organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

12-(2-Methoxyphenyl)-9,9-di­methyl-8,9-di­hydro-12H-benzo[a]xanthen-11(10H)-one

aDepartment of Chemistry, Tangshan Normal College, Tangshan 063000, People's Republic of China
*Correspondence e-mail: deling1@126.com

(Received 6 November 2009; accepted 4 December 2009; online 12 December 2009)

The title compound, C26H24O3, was synthesized via the coupling of 2-methoxy­benzaldehyde, 2-naphthol and 5,5-dimethyl­cyclo­hexane-1,3-dione. The pyran ring adopts a boat conformation, while the cyclo­hexenone ring is in an envelope conformation. The 2-methoxy­phenyl ring is almost perpendic­ular to the plane through the four C atoms of the pyran ring [dihedral angle = 88.76 (9)°].

Related literature

For the antiviral activity of xanthenes and benzoxanthenes, see: Lambert et al. (1997[Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24O3

  • Mr = 384.45

  • Monoclinic, P 21 /n

  • a = 7.8454 (11) Å

  • b = 22.670 (3) Å

  • c = 11.3100 (13) Å

  • β = 98.893 (4)°

  • V = 1987.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 113 K

  • 0.36 × 0.28 × 0.20 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.970, Tmax = 0.985

  • 12038 measured reflections

  • 3860 independent reflections

  • 3274 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.122

  • S = 1.09

  • 3860 reflections

  • 266 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

For the antiviral activity of xanthenes and benzoxanthenes, see: (Lambert et al. (1997).

Experimental top

To a mixture of 2-naphthol (1.0 mmol), 2-methoxybenzaldehyde (1.0 mmol), and 5,5-dimethylcyclohexane-1,3-dione (1.1 mmol) strontium trifluoromethanesulfonate (0.1 mmol) in 1,2-dichloroethane (2 ml) was added. The mixture was stirred at 80 °C for 5 h and the progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, 5 ml of water were added and the product was extracted three times with 10 ml of ethyl acetate. The organic layer was dried over MgSO4 filtered off and the solvent was evaporated. The crude was product dissolved in ethylacetate and purified by flash chromatography on silica gel. The solvent was evaporated and the product was dissolved in ethanol. A single crystal was obtained by slow evaporation of the solvent from a solution in ethanol.

