PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1400.
Published online 2009 May 23. doi:  10.1107/S1600536809019096
PMCID: PMC2969739

1-[(2-Anilinoeth­yl)iminiometh­yl]-2-naph­thol­ate

Abstract

The title Schiff base compound, C19H18N2O, was prepared by the reaction of equimolar quanti­ties of 2-hydr­oxy-1-naphthaldehyde with N-phenyl­ethane-1,2-diamine in a methanol solution. The mol­ecule adopts a zwitterionic conformation with the naphthyl OH group deprotonated and the imine N atom protonated. An intra­molecular N—H(...)O hydrogen bond forms between them. The dihedral angle between the benzene ring and the naphthyl system is 86.9 (2)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds, forming chains running along the b axis.

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000 [triangle]); Sriram et al. (2006 [triangle]); Karthikeyan et al. (2006 [triangle]). For Schiff base coordination chemistry, see: Ali et al. (2008 [triangle]); Kargar et al. (2009 [triangle]); Yeap et al. (2009 [triangle]). For related structures, see: Fun et al. (2009 [triangle]); Nadeem et al. (2009 [triangle]); Eltayeb et al. (2008 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1400-scheme1.jpg

Experimental

Crystal data

  • C19H18N2O
  • M r = 290.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1400-efi1.jpg
  • a = 27.511 (3) Å
  • b = 6.845 (2) Å
  • c = 8.543 (2) Å
  • β = 104.263 (2)°
  • V = 1559.2 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.23 × 0.21 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.982, T max = 0.986
  • 4485 measured reflections
  • 1753 independent reflections
  • 1312 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.105
  • S = 1.06
  • 1753 reflections
  • 202 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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 global, I. DOI: 10.1107/S1600536809019096/sj2625sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019096/sj2625Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff base compounds are an important class of materials used in the pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). They are also used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of several Schiff base compounds have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). In this paper, the new Schiff base title compound, (I), Fig. 1, is reported.

In (I), the H atom of the phenol group is transferred to the imine N atom, forming an intramolecular N–H···O hydrogen bond (Table 1). The dihedral angle between the benzene ring and the naphthyl ring is 86.9 (2)°. All the bond lengths are within normal values (Allen et al., 1987). In the crystal structure of the compound, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

Experimental

2-Hydroxy-1-naphthylaldehyde (0.1 mmol, 17.2 mg) and N-phenylethane-1,2-diamine (0.1 mmol, 13.6 mg) were refluxed in a 30 ml methanol solution for 30 min to give a clear orange solution. Yellow block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.

Refinement

In the absence of significant anomalous dispersion effects, 1421 Freidel pairs were merged. H1 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1)Å, and with Uiso restrained to 0.08Å2. Other H atoms were constrained to ideal geometries, with d(C–H) = 0.93–0.97Å, d(N–H) = 0.86Å, and with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of (I) with 30% probability ellipsoids. The intramolecular N–H···O hydrogen bond is shown as a dashed line.
Fig. 2.
Molecular packing of (I) with hydrogen bonds drawn as dashed lines.

Crystal data

C19H18N2OF(000) = 616
Mr = 290.35Dx = 1.237 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1258 reflections
a = 27.511 (3) Åθ = 2.5–24.5°
b = 6.845 (2) ŵ = 0.08 mm1
c = 8.543 (2) ÅT = 298 K
β = 104.263 (2)°Block, yellow
V = 1559.2 (6) Å30.23 × 0.21 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1753 independent reflections
Radiation source: fine-focus sealed tube1312 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −31→35
Tmin = 0.982, Tmax = 0.986k = −6→8
4485 measured reflectionsl = −11→11

