Diastereodivergent construction of bispiro[oxindole-bi-pyrrolidine]s with four consecutive stereocenters via asymmetric [3 + 2] cycloaddition of 2,3-dioxopyrrolidines using identical catalysts
Zhao, Xiaoyun; Xiong, Jiale; An, Junkai; Yu, Jicong; Zhu, Liping; Feng, Xing; Jiang, Xianxing; Organic Chemistry Frontiers 6 (2019) 1989–; doi:10.1039/C9QO00452A

data_1554919
_publ_section_title
;
 Diastereodivergent construction of bispiro[oxindole-bi-pyrrolidine]s with
 four consecutive stereocenters via asymmetric [3 + 2] cycloaddition of
 2,3-dioxopyrrolidines using identical catalysts
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1989
_journal_paper_doi               10.1039/C9QO00452A
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H30 F3 N3 O3, C H2 Cl2'
_chemical_formula_sum            'C40 H31 Cl2 F4 N2 O3'
_chemical_formula_weight         734.57
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-26 deposited with the CCDC.	2019-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9726(2)
_cell_length_b                   16.0021(3)
_cell_length_c                   18.2529(4)
_cell_measurement_reflns_used    9135
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.8590
_cell_measurement_theta_min      4.2700
_cell_volume                     3497.01(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -61.00  33.00   1.00    2.72    --  -41.14  38.00   0.00   94
  2  \w     -6.00  31.00   1.00    2.72    --  -41.14  38.00  30.00   37
  3  \w     55.00  96.00   1.00    2.72    --   41.14-125.00   0.00   41
  4  \w     40.00  69.00   1.00    2.72    --   41.14-125.00 -90.00   29
  5  \w     51.00 110.00   1.00   10.00    --  107.79 -94.00 120.00   59
  6  \w     51.00 106.00   1.00   10.00    --  107.79-125.00 120.00   55
  7  \w     35.00  60.00   1.00   10.00    --  107.79 -45.00 120.00   25
  8  \w     32.00 101.00   1.00   10.00    --  107.79 -30.00   0.00   69
  9  \w     55.00 178.00   1.00   10.00    --  107.79  15.00 -60.00  123
 10  \w     82.00 178.00   1.00   10.00    --  107.79  30.00   0.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0492744000
_diffrn_orient_matrix_UB_12      -0.0888831000
_diffrn_orient_matrix_UB_13      -0.0010571000
_diffrn_orient_matrix_UB_21      -0.0536561000
_diffrn_orient_matrix_UB_22      0.0154693000
_diffrn_orient_matrix_UB_23      0.0755909000
_diffrn_orient_matrix_UB_31      -0.1059794000
_diffrn_orient_matrix_UB_32      0.0334896000
_diffrn_orient_matrix_UB_33      -0.0377074000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13408
_diffrn_reflns_theta_full        74.04
_diffrn_reflns_theta_max         74.04
_diffrn_reflns_theta_min         3.67
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1516
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         6886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+1.4323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1448
_reflns_number_gt                6517
_reflns_number_total             6886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9qo00452a2.cif
_cod_data_source_block           19010704
_cod_database_code               1554919
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     'ZXY-FN-13 Dn'
_reflns_odcompleteness_completeness 99.91
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B), C27(H27A,H27B), C49(H49A,H49B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C23(H23), C24(H24),
 C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C40(H40),
  C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47)
;
_olex2_date_sample_data_collection 2019-01-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.522
_oxdiff_exptl_absorpt_empirical_full_min 0.684