Poly[μ2-aqua-bis­[μ4-2-(1H-1,2,3-benzotriazol-1-yl)acetato]­dipotassium]

Liu, Q.

doi:10.1107/S1600536812008963

metal-organic compounds

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Volume 68| Part 4| April 2012| Page m379

doi:10.1107/S1600536812008963

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Poly[μ₂-aqua-bis[μ₄-2-(1H-1,2,3-benzotriazol-1-yl)acetato]dipotassium]

Qiong Liu ^a ^*

^aDepartment of Environment Engineering and Chemistry, Luoyang Institute of Science and Technology, 471023 Luoyang, People's Republic of China
^*Correspondence e-mail: shujianrufeng@yahoo.com.cn

(Received 19 February 2012; accepted 29 February 2012; online 7 March 2012)

In the title compound, [K₂(C₈H₆N₃O₂)₂(H₂O)]_n, each K⁺ ion is seven-coordinated by one O atom from a bridging water molecule, five carboxylate O atoms and one N atom from a benzotriazole group, forming a distorted mono-capped octahedral geometry. In the crystal, the carboxylate groups act as bridging ligands, forming a two-dimensional polymer parallel to (001). The aqua ligand, which lies on a twofold rotation axis, forms intermolecular O—H⋯O hydrogen bonds within these layers.

Related literature

For background and the synthesis, see: Hu et al. (2008 ).

Experimental

Crystal data

[K₂(C₈H₆N₃O₂)₂(H₂O)]
M_r = 448.53
Monoclinic, C 2
a = 12.159 (2) Å
b = 4.5893 (9) Å
c = 17.666 (4) Å
β = 104.98 (3)°
V = 952.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.878, T_max = 0.937
4827 measured reflections
2140 independent reflections
1508 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.135
S = 1.05
2140 reflections
136 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 925 Friedel pairs
Flack parameter: −0.02 (9)

Table 1
Selected bond lengths (Å)

K1—O2ⁱ	2.718 (4)
K1—O3	2.760 (3)
K1—O2ⁱⁱ	2.829 (3)
K1—O2ⁱⁱⁱ	2.835 (4)
K1—O1	2.872 (4)
K1—N2	2.934 (4)
K1—O1ⁱⁱ	3.287 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) -x+1, y, -z+1; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1^iv	0.87 (6)	1.87 (7)	2.729 (5)	167 (7)
Symmetry code: (iv) x, y-1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008963/lh5422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008963/lh5422Isup2.hkl

checkCIF report

Comment top

Organic ligands based on azole heterocycles or carboxylate groups which contain N and O donors have both good coordination ability and diverse coordination modes (Hu et al., 2008). Therefore, the ligand 1H-benzotriazole-1-acetic acid was chosen to create coordination architectures. The synthesis of the ligand was the first step. But, when we synthesized the ligand according to the method of literature (see experimental section), the title complex (I) was obtained instead of the target ligand.

The title complex (I) is a polymeric potassium(I) complex of which the asymmetric is shown in Fig. 1. The environment of the K^I ion is a distorted mono-capped octahedral geometry. Each K^I ion is coordinated by one O atom from a water molecule, five carboxylate O atoms and one N atom from the ligands. The polymeric structure is a two-dimensional layer parallel to (001) (see, Fig .2).

Related literature top

For background and the synthesis, see: Hu et al. (2008).

Experimental top

Reagents and solvents were of commercially available quality. The title compound was synthesized according to the method of Hu et al. 2008. To a bromoacetonitrile solution of 1H-Benzotriazole (11.9 g), potassium hydroxide (6.8 g), anhydrous K₂CO₃ (13.8 g) and TEBA (benzyltriethylammoniumchloride, 99%, 0.15 g) were added. The mixture was stirred at room temperature for 30 min. After cooling to 283 K, 8.4 ml (0.075 mol) ethyl bromoacetate was added dropwise with further stirring. After standing at room temperature overnight the mixture was filtered and the filtrate was distilled under diminished pressure to obtain a yellow liquid. 100 ml water was added to the yellow liquid and the mixture was left to stand for 12 h at a condition of circumfluence. Single crystals suitable for X-ray diffraction were obtained after removing the solvent and recrystallizing in water and methanol solution (30 mL, 5: 1, v/v) at room temperature. Yield: 20%.

