(E)-2-(2-Furylmethyl-idene)-2,3-dihydro-1H-pyrrolizin-1-one.

The title compound, C(12)H(9)NO(2), was prepared by an Aldol reaction of furfuraldehyde with 2,3-dihydro-1H-pyrrolizin-1-one. The mol-ecule is almost planar, with an r.m.s. deviation of 0.045 Å, excluding the methyl-ene H atoms. In the crystal structure, mol-ecules are linked via weak inter-molecular C-H⋯O hydrogen bonding and aromatic π-π stacking [centroid-centroid distance = 3.6151 (9) Å].

Related literature

For general background to synthetic dihydro­pyrrolizines and for the biological activity of related structures, see: Meinwald & Meinwald (1965 ▶); Skvortsov & Astakhova (1992 ▶). For the preparation of the starting material, see: Clemo & Ramage (1931 ▶); Braunholtz et al. (1962 ▶).

Experimental

Crystal data

C12H9NO2

M = 199.20

Monoclinic,

a = 11.8170 (16) Å

b = 6.1242 (6) Å

c = 14.432 (2) Å

β = 113.157 (3)°

V = 960.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.22 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD camera diffractometer

9348 measured reflections

2271 independent reflections

1796 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.07

2271 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2009 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017939/xu2760sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017939/xu2760Isup2.hkl

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

C12H9NO2	F(000) = 416
Mr = 199.20	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 2971 reflections
a = 11.8170 (16) Å	θ = 1.5–28.0°
b = 6.1242 (6) Å	µ = 0.10 mm−1
c = 14.432 (2) Å	T = 113 K
β = 113.157 (3)°	Prism, colourless
V = 960.3 (2) Å3	0.22 × 0.18 × 0.12 mm
Z = 4

Rigaku Saturn724 CCD camera diffractometer	1796 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.025
multilayer	θmax = 27.9°, θmin = 1.9°
ω scans	h = −14→15
9348 measured reflections	k = −7→7
2271 independent reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.0917P] where P = (Fo2 + 2Fc2)/3
2271 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. Single crystals suitable for X-ray crystallography were grown by slow evaporatin from ethyl acetate solution and of by slow cooling of a hot saturated solution of Petroleum Ether. Crystals obtained from later were found more suitable for X ray analysis.

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
O1	0.81898 (7)	0.03138 (13)	0.87581 (6)	0.0268 (2)
O2	1.15722 (7)	0.60788 (13)	0.91369 (6)	0.0239 (2)
N1	0.76145 (8)	0.52826 (15)	0.74753 (7)	0.0190 (2)
C1	0.82061 (10)	0.21177 (18)	0.83928 (8)	0.0190 (2)
C2	0.71886 (10)	0.33225 (17)	0.76750 (8)	0.0187 (2)
C3	0.59277 (10)	0.32408 (19)	0.71216 (8)	0.0219 (3)
H3	0.5387	0.2083	0.7110	0.026*
C4	0.56100 (11)	0.52063 (19)	0.65837 (9)	0.0254 (3)
H4	0.4806	0.5618	0.6133	0.030*
C5	0.66732 (10)	0.64550 (18)	0.68219 (8)	0.0229 (3)
H5	0.6725	0.7869	0.6571	0.027*
C6	0.89436 (10)	0.56200 (19)	0.80194 (8)	0.0209 (2)
H6A	0.9119	0.6913	0.8466	0.025*
H6B	0.9363	0.5784	0.7550	0.025*
C7	0.93162 (10)	0.35275 (17)	0.86190 (8)	0.0182 (2)
C8	1.04282 (10)	0.29109 (18)	0.92790 (8)	0.0194 (2)
H8	1.0468	0.1525	0.9586	0.023*
C9	1.15627 (10)	0.40818 (18)	0.95782 (8)	0.0197 (2)
C10	1.27159 (10)	0.35966 (18)	1.02555 (8)	0.0221 (3)
H10	1.2959	0.2323	1.0662	0.026*
C11	1.34842 (10)	0.5362 (2)	1.02364 (8)	0.0238 (3)
H11	1.4342	0.5499	1.0626	0.029*
C12	1.27594 (10)	0.6803 (2)	0.95590 (8)	0.0247 (3)
H12	1.3037	0.8148	0.9396	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0259 (4)	0.0196 (4)	0.0298 (4)	−0.0021 (3)	0.0056 (4)	0.0068 (3)
O2	0.0229 (4)	0.0244 (4)	0.0219 (4)	−0.0043 (3)	0.0061 (3)	0.0043 (3)
N1	0.0198 (5)	0.0185 (5)	0.0183 (4)	0.0014 (4)	0.0070 (4)	0.0023 (4)
C1	0.0218 (6)	0.0175 (5)	0.0178 (5)	−0.0001 (4)	0.0079 (4)	−0.0011 (4)
C2	0.0212 (6)	0.0179 (5)	0.0180 (5)	0.0000 (4)	0.0087 (4)	0.0000 (4)
C3	0.0206 (6)	0.0244 (6)	0.0208 (5)	0.0000 (4)	0.0082 (4)	−0.0007 (4)
C4	0.0216 (6)	0.0292 (7)	0.0236 (5)	0.0067 (5)	0.0070 (5)	0.0015 (5)
C5	0.0256 (6)	0.0204 (6)	0.0218 (5)	0.0066 (5)	0.0084 (5)	0.0044 (4)
C6	0.0202 (6)	0.0203 (6)	0.0212 (5)	−0.0011 (4)	0.0072 (4)	0.0029 (4)
C7	0.0203 (6)	0.0177 (5)	0.0174 (5)	−0.0001 (4)	0.0083 (4)	0.0002 (4)
C8	0.0219 (5)	0.0187 (5)	0.0182 (5)	0.0002 (4)	0.0085 (4)	0.0006 (4)
C9	0.0227 (6)	0.0192 (5)	0.0186 (5)	−0.0001 (4)	0.0095 (4)	0.0002 (4)
C10	0.0211 (6)	0.0237 (6)	0.0207 (5)	−0.0003 (4)	0.0075 (4)	−0.0009 (4)
C11	0.0198 (6)	0.0297 (6)	0.0217 (5)	−0.0037 (5)	0.0078 (4)	−0.0036 (5)
C12	0.0236 (6)	0.0286 (6)	0.0222 (5)	−0.0090 (5)	0.0094 (5)	−0.0020 (5)

O1—C1	1.2274 (13)	C5—H5	0.9500
O2—C12	1.3652 (14)	C6—C7	1.5117 (14)
O2—C9	1.3810 (13)	C6—H6A	0.9900
N1—C5	1.3480 (14)	C6—H6B	0.9900
N1—C2	1.3754 (14)	C7—C8	1.3388 (14)
N1—C6	1.4683 (14)	C8—C9	1.4292 (15)
C1—C2	1.4435 (14)	C8—H8	0.9500
C1—C7	1.4953 (15)	C9—C10	1.3613 (15)
C2—C3	1.3873 (15)	C10—C11	1.4191 (16)
C3—C4	1.4011 (15)	C10—H10	0.9500
C3—H3	0.9500	C11—C12	1.3451 (17)
C4—C5	1.3935 (17)	C11—H11	0.9500
C4—H4	0.9500	C12—H12	0.9500
C12—O2—C9	105.97 (9)	N1—C6—H6B	111.5
C5—N1—C2	110.01 (9)	C7—C6—H6B	111.5
C5—N1—C6	135.57 (10)	H6A—C6—H6B	109.3
C2—N1—C6	114.42 (9)	C8—C7—C1	121.59 (10)
O1—C1—C2	128.24 (10)	C8—C7—C6	129.04 (10)
O1—C1—C7	125.91 (10)	C1—C7—C6	109.36 (9)
C2—C1—C7	105.85 (9)	C7—C8—C9	127.96 (11)
N1—C2—C3	108.03 (9)	C7—C8—H8	116.0
N1—C2—C1	109.05 (9)	C9—C8—H8	116.0
C3—C2—C1	142.91 (10)	C10—C9—O2	109.70 (10)
C2—C3—C4	106.33 (10)	C10—C9—C8	131.50 (11)
C2—C3—H3	126.8	O2—C9—C8	118.80 (9)
C4—C3—H3	126.8	C9—C10—C11	106.69 (10)
C5—C4—C3	108.40 (10)	C9—C10—H10	126.7
C5—C4—H4	125.8	C11—C10—H10	126.7
C3—C4—H4	125.8	C12—C11—C10	106.53 (10)
N1—C5—C4	107.23 (10)	C12—C11—H11	126.7
N1—C5—H5	126.4	C10—C11—H11	126.7
C4—C5—H5	126.4	C11—C12—O2	111.11 (10)
N1—C6—C7	101.32 (8)	C11—C12—H12	124.4
N1—C6—H6A	111.5	O2—C12—H12	124.4
C7—C6—H6A	111.5
C5—N1—C2—C3	0.38 (12)	C2—C1—C7—C8	178.79 (10)
C6—N1—C2—C3	179.39 (9)	O1—C1—C7—C6	−179.66 (11)
C5—N1—C2—C1	−178.70 (9)	C2—C1—C7—C6	0.05 (12)
C6—N1—C2—C1	0.31 (12)	N1—C6—C7—C8	−178.51 (11)
O1—C1—C2—N1	179.49 (11)	N1—C6—C7—C1	0.11 (11)
C7—C1—C2—N1	−0.21 (12)	C1—C7—C8—C9	−179.33 (10)
O1—C1—C2—C3	0.9 (2)	C6—C7—C8—C9	−0.85 (19)
C7—C1—C2—C3	−178.76 (14)	C12—O2—C9—C10	0.11 (12)
N1—C2—C3—C4	0.06 (12)	C12—O2—C9—C8	−179.84 (10)
C1—C2—C3—C4	178.62 (14)	C7—C8—C9—C10	178.22 (11)
C2—C3—C4—C5	−0.46 (12)	C7—C8—C9—O2	−1.85 (17)
C2—N1—C5—C4	−0.67 (13)	O2—C9—C10—C11	−0.21 (12)
C6—N1—C5—C4	−179.37 (11)	C8—C9—C10—C11	179.73 (11)
C3—C4—C5—N1	0.69 (13)	C9—C10—C11—C12	0.23 (13)
C5—N1—C6—C7	178.40 (12)	C10—C11—C12—O2	−0.17 (13)
C2—N1—C6—C7	−0.26 (11)	C9—O2—C12—C11	0.04 (12)
O1—C1—C7—C8	−0.91 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1i	0.99	2.47	3.3076 (15)	142
C8—H8···O1ii	0.95	2.55	3.3096 (14)	137
C10—H10···O1ii	0.95	2.46	3.1789 (15)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1i	0.99	2.47	3.3076 (15)	142
C8—H8⋯O1ii	0.95	2.55	3.3096 (14)	137
C10—H10⋯O1ii	0.95	2.46	3.1789 (15)	133

Symmetry codes: (i) ; (ii) .