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Two binary cocrystals of 1,4-di­iodo­tetra­fluoro­benzene (1,4-DITFB, C6F4I2) and 1,3,5-tri­fluoro-2,4,6-tri­iodo­benzene (1,3,5-TITFB, C6F3I3) with the flexible 2-{[(naphthalen-2-yl)meth­yl]sulfan­yl}pyridine 1-oxide (NTPO, C16H13NOS) mol­ecule were successfully prepared and characterized by X-ray diffraction and quantum chemistry calculation methods. X-ray diffraction analysis reveals that the conformation of the flexible NTPO mol­ecule has been changed significantly after introducing the 1,4-DITFB or 1,3,5-TITFB mol­ecule into the NTPO lattice. Also the formation of the binary cocrystals is driven mainly by robust C—I...O—N+ halogen bonds and π-hole...π-bond inter­actions, and they possess `sandwich' structural frameworks. Moreover, inter­action energy analysis and AIM analysis were used to explore the contribution of different fragments to the structural stability and the corresponding electronic properties, which reveals that the robust halogen bonds with shorter bonding lengths [2.768 (4) and 2.789 (3) Å] are suggested to be covalent to a certain degree.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622011822/bs3005sup1.cif
Contains datablocks 1, 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622011822/bs30051sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622011822/bs30052sup3.hkl
Contains datablock 2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622011822/bs30051sup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622011822/bs30052sup5.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229622011822/bs3005sup6.pdf
Supplementary material

CCDC references: 2181569; 2181570

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2019 (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1,4-Diiodotetrafluorobenzene–2-{[(naphthalen-2-yl)methyl]sulfanyl}pyridine 1-oxide (1/1) (1) top
Crystal data top
C6F4I2·C16H13NOSZ = 2
Mr = 669.19F(000) = 636
Triclinic, P1Dx = 2.060 Mg m3
a = 6.9303 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 12.6026 (5) ÅCell parameters from 5647 reflections
c = 13.1299 (6) Åθ = 3.6–73.1°
α = 71.495 (4)°µ = 24.25 mm1
β = 82.851 (4)°T = 100 K
γ = 87.566 (4)°Plate, colourless
V = 1079.01 (8) Å30.1 × 0.1 × 0.05 × 0.08 (radius) mm
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an AtlasS2 detector
3808 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source3699 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.034
Detector resolution: 5.3127 pixels mm-1θmax = 66.6°, θmin = 3.6°
ω scansh = 87
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2017)
k = 1014
Tmin = 0.580, Tmax = 1.000l = 1415
6503 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0661P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095(Δ/σ)max = 0.002
S = 1.09Δρmax = 1.54 e Å3
3808 reflectionsΔρmin = 1.37 e Å3
281 parametersExtinction correction: SHELXL2019 (Sheldrick, 2015a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00114 (12)
Primary atom site location: dual
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.79225 (3)0.52096 (2)0.77202 (2)0.01851 (12)
I20.80214 (3)1.07529 (2)0.77351 (2)0.01806 (13)
S10.75615 (13)0.37118 (8)0.53046 (7)0.0185 (2)
F10.7572 (4)0.6289 (2)0.9685 (2)0.0257 (5)
F20.7629 (4)0.8404 (2)0.96789 (19)0.0220 (5)
F30.8456 (4)0.9653 (2)0.58559 (19)0.0238 (5)
F40.8460 (4)0.7542 (2)0.58543 (19)0.0240 (5)
O10.7436 (4)0.3122 (2)0.7475 (2)0.0165 (5)
N10.5640 (5)0.3111 (3)0.7223 (3)0.0158 (6)
C10.4115 (6)0.2886 (3)0.8008 (3)0.0205 (8)
H10.4325180.2772210.8736730.025*
C20.2257 (6)0.2822 (4)0.7759 (4)0.0239 (9)
H20.1182400.2667200.8308560.029*
C30.1991 (6)0.2987 (3)0.6691 (4)0.0245 (8)
H30.0725340.2922800.6508960.029*
C40.3542 (6)0.3242 (3)0.5889 (3)0.0211 (8)
H40.3349570.3358910.5157550.025*
C50.5402 (6)0.3327 (3)0.6163 (3)0.0171 (7)
C60.6741 (6)0.4039 (3)0.3981 (3)0.0215 (8)
H6A0.5389400.4322720.4025710.026*
H6B0.7555860.4652760.3471650.026*
C70.6788 (6)0.3083 (4)0.3509 (3)0.0189 (8)
C80.7032 (6)0.3338 (4)0.2402 (3)0.0199 (8)
H80.7179330.4099590.1968030.024*
C90.7072 (6)0.2508 (4)0.1892 (3)0.0196 (8)
C100.7345 (6)0.2772 (4)0.0752 (3)0.0226 (9)
H100.7449410.3532420.0309310.027*
C110.7460 (7)0.1937 (4)0.0281 (4)0.0272 (10)
H110.7687780.2121360.0483260.033*
C120.7242 (6)0.0804 (4)0.0932 (4)0.0263 (9)
H120.7295140.0232430.0600290.032*
C130.6954 (6)0.0526 (4)0.2033 (4)0.0236 (9)
H130.6795850.0237260.2458240.028*
C140.6888 (6)0.1357 (4)0.2549 (3)0.0208 (8)
C150.6633 (6)0.1109 (4)0.3685 (3)0.0205 (8)
H150.6498190.0350910.4130660.025*
C160.6577 (6)0.1943 (4)0.4159 (3)0.0207 (8)
H160.6395830.1755240.4924950.025*
