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The title compound, C18H18O7, is an anti-Helicobacter pyl­ori compound. It was characterized from the chloro­form-methanol (1:1) extract of Fusarium sp. IFB-121, an endophytic fungus in Quercus variabilis. The two benzene rings form a dihedral angle of 79.0 (2)° and intramolecular hydrogen bonds keep the phenolic hydroxy and carbonyl groups coplanar with one of the aromatic rings. The strong intermolecular hydrogen-bond contacts are consistent with the high melting point of the compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680403346X/kp6028sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680403346X/kp6028Isup2.hkl
Contains datablock I

CCDC reference: 262493

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.063
  • wR factor = 0.150
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Methyl 5-hydroxy-2-(2-hydroxy-6-methoxy-4-methylbenzoyl)-3-methoxybenzoate top
Crystal data top
C18H18O7Z = 2
Mr = 346.32F(000) = 364
Triclinic, P1Dx = 1.377 Mg m3
a = 8.5896 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.3966 (15) ÅCell parameters from 1035 reflections
c = 10.9312 (18) Åθ = 2.7–27.8°
α = 96.489 (2)°µ = 0.11 mm1
β = 99.109 (2)°T = 293 K
γ = 103.805 (2)°Prism, colourless
V = 835.5 (2) Å30.25 × 0.12 × 0.10 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3602 independent reflections
Radiation source: fine-focus sealed tube3035 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.974, Tmax = 0.989k = 1111
9287 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.4501P]
where P = (Fo2 + 2Fc2)/3
3602 reflections(Δ/σ)max = 0.010
238 parametersΔρmax = 0.23 e Å3
2 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
C10.1416 (2)0.2994 (2)0.6663 (2)0.0318 (5)
C20.0144 (3)0.2149 (2)0.6710 (2)0.0372 (5)
H20.03540.11260.66760.045*
C30.1371 (2)0.2852 (3)0.6809 (2)0.0365 (5)
C40.1090 (2)0.4368 (2)0.6850 (2)0.0350 (5)
H40.19260.48280.69150.042*
C50.0463 (3)0.5193 (2)0.6792 (2)0.0339 (5)
C60.1740 (2)0.4522 (2)0.6712 (2)0.0309 (4)
C70.2765 (2)0.2255 (2)0.6586 (2)0.0316 (5)
C80.0391 (3)0.7424 (3)0.6818 (3)0.0527 (7)
H8A0.12730.69680.61260.079*
H8B0.00290.84490.67530.079*
H8C0.07800.73520.75910.079*
C90.3341 (2)0.5491 (2)0.6556 (2)0.0312 (4)
C100.4456 (2)0.6556 (2)0.7599 (2)0.0322 (5)
C110.4310 (3)0.6571 (3)0.8875 (2)0.0418 (5)
C120.5328 (3)0.7657 (3)0.9802 (2)0.0513 (6)
H120.52120.76471.06330.062*
C130.6533 (3)0.8772 (3)0.9502 (2)0.0496 (6)
C140.6706 (3)0.8783 (3)0.8280 (3)0.0455 (6)
H140.75020.95340.80810.055*
C150.5705 (3)0.7682 (2)0.7331 (2)0.0363 (5)
C160.2721 (4)0.5500 (4)1.0317 (3)0.0709 (9)
H16A0.36390.54601.09270.106*
H16B0.18120.46741.03150.106*
H16C0.24290.64101.05240.106*
C170.7664 (4)0.9950 (4)1.0535 (3)0.0776 (10)
H17A0.83570.95031.10570.116*
