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_7135455
_publ_section_title
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 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         'C20 H18 Br N O S'
_chemical_formula_sum            'C20 H18 Br N O S'
_chemical_formula_weight         400.32
_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     iterative
_audit_creation_date             2025-02-13
_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                65.113(6)
_cell_angle_beta                 87.985(5)
_cell_angle_gamma                89.238(6)
_cell_formula_units_Z            4
_cell_length_a                   7.0549(11)
_cell_length_b                   15.033(3)
_cell_length_c                   17.847(4)
_cell_measurement_reflns_used    5348
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      24.44
_cell_measurement_theta_min      2.32
_cell_volume                     1716.0(6)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1142
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34519
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.323
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.523
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4933
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1855 before and 0.0914 after correction.
The Ratio of minimum to maximum transmission is 0.6619.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.929
_refine_diff_density_min         -1.140
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0730
_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^)+(0.1055P)^2^+5.5948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1970
_refine_ls_wR_factor_ref         0.2179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4335
_reflns_number_total             6044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06578j2.cif
_cod_data_source_block           1_CCDC3
_cod_original_cell_volume        1716.0(5)
_cod_database_code               7135455
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.786
_shelx_estimated_absorpt_t_min   0.719
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9189(13)
 0.0811(13)
2. 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
3.a Ternary CH refined with riding coordinates:
 C00J(H00J), C018(H018)
3.b Secondary CH2 refined with riding coordinates:
 C00G(H00F,H00G), C00O(H00H,H00K), C00Y(H00L,H00O), C00Z(H00D,H00E), C017(H01D,
 H01E), C01C(H01G,H01H)
3.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00I(H00I), C00M(H00M), C00N(H00N),
 C00S(H00S), C00V(H00V), C00X(H00X), C012(H012), C013(H013), C014(H014),
 C015(H015), C019(H019), C01A(H01L), C01B(H01F)
3.d Idealised Me refined as rotating group:
 C010(H01I,H01J,H01K), C016(H01A,H01B,H01C)
;
_shelx_res_checksum              18715
_olex2_submission_special_instructions 'No special instructions were received'