Nickel(ii)-catalyzed enantioselective α-alkylation of β-ketoamides with phenyliodonium ylide via a radical process.
Guo, Jing; Liu, Xiaohua; He, Changqiang; Tan, Fei; Dong, Shunxi; Feng, Xiaoming; Chemical communications (Cambridge, England) 54 (2018) 12254–12257; doi:10.1039/c8cc07140c

data_7122420
_publ_section_title
;
 Nickel(ii)-catalyzed enantioselective \a-alkylation of \b-ketoamides with
 phenyliodonium ylide via a radical process.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12254
_journal_page_last               12257
_journal_paper_doi               10.1039/c8cc07140c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C23 H33 Cl N2 O3'
_chemical_formula_sum            'C23 H33 Cl N2 O3'
_chemical_formula_weight         420.96
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-01-18 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.949(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7530(5)
_cell_length_b                   11.5829(4)
_cell_length_c                   19.2555(7)
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    292.6(10)
_cell_measurement_theta_max      72.3300
_cell_measurement_theta_min      4.4450
_cell_volume                     2354.63(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      air
_diffrn_ambient_temperature      292.6(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000   90.0000 94

  2 omega   20.00  104.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -60.0000 84

  3 omega    1.00   75.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   90.0000 74

  4 omega  -33.00   55.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000  -90.0000 88

  5 omega  -31.00   63.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000 -150.0000 94

  6 omega  -31.00   63.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000  -30.0000 94

  7 omega   20.00  104.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000    0.0000 84

  8 omega  -31.00   53.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   30.0000 84

  9 omega   40.00   98.00   1.0000   20.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 10 omega   70.00  178.00   1.0000   20.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 108

 11 omega   38.00   91.00   1.0000   20.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 12 omega   37.00  146.00   1.0000   20.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 109

 13 omega   39.00  109.00   1.0000   20.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 14 omega   39.00  109.00   1.0000   20.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 15 omega   41.00  126.00   1.0000   20.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 85

 16 omega   20.00   73.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -180.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1410921000
_diffrn_orient_matrix_UB_12      -0.0161646000
_diffrn_orient_matrix_UB_13      -0.0029961000
_diffrn_orient_matrix_UB_21      -0.0343619000
_diffrn_orient_matrix_UB_22      -0.0108932000
_diffrn_orient_matrix_UB_23      -0.0811291000
_diffrn_orient_matrix_UB_31      0.0143983000
_diffrn_orient_matrix_UB_32      0.1315496000
_diffrn_orient_matrix_UB_33      -0.0071808000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13310
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.701
_diffrn_reflns_theta_min         4.477
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0574
_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^)+(0.1064P)^2^+0.3901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3734
_reflns_number_total             4551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07140c2.cif
_cod_data_source_block           fxm-gj-5-cl-tempo
_cod_depositor_comments
'Adding full bibliography for 7122420--7122421.cif.'
_cod_original_cell_volume        2354.65(16)
_cod_database_code               7122420
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00J(H00H,H00I), C00L(H00J,H00L), C00N(H00P,H00Q)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00E(H00E), C00F(H00F), C00K(H00K)
2.c Idealised Me refined as rotating group:
 C00I(H00C,H00D,H00G), C00M(H00M,H00N,H00O), C00O(H00R,H00S,H00T), C00P(H00U,
 H00V,H00W), C00R(H00X,H00Y,H), C00S(H00Z,HA,HB), C00T(H00,HC,HD)
;
_olex2_date_sample_data_collection 2017-12-14
_olex2_submission_special_instructions 'No special instructions were received'