1,2,4,5-Tetra-fluoro-3,6-diiodo-benzene-4-(pyridin-4-ylsulfan-yl)pyridine (1/1).

The asymmetric unit of the title 1:1 adduct, C(10)H(8)N(2)S·C(6)F(4)I(2), comprises a half-mol-ecule of 1,2,4,5-tetra-fluoro-3,6-diiodo-benzene, and half a 4-(pyridin-4-ylsulfan-yl)pyridine mol-ecule. The former is completed by crystallographic inversion symmetry, the latter by twofold symmetry, with the S atom lying on the rotation axis. The almost planar 1,2,4,5-tetra-fluoro-3,6-diiodo-benzene mol-ecule (r.m.s. deviation of all 12 atoms = 0.016 Å) and twisted 4-(pyridin-4-ylsulfan-yl)pyridine mol-ecule [dihedral angle between pyridyl rings = 54.88 (13)°] are connected by N⋯I inter-actions [2.838 (4) Å], generating a supra-molecular chain with a step-ladder topology. These chains are connected in the crystal by C-H⋯F and C-H⋯π(pyrid-yl) inter-actions.

Related literature

For related studies on co-crystal formation, see: Broker et al. (2008 ▶); Arman et al. (2010 ▶). For background to halogen bonding, see: Metrangolo et al. (2008 ▶); Pennington et al. (2008 ▶). For the desulfurization of 4-(pyridin-4-yldisulfan­yl)pyridine, see: Aragoni et al. (2007 ▶).

Experimental

Crystal data

C10H8N2S·C6F4I2

M = 590.10

Monoclinic,

a = 13.804 (5) Å

b = 5.829 (2) Å

c = 22.164 (8) Å

β = 97.989 (7)°

V = 1766.1 (11) Å3

Z = 4

Mo Kα radiation

μ = 3.72 mm−1

T = 98 K

0.30 × 0.20 × 0.05 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.757, T max = 1.000

5209 measured reflections

1823 independent reflections

1733 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.073

S = 1.07

1823 reflections

114 parameters

H-atom parameters constrained

Δρmax = 1.34 e Å−3

Δρmin = −0.63 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038316/hb5647sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038316/hb5647Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H8N2S·C6F4I2	F(000) = 1104
Mr = 590.10	Dx = 2.219 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3043 reflections
a = 13.804 (5) Å	θ = 3.0–40.2°
b = 5.829 (2) Å	µ = 3.72 mm−1
c = 22.164 (8) Å	T = 98 K
β = 97.989 (7)°	Block, yellow
V = 1766.1 (11) Å3	0.30 × 0.20 × 0.05 mm
Z = 4

Rigaku AFC12K/SATURN724 diffractometer	1823 independent reflections
Radiation source: fine-focus sealed tube	1733 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 26.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→14
Tmin = 0.757, Tmax = 1.000	k = −5→7
5209 measured reflections	l = −27→26

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0202P)2 + 21.2619P] where P = (Fo2 + 2Fc2)/3
1823 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 1.34 e Å−3
0 restraints	Δρmin = −0.63 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
I1	0.33988 (2)	0.75767 (5)	0.089898 (12)	0.02060 (11)
F1	0.4107 (2)	0.9003 (5)	−0.03751 (12)	0.0253 (6)
F2	0.5292 (2)	0.6993 (5)	−0.10663 (12)	0.0257 (6)
C1	0.4356 (3)	0.6036 (8)	0.0360 (2)	0.0186 (9)
C2	0.4540 (3)	0.6999 (7)	−0.0181 (2)	0.0180 (9)
C3	0.5168 (3)	0.5980 (8)	−0.0534 (2)	0.0205 (9)
S1	0.0000	0.4266 (3)	0.2500	0.0201 (3)
N1	0.2103 (3)	−0.0202 (7)	0.15987 (18)	0.0248 (9)
C4	0.1787 (3)	0.1842 (9)	0.1379 (2)	0.0239 (10)
H4	0.2032	0.2404	0.1028	0.029*
C5	0.1121 (3)	0.3192 (8)	0.1635 (2)	0.0215 (9)
H5	0.0905	0.4616	0.1455	0.026*
C6	0.0779 (3)	0.2417 (8)	0.2158 (2)	0.0191 (9)
C7	0.1112 (3)	0.0326 (8)	0.2401 (2)	0.0193 (9)
H7	0.0900	−0.0242	0.2763	0.023*
C8	0.1762 (3)	−0.0926 (8)	0.2104 (2)	0.0203 (9)
H8	0.1977	−0.2373	0.2268	0.024*

