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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 67| Part 3| March 2011| Page m359
doi:10.1107/S1600536811005939

Di­iodidobis[4-(4-nitro­benz­yl)pyridine-κN1]zinc

Graham Smith,a* Urs D. Wermutha and Michael L. Williamsb

aFaculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia, and bSchool of Biomolecular and Physical Sciences, Griffith University, Nathan, Queensland 4111, Australia
*Correspondence e-mail: g.smith@qut.edu.au

(Received 1 February 2011; accepted 17 February 2011; online 23 February 2011)

The asymmetric unit of the title compound, [ZnI2(C12H10N2O2)2], obtained from the reaction of 4-(4-nitro­benz­yl)pyridine with zinc(II) iodide, contains two independent discrete distorted tetra­hedral complex units [Zn—I = 2.5472 (8)–2.5666 (7) Å and Zn—N = 2.044 (4)–2.052 (4) Å], which are essentially identical conformationally. The crystal used for measurement was a racemic twin.

Related literature

For the structures of some ZnII–pyridine complexes, see: Le Querler et al. (1977[Le Querler, J. F., Borel, M. M. & Leclaire, A. (1977). Acta Cryst. B33, 2299-2300.]); Pasaoglu et al. (2006[Pasaoglu, H., Guven, S., Haren, Z. & Büyükgüngör, O. (2006). J. Mol. Struct. 794, 270-276.]); Fan & Wu (2006[Fan, L.-Q. & Wu, J.-H. (2006). Acta Cryst. C62, m548-m549.]). For the structure of a mixed-ligand PtII complex with 4-(4-nitro­benz­yl)pyridine, see: Chan et al. (1993[Chan, C.-W., Lai, T.-F., Chi, C.-M. & Peng, S.-M. (1993). J. Am. Chem. Soc. 115, 11245-11253.]).

[Scheme 1]

Experimental

Crystal data

  • [ZnI2(C12H10N2O2)2]

  • Mr = 747.61

  • Orthorhombic, P c a 21

  • a = 18.2091 (2) Å

  • b = 15.8998 (3) Å

  • c = 19.0327 (3) Å

  • V = 5510.37 (15) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.17 mm−1

  • T = 200 K

  • 0.40 × 0.22 × 0.15 mm
Data collection

  • Oxford Diffraction Gemini-S Ultra CCD detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.865, Tmax = 0.980

  • 18536 measured reflections

  • 10102 independent reflections

  • 7499 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.056

  • S = 0.89

  • 10102 reflections

  • 627 parameters

  • 25 restraints

  • H-atom parameters not refined

  • Δρmax = 0.63 e Å−3

  • Δρmin = −0.47 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4516 Friedel pairs

  • Flack parameter: 0.430 (14)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005939/ng5114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005939/ng5114Isup2.hkl

checkCIF report


Comment top

The structures of complexes of ZnI2 with pyridine and substituted pyridine ligands, of the type [ZnI2(py)2] are common in the crystallographic literature e.g. with pyridine (Le Querler et al., 1977), and with nicotinamide and isonicotinamide (Pasaoglu et al., 2006). These complexes are usually discrete with distorted tetrahedral stereochemistry. Polymeric complexes having similar stereochemistry are also formed with bifunctional pyridines such as 4,4'-bipyridine (Fan & Wu, 2006). We obtained the title compound [ZnI2(C12H10N2O2)2] (I) from the reaction of zinc(II) iodide with 4-(4-nitrobenzyl)pyridine (L) and the structure is reported here. This substituted pyridine has only occasionally been used as a ligand in metal complex formation e.g. in the mixed-ligand PtII complex with 2,9-diphenyl-1,10-phenanthroline (Chan et al., 1993).

In the structure of (I), the asymmetric unit contains two independent discrete distorted tetrahedral [ZnI2L2] complex units, involving Zn1 and Zn2 (Figs. 1, 2). The Zn—I range is 2.5472 (8)–2.5666 (7) Å, the Zn—N range is 2.044 (4)–2.052 (4) Å and the bond angle range about Zn is 98.99 (17)–119.96 (2)° (for I1—Zn1—I2 and N1A—Zn1—N1B, respectively). The two complex molecules are essentially identical conformationally and are related by pseudo-symmetry, being treated as a racemic twin in the structure refinement.

In the crystal packing of (I) there are only weak intermolecular aromatic C—H···Onitro interactions [C5A—H···O41D, 3.211 (9) Å and C6B—H···O41B, 3.295 Å] but there are some aromatic ring π–π associations involving the C11B–C61B rings: ring centroid separation, 3.591 (3) Å; inter-ring dihedral angle, 3.46 (1)°] (Fig. 3).

Related literature top

For the structures of some ZnII–pyridine complexes, see: Le Querler et al. (1977); Pasaoglu et al. (2006); Fan & Wu (2006). For the structure of a mixed-ligand PtII complex with 4-(4-nitrobenzyl)pyridine, see: Chan et al. (1993).

Experimental top

The title compound was synthesized by heating together under reflux for 10 minutes, 1 mmol of zinc(II) iodide and 2 mmol of 4-(4-nitrobenzyl)pyridine in 50 ml of 50% ethanol–water. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave pale yellow flattened prisms of (I) from which a suitable specimen was cleaved for the X-ray analysis.

