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_7135453
_publ_section_title
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 Construction of oxindole spiro medium-sized S-heterocycles <i>via</i>
 ring expansion [2,3]-sigmatropic rearrangement.
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_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         'C20 H18 Br N O S'
_chemical_formula_sum            'C20 H18 Br N O S'
_chemical_formula_weight         400.32
_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   geom
_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                 95.778(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.640(5)
_cell_length_b                   13.250(4)
_cell_length_c                   7.717(2)
_cell_measurement_reflns_used    3559
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      19.99
_cell_measurement_theta_min      2.46
_cell_volume                     1692.8(8)
_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      120.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1601
_diffrn_reflns_av_unetI/netI     0.1168
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            29292
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.728
_diffrn_reflns_theta_min         1.969
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5882
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1369 before and 0.1021 after correction.
The Ratio of minimum to maximum transmission is 0.7892.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.279
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0688P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1510
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1884
_reflns_number_total             3228
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06578j2.cif
_cod_data_source_block           1_CCDC1
_cod_original_cell_volume        1692.8(9)
_cod_database_code               7135453
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.784
_shelx_estimated_absorpt_t_min   0.428
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C00E(H00E)
1.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00J(H00C,H00G), C00K(H00J,H00K)
1.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I), C00L(H00L),
 C00N(H00P), C00O(H00Q)
1.d Idealised Me refined as rotating group:
 C00M(H00M,H00N,H00O)
;
_shelx_res_checksum              66307
_olex2_submission_special_instructions 'No special instructions were received'