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_1566742
_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         'C23 H16 O'
_chemical_formula_sum            'C23 H16 O'
_chemical_formula_weight         308.36
_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     iterative
_audit_creation_date             2021-10-13
_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                76.1520(10)
_cell_angle_beta                 85.8840(10)
_cell_angle_gamma                86.2040(10)
_cell_formula_units_Z            16
_cell_length_a                   10.99710(10)
_cell_length_b                   21.3867(2)
_cell_length_c                   28.8610(2)
_cell_measurement_reflns_used    38794
_cell_measurement_temperature    123
_cell_measurement_theta_max      75.8900
_cell_measurement_theta_min      3.3310
_cell_volume                     6565.14(10)
_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    'olex2.solve 1.3 (Bourhis et al., 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 0.962
_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    -24.00  67.00   0.50    0.37    --   47.45 -73.00 -52.00  182
  2  \w     79.00 104.00   0.50    1.49    --   70.50 -99.00 -60.00   50
  3  \w     21.00  46.00   0.50    1.49    --   70.50 -73.00 -52.00   50
  4  \w     19.00  58.00   0.50    1.49    --   70.50 -99.00 -60.00   78
  5  \w    -22.00  18.00   0.50    0.37    --   47.45 -37.00-180.00   80
  6  \w    -95.00 -20.00   0.50    0.37    --  -47.45 125.00  30.00  150
  7  \w    -61.00  -4.00   0.50    0.37    --  -47.45  73.00  76.00  114
  8  \w     74.00 107.00   0.50    0.37    --   47.45  73.00  76.00   66
  9  \w     53.00  79.00   0.50    1.49    --   70.50  73.00  76.00   52
 10  \w     71.00 101.00   0.50    0.37    --   47.45 125.00 -60.00   60
 11  \w     72.00 119.00   0.50    0.37    --   47.45 125.00-180.00   94
 12  \w    -58.00 -33.00   0.50    1.49    -- -106.00  37.00 -60.00   50
 13  \w    -75.00 -50.00   0.50    1.49    -- -106.00  77.00-150.00   50
 14  \w    -77.00 -43.00   0.50    1.49    -- -106.00 125.00 -60.00   68
 15  \w    -76.00 -33.00   0.50    1.49    -- -106.00 125.00  30.00   86
 16  \w    -97.00 -71.00   0.50    1.49    -- -106.00  37.00 -60.00   52
 17  \w   -124.00 -98.00   0.50    1.49    -- -106.00  77.00-150.00   52
 18  \w   -115.00 -33.00   0.50    1.49    -- -106.00 125.00-120.00  164
 19  \w   -115.00 -46.00   0.50    1.49    -- -106.00 125.00-150.00  138
 20  \w   -119.00 -59.00   0.50    1.49    -- -106.00  19.00  30.00  120
 21  \w   -117.00 -26.00   0.50    0.37    --  -47.45 -73.00 -52.00  182
 22  \w   -120.00 -71.00   0.50    0.37    --  -47.45-125.00  60.00   98
 23  \w   -128.00 -95.00   0.50    1.49    -- -106.00 -37.00  90.00   66
 24  \w   -138.00 -93.00   0.50    1.49    -- -106.00 -19.00 150.00   90
 25  \w   -121.00 -56.00   0.50    1.49    -- -106.00  57.00  90.00  130
 26  \w   -117.00 -38.00   0.50    1.49    -- -106.00  73.00  76.00  158
 27  \w   -117.00 -34.00   0.50    1.49    -- -106.00 125.00  90.00  166
 28  \w   -117.00 -91.00   0.50    1.49    -- -106.00 125.00  30.00   52
 29  \w   -164.00-139.00   0.50    1.49    -- -106.00 -19.00 150.00   50
 30  \w   -177.00 -93.00   0.50    1.49    -- -106.00 -37.00  60.00  168
 31  \w   -164.00 -85.00   0.50    1.49    -- -106.00 -73.00 -52.00  158
 32  \w   -126.00-101.00   0.50    1.49    -- -106.00 -37.00-150.00   50
