Piperidinium 3-hydr-oxy-2-naphthoate.

The crystals of the title salt, C(5)H(12)N(+)·C(11)H(7)O(3) (-), were obtained from a methanol/water solution of 3-hydr-oxy-2-naphthoic acid and piperidine at room temperature. In the crystal structure, the piperidinium cations display a chair conformation and link with hydroxy-naphthoate anions via N-H⋯O and C-H⋯O hydrogen bonds. An intra-molecular O-H⋯O inter-action is also present.

Related literature

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

Experimental

Crystal data

C5H12N+·C11H7O3 −

M = 273.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.160

S = 0.99

3385 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C5H12N+·C11H7O3−	F(000) = 584
Mr = 273.32	Dx = 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

Bruker SMART CCD area-detector diffractometer	1512 reflections with I > σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 27.4°, θmin = 2.1°
φ and ω scans	h = −9→11
10640 measured reflections	k = −25→22
3385 independent reflections	l = −12→12

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(Fo2) + (0.0733P)2] where P = (Fo2 + 2Fc2)/3
3385 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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
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*

	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)

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

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

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) ; (ii) .