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Cations and anions of the title compound {systematic name: 1-[4-(amino­carbonyl)butyl]guanidinium bis­(hydrogen­squarate)}, C6H17N5O2+·2C4HO4, are connected into a three-dimensional network by inter­molecular N—H...O hydrogen bonds between the L-argininamidium ammonium, amide and guanidinium functions and the hydrogensquarate carbonyl O atoms. The independent hydrogensquarate monoanions are linked into dimers by pairs of O—H...O′ hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106012108/kp2003sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106012108/kp2003Isup2.hkl
Contains datablock I

CCDC reference: 609431

Comment top

The search for new classes of organic compounds with second-order nonlinear optical properties and high laser beam thresholds is directed towards crystalline materials with high dipole moments, asymmetrically conjugated π-electron systems and non-centrosymmetric crystal structures. Three main classes of organic compounds with different dimensionalities are known in the literature: (a) one-dimensional compounds (dipoles), such as 4-nitroaniline and its derivatives, (b) two-dimensional compounds (quadrupoles), such as 4,6-dinitroresorcinole and its derivatives, and (c) three-dimensional compounds (octupoles), such as the guanidinium cation and its derivatives (Nalwa et al. 1997; Wolff & Wortmann, 1999; Chemla & Zyss, 1987). In the course of our spectroscopic and structural studies of optically active derivatives of amino acids, having nonlinear optical and electro-optical properties, the crystal structure of the title compound, (I), has now been determined. Structurally, (I) belongs to the C-amidated amino acids, whose salts and ester amides of squaric acid represent a new class of compounds, having great biological importance. We also publish the IR and Raman assignments of (I) for the first time. A structural study of some C-amidated amino acids, viz. Ile, Val, Thr, Ser, Met, Trp, Gln and Arg, was performed by In et al. (2001) and the results were similar to those for the C-unamidated counterparts.

The asymmetric unit of (I) is depicted in Fig. 1 and a projection perpendicular to [010] in Fig. 2. The independent hydrogensquarate monoanions, HSq, are linked into dimers by O3'—H3'···O8'viii and O7'—H7'···O4'ix hydrogen bonds (Table 1). Such dimers have previously been reported for argininium hydrogensquarate (Angelova, Velikova et al., 1996) and 4-phenylpyridinium hydrogensquarate (Kolev et al., 2004), but infinite chains are also known, for instance in phenylglycine hydrogensquarate monohydrate (Angelova, Petrova et al., 1996). In contrast to other amino acid amide derivatives, the L-argininamidium cations of (I) are not connected into helical chains by intermolecular N(amide)—H···O(amide) interactions (Kolev et al., 2006). Translation-related cations of (I) are, however, linked by N(ammonium)—H···O(amide) hydrogen bonds (N2—H22···O1iii; Table 1) into chains in the [100] direction. Additional intermolecular N—H···O hydrogen bonds to hydrogensquarate carbonyl O atoms, in which all possible donor NH atoms participate (Table 1), lead to the construction of a three-dimensional network.

Experimental top

The starting compound, L-argininamidium dihydrochloride, is a white powder, which was purchased from Bachem (Switzerland) and recrystallized from methanol. Compound (I) was synthesized by adding a methanol solution (10 ml) of L-argininamidium dihydrochloride (246 mg) to an aqueous solution (28 ml) of squaric acid (228 mg) and leaving the mixture to stand. Colourless crystals that formed after four weeks were filtered off and dried in air at room temperature. Single prismatic and colourless crystals, suitable for X-ray analysis, were grown from a methanol–water solution at room temperature over a period of two months. IR (KBr pellet, cm−1): 3426(s), 3300 (m), 3200 (m) ν(NH2, guanidyl), 3338 νas(NH, aminocarbonyl), 3151 νs(NH, aminocarbonyl), 2865, 2790, 2740 ν(NH3, ammonium), 1804 (w) ν(CO, hydrogensquarate), 1689 (s) ν(C=O), 1655 (NH2, scissoring), 1619 (amide II), 1386 ν(CN, amide III), 1162, 1136 (w) 1109, 908 δ(NH2), 788 (amide VII), 722 (amide V). These data are in accordance with known values for other arginine-containing tri- and tetrapeptides (Kolev, 2006) obtained by IR–LD spectroscopy and theoretical (ab initio HF/6–31++G**) calculations (Ivanova, 2005, 2006; Ivanova & Arnaudov, 2005). The results show a charge redistribution in the guanidyl fragment, leading to an observation of a broad IR-absorption maximum in the whole 3400–2700 cm−1 region assigned to stretching NH+ and NH2+ vibrations.

