Abstract
The title Schiff base compound, C18H14N2O3, has an intermediate state between NH and OH tautomers. The molecular structure is stabilized by an O—H⋯N hydrogen bond. The dihedral angle between the naphthalene ring system and the benzene ring is 37.44 (5)°.
Related literature
For the biological properties of Schiff bases, see: Lozier et al. (1975 ▶). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For Schiff base tautomerism, see: Hökelek et al. (2000 ▶); Karabıyık et al. (2007 ▶); Odabaşoğlu et al. (2005 ▶); Kılıç et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).
Experimental
Crystal data
C18H14N2O3
M r = 306.31
Monoclinic,
a = 12.5520 (9) Å
b = 7.4731 (4) Å
c = 15.8610 (13) Å
β = 90.806 (6)°
V = 1487.65 (18) Å3
Z = 4
Mo Kα radiation
μ = 0.10 mm−1
T = 296 K
0.7 × 0.47 × 0.12 mm
Data collection
Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.989, T max = 0.997
9684 measured reflections
3088 independent reflections
1969 reflections with I > 2σ(I)
R int = 0.061
Refinement
R[F 2 > 2σ(F 2)] = 0.051
wR(F 2) = 0.153
S = 0.94
3088 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.24 e Å−3
Δρmin = −0.19 e Å−3
Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043461/bt5391sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043461/bt5391Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1—H1⋯N1 | 1.10 (3) | 1.48 (3) | 2.5310 (19) | 159 (3) |
Acknowledgments
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the diffractometer (purchased under grant No. F279 of the University Research Fund).
supplementary crystallographic information
Comment
Schiff bases often exhibit various biological activities and in many cases were shown to have antibacterial, anticancer, anti-inflammatory and antitoxic properties (Lozier et al., 1975). Schiff bases have also been used as versatile ligands in coordination chemistry (Kargar et al., 2009; Yeap et al., 2009). There are two types of intramolecular hydrogen bonds in Schiff bases, namely N—H···O in keto (NH) (Hökelek et al., 2000) and N···H—O in enol (OH) (Odabaşoǧlu et al., 2005) tautomeric forms. Our investigations shows that in the title compound is described as an intermediate state between NH and OH tautomers. An ORTEP-3 (Farrugia, 1997) plot of the molecule of (I) is shown in Fig.1. The C2—O1 [1.331 (2) Å] and C11—N1 [1.299 (2) Å] bond lengths are intermediate between the single and double C—O (1.362 and 1.222 Å, respectively) and C—N bond lengths (1.339 and 1.279 Å, respectively) (Allen et al., 1987). The molecular structure is stabilized by an intramolecular O—H···N hydrogen bond. It is a well known fact that H atoms participating in intramolecular hydrogen bonds in Schiff bases are rather mobile. The molecule can be regarded as having an intermediate state between its canonical OH and NH forms, and therefore the O1—H1 bond [1.10 (3) Å] remains somewhat longer than its expected value (Karabıyık et al., 2007). Similar results were observed for 2-[(4-Methoxyphenyl)iminomethyl]-4- nitrophenol (Kılıç et al., 2009). The molecule of the title compound is not planar, with a dihedral angle of 37.44 (5)° between naphthalene and benzene rings.
Experimental
The title compound was prepared by refluxing a mixture of a solution containing 2-hydroxy-1-naphthaldehyde (172 mg, 0,0986 mmol) in ethanol (30 ml) and a solution containing 2-methyl-3-nitroaniline (15 mg, 0,0986 mmol) in ethanol (30 ml. The reaction mixture was stirred for 1 h under reflux. Single crystals of the title compound for x-ray analysis were obtained by slow evaporation of an ethanol solution (Yield 68%; m.p. 428–432 K).
Refinement
H atoms bonded to C were placed in calculated positions and constrained to ride on their parent atoms, with C–H = 0.93–0.96 Å and Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The H atom bonded to O was freely refined.
