Skip to main content
PMC home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 May 29;65(Pt 6):o1433–o1434. doi: 10.1107/S1600536809017607

1,3-Dihydr­oxy-2-methoxy­methyl-9,10-anthraquinone from Rennellia elliptica Korth.

Nor Hadiani Ismail a, Che Puteh Osman a, Rohaya Ahmad a, Khalijah Awang b, Seik Weng Ng b,*
PMCID: PMC2969543  PMID: 21583274

Abstract

The title compound, C16H12O5, common name: lucidin ω-methyl ether, exists as a planar mol­ecule (r.m.s. deviation = 0.04 Å). Within the mol­ecule, the 1-hydr­oxy group forms a hydrogen bond to the adjacent carbonyl O atom, and the 3-hydr­oxy group forms a hydrogen bond to the adjacent meth­oxy O atom. The meth­oxy O atom is disordered over two positions of equal occupancy.

Related literature

The title compound has been isolated from several plants: Rubia tinctorum L. (Boldizsar et al., 2004 ▶), taurina subsp. caucasica (Ozgen et al., 2006 ▶), Prismatomeris fragrans (Kanokmedhakul et al., 2005 ▶), Crucianella maritima L. (El-Lakany et al., 2004 ▶), Rubia wallichiana Decne (Wu et al., 2003 ▶), Morinda elliptica (Ali et al., 2000 ▶; Ismail et al., 1997 ▶; Ismail et al., 2002 ▶), Ophiorrhiza pumila (Kitajima et al., 1998 ▶), Morinda officinalis How. (Yoshikawa et al., 1995 ▶), Galiumspurium var. echinospermon (Koyama et al., 1993 ▶), Damnacanthus indicus (Koyama et al., 1992 ▶), Rubia cordifolia L. (Vidal-Tessier et al., 1987 ▶), Faramea cyanea (Ferrari et al., 1985 ▶), Morinda parvifolia (Chang & Lee, 1984 ▶) and Galium album (Kupier & Labadie, 1984 ▶).graphic file with name e-65-o1433-scheme1.jpg

Experimental

Crystal data

  • C16H12O5

  • M r = 284.26

  • Monoclinic, Inline graphic

  • a = 4.6725 (1) Å

  • b = 39.685 (1) Å

  • c = 6.9869 (2) Å

  • β = 107.654 (2)°

  • V = 1234.55 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 100 K

  • 0.30 × 0.07 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 10046 measured reflections

  • 2825 independent reflections

  • 1888 reflections with I > 2σ(I)

  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054

  • wR(F 2) = 0.156

  • S = 1.01

  • 2825 reflections

  • 201 parameters

  • 4 restraints

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

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.46 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017607/tk2447sup1.cif

e-65-o1433-sup1.cif (18.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017607/tk2447Isup2.hkl

e-65-o1433-Isup2.hkl (138.7KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1o⋯O2 0.85 (1) 1.79 (2) 2.557 (2) 150 (3)
O4—H4o⋯O5 0.84 (1) 1.77 (2) 2.546 (7) 152 (4)
O4—H4o⋯O5′ 0.84 (1) 1.77 (2) 2.539 (7) 152 (4)
Open in a new tab

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 and dichloromethane–methanol in increasing polarity. The fraction eluted with hexane–dichloromethane (2:8 v/v) was purified by thin layer chromatography (2 mm). The product was recrystallized from dichloromethane to furnish yellow crystals. The formulation was established by 1H- and 13C-NMR spectroscopy.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 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 located in a difference Fourier map, and were refined with a distance restraint of O–H 0.84±0.01 Å; their temperature factors were refined.

The methoxy oxygen atom is disordered over two positions, but the occupancy could not be refined. The disorder was assumed to be 50:50. The C–O/C–O' bonds to the aryl group were restrained to within 0.01 Å of each other, as were those to the alkyl group. The anisotropic displacement factors of the primed atom were restrained to those of the umprimed one.

Figures

Fig. 1.

Fig. 1.

Open in a new tab

Thermal ellipsoid plot (Barbour, 2001) of the molecule of C16H12O5 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown

Crystal data

C16H12O5 F(000) = 592
Mr = 284.26 Dx = 1.529 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 1810 reflections
a = 4.6725 (1) Å θ = 3.1–27.9°
b = 39.685 (1) Å µ = 0.12 mm−1
c = 6.9869 (2) Å T = 100 K
β = 107.654 (2)° Plate, yellow
V = 1234.55 (6) Å3 0.30 × 0.07 × 0.02 mm
Z = 4
Open in a new tab

Data collection

Bruker SMART APEX diffractometer 1888 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.041
graphite θmax = 27.5°, θmin = 1.0°
ω scans h = −5→6
10046 measured reflections k = −51→51
2825 independent reflections l = −9→8
Open in a new tab

Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156 H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0691P)2 + 1.3159P] where P = (Fo2 + 2Fc2)/3
2825 reflections (Δ/σ)max = 0.001
201 parameters Δρmax = 0.43 e Å−3
4 restraints Δρmin = −0.46 e Å−3
Open in a new tab

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

x y z Uiso*/Ueq Occ. (<1)
O1 0.5327 (4) 0.35893 (4) 0.3196 (2) 0.0173 (4)
H1o 0.476 (7) 0.3392 (4) 0.338 (5) 0.039 (9)*
O2 0.2892 (4) 0.31121 (4) 0.4610 (3) 0.0200 (4)
O3 0.0049 (4) 0.39767 (4) 0.9709 (2) 0.0189 (4)
O4 0.5244 (4) 0.46858 (4) 0.5956 (3) 0.0202 (4)
H4o 0.601 (8) 0.4724 (9) 0.503 (4) 0.051 (11)*
O5 0.777 (3) 0.45857 (15) 0.3246 (15) 0.027 (2) 0.50
O5' 0.694 (3) 0.46028 (15) 0.2862 (15) 0.027 (2) 0.50
C1 0.4569 (5) 0.43535 (6) 0.5813 (3) 0.0144 (5)
C2 0.3075 (5) 0.42345 (6) 0.7145 (3) 0.0137 (5)
H2 0.2585 0.4386 0.8052 0.016*
C3 0.2318 (5) 0.38992 (6) 0.7142 (3) 0.0129 (5)
C4 0.0737 (5) 0.37804 (6) 0.8575 (3) 0.0135 (5)
C5 0.0051 (5) 0.34142 (6) 0.8590 (3) 0.0139 (5)
C6 −0.1291 (5) 0.32923 (6) 0.9985 (4) 0.0183 (5)
H6 −0.1774 0.3443 1.0900 0.022*
C7 −0.1917 (6) 0.29523 (6) 1.0034 (4) 0.0217 (5)
H7 −0.2798 0.2869 1.1001 0.026*
C8 −0.1268 (6) 0.27307 (6) 0.8677 (4) 0.0229 (6)
H8 −0.1728 0.2498 0.8707 0.028*
C9 0.0054 (6) 0.28509 (6) 0.7283 (4) 0.0203 (5)
H9 0.0490 0.2700 0.6352 0.024*
C10 0.0745 (5) 0.31922 (6) 0.7240 (3) 0.0146 (5)
C11 0.2280 (5) 0.33153 (6) 0.5794 (3) 0.0141 (5)
C12 0.3044 (5) 0.36698 (6) 0.5816 (3) 0.0132 (5)
