Potassium l-2-nitrimino-1,3-diazepane-4-carboxyl­ate monohydrate

Abstract

The title compound, K⁺·C₆H₉N₄O₄ ⁻·H₂O, crystallizes with the K atoms located on special positions related by pseudocentres of symmetry. Each K atom is coordinated by six O-atom donors. The N and water H atoms are involved in inter- and intra­molecular N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonding. The data indicate inversion twinning.

Related literature

For related literature, see: Apreyan & Petrosyan (2008 ▶); Apreyan et al. (2008a ▶,b ▶); Karapetyan (2008a ▶,b ▶); Karapetyan et al. (2007 ▶); Kurtz & Perry (1968 ▶); Paul et al. (1961 ▶); Petrosyan et al. (2005 ▶).

Experimental

Crystal data

• K⁺·C₆H₉N₄O₄ ⁻·H₂O

• M _r = 258.29

• Orthorhombic,

• a = 7.3883 (15) Å

• b = 10.087 (2) Å

• c = 29.031 (6) Å

• V = 2163.5 (8) ų

• Z = 8

• Mo Kα radiation

• μ = 0.51 mm⁻¹

• T = 293 (2) K

• 0.21 × 0.14 × 0.11 mm

Data collection

• Enraf–Nonius CAD-4 diffractometer

• Absorption correction: none

• 5030 measured reflections

• 3141 independent reflections

• 1736 reflections with I > 2σ(I)

• R _int = 0.030

• 3 standard reflections every 400 reflections intensity decay: none

Refinement

• R[F ² > 2σ(F ²)] = 0.065

• wR(F ²) = 0.193

• S = 1.04

• 3141 reflections

• 154 parameters

• 3 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.42 e Å⁻³

• Δρ_min = −0.39 e Å⁻³

• Absolute structure: Flack (1983 ▶), 1350 Friedel pairs

• Flack parameter: 0.48 (20)

Data collection: DATCOL in CAD-4 Software (Enraf–Nonius, 1988 ▶); cell refinement: LS in CAD-4 Software; data reduction: HELENA (Spek, 1997 ▶); 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.

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H11⋯O1i	0.87 (2)	2.09 (5)	2.885 (5)	153 (10)
O5—H10⋯O3ii	0.856 (19)	2.03 (4)	2.793 (4)	148 (6)
N2—H9⋯N3iii	0.86	2.39	3.080 (4)	138
N1—H2⋯O3	0.86	2.09	2.561 (5)	114

Symmetry codes: (i) ; (ii) ; (iii) .

supplementary crystallographic information

Comment

Cyclic L-2-nitrimino-1,3-diazepane-4-carboxylic acid (L-NIDCA), produced by elimination of amine from L-nitroarginine (Paul et al., 1961) , may generate new non-linear optical materials like L-nitroarginine itself [Apreyan et al. (2008a, 2008b); Karapetyan et al.(2007); Petrosyan et al. (2005); the crystal structures of L-NIDCA and its monohydrate have been recently reported [Karapetyan (2008a, 2008b)].

This paper presents a structural study of the potassium salt of L-NIDCA monohydrate. The structure was solved and refined in the orthorhombic unit cell with I222 space group. The choice of the non-centric space group was based on the generation of second harmonic observed on a powder sample (YAG:Nd laser, Kurtz-Perry method [Kurtz & Perry,1968]). In this structure, two independent potassium cations occupy special positions. These potassium atoms are located about pseudo-inversion centers, which is most likely the reason for the presence of high level pseudosymmetry in the structure. Both potassium cations are coordinated by six oxygen atoms with K···O bond lengths in the ranges 2.712 (5)-2.815 (7) Å for K1 and 2.642 (5)-2.783 (6) Å for K2.

A view of the asymmetric unit is shown in Fig. 1. The high value of U_eq of atom C3 of the 1,3-diazepane ring compared to those of its neighbors indicates potential disorder of this atom. In the crystal structure, the nitrogen-bound H atoms and the water H atoms are involved in N—H···O, N—H···N and O—H···O hydrogen bonding (Table 1), one of them being intra- and the other three intermolecular, linking anions and water molecules in infinite layers parallel to the bc plane (Fig. 2).

Experimental

The title compound was synthesized from a mixture of aqueous solutions containing L-nitroarginine (2 g, Sigma-Aldrich) and KOH (0.512 g) at room temperature. Single crystals of the title compound were obtained by slow evaporation of the solution. At 97° C decomposition of the crystals was observed.

Refinement

The data set was collected in a full sphere of reciprocal space. Space group I222 was chosen on the basis of the powder second harmonic of YAG:Nb laser generation property of the crystals of the title compound. In spite of the fact that all H atoms appear in difference Fourier maps in reasonable positions, they became unacceptable after refinement. Because of this, all the H atoms except those belonging to the water molecule were placed in geometrically calculated positions and included in the refinement in a riding model approximation, with U_iso(H) = 1.2U_eq(carrier atom). The positions of the H atoms of the water molecule were located in difference Fourier maps and included in the refinement with fixed O—H (0.85 Å), H···H (1.35 Å) distances and isotropic temperature parameters U_iso(H) = 1.4U_eq(O). The absolute configuration has been determined using L-nitroarginine of known absolute configuration.

Figures

Fig. 1.

A perspective view of the asymmetric unit, showing the atomic numbering and displacement ellipsoids drawn at the 50% probability level.

Fig. 2.

Packing of the molecules. For clarity, only the donors in the original molecule and their corresponding acceptors are labelled. Symmetry codes are: (i) x, y - 1, z; (ii)-x + 1/2, y - 1/2, -z + 1/2; (iii) x, 2 - y, 1 - z. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

K+·C6H9N4O4−·H2O	F(000) = 1072
Mr = 258.29	Dx = 1.586 Mg m−3
Orthorhombic, I222	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 2	Cell parameters from 24 reflections
a = 7.3883 (15) Å	θ = 14–16°
b = 10.087 (2) Å	µ = 0.51 mm−1
c = 29.031 (6) Å	T = 293 K
V = 2163.5 (8) Å3	Prism, yellow
Z = 8	0.21 × 0.14 × 0.11 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.1°
graphite	h = −10→10
ω/2θ scans	k = −13→13
5030 measured reflections	l = −38→38
3141 independent reflections	3 standard reflections every 400 reflections
1726 reflections with I > 2σ(I)	intensity decay: none

