Literature DB >> 21582815

3-Hydr-oxy-1,2-dimethoxy-anthraquinone.

Yong-Jun Xu1, Xiao-Xi Yang, Hong-Bin Zhao.   

Abstract

The title compound, C(16)H(12)O(5), was isolated from Morinda officinalis How. The anthraquinone ring system is almost planar, the dihedral angle between the two benzene rings being 1.12 (4)°. In the crystal structure, O-H⋯O and C-H⋯O hydrogen bonds link the mol-eculesin the crystallographic a-axis direction. Weak π-π stacking inter-actions [centroid-centroid distance between symmetry-related benzene rings of 3.699 (4) Å] are also present.

Entities:  

Year:  2009        PMID： 21582815      PMCID： PMC2969515          DOI： 10.1107/S1600536809021266

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological properties of anthraquinone derivatives, see: Kim et al. (2005 ▶) and of the title compound, see: Ali et al. (2000 ▶); Jia et al. (2007 ▶); Wu et al. (2003 ▶). For related structures, see: Ng et al. (2005 ▶); Boonnak et al. (2005 ▶). For the structure of another compound isolated from Morinda officinalis How., see: Liu & Jiao (2009 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H12O5 M = 284.26 Triclinic, a = 7.4087 (17) Å b = 8.0387 (18) Å c = 11.802 (3) Å α = 95.386 (3)° β = 92.357 (3)° γ = 115.712 (2)° V = 627.9 (3) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 293 K 0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.978 3200 measured reflections 2182 independent reflections 1639 reflections with I > 2σ(I) R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.136 S = 1.06 2182 reflections 210 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.25 e Å−3 Δρmin = −0.17 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021266/pk2164sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021266/pk2164Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H12O5Z = 2
Mr = 284.26F(000) = 296.0
Triclinic, P1Dx = 1.503 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4087 (17) ÅCell parameters from 1305 reflections
b = 8.0387 (18) Åθ = 3.1–27.3°
c = 11.802 (3) ŵ = 0.11 mm−1
α = 95.386 (3)°T = 293 K
β = 92.357 (3)°Block, yellow
γ = 115.712 (2)°0.30 × 0.20 × 0.20 mm
V = 627.9 (3) Å3
Bruker APEXII area-detector diffractometer2182 independent reflections
Radiation source: fine-focus sealed tube1639 reflections with I > 2σ(I)
graphiteRint = 0.013
φ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→8
Tmin = 0.967, Tmax = 0.978k = −9→9
3200 measured reflectionsl = −14→11
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0736P)2 + 0.1017P] where P = (Fo2 + 2Fc2)/3
2182 reflections(Δ/σ)max < 0.001
210 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
O10.2605 (2)0.79647 (18)0.14638 (13)0.0605 (4)
O20.2359 (2)0.18299 (17)−0.09353 (11)0.0560 (4)
O60.2197 (2)0.3418 (2)0.43860 (11)0.0597 (4)
O70.2427 (2)0.64028 (18)0.34133 (12)0.0547 (4)
O80.1946 (2)0.03307 (19)0.30888 (12)0.0582 (4)
C150.2626 (3)0.4756 (3)−0.21242 (16)0.0463 (5)
C160.2985 (3)0.7870 (3)−0.20248 (19)0.0550 (5)
C170.2839 (3)0.6275 (3)−0.26601 (19)0.0546 (5)
C180.2898 (3)0.7953 (3)−0.08620 (19)0.0474 (5)
C190.2686 (2)0.6434 (2)−0.03041 (15)0.0379 (4)
C200.2551 (2)0.4817 (2)−0.09503 (15)0.0372 (4)
C210.2574 (3)0.6545 (2)0.09545 (16)0.0403 (4)
C220.2422 (2)0.4946 (2)0.15295 (15)0.0368 (4)
C230.2284 (2)0.3315 (2)0.08725 (14)0.0350 (4)
C240.2378 (2)0.3203 (2)−0.03826 (15)0.0377 (4)
C250.2095 (3)0.1777 (2)0.13812 (16)0.0399 (4)
C260.2058 (3)0.1783 (2)0.25489 (15)0.0425 (4)
C270.2176 (3)0.3354 (3)0.32218 (15)0.0440 (5)
C280.2364 (3)0.4919 (2)0.27130 (15)0.0405 (4)
C290.0304 (4)0.2459 (4)0.4794 (2)0.0804 (8)
H29A−0.04390.31800.47540.097*
H29B0.04830.22640.55730.097*
H29C−0.04220.12780.43330.097*
C340.4369 (4)0.7632 (3)0.3940 (2)0.0703 (7)
H34A0.48620.69690.44030.084*
H34B0.42950.86360.44120.084*
H34C0.52660.81210.33630.084*
H10.249 (4)0.360 (4)−0.255 (2)0.105*
H40.298 (5)0.897 (4)−0.044 (3)0.105*
H30.323 (4)0.897 (4)−0.239 (2)0.105*
H20.292 (4)0.616 (4)−0.345 (3)0.105*
H50.198 (4)0.069 (4)0.089 (3)0.105*
H60.199 (5)−0.044 (4)0.253 (3)0.105*
U11U22U33U12U13U23
O10.0852 (11)0.0373 (7)0.0687 (9)0.0365 (7)0.0148 (8)−0.0003 (6)
O20.0889 (11)0.0383 (7)0.0479 (8)0.0358 (7)0.0051 (7)−0.0014 (6)
O60.0681 (10)0.0683 (10)0.0419 (8)0.0301 (8)0.0044 (7)0.0023 (7)
O70.0608 (9)0.0478 (8)0.0564 (8)0.0291 (7)0.0023 (7)−0.0142 (6)
O80.0884 (11)0.0506 (9)0.0507 (8)0.0423 (8)0.0151 (7)0.0147 (6)
C150.0462 (11)0.0455 (11)0.0489 (11)0.0220 (9)0.0019 (8)0.0054 (8)
C160.0524 (12)0.0451 (12)0.0689 (14)0.0202 (10)0.0041 (10)0.0208 (10)
C170.0569 (13)0.0551 (12)0.0534 (12)0.0247 (10)0.0048 (10)0.0143 (10)
C180.0420 (11)0.0346 (10)0.0673 (13)0.0183 (9)0.0037 (9)0.0076 (9)
C190.0293 (9)0.0313 (9)0.0540 (11)0.0144 (7)0.0026 (7)0.0046 (8)
C200.0295 (9)0.0320 (9)0.0501 (11)0.0140 (7)0.0020 (7)0.0032 (7)
C210.0349 (9)0.0291 (9)0.0575 (11)0.0161 (8)0.0050 (8)−0.0014 (8)
C220.0312 (9)0.0307 (9)0.0491 (11)0.0152 (7)0.0045 (7)0.0000 (7)
C230.0310 (9)0.0276 (9)0.0460 (10)0.0135 (7)0.0034 (7)−0.0005 (7)
C240.0347 (9)0.0289 (9)0.0480 (10)0.0140 (7)0.0012 (7)−0.0004 (7)
C250.0419 (10)0.0316 (9)0.0476 (11)0.0179 (8)0.0055 (8)0.0020 (7)
C260.0451 (11)0.0388 (10)0.0472 (11)0.0213 (9)0.0067 (8)0.0071 (8)
C270.0439 (11)0.0496 (11)0.0400 (10)0.0228 (9)0.0043 (8)0.0008 (8)
C280.0363 (10)0.0386 (10)0.0470 (10)0.0191 (8)0.0027 (7)−0.0060 (8)
C290.0866 (18)0.102 (2)0.0514 (13)0.0379 (16)0.0221 (12)0.0158 (13)
C340.0775 (16)0.0484 (12)0.0745 (15)0.0243 (12)−0.0103 (12)−0.0172 (11)
O1—C211.230 (2)C19—C211.488 (3)
O2—C241.222 (2)C20—C241.475 (2)
O6—C271.369 (2)C21—C221.473 (3)
O6—C291.407 (3)C22—C281.401 (3)
O7—C281.368 (2)C22—C231.421 (2)
O7—C341.418 (3)C23—C251.380 (3)
O8—C261.355 (2)C23—C241.482 (3)
O8—H60.88 (3)C25—C261.379 (3)
C15—C171.379 (3)C25—H50.97 (3)
C15—C201.386 (3)C26—C271.394 (3)
C15—H10.98 (3)C27—C281.400 (3)
C16—C181.373 (3)C29—H29A0.9600
C16—C171.382 (3)C29—H29B0.9600
C16—H30.97 (3)C29—H29C0.9600
C17—H20.94 (3)C34—H34A0.9600
C18—C191.394 (3)C34—H34B0.9600
C18—H40.90 (3)C34—H34C0.9600
C19—C201.405 (2)
C27—O6—C29114.93 (16)C22—C23—C24121.57 (16)
C28—O7—C34114.31 (15)O2—C24—C20120.49 (16)
C26—O8—H6102 (2)O2—C24—C23121.23 (16)
C17—C15—C20120.31 (19)C20—C24—C23118.26 (15)
C17—C15—H1122.3 (18)C26—C25—C23120.99 (16)
C20—C15—H1117.3 (18)C26—C25—H5121.2 (18)
C18—C16—C17120.59 (19)C23—C25—H5117.8 (18)
C18—C16—H3119.1 (17)O8—C26—C25123.02 (16)
C17—C16—H3120.2 (17)O8—C26—C27117.56 (16)
C15—C17—C16120.0 (2)C25—C26—C27119.41 (17)
C15—C17—H2116.1 (19)O6—C27—C26120.69 (17)
C16—C17—H2123.9 (19)O6—C27—C28119.27 (16)
C16—C18—C19120.33 (19)C26—C27—C28119.98 (17)
C16—C18—H4122 (2)O7—C28—C27117.34 (16)
C19—C18—H4118 (2)O7—C28—C22121.20 (17)
C18—C19—C20119.00 (18)C27—C28—C22121.44 (15)
C18—C19—C21119.49 (16)O6—C29—H29A109.5
C20—C19—C21121.50 (16)O6—C29—H29B109.5
C15—C20—C19119.80 (16)H29A—C29—H29B109.5
C15—C20—C24119.84 (16)O6—C29—H29C109.5
C19—C20—C24120.34 (16)H29A—C29—H29C109.5
O1—C21—C22123.18 (18)H29B—C29—H29C109.5
O1—C21—C19118.37 (17)O7—C34—H34A109.5
C22—C21—C19118.45 (14)O7—C34—H34B109.5
C28—C22—C23116.89 (16)H34A—C34—H34B109.5
C28—C22—C21123.33 (15)O7—C34—H34C109.5
C23—C22—C21119.77 (16)H34A—C34—H34C109.5
C25—C23—C22121.27 (17)H34B—C34—H34C109.5
C25—C23—C24117.15 (15)
C20—C15—C17—C160.1 (3)C19—C20—C24—C232.0 (2)
C18—C16—C17—C15−0.6 (3)C25—C23—C24—O2−2.5 (3)
C17—C16—C18—C190.7 (3)C22—C23—C24—O2176.29 (16)
C16—C18—C19—C20−0.4 (3)C25—C23—C24—C20179.16 (14)
C16—C18—C19—C21−179.35 (16)C22—C23—C24—C20−2.1 (2)
C17—C15—C20—C190.2 (3)C22—C23—C25—C26−0.8 (3)
C17—C15—C20—C24−178.33 (16)C24—C23—C25—C26178.01 (15)
C18—C19—C20—C15−0.1 (3)C23—C25—C26—O8−177.61 (16)
C21—C19—C20—C15178.84 (15)C23—C25—C26—C271.2 (3)
C18—C19—C20—C24178.43 (15)C29—O6—C27—C26−78.9 (2)
C21—C19—C20—C24−2.6 (2)C29—O6—C27—C28103.9 (2)
C18—C19—C21—O12.4 (3)O8—C26—C27—O60.7 (3)
C20—C19—C21—O1−176.58 (15)C25—C26—C27—O6−178.22 (16)
C18—C19—C21—C22−177.85 (15)O8—C26—C27—C28177.81 (16)
C20—C19—C21—C223.2 (2)C25—C26—C27—C28−1.1 (3)
O1—C21—C22—C28−2.1 (3)C34—O7—C28—C2785.1 (2)
C19—C21—C22—C28178.18 (15)C34—O7—C28—C22−96.8 (2)
O1—C21—C22—C23176.54 (16)O6—C27—C28—O7−4.2 (3)
C19—C21—C22—C23−3.2 (2)C26—C27—C28—O7178.56 (15)
C28—C22—C23—C250.2 (3)O6—C27—C28—C22177.70 (15)
C21—C22—C23—C25−178.54 (15)C26—C27—C28—C220.5 (3)
C28—C22—C23—C24−178.54 (14)C23—C22—C28—O7−178.03 (14)
C21—C22—C23—C242.8 (2)C21—C22—C28—O70.6 (3)
C15—C20—C24—O22.2 (3)C23—C22—C28—C270.0 (3)
C19—C20—C24—O2−176.41 (16)C21—C22—C28—C27178.61 (15)
C15—C20—C24—C23−179.46 (15)
D—H···AD—HH···AD···AD—H···A
C25—H5···O1i0.97 (3)2.57 (3)3.256 (2)128 (2)
O8—H6···O1i0.88 (3)1.91 (3)2.781 (2)168 (3)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C25—H5⋯O1i0.97 (3)2.57 (3)3.256 (2)128 (2)
O8—H6⋯O1i0.88 (3)1.91 (3)2.781 (2)168 (3)