C170.8005 (6)0.6846 (3)0.7771 (3)0.0181 (8)
C180.7800 (6)0.7114 (3)0.8725 (3)0.0186 (8)
C190.7830 (6)0.8203 (3)0.8724 (3)0.0171 (8)
C200.8040 (6)0.9095 (3)0.7767 (3)0.0174 (8)
C210.8264 (6)0.8834 (3)0.6807 (3)0.0177 (8)
C220.8239 (6)0.7745 (3)0.6809 (3)0.0179 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01637 (17)0.01961 (17)0.01874 (17)0.00049 (10)0.00222 (11)0.00488 (11)
I20.01732 (17)0.01868 (17)0.01657 (17)0.00037 (11)0.00186 (11)0.00338 (11)
S10.0161 (4)0.0271 (5)0.0102 (4)0.0006 (3)0.0000 (3)0.0037 (3)
F10.0366 (14)0.0225 (11)0.0120 (12)0.0022 (10)0.0005 (10)0.0025 (9)
F20.0271 (12)0.0264 (12)0.0111 (11)0.0001 (10)0.0003 (9)0.0050 (9)
F30.0326 (13)0.0242 (11)0.0091 (11)0.0002 (10)0.0009 (9)0.0018 (9)
F40.0301 (13)0.0308 (12)0.0115 (11)0.0009 (10)0.0001 (10)0.0079 (9)
O10.0136 (13)0.0202 (12)0.0148 (13)0.0019 (10)0.0046 (11)0.0033 (10)
N10.0152 (16)0.0186 (15)0.0123 (15)0.0013 (12)0.0002 (12)0.0039 (12)
C10.019 (2)0.027 (2)0.0127 (18)0.0019 (16)0.0020 (15)0.0031 (15)
C20.017 (2)0.029 (2)0.019 (2)0.0004 (17)0.0023 (16)0.0005 (16)
C30.0171 (19)0.028 (2)0.026 (2)0.0009 (16)0.0049 (16)0.0043 (17)
C40.019 (2)0.024 (2)0.019 (2)0.0001 (15)0.0058 (16)0.0049 (16)
C50.0206 (19)0.0194 (17)0.0083 (17)0.0017 (14)0.0009 (14)0.0009 (14)
C60.024 (2)0.0263 (19)0.0093 (17)0.0012 (16)0.0004 (15)0.0004 (15)
C70.0107 (17)0.029 (2)0.0159 (19)0.0037 (15)0.0001 (14)0.0065 (16)
C80.0170 (19)0.027 (2)0.0124 (18)0.0001 (15)0.0012 (14)0.0015 (16)
C90.0138 (18)0.029 (2)0.0126 (19)0.0002 (16)0.0018 (15)0.0021 (16)
C100.0159 (19)0.035 (2)0.0131 (19)0.0020 (16)0.0013 (15)0.0031 (17)
C110.019 (2)0.050 (3)0.014 (2)0.0048 (19)0.0022 (16)0.0133 (19)
C120.018 (2)0.043 (2)0.024 (2)0.0048 (18)0.0052 (17)0.0188 (19)
C130.018 (2)0.029 (2)0.022 (2)0.0032 (16)0.0029 (16)0.0059 (17)
C140.0125 (19)0.030 (2)0.018 (2)0.0005 (15)0.0023 (15)0.0042 (17)
C150.0143 (19)0.0254 (19)0.018 (2)0.0037 (15)0.0014 (15)0.0020 (16)
C160.021 (2)0.026 (2)0.0101 (18)0.0009 (16)0.0019 (15)0.0006 (16)
C170.0166 (19)0.0186 (18)0.016 (2)0.0006 (15)0.0018 (15)0.0005 (15)
C180.0183 (19)0.0223 (19)0.0097 (18)0.0027 (15)0.0007 (14)0.0020 (15)
C190.0140 (18)0.0241 (19)0.0108 (18)0.0022 (15)0.0008 (14)0.0028 (15)
C200.0182 (19)0.0173 (18)0.0127 (19)0.0013 (15)0.0016 (14)0.0001 (15)
C210.0172 (19)0.0237 (19)0.0076 (18)0.0010 (15)0.0009 (14)0.0006 (15)
C220.0152 (19)0.0230 (19)0.0136 (19)0.0030 (15)0.0027 (14)0.0030 (15)
Geometric parameters (Å, º) top
I1—C172.088 (4)C7—C161.422 (6)
I2—C202.076 (4)C8—C91.409 (6)
S1—C51.744 (4)C8—H80.9500
S1—C61.812 (4)C9—C101.416 (6)
F1—C181.352 (5)C9—C141.434 (7)
F2—C191.345 (5)C10—C111.374 (7)
F3—C211.339 (5)C10—H100.9500
F4—C221.347 (5)C11—C121.416 (7)
O1—N11.328 (4)C11—H110.9500
N1—C11.352 (5)C12—C131.365 (6)
N1—C51.361 (5)C12—H120.9500
C1—C21.379 (6)C13—C141.413 (6)
C1—H10.9500C13—H130.9500
C2—C31.386 (6)C14—C151.413 (6)
C2—H20.9500C15—C161.379 (6)
C3—C41.379 (6)C15—H150.9500
C3—H30.9500C16—H160.9500
C4—C51.397 (6)C17—C181.388 (6)
C4—H40.9500C17—C221.400 (6)
C6—C71.517 (6)C18—C191.373 (7)
C6—H6A0.9900C19—C201.391 (6)
C6—H6B0.9900C20—C211.390 (6)
C7—C81.375 (6)C21—C221.372 (6)
C5—S1—C6102.10 (19)C10—C11—C12120.2 (4)
O1—N1—C1120.2 (3)C10—C11—H11119.9
O1—N1—C5118.0 (3)C12—C11—H11119.9
C1—N1—C5121.8 (3)C13—C12—C11120.5 (4)
N1—C1—C2120.5 (4)C13—C12—H12119.8
N1—C1—H1119.7C11—C12—H12119.8
C2—C1—H1119.7C12—C13—C14121.0 (4)
C1—C2—C3118.6 (4)C12—C13—H13119.5
C1—C2—H2120.7C14—C13—H13119.5
C3—C2—H2120.7C15—C14—C13123.0 (4)
C4—C3—C2120.7 (4)C15—C14—C9118.3 (4)
C4—C3—H3119.7C13—C14—C9118.7 (4)
C2—C3—H3119.7C16—C15—C14121.4 (4)
C3—C4—C5119.4 (4)C16—C15—H15119.3
C3—C4—H4120.3C14—C15—H15119.3
C5—C4—H4120.3C15—C16—C7120.4 (4)
N1—C5—C4118.8 (4)C15—C16—H16119.8
N1—C5—S1112.8 (3)C7—C16—H16119.8
C4—C5—S1128.4 (3)C18—C17—C22116.4 (4)
C7—C6—S1116.2 (3)C18—C17—I1123.4 (3)
C7—C6—H6A108.2C22—C17—I1120.2 (3)
S1—C6—H6A108.2F1—C18—C19118.7 (4)
C7—C6—H6B108.2F1—C18—C17119.7 (4)
S1—C6—H6B108.2C19—C18—C17121.6 (4)
H6A—C6—H6B107.4F2—C19—C18118.6 (4)
C8—C7—C16118.9 (4)F2—C19—C20119.7 (4)
C8—C7—C6118.1 (4)C18—C19—C20121.8 (4)
C16—C7—C6122.9 (4)C21—C20—C19117.0 (4)
C7—C8—C9122.1 (4)C21—C20—I2120.2 (3)
C7—C8—H8118.9C19—C20—I2122.8 (3)
C9—C8—H8118.9F3—C21—C22118.7 (4)
C8—C9—C10122.0 (4)F3—C21—C20120.1 (4)
C8—C9—C14118.9 (4)C22—C21—C20121.2 (4)
C10—C9—C14119.1 (4)F4—C22—C21118.6 (4)
C11—C10—C9120.5 (4)F4—C22—C17119.4 (4)
C11—C10—H10119.8C21—C22—C17122.0 (4)
C9—C10—H10119.8
O1—N1—C1—C2176.9 (4)C10—C9—C14—C131.0 (7)
C5—N1—C1—C22.8 (6)C13—C14—C15—C16180.0 (4)
N1—C1—C2—C30.3 (6)C9—C14—C15—C160.5 (7)
C1—C2—C3—C41.9 (6)C14—C15—C16—C70.4 (7)
C2—C3—C4—C50.4 (6)C8—C7—C16—C150.5 (6)
O1—N1—C5—C4175.5 (3)C6—C7—C16—C15179.9 (4)
C1—N1—C5—C44.2 (6)C22—C17—C18—F1179.9 (3)
O1—N1—C5—S15.6 (4)I1—C17—C18—F11.4 (6)
C1—N1—C5—S1174.7 (3)C22—C17—C18—C190.1 (6)
C3—C4—C5—N12.6 (6)I1—C17—C18—C19178.9 (3)
C3—C4—C5—S1176.1 (3)F1—C18—C19—F20.1 (6)
C6—S1—C5—N1175.9 (3)C17—C18—C19—F2179.8 (3)
C6—S1—C5—C42.9 (4)F1—C18—C19—C20179.3 (4)
C5—S1—C6—C791.4 (3)C17—C18—C19—C200.9 (7)
S1—C6—C7—C8151.7 (3)F2—C19—C20—C21179.3 (3)
S1—C6—C7—C1628.7 (5)C18—C19—C20—C211.4 (6)
C16—C7—C8—C90.3 (6)F2—C19—C20—I20.8 (5)
C6—C7—C8—C9179.3 (4)C18—C19—C20—I2178.4 (3)
C7—C8—C9—C10179.3 (4)C19—C20—C21—F3179.4 (3)
C7—C8—C9—C141.2 (7)I2—C20—C21—F30.4 (5)
C8—C9—C10—C11177.2 (4)C19—C20—C21—C221.3 (6)
C14—C9—C10—C110.9 (7)I2—C20—C21—C22178.6 (3)
C9—C10—C11—C122.1 (7)F3—C21—C22—F41.7 (6)
C10—C11—C12—C131.3 (7)C20—C21—C22—F4179.9 (3)
C11—C12—C13—C140.7 (7)F3—C21—C22—C17178.7 (3)
C12—C13—C14—C15178.7 (4)C20—C21—C22—C170.5 (7)
C12—C13—C14—C91.8 (7)C18—C17—C22—F4179.5 (4)
C8—C9—C14—C151.3 (7)I1—C17—C22—F41.7 (5)
C10—C9—C14—C15179.5 (3)C18—C17—C22—C210.1 (6)
C8—C9—C14—C13179.2 (3)I1—C17—C22—C21178.7 (3)
1,3,5-Trifluoro-2,4,6-triiodobenzene–2-{[(naphthalen-2-yl)methyl]sulfanyl}pyridine 1-oxide (1/1) (2) top
Crystal data top
C6F3I3·C16H13NOSF(000) = 1448
Mr = 777.09Dx = 2.256 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 7.0073 (1) ÅCell parameters from 9636 reflections
b = 15.6551 (3) Åθ = 5.1–71.8°
c = 20.8676 (4) ŵ = 33.39 mm1
β = 91.727 (2)°T = 119 K
V = 2288.14 (7) Å3Block, colourless
Z = 40.2 × 0.1 × 0.05 × 0.10 (radius) mm
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an AtlasS2 detector
4447 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source4273 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.048
Detector resolution: 5.3127 pixels mm-1θmax = 72.0°, θmin = 3.5°
ω scansh = 87
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2017)
k = 1919
Tmin = 0.210, Tmax = 1.000l = 1725
15814 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0546P)2 + 5.5786P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.002
4447 reflectionsΔρmax = 2.92 e Å3
280 parametersΔρmin = 0.76 e Å3
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.80960 (4)0.37502 (2)0.35422 (2)0.01680 (11)
I20.80477 (6)0.69455 (2)0.19198 (2)0.02615 (12)
I30.82285 (5)0.34574 (2)0.06669 (2)0.01881 (11)
S10.76937 (18)0.42931 (8)0.54423 (6)0.0196 (3)
F10.8094 (5)0.5708 (2)0.31102 (14)0.0222 (6)
F20.8059 (5)0.5493 (2)0.08650 (14)0.0236 (7)
F30.8241 (5)0.30148 (19)0.21272 (15)0.0245 (7)
O10.7664 (5)0.2888 (2)0.46872 (17)0.0193 (8)
N10.5910 (7)0.3041 (3)0.4877 (2)0.0175 (9)
C10.4459 (8)0.2539 (4)0.4662 (3)0.0214 (11)
H10.4686230.2104710.4355930.026*
C20.2644 (8)0.2658 (4)0.4888 (3)0.0211 (11)
H20.1618090.2310700.4733460.025*
C30.2325 (8)0.3288 (4)0.5342 (3)0.0243 (12)
H30.1093950.3362640.5512070.029*
C40.3839 (8)0.3806 (4)0.5541 (3)0.0221 (11)
H40.3639530.4243850.5847450.027*
C50.5640 (8)0.3689 (3)0.5297 (2)0.0174 (10)
C60.6876 (8)0.5106 (3)0.5980 (2)0.0205 (11)
H6A0.7683720.5618480.5927400.025*
H6B0.5557550.5264020.5844340.025*
C70.6879 (8)0.4884 (3)0.6690 (3)0.0189 (10)
C80.6779 (8)0.5543 (3)0.7120 (3)0.0201 (10)
H80.6681760.6111790.6964160.024*
C90.6817 (8)0.5398 (4)0.7792 (3)0.0207 (11)
C100.6711 (8)0.6071 (4)0.8241 (3)0.0251 (12)
H100.6595670.6644060.8094630.030*
C110.6773 (9)0.5902 (5)0.8888 (3)0.0295 (13)
H110.6698780.6358180.9186700.035*
C120.6946 (9)0.5057 (4)0.9108 (3)0.0291 (13)
H120.7001260.4947770.9556390.035*
C130.7035 (9)0.4386 (4)0.8688 (3)0.0259 (12)
H130.7149360.3818320.8845250.031*
C140.6957 (7)0.4542 (4)0.8015 (3)0.0200 (11)
C150.7029 (8)0.3871 (4)0.7564 (3)0.0224 (11)
H150.7112440.3297360.7711680.027*
C160.6980 (8)0.4030 (4)0.6916 (3)0.0221 (11)
H160.7014560.3569290.6620080.027*
C170.8172 (7)0.4346 (3)0.2645 (2)0.0156 (10)
C180.8110 (7)0.5221 (3)0.2577 (3)0.0182 (10)
C190.8078 (8)0.5627 (3)0.1986 (2)0.0185 (10)
C200.8113 (7)0.5113 (4)0.1442 (2)0.0179 (10)
C210.8192 (7)0.4234 (3)0.1475 (2)0.0157 (10)
C220.8192 (7)0.3870 (3)0.2082 (3)0.0184 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02111 (18)0.01545 (17)0.01386 (17)0.00315 (11)0.00099 (12)0.00237 (11)
I20.0408 (2)0.01098 (17)0.0261 (2)0.00225 (13)0.00828 (15)0.00232 (12)
I30.02116 (18)0.01924 (18)0.01594 (17)0.00141 (12)0.00088 (12)0.00438 (11)
S10.0204 (6)0.0194 (6)0.0188 (6)0.0013 (5)0.0003 (5)0.0016 (5)
F10.0354 (18)0.0158 (14)0.0153 (14)0.0017 (13)0.0002 (13)0.0051 (11)
F20.0336 (18)0.0227 (16)0.0143 (14)0.0044 (14)0.0035 (12)0.0050 (12)
F30.042 (2)0.0108 (14)0.0206 (16)0.0009 (13)0.0011 (14)0.0009 (11)
O10.0201 (19)0.0206 (18)0.0174 (17)0.0082 (15)0.0039 (14)0.0061 (14)
N10.020 (2)0.020 (2)0.0123 (19)0.0052 (17)0.0004 (16)0.0035 (16)
