.00  45.00-150.00   60
 19  \w    -74.00 -29.00   0.50   13.00    -- -100.00  61.00   0.00   90
 20  \w    -54.00 -24.00   0.50   13.00    -- -100.00  45.00-120.00   60
 21  \w     88.00 175.00   0.50   13.00    --  100.18  15.00 150.00  174
 22  \w     29.00  68.00   0.50   13.00    --  100.18 -61.00-150.00   78
 23  \w     29.00  68.00   0.50   13.00    --  100.18 -61.00 -90.00   78
 24  \w     29.00  68.00   0.50   13.00    --  100.18 -61.00 150.00   78
 25  \w     29.00  68.00   0.50   13.00    --  100.18 -61.00-180.00   78
 26  \w     87.00 175.00   0.50   13.00    --  100.18  30.00-180.00  176
 27  \w    -13.00  22.00   0.50    3.00    --    0.00  38.00 -60.00   70
 28  \w    -13.00  80.00   0.50    3.00    --    0.00  19.00-150.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0512103000
_diffrn_orient_matrix_UB_12      0.0407996000
_diffrn_orient_matrix_UB_13      0.0026490000
_diffrn_orient_matrix_UB_21      0.0113871000
_diffrn_orient_matrix_UB_22      0.0152355000
_diffrn_orient_matrix_UB_23      -0.2465029000
_diffrn_orient_matrix_UB_31      -0.0391817000
_diffrn_orient_matrix_UB_32      -0.0488828000
_diffrn_orient_matrix_UB_33      -0.0746586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            32348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.282
_diffrn_reflns_theta_min         2.656
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1046P)^2^+0.7782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1723
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3164
_reflns_number_total             3522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00945a2.cif
_cod_data_source_block           IB008_Sarpong
_cod_depositor_comments
'Adding full bibliography for 7131392--7131393.cif.'
_cod_original_cell_volume        3311.31(10)
_cod_database_code               7131392
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C O H'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.933
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(4)
 0.0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C7B-C8B
 1.5 with sigma of 0.01
4. Rigid body (RIGU) restrains
 C1B, C2B, C3B, C9B, C10B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O1B(0.5) H1B(0.5) O2B(0.5) H2B(0.5) C1B(0.5) C2B(0.5) H2BA(0.5)
 C3B(0.5) H3B(0.5) C4B(0.5) C5B(0.5) H5BA(0.5) H5BB(0.5) H5BC(0.5) C6B(0.5)
 H6BA(0.5) H6BB(0.5) H6BC(0.5) C7B(0.5) H7B(0.5) C8B(0.5) H8BA(0.5) H8BB(0.5)
 C9B(0.5) H9B(0.5) C10B(0.5) H10B(0.5) C11B(0.5) H11D(0.5) H11E(0.5) H11F(0.5)
6.a Ternary CH refined with riding coordinates:
 C2A(H2AA), C3A(H3A), C7A(H7A), C9A(H9A), C10A(H10A), C2B(H2BA), C3B(H3B),
 C7B(H7B), C9B(H9B), C10B(H10B)
6.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C8B(H8BA,H8BB)
6.c Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C6A(H6AA,H6AB,H6AC), C11A(H11A,H11B,H11C), C5B(H5BA,H5BB,
 H5BC), C6B(H6BA,H6BB,H6BC), C11B(H11D,H11E,H11F)
6.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O2A(H2A), O1B(H1B), O2B(H2B)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              35266
_shelx_hkl_checksum              99220
_shelx_fab_checksum              17698
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.931
_oxdiff_exptl_absorpt_empirical_full_min 0.592