l-2-Nitrimino-1,3-diazepane-4-carboxylic acid monohydrate.

The title compound, C(6)H(10)N(4)O(4)·H(2)O, crystallizes with two independent formula units in the asymmetric unit, their geometric parameters being quite similar. The conformations of the 1,3-diazepane rings are also similar and close to a twist-boat. All ten O- and N-bound H atoms are involved in hydrogen bonds, two of which are intra- and eight inter-molecular linking crystallographically independent mol-ecules, into a three-dimensional hydrogen-bonded network.

Related literature

For the crystal structures of some analogues of the title compound, see: Apreyan et al. (2008a ▶, 2008b ▶); Karapetyan et al. (2007 ▶); Petrosyan et al. (2005 ▶); Karapetyan (2008 ▶). For related literature, see: Paul et al. (1961 ▶); Apreyan & Petrosyan (2008 ▶).

Experimental

Crystal data

C6H10N4O4·H2O

M = 220.20

Orthorhombic,

a = 9.0115 (18) Å

b = 14.729 (3) Å

c = 15.257 (3) Å

V = 2025.0 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 293 (2) K

0.22 × 0.17 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

6714 measured reflections

2512 independent reflections

1583 reflections with I > 2σ(I)

R int = 0.040

3 standard reflections every 400 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 1.02

2512 reflections

286 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.27 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015146/bg2187sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015146/bg2187Isup2.hkl

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

C6H10N4O4·H2O	F(000) = 928
Mr = 220.20	Dx = 1.445 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 24 reflections
a = 9.0115 (18) Å	θ = 14–16°
b = 14.729 (3) Å	µ = 0.13 mm−1
c = 15.257 (3) Å	T = 293 K
V = 2025.0 (7) Å3	Prismatic, yellow
Z = 8	0.22 × 0.17 × 0.12 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.040
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 2.6°
graphite	h = 0→11
ω/2θ scans	k = −17→18
6714 measured reflections	l = −19→19
2512 independent reflections	3 standard reflections every 400 reflections
1583 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0704P)2 + 0.3433P] where P = (Fo2 + 2Fc2)/3
2512 reflections	(Δ/σ)max = 0.014
286 parameters	Δρmax = 0.44 e Å−3
6 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.8550 (4)	0.81385 (17)	0.6510 (2)	0.0559 (8)
H1	0.8648	0.7605	0.6653	0.084*
O2	1.0592 (4)	0.83261 (16)	0.7324 (2)	0.0556 (8)
O3	1.2651 (4)	1.00838 (17)	0.83155 (19)	0.0592 (8)
O4	1.2868 (4)	1.1299 (2)	0.90927 (18)	0.0591 (8)
N1	1.0627 (4)	1.00945 (18)	0.7113 (2)	0.0421 (7)
H3	1.1404	0.9789	0.7256	0.051*
N2	0.9663 (4)	1.1533 (2)	0.6923 (2)	0.0507 (9)
H10	0.9437	1.2018	0.7207	0.061*
N3	1.1385 (4)	1.13746 (18)	0.7971 (2)	0.0407 (7)
N4	1.2311 (4)	1.0889 (2)	0.8470 (2)	0.0431 (8)
C1	0.9593 (5)	0.8623 (2)	0.6876 (2)	0.0399 (9)
C2	0.9446 (5)	0.9624 (2)	0.6654 (2)	0.0409 (9)
H2	0.8492	0.9843	0.6879	0.049*
C3	0.9495 (6)	0.9789 (3)	0.5664 (2)	0.0561 (11)
H4	1.0283	0.9428	0.5406	0.067*
H5	0.8563	0.9601	0.5403	0.067*
C4	0.9765 (8)	1.0790 (3)	0.5471 (3)	0.0733 (16)
H6	1.0822	1.0907	0.5512	0.088*
H7	0.9467	1.0911	0.4872	0.088*
C5	0.8980 (6)	1.1435 (3)	0.6055 (3)	0.0688 (15)
H9	0.8951	1.2026	0.5774	0.083*
H8	0.7964	1.1231	0.6129	0.083*
C6	1.0582 (5)	1.0969 (2)	0.7326 (2)	0.0382 (8)
O5	0.2203 (4)	0.6209 (2)	0.6113 (2)	0.0681 (9)
H11	0.1992	0.5667	0.6112	0.102*
O6	0.3842 (4)	0.5793 (2)	0.7134 (2)	0.0702 (9)
O7	0.6264 (5)	0.6721 (2)	0.8634 (2)	0.0816 (12)
O8	0.7679 (5)	0.7592 (2)	0.9383 (2)	0.0785 (11)
N5	0.5019 (4)	0.7416 (2)	0.7264 (2)	0.0474 (8)
H13	0.5467	0.6920	0.7399	0.057*
N6	0.5183 (5)	0.8983 (2)	0.7299 (2)	0.0581 (10)
H20	0.5327	0.9434	0.7646	0.070*
N7	0.6483 (5)	0.8224 (2)	0.8311 (2)	0.0564 (10)
N8	0.6787 (5)	0.7483 (3)	0.8780 (2)	0.0594 (10)
C7	0.3282 (5)	0.6353 (3)	0.6665 (3)	0.0518 (10)
C8	0.3764 (5)	0.7345 (2)	0.6670 (3)	0.0479 (10)
H12	0.2949	0.7710	0.6908	0.057*
C9	0.4115 (6)	0.7691 (3)	0.5742 (3)	0.0577 (12)
H14	0.4718	0.7244	0.5441	0.069*
H15	0.3195	0.7757	0.5419	0.069*
C10	0.4921 (8)	0.8586 (4)	0.5744 (3)	0.0860 (17)
H16	0.5977	0.8462	0.5761	0.103*
H17	0.4717	0.8888	0.5191	0.103*
C11	0.4585 (9)	0.9205 (3)	0.6433 (3)	0.0859 (19)
H18	0.3515	0.9250	0.6482	0.103*
H19	0.4953	0.9799	0.6267	0.103*
C12	0.5530 (5)	0.8170 (2)	0.7613 (2)	0.0453 (9)
O9	0.8626 (5)	0.9582 (3)	0.8857 (4)	0.0980 (13)
H21	0.799 (5)	0.918 (3)	0.883 (4)	0.118*
H22	0.927 (6)	0.944 (4)	0.923 (4)	0.118*
O10	1.1127 (6)	0.9147 (4)	0.9685 (4)	0.134 (2)
H23	1.132 (9)	0.882 (5)	1.014 (3)	0.161*
H24	1.170 (9)	0.893 (6)	0.929 (4)	0.161*

	U11	U22	U33	U12	U13	U23
O1	0.063 (2)	0.0304 (13)	0.0741 (19)	−0.0079 (14)	−0.0175 (17)	0.0017 (13)
O2	0.0548 (17)	0.0305 (13)	0.081 (2)	0.0015 (13)	−0.0159 (18)	0.0023 (14)
O3	0.0668 (19)	0.0344 (13)	0.0765 (18)	0.0104 (14)	−0.0205 (18)	−0.0031 (13)
O4	0.070 (2)	0.0534 (16)	0.0541 (16)	0.0008 (17)	−0.0194 (16)	−0.0042 (14)
N1	0.0486 (19)	0.0241 (13)	0.0536 (17)	0.0017 (14)	−0.0098 (16)	−0.0009 (13)
N2	0.065 (2)	0.0289 (15)	0.058 (2)	0.0053 (16)	−0.0198 (19)	−0.0017 (14)
N3	0.0478 (19)	0.0276 (14)	0.0467 (16)	0.0026 (15)	−0.0085 (16)	−0.0011 (13)
N4	0.051 (2)	0.0338 (15)	0.0446 (16)	−0.0019 (16)	−0.0056 (17)	0.0014 (13)
C1	0.042 (2)	0.0301 (16)	0.047 (2)	0.0002 (18)	0.0023 (19)	−0.0020 (16)
C2	0.048 (2)	0.0291 (17)	0.0456 (19)	−0.0018 (17)	−0.008 (2)	−0.0025 (15)
C3	0.082 (3)	0.042 (2)	0.045 (2)	−0.008 (2)	−0.006 (2)	−0.0004 (17)
C4	0.117 (5)	0.057 (3)	0.047 (2)	−0.008 (3)	−0.011 (3)	0.008 (2)
C5	0.099 (4)	0.040 (2)	0.068 (3)	0.006 (3)	−0.031 (3)	0.007 (2)
C6	0.046 (2)	0.0289 (16)	0.0402 (18)	−0.0023 (17)	0.0028 (18)	−0.0001 (15)
O5	0.072 (2)	0.0556 (18)	0.077 (2)	−0.0083 (17)	−0.010 (2)	0.0005 (17)
O6	0.086 (2)	0.0405 (15)	0.085 (2)	0.0007 (16)	−0.015 (2)	0.0082 (16)
O7	0.123 (3)	0.0527 (19)	0.069 (2)	−0.007 (2)	−0.022 (2)	0.0136 (16)
O8	0.111 (3)	0.074 (2)	0.0512 (16)	0.024 (2)	−0.021 (2)	−0.0030 (15)
N5	0.060 (2)	0.0358 (15)	0.0461 (18)	0.0087 (16)	−0.0062 (19)	−0.0002 (14)
N6	0.082 (3)	0.0379 (17)	0.055 (2)	0.0094 (18)	−0.006 (2)	−0.0026 (15)
N7	0.081 (3)	0.0446 (18)	0.0435 (17)	0.0112 (19)	−0.010 (2)	−0.0004 (15)
N8	0.082 (3)	0.057 (2)	0.0387 (17)	0.018 (2)	−0.003 (2)	−0.0031 (17)
C7	0.053 (3)	0.047 (2)	0.056 (2)	0.005 (2)	0.000 (2)	−0.003 (2)
C8	0.050 (2)	0.039 (2)	0.055 (2)	0.0087 (19)	0.001 (2)	−0.0025 (18)
C9	0.069 (3)	0.055 (3)	0.049 (2)	0.000 (2)	−0.011 (2)	0.0107 (19)
C10	0.114 (5)	0.084 (4)	0.059 (3)	−0.012 (4)	−0.005 (3)	0.017 (3)
C11	0.140 (6)	0.040 (2)	0.078 (3)	0.008 (3)	−0.035 (4)	0.013 (2)
C12	0.059 (2)	0.0377 (19)	0.0396 (19)	0.009 (2)	0.006 (2)	0.0003 (16)
O9	0.082 (3)	0.059 (2)	0.152 (4)	0.013 (2)	−0.013 (3)	0.009 (2)
O10	0.110 (4)	0.172 (5)	0.120 (4)	0.017 (4)	−0.016 (3)	0.082 (4)

O1—C1	1.306 (5)	O6—C7	1.203 (5)
O1—H1	0.8200	O7—N8	1.238 (5)
O2—C1	1.212 (5)	O8—N8	1.232 (5)
O3—N4	1.247 (4)	N5—C12	1.316 (5)
O4—N4	1.232 (4)	N5—C8	1.453 (5)
N1—C6	1.329 (4)	N5—H13	0.8600
N1—C2	1.450 (5)	N6—C12	1.326 (5)
N1—H3	0.8600	N6—C11	1.463 (6)
N2—C6	1.324 (5)	N6—H20	0.8600
N2—C5	1.467 (5)	N7—N8	1.334 (5)
N2—H10	0.8600	N7—C12	1.371 (6)
N3—N4	1.338 (4)	C7—C8	1.525 (6)
N3—C6	1.359 (5)	C8—C9	1.536 (6)
C1—C2	1.518 (5)	C8—H12	0.9800
C2—C3	1.531 (5)	C9—C10	1.505 (7)
C2—H2	0.9800	C9—H14	0.9700
C3—C4	1.523 (6)	C9—H15	0.9700
C3—H4	0.9700	C10—C11	1.424 (7)
C3—H5	0.9700	C10—H16	0.9700
C4—C5	1.482 (7)	C10—H17	0.9700
C4—H6	0.9700	C11—H18	0.9700
C4—H7	0.9700	C11—H19	0.9700
C5—H9	0.9700	O9—H21	0.83 (4)
C5—H8	0.9700	O9—H22	0.84 (4)
O5—C7	1.304 (5)	O10—H23	0.86 (4)
O5—H11	0.8200	O10—H24	0.86 (4)
C1—O1—H1	109.5	C12—N5—C8	125.8 (3)
C6—N1—C2	124.0 (3)	C12—N5—H13	117.1
C6—N1—H3	118.0	C8—N5—H13	117.1
C2—N1—H3	118.0	C12—N6—C11	127.9 (3)
C6—N2—C5	128.3 (3)	C12—N6—H20	116.1
C6—N2—H10	115.9	C11—N6—H20	116.1
C5—N2—H10	115.9	N8—N7—C12	119.9 (3)
N4—N3—C6	120.6 (3)	O8—N8—O7	120.1 (4)
O4—N4—O3	120.8 (3)	O8—N8—N7	115.3 (4)
O4—N4—N3	115.5 (3)	O7—N8—N7	124.6 (4)
O3—N4—N3	123.6 (3)	O6—C7—O5	125.8 (4)
O2—C1—O1	125.4 (3)	O6—C7—C8	122.4 (4)
O2—C1—C2	122.7 (4)	O5—C7—C8	111.8 (4)
O1—C1—C2	111.9 (3)	N5—C8—C7	107.0 (3)
N1—C2—C1	107.0 (3)	N5—C8—C9	113.0 (3)
N1—C2—C3	112.3 (3)	C7—C8—C9	111.9 (3)
C1—C2—C3	111.8 (3)	N5—C8—H12	108.3
N1—C2—H2	108.5	C7—C8—H12	108.3
C1—C2—H2	108.5	C9—C8—H12	108.3
C3—C2—H2	108.5	C10—C9—C8	112.9 (4)
C4—C3—C2	110.4 (3)	C10—C9—H14	109.0
C4—C3—H4	109.6	C8—C9—H14	109.0
C2—C3—H4	109.6	C10—C9—H15	109.0
C4—C3—H5	109.6	C8—C9—H15	109.0
C2—C3—H5	109.6	H14—C9—H15	107.8
H4—C3—H5	108.1	C11—C10—C9	117.3 (5)
C5—C4—C3	115.4 (4)	C11—C10—H16	108.0
C5—C4—H6	108.4	C9—C10—H16	108.0
C3—C4—H6	108.4	C11—C10—H17	108.0
C5—C4—H7	108.4	C9—C10—H17	108.0
C3—C4—H7	108.4	H16—C10—H17	107.2
H6—C4—H7	107.5	C10—C11—N6	116.5 (4)
N2—C5—C4	113.9 (4)	C10—C11—H18	108.2
N2—C5—H9	108.8	N6—C11—H18	108.2
C4—C5—H9	108.8	C10—C11—H19	108.2
N2—C5—H8	108.8	N6—C11—H19	108.2
C4—C5—H8	108.8	H18—C11—H19	107.3
H9—C5—H8	107.7	N5—C12—N6	122.2 (4)
N2—C6—N1	120.9 (4)	N5—C12—N7	125.7 (3)
N2—C6—N3	113.2 (3)	N6—C12—N7	112.1 (3)
N1—C6—N3	125.9 (3)	H21—O9—H22	109 (5)
C7—O5—H11	109.5	H23—O10—H24	104 (5)
C6—N3—N4—O4	−172.7 (4)	C12—N7—N8—O8	178.5 (4)
C6—N3—N4—O3	9.7 (6)	C12—N7—N8—O7	0.0 (7)
C6—N1—C2—C1	−156.2 (3)	C12—N5—C8—C7	−162.6 (4)
C6—N1—C2—C3	80.7 (5)	C12—N5—C8—C9	73.8 (5)
O2—C1—C2—N1	−3.2 (5)	O6—C7—C8—N5	4.4 (6)
O1—C1—C2—N1	178.4 (3)	O5—C7—C8—N5	−176.7 (3)
O2—C1—C2—C3	120.1 (4)	O6—C7—C8—C9	128.7 (5)
O1—C1—C2—C3	−58.3 (5)	O5—C7—C8—C9	−52.4 (5)
N1—C2—C3—C4	−44.5 (6)	N5—C8—C9—C10	−45.9 (5)
C1—C2—C3—C4	−164.7 (4)	C7—C8—C9—C10	−166.7 (4)
C2—C3—C4—C5	−39.4 (7)	C8—C9—C10—C11	−32.6 (7)
C6—N2—C5—C4	−20.4 (7)	C9—C10—C11—N6	73.8 (8)
C3—C4—C5—N2	77.0 (6)	C12—N6—C11—C10	−26.1 (9)
C5—N2—C6—N1	−22.8 (7)	C8—N5—C12—N6	−16.8 (7)
C5—N2—C6—N3	159.5 (4)	C8—N5—C12—N7	164.7 (4)
C2—N1—C6—N2	−19.6 (6)	C11—N6—C12—N5	−18.4 (8)
C2—N1—C6—N3	157.9 (4)	C11—N6—C12—N7	160.3 (5)
N4—N3—C6—N2	176.6 (3)	N8—N7—C12—N5	−10.4 (6)
N4—N3—C6—N1	−1.0 (6)	N8—N7—C12—N6	170.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3i	0.82	1.90	2.716 (4)	173.
N1—H3···O3i	0.86	2.02	2.586 (4)	123.
N2—H10···O2i	0.86	2.05	2.889 (4)	163.
O5—H11···O9i	0.82	1.69	2.510 (5)	174.
N5—H13···O7i	0.86	2.04	2.584 (5)	121.
N6—H20···O6i	0.86	2.16	2.937 (5)	150.
O9—H21···N7i	0.83 (4)	2.11 (3)	2.902 (6)	160 (7)
O9—H22···O10i	0.84 (4)	1.86 (3)	2.662 (7)	159 (7)
O10—H23···O7i	0.86 (4)	2.04 (4)	2.869 (6)	163 (6)
O10—H24···O3i	0.86 (4)	2.41 (8)	2.856 (6)	113 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3i	0.82	1.90	2.716 (4)	173
N1—H3⋯O3	0.86	2.02	2.586 (4)	123
N2—H10⋯O2ii	0.86	2.05	2.889 (4)	163
O5—H11⋯O9iii	0.82	1.69	2.510 (5)	174
N5—H13⋯O7	0.86	2.04	2.584 (5)	121
N6—H20⋯O6iv	0.86	2.16	2.937 (5)	150
O9—H21⋯N7	0.83 (4)	2.11 (3)	2.902 (6)	160 (7)
O9—H22⋯O10	0.84 (4)	1.86 (3)	2.662 (7)	159 (7)
O10—H23⋯O7v	0.86 (4)	2.04 (4)	2.869 (6)	163 (6)
O10—H24⋯O3	0.86 (4)	2.41 (8)	2.856 (6)	113 (5)

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