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

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ISSN: 2056-9890

1-Hydr­­oxy-2-meth­­oxy-6-methyl-9,10-anthra­quinone from Rennellia elliptica Korth.

aFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor Darul Ehsan, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 8 May 2009; accepted 11 May 2009; online 29 May 2009)

The title compound, C16H12O4, exists as planar molecules in the solid state (r.m.s. deviation of 0.02 Å in one mol­ecule and 0.07 Å in the second independent mol­ecule comprising the asymmetric unit). In each mol­ecule, the 1-hydr­oxy group forms an intra­molecular hydrogen bond to the adjacent carbonyl O atom.

Related literature

The existence of the title natural product has only been reported for Crucianella maritima L. (El-Lakany et al., 2004[El-Lakany, A. M., Aboul-Ela, M. A., Abdel-Kader, M. S., Badr, J. M., Sabri, N. N. & Goher, Y. (2004). Nat. Prod. Sci. 10, 63-68.]). For another anthraquinone isolated from Rennellia elliptica Korth., see: Ismail et al. (2009[Ismail, N. H., Osman, C. P., Ahmad, R., Awang, K. & Ng, S. W. (2009). Acta Cryst. E65, o1433-o1434.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12O4

  • Mr = 268.26

  • Triclinic, [P \overline 1]

  • a = 7.1755 (3) Å

  • b = 11.9082 (5) Å

  • c = 14.9683 (7) Å

  • α = 91.409 (3)°

  • β = 100.603 (3)°

  • γ = 105.666 (3)°

  • V = 1206.73 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.25 × 0.20 × 0.01 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 6750 measured reflections

  • 4142 independent reflections

  • 2248 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.082

  • wR(F2) = 0.267

  • S = 1.08

  • 4142 reflections

  • 367 parameters

  • H-atom parameters constrained

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O2 0.84 1.80 2.538 (4) 147
O7—H7⋯O6 0.84 1.81 2.551 (5) 146

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

The existence of the title natural product has only been reported for Crucianella maritima L. (El-Lakany et al., 2004). For another anthraquinone isolated from Rennellia elliptica Korth., see: Ismail et al. (2009).

