Dimethyl 3-(cyclo­propyl­carbon­yl)pyrrolo­[2,1-a]isoquinoline-1,2-dicarboxyl­ate

Xing, H.; Tang, F.; Wang, W.

doi:10.1107/S1600536812015656

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1430

doi:10.1107/S1600536812015656

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Dimethyl 3-(cyclopropylcarbonyl)pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate

Honglong Xing,^a Fan Tang ^a and Wei Wang ^b ^*

^aSchool of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, People's Republic of China, and ^bKey Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province, School of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng 224051, People's Republic of China
^*Correspondence e-mail: wangw@ycit.edu.cn

(Received 30 March 2012; accepted 10 April 2012; online 18 April 2012)

In the molecular structure of the title compound, C₂₀H₁₇NO₅, two intramolecular 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 methoxycarbonyl 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_r = 351.35
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.179
S = 1.01
3078 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812015656/ff2061sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812015656/ff2061Isup3.cml

checkCIF report

Comment top

The indolizine and hydrogenated indolizine structures are found in many alkaloids such as amorine, crythraline, swainsonine, cryptaustoline, cryptowoline (Sriram et al. 2005), camptothesin(Michael, 2004), nuevamine (Alonso et al., 1985), etc. These natural and many synthetic indolizine derivatives have been found to have a variety of biological activity (Shen et al., 2010).

We report here the synthesis and crystal structure of the title compound (I). The molecular structure of (I) is shown in Fig.1. In the title compound, intramolecular C13 —H13A···O1 and C20—H20A···O4 hydrogen bond generates extra two ring motifs. The dihedral angle between the indolizine ring system and the C20—H20A···O4 plane is 20.40 (4)°.

Related literature top

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 top

A mixture of the 2-(2-cyclopropyl-2-oxoethyl)isoquinolinium bromide (10 mmol), acrylonitrile (40 mmol), triethylamine (2 ml) and TPCD (4 g) in DMF (40 ml) was heated at 90° C for 5 h. After cooling, the reaction mixture was poured into an aqueous hydrochloric acid solution (5%, 100 ml), the precipitated crude product was collected by filtration and further purified by silica gel column chromatography with petroleum ether (bp 60–90 °C)-ethyl acetate as eluents. Yellow crystal. m.p. 388–389 K, Yield 76%. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in petroleum ether -ethyl acetate(4:1), at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds.

Dimethyl 3-(cyclopropylcarbonyl)pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate top

Crystal data top

C₂₀H₁₇NO₅	F(000) = 736
M_r = 351.35	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1P)² + 0.4P] where P = (F_o² + 2F_c²)/3
3078 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₁₇NO₅	V = 1697.0 (6) Å³
M_r = 351.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5910 (15) Å	µ = 0.10 mm⁻¹
b = 18.436 (4) Å	T = 293 K
c = 12.162 (2) Å	0.30 × 0.20 × 0.10 mm
β = 94.43 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2060 reflections with I > 2σ(I)
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	R_int = 0.048
T_min = 0.971, T_max = 0.990	3 standard reflections every 200 reflections
3321 measured reflections	intensity decay: 1%
3078 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
3078 reflections	Δρ_min = −0.24 e Å⁻³
235 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇NO₅
M_r	351.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.5910 (15), 18.436 (4), 12.162 (2)
β (°)	94.43 (3)
V (Å³)	1697.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (XCAD4; Harms & Wocadlo, 1995)
T_min, T_max	0.971, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3321, 3078, 2060
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.179, 1.01
No. of reflections	3078
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.24

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

We greatly appreciate the financial support of the Foundation of the Key Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province (AE201017).

References

Alonso, R., Castedo, L. & Dominguez, D. (1985). Tetrahedron Lett. 26, 2925–2928. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Michael, J. P. (2004). Nat. Prod. Rep. 21, 625–649. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, Y. M., Lv, P. C., Chen, W., Liu, P. G., Zhang, M. Z. & Zhu, H. L. (2010). Eur. J. Med. Chem. 45, 3184–3190. Web of Science CrossRef CAS PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sriram, D., Yogeeswari, P., Thirumurugan, R. & Bal, T. R. (2005). Nat. Prod. Res. 19, 393–412. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 68| Part 5| May 2012| Page o1430

doi:10.1107/S1600536812015656

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­methyl 3-(cyclo­propyl­carbon­yl)pyrrolo­[2,1-a]iso­quinoline-1,2-di­carboxyl­ate

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Dimethyl 3-(cyclopropylcarbonyl)pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate