Poly[aquadi-μ-hippurato-potassium(I)]

Athimoolam, S.; Dhas, S.A.M.B.; Natarajan, S.; Suresh, J.

doi:10.1107/S1600536807028796

Poly[aquadi-μ-hippurato-potassium(I)]

S. Natarajan, S. A. M. B. Dhas, J. Suresh and S. Athimoolam

The title compound, [K(C₉H₈N₂O₃)₂(H₂O)], has one potassium cation, two hippurate anions and one coordinated water molecule in the asymmetric unit. The coordination number of the K⁺ cation is seven, leading to a pentagonal–bipyramidal structure in which the polyhedron is constituted by a central K atom coordinated by six carboxylate O atoms and one water O atom. The benzene rings exhibit orientational disorder (0.55:0.45), leading to two different orientations in both hippurates. Even though the metal coordination dominates the crystal packing, it is further stabilized by hydrogen-bonding interactions. The hydrogen-bonding interactions form an intramolecular S(7) motif and an intermolecularly connected C₂²(7) chain motif.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028796/dn2185sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028796/dn2185Isup2.hkl Contains datablock I

CCDC reference: 654785

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.074
wR factor = 0.248
Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    -   H1W    ...          ?

Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.99
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT301_ALERT_3_C Main Residue  Disorder .........................      22.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.13 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.30 Deg.
              C19' -C14  -C19     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.30 Deg.
              C15  -C14  -C15'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.50 Deg.
              C16' -C17  -C16     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      42.20 Deg.
              C29  -C24  -C29'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.80 Deg.
              C28  -C27  -C28'    1.555   1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

Comment top

Hippuric acid (HA) is an organic acid found in the urine of horses and other animals. High concentrations of HA can also indicate a toluene intoxication. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to HA by reaction with the amino acid glycine. Exposure to toluene may result in central nervous system depression and decreased memory. The crystal growth and morphological studies on HA, which is also one of the minor constituents of urinary stones were carried out in the author's laboratory, recently (Ramachandran & Natarajan, 2005). Presently the structure eluzidation of a series of metal hippurates are undertaken and the title compound (I) is one such case. From the Cambridge Structural Database (Version 5.28; Allen, 2002), it is observed that, among the 24 related structures of hippuric acid, 17 complexes are metal coordinated complexes which clearly indicates the interest of coordination complexes in HA. Recently, we have reported the structure of HA with Ba (Natarajan et al., 2007).

In the present structure (I), potassium has a sevenfold coordination and the polyhedra is a pentagonal bipyramid (Fig. 1). The corners of the pentagon are occupied by four carboxylate O atoms from different hippurates and one water O atom, viz., O12, O11ⁱ, O21ⁱⁱ, O22ⁱⁱⁱ and O1w. Further two carboxylate O atoms (O22 & O11ⁱ) are situated on top and bottom of the sheet of the pentagon forming two five-faced pyramids taking this pentagon as base [Symmetry codes are as given in Table 1]. The K—O coordination distances vary from 2.761 (5) to 3.049 (4) Å. The asymmetric unit of the title compound contains one potassium, two hippurate anions and one coordinated water molecule. The benzene rings of the hippurates are in 'orientational disorder' adopting two different orientations. The angles between the two different orientations are 45.8 (6)° and 46.0 (7)° for residue A (C11–17/N11/O11—O13) and B (C21–27/N21/O21—O23), respectively.