Structure description top

For background and the synthesis, see: Hu et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title complex showing 40% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. A packing diagram of the title compound, viewed along the b axis, showing the two-dimensional layered structure.

Poly[µ₂-aqua-bis[µ₄-2-(1H-1,2,3-benzotriazol-1- yl)acetato]dipotassium] top

Crystal data top

[K₂(C₈H₆N₃O₂)₂(H₂O)]	F(000) = 460
M_r = 448.53	D_x = 1.564 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 4308 reflections
a = 12.159 (2) Å	θ = 3.4–27.6°
b = 4.5893 (9) Å	µ = 0.54 mm⁻¹
c = 17.666 (4) Å	T = 296 K
β = 104.98 (3)°	Prism, colorless
V = 952.2 (3) Å³	0.3 × 0.2 × 0.12 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2140 independent reflections
Radiation source: fine-focus sealed tube	1508 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
φ and ω scans	θ_max = 27.5°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.878, T_max = 0.937	k = −5→5
4827 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0551P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2140 reflections	Δρ_max = 0.46 e Å⁻³
136 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 925 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (9)

Crystal data top

[K₂(C₈H₆N₃O₂)₂(H₂O)]	V = 952.2 (3) Å³
M_r = 448.53	Z = 2
Monoclinic, C2	Mo Kα radiation
a = 12.159 (2) Å	µ = 0.54 mm⁻¹
b = 4.5893 (9) Å	T = 296 K
c = 17.666 (4) Å	0.3 × 0.2 × 0.12 mm
β = 104.98 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2140 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1508 reflections with I > 2σ(I)
T_min = 0.878, T_max = 0.937	R_int = 0.053
4827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.135	Δρ_max = 0.46 e Å⁻³
S = 1.05	Δρ_min = −0.24 e Å⁻³
2140 reflections	Absolute structure: Flack (1983), 925 Friedel pairs
136 parameters	Absolute structure parameter: −0.02 (9)
0 restraints

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
K1	0.62160 (7)	0.3984 (3)	0.43153 (5)	0.0478 (3)
O1	0.3919 (3)	0.6125 (7)	0.39356 (19)	0.0563 (9)
O2	0.2403 (2)	0.3829 (10)	0.41277 (15)	0.0495 (7)
N1	0.3763 (3)	0.3467 (9)	0.2538 (2)	0.0481 (10)
N2	0.4845 (3)	0.2466 (10)	0.2740 (2)	0.0601 (12)
N3	0.5400 (3)	0.3627 (15)	0.2268 (2)	0.0670 (13)
C1	0.3119 (3)	0.4388 (11)	0.3754 (2)	0.0388 (11)
C2	0.2979 (4)	0.2654 (12)	0.2991 (3)	0.0541 (13)
H2A	0.3078	0.0599	0.3119	0.065*
H2B	0.2208	0.2920	0.2670	0.065*
C3	0.4673 (4)	0.5401 (12)	0.1754 (3)	0.0489 (12)
C4	0.4849 (5)	0.7071 (14)	0.1142 (3)	0.0687 (16)
H4A	0.5550	0.7097	0.1023	0.082*
C5	0.3952 (5)	0.8677 (19)	0.0721 (3)	0.0718 (16)
H5A	0.4048	0.9844	0.0313	0.086*
C6	0.2893 (5)	0.8601 (15)	0.0894 (3)	0.0667 (15)
H6A	0.2297	0.9691	0.0588	0.080*
C7	0.2702 (4)	0.6970 (12)	0.1501 (3)	0.0562 (13)
H7A	0.2001	0.6952	0.1620	0.067*
C8	0.3618 (4)	0.5360 (11)	0.1923 (3)	0.0442 (11)
O3	0.5000	0.0180 (11)	0.5000	0.0529 (13)
H3	0.465 (4)	−0.090 (18)	0.461 (3)	0.083 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0443 (5)	0.0509 (5)	0.0467 (6)	−0.0037 (6)	0.0089 (4)	0.0024 (6)
O1	0.060 (2)	0.054 (2)	0.055 (2)	−0.0158 (18)	0.0148 (16)	−0.0082 (17)
O2	0.0438 (15)	0.0609 (18)	0.0465 (17)	0.003 (2)	0.0165 (12)	0.004 (2)
N1	0.044 (2)	0.062 (3)	0.041 (2)	−0.008 (2)	0.0158 (16)	−0.006 (2)
N2	0.052 (3)	0.081 (3)	0.046 (3)	0.001 (2)	0.0098 (19)	−0.003 (2)
N3	0.050 (2)	0.095 (4)	0.058 (3)	−0.005 (3)	0.017 (2)	−0.008 (3)
C1	0.039 (2)	0.035 (3)	0.038 (2)	0.004 (2)	0.0025 (17)	0.007 (2)
C2	0.057 (3)	0.062 (3)	0.045 (3)	−0.020 (2)	0.016 (2)	−0.007 (2)
C3	0.052 (3)	0.058 (3)	0.037 (3)	−0.010 (3)	0.013 (2)	−0.016 (2)
C4	0.064 (4)	0.085 (4)	0.063 (4)	−0.015 (3)	0.028 (3)	−0.013 (3)
C5	0.103 (4)	0.069 (4)	0.051 (3)	−0.011 (5)	0.032 (3)	−0.003 (4)
C6	0.087 (4)	0.060 (4)	0.050 (3)	0.007 (4)	0.012 (3)	0.002 (3)
C7	0.052 (3)	0.061 (3)	0.057 (3)	0.004 (3)	0.016 (2)	−0.016 (3)
C8	0.045 (3)	0.052 (3)	0.037 (3)	−0.007 (2)	0.013 (2)	−0.017 (2)
O3	0.065 (3)	0.042 (3)	0.048 (3)	0.000	0.008 (3)	0.000

Geometric parameters (Å, º) top

K1—O2ⁱ	2.718 (4)	C1—C2	1.536 (6)
K1—O3	2.760 (3)	C1—K1ⁱⁱ	3.301 (4)
K1—O2ⁱⁱ	2.829 (3)	C1—K1^v	3.461 (5)
K1—O2ⁱⁱⁱ	2.835 (4)	C2—H2A	0.9700
K1—O1	2.872 (4)	C2—H2B	0.9700
K1—N2	2.934 (4)	C3—C4	1.386 (7)
K1—O1ⁱⁱ	3.287 (3)	C3—C8	1.389 (6)
O1—C1	1.234 (5)	C4—C5	1.366 (8)
O1—K1ⁱⁱ	3.287 (3)	C4—H4A	0.9300
O2—C1	1.248 (4)	C5—C6	1.399 (6)
O2—K1^iv	2.718 (4)	C5—H5A	0.9300
O2—K1ⁱⁱ	2.829 (3)	C6—C7	1.376 (7)
O2—K1^v	2.835 (4)	C6—H6A	0.9300
N1—N2	1.351 (5)	C7—C8	1.383 (7)
N1—C8	1.367 (6)	C7—H7A	0.9300
N1—C2	1.444 (5)	O3—K1ⁱⁱ	2.760 (3)
N2—N3	1.314 (6)	O3—H3	0.87 (6)
N3—C3	1.362 (7)

O2ⁱ—K1—O3	158.80 (10)	O2ⁱ—K1—H3	171.8 (13)
O2ⁱ—K1—O2ⁱⁱ	86.48 (10)	O3—K1—H3	16.0 (9)
O3—K1—O2ⁱⁱ	78.97 (8)	O2ⁱⁱ—K1—H3	93.3 (9)
O2ⁱ—K1—O2ⁱⁱⁱ	111.47 (9)	O2ⁱⁱⁱ—K1—H3	76.6 (13)
O3—K1—O2ⁱⁱⁱ	82.54 (10)	O1—K1—H3	71.3 (12)
O2ⁱⁱ—K1—O2ⁱⁱⁱ	84.30 (10)	N2—K1—H3	76.2 (9)
O2ⁱ—K1—O1	101.92 (10)	O1ⁱⁱ—K1—H3	82.9 (10)
O3—K1—O1	73.74 (9)	C1ⁱⁱ—K1—H3	82.2 (9)
O2ⁱⁱ—K1—O1	122.19 (10)	C1ⁱⁱⁱ—K1—H3	95.4 (13)
O2ⁱⁱⁱ—K1—O1	138.77 (10)	K1^vi—K1—H3	135.8 (9)
O2ⁱ—K1—N2	105.55 (11)	K1^vii—K1—H3	84.5 (11)
O3—K1—N2	91.61 (10)	K1ⁱⁱ—K1—H3	49.8 (12)
O2ⁱⁱ—K1—N2	164.82 (13)	C1—O1—K1	119.5 (3)
O2ⁱⁱⁱ—K1—N2	82.69 (10)	C1—O1—K1ⁱⁱ	79.9 (3)
O1—K1—N2	65.15 (10)	K1—O1—K1ⁱⁱ	87.70 (10)
O2ⁱ—K1—O1ⁱⁱ	91.55 (9)	C1—O2—K1^iv	134.2 (4)
O3—K1—O1ⁱⁱ	67.34 (9)	C1—O2—K1ⁱⁱ	100.9 (2)
O2ⁱⁱ—K1—O1ⁱⁱ	41.81 (9)	K1^iv—O2—K1ⁱⁱ	95.88 (10)
O2ⁱⁱⁱ—K1—O1ⁱⁱ	120.67 (8)	C1—O2—K1^v	109.7 (3)
O1—K1—O1ⁱⁱ	80.53 (11)	K1^iv—O2—K1^v	111.47 (8)
N2—K1—O1ⁱⁱ	143.94 (10)	K1ⁱⁱ—O2—K1^v	93.30 (11)
O2ⁱ—K1—C1ⁱⁱ	94.83 (10)	N2—N1—C8	110.1 (3)
O3—K1—C1ⁱⁱ	66.33 (9)	N2—N1—C2	120.2 (4)
O2ⁱⁱ—K1—C1ⁱⁱ	21.80 (8)	C8—N1—C2	129.6 (4)
O2ⁱⁱⁱ—K1—C1ⁱⁱ	99.89 (11)	N3—N2—N1	108.6 (4)
O1—K1—C1ⁱⁱ	100.70 (11)	N3—N2—K1	104.3 (3)
N2—K1—C1ⁱⁱ	157.01 (12)	N1—N2—K1	116.5 (3)
O1ⁱⁱ—K1—C1ⁱⁱ	21.59 (9)	N2—N3—C3	108.3 (4)
O2ⁱ—K1—C1ⁱⁱⁱ	92.76 (12)	O1—C1—O2	127.2 (4)
O3—K1—C1ⁱⁱⁱ	102.35 (12)	O1—C1—C2	117.7 (4)
O2ⁱⁱ—K1—C1ⁱⁱⁱ	89.46 (10)	O2—C1—C2	115.0 (4)
O2ⁱⁱⁱ—K1—C1ⁱⁱⁱ	19.86 (9)	O1—C1—K1ⁱⁱ	78.5 (2)
