Acta Cryst. (2008). E64, o682 [ doi:10.1107/S1600536808006107 ]
The molecule of the title compound, C18H13NO3, is almost planar, the dihedral angle between the naphthalene and benzene ring systems being 4.04 (6)°. The molecular conformation and packing are stabilized by intramolecular O-H
N and intermolecular O-HO and C-HO interactions.
A solution of 4-aminobenzoic acid (5.0 g, 36.5 mmol) in hot ethanol was mixed with an ethanolic solution of 2-hydroxynaphthaldehyde (7.23 g, 36.5 mmol) and the resulting mixture was refluxed for 3 h. The mxiture was cooled to recover the crude product. Orange laths of (I) were recrystalized from ethanol. IR ν (cm-1); 1683.3 (C?O), 1588.1 (C?N), 1427.1 (C?C), 1301.4 (C—O) and 1152 (C—N). [M.p.: > 573 K, yield: 54.7%].
The H atoms were positioned geometrically (C—H = 0.93 Å, O—H = 0.82 Å) and refined as riding with with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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).
![[Figure 1]](./hb2705fig1thm.gif)
| Fig. 1. The molecular structure of (I), with displacement ellipsoids for the non-H atoms are drawn at the 50% probability level. |
![[Figure 2]](./hb2705fig2thm.gif)
| Fig. 2. The packing for (I) showing hydrogen bonds as dashed lines. |
| C18H13NO3 | F000 = 1216 |
| Mr = 291.29 | Dx = 1.433 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation λ = 0.71069 Å |
| Hall symbol: -C 2yc | Cell parameters from 3973 reflections |
| a = 14.7490 (12) Å | θ = 2.2–28.8º |
| b = 4.9850 (4) Å | µ = 0.10 mm−1 |
| c = 36.750 (3) Å | T = 150 (2) K |
| β = 91.305 (1)º | Lath, orange |
| V = 2701.3 (4) Å3 | 0.31 × 0.19 × 0.09 mm |
| Z = 8 |
| Bruker APEXII CCD diffractometer | 3520 independent reflections |
| Radiation source: sealed tube | 2761 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.031 |
| T = 150(2) K | θmax = 28.9º |
| φ and ω scans | θmin = 2.2º |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −20→19 |
| Tmin = 0.970, Tmax = 0.991 | k = −6→6 |
| 13445 measured reflections | l = −49→49 |
| 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)] = 0.050 | H-atom parameters constrained |
| wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0792P)2 + 1.0642P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 3520 reflections | Δρmax = 0.59 e Å−3 |
| 210 parameters | Δρmin = −0.33 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C18H13NO3 | V = 2701.3 (4) Å3 |
| Mr = 291.29 | Z = 8 |
| Monoclinic, C2/c | Mo Kα |
| a = 14.7490 (12) Å | µ = 0.10 mm−1 |
| b = 4.9850 (4) Å | T = 150 (2) K |
| c = 36.750 (3) Å | 0.31 × 0.19 × 0.09 mm |
| β = 91.305 (1)º |
| Bruker APEXII CCD diffractometer | 3520 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2761 reflections with I > 2σ(I) |
| Tmin = 0.970, Tmax = 0.991 | Rint = 0.031 |
| 13445 measured reflections |
| R[F2 > 2σ(F2)] = 0.050 | 210 parameters |
| wR(F2) = 0.145 | H-atom parameters constrained |
| S = 1.07 | Δρmax = 0.59 e Å−3 |
| 3520 reflections | Δρmin = −0.33 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.11588 (7) | 0.8430 (3) | 0.11623 (4) | 0.0398 (4) | |
| O2 | 0.39188 (7) | −0.3435 (2) | 0.00066 (3) | 0.0295 (3) | |
| O3 | 0.52323 (6) | −0.2551 (2) | 0.03002 (3) | 0.0277 (3) | |
| N1 | 0.26607 (8) | 0.6069 (2) | 0.10400 (3) | 0.0232 (3) | |
| C1 | 0.15748 (10) | 0.9891 (3) | 0.13926 (4) | 0.0293 (4) | |
| C2 | 0.10809 (11) | 1.1871 (4) | 0.15946 (5) | 0.0387 (5) | |
| C3 | 0.14890 (11) | 1.3471 (3) | 0.18415 (5) | 0.0368 (5) | |
| C4 | 0.24458 (10) | 1.3336 (3) | 0.19194 (4) | 0.0273 (4) | |
| C5 | 0.28528 (12) | 1.5100 (3) | 0.21737 (4) | 0.0333 (4) | |
| C6 | 0.37653 (13) | 1.5035 (3) | 0.22449 (4) | 0.0367 (5) | |
| C7 | 0.43000 (12) | 1.3207 (3) | 0.20591 (5) | 0.0382 (5) | |
| C8 | 0.39165 (11) | 1.1460 (3) | 0.18077 (4) | 0.0328 (4) | |
| C9 | 0.29754 (10) | 1.1446 (3) | 0.17322 (4) | 0.0235 (4) | |
| C10 | 0.25387 (9) | 0.9658 (3) | 0.14694 (4) | 0.0227 (3) | |
| C11 | 0.30277 (9) | 0.7702 (3) | 0.12869 (4) | 0.0222 (3) | |
| C12 | 0.31172 (9) | 0.4082 (3) | 0.08444 (4) | 0.0216 (3) | |
| C13 | 0.26106 (9) | 0.2595 (3) | 0.05899 (4) | 0.0237 (4) | |
| C14 | 0.30229 (9) | 0.0589 (3) | 0.03908 (4) | 0.0236 (4) | |
| C15 | 0.39461 (9) | 0.0041 (3) | 0.04452 (4) | 0.0212 (3) | |
| C16 | 0.44479 (9) | 0.1537 (3) | 0.07000 (4) | 0.0237 (4) | |
| C17 | 0.40437 (9) | 0.3544 (3) | 0.08974 (4) | 0.0237 (4) | |
| C18 | 0.44065 (9) | −0.2106 (3) | 0.02406 (4) | 0.0224 (3) | |
| HO1 | 0.15250 | 0.74990 | 0.10550 | 0.0600* | |
| H2 | 0.04600 | 1.20430 | 0.15520 | 0.053 (6)* | |
| HO2 | 0.42310 | −0.45920 | −0.00880 | 0.0440* | |
| H3 | 0.11410 | 1.47080 | 0.19660 | 0.046 (5)* | |
| H5 | 0.24950 | 1.63300 | 0.22950 | 0.041 (5)* | |
| H6 | 0.40270 | 1.61950 | 0.24150 | 0.045 (5)* | |
| H7 | 0.49230 | 1.31630 | 0.21050 | 0.058 (6)* | |
| H8 | 0.42870 | 1.02670 | 0.16860 | 0.037 (5)* | |
| H11 | 0.36440 | 0.75340 | 0.13410 | 0.0270* | |
| H13 | 0.19960 | 0.29500 | 0.05540 | 0.0280* | |