Refinement top

The S configuration of the argininamidium Cα atom C2 is known for the natural amino acid and was assigned to C2. As atoms heavier than Si are not present in (I), anomalous scattering contributions are negligible and no Friedel pairs were measured. H atoms were treated as riding, with C—H distances of 0.97 Å for the methylene C atoms and 0.98 Å for atom C2, N—H distances of 0.89 Å for ammonium atom N2 and 0.86 for all other N atoms, and O—H distances of 0.82 Å [Uiso(H) = 1.2 Ueq(C) for the H atoms of C2 and C5; Uiso(H) = 1.35 Ueq(N) for the H atoms of N2 and 1.2 Ueq(N) for the H atoms of N6, N8 and N9; Uiso(H) = 1.2 Ueq(O) for the H atom of O7'; all other Uiso(H) values were refined freely].

Computing details top

Data collection: R3m/V (Siemens, 1989); cell refinement: R3m/V; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1995); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and the N2—H···O hydrogen bonds as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A projection of (I) perpendicular to [010], showing the construction of a three-dimensional network through intermolecular hydrogen bonds (dashed lines).
1-[4-(Aminocarbonyl)butyl]guanidinium bis(hydrogensquarate) top
Crystal data top
C6H17N5O2+·2C4HO4F(000) = 420
Mr = 401.34Dx = 1.507 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 15 reflections
a = 5.185 (1) Åθ = 8.0–14.4°
b = 16.668 (3) ŵ = 0.13 mm1
c = 10.458 (2) ÅT = 294 K
β = 101.90 (3)°Prism, colourless
V = 884.5 (3) Å30.54 × 0.24 × 0.22 mm
Z = 2
Data collection top
Siemens P4 four-circle
diffractometer
1972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 30.0°, θmin = 2.3°
Profile fitted ω scansh = 07
Absorption correction: ψ scan
(XPREP in SHELXTL; Sheldrick, 1995)
k = 023
Tmin = 0.945, Tmax = 0.977l = 1414
2919 measured reflections3 standard reflections every 100 reflections
2659 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.046P)2 + 0.0784P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2659 reflectionsΔρmax = 0.23 e Å3
260 parametersΔρmin = 0.19 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.023 (4)
Crystal data top
C6H17N5O2+·2C4HO4V = 884.5 (3) Å3
Mr = 401.34Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.185 (1) ŵ = 0.13 mm1
b = 16.668 (3) ÅT = 294 K
c = 10.458 (2) Å0.54 × 0.24 × 0.22 mm
β = 101.90 (3)°
Data collection top
Siemens P4 four-circle
diffractometer
1972 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XPREP in SHELXTL; Sheldrick, 1995)
Rint = 0.030
Tmin = 0.945, Tmax = 0.9773 standard reflections every 100 reflections
2919 measured reflections intensity decay: 2%
2659 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.099H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å3
2659 reflectionsΔρmin = 0.19 e Å3
260 parameters
Special details top

Experimental. The IR spectrum of (I) (KBr pellet) exhibits no characteristic sharp bands for ν (OH) connected via hydrogen bonds. The bands at 2865 and 1790 and 2740 cm−1 could be assigned to the ν NH3 vibrations, an assignment that is supported by quantum-chemical calculations. Detailed experimental linear-dichroic infrared spectral analysis and ab initio (UHF/6–31G**) calculations of amino acids, peptides and amides, as well as their Au(III) complexes by Ivanova, have indicated a multiple 3400–2200 cm−1 range for ν NH3 stretching vibrations. The strong Raman bands at 2998, 2942, 2923 and 2905 cm−1 belong to the C—H stretching vibrations of the methylene groups. Streching vibrations of the aminocarbonyl group generate the following bands in the IR spectrum: the antisymmetric vibration at 3338 cm−1 and the symmetric one at ca 3151 cm−1. The guanidyl group can be characterized by a strong IR band at 3426, and moderate ones at 3300 and 3200 cm−1belonging to ν NH2 vibrations. A very intensive ν (C=O) (amide I) band of (I) is observed at 1689 cm−1 (IR) with its Raman counterpart lying at 1682 cm−1 and being of intermediate intensity.

The –NH2 deformation (amide II) is expected in the region 1580–1640 cm−1 and we assign the bands at 1619 cm−1 (IR) and 1620 cm−1 (Raman) to amide II modes. In this region, absorbtion of the amino groups of the guanidyl function is also expected, and the scissoring vibrations of this group could not be satifactorily assigned because they overlap with the –NH3-group. The C—N stretching vibration (amide III) is presumalty at 1386 cm−1 but this attribution is not certain. The –NH2 rocking mode absorbs at 1136 cm−1 and is weak in the IR but strong in the Raman spectrum. An amide VII band absorbing at 788 1–1 in the IR has a very weak Raman counterpart at nearly 790 cm−1. A mixed vibration atributed to the –NH2 wag with a contribition from the C=O out-of-plane deformation is responsible for the amide V band at 722 cm−1. The band belonging to the asymetric scissoring vibration of the –NH2 group is observed at 1655 cm−1(IR) and at 1650 cm−1 (Raman). Other prominent bands are those at 1596 and 1498 cm−1 (IR) belonging to the symmetric deformation vibrations of the –NH2 group. Assignment of the band at 1498 cm−1 is not unambiguous because this band overlaps with the band attributed to the mixed C=O and C=C vibration of the hydrogensquarate anion. For the –NH2 rocks, three bands can be taken into account at 1168, 1109 and 908 cm−1, respectively. Characteristic bands for hydrogensquarate anions are recorded at 1804 (w) cm−1 (IR) and 1810 (m) cm−1 (Raman) and can be assigned to a mixed C—O and C=O vibration. The strong Raman bands at 1123 and 629 cm−1 as well as an intermediate one at 1082 cm−1 are attributed to the in and out-of-plane vibrations of the aforementioned anion. CH2 deformation vibrations are found at 1442 and 1344 cm−1.

