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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Feb 24;68(Pt 3):o789. doi: 10.1107/S1600536812005727

2,4-Diiodo-6-[(propyl­imino)­meth­yl]phenol

Peng-Gang Liu a, Xiao-Ning Wang a, Yong-An Yang a, Hai-Liang Zhu a,*
PMCID: PMC3297858  PMID: 22412661

Abstract

The title compound, C10H11I2NO, was prepared by the reaction of 3,5-diiodo­salicyl­aldehyde with propyl­amine in ethanol. The mol­ecule adopts an E conformation with respect to the C=N bond and the aromatic ring. The aromatic ring and the imino unit are close to being coplanar, with a dihedral angle of 2.6 (3)° between their planes. This planarity is assisted by the formation of an intra­molecular O—H⋯O hydrogen bond.

Related literature  

For the biological activity of Schiff base compounds, see: Chohan et al. (2012 ▶); Yan et al. (2011 ▶); Zhang et al. (2011 ▶). For their use as ligands in coordination chemistry, see: You et al. (2008 ▶); Xu et al. (2009 ▶); Chen et al. (2010 ▶); Cui et al. (2011 ▶). For standard bond distances, see: Allen et al. (1987 ▶).graphic file with name e-68-0o789-scheme1.jpg

Experimental  

Crystal data  

  • C10H11I2NO

  • M r = 415.00

  • Orthorhombic, Inline graphic

  • a = 10.7019 (14) Å

  • b = 7.1483 (9) Å

  • c = 32.404 (4) Å

  • V = 2478.9 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 5.05 mm−1

  • T = 298 K

  • 0.21 × 0.20 × 0.20 mm

Data collection  

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.417, T max = 0.432

  • 18976 measured reflections

  • 2704 independent reflections

  • 2224 reflections with I > 2σ(I)

  • R int = 0.030

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.035

  • wR(F 2) = 0.104

  • S = 1.23

  • 2704 reflections

  • 131 parameters

  • 1 restraint

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

  • Δρmax = 0.96 e Å−3

  • Δρmin = −0.89 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005727/sj5194sup1.cif

e-68-0o789-sup1.cif (14.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005727/sj5194Isup2.hkl

e-68-0o789-Isup2.hkl (132.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812005727/sj5194Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.90 (1) 1.82 (5) 2.567 (6) 138 (7)
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supplementary crystallographic information

Comment

Schiff bases have been extensively studied because of their biological activity (Chohan et al., 2012; Yan et al., 2011; Zhang et al., 2011). In addition, Schiff bases have been shown to be versatile ligands for the preparation of coordination complexes (You et al., 2008; Xu et al., 2009; Chen et al., 2010; Cui et al., 2011). In the present paper, the structure of the new title Schiff base compound is reported.

The molecule of the compound exists in a trans of E configuration with respect to the methylidene unit. The torsion angles C1—C7—N1—C8, C7—N1—C8—C9, and N1—C8—C9—C10 are 0.9 (2), 60.5 (2), and 4.6 (2)°, respectively. Bond distances are within normal values (Allen et al., 1987). An intramolecular O1—H1···N1 hydrogen bond stabilises the molecular structure.

Experimental

3,5-Diiodosalicylaldehyde (0.37 g, 1 mmol) and propylamine (0.06 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 this solution in air.

Refinement

H1 was located from a difference Fourier map and refined isotropically, with the O—H distance restrained to 0.90 (1) Å. The remaining H-atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å, and with Uiso(H) set to 1.2Ueq(C) and 1.5Ueq(C10).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. An intramolecular hydrogen bond is indicated by a dashed line.

Crystal data

C10H11I2NO F(000) = 1536
Mr = 415.00 Dx = 2.224 Mg m−3
Orthorhombic, Pbca Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab Cell parameters from 1027 reflections
a = 10.7019 (14) Å θ = 2.3–24.5°
b = 7.1483 (9) Å µ = 5.05 mm−1
c = 32.404 (4) Å T = 298 K
V = 2478.9 (5) Å3 Block, yellow
Z = 8 0.21 × 0.20 × 0.20 mm
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Data collection

