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_7119570
_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 H38 N2 O7'
_chemical_formula_sum            'C32 H38 N2 O7'
_chemical_formula_weight         562.64
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-04-19 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6636(3)
_cell_length_b                   13.5571(3)
_cell_length_c                   21.8099(8)
_cell_measurement_reflns_used    7151
_cell_measurement_temperature    295.3(10)
_cell_measurement_theta_max      72.5170
_cell_measurement_theta_min      3.8050
_cell_volume                     3153.00(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      295.3(10)
_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   63.00   1.0000    1.5400
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -150.0000 94

  2 omega   20.00  104.00   1.0000    1.5400
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

  3 omega  -31.00   63.00   1.0000    1.5400
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  120.0000 94

  4 omega   23.00   90.00   1.0000    1.5400
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   90.0000 67

  5 omega  -31.00   63.00   1.0000    1.5400
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -90.0000 94

  6 omega   20.00  104.00   1.0000    1.5400
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

  7 omega   39.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

  8 omega   38.00  116.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

  9 omega   38.00   91.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 10 omega   38.00   91.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 11 omega   40.00   98.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 12 omega   38.00   91.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 13 omega   57.00  150.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -60.0000 93

 14 omega   39.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 15 omega   37.00  146.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   30.0000 109

 16 omega   10.00   70.00   1.0000    1.5400
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 60
;
_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      -0.0021989000
_diffrn_orient_matrix_UB_12      -0.0115509000
_diffrn_orient_matrix_UB_13      -0.0702217000
_diffrn_orient_matrix_UB_21      -0.1444242000
_diffrn_orient_matrix_UB_22      0.0019250000
_diffrn_orient_matrix_UB_23      0.0009432000
_diffrn_orient_matrix_UB_31      0.0022121000
_diffrn_orient_matrix_UB_32      0.1131071000
_diffrn_orient_matrix_UB_33      -0.0072505000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16766
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.046
_diffrn_reflns_theta_max         67.046
_diffrn_reflns_theta_min         5.205
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47879
_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    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1987 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0664
_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^)+(0.1357P)^2^+0.3089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5072
_reflns_number_total             5635
_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        3153.00(17)
_cod_database_code               7119570
_reflns_odcompleteness_completeness 99.81
_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 Ternary CH refined with riding coordinates:
 C20(H20), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C8(H8), C11(H11), C22(H22), C23(H23), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32)
2.d Fitted hexagon refined as free rotating group:
 C27(C28,C29,C30,C31,C32)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C10(H10A,H10B,H10C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              23349
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'