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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1430

Di­methyl 3-(cyclo­propyl­carbon­yl)pyrrolo­[2,1-a]iso­quinoline-1,2-di­carboxyl­ate

aSchool of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, People's Republic of China, and bKey Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province, School of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng 224051, People's Republic of China
*Correspondence e-mail: wangw@ycit.edu.cn

(Received 30 March 2012; accepted 10 April 2012; online 18 April 2012)

In the mol­ecular structure of the title compound, C20H17NO5, two intra­molecular C—H⋯O hydrogen bond generate six- and seven-membered ring motifs. The dihedral angles between the almost planar 13-atom triple-fused-ring system (r.m.s. deviation = 0.003 Å) and the planes of the two meth­oxy­carbonyl substituents are 61.7 (2) and 33.01 (10)°.

Related literature

For chemical background, see: Michael (2004[Michael, J. P. (2004). Nat. Prod. Rep. 21, 625-649.]); Sriram et al. (2005[Sriram, D., Yogeeswari, P., Thirumurugan, R. & Bal, T. R. (2005). Nat. Prod. Res. 19, 393-412.]); Alonso et al. (1985[Alonso, R., Castedo, L. & Dominguez, D. (1985). Tetrahedron Lett. 26, 2925-2928.]). For the biological activity of indolizine derivatives, see: Shen et al. (2010[Shen, Y. M., Lv, P. C., Chen, W., Liu, P. G., Zhang, M. Z. & Zhu, H. L. (2010). Eur. J. Med. Chem. 45, 3184-3190.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17NO5

  • Mr = 351.35

  • Monoclinic, P 21 /c

  • a = 7.5910 (15) Å

  • b = 18.436 (4) Å

  • c = 12.162 (2) Å

  • β = 94.43 (3)°

  • V = 1697.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]) Tmin = 0.971, Tmax = 0.990

  • 3321 measured reflections

  • 3078 independent reflections

  • 2060 reflections with I > 2σ(I)

  • Rint = 0.048

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.179

  • S = 1.01

  • 3078 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13A⋯O1 0.93 2.27 2.872 (4) 122
C20—H20A⋯O4 0.93 2.18 3.019 (4) 150

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The indolizine and hydrogenated indolizine structures are found in many alkaloids such as amorine, crythraline, swainsonine, cryptaustoline, cryptowoline (Sriram et al. 2005), camptothesin(Michael, 2004), nuevamine (Alonso et al., 1985), etc. These natural and many synthetic indolizine derivatives have been found to have a variety of biological activity (Shen et al., 2010).

We report here the synthesis and crystal structure of the title compound (I). The molecular structure of (I) is shown in Fig.1. In the title compound, intramolecular C13 —H13A···O1 and C20—H20A···O4 hydrogen bond generates extra two ring motifs. The dihedral angle between the indolizine ring system and the C20—H20A···O4 plane is 20.40 (4)°.

Related literature top

For chemical background, see: Michael (2004); Sriram et al. (2005); Alonso et al. (1985). For the biological activity of indolizine derivatives, see: Shen et al. (2010).

Experimental top

A mixture of the 2-(2-cyclopropyl-2-oxoethyl)isoquinolinium bromide (10 mmol), acrylonitrile (40 mmol), triethylamine (2 ml) and TPCD (4 g) in DMF (40 ml) was heated at 90° C for 5 h. After cooling, the reaction mixture was poured into an aqueous hydrochloric acid solution (5%, 100 ml), the precipitated crude product was collected by filtration and further purified by silica gel column chromatography with petroleum ether (bp 60–90 °C)-ethyl acetate as eluents. Yellow crystal. m.p. 388–389 K, Yield 76%. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in petroleum ether -ethyl acetate(4:1), at room temperature.

Refinement top

The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with C—H distances in the range of 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(parent atom), or Uiso(H) = 1.5Ueq(Cmethyl).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds.
Dimethyl 3-(cyclopropylcarbonyl)pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate top
Crystal data top
C20H17NO5F(000) = 736
Mr = 351.35Dx = 1.375 Mg m3
Monoclinic, P21/cMelting point: 388 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.5910 (15) ÅCell parameters from 25 reflections
b = 18.436 (4) Åθ = 9–12°
c = 12.162 (2) ŵ = 0.10 mm1
β = 94.43 (3)°T = 293 K
V = 1697.0 (6) Å3Block, yellow
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.3°, θmin = 2.0°
ω/2θ scansh = 09
Absorption correction: ψ scan
(XCAD4; Harms & Wocadlo, 1995)
k = 022
Tmin = 0.971, Tmax = 0.990l = 1414
3321 measured reflections3 standard reflections every 200 reflections
3078 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1P)2 + 0.4P]
where P = (Fo2 + 2Fc2)/3
3078 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C20H17NO5V = 1697.0 (6) Å3
Mr = 351.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.5910 (15) ŵ = 0.10 mm1
b = 18.436 (4) ÅT = 293 K
c = 12.162 (2) Å0.30 × 0.20 × 0.10 mm
β = 94.43 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2060 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XCAD4; Harms & Wocadlo, 1995)
Rint = 0.048
Tmin = 0.971, Tmax = 0.9903 standard reflections every 200 reflections
3321 measured reflections intensity decay: 1%
3078 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.179H-atom parameters constrained
S = 1.01Δρmax = 0.30 e Å3
3078 reflectionsΔρmin = 0.24 e Å3
235 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
N0.2043 (3)0.45752 (11)0.56131 (17)0.0407 (5)
O10.0490 (3)0.31335 (12)0.57398 (18)0.0729 (7)
C10.0128 (5)0.2518 (2)0.7977 (3)0.0763 (10)
H1A0.00350.24740.87650.092*
H1B0.09870.24850.75330.092*
O20.3127 (2)0.44915 (12)0.92593 (15)0.0583 (6)
C20.1687 (5)0.22111 (19)0.7524 (4)0.0815 (11)
H2A0.15370.19910.67990.098*
H2B0.25600.19790.80320.098*
O30.0196 (3)0.44054 (13)0.88912 (17)0.0657 (6)
C30.1495 (4)0.30195 (16)0.7597 (3)0.0591 (8)
H3A0.22470.32600.81790.071*
O40.4069 (3)0.64344 (13)0.76734 (18)0.0715 (7)
C40.1160 (4)0.34276 (15)0.6567 (2)0.0463 (7)
O50.1973 (3)0.59404 (11)0.86128 (17)0.0613 (6)
C50.2880 (5)0.4387 (3)1.0410 (3)0.0879 (13)
H5A0.40090.43811.08240.132*
H5B0.22870.39341.05070.132*
H5C0.21790.47761.06670.132*
C60.1646 (4)0.45114 (15)0.8593 (2)0.0462 (7)
C70.2330 (5)0.64687 (18)0.9471 (3)0.0694 (10)
H7A0.15100.64071.00260.104*
H7B0.22060.69470.91640.104*
H7C0.35130.64050.97950.104*
C80.3006 (3)0.59626 (15)0.7761 (2)0.0452 (7)
C90.2639 (3)0.53321 (14)0.7048 (2)0.0403 (6)
C100.2004 (3)0.46707 (14)0.7437 (2)0.0403 (6)
C110.1670 (3)0.41976 (14)0.6564 (2)0.0405 (6)
C120.2688 (3)0.52648 (14)0.5891 (2)0.0406 (6)
C130.1793 (3)0.43333 (16)0.4534 (2)0.0472 (7)
H13A0.13530.38700.43870.057*
C140.2183 (4)0.47657 (17)0.3706 (2)0.0555 (8)
H14A0.19570.46070.29830.067*
C150.2945 (4)0.54702 (17)0.3911 (2)0.0512 (7)
C160.3216 (3)0.57249 (15)0.5008 (2)0.0449 (7)
C170.3413 (4)0.5916 (2)0.3040 (3)0.0644 (9)
H17A0.32160.57540.23170.077*
C180.4146 (4)0.6579 (2)0.3238 (3)0.0693 (10)
H18A0.44290.68710.26540.083*
C190.4473 (4)0.68183 (18)0.4315 (3)0.0653 (9)
H19A0.50200.72640.44490.078*
C200.4002 (4)0.64068 (16)0.5189 (3)0.0553 (8)
H20A0.42060.65820.59050.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0414 (12)0.0421 (12)0.0390 (12)0.0036 (10)0.0048 (9)0.0006 (10)
O10.0976 (17)0.0614 (14)0.0594 (14)0.0228 (13)0.0031 (12)0.0076 (11)
C10.076 (2)0.080 (3)0.075 (2)0.0009 (19)0.0169 (19)0.0190 (19)
O20.0539 (12)0.0747 (15)0.0457 (12)0.0098 (11)0.0005 (9)0.0041 (10)
C20.101 (3)0.053 (2)0.092 (3)0.0147 (19)0.022 (2)0.0156 (19)
O30.0523 (12)0.0861 (16)0.0604 (13)0.0108 (12)0.0159 (10)0.0020 (12)
C30.074 (2)0.0412 (16)0.061 (2)0.0008 (15)0.0017 (16)0.0013 (14)
O40.0759 (15)0.0702 (15)0.0703 (15)0.0316 (13)0.0186 (12)0.0128 (12)
C40.0449 (15)0.0450 (16)0.0495 (16)0.0019 (13)0.0059 (12)0.0051 (13)
O50.0749 (14)0.0487 (12)0.0634 (14)0.0122 (10)0.0248 (11)0.0177 (10)
C50.092 (3)0.130 (4)0.0406 (19)0.021 (3)0.0004 (17)0.008 (2)
C60.0499 (16)0.0419 (15)0.0471 (16)0.0023 (13)0.0060 (13)0.0026 (12)
C70.086 (2)0.062 (2)0.062 (2)0.0102 (18)0.0194 (18)0.0194 (17)
C80.0352 (13)0.0472 (16)0.0531 (17)0.0003 (13)0.0036 (12)0.0001 (13)
C90.0349 (13)0.0427 (15)0.0437 (15)0.0056 (11)0.0049 (11)0.0003 (12)
C100.0379 (13)0.0417 (15)0.0413 (15)0.0045 (11)0.0035 (11)0.0006 (11)
C110.0373 (13)0.0423 (15)0.0421 (15)0.0050 (11)0.0038 (11)0.0011 (12)
C120.0339 (13)0.0402 (14)0.0479 (16)0.0071 (11)0.0039 (11)0.0020 (12)
C130.0448 (15)0.0531 (17)0.0428 (16)0.0060 (13)0.0014 (12)0.0032 (13)
C140.0547 (17)0.069 (2)0.0426 (17)0.0116 (15)0.0020 (13)0.0036 (15)
C150.0462 (15)0.0619 (19)0.0461 (17)0.0136 (14)0.0069 (12)0.0123 (14)
C160.0330 (13)0.0472 (16)0.0551 (17)0.0110 (12)0.0066 (11)0.0095 (13)
C170.0523 (18)0.083 (2)0.059 (2)0.0119 (17)0.0109 (14)0.0175 (18)
C180.057 (2)0.078 (2)0.075 (2)0.0110 (18)0.0161 (17)0.034 (2)
C190.0588 (19)0.0517 (18)0.087 (3)0.0033 (15)0.0161 (17)0.0196 (18)
C200.0491 (16)0.0516 (17)0.066 (2)0.0040 (14)0.0112 (14)0.0080 (15)
Geometric parameters (Å, º) top
N—C131.385 (3)C6—C101.483 (4)
N—C121.395 (3)C7—H7A0.9600
N—C111.398 (3)C7—H7B0.9600
O1—C41.218 (3)C7—H7C0.9600
C1—C21.458 (5)C8—C91.464 (4)
C1—C31.490 (5)C9—C101.406 (4)
C1—H1A0.9700C9—C121.416 (4)
C1—H1B0.9700C10—C111.382 (4)
O2—C61.334 (3)C12—C161.449 (4)
O2—C51.440 (4)C13—C141.335 (4)
C2—C31.501 (4)C13—H13A0.9300
C2—H2A0.9700C14—C151.436 (4)
C2—H2B0.9700C14—H14A0.9300
O3—C61.201 (3)C15—C171.408 (4)
C3—C41.467 (4)C15—C161.414 (4)
C3—H3A0.9800C16—C201.402 (4)
O4—C81.197 (3)C17—C181.356 (5)
C4—C111.472 (4)C17—H17A0.9300
O5—C81.347 (3)C18—C191.387 (5)
O5—C71.438 (3)C18—H18A0.9300
C5—H5A0.9600C19—C201.376 (4)
C5—H5B0.9600C19—H19A0.9300
C5—H5C0.9600C20—H20A0.9300
C13—N—C12122.9 (2)H7B—C7—H7C109.5
C13—N—C11127.0 (2)O4—C8—O5121.8 (3)
C12—N—C11110.1 (2)O4—C8—C9128.5 (3)
C2—C1—C361.2 (2)O5—C8—C9109.6 (2)
C2—C1—H1A117.6C10—C9—C12107.1 (2)
C3—C1—H1A117.6C10—C9—C8122.9 (2)
C2—C1—H1B117.6C12—C9—C8129.8 (2)
C3—C1—H1B117.6C11—C10—C9109.7 (2)
H1A—C1—H1B114.8C11—C10—C6124.6 (2)
C6—O2—C5115.3 (2)C9—C10—C6125.7 (2)
C1—C2—C360.5 (2)C10—C11—N106.5 (2)
C1—C2—H2A117.7C10—C11—C4129.8 (2)
C3—C2—H2A117.7N—C11—C4123.5 (2)
C1—C2—H2B117.7N—C12—C9106.6 (2)
C3—C2—H2B117.7N—C12—C16117.8 (2)
H2A—C2—H2B114.8C9—C12—C16135.7 (3)
C4—C3—C1120.3 (3)C14—C13—N120.0 (3)
C4—C3—C2118.0 (3)C14—C13—H13A120.0
