Functionalization and solubilization of polycyclic aromatic compounds by sulfoniumization
Erchinger, Johannes E.; Okumura, Tsubasa; Nakata, Kanami; Shimizu, Daisuke; Daniliuc, Constanstin G.; Amaike, Kazuma; Glorius, Frank; Itami, Kenichiro; Ito, Hideto; Chemical Science 16 (2025) 8262–8267; doi:10.1039/D5SC01415H

data_1574399
_publ_section_title
;
 Functionalization and solubilization of polycyclic aromatic compounds by
 sulfoniumization
;
_journal_issue                   19
_journal_name_full               'Chemical Science'
_journal_page_first              8262
_journal_page_last               8267
_journal_paper_doi               10.1039/D5SC01415H
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C28 H19 B F4 S2'
_chemical_formula_weight         506.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'APEX5 v2023.9-2'
_audit_update_record
;
2024-12-09 deposited with the CCDC.	2025-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.849(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1406(8)
_cell_length_b                   10.3948(5)
_cell_length_c                   32.4934(17)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      27.4897
_cell_measurement_theta_min      2.3906
_cell_volume                     5022.5(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            54106
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.39
_diffrn_source                   'Mo ImS'
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_type              'micro focus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).

"Comparison of silver and molybdenum microfocus X-ray sources for

single-crystal structure determination"

J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5311
_refine_ls_number_restraints     133
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0427P)^2^+6.1615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4840
_reflns_number_total             5311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01415h2.cif
_cod_data_source_block           glo10731_3b
_cod_depositor_comments
'Adding full bibliography for 1574397--1574400.cif.'
_cod_database_code               1574399
_shelx_res_checksum              71023
_shelx_fab_checksum              92108