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

Sarrafi, Y.; Alimohammadi, K.

doi:10.1107/S1600536808020837

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1490

doi:10.1107/S1600536808020837

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2′-Methyl-2′-nitro-1′-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: ysarrfi@umz.ac.ir

(Received 23 June 2008; accepted 5 July 2008; online 16 July 2008)

The title compound, C₂₁H₂₁N₃O₃, was synthesized by a multi-component 1,3-dipolar cycloaddition of azomethine ylide, derived from isatin and proline by a decarboxylative route, and (E)-1-phenyl-2-nitropropene. In the molecule, the spiro junction links a planar oxindole ring and a pyrrolidine ring in an envelope conformation. The molecular packing is stabilized by an intermolecular N—H⋯N interaction of the oxindole and pyrrolizidine rings.

Related literature

For related literature, see: Daly et al. (1986 ); Grigg & Sridharan (1993 ); Padwa (1984 ); Usha, Selvanayagam, Velmurugan, Ravikumar & Poornachandran (2005 ); Usha, Selvanayagam, Velmurugan, Ravikumar & Raghunathan (2005 ); Waldmann (1995 ).

Experimental

Crystal data

C₂₁H₂₁N₃O₃
M_r = 363.41
Monoclinic, P 2₁ /n
a = 7.8524 (16) Å
b = 25.656 (6) Å
c = 9.1767 (19) Å
β = 110.489 (4)°
V = 1731.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 (2) K
0.21 × 0.18 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.989
16064 measured reflections
3773 independent reflections
2183 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.102
S = 1.01
3773 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1′—H1′⋯N1ⁱ	0.85	2.21	2.992 (3)	151
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536808020837/om2246sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020837/om2246Isup2.hkl

checkCIF report

Comment top

Multicomponent 1,3-dipolar cycloaddition reactions are considered to be one of the most useful processes for the construction of five-membered heterocyclic ring systems (Padwa, 1984; Grigg & Sridharan, 1993). These strategies offer significant advantages over more traditional approaches, allowing the construction of complex molecular architectures from easily available starting materials in a single synthetic operation without the need for isolation of intermediates. Particularly, the chemistry of the azomethine ylide has gained significance in recent years for the construction of nitrogen containing five-membered heterocycles, which are often the central ring systems of numerous natural products (Daly et al., 1986; Waldmann, 1995). In contrast to similar compounds (Usha, Selvanayagam, Velmurugan, Ravikumar & Poornachandran, 2005; Usha, Selvanayagam, Velmurugan, Ravikumar & Raghunathan, 2005); Waldmann (1995)), in which the carbon atom bearing nitro group is bonded to the pyrrolidine ring, in the title compound it is bonded to the oxindole ring (Fig. 1). In the crystal structure, N—H···H hydrogen bonds link neighboring molecules. Molecules (Fig. 2) are also stacked in a side by side fashion along the c axis through π···π interaction and are further linked by a few intermolecular C—H···π interactions,

Related literature top

For related literature, see: Daly et al. (1986); Grigg & Sridharan (1993); Padwa (1984); Usha, Selvanayagam, Velmurugan, Ravikumar & Poornachandran (2005); Usha, Selvanayagam, Velmurugan, Ravikumar & Raghunathan (2005); Waldmann (1995).

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 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the molecules, viewed down the c axis.

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

Crystal data top

C₂₁H₂₁N₃O₃	F(000) = 768
M_r = 363.41	D_x = 1.394 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 792 reflections
a = 7.8524 (16) Å	θ = 3–23°
b = 25.656 (6) Å	µ = 0.10 mm⁻¹
c = 9.1767 (19) Å	T = 120 K
β = 110.489 (4)°	Prism, colorless
V = 1731.8 (6) Å³	0.21 × 0.18 × 0.15 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3773 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.980, T_max = 0.989	k = −32→32
16064 measured reflections	l = −11→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.01P)² + 1.6P] where P = (F_o² + 2F_c²)/3
3773 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₁H₂₁N₃O₃	V = 1731.8 (6) Å³
M_r = 363.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8524 (16) Å	µ = 0.10 mm⁻¹
b = 25.656 (6) Å	T = 120 K
c = 9.1767 (19) Å	0.21 × 0.18 × 0.15 mm
β = 110.489 (4)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3773 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2183 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.989	R_int = 0.064
16064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.01	Δρ_max = 0.25 e Å⁻³
3773 reflections	Δρ_min = −0.28 e Å⁻³
245 parameters

