Nickel-Catalyzed Skeletal Transformation of Tropone Derivatives via C–C Bond Activation: Catalyst-Controlled Access to Diverse Ring Systems
Kodama, Takuya; Saito, Kanako; Tobisu, Mamoru; Chemical Science  (2022) –; doi:10.1039/D2SC01394K

data_1566744
_publ_section_title
;
 Nickel-Catalyzed Skeletal Transformation of Tropone Derivatives via C--C
 Bond Activation: Catalyst-Controlled Access to Diverse Ring Systems
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01394K
_journal_year                    2022
_chemical_formula_moiety         'C41 H26 O'
_chemical_formula_sum            'C41 H26 O'
_chemical_formula_weight         534.62
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-14 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                103.578(2)
_cell_angle_beta                 103.147(2)
_cell_angle_gamma                112.391(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4122(3)
_cell_length_b                   11.1627(3)
_cell_length_c                   14.3485(3)
_cell_measurement_reflns_used    8950
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.0450
_cell_measurement_theta_min      4.5400
_cell_volume                     1402.62(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_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     17.00  46.00   0.50    0.50    --   42.80  77.00   0.00   58
  2  \w     52.00 111.00   0.50    0.50    --   42.80  77.00   0.00  118
  3  \w     89.00 114.00   0.50    2.00    --   76.50 118.00 -71.00   50
  4  \w     71.00 116.00   0.50    0.50    --   42.80 125.00-120.00   90
  5  \w     74.00 104.00   0.50    0.50    --   42.80 125.00-180.00   60
  6  \w     73.00 100.00   0.50    0.50    --   42.80 159.00  81.00   54
  7  \w     75.00 100.00   0.50    2.00    --   76.50 159.00  81.00   50
  8  \w     73.00 105.00   0.50    0.50    --   42.80 125.00 150.00   64
  9  \w    -56.00 -30.00   0.50    2.00    -- -106.00  37.00 -30.00   52
 10  \w    -61.00 -35.00   0.50    2.00    -- -106.00  19.00 -90.00   52
 11  \w    -63.00 -25.00   0.50    2.00    -- -106.00  19.00-150.00   76
 12  \w    -80.00 -54.00   0.50    2.00    -- -106.00  57.00 -60.00   52
 13  \w   -105.00 -80.00   0.50    2.00    -- -106.00 118.00 -71.00   50
 14  \w    -97.00 -32.00   0.50    2.00    -- -106.00 125.00-120.00  130
 15  \w    -68.00 -37.00   0.50    2.00    -- -106.00 125.00 -30.00   62
 16  \w    -71.00 -32.00   0.50    2.00    -- -106.00 125.00  60.00   78
 17  \w    -87.00 -50.00   0.50    2.00    -- -106.00  57.00 120.00   74
 18  \w   -107.00 -32.00   0.50    2.00    -- -106.00 125.00 150.00  150
 19  \w    -82.00 -43.00   0.50    0.50    --  -42.80 159.00  81.00   78
 20  \w   -113.00 -85.00   0.50    2.00    -- -106.00 159.00  81.00   56
 21  \w   -116.00 -33.00   0.50    2.00    -- -106.00 125.00  90.00  166
 22  \w    -87.00 -33.00   0.50    2.00    -- -106.00 129.00  26.18  108
 23  \w    -89.00 -63.00   0.50    2.00    -- -106.00 125.00   0.00   52
 24  \w   -107.00 -81.00   0.50    2.00    -- -106.00  77.00 -60.00   52
 25  \w   -103.00 -78.00   0.50    2.00    -- -106.00  77.00 -30.00   50
 26  \w   -104.00 -64.00   0.50    2.00    -- -106.00  37.00 -30.00   80
 27  \w   -101.00 -75.00   0.50    2.00    -- -106.00 -19.00 -30.00   52
 28  \w   -118.00 -92.00   0.50    2.00    -- -106.00  61.00 -24.74   52
 29  \w   -120.00 -87.00   0.50    2.00    -- -106.00  19.00 -90.00   66
 30  \w   -103.00 -78.00   0.50    2.00    -- -106.00  19.00-150.00   50
 31  \w   -103.00 -44.00   0.50    2.00    -- -106.00  77.00-180.00  118
 32  \w    -93.00  -5.00   0.50    0.50    --  -42.80 118.00 -71.00  176
 33  \w   -113.00 -80.00   0.50    2.00    -- -106.00 125.00 -60.00   66
 34  \w   -116.00 -90.00   0.50    2.00    -- -106.00 125.00 -30.00   52
 35  \w   -118.00 -93.00   0.50    2.00    -- -106.00 129.00  26.18   50
 36  \w   -113.00 -88.00   0.50    2.00    -- -106.00 125.00  60.00   50
 37  \w   -108.00 -38.00   0.50    2.00    -- -106.00  92.00  89.39  140
 38  \w   -121.00 -58.00   0.50    2.00    -- -106.00  57.00  90.00  126
 39  \w   -128.00 -29.00   0.50    2.00    -- -106.00  37.00  60.00  198
 40  \w    -78.00 -36.00   0.50    0.50    --  -42.80 -77.00  90.00   84
 41  \w   -106.00 -81.00   0.50    0.50    --  -42.80-159.00  48.00   50
 42  \w      7.00  73.00   0.50    0.50    --   42.80-118.00-158.00  132
 43  \w     35.00  60.00   0.50    2.00    --   76.50-118.00-158.00   50
 44  \w     68.00 115.00   0.50    0.50    --   42.80-159.00  48.00   94
 45  \w     59.00  84.00   0.50    2.00    --   76.50-159.00  48.00   50
 46  \w   -107.00 -82.00   0.50    2.00    -- -106.00-125.00-180.00   50
 47  \w   -135.00-110.00   0.50    2.00    -- -106.00 -57.00 -60.00   50
 48  \w   -139.00 -84.00   0.50    2.00    -- -106.00 -99.00 -90.00  110
 49  \w   -105.00 -79.00   0.50    2.00    -- -106.00-125.00 -30.00   52
 50  \w   -129.00-104.00   0.50    2.00    -- -106.00-159.00  48.00   50
 51  \w   -116.00 -82.00   0.50    0.50    --  -42.80 -77.00  90.00   68
 52  \w   -115.00 -86.00   0.50    0.50    --  -42.80-125.00 120.00   58
 53  \w   -161.00-108.00   0.50    2.00    -- -106.00 -37.00  60.00  106
 54  \w   -125.00 -89.00   0.50    2.00    -- -106.00  57.00 -60.00   72
 55  \w   -120.00 -95.00   0.50    2.00    -- -106.00  77.00 -90.00   50
 56  \w   -118.00 -70.00   0.50    2.00    -- -106.00  37.00-150.00   96
 57  \w   -106.00 -77.00   0.50    2.00    -- -106.00 -19.00-150.00   58
 58  \w   -157.00 -87.00   0.50    2.00    -- -106.00 -77.00-150.00  140
 59  \w   -170.00-113.00   0.50    2.00    -- -106.00-118.00-158.00  114
 60  \w   -160.00 -80.00   0.50    2.00    -- -106.00-125.00 -90.00  160
 61  \w   -161.00-109.00   0.50    2.00    -- -106.00 -37.00-180.00  104
 62  \w   -170.00-136.00   0.50    2.00    -- -106.00-125.00-120.00   68
 63  \w   -166.00-140.00   0.50    2.00    -- -106.00-125.00-150.00   52
 64  \w   -177.00-141.00   0.50    2.00    -- -106.00-125.00-180.00   72
 65  \w   -175.00-150.00   0.50    2.00    -- -106.00 -57.00 -90.00   50
 66  \w   -175.00 -95.00   0.50    2.00    -- -106.00 -19.00 -90.00  160
 67  \w   -165.00-140.00   0.50    2.00    -- -106.00 -99.00   0.00   50
 68  \w   -177.00-120.00   0.50    2.00    -- -106.00 -19.00 -30.00  114
 69  \w   -128.00-103.00   0.50    2.00    -- -106.00  90.00  74.82   50
 70  \w   -121.00 -96.00   0.50    2.00    -- -106.00 131.00-136.55   50
 71  \w   -108.00 -44.00   0.50    2.00    -- -106.00 125.00-180.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1056643000
_diffrn_orient_matrix_UB_12      0.0502578000
_diffrn_orient_matrix_UB_13      -0.0518955000
_diffrn_orient_matrix_UB_21      0.0053545000
_diffrn_orient_matrix_UB_22      -0.0680423000
_diffrn_orient_matrix_UB_23      -0.1047490000
_diffrn_orient_matrix_UB_31      -0.1343443000
_diffrn_orient_matrix_UB_32      -0.1355649000
_diffrn_orient_matrix_UB_33      -0.0163299000
_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  0.1002
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23396
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.517
_diffrn_reflns_theta_min         3.386
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0939P)^2^+0.0908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4510
_reflns_number_total             5623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01394k2.cif
_cod_data_source_block           tk01-151-f2-4
_cod_original_cell_volume        1402.62(7)
_cod_database_code               1566744
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C41 H26 O1'
_chemical_oxdiff_usercomment     'TK01-151-f2-4 C41 H26 O1'
_reflns_odcompleteness_completeness 98.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C35(H35), C34(H34), C40(H40), C31(H31), C29(H29), C23(H23), C37(H37),
 C33(H33), C25(H25), C16(H16), C27(H27), C24(H24), C32(H32), C41(H41), C28(H28),
  C12(H12), C39(H39), C38(H38), C22(H22), C14(H14), C15(H15), C18(H18),
 C21(H21), C13(H13), C20(H20), C19(H19)
;
_shelx_res_checksum              28103
_shelx_hkl_checksum              77476
_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 3.746
_oxdiff_exptl_absorpt_empirical_full_min 0.291