Acta Cryst. (2009). E65, o2990 [ doi:10.1107/S1600536809043086 ]
In the title Schiff base compound, C19H16N2O3, the dihedral angle between the mean planes of the benzene ring and the naphthyl ring system is 0.8 (2)°. The mean plane of the hydrazide group forms dihedral angles of 2.0 (2) and 2.2 (2)°, respectively, with the mean planes of the benzene ring and the naphthyl ring system. A strong intramolecular N-H
O hydrogen bond is present. In the crystal, intermolecular O-HO hydrogen bonds form chains along the c axis and help to provide stability in the crystal packing.
2-Methoxybenzaldehyde (0.1 mmol, 13.6 mg) and 3-hydroxy-2-naphthohydrazide (0.1 mmol) were refluxed in a 30 ml methanol solution for 30 min to give a clear colorless solution. Colorless block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.
H2 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) = 0.93-0.96 Å, d(O—H) = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O3 and C7).
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: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./jj2010fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids. A strong intramolecular N—H···O hydrogen bond is shown as a dashed line. |
![[Figure 2]](./jj2010fig2thm.gif)
| Fig. 2. Molecular packing of the title compound. Strong intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (shown as dashed lines) form chains of molecules along the c axis of the unit cell help to provide stability in crystal packing. . |
| C19H16N2O3 | F(000) = 672 |
| Mr = 320.34 | Dx = 1.383 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3028 reflections |
| a = 7.4990 (6) Å | θ = 2.6–30.0° |
| b = 15.4256 (13) Å | µ = 0.10 mm−1 |
| c = 13.3903 (12) Å | T = 298 K |
| β = 96.709 (4)° | Block, yellow |
| V = 1538.3 (2) Å3 | 0.18 × 0.17 × 0.17 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 3349 independent reflections |
| Radiation source: fine-focus sealed tube | 2520 reflections with I > 2σ(I) |
| graphite | Rint = 0.023 |
| ω scans | θmax = 27.0°, θmin = 2.0° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
| Tmin = 0.983, Tmax = 0.984 | k = −19→19 |
| 9323 measured reflections | l = −17→14 |
| 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)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.2454P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max = 0.001 |
| 3349 reflections | Δρmax = 0.20 e Å−3 |
| 223 parameters | Δρmin = −0.16 e Å−3 |
| 1 restraint | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0080 (13) |
| C19H16N2O3 | V = 1538.3 (2) Å3 |
| Mr = 320.34 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 7.4990 (6) Å | µ = 0.10 mm−1 |
| b = 15.4256 (13) Å | T = 298 K |
| c = 13.3903 (12) Å | 0.18 × 0.17 × 0.17 mm |
| β = 96.709 (4)° |
| Bruker SMART CCD area-detector diffractometer | 3349 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2520 reflections with I > 2σ(I) |
| Tmin = 0.983, Tmax = 0.984 | Rint = 0.023 |
| 9323 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.119 | Δρmax = 0.20 e Å−3 |
| S = 1.04 | Δρmin = −0.16 e Å−3 |
| 3349 reflections | Absolute structure: ? |
| 223 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
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 > 2σ(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 | 0.12815 (15) | 1.07729 (7) | 0.87156 (7) | 0.0541 (3) | |
| O2 | 0.53258 (17) | 0.75013 (6) | 1.13388 (7) | 0.0558 (3) | |
| O3 | 0.43652 (16) | 0.74188 (7) | 0.81939 (7) | 0.0526 (3) | |
| H3 | 0.4525 | 0.7391 | 0.7599 | 0.079* | |
| N1 | 0.36704 (15) | 0.89208 (7) | 1.04707 (8) | 0.0409 (3) | |
| N2 | 0.41657 (16) | 0.82106 (7) | 0.99432 (8) | 0.0408 (3) | |
| C1 | 0.23017 (18) | 1.03244 (9) | 1.03531 (10) | 0.0394 (3) | |
| C2 | 0.14420 (18) | 1.09540 (9) | 0.97151 (10) | 0.0399 (3) | |
| C3 | 0.0791 (2) | 1.17049 (10) | 1.01086 (12) | 0.0502 (4) | |
| H3A | 0.0221 | 1.2122 | 0.9682 | 0.060* | |
| C4 | 0.0989 (3) | 1.18316 (11) | 1.11277 (13) | 0.0663 (5) | |
| H4 | 0.0542 | 1.2334 | 1.1391 | 0.080* | |
| C5 | 0.1840 (3) | 1.12260 (12) | 1.17626 (12) | 0.0731 (6) | |
| H5 | 0.1976 | 1.1321 | 1.2453 | 0.088* | |
| C6 | 0.2491 (2) | 1.04788 (10) | 1.13819 (11) | 0.0553 (4) | |
| H6 | 0.3067 | 1.0071 | 1.1818 | 0.066* | |
| C7 | 0.0339 (3) | 1.13737 (12) | 0.80462 (11) | 0.0631 (5) | |
| H7A | −0.0867 | 1.1436 | 0.8210 | 0.095* | |
| H7B | 0.0313 | 1.1166 | 0.7369 | 0.095* | |
| H7C | 0.0934 | 1.1925 | 0.8107 | 0.095* | |
| C8 | 0.29350 (19) | 0.95271 (9) | 0.99292 (10) | 0.0422 (3) | |
| H8 | 0.2795 | 0.9460 | 0.9234 | 0.051* | |
| C9 | 0.49987 (18) | 0.75329 (8) | 1.04213 (9) | 0.0371 (3) | |
| C10 | 0.55517 (17) | 0.68060 (8) | 0.97827 (9) | 0.0348 (3) | |
| C11 | 0.52607 (18) | 0.67543 (9) | 0.87108 (9) | 0.0381 (3) | |
| C12 | 0.5848 (2) | 0.60516 (9) | 0.82249 (10) | 0.0439 (3) | |
| H12 | 0.5655 | 0.6030 | 0.7526 | 0.053* | |
| C13 | 0.67397 (19) | 0.53573 (9) | 0.87531 (10) | 0.0410 (3) | |
| C14 | 0.7369 (2) | 0.46152 (10) | 0.82747 (12) | 0.0561 (4) | |
| H14 | 0.7206 | 0.4577 | 0.7577 | 0.067* | |
| C15 | 0.8204 (2) | 0.39614 (10) | 0.88198 (14) | 0.0615 (5) | |
| H15 | 0.8599 | 0.3480 | 0.8490 | 0.074* | |
| C16 | 0.8481 (2) | 0.39985 (10) | 0.98705 (13) | 0.0558 (4) | |
| H16 | 0.9060 | 0.3546 | 1.0235 | 0.067* | |
| C17 | 0.79016 (19) | 0.46984 (9) | 1.03570 (11) | 0.0459 (3) | |
| H17 | 0.8084 | 0.4720 | 1.1056 | 0.055* | |
| C18 | 0.70267 (17) | 0.53921 (8) | 0.98165 (10) | 0.0370 (3) | |
| C19 | 0.64040 (17) | 0.61253 (9) | 1.02959 (9) | 0.0376 (3) | |
| H19 | 0.6579 | 0.6150 | 1.0994 | 0.045* | |
| H2 | 0.398 (2) | 0.8200 (12) | 0.9273 (7) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0763 (8) | 0.0503 (6) | 0.0362 (5) | 0.0137 (5) | 0.0089 (5) | 0.0025 (4) |
| O2 | 0.0943 (9) | 0.0461 (6) | 0.0267 (5) | 0.0082 (5) | 0.0067 (5) | −0.0025 (4) |
| O3 | 0.0792 (8) | 0.0541 (6) | 0.0249 (5) | 0.0150 (5) | 0.0074 (5) | 0.0044 (4) |
