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Acta Cryst. (2007). E63, m2370    [ doi:10.1107/S1600536807040329 ]

Potassium salt of salicylidene-[beta]-hydroxyalanine

X.-S. Gao, Y.-M. Wan, Z.-F. Lv, Y.-X. Shi and J.-T. Wang

Abstract top

The title compound, poly[[[mu]-3-hydroxy-2-(2-hydroxybenzylideneamino)propionato]potassium], [K(C10H10NO4)]n, is an effective material for preparing rare earth Eu complexes. It is composed of planar six-membered rings and planar five-membered rings formed by intramolecular O-H...N hydrogen bonding, which are oriented with respect to each other at a dihedral angle of 3.56 (4)°. The K+ ion is surrounded by seven O atoms, five from three carboxylate groups and two from two hydroxyl groups. In the crystal structure, intermolecular O-H...O hydrogen bonds result in the formation of chains along the c axis.

Comment top

The title compound, (I), is an effective material for preparing rare earth complexes (Parekh & Patel, 2005). We herein report its crystal structure.

In the molecule of (I) (Fig. 1), the bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). Intramolecular O—H···N hydrogen bonding (Table 2) results in the formation of planar five-membered ring A (O4/H4/N1/C4–C6). Ring B (C5–C10) is, of course, planar and the dihedral angle between planes A and B is 3.56 (4)°. On the other hand, the C2/C4–C10/N1/O4 unit is nearly planar, with an r.m.s. deviation of 0.0425 Å.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 2 and Fig. 2) result in the formation of chains along the c axis.

Related literature top

For bond-length data, see: Allen et al. (1987). For related literature, see: Parekh & Patel (2005).

Experimental top

The title compound was prepared by the literature method (Parekh & Patel, 2005). The resulting solid was recrystallized from ethanol-ether (1:1) mixture to give suitable crystals of (I) for X-ray analysis (yield; 65%).

