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Acta Cryst. (2008). E64, o1753    [ doi:10.1107/S1600536808025567 ]

Piperidinium 3-hydroxy-2-naphthoate

Y.-T. Wang, G.-M. Tang, Y.-C. Zhang and W.-Z. Wan

Abstract top

The crystals of the title salt, C5H12N+·C11H7O3-, were obtained from a methanol/water solution of 3-hydroxy-2-naphthoic acid and piperidine at room temperature. In the crystal structure, the piperidinium cations display a chair conformation and link with hydroxynaphthoate anions via N-H...O and C-H...O hydrogen bonds. An intramolecular O-H...O interaction is also present.

Comment top

In some biological system, intermolecular interactions play the important role (Shen et al., 2008), these interactions have attracted our much attention in past years. A series of compounds with weak intermolecular interactions have been synthesized and their crystal structures have been characterized (Wang et al., 2005a,b, 2006). As part of our investigation, we recently prepared the title compound and present here its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit contains one 3-hydroxy-2-naphthoate anion and one piperidinium cation. The piperidinium cation displays a typical chair conformation. The carboxylate group is coplanar with the naphthalene ring. Intermolecular N—H···O and C—H···O hydrogen bonding presents in the crystal structure (Table 1).

Related literature top

For background, see: Shen et al. (2008); Wang et al. (2005a,b, 2006).

Experimental top

3-Hydroxy-2-naphthoic acid (94 mg, 0.5 mmol) and piperidine (43 mg, 0.5 mmol) were dissolved in methanol (5 ml) and water (1 ml) at room temperature. The single crystals of the title compound were obtained from the solution after several days.

