(E)-3-(9-Anthr­yl)-1-(4-fluoro­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Wang, X.-L.; Wang, G.-Z.; Geng, R.-X.; Zhou, C.-H.

doi:10.1107/S1600536809055524

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o320

https://doi.org/10.1107/S1600536809055524

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(E)-3-(9-Anthryl)-1-(4-fluorophenyl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Xiao-Ling Wang,^a Guang-Zhou Wang,^a Rong-Xia Geng ^a and Cheng-He Zhou ^a ^*

^aSchool of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 14 December 2009; accepted 28 December 2009; online 9 January 2010)

In the title compound, C₂₆H₁₆FN₃O₃, the dihedral angle between the anthryl and fluorophenyl groups is 37.8 (1)°. With respect to the imidazolyl group, the twist angles between the imidazolyl group and the anthryl unit and between the imidazoly group and the fluorophenyl group are 64.4 (1) and 74.5 (1)°, respectively.

Related literature

For general background to chalcone derivatives, see: Detsi et al. (2009 ). For the synthesis, see: Erhardt et al. (1985 ); Kranz et al. (1980 ). For related structures, see: Lu et al. (2009 ); Wang et al. (2009 ). For a comment on the molecular shape, see: Hou et al. (2009 ).

Experimental

Crystal data

C₂₆H₁₆FN₃O₃
M_r = 437.42
Triclinic, $[P \overline 1]$
a = 9.3362 (6) Å
b = 10.9587 (6) Å
c = 11.6018 (5) Å
α = 70.371 (5)°
β = 88.062 (4)°
γ = 66.781 (6)°
V = 1020.78 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.49 × 0.41 × 0.30 mm

Data collection

Oxford Diffraction Xcaliber diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.951, T_max = 0.970
8826 measured reflections
4374 independent reflections
3193 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.01
4374 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809055524/ng2707sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055524/ng2707Isup2.hkl

checkCIF report

Comment top

Chalcones (1,3-diaryl-2-propen-1-ones) are flavonoid and isoflavnoid precursors which are abundant in edible plants and display wide biological activities such as antioxidant, antibacterial, antileishmanial, anticancer, antiangiogenic, anti-infective and anti-inflammatory activities. Chalcone derivatives have received much attention due to their relatively simple structures, and wide variety of biological activities (Detsi et al. 2009). A series of chalcone derivatives containing imidazole ring have been synthesized and crystal structures of some of them have been reported (Lu et al. 2009; Wang et al. 2009). We report here the structure of the title compound (I).

The title compound (I), C₂₆H₁₆FN₃O₃, shows an organic-clip-shaped motif (Hou et al. 2009). The ringent dihedral angle between the anthryl unit and the fluorophenyl group is 37.80°. The imidazolyl group can be seen as the handle of organic clip, and the dihedral angles between the imidazolyl group and the anthryl unit or the fluorophenyl group are 64.40° and 74.51° respectively. In the solid state, the compound (I) is stabilized by weak intermolecule C—H···O and C—H···F hydrogen bonds generating an infinite two-dimensional network.

Related literature top

For general background to chalcone derivatives, see: Detsi et al. (2009). For the synthesis, see: Erhardt et al. (1985); Kranz et al. (1980). For related structures, see: Lu et al. (2009); Wang et al. (2009). For a comment on the molecular shape, see: Hou et al. (2009).

Experimental top

Compound (I) was synthesized according to the procedure of Erhardt et al. (1985) and Kranz et al. (1980). Single crystals (I) suitable for X-ray analysis were grown in dichloromethane by slow evaporation at room temperature.

Structure description top

For general background to chalcone derivatives, see: Detsi et al. (2009). For the synthesis, see: Erhardt et al. (1985); Kranz et al. (1980). For related structures, see: Lu et al. (2009); Wang et al. (2009). For a comment on the molecular shape, see: Hou et al. (2009).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), showing theatom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the CrystalStructure of (I), showing the formation of the three-dimensional network.

(E)-3-(9-Anthryl)-1-(4-fluorophenyl)-2-(4-nitro-1H-imidazol- 1-yl)prop-2-en-1-one top

Crystal data top

C₂₆H₁₆FN₃O₃	Z = 2
M_r = 437.42	F(000) = 452
Triclinic, P1	D_x = 1.423 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3362 (6) Å	Cell parameters from 8826 reflections
b = 10.9587 (6) Å	θ = 2.8–27.0°
c = 11.6018 (5) Å	µ = 0.10 mm⁻¹
α = 70.371 (5)°	T = 173 K
β = 88.062 (4)°	Block, yellow
γ = 66.781 (6)°	0.49 × 0.41 × 0.30 mm
V = 1020.78 (10) Å³

Data collection top

Oxford Diffraction Xcaliber diffractometer	4374 independent reflections
Radiation source: fine-focus sealed tube	3193 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 0.01 pixels mm^-1	θ_max = 27.0°, θ_min = 2.8°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −13→12
T_min = 0.951, T_max = 0.970	l = −14→14
8826 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0501P)²] where P = (F_o² + 2F_c²)/3
4374 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₆H₁₆FN₃O₃	γ = 66.781 (6)°
M_r = 437.42	V = 1020.78 (10) Å³
Triclinic, P1	Z = 2
a = 9.3362 (6) Å	Mo Kα radiation
b = 10.9587 (6) Å	µ = 0.10 mm⁻¹
c = 11.6018 (5) Å	T = 173 K
α = 70.371 (5)°	0.49 × 0.41 × 0.30 mm
β = 88.062 (4)°

Data collection top

Oxford Diffraction Xcaliber diffractometer	4374 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3193 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.970	R_int = 0.020
8826 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
4374 reflections	Δρ_min = −0.19 e Å⁻³
298 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 > 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

