Ethyl 4-(2-eth-oxy-2-oxoeth-yl)-3-oxo-4,13-di-aza-penta-cyclo-[11.8.0.0(2,11).0(5,10).0(14,19)]henicosa-1,5(10),6,8,11,14(19),15,17,20-nona-ene-12-carboxyl-ate.

In the title compound, C26H22N2O5, the system consisting of five fused rings, being essentially planar with an r.m.s. deviation from the least-squares plane of 0.049 (3) Å, makes a dihedral angle of 58.72 (12)° with the plane of the ethyl carboxyl-ate group immediately attached to it, and a dihedral angle of 89.48 (14)° with the plane of the ethyl carboxyl-ate group attached via the -CH2- bridge. Bond lengths indicate π-delocalization over the whole penta-cyclic system. The mol-ecular conformation is stabilized by a weak intra-molecular C-H⋯O hydrogen bond. In the crystal, mol-ecules form stacks along the b-axis direction, neighboring mol-ecules within each stack being related by inversion and the shortest distance between the centroids of the pyridine rings within the stack being 3.667 (2) Å.

Related literature

For pharmaceutical properties of indolizines and related compounds, see: Olden et al. (1991 ▶); Jaffrezou et al. (1992 ▶). For the preparation of annulated indolizine, see: Liu et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H22N2O5

M = 442.46

Triclinic,

a = 8.4000 (17) Å

b = 11.008 (2) Å

c = 12.304 (3) Å

α = 74.33 (3)°

β = 75.38 (3)°

γ = 86.18 (3)°

V = 1060.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.3 × 0.2 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.977, T max = 0.981

4095 measured reflections

3811 independent reflections

2855 reflections with I > 2σ(I)

R int = 0.021

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.153

S = 1.01

3809 reflections

301 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813015833/yk2094sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015833/yk2094Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015833/yk2094Isup3.cml

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

C26H22N2O5	Z = 2
Mr = 442.46	F(000) = 464
Triclinic, P1	Dx = 1.386 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4000 (17) Å	Cell parameters from 25 reflections
b = 11.008 (2) Å	θ = 9–12°
c = 12.304 (3) Å	µ = 0.10 mm−1
α = 74.33 (3)°	T = 295 K
β = 75.38 (3)°	Block, colourless
γ = 86.18 (3)°	0.3 × 0.2 × 0.2 mm
V = 1060.0 (4) Å3

Enraf–Nonius CAD-4 diffractometer	2855 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.2°, θmin = 1.8°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
Tmin = 0.977, Tmax = 0.981	l = −14→14
4095 measured reflections	3 standard reflections every 200 reflections
3811 independent reflections	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.067P)2 + 0.6558P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3809 reflections	Δρmax = 0.22 e Å−3
301 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.056 (4)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.Two reflections were omitted from the initial data set of 3811 reflections, thus 3809 is the correct number of reflections in the L.S. refinement procedure

