2-Meth­oxy­naphthalene-1,4-dione

Jin, B.; Song, Z.-C.; Jiang, F.-S.; Liu, W.-H.; Ding, Z.-S.

doi:10.1107/S1600536811009883

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o947

doi:10.1107/S1600536811009883

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2-Methoxynaphthalene-1,4-dione

Bo Jin,^a Zhong-Cheng Song,^b Fu-Sheng Jiang,^a Wen-Hong Liu ^b and Zhi-Shan Ding ^a ^*

^aDepartment of Life Science, Zhejiang Traditional Chinese Medicine University, Hangzhou 310053, People's Republic of China, and ^bBioengineering Department, Zhejiang Traditional Chinese Medicine University, Hangzhou 310053, People's Republic of China
^*Correspondence e-mail: zjtcmbio@163.com

(Received 7 March 2011; accepted 16 March 2011; online 23 March 2011)

The title compound, C₁₁H₈O₃, was isolated from Impatiens balsamina plants (balsam, LIB) grown in our laboratory. The two six-membered rings of the naphthalene-1,4-dione unit are coplanar [maximum deviation = 0.009 (1) Å]. The O and C atoms of the methoxy substituent also lie close to the naphthalene plane, with deviations of 0.0090 (2) and 0.047 (2) Å, respectively.

Related literature

For background to compounds extracted from Impatiens balsamina, see: Ding et al. (2008 ). For the antimicrobial activity of flavonol and naphthoquinone derivatives, see: Yang et al. (2001 ). For their anti-anaphylaxis properties, see: Yoshimi et al. (2003 ); Ishiguro et al. (1994 ) and for their use as anti-inflammatories, see: Hisae & Kyoko (2002 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₈O₃
M_r = 188.17
Monoclinic, P 2₁ /c
a = 3.904 (3) Å
b = 7.662 (6) Å
c = 28.81 (2) Å
β = 93.562 (7)°
V = 860.1 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 . T_min = 0.979, T_max = 0.989
7068 measured reflections
2082 independent reflections
1458 reflections with I > 2σ(I)
R_int = 0.032
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.136
S = 1.08
2082 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009883/sj5115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009883/sj5115Isup2.hkl

checkCIF report

Comment top

Modern chemical and pharmacological studies have identified flavonol and naphthoquinone derivatives, some of which have strong antimicrobial (Yang et al., 2001) anti-anaphylaxis (Yoshimi et al., 2003, Ishiguro et al., 1994) and anti-inflammatory properties (Hisae & Kyoko, 2002). We have purified and identified an active component of the Impatiens balsamina plant (balsam, LIB) which was grown in our laboratory (Ding et al., 2008) and authenticated by Professor Yao Zhensheng (Zhejiang Traditional Chinese Medicinal University). The molecular structure of the title compound is shown in Fig. 1. In the crystal, all bond lengths are within normal ranges (Allen et al., 1987). The C1···C4,C9,C10 and C5···C10 rings of the naphthalene-1,4-dione unit are co-planar, maximum deviation 0.009 (1) Å. The O2 and C11 atoms of the methoxy substituent also lie close to the naphthalene plane with deviations of 0.0090 (2) Å and 0.047 (2) Å respectively.

Related literature top

For background to compounds extracted from Impatiens balsamina, see: Ding et al. (2008). For the antimicrobial activity of flavonol and naphthoquinone derivatives, see: Yang et al. (2001). For their anti-anaphylaxis properties, see: Yoshimi et al. (2003); Ishiguro et al. (1994) and for their use as anti-inflammatories, see: Hisae & Kyoko (2002). For standard bond-length data, see: Allen et al. (1987).

Experimental top

Dried leaves (200 g) of Impatiens balsamina were crushed, soaked with 55% alcohol (1500 ml) for 24 h and then reflux extracted for 40 min (1500 ml\3). Extracts were filtered and vacuum evaporated. In addition, 200 g of dried leaves were directly reflux extracted using chloroform (3000 ml\2). Next these extracts were filtered, combined, vacuum evaporated and the residue dried for further use. A portion of residue was re-chromatographed on silica gel using a petroleum ether-acetone (8:2) system and the isolated product was recrystallized from chloroform to yield the active component as light yellow crystals.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compounds with atom labels and 50% probability displacement ellipsoids for non-hydrogen atoms.

