The metal-free or Lewis acid-catalyzed C5-H methylthiomethylation of oxindoles with DMSO.
Zhang, Xiya; Yu, Mingming; Zhou, Junyu; Wang, Jinhua; Li, Shiqing; Organic & biomolecular chemistry 23 (2025) 9158–9163; doi:10.1039/d5ob01356a

data_7160750
_publ_section_title
;
 The metal-free or Lewis acid-catalyzed C5-H methylthiomethylation of
 oxindoles with DMSO.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9158
_journal_page_last               9163
_journal_paper_doi               10.1039/d5ob01356a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '2(C13 H17 N O3 S)'
_chemical_formula_sum            'C26 H34 N2 O6 S2'
_chemical_formula_weight         534.67
_chemical_name_systematic        ZXY-603
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-04 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                114.409(9)
_cell_angle_beta                 101.026(9)
_cell_angle_gamma                93.038(10)
_cell_formula_units_Z            1
_cell_length_a                   8.395(2)
_cell_length_b                   9.021(3)
_cell_length_c                   9.771(3)
_cell_measurement_reflns_used    2603
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      27.465
_cell_measurement_theta_min      2.499
_cell_volume                     654.1(3)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6069
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.634
_diffrn_reflns_theta_min         2.499
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5227
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0797 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.7010.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0386P)^2^+0.3095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2215
_reflns_number_total             2972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01356a2.cif
_cod_data_source_block           250302lu_lgpz2506831_zcs_0m
_cod_depositor_comments
'Adding full bibliography for 7160749--7160750.cif.'
_cod_database_code               7160750
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              69426
_olex2_submission_original_sample_id ZXY-603
_olex2_submission_special_instructions 'No special instructions were received'