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

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ISSN: 2056-9890

(E)-3-[3,4-Bis(meth­­oxy­meth­oxy)phen­yl]-1-(7-hy­dr­oxy-5-meth­­oxy-2,2-di­methyl­chroman-8-yl)prop-2-en-1-one

aDepartment of Chemistry, Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 2 August 2011; accepted 3 August 2011; online 11 August 2011)

The reaction of 5,6-(2,2-dimethyl­chroman­yl)-2-hy­droxy-4-meth­oxy­acetophenone and 3,4-bis­(meth­oxy­meth­yloxy)benzaldehyde affords the intense orange title chalcone derivative, C25H30O8. The two benzene rings are connected through a —C(=O)—CH=CH— (propenone) unit, which is in an E conformation; the ring with the hy­droxy substitutent is aligned at 19.5 (2)° with respect to this unit, whereas the ring with the meth­oxy­meth­yloxy substituent is aligned at 9.3 (3)°. The dihedral angle between the rings is 19.38 (10)°. The hy­droxy group engages in an intra­molecular O—H⋯O hydrogen bond with the carbonyl O atom of the propenone unit, generating an S(5) ring.

Related literature

For background to chalcones, see: Avila et al. (2008[Avila, H. P., Smania, E. F. A., Monache, F. D. & Junior, A. S. (2008). Bioorg. Med. Chem. 16, 9790-9794.]); Narender et al. (2007[Narender, T., Reddy, K.P., Shweta, Srivastava, K., Mishra, D.K., & Puri, S. K. (2007). Org. Lett. 9, 5369-5372.]); Reddy et al. (2010[Reddy, N. P., Aparoy, P., Reddy, T. C. M., Achari, C., Sridhar, P. R. & Reddanna, P. (2010). Bioorg. Med. Chem. 18, 5807-5815.]).

[Scheme 1]

Experimental

Crystal data
  • C25H30O8

  • Mr = 458.49

  • Monoclinic, P c

  • a = 9.5990 (8) Å

  • b = 8.3294 (7) Å

  • c = 14.7444 (12) Å

  • β = 107.684 (1)°

  • V = 1123.17 (16) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.30 × 0.25 × 0.05 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • 10316 measured reflections

  • 2576 independent reflections

  • 2433 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.082

  • S = 1.06

  • 2576 reflections

  • 302 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O4 0.90 (4) 1.65 (4) 2.480 (2) 153 (3)

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Chalcones or 1,3-diphenyl-2-propen-1-one derivatives flavonoids consist of two aromatic rings that are linked by a three-carbon α, β-unsaturated carbonyl unit (Avila et al., 2008; Reddy et al., 2010), and key precursors for the synthesis of a various flavonoids, some of which are components in food (Narender et al., 2007). We intend to use the intensely-orange title compound, (I), in the synthesis of other compounds. Its two benzene rings are connected through the –C( O)–CHCH– unit, which is of an E configuration; the ring with the hydroxy substitutent is aligned at 19.5 (2) ° with this unit whereas the ring with the methoxymethyloxy substituents is aligned at 9.3 (3) °. The hydroxy group engages in intramolecular hydrogen bonding with the carbonyl O atom of the unit (Fig.1).

Related literature top

For background to chalcones, see: Avila et al. (2008); Narender et al. (2007); Reddy et al. (2010).

Experimental top

A solution of 2-hydroxy-4-methoxy-5,6-(2,2-dimethylchromane)acetophenone (100 mg, 0.45 mmol) and 3,4-bis(methoxymethyloxy)benzaldehyde (100 mg, 0.45 mmol) in ethanol (10 ml) was treated with 50% potassium hydroxide (1 ml). The mixture was stirred for 48 h. The mixture was poured into iced water (30 ml); this was acidified with 10% hydrochloric acid. The mixture was extracted with dichloromethane (3 x 20 ml). The organic layer was washed with water (3 x 10 ml) and brine (3 x 5 ml) followed by drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to yield a dark greenish syrup. The syrup was subjected to VLC for purification by using silica gel and eluting with a hexane:ethyl acetate solvent system (9:1) to give the title compound (520 mg, 30%) as orange prisms of (I), m.p. 363–368 K. The formulation was established by 1H– and 13C-NMR spectroscopy.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5Ueq(C).

