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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o31
https://doi.org/10.1107/S1600536810049822

Piperazine-1,4-diium bis­­(hydrogen 2-propyl-1H-imidazole-4,5-dicarbox­ylate) monohydrate

Zhu-Qing Gaoa* and Jin-Zhong Gub

aSchool of Chemistry and Biology Engineering, Taiyuan University of Science and Technology, Taiyuan 030021, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China
*Correspondence e-mail: zqgao2008@163.com

(Received 25 November 2010; accepted 29 November 2010; online 4 December 2010)

The title compound, C4H12N22+·2C8H9N2O4−·H2O, is a hydrated proton-transfer compound obtained from 2-propyl-1H-imidazole-4,5-dicarb­oxy­lic acid and piperazine. The asymmetric unit contains one half-cation, one anion and half a water mol­ecule. There is a centre of inversion at the centre of the cation ring and the water molecule O atom lies on a twofold rotation axis. In the crystal, inter­molecular N—H⋯O and N—H⋯N hydrogen bonds help to construct a three-dimensional framework. Almost symmetrical, intramolecular O—H⋯O inter­actions are also observed.

Related literature

For the structures and properties of proton-transfer compounds, see: Aghabozorg et al. (2006[Aghabozorg, H., Ghadermazi, M. & Sadr Khanlou, E. (2006). Anal. Sci. 22, x253-x254.]). For the use of multi-carboxyl­ate heterocyclic acids and piperazine in coord­ination chemistry, see: Murugavel et al. (2009[Murugavel, S., Selvakumar, R., Govindarajan, S., Kannan, P. S. & SubbiahPandi, A. (2009). Acta Cryst. E65, o1004.]); Sheshmani et al. (2006[Sheshmani, S., Ghadermazi, M. & Aghabozorg, H. (2006). Acta Cryst. E62, o3620-o3622.]) and for piperazinium structures, see: Murugavel et al. (2009[Murugavel, S., Selvakumar, R., Govindarajan, S., Kannan, P. S. & SubbiahPandi, A. (2009). Acta Cryst. E65, o1004.]); Sheshmani et al. (2007[Sheshmani, S., Aghabozorg, H. & Ghadermazi, M. (2007). Acta Cryst. E63, o2869.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C4H12N22+·2C8H9N2O4−·H2O

  • Mr = 500.52

  • Monoclinic, I 2/a

  • a = 11.288 (2) Å

  • b = 15.965 (3) Å

  • c = 14.449 (4) Å

  • β = 101.296 (12)°

  • V = 2553.6 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 273 K

  • 0.20 × 0.18 × 0.16 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.984

  • 6239 measured reflections

  • 2066 independent reflections

  • 1499 reflections with I > 2σ(I)

  • Rint = 0.039
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.136

  • S = 1.05

  • 2066 reflections

  • 165 parameters

  • 13 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H2⋯O1 1.19 (3) 1.26 (3) 2.447 (3) 172 (3)
O5—H1W⋯O1i 0.87 2.24 3.065 (3) 158
N1—H1⋯O2ii 0.86 1.94 2.773 (3) 162
N3—H3A⋯N2 0.90 1.94 2.820 (3) 165
N3—H3B⋯O4iii 0.90 1.96 2.826 (3) 161
Symmetry codes: (i) x+1, y, z; (ii) [-x+{\script{1\over 2}}, y, -z]; (iii) [-x+{\script{1\over 2}}, y, -z+1].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810049822/jh2238sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049822/jh2238Isup2.hkl

checkCIF report


Comment top

t;text-indent:12.0 pt;mso-char-indent-count: 1.0;line-height:200%'>In the past decades, much attention has been focused on the design and synthesis of proton-transfer compounds, owing to their importance in physics, chemistry and biochemistry (Aghabozorg et al., 2006; Allen et al., 1987). Many multi-carboxylate or heterocyclic acids and piperazine are used for this purpose (Murugavel et al., 2009; Sheshmani et al., 2006). In order to extend the investigation, we have prepared the title compound, (I), and report its crystal structure here.

As shown in Fig.1, The asymmetric unit contains one half-cation, one anion and half a water molecule. There is a centre of inversion at the centre of the cation ring and one water molecule lies on a twofold rotation axis. The organic piperazinium dication lies at an inversion centre and adopts a typical chair geometry with normal valence bond lengths (Murugavel et al., 2009) and angles, as observed in the related structures (Sheshmani et al., 2007). The anionic fragment individually has two intramolecular hydrogen bonds, a O–H···O bond between adjacent carboxylate groups and a N–H···O bond between the imidazole ring and the carboxylate group (Fig. 2 and Table 1). In the crystal structure, intermolecular N–H···O and N–H···N hydrogen bonds play an important role in the construction of the three-dimensional framework (Fig. 3).

