3-Carb­oxy-2-(piperidin-1-ium-1-yl)propano­ate

Sudhahar, S.; Sankaranarayanan, K.; Ravi, G.; Kumar, R.M.; Chakkaravarthi, G.

doi:10.1107/S2414314616007483

organic compounds

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160748

doi:10.1107/S2414314616007483

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3-Carboxy-2-(piperidin-1-ium-1-yl)propanoate

S. Sudhahar,^a ^* K. Sankaranarayanan,^a G. Ravi,^a R. Mohan Kumar ^b and G. Chakkaravarthi ^c ^*

^aDepartment of Physics, Alagappa University, Karaikkudi 630 003, India, ^bDepartment of Physics, Presidency College, Chennai 600 005, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: sudhaharphdphysics@gmail.com, chakkaravarthi_2005@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 2 May 2016; accepted 4 May 2016; online 20 May 2016)

In the zwitterionic title compound, C₉H₁₅NO₄, the piperidinium N atom is protonated and the OH group of one of the carboxylate groups is deprotonated. The piperidinium ring adopts a chair conformation. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds generate an R₃³(15) ring motif and link the molecules into infinite chains propagating along [010]. The structure is further consolidated by weak C—H⋯O interactions to form a three-dimensional network.

Keywords: crystal structure; hydrogen bonding; zwitterion..

CCDC reference: 1478206

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Chemical scheme

Structure description

Piperidine and its derivatives find extensive applications in some areas of biochemistry and material chemistry. They also exhibit good bioactivity (Cardellicchio et al. 2010 ; Huang et al. 2008 ). We report here the synthesis and the crystal structure of the title compound (Fig. 1). The N atom of the the piperidinium ring is protonated while the OH substituent of one of the carboxylate groups is deprotonated. The geometric parameters are comparable to those reported for similar structures (Aravindhan et al., 2009 ; Sankar et al., 2014 ).

Figure 1
The molecular structure of the title compound, with atom labelling and 30% probability displacement ellipsoids.

The piperidine ring (N1/C1–C5) adopts a chair conformation with puckering parameters of Q = 0.579 (3) Å; θ = 1.0 (3)° and φ = 134 (15)°. An intramolecular N—H⋯O hydrogen bond occurs (Table 1). In the crystal, N—H⋯O and O—H⋯O hydrogen bonds generate R₃³(15) ring motifs (Fig. 2) and link the molecules into infinite chains along [010]. The structure is further consolidated by weak C—H⋯O interactions (Table 1 and Fig. 3) to form a three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.89 (1)	2.42 (2)	2.736 (2)	101 (2)
N1—H1⋯O1ⁱ	0.89 (1)	1.93 (1)	2.759 (2)	154 (2)
O4—H4⋯O2ⁱⁱ	0.83 (1)	1.73 (1)	2.557 (2)	173 (3)
C1—H1A⋯O1ⁱⁱⁱ	0.97	2.60	3.528 (3)	160
C1—H1B⋯O3^iv	0.97	2.44	3.381 (3)	163
C5—H5A⋯O4^iv	0.97	2.51	3.439 (3)	161
C8—H8A⋯O2ⁱⁱ	0.97	2.45	3.142 (3)	128
C8—H8A⋯O1ⁱ	0.97	2.55	3.368 (2)	143
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y-1, z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
A partial packing diagram showing the ring motif.

Figure 3
Crystal packing of the title compound viewed along the b axis. Hydrogen bonds (see Table 1

) are shown as dashed lines and C-bound H atoms have been omitted for clarity.

Synthesis and crystallization

The title compound was synthesized from piperidine (0.85 g) and maleic acid (1.16 g) in a methanol:water mixed solvent system. Colourless block-like crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation from methanol:water (1:1) mixed solvent.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₉H₁₅NO₄
M_r	201.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	9.8364 (8), 5.9731 (5), 17.0805 (15)
β (°)	98.152 (5)
V (Å³)	993.40 (15)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.975, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	8624, 2431, 1446
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.172, 1.04
No. of reflections	2431
No. of parameters	134
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1478206

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616007483/sj4031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616007483/sj4031Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616007483/sj4031Isup3.cml

checkCIF report

Synthesis and crystallization top

The title compound was synthesized from piperidine (0.85 g) and maleic acid (1.16 g) in a methonol:water mixed solvent system. Colourless block-like crystals suitable for single crystal X-ray diffraction were grown by slow evaporation.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1

Experimental top

Structure description top

Piperidine and its derivatives find extensive applications in some areas of biochemistry and material chemistry. They also exhibit good bioactivity (Cardellicchio et al. 2010; Huang et al. 2008). We report here the synthesis and the crystal structure of the title compound (Fig. 1). The N atom of the the piperidinium ring is protonated while the OH substituent of one of the carboxylate groups is deprotonated. The geometric parameters are comparable to those reported for similar structures (Aravindhan et al., 2009; Sankar et al., 2014).

The piperidine ring (N1/C1–C5) adopts a chair conformation with puckering parameters of Q = 0.579 (3) Å; θ = 1.0 (3)° and φ = 134 (15)°. In the crystal, C—H1B···O3 and C5—H5A···O4 contacts generate R₂²(8) ring motifs (Fig. 2). O—H···O and N—H···O hydrogen bonds form infinite chains along [010] and these chains are further consolidated by weak C—H···O interactions (Table 1 and Fig. 2) to form a three-dimensional network.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling and 30% probability displacement ellipsoids.
	Fig. 2. A partial packing diagram showing the ring motif.
	Fig. 3. Crystal packing of the title compound viewed along the b axis. Hydrogen bonds (see Table 1) are shown as dashed lines and C-bound H atoms have been omitted for clarity.

3-Carboxy-2-(piperidin-1-ium-1-yl)propanoate top

Crystal data top

C₉H₁₅NO₄	F(000) = 432
M_r = 201.22	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5733 reflections
a = 9.8364 (8) Å	θ = 2.1–28.3°
b = 5.9731 (5) Å	µ = 0.11 mm⁻¹
c = 17.0805 (15) Å	T = 295 K
β = 98.152 (5)°	Block, colourless
V = 993.40 (15) Å³	0.24 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2431 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω and φ scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→13
T_min = 0.975, T_max = 0.981	k = −7→7
8624 measured reflections	l = −22→22

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.090P)² + 0.0823P] where P = (F_o² + 2F_c²)/3
2431 reflections	(Δ/σ)_max < 0.001
134 parameters	Δρ_max = 0.28 e Å⁻³
2 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₉H₁₅NO₄	V = 993.40 (15) Å³
M_r = 201.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8364 (8) Å	µ = 0.11 mm⁻¹
b = 5.9731 (5) Å	T = 295 K
c = 17.0805 (15) Å	0.24 × 0.22 × 0.18 mm
β = 98.152 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2431 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1446 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.981	R_int = 0.054
8624 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	2 restraints
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.28 e Å⁻³
2431 reflections	Δρ_min = −0.19 e Å⁻³
134 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.2180 (2)	0.4085 (3)	0.85245 (13)	0.0411 (5)
H1A	0.1439	0.5094	0.8324	0.049*
H1B	0.3042	0.4866	0.8513	0.049*
C2	0.2051 (3)	0.3451 (4)	0.93646 (14)	0.0516 (6)
H2A	0.1164	0.2757	0.9381	0.062*
H2B	0.2103	0.4788	0.9690	0.062*
C3	0.3179 (3)	0.1844 (4)	0.96931 (15)	0.0592 (7)
H3A	0.4066	0.2570	0.9714	0.071*
H3B	0.3060	0.1407	1.0226	0.071*
C4	0.3125 (3)	−0.0200 (4)	0.91702 (15)	0.0539 (6)
H4A	0.2267	−0.0985	0.9187	0.065*
H4B	0.3870	−0.1203	0.9369	0.065*
C5	0.3241 (2)	0.0422 (4)	0.83234 (14)	0.0421 (5)
H5A	0.4133	0.1089	0.8299	0.051*
H5B	0.3167	−0.0918	0.7999	0.051*
C6	0.0979 (2)	0.4225 (3)	0.68531 (12)	0.0369 (5)
C7	0.22115 (18)	0.2712 (3)	0.71628 (12)	0.0344 (5)
H7	0.3069	0.3526	0.7138	0.041*
C8	0.21416 (19)	0.0678 (3)	0.66188 (13)	0.0380 (5)
H8A	0.1588	−0.0464	0.6825	0.046*
H8B	0.1676	0.1110	0.6102	0.046*
C9	0.3517 (2)	−0.0332 (4)	0.65187 (14)	0.0450 (6)
N1	0.21295 (15)	0.2051 (3)	0.80041 (10)	0.0338 (4)
O1	−0.01285 (13)	0.3786 (2)	0.70850 (9)	0.0445 (4)
H1	0.1320 (13)	0.137 (3)	0.7984 (13)	0.039 (6)*
O2	0.11830 (16)	0.5682 (3)	0.63616 (10)	0.0505 (4)
O3	0.45737 (16)	0.0721 (3)	0.66196 (12)	0.0654 (6)
O4	0.34903 (16)	−0.2428 (3)	0.62772 (12)	0.0605 (5)
H4	0.2710 (17)	−0.298 (5)	0.6272 (19)	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0414 (11)	0.0339 (12)	0.0483 (13)	−0.0003 (9)	0.0073 (9)	−0.0037 (10)
C2	0.0614 (14)	0.0503 (14)	0.0444 (13)	−0.0025 (11)	0.0113 (11)	−0.0060 (11)
C3	0.0712 (16)	0.0597 (17)	0.0442 (14)	−0.0016 (13)	−0.0002 (12)	0.0022 (12)
C4	0.0599 (14)	0.0508 (15)	0.0493 (14)	0.0055 (12)	0.0018 (11)	0.0083 (12)
C5	0.0354 (10)	0.0402 (13)	0.0501 (13)	0.0051 (9)	0.0041 (9)	0.0031 (10)
C6	0.0394 (10)	0.0315 (12)	0.0404 (12)	0.0015 (8)	0.0080 (9)	−0.0046 (9)
C7	0.0291 (9)	0.0343 (11)	0.0417 (11)	−0.0007 (8)	0.0117 (8)	0.0031 (9)
C8	0.0362 (10)	0.0388 (12)	0.0406 (11)	0.0061 (8)	0.0112 (8)	0.0004 (9)
C9	0.0431 (11)	0.0461 (14)	0.0500 (13)	0.0084 (10)	0.0211 (10)	0.0042 (11)
N1	0.0291 (8)	0.0333 (10)	0.0399 (9)	−0.0015 (7)	0.0082 (7)	0.0005 (7)
O1	0.0331 (7)	0.0460 (10)	0.0559 (10)	0.0063 (6)	0.0112 (7)	0.0024 (7)
O2	0.0545 (9)	0.0429 (10)	0.0549 (10)	0.0052 (7)	0.0105 (7)	0.0122 (8)
O3	0.0414 (9)	0.0641 (12)	0.0967 (15)	0.0007 (8)	0.0303 (9)	−0.0062 (10)
O4	0.0533 (10)	0.0460 (11)	0.0875 (13)	0.0113 (8)	0.0282 (9)	−0.0067 (9)

Geometric parameters (Å, º) top

C1—N1	1.503 (3)	C5—H5B	0.9700
C1—C2	1.507 (3)	C6—O1	1.239 (2)
C1—H1A	0.9700	C6—O2	1.245 (2)
C1—H1B	0.9700	C6—C7	1.544 (3)
C2—C3	1.513 (3)	C7—N1	1.503 (2)
C2—H2A	0.9700	C7—C8	1.525 (3)
C2—H2B	0.9700	C7—H7	0.9800
C3—C4	1.509 (3)	C8—C9	1.513 (3)
C3—H3A	0.9700	C8—H8A	0.9700
C3—H3B	0.9700	C8—H8B	0.9700
C4—C5	1.513 (3)	C9—O3	1.206 (3)
C4—H4A	0.9700	C9—O4	1.317 (3)
C4—H4B	0.9700	N1—H1	0.891 (9)
C5—N1	1.507 (3)	O4—H4	0.834 (10)
C5—H5A	0.9700

N1—C1—C2	111.08 (18)	C4—C5—H5B	109.5
N1—C1—H1A	109.4	H5A—C5—H5B	108.1
C2—C1—H1A	109.4	O1—C6—O2	126.62 (19)
N1—C1—H1B	109.4	O1—C6—C7	116.74 (18)
C2—C1—H1B	109.4	O2—C6—C7	116.51 (16)
H1A—C1—H1B	108.0	N1—C7—C8	111.65 (16)
C1—C2—C3	110.87 (19)	N1—C7—C6	109.60 (14)
C1—C2—H2A	109.5	C8—C7—C6	106.99 (17)
C3—C2—H2A	109.5	N1—C7—H7	109.5
C1—C2—H2B	109.5	C8—C7—H7	109.5
C3—C2—H2B	109.5	C6—C7—H7	109.5
H2A—C2—H2B	108.1	C9—C8—C7	115.00 (18)
C4—C3—C2	109.4 (2)	C9—C8—H8A	108.5
C4—C3—H3A	109.8	C7—C8—H8A	108.5
C2—C3—H3A	109.8	C9—C8—H8B	108.5
C4—C3—H3B	109.8	C7—C8—H8B	108.5
C2—C3—H3B	109.8	H8A—C8—H8B	107.5
H3A—C3—H3B	108.3	O3—C9—O4	121.26 (19)
C3—C4—C5	111.5 (2)	O3—C9—C8	122.8 (2)
C3—C4—H4A	109.3	O4—C9—C8	115.82 (19)
C5—C4—H4A	109.3	C1—N1—C7	110.55 (15)
C3—C4—H4B	109.3	C1—N1—C5	110.28 (16)
C5—C4—H4B	109.3	C7—N1—C5	112.41 (14)
H4A—C4—H4B	108.0	C1—N1—H1	110.3 (14)
N1—C5—C4	110.80 (17)	C7—N1—H1	104.6 (14)
N1—C5—H5A	109.5	C5—N1—H1	108.6 (14)
C4—C5—H5A	109.5	C9—O4—H4	111 (2)
N1—C5—H5B	109.5

