7′-Methyl-5′-oxo-2′,3′-dihydro­spiro­[1,3-dioxolane-2,1′(5′H)-indolizine]-6′-carbonitrile

Wang, K.; Yang, W.; Wang, L.-L.; Zhu, J.; Hu, Y.

doi:10.1107/S160053681003285X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2431

https://doi.org/10.1107/S160053681003285X

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7′-Methyl-5′-oxo-2′,3′-dihydrospiro[1,3-dioxolane-2,1′(5′H)-indolizine]-6′-carbonitrile

Kai Wang,^a Wen-ge Yang,^a ^* Lu-Lu Wang,^a Jing Zhu ^a and Yong-hong Hu ^b

^aState Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bState Key Laboratory of Materials-Oriented Chemical Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: chemywg@126.com

(Received 22 July 2010; accepted 16 August 2010; online 28 August 2010)

In the title compound, C₁₂H₁₂N₂O₃, the five-membered ring attached to the aromatic ring adopts an envelope conformation with a C atom in the flap position. The spiro-linked five-membered ring adopts a twisted conformation. In the crystal, C—H⋯O hydrogen bonds link the molecules into C(5) chains propagating in [001].

Related literature

For medicinal background, see: Takimoto & Calvo (2008 ). For further synthetic details, see: Wani et al. (1980 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₂N₂O₃
M_r = 232.24
Orthorhombic, P n a 2₁
a = 7.9460 (16) Å
b = 25.945 (5) Å
c = 5.3430 (11) Å
V = 1101.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.970, T_max = 0.990
2217 measured reflections
1123 independent reflections
821 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.112
S = 1.00
1123 reflections
155 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯O3ⁱ	0.97	2.49	3.275 (5)	138
Symmetry code: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681003285X/hb5573sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003285X/hb5573Isup2.hkl

checkCIF report

Comment top

Camptothecin(CPT), with the chemical name (S)-4-ethyl-4-hydroxy-1H-pyr- ano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione, is a pentacyclic alkaloid. Two CPT analogues, topotecan and irinotecan, have been approved and are used in cancer chemotherapy (Takimoto & Calvo, 2008). As part of our studies into the synthesis of Camptothecin, the title compound, (I), was synthesized (Wani et al., 1980). We report herein the crystal structure of the title compound.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. In the crystal structure, C—H···O hydrogen bonds link the molecules (Fig. 2), based on the geometrically positioned H5B atom, in which they may be effective in the stabilization of the structure.

Related literature top

For medicinal background, see: Takimoto & Calvo (2008). For further synthetic details, see: Wani et al. (1980). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 1,2,3,5-tetrahydro-7-methyl-1,5-dioxo-6- Indolizinecarbonitrile, (13.0 g,0.069 mol), ethylene glycol (210 ml), and p-toluenesulfonic acid (1.1 g) in toluene (1.0 L) was refluxed using a Dean-Stark trap for 5 h. The toluene layer was decanted and another liter of toluene was added. The reaction mixture was refluxed for an additional 5 h and the toluene layer decanted as before. After repeating this procedure two more times, the toluene layers were combined, washed with brine, dried, and evaporated to yield the crude product, which was crystallized from MeOH to give the title compound (93%) (Wani et al., 1980). Colourless blocks of (I) were obtained by slow evaporation of an MeOH solution.

Structure description top

For medicinal background, see: Takimoto & Calvo (2008). For further synthetic details, see: Wani et al. (1980). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids are drawn at 30% probability levels.
	Fig. 2. A practical packing diagram of the title compound. Hydron bonds are shown as dashed lines.

