Highly diastereo- and enantioselective synthesis of spirooxindole-cyclohexaneamides through N,N'-dioxide/Ni(ii)-catalyzed Diels-Alder reactions.
Zhou, Yuhang; Lu, Yan; Hu, Xinyue; Mei, Hongjiang; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 53 (2017) 2060–2063; doi:10.1039/c6cc10125a

data_7119571
_publ_section_title
;
 Highly diastereo- and enantioselective synthesis of
 spirooxindole-cyclohexaneamides through N,N'-dioxide/Ni(ii)-catalyzed
 Diels-Alder reactions.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2060
_journal_page_last               2063
_journal_paper_doi               10.1039/c6cc10125a
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H35 Cl N2 O7'
_chemical_formula_sum            'C32 H35 Cl N2 O7'
_chemical_formula_weight         595.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-19 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.088(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1960(4)
_cell_length_b                   10.2666(4)
_cell_length_c                   22.5256(6)
_cell_measurement_reflns_used    7421
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      72.0380
_cell_measurement_theta_min      4.7940
_cell_volume                     3184.24(18)
_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      293(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   30.0000 84

  2 omega   20.00  104.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 84

  3 omega  -31.00   53.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  -60.0000 84

  4 omega   81.00  108.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 27

  5 omega    2.00   29.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   91.0000 -159.8784 27

  6 omega    1.00   75.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   60.0000 74

  7 omega   18.00  106.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000 -180.0000 88

  8 omega   10.00  104.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000   30.0000 94

  9 omega   10.00  104.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -30.0000 94

 10 omega   20.00  104.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -30.0000 84

 11 omega   18.00  106.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000 -150.0000 88

 12 omega   10.00  104.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -120.0000 94

 13 omega   81.00  176.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

 14 omega   81.00  176.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 15 omega   82.00  176.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 94

 16 omega  151.00  176.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

 17 omega   88.00  133.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 45

 18 omega   38.00   88.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 50

 19 omega  138.00  176.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 38

 20 omega   87.00  114.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 27

 21 omega   82.00  107.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 25

 22 omega  115.00  176.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 61

 23 omega   92.00  117.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 25

 24 omega   87.00  117.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 30

 25 omega   84.00  109.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 25

 26 omega   90.00  117.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 27

 27 omega   81.00  107.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

 28 omega  126.00  168.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 42

 29 omega   81.00  107.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 30 omega   88.00  118.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 30

 31 omega   76.00  106.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 30

 32 omega   91.00  116.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 25

 33 omega   91.00  116.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 25

 34 omega   41.00   95.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 54

 35 omega   88.00  129.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 41

 36 omega   41.00   66.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 25

 37 omega   90.00  117.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 27

 38 omega   41.00  105.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 64

 39 omega   91.00  118.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 27

 40 omega   71.00  101.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 30

 41 omega   91.00  169.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 78

 42 omega  137.00  163.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 26
;
_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      0.1007972000
_diffrn_orient_matrix_UB_12      0.0343624000
_diffrn_orient_matrix_UB_13      0.0407415000
_diffrn_orient_matrix_UB_21      0.0418489000
_diffrn_orient_matrix_UB_22      0.0030894000
_diffrn_orient_matrix_UB_23      -0.0569898000
_diffrn_orient_matrix_UB_31      -0.0246057000
_diffrn_orient_matrix_UB_32      0.1459896000
_diffrn_orient_matrix_UB_33      -0.0083579000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15282
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.759
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55057
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5150
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1253P)^2^+0.5146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.799
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                4866
_reflns_number_total             5150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc10125a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7119570--7119571.cif.'
_cod_original_cell_volume        3184.25(18)
_cod_database_code               7119571
_reflns_odcompleteness_completeness 99.87
_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), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C23(H23), C25(H25),
 C26(H26)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C27(H27A,H27B,
 H27C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              94292
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'