Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
Guo, Jing; Liu, Yangbin; Li, Xiangqiang; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Chem. Sci. 7 (2016) 2717–; doi:10.1039/C5SC03658E

data_1541884
_publ_section_title
;
 Nickel(ii)-catalyzed enantioselective cyclopropanation of
 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
;
_journal_issue                   4
_journal_name_full               'Chem. Sci.'
_journal_page_first              2717
_journal_paper_doi               10.1039/C5SC03658E
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H28 I N O9'
_chemical_formula_sum            'C24 H28 I N O9'
_chemical_formula_weight         601.37
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-12-09 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.52245(15)
_cell_length_b                   10.52245(15)
_cell_length_c                   48.9522(16)
_cell_measurement_reflns_used    5792
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.3450
_cell_measurement_theta_min      4.2870
_cell_volume                     5420.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    6.1500
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000  -90.0000 84

  2 omega   18.00  106.00   1.0000    6.1500
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000    0.0000 88

  3 omega  -31.00   53.00   1.0000    6.1500
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000   90.0000 84

  4 omega   18.00  106.00   1.0000    6.1500
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000  -60.0000 88

  5 omega   40.00   94.00   1.0000   24.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 54

  6 omega   50.00  101.00   1.0000   24.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 51

  7 omega   97.00  176.00   1.0000   24.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 79

  8 omega   49.00   75.00   1.0000   24.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 26

  9 omega   38.00   72.00   1.0000   24.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 34

 10 omega   44.00   88.00   1.0000   24.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 44
;
_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      -0.0019891000
_diffrn_orient_matrix_UB_12      0.0529647000
_diffrn_orient_matrix_UB_13      -0.0293549000
_diffrn_orient_matrix_UB_21      -0.0881634000
_diffrn_orient_matrix_UB_22      0.1085253000
_diffrn_orient_matrix_UB_23      0.0093295000
_diffrn_orient_matrix_UB_31      0.1168571000
_diffrn_orient_matrix_UB_32      0.0826891000
_diffrn_orient_matrix_UB_33      0.0065155000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            14454
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.018
_diffrn_reflns_theta_min         5.545
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.474
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.042
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1121P)^2^+2.0027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1685
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4332
_reflns_number_total             4801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc03658e2.cif
_cod_data_source_block           fxm-5i(bio)
_cod_depositor_comments
'Adding full bibliography for 1541883--1541884.cif.'
_cod_database_code               1541884
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.73
_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:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C74(H74), C6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              83396
_olex2_submission_special_instructions 'No special instructions were received'