Refinement top

Hydrogen atoms were included in the refinement in calculated positions with C–H = 0.93 Å (aromatic) or 0.97 Å (aliphatic) and allowed to ride, with Uiso(H) = 1.2Ueq(C). A racemic twin was identified and treated as such using the appropriate SHELXL97 function [BASF factor, 0.430 (14)]. Oxygen atoms of the terminal nitro groups were significantly disordered, one in particular (O41C, Uiso = 0.142 Å2) subsequently being refined isotropically.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for the first of the two independent complex units (about Zn1) in the asymmetric unit of (I), with non-H atoms drawn as 30% probability ellipsoids.
[Figure 2] Fig. 2. The molecular configuration and atom-numbering scheme for the second complex unit (about Zn2) in (I) (30% probability).
[Figure 3] Fig. 3. The packing of (I) in the unit cell, viewed down the a cell direction. Hydrogen atoms are omitted.
Diiodidobis[4-(4-nitrobenzyl)pyridine-κN1]zinc top
Crystal data top
[ZnI2(C12H10N2O2)2]Dx = 1.802 Mg m−3
Mr = 747.61Melting point = 473–475 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 5528 reflections
a = 18.2091 (2) Åθ = 3.3–28.7°
b = 15.8998 (3) ŵ = 3.17 mm−1
c = 19.0327 (3) ÅT = 200 K
V = 5510.37 (15) Å3Prism, pale yellow
Z = 80.40 × 0.22 × 0.15 mm
F(000) = 2880
Data collection top
Oxford Diffraction Gemini-S Ultra CCD detector
diffractometer		10102 independent reflections
Radiation source: Enhance (Mo) X-ray source7499 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 16.077 pixels mm-1θmax = 26.0°, θmin = 3.4°
ω scansh = −22→22
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = −19→19
Tmin = 0.865, Tmax = 0.980l = −23→22
18536 measured reflections
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)] = 0.032H-atom parameters not refined
wR(F2) = 0.056 w = 1/[σ2(Fo2) + (0.0262P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max = 0.024
10102 reflectionsΔρmax = 0.63 e Å−3
627 parametersΔρmin = −0.47 e Å−3
25 restraintsAbsolute structure: Flack (1983), 4516 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.430 (14)
Crystal data top
[ZnI2(C12H10N2O2)2]V = 5510.37 (15) Å3
Mr = 747.61Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 18.2091 (2) ŵ = 3.17 mm−1
b = 15.8998 (3) ÅT = 200 K
c = 19.0327 (3) Å0.40 × 0.22 × 0.15 mm
Data collection top
Oxford Diffraction Gemini-S Ultra CCD detector
diffractometer		10102 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		7499 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.980Rint = 0.024
18536 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters not refined
wR(F2) = 0.056Δρmax = 0.63 e Å−3
S = 0.89Δρmin = −0.47 e Å−3
10102 reflectionsAbsolute structure: Flack (1983), 4516 Friedel pairs
627 parametersAbsolute structure parameter: 0.430 (14)
25 restraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
I10.95618 (2)0.12807 (3)0.69072 (2)0.0518 (1)
I21.15212 (2)0.14231 (3)0.82772 (2)0.0567 (1)
Zn11.01354 (3)0.12528 (4)0.81338 (3)0.0432 (2)
O41A0.6840 (4)0.3754 (6)1.2662 (4)0.179 (5)
O41B0.6256 (3)−0.0954 (3)1.1910 (3)0.0767 (19)
O42A0.7998 (4)0.3645 (5)1.3010 (4)0.123 (3)
O42B0.5740 (3)−0.1013 (4)1.0908 (3)0.100 (3)
N1A0.9587 (2)0.2149 (3)0.8705 (2)0.0440 (17)
