Potassium salt of salicyl­idene-β-hydroxy­alanine

The title compound, poly[[μ-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.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.024
• wR factor = 0.068
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.43 Ratio

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               1782
           Count of symmetry unique reflns         1155
           Completeness (_total/calc)            154.29%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       627
           Fraction of Friedel pairs measured     0.543
           Are heavy atom types Z>Si present        yes
PLAT792_ALERT_1_G Check the Absolute Configuration of C2     = ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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%).

S3. Refinement

H3 and H4A (for OH groups) were located in difference syntheses and refined isotropically [O3—H3 = 0.79 (3) Å, U_iso(H) = 0.053 (8) Ų and O4—H4A = 0.85 (3) Å, U_iso(H) = 0.087 (11) Ų]. 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 U_iso(H) = 1.2U_eq(C).

Computing details

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

	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].
	Fig. 2. A packing diagram for (I).

poly[[µ-3-hydroxy-2-(2-hydroxybenzylideneamino)propionato]potassium]

Crystal data

[K(C10H10NO4)]	F(000) = 512
Mr = 247.29	Dx = 1.504 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1145 reflections
a = 7.9571 (6) Å	θ = 3.0–25.1°
b = 17.7596 (13) Å	µ = 0.48 mm^−1
c = 7.7258 (6) Å	T = 291 K
V = 1091.77 (14) Å^3	Block, yellow
Z = 4	0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1782 independent reflections
Radiation source: fine-focus sealed tube	1689 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.927, Tmax = 0.953	k = −20→21
5642 measured reflections	l = −9→7

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.068	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.0126P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
1782 reflections	Δρmax = 0.17 e Å^−3
153 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Absolute structure: Flack (1983), 630 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
K1	0.91131 (5)	1.03625 (2)	1.40599 (7)	0.04057 (13)
O1	0.86842 (16)	1.08264 (8)	1.0595 (2)	0.0402 (3)
O2	1.13102 (19)	1.09544 (8)	1.1450 (2)	0.0440 (4)
O3	1.0429 (2)	1.10354 (8)	0.70054 (19)	0.0427 (4)
H3	1.141 (3)	1.1124 (14)	0.700 (4)	0.053 (8)*
O4	1.49653 (19)	1.22892 (9)	0.8458 (2)	0.0483 (4)
H4A	1.400 (4)	1.2107 (18)	0.872 (6)	0.087 (11)*
N1	1.18204 (19)	1.22190 (8)	0.9470 (2)	0.0345 (4)
C1	1.0058 (2)	1.11657 (10)	1.0608 (3)	0.0309 (4)
C2	1.0143 (2)	1.18757 (11)	0.9488 (3)	0.0339 (4)
H2	0.9347	1.2244	0.9955	0.041*
C3	0.9613 (3)	1.16839 (12)	0.7653 (3)	0.0387 (5)
H3A	0.8408	1.1603	0.7628	0.046*
H3B	0.9864	1.2108	0.6904	0.046*
C4	1.1984 (2)	1.28810 (11)	1.0049 (3)	0.0392 (5)
H4	1.1057	1.3115	1.0546	0.047*
C5	1.3570 (3)	1.32923 (11)	0.9967 (3)	0.0405 (5)
C6	1.4980 (2)	1.29850 (11)	0.9128 (3)	0.0412 (4)
C7	1.6432 (3)	1.34175 (13)	0.8968 (5)	0.0607 (6)
H7	1.7358	1.3227	0.8378	0.073*
C8	1.6498 (4)	1.41259 (15)	0.9681 (5)	0.0789 (10)
H8	1.7470	1.4411	0.9560	0.095*
C9	1.5147 (4)	1.44216 (14)	1.0573 (6)	0.0828 (10)
H9	1.5219	1.4897	1.1070	0.099*
C10	1.3691 (3)	1.40066 (12)	1.0720 (5)	0.0609 (7)
H10	1.2780	1.4203	1.1324	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.0396 (2)	0.0493 (2)	0.0329 (2)	0.00844 (17)	0.00437 (19)	0.0037 (2)
O1	0.0326 (7)	0.0483 (8)	0.0398 (8)	−0.0112 (6)	−0.0002 (7)	0.0046 (6)
O2	0.0336 (7)	0.0456 (8)	0.0527 (10)	−0.0037 (6)	−0.0075 (7)	0.0111 (7)
O3	0.0347 (7)	0.0539 (9)	0.0396 (9)	−0.0066 (7)	0.0036 (7)	−0.0091 (7)
O4	0.0450 (9)	0.0563 (10)	0.0435 (9)	−0.0054 (7)	0.0029 (7)	−0.0065 (7)
N1	0.0340 (8)	0.0359 (8)	0.0335 (10)	−0.0056 (6)	0.0020 (6)	0.0014 (6)
C1	0.0285 (9)	0.0362 (9)	0.0279 (10)	−0.0004 (7)	0.0023 (8)	−0.0031 (8)
C2	0.0297 (9)	0.0363 (9)	0.0356 (11)	−0.0003 (7)	0.0040 (7)	0.0007 (8)
C3	0.0352 (10)	0.0464 (11)	0.0346 (11)	−0.0021 (8)	−0.0007 (8)	0.0062 (9)
C4	0.0395 (11)	0.0370 (11)	0.0411 (12)	−0.0005 (8)	0.0036 (9)	0.0045 (8)
C5	0.0464 (11)	0.0328 (10)	0.0424 (12)	−0.0067 (8)	−0.0073 (9)	0.0062 (8)
C6	0.0413 (11)	0.0452 (10)	0.0371 (11)	−0.0061 (7)	−0.0066 (10)	0.0115 (10)
C7	0.0429 (11)	0.0652 (14)	0.0741 (17)	−0.0118 (10)	−0.0057 (15)	0.0092 (16)
C8	0.0565 (15)	0.0589 (16)	0.121 (3)	−0.0256 (12)	−0.0184 (18)	0.0143 (15)
C9	0.0706 (19)	0.0418 (14)	0.136 (3)	−0.0157 (12)	−0.021 (2)	−0.0080 (18)
C10	0.0587 (14)	0.0380 (12)	0.086 (2)	−0.0021 (10)	−0.0047 (15)	−0.0068 (12)

Geometric parameters (Å, º)

K1—O1^i	2.6533 (14)	C4—N1	1.265 (2)
K1—O3^ii	2.7755 (16)	C4—C5	1.460 (3)
K1—O1	2.8215 (16)	C4—H4	0.9300
K1—O2	2.8685 (17)	C5—C10	1.399 (3)
K1—O3^iii	2.9691 (16)	C5—C6	1.406 (3)
K1—O1^iii	2.9896 (15)	C6—O4	1.340 (3)
K1—O2^iii	2.9986 (17)	C6—C7	1.393 (3)
K1—C1^iii	3.0384 (19)	C7—C8	1.374 (4)
K1—K1^iv	4.1817 (4)	C7—H7	0.9300
K1—K1^v	4.1817 (4)	C8—C9	1.380 (5)
K1—K1^vi	4.3095 (4)	C8—H8	0.9300
K1—K1^iii	4.3095 (4)	C9—C10	1.378 (4)
C1—O2	1.248 (2)	C9—H9	0.9300
C1—O1	1.248 (2)	C10—H10	0.9300
C1—C2	1.531 (3)	O1—K1^vii	2.6533 (14)
C1—K1^vi	3.0384 (19)	O1—K1^vi	2.9896 (15)
C2—N1	1.468 (2)	O2—K1^vi	2.9986 (17)
C2—C3	1.517 (3)	O3—K1^viii	2.7755 (16)
C2—H2	0.9800	O3—K1^vi	2.9691 (16)
C3—O3	1.414 (3)	O3—H3	0.79 (3)
C3—H3A	0.9700	O4—H4A	0.85 (3)
C3—H3B	0.9700
O1^i—K1—O3^ii	79.42 (5)	O2^iii—K1—K1^iii	41.57 (3)
O1^i—K1—O1	103.41 (4)	C1^iii—K1—K1^iii	46.30 (4)
O3^ii—K1—O1	134.25 (4)	K1^iv—K1—K1^iii	102.687 (14)
O1^i—K1—O2	135.38 (4)	K1^v—K1—K1^iii	66.196 (10)
O3^ii—K1—O2	100.87 (5)	K1^vi—K1—K1^iii	127.367 (19)
O1—K1—O2	45.55 (4)	O2—C1—O1	123.94 (19)
O1^i—K1—O3^iii	126.98 (5)	O2—C1—C2	120.46 (16)
O3^ii—K1—O3^iii	138.77 (3)	O1—C1—C2	115.60 (16)
O1—K1—O3^iii	75.63 (4)	O2—C1—K1^vi	76.29 (11)
O2—K1—O3^iii	81.71 (4)	O1—C1—K1^vi	75.87 (11)
O1^i—K1—O1^iii	122.26 (6)	C2—C1—K1^vi	120.25 (12)
O3^ii—K1—O1^iii	75.97 (4)	N1—C2—C3	109.69 (15)
O1—K1—O1^iii	130.81 (4)	N1—C2—C1	112.83 (15)
O2—K1—O1^iii	100.39 (4)	C3—C2—C1	109.32 (16)
O3^iii—K1—O1^iii	63.23 (4)	N1—C2—H2	108.3
O1^i—K1—O2^iii	82.69 (4)	C3—C2—H2	108.3
O3^ii—K1—O2^iii	82.73 (5)	C1—C2—H2	108.3
O1—K1—O2^iii	142.97 (4)	O3—C3—C2	112.71 (17)
O2—K1—O2^iii	141.92 (2)	O3—C3—H3A	109.0
O3^iii—K1—O2^iii	71.99 (4)	C2—C3—H3A	109.0
O1^iii—K1—O2^iii	43.17 (4)	O3—C3—H3B	109.0
O1^i—K1—C1^iii	106.48 (5)	C2—C3—H3B	109.0
O3^ii—K1—C1^iii	88.85 (5)	H3A—C3—H3B	107.8
O1—K1—C1^iii	131.34 (5)	N1—C4—C5	122.61 (18)
