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

Karapetyan, H.A.

doi:10.1107/S1600536808011835

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o943

doi:10.1107/S1600536808011835

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L-2-Nitrimino-1,3-diazepane-4-carboxylic acid

Harutyun A. Karapetyan ^a ^*

^aMolecular Structure Research Center, National Academy of Sciences RA, Azatutyan ave. 26, 375014 Yerevan, Republic of Armenia
^*Correspondence e-mail: harkar@nfsat.am

(Received 31 March 2008; accepted 24 April 2008; online 30 April 2008)

The cyclic form of L-nitroarginine, C₆H₁₀N₄O₄, crystallizes with two independent molecules in the asymmetric unit. According to the geometrical parameters, similar in both molecules, the structure corresponds to that of L-2-nitrimino-1,3-diazepane-4-carboxylic acid; there are, however, conformational differences between the independent molecules, one of them being close to a twisted chair while the other might be described as a rather flattened boat. All six active H atoms in the two molecules are involved in hydrogen bonds, two of which are intramolecular and four intermolecular, forming an infinite chain of molecules along the b axis.

Related literature

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

Experimental

Crystal data

C₆H₁₀N₄O₄
M_r = 202.18
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9787 (14) Å
b = 15.233 (3) Å
c = 16.637 (3) Å
V = 1768.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 (2) K
0.20 × 0.17 × 0.14 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
13278 measured reflections
2211 independent reflections
1509 reflections with I > 2σ(I)
R_int = 0.046
3 standard reflections every 400 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.06
2211 reflections
255 parameters
H-atom parameters constraned
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H10⋯O6	0.86	2.27	2.938 (4)	134
N6—H20⋯O2ⁱ	0.86	2.17	2.988 (4)	158
N1—H3⋯O3	0.86	2.05	2.591 (4)	121
N5—H13⋯O7	0.86	1.92	2.571 (4)	132
O5—H11⋯N3	0.82	1.88	2.690 (4)	172
O1—H1⋯N7ⁱⁱ	0.82	1.88	2.685 (3)	169
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011835/bg2177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011835/bg2177Isup2.hkl

checkCIF report

Comment top

The salts of the L-arginine have been intensively investigated as non-linear optical materials [Petrosyan et al.(2005) and Karapetyan et al.(2007)]. Recently, reports about L-nitroarginine [Apreyan et al.(2008)] and its crystalline salts [Apreyan et al.(2007)] (a promising line of non-linear optical materials) have appeared.

We present herein a structural study of the cyclic form of L-nitroarginine, C₆H₁₀N₄O₄ (I), which crystallizes with two independent molecules in the unit cell. The molecule was reported for the first time by (Paul et al., 1961) where it was suggested to be 2-nitro-4-carboxy-1,3- -diazacycloheptane, on the basis of chemical properties and IR spectra. According to the present single-crystal X-ray diffraction results the L-2-nitrimino-1,3-diazepane-4-carboxylic acid (L-NIDCA) form is suggested instead. A view of the H-bonded pair of crystallographically independent molecules is shown in Fig. 1. The values of bond distances and angles are in agreement with common accepted values which lead to the proposed structural interpretation. In spite of the metric similarities there are conformational differences between the independent moieties, one of them being close to a twist-chair while the other may be described as an essentially flattened boat. All six active H atoms in the crystal are involved in hydrogen bonding (Table 1), two of them being intra- and four inter-molecular, linking crystallographically independent units and by way of which an infinite chain of molecules along the b axis is formed (Fig. 2).

Related literature top

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

Experimental top

The obtainement of crystals of the title compound consisted of a two step process.First of all, the potassium salt of (I) was obtained by the reaction of L-nitroarginine with KOH. Afterwards, by the interaction of this potassium salt with HBF4 and further separation of the poorly soluble KBF4 salt, single crystals of (I) were obtained by slow evaporation at room temperature. The compound obtained is more correctly named L-2-nitrimino-1,3-diazepane-4-carboxylic acid (L-NIDCA). Details of the obtainment of L-NIDCA and L-NIDCA^.H₂O, as well as vibrational spectra, thermal properties and SHG will be reported soon separately [Apreyan and Petrosyan, 2008].

Computing details top

Data collection: CAD-4 Manual (Enraf–Nonius, 1988); cell refinement: 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A perspective view of the crystallographically independent molecules paired via intermolecular H-bonds showing atomic numbering and displacement ellipsoids at the 50% probability.
	Fig. 2. Packing of the molecules (without non-active H atoms). For clarity the non-hydrogen atoms of the crystallographically independent molecules participating in H-bonds are numbered only.

L-2-Nitrimino-1,3-diazepane-4-carboxylic acid top

Crystal data top

C₆H₁₀N₄O₄	F(000) = 848
M_r = 202.18	D_x = 1.519 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 24 reflections
a = 6.9787 (14) Å	θ = 14–16°
b = 15.233 (3) Å	µ = 0.13 mm⁻¹
c = 16.637 (3) Å	T = 293 K
V = 1768.6 (6) Å³	Block, colourless
Z = 8	0.20 × 0.17 × 0.14 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.046
Radiation source: fine-focus sealed tube	θ_max = 27.0°, θ_min = 2.5°
Graphite monochromator	h = −7→8
ω/2θ scans	k = −19→19
13278 measured reflections	l = −21→21
2211 independent reflections	3 standard reflections every 400 reflections
1509 reflections with I > 2σ(I)	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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0543P)² + 0.5039P] where P = (F_o² + 2F_c²)/3
2211 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₆H₁₀N₄O₄	V = 1768.6 (6) Å³
M_r = 202.18	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.9787 (14) Å	µ = 0.13 mm⁻¹
b = 15.233 (3) Å	T = 293 K
c = 16.637 (3) Å	0.20 × 0.17 × 0.14 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.046
13278 measured reflections	3 standard reflections every 400 reflections
2211 independent reflections	intensity decay: none
1509 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.06	Δρ_max = 0.25 e Å⁻³
2211 reflections	Δρ_min = −0.21 e Å⁻³
255 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
O1	0.7754 (5)	0.88281 (14)	0.60814 (15)	0.0563 (8)
H1	0.7796	0.9337	0.5922	0.085*
O2	0.8669 (4)	0.85314 (15)	0.48298 (16)	0.0472 (7)
O3	0.8340 (4)	0.67954 (15)	0.34868 (15)	0.0530 (8)
O4	0.7646 (6)	0.55602 (18)	0.29427 (15)	0.0723 (10)
O5	0.8340 (6)	0.38278 (15)	0.38570 (16)	0.0659 (10)
H11	0.8210	0.4336	0.4009	0.099*
O6	0.8143 (4)	0.35371 (15)	0.51572 (15)	0.0442 (7)
O7	0.8020 (5)	0.17963 (15)	0.64914 (14)	0.0525 (8)
O8	0.7484 (6)	0.05314 (16)	0.70190 (15)	0.0632 (9)
N1	0.8515 (4)	0.68230 (16)	0.50423 (17)	0.0333 (7)
H3	0.9030	0.7103	0.4649	0.040*
N2	0.8213 (5)	0.54128 (18)	0.55682 (17)	0.0392 (8)
H10	0.7518	0.4952	0.5506	0.047*
N3	0.8130 (5)	0.55431 (18)	0.42317 (17)	0.0384 (8)
N4	0.8015 (5)	0.59993 (18)	0.35350 (18)	0.0426 (8)
N5	0.8587 (4)	0.18391 (17)	0.49647 (17)	0.0366 (7)
H13	0.8600	0.2132	0.5407	0.044*
N6	0.8668 (5)	0.04394 (18)	0.44140 (17)	0.0393 (7)
H20	0.8344	−0.0099	0.4491	0.047*
N7	0.8136 (4)	0.05420 (18)	0.57390 (16)	0.0356 (7)
N8	0.7869 (5)	0.09867 (18)	0.64405 (18)	0.0405 (7)
C1	0.8179 (5)	0.8301 (2)	0.5493 (2)	0.0348 (9)
C2	0.7977 (5)	0.73407 (19)	0.57448 (18)	0.0313 (8)
H2	0.6619	0.7230	0.5854	0.038*
C3	0.9090 (6)	0.7139 (2)	0.6508 (2)	0.0442 (9)
H5	1.0450	0.7133	0.6388	0.053*
H4	0.8857	0.7598	0.6900	0.053*
C4	0.8511 (6)	0.6259 (2)	0.6862 (2)	0.0429 (9)
H6	0.9056	0.6202	0.7396	0.052*
H7	0.7128	0.6236	0.6912	0.052*
C5	0.9179 (6)	0.5504 (2)	0.6348 (2)	0.0428 (9)
H8	1.0542	0.5571	0.6253	0.051*
H9	0.9000	0.4964	0.6649	0.051*
C6	0.8289 (5)	0.5961 (2)	0.4948 (2)	0.0313 (8)
C7	0.8343 (5)	0.3309 (2)	0.4473 (2)	0.0343 (8)
C8	0.8689 (5)	0.2356 (2)	0.42267 (19)	0.0336 (8)
H12	0.9992	0.2310	0.4011	0.040*
C9	0.7300 (6)	0.2026 (2)	0.3592 (2)	0.0455 (9)
H15	0.6101	0.1870	0.3849	0.055*
H14	0.7039	0.2496	0.3214	0.055*
C10	0.8042 (6)	0.1241 (2)	0.3135 (2)	0.0483 (10)
H17	0.6959	0.0893	0.2955	0.058*
H16	0.8716	0.1446	0.2661	0.058*
C11	0.9367 (6)	0.0661 (2)	0.36141 (19)	0.0437 (9)
H19	0.9578	0.0122	0.3317	0.052*
H18	1.0594	0.0955	0.3667	0.052*
C12	0.8479 (5)	0.09769 (19)	0.5036 (2)	0.0306 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.107 (2)	0.0200 (12)	0.0418 (15)	−0.0005 (15)	0.0200 (17)	−0.0027 (11)
O2	0.0777 (19)	0.0213 (11)	0.0427 (15)	−0.0003 (12)	0.0161 (14)	0.0023 (11)
O3	0.093 (2)	0.0271 (13)	0.0389 (15)	0.0039 (13)	0.0023 (15)	0.0058 (12)
O4	0.137 (3)	0.0472 (18)	0.0325 (15)	−0.009 (2)	−0.009 (2)	−0.0075 (14)
O5	0.137 (3)	0.0214 (13)	0.0387 (15)	0.0028 (16)	0.0074 (17)	0.0042 (11)
O6	0.0735 (18)	0.0234 (12)	0.0357 (13)	0.0021 (12)	0.0036 (13)	−0.0026 (11)
O7	0.096 (2)	0.0264 (12)	0.0353 (14)	−0.0023 (14)	0.0031 (15)	−0.0035 (12)
O8	0.115 (3)	0.0393 (15)	0.0347 (15)	−0.0006 (19)	0.0091 (18)	0.0087 (13)
N1	0.0498 (18)	0.0193 (13)	0.0307 (16)	−0.0017 (13)	0.0056 (14)	0.0026 (13)
N2	0.064 (2)	0.0215 (13)	0.0319 (15)	−0.0086 (13)	0.0034 (15)	0.0008 (13)
N3	0.062 (2)	0.0205 (14)	0.0325 (16)	−0.0005 (14)	0.0049 (15)	−0.0004 (13)
N4	0.067 (2)	0.0277 (14)	0.0334 (17)	0.0067 (15)	−0.0013 (17)	−0.0016 (15)
N5	0.063 (2)	0.0188 (13)	0.0278 (16)	−0.0042 (14)	0.0032 (15)	0.0005 (13)
N6	0.064 (2)	0.0198 (13)	0.0339 (16)	0.0009 (14)	0.0020 (15)	−0.0001 (13)
N7	0.0563 (19)	0.0212 (14)	0.0294 (15)	−0.0001 (13)	0.0012 (15)	−0.0011 (12)
N8	0.063 (2)	0.0258 (14)	0.0332 (17)	−0.0007 (14)	0.0005 (17)	0.0020 (14)
C1	0.042 (2)	0.0233 (18)	0.039 (2)	−0.0016 (14)	0.0035 (17)	−0.0020 (17)
C2	0.0437 (19)	0.0193 (14)	0.0310 (17)	−0.0004 (14)	0.0016 (16)	−0.0015 (13)
C3	0.063 (2)	0.0331 (16)	0.0363 (18)	−0.0035 (17)	−0.0063 (19)	−0.0031 (14)
C4	0.067 (2)	0.0336 (18)	0.0278 (18)	0.0030 (17)	−0.0058 (17)	0.0015 (15)
C5	0.061 (2)	0.0317 (17)	0.036 (2)	0.0055 (18)	−0.0003 (19)	0.0027 (15)
C6	0.037 (2)	0.0225 (16)	0.0344 (19)	−0.0017 (13)	0.0061 (15)	0.0002 (15)
C7	0.050 (2)	0.0197 (17)	0.0335 (19)	−0.0037 (14)	−0.0001 (16)	0.0014 (15)
C8	0.046 (2)	0.0205 (14)	0.0345 (18)	0.0019 (14)	0.0019 (16)	0.0002 (13)
C9	0.061 (2)	0.0350 (17)	0.0401 (19)	0.0117 (17)	−0.0133 (19)	−0.0061 (15)
C10	0.078 (3)	0.0290 (18)	0.038 (2)	0.0057 (18)	−0.006 (2)	−0.0030 (16)
C11	0.069 (3)	0.0296 (17)	0.0326 (19)	0.0080 (17)	0.0094 (19)	−0.0046 (15)
C12	0.041 (2)	0.0198 (15)	0.0309 (18)	0.0005 (13)	−0.0014 (15)	0.0023 (14)

