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Acta Cryst. (2012). E68, o3431    [ doi:10.1107/S1600536812046922 ]

Morpholine-4-carboxamidinium ethyl carbonate

I. Tiritiris

Abstract top

The asymmetric unit of the title salt, C5H12N3O+·C3H5O3-, contains two carboxamidinium and two ethyl carbonate ions. In the crystal, the C-N bond lengths in the central CN3 units of the cations range between 1.324 (2) and 1.352 (2) Å, indicating partial double-bond character. The central C atoms are bonded to the three N atoms in a nearly ideal trigonal-planar geometry and the positive charges are delocalized in the CN3 planes. The morpholine rings are in chair conformations. The C-O bond lengths in both ethyl carbonate ions are characteristic for delocalized double bonds [1.243 (2)-1.251 (2) Å] and typical single bonds [1.368 (2) and 1.375 (2) Å]. In the crystal, N-H...O hydrogen bonds between cations and anions generate a two-dimensional network in the ac plane.

Comment top

The reaction of several guanidines with CO2 in undried aprotic solvents are well described in the literature (Tiritiris et al., 2011). Here, the corresponding guanidinium hydrogen carbonate salts were obtained and their crystal structures could be determined. By reacting carboxamidines with CO2 we first used aprotic solvents and due to their water content, sparingly soluble and non crystalline hydrogen carbonate salts were also formed. By using alcohols as solvents for the reaction, we obtained a few crystalline alkyl carbonate salts. One of them is the here presented title compound. According to the structure analysis, the asymmetric unit contains two carboxamidinium and two ethyl carbonate ions. The C–N bonds of the CN3 units are ranging from 1.324 (2) to 1.352 (2) Å, showing partial double-bond character. The N–C1–N and N–C6–N angles are indicating a nearly ideal trigonal-planar surrounding of the carbon centres by the nitrogen atoms. The positive charges are completely delocalized on the CN3 planes (Fig. 1). The structural parameters of the morpholine rings in the here presented title compound agree very well with the data obtained from the X-ray analysis of the starting compound 4-morpholinecarboxamidine (Tiritiris, 2012a). The morpholine rings adopt a chair conformation. The C–O bond lengths in both ethyl carbonate ions indicate evenly distributed double bonds [1.243 (2)–1.251 (2) Å] and typical single bonds [1.368 (2) and 1.375 (2) Å]. The data fit with the C–O bond lengths and angles of the anion in piperidine-1-carboxamidinium ethyl carbonate (Tiritiris, 2012b). In the crystal structure, strong N—H···O hydrogen bonds between hydrogen atoms of carboxamidinium ions and oxygen atoms of neighboring ethyl carbonate ions are observed, generating an infinite two-dimensional network [d(H···O) = 1.91 (2)–2.12 (2) Å] (Tab. 1) with base vectors [0 0 1] and [1 0 0] (Fig. 2). In contrast to the crystal structure of 4-morpholinecarboxamidine (Tiritiris, 2012a), the oxygen atoms of the morpholine rings are not involved in the N—H···O hydrogen bonding system.

Related literature top

For the synthesis and crystal structures of guanidinium hydrogen carbonates, see: Tiritiris et al. (2011). For the crystal structure of 4-morpholinecarboxamidine, see: Tiritiris (2012a). For the crystal structure of piperidine-1-carboxamidinium ethyl carbonate, see: Tiritiris (2012b).

Experimental top

The title compound was prepared by bubbling excess CO2 gas into an ethanolic solution of 2.0 g (15.5 mmol) 4-morpholinecarboxamidine (Tiritiris, 2012a). The resulting colorless precipitate was recrystallized from a small amount of ethanol and single crystals suitable for X-ray analysis were obtained. Yield: 3.05 g (90%). 1H NMR (500 MHz, D2O/DSS): δ = 1.17–1.20 [t, 3 H, –CH3], 3.49–3.52 [m, 4 H, –CH2], 3.64–3.68 [q, 2 H, –CH2], 3.80–3.83 [m, 4 H, –CH2]. Because of the H/D exchange, the hydrogen atoms of the –NH2 groups were not observed. 13C NMR (125 MHz, D2O/DSS): δ = 16.8 (–CH3), 45.2 (–CH2), 57.4 (–CH2), 65.4 (–CH2), 156.6 (N3C+), 160.3 (C═O).

Refinement top

The N-bound H atoms were located in a difference Fourier map and were refined freely [N—H = 0.84 (2)–0.93 (2) Å]. The hydrogen atoms of the methyl groups were allowed to rotate with a fixed angle around the C–C bond to best fit the experimental electron density, with U(H) set to 1.5 Ueq(C) and d(C—H) = 0.98 Å. The H atoms of the methylene groups were placed in calculated positions with d(C—H) = 0.99 Å. They were included in the refinement in the riding model approximation, with U(H) set to 1.2 Ueq(C).

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound with displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. N–H···O hydrogen bonds generating a two-dimensional network in the (ac) plane. The hydrogen bonds are indicated by dashed lines.
Morpholine-4-carboxamidinium ethyl carbonate top
Crystal data top
C5H12N3O+·C3H5O3−F(000) = 944
Mr = 219.25Dx = 1.384 Mg m−3
Monoclinic, P21/nMelting point: 413 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.2163 (5) ÅCell parameters from 5142 reflections
b = 20.8874 (9) Åθ = 0.4–28.3°
c = 10.4616 (5) ŵ = 0.11 mm−1
β = 109.505 (2)°T = 100 K
V = 2104.31 (17) Å3Block, colourless
Z = 80.30 × 0.25 × 0.15 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer		2981 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.055
Graphite monochromatorθmax = 28.3°, θmin = 2.3°
φ scans, and ω scansh = −13→13
9902 measured reflectionsk = −27→27
5199 independent reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: difference Fourier map
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0468P)2]
where P = (Fo2 + 2Fc2)/3
5199 reflections(Δ/σ)max < 0.001
305 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C5H12N3O+·C3H5O3−V = 2104.31 (17) Å3
Mr = 219.25Z = 8
Monoclinic, P21/nMo Kα radiation
a = 10.2163 (5) ŵ = 0.11 mm−1
b = 20.8874 (9) ÅT = 100 K
c = 10.4616 (5) Å0.30 × 0.25 × 0.15 mm
β = 109.505 (2)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer		2981 reflections with I > 2σ(I)
9902 measured reflectionsRint = 0.055
5199 independent reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112Δρmax = 0.25 e Å−3
S = 1.00Δρmin = −0.30 e Å−3
5199 reflectionsAbsolute structure: ?
305 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C10.14782 (18)0.19683 (9)0.08078 (17)0.0138 (4)
N10.14407 (18)0.21777 (9)−0.03987 (16)0.0186 (4)
H110.082 (2)0.2060 (11)−0.111 (2)0.027 (6)*
H120.209 (2)0.2468 (11)−0.039 (2)0.028 (6)*
N20.24717 (16)0.21987 (9)0.18879 (16)0.0168 (4)
H210.2567 (18)0.2083 (9)0.269 (2)0.013 (5)*
H220.308 (2)0.2486 (11)0.171 (2)0.032 (6)*
N30.05782 (14)0.15198 (8)0.09382 (13)0.0138 (3)
C20.04415 (18)0.14053 (10)0.22786 (16)0.0174 (4)
H2A−0.01060.17550.24910.021*
H2B0.13740.14040.29820.021*
C3−0.02671 (19)0.07728 (10)0.22976 (17)0.0239 (5)
H3A0.03430.04210.22030.029*
H3B−0.04100.07210.31820.029*
O1−0.15763 (13)0.07261 (7)0.12343 (12)0.0227 (3)
C4−0.13597 (19)0.07748 (10)−0.00376 (17)0.0194 (4)
H4A−0.22610.0727−0.07770.023*
H4B−0.07460.0422−0.01200.023*
C5−0.07145 (18)0.14066 (9)−0.01951 (17)0.0168 (4)
H5A−0.05150.1408−0.10580.020*
H5B−0.13790.1757−0.02330.020*
C60.61678 (17)0.19115 (9)0.08546 (16)0.0122 (4)
N40.60204 (17)0.21566 (9)−0.03589 (15)0.0161 (4)
H410.656 (2)0.2472 (11)−0.038 (2)0.026 (6)*
H420.533 (2)0.2013 (12)−0.113 (2)0.041 (7)*
N50.71439 (16)0.21538 (8)0.19268 (15)0.0144 (4)
H510.773 (2)0.2459 (11)0.185 (2)0.023 (6)*
H520.745 (2)0.1933 (11)0.271 (2)0.035 (6)*
N60.53305 (14)0.14360 (7)0.10007 (13)0.0134 (3)
C70.56842 (19)0.11205 (10)0.23299 (16)0.0176 (4)
H7A0.59060.14490.30530.021*
H7B0.65170.08500.24800.021*
C80.4493 (2)0.07110 (10)0.24096 (17)0.0189 (4)
H8A0.47910.04720.32770.023*
H8B0.37090.09910.24010.023*
O20.40359 (13)0.02701 (6)0.13163 (11)0.0198 (3)
C90.35206 (18)0.06230 (10)0.00799 (17)0.0182 (4)
H9A0.27580.09070.01170.022*
H9B0.31370.0321−0.06840.022*
C100.46389 (18)0.10203 (9)−0.01694 (17)0.0169 (4)
H10A0.53350.0734−0.03410.020*
H10B0.42260.1288−0.09860.020*
C11−0.07231 (18)0.16716 (9)0.57058 (16)0.0133 (4)
O3−0.16622 (12)0.18499 (7)0.46539 (11)0.0196 (3)
O4−0.04966 (12)0.18664 (6)0.68830 (11)0.0179 (3)
O50.01060 (12)0.11991 (7)0.54704 (11)0.0181 (3)
C120.12224 (18)0.09664 (10)0.66226 (17)0.0188 (4)
H12A0.08490.07610.72810.023*
H12B0.18360.13240.70810.023*
C130.20159 (19)0.04887 (10)0.60972 (18)0.0224 (5)
H13A0.23550.06950.54270.034*
H13B0.14050.01310.56710.034*
H13C0.28060.03280.68510.034*
C140.40406 (17)0.17608 (9)0.57044 (16)0.0130 (4)
O60.31041 (12)0.19554 (6)0.46676 (11)0.0180 (3)
O70.42103 (13)0.19133 (6)0.69029 (11)0.0183 (3)
O80.49287 (12)0.13310 (6)0.54411 (11)0.0166 (3)
C150.60379 (18)0.10913 (10)0.65905 (17)0.0179 (4)
H15A0.56550.08770.72320.021*
H15B0.66410.14480.70700.021*
C160.68612 (19)0.06219 (10)0.60715 (18)0.0199 (4)
H16A0.62700.02570.56510.030*
H16B0.76590.04700.68280.030*
H16C0.71900.08330.53980.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0137 (9)0.0140 (11)0.0127 (9)0.0045 (8)0.0031 (7)0.0005 (7)
N10.0180 (9)0.0236 (10)0.0114 (8)−0.0068 (8)0.0011 (7)0.0008 (7)
N20.0189 (9)0.0223 (10)0.0080 (8)−0.0050 (7)0.0031 (7)0.0016 (7)
N30.0118 (7)0.0192 (9)0.0088 (7)−0.0017 (7)0.0012 (6)−0.0003 (6)
C20.0178 (9)0.0251 (12)0.0085 (8)−0.0042 (8)0.0033 (7)−0.0007 (8)
C30.0261 (11)0.0301 (13)0.0102 (9)−0.0091 (9)−0.0011 (8)0.0013 (8)
O10.0251 (7)0.0279 (9)0.0138 (6)−0.0121 (6)0.0048 (5)−0.0029 (6)
C40.0217 (10)0.0216 (12)0.0130 (9)−0.0007 (9)0.0032 (8)−0.0024 (8)
C50.0148 (9)0.0201 (11)0.0115 (8)−0.0027 (8)−0.0007 (7)0.0001 (8)
C60.0143 (9)0.0123 (10)0.0107 (9)0.0040 (8)0.0051 (7)−0.0004 (7)
N40.0166 (8)0.0182 (10)0.0107 (8)−0.0043 (8)0.0009 (7)0.0016 (7)
N50.0164 (8)0.0145 (10)0.0103 (8)−0.0029 (7)0.0018 (6)0.0000 (6)
N60.0158 (8)0.0148 (9)0.0083 (7)−0.0017 (7)0.0023 (6)−0.0007 (6)
C70.0218 (10)0.0185 (11)0.0105 (9)−0.0053 (8)0.0027 (7)0.0016 (7)
C80.0268 (10)0.0179 (12)0.0125 (9)−0.0045 (9)0.0074 (8)−0.0022 (8)
O20.0281 (7)0.0145 (8)0.0147 (6)−0.0057 (6)0.0043 (5)−0.0011 (5)
C90.0187 (10)0.0187 (12)0.0137 (9)−0.0021 (8)0.0006 (7)0.0008 (8)
C100.0200 (10)0.0167 (11)0.0117 (8)−0.0022 (8)0.0025 (7)−0.0013 (7)
C110.0130 (9)0.0173 (11)0.0095 (9)−0.0009 (8)0.0037 (7)0.0013 (7)
O30.0191 (7)0.0258 (9)0.0101 (6)0.0043 (6)−0.0001 (5)0.0003 (5)
O40.0183 (7)0.0231 (8)0.0102 (6)0.0030 (6)0.0020 (5)−0.0016 (5)
O50.0175 (7)0.0238 (8)0.0108 (6)0.0056 (6)0.0016 (5)−0.0002 (5)
C120.0167 (10)0.0226 (12)0.0138 (9)0.0045 (8)0.0007 (7)0.0022 (8)
C130.0234 (10)0.0219 (12)0.0211 (10)0.0027 (9)0.0064 (8)0.0014 (8)
C140.0131 (9)0.0131 (11)0.0116 (9)−0.0027 (8)0.0027 (7)0.0001 (7)
O60.0179 (7)0.0231 (8)0.0101 (6)0.0050 (6)0.0010 (5)0.0010 (5)
O70.0208 (7)0.0215 (8)0.0096 (6)0.0050 (6)0.0010 (5)−0.0021 (5)
O80.0163 (7)0.0211 (8)0.0103 (6)0.0056 (6)0.0014 (5)0.0005 (5)
C150.0177 (9)0.0214 (12)0.0113 (9)0.0057 (8)0.0005 (7)0.0012 (8)
C160.0171 (10)0.0218 (12)0.0198 (10)0.0037 (8)0.0047 (8)0.0023 (8)
Geometric parameters (Å, º) top
C1—N11.324 (2)C7—H7A0.9900
C1—N21.331 (2)C7—H7B0.9900
C1—N31.351 (2)C8—O21.420 (2)
N1—H110.84 (2)C8—H8A0.9900
N1—H120.89 (2)C8—H8B0.9900
N2—H210.85 (2)O2—C91.428 (2)
N2—H220.92 (2)C9—C101.504 (3)
N3—C51.470 (2)C9—H9A0.9900
N3—C21.474 (2)C9—H9B0.9900
C2—C31.510 (3)C10—H10A0.9900
C2—H2A0.9900C10—H10B0.9900
C2—H2B0.9900C11—O41.243 (2)
C3—O11.429 (2)C11—O31.251 (2)
C3—H3A0.9900C11—O51.375 (2)
C3—H3B0.9900O5—C121.439 (2)
O1—C41.424 (2)C12—C131.501 (3)
C4—C51.508 (3)C12—H12A0.9900
C4—H4A0.9900C12—H12B0.9900
C4—H4B0.9900C13—H13A0.9800
C5—H5A0.9900C13—H13B0.9800
C5—H5B0.9900C13—H13C0.9800
C6—N51.327 (2)C14—O71.248 (2)
C6—N41.330 (2)C14—O61.2507 (19)
C6—N61.352 (2)C14—O81.368 (2)
N4—H410.86 (2)O8—C151.4390 (19)
N4—H420.93 (2)C15—C161.506 (3)
N5—H510.90 (2)C15—H15A0.9900
N5—H520.90 (2)C15—H15B0.9900
N6—C71.471 (2)C16—H16A0.9800
N6—C101.474 (2)C16—H16B0.9800
C7—C81.512 (3)C16—H16C0.9800
N1—C1—N2117.44 (18)C8—C7—H7B109.5
N1—C1—N3121.41 (16)H7A—C7—H7B108.0
N2—C1—N3121.10 (16)O2—C8—C7112.11 (14)
C1—N1—H11121.6 (14)O2—C8—H8A109.2
C1—N1—H12115.2 (13)C7—C8—H8A109.2
H11—N1—H12123.1 (19)O2—C8—H8B109.2
C1—N2—H21122.7 (13)C7—C8—H8B109.2
C1—N2—H22116.0 (13)H8A—C8—H8B107.9
H21—N2—H22121.3 (17)C8—O2—C9108.51 (14)
C1—N3—C5119.25 (14)O2—C9—C10111.74 (14)
C1—N3—C2119.50 (14)O2—C9—H9A109.3
C5—N3—C2113.33 (13)C10—C9—H9A109.3
N3—C2—C3110.65 (14)O2—C9—H9B109.3
N3—C2—H2A109.5C10—C9—H9B109.3
C3—C2—H2A109.5H9A—C9—H9B107.9
N3—C2—H2B109.5N6—C10—C9111.24 (14)
C3—C2—H2B109.5N6—C10—H10A109.4
H2A—C2—H2B108.1C9—C10—H10A109.4
O1—C3—C2112.19 (15)N6—C10—H10B109.4
O1—C3—H3A109.2C9—C10—H10B109.4
C2—C3—H3A109.2H10A—C10—H10B108.0
O1—C3—H3B109.2O4—C11—O3127.48 (17)
C2—C3—H3B109.2O4—C11—O5119.35 (15)
H3A—C3—H3B107.9O3—C11—O5113.17 (14)
C4—O1—C3109.00 (13)C11—O5—C12117.10 (13)
O1—C4—C5112.00 (15)O5—C12—C13106.96 (14)
O1—C4—H4A109.2O5—C12—H12A110.3
C5—C4—H4A109.2C13—C12—H12A110.3
O1—C4—H4B109.2O5—C12—H12B110.3
C5—C4—H4B109.2C13—C12—H12B110.3
H4A—C4—H4B107.9H12A—C12—H12B108.6
N3—C5—C4111.13 (14)C12—C13—H13A109.5
N3—C5—H5A109.4C12—C13—H13B109.5
C4—C5—H5A109.4H13A—C13—H13B109.5
N3—C5—H5B109.4C12—C13—H13C109.5
C4—C5—H5B109.4H13A—C13—H13C109.5
H5A—C5—H5B108.0H13B—C13—H13C109.5
N5—C6—N4118.27 (17)O7—C14—O6126.70 (17)
N5—C6—N6120.64 (15)O7—C14—O8119.38 (14)
N4—C6—N6121.08 (16)O6—C14—O8113.91 (14)