 33  \w   -176.00-141.00   0.50    1.49    -- -106.00 -37.00-150.00   70
 34  \w   -172.00 -75.00   0.50    1.49    -- -106.00-125.00  30.00  194
 35  \w   -173.00 -81.00   0.50    1.49    -- -106.00-125.00  90.00  184
;
_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      0.0776833000
_diffrn_orient_matrix_UB_12      -0.0254644000
_diffrn_orient_matrix_UB_13      0.0435832000
_diffrn_orient_matrix_UB_21      -0.0587226000
_diffrn_orient_matrix_UB_22      -0.0656352000
_diffrn_orient_matrix_UB_23      0.0094507000
_diffrn_orient_matrix_UB_31      0.1014584000
_diffrn_orient_matrix_UB_32      -0.0237044000
_diffrn_orient_matrix_UB_33      -0.0323070000
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            85463
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.608
_diffrn_reflns_theta_min         3.369
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71295
_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    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1729
_refine_ls_number_reflns         26553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+1.2413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22157
_reflns_number_total             26553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01394k2.cif
_cod_data_source_block           x191213_tk01-0140-1_ph2-bztrop
_cod_depositor_comments
;

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C184 H128 O8'
_cod_original_formula_weight         2466.86
_cod_original_formula_moiety         '8(C23 H16 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        6565.15(10)
_cod_database_code               1566742
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H14 O1'
_chemical_oxdiff_usercomment     'X191213_TK01-XXX-1_Ph2-BzTrop C23 H14 O1'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C122(H122), C57(H57), C43(H43), C98(H98), C153(H153), C129(H129), C9(H9),
 C19(H19), C116(H116), C26(H26), C33(H33), C47(H47), C146(H146), C170(H170),
 C127(H127), C148(H148), C74(H74), C163(H163), C81(H81), C103(H103), C2(H2),
 C67(H67), C85(H85), C28(H28), C175(H175), C50(H50), C151(H151), C89(H89),
 C22(H22), C137(H137), C174(H174), C149(H149), C100(H100), C88(H88), C126(H126),
  C20(H20), C30(H30), C172(H172), C177(H177), C4(H4), C105(H105), C46(H46),
 C44(H44), C173(H173), C124(H124), C79(H79), C23(H23), C29(H29), C125(H125),
 C102(H102), C6(H6), C115(H115), C117(H117), C150(H150), C55(H55), C157(H157),
 C21(H21), C101(H101), C45(H45), C7(H7), C31(H31), C52(H52), C71(H71), C87(H87),
  C161(H161), C86(H86), C139(H139), C119(H119), C113(H113), C187(H187),
 C109(H109), C5(H5), C133(H133), C167(H167), C91(H91), C65(H65), C185(H185),
 C136(H136), C68(H68), C95(H95), C17(H17), C181(H181), C54(H54), C61(H61),
 C118(H118), C78(H78), C164(H164), C76(H76), C160(H160), C53(H53), C13(H13),
 C70(H70), C41(H41), C69(H69), C158(H158), C135(H135), C188(H188), C77(H77),
 C143(H143), C165(H165), C134(H134), C159(H159), C140(H140), C16(H16),
 C184(H184), C37(H37), C112(H112), C64(H64), C166(H166), C94(H94), C14(H14),
 C62(H62), C111(H111), C15(H15), C110(H110), C92(H92), C182(H182), C189(H189),
 C191(H191), C93(H93), C183(H183), C63(H63), C141(H141), C142(H142), C40(H40),
 C38(H38), C190(H190), C39(H39)
;
_shelx_res_checksum              27627
_shelx_hkl_checksum              30285
_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 1.449
_oxdiff_exptl_absorpt_empirical_full_min 0.612