Piperidinium 3-hydr­oxy-2-naphthoate

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

doi:10.1107/S1600536808025567

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1753

doi:10.1107/S1600536808025567

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Piperidinium 3-hydroxy-2-naphthoate

Yong-Tao Wang,^a ^* Gui-Mei Tang,^a Yong-Chun Zhang ^a and Wen-Zhu Wan ^a

^aDepartment of Chemical Engineering, Shandong Institute of Light Industry, Jinan, Shandong 250353, People's Republic of China
^*Correspondence e-mail: ceswyt@sohu.com

(Received 30 July 2008; accepted 8 August 2008; online 13 August 2008)

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.

Related literature

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

Experimental

Crystal data

C₅H₁₂N⁺·C₁₁H₇O₃⁻
M_r = 273.32
Monoclinic, P 2₁ /n
a = 8.6683 (3) Å
b = 19.4537 (5) Å
c = 9.5932 (3) Å
β = 111.959 (2)°
V = 1500.34 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
10640 measured reflections
3385 independent reflections
1512 reflections with I > σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.160
S = 0.99
3385 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O3	0.82	1.77	2.504 (2)	149
N1—H1C⋯O2ⁱ	0.96	1.83	2.783 (2)	173
N1—H1D⋯O3	0.96	1.75	2.709 (2)	173
C12—H12A⋯O1ⁱⁱ	0.97	2.40	3.336 (3)	161
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025567/xu2446sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025567/xu2446Isup2.hkl

checkCIF report

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.

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

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
M_r = 273.32	D_x = 1.210 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1627 reflections
a = 8.6683 (3) Å	θ = 2.5–20.5°
b = 19.4537 (5) Å	µ = 0.08 mm⁻¹
c = 9.5932 (3) Å	T = 298 K
β = 111.959 (2)°	Block, colourless
V = 1500.34 (8) Å³	0.40 × 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 tube	R_int = 0.035
Graphite monochromator	θ_max = 27.4°, θ_min = 2.1°
ϕ and ω scans	h = −9→11
10640 measured reflections	k = −25→22
3385 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0733P)²] where P = (F_o² + 2F_c²)/3
3385 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₅H₁₂N⁺·C₁₁H₇O₃⁻	V = 1500.34 (8) Å³
M_r = 273.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6683 (3) Å	µ = 0.08 mm⁻¹
b = 19.4537 (5) Å	T = 298 K
c = 9.5932 (3) Å	0.40 × 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 reflections	R_int = 0.035
3385 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 0.99	Δρ_max = 0.13 e Å⁻³
3385 reflections	Δρ_min = −0.13 e Å⁻³
181 parameters

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

	x	y	z	U_iso*/U_eq
N1	−0.1726 (2)	0.09197 (8)	0.39856 (18)	0.0718 (5)
H1C	−0.1979	0.0491	0.4346	0.108*
H1D	−0.0626	0.1054	0.4635	0.108*
O1	0.31760 (19)	0.22455 (7)	0.73435 (18)	0.0944 (5)
H1B	0.2331	0.2051	0.6786	0.142*
O2	0.24997 (18)	0.03674 (7)	0.51894 (15)	0.0832 (5)
O3	0.14101 (19)	0.13370 (8)	0.56381 (18)	0.0948 (5)
C1	0.6069 (3)	0.20988 (10)	0.8318 (2)	0.0692 (6)
H1A	0.6176	0.2530	0.8763	0.083*
C2	0.4523 (3)	0.18561 (9)	0.7481 (2)	0.0636 (5)
C3	0.4321 (2)	0.12071 (9)	0.67629 (19)	0.0561 (5)
C4	0.5718 (3)	0.08253 (9)	0.69633 (19)	0.0604 (5)
H4A	0.5597	0.0398	0.6498	0.072*
C5	0.7325 (3)	0.10544 (10)	0.7844 (2)	0.0629 (5)
C6	0.8758 (3)	0.06627 (12)	0.8062 (3)	0.0930 (7)
H6A	0.8654	0.0229	0.7626	0.112*
C7	1.0287 (3)	0.09073 (16)	0.8897 (3)	0.1178 (10)
H7A	1.1223	0.0642	0.9027	0.141*
C8	1.0468 (3)	0.15586 (15)	0.9569 (3)	0.1102 (9)
H8A	1.1524	0.1724	1.0137	0.132*
C9	0.9119 (3)	0.19463 (12)	0.9394 (2)	0.0838 (6)
H9A	0.9256	0.2375	0.9852	0.101*
C10	0.7497 (3)	0.17107 (10)	0.8523 (2)	0.0623 (5)
C11	0.2638 (3)	0.09412 (11)	0.5796 (2)	0.0669 (6)
C12	−0.2927 (3)	0.14545 (10)	0.4042 (2)	0.0772 (6)
H12A	−0.2619	0.1895	0.3749	0.093*
H12B	−0.2893	0.1495	0.5061	0.093*
C13	−0.4652 (3)	0.12680 (12)	0.3005 (3)	0.0900 (7)
H13A	−0.5412	0.1634	0.3004	0.108*
H13B	−0.5001	0.0853	0.3366	0.108*
C14	−0.4732 (3)	0.11527 (13)	0.1424 (3)	0.0995 (8)
H14A	−0.5837	0.0996	0.0798	0.119*
H14B	−0.4525	0.1583	0.1015	0.119*
C15	−0.3471 (3)	0.06288 (13)	0.1397 (2)	0.0857 (7)
H15A	−0.3759	0.0184	0.1690	0.103*
H15B	−0.3490	0.0589	0.0383	0.103*
C16	−0.1763 (3)	0.08263 (11)	0.2440 (3)	0.0852 (7)
H16A	−0.0979	0.0471	0.2439	0.102*
H16B	−0.1434	0.1251	0.2097	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0655 (12)	0.0642 (11)	0.0731 (11)	−0.0064 (8)	0.0116 (9)	0.0044 (8)
O1	0.0755 (11)	0.0761 (10)	0.1167 (13)	0.0101 (8)	0.0186 (9)	−0.0260 (8)
O2	0.0942 (12)	0.0604 (9)	0.0768 (10)	−0.0154 (7)	0.0110 (8)	−0.0074 (7)
O3	0.0677 (11)	0.0869 (11)	0.1111 (13)	−0.0032 (9)	0.0121 (9)	−0.0172 (9)
C1	0.0774 (16)	0.0539 (11)	0.0683 (13)	−0.0059 (11)	0.0182 (12)	−0.0120 (9)
C2	0.0689 (15)	0.0538 (12)	0.0641 (12)	0.0031 (11)	0.0203 (11)	−0.0032 (9)
C3	0.0682 (14)	0.0483 (10)	0.0481 (10)	−0.0035 (9)	0.0176 (9)	0.0014 (8)
C4	0.0753 (15)	0.0505 (11)	0.0529 (11)	−0.0009 (10)	0.0211 (10)	−0.0031 (8)
C5	0.0656 (14)	0.0660 (13)	0.0545 (11)	0.0015 (11)	0.0192 (10)	−0.0012 (9)
C6	0.0789 (19)	0.0897 (16)	0.0979 (17)	0.0125 (14)	0.0187 (14)	−0.0205 (13)
C7	0.071 (2)	0.130 (2)	0.131 (2)	0.0165 (16)	0.0138 (17)	−0.0327 (19)
C8	0.0669 (19)	0.126 (2)	0.119 (2)	−0.0029 (16)	0.0122 (15)	−0.0265 (18)
C9	0.0794 (17)	0.0836 (15)	0.0786 (15)	−0.0114 (13)	0.0181 (13)	−0.0138 (12)
C10	0.0655 (14)	0.0637 (13)	0.0536 (11)	−0.0056 (10)	0.0174 (10)	−0.0023 (9)
C11	0.0755 (16)	0.0566 (13)	0.0604 (12)	−0.0084 (12)	0.0160 (11)	0.0031 (10)
C12	0.1010 (19)	0.0594 (13)	0.0748 (14)	−0.0006 (12)	0.0371 (14)	0.0028 (10)
C13	0.0788 (18)	0.0879 (16)	0.1040 (19)	0.0125 (13)	0.0351 (15)	0.0085 (14)
C14	0.0805 (18)	0.116 (2)	0.0847 (17)	0.0087 (15)	0.0112 (13)	0.0173 (15)
C15	0.0853 (19)	0.1038 (18)	0.0645 (13)	−0.0124 (14)	0.0239 (13)	−0.0070 (12)
C16	0.0800 (18)	0.0910 (16)	0.0915 (16)	−0.0034 (13)	0.0401 (14)	−0.0088 (13)

Geometric parameters (Å, º) top

N1—C12	1.487 (2)	C7—C8	1.403 (3)
N1—C16	1.482 (3)	C7—H7A	0.9300
N1—H1C	0.9601	C8—C9	1.348 (3)
N1—H1D	0.9600	C8—H8A	0.9300
O1—C2	1.357 (2)	C9—C10	1.417 (3)
O1—H1B	0.8200	C9—H9A	0.9300
O2—C11	1.244 (2)	C12—C13	1.498 (3)
O3—C11	1.276 (2)	C12—H12A	0.9700
C1—C2	1.363 (3)	C12—H12B	0.9700
C1—C10	1.400 (3)	C13—C14	1.509 (3)
C1—H1A	0.9300	C13—H13A	0.9700
C2—C3	1.417 (2)	C13—H13B	0.9700
C3—C4	1.372 (3)	C14—C15	1.502 (3)
C3—C11	1.498 (3)	C14—H14A	0.9700
C4—C5	1.404 (3)	C14—H14B	0.9700
C4—H4A	0.9300	C15—C16	1.494 (3)
C5—C6	1.404 (3)	C15—H15A	0.9700
C5—C10	1.416 (2)	C15—H15B	0.9700
C6—C7	1.353 (3)	C16—H16A	0.9700
C6—H6A	0.9300	C16—H16B	0.9700

C12—N1—C16	111.63 (16)	C1—C10—C9	122.6 (2)
C12—N1—H1C	109.7	C5—C10—C9	118.3 (2)
C16—N1—H1C	109.4	O2—C11—O3	123.8 (2)
C12—N1—H1D	108.9	O2—C11—C3	120.0 (2)
C16—N1—H1D	109.2	O3—C11—C3	116.16 (19)
H1C—N1—H1D	108.0	N1—C12—C13	110.18 (17)
C2—O1—H1B	109.5	N1—C12—H12A	109.6
C2—C1—C10	121.22 (18)	C13—C12—H12A	109.6
C2—C1—H1A	119.4	N1—C12—H12B	109.6
C10—C1—H1A	119.4	C13—C12—H12B	109.6
O1—C2—C1	118.97 (18)	H12A—C12—H12B	108.1
O1—C2—C3	120.30 (19)	C12—C13—C14	111.27 (19)
C1—C2—C3	120.74 (19)	C12—C13—H13A	109.4
C4—C3—C2	118.14 (18)	C14—C13—H13A	109.4
C4—C3—C11	120.27 (18)	C12—C13—H13B	109.4
C2—C3—C11	121.58 (19)	C14—C13—H13B	109.4
C3—C4—C5	122.53 (18)	H13A—C13—H13B	108.0
C3—C4—H4A	118.7	C15—C14—C13	110.99 (19)
C5—C4—H4A	118.7	C15—C14—H14A	109.4
C6—C5—C4	122.70 (19)	C13—C14—H14A	109.4
C6—C5—C10	119.1 (2)	C15—C14—H14B	109.4
C4—C5—C10	118.21 (18)	C13—C14—H14B	109.4
C7—C6—C5	120.9 (2)	H14A—C14—H14B	108.0
C7—C6—H6A	119.6	C16—C15—C14	111.0 (2)
C5—C6—H6A	119.6	C16—C15—H15A	109.4
C6—C7—C8	120.4 (2)	C14—C15—H15A	109.4
C6—C7—H7A	119.8	C16—C15—H15B	109.4
C8—C7—H7A	119.8	C14—C15—H15B	109.4
C9—C8—C7	120.3 (2)	H15A—C15—H15B	108.0
C9—C8—H8A	119.8	N1—C16—C15	110.30 (17)
C7—C8—H8A	119.8	N1—C16—H16A	109.6
C8—C9—C10	121.0 (2)	C15—C16—H16A	109.6
C8—C9—H9A	119.5	N1—C16—H16B	109.6
C10—C9—H9A	119.5	C15—C16—H16B	109.6
C1—C10—C5	119.13 (19)	H16A—C16—H16B	108.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3	0.82	1.77	2.504 (2)	149
N1—H1C···O2ⁱ	0.96	1.83	2.783 (2)	173
N1—H1D···O3	0.96	1.75	2.709 (2)	173
C12—H12A···O1ⁱⁱ	0.97	2.40	3.336 (3)	161

Symmetry codes: (i) −x, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₅H₁₂N⁺·C₁₁H₇O₃⁻
M_r	273.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.6683 (3), 19.4537 (5), 9.5932 (3)
β (°)	111.959 (2)
V (Å³)	1500.34 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > σ(I)] reflections	10640, 3385, 1512
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.160, 0.99
No. of reflections	3385
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3	0.82	1.77	2.504 (2)	149
N1—H1C···O2ⁱ	0.96	1.83	2.783 (2)	173
N1—H1D···O3	0.96	1.75	2.709 (2)	173
C12—H12A···O1ⁱⁱ	0.97	2.40	3.336 (3)	161

Symmetry codes: (i) −x, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2.

Acknowledgements

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

References

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