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In the title compound, methyl 4-(3-formyl-2,4-di­hydroxy-6-methyl-benzoyl­oxy)-2-hydroxy-3,6-di­methyl­benzoate, C19H18O8, there are three intramolecular O—H...O hydrogen bonds, with lengths 2.5515 (14), 2.5711 (15), and 2.5437 (13) Å. The two aromatic rings form a dihedral angle of 60.38 (3)°, differing from that in the previously reported Pbca polymorph, viz. 84 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011856/om6098sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011856/om6098Isup2.hkl
Contains datablock I

CCDC reference: 193756

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.050
  • wR factor = 0.137
  • Data-to-parameter ratio = 22.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Methyl 4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy- 3,6-dimethyl-benzoate top
Crystal data top
C19H18O8F(000) = 784
Mr = 374.33Dx = 1.484 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5466 reflections
a = 10.929 (3) Åθ = 2.5–32.0°
b = 10.976 (3) ŵ = 0.12 mm1
c = 14.843 (3) ÅT = 120 K
β = 109.745 (12)°Prism, colorless
V = 1675.7 (7) Å30.40 × 0.30 × 0.15 mm
Z = 4
Data collection top
KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
4257 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 32.0°, θmin = 2.7°
ω scans with κ offsetsh = 1616
21781 measured reflectionsk = 1615
5796 independent reflectionsl = 2222
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0551P)2 + 0.7055P]
where P = (Fo2 + 2Fc2)/3
5796 reflections(Δ/σ)max < 0.001
260 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.29 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
O10.00936 (9)0.22817 (10)0.12734 (7)0.0280 (2)
O20.28830 (10)0.07016 (9)0.03346 (7)0.0248 (2)
H2O0.2043 (19)0.0886 (17)0.0052 (14)0.037*
O30.05911 (10)0.15003 (10)0.00532 (7)0.0294 (2)
O40.61784 (8)0.15025 (9)0.32857 (6)0.0216 (2)
O50.56142 (9)0.04303 (10)0.43694 (7)0.0277 (2)
O61.16021 (9)0.12662 (10)0.66952 (7)0.0274 (2)
H6O1.1607 (19)0.0925 (18)0.7251 (15)0.041*
O70.72501 (9)0.00250 (9)0.60260 (7)0.0240 (2)
H7O0.6519 (19)0.0059 (17)0.5546 (14)0.036*
O81.08114 (10)0.02204 (10)0.79484 (7)0.0299 (2)
C10.48601 (11)0.15799 (12)0.26991 (8)0.0182 (2)
C20.40202 (12)0.22551 (12)0.30214 (8)0.0199 (2)
H20.43310.26250.36360.024*
C30.27324 (12)0.23953 (12)0.24560 (8)0.0186 (2)
C40.23023 (11)0.18357 (11)0.15373 (8)0.0177 (2)
C50.32103 (12)0.12114 (11)0.12148 (8)0.0185 (2)
C60.45190 (12)0.10629 (11)0.18017 (9)0.0189 (2)
C70.54606 (14)0.03773 (14)0.14543 (11)0.0289 (3)
H7A0.58910.09450.11480.043*
H7B0.49920.02420.09900.043*
H7C0.61140.00190.19980.043*
C80.18933 (13)0.31664 (14)0.28570 (10)0.0275 (3)
H8A0.12570.26470.30050.041*
H8B0.14370.37810.23840.041*
H8C0.24410.35720.34430.041*
C90.09397 (12)0.18620 (12)0.08857 (9)0.0203 (2)
C100.12623 (13)0.22889 (16)0.06652 (11)0.0325 (3)
H10A0.13690.28100.01070.049*
H10B0.17970.26050.10270.049*
H10C0.15370.14570.04510.049*
C110.64570 (12)0.09578 (11)0.41488 (9)0.0186 (2)
C120.78207 (11)0.10492 (11)0.47735 (8)0.0163 (2)
C130.81263 (12)0.05667 (11)0.57094 (8)0.0172 (2)
C140.94016 (12)0.06362 (11)0.63768 (9)0.0185 (2)
C151.03717 (12)0.11816 (12)0.60878 (9)0.0197 (2)
C161.00832 (12)0.16495 (12)0.51672 (9)0.0199 (2)
H161.07550.20100.49860.024*
C170.88335 (12)0.15983 (11)0.45121 (9)0.0181 (2)
C180.86281 (13)0.21517 (14)0.35434 (9)0.0256 (3)
H18A0.94660.24170.35060.038*
H18B0.80450.28550.34490.038*
H18C0.82400.15440.30450.038*
C190.97066 (13)0.01870 (13)0.73465 (9)0.0237 (3)
H190.9011 (17)0.0163 (16)0.7525 (12)0.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0149 (4)0.0405 (6)0.0255 (5)0.0023 (4)0.0026 (4)0.0024 (4)
O20.0237 (5)0.0279 (5)0.0187 (4)0.0030 (4)0.0018 (4)0.0059 (4)
O30.0236 (5)0.0391 (6)0.0192 (4)0.0040 (4)0.0012 (4)0.0018 (4)
O40.0131 (4)0.0316 (5)0.0180 (4)0.0019 (3)0.0024 (3)0.0060 (4)
O50.0158 (4)0.0371 (6)0.0268 (5)0.0050 (4)0.0028 (4)0.0116 (4)
O60.0158 (4)0.0377 (6)0.0233 (5)0.0030 (4)0.0003 (4)0.0010 (4)
O70.0181 (4)0.0317 (5)0.0207 (4)0.0035 (4)0.0045 (4)0.0069 (4)
O80.0259 (5)0.0355 (6)0.0219 (4)0.0043 (4)0.0003 (4)0.0014 (4)
C10.0134 (5)0.0219 (6)0.0174 (5)0.0014 (4)0.0025 (4)0.0046 (4)
C20.0189 (6)0.0245 (6)0.0152 (5)0.0025 (5)0.0045 (4)0.0008 (4)
C30.0176 (5)0.0214 (6)0.0171 (5)0.0005 (4)0.0061 (4)0.0011 (4)
C40.0159 (5)0.0185 (5)0.0166 (5)0.0003 (4)0.0028 (4)0.0026 (4)
C50.0207 (6)0.0176 (5)0.0161 (5)0.0006 (4)0.0047 (4)0.0008 (4)
C60.0187 (6)0.0174 (5)0.0198 (5)0.0008 (4)0.0052 (4)0.0023 (4)
C70.0257 (7)0.0302 (7)0.0312 (7)0.0082 (6)0.0104 (6)0.0001 (6)
C80.0230 (6)0.0368 (8)0.0227 (6)0.0035 (6)0.0078 (5)0.0048 (6)
C90.0182 (6)0.0201 (6)0.0203 (5)0.0009 (5)0.0035 (4)0.0048 (5)
C100.0160 (6)0.0433 (9)0.0336 (7)0.0030 (6)0.0023 (5)0.0008 (6)
C110.0164 (5)0.0200 (6)0.0186 (5)0.0002 (4)0.0048 (4)0.0024 (4)
C120.0137 (5)0.0171 (5)0.0170 (5)0.0000 (4)0.0037 (4)0.0008 (4)
C130.0162 (5)0.0166 (5)0.0189 (5)0.0004 (4)0.0058 (4)0.0002 (4)
C140.0178 (5)0.0185 (6)0.0176 (5)0.0013 (4)0.0041 (4)0.0001 (4)
C150.0144 (5)0.0205 (6)0.0213 (5)0.0002 (4)0.0023 (4)0.0045 (5)
C160.0154 (5)0.0214 (6)0.0233 (6)0.0025 (4)0.0068 (5)0.0014 (5)
C170.0172 (5)0.0173 (5)0.0202 (5)0.0007 (4)0.0068 (4)0.0004 (4)
C180.0173 (6)0.0346 (7)0.0246 (6)0.0032 (5)0.0069 (5)0.0076 (5)
C190.0230 (6)0.0250 (6)0.0205 (6)0.0028 (5)0.0040 (5)0.0021 (5)
Geometric parameters (Å, º) top
O1—C91.3260 (16)C7—H7A0.9800
O1—C101.4515 (16)C7—H7B0.9800
O2—C51.3536 (15)C7—H7C0.9800
O2—H2O0.89 (2)C8—H8A0.9800
O3—C91.2294 (16)C8—H8B0.9800
O4—C111.3520 (15)C8—H8C0.9800
O4—C11.4119 (14)C10—H10A0.9800
O5—C111.2225 (15)C10—H10B0.9800
O6—C151.3456 (15)C10—H10C0.9800
O6—H6O0.90 (2)C11—C121.4688 (16)
O7—C131.3398 (15)C12—C131.4172 (16)
O7—H7O0.87 (2)C12—C171.4244 (17)
O8—C191.2363 (16)C13—C141.4131 (17)
C1—C61.3783 (17)C14—C151.4050 (18)
C1—C21.3847 (18)C14—C191.4497 (17)
C2—C31.3823 (17)C15—C161.3926 (18)
C2—H20.9500C16—C171.3844 (17)
C3—C41.4230 (17)C16—H160.9500
C3—C81.5099 (18)C17—C181.5063 (17)
C4—C51.4158 (17)C18—H18A0.9800
C4—C91.4767 (16)C18—H18B0.9800
C5—C61.4104 (17)C18—H18C0.9800
C6—C71.4998 (18)C19—H190.966 (18)
C9—O1—C10116.55 (11)O1—C9—C4114.79 (11)
C5—O2—H2O104.7 (12)O1—C10—H10A109.5
C11—O4—C1117.86 (9)O1—C10—H10B109.5
C15—O6—H6O106.2 (13)H10A—C10—H10B109.5
C13—O7—H7O105.0 (13)O1—C10—H10C109.5
C6—C1—C2124.04 (11)H10A—C10—H10C109.5
C6—C1—O4117.24 (11)H10B—C10—H10C109.5
C2—C1—O4118.46 (11)O5—C11—O4120.96 (11)
C3—C2—C1120.51 (11)O5—C11—C12123.98 (11)
C3—C2—H2119.7O4—C11—C12115.06 (10)
C1—C2—H2119.7C13—C12—C17118.53 (11)
C2—C3—C4118.21 (11)C13—C12—C11116.49 (10)
C2—C3—C8116.90 (11)C17—C12—C11124.97 (11)
C4—C3—C8124.87 (11)O7—C13—C14115.50 (10)
C5—C4—C3119.39 (11)O7—C13—C12123.37 (11)
C5—C4—C9117.05 (11)C14—C13—C12121.13 (11)
C3—C4—C9123.56 (11)C15—C14—C13118.44 (11)
O2—C5—C6115.51 (11)C15—C14—C19120.26 (11)
O2—C5—C4122.66 (11)C13—C14—C19121.28 (11)
C6—C5—C4121.83 (11)O6—C15—C16118.41 (11)
C1—C6—C5115.86 (11)O6—C15—C14120.74 (11)
C1—C6—C7123.08 (11)C16—C15—C14120.85 (11)
C5—C6—C7121.06 (11)C17—C16—C15121.12 (11)
C6—C7—H7A109.5C17—C16—H16119.4
C6—C7—H7B109.5C15—C16—H16119.4
H7A—C7—H7B109.5C16—C17—C12119.93 (11)
C6—C7—H7C109.5C16—C17—C18116.59 (11)
H7A—C7—H7C109.5C12—C17—C18123.48 (11)
H7B—C7—H7C109.5C17—C18—H18A109.5
C3—C8—H8A109.5C17—C18—H18B109.5
C3—C8—H8B109.5H18A—C18—H18B109.5
H8A—C8—H8B109.5C17—C18—H18C109.5
C3—C8—H8C109.5H18A—C18—H18C109.5
H8A—C8—H8C109.5H18B—C18—H18C109.5
H8B—C8—H8C109.5O8—C19—C14123.25 (13)
O3—C9—O1121.58 (12)O8—C19—H19118.7 (10)
O3—C9—C4123.61 (12)C14—C19—H19118.0 (10)
C11—O4—C1—C6122.35 (13)C1—O4—C11—O58.02 (18)
C11—O4—C1—C263.23 (15)C1—O4—C11—C12172.30 (11)
C6—C1—C2—C33.5 (2)O5—C11—C12—C134.84 (19)
O4—C1—C2—C3177.52 (11)O4—C11—C12—C13175.49 (11)
C1—C2—C3—C40.42 (18)O5—C11—C12—C17176.26 (13)
C1—C2—C3—C8178.85 (12)O4—C11—C12—C173.41 (18)
C2—C3—C4—C53.11 (18)C17—C12—C13—O7179.56 (11)
C8—C3—C4—C5175.18 (12)C11—C12—C13—O71.46 (18)
C2—C3—C4—C9176.71 (12)C17—C12—C13—C140.67 (18)
C8—C3—C4—C95.0 (2)C11—C12—C13—C14178.30 (11)
C3—C4—C5—O2177.17 (11)O7—C13—C14—C15179.32 (11)
C9—C4—C5—O23.00 (18)C12—C13—C14—C150.90 (18)
C3—C4—C5—C63.92 (18)O7—C13—C14—C192.26 (18)
C9—C4—C5—C6175.91 (11)C12—C13—C14—C19177.52 (12)
C2—C1—C6—C52.70 (18)C13—C14—C15—O6179.76 (11)
O4—C1—C6—C5176.78 (11)C19—C14—C15—O61.80 (19)
C2—C1—C6—C7177.47 (13)C13—C14—C15—C160.37 (18)
O4—C1—C6—C73.39 (18)C19—C14—C15—C16178.07 (12)
O2—C5—C6—C1179.97 (11)O6—C15—C16—C17179.49 (12)
C4—C5—C6—C11.05 (18)C14—C15—C16—C170.38 (19)
O2—C5—C6—C70.19 (18)C15—C16—C17—C120.61 (19)
C4—C5—C6—C7178.79 (12)C15—C16—C17—C18178.97 (12)
C10—O1—C9—O30.13 (19)C13—C12—C17—C160.09 (18)
C10—O1—C9—C4178.22 (12)C11—C12—C17—C16178.97 (12)
C5—C4—C9—O38.62 (19)C13—C12—C17—C18179.46 (12)
C3—C4—C9—O3171.55 (13)C11—C12—C17—C180.6 (2)
C5—C4—C9—O1169.70 (11)C15—C14—C19—O82.3 (2)
C3—C4—C9—O110.13 (18)C13—C14—C19—O8179.28 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O30.89 (2)1.72 (2)2.5515 (14)152.5 (18)
O6—H6O···O80.90 (2)1.74 (2)2.5711 (15)151.1 (18)
O7—H7O···O50.87 (2)1.74 (2)2.5437 (13)151.9 (18)
O7—H7O···O5i0.87 (2)2.437 (19)3.0251 (14)125.1 (16)
Symmetry code: (i) x+1, y, z+1.
 

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