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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o101.
Published online 2007 December 6. doi:  10.1107/S1600536807062861
PMCID: PMC2915176

3,5-Dihydr­oxy-N′-[(2-hydr­oxy-1-naph­thyl)methyl­ene]benzohydrazide

Abstract

In the title compound, C18H14N2O4, the dihedral angle between the benzene ring and the naphthyl ring system is 10.1 (2)°. The mol­ecule is nearly planar, with a mean deviation from the plane of 0.141 (2) Å for 24 non-H atoms. An intra­molecular O—H(...)N hydrogen bond forms a pseudo-6-membered ring and the mol­ecules are linked into sheets by inter­molecular N—H(...)O and O—H(...)O hydrogen bonds.

Related literature

For related structures, see: Brückner et al. (2000 [triangle]); Diao (2007 [triangle]); Diao et al. (2007 [triangle]); Harrop et al. (2003 [triangle]); Huang et al. (2007 [triangle]); Li et al. (2007 [triangle]); Ren et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o101-scheme1.jpg

Experimental

Crystal data

  • C18H14N2O4
  • M r = 322.31
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o101-efi1.jpg
  • a = 13.354 (3) Å
  • b = 14.133 (3) Å
  • c = 15.077 (3) Å
  • V = 2845.5 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 (2) K
  • 0.30 × 0.28 × 0.27 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.968, T max = 0.971
  • 15775 measured reflections
  • 2949 independent reflections
  • 2433 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.110
  • S = 1.03
  • 2949 reflections
  • 223 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062861/bi2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062861/bi2266Isup2.hkl

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

Acknowledgments

This project is supported by a research grant from Dalian Medical University.

supplementary crystallographic information

Comment

Schiff base compounds have received much attention in recent years. Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on Schiff base compounds (Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title compound.

Experimental

2-Hydroxy-1-naphthylaldehyde (1.0 mmol, 172.2 mg) and 3,5-dihydroxybenzoic acid hydrazide (1.0 mmol, 168.2 mg) were dissolved in a methanol solution (70 ml). The mixture was stirred at reflux for 1 h and cooled to room temperature. After keeping the solution in air for two days, yellow block-like crystals were formed.

Refinement

H1A was located from a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H distances of 0.93 Å, O—H distances of 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Figures

Fig. 1.
Molecular structure with displacement parameters drawn at the 30% probability level for non-H atoms.

Crystal data

C18H14N2O4F000 = 1344
Mr = 322.31Dx = 1.505 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5426 reflections
a = 13.354 (3) Åθ = 2.4–27.8º
b = 14.133 (3) ŵ = 0.11 mm1
c = 15.077 (3) ÅT = 298 (2) K
V = 2845.5 (10) Å3Block, yellow
Z = 80.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer2949 independent reflections
Radiation source: fine-focus sealed tube2433 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 298(2) Kθmax = 26.5º
ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −16→15
Tmin = 0.968, Tmax = 0.971k = −17→11
15775 measured reflectionsl = −18→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110  w = 1/[σ2(Fo2) + (0.0562P)2 + 0.7945P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2949 reflectionsΔρmax = 0.20 e Å3
223 parametersΔρmin = −0.19 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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.

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

xyzUiso*/Ueq
O10.70957 (9)−0.44067 (6)0.65672 (7)0.0446 (3)
H10.6882−0.47160.69870.067*
O20.64726 (9)−0.17869 (7)0.84818 (6)0.0425 (3)
H20.6418−0.22140.88470.064*
O30.61626 (10)−0.17124 (7)0.45805 (7)0.0468 (3)
O40.61263 (10)0.02287 (7)0.29946 (7)0.0486 (3)
H40.6170−0.00310.34800.073*
N10.64522 (10)−0.04149 (8)0.53870 (8)0.0359 (3)
N20.62939 (10)0.01212 (8)0.46461 (8)0.0363 (3)
C10.65842 (10)−0.19422 (9)0.60952 (9)0.0308 (3)
C20.67691 (11)−0.28981 (9)0.59712 (9)0.0336 (3)
H2A0.6811−0.31500.54020.040*
C30.68890 (11)−0.34676 (9)0.67002 (9)0.0320 (3)
C40.68089 (11)−0.31096 (9)0.75469 (9)0.0317 (3)
H4A0.6893−0.35040.80350.038*
C50.66031 (10)−0.21629 (9)0.76661 (9)0.0308 (3)
C60.65109 (10)−0.15717 (9)0.69414 (9)0.0317 (3)
H60.6400−0.09280.70220.038*
C70.63939 (11)−0.13645 (9)0.52904 (9)0.0330 (3)
C80.62525 (11)0.10148 (9)0.47179 (9)0.0329 (3)
H80.63240.12990.52710.040*
C90.60931 (10)0.15896 (9)0.39384 (9)0.0306 (3)
C100.60344 (11)0.11717 (10)0.31095 (9)0.0350 (3)
C110.58622 (12)0.17008 (11)0.23410 (10)0.0423 (4)
H110.58230.14010.17930.051*
C120.57537 (12)0.26432 (11)0.23968 (10)0.0428 (4)
H120.56210.29880.18850.051*
C130.58356 (11)0.31214 (10)0.32116 (10)0.0373 (3)
C140.57676 (13)0.41122 (11)0.32600 (12)0.0503 (4)
H140.56440.44570.27460.060*
C150.58771 (15)0.45740 (11)0.40359 (14)0.0577 (5)
H150.58480.52310.40530.069*
C160.60341 (14)0.40619 (11)0.48111 (13)0.0540 (5)
H160.61030.43800.53470.065*
C170.60877 (12)0.30993 (10)0.47952 (11)0.0433 (4)
H170.61820.27700.53230.052*
C180.60030 (10)0.25964 (9)0.39969 (10)0.0325 (3)
H1A0.6770 (14)−0.0170 (14)0.5862 (10)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0747 (8)0.0223 (5)0.0367 (6)0.0096 (5)0.0150 (5)0.0020 (4)
O20.0740 (8)0.0276 (5)0.0261 (5)0.0017 (5)0.0004 (5)−0.0018 (4)
O30.0836 (9)0.0298 (5)0.0271 (5)−0.0008 (5)−0.0043 (5)−0.0024 (4)
O40.0827 (9)0.0315 (6)0.0316 (6)0.0044 (5)−0.0025 (6)−0.0048 (4)
N10.0559 (8)0.0243 (6)0.0275 (6)0.0007 (5)−0.0070 (5)0.0027 (5)
N20.0542 (8)0.0258 (6)0.0290 (6)0.0012 (5)−0.0034 (5)0.0028 (5)
C10.0384 (7)0.0249 (6)0.0291 (7)0.0001 (5)0.0015 (5)0.0017 (5)
C20.0453 (8)0.0275 (7)0.0280 (7)0.0016 (6)0.0047 (6)−0.0022 (5)
C30.0388 (7)0.0219 (6)0.0352 (7)0.0032 (5)0.0054 (6)−0.0003 (5)
C40.0396 (7)0.0267 (6)0.0288 (7)0.0019 (5)0.0017 (6)0.0042 (5)
C50.0380 (7)0.0269 (6)0.0275 (7)−0.0019 (5)0.0007 (5)−0.0027 (5)
C60.0413 (8)0.0224 (6)0.0315 (7)0.0010 (5)0.0006 (6)−0.0010 (5)
C70.0445 (8)0.0257 (6)0.0288 (7)0.0014 (6)0.0020 (6)−0.0011 (5)
C80.0434 (8)0.0262 (6)0.0292 (7)0.0011 (5)−0.0024 (6)−0.0012 (5)
C90.0348 (7)0.0255 (6)0.0315 (7)0.0011 (5)−0.0005 (5)0.0021 (5)
C100.0408 (8)0.0318 (7)0.0324 (7)0.0021 (6)0.0004 (6)0.0007 (6)
C110.0500 (9)0.0474 (9)0.0296 (8)0.0016 (7)−0.0006 (6)0.0010 (6)
C120.0463 (8)0.0475 (9)0.0346 (8)0.0041 (7)0.0014 (7)0.0164 (7)
C130.0350 (7)0.0335 (7)0.0435 (8)0.0025 (6)0.0041 (6)0.0101 (6)
C140.0563 (10)0.0338 (8)0.0607 (11)0.0060 (7)0.0075 (8)0.0189 (7)
C150.0718 (12)0.0246 (7)0.0767 (13)0.0041 (7)0.0076 (10)0.0062 (8)
C160.0724 (12)0.0295 (8)0.0602 (11)0.0032 (7)−0.0002 (9)−0.0059 (7)
C170.0588 (10)0.0289 (7)0.0422 (9)0.0034 (6)−0.0019 (7)−0.0004 (6)
C180.0337 (7)0.0261 (7)0.0378 (8)0.0016 (5)0.0015 (6)0.0040 (6)

