Cocrystals assembled from iodo­perfluoro­benzene and flexible NTPO via halogen and π-hole bonds

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.

Computing details

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)

Crystal data

C6F4I2·C16H13NOS	Z = 2
Mr = 669.19	F(000) = 636
Triclinic, P1	Dx = 2.060 Mg m^−3
a = 6.9303 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 12.6026 (5) Å	Cell parameters from 5647 reflections
c = 13.1299 (6) Å	θ = 3.6–73.1°
α = 71.495 (4)°	µ = 24.25 mm^−1
β = 82.851 (4)°	T = 100 K
γ = 87.566 (4)°	Plate, colourless
V = 1079.01 (8) Å^3	0.1 × 0.1 × 0.05 × 0.08 (radius) mm

Data collection

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 Source	3699 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 5.3127 pixels mm^-1	θmax = 66.6°, θmin = 3.6°
ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	k = −10→14
Tmin = 0.580, Tmax = 1.000	l = −14→15
6503 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0661P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max = 0.002
S = 1.09	Δρmax = 1.54 e Å^−3
3808 reflections	Δρmin = −1.37 e Å^−3
281 parameters	Extinction correction: SHELXL2019 (Sheldrick, 2015a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00114 (12)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.79225 (3)	0.52096 (2)	0.77202 (2)	0.01851 (12)
I2	0.80214 (3)	1.07529 (2)	0.77351 (2)	0.01806 (13)
S1	0.75615 (13)	0.37118 (8)	0.53046 (7)	0.0185 (2)
F1	0.7572 (4)	0.6289 (2)	0.9685 (2)	0.0257 (5)
F2	0.7629 (4)	0.8404 (2)	0.96789 (19)	0.0220 (5)
F3	0.8456 (4)	0.9653 (2)	0.58559 (19)	0.0238 (5)
F4	0.8460 (4)	0.7542 (2)	0.58543 (19)	0.0240 (5)
O1	0.7436 (4)	0.3122 (2)	0.7475 (2)	0.0165 (5)
N1	0.5640 (5)	0.3111 (3)	0.7223 (3)	0.0158 (6)
C1	0.4115 (6)	0.2886 (3)	0.8008 (3)	0.0205 (8)
H1	0.432518	0.277221	0.873673	0.025*
C2	0.2257 (6)	0.2822 (4)	0.7759 (4)	0.0239 (9)
H2	0.118240	0.266720	0.830856	0.029*
C3	0.1991 (6)	0.2987 (3)	0.6691 (4)	0.0245 (8)
H3	0.072534	0.292280	0.650896	0.029*
C4	0.3542 (6)	0.3242 (3)	0.5889 (3)	0.0211 (8)
H4	0.334957	0.335891	0.515755	0.025*
C5	0.5402 (6)	0.3327 (3)	0.6163 (3)	0.0171 (7)
C6	0.6741 (6)	0.4039 (3)	0.3981 (3)	0.0215 (8)
H6A	0.538940	0.432272	0.402571	0.026*
H6B	0.755586	0.465276	0.347165	0.026*
C7	0.6788 (6)	0.3083 (4)	0.3509 (3)	0.0189 (8)
C8	0.7032 (6)	0.3338 (4)	0.2402 (3)	0.0199 (8)
H8	0.717933	0.409959	0.196803	0.024*
C9	0.7072 (6)	0.2508 (4)	0.1892 (3)	0.0196 (8)
C10	0.7345 (6)	0.2772 (4)	0.0752 (3)	0.0226 (9)
H10	0.744941	0.353242	0.030931	0.027*
C11	0.7460 (7)	0.1937 (4)	0.0281 (4)	0.0272 (10)
H11	0.768778	0.212136	−0.048326	0.033*
C12	0.7242 (6)	0.0804 (4)	0.0932 (4)	0.0263 (9)
H12	0.729514	0.023243	0.060029	0.032*
C13	0.6954 (6)	0.0526 (4)	0.2033 (4)	0.0236 (9)
H13	0.679585	−0.023726	0.245824	0.028*
C14	0.6888 (6)	0.1357 (4)	0.2549 (3)	0.0208 (8)