2-Methoxynaphthalene-1,4-dione top

Crystal data top

C₁₁H₈O₃	F(000) = 392
M_r = 188.17	D_x = 1.453 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 1421 reflections
a = 3.904 (3) Å	θ = 3.0–26.7°
b = 7.662 (6) Å	µ = 0.11 mm⁻¹
c = 28.81 (2) Å	T = 296 K
β = 93.562 (7)°	Block, yellow
V = 860.1 (12) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enrfa–Nonius CAD-4 diffractometer	1458 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 28.3°, θ_min = 2.8°
ω/2θ scans	h = −5→5
Absorption correction: ψ scan (North et al., 1968.	k = −10→10
T_min = 0.979, T_max = 0.989	l = −38→36
7068 measured reflections	3 standard reflections every 200 reflections
2082 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0386P)² + 0.5448P] where P = (F_o² + 2F_c²)/3
2082 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₁H₈O₃	V = 860.1 (12) Å³
M_r = 188.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.904 (3) Å	µ = 0.11 mm⁻¹
b = 7.662 (6) Å	T = 296 K
c = 28.81 (2) Å	0.20 × 0.20 × 0.10 mm
β = 93.562 (7)°

Data collection top

Enrfa–Nonius CAD-4 diffractometer	1458 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968.	R_int = 0.032
T_min = 0.979, T_max = 0.989	3 standard reflections every 200 reflections
7068 measured reflections	intensity decay: 1%
2082 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.08	Δρ_max = 0.19 e Å⁻³
2082 reflections	Δρ_min = −0.25 e Å⁻³
128 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O2	0.5248 (4)	1.29754 (19)	0.09145 (5)	0.0460 (4)
C10	0.8859 (5)	0.7924 (3)	0.12534 (7)	0.0351 (5)
C1	0.6106 (5)	1.0740 (3)	0.14687 (7)	0.0389 (5)
C9	0.7444 (5)	0.8979 (3)	0.15900 (7)	0.0347 (4)
C2	0.6487 (5)	1.1357 (3)	0.09790 (7)	0.0369 (5)
O3	1.0374 (5)	0.7687 (2)	0.04711 (5)	0.0549 (5)
C5	1.0035 (6)	0.6270 (3)	0.13751 (8)	0.0423 (5)
H5	1.0976	0.5566	0.1153	0.051*
O1	0.4735 (5)	1.1666 (2)	0.17443 (6)	0.0636 (5)
C3	0.7874 (5)	1.0345 (3)	0.06610 (7)	0.0393 (5)
H3	0.8047	1.0774	0.0361	0.047*
C6	0.9824 (6)	0.5657 (3)	0.18238 (8)	0.0483 (6)
H6	1.0607	0.4542	0.1902	0.058*
C4	0.9122 (5)	0.8589 (3)	0.07713 (7)	0.0384 (5)
C7	0.8444 (6)	0.6705 (3)	0.21567 (8)	0.0482 (6)
H7	0.8321	0.6295	0.2459	0.058*
C8	0.7251 (6)	0.8354 (3)	0.20418 (7)	0.0426 (5)
H8	0.6317	0.9049	0.2266	0.051*
C11	0.5484 (6)	1.3721 (3)	0.04595 (8)	0.0508 (6)
H11A	0.7849	1.3784	0.0388	0.076*
H11B	0.4516	1.4874	0.0454	0.076*
H11C	0.4243	1.3005	0.0233	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0583 (10)	0.0385 (8)	0.0422 (8)	0.0075 (7)	0.0122 (7)	−0.0003 (7)
C10	0.0342 (11)	0.0366 (11)	0.0347 (10)	−0.0011 (8)	0.0035 (8)	−0.0051 (8)
C1	0.0426 (12)	0.0375 (11)	0.0379 (11)	−0.0023 (9)	0.0124 (9)	−0.0080 (9)
C9	0.0341 (10)	0.0352 (10)	0.0354 (10)	−0.0059 (8)	0.0057 (8)	−0.0060 (8)
C2	0.0383 (11)	0.0331 (11)	0.0395 (11)	−0.0010 (8)	0.0053 (9)	−0.0030 (8)
O3	0.0747 (12)	0.0500 (10)	0.0418 (9)	0.0127 (9)	0.0185 (8)	−0.0096 (7)
C5	0.0440 (12)	0.0378 (11)	0.0453 (12)	0.0035 (9)	0.0037 (9)	−0.0076 (9)
O1	0.0953 (14)	0.0488 (10)	0.0502 (10)	0.0166 (9)	0.0325 (9)	−0.0034 (8)
C3	0.0444 (12)	0.0416 (11)	0.0324 (10)	0.0007 (9)	0.0070 (9)	−0.0023 (9)
C6	0.0534 (14)	0.0383 (12)	0.0528 (14)	0.0013 (10)	−0.0003 (11)	0.0024 (10)
C4	0.0372 (11)	0.0406 (12)	0.0379 (11)	−0.0007 (9)	0.0076 (9)	−0.0091 (9)
C7	0.0553 (14)	0.0495 (13)	0.0400 (12)	−0.0014 (11)	0.0037 (10)	0.0053 (10)
C8	0.0473 (13)	0.0440 (12)	0.0375 (11)	−0.0036 (10)	0.0102 (9)	−0.0049 (9)
C11	0.0607 (15)	0.0482 (13)	0.0442 (13)	0.0094 (11)	0.0090 (11)	0.0078 (10)

