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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 10| October 2008| Pages m1238-m1239
doi:10.1107/S160053680802792X

A two-dimensional organic–inorganic hybrid compound, poly[(ethylenedi­amine)tri-μ-oxido-oxidocopper(II)molybdenum(VI)]

Ozgul Gun,a Don VanDerveerb and Mehtap Emirdag-Eanesa*

aIzmir Institute of Technology, Department of Chemistry, Izmir 35430, Turkey, and bDepartment of Chemistry, Clemson University, Hunter Research Laboratory, Clemson, SC 29634-0973, USA
*Correspondence e-mail: mehtapemirdag@iyte.edu.tr

(Received 20 August 2008; accepted 1 September 2008; online 6 September 2008)

A new organic–inorganic two-dimensional hybrid compound, [CuMoO4(C2H8N2)], has been hydro­thermally synthesized at 443 K. The unit cell contains layers composed of CuN2O4 octa­hedra and MoO4 tetra­hedra. Corner-sharing MoO4 and CuN2O4 polyhedra form CuMoO4 bimetallic sites that are joined together through O atoms, forming an edge-sharing Cu2Mo2O4 chain along the c axis. The one-dimensional chains are further linked through bridging O atoms that join the Cu and Mo atoms into respective chains along the b axis, thus establishing layers in the bc plane. The ethyl­enediamine ligand is coordinated to the Cu atom through its two N atoms and is oriented perpendicularly to the two-dimensional –Cu—O—Mo– layers. The average distance between adjacent layers, as calculated by consideration of the closest and furthest distances between two layers, is 8.7 Å. The oxidation states of the Mo and Cu atoms of VI and II, respectively, were confirmed by bond-valence sum calculations.

Related literature

For related literature on inorganic–organic hybrid materials, see: Gopalakrishnan (1995[Gopalakrishnan, J. (1995). Chem. Mater. 7, 1265-1275.]); Katsoulis (1998[Katsoulis, D. E. (1998). Chem. Rev. 98, 359-387.]); Kresge et al. (1992[Kresge, C. T., Leonowicz, M. E., Roth, W. J., Vartuli, J. C. & Beck, J. S. (1992). Nature (London), 359, 710-712.]). For related structures containing molybdate(VI) units, see: Cui et al. (2005[Cui, X.-B., Lü, K., Fan, Y., Xu, J.-Q., Ye, L., Sun, Y.-H., Li, Y., Yu, H.-H. & Yi, Z.-H. (2005). J. Mol. Struct. 743, 151-155.]); Niven et al. (1991[Niven, M. L., Cruywagen, J. J. & Heyns, J. B. B. (1991). J. Chem. Soc. Dalton Trans. pp. 2007-2011.]). For the thermal behaviour of a related ethyl­enediamine-containing compound, see: Han et al. (2005[Han, G.-H., Lin, B.-Z., Li, Z., Sun, D.-Y. & Liu, P.-D. (2005). J. Mol. Struct. 741, 31-35.]). For general background, see: Brown & Altermatt (1985[Brown, I. D. & Altermatt, D. (1985). Acta Cryst. B41, 244-247.]).

[Scheme 1]

Experimental

Crystal data

  • [CuMoO4(C2H8N2)]

  • Mr = 283.58

  • Monoclinic, P 21 /c

  • a = 9.954 (4) Å

  • b = 9.436 (4) Å

  • c = 7.674 (3) Å

  • β = 107.734 (18)°

  • V = 686.6 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.88 mm−1

  • T = 303 (2) K

  • 0.41 × 0.06 × 0.02 mm
Data collection

  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. A. (1998). REQAB. MSC, The Woodlands, Texas, USA.]) Tmin = 0.678, Tmax = 1.000 (expected range = 0.615–0.907)

  • 5616 measured reflections

  • 1209 independent reflections

  • 1098 reflections with I > 2σ(I)

  • Rint = 0.089
Refinement

  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.111

  • S = 1.10

  • 1209 reflections

  • 91 parameters

  • H-atom parameters constrained

  • Δρmax = 0.79 e Å−3

  • Δρmin = −0.92 e Å−3

Table 1
Selected bond lengths (Å)

Mo1—O2 1.739 (7)
Mo1—O3 1.740 (7)
Mo1—O4 1.789 (7)
Mo1—O1 1.803 (6)
Cu2—O1 1.947 (7)
Cu2—O4i 1.951 (7)
Cu2—O1Aii 2.574 (7)
Cu2—O3Aiii 2.460 (7)
Cu2—N2 2.014 (8)
Cu2—N1 2.020 (9)
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+2, -z+1; (iii) -x, -y+2, -z.