Refinement top

H atoms were placed in calculated positions with O—H = 0.82, N—H = 0.96, C—H = 0.93 (aromatic) or 0.97 Å (methylene), and refined in riding mode with Uiso(H) = 1.5Ueq(O,N) and 1.2Uiso(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A drawing of (I), with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Piperidinium 3-hydroxy-2-naphthoate top
Crystal data top
C5H12N+·C11H7O3−F(000) = 584
Mr = 273.32Dx = 1.210 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1627 reflections
a = 8.6683 (3) Åθ = 2.5–20.5°
b = 19.4537 (5) ŵ = 0.08 mm−1
c = 9.5932 (3) ÅT = 298 K
β = 111.959 (2)°Block, colourless
V = 1500.34 (8) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		1512 reflections with I > σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
graphiteθmax = 27.4°, θmin = 2.1°
φ and ω scansh = −9→11
10640 measured reflectionsk = −25→22
3385 independent reflectionsl = −12→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0733P)2]
where P = (Fo2 + 2Fc2)/3
3385 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.13 e Å−3
Crystal data top
C5H12N+·C11H7O3−V = 1500.34 (8) Å3
Mr = 273.32Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.6683 (3) ŵ = 0.08 mm−1
b = 19.4537 (5) ÅT = 298 K
c = 9.5932 (3) Å0.40 × 0.30 × 0.20 mm
β = 111.959 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		1512 reflections with I > σ(I)
10640 measured reflectionsRint = 0.035
3385 independent reflectionsθmax = 27.4°
Refinement top
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.160Δρmax = 0.13 e Å−3
S = 0.99Δρmin = −0.13 e Å−3
3385 reflectionsAbsolute structure: ?
181 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
N1−0.1726 (2)0.09197 (8)0.39856 (18)0.0718 (5)
H1C−0.19790.04910.43460.108*
H1D−0.06260.10540.46350.108*
O10.31760 (19)0.22455 (7)0.73435 (18)0.0944 (5)
H1B0.23310.20510.67860.142*
O20.24997 (18)0.03674 (7)0.51894 (15)0.0832 (5)
O30.14101 (19)0.13370 (8)0.56381 (18)0.0948 (5)
C10.6069 (3)0.20988 (10)0.8318 (2)0.0692 (6)
H1A0.61760.25300.87630.083*
C20.4523 (3)0.18561 (9)0.7481 (2)0.0636 (5)
C30.4321 (2)0.12071 (9)0.67629 (19)0.0561 (5)
C40.5718 (3)0.08253 (9)0.69633 (19)0.0604 (5)
H4A0.55970.03980.64980.072*
C50.7325 (3)0.10544 (10)0.7844 (2)0.0629 (5)
C60.8758 (3)0.06627 (12)0.8062 (3)0.0930 (7)
H6A0.86540.02290.76260.112*
C71.0287 (3)0.09073 (16)0.8897 (3)0.1178 (10)
H7A1.12230.06420.90270.141*
C81.0468 (3)0.15586 (15)0.9569 (3)0.1102 (9)
H8A1.15240.17241.01370.132*
C90.9119 (3)0.19463 (12)0.9394 (2)0.0838 (6)
H9A0.92560.23750.98520.101*
C100.7497 (3)0.17107 (10)0.8523 (2)0.0623 (5)
C110.2638 (3)0.09412 (11)0.5796 (2)0.0669 (6)
C12−0.2927 (3)0.14545 (10)0.4042 (2)0.0772 (6)
H12A−0.26190.18950.37490.093*
H12B−0.28930.14950.50610.093*
C13−0.4652 (3)0.12680 (12)0.3005 (3)0.0900 (7)
H13A−0.54120.16340.30040.108*
H13B−0.50010.08530.33660.108*
C14−0.4732 (3)0.11527 (13)0.1424 (3)0.0995 (8)
H14A−0.58370.09960.07980.119*
H14B−0.45250.15830.10150.119*
C15−0.3471 (3)0.06288 (13)0.1397 (2)0.0857 (7)
H15A−0.37590.01840.16900.103*
H15B−0.34900.05890.03830.103*
C16−0.1763 (3)0.08263 (11)0.2440 (3)0.0852 (7)
H16A−0.09790.04710.24390.102*
H16B−0.14340.12510.20970.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0655 (12)0.0642 (11)0.0731 (11)−0.0064 (8)0.0116 (9)0.0044 (8)
O10.0755 (11)0.0761 (10)0.1167 (13)0.0101 (8)0.0186 (9)−0.0260 (8)
O20.0942 (12)0.0604 (9)0.0768 (10)−0.0154 (7)0.0110 (8)−0.0074 (7)
O30.0677 (11)0.0869 (11)0.1111 (13)−0.0032 (9)0.0121 (9)−0.0172 (9)
C10.0774 (16)0.0539 (11)0.0683 (13)−0.0059 (11)0.0182 (12)−0.0120 (9)
C20.0689 (15)0.0538 (12)0.0641 (12)0.0031 (11)0.0203 (11)−0.0032 (9)
C30.0682 (14)0.0483 (10)0.0481 (10)−0.0035 (9)0.0176 (9)0.0014 (8)
