1,3-Diammonio-1,2,3-tride­oxy-cis-inositol sulfate

Neis, C.; Merten, G.J.; Hegetschweiler, K.

doi:10.1107/S1600536812016029

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1425-o1426

doi:10.1107/S1600536812016029

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1,3-Diammonio-1,2,3-trideoxy-cis-inositol sulfate

Christian Neis,^a Günter J. Merten ^a and Kaspar Hegetschweiler ^a ^*

^aFachrichtung Chemie, Universität des Saarlandes, Postfach 151150, D-66041 Saarbrücken, Germany
^*Correspondence e-mail: hegetschweiler@mx.uni-saarland.de

(Received 13 March 2012; accepted 12 April 2012; online 18 April 2012)

In the crystal structure of the title compound, C₆H₁₆N₂O₃²⁺·SO₄²⁻, each cation forms three O—H⋯O and five N—H⋯O hydrogen bonds to six neighbouring sulfate anions. In addition, interlinking of the cations by N—H⋯O interactions is also observed. The cyclohexane ring adopts a chair conformation with two axial hydroxy groups. Although the separation of 2.928 Å is almost ideal for a hydrogen bond, intramolecular hydrogen bonding between these two hydroxy groups is not observed.

Related literature

The synthesis of the chloride salt, as well as formation of a Cu^II complex of 1,3-diamino-1,2,3-trideoxy-cis-inositol, was reported by Merten et al. (2012 ). A crystal structure determination of the chloride salt was performed by Neis et al. (2012 ). The importance of intramolecular hydrogen bonding in syn-1,3,5-trisubstituted cyclohexane derivatives has been discussed by Gencheva et al. (2000 ), Kramer et al. (1998 ), Kuppert et al. (2006 ), and Neis et al. (2010 ). Puckering parameters were calculated according to Cremer & Pople (1975 ). For the treatment of hydrogen atoms in SHELXL, see: Müller et al. (2006 ).

Experimental

Crystal data

C₆H₁₆N₂O₃²⁺·SO₄²⁻
M_r = 260.27
Monoclinic, P 2₁ /n
a = 9.2151 (18) Å
b = 6.6673 (13) Å
c = 17.267 (4) Å
β = 101.46 (3)°
V = 1039.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 200 K
0.30 × 0.20 × 0.15 mm

Data collection

Stoe IPDS image plate diffractometer
6961 measured reflections
1779 independent reflections
1685 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.066
S = 1.06
1779 reflections
172 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.87 (1)	2.09 (2)	2.9292 (17)	163 (2)
N1—H1B⋯O3ⁱⁱ	0.87 (2)	2.11 (2)	2.8125 (18)	138 (2)
N1—H1C⋯O7ⁱⁱⁱ	0.85 (2)	2.04 (2)	2.882 (2)	170 (2)
N5—H5A⋯O5	0.89 (2)	1.97 (2)	2.8538 (17)	173 (2)
N5—H5B⋯O8^iv	0.86 (1)	2.02 (2)	2.8530 (18)	162 (2)
N5—H5C⋯O7ⁱⁱ	0.87 (2)	2.29 (2)	3.0852 (18)	153 (2)
N5—H5C⋯O6ⁱⁱ	0.87 (2)	2.34 (2)	3.0856 (19)	144 (2)
O4—H4O⋯O6	0.85 (2)	1.86 (2)	2.7017 (16)	177 (2)
O2—H2O⋯O8^v	0.86 (2)	1.97 (2)	2.8161 (15)	170 (2)
O3—H3O⋯O7^vi	0.86 (2)	1.87 (2)	2.7149 (16)	167 (2)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) x-1, y-1, z; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x-1, y, z; (vi) -x+1, -y+1, -z.