Figures
Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Crystal data
| C18H14N2O3 | F(000) = 640 |
| Mr = 306.31 | Dx = 1.368 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 8237 reflections |
| a = 12.5520 (9) Å | θ = 1.3–27.3° |
| b = 7.4731 (4) Å | µ = 0.10 mm−1 |
| c = 15.8610 (13) Å | T = 296 K |
| β = 90.806 (6)° | PRISM., yellow |
| V = 1487.65 (18) Å3 | 0.7 × 0.47 × 0.12 mm |
| Z = 4 |
Data collection
| Stoe IPDS II diffractometer | 3088 independent reflections |
| Radiation source: fine-focus sealed tube | 1969 reflections with I > 2σ(I) |
| graphite | Rint = 0.061 |
| Detector resolution: 6.67 pixels mm-1 | θmax = 26.5°, θmin = 1.6° |
| ω scans | h = −15→15 |
| Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −9→9 |
| Tmin = 0.989, Tmax = 0.997 | l = −19→17 |
| 9684 measured reflections |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.94 | (Δ/σ)max < 0.001 |
| 3088 reflections | Δρmax = 0.24 e Å−3 |
| 213 parameters | Δρmin = −0.19 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (2) |
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)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.41741 (13) | 0.0570 (2) | 0.21696 (11) | 0.0439 (4) | |
| C2 | 0.35899 (13) | 0.0014 (2) | 0.28723 (11) | 0.0489 (4) | |
| C3 | 0.24646 (15) | −0.0112 (3) | 0.28256 (13) | 0.0605 (5) | |
| H3 | 0.2085 | −0.0498 | 0.3291 | 0.073* | |
| C4 | 0.19459 (14) | 0.0329 (3) | 0.21045 (13) | 0.0627 (5) | |
| H4 | 0.1206 | 0.0258 | 0.2086 | 0.075* | |
| C5 | 0.24883 (13) | 0.0898 (3) | 0.13724 (12) | 0.0510 (4) | |
| C6 | 0.19243 (15) | 0.1360 (3) | 0.06252 (14) | 0.0618 (5) | |
| H6 | 0.1184 | 0.1309 | 0.0616 | 0.074* | |
| C7 | 0.24441 (16) | 0.1873 (3) | −0.00749 (14) | 0.0648 (5) | |
| H7 | 0.2062 | 0.2181 | −0.0560 | 0.078* | |
| C8 | 0.35511 (16) | 0.1941 (3) | −0.00694 (13) | 0.0606 (5) | |
| H8 | 0.3907 | 0.2270 | −0.0556 | 0.073* | |
| C9 | 0.41227 (14) | 0.1526 (3) | 0.06482 (11) | 0.0515 (5) | |
| H9 | 0.4862 | 0.1594 | 0.0642 | 0.062* | |
| C10 | 0.36138 (12) | 0.1001 (2) | 0.13924 (11) | 0.0441 (4) | |
| C11 | 0.53047 (13) | 0.0720 (2) | 0.22409 (12) | 0.0471 (4) | |
| H11 | 0.5686 | 0.1078 | 0.1772 | 0.057* | |
| C12 | 0.69421 (13) | 0.0479 (2) | 0.29892 (11) | 0.0487 (4) | |
| C13 | 0.74005 (13) | 0.1057 (2) | 0.37579 (11) | 0.0461 (4) | |
| C14 | 0.85070 (14) | 0.1110 (3) | 0.37726 (12) | 0.0557 (5) | |
