#------------------------------------------------------------------------------
#$Date: 2021-05-05 12:03:13 +0300 (Wed, 05 May 2021) $
#$Revision: 264946 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157958.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7157958
loop_
_publ_author_name
'Li, Zhen'
'Vijaykumar, Gonela'
'Li, Xiangdong'
'Golz, Christopher'
'Alcarazo, Manuel'
_publ_section_title
;
 5-(Diarylimino)- and 5-(sulfoximido)dibenzothiophenium triflates:
 syntheses and applications as electrophilic aminating reagents.
;
_journal_issue                   13
_journal_name_full               'Organic & 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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0414P)²+1.2395P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.82985(3) 0.53993(2) 0.37790(2) 0.01758(7) Uani 1 1 d . . . . .
N1 N 0.66180(12) 0.58004(5) 0.30718(6) 0.01832(18) Uani 1 1 d . . . . .
C1 C 0.72596(14) 0.48429(5) 0.43409(7) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.74524(14) 0.50157(5) 0.52517(7) 0.01646(19) Uani 1 1 d . . . . .
C3 C 0.83696(14) 0.56253(5) 0.54861(7) 0.0169(2) Uani 1 1 d . . . . .
C4 C 0.88592(14) 0.58993(6) 0.47507(7) 0.0179(2) Uani 1 1 d . . . . .
C5 C 0.98054(15) 0.64620(6) 0.48132(8) 0.0221(2) Uani 1 1 d . . . . .
H5 H 1.012368 0.663355 0.430251 0.027 Uiso 1 1 calc R . . . .
C6 C 1.02694(16) 0.67650(6) 0.56544(9) 0.0244(2) Uani 1 1 d . . . . .
H6 H 1.092109 0.715145 0.572514 0.029 Uiso 1 1 calc R . . . .
C7 C 0.97863(16) 0.65063(6) 0.63966(8) 0.0236(2) Uani 1 1 d . . . . .
H7 H 1.011461 0.672083 0.696597 0.028 Uiso 1 1 calc R . . . .
C8 C 0.88342(15) 0.59411(6) 0.63195(8) 0.0202(2) Uani 1 1 d . . . . .
H8 H 0.850522 0.577274 0.682886 0.024 Uiso 1 1 calc R . . . .
C9 C 0.68078(15) 0.46038(6) 0.58013(8) 0.0192(2) Uani 1 1 d . . . . .
H9 H 0.693708 0.470325 0.642377 0.023 Uiso 1 1 calc R . . . .
C10 C 0.59690(15) 0.40428(6) 0.54267(8) 0.0214(2) Uani 1 1 d . . . . .
H10 H 0.551368 0.376222 0.579782 0.026 Uiso 1 1 calc R . . . .
C11 C 0.57853(16) 0.38854(6) 0.45176(8) 0.0226(2) Uani 1 1 d . . . . .
H11 H 0.520026 0.350175 0.427683 0.027 Uiso 1 1 calc R . . . .
C12 C 0.64519(15) 0.42856(6) 0.39575(8) 0.0209(2) Uani 1 1 d . . . . .
H12 H 0.635460 0.417961 0.333999 0.025 Uiso 1 1 calc R . . . .
C13 C 0.67438(14) 0.58478(5) 0.22361(7) 0.01541(19) Uani 1 1 d . . . . .
C14 C 0.54148(14) 0.62358(5) 0.16136(7) 0.01558(19) Uani 1 1 d . . . . .
C15 C 0.44074(15) 0.66742(5) 0.19501(7) 0.0179(2) Uani 1 1 d . . . . .
H15 H 0.462135 0.673948 0.258666 0.021 Uiso 1 1 calc R . . . .
C16 C 0.31010(15) 0.70122(5) 0.13562(8) 0.0188(2) Uani 1 1 d . . . . .
H16 H 0.241930 0.730592 0.159044 0.023 Uiso 1 1 calc R . . . .
C17 C 0.27701(14) 0.69270(5) 0.04136(8) 0.0181(2) Uani 1 1 d . . . . .
C18 C 0.37956(15) 0.65016(6) 0.00811(7) 0.0186(2) Uani 1 1 d . . . . .
H18 H 0.359572 0.644459 -0.055629 0.022 Uiso 1 1 calc R . . . .