C15	0.6633 (6)	0.1109 (4)	0.3685 (3)	0.0205 (8)
H15	0.649819	0.035091	0.413066	0.025*
C16	0.6577 (6)	0.1943 (4)	0.4159 (3)	0.0207 (8)
H16	0.639583	0.175524	0.492495	0.025*
C17	0.8005 (6)	0.6846 (3)	0.7771 (3)	0.0181 (8)
C18	0.7800 (6)	0.7114 (3)	0.8725 (3)	0.0186 (8)
C19	0.7830 (6)	0.8203 (3)	0.8724 (3)	0.0171 (8)
C20	0.8040 (6)	0.9095 (3)	0.7767 (3)	0.0174 (8)
C21	0.8264 (6)	0.8834 (3)	0.6807 (3)	0.0177 (8)
C22	0.8239 (6)	0.7745 (3)	0.6809 (3)	0.0179 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01637 (17)	0.01961 (17)	0.01874 (17)	0.00049 (10)	−0.00222 (11)	−0.00488 (11)
I2	0.01732 (17)	0.01868 (17)	0.01657 (17)	0.00037 (11)	−0.00186 (11)	−0.00338 (11)
S1	0.0161 (4)	0.0271 (5)	0.0102 (4)	−0.0006 (3)	0.0000 (3)	−0.0037 (3)
F1	0.0366 (14)	0.0225 (11)	0.0120 (12)	−0.0022 (10)	−0.0005 (10)	0.0025 (9)
F2	0.0271 (12)	0.0264 (12)	0.0111 (11)	−0.0001 (10)	0.0003 (9)	−0.0050 (9)
F3	0.0326 (13)	0.0242 (11)	0.0091 (11)	0.0002 (10)	−0.0009 (9)	0.0018 (9)
F4	0.0301 (13)	0.0308 (12)	0.0115 (11)	−0.0009 (10)	0.0001 (10)	−0.0079 (9)
O1	0.0136 (13)	0.0202 (12)	0.0148 (13)	0.0019 (10)	−0.0046 (11)	−0.0033 (10)
N1	0.0152 (16)	0.0186 (15)	0.0123 (15)	0.0013 (12)	0.0002 (12)	−0.0039 (12)
C1	0.019 (2)	0.027 (2)	0.0127 (18)	0.0019 (16)	−0.0020 (15)	−0.0031 (15)
C2	0.017 (2)	0.029 (2)	0.019 (2)	0.0004 (17)	0.0023 (16)	−0.0005 (16)
C3	0.0171 (19)	0.028 (2)	0.026 (2)	0.0009 (16)	−0.0049 (16)	−0.0043 (17)
C4	0.019 (2)	0.024 (2)	0.019 (2)	0.0001 (15)	−0.0058 (16)	−0.0049 (16)
C5	0.0206 (19)	0.0194 (17)	0.0083 (17)	−0.0017 (14)	0.0009 (14)	−0.0009 (14)
C6	0.024 (2)	0.0263 (19)	0.0093 (17)	−0.0012 (16)	0.0004 (15)	0.0004 (15)
C7	0.0107 (17)	0.029 (2)	0.0159 (19)	0.0037 (15)	0.0001 (14)	−0.0065 (16)
C8	0.0170 (19)	0.027 (2)	0.0124 (18)	−0.0001 (15)	−0.0012 (14)	−0.0015 (16)
C9	0.0138 (18)	0.029 (2)	0.0126 (19)	0.0002 (16)	−0.0018 (15)	−0.0021 (16)
C10	0.0159 (19)	0.035 (2)	0.0131 (19)	0.0020 (16)	−0.0013 (15)	−0.0031 (17)
C11	0.019 (2)	0.050 (3)	0.014 (2)	0.0048 (19)	−0.0022 (16)	−0.0133 (19)
C12	0.018 (2)	0.043 (2)	0.024 (2)	0.0048 (18)	−0.0052 (17)	−0.0188 (19)
C13	0.018 (2)	0.029 (2)	0.022 (2)	−0.0032 (16)	−0.0029 (16)	−0.0059 (17)
C14	0.0125 (19)	0.030 (2)	0.018 (2)	0.0005 (15)	−0.0023 (15)	−0.0042 (17)
C15	0.0143 (19)	0.0254 (19)	0.018 (2)	0.0037 (15)	−0.0014 (15)	−0.0020 (16)
C16	0.021 (2)	0.026 (2)	0.0101 (18)	−0.0009 (16)	0.0019 (15)	−0.0006 (16)
C17	0.0166 (19)	0.0186 (18)	0.016 (2)	0.0006 (15)	−0.0018 (15)	−0.0005 (15)
C18	0.0183 (19)	0.0223 (19)	0.0097 (18)	−0.0027 (15)	0.0007 (14)	0.0020 (15)
C19	0.0140 (18)	0.0241 (19)	0.0108 (18)	0.0022 (15)	−0.0008 (14)	−0.0028 (15)
C20	0.0182 (19)	0.0173 (18)	0.0127 (19)	−0.0013 (15)	0.0016 (14)	−0.0001 (15)
C21	0.0172 (19)	0.0237 (19)	0.0076 (18)	−0.0010 (15)	0.0009 (14)	0.0006 (15)
C22	0.0152 (19)	0.0230 (19)	0.0136 (19)	0.0030 (15)	−0.0027 (14)	−0.0030 (15)

Geometric parameters (Å, º)

I1—C17	2.088 (4)	C7—C16	1.422 (6)
I2—C20	2.076 (4)	C8—C9	1.409 (6)
S1—C5	1.744 (4)	C8—H8	0.9500
S1—C6	1.812 (4)	C9—C10	1.416 (6)
F1—C18	1.352 (5)	C9—C14	1.434 (7)
F2—C19	1.345 (5)	C10—C11	1.374 (7)
F3—C21	1.339 (5)	C10—H10	0.9500
F4—C22	1.347 (5)	C11—C12	1.416 (7)
O1—N1	1.328 (4)	C11—H11	0.9500
N1—C1	1.352 (5)	C12—C13	1.365 (6)
N1—C5	1.361 (5)	C12—H12	0.9500
C1—C2	1.379 (6)	C13—C14	1.413 (6)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.386 (6)	C14—C15	1.413 (6)
C2—H2	0.9500	C15—C16	1.379 (6)
C3—C4	1.379 (6)	C15—H15	0.9500
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.397 (6)	C17—C18	1.388 (6)
C4—H4	0.9500	C17—C22	1.400 (6)
C6—C7	1.517 (6)	C18—C19	1.373 (7)
C6—H6A	0.9900	C19—C20	1.391 (6)
C6—H6B	0.9900	C20—C21	1.390 (6)
C7—C8	1.375 (6)	C21—C22	1.372 (6)
C5—S1—C6	102.10 (19)	C10—C11—C12	120.2 (4)
O1—N1—C1	120.2 (3)	C10—C11—H11	119.9
O1—N1—C5	118.0 (3)	C12—C11—H11	119.9
C1—N1—C5	121.8 (3)	C13—C12—C11	120.5 (4)
N1—C1—C2	120.5 (4)	C13—C12—H12	119.8
N1—C1—H1	119.7	C11—C12—H12	119.8
C2—C1—H1	119.7	C12—C13—C14	121.0 (4)
C1—C2—C3	118.6 (4)	C12—C13—H13	119.5
C1—C2—H2	120.7	C14—C13—H13	119.5
C3—C2—H2	120.7	C15—C14—C13	123.0 (4)
C4—C3—C2	120.7 (4)	C15—C14—C9	118.3 (4)
C4—C3—H3	119.7	C13—C14—C9	118.7 (4)
C2—C3—H3	119.7	C16—C15—C14	121.4 (4)
C3—C4—C5	119.4 (4)	C16—C15—H15	119.3
C3—C4—H4	120.3	C14—C15—H15	119.3
C5—C4—H4	120.3	C15—C16—C7	120.4 (4)
N1—C5—C4	118.8 (4)	C15—C16—H16	119.8
N1—C5—S1	112.8 (3)	C7—C16—H16	119.8
C4—C5—S1	128.4 (3)	C18—C17—C22	116.4 (4)
C7—C6—S1	116.2 (3)	C18—C17—I1	123.4 (3)
C7—C6—H6A	108.2	C22—C17—I1	120.2 (3)
S1—C6—H6A	108.2	F1—C18—C19	118.7 (4)
C7—C6—H6B	108.2	F1—C18—C17	119.7 (4)
S1—C6—H6B	108.2	C19—C18—C17	121.6 (4)
H6A—C6—H6B	107.4	F2—C19—C18	118.6 (4)
C8—C7—C16	118.9 (4)	F2—C19—C20	119.7 (4)
C8—C7—C6	118.1 (4)	C18—C19—C20	121.8 (4)
