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_1566748
_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         'C26 H28 N2 Ni O3, 0.5(C7 H8)'
_chemical_formula_sum            'C29.5 H32 N2 Ni O3'
_chemical_formula_weight         521.28
_chemical_properties_physical    Oxygen-sensitive
_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             2020-02-03
_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                90
_cell_angle_beta                 106.854(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.0889(5)
_cell_length_b                   15.9034(4)
_cell_length_c                   18.9504(7)
_cell_measurement_reflns_used    18930
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.0000
_cell_measurement_theta_min      2.5020
_cell_volume                     5505.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.754
_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     18.00  67.00   0.50   13.02    --   -5.34  59.00-116.00   98
  2  \w    -26.00  21.00   0.50   13.02    --   -5.34 -99.00 -60.00   94
  3  \w    -15.00  28.00   0.50   13.02    --   -5.34 -99.00-180.00   86
  4  \w     -9.00  28.00   0.50   13.02    --   -5.34 -99.00  90.00   74
;
_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      -0.0051492000
_diffrn_orient_matrix_UB_12      0.0095582000
_diffrn_orient_matrix_UB_13      -0.0377106000
_diffrn_orient_matrix_UB_21      0.0053444000
_diffrn_orient_matrix_UB_22      0.0433261000
_diffrn_orient_matrix_UB_23      0.0089070000
_diffrn_orient_matrix_UB_31      0.0380995000
_diffrn_orient_matrix_UB_32      -0.0047884000
_diffrn_orient_matrix_UB_33      0.0052171000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.754
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34156
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.021
_diffrn_reflns_theta_min         2.207
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         13240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0545P)^2^+1.8997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10955
_reflns_number_total             13240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01394k2.cif
_cod_data_source_block           x200202_ks-ni(co)3(imesme)
_cod_depositor_comments
;

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C59 H64 N4 Ni2 O6'
_cod_original_formula_weight         1042.56
_cod_original_formula_moiety         '2(C26 H28 N2 Ni O3), C7 H8'
_cod_original_formula_units_Z            4
_cod_database_code               1566748
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C26 H29 N2 Ni1 O3'
_chemical_oxdiff_usercomment
'X200202_KS-Ni(CO)3(IMesMe) C26 H29 N2 Ni1 O3'
_diffrn_oxdiff_ac3_digest_frames
;
01388db818e3d179c31cbd78033cfd57ec00025a525
;
_diffrn_oxdiff_ac3_digest_hkl
;
01d5c05c2a0d11ae4f980399e51c3a6b0888e4
;
_reflns_odcompleteness_completeness 96.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C36(H36), C45(H45), C34(H34), C18(H18), C47(H47), C7(H7), C5(H5),
 C68(H68), C67(H67), C66(H66), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C51(H51A,H51B,H51C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C55(H55A,H55B,H55C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C), C50(H50A,H50B,H50C), C56(H56A,H56B,H56C), C26(H26A,H26B,H26C),
 C20(H20A,H20B,H20C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C), C49(H49A,H49B,
 H49C), C27(H27A,H27B,H27C), C0AA(H0AA,H0AB,H0AC)
;
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.634