As described in Natarajan et al., 2007, the configuration of the hippurates can be described from the angles between three planes, viz., benzene ring, peptide and carboxylate planes. The angles between the benzene and peptide planes are observed to be 29.4 (6) [23.0 (5)] and 38.7 (5) [9.2 (9)]° for residues A and B respectively (values within the square brackets are attributed to minor components of the disordered benzene rings). The angles between the peptide and carboxylate planes are observed to be 78.7 (4) and 86.3 (3)° for residues A and B respectively. Fig. 2 shows the crystal packing of (I), the coordination polehedra is extended along c=0 plane and phenyl rings are sandwiched between these polyhedra near c=1/2 plane. Eventhough the interesting feature of this structure is the coordination geometry, the crystal packing is further stabilized through the hydrogen bonding interaction (Table 2). Four hydrogen bonding interactions are observed in (I), one as intramolecular and three as intermolecular interactions. The intramolecular H-bond leads to S(7) motif (Etter, 1990). Residue B and water molecule are linked through N21—H21···O1W and O1W—H1W···O22 (x - 1, y, z) hydrogen bonds leading to C₂²(7) chain motif running along the a axis of the unit cell. This forms a layered structure in two directions and bordered by the aromatic rings which block further three dimensional extension.

Related literature top

For related literature on hydrogen-bond motifs, see Etter (1990), and on values of bond lengths, see Allen (2002). For related structures, see Natarajan et al. (2007), and for information about the importance of hippuric acid, see Ramachandran & Natarajan (2005).

Experimental top

The title compound was crystallized by the slow evaporation technique, using an aqueous solution containing potassium hydroxide and hippuric acid in a 1:1 stoichiometric ratio.

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

Figures top

	Fig. 1. The molecular structure of title compound with atom numbering scheme. Ellipsoids are drawn at the 50% probability level. Intramolecular H-bond is shown as dashed line. Only the major components of the disordered atoms are shown for claritly. The complete coordination sphere of the K atom is shown.
	Fig. 2. Partial packing view down the a axis. The minor components of the disordered atoms and the H atoms have been omitted for clariry.

Poly[aquadi-µ-hippurato-potassium(I)] top

Crystal data top

[K(C₉H₈N₂O₃)₂(H₂O)]	Z = 2
M_r = 413.44	F(000) = 430
Triclinic, P1	D_x = 1.447 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.867 (3) Å	Cell parameters from 25 reflections
b = 9.921 (7) Å	θ = 9.8–13.9°
c = 20.076 (9) Å	µ = 0.32 mm⁻¹
α = 92.59 (4)°	T = 293 K
β = 91.45 (3)°	Block, colourless
γ = 101.33 (5)°	0.21 × 0.18 × 0.16 mm
V = 948.9 (10) Å³

Data collection top

Nonius MACH-3 diffractometer	2044 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω–2θ scans	h = −1→5
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.926, T_max = 0.955	l = −23→23
4593 measured reflections	3 standard reflections every 60 min
3327 independent reflections	intensity decay: none

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.248	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.1591P)² + 0.3972P] where P = (F_o² + 2F_c²)/3
3327 reflections	(Δ/σ)_max = 0.001
333 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[K(C₉H₈N₂O₃)₂(H₂O)]	γ = 101.33 (5)°
M_r = 413.44	V = 948.9 (10) Å³
Triclinic, P1	Z = 2
a = 4.867 (3) Å	Mo Kα radiation
b = 9.921 (7) Å	µ = 0.32 mm⁻¹
c = 20.076 (9) Å	T = 293 K
α = 92.59 (4)°	0.21 × 0.18 × 0.16 mm
β = 91.45 (3)°

