2-(2,3,5,6-Tetra-fluoro-4-iodo-anilino)-ethanol.

The reaction of 2-amino-ethanol and iodo-penta-fluoro-benzene in the presence of K(2)CO(3) gave the title compound, C(8)H(6)F(4)INO, in high yield. The structure is characterized by double layers of mol-ecules linked by O-H⋯O and N-H⋯O hydrogen bonds, and linear C-I⋯F [I⋯F = 3.049 (2) Å] and bent C-I⋯I [I⋯I = 3.9388 (7) Å] inter-actions between pairs of nearly parallel iodo-tetra-fluoro-phenyl groups. No O⋯I or N⋯I halogen bonding is found.

Related literature

For related literature, see: Metrangolo & Resnati (2001 ▶); Metrangolo et al. (2005 ▶, 2007 ▶).

Experimental

Crystal data

C8H6F4INO

M = 335.04

Monoclinic,

a = 13.327 (2) Å

b = 17.663 (3) Å

c = 8.3044 (14) Å

β = 96.94 (2)°

V = 1940.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 3.33 mm−1

T = 158 (2) K

0.24 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.691, T max = 1.000 (expected range = 0.529–0.766)

8054 measured reflections

2924 independent reflections

2422 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.04

2924 reflections

162 parameters

8 restraints

All H-atom parameters refined

Δρmax = 1.65 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064197/cf2167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064197/cf2167Isup2.hkl

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

C8H6F4INO	F000 = 1264
Mr = 335.04	Dx = 2.294 Mg m−3
Monoclinic, C2/c	Melting point = 343–348 K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 13.327 (2) Å	Cell parameters from 2964 reflections
b = 17.663 (3) Å	θ = 3.0–29.1º
c = 8.3044 (14) Å	µ = 3.33 mm−1
β = 96.94 (2)º	T = 158 (2) K
V = 1940.5 (6) Å3	Irregular table, colourless
Z = 8	0.24 × 0.16 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	2924 independent reflections
Radiation source: fine-focus sealed tube	2422 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 158(2) K	θmax = 31.3º
ω and φ scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −18→18
Tmin = 0.691, Tmax = 1.000	k = −16→25
8054 measured reflections	l = −11→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	All H-atom parameters refined
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0481P)2 + 2.2775P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2924 reflections	Δρmax = 1.65 e Å−3
162 parameters	Δρmin = −0.47 e Å−3
8 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. Data collection using an OXFORD low temperature device. Below 158 K the structure possibly shows a phase transition.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	Occ. (<1)
I1	0.116120 (18)	0.431723 (13)	1.05305 (3)	0.03962 (10)
F1	0.11489 (13)	0.12833 (11)	1.03239 (18)	0.0310 (4)
F2	0.10979 (15)	0.26089 (11)	1.1821 (2)	0.0341 (4)
F3	0.13483 (15)	0.38552 (11)	0.6853 (2)	0.0375 (4)
F4	0.13603 (14)	0.25397 (11)	0.53509 (19)	0.0320 (4)
N1	0.12288 (19)	0.11508 (15)	0.7067 (3)	0.0256 (5)
H1N	0.120 (3)	0.080 (2)	0.779 (5)	0.032 (10)*
O1	0.06410 (19)	0.02423 (13)	0.3901 (2)	0.0322 (5)
H1O	0.026 (5)	0.027 (5)	0.306 (6)	0.048*	0.50
H2O	0.022 (5)	0.020 (5)	0.454 (8)	0.048*	0.50
C1	0.12620 (19)	0.18530 (16)	0.7785 (3)	0.0211 (5)
C2	0.1188 (2)	0.19221 (15)	0.9451 (3)	0.0220 (5)
C3	0.11614 (19)	0.26044 (18)	1.0212 (3)	0.0239 (5)
C4	0.1225 (2)	0.32801 (16)	0.9396 (4)	0.0257 (5)
C5	0.1307 (2)	0.32223 (17)	0.7744 (4)	0.0266 (6)
C6	0.13237 (19)	0.25369 (15)	0.6968 (3)	0.0235 (5)
C7	0.1830 (2)	0.0964 (2)	0.5749 (3)	0.0300 (6)
H7A	0.216 (3)	0.0485 (14)	0.602 (4)	0.031 (9)*
H7B	0.237 (2)	0.1319 (17)	0.573 (4)	0.032 (9)*
C8	0.1226 (3)	0.0915 (2)	0.4085 (3)	0.0303 (6)
H8A	0.079 (3)	0.136 (2)	0.388 (6)	0.072 (15)*
H8B	0.161 (2)	0.090 (2)	0.319 (3)	0.029 (9)*