C13 0.4545 (5) 0.37961 (6) 0.4486 (3) 0.0129 (5)
C14 0.5296 (5) 0.41375 (6) 0.4458 (3) 0.0131 (5)
C15 0.6804 (5) 0.42442 (6) 0.2919 (3) 0.0153 (5)
H15A 0.8555 0.4097 0.3022 0.018* 0.50
H15B 0.5378 0.4220 0.1551 0.018* 0.50
H15C 0.8858 0.4149 0.3277 0.018* 0.50
H15D 0.5654 0.4157 0.1578 0.018* 0.50
C16 0.8677 (6) 0.47240 (6) 0.1631 (4) 0.0221 (6)
H16A 0.9308 0.4958 0.1938 0.033* 0.50
H16B 0.6989 0.4716 0.0390 0.033* 0.50
H16C 1.0357 0.4592 0.1459 0.033* 0.50
H16D 0.9262 0.4958 0.1984 0.033* 0.50
H16E 0.7474 0.4711 0.0215 0.033* 0.50
H16F 1.0482 0.4585 0.1853 0.033* 0.50
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0221 (9) 0.0145 (9) 0.0194 (9) −0.0005 (7) 0.0124 (7) −0.0022 (7)
O2 0.0264 (9) 0.0162 (8) 0.0209 (9) −0.0008 (7) 0.0122 (8) −0.0020 (7)
O3 0.0220 (9) 0.0190 (9) 0.0184 (9) 0.0000 (7) 0.0102 (7) −0.0021 (7)
O4 0.0303 (10) 0.0136 (8) 0.0205 (9) −0.0041 (7) 0.0134 (8) −0.0010 (7)
O5 0.036 (6) 0.0142 (10) 0.043 (3) 0.0027 (18) 0.033 (4) 0.0050 (14)
O5' 0.036 (6) 0.0142 (10) 0.043 (3) 0.0027 (18) 0.033 (4) 0.0050 (14)
C1 0.0138 (11) 0.0130 (11) 0.0156 (11) −0.0001 (9) 0.0032 (9) 0.0012 (8)
C2 0.0135 (11) 0.0143 (11) 0.0138 (11) 0.0003 (8) 0.0050 (9) −0.0016 (8)
C3 0.0099 (11) 0.0171 (12) 0.0121 (11) 0.0005 (9) 0.0038 (9) 0.0006 (8)
C4 0.0122 (11) 0.0151 (11) 0.0131 (11) 0.0003 (9) 0.0040 (9) 0.0008 (9)
C5 0.0103 (11) 0.0164 (11) 0.0147 (11) −0.0009 (8) 0.0032 (9) 0.0023 (9)
C6 0.0180 (12) 0.0196 (12) 0.0189 (12) 0.0006 (10) 0.0082 (10) 0.0024 (9)
C7 0.0217 (13) 0.0231 (13) 0.0230 (13) −0.0038 (10) 0.0110 (10) 0.0064 (10)
C8 0.0245 (13) 0.0147 (12) 0.0308 (14) −0.0030 (10) 0.0102 (11) 0.0037 (10)
C9 0.0217 (13) 0.0151 (12) 0.0248 (13) −0.0005 (9) 0.0083 (11) −0.0011 (10)
C10 0.0135 (11) 0.0144 (11) 0.0154 (12) 0.0015 (9) 0.0038 (9) 0.0023 (9)
C11 0.0116 (11) 0.0166 (11) 0.0137 (11) 0.0035 (9) 0.0031 (9) 0.0007 (9)
C12 0.0128 (11) 0.0136 (11) 0.0124 (11) 0.0008 (8) 0.0027 (9) 0.0002 (8)
C13 0.0098 (11) 0.0163 (11) 0.0114 (11) 0.0022 (8) 0.0015 (8) −0.0008 (8)
C14 0.0104 (11) 0.0147 (11) 0.0143 (11) 0.0003 (8) 0.0036 (9) 0.0025 (9)
C15 0.0168 (12) 0.0146 (11) 0.0157 (11) −0.0002 (9) 0.0068 (9) 0.0001 (9)
C16 0.0273 (14) 0.0184 (12) 0.0257 (14) −0.0043 (10) 0.0156 (11) 0.0049 (10)
Open in a new tab

Geometric parameters (Å, °)

O1—C13 1.349 (3) C7—C8 1.392 (4)
O1—H1o 0.848 (10) C7—H7 0.9500
O2—C11 1.249 (3) C8—C9 1.387 (3)
O3—C4 1.222 (3) C8—H8 0.9500
O4—C1 1.353 (3) C9—C10 1.395 (3)
O4—H4o 0.842 (10) C9—H9 0.9500
O5—C15 1.425 (6) C10—C11 1.488 (3)
O5—C16 1.431 (6) C11—C12 1.450 (3)
O5'—C15 1.426 (6) C12—C13 1.415 (3)
O5'—C16 1.432 (6) C13—C14 1.401 (3)
C1—C14 1.393 (3) C14—C15 1.514 (3)
C1—C2 1.404 (3) C15—H15A 0.9900
C2—C3 1.377 (3) C15—H15B 0.9900
C2—H2 0.9500 C15—H15C 0.9900
C3—C12 1.412 (3) C15—H15D 0.9900
C3—C4 1.490 (3) C16—H16A 0.9800
C4—C5 1.489 (3) C16—H16B 0.9800
C5—C6 1.396 (3) C16—H16C 0.9800
C5—C10 1.399 (3) C16—H16D 0.9800
C6—C7 1.383 (3) C16—H16E 0.9800
C6—H6 0.9500 C16—H16F 0.9800
C13—O1—H1o 107 (2) C3—C12—C13 117.9 (2)
C1—O4—H4o 105 (2) C3—C12—C11 121.7 (2)
C15—O5—C16 113.1 (5) C13—C12—C11 120.4 (2)
C15—O5'—C16 113.0 (5) O1—C13—C14 117.32 (19)
O4—C1—C14 123.4 (2) O1—C13—C12 120.8 (2)
O4—C1—C2 115.5 (2) C14—C13—C12 121.9 (2)
C14—C1—C2 121.1 (2) C1—C14—C13 118.1 (2)
C3—C2—C1 120.2 (2) C1—C14—C15 124.9 (2)
C3—C2—H2 119.9 C13—C14—C15 116.92 (19)
C1—C2—H2 119.9 O5—C15—C14 110.1 (3)
C2—C3—C12 120.8 (2) O5'—C15—C14 109.5 (3)
C2—C3—C4 119.0 (2) O5—C15—H15A 109.6
C12—C3—C4 120.3 (2) O5'—C15—H15A 123.2
O3—C4—C5 121.2 (2) C14—C15—H15A 109.6
O3—C4—C3 121.1 (2) O5—C15—H15B 109.6
C5—C4—C3 117.73 (19) C14—C15—H15B 109.6
C6—C5—C10 119.8 (2) H15A—C15—H15B 108.2
C6—C5—C4 119.1 (2) O5'—C15—H15C 109.8
C10—C5—C4 121.0 (2) C14—C15—H15C 109.8
C7—C6—C5 119.9 (2) O5'—C15—H15D 109.8
C7—C6—H6 120.0 C14—C15—H15D 109.8
C5—C6—H6 120.0 H15C—C15—H15D 108.2
C6—C7—C8 120.5 (2) O5—C16—H16A 109.5
C6—C7—H7 119.7 O5—C16—H16B 109.5
C8—C7—H7 119.7 H16A—C16—H16B 109.5
C9—C8—C7 119.8 (2) O5—C16—H16C 109.5
C9—C8—H8 120.1 H16A—C16—H16C 109.5
C7—C8—H8 120.1 H16B—C16—H16C 109.5
C8—C9—C10 120.3 (2) O5—C16—H16D 107.0
C8—C9—H9 119.9 O5'—C16—H16D 109.5
C10—C9—H9 119.9 H16B—C16—H16D 110.0
C9—C10—C5 119.7 (2) H16C—C16—H16D 111.3
C9—C10—C11 119.7 (2) O5'—C16—H16E 109.5
C5—C10—C11 120.6 (2) H16D—C16—H16E 109.5
O2—C11—C12 121.9 (2) O5'—C16—H16F 109.5
O2—C11—C10 119.5 (2) H16D—C16—H16F 109.5
C12—C11—C10 118.62 (19) H16E—C16—H16F 109.5
O4—C1—C2—C3 −179.2 (2) C2—C3—C12—C11 179.7 (2)
C14—C1—C2—C3 0.5 (3) C4—C3—C12—C11 0.2 (3)
C1—C2—C3—C12 0.4 (3) O2—C11—C12—C3 179.3 (2)
C1—C2—C3—C4 179.9 (2) C10—C11—C12—C3 −1.2 (3)
C2—C3—C4—O3 1.7 (3) O2—C11—C12—C13 −0.5 (3)
C12—C3—C4—O3 −178.8 (2) C10—C11—C12—C13 179.0 (2)
C2—C3—C4—C5 −177.7 (2) C3—C12—C13—O1 179.4 (2)
C12—C3—C4—C5 1.8 (3) C11—C12—C13—O1 −0.9 (3)
O3—C4—C5—C6 −2.7 (3) C3—C12—C13—C14 −0.3 (3)
C3—C4—C5—C6 176.8 (2) C11—C12—C13—C14 179.5 (2)
O3—C4—C5—C10 177.7 (2) O4—C1—C14—C13 178.4 (2)
C3—C4—C5—C10 −2.9 (3) C2—C1—C14—C13 −1.2 (3)
C10—C5—C6—C7 0.3 (3) O4—C1—C14—C15 −2.6 (4)
C4—C5—C6—C7 −179.4 (2) C2—C1—C14—C15 177.8 (2)
C5—C6—C7—C8 −1.1 (4) O1—C13—C14—C1 −178.5 (2)
C6—C7—C8—C9 0.8 (4) C12—C13—C14—C1 1.1 (3)
C7—C8—C9—C10 0.3 (4) O1—C13—C14—C15 2.4 (3)
C8—C9—C10—C5 −1.1 (4) C12—C13—C14—C15 −178.0 (2)
C8—C9—C10—C11 177.4 (2) C16—O5—C15—O5' −77.9 (18)
C6—C5—C10—C9 0.8 (3) C16—O5—C15—C14 −168.5 (6)
C4—C5—C10—C9 −179.5 (2) C16—O5'—C15—O5 77.2 (17)
C6—C5—C10—C11 −177.7 (2) C16—O5'—C15—C14 172.5 (6)
C4—C5—C10—C11 2.0 (3) C1—C14—C15—O5 8.4 (6)
C9—C10—C11—O2 1.1 (3) C13—C14—C15—O5 −172.6 (6)
C5—C10—C11—O2 179.6 (2) C1—C14—C15—O5' −8.8 (6)
C9—C10—C11—C12 −178.4 (2) C13—C14—C15—O5' 170.2 (6)
C5—C10—C11—C12 0.1 (3) C15—O5—C16—O5' 77.8 (18)
C2—C3—C12—C13 −0.5 (3) C15—O5'—C16—O5 −77.3 (17)
C4—C3—C12—C13 179.98 (19)
Open in a new tab

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O1—H1o···O2 0.85 (1) 1.79 (2) 2.557 (2) 150 (3)
O4—H4o···O5 0.84 (1) 1.77 (2) 2.546 (7) 152 (4)
O4—H4o···O5' 0.84 (1) 1.77 (2) 2.539 (7) 152 (4)
Open in a new tab

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2447).

References

  1. Ali, A. M., Ismail, N. H., Mackeen, M. M., Yazan, L. S., Mohamed, S. M., Ho, A. S. H. & Lajis, N. H. (2000). Pharm. Biol.38, 298–301. [DOI] [PubMed]
  2. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  3. Boldizsar, I., Laszlo-Bencsik, A., Szucs, Z. & Danos, B. (2004). Acta Pharm. Hung.74, 142–148. [PubMed]
  4. Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  5. Chang, P. & Lee, K. S. (1984). Phytochemistry, 23, 1733–1736.
  6. 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.
  7. Ferrari, F., Delle Monache, G. & Alves de Lima, R. (1985). Phytochemistry, 24, 2753–2755.
  8. Ismail, N. H., Ali, A. M., Aimi, N., Kitajima, M., Takayama, H. & Lajis, N. H. (1997). Phytochemistry, 45, 1723–1725.
  9. Ismail, N. H., Mohamad, H., Mohidin, A. & Lajis, N. H. (2002). Nat. Prod. Sci.8, 48–51.
  10. Kanokmedhakul, K., Kanokmedhakul, S. & Phatchana, R. (2005). J. Ethnopharmacol.100, 284–288. [DOI] [PubMed]
  11. Kitajima, M., Fischer, U., Nakamura, M., Ohsawa, M., Ueno, M., Takayama, H. & Unger, M. (1998). Phytochemistry, 48, 107–111.
  12. Koyama, J., Ogura, T. & Tagahara, K. (1993). Phytochemistry, 33, 1540–1542.
  13. Koyama, J., Okatani, T., Tagahara, K., Kouno, I. & Irie, H. (1992). Phytochemistry, 31, 709–710.
  14. Kupier, J. & Labadie, R. P. (1984). Planta Med.42, 390–399. [DOI] [PubMed]
  15. Ozgen, U., Kazaz, C., Secen, H. & Coskun, M. (2006). Turk. J. Chem.30, 15–20.
  16. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  17. Vidal-Tessier, A. M., Delaveau, P. & Champion, B. (1987). Ann. Pharm. Fr.45, 261–267. [PubMed]
  18. Westrip, S. P. (2009). publCIF In preparation.
  19. Wu, T.-S., Lin, D.-M., Shi, L.-S., Damu, A. G., Kuo, P.-C. & Kuo, Y.-H. (2003). Chem. Pharm. Bull.51, 948–950. [DOI] [PubMed]
  20. Yoshikawa, M., Yamaguchi, S., Nishisaka, H., Yamahara, J. & Murakami, N. (1995). Chem. Pharm. Bull.43, 1462–1465. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017607/tk2447sup1.cif

e-65-o1433-sup1.cif (18.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017607/tk2447Isup2.hkl

e-65-o1433-Isup2.hkl (138.7KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES