Chemo- and diastereoselective synthesis of spiro-iminoindoline-pyrazolines as potential antioxidant reagents.
Tian, Yuan-Hang; Yang, Qi-Chun; Liu, Yu-Xuan; Qin, Peng; Li, Jun-Long; Wu, Yi-Qi; Zeng, Rong; Zhang, Dong-Ming; Zhang, Xiang; Leng, Hai-Jun; Organic & biomolecular chemistry 24 (2026) 1488–1495; doi:10.1039/d5ob01910a

data_7160990
_publ_section_title
;
 Chemo- and diastereoselective synthesis of
 spiro-iminoindoline-pyrazolines as potential antioxidant reagents.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1488
_journal_page_last               1495
_journal_paper_doi               10.1039/d5ob01910a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         '2(C36 H29 Br N4 O2 S), C5.445 H8.113 O2.445'
_chemical_formula_sum            'C77 H66 Br2 N8 O6 S2'
_chemical_formula_weight         1423.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.504(9)
_cell_angle_beta                 97.493(10)
_cell_angle_gamma                103.217(9)
_cell_formula_units_Z            1
_cell_length_a                   8.4871(19)
_cell_length_b                   12.362(3)
_cell_length_c                   17.148(4)
_cell_measurement_reflns_used    5559
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.67
_cell_volume                     1735.1(7)
_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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      178.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_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  0.0780
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24833
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.647
_diffrn_reflns_theta_min         2.035
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6083
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1428 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.8159.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       needle
_exptl_crystal_F_000             734
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.391
_refine_diff_density_min         -1.077
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         7979
_refine_ls_number_restraints     411
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0595
_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^)+(0.1012P)^2^+0.4915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5460
_reflns_number_total             7979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01910a2.cif
_cod_data_source_block           mo_ljl_yqc_1_2_0m_a
_cod_database_code               7160990
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.683
_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. Uiso/Uaniso restraints and constraints
Uanis(C41) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.001
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O3)=Sof(O4)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=Sof(H39A)=
 Sof(H39B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18),
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              96276
_olex2_submission_special_instructions 'No special instructions were received'