Data collection: CrystalClear (Rigaku/MSC, 2001[Rigaku/MSC (2001). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802792X/wm2192sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802792X/wm2192Isup2.hkl

checkCIF report


Comment top

The synthesis and characterization of organic inorganic solid state hybrid materials has attracted great attention due to their structural diversity (Kresge et al., 1992) and widely promising potential applications in chemistry, biology and material science (Katsoulis, 1998). Recent studies have shown that hydrothermal synthesis at low temperature and pressure provides a powerful tool for the synthesis of organic inorganic hybrid materials (Gopalakrishnan, 1995).

The unit cell of the title compound, (I), [Cu(en)MoO4] (en = ethylenediamine), contains layers composed of distorted CuN2O4 octahedra and MoO4 tetrahedra. The coordination environment of the Cu atom comprises two nitrogen atoms (N1 and N2) from the ethylenediamine ligand with Cu—N distances of 2.020 (9) and 2.014 (8) Å, and four bridging oxygen atoms from four adjacent MoO4 tetrahedra with Cu—O distances in the range 1.947 (7) to 2.574 (7) Å (Fig. 1), representing the usual Jahn-Teller distorted coordination.

The Mo atom is coordinated by one terminal oxygen atom (O2) with a distance of 1.739 (7) Å that is indicative of a double bond (Cui et al., 2005) and comparable to other molybdate complexes (Niven et al., 1991). The Mo centre also has two µ2 bridging O atoms (O1 and O4), as well as a µ3 bridging O atom (O1) with Mo—O bond lengths between 1.739 (7) and 1.803 (6) Å. Corner-sharing MoO4 and CuN2O4 polyhedra form CuMoO4 bimetallic sites, and the CuMoO4 groups are joined together through the O1 atoms forming an edge-sharing Cu2Mo2O4 chain along the c axis (Fig. 2). The one-dimensional chains are linked through bridging O4 atoms, that bind the Cu and Mo atoms in the respective chains along the b axis, to establish layers in the bc-plane. The en ligand is coordinated to the copper atom through its two nitrogen atoms and is oriented perpendicularly to the two-dimensional –Cu—O—Mo- layers (Fig. 3). The average distance between two layers, as calculated under consideration of the closest and furthest distances between two adjacent layers, is 8.7 Å.

The +VI oxidation state of the Mo atoms and the +II oxidation state of the Cu atoms were confirmed by bond valence sum calculations (Brown & Altermatt, 1985). The calculated bond valence values for the Mo and Cu atoms are 5.86 and 1.94 Å, respectively.

The thermal behaviour of the title compound was studied in the range 298–923 K under nitrogen atmosphere, demonstrating that the compound is stable up to 468 K. The TG curve exhibits two steps of weight loss. While the first weight loss is 14.61% in the temperature range 468 to 513 K, the second is 6.78% between 513 to 723 K. The total weight loss from 468 to 723 K thus becomes 21.39%, corresponding to the removal of an ethylenediamine group in agreement with the calculated value of 21.15%. These results are comparable to the thermal behaviour of the related compound [Cd(en)3]MoO4 (Han et al., 2005).

Related literature top

For related literature on inorganic–organic hybrid materials, see: Gopalakrishnan (1995); Katsoulis (1998); Kresge et al. (1992). For related structures containing molybdate(VI) units, see: Cui et al. (2005); Niven et al. (1991). For the thermal behaviour of a related ethylenediamine-containing compound, see: Han et al. (2005). For general background, see: Brown & Altermatt (1985).