H17B0.70261.03931.10330.116*
H17C0.83231.06991.01690.116*
C220.3390 (3)0.0035 (3)0.6115 (3)0.0509 (7)
H22A0.39700.02740.54680.076*
H22B0.28430.10730.59000.076*
H22C0.41470.01360.68960.076*
O10.41992 (18)0.29078 (17)0.68263 (16)0.0418 (4)
O20.21992 (18)0.08047 (17)0.62351 (17)0.0454 (4)
O30.28675 (19)0.19778 (19)0.6866 (2)0.0527 (5)
O40.08703 (19)0.66868 (17)0.67966 (18)0.0481 (5)
O50.36252 (19)0.54366 (19)0.54860 (15)0.0434 (4)
O60.3139 (2)0.5435 (2)0.91103 (16)0.0624 (6)
O70.5957 (2)0.7757 (2)0.61557 (17)0.0471 (4)
H30.366 (3)0.249 (3)0.680 (3)0.086 (11)*
H70.521 (3)0.694 (3)0.564 (3)0.080 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0271 (10)0.0379 (12)0.0328 (11)0.0129 (8)0.0065 (8)0.0042 (9)
C20.0325 (11)0.0317 (11)0.0504 (14)0.0112 (9)0.0109 (10)0.0081 (10)
C30.0245 (10)0.0413 (12)0.0440 (13)0.0090 (9)0.0088 (9)0.0049 (10)
C40.0266 (10)0.0415 (12)0.0400 (12)0.0152 (9)0.0077 (9)0.0039 (9)
C50.0307 (10)0.0351 (11)0.0376 (12)0.0125 (9)0.0062 (9)0.0051 (9)
C60.0253 (10)0.0350 (11)0.0340 (11)0.0110 (8)0.0063 (8)0.0042 (9)
C70.0288 (10)0.0342 (11)0.0350 (11)0.0124 (8)0.0088 (9)0.0062 (9)
C80.0433 (13)0.0368 (13)0.084 (2)0.0204 (11)0.0151 (13)0.0068 (13)
C90.0285 (10)0.0330 (11)0.0363 (11)0.0137 (8)0.0087 (8)0.0068 (9)
C100.0292 (10)0.0346 (11)0.0344 (11)0.0114 (8)0.0057 (9)0.0059 (9)
C110.0391 (12)0.0472 (13)0.0373 (12)0.0066 (10)0.0081 (10)0.0074 (10)
C120.0547 (15)0.0600 (16)0.0344 (13)0.0106 (13)0.0062 (11)0.0009 (12)
C130.0451 (14)0.0478 (14)0.0492 (15)0.0108 (11)0.0008 (11)0.0027 (12)
C140.0344 (12)0.0395 (13)0.0587 (16)0.0040 (10)0.0062 (11)0.0066 (11)
C150.0307 (11)0.0402 (12)0.0423 (12)0.0139 (9)0.0097 (9)0.0113 (10)
C160.074 (2)0.091 (2)0.0463 (16)0.0059 (18)0.0259 (15)0.0192 (16)
C170.072 (2)0.071 (2)0.066 (2)0.0031 (17)0.0035 (17)0.0151 (16)
C220.0392 (13)0.0372 (13)0.084 (2)0.0182 (10)0.0224 (13)0.0074 (12)
O10.0277 (8)0.0399 (9)0.0579 (10)0.0125 (7)0.0074 (7)0.0015 (7)
O20.0328 (8)0.0325 (8)0.0746 (12)0.0132 (7)0.0162 (8)0.0045 (8)
O30.0264 (8)0.0437 (10)0.0919 (15)0.0106 (7)0.0203 (9)0.0117 (9)
O40.0332 (8)0.0319 (8)0.0835 (13)0.0134 (7)0.0168 (8)0.0084 (8)
O50.0382 (9)0.0548 (10)0.0348 (9)0.0073 (7)0.0105 (7)0.0020 (7)
O60.0650 (12)0.0729 (13)0.0352 (9)0.0121 (10)0.0149 (9)0.0079 (9)
O70.0412 (9)0.0516 (11)0.0477 (10)0.0032 (8)0.0155 (8)0.0137 (8)
Geometric parameters (Å, º) top
C1—C61.389 (3)C11—O61.360 (3)
C1—C21.397 (3)C11—C121.376 (3)
C1—C71.495 (3)C12—C131.394 (4)
C2—C31.383 (3)C12—H120.9300
C2—H20.9300C13—C141.369 (4)
C3—O31.365 (3)C13—C171.517 (4)
C3—C41.381 (3)C14—C151.391 (3)
C4—C51.389 (3)C14—H140.9300
C4—H40.9300C15—O71.343 (3)
C5—O41.362 (3)C16—O61.419 (3)
C5—C61.398 (3)C16—H16A0.9600
C6—C91.504 (3)C16—H16B0.9600
C7—O11.209 (3)C16—H16C0.9600
C7—O21.322 (3)C17—H17A0.9600
C8—O41.420 (3)C17—H17B0.9600
C8—H8A0.9600C17—H17C0.9600
C8—H8B0.9600C22—O21.446 (3)
C8—H8C0.9600C22—H22A0.9600
C9—O51.230 (3)C22—H22B0.9600
C9—C101.469 (3)C22—H22C0.9600
C10—C151.409 (3)O3—H30.920 (18)
C10—C111.418 (3)O7—H70.934 (18)
C6—C1—C2120.76 (19)C11—C12—C13120.3 (2)
C6—C1—C7119.38 (18)C11—C12—H12119.8
C2—C1—C7119.85 (19)C13—C12—H12119.8
C3—C2—C1119.2 (2)C14—C13—C12119.8 (2)
C3—C2—H2120.4C14—C13—C17120.4 (3)
C1—C2—H2120.4C12—C13—C17119.8 (3)
O3—C3—C4121.77 (19)C13—C14—C15120.8 (2)
O3—C3—C2116.9 (2)C13—C14—H14119.6
C4—C3—C2121.4 (2)C15—C14—H14119.6
C3—C4—C5118.85 (19)O7—C15—C14117.4 (2)
C3—C4—H4120.6O7—C15—C10121.7 (2)
C5—C4—H4120.6C14—C15—C10120.9 (2)
O4—C5—C4123.90 (19)O6—C16—H16A109.5
O4—C5—C6114.79 (18)O6—C16—H16B109.5
C4—C5—C6121.3 (2)H16A—C16—H16B109.5
C1—C6—C5118.49 (19)O6—C16—H16C109.5
C1—C6—C9123.95 (18)H16A—C16—H16C109.5
C5—C6—C9117.27 (18)H16B—C16—H16C109.5
O1—C7—O2124.33 (19)C13—C17—H17A109.5
O1—C7—C1123.9 (2)C13—C17—H17B109.5
O2—C7—C1111.74 (17)H17A—C17—H17B109.5
O4—C8—H8A109.5C13—C17—H17C109.5
O4—C8—H8B109.5H17A—C17—H17C109.5
H8A—C8—H8B109.5H17B—C17—H17C109.5
O4—C8—H8C109.5O2—C22—H22A109.5
H8A—C8—H8C109.5O2—C22—H22B109.5
H8B—C8—H8C109.5H22A—C22—H22B109.5
O5—C9—C10120.83 (19)O2—C22—H22C109.5
O5—C9—C6116.75 (19)H22A—C22—H22C109.5
C10—C9—C6122.19 (18)H22B—C22—H22C109.5
C15—C10—C11117.1 (2)C7—O2—C22116.97 (17)
C15—C10—C9118.95 (19)C3—O3—H3112 (2)
C11—C10—C9123.92 (19)C5—O4—C8117.52 (18)
O6—C11—C12123.1 (2)C11—O6—C16119.2 (2)
O6—C11—C10115.7 (2)C15—O7—H7107 (2)
C12—C11—C10121.2 (2)
C6—C1—C2—C30.1 (3)C6—C9—C10—C15163.65 (19)
C7—C1—C2—C3178.6 (2)O5—C9—C10—C11172.6 (2)
C1—C2—C3—O3179.3 (2)C6—C9—C10—C1113.1 (3)
C1—C2—C3—C40.6 (4)C15—C10—C11—O6177.3 (2)
O3—C3—C4—C5179.8 (2)C9—C10—C11—O65.8 (3)
C2—C3—C4—C50.1 (3)C15—C10—C11—C121.1 (3)
C3—C4—C5—O4178.5 (2)C9—C10—C11—C12175.7 (2)
C3—C4—C5—C60.9 (3)O6—C11—C12—C13178.3 (2)
C2—C1—C6—C50.9 (3)C10—C11—C12—C130.0 (4)
C7—C1—C6—C5179.59 (19)C11—C12—C13—C140.2 (4)
C2—C1—C6—C9174.6 (2)C11—C12—C13—C17179.1 (3)
C7—C1—C6—C96.8 (3)C12—C13—C14—C150.8 (4)
O4—C5—C6—C1178.05 (19)C17—C13—C14—C15178.2 (3)
C4—C5—C6—C11.5 (3)C13—C14—C15—O7179.3 (2)
O4—C5—C6—C94.0 (3)C13—C14—C15—C101.9 (3)
C4—C5—C6—C9175.5 (2)C11—C10—C15—O7179.2 (2)
C6—C1—C7—O116.3 (3)C9—C10—C15—O73.8 (3)
C2—C1—C7—O1162.4 (2)C11—C10—C15—C142.1 (3)
C6—C1—C7—O2164.3 (2)C9—C10—C15—C14174.93 (19)
C2—C1—C7—O217.1 (3)O1—C7—O2—C221.1 (3)
C1—C6—C9—O574.5 (3)C1—C7—O2—C22179.4 (2)
C5—C6—C9—O599.2 (2)C4—C5—O4—C82.3 (3)
C1—C6—C9—C10111.0 (2)C6—C5—O4—C8177.2 (2)
C5—C6—C9—C1075.3 (3)C12—C11—O6—C1612.3 (4)
O5—C9—C10—C1510.6 (3)C10—C11—O6—C16169.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.92 (2)1.98 (2)2.853 (2)159 (3)
O7—H7···O50.93 (2)1.68 (2)2.529 (2)149 (3)
Symmetry code: (i) x1, y, z.
 

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