Three-component [3 + 2] cycloaddition for regio- and diastereoselective synthesis of spirooxindole-pyrrolidines
Zhang, Xiaofeng; Liu, Miao; Zhan, Desheng; Kaur, Manpreet; Jasinski, Jerry P.; Zhang, Wei; New Journal of Chemistry 46 (2022) 3866–3870; doi:10.1039/D1NJ05538K

data_7061214
_publ_section_title
;
 Three-component [3 + 2] cycloaddition for regio- and diastereoselective
 synthesis of spirooxindole-pyrrolidines
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3866
_journal_page_last               3870
_journal_paper_doi               10.1039/D1NJ05538K
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C29 H27 Br N2 O3'
_chemical_formula_sum            'C29 H27 Br N2 O3'
_chemical_formula_weight         531.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2021-07-21 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                101.462(5)
_cell_angle_beta                 112.148(5)
_cell_angle_gamma                105.775(6)
_cell_formula_units_Z            2
_cell_length_a                   10.4594(6)
_cell_length_b                   10.8089(8)
_cell_length_c                   13.2837(7)
_cell_measurement_reflns_used    3998
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      71.2890
_cell_measurement_theta_min      4.6420
_cell_volume                     1259.83(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0416
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9774
_diffrn_measurement_details
;
  1 omega   20.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.1697   57.0000   60.0000 65

  2 omega   41.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 37

  3 omega   68.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000    0.0000 26

  4 omega   43.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 54

  5 omega   68.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 48

  6 omega   76.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.1697 -178.0000   60.0000 28

  7 omega   47.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 33

  8 omega   40.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 40

  9 omega   39.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 48

 10 omega   80.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 94

 11 omega   75.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   16.0000  174.0000 98

 12 omega   43.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 61

 13 omega   44.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 45

 14 omega   24.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.1697  -99.0000   90.0000 49

 15 omega   38.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 49

 16 omega   54.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 54

 17 omega   60.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 41

 18 omega   52.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 36

 19 omega   40.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 59

 20 omega   45.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 66

 21 omega   -4.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.1697  -99.0000  -90.0000 76

 22 omega  -33.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   90.0000 26

 23 omega  -87.00  -58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -178.0000  120.0000 29

 24 omega -101.00  -55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -178.0000   90.0000 46

 25 omega  -96.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  120.0000 89

 26 omega  -97.00  -70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 27

 27 omega  -67.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000  -90.0000 60

 28 omega   -6.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  -30.0000 25

 29 omega  -59.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  -30.0000 30

 30 omega  -98.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000 -180.0000 70

 31 omega  -61.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -178.0000 -150.0000 25

 32 omega -100.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   90.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, Oxford diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0000313000
_diffrn_orient_matrix_UB_12      -0.1424246000
_diffrn_orient_matrix_UB_13      0.0000102000
_diffrn_orient_matrix_UB_21      0.1328303000
_diffrn_orient_matrix_UB_22      0.0280996000
_diffrn_orient_matrix_UB_23      -0.0281649000
_diffrn_orient_matrix_UB_31      0.1092287000
_diffrn_orient_matrix_UB_32      0.0604730000
_diffrn_orient_matrix_UB_33      0.1299312000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8897
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         71.637
_diffrn_reflns_theta_min         3.817
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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    1.401
_exptl_crystal_description       prism
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.916
_refine_diff_density_min         -1.219
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0824P)^2^+0.9171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4122
_reflns_number_total             4792
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05538k2.cif
_cod_data_source_block           zhang-110a-531-p1
_cod_depositor_comments          'Adding full bibliography for 7061214.cif.'
_cod_original_cell_volume        1259.83(15)
_cod_database_code               7061214
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C29 H27 N2 O3 Br'
_chemical_oxdiff_usercomment     'Wei Zhang's Zhang-110A-531-P1'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Uiso/Uaniso restraints and constraints
Uanis(Br1A) = Uanis(Br1B)
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
3. Others
 Sof(Br1A)=Sof(H19A)=Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=
 Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=1-FVAR(1)
 Sof(Br1B)=Sof(H19)=Sof(C20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=
 Sof(C23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C10(H10), C19(H19A), C19(H19), C26(H26)
4.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C28(H28A,H28B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C21(H21), C22(H22), C24(H24), C25(H25), C21A(H21A), C22A(H22A), C24A(H24A),
 C25A(H25A)
4.d Fitted hexagon refined as free rotating group:
 C20(C21,C22,C23,C24,C25), C20A(C21A,C22A,C23A,C24A,C25A)
4.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              26759
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'