1-(2-Phenyl­eth­yl)adamantane

Rouchal, M.; Nečas, M.; Vícha, R.

doi:10.1107/S1600536810023251

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1736

doi:10.1107/S1600536810023251

Open

access

1-(2-Phenylethyl)adamantane

Michal Rouchal,^a Marek Nečas ^b and Robert Vícha ^a ^*

^aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and ^bDepartment of Chemistry, Faculty of Science, Masaryk University in Brno, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
^*Correspondence e-mail: rvicha@ft.utb.cz

(Received 24 May 2010; accepted 16 June 2010; online 23 June 2010)

In the title compound, C₁₈H₂₄, the adamantane cage consists of three fused cyclohexane rings in almost ideal chair conformations, with C—C—C angles in the range 108.0 (14)–111.1 (15)°. The phenyl and 1-adamantyl substituents adopt anti orientations with a C—C—C—C torsion angle of 177.10 (16)°. In the crystal packing, the molecules are linked by weak C—H⋯π interactions into chains along the a axis.

Related literature

The title compound was prepared according to a modified procedure of Adkins & Billica (1948 ). For some important properties of compounds bearing the adamantane scaffold, see: van der Schyf et al. (2009 ); van Bommel et al. (2001 ). For a related structure, see: Raine et al. (2002 ).

Experimental

Crystal data

C₁₈H₂₄
M_r = 240.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.4844 (5) Å
b = 7.5109 (5) Å
c = 28.5305 (19) Å
V = 1389.55 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 120 K
0.40 × 0.20 × 0.20 mm

Data collection

Kuma KM-4-CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.924, T_max = 1.000
11994 measured reflections
1452 independent reflections
1277 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.127
S = 1.30
1452 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯Cg1ⁱ	0.95	2.64	3.529 (3)	156
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023251/ez2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023251/ez2215Isup2.hkl

checkCIF report

Comment top

Adamantane is a molecule with an elegant structure and unique properties. The addition of the highly lipophilic adamantane cage to a known biologically active compound can significantly improve the pharmacokinetic profile of the resulting molecule, e.g. its oral bioavailability (van der Schyf et al. 2009). Moreover, the relatively stable host–guest interactions of the adamantane scaffold with β-cyclodextrin might increase the solubility of non-polar substances in polar media (van Bommel et al. 2001). Both these characteristics have an important role in drug design. This structure represents one of the few low-molecular-weight molecules bearing an adamantane moiety that has no polar function group. Therefore, this compound may be used as a standard molecule for investigations of non-polar interactions.

The asymmetric unit of the title compound consists of a single molecule (Fig. 1). The benzene ring is nearly planar with a maximum deviation from the best plane being 0.007 (2) Å for C16. The torsion angles describing mutual alignment of the 1-adamantyl and phenyl substituents C18—C13—C12—C11, C13—C12—C11—C1 and C12—C11—C1—C2 are -73.4 (2), -177.10 (16) and 179.59 (16)°, respectively. In the crystal packing, the molecules are arranged into chains parallel to the a-axis linked by weak C—H···π interactions (Fig. 2, Table 1).

Related literature top

The title compound was prepared according to a modified procedure of Adkins & Billica (1948). For some important properties of compounds bearing the adamantane scaffold, see: van der Schyf et al. (2009); van Bommel et al. (2001). For a related structure, see: Raine et al. (2002).

Experimental top

The title compound was prepared according to a modified literature procedure published by Adkins & Billica (1948). 2-(1-Adamantyl)-2-benzyl-1,3-dithiane (0.33 mmol, 114 mg) was dissolved in 5 ml of dioxane and a large excess of Raney nickel catalyst was added to this solution. The reaction mixture was stirred and refluxed under Ar atmosphere. Further portions of Raney nickel were added until the starting material was completely consumed (monitored by GC). Subsequently, the Raney nickel was filtered off, the filtrate was diluted with water and extracted with diethyl ether. The combined organic layers were washed twice with brine and dried over Na₂SO₄. The required product was obtained after evaporation of solvent in vacuum as a colorless crystalline powder (72 mg, 91%, mp 318–324 K). The crystal used for data collection was grown by spontaneous evaporation from deuterochloroform at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP diagram of the asymmetric unit showing the atom labelling scheme with atoms represented as 50% probability ellipsoids.

Fig. 2. A partial view of the crystal packing viewed along the b-axis showing the arrangement of the molecules into chains parallel to the a-axis stabilized by weak C—H···π interactions (dotted lines). Cg1 is the center of gravity of C13–C18. H-atoms (except those which are involved in H-bonding) have been omitted for clarity. Symmetry codes: (i) -x + 1.5, -y + 1, z + 1/2; (ii) –x+2, y - 1/2, -z + 1/2.

