5,7 Di­iodo­quinolin 8 ol

organic papers

Acta Cryst.(2007). E63, o15–o16 doi:10.1107/S1600536806050690 Buttet al. _C

9H5I2NO

o15

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

5,7-Diiodoquinolin-8-ol

M. Saeed Butt,aZareen Akhter,a* Michael Bolteband Humaira M. Siddiqia

a_{Department of Chemistry, Quaid-I-Azam}

University, Islamabad 45320, Pakistan, and

b

Institut fu¨r Anorganische Chemie, J.-W.-Goethe-Universita¨t Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 173 K

Mean(C–C) = 0.006 A˚

Rfactor = 0.031

wRfactor = 0.077

Data-to-parameter ratio = 18.7

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 31 August 2006 Accepted 24 November 2006

#2007 International Union of Crystallography All rights reserved

The title compound, C9H5I2NO, features an almost planar

molecule. Geometric parameters are in the usual ranges. The crystal packing shows that two hydrogen-bonded molecules are related by a twofold rotation axis.

Comment

5,7-Diiodoquinolin-8-ol, (I), is of therapeutic interest.

Quinolin-8-ol and its derivatives have antibacterial activity and form chelate complexes with divalent metal ions (Rohde

et al., 1976). The importance of metallic oxinates in analytical chemistry is also well known. Oxine and its derivatives have found extensive application as analytical reagents (Guerreiro

et al., 2002) in absorption spectroscopy, fluorimetry, extraction with solvents and chromatography. In an attempt to prepare the manganese complex of 5,7-diiodo-8-hydroxyquinoline we obtained crystals of the ligand, (I). A perspective view of the title compound is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Structural Database; Version 5.27, November 2005, updated August 2006; Allen, 2002). The molecule is essentially planar (r.m.s. deviation for all non-H atoms is 0.058 A˚ ). The packing diagram (Fig. 2) reveals that two molecules, which are related by a twofold rotation axis, are connected by an O—H N hydrogen bonds (Table 1).

Experimental

An attempt was made to complex 5,7-diiodoquinolin-8-ol with manganese. Unfortunately, ligand (I) crystallized out in an attempt to recrystallize the complex (m.p. 471–473 K) from toluene.

Crystal data

C9H5I2NO

Mr= 396.94

Monoclinic,P2=c a= 14.1699 (13) A˚

b= 4.2915 (4) A˚

c= 16.1565 (13) A˚

= 96.801 (7) V= 975.57 (15) A˚3

Z= 4

Dx= 2.703 Mg m

3

MoKradiation

= 6.40 mm1

T= 173 (2) K Rod, yellow

Data collection

Stoe IPDS-II two-circle diffractometer

!scans

Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)

Tmin= 0.318,Tmax= 0.527

7396 measured reflections 2244 independent reflections 2163 reflections withI> 2(I)

Rint= 0.046

max= 27.5

Refinement

Refinement onF2

R[F2_{> 2(F}2_{)] = 0.031}

wR(F2_{) = 0.077}

S= 1.17 2244 reflections 120 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0385P)2

+ 2.4632P]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.001

max= 1.25 e A˚

3

min=1.23 e A˚

3

Extinction correction:SHELXL97

Extinction coefficient: 0.0083 (5)

Table 1

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

O1—H1 N7i

0.84 1.98 2.757 (5) 154

Symmetry code: (i)xþ1;y;zþ3 2.

H atoms were found in a difference Fourier map but they were constrained, with C—H = 0.95 A˚ and O—H = 0.84 A˚, and were refined using a riding model;Uiso(H) = 1.2Ueq(C,O). The hydroxyl

group was allowed to rotate but not to tip. The highest peak in the final difference Fourier map is located at 0.77 A˚ from I1 and the deepest hole is at 0.98 A˚ from I2.

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement:

X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS86(Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

PLATON(Spek, 2003) andXPinSHELXTL-Plus(Sheldrick, 1991); software used to prepare material for publication:SHELXL97and

PLATON.

The authors are grateful to the Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan.

References

Allen, F. H. (2002).Acta Cryst.B58, 380–388. Blessing, R. H. (1995).Acta Cryst.A51, 33–38.

Guerreiro, C. T. R., Ribeiro, C. A. & Crespi, M. S. (2002).J. Therm. Anal. Calorim.70, 437–445.

Rohde, W., Mikelens, P., Jackson, J., Blackman, J., Whitcher, J. & Levinson, W. (1976).Antimicrob. Agents Chemother.10, 234–240.

Sheldrick, G. M. (1990).Acta Cryst.A46, 467–473.

Sheldrick, G. M. (1991).SHELXTL-Plus. Release 4.1. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1997).SHELXL97. University of Go¨ttingen, Germany. Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Stoe & Cie (2001).X-AREA. Stoe & Cie, Darmstadt, Germany.

Figure 1

Molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.

Figure 2

supporting information

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Acta Cryst. (2007). E63, o15–o16

supporting information

Acta Cryst. (2007). E63, o15–o16 [https://doi.org/10.1107/S1600536806050690]

5,7-Diiodoquinolin-8-ol

M. Saeed Butt, Zareen Akhter, Michael Bolte and Humaira M. Siddiqi

5,7-Diiodoquinolin-8-ol

Crystal data

C9H5I2NO Mr = 396.94

Monoclinic, P2/c

Hall symbol: -P 2yc

a = 14.1699 (13) Å

b = 4.2915 (4) Å

c = 16.1565 (13) Å

β = 96.801 (7)°

V = 975.57 (15) Å3 Z = 4

F(000) = 720

Dx = 2.703 Mg m−3 Melting point: 472(1) K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 7152 reflections

θ = 3.6–27.2°

µ = 6.40 mm−1 T = 173 K Rod, yellow

0.31 × 0.11 × 0.10 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω scans

Absorption correction: multi-scan

(MULABS; Spek, 2003; Blessing, 1995)

Tmin = 0.318, Tmax = 0.527

7396 measured reflections 2244 independent reflections 2163 reflections with I > 2σ(I)

Rint = 0.046

θmax = 27.5°, θmin = 3.6°

h = −18→18

k = −5→5

l = −20→21

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.031} wR(F2_{) = 0.077} S = 1.17 2244 reflections 120 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0385P)2 + 2.4632P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001 Δρmax = 1.25 e Å−3 Δρmin = −1.23 e Å−3

Special details

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 F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2₎

x y z Uiso*/Ueq

I1 0.199166 (19) 1.16860 (6) 0.595651 (15) 0.02198 (12)

I2 0.062028 (18) 0.50962 (6) 0.884895 (17) 0.02272 (12)

O1 0.3950 (2) 0.8966 (8) 0.68130 (19) 0.0244 (6)

H1 0.4428 0.7834 0.6942 0.029*

C1 0.3270 (3) 0.8246 (9) 0.7300 (2) 0.0179 (7)

C2 0.2343 (3) 0.9234 (9) 0.7074 (2) 0.0168 (7)

C3 0.1599 (3) 0.8430 (9) 0.7548 (2) 0.0167 (7)

H3 0.0975 0.9198 0.7390 0.020*

C4 0.1780 (3) 0.6540 (9) 0.8236 (2) 0.0168 (7)

C5 0.2723 (3) 0.5472 (9) 0.8502 (2) 0.0159 (7)

C6 0.3471 (3) 0.6446 (9) 0.8039 (2) 0.0178 (7)

N7 0.4399 (3) 0.5647 (9) 0.8275 (2) 0.0211 (7)

C8 0.4603 (3) 0.3821 (11) 0.8938 (3) 0.0244 (8)

H8 0.5248 0.3261 0.9097 0.029*

C9 0.3907 (3) 0.2676 (11) 0.9418 (3) 0.0228 (8)

H9 0.4081 0.1343 0.9880 0.027*

C10 0.2973 (3) 0.3523 (10) 0.9205 (3) 0.0206 (8)

H10 0.2497 0.2806 0.9526 0.025*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

I1 0.02860 (18) 0.02110 (17) 0.01693 (16) 0.00530 (10) 0.00559 (10) 0.00259 (9)

I2 0.01802 (17) 0.02671 (18) 0.02479 (17) −0.00249 (9) 0.00822 (11) 0.00300 (10)

O1 0.0171 (13) 0.0334 (16) 0.0241 (14) 0.0032 (13) 0.0079 (11) 0.0093 (14)

C1 0.0193 (18) 0.0184 (18) 0.0166 (17) −0.0029 (14) 0.0044 (14) −0.0008 (15)

C2 0.0219 (19) 0.0141 (16) 0.0146 (16) −0.0002 (14) 0.0023 (14) −0.0009 (14)

C3 0.0138 (16) 0.0178 (17) 0.0185 (17) −0.0010 (13) 0.0016 (13) −0.0024 (14)

C4 0.0131 (17) 0.0203 (18) 0.0176 (17) −0.0038 (13) 0.0048 (13) −0.0040 (15)

C5 0.0169 (17) 0.0154 (16) 0.0154 (16) −0.0031 (14) 0.0019 (13) −0.0011 (14)

C6 0.0161 (17) 0.0189 (18) 0.0187 (17) −0.0014 (14) 0.0026 (13) −0.0052 (15)

N7 0.0188 (16) 0.0257 (17) 0.0191 (16) 0.0013 (14) 0.0039 (13) −0.0005 (14)

C8 0.0211 (19) 0.028 (2) 0.0237 (19) 0.0050 (17) 0.0008 (15) −0.0021 (18)

C9 0.024 (2) 0.0229 (19) 0.0203 (19) 0.0025 (16) −0.0005 (15) 0.0028 (16)

supporting information

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Acta Cryst. (2007). E63, o15–o16

Geometric parameters (Å, º)

I1—C2 2.098 (4) C5—C10 1.420 (6)

I2—C4 2.110 (4) C5—C6 1.430 (5)

O1—C1 1.350 (5) C6—N7 1.370 (5)

O1—H1 0.8400 N7—C8 1.332 (6)

C1—C2 1.388 (6) C8—C9 1.413 (6)

C1—C6 1.421 (6) C8—H8 0.9500

C2—C3 1.417 (5) C9—C10 1.376 (6)

C3—C4 1.375 (6) C9—H9 0.9500

C3—H3 0.9500 C10—H10 0.9500

C4—C5 1.430 (5)

C1—O1—H1 109.5 C4—C5—C6 118.2 (4)

O1—C1—C2 119.7 (4) N7—C6—C1 117.4 (4)

O1—C1—C6 121.9 (4) N7—C6—C5 121.8 (4)

C2—C1—C6 118.4 (4) C1—C6—C5 120.8 (4)

C1—C2—C3 121.6 (4) C8—N7—C6 118.8 (4)

C1—C2—I1 120.1 (3) N7—C8—C9 123.2 (4)

C3—C2—I1 118.1 (3) N7—C8—H8 118.4

C4—C3—C2 120.1 (3) C9—C8—H8 118.4

C4—C3—H3 120.0 C10—C9—C8 119.0 (4)

C2—C3—H3 120.0 C10—C9—H9 120.5

C3—C4—C5 120.7 (3) C8—C9—H9 120.5

C3—C4—I2 118.2 (3) C9—C10—C5 119.8 (4)

C5—C4—I2 121.1 (3) C9—C10—H10 120.1

C10—C5—C4 124.4 (4) C5—C10—H10 120.1

C10—C5—C6 117.4 (4)

O1—C1—C2—C3 177.5 (4) O1—C1—C6—C5 −174.2 (4)

C6—C1—C2—C3 −1.5 (6) C2—C1—C6—C5 4.7 (6)

O1—C1—C2—I1 2.3 (5) C10—C5—C6—N7 −2.5 (6)

C6—C1—C2—I1 −176.6 (3) C4—C5—C6—N7 176.9 (4)

C1—C2—C3—C4 −2.2 (6) C10—C5—C6—C1 176.3 (4)

I1—C2—C3—C4 173.0 (3) C4—C5—C6—C1 −4.3 (6)

C2—C3—C4—C5 2.7 (6) C1—C6—N7—C8 −176.4 (4)

C2—C3—C4—I2 −174.5 (3) C5—C6—N7—C8 2.4 (6)

C3—C4—C5—C10 179.9 (4) C6—N7—C8—C9 −0.5 (7)

I2—C4—C5—C10 −3.0 (6) N7—C8—C9—C10 −1.3 (7)

C3—C4—C5—C6 0.5 (6) C8—C9—C10—C5 1.2 (7)

I2—C4—C5—C6 177.6 (3) C4—C5—C10—C9 −178.7 (4)

O1—C1—C6—N7 4.7 (6) C6—C5—C10—C9 0.6 (6)

C2—C1—C6—N7 −176.4 (4)

Hydrogen-bond geometry (Å, º)

O1—H1···N7i _{0.84 1.98 2.757 (5) 154}