Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles.
Wen, Jiang-Bo; Du, Da-Ming; Organic & biomolecular chemistry 18 (2020) 1647–1656; doi:10.1039/c9ob02663k

data_7157342
_publ_section_title
;
 Squaramide-catalysed asymmetric cascade reactions of
 2,3-dioxopyrrolidines with 3-chlorooxindoles.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1647
_journal_page_last               1656
_journal_paper_doi               10.1039/c9ob02663k
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H17 Br N2 O3'
_chemical_formula_sum            'C25 H17 Br N2 O3'
_chemical_formula_weight         473.31
_chemical_melting_point          437.0(10)
_chemical_name_systematic
(2'S,3R,3'S)-3'-(2-Bromophenyl)-1''-phenyldispiro[indoline-3,1'-cyclopropane-2',3''-pyrrolidine]-2,4'',5''-trione
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-12 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.21(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0885(16)
_cell_length_b                   14.698(3)
_cell_length_c                   8.9850(18)
_cell_measurement_reflns_used    4012
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.4700
_cell_measurement_theta_min      1.3854
_cell_volume                     1047.8(4)
_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      163.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8231
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         2.567
_exptl_absorpt_coefficient_mu    1.992
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether/ethyl acetate 3:1'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4268
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.0608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.828
_reflns_Friedel_fraction_max     0.777
_reflns_number_gt                4173
_reflns_number_total             4268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02663k2.cif
_cod_data_source_block           bwn19456
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '436-438' was changed to
'437.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157342.cif.
;
_cod_database_code               7157342
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.826
_shelx_estimated_absorpt_t_min   0.657
_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 Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'