Ni-Catalyzed 1,2-Acyl Migration Reactions Triggered by C–C Bond Activation of Ketones
Jiang, Cheng; Lu, Hong; Xu, Wen-Hua; Wu, Jianing; Yu, Tian-Yang; Xu, Peng-Fei; Wei, Hao; ACS Catalysis  (2020) 1947–1953; doi:10.1021/acscatal.9b04112

data_4517319
_publ_section_title
;
 Ni-Catalyzed 1,2-Acyl Migration Reactions Triggered by C--C Bond
 Activation of Ketones
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1947
_journal_page_last               1953
_journal_paper_doi               10.1021/acscatal.9b04112
_journal_year                    2020
_chemical_formula_moiety         'C18 H18 O'
_chemical_formula_sum            'C18 H18 O'
_chemical_formula_weight         250.32
_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             2019-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.205(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5972(5)
_cell_length_b                   9.6059(4)
_cell_length_c                   13.0289(5)
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.8010
_cell_measurement_theta_min      3.9860
_cell_volume                     1386.49(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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    -62.00   7.00   0.50    0.06    --  -43.05  83.00 113.00  138
  2  \w     60.00 120.00   0.50    0.06    --   43.05 178.00  30.00  120
  3  \w     80.00 166.00   0.50    0.25    --  109.88  83.00 113.00  172
  4  \w    129.00 176.00   0.50    0.25    --  109.88  61.00  60.00   94
  5  \w     89.00 118.00   0.50    0.25    --  109.88  61.00  60.00   58
  6  \w     83.00 109.00   0.50    0.25    --  109.88 -45.00 -30.00   52
  7  \w     86.00 140.00   0.50    0.25    --  109.88 -83.00  -6.00  108
  8  \w     63.00 108.00   0.50    0.25    --  109.88 -94.00 -60.00   90
  9  \w     36.00 104.00   0.50    0.25    --  109.88 -94.00-180.00  136
 10  \w     34.00  65.00   0.50    0.25    --  109.88 -45.00 -30.00   62
 11  \w     93.00 135.00   0.50    0.25    --  109.88  45.00-120.00   84
 12  \w    144.00 170.00   0.50    0.25    --  109.88  45.00-120.00   52
 13  \w     66.00  91.00   0.50    0.06    --   43.05 178.00-120.00   50
 14  \w     41.00  68.00   0.50    0.06    --   43.05  83.00 113.00   54
 15  \w    -49.00 -20.00   0.50    0.06    --  -43.05 -83.00  -6.00   58
 16  \w   -115.00 -53.00   0.50    0.06    --  -43.05 -83.00  -6.00  124
 17  \w   -136.00-111.00   0.50    0.25    --  -90.25 -83.00  -6.00   50
 18  \w   -161.00-104.00   0.50    0.25    --  -90.25 -94.00  60.00  114
 19  \w    -85.00 -16.00   0.50    0.25    --  -90.25  61.00 -60.00  138
 20  \w   -121.00 -61.00   0.50    0.25    --  -90.25  83.00 113.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1155256000
_diffrn_orient_matrix_UB_12      0.0832554000
_diffrn_orient_matrix_UB_13      0.0065895000
_diffrn_orient_matrix_UB_21      -0.0397381000
_diffrn_orient_matrix_UB_22      0.1134811000
_diffrn_orient_matrix_UB_23      0.0658814000
_diffrn_orient_matrix_UB_31      0.0664781000
_diffrn_orient_matrix_UB_32      -0.0767526000
_diffrn_orient_matrix_UB_33      0.1046308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6988
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.044
_diffrn_reflns_theta_max         67.044
_diffrn_reflns_theta_min         3.990
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0831P)^2^+0.6864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2078
_reflns_number_total             2419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04112_si_003.cif
_cod_data_source_block           exp_2463
_cod_depositor_comments
'Adding full bibliography for 4517319--4517320.cif.'
_cod_database_code               4517319
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 97.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              28826
_shelx_hkl_checksum              18072
_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 1.875
_oxdiff_exptl_absorpt_empirical_full_min 0.497