Diastereodivergent synthesis of bispirooxindoles via asymmetric Friedel-Crafts/aldol cascade reaction: co-catalyst effects on diastereoselective outcomes.
Li, Nai-Kai; Fan, Wei-Tai; Zhang, Jun-Qi; Sun, Bing-Bing; Chen, Jun-Bo; Wang, Xing-Wang; Chemical communications (Cambridge, England) 54 (2018) 2260–2263; doi:10.1039/c7cc09489b

data_7121216
_publ_section_title
;
 Diastereodivergent synthesis of bispirooxindoles via asymmetric
 Friedel-Crafts/aldol cascade reaction: co-catalyst effects on
 diastereoselective outcomes.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2260
_journal_page_last               2263
_journal_paper_doi               10.1039/c7cc09489b
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H29 N3 O5'
_chemical_formula_sum            'C29 H29 N3 O5'
_chemical_formula_weight         499.55
_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     iterative
_audit_creation_date             2017-05-06
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
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_audit_update_record
;
2017-05-06 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6120(5)
_cell_length_b                   9.9405(4)
_cell_length_c                   52.933(3)
_cell_measurement_reflns_used    3129
_cell_measurement_temperature    210.01(10)
_cell_measurement_theta_max      72.3870
_cell_measurement_theta_min      4.5040
_cell_volume                     5057.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      210.01(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -113.00  -11.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  -57.0000 -180.0000 102

  2 omega  -39.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2343    0.0000 -150.0000 96

  3 omega   44.00   71.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000 -150.0000 27

  4 omega   29.00   90.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000    0.0000 61

  5 omega   39.00   99.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000  -60.0000 60

  6 omega   41.00   97.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522 -111.0000  -90.0000 56

  7 omega   33.00   95.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000 -120.0000 62

  8 omega   40.00   90.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000   90.0000 50

  9 omega  148.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  114.0000  -80.0000 29

 10 omega  122.00  175.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  111.0000  -30.0000 53

 11 omega -114.00  -60.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  -57.0000  -30.0000 54
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0919468000
_diffrn_orient_matrix_UB_12      0.0560058000
_diffrn_orient_matrix_UB_13      -0.0213975000
_diffrn_orient_matrix_UB_21      0.1281992000
_diffrn_orient_matrix_UB_22      -0.0088503000
_diffrn_orient_matrix_UB_23      0.0173860000
_diffrn_orient_matrix_UB_31      0.0277541000
_diffrn_orient_matrix_UB_32      -0.1442318000
_diffrn_orient_matrix_UB_33      -0.0093779000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0932
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            18051
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.526
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         9040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0260P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6565
_reflns_number_total             9040
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09489b2.cif
_cod_data_source_block           g170505d
_cod_depositor_comments
'Adding full bibliography for 7121214--7121216.cif.'
_cod_original_cell_volume        5057.7(4)
_cod_database_code               7121216
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.88
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B), C46(H46A,H46B), C49(H49A,H49B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C12(H12), C13(H13), C14(H14), C25(H25), C26(H26), C27(H27),
 C28(H28), C31(H31), C33(H33), C41(H41), C42(H42), C43(H43), C54(H54), C55(H55),
  C56(H56), C57(H57)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C),
 C23(H23A,H23B,H23C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C40(H40A,H40B,
 H40C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'