Ethyl 3′-cyano-1′-methyl-2-oxo-4′-phenylspiro­[acenaphthene-1,2′-pyrrolidine]-3′-carboxyl­ate

Yang, W.-L.; Zuo, Z.-Q.; Li, M.

doi:10.1107/S1600536807067530

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o440

doi:10.1107/S1600536807067530

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Ethyl 3′-cyano-1′-methyl-2-oxo-4′-phenylspiro[acenaphthene-1,2′-pyrrolidine]-3′-carboxylate

Wen-Long Yang,^a Zheng-Quan Zuo ^a and Ming Li ^a ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: liming928@qust.edu.cn

(Received 16 November 2007; accepted 18 December 2007; online 16 January 2008)

In the title compound, C₂₆H₂₂N₂O₃, the acenaphthen-1-one ring system is nearly planar and the pyrrolidine ring adopts a distorted envelope conformation. An intermolecular C—H⋯O hydrogen bond stabilizes the crystal structure.

Related literature

For related literature, see: Ma & Hecht (2004 ); Usui et al. (1998 ); Raghunathan & Suresh Babu (2004 ).

Experimental

Crystal data

C₂₆H₂₂N₂O₃
M_r = 410.46
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.564 (3) Å
b = 14.549 (6) Å
c = 19.397 (8) Å
V = 2134.7 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 (2) K
0.22 × 0.18 × 0.14 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.988
12376 measured reflections
2513 independent reflections
1924 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.101
S = 1.13
2513 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26B⋯O1ⁱ	0.96	2.53	3.276 (5)	135
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067530/rz2186sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067530/rz2186Isup2.hkl

checkCIF report

Comment top

Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties. The spirooxindole system is the core structure of many pharmacological agents and natural alkaloids (Ma & Hecht, 2004). Spirotryprostatin A, a natural alkaloid isolated from the fermentation broth of Aspergillus fumigatus, has been identified as a novel inhibitor of microtubule assembly (Usui et al., 1998). Because of their synthetic and biological potential, considerable interest has been focused on the synthesis of spirooxindole derivatives via 1,3-dipolar cycloaddition reactions (Raghunathan & Suresh Babu, 2006). In order to develop new biological activities, we synthesized the title compound, the structure of which is reported here.

In the molecule of the title compound (Fig. 1) there is one spiro junction at atom C12. The 2H-acenaphthylen-1-one ring system (C1—C12) is nearly planar, with a maximum displacement of 0.081 (3) Å for atom C1. The pyrrolidine ring adopts a distorted envelope conformation, with atom C12 forming the flap of the envelope displaced by 0.288 (2) A%. The mean plane through the pyrrolidine ring is almost perpendicular to the 2H-acenaphthylen-1-one ring (dihedral angle 86.62 (7)°). The crystal structure (Fig. 2) is stabilized by an intermolecular C—H···O hydrogen bond (Table 1).

Related literature top

For related literature, see: Ma & Hecht (2004); Usui et al. (1998); Raghunathan & Suresh Babu (2006).

Experimental top

A mixture of acenaphthylene-1,2-dione (1 mmol, 0.182 g), sarcosine (1 mmol, 0.089 g), benzaldehyde (1 mmol, 0.106 g), cyanoacetic acid ethyl ester (1 mmol, 0.113 g), and acetonitrile (15 ml) in a 25 ml flask was stirred for 3 h under reflux and monitored by TLC). After cooling to room temperature, the solid product was filtered off. Single crystals of the title compound were obtained by slow evaporation of an ethanol solution (m.p. 458 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with 35% probability ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the b axis. Intermolecular H bonds are shown as dashed lines.

Ethyl 3'-cyano-1'-methyl-2-oxo-4'-phenyl-spiro[acenaphthene-1,2'- pyrrolidine]-3'-carboxylate top

Crystal data top

C₂₆H₂₂N₂O₃	D_x = 1.277 Mg m⁻³
M_r = 410.46	Melting point: 458 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3377 reflections
a = 7.564 (3) Å	θ = 2.5–22.3°
b = 14.549 (6) Å	µ = 0.08 mm⁻¹
c = 19.397 (8) Å	T = 294 K
V = 2134.7 (15) Å³	Prism, brown
Z = 4	0.22 × 0.18 × 0.14 mm
F(000) = 864

