Lewis Acid Catalysed Cyclization of Pyridinium 1,4-Zwitterionic Thiolates with Propargyl Alcohols and Fluorescence Applications
Yang, Zhi-Yuan; Li, Xue-Song; Zhang, Ming-Li; You, Zi-Xin; Liang, Yong-Min; Zhou, Ming-Dong; Chemical Communications  (2026) –; doi:10.1039/D5CC06010A

data_7135300
_publ_section_title
;
 Lewis Acid Catalysed Cyclization of Pyridinium 1,4-Zwitterionic Thiolates
 with Propargyl Alcohols and Fluorescence Applications
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC06010A
_journal_year                    2026
_chemical_formula_moiety         'C27 H20 O5 S'
_chemical_formula_sum            'C27 H20 O5 S'
_chemical_formula_weight         456.49
_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_block_doi                 10.5517/ccdc.csd.cc2n5ymf
_audit_creation_date             2025-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-10-20 deposited with the CCDC.	2025-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.017(3)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   14.2771(4)
_cell_length_b                   37.7540(10)
_cell_length_c                   17.4551(5)
_cell_measurement_reflns_used    28018
_cell_measurement_temperature    303.09(13)
_cell_measurement_theta_max      30.0010
_cell_measurement_theta_min      1.7510
_cell_volume                     8996.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.09(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.806
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -10.00  15.00   0.50   12.00    --    3.89  89.00  39.00   50
  2  \w    -36.00  -7.00   0.50   12.00    --    3.89 -89.00 -75.00   58
  3  \w      1.00  36.00   0.50   12.00    --    3.89 -99.00   0.00   70
  4  \w    -14.00  34.00   0.50   12.00    --    3.89 -99.00-150.00   96
  5  \w    -19.00  77.00   0.50   12.00    --    3.89  77.00-150.00  192
  6  \w      3.00  36.00   0.50   12.00    --    3.89 -99.00 120.00   66
  7  \w    -18.00  31.00   0.50   12.00    --    3.89 -99.00  60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0129710000
_diffrn_orient_matrix_UB_12      -0.0164176000
_diffrn_orient_matrix_UB_13      0.0200445000
_diffrn_orient_matrix_UB_21      0.0497935000
_diffrn_orient_matrix_UB_22      0.0053467000
_diffrn_orient_matrix_UB_23      0.0128638000
_diffrn_orient_matrix_UB_31      -0.0072166000
_diffrn_orient_matrix_UB_32      0.0074013000
_diffrn_orient_matrix_UB_33      0.0352014000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.806
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            100715
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.758
_diffrn_reflns_theta_min         1.629
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             3808
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.113
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1260
_refine_ls_number_reflns         22645
_refine_ls_number_restraints     2909
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.1510
_refine_ls_R_factor_gt           0.1055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1316P)^2^+11.7357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2812
_refine_ls_wR_factor_ref         0.3114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14135
_reflns_number_total             22645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06010a2.cif
_cod_data_source_block           panglinh_0118_5_autored
_cod_database_code               7135300
_shelx_shelxl_version_number     2019/3
_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. Restrained distances
 O17A-C111
 2.2 with sigma of 0.01
 C108-O17 \\sim C108-O17A
 with sigma of 0.02
 O17-C99 \\sim O17A-C99A
 with sigma of 0.02
 C108-C99 \\sim C108-C99A
 with sigma of 0.04
3. Rigid bond restraints
 O3, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O12, C79
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O14, C79
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 S4, C94
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S2, C45
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S3, C65
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C108, C110
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57
\\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65
\\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C73
\\sim C74 \\sim C75 \\sim C76 \\sim C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81
\\sim C82 \\sim C83 \\sim C84 \\sim C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89
\\sim C90 \\sim C91 \\sim C92 \\sim C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97
\\sim C98 \\sim C100 \\sim C101 \\sim C102 \\sim C103 \\sim C104 \\sim C105
\\sim C106 \\sim C108 \\sim C109 \\sim C110 \\sim C111 \\sim C112: within 3.8A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 3.8A
O17 \\sim O17A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
Uanis(C101) \\sim Ueq, Uanis(C102) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Fixed Sof: O18(0.5) O19(0.5) C101(0.55) H10G(0.55) H10H(0.55) H10I(0.55)
 C102(0.45) H10J(0.45) H10K(0.45) H10L(0.45) O20(0.5) O21(0.5) O22(0.5)
 O23(0.5) C103(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C104(0.5) C105(0.5) H10D(0.5)
 H10E(0.5) H10F(0.5) C106(0.5) O17(0.75) C99(0.5) H99A(0.5) H99B(0.5) H99C(0.5)
 O17A(0.25) C99A(0.5) H99D(0.5) H99E(0.5) H99F(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C27(H27), C29(H29), C33(H33), C34(H34), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43), C44(H44), C47(H47),
  C48(H48), C49(H49), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55),
 C56(H56), C57(H57), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C64(H64),
  C67(H67), C68(H68), C69(H69), C70(H70), C71(H71), C72(H72), C73(H73),
 C76(H76), C77(H77), C78(H78), C80(H80), C81(H81), C82(H82), C83(H83), C84(H84),
  C85(H85), C86(H86), C87(H87), C88(H88), C90(H90), C93(H93), C95(H95),
 C111(H111), C112(H112), C109(H109), C110(H110)
6.b Fitted hexagon refined as free rotating group:
 C108(C111,C112,C63,C109,C110)
6.c Idealised Me refined as rotating group:
 C91(H91A,H91B,H91C), C96(H96A,H96B,H96C), C97(H97A,H97B,H97C), C98(H98A,H98B,
 H98C), C100(H10M,H10N,H10O), C101(H10G,H10H,H10I), C102(H10J,H10K,H10L),
 C103(H10A,H10B,H10C), C105(H10D,H10E,H10F), C99(H99A,H99B,H99C), C99A(H99D,
 H99E,H99F)
;
_shelx_res_checksum              90391
_shelx_hkl_checksum              2409
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.574