Related literature top

For the structures and properties of proton-transfer compounds, see: Aghabozorg et al. (2006). For the use of multi-carboxylate heterocyclic acids and piperazine in coordination chemistry, see: Murugavel et al. (2009); Sheshmani et al. (2006) and for piperazinium structures, see: Murugavel et al. (2009); Sheshmani et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

To a solution of 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.100 g, 0.5 mmol) in water (5 ml) was added an aqueous solution (5 ml) of piperazine (0.089 g, 0.5 mmol). The reactants were sealed in a 25-ml Teflon-lined, stainless-steel Parr bomb. The bomb was heated at 433 K for 3 days. The cool solution yielded single crystals in ca 70% yield. Anal. Calcd for C10H16N3O4.5: C, 47.99; H, 6.44; N, 16.79. Found: C, 47.61; H, 6.77; N, 16.42.

Refinement top

The free water H atoms attached to oxygen atoms were placed at calculated positions and refined with the riding model, considering the position of oxygen atoms and the quantity of H atoms. The H atoms were placed in geometrically idealized positions, withN–H = 0.86–0.90 Å and C–H = 0.93 Å, and constrained to ride on their respective parent atoms, with Uiso(H) = 1.2 Ueq.

Structure description top

t;text-indent:12.0 pt;mso-char-indent-count: 1.0;line-height:200%'>In the past decades, much attention has been focused on the design and synthesis of proton-transfer compounds, owing to their importance in physics, chemistry and biochemistry (Aghabozorg et al., 2006; Allen et al., 1987). Many multi-carboxylate or heterocyclic acids and piperazine are used for this purpose (Murugavel et al., 2009; Sheshmani et al., 2006). In order to extend the investigation, we have prepared the title compound, (I), and report its crystal structure here.

As shown in Fig.1, The asymmetric unit contains one half-cation, one anion and half a water molecule. There is a centre of inversion at the centre of the cation ring and one water molecule lies on a twofold rotation axis. The organic piperazinium dication lies at an inversion centre and adopts a typical chair geometry with normal valence bond lengths (Murugavel et al., 2009) and angles, as observed in the related structures (Sheshmani et al., 2007). The anionic fragment individually has two intramolecular hydrogen bonds, a O–H···O bond between adjacent carboxylate groups and a N–H···O bond between the imidazole ring and the carboxylate group (Fig. 2 and Table 1). In the crystal structure, intermolecular N–H···O and N–H···N hydrogen bonds play an important role in the construction of the three-dimensional framework (Fig. 3).

