#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:15:24 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257335 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/76/1557688.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_1557688
loop_
_publ_author_name
'Messelberger, Julian'
'Grünwald, Annette'
'Goodner, Stephen J.'
'Zeilinger, Florian'
'Pinter, Piermaria'
'Miehlich, Matthias E.'
'Heinemann, Frank W.'
'Hansmann, Max M.'
'Munz, Dominik'
_publ_section_title
;
 Aromaticity and sterics control whether a cationic olefin radical is
 resistant to disproportionation
;
_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              4138
_journal_page_last               4149
_journal_paper_doi               10.1039/D0SC00699H
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C25 H39 N3, C F3 O3 S'
_chemical_formula_sum            'C26 H39 F3 N3 O3 S'
_chemical_formula_weight         530.66
_chemical_properties_physical    Moisture-sensitive,Oxygen-sensitive
_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
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-08 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.508(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9305(9)
_cell_length_b                   11.6700(7)
_cell_length_c                   16.4062(9)
_cell_measurement_reflns_used    9691
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      2.27
_cell_volume                     2694.5(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'Bruker APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXTL 6.12 (Bruker AXS, 2002)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa ImuS Duo Photon II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar focussing montel optics'
_diffrn_radiation_source         'ImuS high brilliance micro-focus tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            94277
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_min         2.186
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1223 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.9647.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       needle
_exptl_crystal_F_000             1132
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: tetrahydrofuran, diethyl ether'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0374P)²+3.6010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5782
_reflns_number_total             6421
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc00699h2.cif
_cod_data_source_block           jm1903
_cod_depositor_comments
;Adding full bibliography for 1557687--1557688.cif.

 Adding full bibliography for 1557687--1557688.cif.
;
_cod_database_code               1557688
_shelx_shelxl_version_number     2016/6
_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   0.991
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=
 Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C11)=
 Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C20(H20), C23(H23)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C8A(H8AA,H8AB)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C16(H16), C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C10A(H10D,H10E,H10F),
 C11A(H11D,H11E,H11F)
;
_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
N1 N 0.64121(11) 0.23941(14) 0.52294(10) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.70709(12) 0.11113(14) 0.46649(10) 0.0231(3) Uani 1 1 d . . . . .
N3 N 0.84967(10) 0.31805(12) 0.62271(9) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.72441(13) 0.21063(15) 0.51170(11) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.57370(14) 0.15720(18) 0.48600(13) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.509893 0.156859 0.485502 0.033 Uiso 1 1 calc R . . . .
C3 C 0.61443(15) 0.07782(18) 0.45092(13) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.584848 0.010917 0.420847 0.034 Uiso 1 1 calc R . . . .
C4 C 0.61712(14) 0.35394(17) 0.54602(13) 0.0250(4) Uani 1 1 d . . . . .
H4A H 0.564137 0.348224 0.568470 0.037 Uiso 1 1 calc GR . . . .
H4B H 0.598686 0.403046 0.494614 0.037 Uiso 1 1 calc GR . . . .
H4C H 0.672430 0.387108 0.590406 0.037 Uiso 1 1 calc GR . . . .
C5 C 0.77262(16) 0.0463(2) 0.43491(16) 0.0357(5) Uani 1 1 d . . . . .
H5A H 0.768839 -0.035211 0.447691 0.054 Uiso 1 1 calc GR . . . .
H5B H 0.837598 0.073783 0.463562 0.054 Uiso 1 1 calc GR . . . .
H5C H 0.755346 0.056938 0.372285 0.054 Uiso 1 1 calc GR . . . .
C6 C 0.81168(13) 0.27647(15) 0.53834(11) 0.0175(3) Uani 1 1 d . . . . .
C7 C 0.90548(14) 0.42658(16) 0.62393(12) 0.0229(4) Uani 1 1 d . . . . .