C19 C 0.51097(14) 0.61588(6) 0.06709(7) 0.0177(2) Uani 1 1 d . . . . .
H19 H 0.580349 0.587144 0.043436 0.021 Uiso 1 1 calc R . . . .
C20 C 0.13456(16) 0.72983(6) -0.02182(9) 0.0254(2) Uani 1 1 d D . . . .
H20A H 0.022812 0.715115 -0.014690 0.038 Uiso 0.58(3) 1 calc DGR . P A 1
H20B H 0.139380 0.722875 -0.084688 0.038 Uiso 0.58(3) 1 calc DGR . P A 1
H20C H 0.148537 0.775709 -0.007291 0.038 Uiso 0.58(3) 1 calc DGR . P A 1
H20D H 0.048586 0.742341 0.010325 0.038 Uiso 0.42(3) 1 calc DGR . P A 2
H20E H 0.079640 0.702932 -0.074159 0.038 Uiso 0.42(3) 1 calc DGR . P A 2
H20F H 0.182503 0.768427 -0.042835 0.038 Uiso 0.42(3) 1 calc DGR . P A 2
C21 C 0.80967(14) 0.55276(5) 0.18802(7) 0.01524(19) Uani 1 1 d . . . . .
C22 C 0.80778(15) 0.48627(5) 0.17627(7) 0.0186(2) Uani 1 1 d . . . . .
H22 H 0.718569 0.461172 0.189599 0.022 Uiso 1 1 calc R . . . .
C23 C 0.93715(15) 0.45675(5) 0.14491(8) 0.0197(2) Uani 1 1 d . . . . .
H23 H 0.934064 0.411536 0.136074 0.024 Uiso 1 1 calc R . . . .
C24 C 1.07072(15) 0.49232(6) 0.12632(8) 0.0199(2) Uani 1 1 d . . . . .
C25 C 1.06924(16) 0.55879(6) 0.13758(9) 0.0230(2) Uani 1 1 d . . . . .
H25 H 1.159118 0.583807 0.124802 0.028 Uiso 1 1 calc R . . . .
C26 C 0.93957(15) 0.58944(6) 0.16705(8) 0.0204(2) Uani 1 1 d . . . . .
H26 H 0.939494 0.634894 0.172825 0.024 Uiso 1 1 calc R . . . .
C27 C 1.21430(18) 0.46037(7) 0.09521(10) 0.0290(3) Uani 1 1 d . . . . .
H27A H 1.306132 0.447320 0.148312 0.044 Uiso 1 1 calc GR . . . .
H27B H 1.260951 0.490637 0.058452 0.044 Uiso 1 1 calc GR . . . .
H27C H 1.169008 0.422418 0.058668 0.044 Uiso 1 1 calc GR . . . .
S2 S 0.92885(4) 0.77972(2) 0.26879(2) 0.02148(7) Uani 1 1 d . . . . .
F1 F 1.21447(11) 0.71464(4) 0.33421(6) 0.03077(18) Uani 1 1 d . . . . .
F2 F 1.17071(10) 0.78934(4) 0.42314(5) 0.03126(18) Uani 1 1 d . . . . .
F3 F 1.25581(11) 0.81341(4) 0.30413(6) 0.03373(19) Uani 1 1 d . . . . .
O1 O 0.84252(13) 0.73169(6) 0.30867(7) 0.0341(2) Uani 1 1 d . . . . .
O2 O 0.94168(13) 0.76560(5) 0.17809(6) 0.02708(19) Uani 1 1 d . . . . .
O3 O 0.88503(15) 0.84537(5) 0.28422(6) 0.0333(2) Uani 1 1 d . . . . .
C28 C 1.15327(16) 0.77427(6) 0.33602(8) 0.0219(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C1 103.34(5) . . ?
N1 S1 C4 103.13(5) . . ?
C4 S1 C1 91.62(5) . . ?
C13 N1 S1 113.74(8) . . ?
C2 C1 S1 111.51(9) . . ?
C12 C1 S1 124.87(9) . . ?
C12 C1 C2 123.51(11) . . ?
C1 C2 C3 112.47(10) . . ?
C9 C2 C1 118.45(11) . . ?
C9 C2 C3 129.07(10) . . ?
C4 C3 C2 112.67(10) . . ?
C8 C3 C2 129.04(10) . . ?
C8 C3 C4 118.26(11) . . ?
C3 C4 S1 111.54(9) . . ?
C5 C4 S1 124.72(9) . . ?
C5 C4 C3 123.49(11) . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.18(11) . . ?
C6 C5 H5 121.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.58(12) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.35(11) . . ?
C8 C7 H7 119.3 . . ?
C3 C8 H8 120.4 . . ?
C7 C8 C3 119.13(11) . . ?
C7 C8 H8 120.4 . . ?
C2 C9 H9 120.5 . . ?
C2 C9 C10 119.06(10) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.25(11) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.68(11) . . ?
C12 C11 H11 119.7 . . ?
C1 C12 C11 117.04(11) . . ?
C1 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
N1 C13 C14 116.28(9) . . ?
N1 C13 C21 124.71(9) . . ?
C14 C13 C21 119.00(9) . . ?
C15 C14 C13 120.77(9) . . ?
C15 C14 C19 119.10(10) . . ?
C19 C14 C13 120.12(10) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.11(10) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.93(10) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C20 120.04(11) . . ?
C18 C17 C16 118.81(10) . . ?
C18 C17 C20 121.14(10) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.77(10) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.25(10) . . ?
C18 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
C17 C20 H20D 109.5 . . ?
C17 C20 H20E 109.5 . . ?
C17 C20 H20F 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H20D C20 H20E 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
C22 C21 C13 120.35(10) . . ?
C26 C21 C13 119.83(10) . . ?
C26 C21 C22 119.81(10) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.81(10) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.19(11) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 118.09(11) . . ?
C23 C24 C27 121.42(11) . . ?
C25 C24 C27 120.48(11) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.72(11) . . ?
C26 C25 H25 119.1 . . ?
C21 C26 H26 120.3 . . ?
C25 C26 C21 119.33(11) . . ?
C25 C26 H26 120.3 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 S2 O2 115.23(7) . . ?
O1 S2 O3 115.06(7) . . ?
O1 S2 C28 103.45(6) . . ?
O2 S2 O3 115.45(6) . . ?
O2 S2 C28 102.60(6) . . ?
O3 S2 C28 102.32(6) . . ?
F1 C28 S2 111.05(9) . . ?
F2 C28 S2 112.01(8) . . ?
F2 C28 F1 107.14(10) . . ?
F2 C28 F3 107.70(10) . . ?
F3 C28 S2 111.60(8) . . ?
F3 C28 F1 107.08(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.7081(9) . ?
S1 C1 1.7728(12) . ?
S1 C4 1.7695(12) . ?
N1 C13 1.3078(13) . ?
C1 C2 1.4031(15) . ?
C1 C12 1.3816(17) . ?
C2 C3 1.4633(16) . ?
C2 C9 1.3895(15) . ?
C3 C4 1.4023(15) . ?
C3 C8 1.3919(15) . ?
C4 C5 1.3853(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3897(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3961(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3908(18) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.3933(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3938(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3955(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.4701(14) . ?
C13 C21 1.4915(15) . ?
C14 C15 1.4020(15) . ?
C14 C19 1.4024(14) . ?
C15 H15 0.9500 . ?
C15 C16 1.3847(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.4026(15) . ?
C17 C18 1.3913(16) . ?
C17 C20 1.5019(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3906(15) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 H20D 0.9800 . ?
C20 H20E 0.9800 . ?
C20 H20F 0.9800 . ?
C21 C22 1.3949(15) . ?
C21 C26 1.3948(15) . ?
C22 H22 0.9500 . ?
C22 C23 1.3938(16) . ?
C23 H23 0.9500 . ?
C23 C24 1.3913(17) . ?
C24 C25 1.3944(17) . ?
C24 C27 1.5099(16) . ?
C25 H25 0.9500 . ?
C25 C26 1.3911(16) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
S2 O1 1.4382(11) . ?
S2 O2 1.4433(9) . ?
S2 O3 1.4453(10) . ?
S2 C28 1.8280(13) . ?
F1 C28 1.3374(14) . ?
F2 C28 1.3360(14) . ?
F3 C28 1.3364(14) . ?
