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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2703.
Published online 2010 October 2. doi:  10.1107/S1600536810038407
PMCID: PMC3009371

2-{[(E)-2-Hy­droxy­benzyl­idene]amino}-1H-isoindole-1,3(2H)-dione

Abstract

In the title compound, C15H10N2O3, the isoindoline ring system is almost planar [maximum deviation = 0.020 (2) Å] and makes a dihedral angle of 1.57 (7)° with the benzene ring. Intra­molecular O—H(...)N and C—H(...)O hydrogen bonds are observed.

Related literature

Based on the multiple binding sites of acetyl­cholinesterase (AChE), a series of AChE inhibitors involving phthalimide derivatives have been designed and synthesized, see: Zhao et al. (2009 [triangle]). Phthalimide derivatives have also been developed as LXRa-selective antagonists, see: Motoshima et al. (2009 [triangle]). For the biological activity of Schiff bases, see: Singh et al. (2006 [triangle]); Sithambaram et al. (2006 [triangle]); Walsh et al. (1996 [triangle]). For a related structure, see: Jing et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2703-scheme1.jpg

Experimental

Crystal data

  • C15H10N2O3
  • M r = 266.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2703-efi1.jpg
  • a = 7.0877 (2) Å
  • b = 8.2400 (4) Å
  • c = 21.2752 (7) Å
  • β = 92.659 (3)°
  • V = 1241.19 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.22 × 0.15 × 0.12 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.982, T max = 0.988
  • 11806 measured reflections
  • 2184 independent reflections
  • 1541 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.098
  • S = 1.10
  • 2184 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.10 e Å−3
  • Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038407/wn2411sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038407/wn2411Isup2.hkl

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

Acknowledgments

The authors thank Professor T. N. Guru Row and Mr Venkatesha R. Hathwar, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help with the data collection and the UGC-MRP(S) – 541/09 – 10/KAMY002/UGC/SWRO dated 8.1.2010 for financial assistance.

supplementary crystallographic information

Comment

Based on the multiple binding sites of acetylcholinesterase (AChE), a series of AChE inhibitors involving phthalimide derivatives were designed and synthesized (Zhao et al., 2009). Phthalimide derivatives have also been developed as LXRa-selective antagonists (Motoshima et al., 2009). Azomethine group-containing compounds, typically known as Schiff bases, form a significant class of compounds in medicinal and pharmaceutical chemistry, with several biological applications that include antibacterial (Sithambaram Karthikeyan et al., 2006), antifungal (Singh et al., 2006) and antitumor activity (Walsh et al., 1996).

The asymmetric unit of 2-{[(1E)-(2-hydroxyphenyl)methylene]amino} -1H-isoindole-1,3(2H)-dione contains one molecule (Fig. 1). The isoindoline ring system is almost planar [maximum deviation = 0.020 (2) Å] and makes a dihedral angle of 1.57 (7)° with the benzene ring. The bond distances and bond angles are in good agreement with those in a closely related crystal structure (Jing et al., 2007).

In the crystal structure, molecules intramolecula O5—H5···N2 and C9—H9···O4 hydrogen bonds are observed (Table 1). The packing of the molecules shows stacking when viewed along the b axis (Fig. 2).

Experimental

Salicylaldehyde (1.221 g, 10 mmol) was dissolved in 20 ml ethanol and added, with continuous stirring, to a hot ethanolic solution (30 ml) containing N-aminophthalimide (1.621 g, 10 mmol). The mixture was further stirred, refluxed for 5 h and allowed to stand overnight. The final yellow product was dissolved in ethanol and a single crystal of the title compound was obtained after slow evaporation of the solvent at room temperature (Yield: 89%; M.p. 465 K).

Refinement

All H atoms were positioned at calculated positions with O—H = 0.82 Å, Csp2—H = 0.93 Å and refined using a riding model; Uiso(H) = kUeq(attached atom), where k = 1.2 for Csp2 and 1.5 for O.

Figures

Fig. 1.
The title molecule with the displacement ellipsoids drawn at the 50% probability level. The H atoms are shown as spheres of arbitrary radius. Dashed lines indicate intramolecular hydrogen bonds.
Fig. 2.
A view of the crystal structure down the b axis. Dashed lines indicate intramolecular hydrogen bonds.

Crystal data

C15H10N2O3F(000) = 552
Mr = 266.25Dx = 1.425 Mg m3
Monoclinic, P21/cMelting point: 465 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.0877 (2) ÅCell parameters from 2184 reflections
b = 8.2400 (4) Åθ = 2.7–25.0°
c = 21.2752 (7) ŵ = 0.10 mm1
β = 92.659 (3)°T = 293 K
V = 1241.19 (8) Å3Plate, yellow
Z = 40.22 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer2184 independent reflections
Radiation source: fine-focus sealed tube1541 reflections with I > 2σ(I)
graphiteRint = 0.023
ω and [var phi] scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −8→8
Tmin = 0.982, Tmax = 0.988k = −9→9
11806 measured reflectionsl = −25→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.098w = 1/[σ2(Fo2) + (0.0449P)2 + 0.0801P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
2184 reflectionsΔρmax = 0.10 e Å3
182 parametersΔρmin = −0.11 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0088 (16)

Special details

Experimental. IR ν(Nujolmull, cm-1): 1768 and 1725 (C=O), 1617 (HC=N), 3386 (Ph—OH). 1H NMR (DMSO-d6, p.p.m.): 10.67 (s, 1H, Ph—OH), 9.45 (s, 1H, HC=N), 6.92–7.91 (m, 4H, Ar—H). FAB-MS: m/z = 267 [M+1]+, Anal. Calc. for C15H10N2O3; C, 67.67; H, 3.79; N, 10.52; O, 18.03; Found: C, 67.05; H, 3.81; N, 10.68; O, 17.98,; Electronic spectra: 289 nm and 334 nm.
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.

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

xyzUiso*/Ueq
O3−0.27271 (15)0.27296 (16)0.07498 (5)0.0836 (4)
O40.28488 (17)0.31121 (18)−0.02433 (5)0.0877 (4)
O50.00226 (15)0.52524 (17)0.19986 (5)0.0846 (4)
H5−0.01940.47520.16700.127*
N10.02621 (17)0.31346 (16)0.03847 (5)0.0579 (4)
N20.08319 (18)0.40089 (16)0.09127 (5)0.0591 (4)
C1−0.3130 (3)0.0248 (2)−0.11364 (9)0.0780 (5)
H1−0.4146−0.0282−0.13380.094*
C2−0.1434 (3)0.0318 (2)−0.14198 (8)0.0798 (5)
H2−0.1320−0.0162−0.18120.096*
C30.0112 (3)0.1090 (2)−0.11336 (8)0.0739 (5)
H30.12620.1138−0.13270.089*
C4−0.0109 (2)0.1786 (2)−0.05531 (7)0.0580 (4)
C5−0.1815 (2)0.1703 (2)−0.02662 (7)0.0578 (4)
C6−0.3351 (2)0.0955 (2)−0.05535 (8)0.0716 (5)
H6−0.45060.0923−0.03630.086*
C70.1244 (2)0.2722 (2)−0.01510 (7)0.0614 (4)
C8−0.1610 (2)0.2551 (2)0.03459 (7)0.0607 (4)
C90.2541 (2)0.4496 (2)0.09978 (7)0.0610 (4)
H90.34220.42660.07000.073*
C100.3099 (2)0.54030 (19)0.15573 (7)0.0557 (4)
C110.4953 (2)0.5961 (2)0.16350 (8)0.0700 (5)
H110.57980.57480.13240.084*
C120.5558 (3)0.6816 (2)0.21590 (9)0.0783 (5)
H120.68010.71760.22040.094*
C130.4304 (3)0.7134 (2)0.26175 (9)0.0781 (5)
H130.47050.77200.29730.094*
C140.2476 (3)0.6602 (2)0.25587 (8)0.0741 (5)
H140.16480.68230.28740.089*
C150.1854 (2)0.5737 (2)0.20321 (8)0.0610 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O30.0731 (8)0.1092 (11)0.0704 (7)−0.0031 (7)0.0216 (6)−0.0101 (7)
O40.0713 (8)0.1189 (12)0.0746 (8)−0.0043 (7)0.0206 (6)−0.0070 (7)
O50.0675 (8)0.1089 (11)0.0789 (8)−0.0129 (7)0.0191 (6)−0.0184 (7)
N10.0613 (8)0.0631 (9)0.0498 (7)0.0052 (6)0.0078 (6)0.0018 (7)
N20.0640 (9)0.0584 (9)0.0550 (8)0.0062 (7)0.0045 (6)0.0027 (6)
C10.0967 (14)0.0658 (13)0.0705 (11)0.0020 (10)−0.0077 (10)−0.0015 (10)
C20.1067 (15)0.0726 (14)0.0597 (10)0.0146 (11)0.0006 (10)−0.0049 (9)
C30.0871 (12)0.0750 (13)0.0606 (10)0.0132 (10)0.0139 (9)0.0029 (9)
C40.0706 (10)0.0528 (10)0.0510 (8)0.0114 (8)0.0071 (7)0.0108 (8)
C50.0692 (10)0.0525 (10)0.0520 (8)0.0090 (8)0.0047 (7)0.0111 (7)
C60.0745 (11)0.0693 (12)0.0711 (11)0.0009 (9)0.0043 (9)0.0073 (10)
C70.0654 (10)0.0640 (12)0.0558 (9)0.0106 (9)0.0127 (8)0.0093 (8)
C80.0641 (10)0.0632 (12)0.0556 (9)0.0072 (8)0.0105 (8)0.0083 (8)
C90.0626 (10)0.0622 (11)0.0589 (9)0.0106 (8)0.0100 (7)0.0092 (8)
C100.0587 (9)0.0502 (10)0.0581 (9)0.0058 (7)0.0031 (7)0.0097 (7)
C110.0626 (11)0.0696 (13)0.0781 (11)0.0025 (9)0.0079 (8)0.0107 (10)
C120.0713 (11)0.0699 (13)0.0928 (14)−0.0089 (9)−0.0062 (10)0.0072 (11)
C130.0924 (14)0.0607 (13)0.0797 (12)−0.0031 (10)−0.0130 (10)−0.0018 (10)
C140.0827 (12)0.0714 (13)0.0687 (11)0.0012 (10)0.0076 (9)−0.0059 (10)
C150.0612 (10)0.0568 (11)0.0653 (10)0.0005 (8)0.0048 (8)0.0043 (8)

Geometric parameters (Å, °)

O3—C81.2041 (17)C4—C71.473 (2)
O4—C71.2068 (17)C5—C61.370 (2)
O5—C151.3568 (18)C5—C81.479 (2)
O5—H50.8200C6—H60.9300
N1—N21.3791 (17)C9—C101.445 (2)
N1—C71.4044 (19)C9—H90.9300
N1—C81.4105 (19)C10—C111.395 (2)
N2—C91.2811 (18)C10—C151.399 (2)
C1—C21.371 (2)C11—C121.371 (2)
C1—C61.386 (2)C11—H110.9300
C1—H10.9300C12—C131.375 (2)
C2—C31.384 (2)C12—H120.9300
C2—H20.9300C13—C141.368 (2)
C3—C41.377 (2)C13—H130.9300
C3—H30.9300C14—C151.383 (2)
C4—C51.381 (2)C14—H140.9300
C15—O5—H5109.5N1—C7—C4105.31 (13)
N2—N1—C7130.54 (13)O3—C8—N1124.36 (15)
N2—N1—C8117.71 (11)O3—C8—C5130.20 (15)
C7—N1—C8111.74 (13)N1—C8—C5105.43 (12)
C9—N2—N1121.21 (13)N2—C9—C10119.96 (14)
C2—C1—C6120.94 (17)N2—C9—H9120.0
C2—C1—H1119.5C10—C9—H9120.0
C6—C1—H1119.5C11—C10—C15118.16 (15)
C1—C2—C3121.24 (17)C11—C10—C9119.24 (15)
C1—C2—H2119.4C15—C10—C9122.60 (14)
C3—C2—H2119.4C12—C11—C10121.56 (16)
C4—C3—C2117.71 (16)C12—C11—H11119.2
C4—C3—H3121.1C10—C11—H11119.2
C2—C3—H3121.1C11—C12—C13119.14 (17)
C3—C4—C5120.97 (16)C11—C12—H12120.4
C3—C4—C7129.82 (15)C13—C12—H12120.4
C5—C4—C7109.20 (13)C14—C13—C12120.96 (18)
C6—C5—C4121.26 (15)C14—C13—H13119.5
C6—C5—C8130.43 (14)C12—C13—H13119.5
C4—C5—C8108.30 (14)C13—C14—C15120.29 (17)
C5—C6—C1117.88 (16)C13—C14—H14119.9
C5—C6—H6121.1C15—C14—H14119.9
C1—C6—H6121.1O5—C15—C14117.54 (14)
O4—C7—N1125.03 (16)O5—C15—C10122.57 (15)
O4—C7—C4129.65 (15)C14—C15—C10119.88 (15)
C7—N1—N2—C9−5.3 (2)C7—N1—C8—O3178.98 (14)
C8—N1—N2—C9175.89 (14)N2—N1—C8—C5178.99 (12)
C6—C1—C2—C30.2 (3)C7—N1—C8—C5−0.04 (17)
C1—C2—C3—C40.1 (3)C6—C5—C8—O33.4 (3)
C2—C3—C4—C50.4 (2)C4—C5—C8—O3−177.93 (16)
C2—C3—C4—C7−177.72 (16)C6—C5—C8—N1−177.66 (16)
C3—C4—C5—C6−1.3 (2)C4—C5—C8—N11.02 (17)
C7—C4—C5—C6177.25 (15)N1—N2—C9—C10−179.69 (13)
C3—C4—C5—C8179.92 (15)N2—C9—C10—C11−178.34 (14)
C7—C4—C5—C8−1.58 (17)N2—C9—C10—C152.3 (2)
C4—C5—C6—C11.5 (2)C15—C10—C11—C12−0.1 (2)
C8—C5—C6—C1−179.97 (16)C9—C10—C11—C12−179.50 (15)
C2—C1—C6—C5−1.0 (3)C10—C11—C12—C13−0.2 (3)
N2—N1—C7—O4−1.0 (3)C11—C12—C13—C140.4 (3)
C8—N1—C7—O4177.88 (15)C12—C13—C14—C15−0.3 (3)
N2—N1—C7—C4−179.74 (14)C13—C14—C15—O5−179.50 (15)
C8—N1—C7—C4−0.87 (17)C13—C14—C15—C100.0 (3)
C3—C4—C7—O41.2 (3)C11—C10—C15—O5179.69 (14)
C5—C4—C7—O4−177.15 (17)C9—C10—C15—O5−0.9 (2)
C3—C4—C7—N1179.85 (16)C11—C10—C15—C140.2 (2)
C5—C4—C7—N11.52 (17)C9—C10—C15—C14179.56 (15)
N2—N1—C8—O3−2.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5···N20.821.902.6152 (16)145
C9—H9···O40.932.242.8937 (19)127

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2411).

References

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  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
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