Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Jun 5;66(Pt 7):o1593–o1594. doi: 10.1107/S1600536810021045

4-(2-Methyl­anilino)pent-3-en-2-one

Gertruida J S Venter a,*, Gideon Steyl a, Andreas Roodt a
PMCID: PMC3006949  PMID: 21587831

Abstract

The title enamino ketone, C12H15NO, a derivative of 4-(phenyl­amino)­pent-3-en-2-one, presents a roughly planar [greatest displacement of an atom from the pentenone plane is 0.033 (2) Å] pentenone backbone, enhanced by an intra­molecular N—H⋯O hydrogen bond; the asymmetry in C—C distances in the group suggests the presence of unsaturated bonds. The overall geometry in the free ligand differs significantly from that in other reported compounds, in which it is coordinated to rhodium; this is reflected in the bond distances [the N⋯O distance is significantly increased (0.2 Å) upon coordination to the metal] and the dihedral angle between the benzene ring and the pentenone backbone [49.53 (5)°]. All of the methyl goups are rotationally disordered over two orientations of equal occupancy.

Related literature

For synthetic background, see: Shaheen et al. (2006 ▶). For applications of enamino­ketones in liquid crystals, see: Pyżuk et al. (1993 ▶), in fluorescence, see: Xia et al. (2008 ▶), in complexes of medical inter­est, see: Tan et al. (2008 ▶); Chen & Rhodes (1996 ▶), in catalysis, see: Nair et al. (2002 ▶); Van Aswegen et al. (1991 ▶); Steyn et al. (1992 ▶, 1997 ▶); Otto et al. (1998 ▶); Roodt & Steyn (2000 ▶); Brink et al. (2010 ▶). For the structures of related ligand systems, see: Damoense et al. (1994 ▶); Venter et al. (2009a ▶,b ▶). graphic file with name e-66-o1593-scheme1.jpg

Experimental

Crystal data

  • C12H15NO

  • M r = 189.25

  • Monoclinic, Inline graphic

  • a = 7.5674 (7) Å

  • b = 11.5075 (9) Å

  • c = 12.0996 (11) Å

  • β = 92.154 (5)°

  • V = 1052.91 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.55 × 0.23 × 0.12 mm

Data collection

  • Bruker X8 APEXII 4K Kappa CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.960, T max = 0.991

  • 10022 measured reflections

  • 2308 independent reflections

  • 1854 reflections with I > 2σ(I)

  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053

  • wR(F 2) = 0.150

  • S = 1.07

  • 2308 reflections

  • 129 parameters

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; 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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021045/bg2348sup1.cif

e-66-o1593-sup1.cif (17KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021045/bg2348Isup2.hkl

e-66-o1593-Isup2.hkl (111.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N11—H11⋯O12 0.91 1.90 2.6345 (19) 136
Open in a new tab

Table 2. Comparative geometrical parameters (Å, °) for free and coordinated N,O-bidendate (N,O-bid) compounds.

Parameters (I) (II) (III) (IV)
C111—N11 1.422 (2) 1.521 (4)/1.463 (3) 1.440 (4) -
C2—N11 1.345 (2) 1.320 (4) 1.319 (4) 1.303 (6)
C4—O12 1.257 (2) 1.290 (3) 1.291 (4) 1.281 (6)
C2—C3 1.383 (3) 1.410 (4) 1.423 (4) 1.396 (7)
C3—C4 1.420 (2) 1.365 (3) 1.382 (3) 1.388 (9)
O12⋯N11 2.635 (2) 2.885 (3) 2.886 (3) 2.826 (6)
N11—C2—C4—O12 −0.5 (1) 4.1 (2) −2.6 (2) 1.2 (4)
Dihedral angle 49.53 (5) 87.47 (4)/89.36 (8) 85.58 (8) -
Open in a new tab

Notes: (I) This work; (II) N,O-bid = 4-(2,3-dimethyl phenyl­amino)­pent-3-en-2-onato (Venter et al., 2009a ▶); (III) N,O-bid = 4-(2,6-dimethyl phenyl­amino)­pent-3-en-2-onato (Venter et al., 2009b ▶). (IV) N,O-bid = 4-amino-pent-3-en-2-onato (Damoense et al., 1994 ▶). The dihedral angle is defined as the torsion angle between the N–C–C–C–O plane and the benzene ring. A positive angle denotes a clockwise rotation.