Data collection top

Bruker SMART 100 CCD area-detector diffractometer	2513 independent reflections
Radiation source: fine-focus sealed tube	1924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→7
T_min = 0.982, T_max = 0.988	k = −17→18
12376 measured reflections	l = −23→24

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0449P)² + 0.2087P] where P = (F_o² + 2F_c²)/3
2513 reflections	(Δ/σ)_max < 0.001
282 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₆H₂₂N₂O₃	V = 2134.7 (15) Å³
M_r = 410.46	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.564 (3) Å	µ = 0.08 mm⁻¹
b = 14.549 (6) Å	T = 294 K
c = 19.397 (8) Å	0.22 × 0.18 × 0.14 mm

Data collection top

Bruker SMART 100 CCD area-detector diffractometer	2513 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1924 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.988	R_int = 0.049
12376 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.13	Δρ_max = 0.15 e Å⁻³
2513 reflections	Δρ_min = −0.16 e Å⁻³
282 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
O1	1.0623 (3)	0.94458 (13)	0.30244 (11)	0.0575 (6)
O2	0.5975 (3)	0.73612 (15)	0.19934 (13)	0.0628 (6)
O3	0.6641 (2)	0.88028 (13)	0.22923 (11)	0.0481 (5)
N1	1.1489 (3)	0.74780 (15)	0.28010 (11)	0.0376 (5)
N2	1.0479 (4)	0.90974 (17)	0.13933 (13)	0.0585 (8)
C1	0.9708 (4)	0.88274 (18)	0.32249 (14)	0.0374 (6)
C2	0.8422 (4)	0.88321 (19)	0.37975 (13)	0.0376 (6)
C3	0.7857 (4)	0.9520 (2)	0.42294 (16)	0.0505 (8)
H3	0.8282	1.0117	0.4183	0.061*
C4	0.6623 (5)	0.9298 (3)	0.47409 (16)	0.0612 (9)
H4	0.6204	0.9760	0.5029	0.073*
C5	0.6013 (4)	0.8416 (3)	0.48296 (15)	0.0557 (9)
H5	0.5186	0.8295	0.5173	0.067*
C6	0.6615 (4)	0.7694 (2)	0.44122 (14)	0.0423 (7)
C7	0.6195 (4)	0.6742 (2)	0.44642 (15)	0.0524 (8)
H7	0.5406	0.6539	0.4799	0.063*
C8	0.6951 (4)	0.6131 (2)	0.40222 (15)	0.0525 (8)
H8	0.6690	0.5510	0.4075	0.063*
C9	0.8115 (4)	0.63939 (19)	0.34877 (14)	0.0433 (7)
H9	0.8600	0.5955	0.3195	0.052*
C10	0.8515 (3)	0.73065 (18)	0.34083 (13)	0.0341 (6)
C11	0.7806 (3)	0.79340 (18)	0.38829 (12)	0.0338 (6)
C12	0.9724 (3)	0.78274 (17)	0.29125 (12)	0.0320 (6)
C13	1.1399 (4)	0.6722 (2)	0.23060 (15)	0.0463 (7)
H13A	1.1395	0.6136	0.2543	0.056*
H13B	1.2406	0.6740	0.1996	0.056*
C14	0.9672 (4)	0.68563 (16)	0.19040 (13)	0.0357 (6)
H14	0.8830	0.6407	0.2088	0.043*
C15	0.9028 (3)	0.78135 (17)	0.21481 (12)	0.0314 (6)
C16	1.2531 (4)	0.7268 (3)	0.34135 (17)	0.0578 (9)
H16A	1.2516	0.7786	0.3720	0.087*
H16B	1.3727	0.7136	0.3281	0.087*
H16C	1.2035	0.6743	0.3643	0.087*
C17	0.9744 (5)	0.67010 (18)	0.11349 (14)	0.0460 (8)
C18	1.1162 (6)	0.6991 (2)	0.07389 (17)	0.0716 (12)
H18	1.2091	0.7311	0.0941	0.086*
C19	1.1185 (9)	0.6799 (3)	0.0032 (2)	0.1023 (19)
H19	1.2134	0.6990	−0.0238	0.123*
C20	0.9814 (10)	0.6332 (3)	−0.0262 (2)	0.107 (2)
H20	0.9847	0.6201	−0.0731	0.128*
C21	0.8409 (8)	0.6057 (3)	0.0116 (2)	0.0861 (14)
