organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-[(2-Chloro­phen­yl)imino­meth­yl]-4,6-di­iodo­phenol

aState Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China, and Jiangsu Tiansheng Pharmaceutical Company Limited, Jurong Jiangsu 212415, People's Republic of China
*Correspondence e-mail: hailiang_zhu@163.com

(Received 8 February 2012; accepted 18 February 2012; online 24 February 2012)

The asymmetric unit of the title compound, C13H8ClI2NO, contains half of the mol­ecule situated on a mirror plane. The hy­droxy group is involved in the formation of an intra­molecular O—H⋯N hydrogen bond. ππ inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.629 (3) Å] form stacks along the b axis. In the crystal, weak C—H⋯O and C—H⋯Cl inter­actions are observed.

Related literature

For standard bond distances, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the crystal structures of related compounds, see: Francis et al. (2003[Francis, S., Mu­thiah, P. T., Venkatachalam, G. & Ramesh, R. (2003). Acta Cryst. E59, o1045-o1047.]); Weiser et al. (2006[Weiser, M.-S., Wesolek, M. & Mulhaupt, R. (2006). J. Organomet. Chem. 691, 2945-2952.]); Barba et al. (2009[Barba, V., Hernandez, R., Hopfl, H., Santillan, R. & Farfan, N. (2009). J. Organomet. Chem. 694, 2127-2133.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8ClI2NO

  • Mr = 483.45

  • Orthorhombic, P n m a

  • a = 15.8432 (17) Å

  • b = 6.9942 (8) Å

  • c = 13.1975 (14) Å

  • V = 1462.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.47 mm−1

  • T = 296 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.468, Tmax = 0.663

  • 9861 measured reflections

  • 1829 independent reflections

  • 1659 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.144

  • S = 0.98

  • 1829 reflections

  • 113 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.13 e Å−3

  • Δρmin = −0.76 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯N1 0.84 (2) 1.95 (8) 2.568 (8) 130 (9)
C11—H11A⋯O1i 0.93 2.57 3.496 (8) 178
C12—H12A⋯Cl1i 0.93 2.83 3.640 (8) 147
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Schiff bases have been extensively studied for their structures and applications. In the present paper, we present the title compound (I) (Fig. 1) - a new Schiff base compound.

The asymmetric unit of (I) contains a half of the molecule situated on a mirror plane. The molecule of the compound adopts an E configuration with respect to the C=N bond. The hydroxy group is involved in formation of intramolecular O—H···N hydrogen bond (Table 1). Bond distances are within normal values (Allen et al., 1987), and are comparable with those reported in the literature for related compounds (Weiser et al., 2006; Barba et al., 2009; Francis et al., 2003).

ππ Interactions between the benzene rings of the neighbouring molecules [centroid-centroid distance = 3.629 (3) Å] form stacks along axis b. Weak intermolecular C—H···O and C—H···Cl interactions (Table 1) consolidate further the crystal packing.

Related literature top

For standard bond distances, see: Allen et al. (1987). For the crystal structures of related compounds, see: Francis et al. (2003); Weiser et al. (2006); Barba et al. (2009).

Experimental top

3,5-Diiodosalicylaldehyde (0.37 g, 1 mmol) and 2-chlorophenylamine (0.13 g, 1 mmol) were mixed in ethanol (20 ml). The mixture was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals were obtained by slow evaporation of the solution containing the compound in air.

