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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 68| Part 3| March 2012| Page o777
doi:10.1107/S1600536812006575

N-Benzyl­isatin

M. Schutte,a* H. G. Visser,a A. Roodta and H. Brabandb

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa, and bInstitute of Inorganic Chemistry, University of Zurich, Winterthurerestrasse 190, CH-8057 Zurich, Switzerland
*Correspondence e-mail: schuttem@ufs.ac.za

(Received 31 January 2012; accepted 14 February 2012; online 17 February 2012)

In the title compound, C15H11NO2, two C—H⋯O hydrogen bonds are observed in the crystal structure, as well as π–π stacking with a centroid–centroid distance of 3.623 (2) Å. The planarity of the two ring systems is illustrated by very small deviations of all the atoms from these planes [largest deviations = 0.003 (3) and 0.010 (3) Å for the phenyl and fused-benzene rings, respectively]. The dihedral angle between these two planes is 77.65 (9)°.

Related literature

For literature regarding the biological properties of N-benzyl­isatin, see: Palmer et al. (1987[Palmer, M. H., Blake, A. J. & Gould, R. O. (1987). Chem. Phys. 115, 219-227.]); Goldschmidt & Llewellyn (1950[Goldschmidt, G. H. & Llewellyn, F. J. (1950). Acta Cryst. 3, 294-305.]); Wei et al. (2004[Wei, H.-X., Zhou, C., Ham, S., White, J. M. & Birney, D. M. (2004). Org. Lett. 6, 4289-4292.]); Frolova et al. (1988[Frolova, N. A., Kravtsov, V. Kh., Biyushkin, V. N., Chumakov, Yu. M., Bel'kova, O. N. & Malinovskii, T. I. (1988). Zh. Strukt. Khim. 29, 155-158.]); Akkurt et al. (2006[Akkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575-o1577.]). For background regarding the functionalization of isatin, see: Schutte (2011[Schutte, M. (2011). PhD thesis, University of the Free State, Bloemfontein, South Africa.]). For a similar structure, see: Akkurt et al. (2006[Akkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575-o1577.]).

[Scheme 1]

Experimental

Crystal data

  • C15H11NO2

  • Mr = 237.25

  • Monoclinic, P 21

  • a = 6.5766 (5) Å

  • b = 4.8877 (4) Å

  • c = 18.2211 (13) Å

  • β = 98.316 (7)°

  • V = 579.55 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 183 K

  • 0.34 × 0.07 × 0.02 mm
Data collection

  • Oxford Xcalibur Ruby CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.881, Tmax = 0.921

  • 5347 measured reflections

  • 2095 independent reflections

  • 1264 reflections with I > 2σ(I)

  • Rint = 0.068
Refinement

  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.128

  • S = 0.99

  • 2095 reflections

  • 163 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯O2i 0.95 2.41 3.213 (5) 143
C9—H9A⋯O2ii 0.99 2.59 3.525 (4) 159
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006575/ez2282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006575/ez2282Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006575/ez2282Isup3.cml

checkCIF report


Comment top

The molecule isatin has a variety of biological activities. It can cause anxiety but can also be used as a sedative. It can also act as an anticonvulsant agent and can block the binding of an agonist at the atrial natriuretic peptide receptors (Palmer et al., 1987; Goldschmidt & Llewellyn, 1950; Wei et al., 2004; Frolova et al., 1988; Akkurt et al., 2006). Benzylisatin was synthesized to explore the reactivity of the amide group in the isatin molecule and to investigate its possible biological reactivity as free ligand or as bidentate ligand as part of the Re(I) tricarbonyl complex. The coordination of bi- and tridentate ligand systems to the Re(I) tricarbonyl synthon is part of an ongoing study. The amide group was functionalized in the isatin molecule to illustrate the pH dependent keto-enol tautomerisation of the molecule to coordinate in a bidentate fashion to the Re(I) metal centre. By functionalizing the amide, keto-enol tautomerisation is no longer possible and the derivatized isatin cannot coordinate to the Re(I) core (Schutte, 2011).

The title compound, N-benzylisatin, crystallized in the monoclinic spacegroup P21 with one molecule in the asymmetric unit. The carbonyl carbon to oxygen distances of 1.221 (5) Å and 1.209 (4) Å compare well with the structure of Akkurt et al. (2006) of 1.2061 (18) Å and 1.2091 (17) Å, and the rest of the bond distances and angles of the two structures are also similar. The torsion angles C15—C10—C9—N1 and O1—C8—C7—O2 are 57.0 (5) ° and 0.5 (6) ° for this structure and 53.41 (16) ° and 1.7 (2) ° for the reported structure by Akkurt et al. (2006), respectively. The planarity of the two ring systems, C10—C11—C12—C13—C14—C15 and N1—C1—C2—C3—C4—C5—C6—C7—C8, are illustrated by very small deviations of all the atoms from these planes, with the largest deviations 0.003 (3) Å for C13 and 0.010 (3) for C4 respectively. The isatin group in the structure of Akkurt et al. is almost planar, with a maximum deviation of 0.058 (1) Å for atom O2. The dihedral angle between the two planes is calculated as 77.65 (9) ° in this structure and 87.08 (5) ° in the structure of Akkurt et al..

