High diastereo- and enantioselective Michael addition of 3-acetoxy-2-oxindoles with nitroalkenes catalyzed by nickel/PyBisulidine.
Wu, Ruoran; Chen, Peng; Chai, Yu; Zhou, Junyu; Ou, Jianhua; Min, Yan; Wang, Haoting; Liang, Guojuan; Zhang, Dong; Zhou, Jing; Zhou, Hui; Organic & biomolecular chemistry 21 (2023) 6225–6229; doi:10.1039/d3ob01024d

data_7159482
_publ_section_title
;
 High diastereo- and enantioselective Michael addition of
 3-acetoxy-2-oxindoles with nitroalkenes catalyzed by nickel/PyBisulidine.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6225
_journal_page_last               6229
_journal_paper_doi               10.1039/d3ob01024d
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H15 F N2 O5'
_chemical_formula_sum            'C18 H15 F N2 O5'
_chemical_formula_weight         358.32
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-16 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.98207(19)
_cell_length_b                   13.3543(3)
_cell_length_c                   29.0314(5)
_cell_measurement_reflns_used    3787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8720
_cell_measurement_theta_min      4.4870
_cell_volume                     3482.29(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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     28.00  55.00   0.50    1.00    --    0.00  57.00 -30.00   54
  2  \w   -106.00 -34.00   0.50    1.90    --  -33.50 178.00-120.00  144
  3  \w     61.00  88.00   0.50    1.90    --   36.47  77.00 -90.00   54
  4  \w     62.00 109.00   0.50    1.90    --   36.47 178.00 -90.00   94
  5  \w     62.00  98.00   0.50    1.90    --   36.47-151.00 -57.00   72
  6  \w     17.00  76.00   0.50    1.90    --   36.47  37.00  30.00  118
  7  \w      7.00  38.00   0.50    1.90    --   36.47 -77.00-120.00   62
  8  \w     19.00  98.00   0.50    1.90    --   36.47  57.00  60.00  158
  9  \w      9.00  58.00   0.50    1.90    --   36.47  77.00 -90.00   98
 10  \w     72.00 107.00   0.50   10.00    --  108.00 -94.00-150.00   70
 11  \w     38.00 114.00   0.50   10.00    --  108.00 -45.00-180.00  152
 12  \w     37.00 150.00   0.50   10.00    --  108.00 -15.00 150.00  226
 13  \w     44.00 119.00   0.50   10.00    --  108.00 -61.00 -90.00  150
 14  \w     37.00 133.00   0.50   10.00    --  108.00 -30.00 -90.00  192
 15  \w     69.00 107.00   0.50   10.00    --  108.00 -94.00 120.00   76
 16  \w     78.00 111.00   0.50   10.00    --  108.00-111.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0957683000
_diffrn_orient_matrix_UB_12      -0.0929356000
_diffrn_orient_matrix_UB_13      -0.0103436000
_diffrn_orient_matrix_UB_21      0.1391569000
_diffrn_orient_matrix_UB_22      0.0669440000
_diffrn_orient_matrix_UB_23      -0.0039269000
_diffrn_orient_matrix_UB_31      0.0297304000
_diffrn_orient_matrix_UB_32      -0.0134389000
_diffrn_orient_matrix_UB_33      0.0519156000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13419
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.862
_diffrn_reflns_theta_min         4.499
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         6579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0576P)^2^+0.1302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1288
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                5430
_reflns_number_total             6579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01024d2.cif
_cod_data_source_block           202209186
_cod_depositor_comments          'Adding full bibliography for 7159482.cif.'
_cod_original_cell_volume        3482.30(13)
_cod_database_code               7159482
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2F1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.609
_reflns_odcompleteness_completeness 99.83
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C9'(H9')
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10'(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C15(H15), C16(H16),
 C1'(H1'A), C2'(H2'), C3'(H3'), C4'(H4'), C12'(H12'), C13'(H13'), C15'(H15'),
 C16'(H16')
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18'(H18D,H18E,H18F)
;
_shelx_res_checksum              15701
_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.913