Acknowledgments

Financial assistance from the University of the Free State is gratefully acknowledged. We also express our gratitude towards SASOL, the UFS Materials and Nanosciences Academic Cluster and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the SA-NRF.

supplementary crystallographic information

Comment

A well-known system in organometallic chemistry is the β-diketone compound AcacH (acetylacetone; or when coordinated acetylacetonato, acac-). A multitude of derivatives have been synthesized to date, with enaminoketones being one type. Since enaminoketones contain nitrogen and oxygen atoms as well as an unsaturated C—C bond, these electron-rich compounds are of interest in various fields including liquid crystals [Pyżuk et al. (1993)], fluorescence studies [Xia et al. (2008)] as well as formation of complexes of medical interest [Tan et al. (2008); Chen & Rhodes (1996)]. It also has significant application possibilities in catalysis [Nair et al. (2002); Van Aswegen et al. (1991); Steyn et al. (1992; 1997); Otto et al. (1998); Roodt & Steyn (2000); Brink et al. (2010)].

The title enaminoketone is a derivative of 4-(phenylamino)pent-3-en-2-one [PhonyH; Shaheen et al. (2006)]. Fig. 1 shows a view of the molecule. The C2–C3 distance of 1.383 (3) Å, versus the C3–C4 distance of 1.420 (2)Å indicates an unsaturated bond in the pentenone backbone, which is otherwise planar, probably helped by an intramolecular N1—H1···O1 bond (N1—H1: 0.91Å; H1···O1: 1.90Å; N1···O1:2.635 (2)Å, N1—H1···O: 136.4°). In general terms, the geometry in the free ligand differs significantly from that in other reported compounds where it is coordinated to rhodium [Table1; Venter et al. (2009a; 2009b); Damoense et al. (1994)]; fon instance, the N1···O1 distance is greatly ncreased (~0.2 Å) upon coordination to the metal, as it is the dihedral angle between the phenyl ring and the pentenone backbone. All the methyl goups appear rotationally disordered in two sites of similar occupation.

Experimental

A solution of acetylacetone (11.07 g, 0.1106 mol), 2-Me-aniline (10.73 g, 0.1008 mol) and 2 drops of H2SO4(conc.) in 150 ml benzene was refluxed for 6 hours in a DeanStark trap, filtered and left to crystallize. Crystals suitable for X-Ray diffraction were obtained in 17.86 g (94.32 %) yield. This compound is stable in air and light over a period of several months.

Refinement

The methyl and aromatic H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.95 and 0.98Å and Uiso(H) = 1.5Ueq(C) and 1.2Ueq(C), respectively. The methyl groups were generated to fit the difference electron density and the groups were then refined as rigid rotors. The highest residual electron-density peak is 0.47Å from H1F.

Figures

Fig. 1.

Fig. 1.

Open in a new tab

Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability displacement level.

Crystal data

C12H15NO F(000) = 408
Mr = 189.25 Dx = 1.194 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 2889 reflections
a = 7.5674 (7) Å θ = 2.7–28.2°
b = 11.5075 (9) Å µ = 0.08 mm−1
c = 12.0996 (11) Å T = 100 K
β = 92.154 (5)° Plate, colourless
V = 1052.91 (16) Å3 0.55 × 0.23 × 0.12 mm
Z = 4
Open in a new tab

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer 2308 independent reflections
Radiation source: fine-focus sealed tube 1854 reflections with I > 2σ(I)
graphite Rint = 0.034
ω and φ scans θmax = 27°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004) h = −9→9
Tmin = 0.960, Tmax = 0.991 k = −14→12
10022 measured reflections l = −15→15
Open in a new tab

Refinement

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)] = 0.053 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150 H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0654P)2 + 0.9506P] where P = (Fo2 + 2Fc2)/3
2308 reflections (Δ/σ)max < 0.001
129 parameters Δρmax = 0.45 e Å−3
0 restraints Δρmin = −0.35 e Å−3
Open in a new tab

Special details

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 60 seconds/frame. A total of 688 frames were collected with a frame width of 0.5° covering up to θ = 28.24° with 99.1% completeness accomplished.
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.
Open in a new tab

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
C1 0.4288 (3) 0.30725 (17) 0.73241 (16) 0.0212 (4)
H1A 0.4068 0.3907 0.723 0.032* 0.5
H1B 0.3886 0.2659 0.6653 0.032* 0.5
H1C 0.5557 0.2939 0.7458 0.032* 0.5
H1D 0.4939 0.243 0.6998 0.032* 0.5
H1E 0.5121 0.3678 0.7575 0.032* 0.5
H1F 0.345 0.3397 0.6769 0.032* 0.5
C2 0.3300 (2) 0.26340 (16) 0.82877 (15) 0.0172 (4)
C3 0.3410 (2) 0.14730 (15) 0.85770 (15) 0.0174 (4)
H3 0.4142 0.0982 0.8159 0.021*
C4 0.2494 (2) 0.09702 (15) 0.94616 (14) 0.0162 (4)
C5 0.2647 (3) −0.03183 (16) 0.96633 (16) 0.0217 (4)
H5A 0.1945 −0.0532 1.0296 0.033* 0.5
H5B 0.3889 −0.0521 0.982 0.033* 0.5
H5C 0.2208 −0.0739 0.9005 0.033* 0.5
H5D 0.3417 −0.0663 0.9118 0.033* 0.5
H5E 0.1472 −0.0674 0.9594 0.033* 0.5
H5F 0.3153 −0.0456 1.0409 0.033* 0.5
C12 0.2730 (3) 0.49042 (17) 1.07167 (15) 0.0218 (4)
H12A 0.2961 0.4067 1.0685 0.033* 0.5
H12B 0.1797 0.5055 1.1238 0.033* 0.5
H12C 0.3812 0.5311 1.0964 0.033* 0.5
H12D 0.2752 0.5555 1.1239 0.033* 0.5
H12E 0.3917 0.4567 1.0687 0.033* 0.5
H12F 0.1901 0.4311 1.0961 0.033* 0.5
O12 0.15430 (17) 0.15514 (11) 1.00878 (10) 0.0195 (3)
C111 0.1994 (2) 0.45704 (15) 0.86788 (15) 0.0160 (4)
C112 0.2147 (2) 0.53330 (16) 0.95849 (15) 0.0172 (4)
C113 0.1737 (2) 0.64979 (16) 0.94050 (16) 0.0203 (4)
H113 0.1821 0.7026 1.0008 0.024*
C114 0.1207 (2) 0.69078 (16) 0.83647 (16) 0.0208 (4)
H114 0.0932 0.7707 0.8262 0.025*
C115 0.1081 (2) 0.61469 (16) 0.74784 (15) 0.0192 (4)
H115 0.0738 0.6426 0.6763 0.023*
C116 0.1456 (2) 0.49751 (16) 0.76367 (15) 0.0180 (4)
H116 0.1344 0.445 0.7032 0.022*
N11 0.2320 (2) 0.33691 (13) 0.88747 (13) 0.0176 (3)
H11 0.1801 0.3060 0.9471 0.021*
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0225 (9) 0.0206 (9) 0.0210 (9) 0.0019 (7) 0.0057 (7) 0.0032 (7)
C2 0.0167 (8) 0.0190 (9) 0.0159 (9) 0.0001 (7) 0.0001 (7) −0.0007 (7)
C3 0.0192 (9) 0.0163 (9) 0.0168 (9) 0.0028 (7) 0.0029 (7) −0.0015 (7)
C4 0.0176 (8) 0.0157 (9) 0.0152 (8) 0.0008 (7) −0.0013 (7) −0.0010 (7)
C5 0.0254 (10) 0.0152 (9) 0.0250 (10) 0.0014 (7) 0.0062 (8) 0.0005 (7)
C12 0.0221 (9) 0.0244 (10) 0.0188 (9) −0.0010 (8) 0.0000 (7) −0.0015 (7)
O12 0.0254 (7) 0.0157 (6) 0.0176 (7) 0.0015 (5) 0.0051 (5) −0.0001 (5)
C111 0.0158 (8) 0.0122 (8) 0.0202 (9) −0.0008 (6) 0.0032 (7) 0.0003 (7)
C112 0.0164 (8) 0.0177 (9) 0.0177 (9) −0.0018 (7) 0.0023 (7) −0.0002 (7)
C113 0.0222 (9) 0.0170 (9) 0.0220 (9) −0.0018 (7) 0.0033 (7) −0.0059 (7)
C114 0.0214 (9) 0.0129 (8) 0.0284 (10) 0.0004 (7) 0.0047 (8) 0.0012 (7)
C115 0.0189 (9) 0.0190 (9) 0.0198 (9) −0.0001 (7) 0.0024 (7) 0.0031 (7)
C116 0.0200 (9) 0.0163 (9) 0.0178 (9) −0.0020 (7) 0.0020 (7) −0.0018 (7)
N11 0.0232 (8) 0.0132 (7) 0.0168 (8) 0.0009 (6) 0.0053 (6) 0.0012 (6)
Open in a new tab

Geometric parameters (Å, °)

C1—C2 1.496 (2) C12—C112 1.506 (3)
C1—H1A 0.98 C12—H12A 0.98
C1—H1B 0.98 C12—H12B 0.98
C1—H1C 0.98 C12—H12C 0.98
C1—H1D 0.98 C12—H12D 0.98
C1—H1E 0.98 C12—H12E 0.98
C1—H1F 0.98 C12—H12F 0.98
C2—N11 1.345 (2) C111—C116 1.391 (3)
C2—C3 1.383 (3) C111—C112 1.406 (3)
C3—C4 1.420 (2) C111—N11 1.422 (2)
C3—H3 0.95 C112—C113 1.391 (3)
C4—O12 1.257 (2) C113—C114 1.389 (3)
C4—C5 1.506 (2) C113—H113 0.95
C5—H5A 0.98 C114—C115 1.385 (3)
C5—H5B 0.98 C114—H114 0.95
C5—H5C 0.98 C115—C116 1.390 (3)
C5—H5D 0.98 C115—H115 0.95
C5—H5E 0.98 C116—H116 0.95
C5—H5F 0.98 N11—H11 0.9071
C2—C1—H1A 109.5 H5B—C5—H5F 56.3
C2—C1—H1B 109.5 H5C—C5—H5F 141.1
H1A—C1—H1B 109.5 H5D—C5—H5F 109.5
C2—C1—H1C 109.5 H5E—C5—H5F 109.5
H1A—C1—H1C 109.5 C112—C12—H12A 109.5
H1B—C1—H1C 109.5 C112—C12—H12B 109.5
C2—C1—H1D 109.5 H12A—C12—H12B 109.5
H1A—C1—H1D 141.1 C112—C12—H12C 109.5
H1B—C1—H1D 56.3 H12A—C12—H12C 109.5
H1C—C1—H1D 56.3 H12B—C12—H12C 109.5
C2—C1—H1E 109.5 C112—C12—H12D 109.5
H1A—C1—H1E 56.3 H12A—C12—H12D 141.1
H1B—C1—H1E 141.1 H12B—C12—H12D 56.3
H1C—C1—H1E 56.3 H12C—C12—H12D 56.3
H1D—C1—H1E 109.5 C112—C12—H12E 109.5
C2—C1—H1F 109.5 H12A—C12—H12E 56.3
H1A—C1—H1F 56.3 H12B—C12—H12E 141.1
H1B—C1—H1F 56.3 H12C—C12—H12E 56.3
H1C—C1—H1F 141.1 H12D—C12—H12E 109.5
H1D—C1—H1F 109.5 C112—C12—H12F 109.5
H1E—C1—H1F 109.5 H12A—C12—H12F 56.3
N11—C2—C3 120.21 (16) H12B—C12—H12F 56.3
N11—C2—C1 120.06 (16) H12C—C12—H12F 141.1
C3—C2—C1 119.73 (16) H12D—C12—H12F 109.5
C2—C3—C4 123.91 (16) H12E—C12—H12F 109.5
C2—C3—H3 118 C116—C111—C112 120.72 (16)
C4—C3—H3 118 C116—C111—N11 121.30 (16)
O12—C4—C3 122.97 (16) C112—C111—N11 117.91 (16)
O12—C4—C5 117.93 (16) C113—C112—C111 117.91 (17)
C3—C4—C5 119.10 (15) C113—C112—C12 120.93 (16)
C4—C5—H5A 109.5 C111—C112—C12 121.16 (16)
C4—C5—H5B 109.5 C114—C113—C112 121.61 (17)
H5A—C5—H5B 109.5 C114—C113—H113 119.2
C4—C5—H5C 109.5 C112—C113—H113 119.2
H5A—C5—H5C 109.5 C115—C114—C113 119.74 (17)
H5B—C5—H5C 109.5 C115—C114—H114 120.1
C4—C5—H5D 109.5 C113—C114—H114 120.1
H5A—C5—H5D 141.1 C114—C115—C116 119.93 (17)
H5B—C5—H5D 56.3 C114—C115—H115 120
H5C—C5—H5D 56.3 C116—C115—H115 120
C4—C5—H5E 109.5 C115—C116—C111 120.08 (17)
H5A—C5—H5E 56.3 C115—C116—H116 120
H5B—C5—H5E 141.1 C111—C116—H116 120
H5C—C5—H5E 56.3 C2—N11—C111 128.22 (16)
H5D—C5—H5E 109.5 C2—N11—H11 115.9
C4—C5—H5F 109.5 C111—N11—H11 115.9
H5A—C5—H5F 56.3
N11—C2—C3—C4 1.9 (3) C112—C113—C114—C115 −0.1 (3)
C1—C2—C3—C4 −178.62 (17) C113—C114—C115—C116 1.1 (3)
C2—C3—C4—O12 −2.6 (3) C114—C115—C116—C111 −1.4 (3)
C2—C3—C4—C5 177.01 (17) C112—C111—C116—C115 0.7 (3)
C116—C111—C112—C113 0.3 (3) N11—C111—C116—C115 177.51 (16)
N11—C111—C112—C113 −176.63 (16) C3—C2—N11—C111 −177.32 (17)
C116—C111—C112—C12 −179.96 (16) C1—C2—N11—C111 3.2 (3)
N11—C111—C112—C12 3.1 (3) C116—C111—N11—C2 48.9 (3)
C111—C112—C113—C114 −0.6 (3) C112—C111—N11—C2 −134.19 (19)
C12—C112—C113—C114 179.64 (17)
Open in a new tab

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N11—H11···O12 0.91 1.90 2.6345 (19) 136
Open in a new tab

Table 2 Comparative geometrical parameters (Å, °) for free and coordinated N,O-bidendate (N,O-bid) compounds

