Acta Cryst. (2008). E64, o768 [ doi:10.1107/S1600536808008076 ]
The title Schiff base compound, C19H16N2O3, was derived from the condensation reaction of 2-hydroxy-1-naphthylaldehyde with 4-methoxybenzohydrazide. The dihedral angle between the benzene ring and the naphthyl ring system is 6.8 (2)°. In the crystal structure, molecules are linked through intermolecular N-H
O intermolecular hydrogen bonds, forming chains running along the c axis.
2-Hydroxy-1-naphtylaldehyde (0.1 mmol, 17.2 mg) and 4-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were dissolved in an ethanol solution (20 ml). The mixture was stirred at reflux for 10 min to give a clear colorless solution. Colorless needle-like crystals of the compound were formed by slow evaporation of the solvent over several days.
H2 atom was located from a difference Fourier map and refined isotropically, with N—H distance restrained to 0.90 (1) Å. Other H atoms were constrained to ideal geometries, with C—H = 0.93–0.96 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C), 1.5Ueq(C19 and O1).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./sj2478fig1thm.gif)
| Fig. 1. The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./sj2478fig2thm.gif)
| Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines. |
| C19H16N2O3 | F000 = 672 |
| Mr = 320.34 | Dx = 1.368 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1378 reflections |
| a = 11.159 (2) Å | θ = 2.2–24.5º |
| b = 15.790 (3) Å | µ = 0.09 mm−1 |
| c = 8.8300 (18) Å | T = 298 (2) K |
| β = 91.70 (3)º | Cut from a needle, colorless |
| V = 1555.2 (5) Å3 | 0.32 × 0.32 × 0.30 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 3550 independent reflections |
| Radiation source: fine-focus sealed tube | 2161 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.052 |
| T = 298(2) K | θmax = 27.5º |
| ω scans | θmin = 1.8º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
| Tmin = 0.971, Tmax = 0.972 | k = −20→20 |
| 13232 measured reflections | l = −11→11 |
| 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)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0391P)2 + 0.168P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max = 0.001 |
| 3550 reflections | Δρmax = 0.18 e Å−3 |
| 222 parameters | Δρmin = −0.20 e Å−3 |
| 1 restraint | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C19H16N2O3 | V = 1555.2 (5) Å3 |
| Mr = 320.34 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 11.159 (2) Å | µ = 0.09 mm−1 |
| b = 15.790 (3) Å | T = 298 (2) K |
| c = 8.8300 (18) Å | 0.32 × 0.32 × 0.30 mm |
| β = 91.70 (3)º |
| Bruker SMART CCD area-detector diffractometer | 3550 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2161 reflections with I > 2σ(I) |
| Tmin = 0.971, Tmax = 0.972 | Rint = 0.052 |
| 13232 measured reflections |
| R[F2 > 2σ(F2)] = 0.056 | 1 restraint |
| wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | Δρmax = 0.18 e Å−3 |
