Synthesis of enantioenriched spirocyclic oxindoles catalyzed by bifunctional thiourea
Qian, Xue-Wei; Lin, Hong; Hu, Tianjiao; Yang, Xiaodi; Sun, Xing-Wen; Chemical Communications 61 (2025) 6348–6351; doi:10.1039/D5CC00165J

data_7134366
_publ_section_title
;
 Synthesis of enantioenriched spirocyclic oxindoles catalyzed by
 bifunctional thiourea
;
_journal_issue                   34
_journal_name_full               'Chemical Communications'
_journal_page_first              6348
_journal_page_last               6351
_journal_paper_doi               10.1039/D5CC00165J
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C28 H30 N2 O8'
_chemical_formula_sum            'C28 H30 N2 O8'
_chemical_formula_weight         522.54
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2j6zh7
_audit_creation_date             2024-02-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-02 deposited with the CCDC.	2025-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.742(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0574(5)
_cell_length_b                   30.2497(16)
_cell_length_c                   9.2025(5)
_cell_measurement_reflns_used    9510
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      59.416
_cell_measurement_theta_min      3.993
_cell_volume                     2681.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            90454
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.585
_diffrn_reflns_theta_min         4.736
_diffrn_source_current           2.86
_diffrn_source_power             0.1999426
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.8087.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 5016 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.34(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     697
_refine_ls_number_reflns         11743
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.7515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.960
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                10906
_reflns_number_total             11743
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00165j2.cif
_cod_data_source_block           ga_240201b
_cod_depositor_comments          'Adding full bibliography for 7134366.cif.'
_cod_database_code               7134366
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.786
_shelx_estimated_absorpt_t_min   0.632
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C39) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O7) \\sim Ueq, Uanis(C35) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C14(H14), C11(H11), C40(H40), C43(H43)
3.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N7(H7A), C7(H7), C57(H57), C9(H9), C18(H18), C19(H19), C20(H20),
 C21(H21), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C45(H45), C46(H46),
  C50(H50), C51(H51), C52(H52), C53(H53)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C37(H37A,H37B,H37C), C38(H38A,
 H38B,H38C), C39(H39A,H39B,H39C), C42(H42A,H42B,H42C), C48(H48A,H48B,H48C),
 C49(H49A,H49B,H49C)
;
_shelx_res_checksum              79842
_shelx_hkl_checksum              20922
_olex2_submission_special_instructions 'No special instructions were received'