2,5-Dioxopyrrolidin-1-yl 3-(furan-2-yl)acrylate

Zhu, H.; Guo, M.; Chen, H.; Jin, H.; Liang, H.

doi:10.1107/S1600536811040566

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2863

doi:10.1107/S1600536811040566

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2,5-Dioxopyrrolidin-1-yl 3-(furan-2-yl)acrylate

Haifeng Zhu,^a Miao Guo,^a Han Chen,^a Haixiao Jin ^a and Hongze Liang ^a ^*

^aFaculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: lianghongze@nbu.edu.cn

(Received 2 September 2011; accepted 3 October 2011; online 8 October 2011)

The title compound, C₁₁H₉NO₅, was prepared by the reaction of 2-furanacrylic acid and N-hydroxysuccinimide. The molecule consists of two approximately planar moieties, viz. a succinimide group and the rest of the molecule [the largest deviations from the least-squares planes are 0.120 (1) and 0.210 (1) Å, respectively]. The dihedral angle between these fragments is 63.70 (5)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into two-dimensional nets.

Related literature

For derivatives of N-hydroxysuccinimide, see: Anderson et al. (1964 ); Blumberg & Vallee (1975 ); Brown et al. (2005 ); Cheng et al. (2007 ); Jones (2003 ).

Experimental

Crystal data

C₁₁H₉NO₅
M_r = 235.19
Orthorhombic, P b c a
a = 10.3054 (13) Å
b = 9.2376 (12) Å
c = 21.892 (3) Å
V = 2084.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.977, T_max = 0.977
16939 measured reflections
2399 independent reflections
1900 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.082
S = 1.02
2399 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.93	2.48	3.3533 (17)	156
C14—H14A⋯O5ⁱⁱ	0.93	2.45	3.3672 (18)	169
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y-1, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040566/yk2020sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040566/yk2020Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040566/yk2020Isup3.cml

checkCIF report

Comment top

N-Hydroxysuccinimide is frequently used in organic chemistry as an activating reagent, which readily form crystalline adducts with amines or acids (Jones, 2003). N-Hydroxysuccinimide esters are widely used as leaving groups to activate carboxylic acids (Cheng et al., 2007). The title compound N-(2-furanacryloyl)-succinimide ester is an intermediate of FAPGG which is the substrate of diagnostic reagent. We have used a simple procedure to synthesize the title compound in reasonable yields (Blumberg & Vallee, 1975; Brown et al., 2005).

The molecular structure of the title compound (I) is shown in Fig.1. In the molecule, the dihedral angle between the furan and succinimide rings is 56.26 (43)°. In the crystal structure, molecules are linked by the C12—H12···O1ⁱ hydrogen bonds to form chains along a and C14—H14···O5ⁱⁱ hydrogen bonds to form chains along b directions.

Related literature top

For derivatives of N-hydroxysuccinimide, see: Anderson et al. (1964); Blumberg & Vallee (1975); Brown et al. (2005); Cheng et al. (2007); Jones (2003).

Experimental top

2-Furanacrylic acid (13.81 g, 0.10 mol), N-hydroxysuccinimide (11.51 g, 0.10 mol) and dicyclohexylcarbodiimide (20.63 g, 0.10 mol) were added to 200 ml dioxane in a round flask. This mixture was stirred at 4°C for 14 h before the dicyclohexylurea was removed by filtration. Then the resulting dark brown filtrate was evaporated in vacuum to give the dark brown residue. Slight brown crystals were obtained by recrystallization from 2-propanol (15.29 g, 65%). 1H NMR(400 MHz, CDCl3): \d 7.62 (d, J=16 Hz, 1H), 7.56 (d, J=1.6 Hz, 1H), 6.77 (d, J=3.6 Hz, 1H), 6.53–6.52 (dd, J=3.6 Hz, J=1.6 Hz, 1H), 6.47 (d, J=16 Hz, 1H), 2.87 (s, 4H).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 30% probability level.

2,5-Dioxopyrrolidin-1-yl 3-(furan-2-yl)acrylate top

Crystal data top

C₁₁H₉NO₅	F(000) = 976
M_r = 235.19	D_x = 1.499 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ac 2ab	Cell parameters from 3779 reflections
a = 10.3054 (13) Å	θ = 2.7–27.4°
b = 9.2376 (12) Å	µ = 0.12 mm⁻¹
c = 21.892 (3) Å	T = 296 K
V = 2084.0 (5) Å³	Needle, brown
Z = 8	0.30 × 0.30 × 0.10 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2399 independent reflections
Radiation source: fine-focus sealed tube	1900 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 0 pixels mm^-1	θ_max = 27.6°, θ_min = 1.9°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
T_min = 0.977, T_max = 0.977	l = −28→28
16939 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0285P)² + 0.9232P] where P = (F_o² + 2F_c²)/3
2399 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₁H₉NO₅	V = 2084.0 (5) Å³
M_r = 235.19	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.3054 (13) Å	µ = 0.12 mm⁻¹
b = 9.2376 (12) Å	T = 296 K
c = 21.892 (3) Å	0.30 × 0.30 × 0.10 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2399 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1900 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.977	R_int = 0.041
16939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
2399 reflections	Δρ_min = −0.24 e Å⁻³
154 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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

	x	y	z	U_iso*/U_eq
O1	0.80658 (9)	0.22692 (10)	0.28201 (4)	0.0261 (2)
O2	0.89760 (9)	0.55049 (10)	0.10826 (4)	0.0273 (2)
O3	0.67881 (9)	0.58836 (11)	0.11454 (5)	0.0314 (2)
O4	0.81461 (10)	0.44760 (11)	−0.00431 (5)	0.0356 (3)
O5	1.01727 (10)	0.81990 (11)	0.09170 (5)	0.0349 (3)
C6	0.68207 (13)	0.36659 (14)	0.21024 (6)	0.0237 (3)
H6A	0.6008	0.3944	0.1960	0.028*
C7	0.78634 (13)	0.42777 (14)	0.18443 (6)	0.0244 (3)
H7A	0.8686	0.4048	0.1989	0.029*
N8	0.89355 (11)	0.63213 (12)	0.05495 (5)	0.0246 (3)
C9	0.68679 (12)	0.26114 (14)	0.25831 (6)	0.0220 (3)
C10	0.77299 (13)	0.52965 (14)	0.13407 (6)	0.0233 (3)
C11	0.96337 (13)	0.76125 (14)	0.04991 (6)	0.0243 (3)
C12	0.59420 (14)	0.18035 (14)	0.28687 (6)	0.0255 (3)
H12A	0.5054	0.1829	0.2793	0.031*
C13	0.85503 (13)	0.56972 (15)	0.00020 (6)	0.0250 (3)
C14	0.65847 (14)	0.09163 (15)	0.33025 (6)	0.0270 (3)
H14A	0.6205	0.0249	0.3566	0.032*
C15	0.78534 (14)	0.12362 (15)	0.32556 (6)	0.0279 (3)
H15A	0.8503	0.0810	0.3489	0.034*
C16	0.87575 (15)	0.68378 (15)	−0.04765 (6)	0.0289 (3)
H16A	0.7934	0.7229	−0.0614	0.035*
H16B	0.9214	0.6439	−0.0826	0.035*
C17	0.95729 (14)	0.80146 (15)	−0.01663 (6)	0.0286 (3)
H17A	1.0438	0.8046	−0.0341	0.034*
H17B	0.9170	0.8956	−0.0217	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0231 (5)	0.0287 (5)	0.0264 (5)	−0.0003 (4)	−0.0014 (4)	0.0072 (4)
O2	0.0248 (5)	0.0329 (5)	0.0242 (5)	−0.0006 (4)	−0.0008 (4)	0.0097 (4)
O3	0.0272 (5)	0.0337 (5)	0.0334 (5)	0.0032 (4)	−0.0018 (4)	0.0105 (4)
O4	0.0398 (6)	0.0254 (5)	0.0416 (6)	−0.0037 (5)	−0.0043 (5)	−0.0042 (5)
O5	0.0351 (6)	0.0322 (5)	0.0376 (6)	−0.0055 (5)	−0.0022 (5)	−0.0085 (5)
C6	0.0264 (7)	0.0222 (6)	0.0226 (6)	0.0026 (5)	−0.0019 (5)	−0.0008 (5)
C7	0.0253 (7)	0.0243 (7)	0.0235 (7)	0.0016 (6)	−0.0028 (5)	0.0022 (5)
N8	0.0284 (6)	0.0253 (6)	0.0199 (5)	−0.0037 (5)	−0.0009 (5)	0.0052 (5)
C9	0.0222 (6)	0.0232 (6)	0.0208 (6)	0.0025 (5)	−0.0012 (5)	−0.0009 (5)
C10	0.0245 (7)	0.0215 (6)	0.0238 (6)	−0.0014 (6)	−0.0009 (5)	0.0000 (5)
C11	0.0211 (6)	0.0211 (6)	0.0309 (7)	0.0008 (5)	0.0032 (6)	−0.0016 (6)
C12	0.0245 (7)	0.0251 (7)	0.0268 (7)	−0.0017 (6)	0.0018 (5)	−0.0016 (5)
C13	0.0239 (7)	0.0243 (7)	0.0269 (7)	0.0037 (6)	−0.0016 (6)	−0.0025 (5)
C14	0.0363 (8)	0.0227 (6)	0.0220 (6)	−0.0047 (6)	0.0031 (6)	0.0010 (5)
C15	0.0359 (8)	0.0253 (7)	0.0226 (6)	0.0014 (6)	−0.0030 (6)	0.0065 (6)
C16	0.0355 (8)	0.0283 (7)	0.0229 (7)	0.0055 (6)	0.0013 (6)	0.0007 (6)
C17	0.0280 (7)	0.0246 (7)	0.0333 (8)	0.0012 (6)	0.0048 (6)	0.0068 (6)

Geometric parameters (Å, º) top

O1—C15	1.3664 (16)	C9—C12	1.3632 (18)
O1—C9	1.3759 (15)	C11—C17	1.5044 (19)
O2—N8	1.3900 (13)	C12—C14	1.4185 (19)
O2—C10	1.4162 (16)	C12—H12A	0.9300
O3—C10	1.1912 (16)	C13—C16	1.5011 (19)
O4—C13	1.2066 (16)	C14—C15	1.344 (2)
O5—C11	1.1996 (16)	C14—H14A	0.9300
C6—C7	1.3391 (18)	C15—H15A	0.9300
C6—C9	1.4348 (18)	C16—C17	1.533 (2)
C6—H6A	0.9300	C16—H16A	0.9700
C7—C10	1.4561 (18)	C16—H16B	0.9700
C7—H7A	0.9300	C17—H17A	0.9700
N8—C13	1.3880 (17)	C17—H17B	0.9700
N8—C11	1.3974 (17)

C15—O1—C9	106.25 (10)	C14—C12—H12A	126.4
N8—O2—C10	112.43 (9)	O4—C13—N8	123.89 (13)
C7—C6—C9	124.66 (12)	O4—C13—C16	130.41 (12)
C7—C6—H6A	117.7	N8—C13—C16	105.69 (11)
C9—C6—H6A	117.7	C15—C14—C12	106.01 (12)
C6—C7—C10	121.09 (12)	C15—C14—H14A	127.0
C6—C7—H7A	119.5	C12—C14—H14A	127.0
C10—C7—H7A	119.5	C14—C15—O1	111.26 (12)
C13—N8—O2	120.55 (11)	C14—C15—H15A	124.4
C13—N8—C11	115.69 (11)	O1—C15—H15A	124.4
O2—N8—C11	120.93 (11)	C13—C16—C17	105.46 (11)
C12—C9—O1	109.22 (11)	C13—C16—H16A	110.6
C12—C9—C6	133.19 (13)	C17—C16—H16A	110.6
O1—C9—C6	117.58 (11)	C13—C16—H16B	110.6
O3—C10—O2	122.25 (12)	C17—C16—H16B	110.6
O3—C10—C7	130.02 (13)	H16A—C16—H16B	108.8
O2—C10—C7	107.72 (11)	C11—C17—C16	106.07 (11)
O5—C11—N8	124.31 (13)	C11—C17—H17A	110.5
O5—C11—C17	130.25 (13)	C16—C17—H17A	110.5
N8—C11—C17	105.42 (11)	C11—C17—H17B	110.5
C9—C12—C14	107.25 (12)	C16—C17—H17B	110.5
C9—C12—H12A	126.4	H17A—C17—H17B	108.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.93	2.48	3.3533 (17)	156
C14—H14A···O5ⁱⁱ	0.93	2.45	3.3672 (18)	169

Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x−1/2, y−1, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₉NO₅
M_r	235.19
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	10.3054 (13), 9.2376 (12), 21.892 (3)
V (Å³)	2084.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.977, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	16939, 2399, 1900
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.082, 1.02
No. of reflections	2399
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.93	2.4831	3.3533 (17)	155.80
C14—H14A···O5ⁱⁱ	0.9301	2.4502	3.3672 (18)	168.93

Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x−1/2, y−1, −z+1/2.

Acknowledgements

This project was supported by Zhejiang Provincial Natural Science Foundation of China (grant No. Y4100113), the National Natural Science Foundation of China (grant No. 20903058), the Natural Science Foundation of Ningbo City (grant Nos. 2009 A610047, 2010 A610025, 2010 A610027) and the K. C. Wong Magna Fund of Ningbo University.

References

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