Synthesis of tetrasubstituted thiophenes via a [3+2] cascade cyclization reaction of pyridinium 1,4-zwitterionic thiolates and activated allenes.
Zhai, Shengxian; Zhang, Xinping; Cheng, Bin; Li, Hui; Li, Yuntong; He, Yixuan; Li, Yun; Wang, Taimin; Zhai, Hongbin; Chemical communications (Cambridge, England) 56 (2020) 3085–3088; doi:10.1039/d0cc00262c

data_7125950
_publ_section_title
;
 Synthesis of tetrasubstituted thiophenes via a [3+2] cascade cyclization
 reaction of pyridinium 1,4-zwitterionic thiolates and activated allenes.
;
_journal_issue                   20
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3085
_journal_page_last               3088
_journal_paper_doi               10.1039/d0cc00262c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H16 O5 S'
_chemical_formula_sum            'C22 H16 O5 S'
_chemical_formula_weight         417.71
_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
_audit_creation_date             2018-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-24 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.898(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.903(4)
_cell_length_b                   7.1434(16)
_cell_length_c                   14.656(3)
_cell_measurement_reflns_used    3902
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.87
_cell_measurement_theta_min      2.19
_cell_volume                     1943.3(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12521
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.336
_diffrn_reflns_theta_min         2.194
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1202 before and 0.0678 after correction. The Ratio of minimum to maximum transmission is 0.7278. The \l/2 correction factor is 0.0015.'
_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    1.428
_exptl_crystal_description       needle
_exptl_crystal_F_000             835
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0780
_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^)+(0.1439P)^2^+0.8108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2272
_refine_ls_wR_factor_ref         0.2553
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3564
_reflns_number_total             5496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc00262c2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7125949--7125950.cif.'
_cod_original_cell_volume        1943.4(8)
_cod_database_code               7125950
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.985
_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:
 C5(H5), C19(H19), C21(H21), C17(H17), C6(H6), C3(H3), C18(H18), C4(H4),
 C20(H20), C2(H2)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C16(H16a,H16b,H16c)
;
_shelx_res_checksum              56371
_olex2_submission_special_instructions 'No special instructions were received'