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Mol­ecules of the title compound C8H10O3, are connected by an inter­molecular hydrogen bond. The mol­ecules form a cylindrical torus stacking along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043145/bt2209sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043145/bt2209Isup2.hkl
Contains datablock I

CCDC reference: 627361

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.053
  • wR factor = 0.169
  • Data-to-parameter ratio = 27.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 1.00 mm
Alert level C PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2 - H2A ... 1.01 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: P3/PC Software (Siemens, 1991); cell refinement: P3/PC Software; data reduction: XDISK in SHELXTL-Plus (Sheldrick, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

3-(5-Methylfuran-2-yl)propanoic acid top
Crystal data top
C8H10O3Z = 2
Mr = 154.16F(000) = 164
Triclinic, P1Dx = 1.267 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.1267 (8) ÅCell parameters from 25 reflections
b = 8.7271 (14) Åθ = 16–17°
c = 9.9620 (16) ŵ = 0.10 mm1
α = 106.035 (13)°T = 293 K
β = 98.723 (13)°Block, colourless
γ = 104.061 (13)°1.0 × 0.8 × 0.5 mm
V = 403.93 (11) Å3
Data collection top
Nicolet P3
diffractometer
Rint = 0.030
Radiation source: fine-focus sealed tubeθmax = 32.5°, θmin = 2.2°
Graphite monochromatorh = 07
Wyckoff–Scan scansk = 1312
3195 measured reflectionsl = 1514
2913 independent reflections3 standard reflections every 50 reflections
2403 reflections with I > 2σ(I) intensity decay: 5%
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)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0963P)2 + 0.0182P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
2913 reflectionsΔρmax = 0.23 e Å3
106 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.64 (6)
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
O10.08969 (16)0.81541 (9)0.39090 (8)0.0494 (2)
C10.1914 (2)0.74273 (12)0.27786 (10)0.0451 (2)
C20.0752 (3)0.57570 (14)0.23212 (13)0.0557 (3)
H20.10870.49780.15710.067*
C30.1102 (3)0.54167 (14)0.32177 (13)0.0587 (3)
H30.22010.43710.31590.070*
C40.0954 (2)0.68973 (13)0.41621 (11)0.0488 (2)
C50.2285 (3)0.74009 (18)0.53657 (14)0.0646 (3)
H5A0.32230.81880.52120.097*
H5B0.09000.79080.62520.097*
H5C0.35960.64330.54110.097*
C60.4014 (2)0.85767 (13)0.23428 (11)0.0493 (2)
H6A0.56010.91740.31470.059*
H6B0.32350.93920.20830.059*
C70.4942 (2)0.76207 (13)0.10774 (11)0.0507 (2)
H7A0.56770.67920.13410.061*
H7B0.33420.70300.02790.061*
C80.7078 (2)0.86955 (13)0.05938 (10)0.0463 (2)
O20.7885 (2)0.78570 (11)0.04949 (10)0.0660 (3)
H2A0.949 (5)0.861 (3)0.071 (2)0.093 (6)*
O30.80123 (18)1.02164 (10)0.11528 (9)0.0587 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0553 (4)0.0416 (3)0.0513 (4)0.0128 (3)0.0209 (3)0.0123 (3)
C10.0461 (4)0.0439 (4)0.0467 (4)0.0155 (3)0.0149 (3)0.0131 (3)
C20.0625 (6)0.0431 (5)0.0592 (6)0.0145 (4)0.0221 (5)0.0102 (4)
C30.0671 (6)0.0436 (5)0.0638 (6)0.0095 (4)0.0231 (5)0.0170 (4)
C40.0522 (5)0.0471 (5)0.0495 (5)0.0128 (4)0.0169 (4)0.0186 (4)
C50.0731 (7)0.0661 (7)0.0590 (6)0.0177 (6)0.0310 (5)0.0216 (5)
C60.0497 (5)0.0455 (5)0.0529 (5)0.0131 (4)0.0185 (4)0.0138 (4)
C70.0504 (5)0.0476 (5)0.0537 (5)0.0142 (4)0.0188 (4)0.0128 (4)
C80.0461 (4)0.0494 (5)0.0440 (4)0.0171 (4)0.0132 (3)0.0124 (4)
O20.0787 (6)0.0513 (4)0.0681 (5)0.0172 (4)0.0405 (4)0.0091 (4)
O30.0640 (5)0.0492 (4)0.0584 (4)0.0112 (3)0.0274 (4)0.0085 (3)
Geometric parameters (Å, º) top
O1—C41.3734 (13)C5—H5C0.9600
O1—C11.3735 (11)C6—C71.5181 (14)
C1—C21.3477 (14)C6—H6A0.9700
C1—C61.4873 (14)C6—H6B0.9700
C2—C31.4337 (18)C7—C81.4906 (14)
C2—H20.9300C7—H7A0.9700
C3—C41.3489 (17)C7—H7B0.9700
C3—H30.9300C8—O31.2260 (13)
C4—C51.4833 (15)C8—O21.3145 (12)
C5—H5A0.9600O2—H2A1.01 (2)
C5—H5B0.9600
C4—O1—C1107.56 (8)H5B—C5—H5C109.5
C2—C1—O1109.60 (9)C1—C6—C7111.06 (9)
C2—C1—C6134.01 (9)C1—C6—H6A109.4
O1—C1—C6116.37 (8)C7—C6—H6A109.4
C1—C2—C3106.53 (10)C1—C6—H6B109.4
C1—C2—H2126.7C7—C6—H6B109.4
C3—C2—H2126.7H6A—C6—H6B108.0
C4—C3—C2107.20 (10)C8—C7—C6113.96 (9)
C4—C3—H3126.4C8—C7—H7A108.8
C2—C3—H3126.4C6—C7—H7A108.8
C3—C4—O1109.11 (9)C8—C7—H7B108.8
C3—C4—C5134.08 (11)C6—C7—H7B108.8
O1—C4—C5116.80 (9)H7A—C7—H7B107.7
C4—C5—H5A109.5O3—C8—O2122.73 (10)
C4—C5—H5B109.5O3—C8—C7123.69 (9)
H5A—C5—H5B109.5O2—C8—C7113.58 (9)
C4—C5—H5C109.5C8—O2—H2A110.8 (12)
H5A—C5—H5C109.5
C4—O1—C1—C20.00 (12)C1—O1—C4—C30.01 (12)
C4—O1—C1—C6178.85 (8)C1—O1—C4—C5179.07 (9)
O1—C1—C2—C30.01 (13)C2—C1—C6—C72.10 (18)
C6—C1—C2—C3178.55 (11)O1—C1—C6—C7179.42 (8)
C1—C2—C3—C40.02 (14)C1—C6—C7—C8179.29 (8)
C2—C3—C4—O10.02 (14)C6—C7—C8—O30.31 (15)
C2—C3—C4—C5178.85 (13)C6—C7—C8—O2179.50 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O3i1.01 (2)1.63 (2)2.6436 (14)176.5 (18)
Symmetry code: (i) x+2, y+2, z.
 

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