Geometric parameters (Å, º) top

O1—C1	1.300 (4)	N7—N8	1.362 (4)
O1—H1	0.8200	N7—C12	1.365 (4)
O2—C1	1.207 (4)	C1—C2	1.528 (4)
O3—N4	1.236 (3)	C2—C3	1.519 (4)
O4—N4	1.219 (4)	C2—H2	0.9800
O5—C7	1.294 (4)	C3—C4	1.519 (5)
O5—H11	0.8200	C3—H5	0.9700
O6—C7	1.199 (4)	C3—H4	0.9700
O7—N8	1.241 (3)	C4—C5	1.507 (5)
O8—N8	1.216 (3)	C4—H6	0.9700
N1—C6	1.332 (4)	C4—H7	0.9700
N1—C2	1.459 (4)	C5—H8	0.9700
N1—H3	0.8600	C5—H9	0.9700
N2—C6	1.328 (4)	C7—C8	1.527 (4)
N2—C5	1.469 (4)	C8—C9	1.520 (5)
N2—H10	0.8600	C8—H12	0.9800
N3—N4	1.354 (4)	C9—C10	1.508 (5)
N3—C6	1.356 (4)	C9—H15	0.9700
N5—C12	1.321 (4)	C9—H14	0.9700
N5—C8	1.460 (4)	C10—C11	1.506 (5)
N5—H13	0.8600	C10—H17	0.9700
N6—C12	1.327 (4)	C10—H16	0.9700
N6—C11	1.457 (4)	C11—H19	0.9700
N6—H20	0.8600	C11—H18	0.9700

C1—O1—H1	109.5	C3—C4—H7	109.2
C7—O5—H11	109.5	H6—C4—H7	107.9
C6—N1—C2	126.6 (3)	N2—C5—C4	115.5 (3)
C6—N1—H3	116.7	N2—C5—H8	108.4
C2—N1—H3	116.7	C4—C5—H8	108.4
C6—N2—C5	127.5 (3)	N2—C5—H9	108.4
C6—N2—H10	116.3	C4—C5—H9	108.4
C5—N2—H10	116.3	H8—C5—H9	107.5
N4—N3—C6	121.1 (3)	N2—C6—N1	122.2 (3)
O4—N4—O3	121.6 (3)	N2—C6—N3	112.6 (3)
O4—N4—N3	115.0 (3)	N1—C6—N3	125.2 (3)
O3—N4—N3	123.2 (3)	O6—C7—O5	125.1 (3)
C12—N5—C8	127.9 (3)	O6—C7—C8	123.3 (3)
C12—N5—H13	116.0	O5—C7—C8	111.6 (3)
C8—N5—H13	116.0	N5—C8—C9	112.0 (3)
C12—N6—C11	127.1 (3)	N5—C8—C7	106.2 (3)
C12—N6—H20	116.5	C9—C8—C7	113.6 (3)
C11—N6—H20	116.5	N5—C8—H12	108.3
N8—N7—C12	121.1 (3)	C9—C8—H12	108.3
O8—N8—O7	122.1 (3)	C7—C8—H12	108.3
O8—N8—N7	115.1 (3)	C10—C9—C8	113.2 (3)
O7—N8—N7	122.8 (3)	C10—C9—H15	108.9
O2—C1—O1	125.0 (3)	C8—C9—H15	108.9
O2—C1—C2	123.7 (3)	C10—C9—H14	108.9
O1—C1—C2	111.4 (3)	C8—C9—H14	108.9
N1—C2—C3	115.4 (3)	H15—C9—H14	107.8
N1—C2—C1	105.9 (3)	C11—C10—C9	114.1 (3)
C3—C2—C1	112.0 (3)	C11—C10—H17	108.7
N1—C2—H2	107.7	C9—C10—H17	108.7
C3—C2—H2	107.7	C11—C10—H16	108.7
C1—C2—H2	107.7	C9—C10—H16	108.7
C4—C3—C2	111.5 (3)	H17—C10—H16	107.6
C4—C3—H5	109.3	N6—C11—C10	114.5 (3)
C2—C3—H5	109.3	N6—C11—H19	108.6
C4—C3—H4	109.3	C10—C11—H19	108.6
C2—C3—H4	109.3	N6—C11—H18	108.6
H5—C3—H4	108.0	C10—C11—H18	108.6
C5—C4—C3	111.9 (3)	H19—C11—H18	107.6
C5—C4—H6	109.2	N5—C12—N6	122.5 (3)
C3—C4—H6	109.2	N5—C12—N7	124.8 (3)
C5—C4—H7	109.2	N6—C12—N7	112.7 (3)

C6—N3—N4—O4	−171.5 (4)	N4—N3—C6—N2	174.4 (3)
C6—N3—N4—O3	11.6 (6)	N4—N3—C6—N1	−6.2 (5)
C12—N7—N8—O8	176.6 (4)	C12—N5—C8—C9	43.1 (5)
C12—N7—N8—O7	−3.9 (6)	C12—N5—C8—C7	167.7 (4)
C6—N1—C2—C3	65.9 (5)	O6—C7—C8—N5	3.5 (5)
C6—N1—C2—C1	−169.6 (3)	O5—C7—C8—N5	−177.9 (3)
O2—C1—C2—N1	0.9 (5)	O6—C7—C8—C9	127.1 (4)
O1—C1—C2—N1	−179.2 (3)	O5—C7—C8—C9	−54.3 (4)
O2—C1—C2—C3	127.5 (4)	N5—C8—C9—C10	−80.9 (4)
O1—C1—C2—C3	−52.6 (4)	C7—C8—C9—C10	158.7 (3)
N1—C2—C3—C4	−72.3 (4)	C8—C9—C10—C11	30.0 (5)
C1—C2—C3—C4	166.4 (3)	C12—N6—C11—C10	−69.0 (5)
C2—C3—C4—C5	69.8 (4)	C9—C10—C11—N6	47.6 (5)
C6—N2—C5—C4	66.1 (5)	C8—N5—C12—N6	8.0 (6)
C3—C4—C5—N2	−69.2 (4)	C8—N5—C12—N7	−171.0 (3)
C5—N2—C6—N1	−30.9 (6)	C11—N6—C12—N5	12.6 (6)
C5—N2—C6—N3	148.5 (3)	C11—N6—C12—N7	−168.3 (3)
C2—N1—C6—N2	−25.9 (5)	N8—N7—C12—N5	0.1 (5)
C2—N1—C6—N3	154.8 (3)	N8—N7—C12—N6	−178.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H10···O6	0.86	2.27	2.938 (4)	134
N6—H20···O2ⁱ	0.86	2.17	2.988 (4)	158
N1—H3···O2	0.86	2.21	2.629 (3)	110
N1—H3···O3	0.86	2.05	2.591 (4)	121
N5—H13···O6	0.86	2.20	2.625 (4)	110
N5—H13···O7	0.86	1.92	2.571 (4)	132
O5—H11···N3	0.82	1.88	2.690 (4)	172
O5—H11···O4	0.82	2.60	3.084 (4)	119
O1—H1···N7ⁱⁱ	0.82	1.88	2.685 (3)	169
O1—H1···O8ⁱⁱ	0.82	2.59	3.033 (3)	116

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

Experimental details

Crystal data
Chemical formula	C₆H₁₀N₄O₄
M_r	202.18
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.9787 (14), 15.233 (3), 16.637 (3)
V (Å³)	1768.6 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.20 × 0.17 × 0.14

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13278, 2211, 1509
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.06
No. of reflections	2211
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21

Computer programs: CAD-4 Manual (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
N2—H10···O6	0.86	2.27	2.938 (4)	134.2
N6—H20···O2ⁱ	0.86	2.17	2.988 (4)	157.9
N1—H3···O3	0.86	2.05	2.591 (4)	120.5
N5—H13···O7	0.86	1.92	2.571 (4)	131.6
O5—H11···N3	0.82	1.88	2.690 (4)	171.9
O1—H1···N7ⁱⁱ	0.82	1.88	2.685 (3)	169.3

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

Acknowledgements

The author expresses his thanks to Dr R. A. Apreyan and Dr A. M. Petrosyan for providing the crystals and for valuable discussion of the results.

References

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