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_1575618
_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         'C16 H18 O2'
_chemical_formula_sum            'C16 H18 O2'
_chemical_formula_weight         242.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-20
_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                90
_cell_angle_beta                 94.587(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2890(3)
_cell_length_b                   6.6058(2)
_cell_length_c                   15.8019(5)
_cell_measurement_reflns_used    4578
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.8240
_cell_measurement_theta_min      4.6710
_cell_volume                     1278.67(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.958
_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    105.00 178.00   0.50    0.20    --  107.56  61.00-180.00  146
  2  \w    134.00 160.00   0.50    0.20    --  107.56  45.00-150.00   52
  3  \w     95.00 131.00   0.50    0.20    --  107.56  45.00-150.00   72
  4  \w     71.00 138.00   0.50    0.20    --  107.56  18.00 136.00  134
  5  \w     13.00 119.00   0.50    0.10    --   43.13  18.00 136.00  212
  6  \w   -119.00 -14.00   0.50    0.10    --  -43.13 -18.00 -31.00  210
  7  \w    -70.00 -34.00   0.50    0.20    -- -106.00  61.00  90.00   72
  8  \w    -68.00 -43.00   0.50    0.20    -- -106.00  61.00 120.00   50
  9  \w    -18.00   7.00   0.50    0.10    --  -43.13  18.00 136.00   50
 10  \w   -163.00 -73.00   0.50    0.20    -- -106.00 -18.00 -31.00  180
 11  \w    -70.00 -33.00   0.50    0.20    -- -106.00  61.00-180.00   74
 12  \w    -71.00 -33.00   0.50    0.20    -- -106.00  61.00-120.00   76
 13  \w   -111.00 -85.00   0.50    0.20    -- -106.00 125.00-120.00   52
 14  \w    -71.00 -32.00   0.50    0.20    -- -106.00 125.00-120.00   78
 15  \w    -97.00 -28.00   0.50    0.10    --  -43.13 125.00-150.00  138
 16  \w     -5.00  20.00   0.50    0.10    --   43.13 -18.00 -31.00   50
 17  \w     47.00  95.00   0.50    0.20    --  107.56 -95.00 -60.00   96
 18  \w     41.00  69.00   0.50    0.20    --  107.56 -61.00 -60.00   56
 19  \w     36.00  71.00   0.50    0.20    --  107.56 -61.00-150.00   70
 20  \w     45.00  70.00   0.50    0.20    --  107.56 -77.00-180.00   50
;
_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      -0.1072990000
_diffrn_orient_matrix_UB_12      0.0336125000
_diffrn_orient_matrix_UB_13      0.0421905000
_diffrn_orient_matrix_UB_21      -0.0595347000
_diffrn_orient_matrix_UB_22      0.0445765000
_diffrn_orient_matrix_UB_23      -0.0875530000
_diffrn_orient_matrix_UB_31      -0.0276609000
_diffrn_orient_matrix_UB_32      -0.2264159000
_diffrn_orient_matrix_UB_33      -0.0108784000
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7219
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.177
_diffrn_reflns_theta_min         4.392
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.577
_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    1.259
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.638
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0671P)^2^+0.3231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2250
_reflns_number_total             2534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04790k2.cif
_cod_data_source_block           20220920y_auto
_cod_depositor_comments
'Adding full bibliography for 1575616--1575620.cif.'
_cod_database_code               1575618
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.92
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C13(H13), C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              2359
_shelx_hkl_checksum              22582
_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 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.680