For the structures and properties of proton-transfer compounds, see: Aghabozorg et al. (2006). For the use of multi-carboxylate heterocyclic acids and piperazine in coordination chemistry, see: Murugavel et al. (2009); Sheshmani et al. (2006) and for piperazinium structures, see: Murugavel et al. (2009); Sheshmani et al. (2007). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 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
[Figure 1] Fig. 1. A drawing of the asymmetric unit in the structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The hydrogen bonds are shown and are depicted by blue dashed lines. Hydrogen atoms that bonded to carbon atoms were omitted for clarity. [Symmetry codes: (i) x, -y + 3/2, z - 1/2; (ii) –x + 1/2, -y + 3/2, -z + 1/2; (iii) x, -y + 3/2, z - 1/2; (iv) –x + 3/2, -y + 3/2, -z + 1/2].
[Figure 3] Fig. 3. A view along the a axis, showing a three-dimensional framework.
Piperazine-1,4-diium bis(hydrogen 2-propyl-1H-imidazole-4,5-dicarboxylate) monohydrate top
Crystal data top
C4H12N22+·2C8H9N2O4−·H2OF(000) = 1064
Mr = 500.52Dx = 1.302 Mg m−3
Monoclinic, I2/aMo Kα radiation, λ = 0.71073 Å
a = 11.288 (2) ÅCell parameters from 1047 reflections
b = 15.965 (3) Åθ = 0.0–0.0°
c = 14.449 (4) ŵ = 0.10 mm−1
β = 101.296 (12)°T = 273 K
V = 2553.6 (10) Å3Block, colorless
Z = 40.20 × 0.18 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2066 independent reflections
Radiation source: fine-focus sealed tube1499 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 24.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −10→13
Tmin = 0.980, Tmax = 0.984k = −18→17
6239 measured reflectionsl = −16→16
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: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0619P)2 + 1.5738P]
where P = (Fo2 + 2Fc2)/3
2066 reflections(Δ/σ)max = 0.001
165 parametersΔρmax = 0.43 e Å−3
13 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C4H12N22+·2C8H9N2O4−·H2OV = 2553.6 (10) Å3
Mr = 500.52Z = 4
Monoclinic, I2/aMo Kα radiation
a = 11.288 (2) ŵ = 0.10 mm−1
b = 15.965 (3) ÅT = 273 K
c = 14.449 (4) Å0.20 × 0.18 × 0.16 mm
β = 101.296 (12)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2066 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		1499 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.984Rint = 0.039
6239 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05013 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.43 e Å−3
2066 reflectionsΔρmin = −0.21 e Å−3
165 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
xyzUiso*/Ueq
C10.0849 (2)0.71261 (16)0.09103 (17)0.0422 (6)
C20.1935 (2)0.67934 (14)0.15314 (16)0.0364 (6)
C30.2144 (2)0.64165 (14)0.24013 (16)0.0363 (6)
C40.1292 (2)0.62027 (16)0.30292 (18)0.0424 (6)
C50.5184 (2)0.6485 (2)0.1969 (2)0.0611 (8)
H5A0.56490.64780.26090.073*
H5B0.54090.69840.16610.073*
C60.5505 (3)0.5713 (3)0.1446 (4)0.1233 (18)
H6A0.50280.57100.08100.148*
H6B0.53080.52120.17650.148*
C70.6847 (4)0.5704 (3)0.1403 (5)0.171 (3)
H7A0.70390.61950.10780.205*
H7B0.70240.52130.10720.205*
H7C0.73200.56990.20320.205*
C80.5499 (2)0.57768 (16)0.47554 (19)0.0483 (7)
H8A0.56430.63700.48720.058*
H8B0.58640.56170.42270.058*
C90.3930 (2)0.47110 (16)0.43879 (17)0.0456 (7)
H9A0.42310.45090.38450.055*
H9B0.30620.46270.42670.055*
C120.3877 (2)0.65313 (16)0.20022 (17)0.0429 (6)
H2−0.004 (2)0.6647 (18)0.195 (2)0.103 (11)*
H1W0.81400.74430.02090.31 (5)*
N10.30493 (17)0.68560 (13)0.12993 (13)0.0410 (5)
H10.31960.70690.07870.049*
N20.33568 (18)0.62552 (13)0.26903 (14)0.0426 (5)
N30.42026 (17)0.56200 (13)0.45216 (14)0.0426 (5)
H3A0.38830.58970.39890.051*
H3B0.38560.58180.49880.051*
O1−0.01641 (15)0.70340 (13)0.11795 (13)0.0582 (6)
O20.09473 (15)0.74761 (12)0.01667 (12)0.0510 (5)
O30.01637 (15)0.63600 (13)0.27299 (13)0.0566 (5)
O40.16861 (16)0.58907 (12)0.38055 (12)0.0537 (5)
O50.75000.7747 (3)0.00000.170 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0499 (16)0.0430 (15)0.0338 (14)0.0040 (12)0.0083 (12)−0.0025 (12)