C16—C7—C6	122.9 (4)	C21—C20—C19	117.0 (4)
C7—C8—C9	122.1 (4)	C21—C20—I2	120.2 (3)
C7—C8—H8	118.9	C19—C20—I2	122.8 (3)
C9—C8—H8	118.9	F3—C21—C22	118.7 (4)
C8—C9—C10	122.0 (4)	F3—C21—C20	120.1 (4)
C8—C9—C14	118.9 (4)	C22—C21—C20	121.2 (4)
C10—C9—C14	119.1 (4)	F4—C22—C21	118.6 (4)
C11—C10—C9	120.5 (4)	F4—C22—C17	119.4 (4)
C11—C10—H10	119.8	C21—C22—C17	122.0 (4)
C9—C10—H10	119.8
O1—N1—C1—C2	−176.9 (4)	C10—C9—C14—C13	−1.0 (7)
C5—N1—C1—C2	2.8 (6)	C13—C14—C15—C16	180.0 (4)
N1—C1—C2—C3	0.3 (6)	C9—C14—C15—C16	−0.5 (7)
C1—C2—C3—C4	−1.9 (6)	C14—C15—C16—C7	−0.4 (7)
C2—C3—C4—C5	0.4 (6)	C8—C7—C16—C15	0.5 (6)
O1—N1—C5—C4	175.5 (3)	C6—C7—C16—C15	−179.9 (4)
C1—N1—C5—C4	−4.2 (6)	C22—C17—C18—F1	−179.9 (3)
O1—N1—C5—S1	−5.6 (4)	I1—C17—C18—F1	1.4 (6)
C1—N1—C5—S1	174.7 (3)	C22—C17—C18—C19	−0.1 (6)
C3—C4—C5—N1	2.6 (6)	I1—C17—C18—C19	−178.9 (3)
C3—C4—C5—S1	−176.1 (3)	F1—C18—C19—F2	−0.1 (6)
C6—S1—C5—N1	−175.9 (3)	C17—C18—C19—F2	−179.8 (3)
C6—S1—C5—C4	2.9 (4)	F1—C18—C19—C20	−179.3 (4)
C5—S1—C6—C7	−91.4 (3)	C17—C18—C19—C20	0.9 (7)
S1—C6—C7—C8	−151.7 (3)	F2—C19—C20—C21	179.3 (3)
S1—C6—C7—C16	28.7 (5)	C18—C19—C20—C21	−1.4 (6)
C16—C7—C8—C9	0.3 (6)	F2—C19—C20—I2	−0.8 (5)
C6—C7—C8—C9	−179.3 (4)	C18—C19—C20—I2	178.4 (3)
C7—C8—C9—C10	−179.3 (4)	C19—C20—C21—F3	179.4 (3)
C7—C8—C9—C14	−1.2 (7)	I2—C20—C21—F3	−0.4 (5)
C8—C9—C10—C11	177.2 (4)	C19—C20—C21—C22	1.3 (6)
C14—C9—C10—C11	−0.9 (7)	I2—C20—C21—C22	−178.6 (3)
C9—C10—C11—C12	2.1 (7)	F3—C21—C22—F4	1.7 (6)
C10—C11—C12—C13	−1.3 (7)	C20—C21—C22—F4	179.9 (3)
C11—C12—C13—C14	−0.7 (7)	F3—C21—C22—C17	−178.7 (3)
C12—C13—C14—C15	−178.7 (4)	C20—C21—C22—C17	−0.5 (7)
C12—C13—C14—C9	1.8 (7)	C18—C17—C22—F4	179.5 (4)
C8—C9—C14—C15	1.3 (7)	I1—C17—C22—F4	−1.7 (5)
C10—C9—C14—C15	179.5 (3)	C18—C17—C22—C21	−0.1 (6)
C8—C9—C14—C13	−179.2 (3)	I1—C17—C22—C21	178.7 (3)