C6—N4—H41116.3 (13)C14—O8—C15116.75 (12)
C6—N4—H42121.0 (14)O8—C15—C16107.70 (14)
H41—N4—H42122.5 (19)O8—C15—H15A110.2
C6—N5—H51121.8 (13)C16—C15—H15A110.2
C6—N5—H52120.7 (14)O8—C15—H15B110.2
H51—N5—H52114.0 (18)C16—C15—H15B110.2
C6—N6—C7118.09 (13)H15A—C15—H15B108.5
C6—N6—C10118.98 (14)C15—C16—H16A109.5
C7—N6—C10114.80 (15)C15—C16—H16B109.5
N6—C7—C8110.93 (14)H16A—C16—H16B109.5
N6—C7—H7A109.5C15—C16—H16C109.5
C8—C7—H7A109.5H16A—C16—H16C109.5
N6—C7—H7B109.5H16B—C16—H16C109.5
N1—C1—N3—C5−19.3 (3)N4—C6—N6—C1023.7 (2)
N2—C1—N3—C5163.26 (16)C6—N6—C7—C8167.46 (16)
N1—C1—N3—C2−166.30 (17)C10—N6—C7—C8−44.1 (2)
N2—C1—N3—C216.3 (3)N6—C7—C8—O253.4 (2)
C1—N3—C2—C3−163.24 (16)C7—C8—O2—C9−62.83 (19)
C5—N3—C2—C347.9 (2)C8—O2—C9—C1062.98 (19)
N3—C2—C3—O1−54.7 (2)C6—N6—C10—C9−167.27 (15)
C2—C3—O1—C461.1 (2)C7—N6—C10—C944.6 (2)
C3—O1—C4—C5−60.9 (2)O2—C9—C10—N6−53.8 (2)
C1—N3—C5—C4163.03 (16)O4—C11—O5—C12−1.3 (2)
C2—N3—C5—C4−48.1 (2)O3—C11—O5—C12179.62 (15)
O1—C4—C5—N354.7 (2)C11—O5—C12—C13−176.69 (15)
N5—C6—N6—C7−10.5 (2)O7—C14—O8—C15−1.3 (2)
N4—C6—N6—C7170.74 (16)O6—C14—O8—C15179.56 (15)
N5—C6—N6—C10−157.57 (16)C14—O8—C15—C16179.01 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O4i0.84 (2)2.12 (2)2.944 (1)168 (1)
N1—H12···O3ii0.89 (2)1.91 (2)2.795 (1)174 (1)
N2—H21···O60.85 (2)1.97 (2)2.807 (1)168 (1)
N2—H22···O4ii0.92 (2)1.95 (2)2.851 (1)164 (1)
N4—H41···O6ii0.86 (2)1.97 (2)2.817 (1)167 (1)
N4—H42···O7i0.93 (2)2.00 (2)2.889 (1)159 (1)
N5—H51···O7ii0.90 (2)1.99 (2)2.879 (1)172 (1)
N5—H52···O3iii0.90 (2)1.94 (2)2.776 (1)154 (1)
Symmetry codes: (i) x, y, z−1; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O4i0.84 (2)2.12 (2)2.944 (1)168 (1)
N1—H12···O3ii0.89 (2)1.91 (2)2.795 (1)174 (1)
N2—H21···O60.85 (2)1.97 (2)2.807 (1)168 (1)
N2—H22···O4ii0.92 (2)1.95 (2)2.851 (1)164 (1)
N4—H41···O6ii0.86 (2)1.97 (2)2.817 (1)167 (1)
N4—H42···O7i0.93 (2)2.00 (2)2.889 (1)159 (1)
N5—H51···O7ii0.90 (2)1.99 (2)2.879 (1)172 (1)
N5—H52···O3iii0.90 (2)1.94 (2)2.776 (1)154 (1)
Symmetry codes: (i) x, y, z−1; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1, y, z.
Acknowledgements top

The author thanks Dr F. Lissner (Institut für Anorganische Chemie, Universität Stuttgart) for the data collection.

references
References top

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