C1—C3—C258.3 (2)N—C13—H13A120.0
C4—C3—H3A116.0C13—C14—C15121.3 (3)
C1—C3—H3A116.0C13—C14—H14A119.4
C2—C3—H3A116.0C15—C14—H14A119.4
O1—C4—C3120.7 (3)C17—C15—C16119.3 (3)
O1—C4—C11121.4 (3)C17—C15—C14121.3 (3)
C3—C4—C11117.9 (2)C16—C15—C14119.4 (3)
C8—O5—C7116.7 (2)C20—C16—C15118.4 (3)
O2—C5—H5A109.5C20—C16—C12123.1 (3)
O2—C5—H5B109.5C15—C16—C12118.5 (3)
H5A—C5—H5B109.5C18—C17—C15121.1 (3)
O2—C5—H5C109.5C18—C17—H17A119.4
H5A—C5—H5C109.5C15—C17—H17A119.4
H5B—C5—H5C109.5C17—C18—C19119.7 (3)
O3—C6—O2124.1 (3)C17—C18—H18A120.1
O3—C6—C10123.9 (3)C19—C18—H18A120.1
O2—C6—C10111.9 (2)C20—C19—C18121.1 (3)
O5—C7—H7A109.5C20—C19—H19A119.5
O5—C7—H7B109.5C18—C19—H19A119.5
H7A—C7—H7B109.5C19—C20—C16120.4 (3)
O5—C7—H7C109.5C19—C20—H20A119.8
H7A—C7—H7C109.5C16—C20—H20A119.8
C2—C1—C3—C4106.2 (3)C3—C4—C11—C1019.1 (4)
C1—C2—C3—C4110.1 (3)O1—C4—C11—N23.9 (4)
C1—C3—C4—O144.0 (4)C3—C4—C11—N155.6 (2)
C2—C3—C4—O123.8 (5)C13—N—C12—C9175.8 (2)
C1—C3—C4—C11136.5 (3)C11—N—C12—C92.7 (3)
C2—C3—C4—C11155.7 (3)C13—N—C12—C163.9 (3)
C5—O2—C6—O34.7 (4)C11—N—C12—C16177.5 (2)
C5—O2—C6—C10176.1 (3)C10—C9—C12—N1.4 (3)
C7—O5—C8—O46.1 (4)C8—C9—C12—N173.7 (2)
C7—O5—C8—C9172.0 (3)C10—C9—C12—C16178.9 (3)
O4—C8—C9—C10150.7 (3)C8—C9—C12—C166.0 (5)
O5—C8—C9—C1027.3 (3)C12—N—C13—C140.4 (4)
O4—C8—C9—C1234.9 (5)C11—N—C13—C14178.7 (2)
O5—C8—C9—C12147.1 (3)N—C13—C14—C153.1 (4)
C12—C9—C10—C110.3 (3)C13—C14—C15—C17177.8 (3)
C8—C9—C10—C11175.9 (2)C13—C14—C15—C162.9 (4)
C12—C9—C10—C6176.5 (2)C17—C15—C16—C202.2 (4)
C8—C9—C10—C61.0 (4)C14—C15—C16—C20178.5 (2)
O3—C6—C10—C1163.4 (4)C17—C15—C16—C12178.6 (2)
O2—C6—C10—C11115.8 (3)C14—C15—C16—C120.8 (4)
O3—C6—C10—C9113.0 (3)N—C12—C16—C20175.2 (2)
O2—C6—C10—C967.8 (3)C9—C12—C16—C205.1 (4)
C9—C10—C11—N2.0 (3)N—C12—C16—C154.0 (3)
C6—C10—C11—N174.9 (2)C9—C12—C16—C15175.7 (3)
C9—C10—C11—C4173.5 (2)C16—C15—C17—C181.2 (4)
C6—C10—C11—C49.6 (4)C14—C15—C17—C18179.4 (3)
C13—N—C11—C10175.5 (2)C15—C17—C18—C191.2 (5)
C12—N—C11—C102.9 (3)C17—C18—C19—C202.6 (5)
C13—N—C11—C48.6 (4)C18—C19—C20—C161.6 (5)
C12—N—C11—C4172.9 (2)C15—C16—C20—C190.8 (4)
O1—C4—C11—C10161.3 (3)C12—C16—C20—C19180.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O10.932.272.872 (4)122
C20—H20A···O40.932.183.019 (4)150

Experimental details

Crystal data
Chemical formulaC20H17NO5
Mr351.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.5910 (15), 18.436 (4), 12.162 (2)
β (°) 94.43 (3)
V3)1697.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(XCAD4; Harms & Wocadlo, 1995)
Tmin, Tmax0.971, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
3321, 3078, 2060
Rint0.048
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.179, 1.01
No. of reflections3078
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.24

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O10.932.272.872 (4)122
C20—H20A···O40.932.183.019 (4)150
 

Acknowledgements

We greatly appreciate the financial support of the Foundation of the Key Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province (AE201017).

References

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First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
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Volume 68| Part 5| May 2012| Page o1430
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