3-Hy­droxy-2-[(4-hy­droxy­benz­yl)aza­nium­yl]propano­ate monohydrate

Gao, M.; Lu, L.-P.

doi:10.1107/S2414314617002711

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170271

https://doi.org/10.1107/S2414314617002711

Open

access

3-Hydroxy-2-[(4-hydroxybenzyl)azaniumyl]propanoate monohydrate

Min Gao ^a and Li-Ping Lu ^a ^*

^aInstitute of Molecular Science, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
^*Correspondence e-mail: luliping@sxu.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 February 2017; accepted 17 February 2017; online 21 February 2017)

In the title hydrated zwitterion, C₁₀H₁₃NO₄·H₂O, the N—C—C—OH side chain shows a gauche conformation [torsion angle = −59.05 (18)°]. In the crystal, the components are linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds to generate a three-dimensional supramolecular network.

Keywords: crystal structure; hydrate; 3-hydroxy-2-[(4-hydroxybenzyl)azaniumyl]propanoate; C—H⋯O hydrogen bonding; O—H⋯O hydrogen bonding; N—H⋯O hydrogen bonding; synchrotron.

CCDC reference: 1533317

Structure description

Recently, a copper(II) complex with a reduced amino acid Schiff base was shown to exhibit inhibiting activity with respect to protein tyrosine phosphatase (Li et al., 2016 ). In our previous reports, we have shown that VO(II) complexes have very strong inhibitory activity towards protein tyrosine phosphatase (Lu & Zhu, 2014 ; Han et al., 2012 ; Li et al. 2016). Thus, 3-hydroxy-2-[(4-hydroxybenzyl)amino]propanoic acid was reacted with VOSO₄ in alkaline solution to prepare its VO complex in order to test its biological activity. However, no complex of VO(II) was formed; instead crystals of the title compound were obtained.

The molecular structure of the title compound is illustrated in Fig. 1. The asymmetric unit consists of a 3-hydroxy-2-[(4-hydroxybenzyl)azaniumyl]propanoate zwitterion (nominal proton transfer from the carboxylic acid group to the secondary amine group) and a water molecule. The zwitterionic form found agrees with that of many amino acids. The C5—C4—N1—C2 and N1—C1—C2—O3 links both show a gauche conformation [torsion angles = 65.0 (2) and −59.05 (18)°, respectively].

Figure 1
The molecular structure of the title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.

In the crystal, molecules are connected through a network of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds (Table 1), leading to the formation of a three-dimensional supramolecular network (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5	0.98 (3)	1.79 (3)	2.759 (2)	166 (2)
O4—H4⋯O2ⁱ	0.90 (3)	1.72 (3)	2.624 (2)	174 (3)
N1—H1A⋯O1ⁱⁱ	0.94 (2)	1.98 (2)	2.8390 (19)	150 (2)
N1—H1B⋯O1ⁱⁱⁱ	0.96 (3)	1.84 (3)	2.782 (2)	170 (2)
C2—H2⋯O4^iv	1.00	2.54	3.300 (2)	132
C4—H4A⋯O3ⁱⁱ	0.99	2.55	3.392 (2)	143
O5—H5A⋯O2^v	0.85 (3)	1.99 (3)	2.8380 (19)	172 (3)
O5—H5B⋯O4^vi	0.87 (3)	1.92 (3)	2.785 (2)	171 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) x+1, y, z; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (v) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Figure 2
The C—H⋯O, O—H⋯O and N—H⋯O hydrogen-bonded (dotted lines) network. [Symmetry codes: (A) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , 1 − z; (B) x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , 1 − z; (C) x + 1, y, z; (D) x − $[{1\over 2}]$ , −y + $[{1\over 2}]$ , 1 − z; (E) −x, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (F) −x + $[{3\over 2}]$ , 1 − y, z − $[{1\over 2}]$ .]

Synthesis and crystallization

A mixture containing VOSO₄·xH₂O (0.1 mmol), 3-hydroxy-2-[(4-hydroxybenzyl)amino]propanoic acid (0.1 mmol), KOH (0.2 mmol) and H₂O (6.0 ml) was stirred for 30 min at room temperature. The reaction mixture was filtered and the liquor was kept at room temperature. Light-yellow block-shaped crystals of the title compound appeared after 3 d in 40% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The DISP instruction was used in the SHELXL2016 (Sheldrick, 2015 ) refinements in order to correct anomalous scattering values (f′ and f′′) of elements for the synchrotron wavelength used.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₄·H₂O
M_r	229.23
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.5140 (11), 12.418 (3), 15.372 (3)
V (Å³)	1052.6 (4)
Z	4
Radiation type	Synchrotron, λ = 0.7200 Å
μ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Mar165
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997 )
T_min, T_max	0.965, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	5039, 2721, 2624
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.681

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.11
No. of reflections	2721
No. of parameters	164
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.2 (12)
Computer programs: SCALEPACK (Otwinowski & Minor, 1997), HKL-2000 (Otwinowski & Minor, 1997), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2016 (Sheldrick, 2015) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1533317

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002711/hb4124sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002711/hb4124Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617002711/hb4124Isup3.cml

checkCIF report

Computing details top

Data collection: mar165; cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL-2000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: pubCIF (Westrip, 2010).

3-Hydroxy-2-[(4-hydroxybenzyl)azaniumyl]propanoate monohydrate top

Crystal data top

C₁₀H₁₃NO₄·H₂O	D_x = 1.447 Mg m⁻³
M_r = 229.23	Synchrotron radiation, λ = 0.7200 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 5057 reflections
a = 5.5140 (11) Å	θ = 2.7–29.6°
b = 12.418 (3) Å	µ = 0.12 mm⁻¹
c = 15.372 (3) Å	T = 100 K
V = 1052.6 (4) Å³	Block, light yelloe
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 488

Data collection top

Mar165 diffractometer	2624 reflections with I > 2σ(I)
Radiation source: synchrotron, 3W1A at BSRF	R_int = 0.025
oscillation mode scans	θ_max = 29.3°, θ_min = 2.7°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = 0→7
T_min = 0.965, T_max = 0.977	k = −16→16
5039 measured reflections	l = −20→20
2721 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0569P)² + 0.2819P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.097	(Δ/σ)_max < 0.001
S = 1.11	Δρ_max = 0.19 e Å⁻³
2721 reflections	Δρ_min = −0.22 e Å⁻³
164 parameters	Absolute structure: Refined as an inversion twin
0 restraints	Absolute structure parameter: 0.2 (12)
Primary atom site location: structure-invariant direct methods

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.1740 (2)	0.64457 (10)	0.46536 (8)	0.0124 (3)
O2	−0.1669 (3)	0.49448 (10)	0.38500 (9)	0.0145 (3)
O3	0.2072 (3)	0.74505 (10)	0.34128 (9)	0.0153 (3)
H3	0.297 (6)	0.788 (2)	0.2981 (18)	0.023*
O4	0.6113 (3)	0.16978 (11)	0.65474 (10)	0.0157 (3)
H4	0.507 (5)	0.116 (2)	0.6406 (18)	0.024*
N1	0.3273 (3)	0.63321 (11)	0.49124 (9)	0.0087 (3)
H1A	0.282 (5)	0.7061 (19)	0.4913 (15)	0.010*
H1B	0.499 (5)	0.6282 (19)	0.4830 (16)	0.010*
C1	−0.0667 (3)	0.57215 (13)	0.42362 (11)	0.0094 (3)
C2	0.2125 (3)	0.57711 (13)	0.41594 (11)	0.0097 (3)
H2	0.276793	0.501896	0.413099	0.012*
C3	0.2880 (4)	0.63678 (14)	0.33320 (11)	0.0118 (3)
H3A	0.466456	0.634670	0.326401	0.014*
H3B	0.213318	0.602571	0.281565	0.014*
C4	0.2672 (3)	0.59029 (14)	0.58072 (11)	0.0113 (3)
H4A	0.338442	0.638592	0.625116	0.014*
H4B	0.088978	0.590776	0.588583	0.014*
C5	0.3605 (3)	0.47754 (14)	0.59503 (11)	0.0104 (3)
C6	0.2266 (4)	0.38722 (13)	0.56981 (11)	0.0120 (3)
H6	0.077310	0.396915	0.539990	0.014*
C7	0.3078 (4)	0.28317 (14)	0.58753 (11)	0.0132 (3)
H7	0.215956	0.222503	0.569270	0.016*
C8	0.5258 (3)	0.26924 (14)	0.63247 (11)	0.0122 (3)
C9	0.6632 (3)	0.35835 (15)	0.65700 (12)	0.0132 (3)
H9	0.812625	0.348687	0.686782	0.016*
C10	0.5809 (4)	0.46163 (13)	0.63769 (12)	0.0121 (3)
H10	0.676154	0.522158	0.653820	0.014*
O5	0.4627 (3)	0.88897 (11)	0.23976 (9)	0.0154 (3)
H5A	0.381 (5)	0.927 (2)	0.2039 (19)	0.023*
H5B	0.595 (6)	0.864 (2)	0.2161 (19)	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0082 (6)	0.0102 (5)	0.0188 (6)	0.0008 (5)	0.0009 (5)	−0.0022 (5)
O2	0.0108 (7)	0.0111 (6)	0.0216 (6)	−0.0021 (5)	−0.0026 (5)	−0.0048 (5)
O3	0.0190 (7)	0.0096 (5)	0.0173 (6)	0.0027 (5)	0.0047 (5)	0.0035 (5)
O4	0.0141 (7)	0.0085 (6)	0.0246 (7)	0.0025 (5)	−0.0049 (5)	−0.0007 (5)
N1	0.0074 (7)	0.0066 (6)	0.0122 (6)	−0.0005 (5)	0.0002 (5)	0.0003 (5)
C1	0.0101 (8)	0.0066 (6)	0.0117 (7)	−0.0001 (6)	0.0001 (6)	0.0003 (5)
C2	0.0092 (8)	0.0083 (6)	0.0117 (7)	0.0002 (6)	0.0001 (6)	−0.0008 (5)
C3	0.0105 (8)	0.0111 (7)	0.0137 (7)	0.0016 (6)	0.0014 (6)	0.0007 (6)
C4	0.0112 (9)	0.0114 (7)	0.0113 (7)	0.0008 (6)	0.0007 (6)	0.0003 (6)
C5	0.0098 (8)	0.0110 (7)	0.0106 (7)	−0.0003 (6)	0.0007 (6)	0.0011 (5)
C6	0.0108 (9)	0.0119 (7)	0.0134 (7)	−0.0016 (6)	−0.0012 (6)	0.0019 (6)
C7	0.0142 (9)	0.0106 (7)	0.0149 (7)	−0.0024 (6)	−0.0020 (7)	−0.0002 (6)
C8	0.0126 (9)	0.0112 (7)	0.0127 (7)	0.0009 (6)	0.0015 (6)	−0.0004 (6)
C9	0.0101 (8)	0.0139 (7)	0.0155 (7)	0.0001 (6)	−0.0022 (6)	−0.0001 (6)
C10	0.0106 (8)	0.0115 (7)	0.0141 (7)	−0.0031 (6)	−0.0014 (6)	−0.0006 (6)
O5	0.0146 (8)	0.0158 (6)	0.0157 (6)	0.0026 (5)	0.0016 (5)	0.0035 (5)

Geometric parameters (Å, º) top

O1—C1	1.253 (2)	C4—C5	1.508 (2)
O2—C1	1.260 (2)	C4—H4A	0.9900
O3—C3	1.422 (2)	C4—H4B	0.9900
O3—H3	0.98 (3)	C5—C10	1.395 (3)
O4—C8	1.366 (2)	C5—C6	1.398 (2)
O4—H4	0.90 (3)	C6—C7	1.394 (2)
N1—C2	1.492 (2)	C6—H6	0.9500
N1—C4	1.512 (2)	C7—C8	1.397 (3)
N1—H1A	0.94 (2)	C7—H7	0.9500
N1—H1B	0.96 (3)	C8—C9	1.393 (2)
C1—C2	1.545 (3)	C9—C10	1.393 (2)
C2—C3	1.530 (2)	C9—H9	0.9500
C2—H2	1.0000	C10—H10	0.9500
C3—H3A	0.9900	O5—H5A	0.85 (3)
C3—H3B	0.9900	O5—H5B	0.87 (3)