N1—C1—C2—C3	58.1 (2)	C7—C8—C9—O3	−24.1 (3)
C1—C2—C3—C4	−57.2 (3)	C7—C8—C9—O4	158.87 (19)
C2—C3—C4—C5	56.8 (3)	C2—C1—N1—C7	178.09 (16)
C3—C4—C5—N1	−56.9 (3)	C2—C1—N1—C5	−57.0 (2)
O1—C6—C7—N1	−36.0 (2)	C8—C7—N1—C1	−179.20 (14)
O2—C6—C7—N1	147.90 (18)	C6—C7—N1—C1	−60.8 (2)
O1—C6—C7—C8	85.2 (2)	C8—C7—N1—C5	57.1 (2)
O2—C6—C7—C8	−90.9 (2)	C6—C7—N1—C5	175.46 (16)
N1—C7—C8—C9	−91.2 (2)	C4—C5—N1—C1	56.1 (2)
C6—C7—C8—C9	148.93 (18)	C4—C5—N1—C7	179.93 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.89 (1)	2.42 (2)	2.736 (2)	101 (2)
C1—H1A···O1	0.97	2.56	3.107 (3)	116
C7—H7···O3	0.98	2.48	2.879 (2)	104
N1—H1···O1ⁱ	0.89 (1)	1.93 (1)	2.759 (2)	154 (2)
O4—H4···O2ⁱⁱ	0.83 (1)	1.73 (1)	2.557 (2)	173 (3)
C1—H1A···O1ⁱⁱⁱ	0.97	2.60	3.528 (3)	160
C1—H1B···O3^iv	0.97	2.44	3.381 (3)	163
C5—H5A···O4^iv	0.97	2.51	3.439 (3)	161
C8—H8A···O2ⁱⁱ	0.97	2.45	3.142 (3)	128
C8—H8A···O1ⁱ	0.97	2.55	3.368 (2)	143

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x, y−1, z; (iii) −x, y+1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.891 (9)	2.42 (2)	2.736 (2)	101.2 (15)
C1—H1A···O1	0.97	2.56	3.107 (3)	116
C7—H7···O3	0.98	2.48	2.879 (2)	104
N1—H1···O1ⁱ	0.891 (9)	1.931 (12)	2.759 (2)	154.0 (19)
O4—H4···O2ⁱⁱ	0.834 (10)	1.728 (11)	2.557 (2)	173 (3)
C1—H1A···O1ⁱⁱⁱ	0.97	2.60	3.528 (3)	160
C1—H1B···O3^iv	0.97	2.44	3.381 (3)	163
C5—H5A···O4^iv	0.97	2.51	3.439 (3)	161
C8—H8A···O2ⁱⁱ	0.97	2.45	3.142 (3)	128
C8—H8A···O1ⁱ	0.97	2.55	3.368 (2)	143

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x, y−1, z; (iii) −x, y+1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₉H₁₅NO₄
M_r	201.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	9.8364 (8), 5.9731 (5), 17.0805 (15)
β (°)	98.152 (5)
V (Å³)	993.40 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.975, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	8624, 2431, 1446
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.172, 1.04
No. of reflections	2431
No. of parameters	134
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

Aravindhan, S., Ponnuswamy, S., Jamesh, M., Ramesh, P. & Ponnuswamy, M. N. (2009). Acta Cryst. E65, o1974. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cardellicchio, C., Capozzi, M. A. M. & Naso, F. (2010). Tetrahedron Asymmetry, 21, 507–517. Web of Science CrossRef CAS Google Scholar
Huang, P. J. J., Youssef, D., Cameron, T. S. & Jha, A. (2008). Arkivoc, pp. 165–177. CrossRef Google Scholar
Sankar, A., Ambalatharasu, S., Peramaiyan, G., Chakkaravarthi, G. & Kanagadurai, R. (2014). Acta Cryst. E70, o450. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 1| Part 5| May 2016| x160748

doi:10.1107/S2414314616007483

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Carb­­oxy-2-(piperidin-1-ium-1-yl)propano­ate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

3-Carboxy-2-(piperidin-1-ium-1-yl)propanoate