H21	0.7473	0.5750	−0.0094	0.103*
C22	0.8374 (5)	0.6235 (2)	0.08185 (16)	0.0591 (9)
H22	0.7416	0.6037	0.1080	0.071*
C23	0.9873 (4)	0.85531 (18)	0.17424 (14)	0.0365 (6)
C24	0.7021 (4)	0.79504 (19)	0.21206 (14)	0.0370 (6)
C25	0.4781 (4)	0.9068 (2)	0.2361 (2)	0.0607 (9)
H25A	0.4209	0.9062	0.1914	0.073*
H25B	0.4168	0.8639	0.2660	0.073*
C26	0.4721 (5)	0.9978 (3)	0.2651 (3)	0.0941 (14)
H26A	0.5226	0.9969	0.3105	0.141*
H26B	0.3516	1.0181	0.2677	0.141*
H26C	0.5383	1.0391	0.2364	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0665 (15)	0.0462 (12)	0.0598 (13)	−0.0230 (12)	0.0173 (12)	−0.0112 (10)
O2	0.0395 (12)	0.0543 (13)	0.0945 (18)	−0.0096 (11)	−0.0045 (12)	−0.0145 (13)
O3	0.0324 (10)	0.0414 (11)	0.0706 (14)	0.0034 (9)	0.0027 (10)	−0.0039 (10)
N1	0.0311 (11)	0.0483 (13)	0.0335 (12)	0.0031 (10)	−0.0026 (10)	−0.0012 (10)
N2	0.0741 (19)	0.0453 (15)	0.0561 (16)	−0.0064 (14)	0.0201 (15)	0.0074 (13)
C1	0.0370 (15)	0.0385 (14)	0.0365 (14)	−0.0067 (13)	−0.0005 (12)	−0.0024 (12)
C2	0.0384 (15)	0.0433 (15)	0.0312 (13)	0.0010 (13)	0.0001 (12)	−0.0016 (12)
C3	0.0575 (19)	0.0464 (17)	0.0477 (17)	0.0045 (15)	0.0032 (16)	−0.0073 (14)
C4	0.065 (2)	0.073 (2)	0.0458 (18)	0.016 (2)	0.0149 (17)	−0.0116 (17)
C5	0.0451 (19)	0.083 (3)	0.0386 (17)	0.0052 (17)	0.0114 (14)	0.0015 (16)
C6	0.0340 (15)	0.0610 (18)	0.0320 (14)	−0.0032 (15)	−0.0006 (13)	0.0070 (13)
C7	0.0482 (19)	0.071 (2)	0.0380 (17)	−0.0146 (16)	−0.0013 (14)	0.0183 (16)
C8	0.060 (2)	0.0519 (18)	0.0456 (17)	−0.0141 (17)	−0.0057 (16)	0.0170 (15)
C9	0.0525 (18)	0.0398 (16)	0.0377 (15)	−0.0043 (14)	−0.0028 (14)	0.0046 (12)
C10	0.0338 (14)	0.0377 (14)	0.0307 (14)	−0.0025 (12)	−0.0028 (11)	0.0041 (11)
C11	0.0319 (14)	0.0426 (15)	0.0269 (13)	−0.0009 (12)	−0.0054 (11)	0.0015 (11)
C12	0.0301 (13)	0.0373 (14)	0.0287 (13)	−0.0023 (11)	0.0002 (11)	−0.0005 (10)
C13	0.0448 (16)	0.0455 (16)	0.0486 (17)	0.0104 (14)	0.0008 (14)	−0.0063 (14)
C14	0.0438 (15)	0.0297 (13)	0.0336 (14)	−0.0011 (12)	0.0025 (12)	−0.0001 (11)
C15	0.0328 (13)	0.0319 (13)	0.0293 (13)	−0.0014 (11)	0.0007 (11)	0.0003 (11)
C16	0.0418 (18)	0.081 (2)	0.0503 (19)	0.0054 (17)	−0.0088 (14)	0.0014 (17)
C17	0.074 (2)	0.0295 (14)	0.0348 (15)	0.0050 (15)	0.0030 (16)	−0.0001 (11)
C18	0.120 (3)	0.0406 (17)	0.055 (2)	−0.018 (2)	0.033 (2)	−0.0067 (15)
C19	0.200 (6)	0.048 (2)	0.059 (2)	−0.013 (3)	0.060 (3)	0.0018 (19)
C20	0.228 (7)	0.055 (2)	0.038 (2)	0.008 (4)	0.001 (3)	−0.0052 (18)
C21	0.141 (4)	0.065 (2)	0.052 (2)	0.016 (3)	−0.029 (3)	−0.012 (2)
C22	0.081 (2)	0.0478 (17)	0.0484 (18)	0.0094 (19)	−0.0120 (18)	−0.0104 (15)
C23	0.0376 (16)	0.0357 (14)	0.0363 (14)	0.0031 (12)	0.0035 (13)	0.0001 (12)
C24	0.0373 (15)	0.0394 (16)	0.0343 (14)	−0.0020 (13)	0.0005 (12)	0.0038 (12)
C25	0.0289 (16)	0.065 (2)	0.089 (2)	0.0090 (15)	0.0051 (17)	−0.0028 (18)
C26	0.045 (2)	0.068 (2)	0.169 (4)	0.0164 (19)	−0.002 (3)	−0.025 (3)