Refinement top

All H atoms were included in the refinement in the riding model approximation, with C—H = 0.95–1.00 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing the atom-numbering scheme. Dispacement ellipsoids are drawn at the 30% probability level.
12-(2-Methoxyphenyl)-9,9-dimethyl-9,10-dihydro-8H- benzo[a]xanthen-11(12H)-one top
Crystal data top
C26H24O3F(000) = 816
Mr = 384.45Dx = 1.285 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
a = 7.8454 (11) ÅCell parameters from 3867 reflections
b = 22.670 (3) Åθ = 1.8–27.2°
c = 11.3100 (13) ŵ = 0.08 mm1
β = 98.893 (4)°T = 113 K
V = 1987.4 (5) Å3Block, colorless
Z = 40.36 × 0.28 × 0.20 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3860 independent reflections
Radiation source: rotating anode3274 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.035
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω and ϕ scansh = 98
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2720
Tmin = 0.970, Tmax = 0.985l = 1313
12038 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)] = 0.049H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0629P)2 + 0.2114P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
3860 reflectionsΔρmax = 0.29 e Å3
266 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (2)
Crystal data top
C26H24O3V = 1987.4 (5) Å3
Mr = 384.45Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.8454 (11) ŵ = 0.08 mm1
b = 22.670 (3) ÅT = 113 K
c = 11.3100 (13) Å0.36 × 0.28 × 0.20 mm
β = 98.893 (4)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3860 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
3274 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.985Rint = 0.035
12038 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.09Δρmax = 0.29 e Å3
3860 reflectionsΔρmin = 0.21 e Å3
266 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
xyzUiso*/Ueq
O10.32998 (13)0.05276 (4)0.89201 (9)0.0251 (3)
O20.07739 (15)0.20650 (5)0.81569 (13)0.0444 (4)
O30.19539 (13)0.05495 (5)0.63209 (9)0.0249 (3)
C10.2801 (2)0.11049 (7)0.87702 (13)0.0239 (4)
C20.11615 (19)0.12678 (7)0.84090 (13)0.0237 (4)
C30.0248 (2)0.08279 (6)0.79729 (13)0.0226 (3)
H30.12740.09300.83580.027*
C40.03259 (19)0.02110 (7)0.83795 (12)0.0220 (3)
C50.20193 (19)0.00984 (7)0.88233 (12)0.0229 (3)
C60.2635 (2)0.04641 (7)0.92099 (13)0.0259 (4)
H60.38130.05180.95430.031*
C70.1525 (2)0.09314 (7)0.91012 (13)0.0266 (4)
H70.19360.13120.93570.032*
C80.0236 (2)0.08537 (7)0.86104 (13)0.0249 (4)
C90.08557 (19)0.02749 (7)0.82836 (12)0.0238 (4)
C100.2640 (2)0.02089 (7)0.78388 (13)0.0272 (4)
H100.30970.01740.76530.033*
C110.3711 (2)0.06874 (8)0.76733 (14)0.0328 (4)
H110.48990.06320.73720.039*
C120.3080 (2)0.12620 (8)0.79428 (15)0.0342 (4)
H120.38250.15930.77920.041*
C130.1390 (2)0.13381 (7)0.84225 (14)0.0311 (4)
H130.09780.17240.86350.037*
C140.0722 (2)0.18961 (7)0.84212 (15)0.0305 (4)
C150.2164 (2)0.23259 (7)0.88335 (17)0.0352 (4)
H15A0.22390.23830.97080.042*
H15B0.18680.27110.84440.042*
C160.3943 (2)0.21341 (7)0.85643 (16)0.0322 (4)
C170.4295 (2)0.15108 (7)0.90742 (14)0.0275 (4)
H17A0.53030.13440.87610.033*
H17B0.45940.15370.99560.033*
C180.3939 (2)0.21340 (8)0.72089 (17)0.0412 (5)
H18A0.35640.25210.68800.062*
H18B0.31460.18300.68360.062*
H18C0.51060.20510.70440.062*
C190.5342 (2)0.25523 (8)0.9164 (2)0.0473 (5)
H19A0.64790.24010.90580.071*
H19B0.52740.25811.00200.071*
H19C0.51730.29440.87980.071*
C200.07830 (19)0.08847 (6)0.66195 (13)0.0217 (3)
C210.03606 (19)0.07426 (6)0.58126 (13)0.0218 (3)
C220.0157 (2)0.08026 (7)0.45887 (13)0.0250 (4)
H220.06090.06970.40500.030*
C230.1784 (2)0.10161 (7)0.41493 (14)0.0279 (4)
H230.21320.10540.33100.033*
C240.2910 (2)0.11751 (7)0.49250 (14)0.0277 (4)
H240.40170.13300.46250.033*
C250.2392 (2)0.11041 (6)0.61498 (14)0.0245 (4)
H250.31690.12100.66810.029*
C260.3182 (2)0.04429 (7)0.55369 (15)0.0296 (4)
H26A0.27630.01260.49780.044*
H26B0.42860.03270.60070.044*
H26C0.33410.08030.50870.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0227 (6)0.0247 (6)0.0265 (6)0.0001 (4)0.0007 (5)0.0011 (4)
O20.0281 (7)0.0341 (7)0.0693 (9)0.0077 (5)0.0024 (6)0.0136 (6)
O30.0208 (6)0.0320 (6)0.0223 (6)0.0042 (5)0.0041 (5)0.0003 (4)
C10.0275 (9)0.0259 (8)0.0182 (7)0.0012 (7)0.0032 (6)0.0024 (6)
C20.0232 (8)0.0276 (8)0.0203 (8)0.0011 (6)0.0037 (6)0.0042 (6)
C30.0216 (8)0.0261 (8)0.0205 (8)0.0023 (6)0.0046 (6)0.0024 (6)
C40.0246 (9)0.0281 (8)0.0137 (7)0.0012 (6)0.0039 (6)0.0012 (6)
C50.0234 (8)0.0280 (8)0.0173 (7)0.0028 (6)0.0032 (6)0.0013 (6)
C60.0251 (9)0.0316 (9)0.0201 (8)0.0023 (7)0.0007 (7)0.0005 (6)
C70.0336 (9)0.0256 (8)0.0210 (8)0.0021 (7)0.0055 (7)0.0011 (6)
C80.0292 (9)0.0292 (8)0.0171 (7)0.0016 (7)0.0061 (7)0.0012 (6)
C90.0253 (9)0.0314 (8)0.0151 (7)0.0016 (7)0.0047 (6)0.0018 (6)
C100.0266 (9)0.0344 (9)0.0209 (8)0.0023 (7)0.0050 (7)0.0002 (6)
C110.0286 (9)0.0461 (10)0.0239 (8)0.0055 (8)0.0049 (7)0.0000 (7)
C120.0367 (10)0.0386 (10)0.0282 (9)0.0131 (8)0.0073 (8)0.0026 (7)
C130.0382 (10)0.0309 (9)0.0256 (8)0.0041 (7)0.0090 (7)0.0009 (7)
C140.0265 (9)0.0308 (9)0.0346 (9)0.0035 (7)0.0060 (7)0.0067 (7)
C150.0310 (10)0.0276 (9)0.0471 (11)0.0017 (7)0.0061 (8)0.0097 (7)
C160.0278 (9)0.0250 (8)0.0438 (10)0.0013 (7)0.0054 (8)0.0029 (7)
C170.0245 (9)0.0288 (9)0.0289 (8)0.0014 (7)0.0026 (7)0.0037 (7)
C180.0436 (11)0.0340 (10)0.0483 (11)0.0069 (8)0.0148 (9)0.0105 (8)
C190.0320 (11)0.0333 (10)0.0761 (15)0.0040 (8)0.0066 (10)0.0085 (9)
C200.0224 (8)0.0193 (7)0.0231 (8)0.0006 (6)0.0024 (6)0.0003 (6)
C210.0210 (8)0.0207 (7)0.0228 (8)0.0007 (6)0.0008 (6)0.0004 (6)
C220.0275 (9)0.0256 (8)0.0220 (8)0.0028 (6)0.0045 (7)0.0006 (6)
C230.0303 (9)0.0304 (9)0.0212 (8)0.0051 (7)0.0016 (7)0.0055 (6)
C240.0225 (9)0.0279 (8)0.0306 (9)0.0012 (7)0.0027 (7)0.0071 (7)
C250.0224 (8)0.0235 (8)0.0281 (8)0.0002 (6)0.0053 (7)0.0009 (6)
C260.0253 (9)0.0351 (9)0.0303 (9)0.0033 (7)0.0106 (7)0.0013 (7)
Geometric parameters (Å, º) top
O1—C11.3689 (18)C14—C151.511 (2)
O1—C51.3907 (18)C15—C161.537 (2)
O2—C141.227 (2)C15—H15A0.9900
O3—C211.3647 (18)C15—H15B0.9900
O3—C261.4274 (17)C16—C191.528 (2)
C1—C21.340 (2)C16—C181.532 (2)
C1—C171.488 (2)C16—C171.535 (2)
C2—C141.466 (2)C17—H17A0.9900
C2—C31.514 (2)C17—H17B0.9900
C3—C41.519 (2)C18—H18A0.9800
C3—C201.529 (2)C18—H18B0.9800
C3—H31.0000C18—H18C0.9800
C4—C51.370 (2)C19—H19A0.9800
C4—C91.433 (2)C19—H19B0.9800
C5—C61.409 (2)C19—H19C0.9800
C6—C71.365 (2)C20—C251.384 (2)
C6—H60.9500C20—C211.412 (2)
C7—C81.418 (2)C21—C221.388 (2)
C7—H70.9500C22—C231.384 (2)
C8—C131.418 (2)C22—H220.9500
C8—C91.428 (2)C23—C241.385 (2)
C9—C101.420 (2)C23—H230.9500
C10—C111.367 (2)C24—C251.391 (2)
C10—H100.9500C24—H240.9500
C11—C121.410 (2)C25—H250.9500
C11—H110.9500C26—H26A0.9800
C12—C131.364 (2)C26—H26B0.9800
C12—H120.9500C26—H26C0.9800
C13—H130.9500
C1—O1—C5118.04 (12)C16—C15—H15B108.6
C21—O3—C26117.06 (11)H15A—C15—H15B107.6
C2—C1—O1122.93 (14)C19—C16—C18109.51 (15)
C2—C1—C17125.79 (14)C19—C16—C17109.22 (14)
O1—C1—C17111.27 (13)C18—C16—C17110.37 (13)
C1—C2—C14118.75 (14)C19—C16—C15110.43 (14)
C1—C2—C3122.43 (14)C18—C16—C15109.70 (15)
C14—C2—C3118.82 (13)C17—C16—C15107.60 (13)
C2—C3—C4109.91 (13)C1—C17—C16113.13 (13)
C2—C3—C20110.14 (12)C1—C17—H17A109.0
C4—C3—C20113.79 (12)C16—C17—H17A109.0
C2—C3—H3107.6C1—C17—H17B109.0
C4—C3—H3107.6C16—C17—H17B109.0
C20—C3—H3107.6H17A—C17—H17B107.8
C5—C4—C9117.64 (14)C16—C18—H18A109.5
C5—C4—C3120.53 (14)C16—C18—H18B109.5
C9—C4—C3121.81 (14)H18A—C18—H18B109.5
C4—C5—O1123.12 (14)C16—C18—H18C109.5
C4—C5—C6123.30 (14)H18A—C18—H18C109.5
O1—C5—C6113.58 (13)H18B—C18—H18C109.5
C7—C6—C5119.42 (15)C16—C19—H19A109.5
C7—C6—H6120.3C16—C19—H19B109.5
C5—C6—H6120.3H19A—C19—H19B109.5
C6—C7—C8120.55 (15)C16—C19—H19C109.5
C6—C7—H7119.7H19A—C19—H19C109.5
C8—C7—H7119.7H19B—C19—H19C109.5
C7—C8—C13121.56 (15)C25—C20—C21117.83 (14)
C7—C8—C9119.20 (14)C25—C20—C3120.50 (13)
C13—C8—C9119.24 (15)C21—C20—C3121.61 (13)
C10—C9—C8117.79 (14)O3—C21—C22124.02 (13)
C10—C9—C4122.44 (15)O3—C21—C20115.66 (13)
C8—C9—C4119.75 (14)C22—C21—C20120.32 (14)
C11—C10—C9121.07 (16)C23—C22—C21120.27 (14)
C11—C10—H10119.5C23—C22—H22119.9
C9—C10—H10119.5C21—C22—H22119.9
C10—C11—C12121.03 (16)C22—C23—C24120.44 (14)
C10—C11—H11119.5C22—C23—H23119.8
C12—C11—H11119.5C24—C23—H23119.8
C13—C12—C11119.36 (16)C23—C24—C25118.95 (15)
C13—C12—H12120.3C23—C24—H24120.5
C11—C12—H12120.3C25—C24—H24120.5
C12—C13—C8121.38 (16)C20—C25—C24122.15 (14)
C12—C13—H13119.3C20—C25—H25118.9
C8—C13—H13119.3C24—C25—H25118.9
O2—C14—C2121.23 (15)O3—C26—H26A109.5
O2—C14—C15121.08 (15)O3—C26—H26B109.5
C2—C14—C15117.61 (14)H26A—C26—H26B109.5
C14—C15—C16114.58 (13)O3—C26—H26C109.5
C14—C15—H15A108.6H26A—C26—H26C109.5
C16—C15—H15A108.6H26B—C26—H26C109.5
C14—C15—H15B108.6
C5—O1—C1—C27.5 (2)C10—C11—C12—C132.7 (2)
C5—O1—C1—C17171.74 (11)C11—C12—C13—C82.6 (2)
O1—C1—C2—C14172.34 (13)C7—C8—C13—C12179.56 (14)
C17—C1—C2—C146.8 (2)C9—C8—C13—C120.4 (2)
O1—C1—C2—C38.5 (2)C1—C2—C14—O2176.29 (15)
C17—C1—C2—C3172.37 (13)C3—C2—C14—O24.5 (2)
C1—C2—C3—C418.08 (19)C1—C2—C14—C150.6 (2)
C14—C2—C3—C4162.79 (13)C3—C2—C14—C15178.59 (14)
C1—C2—C3—C20108.08 (16)O2—C14—C15—C16152.27 (17)
C14—C2—C3—C2071.06 (16)C2—C14—C15—C1630.9 (2)
C2—C3—C4—C513.38 (18)C14—C15—C16—C19172.21 (15)
C20—C3—C4—C5110.68 (15)C14—C15—C16—C1867.01 (19)
C2—C3—C4—C9168.47 (12)C14—C15—C16—C1753.1 (2)
C20—C3—C4—C967.47 (17)C2—C1—C17—C1618.7 (2)
C9—C4—C5—O1177.63 (12)O1—C1—C17—C16162.09 (12)
C3—C4—C5—O10.6 (2)C19—C16—C17—C1166.24 (13)
C9—C4—C5—C61.5 (2)C18—C16—C17—C173.32 (17)
C3—C4—C5—C6179.70 (13)C15—C16—C17—C146.35 (18)
C1—O1—C5—C412.10 (19)C2—C3—C20—C25111.05 (15)
C1—O1—C5—C6168.71 (12)C4—C3—C20—C25125.02 (15)
C4—C5—C6—C72.7 (2)C2—C3—C20—C2166.04 (17)
O1—C5—C6—C7176.49 (12)C4—C3—C20—C2157.89 (18)
C5—C6—C7—C80.3 (2)C26—O3—C21—C224.4 (2)
C6—C7—C8—C13176.18 (14)C26—O3—C21—C20175.59 (12)
C6—C7—C8—C93.0 (2)C25—C20—C21—O3177.57 (12)
C7—C8—C9—C10177.55 (13)C3—C20—C21—O30.4 (2)
C13—C8—C9—C103.2 (2)C25—C20—C21—C222.4 (2)
C7—C8—C9—C44.2 (2)C3—C20—C21—C22179.53 (13)
C13—C8—C9—C4175.03 (13)O3—C21—C22—C23178.35 (14)
C5—C4—C9—C10179.85 (12)C20—C21—C22—C231.6 (2)
C3—C4—C9—C102.0 (2)C21—C22—C23—C240.4 (2)
C5—C4—C9—C82.0 (2)C22—C23—C24—C251.4 (2)
C3—C4—C9—C8176.22 (12)C21—C20—C25—C241.3 (2)
C8—C9—C10—C113.2 (2)C3—C20—C25—C24178.48 (14)
C4—C9—C10—C11175.03 (14)C23—C24—C25—C200.6 (2)
C9—C10—C11—C120.2 (2)

Experimental details

Crystal data
Chemical formulaC26H24O3
Mr384.45
Crystal system, space groupMonoclinic, P21/n
Temperature (K)113
a, b, c (Å)7.8454 (11), 22.670 (3), 11.3100 (13)
β (°) 98.893 (4)
V3)1987.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.36 × 0.28 × 0.20
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.970, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
12038, 3860, 3274
Rint0.035
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.122, 1.09
No. of reflections3860
No. of parameters266
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.21

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors thank the Tangshan Municipal Science and Technology Commission (grant No. 07160213B) and Tangshan Normal College (grant No. 07A02) for financial support.

References

First citationLambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178.  Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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