	U11	U22	U33	U12	U13	U23
I1	0.04639 (16)	0.02605 (13)	0.04478 (15)	0.00436 (8)	−0.00122 (10)	−0.00885 (8)
F1	0.0507 (11)	0.0251 (9)	0.0177 (7)	−0.0040 (7)	0.0061 (7)	0.0048 (6)
F2	0.0505 (10)	0.0345 (10)	0.0177 (7)	0.0006 (8)	0.0052 (7)	−0.0053 (7)
F3	0.0486 (11)	0.0235 (9)	0.0403 (10)	−0.0035 (8)	0.0052 (8)	0.0108 (8)
F4	0.0446 (10)	0.0336 (10)	0.0190 (8)	−0.0037 (8)	0.0089 (7)	0.0048 (7)
N1	0.0371 (13)	0.0243 (12)	0.0161 (10)	−0.0009 (10)	0.0068 (9)	0.0017 (9)
O1	0.0516 (14)	0.0244 (10)	0.0190 (9)	0.0051 (10)	−0.0024 (9)	−0.0019 (8)
C1	0.0215 (11)	0.0249 (13)	0.0171 (11)	0.0001 (10)	0.0032 (9)	0.0004 (9)
C2	0.0263 (12)	0.0208 (12)	0.0192 (11)	−0.0011 (10)	0.0040 (9)	0.0039 (9)
C3	0.0248 (13)	0.0273 (14)	0.0195 (12)	−0.0018 (10)	0.0021 (10)	−0.0017 (10)
C4	0.0229 (12)	0.0215 (13)	0.0325 (14)	0.0001 (10)	0.0021 (10)	−0.0011 (11)
C5	0.0243 (12)	0.0253 (13)	0.0297 (14)	−0.0023 (11)	0.0020 (10)	0.0084 (11)
C6	0.0240 (12)	0.0275 (14)	0.0194 (12)	−0.0035 (11)	0.0045 (10)	0.0030 (10)
C7	0.0345 (15)	0.0359 (16)	0.0204 (12)	0.0057 (13)	0.0061 (11)	−0.0026 (11)
C8	0.0408 (16)	0.0331 (15)	0.0172 (12)	0.0021 (13)	0.0049 (11)	0.0016 (11)

I1—C4	2.067 (3)	C1—C6	1.393 (4)
F1—C2	1.345 (3)	C1—C2	1.404 (4)
F2—C3	1.349 (3)	C2—C3	1.363 (4)
F3—C5	1.346 (3)	C3—C4	1.380 (4)
F4—C6	1.350 (3)	C4—C5	1.392 (4)
N1—C1	1.375 (4)	C5—C6	1.373 (4)
N1—C7	1.470 (4)	C7—C8	1.516 (4)
N1—H1N	0.87 (4)	C7—H7A	0.97 (2)
O1—C8	1.419 (4)	C7—H7B	0.96 (2)
O1—H1O	0.818 (10)	C8—H8A	0.97 (2)
O1—H2O	0.818 (10)	C8—H8B	0.96 (2)
C1—N1—C7	122.3 (2)	F3—C5—C6	118.0 (3)
C1—N1—H1N	110 (3)	F3—C5—C4	119.6 (3)
C7—N1—H1N	115 (3)	C6—C5—C4	122.3 (3)
C8—O1—H1O	108 (6)	F4—C6—C5	117.9 (2)
C8—O1—H2O	115 (6)	F4—C6—C1	120.0 (2)
H1O—O1—H2O	99 (8)	C5—C6—C1	122.0 (2)
N1—C1—C6	124.9 (2)	N1—C7—C8	114.5 (3)
N1—C1—C2	120.3 (2)	N1—C7—H7A	107 (2)
C6—C1—C2	114.8 (2)	C8—C7—H7A	110 (2)
F1—C2—C3	119.1 (2)	N1—C7—H7B	110 (2)
F1—C2—C1	118.0 (2)	C8—C7—H7B	110 (2)
C3—C2—C1	122.9 (3)	H7A—C7—H7B	105 (3)
F2—C3—C2	118.2 (3)	O1—C8—C7	111.7 (3)
F2—C3—C4	119.8 (3)	O1—C8—H8A	110 (3)
C2—C3—C4	122.0 (3)	C7—C8—H8A	110 (3)
C3—C4—C5	115.9 (3)	O1—C8—H8B	104 (2)
C3—C4—I1	122.3 (2)	C7—C8—H8B	116 (2)
C5—C4—I1	121.8 (2)	H8A—C8—H8B	105 (4)
C7—N1—C1—C6	38.5 (4)	C3—C4—C5—F3	178.5 (2)
C7—N1—C1—C2	−144.3 (3)	I1—C4—C5—F3	0.1 (4)
N1—C1—C2—F1	4.1 (4)	C3—C4—C5—C6	0.0 (4)
C6—C1—C2—F1	−178.5 (2)	I1—C4—C5—C6	−178.3 (2)
N1—C1—C2—C3	−176.3 (3)	F3—C5—C6—F4	−1.3 (4)
C6—C1—C2—C3	1.1 (4)	C4—C5—C6—F4	177.1 (2)
F1—C2—C3—F2	0.1 (4)	F3—C5—C6—C1	−178.6 (2)
C1—C2—C3—F2	−179.5 (2)	C4—C5—C6—C1	−0.1 (4)
F1—C2—C3—C4	178.3 (2)	N1—C1—C6—F4	−0.3 (4)
C1—C2—C3—C4	−1.3 (4)	C2—C1—C6—F4	−177.6 (2)
F2—C3—C4—C5	178.8 (2)	N1—C1—C6—C5	176.9 (3)
C2—C3—C4—C5	0.7 (4)	C2—C1—C6—C5	−0.4 (4)
F2—C3—C4—I1	−2.8 (4)	C1—N1—C7—C8	−106.0 (3)
C2—C3—C4—I1	179.0 (2)	N1—C7—C8—O1	−74.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.87 (2)	2.23 (3)	3.046 (3)	157 (3)
O1—H1O···O1ii	0.82 (5)	1.90 (7)	2.715 (4)	175 (8)
O1—H2O···O1iii	0.82 (5)	1.99 (5)	2.781 (4)	162 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.87 (2)	2.23 (3)	3.046 (3)	157 (3)
O1—H1O⋯O1ii	0.82 (5)	1.90 (7)	2.715 (4)	175 (8)
O1—H2O⋯O1iii	0.82 (5)	1.99 (5)	2.781 (4)	162 (8)

Symmetry codes: (i) ; (ii) ; (iii) .