| C15 | 0.91392 (15) | 0.0627 (4) | 0.31127 (15) | 0.0757 (7) | |
| H15 | 0.9877 | 0.0702 | 0.3159 | 0.091* | |
| C16 | 0.86568 (16) | 0.0027 (4) | 0.23779 (15) | 0.0813 (7) | |
| H16 | 0.9068 | −0.0323 | 0.1924 | 0.098* | |
| C17 | 0.75641 (15) | −0.0048 (3) | 0.23229 (13) | 0.0655 (6) | |
| H17 | 0.7239 | −0.0461 | 0.1830 | 0.079* | |
| C18 | 0.67164 (14) | 0.1657 (3) | 0.44710 (12) | 0.0562 (5) | |
| H18A | 0.7161 | 0.2005 | 0.4940 | 0.084* | |
| H18B | 0.6260 | 0.0692 | 0.4637 | 0.084* | |
| H18C | 0.6290 | 0.2657 | 0.4292 | 0.084* | |
| N1 | 0.58208 (11) | 0.0375 (2) | 0.29377 (9) | 0.0481 (4) | |
| N2 | 0.90826 (13) | 0.1746 (3) | 0.45348 (12) | 0.0695 (5) | |
| O1 | 0.40602 (11) | −0.0411 (2) | 0.36024 (8) | 0.0609 (4) | |
| O2 | 0.88124 (15) | 0.1224 (3) | 0.52187 (11) | 0.1036 (7) | |
| O3 | 0.98286 (12) | 0.2763 (3) | 0.44235 (12) | 0.0997 (6) | |
| H1 | 0.489 (3) | −0.023 (4) | 0.343 (2) | 0.128 (10)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0467 (8) | 0.0410 (9) | 0.0437 (9) | 0.0020 (7) | −0.0038 (7) | −0.0022 (8) |
| C2 | 0.0532 (9) | 0.0499 (10) | 0.0435 (10) | 0.0026 (7) | 0.0003 (7) | −0.0048 (8) |
| C3 | 0.0548 (10) | 0.0759 (14) | 0.0510 (11) | −0.0020 (9) | 0.0092 (8) | −0.0036 (10) |
| C4 | 0.0419 (9) | 0.0810 (14) | 0.0652 (13) | 0.0029 (9) | 0.0014 (9) | −0.0089 (11) |
| C5 | 0.0472 (9) | 0.0541 (11) | 0.0515 (11) | 0.0041 (7) | −0.0059 (8) | −0.0083 (9) |
| C6 | 0.0506 (10) | 0.0709 (13) | 0.0634 (13) | 0.0104 (9) | −0.0158 (9) | −0.0083 (11) |
| C7 | 0.0716 (12) | 0.0672 (13) | 0.0552 (12) | 0.0102 (10) | −0.0218 (10) | −0.0007 (10) |
| C8 | 0.0738 (12) | 0.0603 (12) | 0.0474 (11) | −0.0026 (9) | −0.0073 (9) | 0.0052 (9) |
| C9 | 0.0531 (9) | 0.0517 (10) | 0.0496 (11) | −0.0050 (8) | −0.0061 (8) | 0.0033 (9) |
| C10 | 0.0478 (9) | 0.0391 (9) | 0.0453 (9) | 0.0011 (7) | −0.0044 (7) | −0.0029 (7) |
| C11 | 0.0493 (9) | 0.0461 (10) | 0.0459 (10) | −0.0011 (7) | −0.0026 (7) | 0.0003 (8) |
| C12 | 0.0470 (9) | 0.0509 (10) | 0.0480 (10) | 0.0015 (7) | −0.0048 (7) | −0.0003 (8) |
| C13 | 0.0473 (8) | 0.0476 (10) | 0.0434 (9) | −0.0002 (7) | −0.0050 (7) | 0.0031 (8) |
| C14 | 0.0487 (9) | 0.0655 (12) | 0.0526 (11) | 0.0008 (8) | −0.0113 (8) | −0.0018 (9) |
| C15 | 0.0443 (10) | 0.1099 (19) | 0.0727 (15) | 0.0034 (10) | −0.0026 (9) | −0.0122 (14) |
| C16 | 0.0546 (11) | 0.122 (2) | 0.0674 (14) | 0.0087 (12) | 0.0058 (10) | −0.0223 (15) |
| C17 | 0.0570 (10) | 0.0860 (15) | 0.0533 (12) | 0.0069 (10) | −0.0049 (9) | −0.0168 (11) |
| C18 | 0.0567 (10) | 0.0636 (12) | 0.0481 (10) | −0.0007 (8) | −0.0018 (8) | 0.0019 (9) |
| N1 | 0.0471 (8) | 0.0497 (8) | 0.0473 (8) | 0.0010 (6) | −0.0083 (6) | −0.0003 (7) |
| N2 | 0.0517 (9) | 0.0915 (14) | 0.0646 (12) | 0.0002 (9) | −0.0173 (8) | −0.0044 (11) |
| O1 | 0.0635 (8) | 0.0769 (10) | 0.0422 (7) | 0.0031 (7) | −0.0009 (6) | 0.0051 (7) |
| O2 | 0.1009 (13) | 0.154 (2) | 0.0552 (10) | −0.0192 (12) | −0.0220 (9) | 0.0058 (11) |
| O3 | 0.0650 (9) | 0.1341 (17) | 0.0991 (13) | −0.0299 (10) | −0.0239 (9) | −0.0091 (12) |
Geometric parameters (Å, °)
| C1—C2 | 1.406 (2) | C11—H11 | 0.9300 |
| C1—C11 | 1.426 (2) | C12—C17 | 1.380 (3) |
| C1—C10 | 1.447 (2) | C12—C13 | 1.409 (2) |
| C2—O1 | 1.331 (2) | C12—N1 | 1.411 (2) |
| C2—C3 | 1.417 (3) | C13—C14 | 1.389 (2) |
| C3—C4 | 1.349 (3) | C13—C18 | 1.498 (3) |
| C3—H3 | 0.9300 | C14—C15 | 1.371 (3) |
| C4—C5 | 1.420 (3) | C14—N2 | 1.478 (3) |
| C4—H4 | 0.9300 | C15—C16 | 1.381 (3) |
| C5—C6 | 1.415 (3) | C15—H15 | 0.9300 |
| C5—C10 | 1.415 (2) | C16—C17 | 1.374 (3) |
| C6—C7 | 1.351 (3) | C16—H16 | 0.9300 |
| C6—H6 | 0.9300 | C17—H17 | 0.9300 |
| C7—C8 | 1.390 (3) | C18—H18A | 0.9600 |
| C7—H7 | 0.9300 | C18—H18B | 0.9600 |
| C8—C9 | 1.372 (3) | C18—H18C | 0.9600 |
| C8—H8 | 0.9300 | N2—O2 | 1.206 (2) |
| C9—C10 | 1.406 (2) | N2—O3 | 1.221 (2) |
| C9—H9 | 0.9300 | O1—H1 | 1.10 (3) |
| C11—N1 | 1.299 (2) | ||
| C2—C1—C11 | 119.33 (16) | C1—C11—H11 | 118.8 |
| C2—C1—C10 | 119.26 (15) | C17—C12—C13 | 121.45 (16) |
| C11—C1—C10 | 121.41 (15) | C17—C12—N1 | 120.96 (16) |
| O1—C2—C1 | 122.05 (15) | C13—C12—N1 | 117.52 (15) |
| O1—C2—C3 | 117.35 (16) | C14—C13—C12 | 114.78 (16) |
| C1—C2—C3 | 120.60 (16) | C14—C13—C18 | 124.22 (16) |
| C4—C3—C2 | 119.81 (18) | C12—C13—C18 | 120.91 (15) |
| C4—C3—H3 | 120.1 | C15—C14—C13 | 124.69 (17) |
| C2—C3—H3 | 120.1 | C15—C14—N2 | 115.32 (16) |
| C3—C4—C5 | 122.38 (17) | C13—C14—N2 | 119.98 (17) |
| C3—C4—H4 | 118.8 | C14—C15—C16 | 118.58 (18) |
| C5—C4—H4 | 118.8 | C14—C15—H15 | 120.7 |
| C6—C5—C10 | 119.57 (18) | C16—C15—H15 | 120.7 |
| C6—C5—C4 | 121.22 (16) | C17—C16—C15 | 119.5 (2) |
| C10—C5—C4 | 119.21 (16) | C17—C16—H16 | 120.3 |
| C7—C6—C5 | 121.06 (17) | C15—C16—H16 | 120.3 |
| C7—C6—H6 | 119.5 | C16—C17—C12 | 120.96 (19) |
| C5—C6—H6 | 119.5 | C16—C17—H17 | 119.5 |