Data collection: IPDS Software (Stoe & Cie, 1997 ); cell refinement: IPDS Software; data reduction: IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016029/bx2402sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016029/bx2402Isup2.hkl

checkCIF report

Comment top

Due to the versatile metal- and hydrogen-binding properties, 1,3-diamino-1,2,3-trideoxy-cis-inositol has been found to be a promising building block for the construction of polynuclear metal complexes and extended hydrogen bonded networks (Merten et al., 2012). The crystal structure of a corresponding hydrochloride C₆H₁₄N₂O₃^.2HCl has recently been reported (Neis et al., 2012). Similar to this chloride salt, the title compound contains 1,3-diammonio-1,2,3-trideoxy-cis-inositol dications with the cyclohexane ring adopting an almost ideal chair conformation (puckering parameters: Q = 0.59 Å, θ = 178.3 °, ϕ = 89.0 °). In both salts, the cation has the same form with the two ammonium groups and one of the hydroxy groups in equatorial and the remaining two hydroxy groups in axial position. In the title compound, each cation is hydrogen-bonded to six sulfate counter ions by O—H···O and N—H···O interactions, one of the latter is bifurcated. These cation···anion interactions constitute an extended three-dimensional network. Direct cation···cation hydrogen bonding is also observed: One of the ammonium groups of each cation donates a hydrogen atom to the equatorial hydroxy group of a neighbouring cation and another hydrogen atom to the axial hydroxy group of an additional neighbour. Each cation is thus connected to a total of four neighbouring cations and these interactions generate double chains, which are oriented parallel to the crystallographic b axis. As already observed for the chloride salt, all O—H and N—H groups act as hydrogen donors, however, one of the axial hydroxy groups does not accept any hydrogen atom. We explain these observations by the well established stronger steric encumbrance of axial substituents. It is again worthy to note that the non-accepting axial hydroxy group does not form an intramolecular O—H···O hydrogen bond, even though the O···O separation of 2.928 Å between the two axial oxygen atoms corresponds almost ideally to the value required for such an interaction. For corresponding structures with three axial hydroxy or amino groups in a syn-1,3,5-triaxial arrangement, it appears, however, that the formation of such intramolecular hydrogen bonds is often a prerequisite for a stable cyclohexane chair (Gencheva et al., 2000; Kramer et al., 1998; Kuppert et al., 2006). The non-observance of such a hydrogen bond in the title compound further supports the conclusion that this type of interactions would be of minor importance in molecules having only two hydroxy groups in a 1,3-syn-axial arrangement.

Related literature top

The synthesis of the chloride salt, as well as formation of a Cu^II complex of 1,3-diamino-1,2,3-trideoxy-cis-inositol, was reported by Merten et al. (2012). A crystal structure determination of the chloride salt was performed by Neis et al. (2012). The importance of intramolecular hydrogen bonding in syn-1,3,5-trisubstituted cyclohexane derivatives has been discussed by Gencheva et al. (2000), Kramer et al. (1998), Kuppert et al. (2006), and Neis et al. (2010). Puckering parameters were calculated according to Cremer & Pople (1975). For the treatment of hydrogen atoms in SHELXL, see: Müller et al. (2006).

Experimental top

The title compound has been obtained following the protocol given by Merten et al. (2012). ¹H-NMR and ¹³C-NMR properties are identical with the chloride salt (Neis et al., 2012). Single crystals were grown from an aqueous solution (pH 2) by slow evaporation at 298 K.

Computing details top

Data collection: IPDS Software (Stoe & Cie, 1997); cell refinement: IPDS Software (Stoe & Cie, 1997); data reduction: IPDS Software (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound with numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The double chain structure which is formed by hydrogen bonding between dication entities (ball and stick model).

1,3-Diammonio-1,2,3-trideoxy-cis-inositol sulfate top

Crystal data top

C₆H₁₆N₂O₃²⁺·SO₄²⁻	F(000) = 552
M_r = 260.27	D_x = 1.663 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3837 reflections
a = 9.2151 (18) Å	θ = 2.6–25.0°
b = 6.6673 (13) Å	µ = 0.34 mm⁻¹
c = 17.267 (4) Å	T = 200 K
β = 101.46 (3)°	Prism, colourless
V = 1039.7 (4) Å³	0.30 × 0.20 × 0.15 mm
Z = 4

Data collection top

Stoe IPDS image plate diffractometer	1685 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
phi scans	h = −10→10
6961 measured reflections	k = −7→7
1779 independent reflections	l = −20→20

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0259P)² + 0.7072P] where P = (F_o² + 2F_c²)/3
1779 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.27 e Å⁻³
9 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₆H₁₆N₂O₃²⁺·SO₄²⁻	V = 1039.7 (4) Å³
M_r = 260.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2151 (18) Å	µ = 0.34 mm⁻¹
b = 6.6673 (13) Å	T = 200 K
c = 17.267 (4) Å	0.30 × 0.20 × 0.15 mm
β = 101.46 (3)°

Data collection top

Stoe IPDS image plate diffractometer	1685 reflections with I > 2σ(I)
6961 measured reflections	R_int = 0.035
1779 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	9 restraints
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
1779 reflections	Δρ_min = −0.29 e Å⁻³
172 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
C5	0.44604 (15)	−0.0876 (2)	0.10574 (8)	0.0129 (3)
H5	0.4373	−0.1399	0.0507	0.015*
C6	0.35712 (15)	−0.2238 (2)	0.15088 (8)	0.0149 (3)
H6A	0.3961	−0.3624	0.1521	0.018*
H6B	0.3684	−0.1762	0.2061	0.018*
C2	0.12716 (15)	−0.0111 (2)	0.10691 (8)	0.0139 (3)
H2	0.0241	−0.0171	0.0749	0.017*
C1	0.19415 (15)	−0.2228 (2)	0.11143 (8)	0.0136 (3)
H1	0.1839	−0.2768	0.0566	0.016*
C3	0.22081 (16)	0.1251 (2)	0.06417 (8)	0.0137 (3)
H3	0.2117	0.0722	0.0092	0.016*
C4	0.38668 (15)	0.1297 (2)	0.10194 (8)	0.0126 (3)
H4	0.4396	0.2105	0.0674	0.015*
N1	0.11358 (15)	−0.3591 (2)	0.15750 (8)	0.0171 (3)
H1A	0.124 (2)	−0.325 (3)	0.2070 (9)	0.026*
H1B	0.142 (2)	−0.481 (2)	0.1514 (10)	0.026*
H1C	0.0204 (17)	−0.360 (3)	0.1393 (10)	0.026*
N5	0.60555 (14)	−0.09248 (19)	0.14663 (8)	0.0151 (3)
H5A	0.6514 (19)	0.006 (3)	0.1269 (10)	0.023*
H5B	0.612 (2)	−0.084 (3)	0.1971 (9)	0.023*
H5C	0.642 (2)	−0.208 (2)	0.1385 (10)	0.023*
O4	0.41236 (12)	0.21890 (16)	0.17886 (6)	0.0177 (2)
H4O	0.4859 (19)	0.294 (3)	0.1786 (11)	0.027*
O2	0.12055 (12)	0.05338 (16)	0.18490 (6)	0.0188 (2)
H2O	0.0491 (19)	0.137 (3)	0.1815 (11)	0.028*
O3	0.15853 (12)	0.32218 (16)	0.05817 (6)	0.0206 (2)
H3O	0.171 (2)	0.369 (3)	0.0137 (9)	0.031*
S1	0.77047 (4)	0.40360 (5)	0.132375 (19)	0.01264 (13)
O7	0.80382 (13)	0.58885 (16)	0.09000 (6)	0.0268 (3)
O8	0.90424 (11)	0.34825 (16)	0.19086 (6)	0.0201 (2)
O5	0.72807 (12)	0.23732 (16)	0.07600 (6)	0.0221 (3)
O6	0.65015 (12)	0.45266 (18)	0.17466 (7)	0.0294 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C5	0.0114 (7)	0.0124 (7)	0.0148 (7)	−0.0003 (5)	0.0022 (5)	−0.0010 (5)
C6	0.0148 (7)	0.0096 (7)	0.0200 (7)	−0.0004 (5)	0.0027 (5)	0.0025 (5)
C2	0.0112 (7)	0.0156 (7)	0.0142 (6)	0.0004 (5)	0.0008 (5)	−0.0008 (5)
C1	0.0151 (7)	0.0118 (7)	0.0146 (6)	−0.0038 (5)	0.0043 (5)	−0.0007 (5)
C3	0.0165 (7)	0.0106 (7)	0.0137 (6)	0.0026 (5)	0.0024 (5)	0.0004 (5)
C4	0.0150 (7)	0.0104 (7)	0.0131 (6)	−0.0017 (5)	0.0044 (5)	−0.0001 (5)
N1	0.0178 (7)	0.0142 (6)	0.0205 (7)	−0.0052 (5)	0.0067 (5)	−0.0017 (5)
N5	0.0129 (6)	0.0132 (6)	0.0191 (6)	0.0008 (5)	0.0032 (5)	−0.0012 (5)
O4	0.0199 (5)	0.0158 (5)	0.0179 (5)	−0.0065 (4)	0.0045 (4)	−0.0047 (4)
O2	0.0209 (6)	0.0195 (5)	0.0172 (5)	0.0050 (4)	0.0069 (4)	−0.0003 (4)
O3	0.0269 (6)	0.0136 (5)	0.0223 (5)	0.0083 (4)	0.0073 (4)	0.0046 (4)
S1	0.0110 (2)	0.01085 (19)	0.0156 (2)	−0.00160 (12)	0.00125 (13)	0.00023 (12)
O7	0.0345 (7)	0.0183 (6)	0.0244 (6)	−0.0064 (5)	−0.0017 (5)	0.0082 (4)
O8	0.0183 (5)	0.0207 (5)	0.0193 (5)	0.0035 (4)	−0.0009 (4)	0.0023 (4)
O5	0.0255 (6)	0.0209 (6)	0.0205 (5)	−0.0077 (4)	0.0055 (4)	−0.0057 (4)
O6	0.0168 (6)	0.0289 (6)	0.0455 (7)	−0.0041 (5)	0.0134 (5)	−0.0149 (5)

Geometric parameters (Å, º) top

C5—N5	1.4993 (18)	C4—O4	1.4312 (17)
C5—C6	1.5355 (19)	C4—H4	1.0000
C5—C4	1.5454 (19)	N1—H1A	0.870 (14)
C5—H5	1.0000	N1—H1B	0.867 (15)
C6—C1	1.521 (2)	N1—H1C	0.853 (15)
C6—H6A	0.9900	N5—H5A	0.885 (15)
C6—H6B	0.9900	N5—H5B	0.864 (14)
C2—O2	1.4265 (17)	N5—H5C	0.866 (15)
C2—C1	1.536 (2)	O4—H4O	0.845 (15)
C2—C3	1.5386 (19)	O2—H2O	0.855 (15)
C2—H2	1.0000	O3—H3O	0.856 (15)
C1—N1	1.4985 (18)	S1—O5	1.4758 (11)
C1—H1	1.0000	S1—O8	1.4768 (11)
C3—O3	1.4297 (17)	S1—O6	1.4802 (12)
C3—C4	1.538 (2)	S1—O7	1.4982 (11)
C3—H3	1.0000

N5—C5—C6	108.67 (11)	C2—C3—H3	107.4
N5—C5—C4	110.25 (11)	O4—C4—C3	111.66 (11)
C6—C5—C4	110.85 (11)	O4—C4—C5	110.99 (11)
N5—C5—H5	109.0	C3—C4—C5	108.20 (11)
C6—C5—H5	109.0	O4—C4—H4	108.6
C4—C5—H5	109.0	C3—C4—H4	108.6
C1—C6—C5	110.43 (11)	C5—C4—H4	108.6
C1—C6—H6A	109.6	C1—N1—H1A	113.0 (13)
C5—C6—H6A	109.6	C1—N1—H1B	108.2 (12)
C1—C6—H6B	109.6	H1A—N1—H1B	112.8 (17)
C5—C6—H6B	109.6	C1—N1—H1C	112.2 (13)
H6A—C6—H6B	108.1	H1A—N1—H1C	105.8 (18)
O2—C2—C1	108.74 (11)	H1B—N1—H1C	104.5 (18)
O2—C2—C3	114.09 (11)	C5—N5—H5A	107.5 (12)
C1—C2—C3	107.97 (11)	C5—N5—H5B	109.5 (12)
O2—C2—H2	108.6	H5A—N5—H5B	113.7 (16)
C1—C2—H2	108.6	C5—N5—H5C	108.8 (12)
C3—C2—H2	108.6	H5A—N5—H5C	111.5 (17)
N1—C1—C6	107.99 (11)	H5B—N5—H5C	105.7 (17)
N1—C1—C2	110.35 (12)	C4—O4—H4O	103.2 (12)
C6—C1—C2	112.20 (11)	C2—O2—H2O	107.9 (12)
N1—C1—H1	108.7	C3—O3—H3O	106.1 (13)
C6—C1—H1	108.7	O5—S1—O8	109.81 (7)
C2—C1—H1	108.7	O5—S1—O6	111.42 (6)
O3—C3—C4	111.27 (11)	O8—S1—O6	108.86 (7)
O3—C3—C2	108.78 (11)	O5—S1—O7	110.50 (6)
C4—C3—C2	114.41 (11)	O8—S1—O7	108.39 (6)
O3—C3—H3	107.4	O6—S1—O7	107.77 (7)
C4—C3—H3	107.4

N5—C5—C6—C1	179.85 (11)	O2—C2—C3—C4	65.11 (15)
C4—C5—C6—C1	58.54 (15)	C1—C2—C3—C4	−55.89 (14)
C5—C6—C1—N1	179.52 (11)	O3—C3—C4—O4	58.04 (15)
C5—C6—C1—C2	−58.64 (15)	C2—C3—C4—O4	−65.75 (15)
O2—C2—C1—N1	51.84 (14)	O3—C3—C4—C5	−179.54 (11)
C3—C2—C1—N1	176.11 (10)	C2—C3—C4—C5	56.67 (15)
O2—C2—C1—C6	−68.64 (14)	N5—C5—C4—O4	−53.77 (15)
C3—C2—C1—C6	55.63 (14)	C6—C5—C4—O4	66.61 (14)
O2—C2—C3—O3	−60.00 (15)	N5—C5—C4—C3	−176.61 (11)
C1—C2—C3—O3	179.00 (10)	C6—C5—C4—C3	−56.23 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.87 (1)	2.09 (2)	2.9292 (17)	163 (2)
N1—H1B···O3ⁱⁱ	0.87 (2)	2.11 (2)	2.8125 (18)	138 (2)
N1—H1C···O7ⁱⁱⁱ	0.85 (2)	2.04 (2)	2.882 (2)	170 (2)
N5—H5A···O5	0.89 (2)	1.97 (2)	2.8538 (17)	173 (2)
N5—H5B···O8^iv	0.86 (1)	2.02 (2)	2.8530 (18)	162 (2)
N5—H5C···O7ⁱⁱ	0.87 (2)	2.29 (2)	3.0852 (18)	153 (2)
N5—H5C···O6ⁱⁱ	0.87 (2)	2.34 (2)	3.0856 (19)	144 (2)
O4—H4O···O6	0.85 (2)	1.86 (2)	2.7017 (16)	177 (2)
O2—H2O···O8^v	0.86 (2)	1.97 (2)	2.8161 (15)	170 (2)
O3—H3O···O7^vi	0.86 (2)	1.87 (2)	2.7149 (16)	167 (2)

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x−1, y−1, z; (iv) −x+3/2, y−1/2, −z+1/2; (v) x−1, y, z; (vi) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₆H₁₆N₂O₃²⁺·SO₄²⁻
M_r	260.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	9.2151 (18), 6.6673 (13), 17.267 (4)
β (°)	101.46 (3)
V (Å³)	1039.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Stoe IPDS image plate diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6961, 1779, 1685
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.066, 1.06
No. of reflections	1779
No. of parameters	172
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.29

Computer programs: IPDS Software (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2011), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.870 (14)	2.086 (15)	2.9292 (17)	163.0 (17)
N1—H1B···O3ⁱⁱ	0.867 (15)	2.105 (16)	2.8125 (18)	138.4 (16)
N1—H1C···O7ⁱⁱⁱ	0.853 (15)	2.037 (16)	2.882 (2)	170.3 (18)
N5—H5A···O5	0.885 (15)	1.974 (15)	2.8538 (17)	172.6 (17)
N5—H5B···O8^iv	0.864 (14)	2.019 (15)	2.8530 (18)	161.8 (17)
N5—H5C···O7ⁱⁱ	0.866 (15)	2.290 (16)	3.0852 (18)	152.8 (16)
N5—H5C···O6ⁱⁱ	0.866 (15)	2.342 (16)	3.0856 (19)	144.2 (15)
O4—H4O···O6	0.845 (15)	1.857 (15)	2.7017 (16)	177.3 (19)
O2—H2O···O8^v	0.855 (15)	1.970 (15)	2.8161 (15)	170.1 (18)
O3—H3O···O7^vi	0.856 (15)	1.873 (15)	2.7149 (16)	167.4 (19)

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x−1, y−1, z; (iv) −x+3/2, y−1/2, −z+1/2; (v) x−1, y, z; (vi) −x+1, −y+1, −z.

Acknowledgements

We thank Dr Volker Huch (Universität des Saarlandes) for the collection of the data set.

References

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