Potassium N-(6-oxo­cyclo­hexa-1,3-dien-5-yl­idene­methyl)­glycinate

We are very interested in characterizing ligands derived from salicyl­aldehyde and [alpha]-amino acids. These ligands form interesting complexes with different transition metals, which are very useful for understanding some biological systems. For Schiff bases derived from salicyl­aldehyde and different alkyl­amines or aryl­amines, the enol-imine form is predominant. The title compound, (I), shows bond distances which are clearly in agreement with the keto-amine form.

S1. Comment

No text

S2. Experimental

No text provided.

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 1997); program(s) used to refine structure: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

N-glicyl-2-hydroxibenzaldiminate potasium salt

Crystal data

K^+·C9H8NO3^−	F(000) = 896
Mr = 217.26	Dx = 1.613 Mg m^−3
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 18191 reflections
a = 13.8864 (2) Å	θ = 2.9–27.5°
b = 18.4943 (7) Å	µ = 0.57 mm^−1
c = 6.9664 (9) Å	T = 100 K
V = 1789.1 (2) Å^3	Plate, orange
Z = 8	0.30 × 0.30 × 0.10 mm

Data collection

KappaCCD diffractometer	2036 independent reflections
Radiation source: fine-focus sealed tube	1580 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ϕ and ω scans with κ offsets	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −18→18
Tmin = 0.848, Tmax = 0.945	k = −24→24
18191 measured reflections	l = −8→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0531P)^2 + 0.085P] where P = (Fo^2 + 2Fc^2)/3
2036 reflections	(Δ/σ)max = 0.001
131 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

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	0.37216 (2)	0.566063 (19)	0.61305 (5)	0.02087 (13)
O1	0.44004 (8)	0.41710 (7)	0.49912 (17)	0.0243 (3)
O2	0.32160 (8)	0.42719 (6)	0.71803 (16)	0.0231 (3)
O3	0.61865 (8)	0.28272 (6)	0.37158 (16)	0.0242 (3)
N1	0.44982 (10)	0.27315 (8)	0.54113 (19)	0.0214 (3)
C1	0.37832 (11)	0.39230 (9)	0.6127 (2)	0.0198 (3)
C2	0.36668 (12)	0.30998 (9)	0.6223 (2)	0.0226 (4)
H2A	0.3584	0.2950	0.7577	0.027*
H2B	0.3081	0.2956	0.5509	0.027*
C3	0.46524 (12)	0.20415 (9)	0.5471 (2)	0.0208 (4)
H3A	0.4185	0.1743	0.6076	0.025*
C4	0.54831 (12)	0.17059 (9)	0.4681 (2)	0.0208 (4)
C5	0.55599 (12)	0.09424 (10)	0.4748 (2)	0.0248 (4)
H5A	0.5088	0.0672	0.5426	0.030*
C6	0.63001 (13)	0.05864 (10)	0.3855 (2)	0.0274 (4)
H6A	0.6353	0.0075	0.3936	0.033*
C7	0.69775 (12)	0.09911 (10)	0.2821 (2)	0.0261 (4)
H7A	0.7473	0.0745	0.2146	0.031*
C8	0.69451 (12)	0.17329 (9)	0.2756 (2)	0.0236 (4)
H8A	0.7423	0.1986	0.2047	0.028*
C9	0.62095 (12)	0.21367 (9)	0.3729 (2)	0.0211 (4)
H1N	0.4944 (16)	0.3002 (11)	0.479 (3)	0.036 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.0176 (2)	0.0228 (2)	0.0222 (2)	−0.00108 (14)	0.00109 (13)	0.00007 (14)
O1	0.0214 (6)	0.0250 (7)	0.0266 (6)	−0.0019 (5)	0.0030 (5)	0.0008 (5)
O2	0.0188 (6)	0.0244 (6)	0.0261 (6)	0.0026 (5)	0.0009 (5)	−0.0018 (5)
O3	0.0239 (6)	0.0217 (6)	0.0271 (6)	−0.0016 (5)	0.0024 (5)	−0.0007 (5)
N1	0.0181 (7)	0.0246 (8)	0.0214 (7)	−0.0008 (6)	0.0007 (6)	−0.0003 (6)
C1	0.0147 (8)	0.0248 (9)	0.0197 (8)	−0.0003 (7)	−0.0032 (6)	0.0002 (6)
C2	0.0168 (8)	0.0237 (9)	0.0272 (9)	0.0009 (7)	0.0042 (7)	−0.0006 (7)
C3	0.0211 (9)	0.0237 (9)	0.0175 (8)	−0.0018 (7)	−0.0021 (6)	0.0005 (6)
C4	0.0195 (8)	0.0238 (9)	0.0191 (8)	0.0009 (7)	−0.0023 (6)	−0.0014 (6)
C5	0.0226 (8)	0.0240 (9)	0.0278 (9)	−0.0009 (7)	−0.0004 (7)	0.0012 (7)
C6	0.0273 (10)	0.0209 (9)	0.0340 (10)	0.0037 (7)	−0.0015 (7)	0.0000 (7)
C7	0.0199 (9)	0.0304 (10)	0.0281 (9)	0.0060 (8)	−0.0013 (7)	−0.0046 (7)
C8	0.0175 (8)	0.0308 (10)	0.0227 (8)	−0.0019 (7)	−0.0010 (6)	−0.0012 (7)
C9	0.0195 (8)	0.0251 (9)	0.0187 (8)	−0.0005 (7)	−0.0038 (6)	−0.0011 (6)