Bruker SMART CCD area-detector diffractometer 2704 independent reflections
Radiation source: fine-focus sealed tube 2224 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.030
ω scans θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −13→13
Tmin = 0.417, Tmax = 0.432 k = −9→8
18976 measured reflections l = −41→41
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Refinement

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)] = 0.035 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104 H atoms treated by a mixture of independent and constrained refinement
S = 1.23 w = 1/[σ2(Fo2) + (0.038P)2 + 7.4143P] where P = (Fo2 + 2Fc2)/3
2704 reflections (Δ/σ)max < 0.001
131 parameters Δρmax = 0.96 e Å−3
1 restraint Δρmin = −0.89 e Å−3
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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 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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
I1 0.14060 (4) 0.18844 (7) 0.522554 (12) 0.05384 (15)
I2 −0.14147 (3) 0.44774 (7) 0.371421 (13) 0.05752 (16)
N1 0.3755 (4) 0.4405 (7) 0.34042 (16) 0.0449 (11)
O1 0.1359 (4) 0.4554 (7) 0.33939 (13) 0.0520 (10)
C1 0.2521 (5) 0.3571 (7) 0.39908 (16) 0.0378 (11)
C2 0.1382 (5) 0.3981 (8) 0.37824 (17) 0.0393 (11)
C3 0.0266 (5) 0.3772 (7) 0.40084 (16) 0.0396 (11)
C4 0.0250 (5) 0.3193 (8) 0.44167 (17) 0.0444 (12)
H4 −0.0501 0.3087 0.4559 0.053*
C5 0.1389 (5) 0.2770 (7) 0.46109 (17) 0.0397 (11)
C6 0.2501 (5) 0.2976 (7) 0.44023 (16) 0.0415 (11)
H6 0.3250 0.2716 0.4537 0.050*
C7 0.3699 (5) 0.3819 (8) 0.37775 (18) 0.0431 (12)
H7 0.4438 0.3544 0.3916 0.052*
C8 0.4981 (6) 0.4653 (9) 0.32071 (19) 0.0520 (14)
H8A 0.5636 0.4343 0.3402 0.062*
H8B 0.5085 0.5952 0.3127 0.062*
C9 0.5099 (6) 0.3412 (10) 0.28282 (19) 0.0572 (16)
H9A 0.4486 0.3791 0.2624 0.069*
H9B 0.4926 0.2126 0.2904 0.069*
C10 0.6403 (7) 0.3541 (14) 0.2642 (2) 0.077 (2)
H10A 0.6567 0.4809 0.2561 0.115*
H10B 0.6453 0.2740 0.2405 0.115*
H10C 0.7009 0.3154 0.2843 0.115*
H1 0.211 (3) 0.471 (11) 0.327 (2) 0.080*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
I1 0.0536 (2) 0.0651 (3) 0.0428 (2) −0.0002 (2) −0.00119 (15) 0.00945 (18)
I2 0.0393 (2) 0.0751 (3) 0.0582 (3) 0.00399 (19) −0.01085 (16) 0.0073 (2)
N1 0.039 (2) 0.045 (3) 0.050 (3) −0.002 (2) 0.0032 (19) −0.001 (2)
O1 0.048 (2) 0.060 (3) 0.048 (2) 0.004 (2) −0.0015 (17) 0.008 (2)
C1 0.037 (2) 0.032 (3) 0.045 (3) 0.003 (2) −0.002 (2) −0.005 (2)
C2 0.044 (3) 0.035 (3) 0.040 (3) 0.001 (2) −0.004 (2) −0.006 (2)
C3 0.039 (3) 0.035 (3) 0.045 (3) 0.004 (2) −0.008 (2) −0.002 (2)
C4 0.040 (3) 0.042 (3) 0.052 (3) 0.002 (2) 0.002 (2) −0.002 (2)
C5 0.045 (3) 0.033 (3) 0.042 (3) 0.002 (2) −0.003 (2) 0.001 (2)
C6 0.040 (3) 0.036 (3) 0.048 (3) 0.004 (2) −0.005 (2) −0.003 (2)
C7 0.041 (3) 0.043 (3) 0.045 (3) 0.002 (2) −0.002 (2) −0.009 (2)
C8 0.041 (3) 0.059 (4) 0.057 (3) −0.006 (3) 0.005 (2) 0.000 (3)
C9 0.057 (4) 0.067 (4) 0.048 (3) −0.006 (3) 0.005 (3) −0.001 (3)
C10 0.070 (5) 0.099 (6) 0.061 (4) −0.003 (4) 0.017 (3) 0.005 (4)
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Geometric parameters (Å, º)

I1—C5 2.090 (5) C5—C6 1.377 (7)
I2—C3 2.097 (5) C6—H6 0.9300
N1—C7 1.282 (8) C7—H7 0.9300
N1—C8 1.471 (7) C8—C9 1.520 (9)
O1—C2 1.324 (7) C8—H8A 0.9700
O1—H1 0.900 (10) C8—H8B 0.9700
C1—C6 1.400 (7) C9—C10 1.523 (9)
C1—C2 1.424 (7) C9—H9A 0.9700
C1—C7 1.449 (7) C9—H9B 0.9700
C2—C3 1.409 (7) C10—H10A 0.9600
C3—C4 1.386 (8) C10—H10B 0.9600
C4—C5 1.405 (7) C10—H10C 0.9600
C4—H4 0.9300
C7—N1—C8 119.4 (5) N1—C7—H7 119.0
C2—O1—H1 116 (5) C1—C7—H7 119.0
C6—C1—C2 120.1 (5) N1—C8—C9 110.7 (5)
C6—C1—C7 120.3 (5) N1—C8—H8A 109.5
C2—C1—C7 119.6 (5) C9—C8—H8A 109.5
O1—C2—C3 120.7 (5) N1—C8—H8B 109.5
O1—C2—C1 122.1 (5) C9—C8—H8B 109.5
C3—C2—C1 117.2 (5) H8A—C8—H8B 108.1
C4—C3—C2 122.6 (5) C8—C9—C10 111.1 (6)
C4—C3—I2 119.7 (4) C8—C9—H9A 109.4
C2—C3—I2 117.7 (4) C10—C9—H9A 109.4
C3—C4—C5 118.7 (5) C8—C9—H9B 109.4
C3—C4—H4 120.6 C10—C9—H9B 109.4
C5—C4—H4 120.6 H9A—C9—H9B 108.0
C6—C5—C4 120.5 (5) C9—C10—H10A 109.5
C6—C5—I1 119.5 (4) C9—C10—H10B 109.5
C4—C5—I1 120.0 (4) H10A—C10—H10B 109.5
C5—C6—C1 120.9 (5) C9—C10—H10C 109.5
C5—C6—H6 119.6 H10A—C10—H10C 109.5
C1—C6—H6 119.6 H10B—C10—H10C 109.5
N1—C7—C1 122.1 (5)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
O1—H1···N1 0.90 (1) 1.82 (5) 2.567 (6) 138 (7)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5194).

References

  1. 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.
  2. Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Chen, W., Li, Y.-G., Cui, Y.-M., Zhang, X.-A., Zhu, H.-L. & Zeng, Q.-F. (2010). Eur. J. Med. Chem. 45, 4473–4478. [DOI] [PubMed]
  4. Chohan, Z. H., Shad, H. A. & Supuran, C. T. (2012). J. Enzyme Inhib. Med. Chem. 27, 58–68. [DOI] [PubMed]
  5. Cui, Y.-M., Li, Y.-G., Cai, Y.-J., Chen, W. & Zhu, H.-L. (2011). J. Coord. Chem. 64, 610–616.
  6. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  7. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  8. Xu, S.-P., Lv, P.-C., Fang, R.-Q. & Zhu, H.-L. (2009). J. Coord. Chem. 62, 2048–2057.
  9. Yan, L., Liu, F. W. & Liu, H. M. (2011). Chin. J. Org. Chem. 31, 1639–1642.
  10. You, Z.-L., Shi, D.-H., Xu, C., Zhang, Q. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 862–871. [DOI] [PubMed]
  11. Zhang, H.-J., Qin, X., Liu, K., Zhu, D.-D., Wang, X.-M. & Zhu, H.-L. (2011). Bioorg. Med. Chem. 19, 5708–5715. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005727/sj5194sup1.cif

e-68-0o789-sup1.cif (14.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005727/sj5194Isup2.hkl

e-68-0o789-Isup2.hkl (132.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812005727/sj5194Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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