Data collection top

Nonius MACH-3 diffractometer	2044 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.040
T_min = 0.926, T_max = 0.955	3 standard reflections every 60 min
4593 measured reflections	intensity decay: none
3327 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.248	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.76 e Å⁻³
3327 reflections	Δρ_min = −0.64 e Å⁻³
333 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O11	0.3738 (7)	0.5273 (4)	0.04916 (17)	0.0452 (9)
K	−0.0752 (2)	0.30691 (11)	0.02817 (6)	0.0440 (4)
O12	0.7805 (8)	0.6516 (4)	0.08733 (19)	0.0550 (10)
C11	0.5384 (10)	0.6037 (5)	0.0949 (2)	0.0374 (11)
C12	0.3837 (12)	0.6258 (7)	0.1571 (3)	0.0573 (16)
H11A	0.2376	0.6755	0.1458	0.069*
H11B	0.2925	0.5365	0.1715	0.069*
C13	0.6991 (12)	0.6366 (5)	0.2522 (3)	0.0443 (12)
C14	0.8172 (11)	0.7091 (5)	0.3171 (2)	0.0408 (12)
C17	1.0128 (16)	0.8194 (8)	0.4422 (3)	0.0713 (19)
H17	1.0911	0.8632	0.4821	0.086*
C15	1.039 (3)	0.6699 (14)	0.3482 (7)	0.058 (3)	0.55
H15	1.1311	0.6080	0.3264	0.069*	0.55
C16	1.127 (4)	0.7209 (18)	0.4112 (8)	0.071 (4)	0.55
H16	1.2677	0.6872	0.4332	0.086*	0.55
C18	0.783 (3)	0.8527 (17)	0.4138 (7)	0.082 (4)	0.55
H18	0.6846	0.9093	0.4375	0.098*	0.55
C19	0.691 (3)	0.8039 (13)	0.3502 (6)	0.059 (3)	0.55
H19	0.5443	0.8352	0.3295	0.071*	0.55
C15'	0.888 (3)	0.6268 (13)	0.3685 (7)	0.046 (3)	0.45
H15'	0.8617	0.5318	0.3611	0.055*	0.45
C16'	0.998 (4)	0.687 (2)	0.4299 (9)	0.060 (5)	0.45
H16'	1.0595	0.6345	0.4620	0.072*	0.45
C18'	0.965 (3)	0.9073 (14)	0.3899 (6)	0.047 (3)	0.45
H18'	1.0088	1.0026	0.3967	0.057*	0.45
C19'	0.853 (3)	0.8465 (12)	0.3287 (6)	0.037 (3)	0.45
H19'	0.8016	0.9009	0.2958	0.045*	0.45
N11	0.5499 (10)	0.6994 (5)	0.2126 (2)	0.0489 (11)
H11	0.5518	0.7856	0.2200	0.059*
O13	0.7350 (11)	0.5198 (4)	0.2387 (2)	0.0720 (13)
O21	−0.3007 (8)	0.0504 (4)	−0.03381 (19)	0.0494 (10)
C21	−0.2419 (11)	−0.0434 (5)	−0.0744 (2)	0.0387 (11)
O22	−0.3492 (8)	−0.1653 (4)	−0.07225 (18)	0.0471 (9)
C22	−0.0232 (11)	0.0059 (5)	−0.1245 (3)	0.0459 (13)
H22A	−0.0269	0.1008	−0.1336	0.055*
H22B	0.1609	0.0031	−0.1056	0.055*
C23	−0.2591 (11)	−0.0581 (6)	−0.2308 (3)	0.0443 (12)
C24	−0.3003 (11)	−0.1504 (6)	−0.2926 (3)	0.0464 (13)
C27	−0.3959 (17)	−0.3087 (9)	−0.4102 (4)	0.079 (2)
H27	−0.4215	−0.3643	−0.4493	0.095*
C25	−0.357 (3)	−0.0844 (16)	−0.3550 (6)	0.075 (4)	0.55
H25	−0.3585	0.0091	−0.3553	0.090*	0.55
C26	−0.407 (4)	−0.1681 (19)	−0.4129 (7)	0.086 (4)	0.55
H26	−0.4479	−0.1319	−0.4531	0.103*	0.55
C28	−0.350 (3)	−0.3623 (17)	−0.3534 (8)	0.078 (4)	0.55
H28	−0.3536	−0.4563	−0.3523	0.093*	0.55
C29	−0.296 (3)	−0.2807 (13)	−0.2954 (6)	0.060 (3)	0.55
H29	−0.2556	−0.3211	−0.2564	0.072*	0.55
C25'	−0.544 (3)	−0.1608 (13)	−0.3305 (6)	0.047 (3)	0.45
H25'	−0.6790	−0.1126	−0.3161	0.056*	0.45
C26'	−0.593 (3)	−0.2394 (16)	−0.3883 (7)	0.059 (4)	0.45
H26'	−0.7599	−0.2457	−0.4127	0.070*	0.45
C28'	−0.160 (4)	−0.3163 (16)	−0.3699 (7)	0.061 (4)	0.45
H28'	−0.0377	−0.3735	−0.3824	0.073*	0.45
C29'	−0.115 (3)	−0.2356 (13)	−0.3106 (6)	0.046 (3)	0.45
H29'	0.0401	−0.2383	−0.2829	0.055*	0.45
N21	−0.0693 (9)	−0.0768 (5)	−0.1859 (2)	0.0454 (11)
H21	0.0280	−0.1391	−0.1935	0.055*
O23	−0.3999 (10)	0.0312 (5)	−0.2215 (2)	0.0738 (14)
O1W	−0.2285 (11)	0.2994 (5)	0.1596 (2)	0.0539 (11)
H1W	−0.386 (14)	0.260 (6)	0.143 (3)	0.050 (18)*
H2W	−0.203 (15)	0.372 (7)	0.180 (3)	0.06 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.039 (2)	0.050 (2)	0.045 (2)	0.0106 (16)	−0.0056 (16)	−0.0148 (16)
K	0.0432 (7)	0.0403 (6)	0.0494 (7)	0.0102 (5)	−0.0011 (5)	0.0050 (5)
O12	0.037 (2)	0.079 (3)	0.045 (2)	0.0051 (19)	−0.0012 (17)	−0.0068 (19)
C11	0.034 (3)	0.038 (3)	0.041 (3)	0.011 (2)	−0.001 (2)	0.002 (2)
C12	0.044 (3)	0.082 (4)	0.044 (3)	0.017 (3)	−0.003 (3)	−0.021 (3)
C13	0.048 (3)	0.043 (3)	0.043 (3)	0.013 (2)	0.006 (2)	−0.007 (2)
C14	0.042 (3)	0.042 (3)	0.040 (3)	0.012 (2)	0.003 (2)	0.001 (2)
C17	0.076 (5)	0.091 (5)	0.047 (4)	0.021 (4)	−0.014 (3)	−0.016 (3)
C15	0.041 (7)	0.076 (9)	0.059 (8)	0.023 (6)	−0.003 (6)	−0.003 (6)
C16	0.080 (12)	0.087 (12)	0.055 (10)	0.034 (10)	−0.012 (8)	0.025 (8)
C18	0.081 (10)	0.102 (11)	0.066 (9)	0.040 (9)	−0.023 (8)	−0.038 (8)
C19	0.070 (9)	0.065 (7)	0.048 (7)	0.029 (7)	−0.012 (6)	−0.014 (6)
C15'	0.052 (9)	0.039 (7)	0.054 (8)	0.023 (6)	0.014 (7)	0.012 (6)
C16'	0.068 (12)	0.072 (12)	0.037 (9)	0.005 (9)	−0.011 (8)	0.019 (8)
C18'	0.055 (8)	0.045 (7)	0.043 (7)	0.011 (6)	0.002 (6)	−0.004 (5)
C19'	0.027 (6)	0.047 (7)	0.036 (6)	0.001 (5)	0.010 (5)	0.009 (5)
N11	0.051 (3)	0.058 (3)	0.039 (2)	0.018 (2)	−0.006 (2)	−0.013 (2)
O13	0.101 (4)	0.050 (2)	0.070 (3)	0.032 (2)	−0.006 (3)	−0.020 (2)
O21	0.047 (2)	0.0400 (19)	0.060 (2)	0.0088 (16)	0.0071 (18)	−0.0132 (17)
C21	0.038 (3)	0.034 (3)	0.044 (3)	0.013 (2)	−0.009 (2)	−0.006 (2)
O22	0.046 (2)	0.040 (2)	0.057 (2)	0.0112 (16)	0.0036 (17)	−0.0016 (16)
C22	0.042 (3)	0.044 (3)	0.052 (3)	0.011 (2)	−0.003 (2)	−0.003 (2)
C23	0.031 (3)	0.054 (3)	0.050 (3)	0.014 (2)	0.003 (2)	0.003 (2)
C24	0.038 (3)	0.059 (3)	0.046 (3)	0.019 (2)	0.001 (2)	0.000 (2)
C27	0.083 (6)	0.100 (6)	0.048 (4)	0.007 (4)	0.002 (4)	−0.017 (4)
C25	0.088 (10)	0.096 (10)	0.057 (7)	0.052 (9)	0.004 (7)	0.019 (7)
C26	0.102 (12)	0.112 (12)	0.051 (8)	0.039 (10)	−0.005 (8)	0.004 (8)
C28	0.060 (9)	0.085 (10)	0.092 (11)	0.027 (8)	0.010 (8)	−0.018 (8)
C29	0.053 (8)	0.066 (8)	0.059 (7)	0.009 (6)	−0.001 (6)	−0.006 (6)
C25'	0.038 (7)	0.056 (7)	0.048 (7)	0.008 (6)	0.000 (6)	0.012 (6)
C26'	0.049 (8)	0.081 (10)	0.042 (7)	0.006 (8)	−0.009 (6)	0.001 (7)
C28'	0.073 (11)	0.065 (9)	0.051 (8)	0.028 (8)	0.012 (8)	−0.006 (6)
C29'	0.046 (8)	0.046 (7)	0.052 (7)	0.023 (6)	0.008 (6)	0.001 (5)
N21	0.047 (3)	0.053 (3)	0.043 (2)	0.027 (2)	−0.001 (2)	−0.0044 (19)
O23	0.071 (3)	0.084 (3)	0.081 (3)	0.057 (3)	−0.017 (2)	−0.016 (2)
O1W	0.057 (3)	0.049 (2)	0.059 (3)	0.023 (2)	−0.005 (2)	−0.014 (2)

Geometric parameters (Å, º) top

O11—C11	1.312 (6)	C18'—C19'	1.393 (17)
O11—K	2.780 (4)	C18'—H18'	0.9300
O11—Kⁱ	2.878 (4)	C19'—H19'	0.9300
K—O1W	2.761 (5)	N11—H11	0.8600
K—O12ⁱⁱ	2.762 (4)	O21—C21	1.288 (6)
K—O21	2.789 (4)	C21—O22	1.223 (6)
K—O22ⁱⁱⁱ	2.861 (4)	C21—C22	1.509 (8)
K—O22^iv	3.049 (4)	C21—Kⁱⁱⁱ	3.437 (5)
K—C21ⁱⁱⁱ	3.437 (5)	O22—Kⁱⁱⁱ	2.861 (4)
K—Kⁱ	3.978 (3)	C22—N21	1.438 (7)
K—K^v	4.867 (3)	C22—H22A	0.9700
K—K^vi	4.867 (3)	C22—H22B	0.9700
K—H1W	2.80 (6)	C23—O23	1.233 (6)
O12—C11	1.197 (6)	C23—N21	1.319 (7)
C11—C12	1.504 (8)	C23—C24	1.494 (8)
C12—N11	1.442 (7)	C24—C29	1.295 (14)
C12—H11A	0.9700	C24—C25'	1.377 (13)
C12—H11B	0.9700	C24—C29'	1.396 (13)
C13—O13	1.225 (6)	C24—C25	1.485 (13)
C13—N11	1.319 (7)	C27—C28	1.313 (18)
C13—C14	1.503 (7)	C27—C26'	1.354 (17)
C14—C19'	1.350 (13)	C27—C28'	1.406 (19)
C14—C15	1.362 (13)	C27—C26	1.410 (19)
C14—C19	1.376 (12)	C27—H27	0.9300
C14—C15'	1.421 (13)	C25—C26	1.38 (2)
C17—C16'	1.31 (2)	C25—H25	0.9300
C17—C18	1.347 (15)	C26—H26	0.9300
C17—C16	1.351 (19)	C28—C29	1.377 (18)
C17—C18'	1.437 (15)	C28—H28	0.9300
C17—H17	0.9300	C29—H29	0.9300
C15—C16	1.37 (2)	C25'—C26'	1.358 (18)
C15—H15	0.9300	C25'—H25'	0.9300
C16—H16	0.9300	C26'—H26'	0.9300
C18—C19	1.376 (16)	C28'—C29'	1.392 (19)
C18—H18	0.9300	C28'—H28'	0.9300
C19—H19	0.9300	C29'—H29'	0.9300
C15'—C16'	1.39 (2)	N21—H21	0.8600
C15'—H15'	0.9300	O1W—H1W	0.84 (6)
C16'—H16'	0.9300	O1W—H2W	0.79 (7)

C11—O11—K	144.3 (3)	C18—C17—H17	120.8
C11—O11—Kⁱ	110.7 (3)	C16—C17—H17	120.8
K—O11—Kⁱ	89.34 (12)	C18'—C17—H17	116.3
O1W—K—O12ⁱⁱ	164.17 (14)	C14—C15—C16	120.6 (12)
O1W—K—O11	95.43 (14)	C14—C15—H15	119.7
O12ⁱⁱ—K—O11	70.21 (12)	C16—C15—H15	119.7
O1W—K—O21	107.51 (14)	C17—C16—C15	121.2 (13)
O12ⁱⁱ—K—O21	83.98 (13)	C17—C16—H16	119.4
O11—K—O21	149.38 (12)	C15—C16—H16	119.4
O1W—K—O22ⁱⁱⁱ	84.39 (13)	C17—C18—C19	120.9 (12)
O12ⁱⁱ—K—O22ⁱⁱⁱ	86.46 (13)	C17—C18—H18	119.5
O11—K—O22ⁱⁱⁱ	79.86 (12)	C19—C18—H18	119.5
O21—K—O22ⁱⁱⁱ	82.44 (12)	C14—C19—C18	120.1 (11)
O1W—K—O11ⁱ	112.56 (12)	C14—C19—H19	119.9
O12ⁱⁱ—K—O11ⁱ	75.28 (12)	C18—C19—H19	119.9
O11—K—O11ⁱ	90.66 (12)	C16'—C15'—C14	120.4 (12)
O21—K—O11ⁱ	98.65 (12)	C16'—C15'—H15'	119.8
O22ⁱⁱⁱ—K—O11ⁱ	161.45 (11)	C14—C15'—H15'	119.8
O1W—K—O22^iv	56.41 (14)	C17—C16'—C15'	119.6 (14)
O12ⁱⁱ—K—O22^iv	139.33 (11)	C17—C16'—H16'	120.2
O11—K—O22^iv	146.83 (11)	C15'—C16'—H16'	120.2
O21—K—O22^iv	63.43 (11)	C19'—C18'—C17	118.5 (11)
O22ⁱⁱⁱ—K—O22^iv	110.86 (13)	C19'—C18'—H18'	120.8
O11ⁱ—K—O22^iv	85.76 (12)	C17—C18'—H18'	120.8
O1W—K—C21ⁱⁱⁱ	81.76 (13)	C14—C19'—C18'	120.2 (10)
O12ⁱⁱ—K—C21ⁱⁱⁱ	93.85 (14)	C14—C19'—H19'	119.9
O11—K—C21ⁱⁱⁱ	99.65 (13)	C18'—C19'—H19'	119.9
O21—K—C21ⁱⁱⁱ	65.03 (12)	C13—N11—C12	121.1 (5)
O22ⁱⁱⁱ—K—C21ⁱⁱⁱ	19.81 (11)	C13—N11—H11	119.5
O11ⁱ—K—C21ⁱⁱⁱ	161.63 (11)	C12—N11—H11	119.5
O22^iv—K—C21ⁱⁱⁱ	93.55 (13)	C21—O21—K	142.5 (3)
O1W—K—Kⁱ	110.10 (11)	O22—C21—O21	123.1 (5)
O12ⁱⁱ—K—Kⁱ	65.14 (10)	O22—C21—C22	121.3 (4)
O11—K—Kⁱ	46.34 (9)	O21—C21—C22	115.6 (4)
O21—K—Kⁱ	135.24 (10)	O22—C21—Kⁱⁱⁱ	52.4 (3)
O22ⁱⁱⁱ—K—Kⁱ	124.25 (10)	O21—C21—Kⁱⁱⁱ	124.6 (3)
O11ⁱ—K—Kⁱ	44.32 (8)	C22—C21—Kⁱⁱⁱ	93.3 (3)
O22^iv—K—Kⁱ	122.10 (9)	C21—O22—Kⁱⁱⁱ	107.8 (3)
C21ⁱⁱⁱ—K—Kⁱ	143.49 (10)	C21—O22—K^iv	131.2 (3)
O1W—K—K^v	106.80 (11)	Kⁱⁱⁱ—O22—K^iv	110.86 (13)
O12ⁱⁱ—K—K^v	59.25 (9)	N21—C22—C21	111.9 (4)
O11—K—K^v	51.11 (9)	N21—C22—H22A	109.2
O21—K—K^v	101.71 (9)	C21—C22—H22A	109.2
O22ⁱⁱⁱ—K—K^v	35.83 (8)	N21—C22—H22B	109.2
O11ⁱ—K—K^v	127.12 (8)	C21—C22—H22B	109.2
O22^iv—K—K^v	146.69 (8)	H22A—C22—H22B	107.9
C21ⁱⁱⁱ—K—K^v	53.72 (10)	O23—C23—N21	121.0 (5)
Kⁱ—K—K^v	89.88 (6)	O23—C23—C24	121.4 (5)
O1W—K—K^vi	73.20 (11)	N21—C23—C24	117.6 (5)
O12ⁱⁱ—K—K^vi	120.75 (9)	C29—C24—C25'	96.2 (9)
O11—K—K^vi	128.89 (9)	C29—C24—C29'	42.2 (7)
O21—K—K^vi	78.29 (9)	C25'—C24—C29'	118.4 (9)
O22ⁱⁱⁱ—K—K^vi	144.17 (8)	C29—C24—C25	118.7 (9)
O11ⁱ—K—K^vi	52.88 (8)	C25'—C24—C25	49.3 (8)
O22^iv—K—K^vi	33.31 (8)	C29'—C24—C25	104.5 (8)
C21ⁱⁱⁱ—K—K^vi	126.28 (10)	C29—C24—C23	125.7 (7)
Kⁱ—K—K^vi	90.12 (6)	C25'—C24—C23	118.4 (7)
K^v—K—K^vi	180.00 (5)	C29'—C24—C23	123.0 (7)
O1W—K—H1W	17.4 (13)	C25—C24—C23	115.6 (7)
O12ⁱⁱ—K—H1W	178.4 (14)	C28—C27—C26'	96.7 (10)
O11—K—H1W	111.3 (13)	C28—C27—C28'	43.8 (8)
O21—K—H1W	94.7 (13)	C26'—C27—C28'	121.0 (10)
O22ⁱⁱⁱ—K—H1W	94.2 (13)	C28—C27—C26	121.1 (10)
O11ⁱ—K—H1W	104.1 (13)	C26'—C27—C26	49.9 (9)
O22^iv—K—H1W	39.1 (14)	C28'—C27—C26	106.9 (11)
C21ⁱⁱⁱ—K—H1W	86.3 (13)	C28—C27—H27	119.5
Kⁱ—K—H1W	115.5 (12)	C26'—C27—H27	122.4
K^v—K—H1W	121.9 (14)	C28'—C27—H27	115.9
K^vi—K—H1W	58.1 (14)	C26—C27—H27	119.5
C11—O12—Kⁱⁱ	130.3 (3)	C26—C25—C24	117.2 (13)
O12—C11—O11	123.9 (5)	C26—C25—H25	121.4
O12—C11—C12	124.5 (5)	C24—C25—H25	121.4
O11—C11—C12	111.6 (4)	C25—C26—C27	119.2 (12)
N11—C12—C11	116.3 (5)	C25—C26—H26	120.4
N11—C12—H11A	108.2	C27—C26—H26	120.4
C11—C12—H11A	108.2	C27—C28—C29	120.5 (14)
N11—C12—H11B	108.2	C27—C28—H28	119.7
C11—C12—H11B	108.2	C29—C28—H28	119.7
H11A—C12—H11B	107.4	C24—C29—C28	123.2 (13)
O13—C13—N11	121.9 (5)	C24—C29—H29	118.4
O13—C13—C14	119.4 (5)	C28—C29—H29	118.4
N11—C13—C14	118.6 (5)	C26'—C25'—C24	121.8 (12)
C19'—C14—C15	106.3 (8)	C26'—C25'—H25'	119.1
C19'—C14—C19	40.3 (6)	C24—C25'—H25'	119.1
C15—C14—C19	118.0 (8)	C27—C26'—C25'	119.7 (12)
C19'—C14—C15'	119.3 (8)	C27—C26'—H26'	120.2
C15—C14—C15'	37.3 (6)	C25'—C26'—H26'	120.2
