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_7131139
_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 H18 O S'
_chemical_formula_sum            'C27 H18 O S'
_chemical_formula_weight         390.47
_chemical_name_systematic        3ha-OH
_chemical_properties_physical    Air-sensitive,Heat-sensitive
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-22
_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                86.3365(19)
_cell_angle_beta                 81.0292(18)
_cell_angle_gamma                87.2974(17)
_cell_formula_units_Z            8
_cell_length_a                   12.4701(3)
_cell_length_b                   13.9402(3)
_cell_length_c                   22.0459(5)
_cell_measurement_reflns_used    13703
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.9960
_cell_measurement_theta_min      1.7230
_cell_volume                     3775.06(15)
_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 1.000
_diffrn_measured_fraction_theta_max 0.837
_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    -41.00  24.00   0.50   20.00    --   -7.83 -57.00   0.00  130
  2  \w    -12.00  37.00   0.50   20.00    --   -7.83 -99.00 -60.00   98
  3  \w     37.00  62.00   0.50   20.00    --    8.45-161.00 -46.00   50
  4  \w     13.00  38.00   0.50   20.00    --    8.45-117.00 103.00   50
  5  \w    -78.00 -47.00   0.50   20.00    --   -7.83 -57.00   0.00   62
  6  \w    -15.00  10.00   0.50   20.00    --    8.45 -99.00-120.00   50
  7  \w    -32.00  -6.00   0.50   20.00    --   -7.83  57.00  90.00   52
  8  \w     42.00  69.00   0.50   20.00    --   -7.83  57.00  90.00   54
  9  \w      5.00  71.00   0.50   20.00    --   -7.83  57.00   0.00  132
 10  \w     46.00  91.00   0.50   20.00    --    8.45 179.00 -60.00   90
 11  \w     39.00  92.00   0.50   20.00    --    8.45 179.00 -90.00  106
 12  \w    -41.00 -15.00   0.50   20.00    --   -7.83  57.00   0.00   52
 13  \w    -41.00  71.00   0.50   20.00    --   -7.83  57.00 -60.00  224
 14  \w    -64.00 -39.00   0.50   20.00    --   -7.83 117.00-168.00   50
 15  \w    -89.00 -48.00   0.50   20.00    --   -7.83 161.00 -17.00   82
 16  \w    -89.00 -64.00   0.50   20.00    --   -7.83-179.00 150.00   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      -0.0122811000
_diffrn_orient_matrix_UB_12      0.0247937000
_diffrn_orient_matrix_UB_13      -0.0273299000
_diffrn_orient_matrix_UB_21      -0.0221671000
_diffrn_orient_matrix_UB_22      0.0395154000
_diffrn_orient_matrix_UB_23      0.0171894000
_diffrn_orient_matrix_UB_31      0.0517539000
_diffrn_orient_matrix_UB_32      0.0206655000
_diffrn_orient_matrix_UB_33      -0.0046955000
_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  0.0764
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            59446
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.248
_diffrn_reflns_theta_min         1.654
_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    0.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77428
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHC3/pentane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1061
_refine_ls_number_reflns         15650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.9446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10400
_reflns_number_total             15650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06706d2.cif
_cod_data_source_block           kohthia187_fr2and3_chcl3_pent_20201222
_cod_depositor_comments
;
Adding full bibliography for 7131138--7131139.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C108 H72 O4 S4'
_cod_original_formula_weight         1561.89
_cod_original_formula_moiety         '4(C27 H18 O S)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        3775.07(14)
_cod_database_code               7131139
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S O Cl'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.981
_diffrn_oxdiff_digest_frames
;
010627aa8c08ad6a5fecc1d5d61059386d00025fd7e
;
_diffrn_oxdiff_digest_hkl
;
01308ae3a770ec85bddab2bdf071e00bb33fef
;
_reflns_odcompleteness_completeness 99.96
_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:
 C16(H16), C24(H24), C7(H7), C36(H36), C19(H19), C111(H111), C11(H11),
 C34(H34), C35(H35), C112(H112), C5(H5), C45(H45), C6(H6), C4(H4), C33(H33),
 C13(H13), C70(H70), C14(H14), C43(H43), C40(H40), C17(H17), C18(H18), C42(H42),
  C94(H94), C12(H12), C62(H62), C113(H113), C53(H53), C28(H28), C115(H115),
 C27(H27), C47(H47), C41(H41), C73(H73), C57(H57), C48(H48), C46(H46), C65(H65),
  C84(H84), C25(H25), C54(H54), C78(H78), C55(H55), C106(H106), C72(H72),
 C71(H71), C64(H64), C56(H56), C26(H26), C63(H63), C103(H103), C82(H82),
 C93(H93), C114(H114), C98(H98), C87(H87), C91(H91), C105(H105), C85(H85),
 C92(H92), C81(H81), C80(H80), C101(H101), C104(H104), C86(H86), C99(H99),
 C100(H100), C79(H79)
;
_shelx_res_checksum              65170
_shelx_hkl_checksum              7484
_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 2.318
_oxdiff_exptl_absorpt_empirical_full_min 0.373