Refinement top

H3 and H4A (for OH groups) were located in difference syntheses and refined isotropically [O3—H3 = 0.79 (3) Å, Uiso(H) = 0.053 (8) Å2 and O4—H4A = 0.85 (3) Å, Uiso(H) = 0.087 (11) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry codes: (A) −x + 3/2, y, z + 1/2; (B) x, y, z + 1].
[Figure 2] Fig. 2. A packing diagram for (I).
poly[[µ-3-hydroxy-2-(2-hydroxybenzylideneamino)propionato]potassium] top
Crystal data top
[K(C10H10NO4)]F000 = 512
Mr = 247.29Dx = 1.504 Mg m−3
Orthorhombic, Pca21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1145 reflections
a = 7.9571 (6) Åθ = 3.0–25.1º
b = 17.7596 (13) ŵ = 0.48 mm−1
c = 7.7258 (6) ÅT = 291 (2) K
V = 1091.77 (14) Å3Block, yellow
Z = 40.16 × 0.12 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		1782 independent reflections
Radiation source: fine-focus sealed tube1689 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 291(2) Kθmax = 26.0º
φ and ω scansθmin = 2.3º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −9→9
Tmin = 0.927, Tmax = 0.953k = −20→21
5642 measured reflectionsl = −9→7
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.024  w = 1/[σ2(Fo2) + (0.0438P)2 + 0.0126P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.068(Δ/σ)max = 0.002
S = 1.06Δρmax = 0.17 e Å−3
1782 reflectionsΔρmin = −0.13 e Å−3
153 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 630 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.06 (4)
Secondary atom site location: difference Fourier map
Crystal data top
[K(C10H10NO4)]V = 1091.77 (14) Å3
Mr = 247.29Z = 4
Orthorhombic, Pca21Mo Kα
a = 7.9571 (6) ŵ = 0.48 mm−1
b = 17.7596 (13) ÅT = 291 (2) K
c = 7.7258 (6) Å0.16 × 0.12 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		1782 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1689 reflections with I > 2σ(I)
Tmin = 0.927, Tmax = 0.953Rint = 0.027
5642 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.024H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.068Δρmax = 0.17 e Å−3
S = 1.06Δρmin = −0.13 e Å−3
1782 reflectionsAbsolute structure: Flack (1983), 630 Friedel pairs
153 parametersFlack parameter: −0.06 (4)
1 restraint
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
K10.91131 (5)1.03625 (2)1.40599 (7)0.04057 (13)
O10.86842 (16)1.08264 (8)1.0595 (2)0.0402 (3)
O21.13102 (19)1.09544 (8)1.1450 (2)0.0440 (4)
O31.0429 (2)1.10354 (8)0.70054 (19)0.0427 (4)
H31.141 (3)1.1124 (14)0.700 (4)0.053 (8)*
O41.49653 (19)1.22892 (9)0.8458 (2)0.0483 (4)
H4A1.400 (4)1.2107 (18)0.872 (6)0.087 (11)*
N11.18204 (19)1.22190 (8)0.9470 (2)0.0345 (4)
C11.0058 (2)1.11657 (10)1.0608 (3)0.0309 (4)
C21.0143 (2)1.18757 (11)0.9488 (3)0.0339 (4)
H20.93471.22440.99550.041*
C30.9613 (3)1.16839 (12)0.7653 (3)0.0387 (5)
H3A0.84081.16030.76280.046*
H3B0.98641.21080.69040.046*
C41.1984 (2)1.28810 (11)1.0049 (3)0.0392 (5)
H41.10571.31151.05460.047*
C51.3570 (3)1.32923 (11)0.9967 (3)0.0405 (5)
C61.4980 (2)1.29850 (11)0.9128 (3)0.0412 (4)
C71.6432 (3)1.34175 (13)0.8968 (5)0.0607 (6)
H71.73581.32270.83780.073*
C81.6498 (4)1.41259 (15)0.9681 (5)0.0789 (10)
H81.74701.44110.95600.095*
C91.5147 (4)1.44216 (14)1.0573 (6)0.0828 (10)
H91.52191.48971.10700.099*
C101.3691 (3)1.40066 (12)1.0720 (5)0.0609 (7)
H101.27801.42031.13240.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K10.0396 (2)0.0493 (2)0.0329 (2)0.00844 (17)0.00437 (19)0.0037 (2)
O10.0326 (7)0.0483 (8)0.0398 (8)−0.0112 (6)−0.0002 (7)0.0046 (6)
O20.0336 (7)0.0456 (8)0.0527 (10)−0.0037 (6)−0.0075 (7)0.0111 (7)
O30.0347 (7)0.0539 (9)0.0396 (9)−0.0066 (7)0.0036 (7)−0.0091 (7)
O40.0450 (9)0.0563 (10)0.0435 (9)−0.0054 (7)0.0029 (7)−0.0065 (7)
N10.0340 (8)0.0359 (8)0.0335 (10)−0.0056 (6)0.0020 (6)0.0014 (6)
C10.0285 (9)0.0362 (9)0.0279 (10)−0.0004 (7)0.0023 (8)−0.0031 (8)
C20.0297 (9)0.0363 (9)0.0356 (11)−0.0003 (7)0.0040 (7)0.0007 (8)
C30.0352 (10)0.0464 (11)0.0346 (11)−0.0021 (8)−0.0007 (8)0.0062 (9)
C40.0395 (11)0.0370 (11)0.0411 (12)−0.0005 (8)0.0036 (9)0.0045 (8)
C50.0464 (11)0.0328 (10)0.0424 (12)−0.0067 (8)−0.0073 (9)0.0062 (8)
C60.0413 (11)0.0452 (10)0.0371 (11)−0.0061 (7)−0.0066 (10)0.0115 (10)
C70.0429 (11)0.0652 (14)0.0741 (17)−0.0118 (10)−0.0057 (15)0.0092 (16)
C80.0565 (15)0.0589 (16)0.121 (3)−0.0256 (12)−0.0184 (18)0.0143 (15)
C90.0706 (19)0.0418 (14)0.136 (3)−0.0157 (12)−0.021 (2)−0.0080 (18)
C100.0587 (14)0.0380 (12)0.086 (2)−0.0021 (10)−0.0047 (15)−0.0068 (12)
Geometric parameters (Å, °) top
K1—O1i2.6533 (14)C4—N11.265 (2)
K1—O3ii2.7755 (16)C4—C51.460 (3)
K1—O12.8215 (16)C4—H40.9300
K1—O22.8685 (17)C5—C101.399 (3)
K1—O3iii2.9691 (16)C5—C61.406 (3)
K1—O1iii2.9896 (15)C6—O41.340 (3)
K1—O2iii2.9986 (17)C6—C71.393 (3)
K1—C1iii3.0384 (19)C7—C81.374 (4)
K1—K1iv4.1817 (4)C7—H70.9300
K1—K1v4.1817 (4)C8—C91.380 (5)
K1—K1vi4.3095 (4)C8—H80.9300
K1—K1iii4.3095 (4)C9—C101.378 (4)
C1—O21.248 (2)C9—H90.9300
C1—O11.248 (2)C10—H100.9300
C1—C21.531 (3)O1—K1vii2.6533 (14)
C1—K1vi3.0384 (19)O1—K1vi2.9896 (15)
C2—N11.468 (2)O2—K1vi2.9986 (17)
C2—C31.517 (3)O3—K1viii2.7755 (16)
C2—H20.9800O3—K1vi2.9691 (16)
C3—O31.414 (3)O3—H30.79 (3)
C3—H3A0.9700O4—H4A0.85 (3)
C3—H3B0.9700
O1i—K1—O3ii79.42 (5)O2iii—K1—K1iii41.57 (3)
O1i—K1—O1103.41 (4)C1iii—K1—K1iii46.30 (4)
O3ii—K1—O1134.25 (4)K1iv—K1—K1iii102.687 (14)
O1i—K1—O2135.38 (4)K1v—K1—K1iii66.196 (10)
O3ii—K1—O2100.87 (5)K1vi—K1—K1iii127.367 (19)
O1—K1—O245.55 (4)O2—C1—O1123.94 (19)
O1i—K1—O3iii126.98 (5)O2—C1—C2120.46 (16)
O3ii—K1—O3iii138.77 (3)O1—C1—C2115.60 (16)
O1—K1—O3iii75.63 (4)O2—C1—K1vi76.29 (11)
O2—K1—O3iii81.71 (4)O1—C1—K1vi75.87 (11)
O1i—K1—O1iii122.26 (6)C2—C1—K1vi120.25 (12)
O3ii—K1—O1iii75.97 (4)N1—C2—C3109.69 (15)
O1—K1—O1iii130.81 (4)N1—C2—C1112.83 (15)
O2—K1—O1iii100.39 (4)C3—C2—C1109.32 (16)
O3iii—K1—O1iii63.23 (4)N1—C2—H2108.3
O1i—K1—O2iii82.69 (4)C3—C2—H2108.3
O3ii—K1—O2iii82.73 (5)C1—C2—H2108.3
O1—K1—O2iii142.97 (4)O3—C3—C2112.71 (17)
O2—K1—O2iii141.92 (2)O3—C3—H3A109.0
O3iii—K1—O2iii71.99 (4)C2—C3—H3A109.0
O1iii—K1—O2iii43.17 (4)O3—C3—H3B109.0
O1i—K1—C1iii106.48 (5)C2—C3—H3B109.0
O3ii—K1—C1iii88.85 (5)H3A—C3—H3B107.8
O1—K1—C1iii131.34 (5)N1—C4—C5122.61 (18)
O2—K1—C1iii118.14 (5)N1—C4—H4118.7
O3iii—K1—C1iii55.73 (5)C5—C4—H4118.7
O1iii—K1—C1iii23.88 (4)C10—C5—C6119.3 (2)
O2iii—K1—C1iii23.85 (4)C10—C5—C4119.7 (2)
O1i—K1—K1iv45.37 (3)C6—C5—C4121.05 (18)
O3ii—K1—K1iv119.44 (3)O4—C6—C7118.8 (2)
O1—K1—K1iv88.56 (3)O4—C6—C5121.93 (17)
O2—K1—K1iv133.84 (3)C7—C6—C5119.3 (2)
O3iii—K1—K1iv81.91 (3)C8—C7—C6120.0 (3)
O1iii—K1—K1iv109.90 (3)C8—C7—H7120.0
O2iii—K1—K1iv69.70 (3)C6—C7—H7120.0
C1iii—K1—K1iv86.08 (4)C7—C8—C9121.2 (2)
O1i—K1—K1v153.35 (3)C7—C8—H8119.4
O3ii—K1—K1v76.91 (3)C9—C8—H8119.4
O1—K1—K1v101.83 (3)C10—C9—C8119.5 (3)
O2—K1—K1v62.16 (3)C10—C9—H9120.2
O3iii—K1—K1v68.03 (3)C8—C9—H9120.2
O1iii—K1—K1v39.17 (3)C9—C10—C5120.6 (3)
O2iii—K1—K1v82.34 (3)C9—C10—H10119.7
C1iii—K1—K1v61.21 (3)C5—C10—H10119.7
K1iv—K1—K1v144.13 (2)C4—N1—C2118.45 (16)
O1i—K1—K1vi140.20 (4)C1—O1—K1vii152.63 (14)
O3ii—K1—K1vi137.73 (4)C1—O1—K191.58 (12)
O1—K1—K1vi43.65 (3)K1vii—O1—K1115.78 (5)
O2—K1—K1vi43.92 (3)C1—O1—K1vi80.25 (10)
O3iii—K1—K1vi39.72 (3)K1vii—O1—K1vi95.46 (4)
O1iii—K1—K1vi87.28 (3)K1—O1—K1vi95.69 (4)
O2iii—K1—K1vi110.83 (3)C1—O2—K189.42 (12)
C1iii—K1—K1vi90.85 (4)C1—O2—K1vi79.86 (11)
K1iv—K1—K1vi102.687 (14)K1—O2—K1vi94.51 (4)
K1v—K1—K1vi66.196 (10)C3—O3—K1viii117.90 (12)
O1i—K1—K1iii88.10 (3)C3—O3—K1vi123.25 (12)
O3ii—K1—K1iii43.13 (3)K1viii—O3—K1vi97.15 (4)
O1—K1—K1iii167.76 (3)C3—O3—H3106.8 (18)
O2—K1—K1iii122.68 (4)K1viii—O3—H3117 (2)
O3iii—K1—K1iii100.91 (3)K1vi—O3—H392.8 (18)
O1iii—K1—K1iii40.65 (3)C6—O4—H4A106 (2)
Symmetry codes: (i) −x+3/2, y, z+1/2; (ii) x, y, z+1; (iii) −x+2, −y+2, z+1/2; (iv) x−1/2, −y+2, z; (v) x+1/2, −y+2, z; (vi) −x+2, −y+2, z−1/2; (vii) −x+3/2, y, z−1/2; (viii) x, y, z−1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2ix0.80 (2)1.89 (2)2.634 (2)156 (3)
O4—H4A···N10.86 (3)1.84 (3)2.625 (2)151 (3)
Symmetry codes: (ix) −x+5/2, y, z−1/2.
Table 1
Selected geometric parameters (Å, °) top
K1—O1i2.6533 (14)K1—C1iii3.0384 (19)
K1—O3ii2.7755 (16)C1—O21.248 (2)
K1—O12.8215 (16)C1—O11.248 (2)
K1—O22.8685 (17)C2—N11.468 (2)
K1—O3iii2.9691 (16)C3—O31.414 (3)
K1—O1iii2.9896 (15)C4—N11.265 (2)
K1—O2iii2.9986 (17)C6—O41.340 (3)
O1i—K1—O3ii79.42 (5)O3ii—K1—O1iii75.97 (4)
O1i—K1—O1103.41 (4)O1—K1—O1iii130.81 (4)
O3ii—K1—O1134.25 (4)O2—K1—O1iii100.39 (4)
O1i—K1—O2135.38 (4)O3iii—K1—O1iii63.23 (4)
O3ii—K1—O2100.87 (5)O1i—K1—O2iii82.69 (4)
O1—K1—O245.55 (4)O3ii—K1—O2iii82.73 (5)
O1i—K1—O3iii126.98 (5)O1—K1—O2iii142.97 (4)
O3ii—K1—O3iii138.77 (3)O2—K1—O2iii141.92 (2)
O1—K1—O3iii75.63 (4)O3iii—K1—O2iii71.99 (4)
O2—K1—O3iii81.71 (4)O1iii—K1—O2iii43.17 (4)
O1i—K1—O1iii122.26 (6)
Symmetry codes: (i) −x+3/2, y, z+1/2; (ii) x, y, z+1; (iii) −x+2, −y+2, z+1/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2iv0.80 (2)1.89 (2)2.634 (2)156 (3)
O4—H4A···N10.86 (3)1.84 (3)2.625 (2)151 (3)
Symmetry codes: (iv) −x+5/2, y, z−1/2.
Acknowledgements top

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bruker (2000). SMART (Version 5.622), SAINT (Version 6.02a), SADABS (Version 2.03) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Parekh, H. M. & Patel, M. N. (2005). Toxicol. Environ. Chem. 87, 449–461.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.