Symmetry code: (i) .

  5 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  In-vitro and in-vivo anti-inflammatory and antinociceptive effects of the methanol extract of the roots of Morinda officinalis.

Authors:  In-Tae Kim; Hee-Juhn Park; Jung-Hwan Nam; Young-Mi Park; Jong-Heon Won; Jongwon Choi; Bong-Keun Choe; Kyung-Tae Lee
Journal:  J Pharm Pharmacol       Date:  2005-05       Impact factor: 3.765

3.  Antiviral, cyototoxic and antimicrobial activities of anthraquinones isolated from the roots of morinda elliptica.

Authors:  A M Ali; N H Ismail; M M Mackeen; L S Yazan; S M Mohamed; A S Ho; N H Lajis
Journal:  Pharm Biol       Date:  2000       Impact factor: 3.503

4.  2-Hydr-oxy-1-methoxy-anthraquinone monohydrate.

Authors:  Zhi-Meng Liu; Yuan-Qi Jiao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-06

5.  Cytotoxic anthraquinones from the stems of Rubia wallichiana Decne.

Authors:  Tian-Shung Wu; Dau-Min Lin; Li-Shian Shi; Amooru Gangaiah Damu; Ping-Chung Kuo; Yao-Hau Kuo
Journal:  Chem Pharm Bull (Tokyo)       Date:  2003-08       Impact factor: 1.645
  5 in total
  1 in total

1.  2-Hydr-oxy-1-methoxy-anthraquinone monohydrate.

Authors:  Zhi-Meng Liu; Yuan-Qi Jiao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-06
  1 in total

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