Iridium-catalyzed [(5+1)-1] annulation of pyridinium 1,4-zwitterionic thiolates and sulfoxonium ylides: a versatile platform to indolizines.
Fang, Sheng; Chen, Wang-Liang; Meng, Yuan-Jie; Zhang, Shang-Shi; Feng, Peng-Ju; Shu, Bing; Chemical communications (Cambridge, England) 61 (2025) 14725–14728; doi:10.1039/d5cc03199k

data_1575486
_publ_section_title
;
 Iridium-catalyzed [(5+1)-1] annulation of pyridinium 1,4-zwitterionic
 thiolates and sulfoxonium ylides: a versatile platform to indolizines.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14725
_journal_page_last               14728
_journal_paper_doi               10.1039/d5cc03199k
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C20 H17 N O5'
_chemical_formula_sum            'C20 H17 N O5'
_chemical_formula_weight         351.35
_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             2024-12-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-05-14 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                88.211(2)
_cell_angle_beta                 79.5740(10)
_cell_angle_gamma                82.8540(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9011(4)
_cell_length_b                   8.6147(4)
_cell_length_c                   12.0695(6)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    112.00
_cell_measurement_theta_max      68.436
_cell_measurement_theta_min      3.724
_cell_volume                     801.65(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      112.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13877
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.430
_diffrn_reflns_theta_min         3.724
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1000 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.8106.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0158(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0470P)^2^+0.4487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2809
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03199k2.cif
_cod_data_source_block           fs_03
_cod_depositor_comments          'Adding full bibliography for 1575486.cif.'
_cod_database_code               1575486
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.880
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              61816
_shelx_hkl_checksum              67674
_olex2_submission_special_instructions 'No special instructions were received'