Refinement

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.193	w = 1/[σ2(Fo2) + (0.0676P)2 + 6.1136P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3141 reflections	Δρmax = 0.43 e Å−3
154 parameters	Δρmin = −0.39 e Å−3
3 restraints	Absolute structure: Flack (1983), 1350 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.48 (20)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.5000	0.5000	0.26313 (7)	0.0481 (5)
K2	0.0000	0.5000	0.26268 (8)	0.0536 (5)
O1	0.2429 (10)	0.6833 (3)	0.28276 (9)	0.0510 (8)
O2	0.2513 (10)	0.8993 (3)	0.29658 (9)	0.0618 (10)
O3	0.2476 (15)	1.1286 (3)	0.37039 (10)	0.0905 (16)
O4	0.2389 (10)	1.2557 (3)	0.42935 (11)	0.0723 (12)
O5	0.2461 (12)	0.3267 (3)	0.30317 (11)	0.0644 (10)
N1	0.2755 (14)	0.8784 (3)	0.38382 (11)	0.0630 (19)
H2	0.3373	0.9320	0.3670	0.076*
N2	0.2659 (10)	0.8275 (3)	0.46137 (11)	0.0583 (14)
H9	0.3224	0.8526	0.4858	0.070*
N3	0.2516 (11)	1.0441 (3)	0.44244 (10)	0.0490 (10)
N4	0.2478 (12)	1.1416 (3)	0.41290 (11)	0.0526 (10)
C1	0.2419 (12)	0.7820 (4)	0.30906 (13)	0.0433 (11)
C2	0.2101 (7)	0.7544 (4)	0.36059 (14)	0.0397 (12)
H1	0.0794	0.7470	0.3657	0.048*
C3	0.294 (2)	0.6381 (6)	0.37834 (19)	0.118 (5)
H4	0.4240	0.6514	0.3793	0.142*
H3	0.2697	0.5645	0.3578	0.142*
C4	0.2262 (15)	0.6022 (4)	0.42740 (17)	0.069 (2)
H5	0.1150	0.5526	0.4232	0.082*
H6	0.3139	0.5404	0.4399	0.082*
C5	0.1931 (9)	0.6894 (5)	0.46054 (17)	0.0601 (19)
H7	0.2319	0.6481	0.4891	0.072*
H8	0.0624	0.6974	0.4624	0.072*
C6	0.2498 (15)	0.9152 (4)	0.42687 (13)	0.0475 (10)
H10	0.288 (8)	0.279 (5)	0.3251 (13)	0.07 (2)*
H11	0.288 (14)	0.287 (8)	0.2790 (13)	0.16 (5)*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
K1	0.0547 (12)	0.0388 (11)	0.0507 (11)	0.0026 (10)	0.000	0.000
K2	0.0566 (12)	0.0404 (12)	0.0637 (13)	−0.0021 (11)	0.000	0.000
O1	0.070 (2)	0.0423 (15)	0.0409 (14)	0.000 (3)	0.008 (3)	−0.0129 (13)
O2	0.115 (3)	0.0374 (15)	0.0326 (13)	0.013 (4)	−0.002 (4)	0.0002 (11)
O3	0.202 (5)	0.0350 (16)	0.0343 (15)	−0.001 (5)	−0.009 (5)	0.0075 (12)
O4	0.136 (4)	0.0279 (13)	0.0534 (18)	0.006 (4)	−0.007 (4)	−0.0024 (13)
O5	0.103 (3)	0.0470 (17)	0.0436 (17)	−0.009 (4)	−0.003 (4)	0.0143 (15)
N1	0.134 (6)	0.0286 (16)	0.0266 (16)	−0.021 (4)	0.012 (3)	−0.0014 (12)
N2	0.115 (4)	0.0309 (16)	0.0291 (15)	−0.017 (3)	0.012 (4)	−0.0006 (13)
N3	0.087 (3)	0.0286 (14)	0.0312 (15)	0.007 (4)	0.006 (4)	0.0001 (12)
N4	0.088 (3)	0.0310 (16)	0.0393 (17)	0.005 (4)	0.014 (4)	0.0017 (13)
C1	0.057 (3)	0.039 (2)	0.0339 (18)	0.007 (4)	−0.010 (3)	−0.0022 (15)
C2	0.049 (3)	0.0352 (19)	0.0344 (19)	0.004 (2)	−0.002 (2)	−0.0046 (16)
C3	0.267 (17)	0.043 (3)	0.043 (3)	0.046 (7)	−0.002 (6)	0.008 (2)
C4	0.125 (6)	0.029 (2)	0.052 (2)	−0.013 (4)	−0.008 (5)	0.0091 (18)
C5	0.098 (6)	0.037 (2)	0.045 (3)	0.001 (3)	0.004 (3)	0.011 (2)
C6	0.079 (3)	0.0335 (17)	0.0298 (17)	−0.002 (5)	0.001 (5)	−0.0016 (14)

Geometric parameters (Å, °)

