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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o309.
Published online 2010 January 9. doi:  10.1107/S1600536810000346
PMCID: PMC2979867

1-[(Z)-(5-Methyl-2-pyrid­yl)iminiometh­yl]-2-naphtholate

Abstract

In the zwitterionic title compound, C17H14N2O, the dihedral angle between the naphthalene and pyridine ring systems is 3.56 (9)° and an intra­molecular N—H(...)O hydrogen bond generates an S(6) ring. In the crystal, mol­ecules are linked by C—H(...)O inter­actions.

Related literature

For a related structure, see: Eltayeb et al. (2007 [triangle]).

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Object name is e-66-0o309-scheme1.jpg

Experimental

Crystal data

  • C17H14N2O
  • M r = 262.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o309-efi1.jpg
  • a = 4.8703 (2) Å
  • b = 9.5525 (5) Å
  • c = 14.0804 (6) Å
  • β = 98.353 (2)°
  • V = 648.12 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.47 × 0.10 × 0.09 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.961, T max = 0.992
  • 6930 measured reflections
  • 1660 independent reflections
  • 1321 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.109
  • S = 0.98
  • 1660 reflections
  • 182 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000346/hb5298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000346/hb5298Isup2.hkl

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

Acknowledgments

The authors acknowledge the National Science Foundation of China for its financial support for this project (grant No. 20971115).

supplementary crystallographic information

Comment

One similar compound as 1-{2-[(2-hydroxy-1-naphthyl)methyleneamino] phenyliminiomethyl}-2-naphtholate methanol hemisolvate has been synthesized and characterized by X-ray diffraction (Eltayeb et al., 2007). We now report on the title compound, (I), whose structure was determined by X-ray diffraction (Fig. 1).

This compound, which has a non-planar molecular structure, contains two aromatic rings linked through a imine group. The dihedral angle between the two aromatic rings C2—C3—C4—C5—N1—C6 and C8—C9—C14—C15—C16—C17 is 3.46(0.16)°. Intramolecular N—H···O hydrogen bonds are observed in the molecular structure, similar to those reported structure (Eltayeb et al., 2007). The molecules is formed a one-dimensional zigzag chain through intermolecular C—H···O hydrogen bonds, which make the molecule more stabile.

As seen in Fig. 2, the molecules are linked into a one-dimensional chain by intermolecular C—H···O hydrogen bonds (Table 2).

Experimental

2-Hydroxy-1-naphthaldehyde (1 mmol, 172.2 mg) were added with stirring to anhydrous ethanol (30 ml) to make a solution. It was slowly dropped into the anhydrous ethanol solution (15 ml) containing (1 mmol, 108.1 mg) 5-methylpyridin-2-amine at 339 K and mixture was stirred at 339 K for 4 h, a mass of deep yellow grain was separated out. The product was collected by filtration and washed several times with anhydrous ethanol and dried under vacuum. Yellow needles of (I) were obtained by slow evaporation at room temperature from anhydrous ethanol solution after 4 days.

Refinement

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. All H-atoms were positioned geometrically (C—H = 0.93–0.96Å, N—H = 0.86Å) and refined as riding with Uiso(H) =1.2Ueq(carrier).

Figures

Fig. 1.
The structure of (I) showing 30% probability displacement ellipsoids.
Fig. 2.
The crystal packing of (I), viewed approximately along the a axis.

Crystal data

C17H14N2OF(000) = 276
Mr = 262.30Dx = 1.344 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1877 reflections
a = 4.8703 (2) Åθ = 2.6–25.6°
b = 9.5525 (5) ŵ = 0.09 mm1
c = 14.0804 (6) ÅT = 296 K
β = 98.353 (2)°Needle, yellow
V = 648.12 (5) Å30.47 × 0.10 × 0.09 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer1660 independent reflections
Radiation source: fine-focus sealed tube1321 reflections with I > 2σ(I)
graphiteRint = 0.029
[var phi] and ω scansθmax = 28.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −6→6
Tmin = 0.961, Tmax = 0.992k = −12→11
6930 measured reflectionsl = −18→15

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 0.98w = 1/[σ2(Fo2) + (0.062P)2 + 0.0757P] where P = (Fo2 + 2Fc2)/3
1660 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = −0.15 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 > 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
C1−0.5458 (5)−0.0508 (3)0.8827 (2)0.0561 (6)
H1A−0.6558−0.07350.82240.084*
H1B−0.6646−0.01780.92660.084*
H1C−0.4484−0.13280.90860.084*
C2−0.3401 (5)0.0616 (2)0.86752 (16)0.0431 (5)
C3−0.2411 (5)0.1558 (3)0.93834 (17)0.0518 (6)
H3−0.30110.15080.99800.062*
C4−0.0533 (5)0.2576 (3)0.92116 (16)0.0492 (6)
H40.01270.32230.96830.059*
C50.0341 (4)0.2610 (2)0.83229 (15)0.0382 (5)
C6−0.2414 (5)0.0762 (3)0.78108 (16)0.0478 (6)
H6−0.30820.01430.73220.057*
C70.3255 (4)0.3752 (2)0.73144 (15)0.0398 (5)
H70.25840.31510.68150.048*
C80.5254 (4)0.4749 (2)0.71574 (15)0.0383 (5)
C90.6227 (4)0.4846 (2)0.62325 (15)0.0371 (5)
C100.5226 (5)0.3996 (3)0.54463 (16)0.0468 (6)
H100.39050.33150.55180.056*
C110.6141 (5)0.4140 (3)0.45734 (16)0.0501 (6)
H110.54230.35660.40640.060*
C120.8133 (5)0.5138 (3)0.44477 (17)0.0525 (6)
H120.87430.52380.38550.063*
C130.9182 (5)0.5968 (3)0.51987 (18)0.0510 (6)
H131.05390.66230.51160.061*
C140.8257 (4)0.5857 (2)0.60997 (16)0.0413 (5)
C150.9323 (5)0.6740 (3)0.68904 (18)0.0499 (6)
H151.06770.73950.68040.060*
C160.8457 (5)0.6663 (3)0.77458 (18)0.0484 (6)
H160.92240.72590.82360.058*
C170.6352 (5)0.5673 (2)0.79247 (16)0.0430 (5)
N1−0.0571 (4)0.1724 (2)0.76194 (13)0.0462 (5)
N20.2284 (4)0.3625 (2)0.81358 (13)0.0424 (4)
H20.28770.42030.85880.051*
O10.5562 (4)0.5643 (2)0.87507 (11)0.0567 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0517 (14)0.0467 (15)0.0725 (16)−0.0048 (12)0.0176 (12)0.0080 (13)
C20.0391 (10)0.0397 (12)0.0520 (12)0.0037 (10)0.0115 (9)0.0067 (11)
C30.0604 (14)0.0536 (15)0.0459 (12)−0.0031 (13)0.0230 (11)0.0044 (12)
C40.0581 (14)0.0484 (14)0.0438 (12)−0.0078 (12)0.0163 (10)−0.0060 (11)
C50.0403 (10)0.0341 (11)0.0416 (11)0.0036 (9)0.0108 (8)0.0026 (9)
C60.0525 (13)0.0435 (13)0.0478 (12)−0.0049 (11)0.0081 (10)−0.0027 (11)
C70.0436 (11)0.0356 (11)0.0418 (11)0.0025 (9)0.0116 (8)0.0036 (9)
C80.0411 (10)0.0322 (11)0.0429 (11)0.0033 (9)0.0106 (8)0.0024 (9)
C90.0370 (10)0.0337 (11)0.0421 (10)0.0038 (9)0.0103 (8)0.0058 (9)
C100.0496 (13)0.0447 (14)0.0481 (12)−0.0016 (11)0.0136 (10)0.0000 (11)
C110.0555 (14)0.0529 (15)0.0437 (12)0.0054 (12)0.0135 (10)−0.0005 (11)
C120.0590 (14)0.0553 (15)0.0475 (13)0.0092 (12)0.0225 (10)0.0091 (11)
C130.0504 (13)0.0447 (14)0.0615 (15)0.0012 (11)0.0203 (11)0.0108 (12)
C140.0404 (11)0.0356 (12)0.0493 (12)0.0033 (10)0.0113 (9)0.0055 (10)
C150.0486 (12)0.0385 (13)0.0645 (14)−0.0057 (11)0.0145 (10)0.0025 (12)
C160.0508 (13)0.0365 (12)0.0582 (14)−0.0035 (11)0.0086 (10)−0.0055 (11)
C170.0492 (12)0.0356 (12)0.0460 (12)0.0033 (10)0.0125 (9)0.0016 (10)
N10.0536 (11)0.0441 (11)0.0430 (10)−0.0029 (10)0.0146 (8)−0.0014 (9)
N20.0497 (11)0.0370 (10)0.0425 (9)−0.0017 (9)0.0134 (8)−0.0010 (8)
O10.0721 (11)0.0548 (11)0.0463 (9)−0.0073 (10)0.0187 (8)−0.0083 (8)

Geometric parameters (Å, °)