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
xyzUiso*/Ueq
C1'0.6409 (6)0.32405 (19)0.2642 (3)0.0369 (7)
O1'0.7821 (5)0.37009 (17)0.3405 (2)0.0555 (7)
C2'0.6141 (6)0.30259 (19)0.1239 (3)0.0356 (6)
O2'0.7203 (5)0.32579 (16)0.0350 (2)0.0528 (6)
C3'0.4086 (6)0.24732 (19)0.1383 (3)0.0347 (6)
O3'0.2690 (5)0.19802 (15)0.0537 (2)0.0478 (6)
H3'0.15690.17620.08680.059 (12)*
C4'0.4284 (6)0.26614 (19)0.2734 (3)0.0350 (6)
O4'0.3218 (5)0.24522 (15)0.3652 (2)0.0474 (6)
C5'0.4129 (6)0.53035 (18)0.7961 (3)0.0310 (6)
O5'0.5537 (4)0.48650 (14)0.8744 (2)0.0426 (5)
C6'0.3731 (6)0.54673 (18)0.6522 (3)0.0316 (6)
O6'0.4717 (4)0.51994 (13)0.56320 (19)0.0396 (5)
C7'0.1743 (6)0.60470 (17)0.6659 (3)0.0324 (6)
O7'0.0293 (5)0.65092 (15)0.5784 (2)0.0481 (6)
H7'0.05510.68200.61460.058*
C8'0.2037 (5)0.58970 (18)0.8027 (3)0.0322 (6)
O8'0.1007 (5)0.61370 (14)0.8947 (2)0.0437 (6)
C11.0043 (5)0.35767 (17)0.7428 (3)0.0289 (5)
O11.1166 (4)0.37749 (14)0.6554 (2)0.0409 (5)
N11.1117 (5)0.36099 (17)0.8694 (2)0.0391 (6)
H111.27060.37800.89470.047*
H121.02230.34620.92600.047*
C20.7251 (5)0.32405 (16)0.7102 (3)0.0268 (5)
H20.62580.34460.77340.032*
N20.6032 (4)0.35426 (15)0.5779 (2)0.0329 (5)
H210.54790.40440.58390.044*
H220.46690.32330.54310.044*
H230.72170.35320.52730.044*
C30.7263 (5)0.23211 (17)0.7149 (3)0.0324 (6)
H310.77470.21140.63640.042 (9)*
H320.85840.21440.78920.052 (10)*
C40.4599 (5)0.19779 (16)0.7259 (3)0.0305 (6)
H410.32580.21910.65550.036 (8)*
H420.41820.21520.80780.047 (10)*
C50.4518 (6)0.10630 (17)0.7200 (3)0.0374 (7)
H510.27890.08790.72890.045*
H520.48010.08870.63550.045*
N60.6516 (5)0.07069 (15)0.8228 (2)0.0394 (6)
H60.66430.08940.90050.047*
C70.8163 (6)0.01196 (17)0.8076 (3)0.0329 (6)
N80.8127 (5)0.02190 (18)0.6928 (2)0.0447 (7)
H810.70130.00600.62480.054*
H820.92180.05980.68610.054*
N90.9916 (6)0.01320 (19)0.9115 (3)0.0518 (7)
H911.10030.05090.90330.062*
H920.99620.00830.98670.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1'0.0361 (15)0.0415 (17)0.0358 (15)0.0083 (14)0.0134 (12)0.0004 (13)
O1'0.0566 (14)0.0678 (17)0.0462 (13)0.0313 (14)0.0204 (11)0.0132 (12)
C2'0.0355 (15)0.0362 (15)0.0363 (15)0.0027 (13)0.0101 (12)0.0037 (13)
O2'0.0561 (14)0.0659 (17)0.0406 (12)0.0165 (12)0.0200 (11)0.0075 (11)
C3'0.0359 (14)0.0385 (16)0.0304 (13)0.0048 (13)0.0085 (11)0.0026 (12)
O3'0.0545 (14)0.0566 (15)0.0344 (11)0.0252 (12)0.0143 (10)0.0056 (10)
C4'0.0327 (14)0.0397 (17)0.0351 (15)0.0068 (12)0.0127 (12)0.0017 (13)
O4'0.0514 (13)0.0590 (15)0.0371 (11)0.0245 (12)0.0214 (10)0.0080 (11)
C5'0.0321 (14)0.0290 (14)0.0303 (13)0.0005 (12)0.0028 (11)0.0014 (11)
O5'0.0443 (12)0.0413 (12)0.0370 (11)0.0074 (11)0.0039 (9)0.0045 (10)
C6'0.0328 (14)0.0306 (14)0.0314 (14)0.0011 (11)0.0064 (11)0.0018 (12)
O6'0.0459 (12)0.0433 (13)0.0314 (10)0.0126 (10)0.0117 (9)0.0024 (9)
C7'0.0362 (15)0.0318 (15)0.0292 (13)0.0067 (12)0.0069 (11)0.0051 (12)
O7'0.0540 (13)0.0613 (15)0.0311 (10)0.0297 (12)0.0135 (10)0.0105 (11)
C8'0.0347 (14)0.0340 (15)0.0277 (13)0.0011 (12)0.0063 (11)0.0030 (11)
O8'0.0556 (14)0.0494 (14)0.0295 (10)0.0162 (11)0.0165 (10)0.0056 (10)
C10.0257 (12)0.0290 (13)0.0333 (13)0.0034 (11)0.0092 (10)0.0017 (11)
O10.0315 (10)0.0567 (14)0.0378 (11)0.0097 (10)0.0153 (9)0.0016 (10)
N10.0313 (12)0.0547 (16)0.0319 (12)0.0095 (13)0.0077 (10)0.0009 (12)
C20.0225 (12)0.0308 (13)0.0280 (13)0.0018 (10)0.0077 (10)0.0005 (10)
N20.0287 (11)0.0352 (12)0.0361 (12)0.0004 (10)0.0096 (9)0.0052 (11)
C30.0275 (13)0.0295 (13)0.0419 (15)0.0017 (11)0.0112 (11)0.0015 (12)
C40.0280 (13)0.0273 (13)0.0383 (15)0.0025 (11)0.0115 (11)0.0012 (12)
C50.0393 (16)0.0269 (14)0.0443 (16)0.0020 (13)0.0048 (13)0.0013 (13)