1-(2-Phenylethyl)adamantane top

Crystal data top

C₁₈H₂₄	D_x = 1.149 Mg m⁻³
M_r = 240.37	Melting point: 321 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5446 reflections
a = 6.4844 (5) Å	θ = 3.1–27.2°
b = 7.5109 (5) Å	µ = 0.06 mm⁻¹
c = 28.5305 (19) Å	T = 120 K
V = 1389.55 (17) Å³	Block, colourless
Z = 4	0.40 × 0.20 × 0.20 mm
F(000) = 528

Data collection top

Kuma KM-4-CCD diffractometer	1452 independent reflections
Radiation source: fine-focus sealed tube	1277 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 0.06 mm pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
ω scan	h = −5→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −8→8
T_min = 0.924, T_max = 1.000	l = −33→33
11994 measured reflections

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.30	w = 1/[σ²(F_o²) + (0.0705P)² + 0.0787P] where P = (F_o² + 2F_c²)/3
1452 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₂₄	V = 1389.55 (17) Å³
M_r = 240.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.4844 (5) Å	µ = 0.06 mm⁻¹
b = 7.5109 (5) Å	T = 120 K
c = 28.5305 (19) Å	0.40 × 0.20 × 0.20 mm

Data collection top

Kuma KM-4-CCD diffractometer	1452 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1277 reflections with I > 2σ(I)
T_min = 0.924, T_max = 1.000	R_int = 0.043
11994 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.30	Δρ_max = 0.24 e Å⁻³
1452 reflections	Δρ_min = −0.15 e Å⁻³
163 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 > 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

	x	y	z	U_iso*/U_eq
C1	0.8116 (4)	0.4428 (3)	0.14870 (8)	0.0172 (6)
C2	0.6166 (4)	0.4772 (3)	0.17845 (9)	0.0207 (6)
H2A	0.6402	0.5812	0.1991	0.025*
H2B	0.4993	0.5052	0.1575	0.025*
C3	0.5633 (4)	0.3148 (3)	0.20840 (8)	0.0206 (6)
H3	0.4366	0.3400	0.2272	0.025*
C4	0.5236 (4)	0.1543 (3)	0.17589 (9)	0.0232 (6)
H4A	0.4887	0.0482	0.1949	0.028*
H4B	0.4059	0.1803	0.1549	0.028*
C5	0.7167 (4)	0.1176 (3)	0.14680 (8)	0.0212 (6)
H5	0.6913	0.0137	0.1257	0.025*
C6	0.8974 (4)	0.0749 (3)	0.17999 (9)	0.0222 (6)
H6A	0.8640	−0.0316	0.1990	0.027*
H6B	1.0230	0.0490	0.1615	0.027*
C7	0.9363 (4)	0.2344 (3)	0.21230 (8)	0.0195 (6)
H7	1.0545	0.2072	0.2337	0.023*
C8	0.9892 (4)	0.3977 (3)	0.18208 (8)	0.0182 (6)
H8A	1.0171	0.5010	0.2027	0.022*
H8B	1.1154	0.3731	0.1637	0.022*
C9	0.7437 (4)	0.2729 (4)	0.24146 (8)	0.0217 (6)
H9A	0.7693	0.3756	0.2624	0.026*
H9B	0.7097	0.1683	0.2611	0.026*
C10	0.7703 (4)	0.2808 (3)	0.11744 (9)	0.0208 (6)
H10A	0.6548	0.3076	0.0959	0.025*
H10B	0.8941	0.2554	0.0983	0.025*
C11	0.8577 (4)	0.6112 (3)	0.12008 (8)	0.0219 (6)
H11A	0.7359	0.6377	0.1004	0.026*
H11B	0.8750	0.7118	0.1421	0.026*
C12	1.0478 (5)	0.6040 (4)	0.08826 (9)	0.0283 (7)
H12A	1.1701	0.5727	0.1073	0.034*
H12B	1.0284	0.5092	0.0646	0.034*
C13	1.0866 (5)	0.7775 (4)	0.06375 (8)	0.0234 (6)
C14	1.2499 (5)	0.8876 (4)	0.07581 (8)	0.0302 (7)
H14	1.3389	0.8539	0.1007	0.036*
C15	1.2855 (5)	1.0453 (4)	0.05228 (9)	0.0349 (8)
H15	1.3969	1.1197	0.0615	0.042*
C16	1.1596 (5)	1.0957 (4)	0.01530 (9)	0.0317 (7)
H16	1.1860	1.2027	−0.0014	0.038*
C17	0.9961 (5)	0.9891 (4)	0.00311 (9)	0.0285 (7)
H17	0.9071	1.0238	−0.0217	0.034*
C18	0.9604 (5)	0.8312 (4)	0.02684 (9)	0.0275 (7)
H18	0.8477	0.7581	0.0178	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0173 (14)	0.0180 (13)	0.0163 (11)	−0.0001 (11)	0.0018 (10)	−0.0003 (10)
C2	0.0141 (13)	0.0236 (14)	0.0244 (13)	0.0037 (11)	0.0005 (12)	−0.0009 (11)
C3	0.0150 (14)	0.0257 (14)	0.0212 (12)	0.0006 (11)	0.0051 (11)	0.0004 (11)
C4	0.0187 (15)	0.0262 (14)	0.0247 (12)	−0.0028 (12)	−0.0013 (12)	0.0051 (11)
C5	0.0238 (15)	0.0188 (13)	0.0210 (12)	−0.0015 (12)	−0.0036 (11)	−0.0037 (11)
C6	0.0196 (14)	0.0202 (13)	0.0269 (13)	0.0012 (12)	0.0022 (12)	0.0028 (11)
C7	0.0157 (14)	0.0246 (14)	0.0184 (12)	0.0004 (12)	−0.0023 (11)	0.0037 (11)
C8	0.0155 (13)	0.0214 (13)	0.0177 (11)	−0.0004 (11)	0.0010 (11)	−0.0020 (11)
C9	0.0196 (15)	0.0278 (15)	0.0176 (11)	−0.0020 (13)	0.0016 (11)	0.0017 (10)
C10	0.0199 (15)	0.0237 (14)	0.0187 (11)	0.0010 (12)	−0.0007 (11)	−0.0012 (10)
C11	0.0216 (14)	0.0217 (14)	0.0223 (12)	0.0016 (12)	−0.0002 (12)	0.0007 (11)
C12	0.0275 (16)	0.0289 (15)	0.0284 (13)	0.0014 (14)	0.0050 (13)	0.0058 (12)
C13	0.0252 (16)	0.0248 (14)	0.0201 (12)	−0.0005 (12)	0.0029 (11)	0.0015 (11)
C14	0.0302 (16)	0.0415 (18)	0.0190 (12)	−0.0061 (15)	−0.0020 (12)	0.0030 (12)
C15	0.040 (2)	0.0352 (17)	0.0291 (14)	−0.0181 (15)	−0.0039 (14)	−0.0028 (13)
C16	0.0468 (19)	0.0250 (14)	0.0235 (13)	−0.0047 (15)	0.0047 (13)	0.0029 (12)
C17	0.0307 (17)	0.0317 (15)	0.0232 (13)	0.0030 (14)	−0.0002 (14)	0.0046 (11)
C18	0.0237 (16)	0.0283 (15)	0.0306 (14)	−0.0033 (13)	−0.0027 (12)	0.0000 (12)

Geometric parameters (Å, º) top

C1—C10	1.532 (3)	C8—H8B	0.9900
C1—C8	1.532 (3)	C9—H9A	0.9900
C1—C11	1.535 (3)	C9—H9B	0.9900
C1—C2	1.544 (3)	C10—H10A	0.9900
C2—C3	1.529 (3)	C10—H10B	0.9900
C2—H2A	0.9900	C11—C12	1.532 (4)
C2—H2B	0.9900	C11—H11A	0.9900
C3—C9	1.535 (4)	C11—H11B	0.9900
C3—C4	1.542 (3)	C12—C13	1.500 (4)
C3—H3	1.0000	C12—H12A	0.9900
C4—C5	1.527 (4)	C12—H12B	0.9900
C4—H4A	0.9900	C13—C14	1.387 (4)
C4—H4B	0.9900	C13—C18	1.393 (4)
C5—C10	1.525 (3)	C14—C15	1.381 (4)
C5—C6	1.540 (4)	C14—H14	0.9500
C5—H5	1.0000	C15—C16	1.387 (4)
C6—C7	1.533 (3)	C15—H15	0.9500
C6—H6A	0.9900	C16—C17	1.373 (4)
C6—H6B	0.9900	C16—H16	0.9500
C7—C9	1.528 (4)	C17—C18	1.385 (4)
C7—C8	1.538 (3)	C17—H17	0.9500
C7—H7	1.0000	C18—H18	0.9500
C8—H8A	0.9900

