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In the mol­ecule of the title compound, C11H14O5, the methyl ester and the two meth­oxy residues in meta positions to the ester residue are almost coplanar, while the meth­oxy residue in the para position is almost perpendicular with respect to the aromatic ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054384/hk2329sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054384/hk2329Isup2.hkl
Contains datablock I

CCDC reference: 674078

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.040
  • wR factor = 0.114
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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No errors found in this datablock

Comment top

The title ester is a constituent of the volatile oils of the genus eucalyptus (Hellyer et al., 1966) and an important intermediate in the synthesis of a variety of natural products. These include lomandrone, the principal pigment of Lomandra hastilis (Cooke & Rainbow 1974), the aglycon of Actinoflavoside (Suzuki et al., 2004), the cactus alkaloid, mescaline well known on account of its interesting effects on the psychic states of human subjects (Aboul-Enein & Eid 1979) and Cercidinin A, an ellagitannin isolated from the bark of Cercidiphyllum japonicum (Tanaka et al., 2001). In addition a number of isocoumarins like kigelin (Saeed & Ehesan, 2005a), reticulol (Saeed & Ehesan, 2005b) and cAMP phosphodiesterase inhibitor 8-hydroxy-6,7-dimethoxy -3-hydroxymethylisocoumarin (Saeed, 2007). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The methyl acetate and the two O—Me residues in meta position to the ester residue are almost coplanar, while the O—Me residue in para-position is almost perpendicular with respect to the aromatic ring.

Related literature top

For related literature, see: Hellyer et al. (1966); Cooke & Rainbow (1974); Suzuki et al. (2004); Aboul-Enein & Eid (1979); Tanaka et al. (2001); Saeed & Ehsan (2005a, 2005b); Saeed (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

Dimethyl sulfate (5.6 g, 45 mmol) and anhydrous potassium carbonate (6.1 g, 50 mmol) were added to a stirred solution of gallic acid (1.7 g, 10 mmol) in acetone (60 ml), and the mixture was refluxed under nitrogen for 6 h. The acetone was rotary evaporated, the residue was mixed with ice-water, and then extracted with ethyl acetate (3 x 50 ml). The extract was washed with NaHCO3 (5%), dried (MgSO4) and evaporated. The residue was recrystallized from aqueous methanol as needles (yield; 2.29 g, 92%, m.p. 355–356 K). The spectroscopic data was in agreement to that reported in literature (Aboul-Enein & Eid, 1979).

Refinement top

H atoms were positioned geometrically, with C—H = 0.95 and 0.98 Å for aromatic and methyl H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.2 for aromatic H and x = 1.5 for methyl H atoms.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Methyl 3,4,5-trimethoxybenzoate top
Crystal data top
C11H14O5F(000) = 480
Mr = 226.22Dx = 1.343 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7934 reflections
a = 17.6930 (15) Åθ = 3.5–25.6°
b = 4.5050 (5) ŵ = 0.11 mm1
c = 14.6383 (12) ÅT = 173 K
β = 106.545 (7)°Block, colorless
V = 1118.47 (18) Å30.42 × 0.37 × 0.21 mm
Z = 4
Data collection top
STOE IPDS-II
diffractometer
1796 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.068
Graphite monochromatorθmax = 25.6°, θmin = 3.6°
ω scansh = 2121
8229 measured reflectionsk = 45
2094 independent reflectionsl = 1517
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0714P)2 + 0.0891P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2094 reflectionsΔρmax = 0.29 e Å3
150 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.035 (5)
Crystal data top
C11H14O5V = 1118.47 (18) Å3
Mr = 226.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.6930 (15) ŵ = 0.11 mm1
b = 4.5050 (5) ÅT = 173 K
c = 14.6383 (12) Å0.42 × 0.37 × 0.21 mm
β = 106.545 (7)°
Data collection top
STOE IPDS-II
diffractometer
1796 reflections with I > 2σ(I)
8229 measured reflectionsRint = 0.068
2094 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.06Δρmax = 0.29 e Å3
2094 reflectionsΔρmin = 0.20 e Å3
150 parameters
Special details top

Experimental. ;

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
xyzUiso*/Ueq
C10.69462 (7)0.3640 (3)0.37200 (9)0.0242 (3)
C20.69852 (7)0.5101 (3)0.28963 (9)0.0257 (3)
H20.65380.61180.25100.031*
C30.76894 (7)0.5054 (3)0.26446 (9)0.0253 (3)
C40.83503 (7)0.3570 (3)0.32254 (9)0.0231 (3)
C50.83048 (7)0.2175 (3)0.40627 (9)0.0233 (3)
C60.75980 (7)0.2157 (3)0.43092 (9)0.0246 (3)
H60.75610.11570.48660.030*
C110.62009 (7)0.3662 (3)0.40168 (9)0.0277 (3)
O110.61194 (5)0.2474 (3)0.47227 (7)0.0393 (3)
O120.56223 (5)0.5192 (3)0.34019 (7)0.0395 (3)
C120.48913 (8)0.5425 (5)0.36571 (12)0.0513 (5)
H12A0.49680.67390.42090.077*
H12B0.47320.34520.38160.077*
H12C0.44800.62410.31180.077*
O310.77982 (5)0.6370 (2)0.18506 (7)0.0333 (3)
C310.71604 (8)0.8117 (3)0.12770 (10)0.0335 (3)
H31A0.70120.96330.16740.050*
H31B0.67070.68300.09990.050*
H31C0.73260.90810.07660.050*
O410.90383 (5)0.34196 (19)0.29594 (7)0.0259 (3)
C410.95168 (8)0.6036 (3)0.32068 (12)0.0336 (3)
H41A0.96770.62910.39000.050*
H41B0.92130.77720.29050.050*
H41C0.99870.58300.29840.050*
O510.89959 (5)0.0934 (2)0.46006 (7)0.0287 (3)
C510.89795 (7)0.0633 (3)0.54457 (10)0.0322 (3)
H51A0.86200.23300.52730.048*
H51B0.87960.07010.58670.048*
H51C0.95110.13420.57750.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0216 (6)0.0282 (7)0.0245 (7)0.0041 (5)0.0092 (5)0.0066 (5)
C20.0232 (6)0.0300 (7)0.0244 (7)0.0002 (5)0.0075 (5)0.0024 (5)
C30.0288 (6)0.0256 (7)0.0246 (7)0.0014 (5)0.0125 (5)0.0023 (5)
C40.0244 (6)0.0211 (6)0.0278 (7)0.0008 (4)0.0137 (5)0.0047 (5)
C50.0245 (6)0.0211 (6)0.0257 (7)0.0008 (5)0.0096 (5)0.0044 (5)
C60.0271 (6)0.0260 (7)0.0231 (6)0.0035 (5)0.0109 (5)0.0027 (5)
C110.0229 (6)0.0367 (8)0.0241 (7)0.0028 (5)0.0076 (5)0.0039 (5)
O110.0280 (5)0.0589 (7)0.0355 (6)0.0020 (4)0.0162 (4)0.0110 (5)
O120.0223 (5)0.0683 (8)0.0305 (5)0.0077 (4)0.0119 (4)0.0096 (5)
C120.0246 (6)0.0905 (14)0.0431 (9)0.0153 (7)0.0166 (6)0.0177 (9)
O310.0325 (5)0.0423 (6)0.0304 (5)0.0080 (4)0.0173 (4)0.0112 (4)
C310.0355 (7)0.0372 (8)0.0299 (7)0.0059 (6)0.0127 (6)0.0062 (6)
O410.0261 (4)0.0219 (5)0.0362 (5)0.0001 (3)0.0191 (4)0.0029 (4)
C410.0311 (6)0.0245 (7)0.0531 (9)0.0036 (5)0.0245 (6)0.0031 (6)
O510.0239 (4)0.0346 (5)0.0301 (5)0.0054 (4)0.0118 (4)0.0057 (4)
C510.0300 (6)0.0367 (8)0.0311 (7)0.0013 (5)0.0105 (5)0.0070 (6)
Geometric parameters (Å, º) top
C1—C21.3925 (19)C12—H12A0.9800
C1—C61.3978 (18)C12—H12B0.9800
C1—C111.5013 (15)C12—H12C0.9800
C2—C31.3964 (17)O31—C311.4345 (16)
C2—H20.9500C31—H31A0.9800
C3—O311.3663 (16)C31—H31B0.9800
