Literature DB >> 21577555

5,7-Dimethoxy-isobenzofuran-1(3H)-one.

Ming-Xue Sun, Xu Li, Wen-Yong Liu, Kai Xiao.   

Abstract

The asymmetric unit of the title compound, C(10)H(10)O(4), which has been isolated from rhizoma Polygonum Cuspidatum, a Chinese folk medicine, contains two crystallographically independent mol-ecules. The mol-ecules are essentially planar, with a maximum deviation of 0.061 (2) Å from the best planes. The crystal packing is stabilized by weak inter-molecular C-H⋯O hydrogen-bonding inter-actions, with a stacking direction of the mol-ecules parallel to [101].

Entities:  

Year:  2009        PMID： 21577555      PMCID： PMC2969903          DOI： 10.1107/S1600536809031183

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


Related literature

For the synthesis of 5,7-dimethoxy­phthalide, see: Talapatra & Monoj (1980 ▶); Dang et al. (1999 ▶); Orito et al. (1995 ▶). For the title compound as an inter­mediate, see: Zuo et al. (2008 ▶); Lee et al. (2001 ▶). For the title compound as a by­product, see: Fürstner et al. (2000 ▶).

Experimental

Crystal data

C10H10O4 M = 194.18 Monoclinic, a = 8.532 (3) Å b = 25.877 (10) Å c = 8.374 (3) Å β = 104.322 (6)° V = 1791.5 (11) Å3 Z = 8 Mo Kα radiation μ = 0.11 mm−1 T = 293 K 0.12 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.987, T max = 0.989 7489 measured reflections 3216 independent reflections 1766 reflections with I > 2σ(I) R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.131 S = 0.93 3216 reflections 258 parameters H-atom parameters constrained Δρmax = 0.18 e Å−3 Δρmin = −0.19 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031183/wm2246sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031183/wm2246Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C10H10O4F(000) = 816
Mr = 194.18Dx = 1.440 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 715 reflections
a = 8.532 (3) Åθ = 2.6–21.3°
b = 25.877 (10) ŵ = 0.11 mm−1
c = 8.374 (3) ÅT = 293 K
β = 104.322 (6)°Prism, colourless
V = 1791.5 (11) Å30.12 × 0.12 × 0.10 mm
Z = 8
Bruker SMART APEX CCD area-detector diffractometer3216 independent reflections
Radiation source: fine-focus sealed tube1766 reflections with I > 2σ(I)
graphiteRint = 0.062
φ and ω scansθmax = 25.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→10