Parameters (I) (II) (III) (IV)
N11—C111 1.422 (2) 1.521 (4)/1.463 (3) 1.440 (4) -
N11—C2 1.345 (2) 1.320 (4) 1.319 (4) 1.303 (6)
O12—C4 1.257 (2) 1.290 (3) 1.291 (4) 1.281 (6)
C2—C3 1.383 (3) 1.410 (4) 1.423 (4) 1.396 (7)
C3—C4 1.420 (2) 1.365 (3) 1.382 (3) 1.388 (9)
N11···O12 2.635 (2) 2.885 (3) 2.886 (3) 2.826 (6)
N11—C2—C4—O12 -0.5 (1) 4.1 (2) -2.6 (2) 1.2 (4)
Dihedral angle 49.53 (5) 87.47 (4)/89.36 (8) 85.58 (8) -
Open in a new tab

Notes: (I) This work; (II) N,O-bid = 4-(2,3-dimethyl phenylamino)pent-3-en-2-onato (Venter et al., 2009a); (III) N,O-bid = 4-(2,6-dimethyl phenylamino)pent-3-en-2-onato (Venter et al., 2009b). (IV) N,O-bid = 4-amino-pent-3-en-2-onato (Damoense, et al., 1994).

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2348).

References

  1. Brandenburg, K. & Putz, H. (2005). DIAMOND Crystal Impact GbR, Bonn, Germany.
  2. Brink, A., Visser, H. G., Steyl, G. & Roodt, A. (2010). Dalton Trans 39, 5572–5578. [DOI] [PubMed]
  3. Bruker (2004). SAINT-Plus and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Bruker (2005). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  5. Chen, H. & Rhodes, J. (1996). J. Mol. Med.74, 497–504. [DOI] [PubMed]
  6. Damoense, L. J., Purcell, W., Roodt, A. & Leipoldt, J. G. (1994). Rhodium Express, 5, 10–13.
  7. Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  8. Nair, V. A., Suni, M. M. & Sreekumar, K. (2002). Proc. Indian Acad. Sci. (Chem. Sci.), 114, 481–486.
  9. Otto, S., Roodt, A., Swarts, J. C. & Erasmus, J. C. (1998). Polyhedron, 17, 2447–2453.
  10. Pyżuk, W., Krówczynsk, A. & Górecka, E. (1993). Mol. Cryst. Liq. Cryst.237, 75–84.
  11. Roodt, A. & Steyn, G. J. J. (2000). Recent Research Developments in Inorganic Chemistry, Vol. 2, pp. 1–23. Trivandrum: Transworld Research Network.
  12. Shaheen, F., Marchio, L., Badshah, A. & Khosa, M. K. (2006). Acta Cryst.E62, o873–o874.
  13. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  14. Steyn, G. J. J., Roodt, A. & Leipoldt, J. G. (1992). Inorg. Chem 31, 3477–3481.
  15. Steyn, G. J. J., Roodt, A., Poletaeva, I. A. & Varshavsky, Y. S. (1997). J. Organomet. Chem.536/7, 197–205.
  16. Tan, H. Y., Loke, W. K., Tan, Y. T. & Nguyen, N.-T. (2008). Lab. Chip, 8, 885–891. [DOI] [PubMed]
  17. Van Aswegen, K. G., Leipoldt, J. G., Potgieter, I. M., Roodt, A. & Van Zyl, G. J. (1991). Transition Met. Chem 16, 369–371.
  18. Venter, G. J. S., Steyl, G. & Roodt, A. (2009a). Acta Cryst. E65, m1321–m1322. [DOI] [PMC free article] [PubMed]
  19. Venter, G. J. S., Steyl, G. & Roodt, A. (2009b). Acta Cryst. E65, m1606–m1607. [DOI] [PMC free article] [PubMed]
  20. Xia, M., Wu, B. & Xiang, G. (2008). J. Fluorine Chem.129, 402–408.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021045/bg2348sup1.cif

e-66-o1593-sup1.cif (17KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021045/bg2348Isup2.hkl

e-66-o1593-Isup2.hkl (111.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES