Pd-catalyzed electrophilic cross-coupling of pyridylphosphonium salts with arylthianthrenium salts to access C4-arylated pyridines.
Chen, Chen; Wang, Zi-Yi; Zhang, Xiao-Xu; Wang, Kui; Zhu, Bolin; Chemical communications (Cambridge, England) 61 (2025) 17185–17188; doi:10.1039/d5cc05044h

data_7135010
_publ_section_title
;
 Pd-catalyzed electrophilic cross-coupling of pyridylphosphonium salts
 with arylthianthrenium salts to access C4-arylated pyridines.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17185
_journal_page_last               17188
_journal_paper_doi               10.1039/d5cc05044h
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C18 H15 Br N O, I'
_chemical_formula_sum            'C18 H15 Br I N O'
_chemical_formula_weight         468.12
_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             2024-12-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-30 deposited with the CCDC.	2025-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                98.770(7)
_cell_angle_beta                 99.305(6)
_cell_angle_gamma                90.041(5)
_cell_formula_units_Z            2
_cell_length_a                   6.3543(3)
_cell_length_b                   8.4335(6)
_cell_length_c                   16.8759(16)
_cell_measurement_reflns_used    2787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3490
_cell_measurement_theta_min      2.4600
_cell_volume                     881.73(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -20.00   9.00   1.00    5.91    --  -10.61 -77.00-180.00   29
  2  \w    -42.00  44.00   1.00    5.91    --   11.47 -77.00 -30.00   86
  3  \w     -7.00  82.00   1.00    5.91    --   11.47  38.00-120.00   89
  4  \w    -17.00  85.00   1.00    5.91    --   11.47  57.00 120.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0572533000
_diffrn_orient_matrix_UB_12      0.0426256000
_diffrn_orient_matrix_UB_13      0.0288743000
_diffrn_orient_matrix_UB_21      -0.0563259000
_diffrn_orient_matrix_UB_22      -0.0717206000
_diffrn_orient_matrix_UB_23      0.0017054000
_diffrn_orient_matrix_UB_31      0.0797046000
_diffrn_orient_matrix_UB_32      -0.0169249000
_diffrn_orient_matrix_UB_33      0.0319632000
_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  0.0416
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6431
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         2.444
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0434P)^2^+0.1540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2484
_reflns_number_total             3097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05044h2.cif
_cod_data_source_block           a241226a_auto
_cod_depositor_comments          'Adding full bibliography for 7135010.cif.'
_cod_original_cell_volume        881.73(12)
_cod_database_code               7135010
_shelx_shelxl_version_number     2019/2
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              92426
_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 3.052
_oxdiff_exptl_absorpt_empirical_full_min 0.567