N1B0.9820 (2)0.0205 (3)0.8686 (2)0.0393 (16)
N41A0.7532 (6)0.3685 (6)1.2560 (5)0.146 (5)
N41B0.6283 (3)−0.1037 (3)1.1280 (4)0.060 (2)
C2A0.8847 (3)0.2146 (4)0.8703 (3)0.064 (3)
C2B1.0121 (3)0.0043 (3)0.9320 (3)0.0413 (19)
C3A0.8434 (3)0.2746 (4)0.9017 (3)0.065 (3)
C3B0.9891 (3)−0.0596 (4)0.9745 (3)0.0447 (19)
C4A0.8780 (4)0.3398 (4)0.9357 (3)0.053 (2)
C4B0.9333 (3)−0.1124 (3)0.9535 (3)0.038 (2)
C5A0.9519 (4)0.3414 (4)0.9358 (4)0.066 (3)
C5B0.9039 (3)−0.0982 (4)0.8879 (3)0.045 (2)
C6A0.9918 (3)0.2776 (4)0.9036 (3)0.058 (3)
C6B0.9289 (3)−0.0329 (3)0.8476 (3)0.0440 (19)
C11A0.8119 (4)0.3939 (4)1.0439 (4)0.056 (3)
C11B0.8332 (3)−0.1589 (3)1.0348 (3)0.0343 (19)
C21A0.7428 (4)0.3758 (6)1.0609 (5)0.098 (4)
C21B0.7678 (3)−0.1709 (3)0.9985 (4)0.049 (2)
C31A0.7239 (4)0.3700 (6)1.1283 (5)0.107 (4)
C31B0.7012 (3)−0.1499 (4)1.0273 (3)0.052 (2)
C41A0.7739 (4)0.3750 (5)1.1802 (5)0.078 (3)
C41B0.7001 (3)−0.1210 (3)1.0951 (3)0.040 (2)
C42A0.8329 (4)0.4105 (4)0.9687 (4)0.080 (3)
C42B0.9056 (3)−0.1818 (3)1.0005 (3)0.0453 (19)
C51A0.8454 (4)0.3902 (4)1.1653 (5)0.072 (3)
C51B0.7630 (3)−0.1092 (3)1.1331 (3)0.042 (2)
C61A0.8651 (4)0.3999 (4)1.0951 (4)0.068 (3)
C61B0.8296 (3)−0.1277 (4)1.1026 (4)0.048 (2)
I31.16361 (2)0.37425 (3)0.36527 (2)0.0519 (2)
I40.97184 (2)0.40341 (3)0.50705 (2)0.0539 (1)
Zn21.02497 (3)0.39353 (4)0.38352 (4)0.0426 (2)
O41C0.6595 (4)0.1413 (4)−0.0106 (4)0.142 (3)*
O41D0.6107 (3)0.6158 (3)−0.0002 (4)0.087 (3)
O42C0.7457 (4)0.0960 (4)−0.0805 (4)0.111 (3)
O42D0.5606 (3)0.6355 (4)0.0996 (3)0.100 (3)
N1C0.9779 (2)0.2952 (3)0.3310 (2)0.0397 (16)
N1D0.9879 (2)0.4909 (3)0.3227 (2)0.0410 (16)
N41C0.7239 (3)0.1135 (5)−0.0243 (4)0.095 (3)
N41D0.6136 (3)0.6286 (4)0.0638 (4)0.072 (3)
C2C0.9348 (3)0.2378 (4)0.3602 (3)0.0467 (19)
C2D1.0279 (3)0.5244 (4)0.2716 (3)0.060 (2)
C3C0.9099 (3)0.1676 (4)0.3250 (3)0.050 (2)
C3D1.0007 (3)0.5839 (4)0.2253 (3)0.056 (2)
C4C0.9291 (3)0.1548 (4)0.2565 (4)0.048 (2)
C4D0.9294 (3)0.6108 (3)0.2306 (3)0.0383 (19)
C5C0.9721 (3)0.2143 (4)0.2250 (3)0.0510 (19)
C5D0.8890 (3)0.5774 (4)0.2850 (3)0.055 (2)
C6C0.9953 (3)0.2838 (4)0.2631 (3)0.054 (2)
C6D0.9198 (3)0.5191 (3)0.3297 (3)0.053 (2)
C11C0.8593 (3)0.0910 (3)0.1544 (3)0.0437 (19)
C11D0.8235 (3)0.6580 (3)0.1517 (3)0.0400 (19)
C21C0.8846 (3)0.0790 (4)0.0877 (4)0.056 (3)
C21D0.8159 (3)0.6233 (3)0.0871 (3)0.040 (2)
C31C0.8426 (3)0.0866 (4)0.0299 (4)0.060 (3)
C31D0.7475 (3)0.6113 (3)0.0565 (4)0.049 (2)
C41C0.7692 (3)0.1101 (4)0.0397 (4)0.058 (3)
C41D0.6878 (3)0.6352 (4)0.0956 (3)0.044 (2)
C42C0.9073 (4)0.0765 (4)0.2176 (3)0.061 (3)
C42D0.8996 (3)0.6763 (4)0.1819 (3)0.049 (2)
C51C0.7415 (4)0.1250 (5)0.1052 (4)0.085 (4)
C51D0.6927 (3)0.6680 (4)0.1617 (3)0.050 (2)
C61C0.7878 (3)0.1152 (4)0.1627 (4)0.069 (3)
C61D0.7615 (3)0.6803 (3)0.1900 (4)0.051 (2)
H2A0.860700.170800.847500.0770*
H2B1.050400.038300.947500.0500*
H3A0.792500.271800.900200.0770*
H3B1.01130−0.067601.018100.0540*
H5A0.976500.385500.957600.0800*
H5B0.86700−0.133000.870900.0540*
H6A1.042800.279000.905200.0690*
H6B0.90830−0.025000.803400.0530*
H21A0.707900.367401.025900.1180*
H21B0.76920−0.193700.953500.0590*
H31A0.674700.362201.139900.1280*
H31B0.65800−0.155201.001600.0630*
H42A0.860900.462300.966600.0960*
H42B0.94180−0.193101.036700.0540*
