Dimethyl 3-(cyclo-propyl-carbon-yl)pyrrolo-[2,1-a]isoquinoline-1,2-dicarboxyl-ate.

In the mol-ecular structure of the title compound, C(20)H(17)NO(5), two intra-molecular C-H⋯O hydrogen bond generate six- and seven-membered ring motifs. The dihedral angles between the almost planar 13-atom triple-fused-ring system (r.m.s. deviation = 0.003 Å) and the planes of the two meth-oxy-carbonyl substituents are 61.7 (2) and 33.01 (10)°.

Related literature

For chemical background, see: Michael (2004 ▶); Sriram et al. (2005 ▶); Alonso et al. (1985 ▶). For the biological activity of indolizine derivatives, see: Shen et al. (2010 ▶).

Experimental

Crystal data

C20H17NO5

M = 351.35

Monoclinic,

a = 7.5910 (15) Å

b = 18.436 (4) Å

c = 12.162 (2) Å

β = 94.43 (3)°

V = 1697.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 ▶) T min = 0.971, T max = 0.990

3321 measured reflections

3078 independent reflections

2060 reflections with I > 2σ(I)

R int = 0.048

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.179

S = 1.01

3078 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.24 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: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015656/ff2061sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015656/ff2061Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015656/ff2061Isup3.cml

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

C20H17NO5	F(000) = 736
Mr = 351.35	Dx = 1.375 Mg m−3
Monoclinic, P21/c	Melting point: 388 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.5910 (15) Å	Cell parameters from 25 reflections
b = 18.436 (4) Å	θ = 9–12°
c = 12.162 (2) Å	µ = 0.10 mm−1
β = 94.43 (3)°	T = 293 K
V = 1697.0 (6) Å3	Block, yellow
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	2060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 25.3°, θmin = 2.0°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = 0→22
Tmin = 0.971, Tmax = 0.990	l = −14→14
3321 measured reflections	3 standard reflections every 200 reflections
3078 independent reflections	intensity decay: 1%

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
3078 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.30 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.

	x	y	z	Uiso*/Ueq
N	0.2043 (3)	0.45752 (11)	0.56131 (17)	0.0407 (5)
O1	0.0490 (3)	0.31335 (12)	0.57398 (18)	0.0729 (7)
C1	0.0128 (5)	0.2518 (2)	0.7977 (3)	0.0763 (10)
H1A	0.0035	0.2474	0.8765	0.092*
H1B	−0.0987	0.2485	0.7533	0.092*
O2	0.3127 (2)	0.44915 (12)	0.92593 (15)	0.0583 (6)
C2	0.1687 (5)	0.22111 (19)	0.7524 (4)	0.0815 (11)
H2A	0.1537	0.1991	0.6799	0.098*
H2B	0.2560	0.1979	0.8032	0.098*
O3	0.0196 (3)	0.44054 (13)	0.88912 (17)	0.0657 (6)
C3	0.1495 (4)	0.30195 (16)	0.7597 (3)	0.0591 (8)
H3A	0.2247	0.3260	0.8179	0.071*
O4	0.4069 (3)	0.64344 (13)	0.76734 (18)	0.0715 (7)
C4	0.1160 (4)	0.34276 (15)	0.6567 (2)	0.0463 (7)
O5	0.1973 (3)	0.59404 (11)	0.86128 (17)	0.0613 (6)
C5	0.2880 (5)	0.4387 (3)	1.0410 (3)	0.0879 (13)
H5A	0.4009	0.4381	1.0824	0.132*
H5B	0.2287	0.3934	1.0507	0.132*
H5C	0.2179	0.4776	1.0667	0.132*
C6	0.1646 (4)	0.45114 (15)	0.8593 (2)	0.0462 (7)
C7	0.2330 (5)	0.64687 (18)	0.9471 (3)	0.0694 (10)
H7A	0.1510	0.6407	1.0026	0.104*
H7B	0.2206	0.6947	0.9164	0.104*
H7C	0.3513	0.6405	0.9795	0.104*
C8	0.3006 (3)	0.59626 (15)	0.7761 (2)	0.0452 (7)
C9	0.2639 (3)	0.53321 (14)	0.7048 (2)	0.0403 (6)
C10	0.2004 (3)	0.46707 (14)	0.7437 (2)	0.0403 (6)
C11	0.1670 (3)	0.41976 (14)	0.6564 (2)	0.0405 (6)
C12	0.2688 (3)	0.52648 (14)	0.5891 (2)	0.0406 (6)
C13	0.1793 (3)	0.43333 (16)	0.4534 (2)	0.0472 (7)
H13A	0.1353	0.3870	0.4387	0.057*
C14	0.2183 (4)	0.47657 (17)	0.3706 (2)	0.0555 (8)
H14A	0.1957	0.4607	0.2983	0.067*
C15	0.2945 (4)	0.54702 (17)	0.3911 (2)	0.0512 (7)
C16	0.3216 (3)	0.57249 (15)	0.5008 (2)	0.0449 (7)
C17	0.3413 (4)	0.5916 (2)	0.3040 (3)	0.0644 (9)
H17A	0.3216	0.5754	0.2317	0.077*
C18	0.4146 (4)	0.6579 (2)	0.3238 (3)	0.0693 (10)
H18A	0.4429	0.6871	0.2654	0.083*
C19	0.4473 (4)	0.68183 (18)	0.4315 (3)	0.0653 (9)
H19A	0.5020	0.7264	0.4449	0.078*
C20	0.4002 (4)	0.64068 (16)	0.5189 (3)	0.0553 (8)
H20A	0.4206	0.6582	0.5905	0.066*

	U11	U22	U33	U12	U13	U23
N	0.0414 (12)	0.0421 (12)	0.0390 (12)	0.0036 (10)	0.0048 (9)	−0.0006 (10)
O1	0.0976 (17)	0.0614 (14)	0.0594 (14)	−0.0228 (13)	0.0031 (12)	−0.0076 (11)
C1	0.076 (2)	0.080 (3)	0.075 (2)	−0.0009 (19)	0.0169 (19)	0.0190 (19)
O2	0.0539 (12)	0.0747 (15)	0.0457 (12)	0.0098 (11)	0.0005 (9)	0.0041 (10)
C2	0.101 (3)	0.053 (2)	0.092 (3)	0.0147 (19)	0.022 (2)	0.0156 (19)
O3	0.0523 (12)	0.0861 (16)	0.0604 (13)	−0.0108 (12)	0.0159 (10)	−0.0020 (12)
C3	0.074 (2)	0.0412 (16)	0.061 (2)	−0.0008 (15)	−0.0017 (16)	0.0013 (14)
O4	0.0759 (15)	0.0702 (15)	0.0703 (15)	−0.0316 (13)	0.0186 (12)	−0.0128 (12)
C4	0.0449 (15)	0.0450 (16)	0.0495 (16)	0.0019 (13)	0.0059 (12)	−0.0051 (13)
O5	0.0749 (14)	0.0487 (12)	0.0634 (14)	−0.0122 (10)	0.0248 (11)	−0.0177 (10)
C5	0.092 (3)	0.130 (4)	0.0406 (19)	0.021 (3)	−0.0004 (17)	0.008 (2)
C6	0.0499 (16)	0.0419 (15)	0.0471 (16)	0.0023 (13)	0.0060 (13)	−0.0026 (12)
C7	0.086 (2)	0.062 (2)	0.062 (2)	−0.0102 (18)	0.0194 (18)	−0.0194 (17)
C8	0.0352 (13)	0.0472 (16)	0.0531 (17)	−0.0003 (13)	0.0036 (12)	0.0001 (13)
C9	0.0349 (13)	0.0427 (15)	0.0437 (15)	0.0056 (11)	0.0049 (11)	−0.0003 (12)
C10	0.0379 (13)	0.0417 (15)	0.0413 (15)	0.0045 (11)	0.0035 (11)	0.0006 (11)
C11	0.0373 (13)	0.0423 (15)	0.0421 (15)	0.0050 (11)	0.0038 (11)	0.0011 (12)
C12	0.0339 (13)	0.0402 (14)	0.0479 (16)	0.0071 (11)	0.0039 (11)	0.0020 (12)
C13	0.0448 (15)	0.0531 (17)	0.0428 (16)	0.0060 (13)	−0.0014 (12)	−0.0032 (13)
C14	0.0547 (17)	0.069 (2)	0.0426 (17)	0.0116 (15)	0.0020 (13)	−0.0036 (15)
C15	0.0462 (15)	0.0619 (19)	0.0461 (17)	0.0136 (14)	0.0069 (12)	0.0123 (14)
C16	0.0330 (13)	0.0472 (16)	0.0551 (17)	0.0110 (12)	0.0066 (11)	0.0095 (13)
C17	0.0523 (18)	0.083 (2)	0.059 (2)	0.0119 (17)	0.0109 (14)	0.0175 (18)
C18	0.057 (2)	0.078 (2)	0.075 (2)	0.0110 (18)	0.0161 (17)	0.034 (2)
C19	0.0588 (19)	0.0517 (18)	0.087 (3)	0.0033 (15)	0.0161 (17)	0.0196 (18)
C20	0.0491 (16)	0.0516 (17)	0.066 (2)	0.0040 (14)	0.0112 (14)	0.0080 (15)

N—C13	1.385 (3)	C6—C10	1.483 (4)
N—C12	1.395 (3)	C7—H7A	0.9600
N—C11	1.398 (3)	C7—H7B	0.9600
O1—C4	1.218 (3)	C7—H7C	0.9600
C1—C2	1.458 (5)	C8—C9	1.464 (4)
C1—C3	1.490 (5)	C9—C10	1.406 (4)
C1—H1A	0.9700	C9—C12	1.416 (4)
C1—H1B	0.9700	C10—C11	1.382 (4)
O2—C6	1.334 (3)	C12—C16	1.449 (4)
O2—C5	1.440 (4)	C13—C14	1.335 (4)
C2—C3	1.501 (4)	C13—H13A	0.9300
C2—H2A	0.9700	C14—C15	1.436 (4)
C2—H2B	0.9700	C14—H14A	0.9300
O3—C6	1.201 (3)	C15—C17	1.408 (4)
C3—C4	1.467 (4)	C15—C16	1.414 (4)
C3—H3A	0.9800	C16—C20	1.402 (4)
O4—C8	1.197 (3)	C17—C18	1.356 (5)
C4—C11	1.472 (4)	C17—H17A	0.9300
O5—C8	1.347 (3)	C18—C19	1.387 (5)
O5—C7	1.438 (3)	C18—H18A	0.9300
C5—H5A	0.9600	C19—C20	1.376 (4)
C5—H5B	0.9600	C19—H19A	0.9300
C5—H5C	0.9600	C20—H20A	0.9300
C13—N—C12	122.9 (2)	H7B—C7—H7C	109.5
C13—N—C11	127.0 (2)	O4—C8—O5	121.8 (3)
C12—N—C11	110.1 (2)	O4—C8—C9	128.5 (3)
C2—C1—C3	61.2 (2)	O5—C8—C9	109.6 (2)
C2—C1—H1A	117.6	C10—C9—C12	107.1 (2)
C3—C1—H1A	117.6	C10—C9—C8	122.9 (2)
C2—C1—H1B	117.6	C12—C9—C8	129.8 (2)
C3—C1—H1B	117.6	C11—C10—C9	109.7 (2)
H1A—C1—H1B	114.8	C11—C10—C6	124.6 (2)
C6—O2—C5	115.3 (2)	C9—C10—C6	125.7 (2)
C1—C2—C3	60.5 (2)	C10—C11—N	106.5 (2)
C1—C2—H2A	117.7	C10—C11—C4	129.8 (2)
C3—C2—H2A	117.7	N—C11—C4	123.5 (2)
C1—C2—H2B	117.7	N—C12—C9	106.6 (2)
C3—C2—H2B	117.7	N—C12—C16	117.8 (2)
H2A—C2—H2B	114.8	C9—C12—C16	135.7 (3)
C4—C3—C1	120.3 (3)	C14—C13—N	120.0 (3)
C4—C3—C2	118.0 (3)	C14—C13—H13A	120.0
C1—C3—C2	58.3 (2)	N—C13—H13A	120.0
C4—C3—H3A	116.0	C13—C14—C15	121.3 (3)
C1—C3—H3A	116.0	C13—C14—H14A	119.4
C2—C3—H3A	116.0	C15—C14—H14A	119.4
O1—C4—C3	120.7 (3)	C17—C15—C16	119.3 (3)
O1—C4—C11	121.4 (3)	C17—C15—C14	121.3 (3)
C3—C4—C11	117.9 (2)	C16—C15—C14	119.4 (3)
C8—O5—C7	116.7 (2)	C20—C16—C15	118.4 (3)
O2—C5—H5A	109.5	C20—C16—C12	123.1 (3)
O2—C5—H5B	109.5	C15—C16—C12	118.5 (3)
H5A—C5—H5B	109.5	C18—C17—C15	121.1 (3)
O2—C5—H5C	109.5	C18—C17—H17A	119.4
H5A—C5—H5C	109.5	C15—C17—H17A	119.4
H5B—C5—H5C	109.5	C17—C18—C19	119.7 (3)
O3—C6—O2	124.1 (3)	C17—C18—H18A	120.1
O3—C6—C10	123.9 (3)	C19—C18—H18A	120.1
O2—C6—C10	111.9 (2)	C20—C19—C18	121.1 (3)
O5—C7—H7A	109.5	C20—C19—H19A	119.5
O5—C7—H7B	109.5	C18—C19—H19A	119.5
H7A—C7—H7B	109.5	C19—C20—C16	120.4 (3)
O5—C7—H7C	109.5	C19—C20—H20A	119.8
H7A—C7—H7C	109.5	C16—C20—H20A	119.8
C2—C1—C3—C4	106.2 (3)	C3—C4—C11—C10	−19.1 (4)
C1—C2—C3—C4	−110.1 (3)	O1—C4—C11—N	−23.9 (4)
C1—C3—C4—O1	−44.0 (4)	C3—C4—C11—N	155.6 (2)
C2—C3—C4—O1	23.8 (5)	C13—N—C12—C9	175.8 (2)
C1—C3—C4—C11	136.5 (3)	C11—N—C12—C9	−2.7 (3)
C2—C3—C4—C11	−155.7 (3)	C13—N—C12—C16	−3.9 (3)
C5—O2—C6—O3	−4.7 (4)	C11—N—C12—C16	177.5 (2)
C5—O2—C6—C10	176.1 (3)	C10—C9—C12—N	1.4 (3)
C7—O5—C8—O4	−6.1 (4)	C8—C9—C12—N	−173.7 (2)
C7—O5—C8—C9	172.0 (3)	C10—C9—C12—C16	−178.9 (3)
O4—C8—C9—C10	150.7 (3)	C8—C9—C12—C16	6.0 (5)
O5—C8—C9—C10	−27.3 (3)	C12—N—C13—C14	0.4 (4)
O4—C8—C9—C12	−34.9 (5)	C11—N—C13—C14	178.7 (2)
O5—C8—C9—C12	147.1 (3)	N—C13—C14—C15	3.1 (4)
C12—C9—C10—C11	0.3 (3)	C13—C14—C15—C17	177.8 (3)
C8—C9—C10—C11	175.9 (2)	C13—C14—C15—C16	−2.9 (4)
C12—C9—C10—C6	−176.5 (2)	C17—C15—C16—C20	−2.2 (4)
C8—C9—C10—C6	−1.0 (4)	C14—C15—C16—C20	178.5 (2)
O3—C6—C10—C11	−63.4 (4)	C17—C15—C16—C12	178.6 (2)
O2—C6—C10—C11	115.8 (3)	C14—C15—C16—C12	−0.8 (4)
O3—C6—C10—C9	113.0 (3)	N—C12—C16—C20	−175.2 (2)
O2—C6—C10—C9	−67.8 (3)	C9—C12—C16—C20	5.1 (4)
C9—C10—C11—N	−2.0 (3)	N—C12—C16—C15	4.0 (3)
C6—C10—C11—N	174.9 (2)	C9—C12—C16—C15	−175.7 (3)
C9—C10—C11—C4	173.5 (2)	C16—C15—C17—C18	1.2 (4)
C6—C10—C11—C4	−9.6 (4)	C14—C15—C17—C18	−179.4 (3)
C13—N—C11—C10	−175.5 (2)	C15—C17—C18—C19	1.2 (5)
C12—N—C11—C10	2.9 (3)	C17—C18—C19—C20	−2.6 (5)
C13—N—C11—C4	8.6 (4)	C18—C19—C20—C16	1.6 (5)
C12—N—C11—C4	−172.9 (2)	C15—C16—C20—C19	0.8 (4)
O1—C4—C11—C10	161.3 (3)	C12—C16—C20—C19	−180.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1	0.93	2.27	2.872 (4)	122
C20—H20A···O4	0.93	2.18	3.019 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1	0.93	2.27	2.872 (4)	122
C20—H20A⋯O4	0.93	2.18	3.019 (4)	150