C40.0753 (15)0.0505 (11)0.0529 (11)−0.0009 (10)0.0211 (10)−0.0031 (8)
C50.0656 (14)0.0660 (13)0.0545 (11)0.0015 (11)0.0192 (10)−0.0012 (9)
C60.0789 (19)0.0897 (16)0.0979 (17)0.0125 (14)0.0187 (14)−0.0205 (13)
C70.071 (2)0.130 (2)0.131 (2)0.0165 (16)0.0138 (17)−0.0327 (19)
C80.0669 (19)0.126 (2)0.119 (2)−0.0029 (16)0.0122 (15)−0.0265 (18)
C90.0794 (17)0.0836 (15)0.0786 (15)−0.0114 (13)0.0181 (13)−0.0138 (12)
C100.0655 (14)0.0637 (13)0.0536 (11)−0.0056 (10)0.0174 (10)−0.0023 (9)
C110.0755 (16)0.0566 (13)0.0604 (12)−0.0084 (12)0.0160 (11)0.0031 (10)
C120.1010 (19)0.0594 (13)0.0748 (14)−0.0006 (12)0.0371 (14)0.0028 (10)
C130.0788 (18)0.0879 (16)0.1040 (19)0.0125 (13)0.0351 (15)0.0085 (14)
C140.0805 (18)0.116 (2)0.0847 (17)0.0087 (15)0.0112 (13)0.0173 (15)
C150.0853 (19)0.1038 (18)0.0645 (13)−0.0124 (14)0.0239 (13)−0.0070 (12)
C160.0800 (18)0.0910 (16)0.0915 (16)−0.0034 (13)0.0401 (14)−0.0088 (13)
Geometric parameters (Å, °) top
N1—C121.487 (2)C7—C81.403 (3)
N1—C161.482 (3)C7—H7A0.9300
N1—H1C0.9601C8—C91.348 (3)
N1—H1D0.9600C8—H8A0.9300
O1—C21.357 (2)C9—C101.417 (3)
O1—H1B0.8200C9—H9A0.9300
O2—C111.244 (2)C12—C131.498 (3)
O3—C111.276 (2)C12—H12A0.9700
C1—C21.363 (3)C12—H12B0.9700
C1—C101.400 (3)C13—C141.509 (3)
C1—H1A0.9300C13—H13A0.9700
C2—C31.417 (2)C13—H13B0.9700
C3—C41.372 (3)C14—C151.502 (3)
C3—C111.498 (3)C14—H14A0.9700
C4—C51.404 (3)C14—H14B0.9700
C4—H4A0.9300C15—C161.494 (3)
C5—C61.404 (3)C15—H15A0.9700
C5—C101.416 (2)C15—H15B0.9700
C6—C71.353 (3)C16—H16A0.9700
C6—H6A0.9300C16—H16B0.9700
C12—N1—C16111.63 (16)C1—C10—C9122.6 (2)
C12—N1—H1C109.7C5—C10—C9118.3 (2)
C16—N1—H1C109.4O2—C11—O3123.8 (2)
C12—N1—H1D108.9O2—C11—C3120.0 (2)
C16—N1—H1D109.2O3—C11—C3116.16 (19)
H1C—N1—H1D108.0N1—C12—C13110.18 (17)
C2—O1—H1B109.5N1—C12—H12A109.6
C2—C1—C10121.22 (18)C13—C12—H12A109.6
C2—C1—H1A119.4N1—C12—H12B109.6
C10—C1—H1A119.4C13—C12—H12B109.6
O1—C2—C1118.97 (18)H12A—C12—H12B108.1
O1—C2—C3120.30 (19)C12—C13—C14111.27 (19)
C1—C2—C3120.74 (19)C12—C13—H13A109.4
C4—C3—C2118.14 (18)C14—C13—H13A109.4
C4—C3—C11120.27 (18)C12—C13—H13B109.4
C2—C3—C11121.58 (19)C14—C13—H13B109.4
C3—C4—C5122.53 (18)H13A—C13—H13B108.0
C3—C4—H4A118.7C15—C14—C13110.99 (19)
C5—C4—H4A118.7C15—C14—H14A109.4
C6—C5—C4122.70 (19)C13—C14—H14A109.4
C6—C5—C10119.1 (2)C15—C14—H14B109.4
C4—C5—C10118.21 (18)C13—C14—H14B109.4
C7—C6—C5120.9 (2)H14A—C14—H14B108.0
C7—C6—H6A119.6C16—C15—C14111.0 (2)
C5—C6—H6A119.6C16—C15—H15A109.4
C6—C7—C8120.4 (2)C14—C15—H15A109.4
C6—C7—H7A119.8C16—C15—H15B109.4
C8—C7—H7A119.8C14—C15—H15B109.4
C9—C8—C7120.3 (2)H15A—C15—H15B108.0
C9—C8—H8A119.8N1—C16—C15110.30 (17)
C7—C8—H8A119.8N1—C16—H16A109.6
C8—C9—C10121.0 (2)C15—C16—H16A109.6
C8—C9—H9A119.5N1—C16—H16B109.6
C10—C9—H9A119.5C15—C16—H16B109.6
C1—C10—C5119.13 (19)H16A—C16—H16B108.1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O30.821.772.504 (2)149
N1—H1C···O2i0.961.832.783 (2)173
N1—H1D···O30.961.752.709 (2)173
C12—H12A···O1ii0.972.403.336 (3)161
Symmetry codes: (i) −x, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O30.821.772.504 (2)149
N1—H1C···O2i0.961.832.783 (2)173
N1—H1D···O30.961.752.709 (2)173
C12—H12A···O1ii0.972.403.336 (3)161
Symmetry codes: (i) −x, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2.
Acknowledgements top

Y-TW thanks the Starting Fund of Shandong Institute of Light Industry for financial support.

references
References top

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Shen, H., Nie, J.-J. & Xu, D.-J. (2008). Acta Cryst. E64, o1146–o1147.

Wang, Y.-T., Tang, G.-M. & Qin, D.-W. (2005a). Acta Cryst. E61, o3623–o3624.

Wang, Y.-T., Tang, G.-M. & Qin, D.-W. (2005b). Acta Cryst. E61, o3979–o3980.

Wang, Y.-T., Tang, G.-M. & Qin, X.-Y. (2006). Acta Cryst. E62, o1496–o1497.