C3—C41.4039 (18)C31—H31C0.9800
C4—O411.3813 (13)O41—C411.4362 (16)
C4—C51.4001 (19)C41—H41A0.9800
C5—O511.3710 (15)C41—H41B0.9800
C5—C61.3967 (15)C41—H41C0.9800
C6—H60.9500O51—C511.4317 (16)
C11—O111.2082 (17)C51—H51A0.9800
C11—O121.3448 (16)C51—H51B0.9800
O12—C121.4485 (15)C51—H51C0.9800
C2—C1—C6121.64 (11)O12—C12—H12C109.5
C2—C1—C11120.77 (11)H12A—C12—H12C109.5
C6—C1—C11117.58 (11)H12B—C12—H12C109.5
C1—C2—C3119.30 (12)C3—O31—C31117.27 (9)
C1—C2—H2120.3O31—C31—H31A109.5
C3—C2—H2120.3O31—C31—H31B109.5
O31—C3—C2124.78 (11)H31A—C31—H31B109.5
O31—C3—C4115.28 (10)O31—C31—H31C109.5
C2—C3—C4119.94 (12)H31A—C31—H31C109.5
O41—C4—C5119.98 (11)H31B—C31—H31C109.5
O41—C4—C3120.10 (11)C4—O41—C41113.09 (9)
C5—C4—C3119.89 (11)O41—C41—H41A109.5
O51—C5—C6124.54 (11)O41—C41—H41B109.5
O51—C5—C4114.94 (10)H41A—C41—H41B109.5
C6—C5—C4120.51 (11)O41—C41—H41C109.5
C5—C6—C1118.68 (12)H41A—C41—H41C109.5
C5—C6—H6120.7H41B—C41—H41C109.5
C1—C6—H6120.7C5—O51—C51117.59 (9)
O11—C11—O12123.08 (11)O51—C51—H51A109.5
O11—C11—C1124.97 (12)O51—C51—H51B109.5
O12—C11—C1111.95 (11)H51A—C51—H51B109.5
C11—O12—C12115.46 (11)O51—C51—H51C109.5
O12—C12—H12A109.5H51A—C51—H51C109.5
O12—C12—H12B109.5H51B—C51—H51C109.5
H12A—C12—H12B109.5
C6—C1—C2—C30.84 (19)C2—C1—C6—C50.49 (19)
C11—C1—C2—C3179.53 (11)C11—C1—C6—C5178.24 (11)
C1—C2—C3—O31179.20 (12)C2—C1—C11—O11179.39 (13)
C1—C2—C3—C40.63 (19)C6—C1—C11—O110.6 (2)
O31—C3—C4—O412.40 (17)C2—C1—C11—O120.29 (17)
C2—C3—C4—O41177.45 (11)C6—C1—C11—O12179.03 (12)
O31—C3—C4—C5179.26 (11)O11—C11—O12—C122.1 (2)
C2—C3—C4—C50.89 (19)C1—C11—O12—C12177.58 (13)
O41—C4—C5—O515.05 (17)C2—C3—O31—C315.12 (19)
C3—C4—C5—O51176.61 (11)C4—C3—O31—C31175.04 (11)
O41—C4—C5—C6176.09 (10)C5—C4—O41—C4199.28 (14)
C3—C4—C5—C62.25 (18)C3—C4—O41—C4182.39 (14)
O51—C5—C6—C1176.71 (11)C6—C5—O51—C513.72 (18)
C4—C5—C6—C12.03 (18)C4—C5—O51—C51177.48 (11)

Experimental details

Crystal data
Chemical formulaC11H14O5
Mr226.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)17.6930 (15), 4.5050 (5), 14.6383 (12)
β (°) 106.545 (7)
V3)1118.47 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.42 × 0.37 × 0.21
Data collection
DiffractometerSTOE IPDS-II
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8229, 2094, 1796
Rint0.068
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.114, 1.06
No. of reflections2094
No. of parameters150
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.20

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

 

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