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_1566747
_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         'C43 H30 O'
_chemical_formula_sum            'C43 H30 O'
_chemical_formula_weight         562.67
_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             2019-06-28
_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                 94.055(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0907(5)
_cell_length_b                   10.1466(3)
_cell_length_c                   22.1188(7)
_cell_measurement_reflns_used    6326
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.9330
_cell_measurement_theta_min      4.0750
_cell_volume                     2930.60(17)
_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    '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 0.9989
_diffrn_measured_fraction_theta_max 0.9625
_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    -83.00   3.00   0.50   11.38    --  -47.45 106.00 -34.00  172
  2  \w    -69.00 -33.00   0.50   61.96    -- -106.00 125.00  90.00   72
  3  \w   -103.00 -76.00   0.50   61.96    -- -106.00 106.00 -34.00   54
  4  \w    -68.00 -33.00   0.50   61.96    -- -106.00  57.00 -60.00   70
  5  \w    -84.00 -36.00   0.50   61.96    -- -106.00  57.00-180.00   96
  6  \w   -111.00 -33.00   0.50   11.38    --  -47.45 -57.00-120.00  156
  7  \w   -115.00 -71.00   0.50   61.96    -- -106.00  57.00 -60.00   88
  8  \w   -115.00 -48.00   0.50   61.96    -- -106.00 125.00-120.00  134
  9  \w   -115.00 -33.00   0.50   61.96    -- -106.00 125.00-180.00  164
 10  \w   -175.00 -95.00   0.50   61.96    -- -106.00 -19.00 -60.00  160
 11  \w   -177.00 -82.00   0.50   61.96    -- -106.00-106.00-133.00  190
 12  \w   -118.00 -90.00   0.50   11.38    --  -47.45-125.00 -60.00   56
 13  \w      2.00  27.00   0.50   11.38    --   47.45-106.00-133.00   50
 14  \w     29.00  54.00   0.50   61.96    --   70.50-106.00-133.00   50
 15  \w     51.00  76.00   0.50   11.38    --   47.45-106.00-133.00   50
 16  \w     87.00 112.00   0.50   61.96    --   70.50 106.00 -34.00   50
 17  \w     71.00 118.00   0.50   11.38    --   47.45 125.00 -90.00   94
 18  \w     71.00  96.00   0.50   11.38    --   47.45 125.00  30.00   50
 19  \w     72.00 108.00   0.50   11.38    --   47.45 125.00 120.00   72
 20  \w   -117.00 -35.00   0.50   61.96    -- -106.00  57.00 120.00  164
;
_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      0.1151770000
_diffrn_orient_matrix_UB_12      0.0173285000
_diffrn_orient_matrix_UB_13      -0.0081136000
_diffrn_orient_matrix_UB_21      0.0182793000
_diffrn_orient_matrix_UB_22      -0.1458672000
_diffrn_orient_matrix_UB_23      0.0166867000
_diffrn_orient_matrix_UB_31      -0.0178667000
_diffrn_orient_matrix_UB_32      -0.0382216000
_diffrn_orient_matrix_UB_33      -0.0673302000
_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  0.1115
_diffrn_reflns_av_unetI/netI     0.1187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.489
_diffrn_reflns_theta_min         3.810
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68841
_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    1.275
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5927
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0647
_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^)+(0.1171P)^2^+0.5267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4393
_reflns_number_total             5927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01394k2.cif
_cod_data_source_block           190627_ks_h2-x190627_ks_h2-ph4_phen_trop
_cod_original_cell_volume        2930.60(18)
_cod_database_code               1566747
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C43 H30 O1'
_chemical_oxdiff_usercomment     'X190627_KS_H2-Ph4_Phen_Trop C43 H30 O1'
_diffrn_oxdiff_ac3_digest_frames
;
01099a88b0643fbd4c72087818cb1c156000025070c
;
_diffrn_oxdiff_ac3_digest_hkl
;
01deb4bf09eb27e8bdeb1485ad519c4efa5c99
;
_reflns_odcompleteness_completeness 99.89
_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 Ternary CH refined with riding coordinates:
 C19(H19), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C13(H13), C25(H25), C39(H39), C27(H27), C31(H31), C24(H24),
 C7(H7), C21(H21), C37(H37), C12(H12), C10(H10), C6(H6), C35(H35), C43(H43),
 C23(H23), C30(H30), C36(H36), C33(H33), C34(H34), C28(H28), C42(H42), C11(H11),
  C29(H29), C22(H22), C40(H40), C41(H41)
;
_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 1.794
_oxdiff_exptl_absorpt_empirical_full_min 0.656