Construction of oxindole spiro medium-sized S-heterocycles <i>via</i> ring expansion [2,3]-sigmatropic rearrangement.
Xu, Yongqiang; Li, Wenkai; Gu, Xiaoli; Zhou, Yuhan; Qu, Jingping; Wang, Baomin; Chemical communications (Cambridge, England) 62 (2026) 4545–4548; doi:10.1039/d5cc06578j

data_7135452
_publ_section_title
;
 Construction of oxindole spiro medium-sized S-heterocycles <i>via</i>
 ring expansion [2,3]-sigmatropic rearrangement.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4545
_journal_page_last               4548
_journal_paper_doi               10.1039/d5cc06578j
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C19 H17 N O S'
_chemical_formula_sum            'C19 H17 N O S'
_chemical_formula_weight         307.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-13 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.312(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2703(15)
_cell_length_b                   9.7437(12)
_cell_length_c                   17.104(2)
_cell_measurement_reflns_used    6405
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.466
_cell_measurement_theta_min      2.389
_cell_volume                     1872.9(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16332
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.888
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3628
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1597 before and 0.0785 after correction. The Ratio of minimum to maximum transmission is 0.4863. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.3628
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0688
_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^)+(0.0557P)^2^+3.0810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2363
_reflns_number_total             3271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06578j2.cif
_cod_data_source_block           1
_cod_database_code               7135452
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00H(H00I,H00J), C00L(H00N,H00O)
1.b Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00B(H00D), C00D(H00E), C00E(H00F), C00F(H00G), C00G(H00H),
 C00I(H00K), C00J(H00L), C00K(H00M), C00M(H00P)
;
_shelx_res_checksum              11445
_shelx_fab_checksum              54173
_olex2_submission_special_instructions 'No special instructions were received'