Special details top

Experimental. A mixture of isatin (0.147 g, 1 mmol), proline (0.115 g, 1 mmol), and (E)-1-phenyl-2-nitropropene (0.163 g, 1 mmol) in ethanol (10 ml) was stirred at reflux for 1 h. After completion of the reaction, as indicated by TLC, to the 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
N1	0.1573 (3)	0.19274 (7)	0.7966 (2)	0.0215 (4)
C2	0.1056 (3)	0.17387 (9)	0.6367 (3)	0.0210 (5)
C3	0.2848 (3)	0.14420 (9)	0.6478 (3)	0.0218 (5)
C4	0.3236 (3)	0.11281 (9)	0.8003 (3)	0.0209 (5)
H4A	0.2295	0.0859	0.7796	0.025*
C5	0.2810 (3)	0.15438 (9)	0.9046 (3)	0.0212 (5)
H5A	0.3944	0.1722	0.9645	0.025*
C6	0.1843 (3)	0.13826 (9)	1.0155 (3)	0.0250 (6)
H6A	0.2702	0.1284	1.1166	0.030*
H6B	0.1005	0.1097	0.9735	0.030*
C7	0.0836 (3)	0.18844 (9)	1.0247 (3)	0.0273 (6)
H7A	−0.0140	0.1817	1.0640	0.033*
H7B	0.1657	0.2141	1.0906	0.033*
C8	0.0098 (3)	0.20643 (10)	0.8562 (3)	0.0250 (6)
H8A	−0.1020	0.1883	0.7986	0.030*
H8B	−0.0129	0.2437	0.8495	0.030*
C9	0.4441 (3)	0.17830 (9)	0.6496 (3)	0.0245 (6)
H9A	0.5437	0.1566	0.6496	0.037*
H9B	0.4812	0.1996	0.7413	0.037*
H9C	0.4079	0.2002	0.5589	0.037*
C10	0.5061 (3)	0.08576 (9)	0.8734 (3)	0.0208 (5)
C11	0.5235 (3)	0.03378 (10)	0.8389 (3)	0.0285 (6)
H11A	0.4285	0.0173	0.7622	0.034*
C12	0.6799 (4)	0.00634 (10)	0.9170 (3)	0.0333 (6)
H12A	0.6905	−0.0282	0.8902	0.040*
C13	0.8199 (3)	0.02934 (10)	1.0338 (3)	0.0298 (6)
H13A	0.9226	0.0101	1.0894	0.036*
C14	0.8070 (3)	0.08119 (10)	1.0682 (3)	0.0280 (6)
H14A	0.9018	0.0972	1.1465	0.034*
C15	0.6529 (3)	0.10927 (10)	0.9861 (3)	0.0254 (6)
H15A	0.6475	0.1446	1.0068	0.030*
N2	0.2395 (3)	0.11023 (8)	0.5039 (2)	0.0241 (5)
O1	0.2495 (2)	0.06314 (7)	0.5158 (2)	0.0346 (4)
O2	0.1929 (2)	0.13377 (7)	0.37859 (19)	0.0310 (4)
N1'	−0.1068 (3)	0.21391 (8)	0.4167 (2)	0.0247 (5)
H1'	−0.1647	0.2377	0.3535	0.030*
C2'	0.0582 (3)	0.22165 (9)	0.5263 (3)	0.0245 (5)
O2'	0.1511 (2)	0.26105 (6)	0.54370 (19)	0.0298 (4)
C3A	−0.0662 (3)	0.14082 (9)	0.5689 (3)	0.0215 (5)
C4'	−0.1202 (3)	0.09354 (9)	0.6109 (3)	0.0248 (6)
H4D	−0.0455	0.0761	0.6989	0.030*
C5'	−0.2865 (3)	0.07228 (10)	0.5209 (3)	0.0271 (6)
H5D	−0.3224	0.0403	0.5482	0.032*
C6'	−0.3983 (3)	0.09824 (10)	0.3915 (3)	0.0266 (6)
H6D	−0.5086	0.0833	0.3316	0.032*
C7'	−0.3494 (3)	0.14616 (10)	0.3490 (3)	0.0252 (6)
H7D	−0.4259	0.1641	0.2628	0.030*
C7A	−0.1828 (3)	0.16639 (9)	0.4391 (3)	0.0231 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0226 (11)	0.0248 (11)	0.0180 (10)	0.0022 (9)	0.0084 (9)	−0.0003 (8)
C2	0.0219 (13)	0.0213 (13)	0.0192 (12)	0.0010 (10)	0.0066 (10)	−0.0011 (10)
C3	0.0227 (13)	0.0227 (13)	0.0187 (12)	−0.0006 (10)	0.0058 (10)	−0.0016 (10)
C4	0.0227 (13)	0.0201 (12)	0.0196 (12)	−0.0022 (10)	0.0072 (10)	−0.0008 (10)
C5	0.0206 (12)	0.0239 (13)	0.0191 (12)	0.0012 (10)	0.0069 (10)	−0.0007 (10)
C6	0.0292 (14)	0.0265 (14)	0.0219 (13)	0.0027 (11)	0.0122 (11)	0.0021 (11)
C7	0.0309 (14)	0.0290 (14)	0.0252 (14)	0.0025 (11)	0.0136 (12)	0.0001 (11)
C8	0.0219 (13)	0.0284 (14)	0.0257 (13)	0.0032 (11)	0.0098 (11)	−0.0006 (11)
C9	0.0234 (13)	0.0292 (14)	0.0227 (13)	−0.0025 (11)	0.0101 (11)	−0.0005 (11)
C10	0.0244 (13)	0.0231 (13)	0.0178 (12)	0.0008 (10)	0.0110 (10)	0.0038 (10)
C11	0.0307 (15)	0.0270 (14)	0.0261 (14)	0.0025 (11)	0.0078 (12)	−0.0007 (11)
C12	0.0392 (16)	0.0280 (15)	0.0337 (15)	0.0072 (13)	0.0141 (13)	−0.0019 (12)
C13	0.0281 (14)	0.0364 (15)	0.0283 (14)	0.0096 (12)	0.0141 (12)	0.0089 (12)
C14	0.0236 (14)	0.0354 (15)	0.0255 (13)	0.0004 (11)	0.0093 (11)	0.0008 (12)
C15	0.0267 (14)	0.0265 (13)	0.0253 (13)	0.0019 (11)	0.0119 (11)	0.0012 (11)
N2	0.0232 (11)	0.0297 (12)	0.0201 (11)	0.0006 (9)	0.0084 (9)	−0.0007 (10)
O1	0.0474 (12)	0.0247 (10)	0.0324 (10)	0.0009 (9)	0.0149 (9)	−0.0043 (8)
O2	0.0330 (10)	0.0415 (11)	0.0188 (9)	0.0023 (8)	0.0093 (8)	0.0017 (8)
N1'	0.0249 (11)	0.0259 (11)	0.0214 (11)	0.0018 (9)	0.0057 (9)	0.0058 (9)
C2'	0.0284 (14)	0.0247 (13)	0.0220 (13)	0.0012 (11)	0.0107 (11)	−0.0031 (11)
O2'	0.0319 (10)	0.0242 (10)	0.0318 (10)	−0.0025 (8)	0.0093 (8)	0.0024 (8)
C3A	0.0217 (13)	0.0231 (13)	0.0204 (12)	0.0022 (10)	0.0083 (10)	−0.0025 (10)
C4'	0.0262 (14)	0.0244 (13)	0.0240 (13)	0.0048 (11)	0.0090 (11)	0.0017 (11)
C5'	0.0278 (14)	0.0259 (14)	0.0298 (14)	−0.0018 (11)	0.0131 (12)	−0.0023 (11)
C6'	0.0205 (13)	0.0325 (15)	0.0267 (14)	−0.0033 (11)	0.0082 (11)	−0.0093 (11)
C7'	0.0266 (14)	0.0293 (14)	0.0190 (12)	0.0033 (11)	0.0071 (11)	−0.0006 (11)
C7A	0.0276 (14)	0.0232 (13)	0.0200 (13)	0.0012 (11)	0.0102 (11)	−0.0019 (10)

Geometric parameters (Å, º) top

N1—C2	1.461 (3)	C10—C11	1.388 (3)
N1—C8	1.486 (3)	C11—C12	1.379 (3)
N1—C5	1.490 (3)	C11—H11A	0.9300
C2—C3A	1.530 (3)	C12—C13	1.372 (3)
C2—C2'	1.550 (3)	C12—H12A	0.9300
C2—C3	1.571 (3)	C13—C14	1.379 (3)
C3—N2	1.517 (3)	C13—H13A	0.9300
C3—C9	1.522 (3)	C14—C15	1.383 (3)
C3—C4	1.550 (3)	C14—H14A	0.9300
C4—C10	1.521 (3)	C15—H15A	0.9300
C4—C5	1.546 (3)	N2—O1	1.213 (2)
C4—H4A	0.9800	N2—O2	1.235 (2)
C5—C6	1.525 (3)	N1'—C2'	1.348 (3)
C5—H5A	0.9800	N1'—C7A	1.404 (3)
C6—C7	1.528 (3)	N1'—H1'	0.8544
C6—H6A	0.9700	C2'—O2'	1.224 (3)
C6—H6B	0.9700	C3A—C4'	1.383 (3)
C7—C8	1.521 (3)	C3A—C7A	1.387 (3)
C7—H7A	0.9700	C4'—C5'	1.389 (3)
C7—H7B	0.9700	C4'—H4D	0.9300
C8—H8A	0.9700	C5'—C6'	1.377 (3)
C8—H8B	0.9700	C5'—H5D	0.9300
C9—H9A	0.9600	C6'—C7'	1.384 (3)
C9—H9B	0.9600	C6'—H6D	0.9300
C9—H9C	0.9600	C7'—C7A	1.381 (3)
C10—C15	1.388 (3)	C7'—H7D	0.9300

C2—N1—C8	118.04 (18)	C3—C9—H9C	109.5
C2—N1—C5	109.64 (18)	H9A—C9—H9C	109.5
C8—N1—C5	108.79 (17)	H9B—C9—H9C	109.5
N1—C2—C3A	119.15 (19)	C15—C10—C11	117.7 (2)
N1—C2—C2'	108.24 (18)	C15—C10—C4	122.6 (2)
C3A—C2—C2'	101.33 (18)	C11—C10—C4	119.4 (2)
N1—C2—C3	99.68 (17)	C12—C11—C10	120.8 (2)
C3A—C2—C3	113.59 (18)	C12—C11—H11A	119.6
C2'—C2—C3	115.5 (2)	C10—C11—H11A	119.6
N2—C3—C9	106.34 (19)	C13—C12—C11	120.7 (2)
N2—C3—C4	113.56 (19)	C13—C12—H12A	119.6
C9—C3—C4	112.82 (19)	C11—C12—H12A	119.6
N2—C3—C2	106.86 (17)	C12—C13—C14	119.4 (2)
C9—C3—C2	115.85 (19)	C12—C13—H13A	120.3
C4—C3—C2	101.46 (18)	C14—C13—H13A	120.3
C10—C4—C5	114.60 (18)	C15—C14—C13	119.9 (2)
C10—C4—C3	119.50 (19)	C15—C14—H14A	120.1
C5—C4—C3	100.59 (18)	C13—C14—H14A	120.1
C10—C4—H4A	107.1	C14—C15—C10	121.3 (2)
C5—C4—H4A	107.1	C14—C15—H15A	119.4
C3—C4—H4A	107.1	C10—C15—H15A	119.4
N1—C5—C6	105.17 (18)	O1—N2—O2	124.0 (2)
N1—C5—C4	106.01 (17)	O1—N2—C3	120.35 (19)
C6—C5—C4	119.5 (2)	O2—N2—C3	115.60 (19)
N1—C5—H5A	108.6	C2'—N1'—C7A	111.4 (2)
C6—C5—H5A	108.6	C2'—N1'—H1'	123.1
C4—C5—H5A	108.6	C7A—N1'—H1'	124.5
C5—C6—C7	101.31 (19)	O2'—C2'—N1'	126.3 (2)
C5—C6—H6A	111.5	O2'—C2'—C2	124.9 (2)
C7—C6—H6A	111.5	N1'—C2'—C2	108.6 (2)
C5—C6—H6B	111.5	C4'—C3A—C7A	118.7 (2)
C7—C6—H6B	111.5	C4'—C3A—C2	133.3 (2)
H6A—C6—H6B	109.3	C7A—C3A—C2	108.1 (2)
C8—C7—C6	102.72 (19)	C3A—C4'—C5'	119.6 (2)
C8—C7—H7A	111.2	C3A—C4'—H4D	120.2
C6—C7—H7A	111.2	C5'—C4'—H4D	120.2
C8—C7—H7B	111.2	C6'—C5'—C4'	120.4 (2)
C6—C7—H7B	111.2	C6'—C5'—H5D	119.8
H7A—C7—H7B	109.1	C4'—C5'—H5D	119.8
N1—C8—C7	103.52 (18)	C5'—C6'—C7'	121.1 (2)
N1—C8—H8A	111.1	C5'—C6'—H6D	119.4
C7—C8—H8A	111.1	C7'—C6'—H6D	119.4
N1—C8—H8B	111.1	C7A—C7'—C6'	117.6 (2)
C7—C8—H8B	111.1	C7A—C7'—H7D	121.2
H8A—C8—H8B	109.0	C6'—C7'—H7D	121.2
C3—C9—H9A	109.5	C7'—C7A—C3A	122.6 (2)
C3—C9—H9B	109.5	C7'—C7A—N1'	126.9 (2)
H9A—C9—H9B	109.5	C3A—C7A—N1'	110.5 (2)

C8—N1—C2—C3A	−34.1 (3)	C4—C10—C11—C12	−172.1 (2)
C5—N1—C2—C3A	91.2 (2)	C10—C11—C12—C13	1.9 (4)
C8—N1—C2—C2'	80.8 (2)	C11—C12—C13—C14	−3.0 (4)
C5—N1—C2—C2'	−153.89 (18)	C12—C13—C14—C15	0.7 (4)
C8—N1—C2—C3	−158.11 (19)	C13—C14—C15—C10	2.9 (4)
C5—N1—C2—C3	−32.8 (2)	C11—C10—C15—C14	−3.9 (3)
N1—C2—C3—N2	165.61 (17)	C4—C10—C15—C14	169.5 (2)
C3A—C2—C3—N2	37.8 (2)	C9—C3—N2—O1	119.1 (2)
C2'—C2—C3—N2	−78.7 (2)	C4—C3—N2—O1	−5.6 (3)
N1—C2—C3—C9	−76.1 (2)	C2—C3—N2—O1	−116.6 (2)
C3A—C2—C3—C9	156.02 (19)	C9—C3—N2—O2	−61.1 (2)
C2'—C2—C3—C9	39.5 (3)	C4—C3—N2—O2	174.21 (19)
N1—C2—C3—C4	46.4 (2)	C2—C3—N2—O2	63.2 (2)
C3A—C2—C3—C4	−81.4 (2)	C7A—N1'—C2'—O2'	−174.3 (2)
C2'—C2—C3—C4	162.10 (19)	C7A—N1'—C2'—C2	1.2 (3)
N2—C3—C4—C10	77.2 (3)	N1—C2—C2'—O2'	47.5 (3)
C9—C3—C4—C10	−43.9 (3)	C3A—C2—C2'—O2'	173.6 (2)
C2—C3—C4—C10	−168.54 (19)	C3—C2—C2'—O2'	−63.2 (3)
N2—C3—C4—C5	−156.50 (18)	N1—C2—C2'—N1'	−128.0 (2)
C9—C3—C4—C5	82.4 (2)	C3A—C2—C2'—N1'	−1.9 (2)
C2—C3—C4—C5	−42.2 (2)	C3—C2—C2'—N1'	121.3 (2)
C2—N1—C5—C6	−120.7 (2)	N1—C2—C3A—C4'	−59.9 (4)
C8—N1—C5—C6	9.7 (2)	C2'—C2—C3A—C4'	−178.4 (3)
C2—N1—C5—C4	6.8 (2)	C3—C2—C3A—C4'	57.1 (3)
C8—N1—C5—C4	137.19 (19)	N1—C2—C3A—C7A	120.6 (2)
C10—C4—C5—N1	152.38 (19)	C2'—C2—C3A—C7A	2.1 (2)
C3—C4—C5—N1	22.8 (2)	C3—C2—C3A—C7A	−122.5 (2)
C10—C4—C5—C6	−89.2 (3)	C7A—C3A—C4'—C5'	1.6 (3)
C3—C4—C5—C6	141.2 (2)	C2—C3A—C4'—C5'	−177.9 (2)
N1—C5—C6—C7	−32.2 (2)	C3A—C4'—C5'—C6'	−0.7 (4)
C4—C5—C6—C7	−151.0 (2)	C4'—C5'—C6'—C7'	−0.7 (4)
C5—C6—C7—C8	42.7 (2)	C5'—C6'—C7'—C7A	1.3 (4)
C2—N1—C8—C7	142.8 (2)	C6'—C7'—C7A—C3A	−0.4 (4)
C5—N1—C8—C7	17.1 (2)	C6'—C7'—C7A—N1'	179.8 (2)
C6—C7—C8—N1	−37.2 (2)	C4'—C3A—C7A—C7'	−1.0 (4)
C5—C4—C10—C15	−27.0 (3)	C2—C3A—C7A—C7'	178.6 (2)
C3—C4—C10—C15	92.4 (3)	C4'—C3A—C7A—N1'	178.8 (2)
C5—C4—C10—C11	146.3 (2)	C2—C3A—C7A—N1'	−1.5 (3)
C3—C4—C10—C11	−94.2 (3)	C2'—N1'—C7A—C7'	−179.9 (2)
C15—C10—C11—C12	1.5 (4)	C2'—N1'—C7A—C3A	0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1′—H1′···N1ⁱ	0.85	2.21	2.992 (3)	151

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O₃
M_r	363.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	7.8524 (16), 25.656 (6), 9.1767 (19)
β (°)	110.489 (4)
V (Å³)	1731.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.21 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	16064, 3773, 2183
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.103, 1.01
No. of reflections	3773
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

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'—H1'···N1ⁱ	0.85	2.21	2.992 (3)	151

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Acknowledgements

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

References

Bruker (2007). SMART and SAINT. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Daly, J. W., Spande, T. W., Whittaker, N., Highet, R. J., Feigl, D., Noshimori, N., Tokuyama, T. & Meyers, C. W. (1986). J. Nat. Prod. 46, 210–???. Google Scholar
Grigg, R. & Sridharan, V. (1993). Advances in Cycloaddition, edited by D. P. Curran, Vol. 3, p. 161. London: Jai. Google Scholar
Padwa, A. (1984). 1,3-Dipolar Cycloaddition Chemistry, Vols. 1 and 2. New York: Wiley. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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. (2005). Acta Cryst. E61, o3312–o3314. Web of Science CSD CrossRef IUCr Journals Google Scholar
Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K. & Raghunathan, R. (2005). Acta Cryst. E61, o3299–o3301. Web of Science CSD CrossRef IUCr Journals Google Scholar
Waldmann, H. (1995). Synlett, pp. 133–141. CrossRef Google Scholar

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

2′-Methyl-2′-nitro-1′-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

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