The main difference between the structure of N-benzylisatin reported here and that by Akkurt et al. is the packing as a result of the different space groups, P21 and P21/c, respectively. In this structure report, the benzylisatin molecules pack in a head-to-toe fashion along the a axis and in layers when viewed along the b axis (Figure 2). In the structure by Akkurt et al. the molecules pack in a staggered head-to-head fashion when viewed along the c axis.

Three C—H···O hydrogen bonds are observed in the structure of N-benzylisatin. One is an intramolecular hydrogen bond and the other two are intermolecular hydrogen bonds to two neighbouring molecules. Some π-stacking is observed in the crystal structure of N-benzylisatin between neighbouring molecules, with a centroid-to-centroid distance of 3.623 (2) Å. This is illustrated in Figure 3.

Related literature top

For literature regarding the biological properties of N-benzylisatin, see: Palmer et al. (1987); Goldschmidt & Llewellyn (1950); Wei et al. (2004); Frolova et al. (1988); Akkurt et al. (2006). For background regarding the functionalization of isatin, see: Schutte (2011). For a similar structure, see: Akkurt et al. (2006).

Experimental top

The preparation was performed under strict Schlenk conditions. Isatin (0.2 g, 1.36 mmol) was dissolved in dry dimethylformamide (3 ml). Powdered calcium hydride (0.191 g, 4.54 mmol) was added to the mixture and stirred at 45 °C for 30 minutes. Benzylchloride (0.258 ml, 2.04 mmol) was added to the mixture and stirred at room temperature for 16 h. The reaction mixture was dried, dissolved in ethylacetate and washed three times with water. The combined ethylacetate layers were dried with Na2SO4. The product was purified with column chromatography with DCM:Hex 1:1 as eluent and monitored with TLC. The resulting orange product was dried under vacuum. Orange crystals were grown from a methanol solution of the product.

Refinement top

Aromatic H atoms were positioned geometrically and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(parent) of the parent atom with a C—H distance of 0.95. The methene H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) and at a distance of 0.99 Å.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); 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: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Representation of the title compound, showing the numbering scheme and displacement ellipsoids (50% probability).
[Figure 2] Fig. 2. Packing of the title compound in the unit cell.
[Figure 3] Fig. 3. Observed π-π stacking in the crystal structure, indicated by dashed lines (hydrogen atoms omitted for clarity).
1-benzylindoline-2,3-dione top
Crystal data top
C15H11NO2F(000) = 248
Mr = 237.25Dx = 1.36 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.5766 (5) ÅCell parameters from 972 reflections
b = 4.8877 (4) Åθ = 3.1–29.2°
c = 18.2211 (13) ŵ = 0.09 mm−1
β = 98.316 (7)°T = 183 K
V = 579.55 (8) Å3Plate, orange
Z = 20.34 × 0.07 × 0.02 mm
Data collection top
Oxford Xcalibur Ruby CCD
diffractometer		2095 independent reflections
Graphite monochromator1264 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm-1Rint = 0.068
ο oscillation scanθmax = 25.3°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)		h = −7→7
Tmin = 0.881, Tmax = 0.921k = −5→5
5347 measured reflectionsl = −21→20
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0406P)2]
where P = (Fo2 + 2Fc2)/3
2095 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.15 e Å−3
1 restraintΔρmin = −0.19 e Å−3
Crystal data top
C15H11NO2V = 579.55 (8) Å3
Mr = 237.25Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.5766 (5) ŵ = 0.09 mm−1
b = 4.8877 (4) ÅT = 183 K
c = 18.2211 (13) Å0.34 × 0.07 × 0.02 mm
β = 98.316 (7)°
Data collection top
Oxford Xcalibur Ruby CCD
diffractometer		2095 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)		1264 reflections with I > 2σ(I)
Tmin = 0.881, Tmax = 0.921Rint = 0.068
5347 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0621 restraint
wR(F2) = 0.128H-atom parameters constrained
S = 0.99Δρmax = 0.15 e Å−3
2095 reflectionsΔρmin = −0.19 e Å−3
163 parameters
Special details top

Experimental. CrysAlis Pro (Oxford Diffraction Ltd, 2007) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C80.7610 (6)−0.1172 (9)0.7201 (2)0.0419 (11)
C70.6174 (6)0.0052 (8)0.6537 (2)0.0398 (10)
C60.7413 (5)0.2130 (8)0.6238 (2)0.0356 (10)
C50.6944 (5)0.3865 (8)0.5635 (2)0.0396 (10)
H50.56290.38270.5340.048*
C40.8453 (6)0.5654 (8)0.5477 (2)0.0406 (11)
H40.81830.68550.50650.049*
C31.0351 (6)0.5702 (8)0.5917 (2)0.0395 (10)
H31.13570.69670.58040.047*
C21.0833 (6)0.3952 (8)0.6520 (2)0.0371 (10)
H21.21460.39860.68150.045*
C10.9315 (5)0.2159 (9)0.6670 (2)0.0339 (10)
C91.1290 (5)−0.0424 (8)0.7759 (2)0.0395 (10)
H9A1.2449−0.06640.74730.047*
H9B1.1091−0.21790.80110.047*
C101.1851 (6)0.1760 (8)0.8340 (2)0.0358 (10)
C111.3769 (6)0.2963 (9)0.8421 (2)0.0456 (11)
H111.47290.24440.81040.055*
C121.4297 (7)0.4925 (10)0.8963 (3)0.0543 (13)
H121.56170.5750.90130.065*
C131.2940 (8)0.5685 (9)0.9425 (2)0.0561 (13)
H131.33160.70190.97990.067*
C141.1016 (7)0.4498 (10)0.9345 (2)0.0550 (12)
H141.00560.50230.96610.066*
C151.0489 (6)0.2540 (8)0.8801 (2)0.0451 (11)
H150.91640.17270.87470.054*
N10.9447 (4)0.0189 (6)0.72476 (17)0.0355 (9)
O10.7208 (4)−0.2996 (6)0.76148 (16)0.0584 (9)
O20.4417 (4)−0.0659 (6)0.63438 (16)0.0561 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C80.052 (3)0.036 (3)0.040 (3)0.004 (2)0.013 (2)−0.007 (2)
C70.039 (2)0.040 (3)0.042 (3)0.000 (2)0.012 (2)−0.012 (2)
C60.038 (2)0.035 (2)0.032 (3)0.006 (2)−0.0002 (19)−0.005 (2)
C50.034 (2)0.044 (3)0.039 (3)0.001 (2)−0.0022 (18)−0.009 (2)
C40.051 (3)0.036 (3)0.033 (3)0.000 (2)0.000 (2)−0.001 (2)
C30.054 (3)0.028 (2)0.038 (3)−0.001 (2)0.013 (2)−0.007 (2)
C20.046 (2)0.035 (2)0.031 (2)0.004 (2)0.0050 (18)−0.003 (2)
C10.040 (2)0.034 (2)0.029 (2)0.001 (2)0.0087 (19)−0.008 (2)
C90.045 (2)0.038 (2)0.034 (2)0.006 (2)0.0028 (18)−0.001 (2)
C100.045 (2)0.032 (2)0.028 (3)0.006 (2)−0.0017 (19)0.007 (2)
C110.045 (3)0.046 (3)0.043 (3)0.004 (2)0.000 (2)0.003 (2)
C120.059 (3)0.048 (3)0.050 (3)−0.002 (2)−0.011 (2)0.010 (3)
C130.084 (4)0.044 (3)0.035 (3)−0.004 (3)−0.010 (3)−0.003 (2)
C140.080 (3)0.046 (3)0.041 (3)0.005 (3)0.014 (2)−0.004 (3)
C150.060 (3)0.039 (3)0.037 (3)−0.005 (2)0.009 (2)−0.001 (2)
N10.0379 (18)0.036 (2)0.032 (2)−0.0020 (17)0.0025 (15)0.0040 (18)
O10.071 (2)0.0487 (19)0.058 (2)−0.0078 (18)0.0194 (16)0.008 (2)
O20.0411 (16)0.057 (2)0.071 (2)−0.0102 (16)0.0099 (14)−0.0093 (18)
Geometric parameters (Å, º) top
C8—O11.221 (5)C9—N11.449 (4)
C8—N11.371 (5)C9—C101.511 (5)
C8—C71.544 (5)C9—H9A0.99
C7—O21.209 (4)C9—H9B0.99
C7—C61.457 (5)C10—C151.368 (5)
C6—C11.379 (5)C10—C111.380 (5)
C6—C51.386 (5)C11—C121.384 (6)
C5—C41.384 (5)C11—H110.95
C5—H50.95C12—C131.364 (6)
C4—C31.382 (5)C12—H120.95
C4—H40.95C13—C141.380 (6)
C3—C21.392 (5)C13—H130.95
C3—H30.95C14—C151.385 (6)
C2—C11.385 (5)C14—H140.95
C2—H20.95C15—H150.95
C1—N11.420 (5)
O1—C8—N1125.7 (4)C10—C9—H9A108.8
O1—C8—C7127.2 (4)N1—C9—H9B108.8
N1—C8—C7107.1 (4)C10—C9—H9B108.8
O2—C7—C6130.8 (4)H9A—C9—H9B107.7
O2—C7—C8124.6 (4)C15—C10—C11119.0 (4)
C6—C7—C8104.6 (3)C15—C10—C9120.8 (4)
C1—C6—C5121.7 (4)C11—C10—C9120.2 (4)
C1—C6—C7107.7 (4)C10—C11—C12120.2 (4)
C5—C6—C7130.6 (4)C10—C11—H11119.9
C4—C5—C6117.9 (4)C12—C11—H11119.9
C4—C5—H5121.1C13—C12—C11120.7 (5)
C6—C5—H5121.1C13—C12—H12119.7
C3—C4—C5120.3 (4)C11—C12—H12119.7
C3—C4—H4119.8C12—C13—C14119.4 (4)
C5—C4—H4119.8C12—C13—H13120.3
C4—C3—C2122.0 (4)C14—C13—H13120.3
C4—C3—H3119C13—C14—C15119.8 (4)
C2—C3—H3119C13—C14—H14120.1
C1—C2—C3117.2 (4)C15—C14—H14120.1
C1—C2—H2121.4C10—C15—C14120.9 (4)
C3—C2—H2121.4C10—C15—H15119.6
C6—C1—C2120.9 (4)C14—C15—H15119.6
C6—C1—N1111.7 (3)C8—N1—C1108.9 (3)
C2—C1—N1127.4 (3)C8—N1—C9125.9 (3)
N1—C9—C10113.6 (3)C1—N1—C9124.9 (3)
N1—C9—H9A108.8
O1—C8—C7—O20.5 (6)N1—C9—C10—C11−124.2 (4)
N1—C8—C7—O2−179.1 (4)C15—C10—C11—C120.1 (6)
O1—C8—C7—C6−179.8 (4)C9—C10—C11—C12−178.7 (4)
N1—C8—C7—C60.6 (4)C10—C11—C12—C130.3 (6)
O2—C7—C6—C1179.0 (4)C11—C12—C13—C14−0.6 (7)
C8—C7—C6—C1−0.7 (4)C12—C13—C14—C150.5 (6)
O2—C7—C6—C5−1.2 (7)C11—C10—C15—C14−0.2 (6)
C8—C7—C6—C5179.1 (4)C9—C10—C15—C14178.6 (4)
C1—C6—C5—C4−0.1 (6)C13—C14—C15—C100.0 (6)
C7—C6—C5—C4−179.8 (4)O1—C8—N1—C1−180.0 (4)
C6—C5—C4—C3−0.7 (6)C7—C8—N1—C1−0.4 (4)
C5—C4—C3—C21.1 (6)O1—C8—N1—C95.0 (6)
C4—C3—C2—C1−0.7 (5)C7—C8—N1—C9−175.4 (3)
C5—C6—C1—C20.4 (6)C6—C1—N1—C8−0.1 (4)
C7—C6—C1—C2−179.8 (3)C2—C1—N1—C8−179.8 (4)
C5—C6—C1—N1−179.3 (3)C6—C1—N1—C9175.0 (3)
C7—C6—C1—N10.5 (4)C2—C1—N1—C9−4.7 (6)
C3—C2—C1—C6−0.1 (5)C10—C9—N1—C8−111.7 (4)
C3—C2—C1—N1179.6 (4)C10—C9—N1—C174.0 (4)
N1—C9—C10—C1557.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.413.213 (5)143
C9—H9A···O2ii0.992.593.525 (4)159
C9—H9B···O10.992.582.941 (5)101
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC15H11NO2
Mr237.25
Crystal system, space groupMonoclinic, P21
Temperature (K)183
a, b, c (Å)6.5766 (5), 4.8877 (4), 18.2211 (13)
β (°) 98.316 (7)
V (Å3)579.55 (8)
Z2
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.34 × 0.07 × 0.02
Data collection
DiffractometerOxford Xcalibur Ruby CCD
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
Tmin, Tmax0.881, 0.921
No. of measured, independent and
observed [I > 2σ(I)] reflections		5347, 2095, 1264
Rint0.068
(sin θ/λ)max (Å−1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.128, 0.99
No. of reflections2095
No. of parameters163
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.15, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Selected torsion angles (º) top
N1—C9—C10—C1557.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.413.213 (5)142.5
C9—H9A···O2ii0.992.593.525 (4)158.5
C9—H9B···O10.992.582.941 (5)101.3
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
 

Acknowledgements

The authors thank Dr Henrik Braband for the data collection, and the Department of Chemistry of the University of the Free State, the NRF and Sasol Ltd for funding. Special thanks go to Professor Roger Alberto from the ACI, University of Zurich.

References

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Volume 68| Part 3| March 2012| Page o777
doi:10.1107/S1600536812006575
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