| C6—C7—C8 | 119.95 (17) | C12—C17—H17 | 119.5 |
| C6—C7—H7 | 120.0 | C13—C18—H18A | 109.5 |
| C8—C7—H7 | 120.0 | C13—C18—H18B | 109.5 |
| C9—C8—C7 | 120.52 (19) | H18A—C18—H18B | 109.5 |
| C9—C8—H8 | 119.7 | C13—C18—H18C | 109.5 |
| C7—C8—H8 | 119.7 | H18A—C18—H18C | 109.5 |
| C8—C9—C10 | 121.39 (17) | H18B—C18—H18C | 109.5 |
| C8—C9—H9 | 119.3 | C11—N1—C12 | 121.57 (15) |
| C10—C9—H9 | 119.3 | C11—N1—H1 | 97.0 (12) |
| C9—C10—C5 | 117.49 (16) | C12—N1—H1 | 141.0 (12) |
| C9—C10—C1 | 123.80 (15) | O2—N2—O3 | 123.89 (19) |
| C5—C10—C1 | 118.71 (16) | O2—N2—C14 | 119.41 (19) |
| N1—C11—C1 | 122.38 (17) | O3—N2—C14 | 116.68 (19) |
| N1—C11—H11 | 118.8 | C2—O1—H1 | 99.5 (17) |
| C11—C1—C2—O1 | −1.2 (3) | C2—C1—C11—N1 | −0.6 (3) |
| C10—C1—C2—O1 | 179.59 (16) | C10—C1—C11—N1 | 178.56 (17) |
| C11—C1—C2—C3 | 178.70 (17) | C17—C12—C13—C14 | 2.2 (3) |
| C10—C1—C2—C3 | −0.5 (3) | N1—C12—C13—C14 | 179.22 (16) |
| O1—C2—C3—C4 | 178.99 (19) | C17—C12—C13—C18 | 178.92 (19) |
| C1—C2—C3—C4 | −0.9 (3) | N1—C12—C13—C18 | −4.1 (3) |
| C2—C3—C4—C5 | 1.0 (3) | C12—C13—C14—C15 | −0.9 (3) |
| C3—C4—C5—C6 | −179.8 (2) | C18—C13—C14—C15 | −177.5 (2) |
| C3—C4—C5—C10 | 0.4 (3) | C12—C13—C14—N2 | 178.16 (18) |
| C10—C5—C6—C7 | 1.0 (3) | C18—C13—C14—N2 | 1.6 (3) |
| C4—C5—C6—C7 | −178.9 (2) | C13—C14—C15—C16 | −0.6 (4) |
| C5—C6—C7—C8 | 0.5 (3) | N2—C14—C15—C16 | −179.7 (2) |
| C6—C7—C8—C9 | −1.4 (3) | C14—C15—C16—C17 | 0.8 (4) |
| C7—C8—C9—C10 | 0.8 (3) | C15—C16—C17—C12 | 0.5 (4) |
| C8—C9—C10—C5 | 0.6 (3) | C13—C12—C17—C16 | −2.1 (3) |
| C8—C9—C10—C1 | −179.21 (17) | N1—C12—C17—C16 | −179.0 (2) |
| C6—C5—C10—C9 | −1.5 (3) | C1—C11—N1—C12 | 178.07 (15) |
| C4—C5—C10—C9 | 178.39 (18) | C17—C12—N1—C11 | −37.0 (3) |
| C6—C5—C10—C1 | 178.35 (17) | C13—C12—N1—C11 | 145.97 (18) |
| C4—C5—C10—C1 | −1.8 (3) | C15—C14—N2—O2 | −135.8 (2) |
| C2—C1—C10—C9 | −178.35 (16) | C13—C14—N2—O2 | 45.0 (3) |
| C11—C1—C10—C9 | 2.5 (3) | C15—C14—N2—O3 | 42.8 (3) |
| C2—C1—C10—C5 | 1.8 (2) | C13—C14—N2—O3 | −136.3 (2) |
| C11—C1—C10—C5 | −177.34 (15) |
Hydrogen-bond geometry (Å, °)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 1.10 (3) | 1.48 (3) | 2.5310 (19) | 159 (3) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5391).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043461/bt5391sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043461/bt5391Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report