H43A0.788500.418600.941300.0960*
H43B0.89930−0.232700.973100.0540*
H51A0.880200.394101.200900.0860*
H51B0.76080−0.088901.178900.0500*
H61A0.913700.410401.082900.0820*
H61B0.87270−0.119201.127900.0570*
H2C0.920800.245200.406700.0560*
H2D1.076400.507100.266700.0720*
H3C0.879900.129000.347900.0600*
H3D1.030900.605800.190400.0670*
H5C0.985700.208200.178200.0610*
H5D0.840600.594300.291600.0660*
H60.891400.498600.366500.0630*
H6C1.023900.324100.240700.0650*
H21C0.933700.064700.081900.0670*
H21D0.857700.607000.062500.0480*
H31C0.861600.07670−0.014700.0720*
H31D0.742400.588100.011900.0580*
H42C0.881500.039600.249800.0730*
H42D0.933700.683000.143100.0590*
H43C0.951500.047600.202500.0730*
H43D0.897600.729400.206800.0590*
H51C0.692900.141300.111200.1020*
H51D0.650600.681700.187000.0600*
H61C0.769700.125200.207700.0830*
H61D0.766500.703400.234600.0610*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0442 (2)0.0799 (3)0.0313 (2)−0.0069 (2)−0.0057 (2)0.0026 (2)
I20.0398 (2)0.0944 (3)0.0359 (2)−0.0126 (2)−0.0025 (2)0.0057 (2)
Zn10.0402 (3)0.0605 (4)0.0289 (4)−0.0065 (3)−0.0014 (3)0.0019 (3)
O41A0.108 (6)0.285 (11)0.143 (8)0.053 (6)0.055 (5)0.074 (6)
O41B0.081 (3)0.107 (4)0.042 (3)0.013 (3)0.015 (3)−0.013 (3)
O42A0.097 (4)0.186 (6)0.085 (5)0.013 (5)0.010 (4)0.029 (5)
O42B0.048 (3)0.181 (6)0.070 (4)0.016 (3)0.000 (3)−0.004 (4)
N1A0.046 (3)0.055 (3)0.031 (3)−0.008 (2)−0.001 (2)−0.005 (2)
N1B0.036 (2)0.054 (3)0.028 (3)−0.002 (2)−0.001 (2)0.003 (2)
N41A0.100 (6)0.260 (12)0.079 (7)0.001 (8)0.027 (5)0.046 (8)
N41B0.068 (4)0.062 (4)0.051 (4)0.005 (3)0.011 (3)0.002 (3)
C2A0.061 (4)0.063 (4)0.068 (5)−0.004 (3)0.005 (4)−0.009 (4)
C2B0.036 (3)0.058 (4)0.030 (3)−0.006 (3)−0.001 (3)0.000 (3)
C3A0.057 (4)0.070 (5)0.067 (5)0.009 (4)−0.003 (3)−0.007 (4)
C3B0.036 (3)0.070 (4)0.028 (3)0.004 (3)−0.001 (3)0.002 (3)
C4A0.062 (4)0.056 (4)0.041 (4)0.013 (4)0.010 (3)0.005 (3)
C4B0.036 (3)0.047 (4)0.032 (4)0.007 (3)0.006 (3)−0.004 (3)
C5A0.084 (5)0.066 (5)0.049 (4)−0.013 (4)−0.002 (4)−0.006 (4)
C5B0.043 (3)0.050 (4)0.041 (4)−0.008 (3)−0.008 (3)−0.002 (3)
C6A0.057 (4)0.072 (5)0.045 (4)−0.001 (4)−0.003 (3)−0.003 (3)
C6B0.046 (3)0.059 (4)0.027 (3)−0.004 (3)−0.009 (2)0.002 (3)
C11A0.063 (4)0.055 (4)0.049 (5)0.023 (3)−0.007 (4)−0.008 (3)
C11B0.038 (3)0.031 (3)0.034 (4)0.003 (3)0.006 (2)0.002 (3)
C21A0.048 (4)0.168 (9)0.079 (7)0.006 (5)−0.014 (4)−0.020 (6)
C21B0.044 (3)0.064 (4)0.039 (4)0.004 (3)0.001 (3)−0.007 (3)
C31A0.056 (5)0.196 (10)0.068 (6)−0.019 (6)0.003 (4)0.014 (7)
C31B0.044 (3)0.066 (4)0.046 (4)0.003 (3)−0.013 (3)−0.001 (3)
C41A0.063 (4)0.108 (6)0.064 (6)0.008 (4)0.005 (4)0.004 (5)
C41B0.041 (3)0.036 (4)0.042 (4)0.007 (3)0.008 (3)0.005 (3)
C42A0.090 (5)0.062 (5)0.089 (6)0.034 (4)−0.017 (5)−0.002 (4)
C42B0.045 (3)0.041 (3)0.050 (4)0.003 (3)−0.004 (3)0.006 (3)
C51A0.050 (4)0.096 (6)0.069 (6)0.012 (4)−0.003 (4)0.000 (4)
C51B0.059 (4)0.039 (4)0.027 (4)0.005 (3)0.007 (3)0.005 (3)
C61A0.049 (4)0.080 (5)0.076 (6)0.004 (4)0.000 (4)0.000 (4)
C61B0.046 (3)0.053 (4)0.045 (4)−0.006 (3)−0.005 (3)0.006 (3)
I30.0382 (2)0.0769 (3)0.0405 (3)0.0048 (2)−0.0001 (2)−0.0048 (2)
I40.0483 (2)0.0798 (3)0.0335 (2)0.0107 (2)0.0042 (2)0.0021 (2)
Zn20.0391 (3)0.0570 (5)0.0317 (4)0.0012 (3)−0.0014 (3)0.0019 (3)
