Acta Cryst. (2008). E64, o813 [ doi:10.1107/S1600536808009082 ]
The title compound, NH4+·C11H7O3-, was obtained by slow evaporation of a 30% ammonia solution of 1-hydroxy-2-naphthoic acid. The crystal structure is stabilized by intermolecular N-H
O hydrogen bonds, forming layers parallel to the bc plane.
Single crystals of the title compound were obtained by slow evaporation of a 30% ammonia solution of 1-hydroxynaphthalene-2-carboxylic acid in air.
Ammonium H atoms were located from a difference Fourier map and refined isotropically, with N–H distances restrained to 0.90 (1) Å, H···H distances restrained to 1.43 (2) Å, and with Uiso(H) values fixed at 0.08 Å2. All other H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances of 0.93 Å, O–H distance of 0.82 Å, and with Uiso(H) set at 1.2Ueq(C) or 1.5Ueq(O).
Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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]](./rz2202fig1thm.gif)
| Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular hydrogen bond is shown as a dashed line. |
![[Figure 2]](./rz2202fig2thm.gif)
| Fig. 2. A perspective view of crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines. |
| N1H4+·C11H7O3– | F000 = 864 |
| Mr = 205.21 | Dx = 1.449 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 1379 reflections |
| a = 30.883 (5) Å | θ = 2.5–24.1º |
| b = 3.880 (1) Å | µ = 0.11 mm−1 |
| c = 15.777 (3) Å | T = 298 (2) K |
| β = 95.567 (2)º | Block, colourless |
| V = 1881.6 (7) Å3 | 0.23 × 0.23 × 0.20 mm |
| Z = 8 |
| Bruker SMART CCD area-detector diffractometer | 1915 independent reflections |
| Radiation source: fine-focus sealed tube | 1351 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.040 |
| T = 298(2) K | θmax = 27.0º |
| ω scans | θmin = 2.6º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −38→38 |
| Tmin = 0.976, Tmax = 0.979 | k = −4→4 |
| 6728 measured reflections | l = −20→19 |
| 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)] = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.226 | w = 1/[σ2(Fo2) + (0.1461P)2 + 0.0944P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 1915 reflections | Δρmax = 0.55 e Å−3 |
| 149 parameters | Δρmin = −0.24 e Å−3 |
| 10 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| N1H4+·C11H7O3– | V = 1881.6 (7) Å3 |
| Mr = 205.21 | Z = 8 |
| Monoclinic, C2/c | Mo Kα |
| a = 30.883 (5) Å | µ = 0.11 mm−1 |
| b = 3.880 (1) Å | T = 298 (2) K |
| c = 15.777 (3) Å | 0.23 × 0.23 × 0.20 mm |
| β = 95.567 (2)º |
| Bruker SMART CCD area-detector diffractometer | 1915 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1351 reflections with I > 2σ(I) |
| Tmin = 0.976, Tmax = 0.979 | Rint = 0.040 |
| 6728 measured reflections |
| R[F2 > 2σ(F2)] = 0.080 | 10 restraints |
| wR(F2) = 0.226 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | Δρmax = 0.55 e Å−3 |
| 1915 reflections | Δρmin = −0.24 e Å−3 |
| 149 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.42976 (6) | 1.0366 (6) | 0.70025 (11) | 0.0383 (6) | |
| H1 | 0.4496 | 1.0981 | 0.7354 | 0.057* | |
| O2 | 0.46982 (6) | 1.1294 (6) | 0.84111 (13) | 0.0472 (6) | |
| O3 | 0.44313 (7) | 0.9570 (6) | 0.95912 (12) | 0.0486 (7) | |
| N1 | 0.46529 (8) | 0.4511 (7) | 0.08424 (16) | 0.0414 (7) | |
| C1 | 0.39678 (8) | 0.9092 (6) | 0.74083 (16) | 0.0259 (6) | |
| C2 | 0.39995 (8) | 0.8798 (7) | 0.82806 (16) | 0.0281 (6) | |
| C3 | 0.36469 (8) | 0.7397 (7) | 0.86694 (16) | 0.0322 (6) | |
| H3 | 0.3666 | 0.7214 | 0.9260 | 0.039* | |
| C4 | 0.32803 (9) | 0.6309 (8) | 0.82012 (17) | 0.0354 (7) | |
| H4 | 0.3052 | 0.5392 | 0.8474 | 0.042* | |
| C5 | 0.32420 (8) | 0.6559 (7) | 0.73053 (17) | 0.0291 (6) | |
| C6 | 0.28703 (9) | 0.5425 (7) | 0.67931 (19) | 0.0380 (7) | |
| H6 | 0.2640 | 0.4471 | 0.7050 | 0.046* | |
| C7 | 0.28423 (9) | 0.5700 (8) | 0.5933 (2) | 0.0441 (8) | |
| H7 | 0.2594 | 0.4931 | 0.5606 | 0.053* | |
| C8 | 0.31858 (10) | 0.7139 (8) | 0.55356 (18) | 0.0424 (8) | |
| H8 | 0.3165 | 0.7321 | 0.4945 | 0.051* | |
| C9 | 0.35487 (9) | 0.8268 (8) | 0.60050 (17) | 0.0358 (7) | |
| H9 | 0.3773 | 0.9242 | 0.5733 | 0.043* | |
| C10 | 0.35900 (8) | 0.7985 (7) | 0.68970 (16) | 0.0268 (6) | |
| C11 | 0.43967 (9) | 0.9947 (7) | 0.88135 (17) | 0.0321 (7) | |
| H1A | 0.4533 (9) | 0.347 (7) | 0.1262 (14) | 0.080* | |
| H1B | 0.4891 (7) | 0.565 (8) | 0.1041 (18) | 0.080* | |
| H1C | 0.4720 (10) | 0.291 (6) | 0.0471 (16) | 0.080* | |
| H1D | 0.4467 (8) | 0.597 (7) | 0.0576 (18) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0294 (10) | 0.0542 (14) | 0.0317 (10) | −0.0088 (9) | 0.0045 (8) | 0.0017 (9) |
| O2 | 0.0307 (10) | 0.0587 (15) | 0.0509 (13) | −0.0139 (9) | −0.0027 (9) | −0.0017 (11) |
| O3 | 0.0537 (13) | 0.0560 (15) | 0.0326 (11) | −0.0071 (10) | −0.0135 (10) | −0.0059 (10) |
| N1 | 0.0445 (14) | 0.0356 (14) | 0.0439 (14) | −0.0050 (11) | 0.0037 (12) | −0.0057 (11) |
| C1 | 0.0240 (12) | 0.0254 (13) | 0.0293 (13) | 0.0014 (9) | 0.0070 (10) | −0.0002 (10) |
| C2 | 0.0273 (13) | 0.0253 (14) | 0.0310 (13) | 0.0001 (10) | 0.0003 (10) | −0.0035 (10) |
| C3 | 0.0371 (14) | 0.0330 (15) | 0.0269 (13) | −0.0017 (12) | 0.0057 (11) | 0.0026 (11) |
| C4 | 0.0329 (14) | 0.0391 (17) | 0.0352 (14) | −0.0060 (11) | 0.0085 (12) | 0.0052 (12) |
| C5 | 0.0246 (12) | 0.0264 (14) | 0.0359 (14) | 0.0022 (10) | 0.0010 (10) | 0.0016 (11) |
| C6 | 0.0306 (14) | 0.0337 (16) | 0.0488 (16) | −0.0029 (11) | −0.0010 (12) | −0.0043 (13) |
| C7 | 0.0338 (15) | 0.0469 (19) | 0.0480 (17) | 0.0026 (12) | −0.0146 (13) | −0.0136 (14) |
| C8 | 0.0440 (16) | 0.0515 (19) | 0.0289 (14) | 0.0107 (14) | −0.0100 (12) | −0.0052 (13) |
| C9 | 0.0343 (14) | 0.0436 (17) | 0.0300 (14) | 0.0060 (12) | 0.0049 (11) | −0.0019 (12) |
| C10 | 0.0263 (12) | 0.0239 (13) | 0.0297 (13) | 0.0024 (10) | 0.0000 (10) | −0.0007 (10) |
| C11 | 0.0346 (14) | 0.0271 (14) | 0.0331 (14) | −0.0008 (11) | −0.0044 (11) | −0.0041 (11) |
| O1—C1 | 1.349 (3) | C3—H3 | 0.9300 |
| O1—H1 | 0.8200 | C4—C5 | 1.410 (4) |
| O2—C11 | 1.287 (3) | C4—H4 | 0.9300 |
| O3—C11 | 1.230 (3) | C5—C6 | 1.409 (4) |
| N1—H1A | 0.89 (2) | C5—C10 | 1.418 (4) |
| N1—H1B | 0.89 (3) | C6—C7 | 1.356 (4) |
| N1—H1C | 0.89 (2) | C6—H6 | 0.9300 |
| N1—H1D | 0.88 (3) | C7—C8 | 1.400 (4) |
| C1—C2 | 1.375 (4) | C7—H7 | 0.9300 |
| C1—C10 | 1.419 (3) | C8—C9 | 1.355 (4) |
| C2—C3 | 1.410 (3) | C8—H8 | 0.9300 |
| C2—C11 | 1.487 (3) | C9—C10 | 1.405 (4) |
| C3—C4 | 1.358 (4) | C9—H9 | 0.9300 |
| C1—O1—H1 | 109.5 | C6—C5—C10 | 118.2 (3) |
| H1A—N1—H1B | 110.8 (19) | C4—C5—C10 | 119.3 (2) |
| H1A—N1—H1C | 108 (2) | C7—C6—C5 | 121.3 (3) |
| H1B—N1—H1C | 110.0 (19) | C7—C6—H6 | 119.4 |
| H1A—N1—H1D | 110 (2) | C5—C6—H6 | 119.4 |
| H1B—N1—H1D | 109 (2) | C6—C7—C8 | 120.1 (3) |
| H1C—N1—H1D | 108.3 (19) | C6—C7—H7 | 119.9 |
| O1—C1—C2 | 121.5 (2) | C8—C7—H7 | 119.9 |
| O1—C1—C10 | 117.3 (2) | C9—C8—C7 | 120.5 (3) |
| C2—C1—C10 | 121.2 (2) | C9—C8—H8 | 119.8 |
| C1—C2—C3 | 119.0 (2) | C7—C8—H8 | 119.8 |
| C1—C2—C11 | 121.1 (2) | C8—C9—C10 | 120.8 (3) |
| C3—C2—C11 | 120.0 (2) | C8—C9—H9 | 119.6 |
| C4—C3—C2 | 121.4 (2) | C10—C9—H9 | 119.6 |
| C4—C3—H3 | 119.3 | C9—C10—C5 | 119.1 (2) |
| C2—C3—H3 | 119.3 | C9—C10—C1 | 122.4 (2) |
| C3—C4—C5 | 120.5 (2) | C5—C10—C1 | 118.5 (2) |
| C3—C4—H4 | 119.7 | O3—C11—O2 | 122.9 (2) |
| C5—C4—H4 | 119.7 | O3—C11—C2 | 121.0 (3) |
| C6—C5—C4 | 122.5 (3) | O2—C11—C2 | 116.1 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2 | 0.82 | 1.73 | 2.463 (3) | 148 |
| N1—H1A···O1i | 0.89 (2) | 2.07 (3) | 2.920 (3) | 161 (3) |
| N1—H1B···O2ii | 0.89 (3) | 1.88 (3) | 2.756 (3) | 167 (3) |
| N1—H1C···O3iii | 0.89 (2) | 2.04 (2) | 2.789 (3) | 141 (3) |
| N1—H1D···O3iv | 0.88 (3) | 2.08 (2) | 2.821 (3) | 140 (3) |
| Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z−1; (iv) x, y, z−1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2 | 0.82 | 1.73 | 2.463 (3) | 148 |
| N1—H1A···O1i | 0.89 (2) | 2.07 (3) | 2.920 (3) | 161 (3) |
| N1—H1B···O2ii | 0.89 (3) | 1.88 (3) | 2.756 (3) | 167 (3) |
| N1—H1C···O3iii | 0.89 (2) | 2.04 (2) | 2.789 (3) | 141 (3) |
| N1—H1D···O3iv | 0.88 (3) | 2.08 (2) | 2.821 (3) | 140 (3) |
| Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z−1; (iv) x, y, z−1. |
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Song, W.-D., Yan, J.-B., Wang, H. & Ji, L.-L. (2008). Acta Cryst. E64, m5.
1-Hydroxynaphthalene-2-carboxylic acid is a widely used ligand for the synthesis of metal complexes (Kickelbick & Schubert, 1999; Ohki et al., 1986; Song et al., 2008). We report herein the crystal structure of the title compound, which was obtained by slow evaporation of a 30% ammonium solution of 1-hydroxynaphthalene-2-carboxylic acid in air.
The compound consists of discrete 1-hydroxynaphthalene-2-carboxylate anions and ammonium cations (Fig. 1). The anion is substantially planar with a mean deviation of 0.015 (3) Å. The crystal structure is stabilized by intermolecular N–H···O hydrogen bonds (Table 1), forming layers parallel to the bc plane (Fig. 2).