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_7157959
_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
'C25.882 H18 F2.646 N O3.646 S1.882, 0.118(C F3 O3 S)'
_chemical_formula_sum            'C26 H18 F3 N O4 S2'
_chemical_formula_weight         529.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-15
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_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                   9.8155(6)
_cell_length_b                   16.0505(14)
_cell_length_c                   29.742(2)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.501
_cell_measurement_theta_min      2.537
_cell_volume                     4685.7(6)
_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 n/a (Sheldrick, 2008)'
_computing_structure_solution    'XT n/a (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0432
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            89715
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.696
_diffrn_reflns_theta_min         2.486
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.6564
_exptl_absorpt_correction_T_min  0.5932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0878 before and 0.0514 after correction. The Ratio of minimum to maximum transmission is 0.9037. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       plate
_exptl_crystal_F_000             2176
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Et2O'
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6055
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0205P)^2^+4.4009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5463
_reflns_number_total             6055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00285f2.cif
_cod_data_source_block           mo_0846_cg_0m
_cod_depositor_comments
'Adding full bibliography for 7157951--7157968.cif.'
_cod_database_code               7157959
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S1-O2 \\sim S1-O2A
 with sigma of 0.02
 S2-O2 \\sim S2A-O2A
 with sigma of 0.02
 S2-O3 \\sim S2A-O3A
 with sigma of 0.02
 S2-O4 \\sim S2A-O4A
 with sigma of 0.02
 S2-C26 \\sim S2A-C26A
 with sigma of 0.02
 F1-C26 \\sim F1A-C26A
 with sigma of 0.02
 F2-C26 \\sim F2A-C26A
 with sigma of 0.02
 F3-C26 \\sim F3A-C26A
 with sigma of 0.02
 S1-S2 \\sim S1-S2A
 with sigma of 0.04
 S2-F1 \\sim S2A-F1A
 with sigma of 0.04
 S2-F2 \\sim S2A-F2A
 with sigma of 0.04
 S2-F3 \\sim S2A-F3A
 with sigma of 0.04
 F1-F2 \\sim F1A-F2A
 with sigma of 0.04
 F1-F3 \\sim F1A-F3A
 with sigma of 0.04
 F2-F3 \\sim F2A-F3A
 with sigma of 0.04
 O2-O3 \\sim O2A-O3A
 with sigma of 0.04
 O2-O4 \\sim O2A-O4A
 with sigma of 0.04
 O2-C26 \\sim O2A-C26A
 with sigma of 0.04
 O3-O4 \\sim O3A-O4A
 with sigma of 0.04
 O3-C26 \\sim O3A-C26A
 with sigma of 0.04
 O4-C26 \\sim O4A-C26A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 S2A, F1A, F2A, F3A, O2A, O3A, O4A, C26A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(S2A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(C26A)=1-
 FVAR(1)
 Sof(S2)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(C26)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25)
;
_shelx_res_checksum              11144
_olex2_submission_special_instructions 'No special instructions were received'