| H14 | 0.26850 | −0.03930 | 0.02210 | 0.031 (4)* | |
| H16 | 0.50620 | 0.11760 | 0.07370 | 0.022 (4)* | |
| H17 | 0.43850 | 0.45380 | 0.10650 | 0.031 (4)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0220 (5) | 0.0457 (7) | 0.0513 (7) | 0.0052 (5) | −0.0055 (5) | −0.0177 (6) |
| O2 | 0.0250 (5) | 0.0288 (5) | 0.0348 (6) | −0.0002 (4) | 0.0003 (4) | −0.0125 (4) |
| O3 | 0.0212 (5) | 0.0280 (5) | 0.0340 (5) | 0.0019 (4) | 0.0017 (4) | −0.0052 (4) |
| N1 | 0.0220 (5) | 0.0239 (6) | 0.0238 (6) | 0.0009 (4) | 0.0003 (4) | −0.0034 (4) |
| C1 | 0.0236 (7) | 0.0307 (7) | 0.0336 (8) | 0.0035 (6) | 0.0012 (6) | −0.0026 (6) |
| C2 | 0.0244 (7) | 0.0432 (9) | 0.0485 (10) | 0.0085 (7) | 0.0031 (7) | −0.0090 (8) |
| C3 | 0.0340 (8) | 0.0371 (8) | 0.0396 (9) | 0.0111 (7) | 0.0078 (7) | −0.0078 (7) |
| C4 | 0.0359 (8) | 0.0237 (7) | 0.0224 (7) | 0.0030 (6) | 0.0047 (5) | 0.0017 (5) |
| C5 | 0.0487 (9) | 0.0257 (7) | 0.0257 (7) | 0.0055 (7) | 0.0049 (6) | −0.0032 (6) |
| C6 | 0.0533 (10) | 0.0281 (7) | 0.0285 (8) | −0.0041 (7) | −0.0049 (7) | −0.0053 (6) |
| C7 | 0.0379 (9) | 0.0361 (8) | 0.0402 (9) | −0.0015 (7) | −0.0091 (7) | −0.0079 (7) |
| C8 | 0.0319 (8) | 0.0295 (7) | 0.0368 (8) | 0.0039 (6) | −0.0038 (6) | −0.0084 (6) |
| C9 | 0.0287 (7) | 0.0204 (6) | 0.0213 (6) | 0.0014 (5) | 0.0020 (5) | 0.0011 (5) |
| C10 | 0.0233 (6) | 0.0226 (6) | 0.0222 (6) | 0.0009 (5) | 0.0012 (5) | 0.0000 (5) |
| C11 | 0.0209 (6) | 0.0230 (6) | 0.0228 (6) | 0.0005 (5) | 0.0000 (5) | 0.0001 (5) |
| C12 | 0.0219 (6) | 0.0215 (6) | 0.0214 (6) | 0.0000 (5) | 0.0016 (5) | −0.0002 (5) |
| C13 | 0.0182 (6) | 0.0264 (7) | 0.0264 (7) | 0.0009 (5) | −0.0023 (5) | −0.0018 (5) |
| C14 | 0.0223 (6) | 0.0246 (6) | 0.0237 (7) | −0.0021 (5) | −0.0022 (5) | −0.0031 (5) |
| C15 | 0.0206 (6) | 0.0210 (6) | 0.0221 (6) | −0.0017 (5) | 0.0018 (5) | −0.0010 (5) |
| C16 | 0.0188 (6) | 0.0261 (7) | 0.0263 (7) | −0.0006 (5) | −0.0001 (5) | −0.0033 (5) |
| C17 | 0.0210 (6) | 0.0258 (7) | 0.0243 (6) | −0.0020 (5) | −0.0016 (5) | −0.0048 (5) |
| C18 | 0.0223 (6) | 0.0214 (6) | 0.0235 (6) | −0.0025 (5) | 0.0027 (5) | −0.0013 (5) |
| O1—C1 | 1.265 (2) | C12—C17 | 1.4018 (19) |
| O2—C18 | 1.2914 (18) | C12—C13 | 1.397 (2) |
| O3—C18 | 1.2524 (16) | C13—C14 | 1.388 (2) |
| O1—HO1 | 0.8200 | C14—C15 | 1.3987 (19) |
| O2—HO2 | 0.8200 | C15—C16 | 1.396 (2) |
| N1—C12 | 1.4047 (18) | C15—C18 | 1.482 (2) |
| N1—C11 | 1.3254 (18) | C16—C17 | 1.379 (2) |
| C1—C2 | 1.442 (2) | C2—H2 | 0.9300 |
| C1—C10 | 1.448 (2) | C3—H3 | 0.9300 |
| C2—C3 | 1.341 (3) | C5—H5 | 0.9300 |
| C3—C4 | 1.435 (2) | C6—H6 | 0.9300 |
| C4—C9 | 1.413 (2) | C7—H7 | 0.9300 |
| C4—C5 | 1.408 (2) | C8—H8 | 0.9300 |
| C5—C6 | 1.366 (3) | C11—H11 | 0.9300 |
| C6—C7 | 1.394 (2) | C13—H13 | 0.9300 |
| C7—C8 | 1.381 (2) | C14—H14 | 0.9300 |
| C8—C9 | 1.409 (2) | C16—H16 | 0.9300 |
| C9—C10 | 1.454 (2) | C17—H17 | 0.9300 |
| C10—C11 | 1.394 (2) | ||
| C1—O1—HO1 | 109.00 | C14—C15—C18 | 121.63 (13) |
| C18—O2—HO2 | 109.00 | C15—C16—C17 | 120.76 (13) |
| C11—N1—C12 | 126.19 (12) | C12—C17—C16 | 119.83 (13) |
| O1—C1—C2 | 119.70 (14) | O3—C18—C15 | 119.63 (13) |
| C2—C1—C10 | 117.37 (13) | O2—C18—O3 | 123.39 (13) |
| O1—C1—C10 | 122.92 (14) | O2—C18—C15 | 116.99 (12) |
| C1—C2—C3 | 122.09 (15) | C1—C2—H2 | 119.00 |
| C2—C3—C4 | 122.11 (15) | C3—C2—H2 | 119.00 |
| C3—C4—C9 | 119.09 (14) | C2—C3—H3 | 119.00 |
| C3—C4—C5 | 120.38 (14) | C4—C3—H3 | 119.00 |
| C5—C4—C9 | 120.52 (14) | C4—C5—H5 | 119.00 |
| C4—C5—C6 | 121.06 (14) | C6—C5—H5 | 119.00 |
| C5—C6—C7 | 119.19 (15) | C5—C6—H6 | 120.00 |
| C6—C7—C8 | 120.81 (16) | C7—C6—H6 | 120.00 |
| C7—C8—C9 | 121.42 (14) | C6—C7—H7 | 120.00 |
| C4—C9—C10 | 119.40 (13) | C8—C7—H7 | 120.00 |
| C4—C9—C8 | 116.99 (13) | C7—C8—H8 | 119.00 |
| C8—C9—C10 | 123.59 (13) | C9—C8—H8 | 119.00 |
| C1—C10—C11 | 118.61 (13) | N1—C11—H11 | 118.00 |
| C1—C10—C9 | 119.90 (13) | C10—C11—H11 | 118.00 |
| C9—C10—C11 | 121.48 (12) | C12—C13—H13 | 120.00 |
| N1—C11—C10 | 123.46 (12) | C14—C13—H13 | 120.00 |
| N1—C12—C17 | 122.74 (13) | C13—C14—H14 | 120.00 |
| C13—C12—C17 | 119.77 (13) | C15—C14—H14 | 120.00 |
| N1—C12—C13 | 117.49 (12) | C15—C16—H16 | 120.00 |
| C12—C13—C14 | 120.09 (12) | C17—C16—H16 | 120.00 |
| C13—C14—C15 | 120.15 (13) | C12—C17—H17 | 120.00 |
| C14—C15—C16 | 119.41 (13) | C16—C17—H17 | 120.00 |
| C16—C15—C18 | 118.96 (12) | ||
| C12—N1—C11—C10 | 179.29 (14) | C7—C8—C9—C10 | 179.74 (15) |
| C11—N1—C12—C13 | −178.82 (14) | C4—C9—C10—C1 | 2.2 (2) |
| C11—N1—C12—C17 | 1.6 (2) | C4—C9—C10—C11 | −177.85 (14) |
| O1—C1—C2—C3 | −179.95 (18) | C8—C9—C10—C1 | −176.23 (14) |
| C10—C1—C2—C3 | 0.8 (3) | C8—C9—C10—C11 | 3.8 (2) |
| O1—C1—C10—C9 | 178.67 (15) | C1—C10—C11—N1 | 1.4 (2) |
| O1—C1—C10—C11 | −1.3 (2) | C9—C10—C11—N1 | −178.55 (14) |
| C2—C1—C10—C9 | −2.1 (2) | N1—C12—C13—C14 | −179.43 (13) |
| C2—C1—C10—C11 | 177.93 (15) | C17—C12—C13—C14 | 0.1 (2) |
| C1—C2—C3—C4 | 0.5 (3) | N1—C12—C17—C16 | 179.04 (13) |
| C2—C3—C4—C5 | 178.31 (16) | C13—C12—C17—C16 | −0.5 (2) |
| C2—C3—C4—C9 | −0.5 (2) | C12—C13—C14—C15 | 0.3 (2) |
| C3—C4—C5—C6 | −178.57 (15) | C13—C14—C15—C16 | −0.3 (2) |
| C9—C4—C5—C6 | 0.2 (2) | C13—C14—C15—C18 | 179.30 (14) |
| C3—C4—C9—C8 | 177.61 (14) | C14—C15—C16—C17 | −0.1 (2) |
| C3—C4—C9—C10 | −0.9 (2) | C18—C15—C16—C17 | −179.67 (14) |
| C5—C4—C9—C8 | −1.1 (2) | C14—C15—C18—O2 | 0.7 (2) |
| C5—C4—C9—C10 | −179.65 (14) | C14—C15—C18—O3 | −179.25 (14) |
| C4—C5—C6—C7 | 0.7 (2) | C16—C15—C18—O2 | −179.75 (13) |
| C5—C6—C7—C8 | −0.5 (2) | C16—C15—C18—O3 | 0.3 (2) |
| C6—C7—C8—C9 | −0.5 (2) | C15—C16—C17—C12 | 0.5 (2) |
| C7—C8—C9—C4 | 1.3 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—HO1···N1 | 0.82 | 1.82 | 2.5572 (16) | 148 |
| O2—HO2···O3i | 0.82 | 1.81 | 2.6281 (14) | 171 |
| C14—H14···O2ii | 0.93 | 2.56 | 3.3611 (17) | 145 |
| C16—H16···O1iii | 0.93 | 2.49 | 3.1542 (19) | 128 |
| Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x+1/2, −y−1/2, −z; (iii) x+1/2, y−1/2, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—HO1···N1 | 0.82 | 1.82 | 2.5572 (16) | 148 |
| O2—HO2···O3i | 0.82 | 1.81 | 2.6281 (14) | 171 |
| C14—H14···O2ii | 0.93 | 2.56 | 3.3611 (17) | 145 |
| C16—H16···O1iii | 0.93 | 2.49 | 3.1542 (19) | 128 |
| Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x+1/2, −y−1/2, −z; (iii) x+1/2, y−1/2, z. |
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.
Asiri, A. M. & Badahdah, K. O. (2007). Molecules, 12, 1796-1804.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
2-Hydroxy Schiff base ligands and their complexes, derived from the reaction of salicylaldehyde and 2-hydroxy-1-naphthaldehyde with amines are of interest due to the existence of (O—H ···N and N—H ···O) type hydrogen bonds and tautomerism between the enol-imine and keto-enamine forms. Tautomerism in 2-hydroxy Schiff bases both in solution and in the solid state was investigated using different spectroscopic techniques (Asiri & Badahdah, 2007).
In the title compound, (I), the molecule is almost planar (Fig. 1). The maximum deviation of the non-H atoms from their mean plane is 0.087 (1) Å for O3. The dihedral angle between the naphthalene ring and the benzene ring is 4.04 (6)°.
The molecular conformation is stabilized by an intramolecular O—H···N hydrogen bond (Table 1). Then, classical inversion dimers are formed by head-to-head O—H···O linkages of the carboxylic acid groups. Finally, C—H ···O interactions link the dimers into sheets (Fig. 2).