Chiral N,N’-Dioxide/Co(II)-Promoted Asymmetric 1,3-Dipolar Cycloaddition of Nitrones with Methyleneindolinones
Zhang, Dong; Yin, Chengkai; Zhou, Yuhang; Xu, Yali; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming; Chem. Commun.  (2017) –; doi:10.1039/C7CC03575F

data_7120313
_publ_section_title
;
 Chiral N,N&#x2019;-Dioxide/Co(II)-Promoted Asymmetric 1,3-Dipolar
 Cycloaddition of Nitrones with Methyleneindolinones
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03575F
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H34 N2 O6'
_chemical_formula_sum            'C32 H34 N2 O6'
_chemical_formula_weight         542.61
_chemical_name_systematic
'di-tert-butyl (3R,3'R,5'R)-2-oxo-2',3'-diphenylspiro[indoline-3,4'-isoxazolidine]-1,5'-dicarboxylate'
_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             2016-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-10-13 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.21904(12)
_cell_length_b                   11.88874(13)
_cell_length_c                   24.5399(3)
_cell_measurement_reflns_used    9598
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.4570
_cell_measurement_theta_min      5.6260
_cell_volume                     2981.39(6)
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9797
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -180.0000 74

  2 omega   23.00   90.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000   30.0000 67

  3 omega    1.00   75.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -90.0000 74

  4 omega   20.00  104.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -120.0000 84

  5 omega    1.00   28.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   92.0000 -165.6918 27

  6 omega  -31.00   53.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -150.0000 84

  7 omega   38.00   91.00   1.0000   23.2950
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

  8 omega   40.00   98.00   1.0000   23.2950
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

  9 omega   40.00   98.00   1.0000   23.2950
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 10 omega   38.00   91.00   1.0000   23.2950
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 11 omega  100.00  178.00   1.0000   23.2950
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 78

 12 omega   40.00   98.00   1.0000   23.2950
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 13 omega   39.00  177.00   1.0000   23.2950
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000    0.0000 138

 14 omega   38.00   91.00   1.0000   23.2950
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 15 omega   20.00  104.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

 16 omega  -31.00   53.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   60.0000 84

 17 omega   10.00  104.00   1.0000    5.8250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -30.0000 94
;
_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      0.0506427000
_diffrn_orient_matrix_UB_12      -0.1131926000
_diffrn_orient_matrix_UB_13      -0.0221358000
_diffrn_orient_matrix_UB_21      -0.0832396000
_diffrn_orient_matrix_UB_22      -0.0629200000
_diffrn_orient_matrix_UB_23      0.0425467000
_diffrn_orient_matrix_UB_31      -0.1150011000
_diffrn_orient_matrix_UB_32      -0.0042465000
_diffrn_orient_matrix_UB_33      -0.0405297000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15833
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.054
_diffrn_reflns_theta_max         67.054
_diffrn_reflns_theta_min         4.687
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40568
_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    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2022 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0946P)^2^+0.1664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4998
_reflns_number_total             5330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03575f2.cif
_cod_data_source_block           1
_cod_database_code               7120313
_reflns_odcompleteness_completeness 99.84
_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:
 C13(H13), C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              37215
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'