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_7131393
_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 H13 Br O2'
_chemical_formula_sum            'C11 H13 Br O2'
_chemical_formula_weight         257.12
_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             2022-12-01
_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                 99.3160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.69110(10)
_cell_length_b                   19.8327(3)
_cell_length_c                   8.71150(10)
_cell_measurement_reflns_used    11563
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.3250
_cell_measurement_theta_min      5.5910
_cell_volume                     1140.79(3)
_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
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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     36.00  68.00   0.50    0.50    --  107.75 -61.00-180.00   64
  2  \w     36.00  68.00   0.50    0.50    --  107.75 -61.00 -90.00   64
  3  \w     36.00  68.00   0.50    0.50    --  107.75 -61.00 -30.00   64
  4  \w    -28.00  24.00   0.50    0.50    --   50.71 -19.00-120.00  104
  5  \w    -28.00  24.00   0.50    0.50    --   50.71 -19.00  90.00  104
  6  \w     36.00  68.00   0.50    0.50    --  107.75 -61.00 150.00   64
  7  \w     36.00  68.00   0.50    0.50    --  107.75 -61.00  90.00   64
  8  \w     36.00  68.00   0.50    0.50    --  107.75 -61.00  60.00   64
  9  \w     35.00 109.00   0.50    0.50    --  107.75-111.00  60.00  148
 10  \w     35.00 109.00   0.50    0.50    --  107.75-111.00-120.00  148
 11  \w     35.00 109.00   0.50    0.50    --  107.75-111.00-180.00  148
 12  \w     32.00 135.00   0.50    0.50    --  107.75 -88.00  59.00  206
 13  \w     35.00 109.00   0.50    0.50    --  107.75-111.00  90.00  148
 14  \w    -25.00  78.00   0.50    0.50    --   50.71 -88.00  59.00  206
 15  \w     31.00 106.00   0.50    0.50    --  107.75 -94.00 150.00  150
 16  \w     96.00 148.00   0.50    0.50    --  107.75  15.00 120.00  104
 17  \w     81.00 124.00   0.50    0.50    --   50.71  77.00 150.00   86
 18  \w     97.00 128.00   0.50    0.50    --  107.75  61.00 120.00   62
 19  \w    136.00 173.00   0.50    0.50    --  107.75  61.00 120.00   74
 20  \w     94.00 175.00   0.50    0.50    --  107.75  45.00 150.00  162
 21  \w    115.00 141.00   0.50    0.50    --  107.75  30.00 150.00   52
 22  \w    102.00 138.00   0.50    0.50    --  107.75  15.00 -30.00   72
 23  \w    146.00 174.00   0.50    0.50    --  107.75  15.00 -30.00   56
 24  \w     85.00 175.00   0.50    0.50    --  107.75  77.00-150.00  180
 25  \w     94.00 175.00   0.50    0.50    --  107.75  45.00-120.00  162
 26  \w     81.00 124.00   0.50    0.50    --   50.71  77.00-150.00   86
 27  \w     76.00 124.00   0.50    0.50    --   50.71 125.00 -90.00   96
 28  \w     76.00 124.00   0.50    0.50    --   50.71 125.00 -60.00   96
 29  \w     83.00 175.00   0.50    0.50    --  107.75 111.00  60.00  184
 30  \w    119.00 175.00   0.50    0.50    --  107.75  88.00 176.00  112
;
_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      -0.2085216000
_diffrn_orient_matrix_UB_12      -0.0322319000
_diffrn_orient_matrix_UB_13      -0.0562698000
_diffrn_orient_matrix_UB_21      -0.0624403000
_diffrn_orient_matrix_UB_22      0.0620718000
_diffrn_orient_matrix_UB_23      -0.1028479000
_diffrn_orient_matrix_UB_31      0.0837087000
_diffrn_orient_matrix_UB_32      -0.0339318000
_diffrn_orient_matrix_UB_33      -0.1355061000
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12788
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.440
_diffrn_reflns_theta_min         4.459
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75728
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.089
_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     130
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0471P)^2^+1.1062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2305
_reflns_number_total             2325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00945a2.cif
_cod_data_source_block           IB007_Sarpong
_cod_depositor_comments
'Adding full bibliography for 7131392--7131393.cif.'
_cod_database_code               7131393
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C N O H'
_shelx_estimated_absorpt_t_max   0.677
_shelx_estimated_absorpt_t_min   0.411
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              34617
_shelx_hkl_checksum              26436
_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 3.865
_oxdiff_exptl_absorpt_empirical_full_min 0.668