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

The title compound, C(10)H(11)NO(4), was extracted from a culture broth of Penicillium verruculosum YL-52. The mol-ecular 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 mol-ecules 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 = 209.20

Triclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.05

1849 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

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 ▶).

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

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

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

C10H11NO4	Z = 2
Mr = 209.20	F(000) = 220
Triclinic, P1	Dx = 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 = 0.00–0.00°
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

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

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(Fo2) + (0.0581P)2 + 0.0541P] where P = (Fo2 + 2Fc2)/3
1849 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .