2,3-Dihydro-1H-pyrrolizin-1-one.

There are two nearly identical mol-ecules in the asymmetric unit of the title compound, C(7)H(7)NO. The mol-ecules are nearly planar (r.m.s. deviations of 0.025 and 0.017 Å) and oriented at a dihedral angle of 28.98 (3)°. The two mol-ecules are linked by a C-H⋯O hydrogen bond. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into zigzag chains along the c axis.

Related literature

For general background to 2,3-dihydro­pyrrolizine derivatives and their biological activity, see: Skvortsov & Astakhova (1992 ▶). For the preparation, see: Braunholtz et al. (1962 ▶); Clemo & Ramage (1931 ▶). For natural sources, see: Meinwald & Meinwald (1965 ▶).

Experimental

Crystal data

C7H7NO

M = 121.14

Monoclinic,

a = 11.301 (1) Å

b = 7.1730 (7) Å

c = 14.3760 (16) Å

β = 90.989 (5)°

V = 1165.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.12 × 0.06 × 0.04 mm

Data collection

Rigaku Saturn724 CCD camera diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ▶) T min = 0.989, T max = 0.996

10183 measured reflections

2284 independent reflections

2003 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.118

S = 1.16

2284 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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/S1600536810034902/bq2209sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034902/bq2209Isup2.hkl

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

C7H7NO	F(000) = 512
Mr = 121.14	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Melting point: 327(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71075 Å
a = 11.301 (1) Å	Cell parameters from 3403 reflections
b = 7.1730 (7) Å	θ = 1.8–28.1°
c = 14.3760 (16) Å	µ = 0.09 mm−1
β = 90.989 (5)°	T = 113 K
V = 1165.2 (2) Å3	Prism, colorless
Z = 8	0.12 × 0.06 × 0.04 mm

Rigaku Saturn724 CCD camera diffractometer	2284 independent reflections
Radiation source: rotating anode	2003 reflections with I > 2σ(I)
multilayer	Rint = 0.051
ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	h = −13→13
Tmin = 0.989, Tmax = 0.996	k = −8→8
10183 measured reflections	l = −17→15

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.043P)2 + 0.3505P] where P = (Fo2 + 2Fc2)/3
2284 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. Single crystals suitable for X-ray crystallography were grown by slow cooling of a hot saturated solution of Petroleum Ether.

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 RSHELXS-97 -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	0.84120 (12)	0.0832 (2)	0.57308 (9)	0.0293 (4)
O2	0.49964 (11)	0.0828 (2)	0.17318 (10)	0.0329 (4)
N1	0.72173 (13)	0.1521 (2)	0.35032 (11)	0.0181 (4)
N2	0.20229 (13)	0.1557 (2)	0.11650 (11)	0.0190 (4)
C1	0.78107 (17)	0.0987 (3)	0.50200 (13)	0.0214 (4)
C2	0.64640 (16)	0.0776 (3)	0.49734 (13)	0.0229 (5)
H2A	0.6086	0.1646	0.5413	0.027*
H2B	0.6233	−0.0513	0.5136	0.027*
C3	0.60795 (16)	0.1231 (3)	0.39650 (13)	0.0222 (4)
H3A	0.5634	0.0183	0.3680	0.027*
H3B	0.5586	0.2371	0.3938	0.027*
C4	0.81910 (16)	0.1386 (3)	0.40853 (13)	0.0186 (4)
C5	0.91883 (17)	0.1737 (3)	0.35603 (13)	0.0226 (4)
H5	0.9988	0.1728	0.3775	0.027*
C6	0.87834 (16)	0.2109 (3)	0.26502 (13)	0.0218 (4)
H6	0.9265	0.2405	0.2136	0.026*
C7	0.75535 (16)	0.1968 (3)	0.26317 (13)	0.0209 (4)
H7	0.7046	0.2152	0.2106	0.025*
C8	0.39292 (16)	0.1181 (3)	0.16955 (14)	0.0219 (4)
C9	0.32016 (16)	0.1840 (3)	0.25181 (13)	0.0223 (4)
H9A	0.3490	0.3065	0.2743	0.027*
H9B	0.3260	0.0934	0.3036	0.027*
C10	0.19132 (16)	0.1993 (3)	0.21584 (13)	0.0208 (4)
H10A	0.1395	0.1084	0.2472	0.025*
H10B	0.1596	0.3265	0.2250	0.025*
C11	0.31432 (15)	0.1065 (3)	0.09001 (13)	0.0186 (4)
C12	0.30999 (17)	0.0643 (3)	−0.00456 (14)	0.0223 (4)
H12	0.3741	0.0258	−0.0419	0.027*
C13	0.19207 (17)	0.0901 (3)	−0.03344 (14)	0.0239 (5)
H13	0.1615	0.0721	−0.0948	0.029*
C14	0.12721 (17)	0.1468 (3)	0.04322 (14)	0.0238 (5)
H14	0.0450	0.1741	0.0435	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0349 (8)	0.0343 (9)	0.0185 (8)	0.0044 (6)	−0.0039 (6)	−0.0005 (6)
O2	0.0195 (7)	0.0467 (10)	0.0324 (9)	0.0055 (6)	−0.0011 (6)	−0.0079 (7)
N1	0.0169 (7)	0.0209 (8)	0.0165 (8)	0.0002 (6)	0.0003 (6)	−0.0004 (7)
N2	0.0187 (8)	0.0195 (9)	0.0188 (9)	0.0013 (6)	0.0020 (7)	−0.0012 (7)
C1	0.0263 (10)	0.0175 (10)	0.0203 (11)	0.0021 (8)	−0.0006 (8)	−0.0020 (8)
C2	0.0280 (10)	0.0213 (10)	0.0196 (10)	−0.0017 (8)	0.0044 (8)	0.0000 (8)
C3	0.0179 (9)	0.0247 (10)	0.0241 (11)	−0.0019 (8)	0.0032 (8)	0.0006 (8)
C4	0.0198 (9)	0.0198 (10)	0.0160 (10)	0.0012 (7)	−0.0031 (8)	−0.0022 (8)
C5	0.0189 (9)	0.0254 (10)	0.0233 (11)	−0.0002 (8)	−0.0016 (8)	−0.0033 (9)
C6	0.0224 (10)	0.0237 (10)	0.0193 (10)	−0.0013 (8)	0.0032 (8)	−0.0003 (8)
C7	0.0238 (10)	0.0227 (10)	0.0161 (10)	0.0015 (8)	−0.0015 (8)	0.0016 (8)
C8	0.0207 (9)	0.0200 (10)	0.0249 (11)	−0.0004 (8)	0.0007 (8)	0.0004 (8)
C9	0.0230 (10)	0.0251 (10)	0.0187 (10)	−0.0004 (8)	0.0007 (8)	−0.0008 (8)
C10	0.0222 (10)	0.0228 (10)	0.0177 (10)	0.0015 (8)	0.0043 (8)	−0.0020 (8)
C11	0.0190 (9)	0.0183 (10)	0.0184 (10)	0.0016 (7)	0.0030 (8)	0.0000 (8)
C12	0.0267 (10)	0.0199 (10)	0.0204 (10)	0.0004 (8)	0.0039 (8)	−0.0003 (8)
C13	0.0307 (11)	0.0233 (11)	0.0176 (10)	0.0011 (8)	−0.0024 (8)	0.0005 (8)
C14	0.0222 (10)	0.0244 (11)	0.0246 (11)	0.0008 (8)	−0.0044 (8)	0.0001 (9)

