supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

bi2361 scheme

Acta Cryst. (2009). E65, o1268    [ doi:10.1107/S1600536809016596 ]

(1-Adamantyl){4-[(2-chloro-9-isopropyl-9H-purin-6-yl)aminomethyl]phenyl}methanone trichloromethane solvate

M. Rouchal, M. Necas and R. Vícha

Abstract top

In the title compound, C26H30ClN5O·CHCl3, the purine molecule consists of essentially planar benzene and purine ring systems [maximum deviation 0.010 (4) Å for both ring systems] forming a dihedral angle of 85.52 (9)°. Intermolecular N-H...N hydrogen bonds link adjacent molecules into centrosymmetric dimers. The structure also contains intermolecular C-H...O and C-H...N interactions. The benzene rings form offset face-to-face [pi]-[pi] stacking interactions with an interplanar distance of 3.541 (4) Å and a centroid-to-centroid distance of 4.022 (4) Å.

Comment top

Purine molecules substituted at C2, C6 and N9 are known as potential ATP-competitive inhibitors of cyclin-dependent kinases (key regulators of the cell division cycle) and due to this fact, they can show an anticancer activity (Legraverend & Grierson, 2006). The adamantane scaffold is often used in order to improve the biological properties of potential or known drugs and a number of compounds with various biological activity have been described, e.g. antitumor agents published by Long et al. (2007).

The asymmetric unit of the title compound (Fig. 1) consists of a trisubstituted purine molecule with trichloromethane solvent in the ratio of one to one. Both benzene and purine rings are essentially planar with maximum deviation from the best plane being 0.010 (4) Å for C19 of the purine ring and 0.010 (4) Å for C16 of the benzene ring. The dihedral angle between purine and benzene rings is 85.52 (9)°. The torsion angles C18/N1/C19/C22, C19/N1/C18/C15, N1/C18/C15/C16 and H24A/C24/N4/C21 are 173.42 (4), -79.52 (4), -36.80 (5) and -34.28 (5)° respectively. Adjacent molecules are linked into centrosymmetric pairs by intermolecular N1—H1A···N5i hydrogen bonds (Table 2, Fig. 2; symmetry code: (i) -x, 1 - y, 1 - z). The trichloromethane molecule forms intermolecular C—H···N and C—H···Cl interactions. Additional intermolecular interactions (Table 2) include C23—H23A···O1, C5—H5B···N3, C—H···Cl contacts and offset face-to-face π–π interactions with an interplanar distance of 3.541 (4) Å and a centroid–centroid distance of 4.022 (4) Å.

Related literature top

The title compound was prepared according to a modified literature procedure (Fiorini & Abel, 1998). For the synthesis and/or biological activity of related compounds, see: Legraverend & Grierson (2006); Long et al. (2007). For related structures, see: Trávníček & Kryštof (2004); Trávníček & Zatloukal (2004); Trávníček & Popa (2007a,b) Rouchal et al. (2009).

Experimental top

The title compound was prepared according to a slightly modified literature procedure (Fiorini & Abel, 1998). 2,6-Dichloro-9-(propan-2-yl)-9H-purine (0.53 mmol, 122.5 mg) and (1-adamantyl)-[4-(aminomethyl)phenyl]methanone hydrochloride (0.56 mmol, 170 mg) were dissolved in a mixture of DMF (2 ml) and triethylamine (1.06 mmol, 0.15 ml). The resulting solution was stirred under reflux for 2 h (the reaction progress was monitored by TLC). After this period, the mixture was diluted with water and extracted five times with 15 ml of diethyl ether. The combined organic layers were washed twice with brine and dried over sodium sulfate. The desired product was obtained by evaporation of the solvent in vacuum and purified by column chromatography (silica gel; petroleum ether/ethyl acetate, v/v 1:1) to give a colourless crystalline powder (210 mg, 86%, mp 190–192°C). The crystal used for data collection was acquired by evaporation from a chloroform solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids drawn at 50% probability for non-H atoms.
[Figure 2] Fig. 2. Centrosymmetric dimer linked by N—H···N hydrogen bonds (dashed lines). Displacement ellipsoids are drawn at 50% probability for non-H atoms.
(1-Adamantyl){4-[(2-chloro-9-isopropyl-9H-purin-6- yl)aminomethyl]phenyl}methanone trichloromethane solvate top
Crystal data top
C26H30ClN5O·CHCl3Dx = 1.365 Mg m−3
Mr = 583.39Melting point: 191 K
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4984 reflections
a = 19.434 (12) Åθ = 2.6–25.0º
b = 13.186 (7) ŵ = 0.45 mm−1
c = 22.149 (11) ÅT = 120 K
V = 5676 (5) Å3Block, colourless
Z = 80.45 × 0.40 × 0.20 mm
F000 = 2432
Data collection top
Kuma KM4 CCD
diffractometer		4984 independent reflections
Radiation source: fine-focus sealed tube2981 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.044
Detector resolution: 0.06 pixels mm-1θmax = 25.0º
T = 120 Kθmin = 2.6º
ω scansh = −23→21
Absorption correction: multi-scan
(CrysAlisRED; Oxford Diffraction, 2006)		k = −15→15
Tmin = 0.738, Tmax = 0.917l = −26→21
32219 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)] = 0.050H-atom parameters constrained
wR(F2) = 0.177  w = 1/[σ2(Fo2) + (0.0729P)2 + 9.6676P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
4984 reflectionsΔρmax = 0.71 e Å−3
334 parametersΔρmin = −0.54 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C26H30ClN5O·CHCl3V = 5676 (5) Å3
Mr = 583.39Z = 8
Orthorhombic, PbcaMo Kα
a = 19.434 (12) ŵ = 0.45 mm−1
b = 13.186 (7) ÅT = 120 K
c = 22.149 (11) Å0.45 × 0.40 × 0.20 mm
Data collection top
Kuma KM4 CCD
diffractometer		4984 independent reflections
Absorption correction: multi-scan
(CrysAlisRED; Oxford Diffraction, 2006)		2981 reflections with I > 2σ(I)
Tmin = 0.738, Tmax = 0.917Rint = 0.044
32219 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050334 parameters
wR(F2) = 0.177H-atom parameters constrained
S = 1.12Δρmax = 0.71 e Å−3
4984 reflectionsΔρmin = −0.54 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 > 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
Cl10.15090 (5)0.68048 (7)0.25476 (4)0.0305 (3)
O10.13811 (13)1.1399 (2)0.50691 (13)0.0320 (7)
N10.00385 (14)0.6307 (2)0.43338 (14)0.0230 (7)
H1A−0.01350.59310.46250.028*
N20.07497 (15)0.6451 (2)0.34920 (14)0.0226 (7)
N30.15847 (14)0.5170 (2)0.32042 (13)0.0217 (7)
N40.15553 (15)0.3704 (2)0.38744 (13)0.0233 (7)
N50.07206 (15)0.4204 (2)0.45195 (14)0.0256 (7)
C10.21373 (18)1.0428 (3)0.56796 (17)0.0254 (9)
C20.2555 (2)1.1416 (3)0.56949 (19)0.0307 (9)
H2B0.22511.19820.58190.037*
H2C0.27291.15660.52840.037*
C30.3165 (2)1.1347 (3)0.61349 (18)0.0322 (10)
H3B0.34281.20000.61320.039*
C40.2899 (2)1.1132 (3)0.67731 (19)0.0355 (10)
H4A0.26001.16960.69080.043*
H4B0.32921.10800.70560.043*
C50.2487 (2)1.0128 (3)0.67746 (18)0.0322 (10)
H5B0.23150.99880.71920.039*
C60.2956 (2)0.9260 (3)0.65710 (19)0.0361 (10)
H6A0.26950.86150.65720.043*
H6B0.33460.91920.68560.043*
C70.3232 (2)0.9470 (3)0.59318 (18)0.0299 (9)
H7A0.35390.89010.58050.036*
C80.26304 (19)0.9563 (3)0.54841 (17)0.0270 (9)
H8A0.23750.89140.54690.032*
H8B0.28110.97050.50750.032*
C90.18688 (19)1.0227 (3)0.63391 (17)0.0282 (9)
H9A0.15701.07940.64690.034*
H9B0.15930.95960.63470.034*
C100.3642 (2)1.0465 (3)0.59343 (19)0.0340 (10)
H10A0.38241.06030.55250.041*
H10B0.40361.04080.62160.041*
C110.15273 (18)1.0551 (3)0.52472 (17)0.0239 (9)
C120.10965 (18)0.9675 (3)0.50235 (17)0.0243 (9)
C130.07214 (18)0.9841 (3)0.44859 (17)0.0271 (9)
H13A0.07491.04790.42880.033*
C140.03137 (19)0.9082 (3)0.42450 (18)0.0300 (9)
H14A0.00660.92090.38830.036*
C150.02571 (18)0.8139 (3)0.45191 (17)0.0241 (8)
C160.06142 (19)0.7977 (3)0.50545 (18)0.0282 (9)
H16A0.05710.73450.52560.034*
C170.10368 (19)0.8731 (3)0.53013 (18)0.0266 (9)
H17A0.12850.85980.56620.032*
C18−0.02097 (19)0.7331 (3)0.42573 (17)0.0248 (9)
H18A−0.06680.73880.44500.030*
H18B−0.02700.74650.38210.030*
C190.05284 (17)0.5906 (3)0.39739 (16)0.0206 (8)
C200.12500 (18)0.6035 (3)0.31567 (16)0.0242 (9)
C210.13385 (17)0.4650 (3)0.36843 (16)0.0213 (8)
C220.08232 (17)0.4945 (3)0.40833 (16)0.0203 (8)
C230.11642 (19)0.3486 (3)0.43759 (17)0.0251 (9)
H23A0.12090.28740.45990.030*
C240.21277 (18)0.3110 (3)0.35970 (18)0.0279 (9)
H24A0.21290.32500.31530.033*
C250.2812 (2)0.3476 (4)0.3856 (2)0.0502 (13)
H25A0.28640.42030.37790.075*
