1′,5-Dinitro-2′-phenyl-2′,3′,5′,6′,7′,7a'-hexa­hydro­spiro­[indoline-3,3′-1′H-pyrrolizin]-2-one

Sarrafi, Y.; Alimohammadi, K.

doi:10.1107/S1600536808025038

organic compounds

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Volume 64| Part 9| September 2008| Page o1740

doi:10.1107/S1600536808025038

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1′,5-Dinitro-2′-phenyl-2′,3′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-1′H-pyrrolizin]-2-one

Yaghoub Sarrafi ^a ^* and Kamal Alimohammadi ^a

^aDepartment of Chemistry, University of Mazandaran, 47415 Babolsar, Iran
^*Correspondence e-mail: ysarrafi@umz.ac.ir

(Received 23 July 2008; accepted 4 August 2008; online 13 August 2008)

In the title cycloadduct, C₂₀H₁₈N₄O₅, the rings of the pyrrolizine system adopt envelope conformations. A centrosymmetric dimer is formed via intermolecular N—H⋯O hydrogen bonds between the indolinone rings.

Related literature

For related literature, see: De March et al. (2002 ); Fejes et al. (2001 ); Karthikeyan et al. (2007 ); Usha et al. (2005a ,b ); Liddell (1998 ); Michael (1997 ).

Experimental

Crystal data

C₂₀H₁₈N₄O₅
M_r = 394.38
Monoclinic, P 2₁ /c
a = 13.998 (4) Å
b = 7.963 (3) Å
c = 16.359 (6) Å
β = 99.695 (11)°
V = 1797.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 120 (2) K
0.26 × 0.18 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: none
13372 measured reflections
4316 independent reflections
2227 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.114
S = 1.00
4316 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	1.97	2.808 (2)	164
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025038/om2253sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025038/om2253Isup2.hkl

checkCIF report

Comment top

1,3-Dipolar cycloadditions form a subject of intensive research in organic synthesis in view of their great synthetic potential (Karthikeyan et al., 2007). Azomethine ylides are reactive and versatile 1,3-dipoles, which readily react with diverse dipolarophiles affording pyrrolizines, pyrrolidines and pyrazolidines (Fejes et al., 2001; De March et al., 2002). The pyrrolizine substructure occurs in many natural products of potential use in medicine and agriculture (Liddell, 1998; Michael, 1997). The title compound was synthesized by the multicomponent 1,3-dipolar cycloaddition of azomethine ylide, derived from 5-nitroisatin and proline by a decarboxylative route, and trans-β-nitrostyrene. The geometry of the crystal structure (Fig. 1) is similar to reported compounds (Usha et al., 2005a, 2005b). The molecular structure of the title compound shows a centrosymmetric dimer (Fig. 2) via N—H···O intermolecular interactions and crystal packing is stabilized through intermolecular C—H···O and C—H···π interactions.

Related literature top

For related literature, see: De March et al. (2002); Fejes et al. (2001); Karthikeyan et al. (2007); Usha et al. (2005a,b); Liddell (1998); Michael (1997).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with the numbering scheme for the atoms and 30% probability displacement ellipsoids.
	Fig. 2. H-bonding dimer diagram of the molecules with hydrogen bonds shown as dashed lines.

1',5-Dinitro-2'-phenyl-2',3',5',6',7',7a'-hexahydrospiro[indoline-3,3'-1'H-pyrrolizin]-2-one top

Crystal data top

C₂₀H₁₈N₄O₅	F(000) = 824
M_r = 394.38	D_x = 1.457 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 438 reflections
a = 13.998 (4) Å	θ = 2.1–19.3°
b = 7.963 (3) Å	µ = 0.11 mm⁻¹
c = 16.359 (6) Å	T = 120 K
β = 99.695 (11)°	Prism, yellow
V = 1797.5 (10) Å³	0.26 × 0.18 × 0.12 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2227 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 28.0°, θ_min = 2.5°
ϕ and ω scans	h = −17→18
13372 measured reflections	k = −10→10
4316 independent reflections	l = −21→21

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)] = 0.057	Hydrogen site location: difference Fourier map
wR(F²) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.02P)² + 1.3P] where P = (F_o² + 2F_c²)/3
4316 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₀H₁₈N₄O₅	V = 1797.5 (10) Å³
M_r = 394.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.998 (4) Å	µ = 0.11 mm⁻¹
b = 7.963 (3) Å	T = 120 K
c = 16.359 (6) Å	0.26 × 0.18 × 0.12 mm
β = 99.695 (11)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2227 reflections with I > 2σ(I)
13372 measured reflections	R_int = 0.044
4316 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.00	Δρ_max = 0.31 e Å⁻³
4316 reflections	Δρ_min = −0.25 e Å⁻³
262 parameters

Special details top

Experimental. A mixture of 5-nitroisatin (0.192 g, 1 mmol), proline (0.115 g, 1 mmol), and trans-β-nitrostyrene (0.149 g, 1 mmol) in ethanol (10 ml) was stirred at refluxed for 1 h. After completion of the reaction, as indicated by TLC, to solution was added water (25 ml) and the precipitated solid was separated by filtration. The pure cycloadduct was obtained by recrystallization from ethanol.

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
O1	0.42737 (11)	0.8306 (2)	0.53311 (9)	0.0310 (4)
O2	−0.02802 (13)	1.0541 (3)	0.22715 (12)	0.0518 (5)
O3	0.03964 (13)	1.2271 (2)	0.15286 (11)	0.0449 (5)
O4	0.27784 (16)	0.2753 (2)	0.54074 (12)	0.0596 (6)
O5	0.17142 (13)	0.3390 (2)	0.43381 (11)	0.0441 (5)
N1	0.39099 (13)	1.0143 (2)	0.42331 (11)	0.0271 (5)
H1A	0.4465	1.0625	0.4266	0.033*
N2	0.21896 (13)	0.8303 (2)	0.52112 (11)	0.0276 (5)
N3	0.04377 (16)	1.1279 (3)	0.21107 (13)	0.0366 (5)
N4	0.23870 (16)	0.3752 (3)	0.48895 (13)	0.0360 (5)
C1	0.37153 (16)	0.8895 (3)	0.47458 (14)	0.0260 (5)
C2	0.26499 (15)	0.8336 (3)	0.44673 (13)	0.0240 (5)
C3	0.23048 (16)	0.9555 (3)	0.37701 (13)	0.0247 (5)
C4	0.14310 (17)	0.9760 (3)	0.32541 (13)	0.0277 (5)
H4A	0.0896	0.9110	0.3315	0.033*
C5	0.13764 (17)	1.0973 (3)	0.26379 (14)	0.0283 (6)
C6	0.21565 (18)	1.1911 (3)	0.24975 (15)	0.0325 (6)
H6A	0.2090	1.2681	0.2064	0.039*
C7	0.30444 (17)	1.1698 (3)	0.30081 (14)	0.0304 (6)
H7A	0.3586	1.2309	0.2924	0.036*
C8	0.30976 (16)	1.0547 (3)	0.36449 (13)	0.0244 (5)
C9	0.12231 (17)	0.9058 (3)	0.52006 (15)	0.0346 (6)
H9A	0.0875	0.9154	0.4638	0.042*
H9B	0.1279	1.0164	0.5453	0.042*
C10	0.07094 (18)	0.7847 (3)	0.57053 (16)	0.0373 (6)
H10A	0.0881	0.8064	0.6295	0.045*
H10B	0.0011	0.7911	0.5544	0.045*
C11	0.10985 (18)	0.6159 (3)	0.54746 (17)	0.0383 (6)
H11A	0.0999	0.5293	0.5868	0.046*
H11B	0.0801	0.5814	0.4922	0.046*
C12	0.21678 (17)	0.6552 (3)	0.55171 (14)	0.0296 (6)
H12A	0.2497	0.6497	0.6095	0.036*
C13	0.27408 (17)	0.5532 (3)	0.49667 (14)	0.0297 (6)
H13A	0.3429	0.5540	0.5215	0.036*
C14	0.26082 (16)	0.6474 (3)	0.41508 (13)	0.0256 (5)
H14A	0.1945	0.6264	0.3867	0.031*
C15	0.32836 (17)	0.6039 (3)	0.35484 (14)	0.0272 (5)
C16	0.42558 (18)	0.5628 (3)	0.38008 (15)	0.0371 (6)
H16A	0.4513	0.5618	0.4363	0.044*
C17	0.48456 (19)	0.5237 (3)	0.32300 (16)	0.0417 (7)
H17A	0.5493	0.4969	0.3411	0.050*
C18	0.44760 (19)	0.5243 (3)	0.23930 (15)	0.0387 (6)
H18A	0.4870	0.4960	0.2010	0.046*
C19	0.35159 (19)	0.5672 (3)	0.21255 (15)	0.0359 (6)
H19A	0.3266	0.5702	0.1562	0.043*
C20	0.29304 (18)	0.6057 (3)	0.27026 (14)	0.0311 (6)
H20A	0.2285	0.6335	0.2519	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0260 (9)	0.0382 (10)	0.0268 (9)	−0.0038 (8)	−0.0010 (7)	0.0041 (8)
O2	0.0293 (11)	0.0701 (15)	0.0526 (12)	0.0004 (10)	−0.0030 (9)	0.0051 (10)
O3	0.0505 (12)	0.0470 (11)	0.0340 (11)	0.0179 (10)	−0.0023 (9)	0.0041 (9)
O4	0.0802 (16)	0.0409 (12)	0.0554 (13)	0.0026 (11)	0.0053 (11)	0.0165 (10)
O5	0.0453 (12)	0.0390 (11)	0.0477 (12)	−0.0096 (9)	0.0067 (10)	−0.0070 (9)
N1	0.0195 (10)	0.0318 (11)	0.0292 (10)	−0.0042 (9)	0.0018 (8)	0.0027 (9)
N2	0.0246 (11)	0.0306 (11)	0.0281 (11)	−0.0027 (9)	0.0060 (8)	−0.0001 (9)
N3	0.0357 (13)	0.0423 (13)	0.0299 (12)	0.0116 (11)	−0.0001 (10)	−0.0051 (10)
N4	0.0405 (13)	0.0319 (12)	0.0369 (13)	−0.0016 (11)	0.0105 (11)	0.0010 (10)
C1	0.0254 (13)	0.0306 (13)	0.0226 (12)	0.0000 (11)	0.0056 (10)	−0.0012 (10)
C2	0.0192 (12)	0.0285 (13)	0.0243 (12)	−0.0016 (10)	0.0037 (9)	−0.0010 (10)
C3	0.0234 (12)	0.0260 (12)	0.0246 (12)	0.0010 (10)	0.0033 (10)	−0.0023 (10)
C4	0.0261 (13)	0.0287 (13)	0.0282 (13)	−0.0024 (11)	0.0039 (10)	−0.0048 (10)
C5	0.0254 (13)	0.0328 (13)	0.0243 (12)	0.0068 (11)	−0.0023 (10)	−0.0042 (10)
C6	0.0379 (15)	0.0292 (14)	0.0294 (13)	0.0040 (12)	0.0028 (11)	0.0026 (11)
C7	0.0283 (13)	0.0313 (13)	0.0315 (13)	−0.0008 (11)	0.0051 (11)	0.0013 (11)
C8	0.0239 (13)	0.0244 (12)	0.0241 (12)	0.0011 (10)	0.0016 (10)	−0.0040 (10)
C9	0.0328 (14)	0.0361 (15)	0.0370 (15)	0.0037 (12)	0.0116 (12)	−0.0014 (12)
C10	0.0324 (14)	0.0451 (16)	0.0360 (15)	0.0002 (13)	0.0099 (12)	−0.0006 (12)
C11	0.0349 (15)	0.0368 (15)	0.0457 (16)	−0.0088 (12)	0.0141 (12)	0.0021 (12)
C12	0.0322 (14)	0.0326 (14)	0.0243 (12)	−0.0009 (11)	0.0057 (10)	0.0022 (10)
C13	0.0281 (13)	0.0275 (13)	0.0340 (14)	−0.0035 (11)	0.0062 (11)	−0.0013 (11)
C14	0.0227 (12)	0.0287 (13)	0.0250 (12)	−0.0018 (10)	0.0029 (10)	−0.0012 (10)
C15	0.0263 (13)	0.0256 (12)	0.0304 (13)	−0.0023 (11)	0.0072 (10)	0.0010 (10)
C16	0.0297 (14)	0.0531 (17)	0.0275 (13)	0.0015 (13)	0.0021 (11)	−0.0005 (12)
C17	0.0239 (14)	0.0599 (19)	0.0413 (16)	0.0031 (13)	0.0054 (12)	−0.0014 (14)
C18	0.0427 (17)	0.0420 (16)	0.0351 (15)	0.0024 (13)	0.0171 (13)	0.0005 (12)
C19	0.0437 (16)	0.0397 (15)	0.0241 (13)	0.0025 (13)	0.0049 (12)	0.0081 (11)
C20	0.0317 (14)	0.0287 (13)	0.0316 (14)	0.0051 (11)	0.0018 (11)	0.0029 (11)

Geometric parameters (Å, º) top

O1—C1	1.223 (2)	C9—H9A	0.9700
O2—N3	1.230 (3)	C9—H9B	0.9700
O3—N3	1.232 (3)	C10—C11	1.521 (3)
O4—N4	1.223 (3)	C10—H10A	0.9700
O5—N4	1.224 (2)	C10—H10B	0.9700
N1—C1	1.357 (3)	C11—C12	1.519 (3)
N1—C8	1.398 (3)	C11—H11A	0.9700
N1—H1A	0.8600	C11—H11B	0.9700
N2—C2	1.470 (3)	C12—C13	1.535 (3)
N2—C9	1.478 (3)	C12—H12A	0.9800
N2—C12	1.483 (3)	C13—C14	1.515 (3)
N3—C5	1.466 (3)	C13—H13A	0.9800
N4—C13	1.500 (3)	C14—C15	1.516 (3)
C1—C2	1.550 (3)	C14—H14A	0.9800
C2—C3	1.513 (3)	C15—C20	1.389 (3)
C2—C14	1.568 (3)	C15—C16	1.393 (3)
C3—C4	1.374 (3)	C16—C17	1.382 (3)
C3—C8	1.405 (3)	C16—H16A	0.9300
C4—C5	1.389 (3)	C17—C18	1.380 (3)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.374 (3)	C18—C19	1.384 (3)
C6—C7	1.386 (3)	C18—H18A	0.9300
C6—H6A	0.9300	C19—C20	1.385 (3)
C7—C8	1.380 (3)	C19—H19A	0.9300
C7—H7A	0.9300	C20—H20A	0.9300
C9—C10	1.526 (3)