C1—C21.504 (3)C8—C91.452 (3)
C1—H1A0.9600C9—C101.402 (3)
C1—H1B0.9600C9—C141.413 (3)
C1—H1C0.9600C10—C111.374 (3)
C2—C31.377 (4)C10—H100.9300
C2—C61.379 (3)C11—C121.390 (4)
C3—C41.380 (4)C11—H110.9300
C3—H30.9300C12—C131.360 (4)
C4—C51.379 (3)C12—H120.9300
C4—H40.9300C13—C141.410 (3)
C5—N11.329 (3)C13—H130.9300
C5—N21.407 (3)C14—C151.433 (3)
C6—N11.339 (3)C15—C161.335 (3)
C6—H60.9300C15—H150.9300
C7—N21.317 (3)C16—C171.444 (3)
C7—C81.402 (3)C16—H160.9300
C7—H70.9300C17—O11.277 (3)
C8—C171.436 (3)N2—H20.8600
C2—C1—H1A109.5C14—C9—C8119.20 (19)
C2—C1—H1B109.5C11—C10—C9121.8 (2)
H1A—C1—H1B109.5C11—C10—H10119.1
C2—C1—H1C109.5C9—C10—H10119.1
H1A—C1—H1C109.5C10—C11—C12120.4 (2)
H1B—C1—H1C109.5C10—C11—H11119.8
C3—C2—C6116.3 (2)C12—C11—H11119.8
C3—C2—C1122.3 (2)C13—C12—C11119.4 (2)
C6—C2—C1121.5 (2)C13—C12—H12120.3
C2—C3—C4120.3 (2)C11—C12—H12120.3
C2—C3—H3119.8C12—C13—C14121.5 (2)
C4—C3—H3119.8C12—C13—H13119.3
C5—C4—C3118.4 (2)C14—C13—H13119.3
C5—C4—H4120.8C13—C14—C9119.4 (2)
C3—C4—H4120.8C13—C14—C15121.8 (2)
N1—C5—C4123.2 (2)C9—C14—C15118.72 (19)
N1—C5—N2117.42 (18)C16—C15—C14122.9 (2)
C4—C5—N2119.4 (2)C16—C15—H15118.6
N1—C6—C2125.2 (2)C14—C15—H15118.6
N1—C6—H6117.4C15—C16—C17121.3 (2)
C2—C6—H6117.4C15—C16—H16119.4
N2—C7—C8123.2 (2)C17—C16—H16119.4
N2—C7—H7118.4O1—C17—C8122.9 (2)
C8—C7—H7118.4O1—C17—C16119.3 (2)
C7—C8—C17119.32 (18)C8—C17—C16117.86 (19)
C7—C8—C9120.61 (19)C5—N1—C6116.61 (19)
C17—C8—C9120.07 (19)C7—N2—C5124.41 (19)
C10—C9—C14117.45 (19)C7—N2—H2117.8
C10—C9—C8123.34 (19)C5—N2—H2117.8
C6—C2—C3—C4−0.1 (4)C10—C9—C14—C130.0 (3)
C1—C2—C3—C4−179.7 (2)C8—C9—C14—C13−179.1 (2)
C2—C3—C4—C5−0.8 (4)C10—C9—C14—C15−179.9 (2)
C3—C4—C5—N11.1 (4)C8—C9—C14—C151.0 (3)
C3—C4—C5—N2−179.1 (2)C13—C14—C15—C16179.2 (2)
C3—C2—C6—N10.9 (4)C9—C14—C15—C16−0.9 (4)
C1—C2—C6—N1−179.5 (2)C14—C15—C16—C17−0.3 (4)
N2—C7—C8—C171.0 (3)C7—C8—C17—O1−1.0 (3)
N2—C7—C8—C9−179.45 (19)C9—C8—C17—O1179.5 (2)
C7—C8—C9—C101.4 (3)C7—C8—C17—C16178.5 (2)
C17—C8—C9—C10−179.1 (2)C9—C8—C17—C16−1.1 (3)
C7—C8—C9—C14−179.55 (19)C15—C16—C17—O1−179.3 (2)
C17—C8—C9—C140.0 (3)C15—C16—C17—C81.2 (3)
C14—C9—C10—C11−0.8 (3)C4—C5—N1—C6−0.3 (3)
C8—C9—C10—C11178.3 (2)N2—C5—N1—C6179.8 (2)
C9—C10—C11—C120.6 (4)C2—C6—N1—C5−0.7 (3)
C10—C11—C12—C130.4 (4)C8—C7—N2—C5−178.1 (2)
C11—C12—C13—C14−1.2 (4)N1—C5—N2—C7−0.1 (3)
C12—C13—C14—C91.0 (3)C4—C5—N2—C7−180.0 (2)
C12—C13—C14—C15−179.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O10.861.892.571 (3)135
C3—H3···O1i0.932.463.346 (3)159

Symmetry codes: (i) −x, y−1/2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5298).

References

  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Eltayeb, N. E., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, o117–o119.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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