H25B0.31910.31060.36640.075*
H25C0.28210.33520.42920.075*
C260.2007 (2)0.1985 (3)0.3687 (2)0.0460 (12)
H26A0.15640.17960.35080.069*
H26B0.20010.18310.41200.069*
H26C0.23770.16020.34910.069*
C270.5087 (2)1.1979 (4)0.7415 (2)0.0520 (14)
H27A0.47511.23340.76830.062*
Cl110.49438 (8)1.06661 (13)0.74624 (7)0.0720 (5)
Cl120.49582 (6)1.23926 (13)0.66603 (5)0.0630 (4)
Cl130.59279 (6)1.22798 (13)0.76534 (6)0.0635 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0316 (5)0.0309 (6)0.0291 (5)0.0028 (4)0.0083 (4)0.0085 (4)
O10.0316 (15)0.0228 (15)0.0416 (18)0.0013 (12)−0.0007 (12)0.0059 (13)
N10.0249 (16)0.0199 (17)0.0242 (17)−0.0002 (13)0.0038 (13)0.0003 (14)
N20.0203 (15)0.0249 (17)0.0224 (17)0.0011 (13)0.0007 (13)0.0029 (14)
N30.0206 (15)0.0228 (17)0.0216 (17)0.0001 (13)0.0018 (13)−0.0025 (14)
N40.0219 (16)0.0286 (19)0.0194 (17)0.0041 (13)0.0006 (13)−0.0001 (14)
N50.0247 (16)0.0278 (19)0.0243 (18)0.0027 (14)−0.0008 (14)−0.0014 (15)
C10.025 (2)0.025 (2)0.026 (2)0.0004 (16)0.0031 (16)−0.0034 (17)
C20.033 (2)0.026 (2)0.033 (2)−0.0035 (18)0.0026 (18)0.0040 (18)
C30.032 (2)0.029 (2)0.035 (2)−0.0052 (18)−0.0028 (18)−0.0020 (19)
C40.040 (2)0.035 (3)0.031 (2)−0.0030 (19)0.0001 (19)−0.0044 (19)
C50.038 (2)0.031 (2)0.027 (2)−0.0051 (19)0.0010 (18)−0.0044 (19)
C60.041 (2)0.032 (2)0.035 (3)−0.0031 (19)−0.0089 (19)0.000 (2)
C70.026 (2)0.030 (2)0.034 (2)0.0021 (17)0.0001 (17)−0.0043 (18)
C80.027 (2)0.027 (2)0.027 (2)0.0045 (17)0.0045 (16)−0.0048 (17)
C90.029 (2)0.027 (2)0.029 (2)−0.0016 (17)0.0082 (17)−0.0007 (18)
C100.025 (2)0.043 (3)0.034 (2)−0.0083 (19)0.0008 (18)−0.003 (2)
C110.0235 (19)0.021 (2)0.028 (2)0.0037 (16)0.0087 (16)0.0004 (17)
C120.0178 (18)0.021 (2)0.034 (2)0.0045 (15)0.0049 (16)−0.0014 (18)
C130.0251 (19)0.026 (2)0.030 (2)0.0045 (17)0.0018 (17)0.0063 (18)
C140.025 (2)0.037 (3)0.029 (2)0.0029 (18)−0.0020 (17)0.0032 (19)
C150.0221 (19)0.025 (2)0.025 (2)0.0013 (16)0.0078 (15)−0.0009 (17)
C160.029 (2)0.029 (2)0.027 (2)−0.0014 (17)0.0030 (17)0.0037 (18)
C170.029 (2)0.022 (2)0.029 (2)−0.0009 (16)−0.0039 (17)0.0028 (17)
C180.0267 (19)0.025 (2)0.023 (2)0.0044 (16)0.0016 (16)0.0000 (17)
C190.0153 (17)0.021 (2)0.025 (2)−0.0035 (15)−0.0049 (15)−0.0059 (17)
C200.0238 (19)0.028 (2)0.021 (2)0.0000 (16)0.0008 (16)0.0018 (17)
C210.0197 (18)0.025 (2)0.020 (2)−0.0020 (15)−0.0032 (15)−0.0002 (17)
C220.0219 (18)0.021 (2)0.0178 (19)−0.0035 (15)−0.0017 (14)−0.0018 (16)
C230.030 (2)0.026 (2)0.020 (2)0.0019 (16)0.0021 (16)0.0025 (17)
C240.0207 (19)0.037 (2)0.026 (2)0.0063 (17)0.0015 (16)−0.0011 (18)
C250.028 (2)0.070 (4)0.053 (3)0.012 (2)−0.006 (2)−0.027 (3)
C260.048 (3)0.036 (3)0.054 (3)0.011 (2)0.023 (2)0.007 (2)