Tmin = 0.987, Tmax = 0.989k = −30→31
7489 measured reflectionsl = −10→8
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.131w = 1/[σ2(Fo2) + (0.053P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
3216 reflectionsΔρmax = 0.18 e Å−3
258 parametersΔρmin = −0.19 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0026 (5)
Experimental. The powder of 5,7-dimethoxyphthalide was solved in acetone and produced colorless crystal.
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
O1A0.3975 (2)0.42391 (7)0.1615 (2)0.0627 (6)
O2A0.2605 (3)0.35976 (8)0.0110 (2)0.0674 (6)
O3A0.4002 (2)0.25798 (7)0.1709 (2)0.0571 (6)
O4A0.8571 (2)0.28610 (7)0.6142 (2)0.0628 (6)
C1A0.3670 (4)0.37248 (11)0.1270 (3)0.0518 (8)
C2A0.4830 (3)0.34270 (10)0.2496 (3)0.0417 (6)
C3A0.5069 (3)0.28902 (10)0.2724 (3)0.0470 (7)
C4A0.6341 (3)0.27237 (10)0.3971 (3)0.0471 (7)
H4A0.65290.23720.41410.057*
C5A0.7359 (3)0.30831 (11)0.4992 (3)0.0487 (7)
C6A0.7112 (3)0.36054 (10)0.4795 (3)0.0486 (7)
H6A0.77800.38420.54780.058*
C7A0.5835 (3)0.37640 (10)0.3545 (3)0.0452 (7)
C8A0.5296 (3)0.43027 (10)0.3046 (3)0.0542 (8)
H8A10.49420.44780.39200.065*
H8A20.61640.45000.27820.065*
C9A0.4125 (4)0.20351 (11)0.2069 (4)0.0644 (9)
H9A10.51770.19140.20250.097*
H9A20.33120.18530.12700.097*
H9A30.39680.19760.31500.097*
C10A0.9664 (4)0.31963 (13)0.7237 (4)0.0764 (10)
H10A1.02020.34150.66140.115*
H10B1.04510.29940.79990.115*
H10C0.90720.34060.78330.115*
O1B−0.0885 (2)0.46776 (7)0.6553 (2)0.0582 (5)
O2B−0.2380 (2)0.53224 (8)0.5190 (2)0.0674 (6)
O3B−0.0891 (2)0.63386 (7)0.6714 (2)0.0551 (5)
O4B0.3667 (2)0.60524 (7)1.1150 (2)0.0539 (5)
C1B−0.1230 (3)0.51938 (12)0.6263 (3)0.0522 (8)
C2B−0.0013 (3)0.54864 (11)0.7460 (3)0.0454 (7)
C3B0.0172 (3)0.60196 (10)0.7725 (3)0.0415 (7)
C4B0.1434 (3)0.61849 (10)0.8969 (3)0.0440 (7)
H4B0.15900.65370.91620.053*
C5B0.2488 (3)0.58354 (10)0.9954 (3)0.0420 (6)
C6B0.2297 (3)0.53046 (10)0.9714 (3)0.0418 (6)
H6B0.29880.50691.03750.050*
C7B0.1032 (3)0.51477 (9)0.8449 (3)0.0403 (6)
C8B0.0538 (3)0.46110 (10)0.7869 (3)0.0522 (7)
H8B10.13860.44420.74770.063*
H8B20.03020.44060.87500.063*
C9B−0.0723 (4)0.68778 (10)0.7035 (4)0.0620 (8)
H9B1−0.08630.69480.81170.093*
H9B2−0.15270.70620.62320.093*
H9B30.03350.69880.69730.093*
C10B0.4778 (3)0.57130 (11)1.2222 (3)0.0589 (8)
H10D0.41920.54851.27690.088*
H10E0.55310.59131.30280.088*
H10F0.53560.55141.15870.088*
U11U22U33U12U13U23
O1A0.0734 (15)0.0519 (13)0.0597 (13)0.0139 (11)0.0105 (11)0.0112 (10)
O2A0.0663 (14)0.0782 (15)0.0517 (13)0.0101 (12)0.0029 (11)0.0066 (11)
O3A0.0585 (13)0.0487 (13)0.0580 (12)0.0039 (10)0.0028 (10)−0.0025 (10)
O4A0.0558 (12)0.0596 (13)0.0618 (13)0.0065 (10)−0.0066 (11)−0.0011 (10)
C1A0.055 (2)0.059 (2)0.0442 (18)0.0101 (16)0.0194 (16)0.0078 (15)
C2A0.0409 (16)0.0434 (16)0.0435 (16)0.0030 (13)0.0157 (13)0.0015 (13)
C3A0.0446 (17)0.0492 (18)0.0479 (18)−0.0023 (14)0.0129 (14)−0.0027 (14)
C4A0.0491 (17)0.0413 (16)0.0515 (17)0.0026 (13)0.0132 (15)−0.0009 (13)
C5A0.0420 (17)0.0535 (19)0.0498 (17)0.0078 (14)0.0095 (14)0.0018 (14)
C6A0.0468 (18)0.0459 (17)0.0530 (18)−0.0022 (13)0.0120 (15)−0.0059 (13)
C7A0.0444 (17)0.0441 (17)0.0520 (17)0.0035 (13)0.0215 (14)0.0037 (14)
C8A0.064 (2)0.0491 (18)0.0544 (18)0.0077 (14)0.0233 (16)0.0054 (14)
C9A0.069 (2)0.0492 (19)0.071 (2)−0.0037 (15)0.0088 (17)−0.0008 (15)
C10A0.068 (2)0.078 (2)0.069 (2)0.0022 (18)−0.0115 (18)−0.0118 (18)
O1B0.0522 (13)0.0547 (13)0.0659 (13)−0.0078 (10)0.0111 (10)−0.0179 (10)
O2B0.0443 (12)0.0910 (16)0.0590 (13)−0.0001 (12)−0.0020 (10)−0.0168 (11)
O3B0.0514 (12)0.0544 (13)0.0538 (12)0.0078 (10)0.0018 (9)0.0017 (10)
O4B0.0504 (12)0.0478 (11)0.0521 (12)0.0024 (9)−0.0089 (10)−0.0010 (9)
C1B0.0381 (18)0.067 (2)0.0520 (19)−0.0063 (15)0.0115 (15)−0.0141 (15)
C2B0.0382 (16)0.0581 (18)0.0409 (16)−0.0021 (14)0.0117 (13)−0.0038 (14)
C3B0.0381 (16)0.0455 (17)0.0410 (16)0.0036 (13)0.0098 (13)0.0033 (13)
C4B0.0428 (16)0.0402 (16)0.0474 (16)−0.0020 (13)0.0080 (14)0.0000 (13)
C5B0.0386 (16)0.0485 (18)0.0387 (15)−0.0018 (13)0.0090 (13)−0.0029 (13)
C6B0.0381 (16)0.0438 (16)0.0437 (16)0.0047 (12)0.0107 (13)0.0030 (12)
C7B0.0417 (16)0.0397 (16)0.0431 (15)0.0003 (13)0.0175 (13)−0.0005 (13)
C8B0.0486 (18)0.0493 (18)0.0581 (18)−0.0027 (14)0.0118 (14)−0.0050 (14)
C9B0.064 (2)0.050 (2)0.068 (2)0.0100 (15)0.0074 (16)0.0063 (15)
C10B0.0473 (19)0.062 (2)0.0578 (19)0.0068 (15)−0.0056 (15)−0.0028 (15)
O1A—C1A1.373 (3)O1B—C1B1.376 (3)
O1A—C8A1.437 (3)O1B—C8B1.434 (3)
O2A—C1A1.200 (3)O2B—C1B1.202 (3)
O3A—C3A1.346 (3)O3B—C3B1.357 (3)
O3A—C9A1.440 (3)O3B—C9B1.422 (3)
O4A—C5A1.355 (3)O4B—C5B1.354 (3)
O4A—C10A1.428 (3)O4B—C10B1.434 (3)
C1A—C2A1.458 (4)C1B—C2B1.463 (4)
C2A—C7A1.377 (3)C2B—C7B1.372 (3)
C2A—C3A1.410 (4)C2B—C3B1.400 (4)
C3A—C4A1.376 (3)C3B—C4B1.368 (3)
C4A—C5A1.408 (4)C4B—C5B1.393 (3)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.371 (4)C5B—C6B1.392 (4)
C6A—C7A1.374 (3)C6B—C7B1.373 (3)
C6A—H6A0.9300C6B—H6B0.9300
C7A—C8A1.495 (3)C7B—C8B1.497 (3)
C8A—H8A10.9700C8B—H8B10.9700
C8A—H8A20.9700C8B—H8B20.9700
C9A—H9A10.9599C9B—H9B10.9599
C9A—H9A20.9599C9B—H9B20.9599
C9A—H9A30.9599C9B—H9B30.9599
C10A—H10A0.9599C10B—H10D0.9599
C10A—H10B0.9599C10B—H10E0.9599
C10A—H10C0.9599C10B—H10F0.9599
C1A—O1A—C8A110.8 (2)C1B—O1B—C8B110.8 (2)
C3A—O3A—C9A116.7 (2)C3B—O3B—C9B117.3 (2)
C5A—O4A—C10A117.5 (2)C5B—O4B—C10B117.7 (2)
O2A—C1A—O1A120.2 (3)O2B—C1B—O1B120.0 (3)
O2A—C1A—C2A132.1 (3)O2B—C1B—C2B132.7 (3)
O1A—C1A—C2A107.7 (2)O1B—C1B—C2B107.3 (2)
C7A—C2A—C3A119.4 (2)C7B—C2B—C3B120.2 (2)
C7A—C2A—C1A108.8 (2)C7B—C2B—C1B109.1 (3)
C3A—C2A—C1A131.8 (3)C3B—C2B—C1B130.6 (3)
O3A—C3A—C4A125.1 (3)O3B—C3B—C4B124.3 (2)
O3A—C3A—C2A116.7 (2)O3B—C3B—C2B118.0 (2)
C4A—C3A—C2A118.2 (2)C4B—C3B—C2B117.7 (2)
C3A—C4A—C5A120.4 (3)C3B—C4B—C5B121.3 (2)
C3A—C4A—H4A119.8C3B—C4B—H4B119.4
C5A—C4A—H4A119.8C5B—C4B—H4B119.4
O4A—C5A—C6A124.8 (3)O4B—C5B—C6B123.7 (2)
O4A—C5A—C4A113.5 (2)O4B—C5B—C4B114.9 (2)
C6A—C5A—C4A121.6 (3)C6B—C5B—C4B121.3 (2)
C5A—C6A—C7A117.1 (2)C7B—C6B—C5B116.4 (2)
C5A—C6A—H6A121.5C7B—C6B—H6B121.8
C7A—C6A—H6A121.5C5B—C6B—H6B121.8
C6A—C7A—C2A123.3 (2)C2B—C7B—C6B123.1 (2)
C6A—C7A—C8A128.5 (3)C2B—C7B—C8B107.9 (2)
C2A—C7A—C8A108.2 (2)C6B—C7B—C8B129.0 (2)
O1A—C8A—C7A104.5 (2)O1B—C8B—C7B104.8 (2)
O1A—C8A—H8A1110.9O1B—C8B—H8B1110.8
C7A—C8A—H8A1110.9C7B—C8B—H8B1110.8
O1A—C8A—H8A2110.9O1B—C8B—H8B2110.8
C7A—C8A—H8A2110.9C7B—C8B—H8B2110.8
H8A1—C8A—H8A2108.9H8B1—C8B—H8B2108.9
O3A—C9A—H9A1109.5O3B—C9B—H9B1109.5
O3A—C9A—H9A2109.5O3B—C9B—H9B2109.5
H9A1—C9A—H9A2109.5H9B1—C9B—H9B2109.5
O3A—C9A—H9A3109.5O3B—C9B—H9B3109.5
H9A1—C9A—H9A3109.5H9B1—C9B—H9B3109.5
H9A2—C9A—H9A3109.5H9B2—C9B—H9B3109.5
O4A—C10A—H10A109.5O4B—C10B—H10D109.5
O4A—C10A—H10B109.5O4B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
O4A—C10A—H10C109.5O4B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
C8A—O1A—C1A—O2A−179.8 (2)C8B—O1B—C1B—O2B179.5 (2)
C8A—O1A—C1A—C2A−0.5 (3)C8B—O1B—C1B—C2B−1.5 (3)
O2A—C1A—C2A—C7A178.2 (3)O2B—C1B—C2B—C7B178.6 (3)