Geometric parameters (Å, º) top

O1—C1	1.200 (3)	C13—C14	1.534 (4)
O2—C24	1.193 (3)	C13—H13A	0.9700
O3—C24	1.316 (3)	C13—H13B	0.9700
O3—C25	1.465 (4)	C14—C17	1.510 (4)
N1—C12	1.445 (3)	C14—C15	1.550 (3)
N1—C16	1.458 (4)	C14—H14	0.9800
N1—C13	1.461 (3)	C15—C23	1.479 (4)
N2—C23	1.138 (3)	C15—C24	1.532 (4)
C1—C2	1.476 (4)	C16—H16A	0.9600
C1—C12	1.576 (4)	C16—H16B	0.9600
C2—C3	1.374 (4)	C16—H16C	0.9600
C2—C11	1.397 (4)	C17—C22	1.382 (4)
C3—C4	1.401 (4)	C17—C18	1.385 (5)
C3—H3	0.9300	C18—C19	1.400 (5)
C4—C5	1.374 (5)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.365 (8)
C5—C6	1.401 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.352 (7)
C6—C11	1.410 (4)	C20—H20	0.9300
C6—C7	1.425 (4)	C21—C22	1.388 (5)
C7—C8	1.362 (5)	C21—H21	0.9300
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.413 (4)	C25—C26	1.440 (5)
C8—H8	0.9300	C25—H25A	0.9700
C9—C10	1.371 (4)	C25—H25B	0.9700
C9—H9	0.9300	C26—H26A	0.9600
C10—C11	1.403 (4)	C26—H26B	0.9600
C10—C12	1.528 (3)	C26—H26C	0.9600
C12—C15	1.574 (3)