C8 C 0.9238(4) 0.4178(4) 0.5428(3) 0.0257(10) Uani 0.474(5) 1 d . . P A 1
H8A H 0.986022 0.380188 0.552814 0.031 Uiso 0.474(5) 1 calc R . P A 1
H8B H 0.926916 0.495609 0.519762 0.031 Uiso 0.474(5) 1 calc R . P A 1
C9 C 0.84370(14) 0.34687(16) 0.47475(12) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.9889(3) 0.4365(4) 0.7061(3) 0.0302(11) Uani 0.474(5) 1 d . . P A 1
H10A H 0.966410 0.435848 0.755788 0.045 Uiso 0.474(5) 1 calc GR . P A 1
H10B H 1.022734 0.508321 0.705651 0.045 Uiso 0.474(5) 1 calc GR . P A 1
H10C H 1.032042 0.371677 0.710453 0.045 Uiso 0.474(5) 1 calc GR . P A 1
C11 C 0.8371(4) 0.5325(4) 0.6236(3) 0.0276(11) Uani 0.474(5) 1 d . . P A 1
H11A H 0.826322 0.536207 0.679261 0.041 Uiso 0.474(5) 1 calc GR . P A 1
H11B H 0.776245 0.522395 0.577019 0.041 Uiso 0.474(5) 1 calc GR . P A 1
H11C H 0.867020 0.603856 0.614295 0.041 Uiso 0.474(5) 1 calc GR . P A 1
C12 C 0.9093(2) 0.2866(3) 0.43482(19) 0.0600(9) Uani 1 1 d . . . . .
H12A H 0.962986 0.252945 0.480720 0.090 Uiso 1 1 calc GR . . . .
H12B H 0.933062 0.342089 0.402090 0.090 Uiso 1 1 calc GR . . . .
H12C H 0.874201 0.225916 0.395903 0.090 Uiso 1 1 calc GR . . . .
C13 C 0.7601(2) 0.3910(4) 0.4003(2) 0.0765(13) Uani 1 1 d . . . . .
H13A H 0.716014 0.431483 0.423079 0.115 Uiso 1 1 calc GR . . . .
H13B H 0.727269 0.326440 0.364541 0.115 Uiso 1 1 calc GR . . . .
H13C H 0.782969 0.443751 0.365068 0.115 Uiso 1 1 calc GR . . . .
C14 C 0.87311(12) 0.24390(15) 0.69830(11) 0.0164(3) Uani 1 1 d . . . . .
C15 C 0.83562(13) 0.26749(15) 0.76488(11) 0.0179(3) Uani 1 1 d . . . . .
C16 C 0.86268(14) 0.19785(16) 0.83856(11) 0.0219(4) Uani 1 1 d . . . . .
H16 H 0.836735 0.212300 0.883132 0.026 Uiso 1 1 calc R . . . .
C17 C 0.92612(14) 0.10872(17) 0.84808(12) 0.0231(4) Uani 1 1 d . . . . .
H17 H 0.943821 0.062782 0.898789 0.028 Uiso 1 1 calc R . . . .
C18 C 0.96363(13) 0.08687(16) 0.78333(12) 0.0219(4) Uani 1 1 d . . . . .
H18 H 1.008152 0.026320 0.790598 0.026 Uiso 1 1 calc R . . . .
C19 C 0.93779(12) 0.15144(15) 0.70750(12) 0.0189(3) Uani 1 1 d . . . . .
C20 C 0.76379(13) 0.36096(16) 0.76164(11) 0.0196(4) Uani 1 1 d . . . . .
H20 H 0.752436 0.405373 0.706981 0.023 Uiso 1 1 calc R . . . .
C21 C 0.66893(15) 0.30762(18) 0.75944(14) 0.0285(4) Uani 1 1 d . . . . .
H21A H 0.620143 0.367422 0.747359 0.043 Uiso 1 1 calc GR . . . .
H21B H 0.676400 0.272301 0.815524 0.043 Uiso 1 1 calc GR . . . .
H21C H 0.649732 0.249127 0.714040 0.043 Uiso 1 1 calc GR . . . .
C22 C 0.79884(16) 0.44489(17) 0.83801(13) 0.0279(4) Uani 1 1 d . . . . .
H22A H 0.753153 0.507765 0.829826 0.042 Uiso 1 1 calc GR . . . .
H22B H 0.860831 0.475875 0.840904 0.042 Uiso 1 1 calc GR . . . .
H22C H 0.804856 0.404528 0.891964 0.042 Uiso 1 1 calc GR . . . .
C23 C 0.98126(14) 0.11546(17) 0.63964(13) 0.0243(4) Uani 1 1 d . . . . .
H23 H 0.953958 0.165209 0.587584 0.029 Uiso 1 1 calc R . . . .
C24 C 0.95591(19) -0.00933(19) 0.61246(15) 0.0369(5) Uani 1 1 d . . . . .
H24A H 0.974748 -0.027054 0.562075 0.055 Uiso 1 1 calc GR . . . .
H24B H 0.887233 -0.020356 0.597579 0.055 Uiso 1 1 calc GR . . . .
H24C H 0.989545 -0.060349 0.660342 0.055 Uiso 1 1 calc GR . . . .
C25 C 1.08987(16) 0.1285(3) 0.67103(17) 0.0467(7) Uani 1 1 d . . . . .