1,3,5-Trifluoro-2,4,6-triiodobenzene–2-{[(naphthalen-2-yl)methyl]sulfanyl}pyridine 1-oxide (1/1) (2)

Crystal data

C6F3I3·C16H13NOS	F(000) = 1448
Mr = 777.09	Dx = 2.256 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.0073 (1) Å	Cell parameters from 9636 reflections
b = 15.6551 (3) Å	θ = 5.1–71.8°
c = 20.8676 (4) Å	µ = 33.39 mm^−1
β = 91.727 (2)°	T = 119 K
V = 2288.14 (7) Å^3	Block, colourless
Z = 4	0.2 × 0.1 × 0.05 × 0.10 (radius) mm

Data collection

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 Source	4273 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.048
Detector resolution: 5.3127 pixels mm^-1	θmax = 72.0°, θmin = 3.5°
ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	k = −19→19
Tmin = 0.210, Tmax = 1.000	l = −17→25
15814 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 5.5786P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.002
4447 reflections	Δρmax = 2.92 e Å^−3
280 parameters	Δρmin = −0.76 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.80960 (4)	0.37502 (2)	0.35422 (2)	0.01680 (11)
I2	0.80477 (6)	0.69455 (2)	0.19198 (2)	0.02615 (12)
I3	0.82285 (5)	0.34574 (2)	0.06669 (2)	0.01881 (11)
S1	0.76937 (18)	0.42931 (8)	0.54423 (6)	0.0196 (3)
F1	0.8094 (5)	0.5708 (2)	0.31102 (14)	0.0222 (6)
F2	0.8059 (5)	0.5493 (2)	0.08650 (14)	0.0236 (7)
F3	0.8241 (5)	0.30148 (19)	0.21272 (15)	0.0245 (7)
O1	0.7664 (5)	0.2888 (2)	0.46872 (17)	0.0193 (8)
N1	0.5910 (7)	0.3041 (3)	0.4877 (2)	0.0175 (9)
C1	0.4459 (8)	0.2539 (4)	0.4662 (3)	0.0214 (11)
H1	0.468623	0.210471	0.435593	0.026*
C2	0.2644 (8)	0.2658 (4)	0.4888 (3)	0.0211 (11)
H2	0.161809	0.231070	0.473346	0.025*
C3	0.2325 (8)	0.3288 (4)	0.5342 (3)	0.0243 (12)
H3	0.109395	0.336264	0.551207	0.029*
C4	0.3839 (8)	0.3806 (4)	0.5541 (3)	0.0221 (11)
H4	0.363953	0.424385	0.584745	0.027*
C5	0.5640 (8)	0.3689 (3)	0.5297 (2)	0.0174 (10)
C6	0.6876 (8)	0.5106 (3)	0.5980 (2)	0.0205 (11)
H6A	0.768372	0.561848	0.592740	0.025*
H6B	0.555755	0.526402	0.584434	0.025*
C7	0.6879 (8)	0.4884 (3)	0.6690 (3)	0.0189 (10)
C8	0.6779 (8)	0.5543 (3)	0.7120 (3)	0.0201 (10)
H8	0.668176	0.611179	0.696416	0.024*
C9	0.6817 (8)	0.5398 (4)	0.7792 (3)	0.0207 (11)
C10	0.6711 (8)	0.6071 (4)	0.8241 (3)	0.0251 (12)
H10	0.659567	0.664406	0.809463	0.030*
C11	0.6773 (9)	0.5902 (5)	0.8888 (3)	0.0295 (13)
H11	0.669878	0.635818	0.918670	0.035*
C12	0.6946 (9)	0.5057 (4)	0.9108 (3)	0.0291 (13)
H12	0.700126	0.494777	0.955639	0.035*
C13	0.7035 (9)	0.4386 (4)	0.8688 (3)	0.0259 (12)
H13	0.714936	0.381832	0.884525	0.031*
C14	0.6957 (7)	0.4542 (4)	0.8015 (3)	0.0200 (11)
C15	0.7029 (8)	0.3871 (4)	0.7564 (3)	0.0224 (11)
H15	0.711244	0.329736	0.771168	0.027*
C16	0.6980 (8)	0.4030 (4)	0.6916 (3)	0.0221 (11)
H16	0.701456	0.356929	0.662008	0.027*
C17	0.8172 (7)	0.4346 (3)	0.2645 (2)	0.0156 (10)
C18	0.8110 (7)	0.5221 (3)	0.2577 (3)	0.0182 (10)
C19	0.8078 (8)	0.5627 (3)	0.1986 (2)	0.0185 (10)
C20	0.8113 (7)	0.5113 (4)	0.1442 (2)	0.0179 (10)
C21	0.8192 (7)	0.4234 (3)	0.1475 (2)	0.0157 (10)
C22	0.8192 (7)	0.3870 (3)	0.2082 (3)	0.0184 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02111 (18)	0.01545 (17)	0.01386 (17)	0.00315 (11)	0.00099 (12)	0.00237 (11)
I2	0.0408 (2)	0.01098 (17)	0.0261 (2)	−0.00225 (13)	−0.00828 (15)	0.00232 (12)
I3	0.02116 (18)	0.01924 (18)	0.01594 (17)	−0.00141 (12)	−0.00088 (12)	−0.00438 (11)
S1	0.0204 (6)	0.0194 (6)	0.0188 (6)	0.0013 (5)	−0.0003 (5)	−0.0016 (5)
F1	0.0354 (18)	0.0158 (14)	0.0153 (14)	0.0017 (13)	0.0002 (13)	−0.0051 (11)
F2	0.0336 (18)	0.0227 (16)	0.0143 (14)	−0.0044 (14)	−0.0035 (12)	0.0050 (12)
F3	0.042 (2)	0.0108 (14)	0.0206 (16)	0.0009 (13)	0.0011 (14)	0.0009 (11)
O1	0.0201 (19)	0.0206 (18)	0.0174 (17)	0.0082 (15)	0.0039 (14)	0.0061 (14)
N1	0.020 (2)	0.020 (2)	0.0123 (19)	0.0052 (17)	−0.0004 (16)	0.0035 (16)
C1	0.024 (3)	0.022 (3)	0.017 (2)	0.000 (2)	0.000 (2)	0.000 (2)
C2	0.019 (3)	0.020 (3)	0.024 (3)	−0.002 (2)	−0.002 (2)	0.008 (2)
C3	0.019 (3)	0.028 (3)	0.027 (3)	0.005 (2)	0.002 (2)	0.009 (2)
C4	0.026 (3)	0.021 (3)	0.020 (3)	0.009 (2)	0.003 (2)	0.003 (2)
C5	0.023 (3)	0.015 (2)	0.015 (2)	0.003 (2)	−0.001 (2)	0.0035 (18)
C6	0.027 (3)	0.016 (2)	0.018 (3)	0.002 (2)	0.000 (2)	−0.0009 (19)
C7	0.018 (3)	0.019 (3)	0.019 (3)	0.002 (2)	−0.0035 (19)	−0.001 (2)
C8	0.020 (3)	0.015 (2)	0.025 (3)	−0.002 (2)	−0.002 (2)	−0.001 (2)
C9	0.017 (3)	0.019 (3)	0.026 (3)	−0.003 (2)	−0.002 (2)	−0.005 (2)
C10	0.024 (3)	0.025 (3)	0.026 (3)	0.001 (2)	−0.005 (2)	−0.003 (2)
C11	0.023 (3)	0.043 (4)	0.023 (3)	−0.003 (3)	−0.002 (2)	−0.010 (3)
C12	0.026 (3)	0.041 (4)	0.020 (3)	−0.003 (3)	−0.001 (2)	−0.002 (2)
C13	0.028 (3)	0.028 (3)	0.022 (3)	−0.005 (2)	0.001 (2)	0.002 (2)
C14	0.014 (2)	0.023 (3)	0.023 (3)	−0.001 (2)	0.000 (2)	0.000 (2)
C15	0.030 (3)	0.018 (3)	0.019 (3)	−0.002 (2)	−0.003 (2)	0.003 (2)
C16	0.026 (3)	0.017 (3)	0.023 (3)	0.001 (2)	−0.003 (2)	−0.003 (2)
C17	0.017 (2)	0.014 (2)	0.015 (2)	−0.0003 (19)	0.0011 (18)	0.0052 (18)
C18	0.018 (2)	0.017 (2)	0.019 (2)	0.001 (2)	−0.001 (2)	−0.003 (2)
C19	0.028 (3)	0.008 (2)	0.019 (2)	−0.002 (2)	−0.002 (2)	−0.0014 (18)
C20	0.015 (2)	0.022 (3)	0.017 (2)	−0.002 (2)	−0.0035 (19)	0.006 (2)
C21	0.016 (2)	0.015 (2)	0.015 (2)	−0.0011 (19)	−0.0012 (18)	−0.0044 (18)
C22	0.019 (3)	0.014 (2)	0.022 (3)	0.0009 (19)	0.002 (2)	−0.001 (2)