K1—O1	2.712 (5)	O4—N4	1.247 (4)
K1—O1i	2.712 (5)	O5—H10	0.856 (19)
K1—O2ii	2.736 (6)	O5—H11	0.87 (2)
K1—O2iii	2.736 (6)	N1—C6	1.318 (5)
K1—O5i	2.815 (7)	N1—C2	1.502 (6)
K1—O5	2.815 (7)	N1—H2	0.8600
K1—C1ii	3.524 (5)	N2—C6	1.342 (5)
K1—C1iii	3.524 (5)	N2—C5	1.494 (7)
K1—K2	3.6942 (8)	N2—H9	0.8600
K1—K2iv	3.6942 (8)	N3—N4	1.305 (4)
K1—H11	2.70 (11)	N3—C6	1.377 (5)
K2—O1	2.642 (5)	C1—C2	1.540 (6)
K2—O1v	2.642 (5)	C1—K1viii	3.524 (5)
K2—O2vi	2.714 (6)	C2—C3	1.423 (9)
K2—O2ii	2.714 (6)	C2—H1	0.9800
K2—O5	2.783 (6)	C3—C4	1.552 (9)
K2—O5v	2.783 (6)	C3—H4	0.9700
K2—K1vii	3.6942 (8)	C3—H3	0.9700
K2—H11	3.06 (6)	C4—C5	1.326 (7)
O1—C1	1.255 (4)	C4—H5	0.9700
O2—C1	1.239 (5)	C4—H6	0.9700
O2—K2viii	2.714 (6)	C5—H7	0.9700
O2—K1viii	2.736 (6)	C5—H8	0.9700
O3—N4	1.241 (4)
O1—K1—O1i	155.74 (15)	O2ii—K2—K1vii	132.78 (15)
O1—K1—O2ii	84.89 (16)	O5—K2—K1vii	130.69 (16)
O1i—K1—O2ii	110.81 (14)	O5v—K2—K1vii	49.08 (15)
O1—K1—O2iii	110.81 (14)	O1—K2—K1	47.16 (12)
O1i—K1—O2iii	84.89 (16)	O1v—K2—K1	132.72 (12)
O2ii—K1—O2iii	101.4 (2)	O2vi—K2—K1	132.78 (15)
O1—K1—O5i	87.51 (15)	O2ii—K2—K1	47.57 (13)
O1i—K1—O5i	82.52 (14)	O5—K2—K1	49.08 (15)
O2ii—K1—O5i	160.81 (11)	O5v—K2—K1	130.69 (16)
O2iii—K1—O5i	65.09 (14)	K1vii—K2—K1	179.60 (13)
O1—K1—O5	82.52 (14)	O1—K2—H11	89 (2)
O1i—K1—O5	87.51 (15)	O1v—K2—H11	87 (2)
O2ii—K1—O5	65.09 (14)	O2vi—K2—H11	146.2 (10)
O2iii—K1—O5	160.81 (11)	O2ii—K2—H11	50.6 (8)
O5i—K1—O5	131.23 (19)	O5—K2—H11	16.1 (6)
O1—K1—C1ii	101.25 (17)	O5v—K2—H11	146.1 (6)
O1i—K1—C1ii	93.15 (14)	K1vii—K2—H11	134 (2)
O2ii—K1—C1ii	17.69 (15)	K1—K2—H11	46 (2)
O2iii—K1—C1ii	101.48 (14)	C1—O1—K2	133.3 (6)
O5i—K1—C1ii	166.12 (17)	C1—O1—K1	132.3 (5)
O5—K1—C1ii	61.33 (12)	K2—O1—K1	87.26 (8)
O1—K1—C1iii	93.15 (14)	C1—O2—K2viii	125.5 (5)
O1i—K1—C1iii	101.25 (17)	C1—O2—K1viii	120.1 (6)
O2ii—K1—C1iii	101.48 (14)	K2viii—O2—K1viii	85.34 (8)
O2iii—K1—C1iii	17.69 (15)	K2—O5—K1	82.59 (8)
O5i—K1—C1iii	61.33 (12)	K2—O5—H10	155 (4)
O5—K1—C1iii	166.12 (17)	K1—O5—H10	114 (5)
C1ii—K1—C1iii	107.02 (17)	K2—O5—H11	101 (5)
O1—K1—K2	45.59 (12)	K1—O5—H11	74 (7)
O1i—K1—K2	134.53 (12)	H10—O5—H11	102 (3)
O2ii—K1—K2	47.09 (13)	C6—N1—C2	127.9 (6)
O2iii—K1—K2	132.56 (15)	C6—N1—H2	116.0
O5i—K1—K2	131.90 (15)	C2—N1—H2	116.0
O5—K1—K2	48.33 (15)	C6—N2—C5	124.8 (5)
C1ii—K1—K2	59.38 (14)	C6—N2—H9	117.6
C1iii—K1—K2	120.34 (15)	C5—N2—H9	117.6
O1—K1—K2iv	134.53 (12)	N4—N3—C6	119.7 (3)
O1i—K1—K2iv	45.59 (12)	O3—N4—O4	118.6 (3)
O2ii—K1—K2iv	132.56 (15)	O3—N4—N3	125.0 (3)
O2iii—K1—K2iv	47.09 (13)	O4—N4—N3	116.4 (3)
O5i—K1—K2iv	48.33 (15)	O2—C1—O1	125.4 (4)
O5—K1—K2iv	131.90 (15)	O2—C1—C2	117.8 (3)
C1ii—K1—K2iv	120.34 (15)	O1—C1—C2	116.6 (4)
C1iii—K1—K2iv	59.38 (14)	O2—C1—K1viii	42.2 (4)
K2—K1—K2iv	179.60 (13)	O1—C1—K1viii	97.8 (3)
O1—K1—H11	95.8 (12)	C2—C1—K1viii	127.8 (4)
O1i—K1—H11	80.1 (15)	C3—C2—N1	112.6 (5)
O2ii—K1—H11	54.4 (13)	C3—C2—C1	115.8 (5)
O2iii—K1—H11	142.9 (4)	N1—C2—C1	103.6 (4)
O5i—K1—H11	144.2 (12)	C3—C2—H1	108.2
O5—K1—H11	17.9 (4)	N1—C2—H1	108.2
C1ii—K1—H11	46.4 (10)	C1—C2—H1	108.2
C1iii—K1—H11	153.2 (8)	C2—C3—C4	112.6 (8)
K2—K1—H11	54.5 (15)	C2—C3—H4	109.1
K2iv—K1—H11	125.5 (15)	C4—C3—H4	109.1
O1—K2—O1v	154.51 (16)	C2—C3—H3	109.1
O1—K2—O2vi	109.73 (14)	C4—C3—H3	109.1
O1v—K2—O2vi	86.68 (16)	H4—C3—H3	107.8
O1—K2—O2ii	86.68 (16)	C5—C4—C3	124.8 (4)
O1v—K2—O2ii	109.73 (14)	C5—C4—H5	106.1
O2vi—K2—O2ii	101.3 (2)	C3—C4—H5	106.1
O1—K2—O5	84.41 (15)	C5—C4—H6	106.1
O1v—K2—O5	84.89 (16)	C3—C4—H6	106.1
O2vi—K2—O5	160.93 (12)	H5—C4—H6	106.3
O2ii—K2—O5	65.81 (15)	C4—C5—N2	124.3 (5)
O1—K2—O5v	84.89 (16)	C4—C5—H7	106.3
O1v—K2—O5v	84.41 (15)	N2—C5—H7	106.3
O2vi—K2—O5v	65.81 (15)	C4—C5—H8	106.3
O2ii—K2—O5v	160.93 (12)	N2—C5—H8	106.3
O5—K2—O5v	130.0 (2)	H7—C5—H8	106.4
O1—K2—K1vii	132.72 (12)	N1—C6—N2	120.6 (4)
O1v—K2—K1vii	47.16 (12)	N1—C6—N3	125.2 (4)
O2vi—K2—K1vii	47.57 (13)	N2—C6—N3	112.1 (3)
O1v—K2—O1—C1	−49.9 (4)	O2ii—K1—O5—K2	−53.73 (14)
O2vi—K2—O1—C1	77.6 (4)	O2iii—K1—O5—K2	−101.4 (5)
O2ii—K2—O1—C1	178.5 (4)	O5i—K1—O5—K2	114.12 (11)
O5—K2—O1—C1	−115.5 (4)	C1ii—K1—O5—K2	−73.12 (16)