C1—N1—C8	111.68 (19)	C9—C10—H10A	111.4
C1—N1—H1A	124.2	C11—C10—H10B	111.4
C8—N1—H1A	124.2	C9—C10—H10B	111.4
C2—N2—C9	120.73 (18)	H10A—C10—H10B	109.3
C2—N2—C12	109.45 (18)	C12—C11—C10	101.42 (19)
C9—N2—C12	108.40 (18)	C12—C11—H11A	111.5
O2—N3—O3	122.6 (2)	C10—C11—H11A	111.5
O2—N3—C5	118.6 (2)	C12—C11—H11B	111.5
O3—N3—C5	118.8 (2)	C10—C11—H11B	111.5
O4—N4—O5	123.8 (2)	H11A—C11—H11B	109.3
O4—N4—C13	117.0 (2)	N2—C12—C11	104.72 (19)
O5—N4—C13	119.1 (2)	N2—C12—C13	104.90 (18)
O1—C1—N1	126.6 (2)	C11—C12—C13	118.2 (2)
O1—C1—C2	125.2 (2)	N2—C12—H12A	109.5
N1—C1—C2	108.18 (19)	C11—C12—H12A	109.5
N2—C2—C3	120.44 (19)	C13—C12—H12A	109.5
N2—C2—C1	107.23 (17)	N4—C13—C14	113.83 (19)
C3—C2—C1	101.93 (18)	N4—C13—C12	110.60 (19)
N2—C2—C14	105.01 (17)	C14—C13—C12	104.84 (19)
C3—C2—C14	111.59 (18)	N4—C13—H13A	109.1
C1—C2—C14	110.43 (18)	C14—C13—H13A	109.1
C4—C3—C8	119.1 (2)	C12—C13—H13A	109.1
C4—C3—C2	132.6 (2)	C13—C14—C15	117.51 (19)
C8—C3—C2	108.11 (18)	C13—C14—C2	100.67 (17)
C3—C4—C5	117.6 (2)	C15—C14—C2	116.00 (18)
C3—C4—H4A	121.2	C13—C14—H14A	107.3
C5—C4—H4A	121.2	C15—C14—H14A	107.3
C6—C5—C4	123.5 (2)	C2—C14—H14A	107.3
C6—C5—N3	118.1 (2)	C20—C15—C16	117.6 (2)
C4—C5—N3	118.5 (2)	C20—C15—C14	119.3 (2)
C5—C6—C7	119.3 (2)	C16—C15—C14	123.1 (2)
C5—C6—H6A	120.3	C17—C16—C15	121.2 (2)
C7—C6—H6A	120.3	C17—C16—H16A	119.4
C8—C7—C6	117.7 (2)	C15—C16—H16A	119.4
C8—C7—H7A	121.1	C18—C17—C16	120.2 (2)
C6—C7—H7A	121.1	C18—C17—H17A	119.9
C7—C8—N1	127.4 (2)	C16—C17—H17A	119.9
C7—C8—C3	122.7 (2)	C17—C18—C19	119.8 (2)
N1—C8—C3	109.93 (19)	C17—C18—H18A	120.1
N2—C9—C10	104.50 (19)	C19—C18—H18A	120.1
N2—C9—H9A	110.9	C18—C19—C20	119.6 (2)
C10—C9—H9A	110.9	C18—C19—H19A	120.2
N2—C9—H9B	110.9	C20—C19—H19A	120.2
C10—C9—H9B	110.9	C19—C20—C15	121.6 (2)
H9A—C9—H9B	108.9	C19—C20—H20A	119.2
C11—C10—C9	101.72 (19)	C15—C20—H20A	119.2
C11—C10—H10A	111.4

C8—N1—C1—O1	−178.1 (2)	C12—N2—C9—C10	13.3 (2)
C8—N1—C1—C2	1.6 (2)	N2—C9—C10—C11	−35.4 (2)
C9—N2—C2—C3	18.2 (3)	C9—C10—C11—C12	43.5 (2)
C12—N2—C2—C3	145.0 (2)	C2—N2—C12—C11	−119.4 (2)
C9—N2—C2—C1	133.9 (2)	C9—N2—C12—C11	14.2 (2)
C12—N2—C2—C1	−99.3 (2)	C2—N2—C12—C13	5.8 (2)
C9—N2—C2—C14	−108.6 (2)	C9—N2—C12—C13	139.27 (19)
C12—N2—C2—C14	18.2 (2)	C10—C11—C12—N2	−35.9 (2)
O1—C1—C2—N2	48.8 (3)	C10—C11—C12—C13	−152.1 (2)
N1—C1—C2—N2	−130.89 (19)	O4—N4—C13—C14	152.6 (2)
O1—C1—C2—C3	176.2 (2)	O5—N4—C13—C14	−29.7 (3)
N1—C1—C2—C3	−3.5 (2)	O4—N4—C13—C12	−89.7 (3)
O1—C1—C2—C14	−65.1 (3)	O5—N4—C13—C12	88.1 (3)
N1—C1—C2—C14	115.2 (2)	N2—C12—C13—N4	−151.47 (18)
N2—C2—C3—C4	−61.6 (3)	C11—C12—C13—N4	−35.3 (3)
C1—C2—C3—C4	180.0 (2)	N2—C12—C13—C14	−28.4 (2)
C14—C2—C3—C4	62.1 (3)	C11—C12—C13—C14	87.8 (2)
N2—C2—C3—C8	122.5 (2)	N4—C13—C14—C15	−73.9 (3)
C1—C2—C3—C8	4.1 (2)	C12—C13—C14—C15	165.08 (19)
C14—C2—C3—C8	−113.7 (2)	N4—C13—C14—C2	159.14 (19)
C8—C3—C4—C5	−1.1 (3)	C12—C13—C14—C2	38.1 (2)
C2—C3—C4—C5	−176.5 (2)	N2—C2—C14—C13	−34.7 (2)
C3—C4—C5—C6	3.1 (3)	C3—C2—C14—C13	−166.78 (18)
C3—C4—C5—N3	−176.6 (2)	C1—C2—C14—C13	80.6 (2)
O2—N3—C5—C6	−174.4 (2)	N2—C2—C14—C15	−162.62 (18)
O3—N3—C5—C6	5.0 (3)	C3—C2—C14—C15	65.3 (2)
O2—N3—C5—C4	5.3 (3)	C1—C2—C14—C15	−47.3 (2)
O3—N3—C5—C4	−175.2 (2)	C13—C14—C15—C20	144.2 (2)
C4—C5—C6—C7	−2.3 (4)	C2—C14—C15—C20	−96.7 (2)
N3—C5—C6—C7	177.4 (2)	C13—C14—C15—C16	−36.4 (3)
C5—C6—C7—C8	−0.5 (3)	C2—C14—C15—C16	82.7 (3)
C6—C7—C8—N1	−179.5 (2)	C20—C15—C16—C17	−0.6 (4)
C6—C7—C8—C3	2.5 (3)	C14—C15—C16—C17	179.9 (2)
C1—N1—C8—C7	−177.0 (2)	C15—C16—C17—C18	−0.2 (4)
C1—N1—C8—C3	1.2 (3)	C16—C17—C18—C19	1.2 (4)
C4—C3—C8—C7	−1.7 (3)	C17—C18—C19—C20	−1.4 (4)
C2—C3—C8—C7	174.8 (2)	C18—C19—C20—C15	0.6 (4)
C4—C3—C8—N1	180.0 (2)	C16—C15—C20—C19	0.4 (4)
C2—C3—C8—N1	−3.5 (2)	C14—C15—C20—C19	179.9 (2)
C2—N2—C9—C10	140.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	1.97	2.808 (2)	164

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₄O₅
M_r	394.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	13.998 (4), 7.963 (3), 16.359 (6)
β (°)	99.695 (11)
V (Å³)	1797.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.26 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13372, 4316, 2227
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.114, 1.00
No. of reflections	4316
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.25

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.860	1.971	2.808 (2)	164.29

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

We are grateful for the financial support of Mazandaran University, Islamic Republic of Iran.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
De March, P., Elias, L., Figueredo, M. & Font, J. (2002). Tetrahedron, 58, 2667–2672. CrossRef CAS Google Scholar
Fejes, I., Nyerges, M., Szollosy, A., Blasko, G. & Toke, L. (2001). Tetrahedron, 57, 1129–1137. Web of Science CrossRef CAS Google Scholar
Karthikeyan, K., Perumal, P. T., Etti, S. & Shanmugam, G. (2007). Tetrahedron, 63, 10581–10586. Web of Science CSD CrossRef CAS Google Scholar
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Michael, J. P. (1997). Nat. Prod. Rep. 14, 619–636. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2005b). Acta Cryst. E61, o3312–o3314. Web of Science CSD CrossRef IUCr Journals Google Scholar
Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K. & Raghunathan, R. (2005a). Acta Cryst. E61, o3299–o3301. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Page o1740

doi:10.1107/S1600536808025038

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

1′,5-Di­nitro-2′-phenyl-2′,3′,5′,6′,7′,7a'-hexa­hydro­spiro­[indoline-3,3′-1′H-pyrrolizin]-2-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1′,5-Dinitro-2′-phenyl-2′,3′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-1′H-pyrrolizin]-2-one