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_1554918
_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         'C35 H27 Br F3 N3 O3'
_chemical_formula_sum            'C35 H27 Br F3 N3 O3'
_chemical_formula_weight         674.50
_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
_audit_creation_date             2018-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-18 deposited with the CCDC.	2019-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.47950(10)
_cell_length_b                   18.03580(10)
_cell_length_c                   21.54370(10)
_cell_measurement_reflns_used    23741
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7980
_cell_measurement_theta_min      3.1730
_cell_volume                     3294.78(5)
_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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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    -65.00  30.00   0.50    0.05    --  -46.62  13.00  49.00  190
  2  \w   -117.00 -27.00   0.50    0.05    -- -100.00 125.00-112.00  180
  3  \w     34.00 112.00   0.50    0.05    --  107.00-116.00  73.00  156
  4  \w     31.00 126.00   0.50    0.05    --  107.00 -13.00-121.00  190
  5  \w     32.00 120.00   0.50    0.05    --   46.62  38.00 -30.00  176
  6  \w    -27.00  61.00   0.50    0.05    --   46.62 -38.00 120.00  176
  7  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00 -30.00  150
  8  \w     93.00 178.00   0.50    0.05    --  107.00  45.00-180.00  170
  9  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00 120.00  150
 10  \w     32.00 123.00   0.50    0.05    --  107.00 -30.00 -30.00  182
 11  \w     92.00 178.00   0.50    0.05    --  107.00  30.00 120.00  172
 12  \w     34.00 125.00   0.50    0.05    --  107.00 -61.00   0.00  182
 13  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00-180.00  150
 14  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00   0.00  150
 15  \w     34.00 117.00   0.50    0.05    --  107.00-125.00-150.00  166
 16  \w     75.00 125.00   0.50    0.05    --  107.00 -61.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0255371000
_diffrn_orient_matrix_UB_12      -0.0750609000
_diffrn_orient_matrix_UB_13      -0.0326485000
_diffrn_orient_matrix_UB_21      -0.0186827000
_diffrn_orient_matrix_UB_22      -0.0403060000
_diffrn_orient_matrix_UB_23      0.0626354000
_diffrn_orient_matrix_UB_31      -0.1788170000
_diffrn_orient_matrix_UB_32      -0.0064971000
_diffrn_orient_matrix_UB_33      -0.0112164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31862
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.867
_diffrn_reflns_theta_min         3.196
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33806
_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    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.903
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Flack x determined using 2766 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.171(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0758P)^2^+11.5344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1528
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6670
_reflns_number_total             6858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00452a2.cif
_cod_data_source_block           zhaoxy_fv2_181128
_cod_database_code               1554918
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.562
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C00I(H00I), C00M(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C011(H01A,H01B), C019(H01C,H01D)
2.c Aromatic/amide H refined with riding coordinates:
 N00C(H00C), C00H(H00H), C00J(H00J), C00N(H00N), C00Q(H00Q), C00S(H00S),
 C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C012(H012),
 C014(H014), C015(H015), C016(H016), C017(H017), C018(H018), C01A(H01E),
 C01B(H01F)
;
_shelx_res_checksum              35519
_shelx_hkl_checksum              15514
_shelx_fab_checksum              4810
_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 2.865
_oxdiff_exptl_absorpt_empirical_full_min 0.441