O41D0.075 (3)0.112 (5)0.075 (5)−0.010 (3)−0.030 (3)0.002 (3)
O42C0.101 (4)0.171 (6)0.062 (5)−0.020 (4)−0.020 (4)0.002 (4)
O42D0.045 (3)0.154 (5)0.100 (5)0.004 (3)0.000 (3)−0.028 (4)
N1C0.035 (2)0.049 (3)0.035 (3)−0.003 (2)0.003 (2)−0.001 (2)
N1D0.038 (2)0.056 (3)0.029 (3)0.001 (2)0.001 (2)0.003 (2)
N41C0.049 (4)0.158 (7)0.077 (6)−0.013 (4)−0.012 (4)0.017 (5)
N41D0.057 (4)0.086 (5)0.073 (5)−0.001 (3)−0.016 (4)0.001 (4)
C2C0.044 (3)0.062 (4)0.034 (3)0.007 (3)0.003 (3)−0.001 (3)
C2D0.035 (3)0.086 (5)0.060 (4)0.013 (3)0.006 (3)0.019 (4)
C3C0.050 (3)0.056 (4)0.044 (4)−0.008 (3)0.003 (3)0.011 (3)
C3D0.037 (3)0.081 (5)0.050 (4)−0.002 (3)0.011 (3)0.031 (4)
C4C0.045 (3)0.044 (4)0.055 (5)0.002 (3)−0.018 (3)0.008 (3)
C4D0.047 (3)0.040 (4)0.028 (3)−0.007 (3)−0.004 (3)0.002 (3)
C5C0.055 (3)0.065 (4)0.033 (3)−0.003 (3)0.003 (3)−0.004 (3)
C5D0.043 (3)0.074 (5)0.047 (4)0.011 (3)0.010 (3)0.020 (4)
C6C0.045 (3)0.074 (5)0.043 (4)−0.010 (3)−0.003 (3)0.007 (3)
C6D0.046 (3)0.069 (4)0.043 (4)−0.003 (3)0.003 (3)0.012 (3)
C11C0.044 (3)0.035 (3)0.052 (4)−0.004 (3)−0.006 (3)−0.007 (3)
C11D0.043 (3)0.038 (3)0.039 (4)−0.010 (3)−0.002 (3)0.017 (3)
C21C0.048 (3)0.066 (5)0.054 (5)0.006 (3)0.003 (3)−0.005 (4)
C21D0.051 (3)0.039 (4)0.030 (4)0.002 (3)0.006 (3)−0.001 (3)
C31C0.051 (4)0.072 (5)0.056 (5)−0.003 (3)0.009 (3)−0.001 (4)
C31D0.054 (3)0.054 (4)0.038 (4)0.006 (3)−0.007 (3)−0.003 (3)
C41C0.045 (3)0.082 (5)0.048 (5)−0.016 (3)−0.015 (3)0.006 (4)
C41D0.043 (3)0.046 (4)0.042 (4)0.005 (3)−0.009 (3)−0.002 (3)
C42C0.083 (5)0.050 (4)0.049 (4)0.001 (3)−0.011 (4)−0.009 (3)
C42D0.047 (3)0.062 (4)0.038 (4)−0.002 (3)0.002 (3)0.002 (3)
C51C0.042 (4)0.160 (8)0.054 (6)0.012 (4)0.007 (4)−0.003 (5)
C51D0.040 (3)0.060 (4)0.050 (4)0.004 (3)0.006 (3)0.002 (3)
C61C0.053 (4)0.107 (6)0.048 (5)0.004 (4)0.014 (3)−0.011 (4)
C61D0.057 (4)0.064 (4)0.031 (3)−0.004 (3)0.006 (3)−0.004 (3)
Geometric parameters (Å, º) top
I1—Zn12.5578 (7)C6A—H6A0.9300
I2—Zn12.5525 (7)C6B—H6B0.9300
I3—Zn22.5666 (7)C21A—H21A0.9300
I4—Zn22.5472 (8)C21B—H21B0.9300
Zn1—N1A2.052 (4)C31A—H31A0.9300
Zn1—N1B2.052 (4)C31B—H31B0.9300
Zn2—N1C2.044 (4)C42A—H42A0.9700
Zn2—N1D2.048 (4)C42A—H43A0.9700
O41A—N41A1.280 (13)C42B—H42B0.9700
O41B—N41B1.207 (9)C42B—H43B0.9700
O42A—N41A1.207 (13)C51A—H51A0.9300
O42B—N41B1.217 (8)C51B—H51B0.9300
O41C—N41C1.280 (9)C61A—H61A0.9300
O41D—N41D1.236 (11)C61B—H61B0.9300
O42C—N41C1.174 (11)C2C—C3C1.379 (9)
O42D—N41D1.187 (8)C2D—C3D1.385 (8)
N1A—C2A1.348 (7)C3C—C4C1.365 (9)
N1A—C6A1.324 (7)C3D—C4D1.371 (8)
N1B—C2B1.350 (7)C4C—C5C1.367 (9)
N1B—C6B1.347 (7)C4C—C42C1.502 (9)
N41A—C41A1.495 (13)C4D—C5D1.377 (8)
N41B—C41B1.476 (8)C4D—C42D1.496 (8)
N1C—C6C1.343 (7)C5C—C6C1.388 (9)
N1C—C2C1.326 (7)C5D—C6D1.378 (8)
N1D—C6D1.325 (7)C11C—C21C1.364 (9)
N1D—C2D1.327 (7)C11C—C42C1.505 (8)
N41C—C41C1.472 (10)C11C—C61C1.367 (8)
N41D—C41D1.484 (8)C11D—C21D1.355 (8)
C2A—C3A1.354 (8)C11D—C42D1.528 (8)
C2B—C3B1.365 (8)C11D—C61D1.390 (8)
C3A—C4A1.375 (9)C21C—C31C1.345 (10)
C3B—C4B1.377 (8)C21D—C31D1.388 (8)
C4A—C5A1.346 (10)C31C—C41C1.400 (8)
C4A—C42A1.527 (9)C31D—C41D1.371 (8)
C4B—C42B1.507 (7)C41C—C51C1.366 (11)
C4B—C5B1.377 (8)C41D—C51D1.365 (8)
C5A—C6A1.390 (9)C51C—C61C1.390 (10)
C5B—C6B1.369 (8)C51D—C61D1.378 (8)