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) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0531P)2 + 0.1092P] where P = (Fo2 + 2Fc2)/3
1753 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.18 e Å3
3 restraintsΔρmin = −0.18 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O10.52924 (7)0.9086 (3)0.4162 (2)0.0576 (5)
N10.53391 (8)0.5581 (3)0.5306 (3)0.0497 (5)
N20.46277 (8)0.2671 (3)0.3271 (3)0.0522 (6)
H20.49120.22020.32070.063*
C10.60256 (9)0.7135 (4)0.4543 (3)0.0465 (6)
C20.57425 (10)0.8886 (4)0.4038 (3)0.0491 (6)
C30.59731 (11)1.0404 (4)0.3330 (4)0.0608 (7)
H30.57931.15370.29740.073*
C40.64475 (12)1.0231 (5)0.3167 (4)0.0658 (8)
H40.65831.12470.26890.079*
C50.67481 (11)0.8544 (5)0.3702 (3)0.0583 (7)
C60.72446 (13)0.8429 (6)0.3537 (5)0.0791 (10)
H60.73740.94330.30270.095*
C70.75394 (13)0.6840 (7)0.4128 (5)0.0908 (12)
H70.78680.67750.40310.109*
C80.73446 (14)0.5358 (7)0.4859 (6)0.0953 (13)
H80.75460.42940.52690.114*
C90.68608 (12)0.5403 (5)0.5000 (5)0.0748 (9)
H90.67380.43600.54870.090*
C100.65441 (10)0.6995 (4)0.4422 (3)0.0541 (7)
C110.57962 (10)0.5575 (4)0.5134 (3)0.0490 (6)
H110.59850.44450.54270.059*
C120.50873 (11)0.3947 (4)0.5875 (4)0.0568 (7)
H12A0.50460.42370.69450.068*
H12B0.52930.27840.59480.068*
C130.45822 (10)0.3570 (4)0.4749 (4)0.0540 (7)
H13A0.43890.27240.52780.065*
H13B0.44030.47960.45040.065*
C140.42170 (10)0.2552 (4)0.1944 (3)0.0477 (6)
C150.42493 (12)0.1449 (4)0.0608 (4)0.0590 (7)
H150.45420.07590.06270.071*
C160.38583 (14)0.1359 (4)−0.0735 (4)0.0689 (9)
H160.38900.0605−0.16090.083*
C170.34208 (13)0.2356 (5)−0.0821 (5)0.0732 (9)
H170.31570.2291−0.17420.088*
C180.33809 (12)0.3459 (5)0.0492 (4)0.0687 (8)
H180.30880.41540.04540.082*
C190.37702 (11)0.3545 (4)0.1862 (4)0.0579 (7)
H190.37340.42760.27430.070*
H10.5170 (12)0.671 (3)0.501 (4)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0519 (11)0.0450 (10)0.0754 (13)0.0099 (8)0.0146 (9)0.0058 (9)
N10.0534 (14)0.0385 (12)0.0542 (13)0.0029 (9)0.0075 (11)0.0009 (9)
N20.0450 (12)0.0432 (12)0.0711 (15)0.0038 (9)0.0196 (11)−0.0043 (10)
C10.0464 (14)0.0426 (13)0.0468 (13)0.0018 (11)0.0048 (11)−0.0035 (11)
C20.0530 (16)0.0412 (14)0.0482 (15)0.0029 (11)0.0032 (12)−0.0041 (11)
C30.0627 (18)0.0502 (17)0.0656 (19)0.0018 (13)0.0084 (15)0.0088 (14)
C40.068 (2)0.0579 (18)0.0687 (19)−0.0112 (14)0.0112 (16)0.0064 (15)
C50.0512 (15)0.064 (2)0.0569 (16)−0.0055 (13)0.0081 (13)−0.0087 (13)
C60.058 (2)0.092 (3)0.088 (2)−0.0136 (18)0.0210 (18)−0.009 (2)
C70.054 (2)0.107 (3)0.112 (3)0.005 (2)0.021 (2)−0.014 (3)
C80.063 (2)0.087 (3)0.136 (4)0.025 (2)0.024 (2)0.004 (3)
C90.0580 (19)0.067 (2)0.098 (2)0.0130 (15)0.0163 (18)0.0022 (19)
C100.0495 (15)0.0532 (16)0.0548 (16)0.0020 (12)0.0039 (12)−0.0087 (12)
C110.0533 (16)0.0392 (14)0.0500 (14)0.0088 (11)0.0041 (11)−0.0025 (11)
C120.0704 (18)0.0447 (14)0.0568 (16)0.0015 (13)0.0184 (14)0.0058 (13)
C130.0594 (16)0.0397 (14)0.0665 (17)−0.0028 (12)0.0226 (14)−0.0025 (12)
C140.0474 (15)0.0345 (12)0.0659 (17)−0.0024 (10)0.0230 (14)0.0004 (11)
C150.0647 (17)0.0372 (13)0.081 (2)−0.0035 (12)0.0301 (16)−0.0078 (13)
C160.086 (2)0.0496 (18)0.074 (2)−0.0129 (17)0.0246 (19)−0.0135 (15)
C170.074 (2)0.0609 (19)0.079 (2)−0.0137 (17)0.0080 (17)0.0017 (17)
C180.0557 (18)0.0620 (19)0.087 (2)0.0049 (15)0.0152 (17)0.0037 (17)
C190.0548 (16)0.0503 (17)0.0725 (19)0.0072 (12)0.0228 (14)−0.0027 (13)

