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_1575616
_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         '2(C10 H13 Br O2)'
_chemical_formula_sum            'C20 H26 Br2 O4'
_chemical_formula_weight         490.23
_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             2024-05-28
_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                 91.188(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1581(2)
_cell_length_b                   27.6045(5)
_cell_length_c                   8.6565(2)
_cell_measurement_reflns_used    14354
_cell_measurement_temperature    150
_cell_measurement_theta_max      77.2190
_cell_measurement_theta_min      3.1500
_cell_volume                     1949.03(7)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     91.00 178.00   0.50    0.05    --  112.36  61.00  30.00  174
  2  \w    140.00 178.00   0.50    0.05    --  112.36  15.00  60.00   76
  3  \w     63.00 117.00   0.50    0.05    --  112.36  15.00  60.00  108
  4  \w    -21.00  26.00   0.50    0.05    --   43.16 -19.00  90.00   94
  5  \w    -33.00   1.00   0.50    0.05    --   43.16 -19.00  60.00   68
  6  \w    -30.00  40.00   0.50    0.05    --   43.16 -38.00 -90.00  140
  7  \w     80.00 105.00   0.50    0.05    --  112.36 -77.00 -90.00   50
  8  \w     40.00  66.00   0.50    0.05    --  112.36 -61.00-120.00   52
  9  \w     40.00  69.00   0.50    0.05    --  112.36 -77.00 -90.00   58
 10  \w     41.00  69.00   0.50    0.05    --  112.36 -61.00 -90.00   56
 11  \w     41.00  70.00   0.50    0.05    --  112.36 -61.00 -60.00   58
 12  \w     73.00  99.00   0.50    0.05    --  112.36 -77.00   0.00   52
 13  \w     39.00  65.00   0.50    0.05    --  112.36 -77.00   0.00   52
 14  \w     42.00  68.00   0.50    0.05    --  112.36 -61.00   0.00   52
 15  \w     70.00 102.00   0.50    0.05    --  112.36 -95.00 -90.00   64
 16  \w     41.00  92.00   0.50    0.05    --  112.36-113.00-140.00  102
 17  \w     13.00  97.00   0.50    0.05    --   43.16-125.00-180.00  168
 18  \w     53.00  78.00   0.50    0.05    --   43.16-113.00-140.00   50
 19  \w      8.00  46.00   0.50    0.05    --   43.16-113.00-140.00   76
 20  \w     79.00 104.00   0.50    0.05    --  112.36 -95.00  90.00   50
 21  \w     73.00 118.00   0.50    0.05    --   43.16 125.00 150.00   90
 22  \w    105.00 130.00   0.50    0.05    --  112.36 113.00 -48.00   50
 23  \w     74.00 109.00   0.50    0.05    --   43.16 125.00-120.00   70
 24  \w   -106.00 -72.00   0.50    0.05    -- -106.00 113.00 -48.00   68
 25  \w   -109.00 -56.00   0.50    0.05    -- -106.00 125.00-150.00  106
 26  \w   -123.00 -98.00   0.50    0.05    -- -106.00 141.00-119.35   50
 27  \w    -90.00 -41.00   0.50    0.05    --  -43.16 125.00   0.00   98
 28  \w   -126.00 -94.00   0.50    0.05    -- -106.00 144.00 138.98   64
 29  \w   -102.00 -32.00   0.50    0.05    -- -106.00 125.00 120.00  140
 30  \w    -85.00 -51.00   0.50    0.05    -- -106.00 144.00 138.98   68
 31  \w   -105.00 -78.00   0.50    0.05    -- -106.00 125.00   0.00   54
 32  \w    -44.00 -19.00   0.50    0.05    --  -43.16 113.00 -48.00   50
 33  \w    -69.00 -32.00   0.50    0.05    -- -106.00  61.00-120.00   74
 34  \w    -62.00 -33.00   0.50    0.05    -- -106.00  61.00  90.00   58
 35  \w    -71.00 -34.00   0.50    0.05    -- -106.00  61.00 150.00   74
 36  \w   -128.00-102.00   0.50    0.05    -- -106.00 -45.00 120.00   52
 37  \w   -176.00-138.00   0.50    0.05    -- -106.00 -45.00 120.00   76
 38  \w   -115.00 -22.00   0.50    0.05    --  -43.16 -57.00 120.00  186
 39  \w   -176.00 -84.00   0.50    0.05    -- -106.00 -30.00  30.00  184
 40  \w   -175.00 -84.00   0.50    0.05    -- -106.00 -45.00 -60.00  182
 41  \w   -177.00 -84.00   0.50    0.05    -- -106.00 -45.00-120.00  186
 42  \w   -148.00-109.00   0.50    0.05    -- -106.00-113.00-140.00   78
;
_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      -0.1281011000
_diffrn_orient_matrix_UB_12      0.0046687000
_diffrn_orient_matrix_UB_13      -0.1323376000
_diffrn_orient_matrix_UB_21      -0.0155134000
_diffrn_orient_matrix_UB_22      0.0546248000
_diffrn_orient_matrix_UB_23      0.0332049000
_diffrn_orient_matrix_UB_31      0.1379209000
_diffrn_orient_matrix_UB_32      0.0104784000
_diffrn_orient_matrix_UB_33      -0.1142922000
_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  0.0628
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19654
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         3.202
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.466
_exptl_absorpt_correction_T_max  0.208
_exptl_absorpt_correction_T_min  0.021
_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    1.671
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0954P)^2^+0.4250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3311
_reflns_number_total             3441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04790k2.cif
_cod_data_source_block           20240528y4_auto
_cod_depositor_comments
'Adding full bibliography for 1575616--1575620.cif.'
_cod_database_code               1575616
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O Br'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C16(H16), C1(H1), C6(H6), C18(H18), C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C5(H5A,H5B), C4(H4A,H4B), C9(H9A,H9B), C19(H19A,H19B),
 C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_shelx_res_checksum              91383
_shelx_hkl_checksum              22136
_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 1.998
_oxdiff_exptl_absorpt_empirical_full_min 0.513