(E)-3-[2,5-Dioxo-3-(propan-2-yl­idene)pyrrolidin-1-yl]acrylic acid

Miao, F.; Qin, B.-F.; Yang, L.-Z.; Yang, X.-J.; Zhou, L.

doi:10.1107/S1600536810005040

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o634

doi:10.1107/S1600536810005040

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(E)-3-[2,5-Dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl]acrylic acid

Fang Miao,^a Bao-Fu Qin,^a Li-Zhen Yang,^b Xin-Juan Yang ^a,^b and Le Zhou ^a,^b ^*

^aCollege of Life Science, Northwest A&F University, Yangling 712100, People's Republic of China, and ^bCollege of Science, Northwest A&F University, Yangling 712100, People's Republic of China
^*Correspondence e-mail: zhoulechem@yahoo.com.cn

(Received 1 February 2010; accepted 8 February 2010; online 13 February 2010)

The title compound, C₁₀H₁₁NO₄, was extracted from a culture broth of Penicillium verruculosum YL-52. The molecular structure is essentially planar, with an r.m.s. deviation of 0.01342 (2) Å for the non-H atoms. In the crystal structure, adjacent molecules are connected into a centrosymmetric dimer through a pair of O—H⋯O hydrogen bonds. The dimers are further extended into a chain by weak C—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Cheng et al. (2009 ). For details of Penicillium verruculosum YL-52, see: Yang et al. (2009 ).

Experimental

Crystal data

C₁₀H₁₁NO₄
M_r = 209.20
Triclinic, $[P \overline 1]$
a = 6.5384 (14) Å
b = 7.5309 (17) Å
c = 10.405 (2) Å
α = 93.009 (3)°
β = 101.247 (2)°
γ = 90.410 (3)°
V = 501.74 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.33 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.991
3845 measured reflections
1849 independent reflections
1255 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.125
S = 1.05
1849 reflections
139 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.83	2.647 (2)	174
C6—H6A⋯O4ⁱⁱ	0.97	2.60	3.399 (3)	140
Symmetry codes: (i) -x+3, -y+1, -z+2; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005040/is2521sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005040/is2521Isup2.hkl

checkCIF report

Comment top

Stellera chamaejasme L belongs to a toxic plant and its root has been used as Chinese traditional herb medicine in China. Our previous study resulted in isolating a fungal strain from the rhizosphere of Stellera Chamaejasme L identified as Penicillium verruculosum YL-52 (Yang et al., 2009). In this controbution, we reported the crystal structure of the title compound which was obtained from the culture broth of Penicillium verruculosum YL-52.

The bond lengths and angles of the title compound are within normal ranges (Cheng et al., 2009). In the crystal structure, the molecule, excluding methyl H atoms, is essentially planar, with an r.m.s. deviation of 0.01342 (2) Å. Moreover, adjacent two molecules are connected into a dimer through two head to head O1—H1···O2 hydrogen bonds. The dimers are further extended into a one-dimensional chain by weak C—H···O hydrogen bonds along the b axis, in which C6—H6A is donor and O4 is acceptor (Table 1 and Fig. 2).

Related literature top

For a related structure, see: Cheng et al. (2009). For details of Penicillium verruculosum YL-52, see: Yang et al. (2009).

Experimental top

The roots of Stellera Chamaejasme L was collected in Qinling mountain of Taibai town in Shaanxi province, P. R. China, in August, 2007, and the fungal strain was isolated from the rhizosphere of the plant above, and deposited in our laboratory of natural product research, Northwest A&F University, Shaanxi Province, the People's Republic of China (culture collection number YL-52), and identified as Penicillium verruculosum YL-52. Repeated column chromatography of ethyl acetate extract of the culture broth of Penicillium verruculosum YL-52 provided the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecular structure with atom numbering scheme and 30% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. View of the two-dimensional sheet (O—H···O and C—H···O hydrogen bonds are indicated as broken lines).

(E)-3-[2,5-Dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl]acrylic acid top

Crystal data top

C₁₀H₁₁NO₄	Z = 2
M_r = 209.20	F(000) = 220
Triclinic, P1	D_x = 1.385 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5384 (14) Å	Cell parameters from 773 reflections
b = 7.5309 (17) Å	θ = 0.0–0.0°
c = 10.405 (2) Å	µ = 0.11 mm⁻¹
α = 93.009 (3)°	T = 296 K
β = 101.247 (2)°	Block, colourless
γ = 90.410 (3)°	0.33 × 0.12 × 0.08 mm
V = 501.74 (19) Å³

Data collection top

Bruker APEXII CCD diffractometer	1849 independent reflections
Radiation source: fine-focus sealed tube	1255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.965, T_max = 0.991	k = −9→9
3845 measured reflections	l = −12→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0581P)² + 0.0541P] where P = (F_o² + 2F_c²)/3
1849 reflections	(Δ/σ)_max < 0.001
139 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₀H₁₁NO₄	γ = 90.410 (3)°
M_r = 209.20	V = 501.74 (19) Å³
Triclinic, P1	Z = 2
a = 6.5384 (14) Å	Mo Kα radiation
b = 7.5309 (17) Å	µ = 0.11 mm⁻¹
c = 10.405 (2) Å	T = 296 K
α = 93.009 (3)°	0.33 × 0.12 × 0.08 mm
β = 101.247 (2)°

Data collection top

Bruker APEXII CCD diffractometer	1849 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1255 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.991	R_int = 0.024
3845 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	Δρ_max = 0.17 e Å⁻³
1849 reflections	Δρ_min = −0.19 e Å⁻³
139 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O2	1.2795 (3)	0.5891 (2)	0.92347 (15)	0.0617 (5)
O1	1.5542 (3)	0.5091 (3)	0.83867 (17)	0.0664 (5)
H1	1.5982	0.4818	0.9142	0.100*
N1	0.9689 (2)	0.7432 (2)	0.55825 (16)	0.0375 (4)
O4	0.6865 (2)	0.8327 (2)	0.64451 (17)	0.0611 (5)
O3	1.2017 (2)	0.6881 (2)	0.42194 (15)	0.0555 (5)
C4	1.0334 (3)	0.7417 (3)	0.4361 (2)	0.0372 (5)
C3	1.0819 (3)	0.6860 (3)	0.6763 (2)	0.0403 (5)
H3	1.0143	0.6904	0.7472	0.048*
C5	0.8620 (3)	0.8155 (3)	0.3422 (2)	0.0382 (5)
C8	0.8650 (3)	0.8428 (3)	0.2160 (2)	0.0445 (6)
C2	1.2744 (3)	0.6264 (3)	0.6983 (2)	0.0437 (6)
H2	1.3491	0.6184	0.6309	0.052*
C1	1.3693 (3)	0.5730 (3)	0.8297 (2)	0.0441 (6)
C6	0.6859 (3)	0.8529 (3)	0.4118 (2)	0.0458 (6)
H6A	0.6463	0.9765	0.4060	0.055*
H6B	0.5654	0.7782	0.3743	0.055*
C7	0.7675 (3)	0.8117 (3)	0.5505 (2)	0.0433 (5)
C10	0.6796 (4)	0.9171 (3)	0.1284 (2)	0.0580 (7)
H10A	0.5714	0.9396	0.1773	0.087*
H10B	0.6294	0.8331	0.0563	0.087*
H10C	0.7192	1.0262	0.0953	0.087*
C9	1.0460 (4)	0.8041 (4)	0.1519 (3)	0.0675 (8)
H9A	1.1076	0.9138	0.1338	0.101*
H9B	0.9992	0.7347	0.0713	0.101*
H9C	1.1476	0.7388	0.2093	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0608 (11)	0.0854 (13)	0.0385 (10)	0.0281 (9)	0.0066 (8)	0.0098 (8)
O1	0.0544 (11)	0.0958 (14)	0.0481 (10)	0.0294 (10)	0.0024 (8)	0.0214 (10)
N1	0.0320 (9)	0.0440 (10)	0.0355 (10)	0.0051 (8)	0.0029 (8)	0.0055 (8)
O4	0.0491 (10)	0.0836 (12)	0.0550 (11)	0.0187 (9)	0.0177 (9)	0.0121 (9)
O3	0.0375 (9)	0.0838 (12)	0.0452 (9)	0.0178 (8)	0.0060 (7)	0.0105 (8)
C4	0.0296 (11)	0.0413 (12)	0.0396 (12)	0.0026 (9)	0.0032 (9)	0.0046 (9)
C3	0.0427 (13)	0.0417 (12)	0.0348 (12)	0.0027 (10)	0.0024 (10)	0.0065 (9)
C5	0.0328 (11)	0.0386 (12)	0.0413 (13)	0.0022 (9)	0.0014 (9)	0.0054 (9)
C8	0.0448 (13)	0.0447 (13)	0.0414 (13)	0.0022 (10)	0.0009 (10)	0.0051 (10)
C2	0.0446 (14)	0.0478 (13)	0.0373 (12)	0.0043 (11)	0.0027 (10)	0.0072 (10)
C1	0.0426 (13)	0.0442 (13)	0.0425 (13)	0.0081 (10)	0.0005 (11)	0.0045 (10)
C6	0.0360 (12)	0.0521 (13)	0.0480 (14)	0.0092 (10)	0.0033 (10)	0.0093 (11)
C7	0.0364 (12)	0.0478 (13)	0.0465 (14)	0.0048 (10)	0.0094 (11)	0.0055 (10)
C10	0.0571 (16)	0.0625 (16)	0.0484 (15)	0.0082 (12)	−0.0073 (12)	0.0138 (12)
C9	0.0633 (17)	0.093 (2)	0.0487 (15)	0.0124 (15)	0.0150 (13)	0.0130 (14)

Geometric parameters (Å, º) top

O2—C1	1.234 (3)	C8—C9	1.491 (3)
O1—C1	1.293 (3)	C8—C10	1.499 (3)
O1—H1	0.8200	C2—C1	1.465 (3)
N1—C3	1.395 (3)	C2—H2	0.9300
N1—C7	1.407 (3)	C6—C7	1.488 (3)
N1—C4	1.415 (3)	C6—H6A	0.9700
O4—C7	1.203 (3)	C6—H6B	0.9700
O3—C4	1.207 (2)	C10—H10A	0.9600
C4—C5	1.469 (3)	C10—H10B	0.9600
C3—C2	1.321 (3)	C10—H10C	0.9600
C3—H3	0.9300	C9—H9A	0.9600
C5—C8	1.343 (3)	C9—H9B	0.9600
C5—C6	1.496 (3)	C9—H9C	0.9600

C1—O1—H1	109.5	C7—C6—C5	105.09 (17)
C3—N1—C7	120.90 (18)	C7—C6—H6A	110.7
C3—N1—C4	127.07 (17)	C5—C6—H6A	110.7
C7—N1—C4	112.03 (17)	C7—C6—H6B	110.7
O3—C4—N1	122.39 (18)	C5—C6—H6B	110.7
O3—C4—C5	130.8 (2)	H6A—C6—H6B	108.8
N1—C4—C5	106.80 (17)	O4—C7—N1	122.9 (2)
C2—C3—N1	127.1 (2)	O4—C7—C6	129.1 (2)
C2—C3—H3	116.5	N1—C7—C6	107.93 (18)
N1—C3—H3	116.5	C8—C10—H10A	109.5
C8—C5—C4	125.4 (2)	C8—C10—H10B	109.5
C8—C5—C6	126.63 (19)	H10A—C10—H10B	109.5
C4—C5—C6	107.97 (18)	C8—C10—H10C	109.5
C5—C8—C9	124.3 (2)	H10A—C10—H10C	109.5
C5—C8—C10	120.9 (2)	H10B—C10—H10C	109.5
C9—C8—C10	114.8 (2)	C8—C9—H9A	109.5
C3—C2—C1	119.5 (2)	C8—C9—H9B	109.5
C3—C2—H2	120.2	H9A—C9—H9B	109.5
C1—C2—H2	120.2	C8—C9—H9C	109.5
O2—C1—O1	123.3 (2)	H9A—C9—H9C	109.5
O2—C1—C2	122.4 (2)	H9B—C9—H9C	109.5
O1—C1—C2	114.3 (2)

C3—N1—C4—O3	−0.1 (3)	C6—C5—C8—C10	−0.4 (3)
C7—N1—C4—O3	179.89 (19)	N1—C3—C2—C1	179.57 (19)
C3—N1—C4—C5	−179.71 (17)	C3—C2—C1—O2	−3.5 (3)
C7—N1—C4—C5	0.3 (2)	C3—C2—C1—O1	177.0 (2)
C7—N1—C3—C2	−176.9 (2)	C8—C5—C6—C7	−176.1 (2)
C4—N1—C3—C2	3.1 (3)	C4—C5—C6—C7	4.3 (2)
O3—C4—C5—C8	−2.1 (4)	C3—N1—C7—O4	3.7 (3)
N1—C4—C5—C8	177.4 (2)	C4—N1—C7—O4	−176.4 (2)
O3—C4—C5—C6	177.6 (2)	C3—N1—C7—C6	−177.54 (18)
N1—C4—C5—C6	−2.9 (2)	C4—N1—C7—C6	2.4 (2)
C4—C5—C8—C9	−0.8 (4)	C5—C6—C7—O4	174.6 (2)
C6—C5—C8—C9	179.6 (2)	C5—C6—C7—N1	−4.1 (2)
C4—C5—C8—C10	179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.83	2.647 (2)	174
C6—H6A···O4ⁱⁱ	0.97	2.60	3.399 (3)	140

Symmetry codes: (i) −x+3, −y+1, −z+2; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁NO₄
M_r	209.20
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.5384 (14), 7.5309 (17), 10.405 (2)
α, β, γ (°)	93.009 (3), 101.247 (2), 90.410 (3)
V (Å³)	501.74 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.33 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3845, 1849, 1255
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.125, 1.05
No. of reflections	1849
No. of parameters	139
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.83	2.647 (2)	174
C6—H6A···O4ⁱⁱ	0.97	2.60	3.399 (3)	140

Symmetry codes: (i) −x+3, −y+1, −z+2; (ii) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 30571402 and 30771454).

References

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