Experimental top

Compound (I) was synthesized via a hydrothermal reaction procedure. The following reagents were used as obtained; Na2MoO4.2H2O (Carlo Erba, 99.5%), CuCl2.2H2O (Sigma, 99.6%), NaCl (Merck, >99%), and en (Merck, >99%). A mixture of Na2MoO4.2H2O (0.2420 g, 1 mmol), CuCl2.2H2O (0.3410 g, 2 mmol), NaCl (0.0585 g, 1 mmol), en (0.2 ml, 3 mmol) and water (9 ml, 500 mmol) in a molar ratio of 1:2:1:3:500, was loaded into a 23 ml Teflon-lined stainless steel autoclave and heated at 443 K for 72 h. After slow cooling to room temperature, blue crystals with columnar habit of the title compound were recovered in a 90% yield by suction filtration and washed with water and acetone.

Refinement top

H atoms were placed in idealised positions and refined in the riding model approximation with a C—H distance of 0.96 Å and Uiso(H) = 1.2× Ueq(C), and with a N—H distance of 0.90 Å and Uiso(H) = 1.2× Ueq(N), respectively.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear (Rigaku/MSC, 2001); data reduction: CrystalClear (Rigaku/MSC, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The coordination spheres around Cu and Mo atoms, drawn with displacement ellipsoids at the 50% probability level. H atoms of the en ligand are omitted for clarity. [Symmetry operators to generate equivalent atoms: O1A = -x, 2-y, 1-z; O3A = -x, 2-y, -z O4A = -x, 1/2+y, 1/2-z.]
[Figure 2] Fig. 2. Polyhedra projection of the 1-D chain. CuN2O4 are shown as lined polyhedra, and MoO4 tetrahedra are hatched polyhedra.
[Figure 3] Fig. 3. The two-dimensional –Cu—O—Mo- layers. Mo atoms are hatched circles, Cu atoms are lined circles, O atoms are open circles, C atoms are dotted circles and N atoms are shaded circles.
poly[(ethylenediamine)tri-µ-oxido-oxidocopper(II)molybdenum(VI)] top
Crystal data top
[CuMoO4(C2H8N2)]F(000) = 548
Mr = 283.58Dx = 2.743 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4208 reflections
a = 9.954 (4) Åθ = 2.2–26.0°
b = 9.436 (4) ŵ = 4.88 mm−1
c = 7.674 (3) ÅT = 303 K
β = 107.734 (18)°Column, blue
V = 686.6 (5) Å30.41 × 0.06 × 0.02 mm
Z = 4
Data collection top
Rigaku Mercury CCD
diffractometer		1209 independent reflections
Radiation source: Sealed Tube1098 reflections with I > 2σ(I)
Graphite Monochromator monochromatorRint = 0.089
Detector resolution: 14.6199 pixels mm-1θmax = 25.0°, θmin = 3.1°
ω–scansh = −11→11
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		k = −11→11
Tmin = 0.678, Tmax = 1.000l = −8→9
5616 measured reflections
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0154P)2 + 14.9224P]
where P = (Fo2 + 2Fc2)/3
1209 reflections(Δ/σ)max = 0.001
91 parametersΔρmax = 0.79 e Å−3
0 restraintsΔρmin = −0.92 e Å−3
Crystal data top
[CuMoO4(C2H8N2)]V = 686.6 (5) Å3
Mr = 283.58Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.954 (4) ŵ = 4.88 mm−1
b = 9.436 (4) ÅT = 303 K
c = 7.674 (3) Å0.41 × 0.06 × 0.02 mm
β = 107.734 (18)°
Data collection top
Rigaku Mercury CCD
diffractometer		1209 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		1098 reflections with I > 2σ(I)
Tmin = 0.678, Tmax = 1.000Rint = 0.089
5616 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0154P)2 + 14.9224P]
where P = (Fo2 + 2Fc2)/3
1209 reflectionsΔρmax = 0.79 e Å−3
91 parametersΔρmin = −0.92 e Å−3
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
Mo10.16945 (9)0.89946 (9)0.21937 (11)0.0186 (3)
Cu2−0.12230 (13)1.03150 (13)0.30706 (17)0.0205 (4)