	x	y	z	U_iso*/U_eq
F1	0.40315 (10)	0.15681 (10)	1.18206 (7)	0.0560 (3)
O1	0.12744 (13)	−0.02448 (11)	0.81580 (8)	0.0455 (3)
N3	0.19905 (12)	0.08673 (11)	0.58002 (8)	0.0261 (2)
C15	0.10394 (14)	0.30540 (13)	0.61663 (11)	0.0282 (3)
H15A	0.1064	0.3481	0.5309	0.034*
C17	0.16584 (14)	0.07397 (13)	0.79428 (10)	0.0275 (3)
C23	0.33391 (14)	0.16396 (13)	0.87665 (11)	0.0270 (3)
H23A	0.3671	0.1929	0.7975	0.032*
C14	0.04204 (14)	0.40033 (13)	0.68792 (10)	0.0272 (3)
C6	−0.08868 (15)	0.40198 (13)	0.75307 (10)	0.0282 (3)
C18	0.22475 (14)	0.10459 (12)	0.89378 (10)	0.0244 (3)
C7	0.11980 (15)	0.48598 (13)	0.69277 (11)	0.0291 (3)
C22	0.39456 (15)	0.18126 (13)	0.97408 (12)	0.0333 (3)
H22A	0.4704	0.2207	0.9636	0.040*
N2	0.18404 (14)	0.02358 (13)	0.41956 (9)	0.0390 (3)
C19	0.17599 (15)	0.06337 (14)	1.01033 (10)	0.0323 (3)
H19A	0.1023	0.0216	1.0226	0.039*
C12	0.07161 (15)	0.56901 (13)	0.77072 (11)	0.0326 (3)
C16	0.15658 (14)	0.16506 (13)	0.66238 (10)	0.0255 (3)
C26	0.32395 (15)	−0.05927 (13)	0.49025 (10)	0.0295 (3)
O2	0.56329 (12)	−0.24366 (12)	0.53163 (10)	0.0525 (3)
C8	0.25072 (16)	0.48911 (14)	0.62676 (12)	0.0368 (3)
H8A	0.2838	0.4365	0.5731	0.044*
C1	−0.13552 (15)	0.48673 (14)	0.83035 (11)	0.0330 (3)
C20	0.23331 (16)	0.08250 (15)	1.10757 (11)	0.0368 (3)
H20A	0.1986	0.0568	1.1866	0.044*
C21	0.34228 (15)	0.13994 (14)	1.08624 (11)	0.0346 (3)
O3	0.41958 (15)	−0.18717 (12)	0.36400 (9)	0.0656 (4)
C13	−0.05363 (16)	0.56575 (14)	0.83786 (12)	0.0358 (3)
H13A	−0.0842	0.6195	0.8907	0.043*
C5	−0.17915 (15)	0.32560 (14)	0.74550 (12)	0.0343 (3)
H5A	−0.1529	0.2715	0.6929	0.041*
C2	−0.26464 (17)	0.48480 (16)	0.89925 (13)	0.0437 (4)
H2A	−0.2949	0.5386	0.9521	0.052*
C11	0.15633 (17)	0.64982 (15)	0.77975 (12)	0.0405 (3)
H11A	0.1242	0.7063	0.8303	0.049*
C9	0.32888 (18)	0.56622 (15)	0.63942 (13)	0.0450 (4)
H9A	0.4165	0.5659	0.5953	0.054*
C4	−0.30200 (17)	0.32892 (16)	0.81208 (13)	0.0433 (4)
H4A	−0.3604	0.2770	0.8057	0.052*
C10	0.28170 (19)	0.64686 (16)	0.71722 (13)	0.0472 (4)
H10A	0.3384	0.6994	0.7257	0.057*
C3	−0.34423 (18)	0.40905 (17)	0.89124 (14)	0.0484 (4)
H3A	−0.4292	0.4089	0.9387	0.058*
N1	0.44252 (15)	−0.17030 (13)	0.45944 (10)	0.0389 (3)
C25	0.33644 (15)	−0.02437 (13)	0.58946 (11)	0.0294 (3)
H25A	0.4225	−0.0681	0.6519	0.035*
C24	0.11069 (16)	0.11104 (15)	0.47696 (11)	0.0357 (3)
H24A	0.0077	0.1832	0.4500	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0625 (6)	0.0621 (6)	0.0440 (5)	−0.0166 (5)	−0.0174 (4)	−0.0276 (5)
O1	0.0783 (8)	0.0471 (6)	0.0291 (5)	−0.0426 (6)	0.0100 (5)	−0.0145 (5)
N3	0.0312 (6)	0.0287 (6)	0.0189 (5)	−0.0111 (5)	0.0027 (4)	−0.0102 (4)
C15	0.0326 (7)	0.0304 (7)	0.0205 (6)	−0.0121 (6)	0.0030 (5)	−0.0088 (5)
C17	0.0327 (7)	0.0276 (7)	0.0239 (6)	−0.0126 (6)	0.0054 (5)	−0.0108 (5)
C23	0.0278 (6)	0.0230 (6)	0.0263 (6)	−0.0074 (5)	0.0035 (5)	−0.0077 (5)
C14	0.0313 (7)	0.0220 (6)	0.0214 (6)	−0.0051 (5)	−0.0018 (5)	−0.0057 (5)
C6	0.0308 (7)	0.0245 (6)	0.0234 (6)	−0.0056 (6)	−0.0015 (5)	−0.0075 (5)
C18	0.0259 (6)	0.0228 (6)	0.0205 (6)	−0.0052 (5)	0.0008 (5)	−0.0083 (5)
C7	0.0330 (7)	0.0205 (6)	0.0246 (6)	−0.0057 (6)	−0.0036 (5)	−0.0026 (5)
C22	0.0286 (7)	0.0277 (7)	0.0419 (7)	−0.0081 (6)	−0.0036 (6)	−0.0135 (6)
N2	0.0484 (7)	0.0445 (7)	0.0244 (5)	−0.0142 (6)	0.0014 (5)	−0.0177 (5)
C19	0.0353 (7)	0.0393 (8)	0.0243 (6)	−0.0178 (6)	0.0060 (5)	−0.0107 (6)
C12	0.0377 (7)	0.0225 (6)	0.0302 (6)	−0.0066 (6)	−0.0049 (6)	−0.0065 (5)
C16	0.0290 (6)	0.0291 (7)	0.0209 (6)	−0.0117 (6)	0.0044 (5)	−0.0122 (5)
C26	0.0372 (7)	0.0302 (7)	0.0245 (6)	−0.0151 (6)	0.0099 (5)	−0.0127 (5)
O2	0.0431 (6)	0.0485 (7)	0.0645 (7)	−0.0085 (6)	0.0074 (6)	−0.0305 (6)
C8	0.0407 (8)	0.0285 (7)	0.0353 (7)	−0.0119 (6)	0.0036 (6)	−0.0069 (6)
C1	0.0354 (7)	0.0281 (7)	0.0298 (6)	−0.0055 (6)	0.0014 (6)	−0.0121 (6)
C20	0.0419 (8)	0.0438 (8)	0.0208 (6)	−0.0119 (7)	0.0033 (6)	−0.0131 (6)
C21	0.0353 (7)	0.0334 (7)	0.0298 (7)	−0.0028 (6)	−0.0101 (6)	−0.0166 (6)
O3	0.0953 (9)	0.0581 (7)	0.0393 (6)	−0.0133 (7)	0.0112 (6)	−0.0341 (6)
C13	0.0430 (8)	0.0282 (7)	0.0336 (7)	−0.0073 (6)	0.0005 (6)	−0.0160 (6)
C5	0.0349 (7)	0.0352 (7)	0.0345 (7)	−0.0116 (6)	0.0036 (6)	−0.0173 (6)
C2	0.0483 (9)	0.0418 (8)	0.0443 (8)	−0.0138 (7)	0.0155 (7)	−0.0254 (7)
C11	0.0521 (9)	0.0298 (7)	0.0375 (7)	−0.0148 (7)	−0.0069 (7)	−0.0100 (6)
C9	0.0450 (9)	0.0385 (8)	0.0485 (8)	−0.0202 (7)	0.0043 (7)	−0.0077 (7)
C4	0.0401 (8)	0.0457 (9)	0.0535 (9)	−0.0208 (7)	0.0118 (7)	−0.0253 (7)
C10	0.0545 (10)	0.0359 (8)	0.0505 (9)	−0.0245 (8)	−0.0082 (8)	−0.0058 (7)
C3	0.0439 (9)	0.0539 (10)	0.0549 (9)	−0.0196 (8)	0.0226 (7)	−0.0301 (8)
N1	0.0520 (8)	0.0349 (7)	0.0357 (6)	−0.0196 (6)	0.0167 (6)	−0.0184 (6)
C25	0.0311 (7)	0.0282 (7)	0.0286 (6)	−0.0099 (6)	0.0008 (5)	−0.0120 (6)
C24	0.0371 (8)	0.0422 (8)	0.0240 (6)	−0.0100 (7)	−0.0023 (6)	−0.0140 (6)

