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

Karapetyan, H.A.

doi:10.1107/S1600536808023817

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808023817/hg2410sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808023817/hg2410Isup2.hkl Contains datablock I

CCDC reference: 709666

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
R factor = 0.065
wR factor = 0.193
Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level A
TYPE089_ALERT_1_A  _refine_ls_abs_structure_Flack is not of type numb.
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for         C3

Author Response: This likely to be a consequence of potential disorder


Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....        100 PerFi
PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem...          c
PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem...          b
PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem...          m
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C2
PLAT360_ALERT_2_B Short  C(sp3)-C(sp3) Bond  C4     -   C5     ...       1.33 Ang.

Alert level C
PLAT213_ALERT_2_C Atom C3      has ADP max/min Ratio .............       3.10 prola
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.99 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N1

Author Response: This likely to be a consequence of potential disorder

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.08
PLAT318_ALERT_2_C Check Hybridisation of  N2     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C2     -   C3     ...       1.42 Ang.
PLAT033_ALERT_4_C Flack Parameter Value Deviates from Zero .......       0.50
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT731_ALERT_1_C Bond    Calc     0.86(5), Rep   0.856(19) ......       2.63 su-Ra
              O5   -H10     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.87(6), Rep     0.87(2) ......       3.00 su-Ra
              O5   -H11     1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    17.9(13), Rep     17.9(4) ......       3.25 su-Ra
              O5   -K1   -H11     1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc    101.8(4), Rep   101.82(8) ......       5.00 su-Ra
              O1  -K2  -O1  -K1     2.565   1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc   -102.5(4), Rep  -102.45(8) ......       5.00 su-Ra
              O1  -K1  -O1  -K2     2.665   1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(6), Rep     0.87(2) ......       3.00 su-Ra
              O5   -H11     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(5), Rep   0.856(19) ......       2.63 su-Ra
              O5   -H10     1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.31 Ratio
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      42.20 Deg.
              O2   -C1   -K1      1.555   1.555   7.555

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           29.97
           From the CIF: _reflns_number_total               1791
           From the CIF: _diffrn_reflns_limit_ max hkl   10.   13.   38.
           From the CIF: _diffrn_reflns_limit_ min hkl  -10.  -13.  -38.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   10.   14.   40.
           Calculated minimum hkl  -10.  -14.  -40.
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           29.97
           From the CIF: _reflns_number_total               1791
           Count of symmetry unique reflns         1809
           Completeness (_total/calc)             99.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_4_G Confirm the Absolute Configuration of C2     ...          R

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

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  15 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: DATCOL in CAD-4 Software (Enraf–Nonius, 1988); cell refinement: LS in CAD-4 Software (Enraf–Nonius, 1988); 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 (Sheldrick, 2008).

Figures top

	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.

Potassium L-2-nitrimino-1,3-diazepane-4-carboxylate monohydrate top

Crystal data top

K⁺·C₆H₉N₄O₄⁻·H₂O	F(000) = 1072
M_r = 258.29	D_x = 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 top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.030
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.1°
Graphite monochromator	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 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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.193	w = 1/[σ²(F_o²) + (0.0676P)² + 6.1136P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3141 reflections	Δρ_max = 0.43 e Å⁻³
154 parameters	Δρ_min = −0.39 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1350 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.48 (20)

Crystal data top

K⁺·C₆H₉N₄O₄⁻·H₂O	V = 2163.5 (8) Å³
M_r = 258.29	Z = 8
Orthorhombic, I222	Mo Kα radiation
a = 7.3883 (15) Å	µ = 0.51 mm⁻¹
b = 10.087 (2) Å	T = 293 K
c = 29.031 (6) Å	0.21 × 0.14 × 0.11 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.030
5030 measured reflections	3 standard reflections every 400 reflections
3141 independent reflections	intensity decay: none
1726 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.193	Δρ_max = 0.43 e Å⁻³
S = 1.04	Δρ_min = −0.39 e Å⁻³
3141 reflections	Absolute structure: Flack (1983), 1350 Friedel pairs
154 parameters	Absolute structure parameter: 0.48 (20)
3 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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—K2^iv	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—O1^v	2.642 (5)	C1—K1^viii	3.524 (5)
K2—O2^vi	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—O5^v	2.783 (6)	C3—H4	0.9700
K2—K1^vii	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—K2^viii	2.714 (6)	C5—H7	0.9700
O2—K1^viii	2.736 (6)	C5—H8	0.9700
O3—N4	1.241 (4)

O1—K1—O1ⁱ	155.74 (15)	O2ⁱⁱ—K2—K1^vii	132.78 (15)
O1—K1—O2ⁱⁱ	84.89 (16)	O5—K2—K1^vii	130.69 (16)
O1ⁱ—K1—O2ⁱⁱ	110.81 (14)	O5^v—K2—K1^vii	49.08 (15)
O1—K1—O2ⁱⁱⁱ	110.81 (14)	O1—K2—K1	47.16 (12)
O1ⁱ—K1—O2ⁱⁱⁱ	84.89 (16)	O1^v—K2—K1	132.72 (12)
O2ⁱⁱ—K1—O2ⁱⁱⁱ	101.4 (2)	O2^vi—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)	O5^v—K2—K1	130.69 (16)
O2ⁱⁱⁱ—K1—O5ⁱ	65.09 (14)	K1^vii—K2—K1	179.60 (13)
O1—K1—O5	82.52 (14)	O1—K2—H11	89 (2)
O1ⁱ—K1—O5	87.51 (15)	O1^v—K2—H11	87 (2)
O2ⁱⁱ—K1—O5	65.09 (14)	O2^vi—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)	O5^v—K2—H11	146.1 (6)
O1ⁱ—K1—C1ⁱⁱ	93.15 (14)	K1^vii—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—K2^viii	125.5 (5)
O1ⁱ—K1—C1ⁱⁱⁱ	101.25 (17)	C1—O2—K1^viii	120.1 (6)
O2ⁱⁱ—K1—C1ⁱⁱⁱ	101.48 (14)	K2^viii—O2—K1^viii	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—K2^iv	134.53 (12)	N4—N3—C6	119.7 (3)
O1ⁱ—K1—K2^iv	45.59 (12)	O3—N4—O4	118.6 (3)
O2ⁱⁱ—K1—K2^iv	132.56 (15)	O3—N4—N3	125.0 (3)
O2ⁱⁱⁱ—K1—K2^iv	47.09 (13)	O4—N4—N3	116.4 (3)
O5ⁱ—K1—K2^iv	48.33 (15)	O2—C1—O1	125.4 (4)
O5—K1—K2^iv	131.90 (15)	O2—C1—C2	117.8 (3)
C1ⁱⁱ—K1—K2^iv	120.34 (15)	O1—C1—C2	116.6 (4)
C1ⁱⁱⁱ—K1—K2^iv	59.38 (14)	O2—C1—K1^viii	42.2 (4)
K2—K1—K2^iv	179.60 (13)	O1—C1—K1^viii	97.8 (3)
O1—K1—H11	95.8 (12)	C2—C1—K1^viii	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
K2^iv—K1—H11	125.5 (15)	C4—C3—H4	109.1
O1—K2—O1^v	154.51 (16)	C2—C3—H3	109.1
O1—K2—O2^vi	109.73 (14)	C4—C3—H3	109.1
O1^v—K2—O2^vi	86.68 (16)	H4—C3—H3	107.8
O1—K2—O2ⁱⁱ	86.68 (16)	C5—C4—C3	124.8 (4)
O1^v—K2—O2ⁱⁱ	109.73 (14)	C5—C4—H5	106.1
O2^vi—K2—O2ⁱⁱ	101.3 (2)	C3—C4—H5	106.1
O1—K2—O5	84.41 (15)	C5—C4—H6	106.1
O1^v—K2—O5	84.89 (16)	C3—C4—H6	106.1
O2^vi—K2—O5	160.93 (12)	H5—C4—H6	106.3
O2ⁱⁱ—K2—O5	65.81 (15)	C4—C5—N2	124.3 (5)
O1—K2—O5^v	84.89 (16)	C4—C5—H7	106.3
O1^v—K2—O5^v	84.41 (15)	N2—C5—H7	106.3
O2^vi—K2—O5^v	65.81 (15)	C4—C5—H8	106.3
O2ⁱⁱ—K2—O5^v	160.93 (12)	N2—C5—H8	106.3
O5—K2—O5^v	130.0 (2)	H7—C5—H8	106.4
O1—K2—K1^vii	132.72 (12)	N1—C6—N2	120.6 (4)
O1^v—K2—K1^vii	47.16 (12)	N1—C6—N3	125.2 (4)
O2^vi—K2—K1^vii	47.57 (13)	N2—C6—N3	112.1 (3)

O1^v—K2—O1—C1	−49.9 (4)	O2ⁱⁱ—K1—O5—K2	−53.73 (14)
O2^vi—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)
O5^v—K2—O1—C1	15.6 (4)	C1ⁱⁱⁱ—K1—O5—K2	−38.4 (6)
K1^vii—K2—O1—C1	27.7 (5)	K2^iv—K1—O5—K2	−179.55 (14)
K1—K2—O1—C1	−151.7 (4)	C6—N3—N4—O3	−2.1 (16)
O1^v—K2—O1—K1	101.82 (8)	C6—N3—N4—O4	175.9 (10)
O2^vi—K2—O1—K1	−130.65 (16)	K2^viii—O2—C1—O1	−49.8 (12)
O2ⁱⁱ—K2—O1—K1	−29.78 (10)	K1^viii—O2—C1—O1	57.6 (12)
O5—K2—O1—K1	36.21 (12)	K2^viii—O2—C1—C2	135.8 (5)
O5^v—K2—O1—K1	167.33 (12)	K1^viii—O2—C1—C2	−116.8 (5)
K1^vii—K2—O1—K1	179.47 (16)	K2^viii—O2—C1—K1^viii	−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—K1^viii	−79.4 (3)
C1ⁱⁱ—K1—O1—C1	175.0 (4)	K1—O1—C1—K1^viii	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)
K2^iv—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)	K1^viii—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)	K1^viii—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)
K2^iv—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)
O1^v—K2—O5—K1	168.20 (12)	C6—N2—C5—C4	52.9 (12)
O2^vi—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)
O5^v—K2—O5—K1	−113.49 (10)	C5—N2—C6—N1	−43.0 (15)
K1^vii—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, º) top

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···O3^ix	0.86 (2)	2.03 (4)	2.793 (4)	148 (6)
N2—H9···N3^x	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.

Experimental details

Crystal data
Chemical formula	K⁺·C₆H₉N₄O₄⁻·H₂O
M_r	258.29
Crystal system, space group	Orthorhombic, I222
Temperature (K)	293
a, b, c (Å)	7.3883 (15), 10.087 (2), 29.031 (6)
V (Å³)	2163.5 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.21 × 0.14 × 0.11

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5030, 3141, 1726
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.193, 1.04
No. of reflections	3141
No. of parameters	154
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.39
Absolute structure	Flack (1983), 1350 Friedel pairs
Absolute structure parameter	0.48 (20)

Computer programs: DATCOL in CAD-4 Software (Enraf–Nonius, 1988), LS in CAD-4 Software (Enraf–Nonius, 1988), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	137.8
N1—H2···O3	0.86	2.09	2.561 (5)	113.6

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

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

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