Experimental top

About 1 kg of the root of Rennelia elliptica Korth., which was collected from the Kuala Keniam National Park, Malaysia, was extracted with dichloromethane. The solvent was removed to give a crude material (approx. 10 g) that was fractionated on a chromatography column (60 x 5 cm) packed with silica. The silica had been previously immersed in 4% oxalic acid and then activated by heating to 363 K. The fractions were eluted with hexane–dichloromethane (3:7 v/v), and those fractions having an identical TLC pattern were combined and then subjected to column chromatography (330 x 15 mm), with dichloromethane as eluent. The compound was further purified on a short glass column (50 x 5 mm). The solvent was removed and the product recrystallized from chloroform to furnish yellow crystals (about 10 mg). The formulation was established by 1H- and 13C-NMR spectroscopy.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C). The hydroxy H-atoms were similarly generated (O–H 0.84 Å).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C16H12O4 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
1-Hydroxy-2-methoxy-6-methyl-9,10-anthraquinone top
Crystal data top
C16H12O4Z = 4
Mr = 268.26F(000) = 560
Triclinic, P1Dx = 1.477 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1755 (3) ÅCell parameters from 1159 reflections
b = 11.9082 (5) Åθ = 2.8–26.8°
c = 14.9683 (7) ŵ = 0.11 mm1
α = 91.409 (3)°T = 100 K
β = 100.603 (3)°Plate, yellow
γ = 105.666 (3)°0.25 × 0.20 × 0.01 mm
V = 1206.73 (9) Å3
Data collection top
Bruker SMART APEX
diffractometer
2248 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω scansh = 88
6750 measured reflectionsk = 1413
4142 independent reflectionsl = 1717
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)] = 0.082Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.267H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1397P)2 + 0.3435P]
where P = (Fo2 + 2Fc2)/3
4142 reflections(Δ/σ)max = 0.001
367 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C16H12O4γ = 105.666 (3)°
Mr = 268.26V = 1206.73 (9) Å3
Triclinic, P1Z = 4
a = 7.1755 (3) ÅMo Kα radiation
b = 11.9082 (5) ŵ = 0.11 mm1
c = 14.9683 (7) ÅT = 100 K
α = 91.409 (3)°0.25 × 0.20 × 0.01 mm
β = 100.603 (3)°
Data collection top
Bruker SMART APEX
diffractometer
2248 reflections with I > 2σ(I)
6750 measured reflectionsRint = 0.051
4142 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0820 restraints
wR(F2) = 0.267H-atom parameters constrained
S = 1.08Δρmax = 0.59 e Å3
4142 reflectionsΔρmin = 0.35 e Å3
367 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2331 (5)0.2601 (3)0.5314 (2)0.0207 (8)
O20.2924 (5)0.7172 (3)0.4917 (2)0.0219 (9)
O30.3202 (5)0.6932 (3)0.3261 (2)0.0205 (8)
H30.30840.72720.37370.031*
O40.3344 (5)0.5601 (3)0.1875 (2)0.0207 (8)
O50.9299 (6)1.2275 (3)1.0962 (2)0.0327 (10)
O60.5739 (6)0.7665 (3)1.0100 (2)0.0281 (9)
O70.5636 (6)0.7944 (3)0.8409 (2)0.0297 (10)
H70.53650.75870.88660.045*
O80.6524 (5)0.9285 (3)0.7122 (2)0.0279 (9)
C10.1303 (8)0.4169 (5)0.8389 (3)0.0247 (13)
H1A0.20630.36080.85550.037*
H1B0.01100.37730.83160.037*
H1C0.16820.48060.88720.037*
C20.1725 (7)0.4662 (4)0.7505 (3)0.0188 (11)
C30.1867 (7)0.3958 (4)0.6786 (3)0.0186 (11)
H3A0.17460.31530.68580.022*
C40.2183 (7)0.4406 (4)0.5959 (3)0.0163 (11)
C50.2389 (7)0.3634 (4)0.5212 (3)0.0158 (11)
C60.2613 (7)0.4126 (4)0.4328 (3)0.0155 (11)
C70.2703 (7)0.3443 (4)0.3595 (3)0.0146 (11)
H7A0.26150.26400.36620.017*
C80.2921 (7)0.3884 (4)0.2752 (3)0.0187 (12)
H80.29510.33850.22530.022*
C90.3092 (7)0.5067 (4)0.2654 (3)0.0179 (11)
C100.3034 (7)0.5792 (4)0.3390 (3)0.0160 (11)
C110.2798 (7)0.5340 (4)0.4234 (3)0.0153 (11)
C120.2727 (7)0.6111 (4)0.4991 (3)0.0176 (11)
C130.2400 (7)0.5601 (4)0.5865 (3)0.0143 (11)
C140.2299 (7)0.6314 (4)0.6590 (3)0.0184 (11)
H140.24620.71250.65270.022*
C150.1964 (7)0.5858 (4)0.7401 (3)0.0195 (12)
H150.18940.63550.78930.023*
C160.3257 (8)0.4888 (5)0.1080 (4)0.0295 (14)
H16A0.33290.53670.05580.044*
H16B0.20140.42610.09590.044*
H16C0.43700.45460.11790.044*
C170.8428 (9)1.0596 (5)1.4057 (3)0.0262 (13)
H17A0.97191.11821.41930.039*
H17B0.84500.99501.44490.039*
H17C0.74091.09571.41710.039*
C180.7980 (7)1.0137 (5)1.3075 (3)0.0204 (12)
C190.8440 (7)1.0856 (5)1.2383 (3)0.0204 (12)
H190.90841.16641.25370.024*
C200.7990 (7)1.0432 (4)1.1479 (3)0.0167 (11)
C210.8479 (8)1.1216 (5)1.0761 (3)0.0221 (12)
C220.7990 (7)1.0732 (4)0.9807 (3)0.0206 (12)
C230.8403 (8)1.1438 (5)0.9115 (3)0.0230 (12)
H230.90191.22510.92590.028*
C240.7944 (8)1.0992 (5)0.8208 (3)0.0236 (12)
H240.82611.15000.77450.028*
C250.7032 (8)0.9821 (5)0.7979 (3)0.0236 (13)
C260.6581 (7)0.9084 (4)0.8672 (4)0.0218 (12)
C270.7028 (7)0.9509 (4)0.9582 (3)0.0193 (12)
C280.6543 (7)0.8737 (4)1.0285 (3)0.0196 (12)
C290.7021 (7)0.9217 (4)1.1244 (3)0.0196 (12)
C300.6537 (7)0.8511 (5)1.1930 (3)0.0221 (12)
H300.58690.77051.17810.027*
C310.7009 (8)0.8955 (4)1.2837 (3)0.0224 (12)
H310.66660.84491.32990.027*
C320.6916 (9)0.9996 (6)0.6386 (4)0.0317 (14)
H32A0.64610.95080.58090.047*
H32B0.83381.03700.64710.047*
H32C0.62161.06000.63740.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.025 (2)0.0202 (19)0.0184 (19)0.0103 (16)0.0018 (15)0.0029 (15)
O20.027 (2)0.0162 (19)0.023 (2)0.0089 (16)0.0025 (16)0.0009 (15)
O30.026 (2)0.0153 (18)0.020 (2)0.0053 (16)0.0048 (16)0.0001 (15)
O40.023 (2)0.025 (2)0.0140 (19)0.0080 (16)0.0030 (15)0.0005 (15)
O50.048 (3)0.018 (2)0.025 (2)0.0013 (19)0.0036 (19)0.0023 (16)
O60.035 (2)0.018 (2)0.028 (2)0.0044 (18)0.0015 (17)0.0022 (16)
O70.037 (2)0.026 (2)0.024 (2)0.0076 (19)0.0049 (18)0.0012 (17)
O80.033 (2)0.038 (2)0.014 (2)0.0150 (19)0.0003 (16)0.0025 (17)