Geometric parameters (Å, º) top

F1—C21	1.3626 (13)	C12—C11	1.4288 (18)
O1—C17	1.2135 (14)	C26—C25	1.3508 (15)
N3—C25	1.3521 (16)	C26—N1	1.4272 (17)
N3—C24	1.3641 (15)	O2—N1	1.2312 (15)
N3—C16	1.4367 (14)	C8—C9	1.3583 (18)
C15—C16	1.3273 (17)	C8—H8A	0.9500
C15—C14	1.4739 (16)	C1—C13	1.3854 (18)
C15—H15A	0.9500	C1—C2	1.4270 (19)
C17—C18	1.4821 (15)	C20—C21	1.3696 (19)
C17—C16	1.5034 (16)	C20—H20A	0.9500
C23—C22	1.3806 (16)	O3—N1	1.2210 (13)
C23—C18	1.3869 (16)	C13—H13A	0.9500
C23—H23A	0.9500	C5—C4	1.3563 (18)
C14—C7	1.4095 (17)	C5—H5A	0.9500
C14—C6	1.4109 (17)	C2—C3	1.339 (2)
C6—C5	1.4260 (17)	C2—H2A	0.9500
C6—C1	1.4389 (16)	C11—C10	1.351 (2)
C18—C19	1.3963 (16)	C11—H11A	0.9500
C7—C8	1.4262 (18)	C9—C10	1.411 (2)
C7—C12	1.4319 (17)	C9—H9A	0.9500
C22—C21	1.3682 (18)	C4—C3	1.4192 (19)
C22—H22A	0.9500	C4—H4A	0.9500
N2—C24	1.3082 (16)	C10—H10A	0.9500
N2—C26	1.3565 (16)	C3—H3A	0.9500
C19—C20	1.3752 (16)	C25—H25A	0.9500
C19—H19A	0.9500	C24—H24A	0.9500
C12—C13	1.3885 (18)