C20.0403 (13)0.0379 (14)0.0322 (13)0.0010 (10)0.0101 (10)−0.0008 (10)
C30.0388 (13)0.0379 (14)0.0331 (13)0.0015 (10)0.0092 (10)0.0022 (10)
C40.0480 (15)0.0419 (15)0.0390 (15)0.0021 (11)0.0124 (12)0.0047 (12)
C50.0471 (17)0.088 (2)0.0514 (17)0.0117 (15)0.0188 (14)0.0195 (16)
C60.090 (3)0.089 (3)0.215 (5)0.042 (2)0.089 (3)0.042 (3)
C70.130 (4)0.149 (5)0.268 (7)0.062 (4)0.126 (5)0.072 (5)
C80.0438 (15)0.0455 (16)0.0572 (17)0.0039 (12)0.0138 (13)0.0078 (13)
C90.0408 (14)0.0511 (17)0.0438 (16)0.0050 (12)0.0055 (11)−0.0065 (12)
C120.0437 (14)0.0530 (16)0.0335 (14)0.0049 (12)0.0110 (11)0.0054 (12)
N10.0469 (12)0.0483 (13)0.0307 (11)0.0027 (10)0.0150 (9)0.0058 (9)
N20.0437 (12)0.0494 (13)0.0366 (12)0.0059 (9)0.0127 (9)0.0089 (9)
N30.0448 (12)0.0479 (13)0.0354 (11)0.0108 (9)0.0090 (9)0.0058 (9)
O10.0429 (11)0.0824 (15)0.0487 (12)0.0088 (9)0.0075 (9)0.0143 (10)
O20.0610 (12)0.0601 (12)0.0334 (10)0.0150 (9)0.0132 (9)0.0053 (8)
O30.0427 (11)0.0766 (14)0.0527 (12)0.0031 (9)0.0146 (9)0.0180 (10)
O40.0540 (11)0.0682 (13)0.0426 (11)0.0087 (9)0.0189 (9)0.0200 (9)
O50.084 (3)0.089 (3)0.315 (8)0.000−0.015 (4)0.000
Geometric parameters (Å, º) top
C1—O21.235 (3)C7—H7C0.9600
C1—O11.286 (3)C8—N31.458 (3)
C1—C21.469 (3)C8—C9i1.497 (3)
C2—N11.368 (3)C8—H8A0.9700
C2—C31.372 (3)C8—H8B0.9700
C3—N21.375 (3)C9—N31.488 (3)
C3—C41.486 (3)C9—C8i1.497 (3)
C4—O41.228 (3)C9—H9A0.9700
C4—O31.287 (3)C9—H9B0.9700
C5—C121.487 (3)C12—N21.325 (3)
C5—C61.526 (5)C12—N11.342 (3)
C5—H5A0.9700N1—H10.8600
C5—H5B0.9700N3—H3A0.9000
C6—C71.528 (5)N3—H3B0.9000
C6—H6A0.9700O1—H21.26 (3)
C6—H6B0.9700O3—H21.19 (3)
C7—H7A0.9600O5—H1W0.8739
C7—H7B0.9600
O2—C1—O1123.5 (2)H7B—C7—H7C109.5
O2—C1—C2119.2 (2)N3—C8—C9i110.6 (2)
O1—C1—C2117.3 (2)N3—C8—H8A109.5
N1—C2—C3104.8 (2)C9i—C8—H8A109.5
N1—C2—C1121.4 (2)N3—C8—H8B109.5
C3—C2—C1133.8 (2)C9i—C8—H8B109.5
C2—C3—N2110.1 (2)H8A—C8—H8B108.1
C2—C3—C4130.1 (2)N3—C9—C8i110.8 (2)
N2—C3—C4119.8 (2)N3—C9—H9A109.5
O4—C4—O3122.9 (2)C8i—C9—H9A109.5
O4—C4—C3119.3 (2)N3—C9—H9B109.5
O3—C4—C3117.8 (2)C8i—C9—H9B109.5
C12—C5—C6112.9 (3)H9A—C9—H9B108.1
C12—C5—H5A109.0N2—C12—N1110.5 (2)
C6—C5—H5A109.0N2—C12—C5126.6 (2)
C12—C5—H5B109.0N1—C12—C5122.9 (2)
C6—C5—H5B109.0C12—N1—C2108.89 (19)
H5A—C5—H5B107.8C12—N1—H1125.6
C5—C6—C7111.2 (4)C2—N1—H1125.6
C5—C6—H6A109.4C12—N2—C3105.7 (2)
C7—C6—H6A109.4C8—N3—C9111.74 (18)
C5—C6—H6B109.4C8—N3—H3A109.3
C7—C6—H6B109.4C9—N3—H3A109.3
H6A—C6—H6B108.0C8—N3—H3B109.3
C6—C7—H7A109.5C9—N3—H3B109.3
C6—C7—H7B109.5H3A—N3—H3B107.9
H7A—C7—H7B109.5C1—O1—H2112.1 (11)
C6—C7—H7C109.5C4—O3—H2112.9 (12)
H7A—C7—H7C109.5
Symmetry code: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H2···O11.19 (3)1.26 (3)2.447 (3)172 (3)
O5—H1W···O1ii0.872.243.065 (3)158
N1—H1···O2iii0.861.942.773 (3)162
N3—H3A···N20.901.942.820 (3)165
N3—H3B···O4iv0.901.962.826 (3)161
Symmetry codes: (ii) x+1, y, z; (iii) −x+1/2, y, −z; (iv) −x+1/2, y, −z+1.

Experimental details

Crystal data
Chemical formulaC4H12N22+·2C8H9N2O4−·H2O
Mr500.52
Crystal system, space groupMonoclinic, I2/a
Temperature (K)273
a, b, c (Å)11.288 (2), 15.965 (3), 14.449 (4)
β (°) 101.296 (12)
V (Å3)2553.6 (10)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.20 × 0.18 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.980, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		6239, 2066, 1499
Rint0.039
(sin θ/λ)max (Å−1)0.578
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.136, 1.05
No. of reflections2066
No. of parameters165
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.43, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H2···O11.19 (3)1.26 (3)2.447 (3)172 (3)
O5—H1W···O1i0.872.243.065 (3)158.0
N1—H1···O2ii0.861.942.773 (3)161.6
N3—H3A···N20.901.942.820 (3)165.4
N3—H3B···O4iii0.901.962.826 (3)160.7
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y, −z; (iii) −x+1/2, y, −z+1.
 

References

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o31
https://doi.org/10.1107/S1600536810049822
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