C19—C14—C15'	103.8 (8)	C29'—C28'—C27	117.8 (13)
C19'—C14—C13	123.1 (6)	C29'—C28'—H28'	121.1
C15—C14—C13	119.3 (7)	C27—C28'—H28'	121.1
C19—C14—C13	122.3 (7)	C28'—C29'—C24	120.3 (12)
C15'—C14—C13	117.6 (7)	C28'—C29'—H29'	119.8
C16'—C17—C18	107.5 (12)	C24—C29'—H29'	119.8
C16'—C17—C16	33.5 (8)	C23—N21—C22	120.7 (4)
C18—C17—C16	118.4 (10)	C23—N21—H21	119.7
C16'—C17—C18'	121.0 (10)	C22—N21—H21	119.7
C18—C17—C18'	45.6 (9)	K—O1W—H1W	84 (4)
C16—C17—C18'	104.3 (10)	K—O1W—H2W	115 (5)
C16'—C17—H17	121.4	H1W—O1W—H2W	123 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O23ⁱ	0.86	2.09	2.905 (7)	158
N21—H21···O1Wⁱⁱⁱ	0.86	2.15	2.929 (6)	151
O1W—H1W···O22^iv	0.84 (6)	1.97 (7)	2.758 (7)	156 (6)
O1W—H2W···O13^vi	0.79 (7)	1.92 (7)	2.680 (6)	160 (7)

Symmetry codes: (i) −x, −y+1, −z; (iii) −x, −y, −z; (iv) −x−1, −y, −z; (vi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[K(C₉H₈N₂O₃)₂(H₂O)]
M_r	413.44
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	4.867 (3), 9.921 (7), 20.076 (9)
α, β, γ (°)	92.59 (4), 91.45 (3), 101.33 (5)
V (Å³)	948.9 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.21 × 0.18 × 0.16

Data collection
Diffractometer	Nonius MACH-3
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.926, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	4593, 3327, 2044
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.248, 1.08
No. of reflections	3327
No. of parameters	333
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.64

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXTL/PC (Bruker, 2000), SHELXTL/PC, ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O23ⁱ	0.86	2.09	2.905 (7)	157.6
N21—H21···O1Wⁱⁱ	0.86	2.15	2.929 (6)	150.7
O1W—H1W···O22ⁱⁱⁱ	0.84 (6)	1.97 (7)	2.758 (7)	156 (6)
O1W—H2W···O13^iv	0.79 (7)	1.92 (7)	2.680 (6)	160 (7)

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

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