Geometric parameters (Å, °)

O1—C21.276 (3)C8—C91.366 (5)
N1—C111.302 (3)C8—H80.9300
N1—C121.460 (3)C9—C101.407 (4)
N1—H10.907 (10)C9—H90.9300
N2—C141.392 (3)C11—H110.9300
N2—C131.437 (3)C12—C131.505 (4)
N2—H20.8600C12—H12A0.9700
C1—C111.397 (4)C12—H12B0.9700
C1—C21.436 (4)C13—H13A0.9700
C1—C101.459 (4)C13—H13B0.9700
C2—C31.427 (4)C14—C151.389 (4)
C3—C41.351 (4)C14—C191.391 (4)
C3—H30.9300C15—C161.367 (5)
C4—C51.428 (5)C15—H150.9300
C4—H40.9300C16—C171.370 (5)
C5—C61.409 (4)C16—H160.9300
C5—C101.410 (4)C17—C181.379 (5)
C6—C71.376 (6)C17—H170.9300
C6—H60.9300C18—C191.379 (4)
C7—C81.368 (6)C18—H180.9300
C7—H70.9300C19—H190.9300
C11—N1—C12125.9 (2)C5—C10—C1118.9 (2)
C11—N1—H1114 (2)N1—C11—C1125.0 (2)
C12—N1—H1120 (2)N1—C11—H11117.5
C14—N2—C13120.8 (2)C1—C11—H11117.5
C14—N2—H2119.6N1—C12—C13111.0 (2)
C13—N2—H2119.6N1—C12—H12A109.4
C11—C1—C2119.1 (2)C13—C12—H12A109.4
C11—C1—C10120.8 (2)N1—C12—H12B109.4
C2—C1—C10120.1 (2)C13—C12—H12B109.4
O1—C2—C3119.9 (2)H12A—C12—H12B108.0
O1—C2—C1122.0 (2)N2—C13—C12111.6 (2)
C3—C2—C1118.0 (2)N2—C13—H13A109.3
C4—C3—C2121.4 (3)C12—C13—H13A109.3
C4—C3—H3119.3N2—C13—H13B109.3
C2—C3—H3119.3C12—C13—H13B109.3
C3—C4—C5122.4 (3)H13A—C13—H13B108.0
C3—C4—H4118.8C15—C14—C19117.3 (3)
C5—C4—H4118.8C15—C14—N2119.9 (2)
C6—C5—C10120.1 (3)C19—C14—N2122.8 (2)
C6—C5—C4120.8 (3)C16—C15—C14121.1 (3)
C10—C5—C4119.1 (3)C16—C15—H15119.4
C7—C6—C5120.4 (4)C14—C15—H15119.4
C7—C6—H6119.8C15—C16—C17121.5 (3)
C5—C6—H6119.8C15—C16—H16119.3
C8—C7—C6119.5 (3)C17—C16—H16119.3
C8—C7—H7120.3C16—C17—C18118.3 (3)
C6—C7—H7120.3C16—C17—H17120.9
C9—C8—C7121.5 (4)C18—C17—H17120.9
C9—C8—H8119.2C17—C18—C19120.8 (3)
C7—C8—H8119.2C17—C18—H18119.6
C8—C9—C10121.3 (4)C19—C18—H18119.6
C8—C9—H9119.4C18—C19—C14120.9 (3)
C10—C9—H9119.4C18—C19—H19119.5
C9—C10—C5117.2 (3)C14—C19—H19119.5
C9—C10—C1123.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O10.91 (1)1.84 (3)2.582 (3)137 (3)
N2—H2···O1i0.862.433.043 (3)129

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2625).

References

  • Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718–m719. [PMC free article] [PubMed]
  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2002). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem.35, 805–813. [PubMed]
  • Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576–o577. [PMC free article] [PubMed]
  • Fun, H.-K., Kia, R., Vijesh, A. M. & Isloor, A. M. (2009). Acta Cryst. E65, o349–o350. [PMC free article] [PubMed]
  • Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403–m404. [PMC free article] [PubMed]
  • Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem.14, 7482–7489. [PubMed]
  • Nadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett.16, 2127–2129. [PubMed]
  • Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570–m571. [PMC free article] [PubMed]

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