O1A—C1A—C2A—C7A−1.0 (3)O1B—C1B—C2B—C7B−0.3 (3)
O2A—C1A—C2A—C3A−0.6 (5)O2B—C1B—C2B—C3B0.5 (5)
O1A—C1A—C2A—C3A−179.8 (3)O1B—C1B—C2B—C3B−178.5 (2)
C9A—O3A—C3A—C4A6.2 (4)C9B—O3B—C3B—C4B−3.4 (4)
C9A—O3A—C3A—C2A−172.6 (2)C9B—O3B—C3B—C2B177.8 (2)
C7A—C2A—C3A—O3A177.0 (2)C7B—C2B—C3B—O3B180.0 (2)
C1A—C2A—C3A—O3A−4.3 (4)C1B—C2B—C3B—O3B−2.0 (4)
C7A—C2A—C3A—C4A−1.9 (4)C7B—C2B—C3B—C4B1.1 (4)
C1A—C2A—C3A—C4A176.8 (3)C1B—C2B—C3B—C4B179.1 (2)
O3A—C3A—C4A—C5A−178.2 (2)O3B—C3B—C4B—C5B−179.5 (2)
C2A—C3A—C4A—C5A0.6 (4)C2B—C3B—C4B—C5B−0.7 (4)
C10A—O4A—C5A—C6A0.5 (4)C10B—O4B—C5B—C6B0.2 (4)
C10A—O4A—C5A—C4A−179.9 (2)C10B—O4B—C5B—C4B179.1 (2)
C3A—C4A—C5A—O4A−178.9 (2)C3B—C4B—C5B—O4B−179.2 (2)
C3A—C4A—C5A—C6A0.7 (4)C3B—C4B—C5B—C6B−0.2 (4)
O4A—C5A—C6A—C7A179.0 (2)O4B—C5B—C6B—C7B179.6 (2)
C4A—C5A—C6A—C7A−0.6 (4)C4B—C5B—C6B—C7B0.8 (4)
C5A—C6A—C7A—C2A−0.8 (4)C3B—C2B—C7B—C6B−0.6 (4)
C5A—C6A—C7A—C8A−179.5 (3)C1B—C2B—C7B—C6B−179.0 (2)
C3A—C2A—C7A—C6A2.1 (4)C3B—C2B—C7B—C8B−179.8 (2)
C1A—C2A—C7A—C6A−176.9 (2)C1B—C2B—C7B—C8B1.8 (3)
C3A—C2A—C7A—C8A−178.9 (2)C5B—C6B—C7B—C2B−0.4 (4)
C1A—C2A—C7A—C8A2.1 (3)C5B—C6B—C7B—C8B178.7 (2)
C1A—O1A—C8A—C7A1.7 (3)C1B—O1B—C8B—C7B2.5 (3)
C6A—C7A—C8A—O1A176.6 (2)C2B—C7B—C8B—O1B−2.6 (3)
C2A—C7A—C8A—O1A−2.3 (3)C6B—C7B—C8B—O1B178.2 (2)
D—H···AD—HH···AD···AD—H···A
C6A—H6A···O1Bi0.932.513.397 (3)161
C8A—H8A1···O2Bii0.972.533.337 (3)140
C6B—H6B···O1Aiii0.932.443.325 (3)159
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C6A—H6A⋯O1Bi0.932.513.397 (3)161
C8A—H8A1⋯O2Bii0.972.533.337 (3)140
C6B—H6B⋯O1Aiii0.932.443.325 (3)159

Symmetry codes: (i) ; (ii) ; (iii) .

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Authors:  A Fürstner; O R Thiel; N Kindler; B Bartkowska
Journal:  J Org Chem       Date:  2000-11-17       Impact factor: 4.354

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  2 in total

1.  6-Meth-oxyisobenzofuran-1(3H)-one.

Authors:  Jorge L Pereira; Róbson R Teixeira; Silvana Guilardi; Drielly A Paixão
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-26

2.  5-Meth-oxy-2-benzofuran-1(3H)-one.

Authors:  Drielly A Paixão; Silvana Guilardi; Jorge L Pereira; Róbson R Teixeira; Júnior F Arantes
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-07
  2 in total

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