7'-Methyl-5'-oxo-2',3'-dihydrospiro[1,3-dioxolane-2,1'(5'H)- indolizine]-6'-carbonitrile top

Crystal data top

C₁₂H₁₂N₂O₃	D_x = 1.400 Mg m⁻³
M_r = 232.24	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 25 reflections
a = 7.9460 (16) Å	θ = 9–12°
b = 25.945 (5) Å	µ = 0.10 mm⁻¹
c = 5.3430 (11) Å	T = 293 K
V = 1101.5 (4) Å³	Block, colorless
Z = 4	0.30 × 0.10 × 0.10 mm
F(000) = 488

Data collection top

Enraf–Nonius CAD-4 diffractometer	821 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.3°, θ_min = 1.6°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −31→31
T_min = 0.970, T_max = 0.990	l = 0→6
2217 measured reflections	3 standard reflections every 200 reflections
1123 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.063P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1123 reflections	Δρ_max = 0.20 e Å⁻³
155 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.047 (6)

Crystal data top

C₁₂H₁₂N₂O₃	V = 1101.5 (4) Å³
M_r = 232.24	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.9460 (16) Å	µ = 0.10 mm⁻¹
b = 25.945 (5) Å	T = 293 K
c = 5.3430 (11) Å	0.30 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	821 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.035
T_min = 0.970, T_max = 0.990	3 standard reflections every 200 reflections
2217 measured reflections	intensity decay: 1%
1123 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.112	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
1123 reflections	Δρ_min = −0.20 e Å⁻³
155 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
N1	0.6878 (4)	0.41701 (10)	0.1075 (7)	0.0350 (8)
O1	1.0548 (3)	0.42931 (10)	−0.0779 (6)	0.0432 (7)
C1	1.1570 (5)	0.39063 (18)	−0.1891 (10)	0.0523 (12)
H1A	1.1499	0.3586	−0.0963	0.063*
H1B	1.2737	0.4015	−0.1965	0.063*
O2	0.9270 (3)	0.41052 (10)	−0.4426 (6)	0.0464 (8)
C2	1.0842 (5)	0.38466 (17)	−0.4486 (10)	0.0532 (12)
H2A	1.1579	0.4001	−0.5724	0.064*
H2B	1.0690	0.3485	−0.4892	0.064*
N2	0.3916 (5)	0.29581 (15)	0.6093 (9)	0.0675 (12)
O3	0.5035 (3)	0.42382 (11)	0.4332 (7)	0.0551 (8)
C3	0.8959 (5)	0.42629 (15)	−0.1938 (8)	0.0382 (9)
C4	0.7840 (4)	0.38909 (13)	−0.0515 (8)	0.0330 (8)
C5	0.7124 (5)	0.47294 (14)	0.0789 (9)	0.0435 (10)
H5A	0.7800	0.4868	0.2142	0.052*
H5B	0.6055	0.4910	0.0735	0.052*
C6	0.8043 (5)	0.47679 (15)	−0.1705 (9)	0.0465 (11)
H6A	0.7254	0.4813	−0.3072	0.056*
H6B	0.8828	0.5054	−0.1701	0.056*
C7	0.7736 (4)	0.33684 (13)	−0.0581 (8)	0.0378 (9)
H7A	0.8364	0.3182	−0.1736	0.045*
C8	0.6665 (4)	0.31108 (13)	0.1120 (8)	0.0361 (9)
C9	0.5774 (4)	0.34061 (15)	0.2809 (8)	0.0384 (9)
C10	0.5825 (5)	0.39580 (15)	0.2880 (8)	0.0411 (10)
C11	0.6517 (5)	0.25394 (13)	0.1031 (9)	0.0484 (11)
H11A	0.5747	0.2426	0.2301	0.073*
H11B	0.7602	0.2387	0.1318	0.073*
H11C	0.6107	0.2436	−0.0583	0.073*
C12	0.4728 (5)	0.31630 (16)	0.4644 (10)	0.0451 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0381 (16)	0.0350 (16)	0.0320 (18)	0.0017 (13)	0.0036 (16)	−0.0016 (17)
O1	0.0423 (14)	0.0509 (14)	0.0365 (15)	−0.0026 (13)	0.0029 (16)	−0.0031 (14)
C1	0.049 (2)	0.059 (3)	0.049 (3)	0.006 (2)	0.006 (3)	0.006 (3)
O2	0.0522 (16)	0.0618 (18)	0.0252 (14)	0.0076 (14)	0.0057 (15)	0.0018 (14)
C2	0.061 (3)	0.057 (2)	0.042 (2)	0.009 (2)	0.018 (2)	0.000 (2)
N2	0.065 (2)	0.081 (3)	0.056 (3)	−0.017 (2)	0.022 (3)	0.002 (2)
O3	0.0598 (18)	0.0526 (16)	0.0528 (18)	0.0025 (14)	0.0263 (18)	−0.0127 (17)
C3	0.043 (2)	0.044 (2)	0.027 (2)	0.0000 (17)	0.003 (2)	−0.0032 (19)
C4	0.0313 (18)	0.0400 (19)	0.0276 (18)	0.0043 (16)	0.0004 (19)	−0.003 (2)
C5	0.054 (2)	0.038 (2)	0.038 (2)	0.0027 (18)	0.009 (2)	0.000 (2)
C6	0.055 (2)	0.042 (2)	0.042 (2)	0.003 (2)	0.006 (2)	0.010 (2)
C7	0.040 (2)	0.039 (2)	0.034 (2)	0.0055 (16)	0.009 (2)	−0.004 (2)
C8	0.0340 (18)	0.041 (2)	0.033 (2)	0.0011 (16)	0.001 (2)	−0.002 (2)
C9	0.037 (2)	0.043 (2)	0.034 (2)	−0.0003 (18)	0.003 (2)	0.001 (2)
C10	0.039 (2)	0.046 (2)	0.038 (2)	0.0061 (18)	0.001 (2)	−0.004 (2)
C11	0.053 (2)	0.042 (2)	0.050 (3)	−0.0047 (17)	0.008 (3)	0.004 (3)
C12	0.041 (2)	0.052 (2)	0.043 (3)	−0.0045 (19)	0.005 (2)	0.000 (2)

Geometric parameters (Å, º) top

N1—C4	1.353 (5)	C4—C7	1.359 (5)
N1—C10	1.390 (5)	C5—C6	1.523 (6)
N1—C5	1.472 (4)	C5—H5A	0.9700
O1—C3	1.408 (5)	C5—H5B	0.9700
O1—C1	1.421 (5)	C6—H6A	0.9700
C1—C2	1.510 (7)	C6—H6B	0.9700
C1—H1A	0.9700	C7—C8	1.413 (5)
C1—H1B	0.9700	C7—H7A	0.9300
O2—C3	1.413 (5)	C8—C9	1.379 (6)
O2—C2	1.419 (5)	C8—C11	1.488 (5)
C2—H2A	0.9700	C9—C12	1.432 (6)
C2—H2B	0.9700	C9—C10	1.433 (5)
N2—C12	1.140 (5)	C11—H11A	0.9600
O3—C10	1.235 (5)	C11—H11B	0.9600
C3—C6	1.504 (6)	C11—H11C	0.9600
C3—C4	1.517 (6)

C4—N1—C10	124.3 (3)	N1—C5—H5B	111.2
C4—N1—C5	112.8 (3)	C6—C5—H5B	111.2
C10—N1—C5	122.8 (3)	H5A—C5—H5B	109.1
C3—O1—C1	106.8 (3)	C3—C6—C5	104.3 (3)
O1—C1—C2	103.7 (4)	C3—C6—H6A	110.9
O1—C1—H1A	111.0	C5—C6—H6A	110.9
C2—C1—H1A	111.0	C3—C6—H6B	110.9
O1—C1—H1B	111.0	C5—C6—H6B	110.9
C2—C1—H1B	111.0	H6A—C6—H6B	108.9
H1A—C1—H1B	109.0	C4—C7—C8	119.5 (4)
C3—O2—C2	108.2 (3)	C4—C7—H7A	120.3
O2—C2—C1	105.6 (4)	C8—C7—H7A	120.3
O2—C2—H2A	110.6	C9—C8—C7	117.9 (3)
C1—C2—H2A	110.6	C9—C8—C11	122.3 (4)
O2—C2—H2B	110.6	C7—C8—C11	119.9 (4)
C1—C2—H2B	110.6	C8—C9—C12	120.1 (3)
H2A—C2—H2B	108.8	C8—C9—C10	123.9 (4)
O1—C3—O2	105.9 (3)	C12—C9—C10	116.0 (4)
O1—C3—C6	110.4 (3)	O3—C10—N1	120.6 (3)
O2—C3—C6	114.5 (4)	O3—C10—C9	126.2 (4)
O1—C3—C4	109.9 (3)	N1—C10—C9	113.2 (3)
O2—C3—C4	112.9 (3)	C8—C11—H11A	109.5
C6—C3—C4	103.2 (3)	C8—C11—H11B	109.5
N1—C4—C7	121.1 (4)	H11A—C11—H11B	109.5
N1—C4—C3	107.8 (3)	C8—C11—H11C	109.5
C7—C4—C3	131.1 (4)	H11A—C11—H11C	109.5
N1—C5—C6	102.7 (3)	H11B—C11—H11C	109.5
N1—C5—H5A	111.2	N2—C12—C9	178.3 (5)
C6—C5—H5A	111.2

C3—O1—C1—C2	28.0 (4)	O1—C3—C6—C5	−87.6 (4)
C3—O2—C2—C1	−5.9 (5)	O2—C3—C6—C5	153.0 (3)
O1—C1—C2—O2	−13.4 (5)	C4—C3—C6—C5	29.8 (4)
C1—O1—C3—O2	−32.5 (4)	N1—C5—C6—C3	−27.3 (4)
C1—O1—C3—C6	−157.0 (4)	N1—C4—C7—C8	−3.0 (6)
C1—O1—C3—C4	89.8 (4)	C3—C4—C7—C8	174.6 (4)
C2—O2—C3—O1	23.4 (4)	C4—C7—C8—C9	−0.6 (6)
C2—O2—C3—C6	145.3 (3)	C4—C7—C8—C11	178.8 (4)
C2—O2—C3—C4	−96.9 (4)	C7—C8—C9—C12	−177.3 (4)
C10—N1—C4—C7	5.3 (6)	C11—C8—C9—C12	3.3 (6)
C5—N1—C4—C7	−177.6 (4)	C7—C8—C9—C10	2.3 (6)
C10—N1—C4—C3	−172.8 (3)	C11—C8—C9—C10	−177.1 (4)
C5—N1—C4—C3	4.3 (5)	C4—N1—C10—O3	177.2 (4)
O1—C3—C4—N1	96.2 (4)	C5—N1—C10—O3	0.4 (6)
O2—C3—C4—N1	−145.8 (3)	C4—N1—C10—C9	−3.5 (6)
C6—C3—C4—N1	−21.6 (4)	C5—N1—C10—C9	179.8 (3)
O1—C3—C4—C7	−81.7 (5)	C8—C9—C10—O3	179.0 (4)
O2—C3—C4—C7	36.3 (6)	C12—C9—C10—O3	−1.5 (6)
C6—C3—C4—C7	160.5 (4)	C8—C9—C10—N1	−0.4 (6)
C4—N1—C5—C6	14.6 (4)	C12—C9—C10—N1	179.2 (3)
C10—N1—C5—C6	−168.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O3ⁱ	0.97	2.49	3.275 (5)	138

Symmetry code: (i) −x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂O₃
M_r	232.24
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	7.9460 (16), 25.945 (5), 5.3430 (11)
V (Å³)	1101.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.970, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	2217, 1123, 821
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.112, 1.00
No. of reflections	1123
No. of parameters	155
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O3ⁱ	0.97	2.49	3.275 (5)	138

Symmetry code: (i) −x+1, −y+1, z−1/2.

Acknowledgements

This research work was supported financially by the Department of Science and Technology of Jiangsu Province (BE200830457) and the `863' project (2007 A A02Z211) of the Ministry of Science and Technology of China.

References

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2431

https://doi.org/10.1107/S160053681003285X

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

7′-Methyl-5′-oxo-2′,3′-di­hydro­spiro­[1,3-dioxolane-2,1′(5′H)-indolizine]-6′-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7′-Methyl-5′-oxo-2′,3′-dihydrospiro[1,3-dioxolane-2,1′(5′H)-indolizine]-6′-carbonitrile