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_1574400
_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            'C22 H15 B F4 S2'
_chemical_formula_weight         430.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 109.437(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6757(6)
_cell_length_b                   15.4534(7)
_cell_length_c                   11.9779(7)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.7397
_cell_measurement_theta_min      2.2172
_cell_volume                     1863.44(17)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35379
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         2.22
_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    0.330
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_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    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.087
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0437P)^2^+1.0537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3359
_reflns_number_total             3939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01415h2.cif
_cod_data_source_block           glo10741_3a-major
_cod_depositor_comments
'Adding full bibliography for 1574397--1574400.cif.'
_cod_database_code               1574400
_shelx_res_checksum              16773