Geometric parameters (Å, º)

K1—O1^i	2.7402 (12)	O2—C1	1.2551 (19)
K1—O2	2.7612 (12)	O2—K1^ii	2.7911 (12)
K1—O2^ii	2.7911 (12)	O2—K1^iv	2.8427 (12)
K1—O3^i	2.8016 (12)	O3—C9	1.277 (2)
K1—O2^iii	2.8427 (12)	O3—K1^i	2.8016 (12)
K1—O1^iv	2.8669 (13)	N1—C3	1.295 (2)
K1—O1	3.0180 (13)	N1—C2	1.455 (2)
K1—C1	3.2147 (18)	C1—C2	1.533 (2)
K1—K1^v	4.0308 (7)	C3—C4	1.421 (2)
K1—K1^ii	4.1811 (7)	C4—C5	1.417 (2)
K1—K1^iii	4.2549 (6)	C4—C9	1.446 (2)
K1—K1^iv	4.2549 (6)	C5—C6	1.370 (2)
O1—C1	1.2533 (19)	C6—C7	1.401 (2)
O1—K1^i	2.7402 (12)	C7—C8	1.373 (2)
O1—K1^iii	2.8669 (13)	C8—C9	1.435 (2)
O1^i—K1—O2	115.04 (4)	O2^iii—K1—K1^iii	39.89 (2)
O1^i—K1—O2^ii	170.80 (4)	O1^iv—K1—K1^iii	146.14 (3)
O2—K1—O2^ii	74.16 (4)	O1—K1—K1^iii	42.31 (2)
O1^i—K1—O3^i	81.61 (4)	C1—K1—K1^iii	54.92 (3)
O2—K1—O3^i	158.43 (3)	K1^v—K1—K1^iii	112.802 (8)
O2^ii—K1—O3^i	89.39 (3)	K1^ii—K1—K1^iii	70.388 (9)
O1^i—K1—O2^iii	87.36 (3)	O1^i—K1—K1^iv	107.38 (3)
O2—K1—O2^iii	103.56 (3)	O2—K1—K1^iv	41.32 (2)
O2^ii—K1—O2^iii	90.78 (3)	O2^ii—K1—K1^iv	79.11 (2)
O3^i—K1—O2^iii	90.26 (3)	O3^i—K1—K1^iv	122.82 (2)
O1^i—K1—O1^iv	86.69 (4)	O2^iii—K1—K1^iv	144.85 (3)
O2—K1—O1^iv	86.34 (4)	O1^iv—K1—K1^iv	45.12 (3)
O2^ii—K1—O1^iv	93.80 (3)	O1—K1—K1^iv	72.00 (3)
O3^i—K1—O1^iv	80.84 (3)	C1—K1—K1^iv	55.01 (3)
O2^iii—K1—O1^iv	169.93 (4)	K1^v—K1—K1^iv	67.198 (8)
O1^i—K1—O1	74.43 (4)	K1^ii—K1—K1^iv	70.388 (9)
O2—K1—O1	45.57 (3)	K1^iii—K1—K1^iv	109.898 (17)
O2^ii—K1—O1	114.25 (3)	C1—O1—K1^i	150.74 (11)
O3^i—K1—O1	155.10 (3)	C1—O1—K1^iii	114.02 (10)
O2^iii—K1—O1	82.10 (3)	K1^i—O1—K1^iii	91.89 (4)
O1^iv—K1—O1	104.07 (3)	C1—O1—K1	87.39 (10)
O1^i—K1—C1	95.05 (4)	K1^i—O1—K1	105.58 (4)
O2—K1—C1	22.65 (3)	K1^iii—O1—K1	92.57 (3)
O2^ii—K1—C1	94.04 (4)	C1—O2—K1	99.43 (10)
O3^i—K1—C1	175.34 (4)	C1—O2—K1^ii	118.34 (10)
O2^iii—K1—C1	92.85 (4)	K1—O2—K1^ii	97.71 (4)
O1^iv—K1—C1	95.77 (4)	C1—O2—K1^iv	115.70 (9)
O1—K1—C1	22.92 (3)	K1—O2—K1^iv	98.79 (4)
O1^i—K1—K1^v	45.31 (3)	K1^ii—O2—K1^iv	119.33 (4)
O2—K1—K1^v	95.66 (2)	C9—O3—K1^i	175.20 (10)
O2^ii—K1—K1^v	136.48 (3)	C3—N1—C2	125.47 (15)
O3^i—K1—K1^v	86.66 (2)	O1—C1—O2	127.59 (16)
O2^iii—K1—K1^v	132.52 (3)	O1—C1—C2	117.59 (14)
O1^iv—K1—K1^v	42.80 (2)	O2—C1—C2	114.78 (14)
O1—K1—K1^v	81.34 (2)	O1—C1—K1	69.69 (9)
C1—K1—K1^v	88.68 (3)	O2—C1—K1	57.92 (9)
O1^i—K1—K1^ii	147.00 (3)	C2—C1—K1	172.00 (10)
O2—K1—K1^ii	41.42 (2)	N1—C2—C1	111.38 (13)
O2^ii—K1—K1^ii	40.88 (2)	N1—C3—C4	123.53 (15)
O3^i—K1—K1^ii	128.34 (3)	C5—C4—C3	118.92 (15)
O2^iii—K1—K1^ii	79.94 (2)	C5—C4—C9	120.77 (15)
O1^iv—K1—K1^ii	109.28 (2)	C3—C4—C9	120.22 (15)
O1—K1—K1^ii	73.74 (2)	C6—C5—C4	121.36 (16)
C1—K1—K1^ii	55.76 (3)	C5—C6—C7	118.71 (17)
K1^v—K1—K1^ii	135.623 (8)	C8—C7—C6	121.91 (16)
O1^i—K1—K1^iii	80.32 (3)	C7—C8—C9	121.82 (15)
O2—K1—K1^iii	71.50 (3)	O3—C9—C8	122.31 (15)
O2^ii—K1—K1^iii	103.90 (2)	O3—C9—C4	122.44 (15)
O3^i—K1—K1^iii	127.20 (2)	C8—C9—C4	115.23 (15)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.91 (2)	1.91 (2)	2.6310 (19)	135.4 (18)