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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o236–o237.
Published online 2009 December 24. doi:  10.1107/S1600536809053793
PMCID: PMC2980095

(E)-3-Hydr­oxy-N′-(2-hydroxy­benzyl­idene)-2-naphthohydrazide

Abstract

The title compound, C18H14N2O3, is an aroylhydrazone with an approximately planar structure [dihedral angle of 15.27 (13)° between the benzene ring and the naphthyl ring system], stabilized by intra­molecular N—H(...)O and O—H(...)N hydrogen bonds. Inter­molecular O—H(...)O hydrogen bonds with the keto group as acceptor lead to strands along [100]. In terms of graph-set analysis, the descriptor on the unitary level is C 1 1(6)S(6)S(6).

Related literature

For historical background to aroylhydrazones, see: Savanini et al. (2002 [triangle]); Craliz et al. (1955 [triangle]); Pickart et al. (1983 [triangle]); Offe et al. (1952 [triangle]); Arapov et al. (1987 [triangle]); Ranford et al. (1998 [triangle]). For related structures, see: Liu et al. (2004 [triangle]); Lei et al. (2008 [triangle]). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 [triangle]); Etter et al. (1990 [triangle]).

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Object name is e-66-0o236-scheme1.jpg

Experimental

Crystal data

  • C18H14N2O3
  • M r = 306.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o236-efi1.jpg
  • a = 12.6749 (4) Å
  • b = 4.9666 (1) Å
  • c = 22.7299 (6) Å
  • V = 1430.87 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 200 K
  • 0.50 × 0.10 × 0.09 mm

Data collection

  • Nonius KappaCCD diffractometer
  • 10328 measured reflections
  • 1676 independent reflections
  • 1416 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.095
  • S = 1.09
  • 1676 reflections
  • 220 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: COLLECT (Hooft, 2004 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO (Otwinowski & Minor, 1997 [triangle]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053793/bg2308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053793/bg2308Isup2.hkl

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

Acknowledgments

The authors are grateful to Zanjan University, the Faculty of Chemistry and Biochemistry of the LMU Munich, and the School of Chemistry for financial support.

supplementary crystallographic information

Comment

As part of our studies on the synthesis and characterization of aroylhydrazone derivatives, we report on the crystal structure of (E)-3-hydroxy-N'-(2-hydroxybenzylidene)-2-naphthohydrazide.

The asymmetric unit contains one molecule of the title compound, which is shown in Figure 1. The molecule is almost planar with a dihedral angle of 15.27 (13)° between the benzene ring and the naphthyl ring. This configuration is stabilized by two intramolecular hydrogen bonds of the types O–H···N and N–H···O. The keto group acts as an acceptor in a hydrogen bond of the type O–H···O leading to infinite chains along [100] (Fig. 2). In terms of graph-set analysis [Bernstein et al. (1995), Etter et al. (1990)], the descriptor on the unitary level is C11(6)S(6)S(6).

The arrangement of the molecules within the chains along [100] formed by hydrogen bonds becomes evident when viewing along the chain axis (Fig. 3). The chains are constituted by the glide planes perpendicular to the b-axis with the glide vectors along [100]. Since the title compound is not oriented parallel or perpendicular to the glide plane, the hydrogen-bond linked molecules do not form layers as one might think when seeing Fig. 2. The repeating unit of the chain consists of two molecules which are oriented approximately perpendicular to each other. The least-square planes (determined by all non-hydrogen atoms of a molecule) of adjacent molecules enclose an angle of 86.33 (1)°.

The same hydrogen bonds as described above are present in the structure of an ethoxy derivative of the title compound [Lei et al. (2008)], however, slightly undulated layers are formed. Stronger undulation of the layers is observed in the structure of a methyl derivative of the title compound [Liu et al. (2004)], in which the keto group is not involved as acceptor in the intramolecular hydrogen bond, but the hydroxyl group bound to the phenyl ring.

Experimental

All reagents were commercially available and used as received. A methanol (10 ml) solution of 2-hydroxybenzaldehyde (1.63 mmol) was drop-wise added to a methanol solution (10 ml) of 3-hydroxy-2-naphthohydrazide (1.63 mmol), and the mixture was refluxed for 3 h. Then the solution was evaporated on a steam bath to 5 cm3 and cooled to room temperature. Yellow precipitates of the title compound were separated and filtered off, washed with 5 ml of cooled methanol and then dried in air. X-ray quality crystals of the title compound were obtained from methanol by slow solvent evaporation. Yield: 75%, mp 317 °C.