Geometric parameters (Å, º) top

O2—C2	1.340 (3)	C5—H5	0.9300
O2—C11	1.438 (3)	C3—C4	1.459 (3)
C10—C5	1.386 (3)	C3—H3	0.9300
C10—C9	1.402 (3)	C6—C7	1.385 (3)
C10—C4	1.489 (3)	C6—H6	0.9300
C1—O1	1.213 (2)	C7—C8	1.380 (3)
C1—C9	1.481 (3)	C7—H7	0.9300
C1—C2	1.504 (3)	C8—H8	0.9300
C9—C8	1.394 (3)	C11—H11A	0.9600
C2—C3	1.340 (3)	C11—H11B	0.9600
O3—C4	1.232 (2)	C11—H11C	0.9600
C5—C6	1.383 (3)

C2—O2—C11	116.82 (16)	C5—C6—C7	119.9 (2)
C5—C10—C9	119.40 (19)	C5—C6—H6	120.0
C5—C10—C4	120.52 (18)	C7—C6—H6	120.0
C9—C10—C4	120.07 (19)	O3—C4—C3	120.4 (2)
O1—C1—C9	122.80 (19)	O3—C4—C10	121.1 (2)
O1—C1—C2	120.2 (2)	C3—C4—C10	118.50 (17)
C9—C1—C2	116.96 (16)	C8—C7—C6	120.3 (2)
C8—C9—C10	119.6 (2)	C8—C7—H7	119.8
C8—C9—C1	119.66 (18)	C6—C7—H7	119.8
C10—C9—C1	120.70 (18)	C7—C8—C9	120.1 (2)
O2—C2—C3	126.77 (19)	C7—C8—H8	119.9
O2—C2—C1	111.40 (16)	C9—C8—H8	119.9
C3—C2—C1	121.83 (19)	O2—C11—H11A	109.5
C6—C5—C10	120.6 (2)	O2—C11—H11B	109.5
C6—C5—H5	119.7	H11A—C11—H11B	109.5
C10—C5—H5	119.7	O2—C11—H11C	109.5
C2—C3—C4	121.89 (19)	H11A—C11—H11C	109.5
C2—C3—H3	119.1	H11B—C11—H11C	109.5
C4—C3—H3	119.1

C5—C10—C9—C8	0.2 (3)	C4—C10—C5—C6	179.4 (2)
C4—C10—C9—C8	−179.15 (19)	O2—C2—C3—C4	−179.6 (2)
C5—C10—C9—C1	−178.86 (19)	C1—C2—C3—C4	−0.5 (3)
C4—C10—C9—C1	1.8 (3)	C10—C5—C6—C7	−0.4 (3)
O1—C1—C9—C8	−2.2 (3)	C2—C3—C4—O3	179.7 (2)
C2—C1—C9—C8	178.25 (19)	C2—C3—C4—C10	−0.5 (3)
O1—C1—C9—C10	176.9 (2)	C5—C10—C4—O3	0.2 (3)
C2—C1—C9—C10	−2.7 (3)	C9—C10—C4—O3	179.6 (2)
C11—O2—C2—C3	−1.2 (3)	C5—C10—C4—C3	−179.5 (2)
C11—O2—C2—C1	179.59 (18)	C9—C10—C4—C3	−0.1 (3)
O1—C1—C2—O2	1.7 (3)	C5—C6—C7—C8	0.6 (4)
C9—C1—C2—O2	−178.74 (17)	C6—C7—C8—C9	−0.3 (3)
O1—C1—C2—C3	−177.6 (2)	C10—C9—C8—C7	−0.1 (3)
C9—C1—C2—C3	2.0 (3)	C1—C9—C8—C7	179.0 (2)
C9—C10—C5—C6	0.0 (3)

Experimental details

Crystal data
Chemical formula	C₁₁H₈O₃
M_r	188.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	3.904 (3), 7.662 (6), 28.81 (2)
β (°)	93.562 (7)
V (Å³)	860.1 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Enrfa–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968.
T_min, T_max	0.979, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	7068, 2082, 1458
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.136, 1.08
No. of reflections	2082
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Administration of Traditional Chinese Medicine of the Zhejiang Province of China (Project 2005Z001 and 2007 C A113).

References

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