	x	y	z	Uiso*/Ueq
O5	0.3913 (2)	0.80663 (16)	0.26370 (14)	0.0453 (4)
N2	0.5328 (2)	0.73427 (18)	0.46629 (17)	0.0413 (5)
O3	0.3219 (3)	0.7099 (2)	0.82722 (16)	0.0659 (6)
C7	0.3563 (3)	0.8813 (2)	0.5236 (2)	0.0394 (5)
N1	0.1884 (2)	0.8865 (2)	0.75042 (17)	0.0475 (5)
C8	0.3822 (3)	0.7900 (2)	0.6224 (2)	0.0428 (6)
O4	0.4712 (3)	1.00189 (17)	0.24670 (17)	0.0650 (6)
C6	0.2412 (3)	0.9830 (2)	0.5397 (2)	0.0411 (6)
C1	0.1577 (3)	0.9812 (2)	0.6552 (2)	0.0437 (6)
C14	0.4914 (3)	0.7000 (2)	0.5869 (2)	0.0437 (6)
C24	0.4415 (3)	0.8959 (2)	0.3036 (2)	0.0426 (6)
C5	0.2067 (3)	1.0811 (2)	0.4496 (2)	0.0474 (6)
H5	0.2624	1.0842	0.3733	0.057*
C23	0.4492 (3)	0.8453 (2)	0.4264 (2)	0.0404 (5)
C21	0.7233 (3)	0.7114 (3)	0.2844 (2)	0.0494 (6)
H21	0.6902	0.7884	0.2427	0.059*
C2	0.0422 (3)	1.0757 (3)	0.6742 (2)	0.0521 (7)
H2	−0.0142	1.0748	0.7499	0.062*
C22	0.6559 (3)	0.6685 (2)	0.4033 (2)	0.0429 (6)
C9	0.2995 (3)	0.7893 (3)	0.7406 (2)	0.0479 (6)
C17	0.7146 (3)	0.5562 (2)	0.4673 (2)	0.0530 (7)
O2	−0.1099 (3)	0.7778 (2)	0.8434 (2)	0.0799 (7)
C4	0.0929 (3)	1.1733 (3)	0.4702 (3)	0.0544 (7)
H4	0.0716	1.2373	0.4087	0.065*
C15	0.5548 (4)	0.5884 (3)	0.6489 (2)	0.0541 (7)
H15	0.5243	0.5646	0.7298	0.065*
C3	0.0109 (3)	1.1694 (3)	0.5831 (3)	0.0552 (7)
H3	−0.0665	1.2311	0.5977	0.066*
O1	−0.1713 (3)	0.8786 (3)	0.9833 (2)	0.0916 (8)
C25	0.3949 (4)	0.8401 (3)	0.1403 (2)	0.0573 (7)
H25A	0.5061	0.8612	0.0938	0.069*
H25B	0.3247	0.9123	0.1213	0.069*
C10	0.1035 (4)	0.8897 (3)	0.8679 (2)	0.0616 (8)
H10A	0.1092	0.9750	0.8748	0.074*
H10B	0.1614	0.8352	0.9215	0.074*
C11	−0.0746 (4)	0.8496 (3)	0.9045 (2)	0.0618 (8)
C16	0.6595 (4)	0.5167 (3)	0.5907 (3)	0.0590 (7)
H16	0.6962	0.4405	0.6314	0.071*
C20	0.8391 (4)	0.6400 (3)	0.2282 (3)	0.0652 (8)
H20	0.8845	0.6694	0.1486	0.078*
C19	0.8888 (4)	0.5240 (3)	0.2896 (3)	0.0799 (10)
H19	0.9619	0.4736	0.2506	0.096*
C13	−0.2873 (6)	0.6002 (5)	0.9349 (5)	0.136 (2)
H13A	−0.2511	0.5893	1.0050	0.205*
H13B	−0.2182	0.5518	0.8871	0.205*
H13C	−0.3990	0.5717	0.9543	0.205*
C18	0.8299 (4)	0.4852 (3)	0.4063 (3)	0.0709 (9)
H18	0.8670	0.4093	0.4472	0.085*
C26	0.3346 (5)	0.7286 (4)	0.1163 (3)	0.0830 (11)
H26A	0.2217	0.7128	0.1580	0.124*
H26B	0.3998	0.6563	0.1410	0.124*
H26C	0.3433	0.7446	0.0343	0.124*
C12	−0.2776 (4)	0.7282 (4)	0.8740 (4)	0.1070 (15)
H12A	−0.3505	0.7763	0.9216	0.128*
H12B	−0.3147	0.7388	0.8035	0.128*

	U11	U22	U33	U12	U13	U23
O5	0.0468 (10)	0.0508 (10)	0.0396 (9)	0.0018 (8)	−0.0118 (7)	−0.0134 (8)
N2	0.0410 (11)	0.0398 (11)	0.0445 (11)	0.0001 (9)	−0.0108 (9)	−0.0132 (9)
O3	0.0785 (14)	0.0722 (13)	0.0418 (11)	0.0085 (11)	−0.0132 (10)	−0.0097 (10)
C7	0.0340 (12)	0.0429 (13)	0.0439 (13)	−0.0032 (10)	−0.0103 (10)	−0.0142 (11)
N1	0.0395 (11)	0.0613 (14)	0.0418 (12)	0.0005 (10)	−0.0062 (9)	−0.0173 (10)
C8	0.0387 (13)	0.0470 (14)	0.0429 (13)	−0.0009 (11)	−0.0099 (10)	−0.0119 (11)
O4	0.0882 (15)	0.0437 (11)	0.0535 (11)	−0.0043 (10)	−0.0101 (10)	−0.0026 (9)
C6	0.0326 (12)	0.0465 (14)	0.0464 (14)	−0.0041 (10)	−0.0080 (10)	−0.0165 (11)
C1	0.0340 (12)	0.0522 (15)	0.0484 (14)	−0.0060 (11)	−0.0090 (11)	−0.0184 (12)
C14	0.0448 (14)	0.0439 (14)	0.0421 (13)	−0.0044 (11)	−0.0119 (11)	−0.0085 (11)
C24	0.0364 (13)	0.0450 (14)	0.0431 (13)	0.0043 (11)	−0.0044 (10)	−0.0117 (11)
C5	0.0417 (14)	0.0495 (15)	0.0492 (15)	0.0006 (11)	−0.0089 (11)	−0.0124 (12)
C23	0.0356 (12)	0.0406 (13)	0.0452 (13)	−0.0011 (10)	−0.0081 (10)	−0.0127 (10)
C21	0.0400 (14)	0.0538 (15)	0.0537 (16)	0.0064 (12)	−0.0098 (12)	−0.0159 (12)
C2	0.0418 (14)	0.0595 (17)	0.0559 (16)	−0.0022 (12)	−0.0016 (12)	−0.0258 (14)
C22	0.0354 (12)	0.0436 (13)	0.0528 (15)	0.0021 (10)	−0.0119 (11)	−0.0171 (11)
C9	0.0486 (15)	0.0540 (15)	0.0422 (14)	−0.0035 (12)	−0.0124 (12)	−0.0121 (12)
C17	0.0508 (16)	0.0495 (15)	0.0601 (17)	0.0073 (12)	−0.0148 (13)	−0.0172 (13)
O2	0.0557 (13)	0.0863 (16)	0.0884 (16)	−0.0132 (11)	0.0051 (11)	−0.0250 (13)
C4	0.0478 (15)	0.0480 (15)	0.0651 (18)	0.0049 (12)	−0.0133 (13)	−0.0126 (13)
C15	0.0614 (17)	0.0506 (15)	0.0490 (15)	0.0015 (13)	−0.0179 (13)	−0.0072 (12)
C3	0.0437 (15)	0.0514 (16)	0.0715 (19)	0.0057 (12)	−0.0091 (13)	−0.0237 (14)
O1	0.0767 (16)	0.1089 (19)	0.0682 (15)	0.0147 (14)	0.0162 (12)	−0.0232 (14)
C25	0.0567 (17)	0.0748 (19)	0.0394 (14)	0.0133 (14)	−0.0130 (12)	−0.0154 (13)
C10	0.0599 (18)	0.083 (2)	0.0438 (15)	0.0119 (15)	−0.0113 (13)	−0.0247 (14)
C11	0.0578 (18)	0.0673 (19)	0.0451 (16)	0.0095 (15)	0.0018 (14)	−0.0050 (14)
C16	0.0662 (18)	0.0453 (15)	0.0630 (18)	0.0106 (13)	−0.0211 (15)	−0.0076 (13)
C20	0.0519 (17)	0.080 (2)	0.0603 (18)	0.0102 (15)	−0.0039 (14)	−0.0240 (16)
C19	0.074 (2)	0.080 (2)	0.080 (2)	0.0343 (18)	−0.0092 (18)	−0.0302 (19)
C13	0.114 (4)	0.101 (4)	0.178 (5)	−0.043 (3)	0.000 (4)	−0.031 (3)
C18	0.073 (2)	0.0600 (18)	0.075 (2)	0.0256 (16)	−0.0161 (17)	−0.0185 (16)
C26	0.093 (3)	0.113 (3)	0.0584 (19)	−0.004 (2)	−0.0301 (18)	−0.037 (2)
C12	0.055 (2)	0.100 (3)	0.136 (4)	−0.023 (2)	0.001 (2)	0.001 (3)

O5—C24	1.344 (3)	O2—C11	1.320 (4)
O5—C25	1.456 (3)	O2—C12	1.466 (4)
N2—C14	1.385 (3)	C4—C3	1.376 (4)
N2—C23	1.401 (3)	C4—H4	0.9300
N2—C22	1.412 (3)	C15—C16	1.344 (4)
O3—C9	1.229 (3)	C15—H15	0.9300
C7—C23	1.392 (3)	C3—H3	0.9300
C7—C8	1.406 (3)	O1—C11	1.199 (4)
C7—C6	1.452 (3)	C25—C26	1.484 (4)
N1—C9	1.383 (3)	C25—H25A	0.9700
N1—C1	1.408 (3)	C25—H25B	0.9700
N1—C10	1.450 (3)	C10—C11	1.509 (4)
C8—C14	1.387 (3)	C10—H10A	0.9700
C8—C9	1.443 (3)	C10—H10B	0.9700
O4—C24	1.192 (3)	C16—H16	0.9300
C6—C5	1.397 (3)	C20—C19	1.394 (5)
C6—C1	1.413 (3)	C20—H20	0.9300
C1—C2	1.400 (4)	C19—C18	1.352 (5)
C14—C15	1.409 (4)	C19—H19	0.9300
C24—C23	1.479 (3)	C13—C12	1.403 (6)
C5—C4	1.377 (4)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C21—C20	1.376 (4)	C13—H13C	0.9600
C21—C22	1.388 (4)	C18—H18	0.9300
C21—H21	0.9300	C26—H26A	0.9600
C2—C3	1.371 (4)	C26—H26B	0.9600
C2—H2	0.9300	C26—H26C	0.9600
C22—C17	1.407 (4)	C12—H12A	0.9700
C17—C18	1.400 (4)	C12—H12B	0.9700
C17—C16	1.423 (4)
C24—O5—C25	116.4 (2)	C16—C15—H15	120.1
C14—N2—C23	109.1 (2)	C14—C15—H15	120.1
C14—N2—C22	120.8 (2)	C2—C3—C4	120.8 (3)
C23—N2—C22	129.7 (2)	C2—C3—H3	119.6
C23—C7—C8	107.1 (2)	C4—C3—H3	119.6
C23—C7—C6	133.9 (2)	O5—C25—C26	107.0 (2)
C8—C7—C6	118.8 (2)	O5—C25—H25A	110.3
C9—N1—C1	124.3 (2)	C26—C25—H25A	110.3
C9—N1—C10	116.1 (2)	O5—C25—H25B	110.3
C1—N1—C10	119.6 (2)	C26—C25—H25B	110.3
C14—C8—C7	109.1 (2)	H25A—C25—H25B	108.6
C14—C8—C9	126.6 (2)	N1—C10—C11	115.0 (2)
C7—C8—C9	124.2 (2)	N1—C10—H10A	108.5
C5—C6—C1	118.2 (2)	C11—C10—H10A	108.5
C5—C6—C7	124.8 (2)	N1—C10—H10B	108.5
C1—C6—C7	117.1 (2)	C11—C10—H10B	108.5
C2—C1—N1	119.9 (2)	H10A—C10—H10B	107.5
C2—C1—C6	118.8 (2)	O1—C11—O2	124.4 (3)
N1—C1—C6	121.2 (2)	O1—C11—C10	122.3 (3)
N2—C14—C8	107.1 (2)	O2—C11—C10	113.2 (2)
N2—C14—C15	120.4 (2)	C15—C16—C17	120.5 (3)
C8—C14—C15	132.5 (2)	C15—C16—H16	119.7
O4—C24—O5	123.4 (2)	C17—C16—H16	119.7
O4—C24—C23	125.8 (2)	C21—C20—C19	120.5 (3)
O5—C24—C23	110.8 (2)	C21—C20—H20	119.8
C4—C5—C6	122.1 (2)	C19—C20—H20	119.8
C4—C5—H5	119.0	C18—C19—C20	119.5 (3)
C6—C5—H5	119.0	C18—C19—H19	120.2
C7—C23—N2	107.6 (2)	C20—C19—H19	120.2
C7—C23—C24	128.1 (2)	C12—C13—H13A	109.5
N2—C23—C24	123.4 (2)	C12—C13—H13B	109.5
C20—C21—C22	120.0 (3)	H13A—C13—H13B	109.5
C20—C21—H21	120.0	C12—C13—H13C	109.5
C22—C21—H21	120.0	H13A—C13—H13C	109.5
C3—C2—C1	121.1 (2)	H13B—C13—H13C	109.5
C3—C2—H2	119.5	C19—C18—C17	121.7 (3)
C1—C2—H2	119.5	C19—C18—H18	119.1
C21—C22—C17	119.7 (2)	C17—C18—H18	119.1
C21—C22—N2	123.3 (2)	C25—C26—H26A	109.5
C17—C22—N2	116.9 (2)	C25—C26—H26B	109.5
O3—C9—N1	121.2 (2)	H26A—C26—H26B	109.5
O3—C9—C8	124.5 (3)	C25—C26—H26C	109.5
N1—C9—C8	114.3 (2)	H26A—C26—H26C	109.5
C18—C17—C22	118.2 (3)	H26B—C26—H26C	109.5
C18—C17—C16	120.9 (3)	C13—C12—O2	112.1 (4)
C22—C17—C16	120.9 (2)	C13—C12—H12A	109.2
C11—O2—C12	118.4 (3)	O2—C12—H12A	109.2
C5—C4—C3	119.1 (3)	C13—C12—H12B	109.2
C5—C4—H4	120.4	O2—C12—H12B	109.2
C3—C4—H4	120.4	H12A—C12—H12B	107.9
C16—C15—C14	119.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1	0.97	2.32	2.712 (5)	103
C10—H10B···O3	0.97	2.21	2.669 (4)	107
C15—H15···O3	0.93	2.56	3.082 (4)	116
C21—H21···O5	0.93	2.46	2.964 (3)	114
C5—H5···O4	0.93	2.34	3.168 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4	0.93	2.34	3.168 (3)	148