C11A—C61A1.377 (11)C2C—H2C0.9300
C11A—C21A1.331 (10)C2D—H2D0.9300
C11A—C42A1.505 (11)C3C—H3C0.9300
C11B—C42B1.516 (8)C3D—H3D0.9300
C11B—C61B1.384 (9)C5C—H5C0.9300
C11B—C21B1.390 (8)C5D—H5D0.9300
C21A—C31A1.331 (13)C6C—H6C0.9300
C21B—C31B1.372 (8)C6D—H60.9300
C31A—C41A1.346 (12)C21C—H21C0.9300
C31B—C41B1.370 (8)C21D—H21D0.9300
C41A—C51A1.354 (10)C31C—H31C0.9300
C41B—C51B1.368 (8)C31D—H31D0.9300
C51A—C61A1.392 (12)C42C—H42C0.9700
C51B—C61B1.376 (8)C42C—H43C0.9700
C2A—H2A0.9300C42D—H42D0.9700
C2B—H2B0.9300C42D—H43D0.9700
C3A—H3A0.9300C51C—H51C0.9300
C3B—H3B0.9300C51D—H51D0.9300
C5A—H5A0.9300C61C—H61C0.9300
C5B—H5B0.9300C61D—H61D0.9300
I1—Zn1—I2119.96 (2)C4A—C42A—H43A109.00
I1—Zn1—N1A105.83 (11)C4A—C42A—H42A109.00
I1—Zn1—N1B111.55 (11)H42A—C42A—H43A108.00
I2—Zn1—N1A110.54 (11)C11A—C42A—H43A109.00
I2—Zn1—N1B107.94 (11)C11A—C42A—H42A109.00
N1A—Zn1—N1B98.99 (17)C11B—C42B—H42B109.00
I4—Zn2—N1D110.49 (11)C4B—C42B—H43B109.00
N1C—Zn2—N1D99.42 (17)C4B—C42B—H42B109.00
I3—Zn2—I4120.39 (3)C11B—C42B—H43B109.00
I3—Zn2—N1C104.77 (11)H42B—C42B—H43B108.00
I3—Zn2—N1D109.76 (11)C41A—C51A—H51A121.00
I4—Zn2—N1C109.83 (11)C61A—C51A—H51A121.00
Zn1—N1A—C6A123.6 (3)C61B—C51B—H51B120.00
C2A—N1A—C6A117.3 (5)C41B—C51B—H51B120.00
Zn1—N1A—C2A118.9 (4)C11A—C61A—H61A120.00
Zn1—N1B—C6B124.1 (3)C51A—C61A—H61A120.00
Zn1—N1B—C2B119.9 (3)C11B—C61B—H61B120.00
C2B—N1B—C6B115.9 (4)C51B—C61B—H61B120.00
O41A—N41A—C41A112.9 (8)N1C—C2C—C3C123.3 (5)
O41A—N41A—O42A126.1 (9)N1D—C2D—C3D123.0 (5)
O42A—N41A—C41A120.7 (9)C2C—C3C—C4C120.0 (6)
O42B—N41B—C41B118.6 (7)C2D—C3D—C4D120.4 (5)
O41B—N41B—O42B122.8 (6)C3C—C4C—C5C117.6 (6)
O41B—N41B—C41B118.6 (6)C3C—C4C—C42C121.8 (6)
Zn2—N1C—C2C124.7 (4)C5C—C4C—C42C120.6 (6)
Zn2—N1C—C6C118.4 (4)C3D—C4D—C5D116.2 (5)
C2C—N1C—C6C116.8 (5)C3D—C4D—C42D121.0 (5)
Zn2—N1D—C2D122.5 (4)C5D—C4D—C42D122.7 (5)
Zn2—N1D—C6D120.5 (3)C4C—C5C—C6C119.8 (6)
C2D—N1D—C6D116.8 (5)C4D—C5D—C6D120.4 (5)
O41C—N41C—O42C125.2 (7)N1C—C6C—C5C122.6 (5)
O41C—N41C—C41C110.9 (7)N1D—C6D—C5D123.1 (5)
O42C—N41C—C41C123.8 (6)C21C—C11C—C42C121.8 (5)
O41D—N41D—C41D116.9 (6)C21C—C11C—C61C118.0 (6)
O42D—N41D—C41D120.0 (7)C42C—C11C—C61C120.3 (6)
O41D—N41D—O42D123.1 (6)C21D—C11D—C42D120.8 (5)
N1A—C2A—C3A123.5 (5)C21D—C11D—C61D119.8 (5)
N1B—C2B—C3B123.2 (5)C42D—C11D—C61D119.4 (5)
C2A—C3A—C4A119.0 (5)C11C—C21C—C31C123.8 (5)
C2B—C3B—C4B120.6 (5)C11D—C21D—C31D121.9 (5)
C3A—C4A—C5A118.2 (6)C21C—C31C—C41C117.2 (7)
C3A—C4A—C42A120.1 (6)C21D—C31D—C41D116.5 (6)
C5A—C4A—C42A121.5 (6)N41C—C41C—C31C115.8 (6)
C3B—C4B—C5B116.7 (5)N41C—C41C—C51C122.8 (6)
C3B—C4B—C42B121.4 (5)C31C—C41C—C51C121.4 (7)
C5B—C4B—C42B121.9 (5)N41D—C41D—C31D118.7 (6)
C4A—C5A—C6A120.5 (6)N41D—C41D—C51D117.5 (5)
C4B—C5B—C6B120.2 (5)C31D—C41D—C51D123.7 (5)
N1A—C6A—C5A121.4 (5)C4C—C42C—C11C114.9 (5)
N1B—C6B—C5B123.4 (5)C4D—C42D—C11D115.4 (5)
C21A—C11A—C42A120.6 (7)C41C—C51C—C61C118.4 (6)
C42A—C11A—C61A118.8 (6)C41D—C51D—C61D118.3 (5)
C21A—C11A—C61A120.5 (8)C11C—C61C—C51C121.2 (7)
C21B—C11B—C61B118.2 (5)C11D—C61D—C51D119.8 (6)
C42B—C11B—C61B121.9 (5)N1C—C2C—H2C118.00
C21B—C11B—C42B119.9 (5)C3C—C2C—H2C118.00
C11A—C21A—C31A119.6 (8)N1D—C2D—H2D118.00
C11B—C21B—C31B121.7 (6)C3D—C2D—H2D119.00
C21A—C31A—C41A121.9 (7)C2C—C3C—H3C120.00
C21B—C31B—C41B118.1 (5)C4C—C3C—H3C120.00
N41A—C41A—C51A117.2 (8)C2D—C3D—H3D120.00
C31A—C41A—C51A120.5 (9)C4D—C3D—H3D120.00
N41A—C41A—C31A122.3 (8)C4C—C5C—H5C120.00
N41B—C41B—C51B119.5 (5)C6C—C5C—H5C120.00
C31B—C41B—C51B122.1 (5)C4D—C5D—H5D120.00
N41B—C41B—C31B118.4 (5)C6D—C5D—H5D120.00
C4A—C42A—C11A113.5 (5)N1C—C6C—H6C119.00
C4B—C42B—C11B111.8 (4)C5C—C6C—H6C119.00
C41A—C51A—C61A117.9 (8)N1D—C6D—H6119.00
C41B—C51B—C61B119.1 (6)C5D—C6D—H6118.00
C11A—C61A—C51A119.4 (7)C11C—C21C—H21C118.00
C11B—C61B—C51B120.8 (5)C31C—C21C—H21C118.00
N1A—C2A—H2A118.00C11D—C21D—H21D119.00
C3A—C2A—H2A118.00C31D—C21D—H21D119.00
N1B—C2B—H2B118.00C21C—C31C—H31C121.00
C3B—C2B—H2B118.00C41C—C31C—H31C121.00
C2A—C3A—H3A120.00C21D—C31D—H31D122.00
C4A—C3A—H3A121.00C41D—C31D—H31D122.00
C4B—C3B—H3B120.00C4C—C42C—H42C109.00
C2B—C3B—H3B120.00C4C—C42C—H43C109.00
C4A—C5A—H5A120.00C11C—C42C—H42C108.00
C6A—C5A—H5A120.00C11C—C42C—H43C109.00
C4B—C5B—H5B120.00H42C—C42C—H43C108.00
C6B—C5B—H5B120.00C4D—C42D—H42D108.00
N1A—C6A—H6A119.00C4D—C42D—H43D108.00
C5A—C6A—H6A119.00C11D—C42D—H42D108.00
C5B—C6B—H6B118.00C11D—C42D—H43D108.00
N1B—C6B—H6B118.00H42D—C42D—H43D107.00
C11A—C21A—H21A120.00C41C—C51C—H51C121.00
C31A—C21A—H21A120.00C61C—C51C—H51C121.00
C11B—C21B—H21B119.00C41D—C51D—H51D121.00
C31B—C21B—H21B119.00C61D—C51D—H51D121.00
C41A—C31A—H31A119.00C11C—C61C—H61C119.00
C21A—C31A—H31A119.00C51C—C61C—H61C119.00
C21B—C31B—H31B121.00C11D—C61D—H61D120.00
C41B—C31B—H31B121.00C51D—C61D—H61D120.00
I1—Zn1—N1A—C2A49.9 (4)C5B—C4B—C42B—C11B−76.6 (7)
I1—Zn1—N1A—C6A−124.7 (4)C3B—C4B—C42B—C11B102.9 (6)
I2—Zn1—N1A—C2A−178.7 (4)C4A—C5A—C6A—N1A1.8 (10)
I2—Zn1—N1A—C6A6.7 (5)C4B—C5B—C6B—N1B−0.3 (9)
N1B—Zn1—N1A—C2A−65.6 (4)C42A—C11A—C61A—C51A175.8 (6)
N1B—Zn1—N1A—C6A119.8 (4)C61A—C11A—C21A—C31A5.3 (13)
I1—Zn1—N1B—C2B173.9 (3)C21A—C11A—C42A—C4A−108.2 (8)
I1—Zn1—N1B—C6B−9.9 (4)C42A—C11A—C21A—C31A−173.0 (8)
I2—Zn1—N1B—C2B40.1 (4)C21A—C11A—C61A—C51A−2.6 (10)
I2—Zn1—N1B—C6B−143.7 (4)C61A—C11A—C42A—C4A73.5 (8)
N1A—Zn1—N1B—C2B−75.0 (4)C61B—C11B—C21B—C31B2.3 (8)
N1A—Zn1—N1B—C6B101.1 (4)C42B—C11B—C21B—C31B−179.1 (5)
I3—Zn2—N1D—C6D−171.8 (4)C21B—C11B—C42B—C4B83.4 (6)
I4—Zn2—N1D—C2D148.3 (4)C61B—C11B—C42B—C4B−98.1 (6)
I4—Zn2—N1D—C6D−36.8 (4)C21B—C11B—C61B—C51B0.1 (8)
N1C—Zn2—N1D—C2D−96.3 (4)C42B—C11B—C61B—C51B−178.5 (5)
N1C—Zn2—N1D—C6D78.6 (4)C11A—C21A—C31A—C41A−5.6 (14)
I4—Zn2—N1C—C2C−9.4 (5)C11B—C21B—C31B—C41B−3.8 (9)
I4—Zn2—N1C—C6C175.3 (4)C21A—C31A—C41A—N41A−180.0 (9)
N1D—Zn2—N1C—C2C−125.4 (4)C21A—C31A—C41A—C51A3.1 (14)
N1D—Zn2—N1C—C6C59.4 (4)C21B—C31B—C41B—N41B−176.0 (5)
I3—Zn2—N1D—C2D13.3 (5)C21B—C31B—C41B—C51B2.9 (8)
I3—Zn2—N1C—C2C121.2 (4)C31A—C41A—C51A—C61A−0.3 (11)
I3—Zn2—N1C—C6C−54.1 (4)N41A—C41A—C51A—C61A−177.4 (7)
C2A—N1A—C6A—C5A−1.1 (8)N41B—C41B—C51B—C61B178.2 (5)
Zn1—N1A—C6A—C5A173.6 (5)C31B—C41B—C51B—C61B−0.7 (8)
Zn1—N1A—C2A—C3A−174.7 (5)C41A—C51A—C61A—C11A0.1 (10)
C6A—N1A—C2A—C3A0.2 (8)C41B—C51B—C61B—C11B−0.9 (9)
Zn1—N1B—C6B—C5B−173.9 (4)N1C—C2C—C3C—C4C−0.4 (9)
C2B—N1B—C6B—C5B2.4 (8)N1D—C2D—C3D—C4D−0.3 (9)
Zn1—N1B—C2B—C3B173.8 (4)C2C—C3C—C4C—C5C−1.1 (9)
C6B—N1B—C2B—C3B−2.7 (8)C2C—C3C—C4C—C42C176.0 (6)
O41A—N41A—C41A—C51A163.4 (8)C2D—C3D—C4D—C5D2.0 (8)
O41A—N41A—C41A—C31A−13.6 (13)C2D—C3D—C4D—C42D178.8 (5)
O42A—N41A—C41A—C31A172.3 (9)C3C—C4C—C5C—C6C0.9 (9)
O42A—N41A—C41A—C51A−10.7 (13)C42C—C4C—C5C—C6C−176.2 (6)
O41B—N41B—C41B—C31B164.8 (5)C3C—C4C—C42C—C11C118.7 (6)
O42B—N41B—C41B—C31B−12.7 (8)C5C—C4C—C42C—C11C−64.4 (8)
O42B—N41B—C41B—C51B168.3 (5)C3D—C4D—C5D—C6D−1.3 (8)
O41B—N41B—C41B—C51B−14.2 (7)C42D—C4D—C5D—C6D−178.0 (5)
Zn2—N1C—C6C—C5C173.4 (4)C3D—C4D—C42D—C11D135.3 (6)
Zn2—N1C—C2C—C3C−173.3 (4)C5D—C4D—C42D—C11D−48.1 (8)
C6C—N1C—C2C—C3C2.1 (8)C4C—C5C—C6C—N1C0.8 (9)
C2C—N1C—C6C—C5C−2.2 (8)C4D—C5D—C6D—N1D−1.3 (9)
Zn2—N1D—C2D—C3D172.8 (4)C42C—C11C—C21C—C31C176.1 (6)
C6D—N1D—C2D—C3D−2.3 (8)C61C—C11C—C21C—C31C−2.5 (9)
C2D—N1D—C6D—C5D3.1 (8)C21C—C11C—C42C—C4C110.0 (6)
Zn2—N1D—C6D—C5D−172.2 (4)C61C—C11C—C42C—C4C−71.4 (7)
O42C—N41C—C41C—C31C1.9 (11)C21C—C11C—C61C—C51C1.8 (9)
O42C—N41C—C41C—C51C−175.3 (8)C42C—C11C—C61C—C51C−176.9 (6)
O41C—N41C—C41C—C31C−175.3 (6)C42D—C11D—C21D—C31D−175.6 (5)
O41C—N41C—C41C—C51C7.5 (10)C61D—C11D—C21D—C31D1.9 (8)
O41D—N41D—C41D—C51D165.3 (6)C21D—C11D—C42D—C4D−97.1 (6)
O42D—N41D—C41D—C31D167.7 (6)C61D—C11D—C42D—C4D85.4 (6)
O42D—N41D—C41D—C51D−14.8 (10)C21D—C11D—C61D—C51D−0.8 (8)
O41D—N41D—C41D—C31D−12.3 (9)C42D—C11D—C61D—C51D176.7 (5)
N1A—C2A—C3A—C4A0.1 (9)C11C—C21C—C31C—C41C1.5 (10)
N1B—C2B—C3B—C4B0.9 (9)C11D—C21D—C31D—C41D−1.0 (8)
C2A—C3A—C4A—C42A177.2 (6)C21C—C31C—C41C—N41C−176.9 (6)
C2A—C3A—C4A—C5A0.5 (9)C21C—C31C—C41C—C51C0.3 (10)
C2B—C3B—C4B—C42B−178.2 (5)C21D—C31D—C41D—N41D176.4 (5)
C2B—C3B—C4B—C5B1.3 (8)C21D—C31D—C41D—C51D−1.1 (9)
C3A—C4A—C42A—C11A89.9 (7)N41C—C41C—C51C—C61C176.1 (7)
C42A—C4A—C5A—C6A−178.1 (6)C31C—C41C—C51C—C61C−0.9 (11)
C3A—C4A—C5A—C6A−1.4 (10)N41D—C41D—C51D—C61D−175.3 (6)
C5A—C4A—C42A—C11A−93.5 (8)C31D—C41D—C51D—C61D2.1 (10)
C3B—C4B—C5B—C6B−1.6 (8)C41C—C51C—C61C—C11C−0.2 (10)
C42B—C4B—C5B—C6B177.9 (5)C41D—C51D—C61D—C11D−1.1 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O41Di0.932.573.211 (9)126
C6B—H6B···O41Bii0.932.493.295 (8)145
Symmetry codes: (i) x+1/2, −y+1, z+1; (ii) −x+3/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula[ZnI2(C12H10N2O2)2]
Mr747.61
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)200
a, b, c (Å)18.2091 (2), 15.8998 (3), 19.0327 (3)
V (Å3)5510.37 (15)
Z8
Radiation typeMo Kα
µ (mm−1)3.17
Crystal size (mm)0.40 × 0.22 × 0.15
Data collection
DiffractometerOxford Diffraction Gemini-S Ultra CCD detector
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.865, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		18536, 10102, 7499
Rint0.024
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.056, 0.89
No. of reflections10102
No. of parameters627
No. of restraints25
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å−3)0.63, −0.47
Absolute structureFlack (1983), 4516 Friedel pairs
Absolute structure parameter0.430 (14)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

 

Acknowledgements

The authors acknowledge financial support from the Australian Research Committee, the Faculty of Science and Technology and the University Library, Queensland University of Technology, and the School of Biomolecular and Physical Sciences, Griffith University.

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 3| March 2011| Page m359
doi:10.1107/S1600536811005939
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