O1—C1	1.222 (2)	C5—H5	0.9500
O2—C8	1.232 (2)	C6—C7	1.393 (2)
N1—C7	1.354 (2)	C6—H6	0.9500
N1—C4	1.374 (2)	C7—H7	0.9500
N1—C3	1.472 (2)	C8—C11	1.438 (3)
N2—C14	1.343 (2)	C8—C9	1.527 (3)
N2—C11	1.374 (2)	C9—C10	1.541 (3)
N2—C10	1.469 (2)	C9—H9A	0.9900
C1—C4	1.446 (3)	C9—H9B	0.9900
C1—C2	1.530 (3)	C10—H10A	0.9900
C2—C3	1.541 (3)	C10—H10B	0.9900
C2—H2A	0.9900	C11—C12	1.393 (3)
C2—H2B	0.9900	C12—C13	1.401 (3)
C3—H3A	0.9900	C12—H12	0.9500
C3—H3B	0.9900	C13—C14	1.395 (3)
C4—C5	1.390 (3)	C13—H13	0.9500
C5—C6	1.404 (3)	C14—H14	0.9500
C7—N1—C4	110.21 (16)	N1—C7—C6	107.17 (17)
C7—N1—C3	135.39 (16)	N1—C7—H7	126.4
C4—N1—C3	114.33 (15)	C6—C7—H7	126.4
C14—N2—C11	110.07 (16)	O2—C8—C11	127.76 (18)
C14—N2—C10	135.23 (16)	O2—C8—C9	124.78 (18)
C11—N2—C10	114.68 (15)	C11—C8—C9	107.47 (15)
O1—C1—C4	128.66 (18)	C8—C9—C10	106.29 (15)
O1—C1—C2	124.46 (18)	C8—C9—H9A	110.5
C4—C1—C2	106.88 (16)	C10—C9—H9A	110.5
C1—C2—C3	106.52 (15)	C8—C9—H9B	110.5
C1—C2—H2A	110.4	C10—C9—H9B	110.5
C3—C2—H2A	110.4	H9A—C9—H9B	108.7
C1—C2—H2B	110.4	N2—C10—C9	102.47 (14)
C3—C2—H2B	110.4	N2—C10—H10A	111.3
H2A—C2—H2B	108.6	C9—C10—H10A	111.3
N1—C3—C2	102.70 (14)	N2—C10—H10B	111.3
N1—C3—H3A	111.2	C9—C10—H10B	111.3
C2—C3—H3A	111.2	H10A—C10—H10B	109.2
N1—C3—H3B	111.2	N2—C11—C12	108.01 (16)
C2—C3—H3B	111.2	N2—C11—C8	108.92 (16)
H3A—C3—H3B	109.1	C12—C11—C8	143.08 (18)
N1—C4—C5	107.75 (16)	C11—C12—C13	106.13 (17)
N1—C4—C1	109.38 (16)	C11—C12—H12	126.9
C5—C4—C1	142.83 (17)	C13—C12—H12	126.9
C4—C5—C6	106.62 (16)	C14—C13—C12	108.33 (17)
C4—C5—H5	126.7	C14—C13—H13	125.8
C6—C5—H5	126.7	C12—C13—H13	125.8
C7—C6—C5	108.24 (17)	N2—C14—C13	107.47 (17)
C7—C6—H6	125.9	N2—C14—H14	126.3
C5—C6—H6	125.9	C13—C14—H14	126.3
O1—C1—C2—C3	175.74 (18)	O2—C8—C9—C10	−176.94 (19)
C4—C1—C2—C3	−4.4 (2)	C11—C8—C9—C10	3.2 (2)
C7—N1—C3—C2	−179.46 (19)	C14—N2—C10—C9	−178.40 (19)
C4—N1—C3—C2	−2.6 (2)	C11—N2—C10—C9	3.8 (2)
C1—C2—C3—N1	4.14 (19)	C8—C9—C10—N2	−4.05 (19)
C7—N1—C4—C5	−0.8 (2)	C14—N2—C11—C12	0.0 (2)
C3—N1—C4—C5	−178.45 (15)	C10—N2—C11—C12	178.29 (15)
C7—N1—C4—C1	177.53 (15)	C14—N2—C11—C8	179.72 (15)
C3—N1—C4—C1	−0.1 (2)	C10—N2—C11—C8	−2.0 (2)
O1—C1—C4—N1	−177.28 (18)	O2—C8—C11—N2	179.24 (19)
C2—C1—C4—N1	2.8 (2)	C9—C8—C11—N2	−0.9 (2)
O1—C1—C4—C5	0.1 (4)	O2—C8—C11—C12	−1.2 (4)
C2—C1—C4—C5	−179.7 (2)	C9—C8—C11—C12	178.7 (2)
N1—C4—C5—C6	0.7 (2)	N2—C11—C12—C13	0.1 (2)
C1—C4—C5—C6	−176.7 (2)	C8—C11—C12—C13	−179.6 (2)
C4—C5—C6—C7	−0.4 (2)	C11—C12—C13—C14	−0.1 (2)
C4—N1—C7—C6	0.6 (2)	C11—N2—C14—C13	0.0 (2)
C3—N1—C7—C6	177.51 (19)	C10—N2—C14—C13	−177.84 (19)
C5—C6—C7—N1	−0.1 (2)	C12—C13—C14—N2	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.55	3.151 (2)	121
C7—H7···O2	0.95	2.55	3.250 (2)	130
C12—H12···O2ii	0.95	2.51	3.435 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.55	3.151 (2)	121
C7—H7⋯O2	0.95	2.55	3.250 (2)	130
C12—H12⋯O2ii	0.95	2.51	3.435 (2)	165

Symmetry codes: (i) ; (ii) .