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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o568.
Published online 2008 February 8. doi:  10.1107/S160053680800370X
PMCID: PMC2960832

1-(Hydroxy­imino­meth­yl)-2-naphthol

Abstract

The title compound, C11H9NO2, was prepared by a condens­ation reaction of 2-hydr­oxy-1-naphthaldehyde with hydroxyl­ammonium chloride in refluxing ethanol. An intra­molecular O—H(...)N hydrogen bond is observed. In the crystal structure, inter­molecular O—H(...)O and C—H(...)O hydrogen-bond inter­actions result in a two-dimensional network.

Related literature

For general background, see: Desai et al. (2001 [triangle]); Hodnett et al. (1970 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o568-scheme1.jpg

Experimental

Crystal data

  • C11H9NO2
  • M r = 187.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o568-efi1.jpg
  • a = 14.8382 (19) Å
  • b = 4.0462 (7) Å
  • c = 16.527 (2) Å
  • β = 114.933 (2)°
  • V = 899.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.56 × 0.45 × 0.18 mm

Data collection

  • Bruker SMART 1K CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.953, T max = 0.984
  • 3977 measured reflections
  • 1573 independent reflections
  • 1009 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.148
  • S = 1.04
  • 1573 reflections
  • 127 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800370X/fj2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800370X/fj2080Isup2.hkl

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

Acknowledgments

The authors thank the Natural Science Foundation of Shandong Province (No. Y2004B02) for a research grant.

supplementary crystallographic information

Comment

Schiff bases have been intensively investigated owing to their strong coordination capability and diverse biological activities, such as antibacterial, antitumor activities(Desai et al., 2001; Hodnett et al., 1970). We report here the synthesis and crystal structure of a new Schiff base compound derived from the condensation of 2-hydroxy-1-naphthaldehyde and hydroxylammonium chioride.

In the molecular structure(Scheme 1 and Fig.1), all the atoms are almost in one plane, with the C?N = 1.266 (3) Å. In the molecule, an intramolecular O2—H2···N1 hydrogen bond is observed(Table 1). The interactions of intermolecular hydrogen bond O1—H1···O2 form a one-dimensional chain-like structure(Fig. 2), which together with another two intermolecular H atoms C1—H1a···O1 and C8—H8···O1 (Table 1) result in the two-dimensional net-shaped structure.

Experimental

2-hydroxy-1-naphthaldehyde (1 mmol, 172.18 mg) in absolute ethanol (5 ml) was added dropwise to a absolute ethanol solution (10 ml) of hydroxylammonium chioride (1 mmol, 69.49 mg). The mixture was heated under reflux with stirring for 2 h and then filtered. The resulting solution was held at room temperature for 14 days, whereupon the colourless needle crystals of the title complex suitable for X-ray diffraction analysis were obtained.

Refinement

All H-atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å (aromatic), 0.82 Å (hydroxyl) and Uiso(H) =1.2Ueq(C).

Figures

Fig. 1.
The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title complex, viewed approximately along the a axis.

Crystal data

C11H9NO2F000 = 392
Mr = 187.19Dx = 1.382 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1237 reflections
a = 14.8382 (19) Åθ = 2.5–27.0º
b = 4.0462 (7) ŵ = 0.10 mm1
c = 16.527 (2) ÅT = 298 (2) K
β = 114.933 (2)ºBlock, yellow
V = 899.8 (2) Å30.56 × 0.45 × 0.18 mm
Z = 4

Data collection

Bruker SMART 1K CCD diffractometer1573 independent reflections
Radiation source: fine-focus sealed tube1009 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.053
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −17→15
Tmin = 0.953, Tmax = 0.984k = −4→4
3977 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.149  w = 1/[σ2(Fo2) + (0.0623P)2 + 0.1603P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1573 reflectionsΔρmax = 0.19 e Å3
127 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
N10.02725 (13)0.4774 (6)0.36227 (12)0.0492 (6)
O1−0.05788 (11)0.5784 (5)0.37113 (10)0.0675 (6)
H1−0.09440.67960.32620.101*
O20.14880 (11)0.4181 (5)0.28864 (9)0.0576 (6)
H20.09780.47580.29250.086*
C10.08718 (16)0.3186 (6)0.42939 (14)0.0450 (6)
H1A0.07090.28050.47710.054*
C20.18092 (14)0.1946 (6)0.43332 (13)0.0398 (6)
C30.20781 (15)0.2491 (6)0.36359 (14)0.0447 (6)
C40.29816 (17)0.1329 (7)0.36695 (16)0.0543 (7)
H40.31490.17460.31970.065*
C50.36087 (17)−0.0385 (7)0.43808 (18)0.0574 (7)
H50.4197−0.11890.43830.069*
C60.33969 (16)−0.1004 (6)0.51308 (16)0.0498 (7)
C70.24800 (15)0.0168 (6)0.50985 (14)0.0426 (6)
C80.22784 (17)−0.0505 (7)0.58514 (15)0.0525 (7)
H80.16800.01890.58490.063*
C90.29445 (19)−0.2143 (7)0.65726 (17)0.0627 (7)
H90.2795−0.25340.70570.075*
C100.38420 (19)−0.3245 (7)0.66013 (19)0.0707 (8)
H100.4294−0.43330.71040.085*
C110.40583 (18)−0.2721 (7)0.58864 (19)0.0634 (8)
H110.4653−0.35140.59000.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0425 (10)0.0617 (16)0.0470 (11)0.0002 (10)0.0225 (9)−0.0005 (10)
O10.0471 (9)0.1046 (17)0.0565 (10)0.0234 (10)0.0274 (8)0.0178 (11)
O20.0556 (10)0.0760 (14)0.0459 (9)−0.0074 (9)0.0260 (8)−0.0040 (9)
C10.0442 (13)0.0525 (17)0.0411 (11)−0.0030 (12)0.0207 (10)−0.0005 (12)
C20.0390 (12)0.0386 (15)0.0440 (11)−0.0084 (11)0.0196 (10)−0.0125 (11)
C30.0429 (12)0.0469 (16)0.0451 (12)−0.0123 (12)0.0195 (10)−0.0131 (12)
C40.0516 (14)0.060 (2)0.0611 (15)−0.0153 (13)0.0333 (13)−0.0238 (15)
C50.0419 (13)0.0546 (19)0.0820 (17)−0.0088 (13)0.0322 (13)−0.0240 (16)
C60.0382 (12)0.0392 (16)0.0676 (15)−0.0088 (11)0.0180 (12)−0.0152 (13)
C70.0398 (12)0.0355 (15)0.0515 (13)−0.0087 (10)0.0184 (10)−0.0121 (12)
C80.0519 (14)0.0489 (18)0.0569 (14)0.0029 (12)0.0232 (12)0.0007 (13)
C90.0660 (17)0.054 (2)0.0632 (15)0.0036 (15)0.0220 (14)0.0115 (15)
C100.0581 (17)0.054 (2)0.0781 (18)0.0009 (14)0.0070 (15)0.0103 (16)
C110.0430 (14)0.0439 (18)0.0911 (19)0.0002 (13)0.0165 (14)−0.0073 (16)

Geometric parameters (Å, °)

N1—C11.266 (3)C5—C61.423 (3)
N1—O11.393 (2)C5—H50.9300
O1—H10.8200C6—C111.404 (3)
O2—C31.362 (3)C6—C71.420 (3)
O2—H20.8200C7—C81.423 (3)
C1—C21.454 (3)C8—C91.358 (3)
C1—H1A0.9300C8—H80.9300
C2—C31.387 (3)C9—C101.386 (3)
C2—C71.431 (3)C9—H90.9300
C3—C41.399 (3)C10—C111.365 (4)
C4—C51.344 (3)C10—H100.9300
C4—H40.9300C11—H110.9300
C1—N1—O1112.96 (16)C11—C6—C7119.9 (2)
N1—O1—H1109.5C11—C6—C5122.2 (2)
C3—O2—H2109.5C7—C6—C5117.9 (2)
N1—C1—C2121.31 (19)C6—C7—C8117.0 (2)
N1—C1—H1A119.3C6—C7—C2119.96 (19)
C2—C1—H1A119.3C8—C7—C2123.0 (2)
C3—C2—C7118.56 (19)C9—C8—C7121.2 (2)
C3—C2—C1120.9 (2)C9—C8—H8119.4
C7—C2—C1120.59 (18)C7—C8—H8119.4
O2—C3—C2122.40 (19)C8—C9—C10121.4 (2)
O2—C3—C4116.27 (19)C8—C9—H9119.3
C2—C3—C4121.3 (2)C10—C9—H9119.3
C5—C4—C3120.4 (2)C11—C10—C9119.6 (3)
C5—C4—H4119.8C11—C10—H10120.2
C3—C4—H4119.8C9—C10—H10120.2
C4—C5—C6121.8 (2)C10—C11—C6121.0 (2)
C4—C5—H5119.1C10—C11—H11119.5
C6—C5—H5119.1C6—C11—H11119.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.862.577 (2)146
O1—H1···O2i0.821.972.771 (2)164
C1—H1A···O1ii0.932.663.527 (3)156
C8—H8···O1ii0.932.623.474 (3)153

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2080).

References

  • Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Hetercycle Commun.7, 83–90.
  • Hodnett, E. M. & Mooney, P. D. (1970). J. Med. Chem.13, 786–788. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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