N60.0579 (16)0.0320 (13)0.0278 (11)0.0091 (12)0.0079 (11)0.0034 (10)
C70.0357 (14)0.0314 (14)0.0314 (14)0.0035 (12)0.0063 (11)0.0008 (12)
N80.0444 (15)0.0524 (17)0.0345 (14)0.0170 (13)0.0016 (11)0.0070 (13)
N90.0631 (18)0.0531 (17)0.0335 (13)0.0162 (16)0.0031 (12)0.0025 (13)
Geometric parameters (Å, º) top
C1'—O1'1.233 (4)C2—N21.486 (3)
C1'—C4'1.483 (4)C2—C31.533 (4)
C1'—C2'1.489 (4)C2—H20.9800
C2'—O2'1.236 (3)N2—H210.8900
C2'—C3'1.440 (4)N2—H220.8900
C3'—O3'1.311 (4)N2—H230.8900
C3'—C4'1.431 (4)C3—C41.521 (4)
O3'—H3'0.8200C3—H310.9700
C4'—O4'1.252 (3)C3—H320.9700
C5'—O5'1.221 (4)C4—C51.526 (4)
C5'—C8'1.480 (4)C4—H410.9700
C5'—C6'1.501 (4)C4—H420.9700
C6'—O6'1.235 (3)C5—N61.457 (4)
C6'—C7'1.441 (4)C5—H510.9700
C7'—O7'1.309 (4)C5—H520.9700
C7'—C8'1.429 (4)N6—C71.330 (4)
O7'—H7'0.8200N6—H60.8600
C8'—O8'1.259 (3)C7—N81.324 (4)
C1—O11.226 (3)C7—N91.332 (4)
C1—N11.327 (4)N8—H810.8600
C1—C21.524 (4)N8—H820.8600
N1—H110.8600N9—H910.8600
N1—H120.8600N9—H920.8600
O1'—C1'—C4'135.4 (3)C3—C2—H2109.1
O1'—C1'—C2'135.2 (3)C2—N2—H21109.5
C4'—C1'—C2'89.3 (2)C2—N2—H22109.5
O2'—C2'—C3'137.2 (3)H21—N2—H22109.5
O2'—C2'—C1'134.4 (3)C2—N2—H23109.5
C3'—C2'—C1'88.4 (2)H21—N2—H23109.5
O3'—C3'—C4'136.2 (3)H22—N2—H23109.5
O3'—C3'—C2'130.4 (3)C4—C3—C2112.4 (2)
C4'—C3'—C2'93.4 (2)C4—C3—H31109.1
C3'—O3'—H3'109.5C2—C3—H31109.1
O4'—C4'—C3'138.0 (3)C4—C3—H32109.1
O4'—C4'—C1'133.1 (3)C2—C3—H32109.1
C3'—C4'—C1'88.9 (2)H31—C3—H32107.9
O5'—C5'—C8'135.4 (3)C3—C4—C5113.0 (2)
O5'—C5'—C6'136.1 (3)C3—C4—H41109.0
C8'—C5'—C6'88.5 (2)C5—C4—H41109.0
O6'—C6'—C7'137.1 (3)C3—C4—H42109.0
O6'—C6'—C5'134.2 (3)C5—C4—H42109.0
C7'—C6'—C5'88.6 (2)H41—C4—H42107.8
O7'—C7'—C8'136.9 (3)N6—C5—C4111.6 (3)
O7'—C7'—C6'130.2 (3)N6—C5—H51109.3
C8'—C7'—C6'92.9 (2)C4—C5—H51109.3
C7'—O7'—H7'109.5N6—C5—H52109.3
O8'—C8'—C7'137.4 (3)C4—C5—H52109.3
O8'—C8'—C5'132.7 (3)H51—C5—H52108.0
C7'—C8'—C5'89.9 (2)C7—N6—C5126.1 (2)
O1—C1—N1124.5 (3)C7—N6—H6117.0
O1—C1—C2120.5 (2)C5—N6—H6117.0
N1—C1—C2115.0 (2)N8—C7—N6122.2 (3)
C1—N1—H11120.0N8—C7—N9119.0 (3)
C1—N1—H12120.0N6—C7—N9118.8 (3)
H11—N1—H12120.0C7—N8—H81120.0
N2—C2—C1106.6 (2)C7—N8—H82120.0
N2—C2—C3111.5 (2)H81—N8—H82120.0
C1—C2—C3111.3 (2)C7—N9—H91120.0
N2—C2—H2109.1C7—N9—H92120.0
C1—C2—H2109.1H91—N9—H92120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O5i0.862.373.095 (3)143
N1—H12···O2ii0.862.152.986 (3)165
N2—H23···O10.892.242.646 (3)107
N2—H22···O1iii0.892.522.831 (3)101
N2—H23···O10.892.062.836 (3)145
N2—H22···O40.892.273.007 (3)140
N2—H21···O60.891.972.841 (3)166
N6—H6···O8iv0.862.273.054 (3)151
N8—H82···O1v0.861.992.842 (3)168
N8—H81···O6vi0.862.032.863 (3)162
N9—H91···O2v0.862.293.066 (4)150
N9—H92···O5vii0.862.512.898 (3)108
N9—H92···O8iv0.862.273.035 (4)149
O3—H3···O8viii0.821.742.523 (3)160
O7—H7···O4ix0.821.792.564 (3)158
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x1, y, z; (iv) x+1, y1/2, z+2; (v) x+2, y1/2, z+1; (vi) x+1, y1/2, z+1; (vii) x+2, y1/2, z+2; (viii) x, y1/2, z+1; (ix) x, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC6H17N5O2+·2C4HO4
Mr401.34
Crystal system, space groupMonoclinic, P21
Temperature (K)294
a, b, c (Å)5.185 (1), 16.668 (3), 10.458 (2)
β (°) 101.90 (3)
V3)884.5 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.54 × 0.24 × 0.22
Data collection
DiffractometerSiemens P4 four-circle
diffractometer
Absorption correctionψ scan
(XPREP in SHELXTL; Sheldrick, 1995)
Tmin, Tmax0.945, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
2919, 2659, 1972
Rint0.030
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.099, 1.01
No. of reflections2659
No. of parameters260
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.19

Computer programs: R3m/V (Siemens, 1989), R3m/V, XDISK (Siemens, 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1995), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O5'i0.862.373.095 (3)142.8
N1—H12···O2'ii0.862.152.986 (3)165.3
N2—H23···O10.892.242.646 (3)107.4
N2—H22···O1iii0.892.522.831 (3)100.9
N2—H23···O1'0.892.062.836 (3)145.0
N2—H22···O4'0.892.273.007 (3)140.3
N2—H21···O6'0.891.972.841 (3)166.1
N6—H6···O8'iv0.862.273.054 (3)151.3
N8—H82···O1'v0.861.992.842 (3)168.4
N8—H81···O6'vi0.862.032.863 (3)162.2
N9—H91···O2'v0.862.293.066 (4)149.7
N9—H92···O5'vii0.862.512.898 (3)108.4
N9—H92···O8'iv0.862.273.035 (4)148.8
O3'—H3'···O8'viii0.821.742.523 (3)160.2
O7'—H7'···O4'ix0.821.792.564 (3)158.1
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x1, y, z; (iv) x+1, y1/2, z+2; (v) x+2, y1/2, z+1; (vi) x+1, y1/2, z+1; (vii) x+2, y1/2, z+2; (viii) x, y1/2, z+1; (ix) x, y+1/2, z+1.
 

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