(8aRS)-8,8a-Dihydro-furo[3,2-f]indolizine-6,9(4H,7H)-dione.

The title compound, C(10)H(9)NO(3), is a chiral mol-ecule with one stereogenic carbon atom, but which crystallizes as a racemate in the centrosymmetric space group P2(1)/n. The central six-membered ring of the indolizine moiety adopts a definite envelope conformation, while the conformation of the oxopyrrolidine ring is close to that of a flat-envelope with a maximum deviation of 0.352 (1) Å for the flap atom.

Related literature

For properties of indolizine derivatives, see: Malonne et al. (1998 ▶); Medda et al. (2003 ▶); Sonnet et al. (2000 ▶); Campagna et al. (1990 ▶); Pearson & Guo (2001 ▶); Gupta et al. (2003 ▶); Teklu et al. (2005 ▶). For their role as synthetic targets for pharmaceuticals, see: Gubin et al. (1992 ▶); Ruprecht et al. (1989 ▶). For the synthesis of the title compound, see: Szemes et al. (1998 ▶). For metric comparison with related compounds, see: Pedersen (1967 ▶).

Experimental

Crystal data

C10H9NO3

M = 191.18

Monoclinic,

a = 7.63534 (19) Å

b = 11.7583 (2) Å

c = 9.9234 (3) Å

β = 105.775 (3)°

V = 857.35 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.49 × 0.23 × 0.13 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.952, T max = 0.992

14552 measured reflections

2213 independent reflections

1646 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 1.03

2213 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027383/bg2407sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027383/bg2407Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027383/bg2407Isup3.cml

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

C10H9NO3	F(000) = 400
Mr = 191.18	Dx = 1.481 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7934 reflections
a = 7.63534 (19) Å	θ = 3.5–29.3°
b = 11.7583 (2) Å	µ = 0.11 mm−1
c = 9.9234 (3) Å	T = 298 K
β = 105.775 (3)°	Block, yellow
V = 857.35 (4) Å3	0.49 × 0.23 × 0.13 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	2213 independent reflections
Radiation source: fine-focus sealed tube	1646 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.4340 pixels mm-1	θmax = 29.4°, θmin = 3.5°
Rotation method data acquisition using ω and φ scans	h = −10→10
Absorption correction: analytical (Clark & Reid, 1995)	k = −15→14
Tmin = 0.952, Tmax = 0.992	l = −13→13
14552 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.063P)2 + 0.130P] where P = (Fo2 + 2Fc2)/3
2213 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Experimental. face-indexed (Oxford Diffraction, 2006)

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
C2	1.15109 (18)	0.99636 (12)	0.67889 (14)	0.0438 (3)
C3	1.3182 (2)	1.01426 (13)	0.62848 (17)	0.0543 (4)
H3B	1.4237	1.0285	0.7068	0.065*
H3A	1.3015	1.0783	0.5647	0.065*
C4	1.3418 (2)	0.90534 (14)	0.55443 (18)	0.0584 (4)
H4B	1.4692	0.8843	0.5756	0.070*
H4A	1.2938	0.9134	0.4538	0.070*
C5	1.23351 (17)	0.81624 (11)	0.61138 (14)	0.0439 (3)
H5A	1.3159	0.7767	0.6906	0.053*
C6	1.13528 (19)	0.72915 (11)	0.50495 (14)	0.0456 (3)
C7	0.96776 (18)	0.69128 (11)	0.53212 (13)	0.0429 (3)
C8	0.7398 (2)	0.58131 (13)	0.53142 (16)	0.0539 (4)
H8A	0.6557	0.5223	0.5095	0.065*
C9	0.74188 (18)	0.66085 (12)	0.62999 (14)	0.0475 (3)
H9A	0.6623	0.6671	0.6858	0.057*
C10	0.89106 (17)	0.73291 (11)	0.63038 (13)	0.0408 (3)
C11	0.96560 (19)	0.83359 (13)	0.71747 (14)	0.0483 (3)
H11B	0.8692	0.8880	0.7146	0.058*
H11A	1.0172	0.8106	0.8140	0.058*
N1	1.10563 (14)	0.88532 (10)	0.66294 (11)	0.0425 (3)
O1	1.07083 (16)	1.06761 (9)	0.72905 (13)	0.0636 (3)
O2	1.19841 (17)	0.69185 (9)	0.41368 (12)	0.0654 (3)
O3	0.87461 (14)	0.59746 (9)	0.46802 (10)	0.0535 (3)

	U11	U22	U33	U12	U13	U23
C2	0.0435 (6)	0.0436 (7)	0.0472 (7)	0.0004 (5)	0.0176 (5)	0.0013 (5)
C3	0.0515 (8)	0.0506 (8)	0.0679 (9)	−0.0066 (6)	0.0282 (7)	0.0042 (7)
C4	0.0544 (8)	0.0586 (9)	0.0760 (10)	−0.0066 (7)	0.0412 (8)	−0.0008 (7)
C5	0.0412 (6)	0.0457 (7)	0.0519 (7)	0.0039 (5)	0.0249 (6)	0.0033 (6)
C6	0.0541 (7)	0.0405 (7)	0.0511 (7)	0.0077 (6)	0.0294 (6)	0.0049 (5)
C7	0.0476 (7)	0.0408 (7)	0.0437 (7)	0.0003 (5)	0.0180 (6)	−0.0004 (5)
C8	0.0480 (8)	0.0501 (8)	0.0624 (9)	−0.0075 (6)	0.0131 (7)	0.0025 (7)
C9	0.0428 (7)	0.0526 (8)	0.0495 (7)	−0.0036 (6)	0.0169 (6)	0.0068 (6)
C10	0.0419 (6)	0.0441 (7)	0.0392 (6)	−0.0003 (5)	0.0161 (5)	0.0044 (5)
C11	0.0504 (7)	0.0550 (8)	0.0492 (7)	−0.0092 (6)	0.0301 (6)	−0.0073 (6)
N1	0.0428 (6)	0.0440 (6)	0.0487 (6)	−0.0026 (5)	0.0263 (5)	−0.0035 (5)
O1	0.0681 (7)	0.0486 (6)	0.0852 (8)	0.0021 (5)	0.0396 (6)	−0.0122 (5)
O2	0.0849 (8)	0.0569 (6)	0.0742 (7)	0.0039 (6)	0.0552 (7)	−0.0080 (5)
O3	0.0584 (6)	0.0480 (6)	0.0559 (6)	−0.0029 (4)	0.0188 (5)	−0.0085 (4)

C2—O1	1.2211 (16)	C6—C7	1.4472 (18)
C2—N1	1.3492 (18)	C7—C10	1.3578 (17)
C2—C3	1.5062 (18)	C7—O3	1.3717 (16)
C3—C4	1.512 (2)	C8—C9	1.350 (2)
C3—H3B	0.9700	C8—O3	1.3579 (18)
C3—H3A	0.9700	C8—H8A	0.9300
C4—C5	1.5345 (19)	C9—C10	1.4188 (18)
C4—H4B	0.9700	C9—H9A	0.9300
C4—H4A	0.9700	C10—C11	1.4848 (19)
C5—N1	1.4651 (15)	C11—N1	1.4562 (15)
C5—C6	1.515 (2)	C11—H11B	0.9700
C5—H5A	0.9800	C11—H11A	0.9700
C6—O2	1.2176 (16)
O1—C2—N1	124.75 (12)	C7—C6—C5	111.91 (10)
O1—C2—C3	127.14 (13)	C10—C7—O3	110.64 (11)
N1—C2—C3	108.08 (11)	C10—C7—C6	126.76 (13)
C2—C3—C4	105.48 (12)	O3—C7—C6	122.29 (11)
C2—C3—H3B	110.6	C9—C8—O3	112.18 (12)
C4—C3—H3B	110.6	C9—C8—H8A	123.9
C2—C3—H3A	110.6	O3—C8—H8A	123.9
C4—C3—H3A	110.6	C8—C9—C10	105.49 (12)
H3B—C3—H3A	108.8	C8—C9—H9A	127.3
C3—C4—C5	104.60 (11)	C10—C9—H9A	127.3
C3—C4—H4B	110.8	C7—C10—C9	106.58 (12)
C5—C4—H4B	110.8	C7—C10—C11	122.24 (11)
C3—C4—H4A	110.8	C9—C10—C11	131.16 (11)
C5—C4—H4A	110.8	N1—C11—C10	108.71 (10)
H4B—C4—H4A	108.9	N1—C11—H11B	109.9
N1—C5—C6	111.56 (10)	C10—C11—H11B	109.9
N1—C5—C4	103.12 (11)	N1—C11—H11A	109.9
C6—C5—C4	114.77 (12)	C10—C11—H11A	109.9
N1—C5—H5A	109.1	H11B—C11—H11A	108.3
C6—C5—H5A	109.1	C2—N1—C11	123.51 (10)
C4—C5—H5A	109.1	C2—N1—C5	113.76 (10)
O2—C6—C7	125.20 (14)	C11—N1—C5	121.64 (11)
O2—C6—C5	122.74 (13)	C8—O3—C7	105.10 (10)
O1—C2—C3—C4	−170.54 (15)	C8—C9—C10—C7	−0.07 (15)
N1—C2—C3—C4	11.15 (17)	C8—C9—C10—C11	−178.40 (15)
C2—C3—C4—C5	−20.30 (17)	C7—C10—C11—N1	9.17 (19)
C3—C4—C5—N1	21.70 (16)	C9—C10—C11—N1	−172.72 (13)
C3—C4—C5—C6	143.24 (13)	O1—C2—N1—C11	−6.8 (2)
N1—C5—C6—O2	152.99 (13)	C3—C2—N1—C11	171.60 (12)
C4—C5—C6—O2	36.17 (19)	O1—C2—N1—C5	−174.95 (14)
N1—C5—C6—C7	−31.17 (16)	C3—C2—N1—C5	3.41 (16)
C4—C5—C6—C7	−147.98 (12)	C10—C11—N1—C2	153.77 (12)
O2—C6—C7—C10	−178.15 (14)	C10—C11—N1—C5	−38.95 (17)
C5—C6—C7—C10	6.1 (2)	C6—C5—N1—C2	−139.84 (12)
O2—C6—C7—O3	9.0 (2)	C4—C5—N1—C2	−16.15 (16)
C5—C6—C7—O3	−166.75 (11)	C6—C5—N1—C11	51.73 (16)
O3—C8—C9—C10	−0.56 (16)	C4—C5—N1—C11	175.42 (12)
O3—C7—C10—C9	0.67 (15)	C9—C8—O3—C7	0.96 (16)
C6—C7—C10—C9	−172.91 (13)	C10—C7—O3—C8	−0.99 (15)
O3—C7—C10—C11	179.19 (12)	C6—C7—O3—C8	172.92 (13)
C6—C7—C10—C11	5.6 (2)