Oxonium 2-carb-oxy-3-(2-fur-yl)acrylate.

In the title compound, H(3)O(+)·C(8)H(5)O(5) (-), neighbouring cations and anions are linked by O-H⋯O hydrogen bonds, forming a one-dimensional chain framework along [001]. The crystal structure is further stabilized by π-π inter-actions, with centroid-centroid distances of 3.734 (3) Å.

Related literature

For the synthesis of β-amino­acids as precursors of novel biologically active compounds, see: O’Callaghan, et al. (1998 ▶); Cohen et al. (2002 ▶); Zeller et al. (1965 ▶).

Experimental

Crystal data

H3O+·C8H5O5 −

M = 200.14

Monoclinic,

a = 13.664 (3) Å

b = 8.7518 (18) Å

c = 7.4664 (15) Å

β = 99.13 (3)°

V = 881.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.50 × 0.45 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.935, T max = 0.980

7954 measured reflections

1727 independent reflections

1406 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.218

S = 1.06

1727 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.75 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017760/rz2321sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017760/rz2321Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

H3O+·C8H5O5−	F(000) = 416
Mr = 200.14	Dx = 1.508 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1406 reflections
a = 13.664 (3) Å	θ = 3.1–27.4°
b = 8.7518 (18) Å	µ = 0.13 mm−1
c = 7.4664 (15) Å	T = 293 K
β = 99.13 (3)°	Prism, colourless
V = 881.5 (3) Å3	0.50 × 0.45 × 0.15 mm
Z = 4

Rigaku SCXmini diffractometer	1727 independent reflections
Radiation source: fine-focus sealed tube	1406 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.0°
CCD profile fitting scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.935, Tmax = 0.980	l = −9→9
7954 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071	H-atom parameters constrained
wR(F2) = 0.218	w = 1/[σ2(Fo2) + (0.1228P)2 + 1.0867P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1727 reflections	Δρmax = 0.46 e Å−3
128 parameters	Δρmin = −0.74 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)

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.

	x	y	z	Uiso*/Ueq
C1	0.6364 (2)	0.3648 (4)	0.3879 (4)	0.0326 (7)
C2	0.6705 (3)	0.2258 (4)	0.3518 (5)	0.0471 (9)
H2	0.7334	0.2021	0.3275	0.057*
C3	0.5905 (3)	0.1220 (4)	0.3582 (6)	0.0552 (10)
H3	0.5918	0.0168	0.3408	0.066*
C4	0.5149 (3)	0.2026 (5)	0.3932 (6)	0.0548 (10)
H4	0.4530	0.1626	0.4032	0.066*
C5	0.6780 (2)	0.5157 (3)	0.4112 (4)	0.0316 (7)
H5	0.6393	0.5894	0.4562	0.038*
C6	0.7666 (2)	0.5621 (3)	0.3751 (4)	0.0294 (7)
C7	0.8392 (2)	0.4604 (3)	0.3007 (4)	0.0281 (7)
C8	0.8008 (2)	0.7221 (3)	0.4080 (4)	0.0299 (7)
O1	0.53944 (18)	0.3521 (3)	0.4129 (4)	0.0502 (7)
O2	0.73994 (16)	0.8126 (3)	0.4760 (3)	0.0389 (6)
H2A	0.7694	0.8902	0.5153	0.058*
O3	0.88184 (17)	0.7637 (3)	0.3750 (3)	0.0436 (7)
O4	0.84296 (16)	0.4683 (2)	0.1332 (3)	0.0354 (6)
O5	0.89313 (18)	0.3763 (3)	0.4078 (3)	0.0431 (6)
O1W	0.9457 (2)	0.4115 (3)	0.7823 (4)	0.0579 (8)
H1WC	0.9463	0.4130	0.8963	0.087*
H1WA	0.9797	0.3362	0.7549	0.087*
H1WB	0.9703	0.4941	0.7495	0.087*