Geometric parameters (Å, °)

O1—C31.3704 (15)C6—H60.930
O1—H10.820C8—C91.4445 (18)
O2—C51.3511 (15)C8—H80.930
O2—H20.820C9—C101.3845 (19)
O3—C71.2177 (17)C9—C181.4307 (18)
O4—C101.3496 (17)C10—C111.398 (2)
O4—H40.820C11—C121.342 (2)
N1—C71.3521 (17)C11—H110.930
N1—N21.3661 (16)C12—C131.406 (2)
N1—H1A0.903 (9)C12—H120.930
N2—C81.2688 (17)C13—C141.405 (2)
C1—C61.3826 (19)C13—C181.4150 (19)
C1—C21.3859 (18)C14—C151.348 (3)
C1—C71.4845 (18)C14—H140.930
C2—C31.3716 (19)C15—C161.391 (3)
C2—H2A0.930C15—H150.930
C3—C41.3774 (19)C16—C171.363 (2)
C4—C51.3776 (17)C16—H160.930
C4—H4A0.930C17—C181.402 (2)
C5—C61.3810 (18)C17—H170.930
C3—O1—H1109.5C10—C9—C18118.36 (12)
C5—O2—H2109.5C10—C9—C8120.20 (12)
C10—O4—H4109.5C18—C9—C8121.44 (12)
C7—N1—N2116.97 (11)O4—C10—C9122.13 (12)
C7—N1—H1A119.6 (14)O4—C10—C11115.90 (13)
N2—N1—H1A120.6 (14)C9—C10—C11121.96 (13)
C8—N2—N1119.28 (12)C12—C11—C10119.77 (14)
C6—C1—C2120.41 (12)C12—C11—H11120.1
C6—C1—C7122.26 (12)C10—C11—H11120.1
C2—C1—C7117.16 (12)C11—C12—C13121.54 (13)
C3—C2—C1118.99 (12)C11—C12—H12119.2
C3—C2—H2A120.5C13—C12—H12119.2
C1—C2—H2A120.5C14—C13—C12121.28 (14)
O1—C3—C2118.34 (12)C14—C13—C18119.30 (15)
O1—C3—C4120.46 (12)C12—C13—C18119.42 (13)
C2—C3—C4121.20 (12)C15—C14—C13121.38 (15)
C3—C4—C5119.55 (12)C15—C14—H14119.3
C3—C4—H4A120.2C13—C14—H14119.3
C5—C4—H4A120.2C14—C15—C16119.60 (15)
O2—C5—C4121.77 (12)C14—C15—H15120.2
O2—C5—C6118.08 (12)C16—C15—H15120.2
C4—C5—C6120.15 (12)C17—C16—C15120.85 (17)
C5—C6—C1119.64 (12)C17—C16—H16119.6
C5—C6—H6120.2C15—C16—H16119.6
C1—C6—H6120.2C16—C17—C18121.13 (15)
O3—C7—N1120.67 (12)C16—C17—H17119.4
O3—C7—C1122.67 (12)C18—C17—H17119.4
N1—C7—C1116.62 (12)C17—C18—C13117.72 (13)
N2—C8—C9119.79 (13)C17—C18—C9123.38 (13)
N2—C8—H8120.1C13—C18—C9118.90 (13)
C9—C8—H8120.1

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.962.7671 (15)167
O2—H2···O3i0.821.912.7227 (15)172
O4—H4···N20.821.782.5046 (16)147
N1—H1A···O1ii0.903 (9)2.141 (12)2.9929 (16)157.0 (19)

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+3/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2266).

References

  • Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem.39, 6100–6106. [PubMed]
  • Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01). SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Diao, Y.-P. (2007). Acta Cryst. E63, m1453–m1454.
  • Diao, Y.-P., Shu, X.-H., Zhang, B.-J., Zhen, Y.-H. & Kang, T.-G. (2007). Acta Cryst. E63, m1816.
  • Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411. [PubMed]
  • Huang, S.-S., Zhou, Q. & Diao, Y.-P. (2007). Acta Cryst. E63, o4659.
  • Li, K., Huang, S.-S., Zhang, B.-J., Meng, D.-L. & Diao, Y.-P. (2007). Acta Cryst. E63, m2291.
  • Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem.45, 410–419. [PubMed]

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