Refinement top

C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å and Uiso = 1.2 Ueq(C). Atom H1 was located on a difference map and isotropically refined.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level. Intramolecular hydrogen bond is indicated by a dashed line.
2-[(2-Chlorophenyl)iminomethyl]-4,6-diiodophenol top
Crystal data top
C13H8ClI2NODx = 2.196 Mg m3
Mr = 483.45Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 897 reflections
a = 15.8432 (17) Åθ = 2.4–24.5°
b = 6.9942 (8) ŵ = 4.47 mm1
c = 13.1975 (14) ÅT = 296 K
V = 1462.4 (3) Å3Block, yellow
Z = 40.20 × 0.10 × 0.10 mm
F(000) = 896
Data collection top
Bruker SMART CCD area-detector
diffractometer
1829 independent reflections
Radiation source: fine-focus sealed tube1659 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2020
Tmin = 0.468, Tmax = 0.663k = 99
9861 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144 w = 1/[σ2(Fo2) + (0.1P)2 + 4.5P]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
1829 reflectionsΔρmax = 1.13 e Å3
113 parametersΔρmin = 0.76 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0030 (6)
Crystal data top
C13H8ClI2NOV = 1462.4 (3) Å3
Mr = 483.45Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 15.8432 (17) ŵ = 4.47 mm1
b = 6.9942 (8) ÅT = 296 K
c = 13.1975 (14) Å0.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1829 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1659 reflections with I > 2σ(I)
Tmin = 0.468, Tmax = 0.663Rint = 0.029
9861 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 1.13 e Å3
1829 reflectionsΔρmin = 0.76 e Å3
113 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.19354 (3)0.25000.09648 (5)0.0692 (3)
I20.44288 (3)0.25000.43751 (4)0.0582 (3)
C30.3198 (4)0.25000.1448 (5)0.0444 (16)
C20.3847 (4)0.25000.0744 (6)0.0470 (17)
C50.4191 (4)0.25000.2817 (5)0.0403 (14)
O10.3668 (3)0.25000.0237 (4)0.076 (2)
C40.3362 (4)0.25000.2491 (5)0.0395 (13)
H4A0.29210.25000.29560.047*
C60.4851 (4)0.25000.2125 (5)0.0404 (14)
H6A0.54060.25000.23520.048*
Cl10.46567 (14)0.25000.26597 (17)0.0654 (6)
C100.6308 (6)0.25000.3086 (7)0.056 (2)
H10A0.61460.25000.37640.068*
N10.5265 (4)0.25000.0572 (4)0.0456 (14)
C120.7400 (5)0.25000.1822 (9)0.073 (3)
H12A0.79680.25000.16470.088*
C130.6773 (5)0.25000.1049 (8)0.065 (2)
H13A0.69320.25000.03700.078*
C80.5925 (4)0.25000.1305 (6)0.0437 (15)
C10.4679 (4)0.25000.1090 (5)0.0353 (13)
C90.5697 (4)0.25000.2316 (6)0.0442 (15)
C110.7168 (7)0.25000.2820 (9)0.078 (3)
H11A0.75790.25000.33230.094*
C70.5388 (4)0.25000.0385 (6)0.0432 (15)
H7A0.59370.25000.06350.052*
H1A0.404 (5)0.25000.069 (6)0.06 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0239 (3)0.1386 (7)0.0450 (4)0.0000.00480 (18)0.000
I20.0463 (3)0.0979 (5)0.0303 (3)0.0000.00509 (18)0.000
C30.025 (3)0.078 (5)0.030 (3)0.0000.005 (2)0.000
C20.024 (3)0.079 (5)0.037 (4)0.0000.006 (3)0.000
C50.028 (3)0.065 (4)0.027 (3)0.0000.004 (2)0.000
O10.027 (3)0.171 (7)0.029 (3)0.0000.002 (2)0.000
C40.032 (3)0.055 (4)0.031 (3)0.0000.001 (2)0.000
C60.025 (3)0.054 (4)0.043 (4)0.0000.006 (2)0.000
Cl10.0433 (10)0.1094 (18)0.0435 (11)0.0000.0023 (8)0.000
C100.057 (5)0.067 (5)0.046 (4)0.0000.024 (4)0.000
N10.032 (3)0.070 (4)0.035 (3)0.0000.008 (2)0.000
C120.018 (3)0.122 (8)0.081 (7)0.0000.010 (4)0.000
C130.028 (3)0.107 (7)0.060 (6)0.0000.004 (3)0.000
C80.033 (3)0.058 (4)0.041 (4)0.0000.011 (3)0.000
C10.023 (3)0.049 (3)0.034 (3)0.0000.002 (2)0.000
C90.033 (3)0.060 (4)0.039 (4)0.0000.008 (3)0.000
C110.070 (6)0.091 (7)0.075 (7)0.0000.050 (6)0.000
C70.023 (3)0.061 (4)0.046 (4)0.0000.003 (3)0.000
Geometric parameters (Å, º) top
I1—C32.100 (6)C10—C111.407 (15)
I2—C52.090 (6)C10—H10A0.9300
C3—C21.386 (10)N1—C71.278 (10)
C3—C41.400 (9)N1—C81.425 (8)
C2—O11.325 (9)C12—C111.368 (16)
C2—C11.395 (9)C12—C131.424 (13)
C5—C41.383 (9)C12—H12A0.9300
C5—C61.388 (9)C13—C81.385 (11)
O1—H1A0.84 (2)C13—H13A0.9300
C4—H4A0.9300C8—C91.382 (11)
C6—C11.393 (9)C1—C71.459 (9)
C6—H6A0.9300C11—H11A0.9300
Cl1—C91.709 (7)C7—H7A0.9300
C10—C91.404 (9)
C2—C3—C4121.4 (6)C11—C12—H12A119.9
C2—C3—I1120.2 (5)C13—C12—H12A119.9
C4—C3—I1118.4 (5)C8—C13—C12120.1 (9)
O1—C2—C3119.8 (6)C8—C13—H13A120.0
O1—C2—C1121.5 (6)C12—C13—H13A120.0
C3—C2—C1118.8 (6)C9—C8—C13119.3 (7)
C4—C5—C6120.7 (6)C9—C8—N1117.6 (6)
C4—C5—I2118.5 (5)C13—C8—N1123.0 (7)
C6—C5—I2120.8 (5)C6—C1—C2120.4 (6)
C2—O1—H1A123 (7)C6—C1—C7118.4 (6)
C5—C4—C3118.9 (6)C2—C1—C7121.3 (6)
C5—C4—H4A120.6C8—C9—C10121.2 (7)
C3—C4—H4A120.6C8—C9—Cl1120.6 (5)
C5—C6—C1119.9 (6)C10—C9—Cl1118.2 (7)
C5—C6—H6A120.0C12—C11—C10120.0 (8)
C1—C6—H6A120.0C12—C11—H11A120.0
C9—C10—C11119.1 (8)C10—C11—H11A120.0
C9—C10—H10A120.4N1—C7—C1120.8 (6)
C11—C10—H10A120.4N1—C7—H7A119.6
C7—N1—C8124.0 (6)C1—C7—H7A119.6
C11—C12—C13120.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.84 (2)1.95 (8)2.568 (8)130 (9)
C11—H11A···O1i0.932.573.496 (8)178
C12—H12A···Cl1i0.932.833.640 (8)147
Symmetry code: (i) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC13H8ClI2NO
Mr483.45
Crystal system, space groupOrthorhombic, Pnma
Temperature (K)296
a, b, c (Å)15.8432 (17), 6.9942 (8), 13.1975 (14)
V3)1462.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)4.47
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.468, 0.663
No. of measured, independent and
observed [I > 2σ(I)] reflections
9861, 1829, 1659
Rint0.029
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.144, 0.98
No. of reflections1829
No. of parameters113
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.13, 0.76

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.84 (2)1.95 (8)2.568 (8)130 (9)
C11—H11A···O1i0.932.573.496 (8)178
C12—H12A···Cl1i0.932.833.640 (8)147
Symmetry code: (i) x+1/2, y+1/2, z1/2.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBarba, V., Hernandez, R., Hopfl, H., Santillan, R. & Farfan, N. (2009). J. Organomet. Chem. 694, 2127–2133.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFrancis, S., Mu­thiah, P. T., Venkatachalam, G. & Ramesh, R. (2003). Acta Cryst. E59, o1045–o1047.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWeiser, M.-S., Wesolek, M. & Mulhaupt, R. (2006). J. Organomet. Chem. 691, 2945–2952.  Web of Science CSD CrossRef CAS Google Scholar

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