Refinement

O– and N-bound H atoms were refined freely. C-bonded H atoms were positioned geometrically (C—H = 0.95 Å) and treated as riding on their parent atoms [Uiso(H) = 1.2Ueq(C)].

1550 Friedel pairs have been merged. The Flack parameter is meaningless.

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
Fig. 2.
Hydrogen bonding in the title compound viewed along [0 - 1 0]. The green and red dashed arrows indicate intramolecular N–H···O and O–H···N hydrogen bonds, respectively. The blue dashed arrows ...
Fig. 3.
Projection of the hydrogen-bond linked chains viewed along [100]. For clarity only the two chains with their axis located within the unit cell are shown. Dashed lines indicate the a glide planes perpendicular to the b-axis.

Crystal data

C18H14N2O3F(000) = 640
Mr = 306.32Dx = 1.422 (1) Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 5508 reflections
a = 12.6749 (4) Åθ = 3.1–27.5°
b = 4.9666 (1) ŵ = 0.10 mm1
c = 22.7299 (6) ÅT = 200 K
V = 1430.87 (7) Å3Rod, yellow
Z = 40.50 × 0.10 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer1416 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.054
MONTEL, graded multilayered X-ray opticsθmax = 27.4°, θmin = 3.3°
Detector resolution: 9 pixels mm-1h = −16→16
CCD; rotation images; thick slices, phi/ω–scank = −6→6
10328 measured reflectionsl = −29→29
1676 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.09w = 1/[σ2(Fo2) + (0.052P)2 + 0.1709P] where P = (Fo2 + 2Fc2)/3
1676 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = −0.17 e Å3

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 > 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
O10.23226 (13)0.2694 (4)0.22862 (9)0.0383 (4)
O20.31563 (16)−0.3045 (5)0.09755 (11)0.0533 (6)
H20.280 (4)−0.182 (9)0.124 (2)0.092 (14)*
O3−0.08649 (14)0.4024 (3)0.18929 (8)0.0325 (4)
H3−0.151 (3)0.377 (6)0.1953 (15)0.044 (8)*
N10.09013 (15)0.1311 (4)0.17680 (9)0.0283 (4)
H10.019 (2)0.157 (5)0.1723 (13)0.037 (7)*
N20.14658 (15)−0.0532 (4)0.14425 (8)0.0290 (4)
C10.13752 (17)0.2878 (5)0.21681 (10)0.0258 (5)
C20.06987 (17)0.4915 (5)0.24682 (10)0.0250 (5)
C3−0.03790 (17)0.5489 (5)0.23284 (10)0.0255 (5)
C4−0.09057 (18)0.7497 (5)0.26178 (11)0.0283 (5)
H4−0.16120.78970.25090.034*
C5−0.04258 (17)0.8986 (5)0.30734 (10)0.0272 (5)
C6−0.0956 (2)1.1070 (5)0.33832 (11)0.0332 (6)
H6−0.16601.15240.32800.040*
C7−0.0461 (2)1.2432 (5)0.38286 (11)0.0353 (6)
H7−0.08281.38070.40350.042*
C80.0589 (2)1.1808 (6)0.39843 (12)0.0380 (6)
H80.09251.27610.42940.046*
C90.1119 (2)0.9845 (5)0.36906 (11)0.0344 (6)
H90.18270.94430.37970.041*
C100.06327 (18)0.8391 (5)0.32300 (10)0.0279 (5)
C110.11661 (18)0.6368 (5)0.29118 (11)0.0282 (5)
H110.18800.59940.30080.034*
C120.0899 (2)−0.1961 (5)0.10947 (11)0.0301 (5)
H120.0156−0.16970.10930.036*
C130.1346 (2)−0.3955 (5)0.07051 (10)0.0310 (5)
C140.2435 (2)−0.4434 (6)0.06574 (12)0.0372 (6)
C150.2796 (2)−0.6364 (7)0.02599 (16)0.0501 (7)
H150.3532−0.66560.02160.060*
C160.2097 (3)−0.7845 (6)−0.00686 (14)0.0488 (8)
H160.2356−0.9187−0.03290.059*
C170.1027 (3)−0.7416 (5)−0.00265 (13)0.0450 (7)
H170.0548−0.8429−0.02590.054*
C180.0665 (2)−0.5492 (5)0.03591 (11)0.0388 (6)
H18−0.0073−0.52010.03910.047*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0226 (8)0.0433 (10)0.0489 (10)0.0037 (7)−0.0027 (8)−0.0084 (9)
O20.0286 (10)0.0615 (14)0.0697 (15)0.0054 (9)−0.0018 (10)−0.0210 (12)
O30.0207 (8)0.0394 (10)0.0373 (10)−0.0008 (7)−0.0018 (7)−0.0050 (8)
N10.0209 (9)0.0316 (10)0.0324 (10)0.0024 (8)0.0015 (8)−0.0025 (8)
N20.0265 (9)0.0297 (10)0.0309 (10)0.0024 (8)0.0038 (8)0.0004 (8)
C10.0216 (10)0.0267 (11)0.0290 (12)0.0000 (9)0.0025 (9)0.0035 (10)
C20.0218 (11)0.0243 (12)0.0288 (11)−0.0016 (9)0.0026 (9)0.0038 (9)
C30.0228 (11)0.0268 (11)0.0270 (11)−0.0034 (9)−0.0004 (9)0.0021 (10)
C40.0213 (10)0.0295 (12)0.0340 (12)0.0016 (9)0.0003 (9)0.0056 (10)
C50.0266 (11)0.0260 (12)0.0292 (11)−0.0020 (9)0.0012 (9)0.0044 (9)
C60.0321 (12)0.0314 (13)0.0362 (14)0.0010 (10)0.0045 (10)0.0029 (11)
C70.0439 (14)0.0290 (13)0.0330 (13)0.0009 (11)0.0056 (11)−0.0026 (11)
C80.0447 (15)0.0367 (14)0.0326 (13)−0.0053 (12)−0.0032 (12)−0.0016 (11)
C90.0341 (12)0.0335 (13)0.0357 (13)−0.0029 (10)−0.0065 (11)0.0020 (11)
C100.0289 (12)0.0263 (12)0.0285 (12)−0.0030 (10)−0.0008 (10)0.0036 (10)
C110.0238 (11)0.0293 (12)0.0315 (12)−0.0007 (9)−0.0016 (9)0.0023 (10)
C120.0270 (11)0.0311 (13)0.0320 (11)0.0009 (10)0.0028 (10)0.0020 (11)
C130.0338 (12)0.0287 (13)0.0305 (13)0.0016 (9)0.0028 (10)0.0023 (10)
C140.0335 (12)0.0361 (15)0.0419 (14)0.0007 (10)0.0018 (11)−0.0029 (12)
C150.0440 (16)0.0484 (17)0.0577 (17)0.0120 (13)0.0099 (15)−0.0050 (15)
C160.072 (2)0.0361 (15)0.0389 (15)0.0052 (14)0.0104 (14)−0.0061 (13)
C170.062 (2)0.0370 (15)0.0365 (15)−0.0039 (14)−0.0021 (13)−0.0023 (13)
C180.0411 (14)0.0380 (15)0.0372 (13)−0.0031 (11)−0.0018 (12)−0.0019 (12)

Geometric parameters (Å, °)

O1—C11.234 (3)C7—H70.9500
O2—C141.354 (3)C8—C91.360 (4)
O2—H20.96 (5)C8—H80.9500
O3—C31.374 (3)C9—C101.413 (3)
O3—H30.84 (4)C9—H90.9500
N1—C11.339 (3)C10—C111.411 (3)
N1—N21.378 (3)C11—H110.9500
N1—H10.92 (3)C12—C131.444 (3)
N2—C121.283 (3)C12—H120.9500
C1—C21.491 (3)C13—C181.395 (3)
C2—C111.374 (3)C13—C141.405 (3)
C2—C31.431 (3)C14—C151.394 (4)
C3—C41.368 (3)C15—C161.372 (5)
C4—C51.410 (3)C15—H150.9500
C4—H40.9500C16—C171.377 (5)
C5—C101.419 (3)C16—H160.9500
C5—C61.421 (3)C17—C181.375 (4)
C6—C71.369 (4)C17—H170.9500
C6—H60.9500C18—H180.9500
C7—C81.411 (4)
C14—O2—H2110 (3)C8—C9—C10121.0 (2)
C3—O3—H3114 (2)C8—C9—H9119.5
C1—N1—N2121.20 (19)C10—C9—H9119.5
C1—N1—H1115.9 (18)C11—C10—C9122.3 (2)
N2—N1—H1122.9 (18)C11—C10—C5118.2 (2)
C12—N2—N1114.05 (19)C9—C10—C5119.5 (2)
O1—C1—N1122.8 (2)C2—C11—C10122.9 (2)
O1—C1—C2120.7 (2)C2—C11—H11118.5
N1—C1—C2116.55 (19)C10—C11—H11118.5
C11—C2—C3118.0 (2)N2—C12—C13122.5 (2)
C11—C2—C1116.35 (19)N2—C12—H12118.8
C3—C2—C1125.6 (2)C13—C12—H12118.8
C4—C3—O3120.88 (19)C18—C13—C14118.1 (2)
C4—C3—C2120.3 (2)C18—C13—C12118.6 (2)
O3—C3—C2118.84 (19)C14—C13—C12123.3 (2)
C3—C4—C5121.6 (2)O2—C14—C15118.4 (2)
C3—C4—H4119.2O2—C14—C13122.4 (2)
C5—C4—H4119.2C15—C14—C13119.2 (3)
C4—C5—C10118.9 (2)C16—C15—C14120.7 (3)
C4—C5—C6122.8 (2)C16—C15—H15119.7
C10—C5—C6118.3 (2)C14—C15—H15119.7
C7—C6—C5120.7 (2)C15—C16—C17121.0 (3)
C7—C6—H6119.7C15—C16—H16119.5
C5—C6—H6119.7C17—C16—H16119.5
C6—C7—C8120.6 (2)C18—C17—C16118.7 (3)
C6—C7—H7119.7C18—C17—H17120.6
C8—C7—H7119.7C16—C17—H17120.6
C9—C8—C7120.0 (2)C17—C18—C13122.2 (3)
C9—C8—H8120.0C17—C18—H18118.9
C7—C8—H8120.0C13—C18—H18118.9
C1—N1—N2—C12177.3 (2)C4—C5—C10—C111.4 (3)
N2—N1—C1—O1−3.1 (3)C6—C5—C10—C11−178.4 (2)
N2—N1—C1—C2176.38 (18)C4—C5—C10—C9−179.2 (2)
O1—C1—C2—C11−5.6 (3)C6—C5—C10—C91.0 (3)
N1—C1—C2—C11174.9 (2)C3—C2—C11—C10−0.3 (3)
O1—C1—C2—C3173.6 (2)C1—C2—C11—C10179.0 (2)
N1—C1—C2—C3−5.9 (3)C9—C10—C11—C2179.1 (2)
C11—C2—C3—C42.3 (3)C5—C10—C11—C2−1.5 (3)
C1—C2—C3—C4−177.0 (2)N1—N2—C12—C13178.3 (2)
C11—C2—C3—O3−178.9 (2)N2—C12—C13—C18177.4 (2)
C1—C2—C3—O31.8 (3)N2—C12—C13—C14−2.4 (4)
O3—C3—C4—C5178.8 (2)C18—C13—C14—O2−179.9 (3)
C2—C3—C4—C5−2.4 (4)C12—C13—C14—O2−0.1 (4)
C3—C4—C5—C100.5 (3)C18—C13—C14—C151.5 (4)
C3—C4—C5—C6−179.7 (2)C12—C13—C14—C15−178.7 (3)
C4—C5—C6—C7179.0 (2)O2—C14—C15—C16179.3 (3)
C10—C5—C6—C7−1.2 (3)C13—C14—C15—C16−2.1 (5)
C5—C6—C7—C80.7 (4)C14—C15—C16—C171.8 (5)
C6—C7—C8—C90.1 (4)C15—C16—C17—C18−0.9 (4)
C7—C8—C9—C10−0.3 (4)C16—C17—C18—C130.4 (4)
C8—C9—C10—C11179.1 (2)C14—C13—C18—C17−0.7 (4)
C8—C9—C10—C5−0.2 (4)C12—C13—C18—C17179.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···N20.96 (5)1.87 (5)2.697 (3)142 (4)
O3—H3···O1i0.84 (4)1.81 (4)2.609 (2)157 (3)
N1—H1···O30.92 (3)1.85 (3)2.628 (3)141 (2)

Symmetry codes: (i) x−1/2, −y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2308).

References

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