O5v—K2—O1—C1	15.6 (4)	C1iii—K1—O5—K2	−38.4 (6)
K1vii—K2—O1—C1	27.7 (5)	K2iv—K1—O5—K2	−179.55 (14)
K1—K2—O1—C1	−151.7 (4)	C6—N3—N4—O3	−2.1 (16)
O1v—K2—O1—K1	101.82 (8)	C6—N3—N4—O4	175.9 (10)
O2vi—K2—O1—K1	−130.65 (16)	K2viii—O2—C1—O1	−49.8 (12)
O2ii—K2—O1—K1	−29.78 (10)	K1viii—O2—C1—O1	57.6 (12)
O5—K2—O1—K1	36.21 (12)	K2viii—O2—C1—C2	135.8 (5)
O5v—K2—O1—K1	167.33 (12)	K1viii—O2—C1—C2	−116.8 (5)
K1vii—K2—O1—K1	179.47 (16)	K2viii—O2—C1—K1viii	−107.4 (3)
O1i—K1—O1—C1	49.8 (4)	K2—O1—C1—O2	−114.3 (9)
O2ii—K1—O1—C1	−178.2 (4)	K1—O1—C1—O2	105.4 (9)
O2iii—K1—O1—C1	−77.9 (4)	K2—O1—C1—C2	60.2 (8)
O5i—K1—O1—C1	−15.8 (4)	K1—O1—C1—C2	−80.1 (8)
O5—K1—O1—C1	116.3 (4)	K2—O1—C1—K1viii	−79.4 (3)
C1ii—K1—O1—C1	175.0 (4)	K1—O1—C1—K1viii	140.3 (2)
C1iii—K1—O1—C1	−76.9 (5)	C6—N1—C2—C3	−67.0 (11)
K2—K1—O1—C1	152.2 (4)	C6—N1—C2—C1	167.2 (9)
K2iv—K1—O1—C1	−28.3 (5)	O2—C1—C2—C3	−146.7 (9)
O1i—K1—O1—K2	−102.45 (8)	O1—C1—C2—C3	38.4 (11)
O2ii—K1—O1—K2	29.60 (10)	K1viii—C1—C2—C3	164.0 (6)
O2iii—K1—O1—K2	129.84 (15)	O2—C1—C2—N1	−22.9 (10)
O5i—K1—O1—K2	−168.04 (12)	O1—C1—C2—N1	162.2 (8)
O5—K1—O1—K2	−35.89 (12)	K1viii—C1—C2—N1	−72.2 (6)
C1ii—K1—O1—K2	22.82 (11)	N1—C2—C3—C4	72.2 (10)
C1iii—K1—O1—K2	130.87 (14)	C1—C2—C3—C4	−168.9 (7)
K2iv—K1—O1—K2	179.46 (17)	C2—C3—C4—C5	−39.8 (16)
O1—K2—O5—K1	−34.97 (11)	C3—C4—C5—N2	−19.3 (15)
O1v—K2—O5—K1	168.20 (12)	C6—N2—C5—C4	52.9 (12)
O2vi—K2—O5—K1	104.1 (5)	C2—N1—C6—N2	42.7 (16)
O2ii—K2—O5—K1	53.89 (13)	C2—N1—C6—N3	−154.9 (9)
O5v—K2—O5—K1	−113.49 (10)	C5—N2—C6—N1	−43.0 (15)
K1vii—K2—O5—K1	−179.56 (14)	C5—N2—C6—N3	152.5 (8)
O1—K1—O5—K2	34.09 (11)	N4—N3—C6—N1	12.3 (17)
O1i—K1—O5—K2	−168.08 (12)	N4—N3—C6—N2	176.0 (9)

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

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H11···O1ii	0.87 (2)	2.09 (5)	2.885 (5)	153 (10)
O5—H10···O3ix	0.86 (2)	2.03 (4)	2.793 (4)	148 (6)
N2—H9···N3x	0.86	2.39	3.080 (4)	138
N1—H2···O3	0.86	2.09	2.561 (5)	114

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