| N1 | 0.0482 (7) | 0.0378 (6) | 0.0375 (6) | −0.0002 (5) | 0.0085 (5) | −0.0037 (5) |
| N2 | 0.0546 (7) | 0.0381 (6) | 0.0302 (6) | 0.0043 (5) | 0.0072 (5) | −0.0025 (5) |
| C1 | 0.0418 (7) | 0.0381 (7) | 0.0388 (7) | −0.0053 (6) | 0.0063 (6) | −0.0028 (6) |
| C2 | 0.0435 (8) | 0.0392 (7) | 0.0375 (7) | −0.0052 (6) | 0.0059 (6) | −0.0016 (6) |
| C3 | 0.0600 (9) | 0.0390 (8) | 0.0502 (8) | 0.0048 (7) | 0.0007 (7) | −0.0027 (6) |
| C4 | 0.0891 (13) | 0.0515 (10) | 0.0554 (10) | 0.0164 (9) | −0.0042 (9) | −0.0200 (8) |
| C5 | 0.1083 (15) | 0.0666 (12) | 0.0402 (9) | 0.0207 (11) | −0.0087 (9) | −0.0189 (8) |
| C6 | 0.0726 (11) | 0.0507 (9) | 0.0398 (8) | 0.0091 (8) | −0.0047 (7) | −0.0034 (7) |
| C7 | 0.0817 (12) | 0.0653 (11) | 0.0412 (8) | 0.0150 (9) | 0.0030 (8) | 0.0094 (8) |
| C8 | 0.0514 (8) | 0.0423 (8) | 0.0338 (7) | 0.0004 (6) | 0.0087 (6) | 0.0007 (6) |
| C9 | 0.0471 (8) | 0.0370 (7) | 0.0279 (6) | −0.0065 (6) | 0.0071 (5) | −0.0007 (5) |
| C10 | 0.0398 (7) | 0.0376 (7) | 0.0274 (6) | −0.0055 (5) | 0.0060 (5) | −0.0005 (5) |
| C11 | 0.0457 (8) | 0.0412 (7) | 0.0279 (6) | −0.0021 (6) | 0.0063 (5) | 0.0036 (5) |
| C12 | 0.0595 (9) | 0.0474 (8) | 0.0261 (6) | −0.0037 (7) | 0.0102 (6) | −0.0022 (6) |
| C13 | 0.0468 (8) | 0.0398 (7) | 0.0385 (7) | −0.0054 (6) | 0.0137 (6) | −0.0024 (6) |
| C14 | 0.0767 (11) | 0.0485 (9) | 0.0469 (9) | −0.0011 (8) | 0.0237 (8) | −0.0075 (7) |
| C15 | 0.0700 (11) | 0.0409 (9) | 0.0788 (12) | 0.0036 (8) | 0.0303 (9) | −0.0059 (8) |
| C16 | 0.0529 (9) | 0.0421 (9) | 0.0737 (11) | 0.0035 (7) | 0.0128 (8) | 0.0066 (8) |
| C17 | 0.0446 (8) | 0.0430 (8) | 0.0498 (8) | −0.0024 (6) | 0.0039 (6) | 0.0051 (6) |
| C18 | 0.0362 (7) | 0.0372 (7) | 0.0381 (7) | −0.0056 (5) | 0.0068 (5) | 0.0009 (5) |
| C19 | 0.0427 (7) | 0.0415 (7) | 0.0280 (6) | −0.0058 (6) | 0.0023 (5) | 0.0003 (5) |
| O1—C2 | 1.3587 (16) | C7—H7B | 0.9600 |
| O1—C7 | 1.4190 (18) | C7—H7C | 0.9600 |
| O2—C9 | 1.2253 (15) | C8—H8 | 0.9300 |
| O3—C11 | 1.3683 (16) | C9—C10 | 1.4978 (18) |
| O3—H3 | 0.8200 | C10—C19 | 1.3713 (18) |
| N1—C8 | 1.2693 (17) | C10—C11 | 1.4287 (17) |
| N1—N2 | 1.3778 (15) | C11—C12 | 1.3635 (19) |
| N2—C9 | 1.3415 (17) | C12—C13 | 1.409 (2) |
| N2—H2 | 0.892 (9) | C12—H12 | 0.9300 |
| C1—C6 | 1.3889 (19) | C13—C18 | 1.4160 (18) |
| C1—C2 | 1.4000 (19) | C13—C14 | 1.419 (2) |
| C1—C8 | 1.4571 (19) | C14—C15 | 1.355 (2) |
| C2—C3 | 1.385 (2) | C14—H14 | 0.9300 |
| C3—C4 | 1.369 (2) | C15—C16 | 1.399 (2) |
| C3—H3A | 0.9300 | C15—H15 | 0.9300 |
| C4—C5 | 1.369 (2) | C16—C17 | 1.358 (2) |
| C4—H4 | 0.9300 | C16—H16 | 0.9300 |
| C5—C6 | 1.373 (2) | C17—C18 | 1.4101 (19) |
| C5—H5 | 0.9300 | C17—H17 | 0.9300 |
| C6—H6 | 0.9300 | C18—C19 | 1.4069 (19) |
| C7—H7A | 0.9600 | C19—H19 | 0.9300 |
| C2—O1—C7 | 117.92 (11) | O2—C9—N2 | 122.48 (12) |
| C11—O3—H3 | 109.5 | O2—C9—C10 | 120.42 (12) |
| C8—N1—N2 | 114.72 (11) | N2—C9—C10 | 117.10 (11) |
| C9—N2—N1 | 120.89 (11) | C19—C10—C11 | 117.92 (12) |
| C9—N2—H2 | 118.3 (12) | C19—C10—C9 | 115.53 (11) |
| N1—N2—H2 | 120.7 (12) | C11—C10—C9 | 126.54 (12) |
| C6—C1—C2 | 118.21 (13) | C12—C11—O3 | 121.40 (11) |
| C6—C1—C8 | 122.06 (13) | C12—C11—C10 | 120.25 (12) |
| C2—C1—C8 | 119.71 (12) | O3—C11—C10 | 118.34 (11) |
| O1—C2—C3 | 123.52 (13) | C11—C12—C13 | 121.71 (12) |
| O1—C2—C1 | 116.10 (12) | C11—C12—H12 | 119.1 |
| C3—C2—C1 | 120.38 (13) | C13—C12—H12 | 119.1 |
| C4—C3—C2 | 119.77 (14) | C12—C13—C18 | 118.92 (12) |
| C4—C3—H3A | 120.1 | C12—C13—C14 | 123.37 (13) |
| C2—C3—H3A | 120.1 | C18—C13—C14 | 117.71 (13) |
| C3—C4—C5 | 120.65 (15) | C15—C14—C13 | 120.96 (15) |
| C3—C4—H4 | 119.7 | C15—C14—H14 | 119.5 |
| C5—C4—H4 | 119.7 | C13—C14—H14 | 119.5 |
| C4—C5—C6 | 120.15 (15) | C14—C15—C16 | 121.09 (15) |
| C4—C5—H5 | 119.9 | C14—C15—H15 | 119.5 |
| C6—C5—H5 | 119.9 | C16—C15—H15 | 119.5 |
| C5—C6—C1 | 120.84 (15) | C17—C16—C15 | 119.77 (15) |
| C5—C6—H6 | 119.6 | C17—C16—H16 | 120.1 |
| C1—C6—H6 | 119.6 | C15—C16—H16 | 120.1 |
| O1—C7—H7A | 109.5 | C16—C17—C18 | 120.85 (14) |
| O1—C7—H7B | 109.5 | C16—C17—H17 | 119.6 |
| H7A—C7—H7B | 109.5 | C18—C17—H17 | 119.6 |
| O1—C7—H7C | 109.5 | C19—C18—C17 | 122.36 (12) |
| H7A—C7—H7C | 109.5 | C19—C18—C13 | 118.02 (12) |
| H7B—C7—H7C | 109.5 | C17—C18—C13 | 119.62 (12) |
| N1—C8—C1 | 122.61 (12) | C10—C19—C18 | 123.16 (12) |
| N1—C8—H8 | 118.7 | C10—C19—H19 | 118.4 |
| C1—C8—H8 | 118.7 | C18—C19—H19 | 118.4 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O3 | 0.89 (1) | 1.93 (1) | 2.6613 (14) | 138 (2) |
| O3—H3···O2i | 0.82 | 1.86 | 2.6689 (13) | 167 |
| Symmetry codes: (i) x, −y+3/2, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O3 | 0.89 (1) | 1.93 (1) | 2.6613 (14) | 138 (2) |
| O3—H3···O2i | 0.82 | 1.86 | 2.6689 (13) | 167 |
| Symmetry codes: (i) x, −y+3/2, z−1/2. |
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Schiff base compounds, important to the pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006), have been used as versatile ligands in a variety of coordination chemistry applications (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). A number of contributions to these areas have been recently reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). With our continued interest in the structural chararcterization of these compounds (Hao, 2009a,b) the title compound, C19H16N2O3, (I), is reported.
In the title compound,(I), the mean plane of the hydrazide group, O2/C9/N2/N1/C8, forms dihedral angles of 2.0 (2) and 2.2 (2)°, with the mean planes of the benzene (C1–C6) and naphthyl rings (C10–C19), respectively (Fig. 1). The dihedral angle between the mean planes of the benzene and naphthyl rings is 0.9 (2)°, indicating the planarity of the molecule. All the bond lengths and angles are within normal values (Allen et al., 1987). Crystal packing is enhanced by strong intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (Table 1), forming infinite one-dimensional chains running along the c axis of the unit cell (Fig. 2).