C25—N3—C24	106.98 (10)	C13—C1—C2	121.72 (11)
C25—N3—C16	126.08 (10)	C13—C1—C6	119.74 (12)
C24—N3—C16	126.93 (11)	C2—C1—C6	118.54 (12)
C16—C15—C14	125.33 (11)	C21—C20—C19	117.49 (12)
C16—C15—H15A	117.3	C21—C20—H20A	121.3
C14—C15—H15A	117.3	C19—C20—H20A	121.3
O1—C17—C18	121.96 (11)	F1—C21—C22	117.71 (12)
O1—C17—C16	118.70 (10)	F1—C21—C20	118.41 (11)
C18—C17—C16	119.33 (10)	C22—C21—C20	123.89 (11)
C22—C23—C18	120.32 (11)	C1—C13—C12	122.18 (11)
C22—C23—H23A	119.8	C1—C13—H13A	118.9
C18—C23—H23A	119.8	C12—C13—H13A	118.9
C7—C14—C6	120.79 (10)	C4—C5—C6	121.13 (12)
C7—C14—C15	118.37 (11)	C4—C5—H5A	119.4
C6—C14—C15	120.80 (11)	C6—C5—H5A	119.4
C14—C6—C5	123.66 (11)	C3—C2—C1	121.60 (12)
C14—C6—C1	118.58 (11)	C3—C2—H2A	119.2
C5—C6—C1	117.76 (11)	C1—C2—H2A	119.2
C23—C18—C19	119.36 (11)	C10—C11—C12	120.76 (13)
C23—C18—C17	122.07 (10)	C10—C11—H11A	119.6
C19—C18—C17	118.43 (11)	C12—C11—H11A	119.6
C14—C7—C8	122.54 (11)	C8—C9—C10	120.93 (14)
C14—C7—C12	119.57 (11)	C8—C9—H9A	119.5
C8—C7—C12	117.84 (11)	C10—C9—H9A	119.5
C21—C22—C23	118.05 (12)	C5—C4—C3	120.74 (13)
C21—C22—H22A	121.0	C5—C4—H4A	119.6
C23—C22—H22A	121.0	C3—C4—H4A	119.6
C24—N2—C26	103.31 (10)	C11—C10—C9	120.38 (13)
C20—C19—C18	120.87 (12)	C11—C10—H10A	119.8
C20—C19—H19A	119.6	C9—C10—H10A	119.8
C18—C19—H19A	119.6	C2—C3—C4	120.17 (13)
C13—C12—C11	121.85 (12)	C2—C3—H3A	119.9
C13—C12—C7	119.02 (11)	C4—C3—H3A	119.9
C11—C12—C7	119.10 (12)	O3—N1—O2	123.78 (12)
C15—C16—N3	119.29 (10)	O3—N1—C26	118.88 (12)
C15—C16—C17	127.06 (10)	O2—N1—C26	117.34 (11)
N3—C16—C17	113.45 (10)	C26—C25—N3	104.56 (11)
C25—C26—N2	112.89 (11)	C26—C25—H25A	127.7
C25—C26—N1	125.20 (12)	N3—C25—H25A	127.7
N2—C26—N1	121.91 (11)	N2—C24—N3	112.26 (12)
C9—C8—C7	120.97 (12)	N2—C24—H24A	123.9
C9—C8—H8A	119.5	N3—C24—H24A	123.9
C7—C8—H8A	119.5

Experimental details

Crystal data
Chemical formula	C₂₆H₁₆FN₃O₃
M_r	437.42
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.3362 (6), 10.9587 (6), 11.6018 (5)
α, β, γ (°)	70.371 (5), 88.062 (4), 66.781 (6)
V (Å³)	1020.78 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.49 × 0.41 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcaliber
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.951, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	8826, 4374, 3193
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.01
No. of reflections	4374
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant Nos. 2007BB5369 and 2006BB4341) for financial support.

References

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