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_7157958
_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         'C27 H22 N S, C F3 O3 S'
_chemical_formula_sum            'C28 H22 F3 N O3 S2'
_chemical_formula_weight         541.58
_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     dual
_audit_creation_date             2019-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-09 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.143(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0241(6)
_cell_length_b                   20.8105(12)
_cell_length_c                   15.2442(8)
_cell_measurement_reflns_used    9003
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      30.500
_cell_measurement_theta_min      2.397
_cell_volume                     2457.2(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47717
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.528
_diffrn_reflns_theta_min         2.397
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.6756
_exptl_absorpt_correction_T_min  0.6377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1240 before and 0.0451 after correction. The Ratio of minimum to maximum transmission is 0.9439. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Et2O'
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         7440
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+1.2395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6580
_reflns_number_total             7440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00285f2.cif
_cod_data_source_block           0749_cg_0m
_cod_depositor_comments
'Adding full bibliography for 7157951--7157968.cif.'
_cod_database_code               7157958
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.914
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C20-H20A \\sim C20-H20E
 with sigma of 0.02
 C20-H20B \\sim C20-H20F
 with sigma of 0.02
 C20-H20C \\sim C20-H20D
 with sigma of 0.02
3. Others
 Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26)
4.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20(H20D,H20E,H20F), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              75970
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in NVH oil'
_olex2_submission_special_instructions 'No special instructions were received'