O1—K1—C1ⁱⁱⁱ	145.45 (10)	O2—C1—K1ⁱⁱ	57.28 (19)
N2—K1—C1ⁱⁱⁱ	80.89 (11)	C2—C1—K1ⁱⁱ	145.0 (3)
O1ⁱⁱ—K1—C1ⁱⁱⁱ	130.64 (9)	O1—C1—K1^v	94.1 (3)
C1ⁱⁱ—K1—C1ⁱⁱⁱ	109.10 (11)	O2—C1—K1^v	50.5 (3)
O2ⁱ—K1—K1^vi	43.10 (5)	C2—C1—K1^v	129.5 (3)
O3—K1—K1^vi	120.37 (5)	K1ⁱⁱ—C1—K1^v	75.00 (9)
O2ⁱⁱ—K1—K1^vi	43.41 (9)	N1—C2—C1	114.4 (4)
O2ⁱⁱⁱ—K1—K1^vi	101.65 (7)	N1—C2—H2A	108.7
O1—K1—K1^vi	119.37 (7)	C1—C2—H2A	108.7
N2—K1—K1^vi	147.99 (10)	N1—C2—H2B	108.7
O1ⁱⁱ—K1—K1^vi	59.71 (6)	C1—C2—H2B	108.7
C1ⁱⁱ—K1—K1^vi	54.26 (8)	H2A—C2—H2B	107.6
C1ⁱⁱⁱ—K1—K1^vi	92.65 (8)	N3—C3—C4	130.2 (5)
O2ⁱ—K1—K1^vii	100.47 (7)	N3—C3—C8	108.9 (4)
O3—K1—K1^vii	78.52 (5)	C4—C3—C8	120.8 (5)
O2ⁱⁱ—K1—K1^vii	41.03 (8)	C5—C4—C3	117.4 (5)
O2ⁱⁱⁱ—K1—K1^vii	43.29 (5)	C5—C4—H4A	121.3
O1—K1—K1^vii	150.66 (8)	C3—C4—H4A	121.3
N2—K1—K1^vii	125.69 (9)	C4—C5—C6	121.2 (6)
O1ⁱⁱ—K1—K1^vii	80.15 (7)	C4—C5—H5A	119.4
C1ⁱⁱ—K1—K1^vii	58.57 (9)	C6—C5—H5A	119.4
C1ⁱⁱⁱ—K1—K1^vii	50.74 (7)	C7—C6—C5	122.3 (6)
K1^vi—K1—K1^vii	67.72 (3)	C7—C6—H6A	118.9
O2ⁱ—K1—K1ⁱⁱ	122.38 (7)	C5—C6—H6A	118.9
O3—K1—K1ⁱⁱ	39.22 (9)	C6—C7—C8	115.9 (5)
O2ⁱⁱ—K1—K1ⁱⁱ	76.91 (6)	C6—C7—H7A	122.1
O2ⁱⁱⁱ—K1—K1ⁱⁱ	120.90 (6)	C8—C7—H7A	122.1
O1—K1—K1ⁱⁱ	50.16 (7)	N1—C8—C7	133.5 (4)
N2—K1—K1ⁱⁱ	103.29 (9)	N1—C8—C3	104.0 (4)
O1ⁱⁱ—K1—K1ⁱⁱ	42.14 (6)	C7—C8—C3	122.4 (5)
C1ⁱⁱ—K1—K1ⁱⁱ	55.66 (8)	K1—O3—K1ⁱⁱ	101.56 (17)
C1ⁱⁱⁱ—K1—K1ⁱⁱ	140.67 (8)	K1—O3—H3	103 (4)
K1^vi—K1—K1ⁱⁱ	101.41 (4)	K1ⁱⁱ—O3—H3	120 (4)
K1^vii—K1—K1ⁱⁱ	101.41 (4)

O2ⁱ—K1—O1—C1	160.5 (3)	K1ⁱⁱ—O1—C1—O2	32.1 (5)
O3—K1—O1—C1	−40.9 (3)	K1—O1—C1—C2	−65.4 (4)
O2ⁱⁱ—K1—O1—C1	−106.1 (3)	K1ⁱⁱ—O1—C1—C2	−146.9 (4)
O2ⁱⁱⁱ—K1—O1—C1	16.6 (4)	K1—O1—C1—K1ⁱⁱ	81.5 (2)
N2—K1—O1—C1	58.8 (3)	K1—O1—C1—K1^v	155.27 (17)
O1ⁱⁱ—K1—O1—C1	−109.9 (3)	K1ⁱⁱ—O1—C1—K1^v	73.78 (9)
C1ⁱⁱ—K1—O1—C1	−102.1 (3)	K1^iv—O2—C1—O1	−147.7 (4)
C1ⁱⁱⁱ—K1—O1—C1	47.4 (4)	K1ⁱⁱ—O2—C1—O1	−38.3 (5)
K1^vi—K1—O1—C1	−157.0 (3)	K1^v—O2—C1—O1	59.3 (5)
K1^vii—K1—O1—C1	−60.5 (4)	K1^iv—O2—C1—C2	31.3 (5)
K1ⁱⁱ—K1—O1—C1	−77.0 (3)	K1ⁱⁱ—O2—C1—C2	140.8 (3)
O2ⁱ—K1—O1—K1ⁱⁱ	−122.46 (8)	K1^v—O2—C1—C2	−121.7 (4)
O3—K1—O1—K1ⁱⁱ	36.13 (8)	K1^iv—O2—C1—K1ⁱⁱ	−109.5 (3)
O2ⁱⁱ—K1—O1—K1ⁱⁱ	−29.10 (15)	K1^v—O2—C1—K1ⁱⁱ	97.5 (2)
O2ⁱⁱⁱ—K1—O1—K1ⁱⁱ	93.58 (13)	K1^iv—O2—C1—K1^v	153.0 (4)
N2—K1—O1—K1ⁱⁱ	135.76 (13)	K1ⁱⁱ—O2—C1—K1^v	−97.5 (2)
O1ⁱⁱ—K1—O1—K1ⁱⁱ	−32.88 (11)	N2—N1—C2—C1	79.5 (6)
C1ⁱⁱ—K1—O1—K1ⁱⁱ	−25.14 (12)	C8—N1—C2—C1	−95.5 (5)
C1ⁱⁱⁱ—K1—O1—K1ⁱⁱ	124.37 (17)	O1—C1—C2—N1	−4.9 (6)
K1^vi—K1—O1—K1ⁱⁱ	−79.99 (9)	O2—C1—C2—N1	175.9 (4)
K1^vii—K1—O1—K1ⁱⁱ	16.52 (19)	K1ⁱⁱ—C1—C2—N1	−116.0 (5)
C8—N1—N2—N3	−0.8 (6)	K1^v—C1—C2—N1	117.6 (4)
C2—N1—N2—N3	−176.7 (4)	N2—N3—C3—C4	−179.2 (5)
C8—N1—N2—K1	116.5 (3)	N2—N3—C3—C8	0.7 (6)
C2—N1—N2—K1	−59.4 (5)	N3—C3—C4—C5	−179.5 (6)
O2ⁱ—K1—N2—N3	24.2 (4)	C8—C3—C4—C5	0.6 (7)
O3—K1—N2—N3	−168.4 (4)	C3—C4—C5—C6	−1.0 (9)
O2ⁱⁱ—K1—N2—N3	−117.3 (5)	C4—C5—C6—C7	1.4 (10)
O2ⁱⁱⁱ—K1—N2—N3	−86.1 (4)	C5—C6—C7—C8	−1.2 (8)
O1—K1—N2—N3	120.4 (4)	N2—N1—C8—C7	−179.7 (5)
O1ⁱⁱ—K1—N2—N3	139.7 (3)	C2—N1—C8—C7	−4.3 (9)
C1ⁱⁱ—K1—N2—N3	175.8 (4)	N2—N1—C8—C3	1.2 (5)
C1ⁱⁱⁱ—K1—N2—N3	−66.1 (4)	C2—N1—C8—C3	176.6 (4)
K1^vi—K1—N2—N3	14.2 (5)	C6—C7—C8—N1	−178.2 (5)
K1^vii—K1—N2—N3	−91.4 (4)	C6—C7—C8—C3	0.7 (7)
K1ⁱⁱ—K1—N2—N3	153.8 (4)	N3—C3—C8—N1	−1.1 (5)
O2ⁱ—K1—N2—N1	−95.4 (3)	C4—C3—C8—N1	178.8 (5)
O3—K1—N2—N1	72.0 (3)	N3—C3—C8—C7	179.6 (5)
O2ⁱⁱ—K1—N2—N1	123.1 (4)	C4—C3—C8—C7	−0.5 (7)
O2ⁱⁱⁱ—K1—N2—N1	154.3 (4)	O2ⁱ—K1—O3—K1ⁱⁱ	35.2 (2)
O1—K1—N2—N1	0.8 (3)	O2ⁱⁱ—K1—O3—K1ⁱⁱ	82.75 (8)
O1ⁱⁱ—K1—N2—N1	20.0 (5)	O2ⁱⁱⁱ—K1—O3—K1ⁱⁱ	168.36 (6)
C1ⁱⁱ—K1—N2—N1	56.2 (5)	O1—K1—O3—K1ⁱⁱ	−45.72 (7)
C1ⁱⁱⁱ—K1—N2—N1	174.2 (4)	N2—K1—O3—K1ⁱⁱ	−109.23 (9)
K1^vi—K1—N2—N1	−105.4 (3)	O1ⁱⁱ—K1—O3—K1ⁱⁱ	40.61 (7)
K1^vii—K1—N2—N1	149.0 (3)	C1ⁱⁱ—K1—O3—K1ⁱⁱ	64.09 (10)
K1ⁱⁱ—K1—N2—N1	34.2 (3)	C1ⁱⁱⁱ—K1—O3—K1ⁱⁱ	169.75 (7)
N1—N2—N3—C3	0.0 (6)	K1^vi—K1—O3—K1ⁱⁱ	69.19 (5)
K1—N2—N3—C3	−124.8 (4)	K1^vii—K1—O3—K1ⁱⁱ	124.62 (4)
K1—O1—C1—O2	113.6 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^viii	0.87 (6)	1.87 (7)	2.729 (5)	167 (7)

Symmetry code: (viii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[K₂(C₈H₆N₃O₂)₂(H₂O)]
M_r	448.53
Crystal system, space group	Monoclinic, C2
Temperature (K)	296
a, b, c (Å)	12.159 (2), 4.5893 (9), 17.666 (4)
β (°)	104.98 (3)
V (Å³)	952.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.3 × 0.2 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.878, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	4827, 2140, 1508
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.135, 1.05
No. of reflections	2140
No. of parameters	136
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.24
Absolute structure	Flack (1983), 925 Friedel pairs
Absolute structure parameter	−0.02 (9)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

K1—O2ⁱ	2.718 (4)	K1—O1	2.872 (4)
K1—O3	2.760 (3)	K1—N2	2.934 (4)
K1—O2ⁱⁱ	2.829 (3)	K1—O1ⁱⁱ	3.287 (3)
K1—O2ⁱⁱⁱ	2.835 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^iv	0.87 (6)	1.87 (7)	2.729 (5)	167 (7)

Symmetry code: (iv) x, y−1, z.

Acknowledgements

This work was supported by a start-up grant from Luoyang Institute of Science and Technology.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hu, T. L., Du, W. P., Hu, B. W., Li, J. R., Bu, X. H. & Cao, R. (2008). CrystEngComm, 10, 1037–1043. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar