Rapid access to polycyclic thiopyrylium compounds from unfunctionalized aromatics by thia-APEX reaction.
Kawahara, Kou P.; Ito, Hideto; Itami, Kenichiro; Chemical communications (Cambridge, England) 59 (2023) 1157–1160; doi:10.1039/d2cc06706d

data_7131138
_publ_section_title
;
 Rapid access to polycyclic thiopyrylium compounds from unfunctionalized
 aromatics by thia-APEX reaction.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1157
_journal_page_last               1160
_journal_paper_doi               10.1039/d2cc06706d
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C27 H17 S, C F3 O3 S'
_chemical_formula_sum            'C28 H17 F3 O3 S2'
_chemical_formula_weight         522.53
_chemical_name_systematic        3ha
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Hygroscopic
_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_creation_date             2021-01-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_audit_update_record
;
2022-10-31 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.755(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1260(7)
_cell_length_b                   29.3015(15)
_cell_length_c                   8.1823(5)
_cell_measurement_reflns_used    7604
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.1190
_cell_measurement_theta_min      2.5880
_cell_volume                     2238.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.852
_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    -24.00  87.00   0.50    1.50    --    8.45  57.00 -60.00  222
  2  \w     12.00  39.00   0.50    1.50    --    8.45 -57.00-180.00   54
  3  \w    -11.00  29.00   0.50    1.50    --    8.45 -99.00 -60.00   80
  4  \w     10.00  38.00   0.50    1.50    --    8.45-119.00  -2.00   56
  5  \w    -12.00  13.00   0.50    1.50    --   -7.83 -99.00 120.00   50
  6  \w     35.00  60.00   0.50    1.50    --    8.45-157.00-158.00   50
  7  \w    -36.00  -7.00   0.50    1.50    --    8.45 -57.00-180.00   58
  8  \w    -65.00 -40.00   0.50    1.50    --   -7.83 119.00  82.00   50
  9  \w     38.00  90.00   0.50    1.50    --    8.45 179.00-120.00  104
 10  \w    -85.00 -60.00   0.50    1.50    --   -7.83 157.00-122.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0490314000
_diffrn_orient_matrix_UB_12      0.0184702000
_diffrn_orient_matrix_UB_13      -0.0263761000
_diffrn_orient_matrix_UB_21      0.0575491000
_diffrn_orient_matrix_UB_22      0.0153314000
_diffrn_orient_matrix_UB_23      0.0138041000
_diffrn_orient_matrix_UB_31      -0.0075640000
_diffrn_orient_matrix_UB_32      -0.0031015000
_diffrn_orient_matrix_UB_33      -0.0891521000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19945
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.146
_diffrn_reflns_theta_min         2.181
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeCN/Et2O'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0573P)^2^+0.3430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3441
_reflns_number_total             4682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06706d2.cif
_cod_data_source_block           kohthia193_et2o_mecn
_cod_depositor_comments
'Adding full bibliography for 7131138--7131139.cif.'
_cod_database_code               7131138
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S O F'
_diffrn_oxdiff_digest_frames
;
01d3e4d4f3dae257d7876d674217bd2a900002662cd
;
_diffrn_oxdiff_digest_hkl
;
0103c595880b0df1a26418d59295308903ca36
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C28(H20), C24(H24), C11(H4), C20(H25), C6(H15), C14(H7), C3(H12), C27(H21),
 C12(H5), C4(H13), C17(H28), C13(H6), C25(H23), C18(H27), C5(H14), C19(H26),
 C26(H22)
;
_shelx_res_checksum              12326
_shelx_hkl_checksum              86763
_olex2_exptl_crystal_mounting_method loop
_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 10.328
_oxdiff_exptl_absorpt_empirical_full_min 0.346