	U11	U22	U33	U12	U13	U23
I1	0.01922 (17)	0.02358 (17)	0.01968 (17)	0.00034 (12)	0.00505 (11)	−0.00148 (11)
F1	0.0271 (15)	0.0212 (14)	0.0285 (15)	0.0061 (12)	0.0072 (12)	0.0045 (11)
F2	0.0288 (16)	0.0283 (14)	0.0218 (14)	0.0026 (12)	0.0099 (11)	0.0084 (11)
C1	0.013 (2)	0.023 (2)	0.020 (2)	−0.0024 (17)	0.0021 (16)	−0.0062 (17)
C2	0.015 (2)	0.017 (2)	0.021 (2)	−0.0005 (17)	−0.0009 (16)	0.0016 (16)
C3	0.021 (2)	0.023 (2)	0.018 (2)	−0.0036 (19)	0.0029 (17)	0.0006 (17)
S1	0.0203 (8)	0.0166 (7)	0.0245 (8)	0.000	0.0068 (6)	0.000
N1	0.020 (2)	0.026 (2)	0.028 (2)	0.0012 (17)	0.0057 (16)	−0.0018 (17)
C4	0.017 (2)	0.031 (3)	0.023 (2)	−0.0047 (19)	0.0040 (18)	0.0002 (19)
C5	0.022 (2)	0.020 (2)	0.022 (2)	−0.0007 (18)	0.0005 (18)	0.0007 (17)
C6	0.015 (2)	0.020 (2)	0.023 (2)	−0.0012 (17)	0.0041 (17)	−0.0043 (17)
C7	0.014 (2)	0.019 (2)	0.024 (2)	−0.0025 (17)	0.0003 (17)	−0.0017 (17)
C8	0.016 (2)	0.018 (2)	0.026 (2)	−0.0010 (17)	−0.0013 (17)	−0.0009 (17)

I1—C1	2.101 (4)	N1—C4	1.337 (6)
F1—C2	1.355 (5)	C4—C5	1.389 (7)
F2—C3	1.352 (5)	C4—H4	0.9500
C1—C2	1.379 (6)	C5—C6	1.387 (6)
C1—C3i	1.375 (6)	C5—H5	0.9500
C2—C3	1.381 (6)	C6—C7	1.385 (6)
C3—C1i	1.375 (6)	C7—C8	1.392 (6)
S1—C6ii	1.766 (4)	C7—H7	0.9500
S1—C6	1.766 (4)	C8—H8	0.9500
N1—C8	1.342 (6)
C2—C1—C3i	116.9 (4)	C5—C4—H4	118.0
C2—C1—I1	121.8 (3)	C6—C5—C4	118.5 (4)
C3i—C1—I1	121.3 (3)	C6—C5—H5	120.7
C1—C2—F1	120.0 (4)	C4—C5—H5	120.7
C1—C2—C3	121.6 (4)	C7—C6—C5	118.6 (4)
F1—C2—C3	118.4 (4)	C7—C6—S1	124.0 (4)
F2—C3—C1i	120.3 (4)	C5—C6—S1	117.3 (3)
F2—C3—C2	118.2 (4)	C6—C7—C8	118.6 (4)
C1i—C3—C2	121.5 (4)	C6—C7—H7	120.7
C6ii—S1—C6	104.8 (3)	C8—C7—H7	120.7
C8—N1—C4	116.7 (4)	N1—C8—C7	123.7 (4)
N1—C4—C5	123.9 (4)	N1—C8—H8	118.2
N1—C4—H4	118.0	C7—C8—H8	118.2
C3i—C1—C2—F1	−179.1 (4)	N1—C4—C5—C6	1.7 (7)
I1—C1—C2—F1	0.6 (6)	C4—C5—C6—C7	−0.3 (7)
C3i—C1—C2—C3	0.4 (7)	C4—C5—C6—S1	175.7 (4)
I1—C1—C2—C3	−179.9 (3)	C6ii—S1—C6—C7	−34.9 (3)
C1—C2—C3—F2	178.2 (4)	C6ii—S1—C6—C5	149.3 (4)
F1—C2—C3—F2	−2.3 (6)	C5—C6—C7—C8	−1.1 (6)
C1—C2—C3—C1i	−0.4 (8)	S1—C6—C7—C8	−176.8 (3)
F1—C2—C3—C1i	179.0 (4)	C4—N1—C8—C7	0.0 (7)
C8—N1—C4—C5	−1.5 (7)	C6—C7—C8—N1	1.3 (7)

Cg1 is the centroid of the N1,C4–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F1iii	0.95	2.52	3.213 (5)	130
C8—H8···Cg1iv	0.95	2.82	3.557 (5)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C4–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F1i	0.95	2.52	3.213 (5)	130
C8—H8⋯Cg1ii	0.95	2.82	3.557 (5)	135

Symmetry codes: (i) ; (ii) .