Geometric parameters (Å, º)

I1—C17	2.093 (5)	C7—C16	1.418 (8)
I2—C19	2.069 (5)	C8—C9	1.421 (8)
I3—C21	2.079 (5)	C8—H8	0.9500
S1—C5	1.741 (6)	C9—C10	1.414 (8)
S1—C6	1.802 (5)	C9—C14	1.420 (8)
F1—C18	1.349 (6)	C10—C11	1.375 (9)
F2—C20	1.343 (6)	C10—H10	0.9500
F3—C22	1.343 (6)	C11—C12	1.406 (10)
O1—N1	1.324 (6)	C11—H11	0.9500
N1—C1	1.350 (8)	C12—C13	1.370 (9)
N1—C5	1.358 (7)	C12—H12	0.9500
C1—C2	1.382 (8)	C13—C14	1.426 (8)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.389 (9)	C14—C15	1.412 (8)
C2—H2	0.9500	C15—C16	1.375 (8)
C3—C4	1.390 (9)	C15—H15	0.9500
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.387 (8)	C17—C18	1.377 (7)
C4—H4	0.9500	C17—C22	1.393 (8)
C6—C7	1.522 (7)	C18—C19	1.387 (8)
C6—H6A	0.9900	C19—C20	1.393 (8)
C6—H6B	0.9900	C20—C21	1.379 (8)
C7—C8	1.370 (8)	C21—C22	1.389 (8)
C5—S1—C6	102.4 (3)	C10—C11—C12	120.1 (6)
O1—N1—C1	119.5 (4)	C10—C11—H11	119.9
O1—N1—C5	118.4 (5)	C12—C11—H11	119.9
C1—N1—C5	122.1 (5)	C13—C12—C11	121.1 (6)
N1—C1—C2	120.0 (5)	C13—C12—H12	119.4
N1—C1—H1	120.0	C11—C12—H12	119.4
C2—C1—H1	120.0	C12—C13—C14	119.9 (6)
C1—C2—C3	119.8 (5)	C12—C13—H13	120.0
C1—C2—H2	120.1	C14—C13—H13	120.0
C3—C2—H2	120.1	C15—C14—C9	119.2 (5)
C2—C3—C4	118.8 (5)	C15—C14—C13	121.9 (5)
C2—C3—H3	120.6	C9—C14—C13	118.9 (5)
C4—C3—H3	120.6	C16—C15—C14	121.3 (5)
C5—C4—C3	120.5 (5)	C16—C15—H15	119.3
C5—C4—H4	119.7	C14—C15—H15	119.3
C3—C4—H4	119.7	C15—C16—C7	119.8 (5)
N1—C5—C4	118.8 (5)	C15—C16—H16	120.1
N1—C5—S1	112.8 (4)	C7—C16—H16	120.1
C4—C5—S1	128.4 (4)	C18—C17—C22	116.5 (5)
C7—C6—S1	117.0 (4)	C18—C17—I1	122.3 (4)
C7—C6—H6A	108.0	C22—C17—I1	121.2 (4)
S1—C6—H6A	108.0	F1—C18—C17	118.6 (5)
C7—C6—H6B	108.0	F1—C18—C19	118.3 (5)
S1—C6—H6B	108.0	C17—C18—C19	123.1 (5)
H6A—C6—H6B	107.3	C18—C19—C20	117.4 (5)
C8—C7—C16	119.7 (5)	C18—C19—I2	121.1 (4)
C8—C7—C6	117.8 (5)	C20—C19—I2	121.5 (4)
C16—C7—C6	122.5 (5)	F2—C20—C21	119.1 (5)
C7—C8—C9	121.7 (5)	F2—C20—C19	118.4 (5)
C7—C8—H8	119.1	C21—C20—C19	122.6 (5)
C9—C8—H8	119.1	C20—C21—C22	116.9 (5)
C10—C9—C14	119.5 (5)	C20—C21—I3	123.0 (4)
C10—C9—C8	122.3 (5)	C22—C21—I3	120.0 (4)
C14—C9—C8	118.2 (5)	F3—C22—C21	118.2 (5)
C11—C10—C9	120.4 (6)	F3—C22—C17	118.4 (5)
C11—C10—H10	119.8	C21—C22—C17	123.4 (5)
C9—C10—H10	119.8
O1—N1—C1—C2	175.9 (5)	C12—C13—C14—C9	1.0 (8)
C5—N1—C1—C2	−2.4 (8)	C9—C14—C15—C16	0.5 (9)
N1—C1—C2—C3	−0.8 (8)	C13—C14—C15—C16	−179.0 (5)
C1—C2—C3—C4	2.3 (8)	C14—C15—C16—C7	0.8 (9)
C2—C3—C4—C5	−0.8 (8)	C8—C7—C16—C15	−1.7 (9)
O1—N1—C5—C4	−174.5 (4)	C6—C7—C16—C15	178.3 (5)
C1—N1—C5—C4	3.8 (7)	C22—C17—C18—F1	−179.8 (5)
O1—N1—C5—S1	7.0 (6)	I1—C17—C18—F1	3.3 (7)
C1—N1—C5—S1	−174.7 (4)	C22—C17—C18—C19	−0.3 (8)
C3—C4—C5—N1	−2.2 (8)	I1—C17—C18—C19	−177.2 (4)
C3—C4—C5—S1	176.1 (4)	F1—C18—C19—C20	179.4 (5)
C6—S1—C5—N1	177.9 (4)	C17—C18—C19—C20	−0.1 (8)
C6—S1—C5—C4	−0.5 (6)	F1—C18—C19—I2	0.9 (7)
C5—S1—C6—C7	85.0 (5)	C17—C18—C19—I2	−178.6 (4)
S1—C6—C7—C8	162.4 (4)	C18—C19—C20—F2	179.2 (5)
S1—C6—C7—C16	−17.6 (7)	I2—C19—C20—F2	−2.3 (7)
C16—C7—C8—C9	1.4 (8)	C18—C19—C20—C21	−0.5 (8)
C6—C7—C8—C9	−178.6 (5)	I2—C19—C20—C21	178.0 (4)
C7—C8—C9—C10	−179.9 (5)	F2—C20—C21—C22	−178.3 (5)
C7—C8—C9—C14	−0.2 (8)	C19—C20—C21—C22	1.5 (8)
C14—C9—C10—C11	1.0 (9)	F2—C20—C21—I3	−0.1 (7)
C8—C9—C10—C11	−179.3 (5)	C19—C20—C21—I3	179.6 (4)
C9—C10—C11—C12	0.1 (9)	C20—C21—C22—F3	179.1 (5)
C10—C11—C12—C13	−0.7 (9)	I3—C21—C22—F3	0.8 (7)
C11—C12—C13—C14	0.1 (9)	C20—C21—C22—C17	−1.9 (8)
C10—C9—C14—C15	178.9 (5)	I3—C21—C22—C17	179.9 (4)
C8—C9—C14—C15	−0.8 (8)	C18—C17—C22—F3	−179.6 (5)
C10—C9—C14—C13	−1.6 (8)	I1—C17—C22—F3	−2.7 (7)
C8—C9—C14—C13	178.7 (5)	C18—C17—C22—C21	1.3 (8)
C12—C13—C14—C15	−179.5 (6)	I1—C17—C22—C21	178.3 (4)