Ethyl 3'-cyano-1'-methyl-2-oxo-4'-phenylspiro-[acenaphthene-1,2'-pyrrolidine]-3'-carboxyl-ate.

In the title compound, C(26)H(22)N(2)O(3), the acenaphthen-1-one ring system is nearly planar and the pyrrolidine ring adopts a distorted envelope conformation. An inter-molecular 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 = 410.46

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.101

S = 1.13

2513 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H22N2O3	Dx = 1.277 Mg m−3
Mr = 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 = 2.5–22.3º
b = 14.549 (6) Å	µ = 0.08 mm−1
c = 19.397 (8) Å	T = 294 (2) K
V = 2134.7 (15) Å3	Prism, brown
Z = 4	0.22 × 0.18 × 0.14 mm
F000 = 864

Bruker SMART 100 CCD area-detector diffractometer	2513 independent reflections
Radiation source: fine-focus sealed tube	1924 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
T = 294(2) K	θmax = 26.4º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→7
Tmin = 0.982, Tmax = 0.988	k = −17→18
12376 measured reflections	l = −23→24

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.2087P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
2513 reflections	Δρmax = 0.15 e Å−3
282 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .