Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100016280/qa0457sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100016280/qa0457Isup2.hkl |
CCDC reference: 156222
The title compound was synthesized according to the procedure of Elix et al. (1984). A solution of 4,6-dimethoxy-2-hydroxy-3-methylbenzoic acid (0.07 mmol) and 2,4,6-trihydroxy-3-methylacetophenone (0.07 mmol) in dry dichloromethane was added to a mixture of N,N-dimethylaminopyridine (0.01 mmol) and N,N-dicyclohexyl-carbodiimide(0.17 mmol). The reaction mixture was stirred in a nitrogen atmosphere at room temperature for 6 h. After purification, the corresponding depside (0.05 mmol) was obtained. For the Smiles rearrangement of the depside, a mixture of the depside (0.27 mmol) and anhydrous potassium carbonate (0.40 mmol) in dimethyl sulfoxide (5 ml) was stirred in a nitrogen atmosphere at room temperature for 16 h. The reaction mixture was acidified with cold diluted hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with water to remove the dimethylsulfoxide. After evaporation of the solvent, the crude product was recrystallized in methanol, giving the title compound as light brown crystals, m.p. 447–449 K.
After checking their presence in the difference map, all H atoms were placed in calculated positions with O—H = 0.82 Å and C—H = 0.93–0.96 Å, and were allowed to ride on their attached atoms with Uiso = 1.5Ueq for the attached atom. Due to large fraction of weak data at higher angles, the 2θ maximum is limited to 50°.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
C19H20O8 | Dx = 1.399 Mg m−3 |
Mr = 376.35 | Melting point = 174–176 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0228 (3) Å | Cell parameters from 3937 reflections |
b = 24.792 (1) Å | θ = 1.6–28.2° |
c = 12.189 (1) Å | µ = 0.11 mm−1 |
β = 100.928 (1)° | T = 293 K |
V = 1787.1 (2) Å3 | Plate, light brown |
Z = 4 | 0.34 × 0.18 × 0.10 mm |
F(000) = 792 |
Siemens SMART CCD area-detector diffractometer | 1529 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.075 |
Graphite monochromator | θmax = 25.0°, θmin = 1.6° |
Detector resolution: 8.33 pixels mm-1 | h = −7→6 |
ω scans | k = −29→29 |
6669 measured reflections | l = −11→14 |
2848 independent reflections |
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)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.231 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.1483P)2] where P = (Fo2 + 2Fc2)/3 |
2848 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C19H20O8 | V = 1787.1 (2) Å3 |
Mr = 376.35 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.0228 (3) Å | µ = 0.11 mm−1 |
b = 24.792 (1) Å | T = 293 K |
c = 12.189 (1) Å | 0.34 × 0.18 × 0.10 mm |
β = 100.928 (1)° |
Siemens SMART CCD area-detector diffractometer | 1529 reflections with I > 2σ(I) |
6669 measured reflections | Rint = 0.075 |
2848 independent reflections |
R[F2 > 2σ(F2)] = 0.080 | 0 restraints |
wR(F2) = 0.231 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.47 e Å−3 |
2848 reflections | Δρmin = −0.36 e Å−3 |
244 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4.023 cm and the detector swing angle was −35°. Coverage of the unique set is over 90% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. After checking their presence in the difference map, all H atoms were placed at the geometrically calculated positions and a riding model was used for their refinement. The isotropic displacment parameters of the hydrogen atoms were fixed at one and a half times of the Ueq value of their parent atoms. Crystal decay was monitored by SAINT (Siemens, 1996) and was found to be negligible. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.1912 (5) | 0.58748 (10) | 0.2336 (2) | 0.0408 (8) | |
O2 | 0.5518 (6) | 0.65014 (13) | −0.0280 (3) | 0.0714 (12) | |
H2A | 0.5548 | 0.6186 | −0.0477 | 0.107* | |
O3 | 0.6996 (7) | 0.80722 (13) | 0.0786 (3) | 0.0742 (12) | |
O4 | 1.0595 (7) | 0.77311 (12) | 0.1958 (3) | 0.0718 (12) | |
H4A | 0.9642 | 0.7950 | 0.1667 | 0.108* | |
O5 | 0.6954 (6) | 0.48547 (12) | 0.4075 (3) | 0.0585 (10) | |
O6 | 1.1350 (5) | 0.39835 (11) | 0.1675 (3) | 0.0469 (9) | |
O7 | 1.4470 (5) | 0.46170 (12) | 0.1015 (3) | 0.0482 (9) | |
O8 | 1.2700 (6) | 0.53787 (13) | 0.0455 (3) | 0.0613 (10) | |
H8A | 1.3684 | 0.5390 | 0.0074 | 0.092* | |
C1 | 0.8631 (8) | 0.61821 (17) | 0.1042 (4) | 0.0462 (12) | |
H1A | 0.8223 | 0.5829 | 0.0843 | 0.055* | |
C2 | 0.7321 (8) | 0.66010 (17) | 0.0563 (4) | 0.0486 (13) | |
C3 | 0.7823 (8) | 0.71442 (16) | 0.0875 (4) | 0.0422 (12) | |
C4 | 0.9890 (8) | 0.72245 (16) | 0.1640 (4) | 0.0442 (12) | |
C5 | 1.1305 (8) | 0.68091 (16) | 0.2101 (4) | 0.0425 (12) | |
C6 | 1.0567 (8) | 0.62856 (16) | 0.1827 (4) | 0.0402 (11) | |
C7 | 1.0854 (7) | 0.53831 (15) | 0.2480 (4) | 0.0336 (10) | |
C8 | 0.9357 (7) | 0.53618 (16) | 0.3208 (4) | 0.0400 (11) | |
C9 | 0.8464 (7) | 0.48542 (17) | 0.3387 (4) | 0.0396 (11) | |
C10 | 0.9128 (7) | 0.43905 (16) | 0.2901 (4) | 0.0402 (11) | |
H10A | 0.8545 | 0.4057 | 0.3052 | 0.048* | |
C11 | 1.0657 (7) | 0.44248 (16) | 0.2190 (4) | 0.0359 (10) | |
C12 | 1.1536 (7) | 0.49248 (15) | 0.1943 (3) | 0.0323 (10) | |
C13 | 0.6371 (9) | 0.76068 (18) | 0.0483 (4) | 0.0543 (14) | |
C14 | 0.4080 (10) | 0.7549 (2) | −0.0252 (5) | 0.0721 (17) | |
H14A | 0.3408 | 0.7899 | −0.0401 | 0.108* | |
H14B | 0.3133 | 0.7330 | 0.0119 | 0.108* | |
H14C | 0.4236 | 0.7381 | −0.0943 | 0.108* | |
C15 | 1.3484 (9) | 0.6915 (2) | 0.2918 (5) | 0.0708 (17) | |
H15A | 1.3722 | 0.7297 | 0.2999 | 0.106* | |
H15B | 1.4723 | 0.6755 | 0.2643 | 0.106* | |
H15C | 1.3389 | 0.6760 | 0.3630 | 0.106* | |
C16 | 0.8672 (9) | 0.58493 (18) | 0.3812 (4) | 0.0535 (13) | |
H16A | 0.9421 | 0.6164 | 0.3601 | 0.080* | |
H16B | 0.9095 | 0.5796 | 0.4604 | 0.080* | |
H16C | 0.7064 | 0.5898 | 0.3614 | 0.080* | |
C17 | 0.5833 (9) | 0.43585 (19) | 0.4250 (5) | 0.0658 (16) | |
H17A | 0.4812 | 0.4420 | 0.4754 | 0.099* | |
H17B | 0.6937 | 0.4094 | 0.4564 | 0.099* | |
H17C | 0.5001 | 0.4230 | 0.3549 | 0.099* | |
C18 | 1.0217 (9) | 0.34841 (17) | 0.1762 (5) | 0.0560 (14) | |
H18A | 1.0858 | 0.3210 | 0.1362 | 0.084* | |
H18B | 0.8639 | 0.3524 | 0.1449 | 0.084* | |
H18C | 1.0393 | 0.3383 | 0.2534 | 0.084* | |
C19 | 1.3050 (8) | 0.49644 (16) | 0.1123 (4) | 0.0384 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0546 (18) | 0.0297 (16) | 0.038 (2) | −0.0020 (13) | 0.0086 (15) | 0.0020 (13) |
O2 | 0.093 (3) | 0.0396 (18) | 0.070 (3) | 0.0101 (18) | −0.013 (2) | −0.0040 (17) |
O3 | 0.104 (3) | 0.032 (2) | 0.084 (3) | 0.0077 (18) | 0.011 (2) | 0.0013 (18) |
O4 | 0.100 (3) | 0.0298 (18) | 0.082 (3) | −0.0069 (18) | 0.008 (2) | −0.0062 (17) |
O5 | 0.079 (2) | 0.047 (2) | 0.061 (3) | 0.0046 (17) | 0.042 (2) | 0.0006 (16) |
O6 | 0.067 (2) | 0.0329 (17) | 0.048 (2) | 0.0005 (14) | 0.0296 (17) | −0.0024 (14) |
O7 | 0.066 (2) | 0.0402 (17) | 0.045 (2) | 0.0076 (16) | 0.0263 (17) | 0.0050 (14) |
O8 | 0.084 (2) | 0.054 (2) | 0.057 (2) | 0.0194 (18) | 0.041 (2) | 0.0228 (17) |
C1 | 0.073 (3) | 0.025 (2) | 0.037 (3) | 0.003 (2) | 0.005 (3) | −0.0011 (19) |
C2 | 0.067 (3) | 0.036 (3) | 0.039 (3) | −0.001 (2) | 0.001 (3) | −0.002 (2) |
C3 | 0.069 (3) | 0.029 (2) | 0.035 (3) | 0.002 (2) | 0.023 (3) | 0.0003 (18) |
C4 | 0.075 (3) | 0.026 (2) | 0.037 (3) | −0.009 (2) | 0.022 (3) | −0.0035 (18) |
C5 | 0.063 (3) | 0.031 (2) | 0.036 (3) | −0.006 (2) | 0.016 (2) | −0.0018 (19) |
C6 | 0.060 (3) | 0.032 (2) | 0.032 (3) | 0.002 (2) | 0.017 (2) | 0.0013 (19) |
C7 | 0.043 (2) | 0.032 (2) | 0.026 (3) | 0.0014 (19) | 0.005 (2) | 0.0047 (17) |
C8 | 0.056 (3) | 0.031 (2) | 0.034 (3) | 0.006 (2) | 0.013 (2) | 0.0014 (19) |
C9 | 0.051 (3) | 0.042 (3) | 0.032 (3) | 0.010 (2) | 0.023 (2) | 0.0045 (19) |
C10 | 0.056 (3) | 0.032 (2) | 0.036 (3) | 0.000 (2) | 0.019 (2) | 0.0052 (19) |
C11 | 0.052 (2) | 0.034 (2) | 0.025 (3) | 0.0054 (19) | 0.016 (2) | 0.0004 (18) |
C12 | 0.043 (2) | 0.036 (2) | 0.021 (3) | 0.0034 (18) | 0.014 (2) | 0.0046 (17) |
C13 | 0.091 (4) | 0.036 (3) | 0.042 (3) | 0.010 (3) | 0.026 (3) | 0.008 (2) |
C14 | 0.088 (4) | 0.051 (3) | 0.076 (4) | 0.018 (3) | 0.012 (3) | 0.012 (3) |
C15 | 0.079 (4) | 0.054 (3) | 0.076 (4) | −0.011 (3) | 0.006 (3) | −0.009 (3) |
C16 | 0.078 (3) | 0.043 (3) | 0.045 (3) | 0.007 (2) | 0.025 (3) | −0.001 (2) |
C17 | 0.077 (4) | 0.053 (3) | 0.078 (4) | −0.004 (3) | 0.043 (3) | 0.009 (3) |
C18 | 0.072 (3) | 0.039 (3) | 0.065 (4) | −0.001 (2) | 0.034 (3) | −0.004 (2) |
C19 | 0.061 (3) | 0.030 (2) | 0.025 (3) | −0.001 (2) | 0.012 (2) | −0.0003 (19) |
O1—C6 | 1.374 (5) | C7—C12 | 1.411 (6) |
O1—C7 | 1.402 (5) | C8—C9 | 1.402 (6) |
O2—C2 | 1.369 (6) | C8—C16 | 1.512 (6) |
O2—H2A | 0.8200 | C9—C10 | 1.387 (6) |
O3—C13 | 1.248 (5) | C10—C11 | 1.381 (6) |
O4—C4 | 1.358 (5) | C10—H10A | 0.9300 |
O4—H4A | 0.8200 | C11—C12 | 1.403 (6) |
O5—C9 | 1.349 (5) | C12—C19 | 1.478 (6) |
O5—C17 | 1.438 (5) | C13—C14 | 1.503 (8) |
O6—C11 | 1.366 (5) | C14—H14A | 0.9600 |
O6—C18 | 1.427 (5) | C14—H14B | 0.9600 |
O7—C19 | 1.239 (5) | C14—H14C | 0.9600 |
O8—C19 | 1.303 (5) | C15—H15A | 0.9600 |
O8—H8A | 0.8200 | C15—H15B | 0.9600 |
C1—C2 | 1.366 (6) | C15—H15C | 0.9600 |
C1—C6 | 1.385 (6) | C16—H16A | 0.9600 |
C1—H1A | 0.9300 | C16—H16B | 0.9600 |
C2—C3 | 1.416 (6) | C16—H16C | 0.9600 |
C3—C4 | 1.421 (7) | C17—H17A | 0.9600 |
C3—C13 | 1.466 (6) | C17—H17B | 0.9600 |
C4—C5 | 1.386 (6) | C17—H17C | 0.9600 |
C5—C6 | 1.392 (6) | C18—H18A | 0.9600 |
C5—C15 | 1.512 (7) | C18—H18B | 0.9600 |
C7—C8 | 1.381 (6) | C18—H18C | 0.9600 |
C6—O1—C7 | 117.3 (3) | C11—C12—C7 | 117.2 (4) |
C2—O2—H2A | 109.5 | C11—C12—C19 | 120.7 (4) |
C4—O4—H4A | 109.5 | C7—C12—C19 | 122.1 (4) |
C9—O5—C17 | 118.8 (4) | O3—C13—C3 | 120.0 (5) |
C11—O6—C18 | 117.9 (3) | O3—C13—C14 | 117.1 (4) |
C19—O8—H8A | 109.5 | C3—C13—C14 | 122.9 (4) |
C2—C1—C6 | 119.8 (4) | C13—C14—H14A | 109.5 |
C2—C1—H1A | 120.1 | C13—C14—H14B | 109.5 |
C6—C1—H1A | 120.1 | H14A—C14—H14B | 109.5 |
C1—C2—O2 | 119.7 (4) | C13—C14—H14C | 109.5 |
C1—C2—C3 | 122.1 (4) | H14A—C14—H14C | 109.5 |
O2—C2—C3 | 118.1 (4) | H14B—C14—H14C | 109.5 |
C2—C3—C4 | 115.2 (4) | C5—C15—H15A | 109.5 |
C2—C3—C13 | 124.9 (4) | C5—C15—H15B | 109.5 |
C4—C3—C13 | 119.9 (4) | H15A—C15—H15B | 109.5 |
O4—C4—C5 | 115.9 (4) | C5—C15—H15C | 109.5 |
O4—C4—C3 | 120.3 (4) | H15A—C15—H15C | 109.5 |
C5—C4—C3 | 123.8 (4) | H15B—C15—H15C | 109.5 |
C4—C5—C6 | 116.9 (4) | C8—C16—H16A | 109.5 |
C4—C5—C15 | 121.9 (4) | C8—C16—H16B | 109.5 |
C6—C5—C15 | 121.2 (4) | H16A—C16—H16B | 109.5 |
O1—C6—C1 | 121.5 (4) | C8—C16—H16C | 109.5 |
O1—C6—C5 | 116.7 (4) | H16A—C16—H16C | 109.5 |
C1—C6—C5 | 121.8 (4) | H16B—C16—H16C | 109.5 |
C8—C7—O1 | 118.8 (4) | O5—C17—H17A | 109.5 |
C8—C7—C12 | 123.4 (4) | O5—C17—H17B | 109.5 |
O1—C7—C12 | 117.6 (4) | H17A—C17—H17B | 109.5 |
C7—C8—C9 | 116.8 (4) | O5—C17—H17C | 109.5 |
C7—C8—C16 | 123.6 (4) | H17A—C17—H17C | 109.5 |
C9—C8—C16 | 119.6 (4) | H17B—C17—H17C | 109.5 |
O5—C9—C10 | 123.3 (4) | O6—C18—H18A | 109.5 |
O5—C9—C8 | 114.8 (4) | O6—C18—H18B | 109.5 |
C10—C9—C8 | 121.8 (4) | H18A—C18—H18B | 109.5 |
C11—C10—C9 | 119.8 (4) | O6—C18—H18C | 109.5 |
C11—C10—H10A | 120.1 | H18A—C18—H18C | 109.5 |
C9—C10—H10A | 120.1 | H18B—C18—H18C | 109.5 |
O6—C11—C10 | 122.5 (4) | O7—C19—O8 | 121.0 (4) |
O6—C11—C12 | 116.6 (4) | O7—C19—C12 | 123.6 (4) |
C10—C11—C12 | 120.8 (4) | O8—C19—C12 | 115.3 (4) |
C6—C1—C2—O2 | 174.4 (4) | C17—O5—C9—C10 | −5.1 (7) |
C6—C1—C2—C3 | −2.7 (7) | C17—O5—C9—C8 | 175.9 (4) |
C1—C2—C3—C4 | 5.6 (7) | C7—C8—C9—O5 | −178.0 (4) |
O2—C2—C3—C4 | −171.5 (4) | C16—C8—C9—O5 | 2.5 (6) |
C1—C2—C3—C13 | −173.3 (4) | C7—C8—C9—C10 | 3.0 (6) |
O2—C2—C3—C13 | 9.6 (7) | C16—C8—C9—C10 | −176.5 (4) |
C2—C3—C4—O4 | 177.0 (4) | O5—C9—C10—C11 | 179.0 (4) |
C13—C3—C4—O4 | −4.1 (7) | C8—C9—C10—C11 | −2.1 (7) |
C2—C3—C4—C5 | −2.6 (7) | C18—O6—C11—C10 | 8.6 (6) |
C13—C3—C4—C5 | 176.3 (4) | C18—O6—C11—C12 | −169.9 (4) |
O4—C4—C5—C6 | 177.2 (4) | C9—C10—C11—O6 | −179.1 (4) |
C3—C4—C5—C6 | −3.2 (7) | C9—C10—C11—C12 | −0.6 (7) |
O4—C4—C5—C15 | 0.7 (7) | O6—C11—C12—C7 | −179.3 (4) |
C3—C4—C5—C15 | −179.7 (5) | C10—C11—C12—C7 | 2.2 (6) |
C7—O1—C6—C1 | −29.9 (6) | O6—C11—C12—C19 | 2.8 (6) |
C7—O1—C6—C5 | 152.9 (4) | C10—C11—C12—C19 | −175.8 (4) |
C2—C1—C6—O1 | 179.2 (4) | C8—C7—C12—C11 | −1.2 (6) |
C2—C1—C6—C5 | −3.8 (7) | O1—C7—C12—C11 | 173.1 (3) |
C4—C5—C6—O1 | −176.3 (4) | C8—C7—C12—C19 | 176.7 (4) |
C15—C5—C6—O1 | 0.2 (7) | O1—C7—C12—C19 | −9.0 (6) |
C4—C5—C6—C1 | 6.5 (7) | C2—C3—C13—O3 | −178.2 (5) |
C15—C5—C6—C1 | −177.0 (5) | C4—C3—C13—O3 | 3.0 (7) |
C6—O1—C7—C8 | −67.2 (5) | C2—C3—C13—C14 | 3.8 (8) |
C6—O1—C7—C12 | 118.3 (4) | C4—C3—C13—C14 | −175.0 (5) |
O1—C7—C8—C9 | −175.6 (4) | C11—C12—C19—O7 | −36.4 (6) |
C12—C7—C8—C9 | −1.4 (6) | C7—C12—C19—O7 | 145.8 (4) |
O1—C7—C8—C16 | 4.0 (6) | C11—C12—C19—O8 | 139.3 (4) |
C12—C7—C8—C16 | 178.2 (4) | C7—C12—C19—O8 | −38.5 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O7i | 0.82 | 2.10 | 2.914 (4) | 178 |
O4—H4A···O3 | 0.82 | 1.77 | 2.506 (6) | 148 |
O8—H8A···O7ii | 0.82 | 1.89 | 2.697 (5) | 170 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+3, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H20O8 |
Mr | 376.35 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 6.0228 (3), 24.792 (1), 12.189 (1) |
β (°) | 100.928 (1) |
V (Å3) | 1787.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.34 × 0.18 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6669, 2848, 1529 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.231, 0.96 |
No. of reflections | 2848 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.36 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 1990).
O1—C6 | 1.374 (5) | O5—C17 | 1.438 (5) |
O1—C7 | 1.402 (5) | O6—C11 | 1.366 (5) |
O2—C2 | 1.369 (6) | O6—C18 | 1.427 (5) |
O3—C13 | 1.248 (5) | O7—C19 | 1.239 (5) |
O4—C4 | 1.358 (5) | O8—C19 | 1.303 (5) |
O5—C9 | 1.349 (5) | ||
C6—O1—C7 | 117.3 (3) | C11—O6—C18 | 117.9 (3) |
C9—O5—C17 | 118.8 (4) | ||
C6—C1—C2—O2 | 174.4 (4) | C17—O5—C9—C10 | −5.1 (7) |
C1—C2—C3—C4 | 5.6 (7) | C17—O5—C9—C8 | 175.9 (4) |
O2—C2—C3—C13 | 9.6 (7) | C18—O6—C11—C10 | 8.6 (6) |
C2—C3—C4—O4 | 177.0 (4) | C9—C10—C11—O6 | −179.1 (4) |
C13—C3—C4—C5 | 176.3 (4) | C8—C7—C12—C19 | 176.7 (4) |
O4—C4—C5—C6 | 177.2 (4) | C2—C3—C13—C14 | 3.8 (8) |
C7—O1—C6—C1 | −29.9 (6) | C7—C12—C19—O8 | −38.5 (6) |
C4—C5—C6—O1 | −176.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O7i | 0.82 | 2.10 | 2.914 (4) | 178 |
O4—H4A···O3 | 0.82 | 1.77 | 2.506 (6) | 148 |
O8—H8A···O7ii | 0.82 | 1.89 | 2.697 (5) | 170 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+3, −y+1, −z. |
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It has been reported that p-depsides could be readily converted into the corresponding diphenyl ether via an intramolecular Smiles rearrangement (Elix et al., 1984). A number of depsides have been prepared as intermediate compounds in the synthesis of corresponding diphenyl ether molecules. Suitable reaction conditions for an intramolecular Smiles rearrangement of the prepared depsides have also been studied extensively (Elix & Jenie, 1989; Elix et al., 1990). The crystal structure determination of the title compound, (I), was undertaken as part of structural studies on diphenyl ether derivatives. Knowledge of the three-dimensional structure of (I) could be useful for the understanding of this synthesis and predicting selectivity of (I). \scheme
It is very difficult to obtain good quality crystals for this compound. Preliminary tests also show that this compound processes anti-bacterial action against S. aureus, though not against E. coli.
The bond lengths and bond angles observed in the structure are normal and agree reasonably with the reported values (Elix et al., 1978; Allen et al., 1987; Chantrapromma et al., 1998). The benzene rings are essentially planar [the atoms having the largest deviations in the two benzene rings are C6 − 0.036 (5) Å and C9 0.017 (5) Å] and they are nearly perpendicular to each other [dihedral angle 80.2 (2)°]. The carboxy group is twisted out of the benzene plane [C7—C12—C19—O8 − 38.5 (6)°] while the two methoxy groups and the acetyl group are nearly coplanar with the benzene rings [C18—O6—C11—C10 8.6 (6)°, C17—O5—C9—C10 − 5.1 (7)° and C2—C3—C13—C14 3.9 (8)°]. The hydroxy group in the molecule is involved in an intramolecular O—H···O hydrogen bond with the acetyl O atom. The compound is connected by intermolecular O—H···O contact to form a dimer (O8—H8A···O7 in Table 2).