C270.035 (2)0.087 (4)0.034 (3)0.009 (3)−0.003 (2)−0.013 (3)
Cl110.0769 (10)0.0811 (11)0.0581 (9)0.0080 (8)0.0082 (7)−0.0164 (8)
Cl120.0379 (7)0.1163 (13)0.0348 (7)0.0103 (7)−0.0040 (5)−0.0052 (7)
Cl130.0324 (6)0.1206 (13)0.0377 (7)0.0056 (7)−0.0026 (5)−0.0095 (7)
Geometric parameters (Å, °) top
Cl1—C201.762 (4)C8—H8A0.990
O1—C111.219 (4)C8—H8B0.990
N1—C191.349 (5)C9—H9A0.990
N1—C181.445 (5)C9—H9B0.990
N1—H1A0.880C10—H10A0.990
N2—C201.341 (5)C10—H10B0.990
N2—C191.357 (5)C11—C121.511 (5)
N3—C201.316 (5)C12—C171.392 (5)
N3—C211.353 (5)C12—C131.413 (5)
N4—C231.376 (5)C13—C141.384 (5)
N4—C211.383 (5)C13—H13A0.950
N4—C241.493 (5)C14—C151.388 (5)
N5—C231.320 (5)C14—H14A0.950
N5—C221.388 (5)C15—C161.390 (5)
C1—C111.532 (5)C15—C181.515 (5)
C1—C21.535 (5)C16—C171.401 (5)
C1—C81.552 (5)C16—H16A0.950
C1—C91.574 (5)C17—H17A0.950
C2—C31.538 (6)C18—H18A0.990
C2—H2B0.990C18—H18B0.990
C2—H2C0.990C19—C221.411 (5)
C3—C41.531 (6)C21—C221.391 (5)
C3—C101.551 (6)C23—H23A0.950
C3—H3B1.000C24—C261.515 (6)
C4—C51.548 (6)C24—C251.526 (6)
C4—H4A0.990C24—H24A1.000
C4—H4B0.990C25—H25A0.980
C5—C61.531 (6)C25—H25B0.980
C5—C91.546 (6)C25—H25C0.980
C5—H5B1.000C26—H26A0.980
C6—C71.539 (6)C26—H26B0.980
C6—H6A0.990C26—H26C0.980
C6—H6B0.990C27—Cl111.756 (6)
C7—C101.535 (6)C27—Cl131.763 (5)
C7—C81.537 (5)C27—Cl121.775 (5)
C7—H7A1.000C27—H27A1.000
C19—N1—C18122.2 (3)H10A—C10—H10B108.2
C19—N1—H1A118.9O1—C11—C12117.8 (3)
C18—N1—H1A118.9O1—C11—C1118.7 (3)
C20—N2—C19116.7 (3)C12—C11—C1123.5 (3)
C20—N3—C21109.1 (3)C17—C12—C13117.9 (3)
C23—N4—C21105.4 (3)C17—C12—C11125.8 (3)
C23—N4—C24129.4 (3)C13—C12—C11116.3 (3)
C21—N4—C24125.1 (3)C14—C13—C12120.5 (4)
C23—N5—C22104.1 (3)C14—C13—H13A119.7
C11—C1—C2109.4 (3)C12—C13—H13A119.7
C11—C1—C8112.4 (3)C13—C14—C15121.7 (4)
C2—C1—C8107.7 (3)C13—C14—H14A119.2
C11—C1—C9110.0 (3)C15—C14—H14A119.2
C2—C1—C9107.3 (3)C14—C15—C16118.1 (4)
C8—C1—C9109.9 (3)C14—C15—C18120.7 (3)
C1—C2—C3111.8 (3)C16—C15—C18121.2 (3)
C1—C2—H2B109.3C15—C16—C17121.1 (4)
C3—C2—H2B109.3C15—C16—H16A119.4
C1—C2—H2C109.3C17—C16—H16A119.4
C3—C2—H2C109.3C12—C17—C16120.7 (4)
H2B—C2—H2C107.9C12—C17—H17A119.7
C4—C3—C2109.6 (3)C16—C17—H17A119.7
C4—C3—C10109.1 (3)N1—C18—C15114.4 (3)
C2—C3—C10108.9 (3)N1—C18—H18A108.7
C4—C3—H3B109.8C15—C18—H18A108.7
C2—C3—H3B109.8N1—C18—H18B108.7
C10—C3—H3B109.8C15—C18—H18B108.7
C3—C4—C5109.6 (3)H18A—C18—H18B107.6
C3—C4—H4A109.8N1—C19—N2118.8 (3)
C5—C4—H4A109.8N1—C19—C22122.5 (3)
C3—C4—H4B109.8N2—C19—C22118.8 (3)
C5—C4—H4B109.8N3—C20—N2131.9 (3)
H4A—C4—H4B108.2N3—C20—Cl1114.8 (3)
C6—C5—C9110.0 (3)N2—C20—Cl1113.3 (3)
C6—C5—C4109.3 (3)N3—C21—N4126.1 (3)
C9—C5—C4109.2 (3)N3—C21—C22127.8 (3)
