Nickel(II)-Catalyzed Enantioselective α-Vinylation of β-Keto Amides/Esters with Hypervalent Iodine Salts.
Guo, Jing; Lin, Lili; Liu, Yangbin; Li, Xiangqiang; Liu, Xiaohua; Feng, Xiaoming; Organic letters 18 (2016) 5540–5543; doi:10.1021/acs.orglett.6b02785

data_1555869
_publ_section_title
;
 Nickel(II)-Catalyzed Enantioselective \a-Vinylation of \b-Keto
 Amides/Esters with Hypervalent Iodine Salts.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5540
_journal_page_last               5543
_journal_paper_doi               10.1021/acs.orglett.6b02785
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H21 Cl N O2'
_chemical_formula_sum            'C22 H21 Cl N O2'
_chemical_formula_weight         366.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.01931(18)
_cell_length_b                   16.3547(7)
_cell_length_c                   19.4786(6)
_cell_measurement_reflns_used    6439
_cell_measurement_temperature    292.3(2)
_cell_measurement_theta_max      26.0850
_cell_measurement_theta_min      3.8650
_cell_volume                     1917.55(12)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.3(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -58.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2806  -19.0000  120.0000 164

  2 omega  -23.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2806   38.0000  -60.0000 128

  3 omega   -9.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2806   57.0000 -180.0000 108

  4 omega  -20.00   78.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2806  -99.0000  -60.0000 98

  5 omega -117.00  -57.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.2962 -178.0000  120.0000 60

  6 omega  -20.00   27.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.2962  -99.0000 -180.0000 47

  7 omega   35.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2806  178.0000  150.0000 81

  8 omega   -9.00   74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2806   57.0000   60.0000 83

  9 omega  -20.00   27.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.2962  -99.0000    0.0000 47
;
_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      -0.0126337000
_diffrn_orient_matrix_UB_12      0.0252434000
_diffrn_orient_matrix_UB_13      0.0293668000
_diffrn_orient_matrix_UB_21      -0.0045087000
_diffrn_orient_matrix_UB_22      -0.0352188000
_diffrn_orient_matrix_UB_23      0.0211739000
_diffrn_orient_matrix_UB_31      0.1170700000
_diffrn_orient_matrix_UB_32      0.0013688000
_diffrn_orient_matrix_UB_33      0.0040061000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22476
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63954
_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    1.271
_exptl_crystal_description
;
;
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1203 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0691P)^2^+0.2852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3382
_reflns_number_total             3933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02785_si_002.cif
_cod_data_source_block           fxm-ztl
_cod_database_code               1555869
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C009(H009), C00B(H00B), C00C(H00C), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00O(H00a,H00d,H00e), C00P(H00f,H00o,H00p), C00Q(H00q,H00r,H00s)
;
_shelx_res_checksum              8434
_shelx_hkl_checksum              49764
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-08-31
_olex2_submission_special_instructions 'No special instructions were received'