N1−0.1618 (9)0.8217 (9)0.3090 (11)0.0226 (19)
H1A−0.14790.77980.21060.027*
H1B−0.10350.78150.41030.027*
O10.0784 (7)1.0015 (7)0.3471 (9)0.0212 (15)
N2−0.3317 (9)1.0540 (10)0.2586 (11)0.025 (2)
H2A−0.35051.07740.36250.030*
H2B−0.36511.12300.17580.030*
O20.3401 (7)0.8692 (8)0.3611 (10)0.0299 (18)
O30.1771 (9)0.9921 (8)0.0266 (10)0.036 (2)
O40.0827 (7)0.7333 (7)0.1511 (10)0.0258 (16)
C2−0.3985 (10)0.9178 (11)0.1886 (14)0.024 (2)
H2C−0.40210.90540.06300.029*
H2D−0.49300.91450.19620.029*
C1−0.3096 (11)0.8039 (12)0.3058 (16)0.031 (3)
H1C−0.31590.81000.42790.038*
H1D−0.34330.71230.25730.0387*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mo10.0228 (5)0.0186 (4)0.0169 (4)−0.0027 (4)0.0104 (3)−0.0023 (4)
Cu20.0204 (7)0.0178 (6)0.0233 (7)0.0005 (5)0.0074 (5)0.0011 (5)
N10.022 (5)0.027 (5)0.019 (4)−0.001 (4)0.007 (4)0.003 (4)
O10.025 (4)0.022 (4)0.018 (4)0.003 (3)0.009 (3)−0.004 (3)
N20.025 (5)0.036 (5)0.015 (4)−0.003 (4)0.008 (4)−0.004 (4)
O20.018 (4)0.037 (5)0.033 (4)−0.001 (3)0.006 (3)−0.011 (4)
O30.055 (5)0.035 (5)0.023 (4)−0.012 (4)0.022 (4)−0.003 (4)
O40.026 (4)0.022 (4)0.026 (4)−0.006 (3)0.005 (3)−0.003 (3)
C20.012 (5)0.033 (6)0.030 (6)−0.005 (4)0.008 (4)0.000 (5)
C10.026 (6)0.036 (7)0.034 (6)0.001 (5)0.014 (5)0.013 (5)
Geometric parameters (Å, º) top
Mo1—O21.739 (7)N1—H1A0.9000
Mo1—O31.740 (7)N1—H1B0.9000
Mo1—O41.789 (7)N2—C21.471 (13)
Mo1—O11.803 (6)N2—H2A0.9000
Cu2—O11.947 (7)N2—H2B0.9000
Cu2—O4i1.951 (7)O4—Cu2iv1.951 (7)
Cu2—O1Aii2.574 (7)C2—C11.505 (15)
Cu2—O3Aiii2.460 (7)C2—H2C0.9600
Cu2—N22.014 (8)C2—H2D0.9600
Cu2—N12.020 (9)C1—H1C0.9600
N1—C11.473 (13)C1—H1D0.9600
O2—Mo1—O3109.1 (4)C2—N2—Cu2107.6 (6)
O2—Mo1—O4109.4 (3)C2—N2—H2A110.2
O3—Mo1—O4109.5 (3)Cu2—N2—H2A110.2
O2—Mo1—O1107.8 (3)C2—N2—H2B110.2
O3—Mo1—O1110.7 (3)Cu2—N2—H2B110.2
O4—Mo1—O1110.4 (3)H2A—N2—H2B108.5
O1—Cu2—O4i88.3 (3)Mo1—O4—Cu2iv138.7 (4)
O1—Cu2—N2177.3 (3)N2—C2—C1106.7 (9)
O4i—Cu2—N294.2 (3)N2—C2—H2C110.4
O1—Cu2—N192.8 (3)C1—C2—H2C110.4
O4i—Cu2—N1170.2 (3)N2—C2—H2D110.4
N2—Cu2—N184.9 (3)C1—C2—H2D110.4
C1—N1—Cu2107.9 (6)H2C—C2—H2D108.6
C1—N1—H1A110.1N1—C1—C2109.3 (8)
Cu2—N1—H1A110.1N1—C1—H1C109.8
C1—N1—H1B110.1C2—C1—H1C109.8
Cu2—N1—H1B110.1N1—C1—H1D109.8
H1A—N1—H1B108.4C2—C1—H1D109.8
Mo1—O1—Cu2130.8 (4)H1C—C1—H1D108.3
O1—Cu2—N1—C1172.4 (6)O4i—Cu2—N2—C2170.1 (6)
O4i—Cu2—N1—C176 (2)N1—Cu2—N2—C2−19.7 (6)
N2—Cu2—N1—C1−9.1 (7)O2—Mo1—O4—Cu2iv1.6 (7)
O2—Mo1—O1—Cu2−161.3 (5)O3—Mo1—O4—Cu2iv121.0 (6)
O3—Mo1—O1—Cu279.4 (5)O1—Mo1—O4—Cu2iv−116.8 (6)
O4—Mo1—O1—Cu2−42.0 (6)Cu2—N2—C2—C143.7 (9)
O4i—Cu2—O1—Mo1−133.4 (5)Cu2—N1—C1—C236.0 (10)
N1—Cu2—O1—Mo156.3 (5)N2—C2—C1—N1−53.4 (11)
O1—Cu2—N2—C214 (7)
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+2, −z+1; (iii) −x, −y+2, −z; (iv) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[CuMoO4(C2H8N2)]
Mr283.58
Crystal system, space groupMonoclinic, P21/c
Temperature (K)303
a, b, c (Å)9.954 (4), 9.436 (4), 7.674 (3)
β (°) 107.734 (18)
V (Å3)686.6 (5)
Z4
Radiation typeMo Kα
µ (mm−1)4.88
Crystal size (mm)0.41 × 0.06 × 0.02
Data collection
DiffractometerRigaku Mercury CCD
diffractometer
Absorption correctionMulti-scan
(REQAB; Jacobson, 1998)
Tmin, Tmax0.678, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		5616, 1209, 1098
Rint0.089
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.111, 1.10
No. of reflections1209
No. of parameters91
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0154P)2 + 14.9224P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)0.79, −0.92

Computer programs: CrystalClear (Rigaku/MSC, 2001), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Mo1—O21.739 (7)Cu2—O4i1.951 (7)
Mo1—O31.740 (7)Cu2—O1Aii2.574 (7)
Mo1—O41.789 (7)Cu2—O3Aiii2.460 (7)
Mo1—O11.803 (6)Cu2—N22.014 (8)
Cu2—O11.947 (7)Cu2—N12.020 (9)
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+2, −z+1; (iii) −x, −y+2, −z.
 

Acknowledgements

We are indebted to TÜBITAK (TBAG-2160) and L'Oreal Türkiye for support of this work.

References

First citationBrown, I. D. & Altermatt, D. (1985). Acta Cryst. B41, 244–247.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationCui, X.-B., Lü, K., Fan, Y., Xu, J.-Q., Ye, L., Sun, Y.-H., Li, Y., Yu, H.-H. & Yi, Z.-H. (2005). J. Mol. Struct. 743, 151–155.  Web of Science CSD CrossRef CAS Google Scholar
 First citationGopalakrishnan, J. (1995). Chem. Mater. 7, 1265–1275.  CrossRef CAS Web of Science Google Scholar
 First citationHan, G.-H., Lin, B.-Z., Li, Z., Sun, D.-Y. & Liu, P.-D. (2005). J. Mol. Struct. 741, 31–35.  Web of Science CrossRef CAS Google Scholar
 First citationJacobson, R. A. (1998). REQAB. MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationKatsoulis, D. E. (1998). Chem. Rev. 98, 359–387.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationKresge, C. T., Leonowicz, M. E., Roth, W. J., Vartuli, J. C. & Beck, J. S. (1992). Nature (London), 359, 710–712.  CrossRef CAS Web of Science Google Scholar
 First citationNiven, M. L., Cruywagen, J. J. & Heyns, J. B. B. (1991). J. Chem. Soc. Dalton Trans. pp. 2007–2011.  CSD CrossRef Web of Science Google Scholar
 First citationRigaku/MSC (2001). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 10| October 2008| Pages m1238-m1239
doi:10.1107/S160053680802792X
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