C10—C1—C8	108.5 (2)	C1—C8—H8B	109.5
C10—C1—C11	112.24 (18)	C7—C8—H8B	109.5
C8—C1—C11	111.5 (2)	H8A—C8—H8B	108.0
C10—C1—C2	108.1 (2)	C7—C9—C3	109.08 (18)
C8—C1—C2	108.09 (18)	C7—C9—H9A	109.9
C11—C1—C2	108.3 (2)	C3—C9—H9A	109.9
C3—C2—C1	111.0 (2)	C7—C9—H9B	109.9
C3—C2—H2A	109.4	C3—C9—H9B	109.9
C1—C2—H2A	109.4	H9A—C9—H9B	108.3
C3—C2—H2B	109.4	C5—C10—C1	110.99 (19)
C1—C2—H2B	109.4	C5—C10—H10A	109.4
H2A—C2—H2B	108.0	C1—C10—H10A	109.4
C2—C3—C9	109.5 (2)	C5—C10—H10B	109.4
C2—C3—C4	108.97 (18)	C1—C10—H10B	109.4
C9—C3—C4	109.7 (2)	H10A—C10—H10B	108.0
C2—C3—H3	109.6	C12—C11—C1	116.3 (2)
C9—C3—H3	109.6	C12—C11—H11A	108.2
C4—C3—H3	109.6	C1—C11—H11A	108.2
C5—C4—C3	109.3 (2)	C12—C11—H11B	108.2
C5—C4—H4A	109.8	C1—C11—H11B	108.2
C3—C4—H4A	109.8	H11A—C11—H11B	107.4
C5—C4—H4B	109.8	C13—C12—C11	112.4 (2)
C3—C4—H4B	109.8	C13—C12—H12A	109.1
H4A—C4—H4B	108.3	C11—C12—H12A	109.1
C10—C5—C4	109.9 (2)	C13—C12—H12B	109.1
C10—C5—C6	109.4 (2)	C11—C12—H12B	109.1
C4—C5—C6	109.09 (18)	H12A—C12—H12B	107.9
C10—C5—H5	109.5	C14—C13—C18	117.6 (2)
C4—C5—H5	109.5	C14—C13—C12	122.0 (2)
C6—C5—H5	109.5	C18—C13—C12	120.4 (3)
C7—C6—C5	109.4 (2)	C15—C14—C13	121.2 (3)
C7—C6—H6A	109.8	C15—C14—H14	119.4
C5—C6—H6A	109.8	C13—C14—H14	119.4
C7—C6—H6B	109.8	C14—C15—C16	120.4 (3)
C5—C6—H6B	109.8	C14—C15—H15	119.8
H6A—C6—H6B	108.2	C16—C15—H15	119.8
C9—C7—C6	109.9 (2)	C17—C16—C15	119.2 (3)
C9—C7—C8	109.7 (2)	C17—C16—H16	120.4
C6—C7—C8	108.84 (18)	C15—C16—H16	120.4
C9—C7—H7	109.5	C16—C17—C18	120.3 (3)
C6—C7—H7	109.5	C16—C17—H17	119.9
C8—C7—H7	109.5	C18—C17—H17	119.9
C1—C8—C7	110.9 (2)	C17—C18—C13	121.3 (3)
C1—C8—H8A	109.5	C17—C18—H18	119.4
C7—C8—H8A	109.5	C13—C18—H18	119.4

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1ⁱ	0.95	2.64	3.529 (3)	156

Symmetry code: (i) x−1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₄
M_r	240.37
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	6.4844 (5), 7.5109 (5), 28.5305 (19)
V (Å³)	1389.55 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Kuma KM-4-CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.924, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11994, 1452, 1277
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.127, 1.30
No. of reflections	1452
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1ⁱ	0.95	2.64	3.529 (3)	156.3

Symmetry code: (i) x−1/2, −y+3/2, −z.

Acknowledgements

Financial support of this work by the Czech Ministry of Education, project No. MSM 7088352101, and by the Tomas Bata Foundation is gratefully acknowledged.

References

Adkins, H. & Billica, H. R. (1948). J. Am. Chem. Soc. 70, 695–698. CrossRef CAS Web of Science Google Scholar
Bommel, K. J. C. van, Metselaar, M. A., Werboom, W. & Reinhoudt, D. N. (2001). J. Org. Chem. 66, 5405–5412. Web of Science PubMed Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Raine, A. L., Williams, C. M. & Bernhardt, P. V. (2002). Acta Cryst. E58, o1439–o1440. Web of Science CSD CrossRef IUCr Journals Google Scholar
Schyf, C. J. van der & Geldenhuys, W. J. (2009). Neurotherapeutics, 6, 175–186. CrossRef PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1736

doi:10.1107/S1600536810023251

Open

access