| 3550 reflections | Δρmin = −0.20 e Å−3 |
| 222 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.44682 (14) | 0.12307 (9) | 0.77419 (16) | 0.0569 (4) | |
| H1 | 0.4089 | 0.1584 | 0.7244 | 0.085* | |
| O2 | 0.24817 (13) | 0.32717 (8) | 0.67361 (14) | 0.0515 (4) | |
| O3 | 0.02184 (13) | 0.57256 (9) | 0.17402 (17) | 0.0602 (5) | |
| N1 | 0.30518 (14) | 0.17750 (9) | 0.55897 (17) | 0.0415 (4) | |
| N2 | 0.25139 (15) | 0.24056 (10) | 0.47098 (17) | 0.0423 (4) | |
| C1 | 0.35505 (16) | 0.03145 (12) | 0.5862 (2) | 0.0362 (4) | |
| C2 | 0.42732 (17) | 0.04559 (13) | 0.7145 (2) | 0.0431 (5) | |
| C3 | 0.48691 (18) | −0.02246 (15) | 0.7874 (2) | 0.0520 (6) | |
| H3 | 0.5370 | −0.0121 | 0.8715 | 0.062* | |
| C4 | 0.47221 (19) | −0.10234 (14) | 0.7367 (2) | 0.0526 (6) | |
| H4 | 0.5124 | −0.1462 | 0.7868 | 0.063* | |
| C5 | 0.39740 (17) | −0.12109 (13) | 0.6096 (2) | 0.0434 (5) | |
| C6 | 0.3824 (2) | −0.20495 (13) | 0.5558 (3) | 0.0561 (6) | |
| H6 | 0.4230 | −0.2489 | 0.6051 | 0.067* | |
| C7 | 0.3101 (2) | −0.22238 (14) | 0.4342 (3) | 0.0608 (6) | |
| H7 | 0.3007 | −0.2779 | 0.4007 | 0.073* | |
| C8 | 0.2498 (2) | −0.15638 (14) | 0.3591 (3) | 0.0586 (6) | |
| H8 | 0.2005 | −0.1683 | 0.2750 | 0.070* | |
| C9 | 0.26197 (18) | −0.07449 (12) | 0.4075 (2) | 0.0458 (5) | |
| H9 | 0.2198 | −0.0318 | 0.3566 | 0.055* | |
| C10 | 0.33734 (16) | −0.05348 (11) | 0.5331 (2) | 0.0371 (5) | |
| C11 | 0.29956 (17) | 0.10221 (12) | 0.5053 (2) | 0.0388 (5) | |
| H11 | 0.2594 | 0.0926 | 0.4131 | 0.047* | |
| C12 | 0.22727 (17) | 0.31534 (11) | 0.5375 (2) | 0.0376 (5) | |
| C13 | 0.17287 (17) | 0.38188 (11) | 0.4404 (2) | 0.0365 (4) | |
| C14 | 0.18459 (18) | 0.46552 (12) | 0.4857 (2) | 0.0454 (5) | |
| H14 | 0.2259 | 0.4778 | 0.5761 | 0.054* | |
| C15 | 0.13651 (19) | 0.53130 (12) | 0.4000 (2) | 0.0493 (5) | |
| H15 | 0.1466 | 0.5871 | 0.4317 | 0.059* | |
| C16 | 0.07353 (17) | 0.51333 (12) | 0.2674 (2) | 0.0427 (5) | |
| C17 | 0.05869 (18) | 0.43022 (12) | 0.2214 (2) | 0.0453 (5) | |
| H17 | 0.0147 | 0.4180 | 0.1329 | 0.054* | |
| C18 | 0.10864 (17) | 0.36569 (12) | 0.3058 (2) | 0.0406 (5) | |
| H18 | 0.0995 | 0.3101 | 0.2725 | 0.049* | |
| C19 | 0.0515 (2) | 0.65852 (13) | 0.2009 (3) | 0.0685 (7) | |
| H19A | 0.0224 | 0.6755 | 0.2974 | 0.103* | |
| H19B | 0.0153 | 0.6931 | 0.1227 | 0.103* | |
| H19C | 0.1370 | 0.6652 | 0.2007 | 0.103* | |
| H2 | 0.251 (2) | 0.2301 (14) | 0.3703 (12) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0614 (11) | 0.0580 (10) | 0.0505 (10) | −0.0051 (8) | −0.0100 (8) | −0.0063 (8) |
| O2 | 0.0791 (11) | 0.0422 (8) | 0.0326 (8) | 0.0005 (7) | −0.0063 (7) | −0.0019 (6) |
| O3 | 0.0683 (11) | 0.0440 (9) | 0.0674 (11) | 0.0126 (7) | −0.0113 (8) | 0.0084 (8) |
| N1 | 0.0508 (11) | 0.0356 (9) | 0.0380 (9) | 0.0008 (8) | 0.0009 (8) | 0.0047 (7) |
| N2 | 0.0608 (11) | 0.0320 (9) | 0.0339 (9) | 0.0046 (8) | −0.0029 (9) | 0.0013 (7) |
| C1 | 0.0350 (10) | 0.0388 (11) | 0.0350 (11) | 0.0019 (8) | 0.0038 (8) | 0.0062 (8) |
| C2 | 0.0391 (11) | 0.0500 (13) | 0.0405 (12) | −0.0026 (10) | 0.0036 (9) | 0.0034 (10) |
| C3 | 0.0414 (12) | 0.0728 (16) | 0.0413 (13) | 0.0038 (11) | −0.0065 (10) | 0.0114 (11) |
| C4 | 0.0465 (13) | 0.0549 (14) | 0.0564 (14) | 0.0122 (10) | 0.0035 (11) | 0.0204 (11) |
| C5 | 0.0371 (11) | 0.0461 (12) | 0.0474 (12) | 0.0058 (9) | 0.0077 (9) | 0.0119 (10) |
| C6 | 0.0589 (15) | 0.0399 (13) | 0.0700 (16) | 0.0138 (11) | 0.0121 (12) | 0.0144 (11) |
| C7 | 0.0684 (16) | 0.0394 (13) | 0.0750 (17) | 0.0035 (11) | 0.0085 (14) | −0.0022 (12) |
| C8 | 0.0658 (16) | 0.0512 (14) | 0.0586 (15) | −0.0033 (11) | −0.0020 (12) | −0.0065 (11) |
| C9 | 0.0500 (13) | 0.0380 (11) | 0.0492 (13) | 0.0013 (9) | −0.0004 (10) | 0.0014 (9) |
| C10 | 0.0349 (11) | 0.0396 (11) | 0.0370 (11) | 0.0022 (9) | 0.0062 (9) | 0.0069 (9) |
| C11 | 0.0421 (12) | 0.0395 (11) | 0.0348 (11) | −0.0008 (9) | 0.0006 (9) | 0.0035 (9) |
| C12 | 0.0423 (11) | 0.0359 (11) | 0.0346 (11) | −0.0056 (8) | 0.0005 (9) | −0.0003 (8) |
| C13 | 0.0397 (11) | 0.0349 (10) | 0.0350 (11) | −0.0017 (8) | 0.0033 (8) | −0.0002 (8) |
| C14 | 0.0545 (13) | 0.0409 (12) | 0.0403 (12) | −0.0017 (10) | −0.0045 (10) | −0.0061 (9) |
| C15 | 0.0609 (14) | 0.0322 (11) | 0.0547 (14) | 0.0017 (10) | −0.0011 (11) | −0.0036 (10) |
| C16 | 0.0408 (11) | 0.0412 (12) | 0.0458 (12) | 0.0050 (9) | −0.0008 (9) | 0.0032 (9) |
| C17 | 0.0454 (13) | 0.0479 (13) | 0.0421 (12) | −0.0002 (10) | −0.0077 (10) | −0.0004 (10) |
| C18 | 0.0467 (12) | 0.0351 (11) | 0.0397 (11) | −0.0029 (9) | −0.0020 (9) | −0.0046 (9) |
| C19 | 0.0857 (19) | 0.0414 (13) | 0.0784 (18) | 0.0172 (12) | 0.0019 (14) | 0.0076 (12) |
| O1—C2 | 1.347 (2) | C7—C8 | 1.397 (3) |
| O1—H1 | 0.8200 | C7—H7 | 0.9300 |
| O2—C12 | 1.231 (2) | C8—C9 | 1.367 (3) |
| O3—C16 | 1.363 (2) | C8—H8 | 0.9300 |
| O3—C19 | 1.415 (2) | C9—C10 | 1.411 (3) |
| N1—C11 | 1.281 (2) | C9—H9 | 0.9300 |
| N1—N2 | 1.388 (2) | C11—H11 | 0.9300 |
| N2—C12 | 1.350 (2) | C12—C13 | 1.475 (3) |
| N2—H2 | 0.904 (9) | C13—C14 | 1.385 (2) |
| C1—C2 | 1.389 (3) | C13—C18 | 1.394 (3) |
| C1—C10 | 1.432 (2) | C14—C15 | 1.384 (3) |
| C1—C11 | 1.455 (2) | C14—H14 | 0.9300 |
| C2—C3 | 1.409 (3) | C15—C16 | 1.377 (3) |
| C3—C4 | 1.347 (3) | C15—H15 | 0.9300 |
| C3—H3 | 0.9300 | C16—C17 | 1.382 (3) |
| C4—C5 | 1.410 (3) | C17—C18 | 1.371 (3) |
| C4—H4 | 0.9300 | C17—H17 | 0.9300 |
| C5—C6 | 1.415 (3) | C18—H18 | 0.9300 |
| C5—C10 | 1.421 (3) | C19—H19A | 0.9600 |
| C6—C7 | 1.352 (3) | C19—H19B | 0.9600 |
| C6—H6 | 0.9300 | C19—H19C | 0.9600 |
| C2—O1—H1 | 109.5 | C9—C10—C5 | 117.31 (18) |
| C16—O3—C19 | 117.63 (17) | C9—C10—C1 | 123.40 (17) |
| C11—N1—N2 | 116.28 (16) | C5—C10—C1 | 119.29 (18) |
| C12—N2—N1 | 118.18 (15) | N1—C11—C1 | 121.04 (18) |
| C12—N2—H2 | 126.4 (15) | N1—C11—H11 | 119.5 |
| N1—N2—H2 | 114.0 (15) | C1—C11—H11 | 119.5 |
| C2—C1—C10 | 119.24 (17) | O2—C12—N2 | 121.54 (17) |
| C2—C1—C11 | 120.36 (18) | O2—C12—C13 | 121.46 (17) |
| C10—C1—C11 | 120.39 (17) | N2—C12—C13 | 116.99 (16) |
| O1—C2—C1 | 123.23 (18) | C14—C13—C18 | 117.57 (18) |
| O1—C2—C3 | 116.45 (18) | C14—C13—C12 | 118.53 (17) |
| C1—C2—C3 | 120.31 (19) | C18—C13—C12 | 123.89 (17) |
| C4—C3—C2 | 120.7 (2) | C15—C14—C13 | 121.75 (19) |
| C4—C3—H3 | 119.6 | C15—C14—H14 | 119.1 |
| C2—C3—H3 | 119.6 | C13—C14—H14 | 119.1 |
| C3—C4—C5 | 121.63 (19) | C16—C15—C14 | 119.34 (19) |
| C3—C4—H4 | 119.2 | C16—C15—H15 | 120.3 |
| C5—C4—H4 | 119.2 | C14—C15—H15 | 120.3 |
| C4—C5—C6 | 121.66 (19) | O3—C16—C15 | 124.67 (18) |
| C4—C5—C10 | 118.73 (19) | O3—C16—C17 | 115.39 (18) |
| C6—C5—C10 | 119.6 (2) | C15—C16—C17 | 119.94 (18) |
| C7—C6—C5 | 121.3 (2) | C18—C17—C16 | 120.17 (18) |
| C7—C6—H6 | 119.4 | C18—C17—H17 | 119.9 |
| C5—C6—H6 | 119.4 | C16—C17—H17 | 119.9 |
| C6—C7—C8 | 119.5 (2) | C17—C18—C13 | 121.20 (18) |
| C6—C7—H7 | 120.2 | C17—C18—H18 | 119.4 |
| C8—C7—H7 | 120.2 | C13—C18—H18 | 119.4 |
| C9—C8—C7 | 121.0 (2) | O3—C19—H19A | 109.5 |
| C9—C8—H8 | 119.5 | O3—C19—H19B | 109.5 |
| C7—C8—H8 | 119.5 | H19A—C19—H19B | 109.5 |
| C8—C9—C10 | 121.29 (19) | O3—C19—H19C | 109.5 |
| C8—C9—H9 | 119.4 | H19A—C19—H19C | 109.5 |
| C10—C9—H9 | 119.4 | H19B—C19—H19C | 109.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 1.86 | 2.582 (2) | 146 |
| N2—H2···O2i | 0.904 (9) | 1.957 (12) | 2.834 (2) | 163 (2) |
| Symmetry codes: (i) x, −y+1/2, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 1.86 | 2.582 (2) | 146 |
| N2—H2···O2i | 0.904 (9) | 1.957 (12) | 2.834 (2) | 163 (2) |
| Symmetry codes: (i) x, −y+1/2, z−1/2. |
Financial support from the Jiaying University Research Fund is gratefully acknowledged.
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 (Version 5.62) and SMART (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Tang, C.-B. (2006). Acta Cryst. E63, m2629–m2630.
Tang, C.-B. (2007a). Acta Cryst. E63, m2654.
Tang, C.-B. (2007b). Acta Cryst. E63, m2785–m2786.
Tang, C.-B. (2007c). Acta Cryst. E63, o4545.
Tang, C.-B. (2007d). Acta Cryst. E63, o4841.
Recently, the author has reported the structures of several Schiff base compounds (Tang, 2006, 2007a,b,c,d) and, in continuation of work in this area, reports herein the structure of the title compound, (I), Fig. 1, a new Schiff base compound.
In the title compound (Fig. 1), the dihedral angle between the benzene ring and the naphtyl ring is 6.8 (2)°. The torsion angles C1—C11—N1—N2, C11—N1—N2—C12, and N1—N2—C12—C13 are 1.3 (2), 17.0 (2), and 1.5 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).
In the crystal structure of the compound, molecules are linked through N—H···O intermolecular hydrogen bonds (Table 1), forming chains running along the c axis (Fig. 2).