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_4517320
_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         'C22 H21 N O3'
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40
_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             2019-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.695(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3444(2)
_cell_length_b                   16.6403(3)
_cell_length_c                   10.0554(2)
_cell_measurement_reflns_used    5592
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8120
_cell_measurement_theta_min      3.9990
_cell_volume                     1844.23(6)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -33.00  63.00   0.50    0.07    --   43.18 -37.00 -60.00  192
  2  \w     82.00 116.00   0.50    0.26    --  109.88-115.00-114.00   68
  3  \w     37.00 125.00   0.50    0.26    --  109.88 -30.00-180.00  176
  4  \w    100.00 171.00   0.50    0.26    --  109.88 115.00 -25.00  142
  5  \w     88.00 117.00   0.50    0.26    --  109.88  61.00 120.00   58
  6  \w    124.00 178.00   0.50    0.26    --  109.88  61.00 120.00  108
  7  \w     87.00 178.00   0.50    0.26    --  109.88  30.00 150.00  182
  8  \w     92.00 137.00   0.50    0.26    --  109.88 -77.00  60.00   90
  9  \w     82.00 112.00   0.50    0.26    --  109.88-125.00 120.00   60
 10  \w     76.00 101.00   0.50    0.26    --  109.88-168.00 100.00   50
 11  \w     49.00 103.00   0.50    0.26    --  109.88 -94.00  90.00  108
 12  \w     40.00  65.00   0.50    0.26    --  109.88 -77.00  60.00   50
 13  \w    -71.00 -46.00   0.50    0.07    --  -43.18 115.00 -25.00   50
 14  \w   -119.00 -76.00   0.50    0.07    --  -43.18 168.00 119.00   86
 15  \w     66.00  92.00   0.50    0.07    --   43.18 168.00 119.00   52
 16  \w     77.00 154.00   0.50    0.26    --  109.88 168.00 119.00  154
 17  \w    -98.00 -56.00   0.50    0.07    --  -43.18-168.00 100.00   84
 18  \w   -116.00 -31.00   0.50    0.07    --  -43.18 -57.00 150.00  170
 19  \w   -146.00-121.00   0.50    0.26    --  -90.25-115.00-114.00   50
 20  \w   -136.00-104.00   0.50    0.26    --  -90.25 -94.00   0.00   64
;
_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      0.1246343000
_diffrn_orient_matrix_UB_12      0.0312499000
_diffrn_orient_matrix_UB_13      -0.0129046000
_diffrn_orient_matrix_UB_21      0.0518793000
_diffrn_orient_matrix_UB_22      -0.0857795000
_diffrn_orient_matrix_UB_23      0.0230112000
_diffrn_orient_matrix_UB_31      -0.0362573000
_diffrn_orient_matrix_UB_32      -0.0152720000
_diffrn_orient_matrix_UB_33      -0.1554908000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10184
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         4.011
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43630
_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    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.050
_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     258
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0689P)^2^+0.5153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2897
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04112_si_002.cif
_cod_data_source_block           exp_2464
_cod_depositor_comments
'Adding full bibliography for 4517319--4517320.cif.'
_cod_database_code               4517320
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.878
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.77
_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. Uiso/Uaniso restraints and constraints
Uanis(C17A) = Uanis(C17B)
Uanis(C19B) = Uanis(C18A)
Uanis(C21A) = Uanis(C21B)
Uanis(C20A) = Uanis(C20B)
Uanis(C18B) = Uanis(C19A)
3. Others
 Sof(C17A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20A)=
 Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(C17B)=Sof(C18B)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19B)=Sof(C20B)=
 Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18B(H18A,H18B,H18C), C20B(H20A,H20B,H20C), C21B(H21A,H21B,
 H21C), C19A(H19A,H19B,H19C), C20A(H20D,H20E,H20F), C21A(H21D,H21E,H21F)
;
_shelx_res_checksum              38825
_shelx_hkl_checksum              79544
_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 1.940
_oxdiff_exptl_absorpt_empirical_full_min 0.570