Diethyl indolizine-1,3-dicarboxyl-ate.

The title compound, C(14)H(15)NO(4), was prepared by a 1,3-dipolar cyclo-addition from N-(eth-oxy-carbonyl-methy)pyridinium bromide and ethyl acrylate. The -CO(2) side chains form dihedral angles of 0.2 (3) and 2.4 (3)° with respect to the ring system. In the crystal, two neighbouring mol-ecules form a dimer through weak C-H⋯O interactions. The dimers form a three-dimensional structure via further weak C-H⋯O inter-actions.

Related literature

For synthetic procedures, see: Teklu et al. (2005 ▶), Wang et al. (2000 ▶). For the pharmaceutical use of related compounds, see: James et al. (2008 ▶), Tukulula et al. (2010 ▶). For the use of related compounds as organic fluorescence probes, see: Shen et al. (2006 ▶, 2008 ▶).

Experimental

Crystal data

C14H15NO4

M = 261.27

Monoclinic,

a = 7.941 (2) Å

b = 19.700 (4) Å

c = 8.622 (2) Å

β = 101.770 (3)°

V = 1320.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 291 K

0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.972, T max = 0.977

7930 measured reflections

2400 independent reflections

1567 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.116

S = 1.05

2400 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050919/im2246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050919/im2246Isup2.hkl

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

C14H15NO4	F(000) = 552
Mr = 261.27	Dx = 1.314 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1756 reflections
a = 7.941 (2) Å	θ = 2.6–22.7°
b = 19.700 (4) Å	µ = 0.10 mm−1
c = 8.622 (2) Å	T = 291 K
β = 101.770 (3)°	Block, colorless
V = 1320.5 (5) Å3	0.30 × 0.26 × 0.24 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2400 independent reflections
Radiation source: sealed tube	1567 reflections with I > 2σ(I)
graphite	Rint = 0.039
phi and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.972, Tmax = 0.977	k = −23→23
7930 measured reflections	l = −10→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.04P)2 + 0.33P] where P = (Fo2 + 2Fc2)/3
2400 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)6.9517 (0.0017) x + 8.0272 (0.0048) y - 3.7352 (0.0022) z = 3.8065 (0.0031)* 0.0092 (0.0021) C1 * -0.0460 (0.0022) C2 * -0.0746 (0.0022) C3 * -0.0551 (0.0020) C4 * -0.0046 (0.0019) C5 * 0.0272 (0.0020) C6 * 0.0632 (0.0020) C7 * 0.0674 (0.0020) C8 * 0.0094 (0.0021) C9 * -0.0124 (0.0023) C10 * -0.0150 (0.0021) C11 * 0.0555 (0.0020) C12 * -0.0638 (0.0022) C13 * -0.0916 (0.0022) C14 * 0.0286 (0.0017) N1 * -0.0164 (0.0017) O1 * 0.0319 (0.0017) O2 * 0.0148 (0.0016) O3 * 0.0723 (0.0017) O4Rms deviation of fitted atoms = 0.0479

	x	y	z	Uiso*/Ueq
C1	0.3394 (3)	0.57688 (11)	0.8498 (3)	0.0612 (6)
H1	0.4111	0.5441	0.9062	0.073*
C2	0.3039 (3)	0.63422 (12)	0.9219 (3)	0.0693 (7)
H2	0.3508	0.6409	1.0288	0.083*
C3	0.1963 (3)	0.68414 (12)	0.8365 (3)	0.0690 (7)
H3	0.1732	0.7237	0.8871	0.083*
C4	0.1266 (3)	0.67502 (11)	0.6820 (3)	0.0599 (6)
H4	0.0555	0.7082	0.6263	0.072*
C5	0.1613 (3)	0.61567 (9)	0.6055 (3)	0.0468 (5)
C6	0.1093 (3)	0.59243 (10)	0.4502 (3)	0.0524 (6)
C7	0.1841 (3)	0.52881 (10)	0.4431 (3)	0.0552 (6)
H7	0.1701	0.5015	0.3534	0.066*
C8	0.2815 (3)	0.51264 (10)	0.5885 (3)	0.0526 (6)
C9	−0.0036 (3)	0.62911 (11)	0.3236 (3)	0.0579 (6)
C10	−0.1463 (3)	0.62404 (12)	0.0531 (3)	0.0710 (7)
H10A	−0.0954	0.6662	0.0268	0.085*
H10B	−0.2587	0.6339	0.0752	0.085*
C11	−0.1616 (4)	0.57481 (13)	−0.0806 (3)	0.0770 (8)
H11A	−0.0491	0.5640	−0.0982	0.116*
H11B	−0.2291	0.5946	−0.1748	0.116*
H11C	−0.2166	0.5341	−0.0549	0.116*
C12	0.3783 (3)	0.45130 (11)	0.6400 (3)	0.0573 (6)
C13	0.4462 (3)	0.34094 (11)	0.5611 (3)	0.0698 (7)
H13A	0.4010	0.3188	0.6445	0.084*
H13B	0.5689	0.3476	0.5979	0.084*
C14	0.4129 (4)	0.29840 (12)	0.4151 (4)	0.0864 (9)
H14A	0.2911	0.2926	0.3791	0.130*
H14B	0.4662	0.2548	0.4382	0.130*
H14C	0.4598	0.3204	0.3340	0.130*
N1	0.2678 (2)	0.56704 (9)	0.6903 (2)	0.0575 (5)
O1	−0.0371 (2)	0.59243 (8)	0.1895 (2)	0.0692 (5)
O2	−0.0599 (2)	0.68564 (8)	0.3343 (2)	0.0728 (5)
O3	0.3616 (2)	0.40572 (7)	0.52177 (19)	0.0630 (5)
O4	0.4634 (2)	0.44071 (8)	0.7710 (2)	0.0758 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0625 (16)	0.0608 (14)	0.0556 (16)	−0.0007 (12)	0.0013 (13)	0.0057 (12)
C2	0.0755 (18)	0.0710 (15)	0.0570 (16)	−0.0005 (13)	0.0032 (14)	−0.0028 (13)
C3	0.0789 (19)	0.0591 (14)	0.0676 (19)	0.0047 (13)	0.0114 (15)	−0.0030 (13)
C4	0.0610 (15)	0.0529 (12)	0.0648 (17)	0.0031 (11)	0.0105 (13)	0.0059 (11)
C5	0.0422 (12)	0.0446 (11)	0.0532 (14)	−0.0059 (9)	0.0090 (11)	0.0060 (10)
C6	0.0486 (14)	0.0472 (11)	0.0598 (16)	−0.0025 (10)	0.0070 (12)	0.0078 (10)
C7	0.0547 (14)	0.0504 (12)	0.0578 (16)	−0.0045 (10)	0.0052 (12)	0.0025 (11)
C8	0.0512 (14)	0.0471 (11)	0.0569 (15)	−0.0010 (10)	0.0050 (12)	0.0060 (10)
C9	0.0558 (15)	0.0535 (13)	0.0628 (17)	−0.0068 (11)	0.0080 (13)	0.0096 (12)
C10	0.0721 (18)	0.0696 (15)	0.0657 (18)	0.0119 (13)	0.0011 (14)	0.0191 (13)
C11	0.0823 (19)	0.0765 (16)	0.0643 (18)	−0.0001 (14)	−0.0039 (14)	0.0078 (14)
C12	0.0528 (15)	0.0543 (13)	0.0637 (17)	−0.0017 (11)	0.0097 (13)	0.0081 (12)
C13	0.0644 (16)	0.0550 (13)	0.089 (2)	0.0107 (12)	0.0126 (15)	0.0112 (13)
C14	0.084 (2)	0.0547 (14)	0.115 (3)	0.0083 (13)	0.0095 (18)	−0.0047 (15)
N1	0.0557 (12)	0.0539 (10)	0.0606 (13)	−0.0007 (9)	0.0066 (10)	0.0058 (10)
O1	0.0786 (12)	0.0619 (9)	0.0586 (11)	0.0126 (8)	−0.0062 (9)	0.0075 (8)
O2	0.0819 (12)	0.0518 (9)	0.0797 (13)	0.0090 (8)	0.0048 (10)	0.0100 (8)
O3	0.0681 (11)	0.0469 (8)	0.0696 (11)	0.0067 (7)	0.0036 (9)	0.0061 (8)
O4	0.0801 (13)	0.0756 (11)	0.0644 (12)	0.0177 (9)	−0.0023 (10)	0.0116 (9)

C1—C2	1.346 (3)	C9—O1	1.344 (3)
C1—N1	1.390 (3)	C10—O1	1.451 (3)
C1—H1	0.9300	C10—C11	1.492 (3)
C2—C3	1.408 (3)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.346 (3)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.397 (3)	C11—H11C	0.9600
C4—H4	0.9300	C12—O4	1.210 (3)
C5—N1	1.384 (3)	C12—O3	1.344 (3)
C5—C6	1.395 (3)	C13—O3	1.450 (2)
C6—C7	1.394 (3)	C13—C14	1.490 (3)
C6—C9	1.455 (3)	C13—H13A	0.9700
C7—C8	1.369 (3)	C13—H13B	0.9700
C7—H7	0.9300	C14—H14A	0.9600
C8—N1	1.404 (3)	C14—H14B	0.9600
C8—C12	1.452 (3)	C14—H14C	0.9600
C9—O2	1.211 (3)
C2—C1—N1	119.5 (2)	O1—C10—H10B	110.4
C2—C1—H1	120.3	C11—C10—H10B	110.4
N1—C1—H1	120.3	H10A—C10—H10B	108.6
C1—C2—C3	120.4 (2)	C10—C11—H11A	109.5
C1—C2—H2	119.8	C10—C11—H11B	109.5
C3—C2—H2	119.8	H11A—C11—H11B	109.5
C4—C3—C2	120.5 (2)	C10—C11—H11C	109.5
C4—C3—H3	119.8	H11A—C11—H11C	109.5
C2—C3—H3	119.8	H11B—C11—H11C	109.5
C3—C4—C5	119.9 (2)	O4—C12—O3	122.9 (2)
C3—C4—H4	120.1	O4—C12—C8	126.1 (2)
C5—C4—H4	120.1	O3—C12—C8	111.1 (2)
N1—C5—C6	108.02 (18)	O3—C13—C14	107.7 (2)
N1—C5—C4	119.2 (2)	O3—C13—H13A	110.2
C6—C5—C4	132.8 (2)	C14—C13—H13A	110.2
C7—C6—C5	107.0 (2)	O3—C13—H13B	110.2
C7—C6—C9	128.1 (2)	C14—C13—H13B	110.2
C5—C6—C9	125.0 (2)	H13A—C13—H13B	108.5
C8—C7—C6	109.6 (2)	C13—C14—H14A	109.5
C8—C7—H7	125.2	C13—C14—H14B	109.5
C6—C7—H7	125.2	H14A—C14—H14B	109.5
C7—C8—N1	107.08 (18)	C13—C14—H14C	109.5
C7—C8—C12	129.7 (2)	H14A—C14—H14C	109.5
N1—C8—C12	123.2 (2)	H14B—C14—H14C	109.5
O2—C9—O1	123.3 (2)	C5—N1—C1	120.57 (19)
O2—C9—C6	125.5 (2)	C5—N1—C8	108.35 (18)
O1—C9—C6	111.2 (2)	C1—N1—C8	131.08 (19)
O1—C10—C11	106.8 (2)	C9—O1—C10	116.56 (18)
O1—C10—H10A	110.4	C12—O3—C13	116.16 (19)
C11—C10—H10A	110.4
N1—C1—C2—C3	−0.4 (4)	C7—C8—C12—O3	−1.1 (3)
C1—C2—C3—C4	0.4 (4)	N1—C8—C12—O3	176.12 (18)
C2—C3—C4—C5	−0.1 (4)	C6—C5—N1—C1	179.92 (18)
C3—C4—C5—N1	−0.2 (3)	C4—C5—N1—C1	0.1 (3)
C3—C4—C5—C6	−179.9 (2)	C6—C5—N1—C8	−0.6 (2)
N1—C5—C6—C7	0.7 (2)	C4—C5—N1—C8	179.61 (18)
C4—C5—C6—C7	−179.5 (2)	C2—C1—N1—C5	0.2 (3)
N1—C5—C6—C9	−179.89 (19)	C2—C1—N1—C8	−179.2 (2)
C4—C5—C6—C9	−0.2 (4)	C7—C8—N1—C5	0.3 (2)
C5—C6—C7—C8	−0.6 (2)	C12—C8—N1—C5	−177.48 (19)
C9—C6—C7—C8	−179.9 (2)	C7—C8—N1—C1	179.6 (2)
C6—C7—C8—N1	0.2 (2)	C12—C8—N1—C1	1.9 (3)
C6—C7—C8—C12	177.7 (2)	O2—C9—O1—C10	0.2 (3)
C7—C6—C9—O2	−176.9 (2)	C6—C9—O1—C10	−178.95 (19)
C5—C6—C9—O2	3.9 (4)	C11—C10—O1—C9	178.84 (19)
C7—C6—C9—O1	2.2 (3)	O4—C12—O3—C13	2.4 (3)
C5—C6—C9—O1	−177.01 (19)	C8—C12—O3—C13	−177.22 (18)
C7—C8—C12—O4	179.3 (2)	C14—C13—O3—C12	−179.72 (19)
N1—C8—C12—O4	−3.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4i	0.93	2.59	3.257 (3)	129
C3—H3···O2ii	0.93	2.55	3.272 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4i	0.93	2.59	3.257 (3)	129
C3—H3⋯O2ii	0.93	2.55	3.272 (3)	135

Symmetry codes: (i) ; (ii) .