Remodelling of tricyclic carbon frameworks with a norbornene scaffold.
Yoshitani, Akihiro; Sasage, Tomonari; Kato, Ranmaru; Suzuki, Takahiro; Ikeuchi, Kazutada; Tanino, Keiji; Chemical communications (Cambridge, England) 61 (2025) 16372–16375; doi:10.1039/d5cc04790k

data_1575620
_publ_section_title
;
 Remodelling of tricyclic carbon frameworks with a norbornene scaffold.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16372
_journal_page_last               16375
_journal_paper_doi               10.1039/d5cc04790k
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C12 H16 O2'
_chemical_formula_sum            'C12 H16 O2'
_chemical_formula_weight         192.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-12-10 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                84.407(8)
_cell_angle_beta                 88.851(6)
_cell_angle_gamma                84.949(6)
_cell_formula_units_Z            2
_cell_length_a                   6.6129(3)
_cell_length_b                   8.1963(9)
_cell_length_c                   9.6111(9)
_cell_measurement_reflns_used    2604
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.9370
_cell_measurement_theta_min      6.6710
_cell_volume                     516.41(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.912
_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     87.00 118.00   0.50    0.30    --   42.88 125.00  30.00   62
  2  \w     77.00 141.00   0.50    1.50    --  107.56 121.00  66.00  128
  3  \w     65.00 113.00   0.50    0.30    --   42.88 153.00-133.00   96
  4  \w     73.00  98.00   0.50    0.30    --   42.88 125.00-180.00   50
  5  \w     57.00 105.00   0.50    1.50    --  107.56 -77.00 -30.00   96
  6  \w     35.00  63.00   0.50    1.50    --  107.56 -61.00 -60.00   56
  7  \w     43.00  70.00   0.50    1.50    --  107.56 -61.00-120.00   54
  8  \w     36.00  71.00   0.50    1.50    --  107.56 -61.00-150.00   70
  9  \w     35.00  60.00   0.50    1.50    --  107.56 -61.00-180.00   50
 10  \w     40.00  68.00   0.50    1.50    --  107.56 -61.00  30.00   56
 11  \w     35.00  69.00   0.50    1.50    --  107.56 -61.00 120.00   68
 12  \w     71.00  96.00   0.50    1.50    --  107.56-121.00 -15.00   50
 13  \w     78.00 103.00   0.50    0.30    --   42.88-153.00-175.00   50
 14  \w     49.00  83.00   0.50    1.50    --  107.56-153.00-175.00   68
 15  \w     60.00 108.00   0.50    1.50    --  107.56-125.00-180.00   96
 16  \w     48.00  74.00   0.50    0.30    --   42.88-121.00 -15.00   52
 17  \w    -24.00  38.00   0.50    0.30    --  -42.88  19.00  90.00  124
 18  \w    -26.00  35.00   0.50    0.30    --  -42.88  19.00 -30.00  122
 19  \w    -26.00  38.00   0.50    0.30    --  -42.88  19.00-150.00  128
 20  \w    -76.00 -51.00   0.50    0.30    --  -42.88 121.00  66.00   50
 21  \w   -102.00 -67.00   0.50    1.50    -- -106.00 121.00  66.00   70
 22  \w   -113.00 -61.00   0.50    0.30    --  -42.88 153.00-133.00  104
 23  \w   -127.00-101.00   0.50    1.50    -- -106.00 153.00-133.00   52
 24  \w   -103.00 -56.00   0.50    1.50    -- -106.00  77.00 -90.00   94
 25  \w    -68.00 -35.00   0.50    1.50    -- -106.00  61.00-150.00   66
 26  \w   -176.00 -28.00   0.50    1.50    -- -106.00   0.00 -30.00  296
 27  \w    -71.00 -37.00   0.50    1.50    -- -106.00  61.00  30.00   68
 28  \w    -67.00 -32.00   0.50    1.50    -- -106.00  61.00  60.00   70
 29  \w    -66.00 -34.00   0.50    1.50    -- -106.00  61.00 120.00   64
 30  \w   -118.00 -82.00   0.50    1.50    -- -106.00 -30.00  30.00   72
 31  \w   -176.00 -99.00   0.50    1.50    -- -106.00 -77.00  90.00  154
 32  \w   -134.00 -97.00   0.50    1.50    -- -106.00-121.00 -15.00   74
 33  \w    -82.00 -56.00   0.50    0.30    --  -42.88-153.00-175.00   52
 34  \w   -162.00-119.00   0.50    1.50    -- -106.00-153.00-175.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0226747000
_diffrn_orient_matrix_UB_12      -0.0954430000
_diffrn_orient_matrix_UB_13      0.1448802000
_diffrn_orient_matrix_UB_21      -0.0179104000
_diffrn_orient_matrix_UB_22      0.1632523000
_diffrn_orient_matrix_UB_23      0.0681533000
_diffrn_orient_matrix_UB_31      -0.2320938000
_diffrn_orient_matrix_UB_32      0.0132544000
_diffrn_orient_matrix_UB_33      -0.0175366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3951
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.979
_diffrn_reflns_theta_min         4.623
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.236
_exptl_crystal_description       needle
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.803
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1378P)^2^+0.0992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1935
_refine_ls_wR_factor_ref         0.2025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1626
_reflns_number_total             1944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04790k2.cif
_cod_data_source_block           20221018y_auto
_cod_depositor_comments
'Adding full bibliography for 1575616--1575620.cif.'
_cod_database_code               1575620
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 96.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              93022
_shelx_hkl_checksum              78973
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.709