C10.024 (3)0.022 (3)0.017 (2)0.000 (2)0.000 (2)0.000 (2)
C20.019 (3)0.020 (3)0.024 (3)0.002 (2)0.002 (2)0.008 (2)
C30.019 (3)0.028 (3)0.027 (3)0.005 (2)0.002 (2)0.009 (2)
C40.026 (3)0.021 (3)0.020 (3)0.009 (2)0.003 (2)0.003 (2)
C50.023 (3)0.015 (2)0.015 (2)0.003 (2)0.001 (2)0.0035 (18)
C60.027 (3)0.016 (2)0.018 (3)0.002 (2)0.000 (2)0.0009 (19)
C70.018 (3)0.019 (3)0.019 (3)0.002 (2)0.0035 (19)0.001 (2)
C80.020 (3)0.015 (2)0.025 (3)0.002 (2)0.002 (2)0.001 (2)
C90.017 (3)0.019 (3)0.026 (3)0.003 (2)0.002 (2)0.005 (2)
C100.024 (3)0.025 (3)0.026 (3)0.001 (2)0.005 (2)0.003 (2)
C110.023 (3)0.043 (4)0.023 (3)0.003 (3)0.002 (2)0.010 (3)
C120.026 (3)0.041 (4)0.020 (3)0.003 (3)0.001 (2)0.002 (2)
C130.028 (3)0.028 (3)0.022 (3)0.005 (2)0.001 (2)0.002 (2)
C140.014 (2)0.023 (3)0.023 (3)0.001 (2)0.000 (2)0.000 (2)
C150.030 (3)0.018 (3)0.019 (3)0.002 (2)0.003 (2)0.003 (2)
C160.026 (3)0.017 (3)0.023 (3)0.001 (2)0.003 (2)0.003 (2)
C170.017 (2)0.014 (2)0.015 (2)0.0003 (19)0.0011 (18)0.0052 (18)
C180.018 (2)0.017 (2)0.019 (2)0.001 (2)0.001 (2)0.003 (2)
C190.028 (3)0.008 (2)0.019 (2)0.002 (2)0.002 (2)0.0014 (18)
C200.015 (2)0.022 (3)0.017 (2)0.002 (2)0.0035 (19)0.006 (2)
C210.016 (2)0.015 (2)0.015 (2)0.0011 (19)0.0012 (18)0.0044 (18)
C220.019 (3)0.014 (2)0.022 (3)0.0009 (19)0.002 (2)0.001 (2)
Geometric parameters (Å, º) top
I1—C172.093 (5)C7—C161.418 (8)
I2—C192.069 (5)C8—C91.421 (8)
I3—C212.079 (5)C8—H80.9500
S1—C51.741 (6)C9—C101.414 (8)
S1—C61.802 (5)C9—C141.420 (8)
F1—C181.349 (6)C10—C111.375 (9)
F2—C201.343 (6)C10—H100.9500
F3—C221.343 (6)C11—C121.406 (10)
O1—N11.324 (6)C11—H110.9500
N1—C11.350 (8)C12—C131.370 (9)
N1—C51.358 (7)C12—H120.9500
C1—C21.382 (8)C13—C141.426 (8)
C1—H10.9500C13—H130.9500
C2—C31.389 (9)C14—C151.412 (8)
C2—H20.9500C15—C161.375 (8)
C3—C41.390 (9)C15—H150.9500
C3—H30.9500C16—H160.9500
C4—C51.387 (8)C17—C181.377 (7)
C4—H40.9500C17—C221.393 (8)
C6—C71.522 (7)C18—C191.387 (8)
C6—H6A0.9900C19—C201.393 (8)
C6—H6B0.9900C20—C211.379 (8)
C7—C81.370 (8)C21—C221.389 (8)
C5—S1—C6102.4 (3)C10—C11—C12120.1 (6)
O1—N1—C1119.5 (4)C10—C11—H11119.9
O1—N1—C5118.4 (5)C12—C11—H11119.9
C1—N1—C5122.1 (5)C13—C12—C11121.1 (6)
N1—C1—C2120.0 (5)C13—C12—H12119.4
N1—C1—H1120.0C11—C12—H12119.4
C2—C1—H1120.0C12—C13—C14119.9 (6)
C1—C2—C3119.8 (5)C12—C13—H13120.0
C1—C2—H2120.1C14—C13—H13120.0
C3—C2—H2120.1C15—C14—C9119.2 (5)
C2—C3—C4118.8 (5)C15—C14—C13121.9 (5)
C2—C3—H3120.6C9—C14—C13118.9 (5)
C4—C3—H3120.6C16—C15—C14121.3 (5)
C5—C4—C3120.5 (5)C16—C15—H15119.3
C5—C4—H4119.7C14—C15—H15119.3
C3—C4—H4119.7C15—C16—C7119.8 (5)
N1—C5—C4118.8 (5)C15—C16—H16120.1
N1—C5—S1112.8 (4)C7—C16—H16120.1
C4—C5—S1128.4 (4)C18—C17—C22116.5 (5)
C7—C6—S1117.0 (4)C18—C17—I1122.3 (4)
C7—C6—H6A108.0C22—C17—I1121.2 (4)
S1—C6—H6A108.0F1—C18—C17118.6 (5)
C7—C6—H6B108.0F1—C18—C19118.3 (5)
S1—C6—H6B108.0C17—C18—C19123.1 (5)
H6A—C6—H6B107.3C18—C19—C20117.4 (5)
C8—C7—C16119.7 (5)C18—C19—I2121.1 (4)
C8—C7—C6117.8 (5)C20—C19—I2121.5 (4)
C16—C7—C6122.5 (5)F2—C20—C21119.1 (5)
C7—C8—C9121.7 (5)F2—C20—C19118.4 (5)
C7—C8—H8119.1C21—C20—C19122.6 (5)
C9—C8—H8119.1C20—C21—C22116.9 (5)
C10—C9—C14119.5 (5)C20—C21—I3123.0 (4)
C10—C9—C8122.3 (5)C22—C21—I3120.0 (4)
C14—C9—C8118.2 (5)F3—C22—C21118.2 (5)
C11—C10—C9120.4 (6)F3—C22—C17118.4 (5)
C11—C10—H10119.8C21—C22—C17123.4 (5)
C9—C10—H10119.8
O1—N1—C1—C2175.9 (5)C12—C13—C14—C91.0 (8)
C5—N1—C1—C22.4 (8)C9—C14—C15—C160.5 (9)
N1—C1—C2—C30.8 (8)C13—C14—C15—C16179.0 (5)
C1—C2—C3—C42.3 (8)C14—C15—C16—C70.8 (9)
C2—C3—C4—C50.8 (8)C8—C7—C16—C151.7 (9)
O1—N1—C5—C4174.5 (4)C6—C7—C16—C15178.3 (5)
C1—N1—C5—C43.8 (7)C22—C17—C18—F1179.8 (5)
O1—N1—C5—S17.0 (6)I1—C17—C18—F13.3 (7)
C1—N1—C5—S1174.7 (4)C22—C17—C18—C190.3 (8)
C3—C4—C5—N12.2 (8)I1—C17—C18—C19177.2 (4)
C3—C4—C5—S1176.1 (4)F1—C18—C19—C20179.4 (5)
C6—S1—C5—N1177.9 (4)C17—C18—C19—C200.1 (8)
C6—S1—C5—C40.5 (6)F1—C18—C19—I20.9 (7)
C5—S1—C6—C785.0 (5)C17—C18—C19—I2178.6 (4)
S1—C6—C7—C8162.4 (4)C18—C19—C20—F2179.2 (5)
S1—C6—C7—C1617.6 (7)I2—C19—C20—F22.3 (7)
C16—C7—C8—C91.4 (8)C18—C19—C20—C210.5 (8)
C6—C7—C8—C9178.6 (5)I2—C19—C20—C21178.0 (4)
C7—C8—C9—C10179.9 (5)F2—C20—C21—C22178.3 (5)
C7—C8—C9—C140.2 (8)C19—C20—C21—C221.5 (8)
C14—C9—C10—C111.0 (9)F2—C20—C21—I30.1 (7)
C8—C9—C10—C11179.3 (5)C19—C20—C21—I3179.6 (4)
C9—C10—C11—C120.1 (9)C20—C21—C22—F3179.1 (5)
C10—C11—C12—C130.7 (9)I3—C21—C22—F30.8 (7)
C11—C12—C13—C140.1 (9)C20—C21—C22—C171.9 (8)
C10—C9—C14—C15178.9 (5)I3—C21—C22—C17179.9 (4)
C8—C9—C14—C150.8 (8)C18—C17—C22—F3179.6 (5)
C10—C9—C14—C131.6 (8)I1—C17—C22—F32.7 (7)
C8—C9—C14—C13178.7 (5)C18—C17—C22—C211.3 (8)
C12—C13—C14—C15179.5 (6)I1—C17—C22—C21178.3 (4)
 

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