The hydroxy H-atom was located in a difference Fourier map, and was freely refined.

In the absence of heavy scatters, 2245 Friedel pairs were merged. Omitted from the refinement were (-3 3 - 8), (-2 8 - 1), (1 1 - 4), (-4 9 3) and (-3 0 16).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
(E)-3-[3,4-Bis(methoxymethoxy)phenyl]-1-(7-hydroxy-5-methoxy- 2,2-dimethylchroman-8-yl)prop-2-en-1-one top
Crystal data top
C25H30O8F(000) = 488
Mr = 458.49Dx = 1.356 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 3857 reflections
a = 9.5990 (8) Åθ = 2.2–28.2°
b = 8.3294 (7) ŵ = 0.10 mm1
c = 14.7444 (12) ÅT = 100 K
β = 107.684 (1)°Prism, orange
V = 1123.17 (16) Å30.30 × 0.25 × 0.05 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer
2433 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ω scansh = 1212
10316 measured reflectionsk = 1010
2576 independent reflectionsl = 1919
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0491P)2 + 0.1273P]
where P = (Fo2 + 2Fc2)/3
2576 reflections(Δ/σ)max = 0.001
302 parametersΔρmax = 0.25 e Å3
2 restraintsΔρmin = 0.20 e Å3
Crystal data top
C25H30O8V = 1123.17 (16) Å3
Mr = 458.49Z = 2
Monoclinic, PcMo Kα radiation
a = 9.5990 (8) ŵ = 0.10 mm1
b = 8.3294 (7) ÅT = 100 K
c = 14.7444 (12) Å0.30 × 0.25 × 0.05 mm
β = 107.684 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer
2433 reflections with I > 2σ(I)
10316 measured reflectionsRint = 0.037
2576 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0322 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.25 e Å3
2576 reflectionsΔρmin = 0.20 e Å3
302 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.50254 (17)0.07085 (17)0.49935 (10)0.0174 (3)
O20.69328 (17)0.04190 (19)0.83437 (11)0.0204 (3)
O30.79441 (18)0.4985 (2)0.67354 (12)0.0221 (3)
H30.777 (4)0.526 (4)0.612 (3)0.042 (9)*
O40.68542 (17)0.51474 (19)0.49826 (11)0.0198 (3)
O50.01705 (16)0.23344 (18)0.10555 (10)0.0178 (3)
O60.06369 (19)0.0284 (2)0.22016 (12)0.0251 (4)
O70.05288 (16)0.41671 (18)0.02881 (10)0.0187 (3)
O80.05354 (17)0.66810 (19)0.10124 (11)0.0210 (3)
C10.4074 (2)0.0676 (2)0.49859 (16)0.0181 (4)
C20.3732 (3)0.1334 (3)0.39786 (16)0.0237 (5)
H2A0.46350.17200.38740.036*
H2B0.33040.04820.35200.036*
H2C0.30360.22240.38940.036*
C30.2692 (2)0.0069 (3)0.51717 (18)0.0228 (5)
H3A0.21990.07010.46750.034*
H3B0.29490.04600.57950.034*
H3C0.20380.09750.51650.034*
C40.4918 (2)0.1879 (3)0.57238 (15)0.0194 (4)
