Diastereoselective construction of structurally diverse polycyclic spiroindolenines <i>via</i> Yb(OTf)<sub>3</sub>-catalyzed cascade [1,5]-hydride transfer/cyclization.
Hu, Song; Hu, Dan; Xu, Jianming; Wang, Jian; Yin, Heng; Xie, Ying; Li, Yulong; Li, Chenyi; Organic & biomolecular chemistry 23 (2025) 7633–7637; doi:10.1039/d5ob01005e

data_7160651
_publ_section_title
;
 Diastereoselective construction of structurally diverse polycyclic
 spiroindolenines <i>via</i> Yb(OTf)<sub>3</sub>-catalyzed cascade
 [1,5]-hydride transfer/cyclization.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7633
_journal_page_last               7637
_journal_paper_doi               10.1039/d5ob01005e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C26 H25 N3 O2 S'
_chemical_formula_sum            'C26 H24 N3 O2 S'
_chemical_formula_weight         442.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-19 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.477(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8910(6)
_cell_length_b                   8.2439(3)
_cell_length_c                   21.5146(10)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      3.12
_cell_volume                     2282.19(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            72813
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.270
_diffrn_reflns_theta_min         2.646
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1151 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.8977.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5611
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0850P)^2^+0.7145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1636
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4293
_reflns_number_total             5611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01005e2.cif
_cod_data_source_block           mo_250108lcy_0ma
_cod_depositor_comments          'Adding full bibliography for 7160651.cif.'
_cod_database_code               7160651
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 O2, O4, O3, O1, S1, S2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Others
 Sof(S1)=Sof(O2)=Sof(O1)=1-FVAR(1)
 Sof(S2)=Sof(O4)=Sof(O3)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C17(H17A,H17B), C19(H19A,H19B), C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C26(H26), C4(H4), C23(H23), C14(H14), C25(H25), C24(H24),
 C12(H12), C13(H13), C6(H6), C3(H3), C7(H7)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'