3-(5-Methyl­furan-2-yl)propanoic acid

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

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

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Computing details

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

Crystal data

C8H10O3	Z = 2
Mr = 154.16	F(000) = 164
Triclinic, P1	Dx = 1.267 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1267 (8) Å	Cell parameters from 25 reflections
b = 8.7271 (14) Å	θ = 16–17°
c = 9.9620 (16) Å	µ = 0.10 mm^−1
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) Å^3

Data collection

Nicolet P3 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 32.5°, θmin = 2.2°
Graphite monochromator	h = 0→7
Wyckoff–Scan scans	k = −13→12
3195 measured reflections	l = −15→14
2913 independent reflections	3 standard reflections every 50 reflections
2403 reflections with I > 2σ(I)	intensity decay: 5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.169	w = 1/[σ^2(Fo^2) + (0.0963P)^2 + 0.0182P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
2913 reflections	Δρmax = 0.23 e Å^−3
106 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.64 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.08969 (16)	0.81541 (9)	0.39090 (8)	0.0494 (2)
C1	0.1914 (2)	0.74273 (12)	0.27786 (10)	0.0451 (2)
C2	0.0752 (3)	0.57570 (14)	0.23212 (13)	0.0557 (3)
H2	0.1087	0.4978	0.1571	0.067*
C3	−0.1102 (3)	0.54167 (14)	0.32177 (13)	0.0587 (3)
H3	−0.2201	0.4371	0.3159	0.070*
C4	−0.0954 (2)	0.68973 (13)	0.41621 (11)	0.0488 (2)
C5	−0.2285 (3)	0.74009 (18)	0.53657 (14)	0.0646 (3)
H5A	−0.3223	0.8188	0.5212	0.097*
H5B	−0.0900	0.7908	0.6252	0.097*
H5C	−0.3596	0.6433	0.5411	0.097*
C6	0.4014 (2)	0.85767 (13)	0.23428 (11)	0.0493 (2)
H6A	0.5601	0.9174	0.3147	0.059*
H6B	0.3235	0.9392	0.2083	0.059*
C7	0.4942 (2)	0.76207 (13)	0.10774 (11)	0.0507 (2)
H7A	0.5677	0.6792	0.1341	0.061*
H7B	0.3342	0.7030	0.0279	0.061*
C8	0.7078 (2)	0.86955 (13)	0.05938 (10)	0.0463 (2)
O2	0.7885 (2)	0.78570 (11)	−0.04949 (10)	0.0660 (3)
H2A	0.949 (5)	0.861 (3)	−0.071 (2)	0.093 (6)*
O3	0.80123 (18)	1.02164 (10)	0.11528 (9)	0.0587 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0553 (4)	0.0416 (3)	0.0513 (4)	0.0128 (3)	0.0209 (3)	0.0123 (3)
C1	0.0461 (4)	0.0439 (4)	0.0467 (4)	0.0155 (3)	0.0149 (3)	0.0131 (3)
C2	0.0625 (6)	0.0431 (5)	0.0592 (6)	0.0145 (4)	0.0221 (5)	0.0102 (4)
C3	0.0671 (6)	0.0436 (5)	0.0638 (6)	0.0095 (4)	0.0231 (5)	0.0170 (4)
C4	0.0522 (5)	0.0471 (5)	0.0495 (5)	0.0128 (4)	0.0169 (4)	0.0186 (4)
C5	0.0731 (7)	0.0661 (7)	0.0590 (6)	0.0177 (6)	0.0310 (5)	0.0216 (5)
C6	0.0497 (5)	0.0455 (5)	0.0529 (5)	0.0131 (4)	0.0185 (4)	0.0138 (4)
C7	0.0504 (5)	0.0476 (5)	0.0537 (5)	0.0142 (4)	0.0188 (4)	0.0128 (4)
C8	0.0461 (4)	0.0494 (5)	0.0440 (4)	0.0171 (4)	0.0132 (3)	0.0124 (4)
O2	0.0787 (6)	0.0513 (4)	0.0681 (5)	0.0172 (4)	0.0405 (4)	0.0091 (4)
O3	0.0640 (5)	0.0492 (4)	0.0584 (4)	0.0112 (3)	0.0274 (4)	0.0085 (3)

Geometric parameters (Å, º)

O1—C4	1.3734 (13)	C5—H5C	0.9600
O1—C1	1.3735 (11)	C6—C7	1.5181 (14)
C1—C2	1.3477 (14)	C6—H6A	0.9700
C1—C6	1.4873 (14)	C6—H6B	0.9700
C2—C3	1.4337 (18)	C7—C8	1.4906 (14)
C2—H2	0.9300	C7—H7A	0.9700
C3—C4	1.3489 (17)	C7—H7B	0.9700
C3—H3	0.9300	C8—O3	1.2260 (13)
C4—C5	1.4833 (15)	C8—O2	1.3145 (12)
C5—H5A	0.9600	O2—H2A	1.01 (2)
C5—H5B	0.9600
C4—O1—C1	107.56 (8)	H5B—C5—H5C	109.5
C2—C1—O1	109.60 (9)	C1—C6—C7	111.06 (9)
C2—C1—C6	134.01 (9)	C1—C6—H6A	109.4
O1—C1—C6	116.37 (8)	C7—C6—H6A	109.4
C1—C2—C3	106.53 (10)	C1—C6—H6B	109.4
C1—C2—H2	126.7	C7—C6—H6B	109.4
C3—C2—H2	126.7	H6A—C6—H6B	108.0
C4—C3—C2	107.20 (10)	C8—C7—C6	113.96 (9)
C4—C3—H3	126.4	C8—C7—H7A	108.8
C2—C3—H3	126.4	C6—C7—H7A	108.8
C3—C4—O1	109.11 (9)	C8—C7—H7B	108.8
C3—C4—C5	134.08 (11)	C6—C7—H7B	108.8
O1—C4—C5	116.80 (9)	H7A—C7—H7B	107.7
C4—C5—H5A	109.5	O3—C8—O2	122.73 (10)
C4—C5—H5B	109.5	O3—C8—C7	123.69 (9)
H5A—C5—H5B	109.5	O2—C8—C7	113.58 (9)
C4—C5—H5C	109.5	C8—O2—H2A	110.8 (12)
H5A—C5—H5C	109.5
C4—O1—C1—C2	0.00 (12)	C1—O1—C4—C3	0.01 (12)
C4—O1—C1—C6	−178.85 (8)	C1—O1—C4—C5	179.07 (9)
O1—C1—C2—C3	−0.01 (13)	C2—C1—C6—C7	2.10 (18)
C6—C1—C2—C3	178.55 (11)	O1—C1—C6—C7	−179.42 (8)
C1—C2—C3—C4	0.02 (14)	C1—C6—C7—C8	−179.29 (8)
C2—C3—C4—O1	−0.02 (14)	C6—C7—C8—O3	−0.31 (15)
C2—C3—C4—C5	−178.85 (13)	C6—C7—C8—O2	179.50 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3^i	1.01 (2)	1.63 (2)	2.6436 (14)	176.5 (18)

Symmetry code: (i) −x+2, −y+2, −z.