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

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ISSN: 2056-9890

2-Ethyl-8-meth­oxy­methyl-4-oxo-4H-chromen-7-yl (1S,4R)-4,7,7-tri­methyl-3-oxo-2-oxabi­cyclo­[2.2.1]heptane-1-carboxyl­ate

aDepartment of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, People's Republic of China
*Correspondence e-mail: pxia@fudan.edu.cn

(Received 26 April 2010; accepted 20 May 2010; online 26 May 2010)

The title compound C23H26O7, was prepared by esterification of 2-ethyl-7-hydr­oxy-8-methoxy­methyl-4H-chromen-4-one with (S)-(−)-camphanic chloride. The two rings of the chromone system are coplanar, making a dihedral angle of 1.99 (19)°, and the camphanoyl unit substituted at 7-O retains the original bicyclo­[2.2.1]heptane conformation of the starting reagent.

Related literature

For background to 3′R,4′R-Di-O-(−)-camphanoyl-2′,2′-di­methyl­dihydro­pyrano[2,3-f]chromone (DCP) analogues as potent anti-HIV agents, see: Yu et al. (2004[Yu, D., Chen, C.-H., Brossi, A. & Lee, K.-H. (2004). J. Med. Chem. 47, 4072-4082]).

[Scheme 1]

Experimental

Crystal data
  • C23H26O7

  • Mr = 414.44

  • Monoclinic, P 21

  • a = 7.632 (3) Å

  • b = 14.159 (6) Å

  • c = 10.579 (4) Å

  • β = 109.240 (5)°

  • V = 1079.3 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.22 × 0.12 × 0.05 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.995

  • 4560 measured reflections

  • 2016 independent reflections

  • 1713 reflections with I > 2σ(I)

  • Rint = 0.056

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.120

  • S = 0.96

  • 2016 reflections

  • 277 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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


Comment top

3'R,4'R-Di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone(DCP) analogues were potent anti-HIV agents (Yu et al. 2004). However, development of DCP analogues as effective anti-AIDS drugs has been hindered by problems of low water solubility and bioavailability. Therefore, we designed and synthesized a series of simplified DCP analogues. As one of the target compounds, the crystal structure of the title compound was reported here.

Fig.1 shows the molecular structure of the title compound, the two rings of chromone are planar and the camphanoyl unit substituted at 7-O retains its original bicyclo[2.2.1]heptane conformation and configuration with the chiralities of C16=S and C19=R in the purchased (S)-(-)-camphanic chloride reagent from Aldrich Company.

Related literature top

3'R,4'R-Di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP) analogues are potent anti-HIV agents, see: Yu et al. (2004).

Experimental top

The title compound was synthesized by the esterification of 2-ethyl-7-hydroxy-8-(methoxymethyl)-4H-chromen-4-one with (S)-(-)-camphanic chloride, which was purchased from Aldrich Company. 2-Ethyl-7-hydroxy-8-(methoxymethyl)-4H-chromen-4-one (250 mg, 1.07 mmol), (S)-(-)-camphanic chloride (255 mg, 1.17 mmol) and DMAP (156 mg, 1.28 mmol) were stirred in CH2Cl2 (8 ml) for 5 hours at room temperature. The mixture was concentrated and the residue was purified by chromatography on silica gel column with petroleum ether/EtOAc (4:1) as eluent, to afford the pure title compound, which was recrystallized from ethyl acetate to give colorless crystals for the single-crystal X-ray diffraction analysis. Yield: 52.5%.

Refinement top

All H atoms were placed in the idealized positions with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2–1.5 Ueq(C). 1764 Friedel pairs were merged for refinement.

Structure description top

3'R,4'R-Di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone(DCP) analogues were potent anti-HIV agents (Yu et al. 2004). However, development of DCP analogues as effective anti-AIDS drugs has been hindered by problems of low water solubility and bioavailability. Therefore, we designed and synthesized a series of simplified DCP analogues. As one of the target compounds, the crystal structure of the title compound was reported here.

