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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1435.
Published online 2009 May 29. doi:  10.1107/S1600536809017619
PMCID: PMC2969574

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

Abstract

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 [triangle]). For another anthraquinone isolated from Rennellia elliptica Korth., see: Ismail et al. (2009 [triangle]).

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Object name is e-65-o1435-scheme1.jpg

Experimental

Crystal data

  • C16H12O4
  • M r = 268.26
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1435-efi1.jpg
  • 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)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.082
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017619/tk2448sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017619/tk2448Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

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

Bruker SMART APEX diffractometer2248 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
graphiteθmax = 25.0°, θmin = 1.8°
ω scansh = −8→8
6750 measured reflectionsk = −14→13
4142 independent reflectionsl = −17→17

Refinement

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 = 1.08w = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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*
H1B−0.01100.37730.83160.037*
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)

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, °)

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—C4−1.8 (7)C31—C18—C19—C20−0.9 (7)
C1—C2—C3—C4177.5 (4)C17—C18—C19—C20−178.7 (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—O1−1.6 (7)C19—C20—C21—O5−0.3 (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—C6−6.6 (6)C29—C20—C21—C22−1.0 (7)
O1—C5—C6—C71.9 (7)O5—C21—C22—C23−0.8 (8)
C4—C5—C6—C7−176.5 (4)C20—C21—C22—C23179.3 (4)
O1—C5—C6—C11−176.2 (4)O5—C21—C22—C27−179.5 (5)
C4—C5—C6—C115.4 (6)C20—C21—C22—C270.6 (7)
C11—C6—C7—C8−1.7 (7)C27—C22—C23—C24−1.1 (7)
C5—C6—C7—C8−179.8 (4)C21—C22—C23—C24−179.8 (5)
C6—C7—C8—C91.3 (7)C22—C23—C24—C250.7 (8)
C16—O4—C9—C10−175.1 (4)C32—O8—C25—C24−1.8 (7)
C16—O4—C9—C85.6 (7)C32—O8—C25—C26178.9 (4)
C7—C8—C9—O4178.8 (4)C23—C24—C25—O8−179.5 (5)
C7—C8—C9—C10−0.4 (7)C23—C24—C25—C26−0.2 (7)
O4—C9—C10—O30.8 (6)O8—C25—C26—O7−2.4 (7)
C8—C9—C10—O3−179.9 (4)C24—C25—C26—O7178.3 (4)
O4—C9—C10—C11−179.4 (4)O8—C25—C26—C27179.5 (4)
C8—C9—C10—C11−0.1 (7)C24—C25—C26—C270.2 (7)
O3—C10—C11—C6179.5 (4)O7—C26—C27—C22−178.6 (4)
C9—C10—C11—C6−0.2 (7)C25—C26—C27—C22−0.5 (7)
O3—C10—C11—C120.1 (7)O7—C26—C27—C281.7 (7)
C9—C10—C11—C12−179.6 (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—C12−179.6 (4)C23—C22—C27—C28−179.2 (4)
C5—C6—C11—C12−1.4 (7)C21—C22—C27—C28−0.5 (7)
C10—C11—C12—O2−2.0 (7)C26—C27—C28—O61.1 (7)
C6—C11—C12—O2178.7 (4)C22—C27—C28—O6−178.6 (5)
C10—C11—C12—C13177.7 (4)C26—C27—C28—C29−179.5 (4)
C6—C11—C12—C13−1.7 (7)C22—C27—C28—C290.8 (7)
C3—C4—C13—C140.0 (7)C19—C20—C29—C301.1 (7)
C5—C4—C13—C14−176.7 (4)C21—C20—C29—C30−178.3 (4)
C3—C4—C13—C12−179.6 (4)C19—C20—C29—C28−179.3 (4)
C5—C4—C13—C123.6 (7)C21—C20—C29—C281.3 (7)
O2—C12—C13—C140.6 (7)O6—C28—C29—C30−2.1 (7)
C11—C12—C13—C14−179.1 (4)C27—C28—C29—C30178.4 (4)
O2—C12—C13—C4−179.7 (4)O6—C28—C29—C20178.3 (4)
C11—C12—C13—C40.6 (6)C27—C28—C29—C20−1.2 (7)
C4—C13—C14—C15−0.8 (7)C20—C29—C30—C31−1.3 (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—C14−178.3 (4)C17—C18—C31—C30178.6 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.802.538 (4)147
O7—H7···O60.841.812.551 (5)146

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2448).

References

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