Download citation
Download citation
link to html
In the crystal structure of the title compound, C10H12O4, mol­ecules are linked into dimers through O—H...O hydrogen bonds. The dimers are further linked through C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041377/hk2147sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041377/hk2147Isup2.hkl
Contains datablock I

CCDC reference: 627802

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C)= 0.001 Å
  • R factor = 0.037
  • wR factor = 0.111
  • Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

(I) top
Crystal data top
C10H12O4Z = 2
Mr = 196.20F(000) = 208.00
Triclinic, P1Dx = 1.366 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 7.3211 (3) ÅCell parameters from 6151 reflections
b = 8.3536 (4) Åθ = 3.1–30.0°
c = 8.5798 (4) ŵ = 0.11 mm1
α = 88.847 (2)°T = 150 K
β = 75.7410 (19)°Block, colorless
γ = 70.0857 (19)°0.55 × 0.50 × 0.25 mm
V = 476.97 (4) Å3
Data collection top
Rigaku RAXIS-RAPID II
diffractometer
2301 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.031
ω scansθmax = 30.0°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.850, Tmax = 0.974k = 1111
7011 measured reflectionsl = 1112
2687 independent reflections
Refinement top
Refinement on F2140 parameters
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0634P)2 + 0.086P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.29 e Å3
2687 reflectionsΔρmin = 0.32 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*/UeqOcc. (<1)
O10.50299 (12)0.20765 (9)0.50292 (10)0.03001 (18)
O20.33729 (11)0.08888 (8)0.38392 (9)0.02661 (17)
O30.39058 (12)0.22523 (8)0.09065 (8)0.02831 (18)
O40.07362 (12)0.82553 (8)0.12510 (9)0.02782 (18)
C10.30530 (13)0.37886 (10)0.34056 (10)0.01800 (17)
C20.30590 (13)0.37919 (10)0.17533 (10)0.01980 (18)
C30.22875 (13)0.53113 (11)0.10681 (10)0.02102 (18)
H30.23060.53120.00200.025*
C40.14833 (13)0.68379 (11)0.20279 (11)0.02028 (18)
C50.14658 (13)0.68605 (10)0.36508 (10)0.01975 (18)
H50.09220.78900.42740.024*
C60.22656 (12)0.53363 (10)0.43470 (10)0.01795 (17)
C70.38594 (13)0.21432 (10)0.41187 (10)0.01870 (17)
C80.38676 (17)0.21950 (13)0.07482 (12)0.0298 (2)
H8A0.25010.26360.08260.045*
H8B0.44800.10360.11980.045*
H8C0.45960.28750.13330.045*
C90.0101 (2)0.98688 (12)0.21640 (14)0.0354 (3)
H9A0.11920.98570.30490.053*
H9B0.05861.07570.14840.053*
H9C0.09151.00750.25710.053*
C100.21727 (14)0.54317 (11)0.61205 (10)0.02157 (18)
H10A0.34910.52500.62550.032*
H10B0.16900.45700.66340.032*
H10C0.12780.65370.66010.032*
H10.544 (4)0.115 (4)0.535 (3)0.025 (8)*0.56 (4)
H20.392 (6)0.004 (5)0.418 (5)0.041 (13)*0.44 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0372 (4)0.0232 (3)0.0361 (4)0.0091 (3)0.0233 (3)0.0089 (3)
O20.0359 (4)0.0165 (3)0.0303 (4)0.0093 (3)0.0135 (3)0.0040 (3)
O30.0426 (4)0.0174 (3)0.0181 (3)0.0006 (3)0.0093 (3)0.0026 (2)
O40.0424 (4)0.0155 (3)0.0233 (3)0.0036 (3)0.0138 (3)0.0044 (2)
C10.0208 (4)0.0148 (3)0.0180 (4)0.0044 (3)0.0068 (3)0.0018 (3)
C20.0235 (4)0.0159 (4)0.0179 (4)0.0039 (3)0.0055 (3)0.0006 (3)
C30.0264 (4)0.0185 (4)0.0165 (4)0.0049 (3)0.0064 (3)0.0018 (3)
C40.0236 (4)0.0158 (3)0.0212 (4)0.0052 (3)0.0079 (3)0.0040 (3)
C50.0234 (4)0.0147 (3)0.0204 (4)0.0050 (3)0.0065 (3)0.0002 (3)
C60.0200 (4)0.0165 (3)0.0179 (4)0.0061 (3)0.0062 (3)0.0014 (3)
C70.0213 (4)0.0154 (3)0.0178 (4)0.0039 (3)0.0056 (3)0.0004 (3)
C80.0423 (6)0.0249 (4)0.0187 (4)0.0062 (4)0.0086 (4)0.0034 (3)
C90.0545 (7)0.0161 (4)0.0300 (5)0.0020 (4)0.0158 (5)0.0031 (4)
C100.0275 (4)0.0205 (4)0.0173 (4)0.0079 (3)0.0072 (3)0.0009 (3)
Geometric parameters (Å, º) top
O1—C71.2819 (11)C4—C51.3898 (12)
O1—H10.80 (3)C5—C61.3980 (11)
O2—C71.2605 (11)C5—H50.9300
O2—H20.83 (4)C6—C101.5088 (12)
O3—C21.3560 (10)C8—H8A0.9599
O3—C81.4289 (11)C8—H8B0.9599
O4—C41.3609 (10)C8—H8C0.9599
O4—C91.4314 (12)C9—H9A0.9599
C1—C61.4004 (11)C9—H9B0.9599
C1—C21.4165 (12)C9—H9C0.9599
C1—C71.4844 (11)C10—H10A0.9599
C2—C31.3859 (11)C10—H10B0.9599
C3—C41.3940 (12)C10—H10C0.9599
C3—H30.9300
C7—O1—H1111.8 (17)O2—C7—O1122.52 (8)
C7—O2—H2119 (2)O2—C7—C1120.32 (8)
C2—O3—C8117.80 (7)O1—C7—C1117.15 (7)
C4—O4—C9117.73 (7)O3—C8—H8A109.5
C6—C1—C2119.52 (7)O3—C8—H8B109.5
C6—C1—C7120.95 (7)H8A—C8—H8B109.5
C2—C1—C7119.52 (7)O3—C8—H8C109.5
O3—C2—C3123.31 (8)H8A—C8—H8C109.5
O3—C2—C1116.18 (7)H8B—C8—H8C109.5
C3—C2—C1120.49 (8)O4—C9—H9A109.5
C2—C3—C4119.25 (8)O4—C9—H9B109.5
C2—C3—H3120.4H9A—C9—H9B109.5
C4—C3—H3120.4O4—C9—H9C109.5
O4—C4—C5124.09 (8)H9A—C9—H9C109.5
O4—C4—C3114.82 (8)H9B—C9—H9C109.5
C5—C4—C3121.09 (8)C6—C10—H10A109.5
C4—C5—C6120.05 (8)C6—C10—H10B109.5
C4—C5—H5120.0H10A—C10—H10B109.5
C6—C5—H5120.0C6—C10—H10C109.5
C5—C6—C1119.59 (8)H10A—C10—H10C109.5
C5—C6—C10117.82 (7)H10B—C10—H10C109.5
C1—C6—C10122.55 (7)
C8—O3—C2—C34.46 (14)O4—C4—C5—C6179.87 (8)
C8—O3—C2—C1177.53 (8)C3—C4—C5—C60.09 (14)
C6—C1—C2—O3177.87 (8)C4—C5—C6—C11.01 (13)
C7—C1—C2—O32.85 (13)C4—C5—C6—C10178.89 (8)
C6—C1—C2—C30.20 (13)C2—C1—C6—C51.07 (13)
C7—C1—C2—C3179.08 (8)C7—C1—C6—C5178.21 (8)
O3—C2—C3—C4178.64 (8)C2—C1—C6—C10178.84 (8)
C1—C2—C3—C40.72 (14)C7—C1—C6—C100.43 (13)
C9—O4—C4—C50.63 (14)C6—C1—C7—O2133.29 (9)
C9—O4—C4—C3179.58 (9)C2—C1—C7—O245.99 (12)
C2—C3—C4—O4179.02 (8)C6—C1—C7—O145.88 (12)
C2—C3—C4—C50.78 (14)C2—C1—C7—O1134.85 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.80 (2)1.84 (2)2.6335 (9)172 (3)
O2—H2···O1i0.83 (4)1.81 (4)2.6335 (9)177 (4)
C9—H9C···O2ii0.962.593.5477 (17)174
C9—H9B···O4iii0.962.493.3536 (14)150
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1, z; (iii) x, y+2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds