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_1575617
_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         'C17 H19 Br O3'
_chemical_formula_sum            'C17 H19 Br O3'
_chemical_formula_weight         351.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-24
_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                 99.531(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8852(3)
_cell_length_b                   12.7120(4)
_cell_length_c                   12.5984(3)
_cell_measurement_reflns_used    5732
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.5880
_cell_measurement_theta_min      3.5350
_cell_volume                     1561.27(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 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     75.00 110.00   0.50    0.05    --   42.91 125.00   0.00   70
  2  \w     79.00 109.00   0.50    0.05    --   42.91 125.00 -90.00   60
  3  \w    111.00 158.00   0.50    0.10    --  112.36 102.00  72.00   94
  4  \w     79.00 112.00   0.50    0.10    --  112.36 125.00 150.00   66
  5  \w    141.00 167.00   0.50    0.10    --  112.36 125.00 150.00   52
  6  \w     90.00 177.00   0.50    0.10    --  112.36  61.00  30.00  174
  7  \w     -9.00  17.00   0.50    0.05    --   42.91-102.00 -30.00   52
  8  \w     37.00  74.00   0.50    0.05    --   42.91-102.00 -30.00   74
  9  \w     62.00 106.00   0.50    0.10    --  112.36-102.00 -30.00   88
 10  \w     41.00  71.00   0.50    0.10    --  112.36 -61.00 -60.00   60
 11  \w     41.00  67.00   0.50    0.10    --  112.36 -61.00 -30.00   52
 12  \w     40.00  98.00   0.50    0.10    --  112.36 -77.00 120.00  116
 13  \w     43.00  70.00   0.50    0.10    --  112.36 -61.00  30.00   54
 14  \w     39.00  65.00   0.50    0.10    --  112.36 -61.00   0.00   52
 15  \w    -36.00  26.00   0.50    0.05    --   42.91 -19.00-180.00  124
 16  \w    -82.00  -7.00   0.50    0.05    --  -42.91 102.00  72.00  150
 17  \w   -105.00 -61.00   0.50    0.10    -- -106.00 102.00  72.00   88
 18  \w   -154.00-103.00   0.50    0.10    -- -106.00 -30.00-120.00  102
 19  \w   -163.00 -89.00   0.50    0.10    -- -106.00-102.00 -30.00  148
 20  \w    -26.00  38.00   0.50    0.05    --  -42.91  19.00   0.00  128
 21  \w    -70.00 -35.00   0.50    0.10    -- -106.00  61.00 -60.00   70
 22  \w    -71.00 -46.00   0.50    0.10    -- -106.00  61.00 -90.00   50
 23  \w    -69.00 -35.00   0.50    0.10    -- -106.00  61.00-120.00   68
;
_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      -0.0587535000
_diffrn_orient_matrix_UB_12      0.1083438000
_diffrn_orient_matrix_UB_13      -0.0383819000
_diffrn_orient_matrix_UB_21      0.1464857000
_diffrn_orient_matrix_UB_22      0.0414741000
_diffrn_orient_matrix_UB_23      0.0005231000
_diffrn_orient_matrix_UB_31      -0.0076443000
_diffrn_orient_matrix_UB_32      -0.0349970000
_diffrn_orient_matrix_UB_33      -0.1179172000
_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  0.0555
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7781
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        65.085
_diffrn_reflns_theta_max         65.085
_diffrn_reflns_theta_min         4.536
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.652
_exptl_absorpt_correction_T_max  0.455
_exptl_absorpt_correction_T_min  0.020
_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    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.686
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.465
_refine_diff_density_min         -1.058
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0752
_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^)+(0.1605P)^2^+1.5430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2192
_refine_ls_wR_factor_ref         0.2225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2492
_reflns_number_total             2659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04790k2.cif
_cod_data_source_block           20241024ay1_auto
_cod_depositor_comments
'Adding full bibliography for 1575616--1575620.cif.'
_cod_database_code               1575617
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H Br O'
_reflns_odcompleteness_completeness 100.00
_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:
 C6(H6), C4(H4), C7(H7), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C11(H11A,H11B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C16(H16), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              80433
_shelx_hkl_checksum              6350
_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 2.036
_oxdiff_exptl_absorpt_empirical_full_min 0.444