Fig.1 shows the molecular structure of the title compound, the two rings of chromone are planar and the camphanoyl unit substituted at 7-O retains its original bicyclo[2.2.1]heptane conformation and configuration with the chiralities of C16=S and C19=R in the purchased (S)-(-)-camphanic chloride reagent from Aldrich Company.

3'R,4'R-Di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP) analogues are potent anti-HIV agents, see: Yu et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
2-Ethyl-8-methoxymethyl-4-oxo-4H-chromen-7-yl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane- 1-carboxylate top
Crystal data top
C23H26O7F(000) = 440
Mr = 414.44Dx = 1.275 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 755 reflections
a = 7.632 (3) Åθ = 2.5–24.2°
b = 14.159 (6) ŵ = 0.09 mm1
c = 10.579 (4) ÅT = 293 K
β = 109.240 (5)°Block, colourless
V = 1079.3 (8) Å30.22 × 0.12 × 0.05 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2016 independent reflections
Radiation source: fine-focus sealed tube1713 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
φ and ω scansθmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 89
Tmin = 0.980, Tmax = 0.995k = 1616
4560 measured reflectionsl = 1012
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0832P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
2016 reflectionsΔρmax = 0.22 e Å3
277 parametersΔρmin = 0.22 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.013 (4)
Primary atom site location: structure-invariant direct methods
Crystal data top
C23H26O7V = 1079.3 (8) Å3
Mr = 414.44Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.632 (3) ŵ = 0.09 mm1
b = 14.159 (6) ÅT = 293 K
c = 10.579 (4) Å0.22 × 0.12 × 0.05 mm
β = 109.240 (5)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2016 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1713 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.995Rint = 0.056
4560 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.120H-atom parameters constrained
S = 0.96Δρmax = 0.22 e Å3
2016 reflectionsΔρmin = 0.22 e Å3
277 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1007 (3)1.16766 (13)0.3383 (2)0.0443 (5)
C20.0842 (5)1.2628 (2)0.3643 (3)0.0460 (8)
C30.0805 (5)1.3053 (2)0.4130 (3)0.0510 (8)
H30.08381.37030.42600.061*
C40.2530 (5)1.2546 (2)0.4464 (3)0.0512 (8)
C4A0.2332 (5)1.1529 (2)0.4138 (3)0.0442 (7)
C50.3855 (5)1.0927 (2)0.4357 (4)0.0520 (8)
H50.50481.11760.46830.062*
C60.3629 (5)0.9984 (2)0.4103 (3)0.0499 (8)
H60.46500.95870.42670.060*
C70.1816 (5)0.9628 (2)0.3586 (3)0.0428 (8)
C80.0253 (4)1.0176 (2)0.3351 (3)0.0384 (7)
C8A0.0561 (4)1.1149 (2)0.3633 (3)0.0392 (7)
O90.1590 (3)0.86439 (13)0.3419 (2)0.0448 (6)
O100.4071 (4)1.29131 (18)0.4995 (3)0.0788 (9)
C110.2707 (5)1.3072 (3)0.3325 (4)0.0577 (9)
H11A0.25531.37520.33970.069*
H11B0.32521.28730.39900.069*
C120.4034 (7)1.2838 (4)0.1956 (5)0.0941 (16)
H12A0.35251.30480.12880.141*
H12B0.51981.31490.18270.141*
H12C0.42251.21670.18810.141*
C130.1664 (4)0.9791 (2)0.2854 (3)0.0443 (7)
H13A0.16480.91270.30860.053*
H13B0.24391.01230.32740.053*
O140.2395 (3)0.9897 (2)0.1462 (2)0.0717 (9)
C150.4332 (6)0.9722 (5)0.0981 (5)0.1000 (19)
H15A0.45570.90640.10840.150*
H15B0.48240.98900.00510.150*
H15C0.49281.00930.14810.150*
C160.1813 (4)0.7210 (2)0.2305 (3)0.0403 (7)
O170.1708 (3)0.68204 (13)0.35476 (19)0.0431 (5)
C180.0979 (5)0.5937 (2)0.3243 (3)0.0497 (8)
C190.0611 (6)0.5780 (2)0.1774 (3)0.0537 (9)
C200.2585 (7)0.5689 (3)0.1692 (4)0.0729 (12)
H20A0.25450.54980.08020.087*
H20B0.33120.52340.23380.087*
C210.3406 (6)0.6700 (3)0.2025 (4)0.0635 (10)
H21A0.45210.67000.28040.076*
H21B0.36790.69790.12720.076*
C220.0037 (5)0.6798 (2)0.1255 (3)0.0510 (8)
O230.0780 (5)0.54276 (18)0.4081 (3)0.0817 (10)
C240.0689 (8)0.4966 (3)0.1177 (5)0.0948 (16)
H24A0.01310.43840.15790.142*
H24B0.09200.49410.02290.142*
H24C0.18400.50570.13440.142*
C250.1748 (6)0.7137 (4)0.1453 (5)0.0755 (12)
H25A0.27790.67860.08780.113*
H25B0.19210.77970.12380.113*
H25C0.16690.70420.23690.113*
C260.0086 (8)0.6956 (3)0.0214 (4)0.0833 (14)
H26A0.11350.66190.07940.125*
H26B0.10280.67290.03440.125*
H26C0.02280.76180.04190.125*
C270.1974 (5)0.8265 (2)0.2372 (3)0.0457 (8)
O280.2358 (5)0.87123 (19)0.1549 (3)0.0764 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0449 (12)0.0358 (11)0.0486 (12)0.0011 (10)0.0106 (10)0.0002 (9)
C20.057 (2)0.0398 (17)0.0396 (16)0.0053 (16)0.0137 (14)0.0023 (13)
C30.063 (2)0.0355 (17)0.053 (2)0.0031 (15)0.0165 (17)0.0045 (13)
C40.051 (2)0.0424 (19)0.054 (2)0.0078 (15)0.0098 (15)0.0022 (15)
C4A0.049 (2)0.0363 (16)0.0424 (17)0.0044 (14)0.0083 (14)0.0008 (13)
C50.0417 (18)0.0453 (19)0.059 (2)0.0062 (15)0.0033 (15)0.0011 (16)
C60.0422 (18)0.0421 (18)0.0583 (19)0.0065 (15)0.0067 (15)0.0036 (15)
C70.053 (2)0.0324 (16)0.0409 (16)0.0031 (14)0.0127 (14)0.0044 (12)