C6—C5—H5B109.4N4—C21—C22106.1 (3)
C9—C5—H5B109.4N5—C22—C21110.4 (3)
C4—C5—H5B109.4N5—C22—C19133.8 (3)
C5—C6—C7110.1 (3)C21—C22—C19115.7 (3)
C5—C6—H6A109.6N5—C23—N4113.9 (3)
C7—C6—H6A109.6N5—C23—H23A123.0
C5—C6—H6B109.6N4—C23—H23A123.0
C7—C6—H6B109.6N4—C24—C26110.1 (3)
H6A—C6—H6B108.2N4—C24—C25109.2 (3)
C10—C7—C8109.2 (3)C26—C24—C25113.3 (4)
C10—C7—C6109.4 (3)N4—C24—H24A108.0
C8—C7—C6110.0 (3)C26—C24—H24A108.0
C10—C7—H7A109.4C25—C24—H24A108.0
C8—C7—H7A109.4C24—C25—H25A109.5
C6—C7—H7A109.4C24—C25—H25B109.5
C7—C8—C1110.4 (3)H25A—C25—H25B109.5
C7—C8—H8A109.6C24—C25—H25C109.5
C1—C8—H8A109.6H25A—C25—H25C109.5
C7—C8—H8B109.6H25B—C25—H25C109.5
C1—C8—H8B109.6C24—C26—H26A109.5
H8A—C8—H8B108.1C24—C26—H26B109.5
C5—C9—C1109.6 (3)H26A—C26—H26B109.5
C5—C9—H9A109.7C24—C26—H26C109.5
C1—C9—H9A109.7H26A—C26—H26C109.5
C5—C9—H9B109.7H26B—C26—H26C109.5
C1—C9—H9B109.7Cl11—C27—Cl13110.5 (3)
H9A—C9—H9B108.2Cl11—C27—Cl12109.7 (3)
C7—C10—C3109.4 (3)Cl13—C27—Cl12110.1 (3)
C7—C10—H10A109.8Cl11—C27—H27A108.8
C3—C10—H10A109.8Cl13—C27—H27A108.8
C7—C10—H10B109.8Cl12—C27—H27A108.8
C3—C10—H10B109.8
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N5i0.882.223.013 (5)150
C27—H27A···N2ii1.002.593.553 (6)161
C5—H5B···N3iii1.002.663.641 (5)166
C23—H23A···O1iv0.952.233.179 (5)175
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, −y+2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N5i0.882.223.013 (5)150
C27—H27A···N2ii1.002.593.553 (6)161
C5—H5B···N3iii1.002.663.641 (5)166
C23—H23A···O1iv0.952.233.179 (5)175
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, −y+2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x, y−1, z.
Acknowledgements top

Financial support of this work by the Science Foundation of the Czech Republic (grant No. 203/06/P362) and the Czech Ministry of Education (project No. MSM 7088352101) is gratefully acknowledged.

references
References top

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Fiorini, M. T. & Abel, Ch. (1998). Tetrahedron Lett. 39, 1827–1830.

Legraverend, M. & Grierson, D. S. (2006). Bioorg. Med. Chem. 14, 3987–4006.

Long, J., Manchandia, T., Ban, K., Gao, S., Miller, C. & Chandra, J. (2007). Cancer Chemother. Pharmacol. 59, 527–535.

Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.

Rouchal, M., Nečas, M., de Carvalho, F. P. & Vícha, R. (2009). Acta Cryst. E65, o298–o299.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Trávníček, Z. & Kryštof, V. (2004). Acta Cryst. E60, o2324–o2327.

Trávníček, Z. & Popa, I. (2007a). Acta Cryst. E63, o629–o631.

Trávníček, Z. & Popa, I. (2007b). Acta Cryst. E63, o728–o730.

Trávníček, Z. & Zatloukal, M. (2004). Acta Cryst. E60, o924–o926.