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_7160749
_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_absolute_configuration unk
_chemical_formula_moiety         '4(C23 H21 N O S)'
_chemical_formula_sum            'C92 H84 N4 O4 S4'
_chemical_formula_weight         1437.981
_chemical_name_systematic        ZXY-1
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-09 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   8.7963(7)
_cell_length_b                   9.8000(7)
_cell_length_c                   22.4394(16)
_cell_measurement_reflns_used    4147
_cell_measurement_temperature    293.30
_cell_measurement_theta_max      21.797
_cell_measurement_theta_min      2.268
_cell_volume                     1934.4(2)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.30
_diffrn_measured_fraction_theta_full 0.9778
_diffrn_measured_fraction_theta_max 0.9812
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.1129
_diffrn_reflns_Laue_measured_fraction_full 0.9778
_diffrn_reflns_Laue_measured_fraction_max 0.9812
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6458
_diffrn_reflns_point_group_measured_fraction_full 0.9447
_diffrn_reflns_point_group_measured_fraction_max 0.9423
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.27
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1019 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.8963.
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    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             760.888
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.3478
_refine_diff_density_min         -0.4274
_refine_diff_density_rms         0.0791
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.04(15)
_refine_ls_d_res_high            0.7687
_refine_ls_d_res_low             8.9809
_refine_ls_extinction_coef       0.040(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0972
_refine_ls_R_factor_all          0.1720
_refine_ls_R_factor_gt           0.0924
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1363P)^2^+0.5829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.3049
_reflns_Friedel_coverage         0.890
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              29
_reflns_limit_l_min              -28
_reflns_number_gt                2169
_reflns_number_total             4200
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01356a2.cif
_cod_data_source_block           241220LU_LGPZ1659553_ZCS_0m
_cod_depositor_comments
'Adding full bibliography for 7160749--7160750.cif.'
_cod_original_cell_volume        1934.4(3)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7160749
_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:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C22(H22), C19(H19), C5(H5), C13(H13), C14(H14), C20(H20), C21(H21),
 C9(H9), C17(H17), C15(H15), C10(H10), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C8(H8a,H8b,H8c)
;
_olex2_submission_special_instructions 'No special instructions were received'