C80.0441 (17)0.0369 (16)0.0331 (14)0.0060 (13)0.0111 (12)0.0006 (11)
C8A0.0431 (17)0.0388 (17)0.0331 (15)0.0015 (14)0.0091 (12)0.0032 (12)
O90.0593 (15)0.0297 (11)0.0472 (12)0.0018 (10)0.0199 (11)0.0027 (9)
O100.0570 (17)0.0515 (16)0.114 (2)0.0144 (13)0.0092 (15)0.0151 (16)
C110.061 (2)0.049 (2)0.062 (2)0.0101 (17)0.0192 (18)0.0024 (16)
C120.084 (3)0.091 (4)0.082 (3)0.031 (3)0.007 (2)0.005 (3)
C130.0460 (18)0.0434 (17)0.0442 (16)0.0052 (14)0.0158 (14)0.0030 (14)
O140.0460 (14)0.123 (3)0.0396 (12)0.0274 (15)0.0050 (10)0.0020 (15)
C150.050 (2)0.169 (6)0.068 (3)0.030 (3)0.002 (2)0.007 (3)
C160.0455 (18)0.0424 (16)0.0326 (14)0.0022 (14)0.0122 (13)0.0018 (12)
O170.0614 (14)0.0323 (11)0.0345 (11)0.0037 (9)0.0144 (10)0.0016 (8)
C180.072 (2)0.0333 (16)0.0446 (18)0.0032 (15)0.0209 (16)0.0025 (14)
C190.074 (2)0.0399 (17)0.0445 (18)0.0042 (17)0.0159 (17)0.0093 (14)
C200.100 (3)0.059 (2)0.064 (2)0.021 (2)0.033 (2)0.0100 (19)
C210.060 (2)0.073 (3)0.063 (2)0.008 (2)0.0279 (19)0.003 (2)
C220.058 (2)0.0506 (19)0.0356 (16)0.0047 (16)0.0033 (14)0.0042 (14)
O230.152 (3)0.0401 (14)0.0610 (17)0.0170 (16)0.0458 (18)0.0006 (12)
C240.134 (4)0.056 (3)0.078 (3)0.028 (3)0.013 (3)0.023 (2)
C250.051 (2)0.079 (3)0.083 (3)0.002 (2)0.003 (2)0.002 (2)
C260.114 (4)0.081 (3)0.036 (2)0.000 (3)0.001 (2)0.0025 (19)
C270.051 (2)0.0419 (17)0.0427 (18)0.0075 (15)0.0140 (15)0.0026 (14)
O280.122 (2)0.0554 (16)0.0639 (16)0.0216 (16)0.0474 (17)0.0042 (13)
Geometric parameters (Å, º) top
O1—C8A1.361 (4)C15—H15B0.9599
O1—C21.372 (4)C15—H15C0.9599
C2—C31.335 (5)C16—O171.452 (3)
C2—C111.489 (5)C16—C271.499 (4)
C3—C41.438 (5)C16—C211.525 (5)
C3—H30.9300C16—C221.555 (5)
C4—O101.238 (4)O17—C181.364 (4)
C4—C4A1.477 (4)C18—O231.190 (4)
C4A—C8A1.388 (4)C18—C191.502 (5)
C4A—C51.397 (5)C19—C241.517 (5)
C5—C61.361 (5)C19—C201.543 (6)
C5—H50.9300C19—C221.554 (5)
C6—C71.403 (5)C20—C211.556 (7)
C6—H60.9300C20—H20A0.9700
C7—C81.375 (4)C20—H20B0.9700
C7—O91.408 (4)C21—H21A0.9700
C8—C8A1.412 (4)C21—H21B0.9700
C8—C131.486 (4)C22—C251.522 (6)
O9—C271.346 (4)C22—C261.542 (5)
C11—C121.506 (6)C24—H24A0.9599
C11—H11A0.9700C24—H24B0.9599
C11—H11B0.9700C24—H24C0.9599
C12—H12A0.9599C25—H25A0.9599
C12—H12B0.9599C25—H25B0.9599
C12—H12C0.9599C25—H25C0.9599
C13—O141.401 (4)C26—H26A0.9599
C13—H13A0.9700C26—H26B0.9599
C13—H13B0.9700C26—H26C0.9599
O14—C151.418 (5)C27—O281.189 (4)
C15—H15A0.9599
C8A—O1—C2118.9 (3)O17—C16—C21106.4 (3)
C3—C2—O1122.2 (3)C27—C16—C21115.0 (3)
C3—C2—C11127.2 (3)O17—C16—C22102.1 (2)
O1—C2—C11110.6 (3)C27—C16—C22116.5 (3)
C2—C3—C4122.6 (3)C21—C16—C22104.3 (3)
C2—C3—H3118.7C18—O17—C16105.9 (2)
C4—C3—H3118.7O23—C18—O17121.5 (3)
O10—C4—C3123.9 (3)O23—C18—C19130.9 (3)
O10—C4—C4A121.6 (3)O17—C18—C19107.6 (3)
C3—C4—C4A114.5 (3)C18—C19—C24114.6 (3)
C8A—C4A—C5118.6 (3)C18—C19—C20102.6 (3)
C8A—C4A—C4118.6 (3)C24—C19—C20115.5 (4)
C5—C4A—C4122.7 (3)C18—C19—C2299.4 (3)
C6—C5—C4A121.4 (3)C24—C19—C22119.2 (3)
C6—C5—H5119.3C20—C19—C22103.0 (3)
C4A—C5—H5119.3C19—C20—C21103.8 (3)
C5—C6—C7118.3 (3)C19—C20—H20A111.0
C5—C6—H6120.9C21—C20—H20A111.0
C7—C6—H6120.9C19—C20—H20B111.0
C8—C7—C6123.6 (3)C21—C20—H20B111.0
C8—C7—O9118.2 (3)H20A—C20—H20B109.0
C6—C7—O9117.9 (3)C16—C21—C20101.1 (3)
C7—C8—C8A116.0 (3)C16—C21—H21A111.6
C7—C8—C13123.5 (3)C20—C21—H21A111.6
C8A—C8—C13120.6 (3)C16—C21—H21B111.6
O1—C8A—C4A123.0 (3)C20—C21—H21B111.6
O1—C8A—C8114.9 (3)H21A—C21—H21B109.4
C4A—C8A—C8122.2 (3)C25—C22—C26109.5 (3)
C27—O9—C7116.5 (2)C25—C22—C19113.9 (3)
C2—C11—C12114.4 (3)C26—C22—C19114.0 (3)
C2—C11—H11A108.7C25—C22—C16113.1 (3)
C12—C11—H11A108.7C26—C22—C16114.5 (3)
C2—C11—H11B108.7C19—C22—C1691.0 (3)
C12—C11—H11B108.7C19—C24—H24A109.5
H11A—C11—H11B107.6C19—C24—H24B109.5
C11—C12—H12A109.5H24A—C24—H24B109.5
C11—C12—H12B109.5C19—C24—H24C109.5
H12A—C12—H12B109.5H24A—C24—H24C109.5
C11—C12—H12C109.5H24B—C24—H24C109.5
H12A—C12—H12C109.5C22—C25—H25A109.5
H12B—C12—H12C109.5C22—C25—H25B109.5
O14—C13—C8109.7 (2)H25A—C25—H25B109.5
O14—C13—H13A109.7C22—C25—H25C109.5
C8—C13—H13A109.7H25A—C25—H25C109.5
O14—C13—H13B109.7H25B—C25—H25C109.5
C8—C13—H13B109.7C22—C26—H26A109.5
H13A—C13—H13B108.2C22—C26—H26B109.5
C13—O14—C15111.4 (3)H26A—C26—H26B109.5
O14—C15—H15A109.5C22—C26—H26C109.5
O14—C15—H15B109.5H26A—C26—H26C109.5
H15A—C15—H15B109.5H26B—C26—H26C109.5
O14—C15—H15C109.5O28—C27—O9124.3 (3)
H15A—C15—H15C109.5O28—C27—C16122.1 (3)
H15B—C15—H15C109.5O9—C27—C16113.6 (3)
O17—C16—C27111.3 (2)
C8A—O1—C2—C30.1 (4)C16—O17—C18—C190.5 (4)
C8A—O1—C2—C11179.1 (3)O23—C18—C19—C2419.0 (7)
O1—C2—C3—C42.1 (5)O17—C18—C19—C24163.2 (4)
C11—C2—C3—C4176.8 (3)O23—C18—C19—C20107.0 (5)
C2—C3—C4—O10175.3 (3)O17—C18—C19—C2070.8 (4)
C2—C3—C4—C4A3.9 (5)O23—C18—C19—C22147.3 (5)
O10—C4—C4A—C8A175.4 (3)O17—C18—C19—C2234.9 (4)
C3—C4—C4A—C8A3.8 (4)C18—C19—C20—C2168.6 (3)
