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_1566743
_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         'C45 H34 O2'
_chemical_formula_sum            'C45 H34 O2'
_chemical_formula_weight         606.72
_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     direct
_audit_creation_date             2020-06-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2021-10-14 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                101.7874(13)
_cell_angle_beta                 98.9295(13)
_cell_angle_gamma                108.9135(15)
_cell_formula_units_Z            2
_cell_length_a                   10.26982(17)
_cell_length_b                   12.9000(2)
_cell_length_c                   13.4161(2)
_cell_measurement_reflns_used    12842
_cell_measurement_temperature    123
_cell_measurement_theta_max      76.2990
_cell_measurement_theta_min      3.4700
_cell_volume                     1598.21(5)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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    -26.00  60.00   0.50    0.16    --   47.45 -19.00  60.00  172
  2  \w     35.00 121.00   0.50    0.16    --   47.45  37.00  60.00  172
  3  \w     81.00 119.00   0.50    0.16    --   47.45 120.00 -23.00   76
  4  \w     61.00  86.00   0.50    0.16    --   47.45 154.00 134.00   50
  5  \w     78.00 104.00   0.50    0.63    --   70.50 154.00 134.00   52
  6  \w    -26.00  60.00   0.50    0.16    --   47.45 -37.00 150.00  172
  7  \w     45.00  70.00   0.50    0.16    --   47.45-154.00  94.00   50
  8  \w     79.00 105.00   0.50    0.63    --   70.50-154.00  94.00   52
  9  \w     36.00  61.00   0.50    0.16    --   47.45-120.00-107.00   50
 10  \w     36.00  61.00   0.50    0.63    --   70.50-120.00-107.00   50
 11  \w     -4.00  83.00   0.50    0.63    --   70.50 -19.00-150.00  174
 12  \w    -86.00 -59.00   0.50    0.16    --  -47.45 154.00 134.00   54
 13  \w    -85.00 -36.00   0.50    0.16    --  -47.45 120.00 -23.00   98
 14  \w    -58.00 -33.00   0.50    0.63    -- -106.00 120.00 -23.00   50
 15  \w    -61.00 -36.00   0.50    0.63    -- -106.00 125.00   0.00   50
 16  \w   -105.00 -55.00   0.50    0.63    -- -106.00  57.00   0.00  100
 17  \w   -109.00 -84.00   0.50    0.63    -- -106.00 154.00 134.00   50
 18  \w    -84.00 -33.00   0.50    0.63    -- -106.00 125.00 150.00  102
 19  \w   -116.00 -89.00   0.50    0.63    -- -106.00 125.00 150.00   54
 20  \w   -118.00 -37.00   0.50    0.63    -- -106.00  37.00 150.00  162
 21  \w   -113.00 -67.00   0.50    0.63    -- -106.00 125.00   0.00   92
 22  \w   -117.00 -35.00   0.50    0.63    -- -106.00 125.00 -30.00  164
 23  \w    -66.00 -34.00   0.50    0.63    -- -106.00  77.00-180.00   64
 24  \w    -97.00 -71.00   0.50    0.63    -- -106.00  77.00-180.00   52
 25  \w   -118.00 -38.00   0.50    0.63    -- -106.00  57.00-180.00  160
 26  \w   -117.00 -33.00   0.50    0.63    -- -106.00 125.00-180.00  168
 27  \w   -104.00 -39.00   0.50    0.63    -- -106.00 125.00 -90.00  130
 28  \w   -119.00 -32.00   0.50    0.63    -- -106.00  19.00 -30.00  174
 29  \w   -114.00 -34.00   0.50    0.63    -- -106.00  37.00   0.00  160
 30  \w   -131.00 -85.00   0.50    0.63    -- -106.00 -77.00   0.00   92
 31  \w   -133.00-108.00   0.50    0.63    -- -106.00-154.00  94.00   50
 32  \w   -109.00 -84.00   0.50    0.16    --  -47.45-154.00  94.00   50
 33  \w   -152.00 -92.00   0.50    0.63    -- -106.00 -57.00   0.00  120
 34  \w   -109.00 -76.00   0.50    0.63    -- -106.00-120.00-107.00   66
 35  \w   -119.00 -93.00   0.50    0.16    --  -47.45-120.00-107.00   52
 36  \w   -167.00-120.00   0.50    0.63    -- -106.00 -57.00 -30.00   94
 37  \w   -169.00-137.00   0.50    0.63    -- -106.00 -77.00   0.00   64
;
_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      -0.0934068000
_diffrn_orient_matrix_UB_12      0.0577787000
_diffrn_orient_matrix_UB_13      -0.0488591000
_diffrn_orient_matrix_UB_21      -0.0157018000
_diffrn_orient_matrix_UB_22      0.0515463000
_diffrn_orient_matrix_UB_23      0.1095847000
_diffrn_orient_matrix_UB_31      0.1330337000
_diffrn_orient_matrix_UB_32      0.1059176000
_diffrn_orient_matrix_UB_33      0.0140895000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20358
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.578
_diffrn_reflns_theta_min         3.466
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81429
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0874P)^2^+0.3087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5620
_reflns_number_total             6464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01394k2.cif
_cod_data_source_block           x200601_ks01-127-1_oet
_cod_original_cell_volume        1598.20(5)
_cod_database_code               1566743
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C45 H34 O2'
_chemical_oxdiff_usercomment     'X200601_KS01-127-1_OEt C45 H34 O2'
_diffrn_oxdiff_ac3_digest_frames
;
01a28d98283cd7cec14d53e333df96c548000558e9b
;
_diffrn_oxdiff_ac3_digest_hkl
;
012021433e9eaab374caee9443bf3d7ab33b0f
;
_reflns_odcompleteness_completeness 99.93
_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
2.a Ternary CH refined with riding coordinates:
 C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C12(H12), C47(H47), C13(H13), C6(H6), C19(H19), C29(H29),
 C35(H35), C21(H21), C46(H46), C5(H5), C31(H31), C10(H10), C44(H44), C33(H33),
 C45(H45), C25(H25), C11(H11), C23(H23), C27(H27), C34(H34), C43(H43), C32(H32),
  C28(H28), C22(H22), C26(H26), C20(H20)
2.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C)
;
_shelx_res_checksum              83621
_shelx_hkl_checksum              83858
_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 3.261
_oxdiff_exptl_absorpt_empirical_full_min 0.364