H25A H 1.113282 0.113973 0.622845 0.070 Uiso 1 1 calc GR . . . .
H25B H 1.118507 0.073309 0.717482 0.070 Uiso 1 1 calc GR . . . .
H25C H 1.107107 0.206450 0.692800 0.070 Uiso 1 1 calc GR . . . .
S1 S 0.35217(4) 0.27634(4) 0.57503(3) 0.02992(14) Uani 1 1 d . . . . .
O1 O 0.38626(13) 0.38986(14) 0.56936(11) 0.0401(4) Uani 1 1 d . . . . .
O2 O 0.41807(17) 0.18812(15) 0.57314(14) 0.0555(6) Uani 1 1 d . . . . .
O3 O 0.25643(16) 0.2536(2) 0.52429(13) 0.0662(7) Uani 1 1 d . . . . .
C26 C 0.35211(17) 0.26519(19) 0.68573(14) 0.0318(5) Uani 1 1 d . . . . .
F1 F 0.32228(10) 0.16314(11) 0.70185(8) 0.0359(3) Uani 1 1 d . . . . .
F2 F 0.29686(17) 0.34229(15) 0.70353(13) 0.0719(6) Uani 1 1 d . . . . .
F3 F 0.43969(13) 0.27894(17) 0.74219(10) 0.0641(5) Uani 1 1 d . . . . .
C8A C 0.8735(3) 0.4591(3) 0.5253(2) 0.0217(8) Uani 0.526(5) 1 d . . P A 2
H8AA H 0.819567 0.513445 0.510528 0.026 Uiso 0.526(5) 1 calc R . P A 2
H8AB H 0.926643 0.495211 0.511379 0.026 Uiso 0.526(5) 1 calc R . P A 2
C10A C 1.0171(3) 0.4014(3) 0.6566(3) 0.0258(9) Uani 0.526(5) 1 d . . P A 2
H10D H 1.031404 0.345628 0.618073 0.039 Uiso 0.526(5) 1 calc GR . P A 2
H10E H 1.036670 0.370452 0.715500 0.039 Uiso 0.526(5) 1 calc GR . P A 2
H10F H 1.051586 0.472783 0.656371 0.039 Uiso 0.526(5) 1 calc GR . P A 2
C11A C 0.8893(3) 0.5223(3) 0.6758(3) 0.0266(10) Uani 0.526(5) 1 d . . P A 2
H11D H 0.923644 0.590203 0.666993 0.040 Uiso 0.526(5) 1 calc GR . P A 2
H11E H 0.912298 0.501208 0.737117 0.040 Uiso 0.526(5) 1 calc GR . P A 2
H11F H 0.821175 0.539342 0.657760 0.040 Uiso 0.526(5) 1 calc GR . P A 2
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
C1 N1 C2 109.66(16) . . ?
C1 N1 C4 125.11(16) . . ?
C2 N1 C4 122.83(16) . . ?
C1 N2 C3 109.86(16) . . ?
C1 N2 C5 127.54(17) . . ?
C3 N2 C5 122.57(17) . . ?
C6 N3 C7 110.11(14) . . ?
C6 N3 C14 122.72(14) . . ?
C14 N3 C7 120.78(14) . . ?
N1 C1 C6 126.83(16) . . ?
N2 C1 N1 105.68(16) . . ?
N2 C1 C6 127.40(17) . . ?
N1 C2 H2 126.3 . . ?
C3 C2 N1 107.49(18) . . ?
C3 C2 H2 126.3 . . ?
N2 C3 H3 126.3 . . ?
C2 C3 N2 107.30(18) . . ?
C2 C3 H3 126.3 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C1 120.68(15) . . ?
N3 C6 C9 112.01(15) . . ?
C1 C6 C9 122.36(15) . . ?
N3 C7 C11 107.4(2) . . ?
N3 C7 C8A 102.22(18) . . ?
N3 C7 C10A 111.02(19) . . ?
C8 C7 N3 101.6(2) . . ?
C8 C7 C10 118.3(3) . . ?
C8 C7 C11 111.5(3) . . ?
C10 C7 N3 111.3(2) . . ?
C10 C7 C11 106.3(3) . . ?
C8A C7 C10A 108.3(2) . . ?
C11A C7 N3 116.6(2) . . ?
C11A C7 C8A 111.1(3) . . ?
C11A C7 C10A 107.4(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 C9 110.9(3) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C6 C9 C8 97.82(19) . . ?
C6 C9 C8A 100.99(18) . . ?
C12 C9 C6 116.09(17) . . ?
C12 C9 C8 95.9(3) . . ?
C12 C9 C8A 121.0(3) . . ?
C13 C9 C6 111.89(18) . . ?
C13 C9 C8 128.3(3) . . ?
C13 C9 C12 106.6(2) . . ?
C13 C9 C8A 99.1(3) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 119.93(15) . . ?
C15 C14 C19 119.79(16) . . ?
C19 C14 N3 120.19(15) . . ?
C14 C15 C20 124.84(16) . . ?
C16 C15 C14 118.73(17) . . ?
C16 C15 C20 116.38(16) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.65(17) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.45(17) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.64(17) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C23 124.87(16) . . ?
C18 C19 C14 118.72(17) . . ?
C18 C19 C23 116.41(16) . . ?
C15 C20 H20 108.1 . . ?
C15 C20 C21 110.16(15) . . ?
C15 C20 C22 112.64(16) . . ?
C21 C20 H20 108.1 . . ?
C21 C20 C22 109.71(16) . . ?
C22 C20 H20 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23 108.2 . . ?
C19 C23 C24 110.52(16) . . ?
C19 C23 C25 112.79(18) . . ?
C24 C23 H23 108.2 . . ?
C24 C23 C25 108.78(19) . . ?
C25 C23 H23 108.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 S1 C26 104.43(10) . . ?
O2 S1 O1 113.68(11) . . ?
O2 S1 C26 101.51(11) . . ?
O3 S1 O1 116.43(13) . . ?
O3 S1 O2 114.70(15) . . ?
O3 S1 C26 103.65(12) . . ?
F1 C26 S1 111.99(14) . . ?
F1 C26 F3 106.6(2) . . ?
F2 C26 S1 112.40(17) . . ?
F2 C26 F1 106.96(18) . . ?
F2 C26 F3 107.7(2) . . ?
F3 C26 S1 110.89(15) . . ?
C7 C8A H8AA 110.4 . . ?
C7 C8A H8AB 110.4 . . ?
C9 C8A C7 106.5(2) . . ?
C9 C8A H8AA 110.4 . . ?
C9 C8A H8AB 110.4 . . ?
H8AA C8A H8AB 108.6 . . ?
C7 C10A H10D 109.5 . . ?
C7 C10A H10E 109.5 . . ?
C7 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C7 C11A H11D 109.5 . . ?
C7 C11A H11E 109.5 . . ?
C7 C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
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
N1 C1 1.357(2) . ?
N1 C2 1.377(3) . ?
N1 C4 1.466(2) . ?
N2 C1 1.355(2) . ?
N2 C3 1.376(3) . ?
N2 C5 1.462(3) . ?
N3 C6 1.396(2) . ?
N3 C7 1.513(2) . ?
N3 C14 1.456(2) . ?
C1 C6 1.449(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.339(3) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C9 1.525(2) . ?
C7 C8 1.450(4) . ?
C7 C10 1.504(5) . ?
C7 C11 1.602(5) . ?
C7 C8A 1.573(4) . ?
C7 C10A 1.598(4) . ?
C7 C11A 1.473(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.572(5) . ?
C9 C12 1.521(3) . ?
C9 C13 1.516(3) . ?
C9 C8A 1.534(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.411(2) . ?
C14 C19 1.422(2) . ?
C15 C16 1.399(2) . ?
C15 C20 1.518(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(2) . ?
C19 C23 1.523(3) . ?
C20 H20 1.0000 . ?
C20 C21 1.536(3) . ?
C20 C22 1.538(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 1.0000 . ?
C23 C24 1.533(3) . ?
C23 C25 1.536(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
S1 O1 1.4333(16) . ?
S1 O2 1.432(2) . ?
S1 O3 1.418(2) . ?
S1 C26 1.821(2) . ?
C26 F1 1.329(2) . ?
C26 F2 1.318(3) . ?
C26 F3 1.336(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C6 N3 50.3(3) . . . . ?
N1 C1 C6 C9 -102.7(2) . . . . ?
N1 C2 C3 N2 0.1(2) . . . . ?
N2 C1 C6 N3 -133.53(19) . . . . ?
N2 C1 C6 C9 73.4(2) . . . . ?
N3 C6 C9 C8 11.8(3) . . . . ?
N3 C6 C9 C12 112.3(2) . . . . ?
N3 C6 C9 C13 -125.0(2) . . . . ?
N3 C6 C9 C8A -20.5(3) . . . . ?
N3 C7 C8 C9 28.1(4) . . . . ?
N3 C7 C8A C9 -26.2(3) . . . . ?
N3 C14 C15 C16 -177.18(16) . . . . ?
N3 C14 C15 C20 5.5(3) . . . . ?
N3 C14 C19 C18 175.73(16) . . . . ?
N3 C14 C19 C23 -5.0(3) . . . . ?
C1 N1 C2 C3 -0.7(2) . . . . ?
C1 N2 C3 C2 0.4(2) . . . . ?
C1 C6 C9 C8 167.0(2) . . . . ?
C1 C6 C9 C12 -92.5(3) . . . . ?
C1 C6 C9 C13 30.1(3) . . . . ?
C1 C6 C9 C8A 134.7(2) . . . . ?
C2 N1 C1 N2 0.9(2) . . . . ?
C2 N1 C1 C6 177.70(17) . . . . ?
C3 N2 C1 N1 -0.8(2) . . . . ?
C3 N2 C1 C6 -177.58(17) . . . . ?
C4 N1 C1 N2 -161.82(17) . . . . ?
C4 N1 C1 C6 15.0(3) . . . . ?
C4 N1 C2 C3 162.52(18) . . . . ?
C5 N2 C1 N1 177.53(19) . . . . ?
C5 N2 C1 C6 0.8(3) . . . . ?
C5 N2 C3 C2 -178.02(19) . . . . ?
C6 N3 C7 C8 -19.8(3) . . . . ?
C6 N3 C7 C10 -146.7(2) . . . . ?
C6 N3 C7 C11 97.4(2) . . . . ?
C6 N3 C7 C8A 13.5(2) . . . . ?
C6 N3 C7 C10A -101.8(2) . . . . ?
C6 N3 C7 C11A 134.8(3) . . . . ?
C6 N3 C14 C15 -126.23(18) . . . . ?
C6 N3 C14 C19 57.2(2) . . . . ?
C6 C9 C8A C7 28.0(3) . . . . ?
C7 N3 C6 C1 -151.34(16) . . . . ?
C7 N3 C6 C9 4.3(2) . . . . ?
C7 N3 C14 C15 84.6(2) . . . . ?
C7 N3 C14 C19 -91.9(2) . . . . ?
C7 C8 C9 C6 -25.2(4) . . . . ?
C7 C8 C9 C12 -142.6(3) . . . . ?
C7 C8 C9 C13 100.8(4) . . . . ?
C10 C7 C8 C9 150.3(3) . . . . ?
C11 C7 C8 C9 -86.1(4) . . . . ?
C12 C9 C8A C7 -101.8(3) . . . . ?
C13 C9 C8A C7 142.5(2) . . . . ?
C14 N3 C6 C1 56.6(2) . . . . ?
C14 N3 C6 C9 -147.72(16) . . . . ?
C14 N3 C7 C8 132.8(3) . . . . ?
C14 N3 C7 C10 5.9(3) . . . . ?
C14 N3 C7 C11 -110.0(2) . . . . ?
C14 N3 C7 C8A 166.2(2) . . . . ?
C14 N3 C7 C10A 50.9(2) . . . . ?
C14 N3 C7 C11A -72.5(3) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C14 C15 C20 C21 113.5(2) . . . . ?
C14 C15 C20 C22 -123.68(19) . . . . ?
C14 C19 C23 C24 -121.1(2) . . . . ?
C14 C19 C23 C25 116.9(2) . . . . ?
C15 C14 C19 C18 -0.8(3) . . . . ?
C15 C14 C19 C23 178.43(17) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C15 C20 C21 -63.9(2) . . . . ?
C16 C15 C20 C22 59.0(2) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C17 C18 C19 C14 1.7(3) . . . . ?
C17 C18 C19 C23 -177.59(18) . . . . ?
C18 C19 C23 C24 58.2(2) . . . . ?
C18 C19 C23 C25 -63.8(2) . . . . ?
C19 C14 C15 C16 -0.6(3) . . . . ?
C19 C14 C15 C20 -177.91(16) . . . . ?
C20 C15 C16 C17 178.77(17) . . . . ?
O1 S1 C26 F1 -179.70(17) . . . . ?
O1 S1 C26 F2 59.86(19) . . . . ?
O1 S1 C26 F3 -60.80(19) . . . . ?
O2 S1 C26 F1 -61.29(19) . . . . ?
O2 S1 C26 F2 178.27(18) . . . . ?
O2 S1 C26 F3 57.61(19) . . . . ?
O3 S1 C26 F1 57.9(2) . . . . ?
O3 S1 C26 F2 -62.5(2) . . . . ?
O3 S1 C26 F3 176.84(19) . . . . ?
C10A C7 C8A C9 91.1(3) . . . . ?
C11A C7 C8A C9 -151.2(3) . . . . ?