O10—C4—C4A—C52.5 (5)C24—C19—C20—C21166.0 (4)
C3—C4—C4A—C5178.3 (3)C22—C19—C20—C2134.3 (3)
C8A—C4A—C5—C60.9 (5)O17—C16—C21—C2069.0 (3)
C4—C4A—C5—C6177.0 (4)C27—C16—C21—C20167.3 (3)
C4A—C5—C6—C71.2 (5)C22—C16—C21—C2038.4 (4)
C5—C6—C7—C81.6 (5)C19—C20—C21—C162.2 (4)
C5—C6—C7—O9175.4 (3)C18—C19—C22—C2564.7 (4)
C6—C7—C8—C8A1.4 (4)C24—C19—C22—C2560.5 (5)
O9—C7—C8—C8A175.3 (2)C20—C19—C22—C25170.1 (3)
C6—C7—C8—C13177.5 (3)C18—C19—C22—C26168.6 (4)
O9—C7—C8—C133.7 (4)C24—C19—C22—C2666.1 (5)
C2—O1—C8A—C4A0.1 (4)C20—C19—C22—C2663.3 (4)
C2—O1—C8A—C8179.2 (3)C18—C19—C22—C1651.2 (3)
C5—C4A—C8A—O1179.8 (3)C24—C19—C22—C16176.4 (4)
C4—C4A—C8A—O12.1 (5)C20—C19—C22—C1654.2 (3)
C5—C4A—C8A—C80.9 (5)O17—C16—C22—C2563.1 (4)
C4—C4A—C8A—C8177.2 (3)C27—C16—C22—C2558.3 (4)
C7—C8—C8A—O1179.6 (2)C21—C16—C22—C25173.7 (3)
C13—C8—C8A—O11.4 (4)O17—C16—C22—C26170.5 (3)
C7—C8—C8A—C4A1.1 (4)C27—C16—C22—C2668.1 (4)
C13—C8—C8A—C4A177.9 (3)C21—C16—C22—C2659.9 (4)
C8—C7—O9—C27110.5 (3)O17—C16—C22—C1953.4 (3)
C6—C7—O9—C2775.4 (4)C27—C16—C22—C19174.9 (3)
C3—C2—C11—C12130.5 (4)C21—C16—C22—C1957.2 (3)
O1—C2—C11—C1250.4 (4)C7—O9—C27—O285.3 (5)
C7—C8—C13—O1496.3 (4)C7—O9—C27—C16176.5 (3)
C8A—C8—C13—O1484.8 (4)O17—C16—C27—O28168.4 (3)
C8—C13—O14—C15167.8 (4)C21—C16—C27—O2847.3 (5)
C27—C16—O17—C18160.9 (3)C22—C16—C27—O2875.2 (4)
C21—C16—O17—C1873.1 (3)O17—C16—C27—O913.5 (4)
C22—C16—O17—C1835.9 (3)C21—C16—C27—O9134.5 (3)
C16—O17—C18—O23177.6 (4)C22—C16—C27—O9102.9 (3)

Experimental details

Crystal data
Chemical formulaC23H26O7
Mr414.44
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)7.632 (3), 14.159 (6), 10.579 (4)
β (°) 109.240 (5)
V3)1079.3 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.22 × 0.12 × 0.05
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.980, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
4560, 2016, 1713
Rint0.056
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.120, 0.96
No. of reflections2016
No. of parameters277
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors acknowledge Miss Wang Jingmei, Center of Analysis and Measurement, Fudan University, for her help with the crystal structure analysis.

References

First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYu, D., Chen, C.-H., Brossi, A. & Lee, K.-H. (2004). J. Med. Chem. 47, 4072–4082  Web of Science CrossRef PubMed CAS Google Scholar

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