	U11	U22	U33	U12	U13	U23
C1	0.0310 (16)	0.0324 (16)	0.0356 (16)	−0.0014 (12)	0.0094 (12)	0.0014 (12)
C2	0.0446 (19)	0.0367 (19)	0.059 (2)	0.0089 (15)	0.0065 (16)	−0.0065 (16)
C3	0.068 (3)	0.0307 (18)	0.064 (2)	−0.0096 (18)	0.001 (2)	−0.0026 (17)
C4	0.050 (2)	0.048 (2)	0.067 (3)	−0.0196 (18)	0.0112 (18)	−0.0031 (19)
C5	0.0362 (17)	0.0269 (15)	0.0333 (15)	0.0027 (12)	0.0106 (12)	−0.0005 (12)
C6	0.0336 (16)	0.0230 (14)	0.0319 (15)	0.0023 (12)	0.0062 (12)	−0.0003 (11)
C7	0.0301 (15)	0.0205 (13)	0.0344 (16)	−0.0016 (11)	0.0074 (12)	0.0002 (11)
C8	0.0331 (16)	0.0250 (14)	0.0318 (15)	0.0008 (12)	0.0061 (12)	−0.0013 (12)
O1	0.0416 (14)	0.0451 (15)	0.0675 (17)	−0.0090 (11)	0.0199 (12)	−0.0047 (12)
O2	0.0382 (12)	0.0280 (11)	0.0521 (14)	0.0001 (9)	0.0120 (10)	−0.0121 (10)
O3	0.0409 (13)	0.0333 (12)	0.0602 (16)	−0.0059 (10)	0.0195 (11)	−0.0077 (11)
O4	0.0447 (13)	0.0290 (12)	0.0352 (12)	0.0061 (9)	0.0149 (9)	0.0025 (9)
O5	0.0481 (14)	0.0401 (13)	0.0397 (12)	0.0148 (11)	0.0030 (10)	0.0027 (10)
O1W	0.0586 (17)	0.0583 (17)	0.0589 (17)	−0.0026 (14)	0.0162 (13)	0.0010 (13)

C1—C2	1.345 (5)	C6—C8	1.485 (4)
C1—O1	1.372 (4)	C6—C7	1.503 (4)
C1—C5	1.437 (4)	C7—O5	1.240 (4)
C2—C3	1.428 (6)	C7—O4	1.262 (4)
C2—H2	0.9300	C8—O3	1.226 (4)
C3—C4	1.311 (6)	C8—O2	1.308 (4)
C3—H3	0.9300	O2—H2A	0.8200
C4—O1	1.352 (5)	O1W—H1WC	0.8500
C4—H4	0.9300	O1W—H1WA	0.8500
C5—C6	1.344 (4)	O1W—H1WB	0.8500
C5—H5	0.9300
C2—C1—O1	109.0 (3)	C5—C6—C8	121.5 (3)
C2—C1—C5	135.4 (3)	C5—C6—C7	124.3 (3)
O1—C1—C5	115.5 (3)	C8—C6—C7	114.3 (2)
C1—C2—C3	106.1 (3)	O5—C7—O4	123.9 (3)
C1—C2—H2	126.9	O5—C7—C6	118.2 (3)
C3—C2—H2	126.9	O4—C7—C6	117.8 (3)
C4—C3—C2	107.2 (3)	O3—C8—O2	123.2 (3)
C4—C3—H3	126.4	O3—C8—C6	121.1 (3)
C2—C3—H3	126.4	O2—C8—C6	115.6 (3)
C3—C4—O1	110.7 (3)	C4—O1—C1	107.0 (3)
C3—C4—H4	124.7	C8—O2—H2A	109.5
O1—C4—H4	124.7	H1WC—O1W—H1WA	109.5
C6—C5—C1	127.2 (3)	H1WC—O1W—H1WB	109.5
C6—C5—H5	116.4	H1WA—O1W—H1WB	109.5
C1—C5—H5	116.4

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O4i	0.85	2.58	3.044 (4)	115
O1W—H1WA···O3i	0.85	2.42	3.188 (4)	150
O1W—H1WC···O4ii	0.85	2.48	3.201 (4)	143
O2—H2A···O4iii	0.82	1.74	2.552 (3)	169

Group 1	Group 2	α /°	DCC /Å	τ /°
Cg1	Cg1i	16.42	3.734 (3)	19.96

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O4i	0.85	2.58	3.044 (4)	115
O1W—H1WA⋯O3i	0.85	2.42	3.188 (4)	150
O1W—H1WC⋯O4ii	0.85	2.48	3.201 (4)	143
O2—H2A⋯O4iii	0.82	1.74	2.552 (3)	169

Symmetry codes: (i) ; (ii) ; (iii) .