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_7157965
_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         'C25 H18 N S2, C F3 O3 S'
_chemical_formula_sum            'C26 H18 F3 N O3 S3'
_chemical_formula_weight         545.59
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-02
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0989(6)
_cell_length_b                   13.0989(6)
_cell_length_c                   27.9396(10)
_cell_measurement_reflns_used    9276
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.395
_cell_measurement_theta_min      2.683
_cell_volume                     4793.9(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture AgMo Dual Source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            265858
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         2.131
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.5962
_exptl_absorpt_correction_T_min  0.5784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0554 before and 0.0437 after correction.
The Ratio of minimum to maximum transmission is 0.9703.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Et2O'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.127
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.47(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         7323
_refine_ls_number_restraints     183
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0618P)^2^+2.9318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6681
_reflns_number_total             7323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00285f2.cif
_cod_data_source_block           mo_1014_cg_0m
_cod_depositor_comments
'Adding full bibliography for 7157951--7157968.cif.'
_cod_original_cell_volume        4793.9(5)
_cod_database_code               7157965
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.53(11)
 0.47(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 S2A-C8A \\sim S1B-C8B
 with sigma of 0.02
 S1-C12A \\sim S1-C12B
 with sigma of 0.04
 S2A-C9A \\sim S1B-C9B
 with sigma of 0.04
 C8A-C12A \\sim C8B-C12B
 with sigma of 0.04
 C8A-C10A \\sim C8B-C10B
 with sigma of 0.04
 S2A-C6 \\sim S1B-C6
 with sigma of 0.02
 S1-C8A \\sim S1-C8B
 with sigma of 0.04
 C7A-C9A \\sim C7B-C9B
 with sigma of 0.04
 S2A-C7A \\sim S1B-C7B
 with sigma of 0.04
 C10A-C12A \\sim C10B-C12B
 with sigma of 0.04
 C6-C8A \\sim C6-C8B
 with sigma of 0.04
 C8A-C7A \\sim C8B-C7B
 with sigma of 0.02
 C8A-C9A \\sim C8B-C9B
 with sigma of 0.02
 C7A-C11A \\sim C7B-C11B
 with sigma of 0.04
 C7A-C12A \\sim C7B-C12B
 with sigma of 0.02
 C10A-C9A \\sim C10B-C9B
 with sigma of 0.02
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.02
 C9A-C11A \\sim C9B-C11B
 with sigma of 0.04
 C12A-C11A \\sim C12B-C11B
 with sigma of 0.02
 S1-C7A \\sim S1-C7B
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 S1, S1B, C1, C2, C3, C4, C5, C6, C7B, C8B, C9B, C10B, C11B, C12B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 S1, S2A, C1, C2, C3, C4, C5, C6, C7A, C8A, C9A, C10A, C11A, C12A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 1*[Sof(C26A)+Sof(S3A)+Sof(F1A)+Sof(F2A)+Sof(F3A)+Sof(O1A)+Sof(O2A)+Sof(O3A)]+
 1*[Sof(C26B)+Sof(S2B)+Sof(F1B)+Sof(F2B)+Sof(F3B)+Sof(O1B)+Sof(O2B)+Sof(O3B)]+1*
 [Sof(C26C)+Sof(S3C)+Sof(F1C)+Sof(F2C)+Sof(F3C)+Sof(O1C)+Sof(O2C)+Sof(O3C)]=1
 with esd of 0.0001
 Sof(S1B)=Sof(C7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=
 Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(S2A)=Sof(C7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=
 Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
 Sof(C26A)=Sof(S3A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=
 FVAR(2)
 Sof(C26B)=Sof(S2B)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(O1B)=Sof(O2B)=Sof(O3B)=
 FVAR(3)
 Sof(C26C)=Sof(S3C)=Sof(F1C)=Sof(F2C)=Sof(F3C)=Sof(O1C)=Sof(O2C)=Sof(O3C)=
 FVAR(4)
6.a Free rotating group:
 C26B(S2B,F1B,F2B,F3B,O1B,O2B,O3B), C26A(S3A,F1A,F2A,F3A,O1A,O2A,O3A),
 C26C(S3C,F1C,F2C,F3C,O1C,O2C,O3C)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9A(H9A), C9B(H9B), C10A(H10A), C10B(H10B),
 C11A(H11A), C11B(H11B), C12A(H12A), C12B(H12B), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_shelx_res_checksum              24420
_olex2_submission_special_instructions 'No special instructions were received'