5-(Diarylimino)- and 5-(sulfoximido)dibenzothiophenium triflates: syntheses and applications as electrophilic aminating reagents.
Li, Zhen; Vijaykumar, Gonela; Li, Xiangdong; Golz, Christopher; Alcarazo, Manuel; Organic & biomolecular chemistry 19 (2021) 2941–2948; doi:10.1039/d1ob00285f

data_7157954
_publ_section_title
;
 5-(Diarylimino)- and 5-(sulfoximido)dibenzothiophenium triflates:
 syntheses and applications as electrophilic aminating reagents.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2941
_journal_page_last               2948
_journal_paper_doi               10.1039/d1ob00285f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C24 H16 N O S2, C F3 O3 S'
_chemical_formula_sum            'C25 H16 F3 N O4 S3'
_chemical_formula_weight         547.57
_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             2020-06-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-02-09 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.771(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7343(9)
_cell_length_b                   11.6345(13)
_cell_length_c                   25.586(2)
_cell_measurement_reflns_used    9308
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.576
_cell_measurement_theta_min      2.645
_cell_volume                     2290.7(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture CuMo Dual Source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            114032
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.651
_diffrn_reflns_theta_min         2.372
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.5796
_exptl_absorpt_correction_T_min  0.5358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0456 after correction.
The Ratio of minimum to maximum transmission is 0.9244.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Et2O'
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6453
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0391P)^2^+1.4294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6192
_reflns_number_total             6453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00285f2.cif
_cod_data_source_block           mo_1018_cg_0m
_cod_depositor_comments
'Adding full bibliography for 7157951--7157968.cif.'
_cod_database_code               7157954
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S3A-O2A \\sim S3B-O2B
 with sigma of 0.02
 S3A-O4A \\sim S3B-O3B
 with sigma of 0.02
 S3A-O3A \\sim S3B-O4B
 with sigma of 0.02
 S3A-C25A \\sim S3B-C25B
 with sigma of 0.02
 O2A-O4A \\sim O2B-O3B
 with sigma of 0.04
 F3A-C25A \\sim F3B-C25B
 with sigma of 0.02
 O2A-C25A \\sim O2B-C25B
 with sigma of 0.04
 O4A-O3A \\sim O3B-O4B
 with sigma of 0.04
 F1A-C25A \\sim F2B-C25B
 with sigma of 0.02
 O3A-C25A \\sim O4B-C25B
 with sigma of 0.04
 F2A-C25A \\sim F1B-C25B
 with sigma of 0.02
 O2A-O3A \\sim O2B-O4B
 with sigma of 0.04
 O4A-C25A \\sim O3B-C25B
 with sigma of 0.04
 S3A-F3A \\sim S3B-F3B
 with sigma of 0.04
 F1A-F2A \\sim F2B-F1B
 with sigma of 0.04
 S3A-F1A \\sim S3B-F2B
 with sigma of 0.04
 S3A-F2A \\sim S3B-F1B
 with sigma of 0.04
 F3A-F1A \\sim F3B-F2B
 with sigma of 0.04
 F3A-F2A \\sim F3B-F1B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C25A \\sim C25B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4. Rigid body (RIGU) restrains
 S3B, F1B, F2B, F3B, O2B, O3B, O4B, C25B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(S3B)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(C25B)=1-
 FVAR(1)
 Sof(S3A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(C25A)=
 FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              60792
_olex2_submission_special_instructions 'No special instructions were received'