C10.021 (3)0.033 (3)0.024 (3)0.010 (3)0.011 (2)0.007 (2)
C20.011 (3)0.028 (3)0.017 (3)0.007 (2)0.001 (2)0.003 (2)
C30.012 (3)0.020 (3)0.023 (3)0.005 (2)0.000 (2)0.005 (2)
C40.006 (2)0.025 (3)0.017 (3)0.005 (2)0.002 (2)0.004 (2)
C50.008 (3)0.020 (3)0.019 (3)0.005 (2)0.000 (2)0.000 (2)
C60.008 (3)0.022 (3)0.015 (3)0.005 (2)0.003 (2)0.000 (2)
C70.010 (3)0.013 (2)0.020 (3)0.002 (2)0.004 (2)0.001 (2)
C80.016 (3)0.023 (3)0.016 (3)0.008 (2)0.001 (2)0.005 (2)
C90.013 (3)0.025 (3)0.016 (3)0.005 (2)0.002 (2)0.004 (2)
C100.010 (3)0.022 (3)0.015 (3)0.004 (2)0.001 (2)0.004 (2)
C110.011 (3)0.018 (3)0.015 (3)0.007 (2)0.004 (2)0.001 (2)
C120.010 (3)0.022 (3)0.019 (3)0.004 (2)0.002 (2)0.000 (2)
C130.007 (2)0.021 (3)0.016 (3)0.007 (2)0.0013 (19)0.002 (2)
C140.017 (3)0.019 (3)0.018 (3)0.007 (2)0.002 (2)0.001 (2)
C150.015 (3)0.027 (3)0.014 (3)0.006 (2)0.003 (2)0.005 (2)
C160.031 (3)0.034 (3)0.020 (3)0.003 (3)0.005 (2)0.000 (2)
C170.034 (3)0.027 (3)0.018 (3)0.011 (3)0.001 (2)0.002 (2)
C180.017 (3)0.028 (3)0.018 (3)0.013 (2)0.000 (2)0.002 (2)
C190.020 (3)0.022 (3)0.019 (3)0.009 (2)0.003 (2)0.002 (2)
C200.017 (3)0.023 (3)0.014 (3)0.013 (2)0.003 (2)0.000 (2)
C210.019 (3)0.025 (3)0.024 (3)0.011 (3)0.001 (2)0.004 (2)
C220.022 (3)0.025 (3)0.017 (3)0.012 (2)0.003 (2)0.004 (2)
C230.021 (3)0.026 (3)0.021 (3)0.005 (2)0.005 (2)0.000 (2)
C240.028 (3)0.031 (3)0.013 (3)0.010 (3)0.003 (2)0.005 (2)
C250.019 (3)0.042 (3)0.015 (3)0.015 (3)0.006 (2)0.002 (2)
C260.015 (3)0.022 (3)0.030 (3)0.010 (2)0.004 (2)0.000 (2)
C270.013 (3)0.025 (3)0.022 (3)0.010 (2)0.003 (2)0.002 (2)
C280.009 (3)0.026 (3)0.025 (3)0.008 (2)0.000 (2)0.000 (2)
C290.014 (3)0.020 (3)0.026 (3)0.010 (2)0.001 (2)0.002 (2)
C300.020 (3)0.025 (3)0.027 (3)0.012 (2)0.007 (2)0.007 (2)
C310.027 (3)0.022 (3)0.022 (3)0.012 (2)0.008 (2)0.010 (2)
C320.030 (3)0.056 (4)0.013 (3)0.017 (3)0.008 (2)0.005 (3)
Geometric parameters (Å, º) top
O1—C51.235 (6)C14—C151.377 (7)
O2—C121.243 (6)C14—H140.9500
O3—C101.351 (6)C15—H150.9500
O3—H30.8400C16—H16A0.9800
O4—C91.360 (6)C16—H16B0.9800
O4—C161.426 (6)C16—H16C0.9800
O5—C211.242 (6)C17—C181.502 (7)
O6—C281.251 (6)C17—H17A0.9800
O7—C261.356 (6)C17—H17B0.9800
O7—H70.8400C17—H17C0.9800
O8—C251.359 (6)C18—C191.390 (7)
O8—C321.429 (6)C18—C311.396 (7)
C1—C21.509 (7)C19—C201.382 (7)
C1—H1A0.9800C19—H190.9500
C1—H1B0.9800C20—C291.429 (7)
C1—H1C0.9800C20—C211.469 (7)
C2—C31.383 (7)C21—C221.470 (7)
C2—C151.404 (7)C22—C231.375 (7)
C3—C41.394 (7)C22—C271.434 (7)
C3—H3A0.9500C23—C241.392 (7)
C4—C131.402 (7)C23—H230.9500
C4—C51.483 (7)C24—C251.376 (8)
C5—C61.478 (7)C24—H240.9500
C6—C71.372 (7)C25—C261.402 (7)
C6—C111.428 (7)C26—C271.390 (7)
C7—C81.397 (7)C27—C281.443 (7)
C7—H7A0.9500C28—C291.476 (7)
C8—C91.395 (7)C29—C301.377 (7)
C8—H80.9500C30—C311.392 (7)
C9—C101.397 (7)C30—H300.9500
C10—C111.406 (7)C31—H310.9500
C11—C121.459 (7)C32—H32A0.9800
C12—C131.487 (7)C32—H32B0.9800
C13—C141.386 (7)C32—H32C0.9800
C10—O3—H3109.5H16A—C16—H16C109.5
C9—O4—C16117.9 (4)H16B—C16—H16C109.5
C26—O7—H7109.5C18—C17—H17A109.5
C25—O8—C32117.7 (4)C18—C17—H17B109.5
C2—C1—H1A109.5H17A—C17—H17B109.5
C2—C1—H1B109.5C18—C17—H17C109.5
H1A—C1—H1B109.5H17A—C17—H17C109.5
C2—C1—H1C109.5H17B—C17—H17C109.5
H1A—C1—H1C109.5C19—C18—C31118.3 (5)
H1B—C1—H1C109.5C19—C18—C17122.3 (5)
C3—C2—C15118.9 (5)C31—C18—C17119.3 (5)
C3—C2—C1121.5 (5)C20—C19—C18122.1 (5)
C15—C2—C1119.7 (5)C20—C19—H19119.0
C2—C3—C4121.4 (5)C18—C19—H19119.0
C2—C3—H3A119.3C19—C20—C29119.1 (5)
C4—C3—H3A119.3C19—C20—C21120.8 (5)
C3—C4—C13118.9 (5)C29—C20—C21120.0 (4)
C3—C4—C5119.9 (4)O5—C21—C22120.6 (5)
C13—C4—C5121.1 (4)O5—C21—C20120.1 (5)
O1—C5—C6120.5 (4)C22—C21—C20119.2 (5)
O1—C5—C4121.3 (4)C23—C22—C27118.8 (5)
C6—C5—C4118.2 (4)C23—C22—C21121.1 (5)
C7—C6—C11118.8 (4)C27—C22—C21120.1 (4)
C7—C6—C5121.2 (4)C22—C23—C24121.7 (5)
C11—C6—C5120.0 (4)C22—C23—H23119.1
C6—C7—C8122.5 (4)C24—C23—H23119.1
C6—C7—H7A118.8C25—C24—C23120.4 (5)
C8—C7—H7A118.8C25—C24—H24119.8
C9—C8—C7119.0 (5)C23—C24—H24119.8
C9—C8—H8120.5O8—C25—C24125.8 (5)
C7—C8—H8120.5O8—C25—C26115.3 (5)
O4—C9—C10115.4 (4)C24—C25—C26119.0 (5)
O4—C9—C8124.5 (5)O7—C26—C27121.6 (5)
C10—C9—C8120.1 (4)O7—C26—C25116.7 (5)
O3—C10—C9117.9 (4)C27—C26—C25121.7 (5)
O3—C10—C11121.6 (4)C26—C27—C22118.5 (5)
C9—C10—C11120.5 (4)C26—C27—C28120.8 (5)
C10—C11—C6119.1 (4)C22—C27—C28120.7 (5)
C10—C11—C12119.6 (4)O6—C28—C27121.4 (5)
C6—C11—C12121.3 (4)O6—C28—C29119.1 (5)
O2—C12—C11121.5 (4)C27—C28—C29119.5 (5)
O2—C12—C13120.0 (4)C30—C29—C20118.6 (5)
C11—C12—C13118.5 (4)C30—C29—C28121.0 (5)
C14—C13—C4119.9 (4)C20—C29—C28120.3 (5)
C14—C13—C12119.5 (4)C29—C30—C31121.3 (5)
C4—C13—C12120.6 (4)C29—C30—H30119.3
C15—C14—C13120.6 (5)C31—C30—H30119.3
C15—C14—H14119.7C30—C31—C18120.5 (5)
C13—C14—H14119.7C30—C31—H31119.7
C14—C15—C2120.3 (5)C18—C31—H31119.7
C14—C15—H15119.8O8—C32—H32A109.5
C2—C15—H15119.8O8—C32—H32B109.5
O4—C16—H16A109.5H32A—C32—H32B109.5
O4—C16—H16B109.5O8—C32—H32C109.5
H16A—C16—H16B109.5H32A—C32—H32C109.5
O4—C16—H16C109.5H32B—C32—H32C109.5
C15—C2—C3—C41.8 (7)C31—C18—C19—C200.9 (7)
C1—C2—C3—C4177.5 (4)C17—C18—C19—C20178.7 (5)
C2—C3—C4—C131.3 (7)C18—C19—C20—C290.0 (7)
C2—C3—C4—C5178.1 (4)C18—C19—C20—C21179.4 (4)
C3—C4—C5—O11.6 (7)C19—C20—C21—O50.3 (7)
C13—C4—C5—O1175.1 (5)C29—C20—C21—O5179.1 (5)
C3—C4—C5—C6176.7 (4)C19—C20—C21—C22179.6 (4)
C13—C4—C5—C66.6 (6)C29—C20—C21—C221.0 (7)
O1—C5—C6—C71.9 (7)O5—C21—C22—C230.8 (8)
C4—C5—C6—C7176.5 (4)C20—C21—C22—C23179.3 (4)
O1—C5—C6—C11176.2 (4)O5—C21—C22—C27179.5 (5)
C4—C5—C6—C115.4 (6)C20—C21—C22—C270.6 (7)
C11—C6—C7—C81.7 (7)C27—C22—C23—C241.1 (7)
C5—C6—C7—C8179.8 (4)C21—C22—C23—C24179.8 (5)
C6—C7—C8—C91.3 (7)C22—C23—C24—C250.7 (8)
C16—O4—C9—C10175.1 (4)C32—O8—C25—C241.8 (7)
C16—O4—C9—C85.6 (7)C32—O8—C25—C26178.9 (4)
C7—C8—C9—O4178.8 (4)C23—C24—C25—O8179.5 (5)
C7—C8—C9—C100.4 (7)C23—C24—C25—C260.2 (7)
O4—C9—C10—O30.8 (6)O8—C25—C26—O72.4 (7)
C8—C9—C10—O3179.9 (4)C24—C25—C26—O7178.3 (4)
O4—C9—C10—C11179.4 (4)O8—C25—C26—C27179.5 (4)
C8—C9—C10—C110.1 (7)C24—C25—C26—C270.2 (7)
O3—C10—C11—C6179.5 (4)O7—C26—C27—C22178.6 (4)
C9—C10—C11—C60.2 (7)C25—C26—C27—C220.5 (7)
O3—C10—C11—C120.1 (7)O7—C26—C27—C281.7 (7)
C9—C10—C11—C12179.6 (4)C25—C26—C27—C28179.7 (4)
C7—C6—C11—C101.1 (7)C23—C22—C27—C261.0 (7)
C5—C6—C11—C10179.2 (4)C21—C22—C27—C26179.7 (4)
C7—C6—C11—C12179.6 (4)C23—C22—C27—C28179.2 (4)
C5—C6—C11—C121.4 (7)C21—C22—C27—C280.5 (7)
C10—C11—C12—O22.0 (7)C26—C27—C28—O61.1 (7)
C6—C11—C12—O2178.7 (4)C22—C27—C28—O6178.6 (5)
C10—C11—C12—C13177.7 (4)C26—C27—C28—C29179.5 (4)
C6—C11—C12—C131.7 (7)C22—C27—C28—C290.8 (7)
C3—C4—C13—C140.0 (7)C19—C20—C29—C301.1 (7)
C5—C4—C13—C14176.7 (4)C21—C20—C29—C30178.3 (4)
C3—C4—C13—C12179.6 (4)C19—C20—C29—C28179.3 (4)
C5—C4—C13—C123.6 (7)C21—C20—C29—C281.3 (7)
O2—C12—C13—C140.6 (7)O6—C28—C29—C302.1 (7)
C11—C12—C13—C14179.1 (4)C27—C28—C29—C30178.4 (4)
O2—C12—C13—C4179.7 (4)O6—C28—C29—C20178.3 (4)
C11—C12—C13—C40.6 (6)C27—C28—C29—C201.2 (7)
C4—C13—C14—C150.8 (7)C20—C29—C30—C311.3 (7)
C12—C13—C14—C15178.9 (4)C28—C29—C30—C31179.1 (4)
C13—C14—C15—C20.2 (7)C29—C30—C31—C180.4 (7)
C3—C2—C15—C141.1 (7)C19—C18—C31—C300.7 (7)
C1—C2—C15—C14178.3 (4)C17—C18—C31—C30178.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.802.538 (4)147
O7—H7···O60.841.812.551 (5)146

Experimental details

Crystal data
Chemical formulaC16H12O4
Mr268.26
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.1755 (3), 11.9082 (5), 14.9683 (7)
α, β, γ (°)91.409 (3), 100.603 (3), 105.666 (3)
V3)1206.73 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.25 × 0.20 × 0.01
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6750, 4142, 2248
Rint0.051
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.082, 0.267, 1.08
No. of reflections4142
No. of parameters367
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.59, 0.35

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.802.538 (4)147
O7—H7···O60.841.812.551 (5)146
 

Acknowledgements

We thank Universiti Teknologi MARA and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEl-Lakany, A. M., Aboul-Ela, M. A., Abdel-Kader, M. S., Badr, J. M., Sabri, N. N. & Goher, Y. (2004). Nat. Prod. Sci. 10, 63–68.  CAS Google Scholar
First citationIsmail, N. H., Osman, C. P., Ahmad, R., Awang, K. & Ng, S. W. (2009). Acta Cryst. E65, o1433–o1434.  Web of Science CSD CrossRef IUCr Journals 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. (2009). publCIF. In preparation.  Google Scholar

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