O2—K1—C1^iii	118.14 (5)	N1—C4—H4	118.7
O3^iii—K1—C1^iii	55.73 (5)	C5—C4—H4	118.7
O1^iii—K1—C1^iii	23.88 (4)	C10—C5—C6	119.3 (2)
O2^iii—K1—C1^iii	23.85 (4)	C10—C5—C4	119.7 (2)
O1^i—K1—K1^iv	45.37 (3)	C6—C5—C4	121.05 (18)
O3^ii—K1—K1^iv	119.44 (3)	O4—C6—C7	118.8 (2)
O1—K1—K1^iv	88.56 (3)	O4—C6—C5	121.93 (17)
O2—K1—K1^iv	133.84 (3)	C7—C6—C5	119.3 (2)
O3^iii—K1—K1^iv	81.91 (3)	C8—C7—C6	120.0 (3)
O1^iii—K1—K1^iv	109.90 (3)	C8—C7—H7	120.0
O2^iii—K1—K1^iv	69.70 (3)	C6—C7—H7	120.0
C1^iii—K1—K1^iv	86.08 (4)	C7—C8—C9	121.2 (2)
O1^i—K1—K1^v	153.35 (3)	C7—C8—H8	119.4
O3^ii—K1—K1^v	76.91 (3)	C9—C8—H8	119.4
O1—K1—K1^v	101.83 (3)	C10—C9—C8	119.5 (3)
O2—K1—K1^v	62.16 (3)	C10—C9—H9	120.2
O3^iii—K1—K1^v	68.03 (3)	C8—C9—H9	120.2
O1^iii—K1—K1^v	39.17 (3)	C9—C10—C5	120.6 (3)
O2^iii—K1—K1^v	82.34 (3)	C9—C10—H10	119.7
C1^iii—K1—K1^v	61.21 (3)	C5—C10—H10	119.7
K1^iv—K1—K1^v	144.13 (2)	C4—N1—C2	118.45 (16)
O1^i—K1—K1^vi	140.20 (4)	C1—O1—K1^vii	152.63 (14)
O3^ii—K1—K1^vi	137.73 (4)	C1—O1—K1	91.58 (12)
O1—K1—K1^vi	43.65 (3)	K1^vii—O1—K1	115.78 (5)
O2—K1—K1^vi	43.92 (3)	C1—O1—K1^vi	80.25 (10)
O3^iii—K1—K1^vi	39.72 (3)	K1^vii—O1—K1^vi	95.46 (4)
O1^iii—K1—K1^vi	87.28 (3)	K1—O1—K1^vi	95.69 (4)
O2^iii—K1—K1^vi	110.83 (3)	C1—O2—K1	89.42 (12)
C1^iii—K1—K1^vi	90.85 (4)	C1—O2—K1^vi	79.86 (11)
K1^iv—K1—K1^vi	102.687 (14)	K1—O2—K1^vi	94.51 (4)
K1^v—K1—K1^vi	66.196 (10)	C3—O3—K1^viii	117.90 (12)
O1^i—K1—K1^iii	88.10 (3)	C3—O3—K1^vi	123.25 (12)
O3^ii—K1—K1^iii	43.13 (3)	K1^viii—O3—K1^vi	97.15 (4)
O1—K1—K1^iii	167.76 (3)	C3—O3—H3	106.8 (18)
O2—K1—K1^iii	122.68 (4)	K1^viii—O3—H3	117 (2)
O3^iii—K1—K1^iii	100.91 (3)	K1^vi—O3—H3	92.8 (18)
O1^iii—K1—K1^iii	40.65 (3)	C6—O4—H4A	106 (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, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^ix	0.80 (2)	1.89 (2)	2.634 (2)	156 (3)
O4—H4A···N1	0.86 (3)	1.84 (3)	2.625 (2)	151 (3)

Symmetry code: (ix) −x+5/2, y, z−1/2.