H4A0.57930.22410.55590.023*
H4B0.42950.28290.57180.023*
C50.5390 (2)0.1138 (3)0.67197 (15)0.0193 (4)
H5A0.45420.10960.69690.023*
H5B0.61520.18190.71530.023*
C60.5981 (2)0.0529 (2)0.66954 (15)0.0160 (4)
C70.5763 (2)0.1365 (3)0.58478 (15)0.0149 (4)
C80.6366 (2)0.2927 (3)0.58144 (15)0.0148 (4)
C90.7257 (2)0.3568 (3)0.66940 (15)0.0166 (4)
C100.7437 (2)0.2780 (3)0.75539 (15)0.0174 (4)
H100.79880.32590.81370.021*
C110.6798 (2)0.1281 (3)0.75453 (15)0.0161 (4)
C120.7820 (3)0.1083 (3)0.92334 (15)0.0225 (5)
H12A0.78260.03460.97530.034*
H12B0.74160.21200.93420.034*
H12C0.88220.12330.92110.034*
C130.6066 (2)0.3942 (3)0.49629 (14)0.0150 (4)
C140.4826 (2)0.3661 (3)0.41004 (15)0.0163 (4)
H140.41620.28070.40810.020*
C150.4642 (2)0.4620 (3)0.33424 (15)0.0167 (4)
H150.53480.54460.34070.020*
C160.3495 (2)0.4553 (3)0.24339 (15)0.0160 (4)
C170.3573 (2)0.5633 (2)0.17258 (15)0.0178 (4)
H170.43180.64280.18690.021*
C180.2588 (2)0.5565 (3)0.08200 (15)0.0174 (4)
H180.26600.63100.03490.021*
C190.1493 (2)0.4408 (3)0.05985 (14)0.0163 (4)
C200.1330 (2)0.3372 (2)0.13222 (15)0.0147 (4)
C210.2341 (2)0.3429 (2)0.22193 (15)0.0159 (4)
H210.22570.27030.26970.019*
C220.0247 (2)0.1575 (3)0.18001 (15)0.0201 (4)
H22A0.02100.23750.23030.024*
H22B0.12700.11990.15430.024*
C230.0360 (3)0.1112 (3)0.16131 (19)0.0282 (5)
H23A0.10170.19790.19340.042*
H23B0.05310.08660.10060.042*
H23C0.06570.14510.14960.042*
C240.0800 (2)0.5048 (3)0.10506 (15)0.0178 (4)
H24A0.18310.48870.10300.021*
H24B0.01710.46160.16640.021*
C250.0952 (3)0.7036 (3)0.10670 (18)0.0271 (5)
H25A0.10740.82000.10340.041*
H25B0.11880.65200.05350.041*
H25C0.16070.66300.16700.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0221 (8)0.0131 (7)0.0157 (7)0.0047 (6)0.0039 (6)0.0013 (6)
O20.0239 (8)0.0202 (8)0.0156 (7)0.0001 (6)0.0038 (6)0.0013 (6)
O30.0244 (8)0.0185 (8)0.0178 (8)0.0070 (6)0.0018 (6)0.0009 (6)
O40.0205 (8)0.0183 (8)0.0175 (7)0.0055 (6)0.0013 (6)0.0006 (6)
O50.0174 (7)0.0182 (8)0.0161 (7)0.0057 (6)0.0026 (6)0.0007 (6)
O60.0279 (9)0.0205 (8)0.0221 (8)0.0044 (7)0.0004 (7)0.0051 (6)
O70.0202 (8)0.0189 (8)0.0149 (7)0.0030 (6)0.0023 (6)0.0022 (6)
O80.0227 (8)0.0182 (8)0.0206 (8)0.0002 (6)0.0044 (7)0.0026 (6)
C10.0199 (11)0.0120 (10)0.0202 (10)0.0048 (8)0.0030 (8)0.0014 (8)
C20.0278 (12)0.0180 (11)0.0216 (11)0.0053 (9)0.0019 (10)0.0033 (9)
C30.0165 (10)0.0197 (10)0.0313 (12)0.0002 (8)0.0061 (9)0.0020 (9)
C40.0200 (11)0.0128 (10)0.0226 (11)0.0019 (8)0.0024 (9)0.0000 (8)
C50.0209 (11)0.0150 (10)0.0191 (11)0.0016 (8)0.0020 (9)0.0025 (8)
C60.0150 (10)0.0137 (10)0.0192 (10)0.0007 (8)0.0050 (8)0.0002 (8)
C70.0116 (9)0.0144 (10)0.0179 (10)0.0010 (7)0.0032 (8)0.0017 (8)
C80.0133 (10)0.0140 (10)0.0165 (9)0.0000 (8)0.0035 (8)0.0017 (7)
C90.0146 (10)0.0151 (10)0.0194 (11)0.0007 (8)0.0039 (8)0.0004 (8)
C100.0149 (10)0.0189 (10)0.0161 (10)0.0004 (8)0.0010 (8)0.0016 (8)
C110.0134 (10)0.0181 (10)0.0167 (10)0.0031 (8)0.0044 (8)0.0030 (8)
C120.0289 (12)0.0225 (11)0.0134 (10)0.0044 (10)0.0022 (9)0.0010 (9)
C130.0143 (10)0.0139 (10)0.0167 (10)0.0004 (8)0.0046 (8)0.0009 (7)
C140.0162 (10)0.0134 (10)0.0179 (10)0.0016 (8)0.0030 (8)0.0014 (8)
C150.0178 (10)0.0138 (10)0.0188 (10)0.0012 (8)0.0058 (8)0.0023 (8)
C160.0167 (10)0.0150 (10)0.0169 (10)0.0001 (8)0.0058 (8)0.0005 (8)
C170.0203 (11)0.0139 (10)0.0189 (10)0.0024 (8)0.0055 (8)0.0005 (8)
C180.0190 (10)0.0162 (11)0.0172 (10)0.0007 (8)0.0059 (8)0.0018 (8)
C190.0189 (10)0.0152 (10)0.0140 (10)0.0018 (8)0.0037 (8)0.0006 (8)
C200.0156 (10)0.0106 (9)0.0189 (10)0.0005 (8)0.0065 (8)0.0020 (8)
C210.0166 (10)0.0143 (10)0.0170 (10)0.0006 (8)0.0054 (8)0.0016 (8)
C220.0206 (11)0.0229 (11)0.0169 (10)0.0047 (9)0.0057 (9)0.0004 (8)
C230.0282 (13)0.0222 (12)0.0345 (14)0.0057 (10)0.0099 (11)0.0002 (10)
C240.0186 (10)0.0193 (11)0.0149 (10)0.0002 (8)0.0043 (8)0.0020 (8)
C250.0267 (13)0.0280 (12)0.0260 (12)0.0072 (10)0.0070 (10)0.0006 (10)
Geometric parameters (Å, º) top
O1—C71.358 (3)C8—C91.423 (3)
O1—C11.469 (2)C8—C131.467 (3)
O2—C111.351 (3)C9—C101.391 (3)
O2—C121.440 (3)C10—C111.390 (3)
O3—C91.344 (3)C10—H100.9500
O3—H30.90 (4)C12—H12A0.9800
O4—C131.253 (3)C12—H12B0.9800
O5—C201.369 (2)C12—H12C0.9800
O5—C221.426 (2)C13—C141.472 (3)
O6—C221.387 (3)C14—C151.341 (3)
O6—C231.427 (3)C14—H140.9500
O7—C191.368 (3)C15—C161.454 (3)
O7—C241.431 (2)C15—H150.9500
O8—C241.388 (3)C16—C171.397 (3)
O8—C251.436 (3)C16—C211.410 (3)
C1—C41.519 (3)C17—C181.384 (3)
C1—C31.520 (3)C17—H170.9500
C1—C21.523 (3)C18—C191.389 (3)
C2—H2A0.9800C18—H180.9500
C2—H2B0.9800C19—C201.418 (3)
C2—H2C0.9800C20—C211.383 (3)
C3—H3A0.9800C21—H210.9500
C3—H3B0.9800C22—H22A0.9900
C3—H3C0.9800C22—H22B0.9900
C4—C51.529 (3)C23—H23A0.9800
C4—H4A0.9900C23—H23B0.9800
C4—H4B0.9900C23—H23C0.9800
C5—C61.504 (3)C24—H24A0.9900
C5—H5A0.9900C24—H24B0.9900
C5—H5B0.9900C25—H25A0.9800
C6—C71.390 (3)C25—H25B0.9800
C6—C111.407 (3)C25—H25C0.9800
C7—C81.431 (3)
C7—O1—C1118.07 (16)O2—C12—H12B109.5
C11—O2—C12117.60 (17)H12A—C12—H12B109.5
C9—O3—H3104 (2)O2—C12—H12C109.5
C20—O5—C22116.93 (16)H12A—C12—H12C109.5
C22—O6—C23113.33 (18)H12B—C12—H12C109.5
C19—O7—C24116.34 (16)O4—C13—C8118.78 (18)
C24—O8—C25113.00 (18)O4—C13—C14118.10 (18)
O1—C1—C4108.51 (17)C8—C13—C14123.03 (18)
O1—C1—C3108.19 (17)C15—C14—C13119.54 (19)
C4—C1—C3113.25 (18)C15—C14—H14120.2
O1—C1—C2103.86 (16)C13—C14—H14120.2
C4—C1—C2111.78 (18)C14—C15—C16128.0 (2)
C3—C1—C2110.74 (19)C14—C15—H15116.0
C1—C2—H2A109.5C16—C15—H15116.0
C1—C2—H2B109.5C17—C16—C21118.45 (19)
H2A—C2—H2B109.5C17—C16—C15117.75 (19)
C1—C2—H2C109.5C21—C16—C15123.77 (18)
H2A—C2—H2C109.5C18—C17—C16121.24 (19)
H2B—C2—H2C109.5C18—C17—H17119.4
C1—C3—H3A109.5C16—C17—H17119.4
C1—C3—H3B109.5C17—C18—C19120.12 (19)
H3A—C3—H3B109.5C17—C18—H18119.9
C1—C3—H3C109.5C19—C18—H18119.9
H3A—C3—H3C109.5O7—C19—C18124.78 (18)
H3B—C3—H3C109.5O7—C19—C20115.63 (18)
C1—C4—C5111.09 (18)C18—C19—C20119.59 (19)
C1—C4—H4A109.4O5—C20—C21124.72 (18)
C5—C4—H4A109.4O5—C20—C19115.73 (18)
C1—C4—H4B109.4C21—C20—C19119.53 (18)
C5—C4—H4B109.4C20—C21—C16120.83 (18)
H4A—C4—H4B108.0C20—C21—H21119.6
C6—C5—C4110.70 (17)C16—C21—H21119.6
C6—C5—H5A109.5O6—C22—O5113.22 (18)
C4—C5—H5A109.5O6—C22—H22A108.9
C6—C5—H5B109.5O5—C22—H22A108.9
C4—C5—H5B109.5O6—C22—H22B108.9
H5A—C5—H5B108.1O5—C22—H22B108.9
C7—C6—C11117.93 (19)H22A—C22—H22B107.7
C7—C6—C5121.93 (19)O6—C23—H23A109.5
C11—C6—C5120.13 (18)O6—C23—H23B109.5
O1—C7—C6121.74 (18)H23A—C23—H23B109.5
O1—C7—C8115.87 (17)O6—C23—H23C109.5
C6—C7—C8122.31 (19)H23A—C23—H23C109.5
C9—C8—C7116.57 (18)H23B—C23—H23C109.5
C9—C8—C13118.11 (18)O8—C24—O7113.05 (17)
C7—C8—C13125.21 (18)O8—C24—H24A109.0
O3—C9—C10116.71 (19)O7—C24—H24A109.0
O3—C9—C8121.45 (19)O8—C24—H24B109.0
C10—C9—C8121.84 (19)O7—C24—H24B109.0
C9—C10—C11118.90 (19)H24A—C24—H24B107.8
C9—C10—H10120.5O8—C25—H25A109.5
C11—C10—H10120.5O8—C25—H25B109.5
O2—C11—C10122.98 (19)H25A—C25—H25B109.5
O2—C11—C6114.77 (18)O8—C25—H25C109.5
C10—C11—C6122.24 (19)H25A—C25—H25C109.5
O2—C12—H12A109.5H25B—C25—H25C109.5
C7—O1—C1—C447.8 (2)C5—C6—C11—C10176.19 (19)
C7—O1—C1—C375.5 (2)C9—C8—C13—O416.7 (3)
C7—O1—C1—C2166.83 (18)C7—C8—C13—O4167.3 (2)
O1—C1—C4—C560.1 (2)C9—C8—C13—C14159.84 (19)
C3—C1—C4—C560.0 (2)C7—C8—C13—C1416.2 (3)
C2—C1—C4—C5174.09 (18)O4—C13—C14—C154.9 (3)
C1—C4—C5—C643.8 (2)C8—C13—C14—C15178.5 (2)
C4—C5—C6—C714.6 (3)C13—C14—C15—C16179.6 (2)
C4—C5—C6—C11164.52 (19)C14—C15—C16—C17176.5 (2)
C1—O1—C7—C618.7 (3)C14—C15—C16—C211.3 (3)
C1—O1—C7—C8164.55 (17)C21—C16—C17—C182.9 (3)
C11—C6—C7—O1177.99 (18)C15—C16—C17—C18175.06 (19)
C5—C6—C7—O11.2 (3)C16—C17—C18—C190.0 (3)
C11—C6—C7—C81.5 (3)C24—O7—C19—C187.9 (3)
C5—C6—C7—C8177.66 (19)C24—O7—C19—C20171.75 (17)
O1—C7—C8—C9174.29 (17)C17—C18—C19—O7175.3 (2)
C6—C7—C8—C92.4 (3)C17—C18—C19—C204.3 (3)
O1—C7—C8—C139.6 (3)C22—O5—C20—C2117.4 (3)
C6—C7—C8—C13173.71 (19)C22—O5—C20—C19164.53 (18)
C7—C8—C9—O3176.20 (19)O7—C19—C20—O54.1 (3)
C13—C8—C9—O37.4 (3)C18—C19—C20—O5176.19 (18)
C7—C8—C9—C105.1 (3)O7—C19—C20—C21174.01 (18)
C13—C8—C9—C10171.26 (19)C18—C19—C20—C215.7 (3)
O3—C9—C10—C11177.43 (19)O5—C20—C21—C16179.29 (19)
C8—C9—C10—C113.8 (3)C19—C20—C21—C162.7 (3)
C12—O2—C11—C101.9 (3)C17—C16—C21—C201.5 (3)
C12—O2—C11—C6176.82 (18)C15—C16—C21—C20176.33 (19)
C9—C10—C11—O2179.01 (19)C23—O6—C22—O575.0 (2)
C9—C10—C11—C60.4 (3)C20—O5—C22—O679.4 (2)
C7—C6—C11—O2178.28 (17)C25—O8—C24—O760.4 (2)
C5—C6—C11—O22.6 (3)C19—O7—C24—O870.3 (2)
C7—C6—C11—C103.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.90 (4)1.65 (4)2.480 (2)153 (3)

Experimental details

Crystal data
Chemical formulaC25H30O8
Mr458.49
Crystal system, space groupMonoclinic, Pc
Temperature (K)100
a, b, c (Å)9.5990 (8), 8.3294 (7), 14.7444 (12)
β (°) 107.684 (1)
V3)1123.17 (16)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.25 × 0.05
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10316, 2576, 2433
Rint0.037
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.082, 1.06
No. of reflections2576
No. of parameters302
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.90 (4)1.65 (4)2.480 (2)153 (3)
 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

First citationAvila, H. P., Smania, E. F. A., Monache, F. D. & Junior, A. S. (2008). Bioorg. Med. Chem. 16, 9790–9794.  CAS Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNarender, T., Reddy, K.P., Shweta, Srivastava, K., Mishra, D.K., & Puri, S. K. (2007). Org. Lett. 9, 5369–5372.  CrossRef CAS Google Scholar
First citationReddy, N. P., Aparoy, P., Reddy, T. C. M., Achari, C., Sridhar, P. R. & Reddanna, P. (2010). Bioorg. Med. Chem. 18, 5807–5815.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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