C24—O3—C25	118.7 (2)	C13—C14—C15	103.1 (2)
C12—N1—C16	116.8 (2)	C17—C14—H14	106.5
C12—N1—C13	108.7 (2)	C13—C14—H14	106.5
C16—N1—C13	113.8 (2)	C15—C14—H14	106.5
O1—C1—C2	128.3 (2)	C23—C15—C24	108.4 (2)
O1—C1—C12	124.3 (2)	C23—C15—C14	110.8 (2)
C2—C1—C12	107.4 (2)	C24—C15—C14	114.7 (2)
C3—C2—C11	120.4 (3)	C23—C15—C12	110.3 (2)
C3—C2—C1	131.8 (3)	C24—C15—C12	111.3 (2)
C11—C2—C1	107.7 (2)	C14—C15—C12	101.19 (19)
C2—C3—C4	118.1 (3)	N1—C16—H16A	109.5
C2—C3—H3	121.0	N1—C16—H16B	109.5
C4—C3—H3	121.0	H16A—C16—H16B	109.5
C5—C4—C3	121.9 (3)	N1—C16—H16C	109.5
C5—C4—H4	119.0	H16A—C16—H16C	109.5
C3—C4—H4	119.0	H16B—C16—H16C	109.5
C4—C5—C6	121.2 (3)	C22—C17—C18	118.9 (3)
C4—C5—H5	119.4	C22—C17—C14	119.0 (3)
C6—C5—H5	119.4	C18—C17—C14	122.0 (3)
C5—C6—C11	116.3 (3)	C17—C18—C19	119.5 (4)
C5—C6—C7	127.9 (3)	C17—C18—H18	120.3
C11—C6—C7	115.8 (3)	C19—C18—H18	120.3
C8—C7—C6	119.8 (3)	C20—C19—C18	120.0 (5)
C8—C7—H7	120.1	C20—C19—H19	120.0
C6—C7—H7	120.1	C18—C19—H19	120.0
C7—C8—C9	123.2 (3)	C21—C20—C19	121.2 (4)
C7—C8—H8	118.4	C21—C20—H20	119.4
C9—C8—H8	118.4	C19—C20—H20	119.4
C10—C9—C8	118.8 (3)	C20—C21—C22	119.5 (5)
C10—C9—H9	120.6	C20—C21—H21	120.2
C8—C9—H9	120.6	C22—C21—H21	120.2
C9—C10—C11	118.2 (2)	C17—C22—C21	120.9 (4)
C9—C10—C12	133.1 (3)	C17—C22—H22	119.6
C11—C10—C12	108.6 (2)	C21—C22—H22	119.6
C2—C11—C10	113.8 (2)	N2—C23—C15	175.6 (3)
C2—C11—C6	122.1 (3)	O2—C24—O3	125.8 (3)
C10—C11—C6	124.1 (3)	O2—C24—C15	124.8 (3)
N1—C12—C10	118.2 (2)	O3—C24—C15	109.3 (2)
N1—C12—C15	99.43 (19)	C26—C25—O3	107.9 (3)
C10—C12—C15	112.7 (2)	C26—C25—H25A	110.1
N1—C12—C1	112.9 (2)	O3—C25—H25A	110.1
C10—C12—C1	102.2 (2)	C26—C25—H25B	110.1
C15—C12—C1	111.8 (2)	O3—C25—H25B	110.1
N1—C13—C14	106.1 (2)	H25A—C25—H25B	108.4
N1—C13—H13A	110.5	C25—C26—H26A	109.5
C14—C13—H13A	110.5	C25—C26—H26B	109.5
N1—C13—H13B	110.5	H26A—C26—H26B	109.5
C14—C13—H13B	110.5	C25—C26—H26C	109.5
H13A—C13—H13B	108.7	H26A—C26—H26C	109.5
C17—C14—C13	116.9 (3)	H26B—C26—H26C	109.5
C17—C14—C15	116.6 (2)

O1—C1—C2—C3	3.3 (5)	C2—C1—C12—C10	−5.6 (3)
C12—C1—C2—C3	−178.0 (3)	O1—C1—C12—C15	−66.0 (3)
O1—C1—C2—C11	−174.2 (3)	C2—C1—C12—C15	115.2 (2)
C12—C1—C2—C11	4.6 (3)	C12—N1—C13—C14	21.8 (3)
C11—C2—C3—C4	−1.6 (4)	C16—N1—C13—C14	153.8 (2)
C1—C2—C3—C4	−178.8 (3)	N1—C13—C14—C17	137.8 (2)
C2—C3—C4—C5	1.7 (5)	N1—C13—C14—C15	8.5 (3)
C3—C4—C5—C6	0.5 (5)	C17—C14—C15—C23	−44.9 (3)
C4—C5—C6—C11	−2.8 (4)	C13—C14—C15—C23	84.6 (2)
C4—C5—C6—C7	176.0 (3)	C17—C14—C15—C24	78.2 (3)
C5—C6—C7—C8	−178.0 (3)	C13—C14—C15—C24	−152.3 (2)
C11—C6—C7—C8	0.8 (4)	C17—C14—C15—C12	−161.9 (2)
C6—C7—C8—C9	−2.1 (5)	C13—C14—C15—C12	−32.4 (2)
C7—C8—C9—C10	0.3 (4)	N1—C12—C15—C23	−72.4 (2)
C8—C9—C10—C11	2.7 (4)	C10—C12—C15—C23	161.5 (2)
C8—C9—C10—C12	178.2 (3)	C1—C12—C15—C23	47.1 (3)
C3—C2—C11—C10	−179.3 (3)	N1—C12—C15—C24	167.3 (2)
C1—C2—C11—C10	−1.5 (3)	C10—C12—C15—C24	41.2 (3)
C3—C2—C11—C6	−0.8 (4)	C1—C12—C15—C24	−73.2 (3)
C1—C2—C11—C6	177.0 (2)	N1—C12—C15—C14	45.0 (2)
C9—C10—C11—C2	174.3 (3)	C10—C12—C15—C14	−81.1 (2)
C12—C10—C11—C2	−2.3 (3)	C1—C12—C15—C14	164.5 (2)
C9—C10—C11—C6	−4.2 (4)	C13—C14—C17—C22	138.3 (3)
C12—C10—C11—C6	179.2 (2)	C15—C14—C17—C22	−99.1 (3)
C5—C6—C11—C2	3.0 (4)	C13—C14—C17—C18	−40.0 (4)
C7—C6—C11—C2	−176.0 (3)	C15—C14—C17—C18	82.5 (4)
C5—C6—C11—C10	−178.7 (3)	C22—C17—C18—C19	−0.6 (5)
C7—C6—C11—C10	2.4 (4)	C14—C17—C18—C19	177.7 (3)
C16—N1—C12—C10	−49.9 (3)	C17—C18—C19—C20	0.2 (6)
C13—N1—C12—C10	80.4 (3)	C18—C19—C20—C21	0.8 (7)
C16—N1—C12—C15	−172.1 (2)	C19—C20—C21—C22	−1.4 (7)
C13—N1—C12—C15	−41.8 (2)	C18—C17—C22—C21	0.0 (5)
C16—N1—C12—C1	69.2 (3)	C14—C17—C22—C21	−178.4 (3)
C13—N1—C12—C1	−160.4 (2)	C20—C21—C22—C17	1.0 (6)
C9—C10—C12—N1	−46.5 (4)	C25—O3—C24—O2	2.2 (5)
C11—C10—C12—N1	129.4 (2)	C25—O3—C24—C15	−174.6 (3)
C9—C10—C12—C15	68.7 (4)	C23—C15—C24—O2	131.9 (3)
C11—C10—C12—C15	−115.4 (2)	C14—C15—C24—O2	7.5 (4)
C9—C10—C12—C1	−171.1 (3)	C12—C15—C24—O2	−106.6 (3)
C11—C10—C12—C1	4.7 (3)	C23—C15—C24—O3	−51.2 (3)
O1—C1—C12—N1	45.1 (4)	C14—C15—C24—O3	−175.7 (2)
C2—C1—C12—N1	−133.6 (2)	C12—C15—C24—O3	70.2 (3)
O1—C1—C12—C10	173.2 (3)	C24—O3—C25—C26	171.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26B···O1ⁱ	0.96	2.53	3.276 (5)	135

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂N₂O₃
M_r	410.46
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	7.564 (3), 14.549 (6), 19.397 (8)
V (Å³)	2134.7 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.18 × 0.14

Data collection
Diffractometer	Bruker SMART 100 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	12376, 2513, 1924
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.13
No. of reflections	2513
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26B···O1ⁱ	0.96	2.53	3.276 (5)	134.9

Symmetry code: (i) x−1, y, z.

Acknowledgements

This project was supported by the National Science Foundation of China (No. 20572057) and the Natural Science Foundation of Shandong Province (Y2006B11) and the Doctoral Foundation of Qingdao University of Science and Technology.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ma, J. & Hecht, S. M. (2004). Chem. Commun. 10, 1190–1191. Web of Science CrossRef Google Scholar
Raghunathan, R. & Suresh Babu, A. R. (2006). Tetrahedron Lett. 47, 9221–9225. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Usui, T., Kondoh, M., Cui, C.-B., Mayumi, T. & Osada, H. (1998). Biochem. J. 333, 543–548. Web of Science CAS PubMed Google Scholar

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Volume 64| Part 2| February 2008| Page o440

doi:10.1107/S1600536807067530

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

Ethyl 3′-cyano-1′-methyl-2-oxo-4′-phenylspiro­[acenaphthene-1,2′-pyrrolidine]-3′-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 3′-cyano-1′-methyl-2-oxo-4′-phenylspiro[acenaphthene-1,2′-pyrrolidine]-3′-carboxylate