C3—O3—H3	107.0 (16)	C5—C4—H4A	109.1
C8—O4—H4	112.6 (18)	N1—C4—H4A	109.1
C2—N1—C4	116.62 (14)	C5—C4—H4B	109.1
C2—N1—H1A	109.8 (15)	N1—C4—H4B	109.1
C4—N1—H1A	106.3 (15)	H4A—C4—H4B	107.8
C2—N1—H1B	106.7 (14)	C10—C5—C6	118.48 (16)
C4—N1—H1B	108.3 (15)	C10—C5—C4	119.83 (16)
H1A—N1—H1B	109 (2)	C6—C5—C4	121.64 (17)
O1—C1—O2	125.72 (17)	C7—C6—C5	121.34 (17)
O1—C1—C2	118.72 (15)	C7—C6—H6	119.3
O2—C1—C2	115.54 (15)	C5—C6—H6	119.3
N1—C2—C3	107.65 (14)	C6—C7—C8	119.17 (16)
N1—C2—C1	112.46 (14)	C6—C7—H7	120.4
C3—C2—C1	110.73 (14)	C8—C7—H7	120.4
N1—C2—H2	108.6	O4—C8—C9	117.56 (16)
C3—C2—H2	108.6	O4—C8—C7	122.21 (16)
C1—C2—H2	108.6	C9—C8—C7	120.23 (16)
O3—C3—C2	107.47 (13)	C10—C9—C8	119.76 (17)
O3—C3—H3A	110.2	C10—C9—H9	120.1
C2—C3—H3A	110.2	C8—C9—H9	120.1
O3—C3—H3B	110.2	C9—C10—C5	120.98 (16)
C2—C3—H3B	110.2	C9—C10—H10	119.5
H3A—C3—H3B	108.5	C5—C10—H10	119.5
C5—C4—N1	112.66 (14)	H5A—O5—H5B	112 (3)

C4—N1—C2—C3	177.31 (14)	C10—C5—C6—C7	0.9 (3)
C4—N1—C2—C1	55.06 (18)	C4—C5—C6—C7	−176.43 (16)
O1—C1—C2—N1	28.0 (2)	C5—C6—C7—C8	0.9 (3)
O2—C1—C2—N1	−153.20 (14)	C6—C7—C8—O4	177.55 (17)
O1—C1—C2—C3	−92.54 (18)	C6—C7—C8—C9	−1.8 (3)
O2—C1—C2—C3	86.31 (18)	O4—C8—C9—C10	−178.43 (17)
N1—C2—C3—O3	−59.05 (18)	C7—C8—C9—C10	0.9 (3)
C1—C2—C3—O3	64.27 (18)	C8—C9—C10—C5	0.9 (3)
C2—N1—C4—C5	65.0 (2)	C6—C5—C10—C9	−1.7 (3)
N1—C4—C5—C10	96.82 (19)	C4—C5—C10—C9	175.60 (17)
N1—C4—C5—C6	−85.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5	0.98 (3)	1.79 (3)	2.759 (2)	166 (2)
O4—H4···O2ⁱ	0.90 (3)	1.72 (3)	2.624 (2)	174 (3)
N1—H1A···O1ⁱⁱ	0.94 (2)	1.98 (2)	2.8390 (19)	150 (2)
N1—H1B···O1ⁱⁱⁱ	0.96 (3)	1.84 (3)	2.782 (2)	170 (2)
C2—H2···O4^iv	1.00	2.54	3.300 (2)	132
C4—H4A···O3ⁱⁱ	0.99	2.55	3.392 (2)	143
O5—H5A···O2^v	0.85 (3)	1.99 (3)	2.8380 (19)	172 (3)
O5—H5B···O4^vi	0.87 (3)	1.92 (3)	2.785 (2)	171 (3)

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

Funding information

Funding for this research was provided by: Natural Science Foundation of China (award No. 21571118).

References

Han, H., Lu, L. P., Wang, Q. M., Zhu, M. L., Yuan, C. X., Xing, S. & Fu, X. Q. (2012). Dalton Trans. 41, 11116–11124. Web of Science CSD CrossRef CAS PubMed Google Scholar
Li, Y. H., Lu, L. P., Zhu, M. L., Yuan, C. X., Feng, S. S. & Gao, Z. Q. (2016). Chin. J. Struct. Chem. 35, 1686–1693. CAS Google Scholar
Lu, L. P. & Zhu, M. L. (2014). Antioxid. Redox Signal. 20, 2210–2224. CrossRef CAS PubMed Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.