(rac-2SR,3RS,5SR)-Spiro­[3-methoxy­carbonyl-1-aza­bi­cyclo­[3.3.0]­octane-2,1'-ace­naphthyl­en]-2'-one

The molecular structure of the title compound, C₂₀H₁₉NO₃, contains a spiro-C atom connecting a bi­cyclo­octane group, consisting of two fused five-membered rings, to an ace­naphthyl­ene moiety. One of the five-membered rings of the bi­cyclo­octane moiety is in an envelope conformation, while the conformation of the other five-membered ring is close to a half-chair. The methoxy­carbonyl substituent is equatorial.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.137
• Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: isomorphous method; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

(rac-2SR,3RS,5SR)-Spiro[3-methoxycarbonyl-1-azabicyclo[3.3.0]octane-2,1'- acenaphthylen]-2'-one

Crystal data

C20H19NO3	F(000) = 680
Mr = 321.36	Dx = 1.332 Mg m^−3
Monoclinic, P21/c	Melting point: 418 K K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54180 Å
a = 9.5206 (1) Å	Cell parameters from 18832 reflections
b = 14.7738 (2) Å	θ = 4.9–69.9°
c = 14.6958 (2) Å	µ = 0.72 mm^−1
β = 129.182 (1)°	T = 293 K
V = 1602.25 (4) Å^3	Rectangular block, yellow
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	2994 independent reflections
Radiation source: fine-focus sealed tube	2476 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0.051
Detector resolution: 9 pixels mm^-1	θmax = 69.9°, θmin = 4.9°
φ scans with κ offsets	h = −11→11
Absorption correction: multi-scan (SORTAV; Blessing 1995)	k = −17→17
Tmin = 0.812, Tmax = 0.931	l = −16→17
35501 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0711P)^2 + 0.3621P] where P = (Fo^2 + 2Fc^2)/3
2994 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7412 (2)	0.28156 (11)	0.46382 (15)	0.0788 (4)
O2	0.58927 (19)	0.28561 (9)	0.53267 (12)	0.0686 (4)
O3	0.2726 (2)	0.09143 (9)	0.45181 (13)	0.0723 (4)
N1	0.28620 (18)	0.08521 (9)	0.25547 (12)	0.0497 (4)
C2	0.3350 (2)	0.16502 (11)	0.33057 (14)	0.0468 (4)
C3	0.5448 (2)	0.15839 (12)	0.42320 (15)	0.0533 (4)
H3	0.5747	0.1196	0.4875	0.064*
C4	0.5994 (2)	0.10913 (13)	0.35938 (17)	0.0584 (4)
H4A	0.6036	0.1501	0.3095	0.070*
H4B	0.7167	0.0803	0.4143	0.070*
C5	0.4512 (2)	0.03992 (12)	0.28754 (15)	0.0534 (4)
H5	0.4784	−0.0141	0.3350	0.064*
C6	0.4059 (3)	0.01289 (13)	0.17109 (17)	0.0612 (5)
H6A	0.5123	0.0164	0.1760	0.073*
H6B	0.3571	−0.0480	0.1485	0.073*
C7	0.2659 (3)	0.08157 (14)	0.08582 (17)	0.0646 (5)
H7A	0.1917	0.0592	0.0058	0.078*
H7B	0.3220	0.1382	0.0906	0.078*
C8	0.1557 (2)	0.09293 (13)	0.12707 (16)	0.0604 (5)
H8A	0.0967	0.1516	0.1039	0.073*
H8B	0.0639	0.0462	0.0939	0.073*
C2'	0.2413 (2)	0.15359 (11)	0.38735 (15)	0.0516 (4)
C3'	−0.0124 (3)	0.24867 (14)	0.36273 (17)	0.0601 (5)
H3'	−0.0272	0.2111	0.4069	0.072*
C4'	−0.1155 (3)	0.32768 (15)	0.31081 (18)	0.0685 (5)
H4'	−0.2008	0.3416	0.3204	0.082*
C5'	−0.0955 (3)	0.38532 (14)	0.24632 (17)	0.0647 (5)
H5'	−0.1659	0.4374	0.2142	0.078*
C6'	0.0656 (3)	0.41787 (12)	0.16258 (16)	0.0593 (5)
H6'	0.0041	0.4719	0.1275	0.071*
C7'	0.1891 (3)	0.38815 (12)	0.15114 (16)	0.0580 (4)
H7'	0.2088	0.4225	0.1071	0.070*
C8'	0.2886 (2)	0.30712 (12)	0.20361 (15)	0.0538 (4)
H8'	0.3729	0.2891	0.1946	0.065*
C9	0.2596 (2)	0.25548 (11)	0.26770 (13)	0.0453 (4)
C10	0.1310 (2)	0.28615 (11)	0.27911 (13)	0.0455 (4)
C11	0.1114 (2)	0.22828 (11)	0.34643 (14)	0.0492 (4)
C12	0.0305 (2)	0.36640 (12)	0.22824 (14)	0.0527 (4)
C13	0.6374 (2)	0.24756 (13)	0.47416 (15)	0.0548 (4)
C14	0.6693 (4)	0.37380 (16)	0.5834 (2)	0.0876 (7)
H14A	0.7874	0.3767	0.6045	0.131*
H14B	0.6797	0.3826	0.6521	0.131*
H14C	0.5936	0.4202	0.5270	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0803 (9)	0.0804 (10)	0.0958 (11)	−0.0233 (8)	0.0651 (9)	−0.0212 (8)
O2	0.0775 (9)	0.0699 (9)	0.0694 (8)	−0.0005 (7)	0.0516 (7)	−0.0085 (7)
O3	0.0922 (10)	0.0680 (9)	0.0803 (9)	0.0125 (7)	0.0657 (9)	0.0233 (7)
N1	0.0479 (7)	0.0486 (8)	0.0539 (8)	0.0023 (6)	0.0327 (7)	0.0009 (6)
C2	0.0464 (8)	0.0471 (9)	0.0490 (8)	0.0018 (6)	0.0312 (7)	0.0058 (7)
C3	0.0482 (9)	0.0534 (9)	0.0493 (9)	0.0013 (7)	0.0265 (8)	0.0052 (7)
C4	0.0485 (9)	0.0607 (10)	0.0629 (10)	0.0091 (8)	0.0337 (8)	0.0028 (8)
C5	0.0543 (9)	0.0496 (9)	0.0572 (10)	0.0079 (7)	0.0357 (8)	0.0069 (7)
C6	0.0687 (11)	0.0564 (10)	0.0683 (11)	0.0017 (8)	0.0480 (10)	−0.0003 (9)
C7	0.0691 (12)	0.0667 (12)	0.0556 (10)	0.0033 (9)	0.0382 (10)	0.0009 (8)
C8	0.0508 (9)	0.0598 (11)	0.0575 (10)	0.0010 (8)	0.0279 (8)	−0.0051 (8)
C2'	0.0583 (9)	0.0509 (9)	0.0504 (9)	−0.0029 (7)	0.0367 (8)	0.0021 (7)
C3'	0.0629 (10)	0.0698 (11)	0.0588 (10)	−0.0055 (9)	0.0438 (9)	−0.0084 (8)
C4'	0.0615 (11)	0.0807 (13)	0.0705 (12)	0.0062 (10)	0.0452 (10)	−0.0127 (10)
C5'	0.0611 (11)	0.0628 (11)	0.0602 (11)	0.0109 (9)	0.0336 (9)	−0.0077 (9)
C6'	0.0633 (11)	0.0442 (9)	0.0517 (9)	0.0022 (8)	0.0274 (9)	0.0033 (7)
C7'	0.0635 (10)	0.0505 (9)	0.0547 (10)	−0.0047 (8)	0.0348 (9)	0.0063 (8)
C8'	0.0540 (9)	0.0534 (10)	0.0562 (10)	−0.0024 (7)	0.0359 (8)	0.0042 (7)
C9	0.0443 (8)	0.0465 (8)	0.0443 (8)	−0.0015 (6)	0.0275 (7)	0.0023 (6)
C10	0.0454 (8)	0.0455 (8)	0.0414 (8)	−0.0021 (6)	0.0254 (7)	−0.0027 (6)
C11	0.0502 (8)	0.0541 (9)	0.0464 (8)	−0.0037 (7)	0.0321 (7)	−0.0062 (7)
C12	0.0502 (9)	0.0496 (9)	0.0454 (8)	0.0017 (7)	0.0240 (8)	−0.0062 (7)
C13	0.0499 (9)	0.0631 (10)	0.0489 (9)	0.0040 (8)	0.0301 (8)	0.0030 (7)
C14	0.1089 (19)	0.0723 (14)	0.0864 (15)	0.0005 (13)	0.0639 (15)	−0.0157 (12)

Geometric parameters (Å, º)

O1—C13	1.201 (2)	C8—H8A	0.9700
O2—C13	1.328 (2)	C8—H8B	0.9700
O2—C14	1.455 (3)	C2'—C11	1.473 (2)
O3—C2'	1.214 (2)	C3'—C11	1.377 (2)
N1—C8	1.468 (2)	C3'—C4'	1.401 (3)
N1—C2	1.475 (2)	C3'—H3'	0.9300
N1—C5	1.484 (2)	C4'—C5'	1.374 (3)
C2—C9	1.522 (2)	C4'—H4'	0.9300
C2—C3	1.554 (2)	C5'—C12	1.411 (3)
C2—C2'	1.569 (2)	C5'—H5'	0.9300
C3—C13	1.497 (3)	C6'—C7'	1.361 (3)
C3—C4	1.516 (3)	C6'—C12	1.424 (3)
C3—H3	0.9800	C6'—H6'	0.9300
C4—C5	1.506 (3)	C7'—C8'	1.415 (3)
C4—H4A	0.9700	C7'—H7'	0.9300
C4—H4B	0.9700	C8'—C9	1.369 (2)
C5—C6	1.530 (3)	C8'—H8'	0.9300
C5—H5	0.9800	C9—C10	1.411 (2)
C6—C7	1.505 (3)	C10—C12	1.406 (2)
C6—H6A	0.9700	C10—C11	1.406 (2)
C6—H6B	0.9700	C14—H14A	0.9600
C7—C8	1.517 (3)	C14—H14B	0.9600
C7—H7A	0.9700	C14—H14C	0.9600
C7—H7B	0.9700
C13—O2—C14	115.30 (16)	C7—C8—H8B	110.6
C8—N1—C2	120.69 (13)	H8A—C8—H8B	108.8
C8—N1—C5	108.04 (13)	O3—C2'—C11	127.88 (16)
C2—N1—C5	110.67 (12)	O3—C2'—C2	123.73 (16)
N1—C2—C9	116.28 (13)	C11—C2'—C2	108.37 (13)
N1—C2—C3	103.18 (12)	C11—C3'—C4'	118.05 (18)
C9—C2—C3	116.06 (13)	C11—C3'—H3'	121.0
N1—C2—C2'	107.20 (12)	C4'—C3'—H3'	121.0
C9—C2—C2'	102.05 (12)	C5'—C4'—C3'	122.50 (18)
C3—C2—C2'	112.02 (13)	C5'—C4'—H4'	118.8
C13—C3—C4	114.07 (15)	C3'—C4'—H4'	118.8
C13—C3—C2	114.07 (14)	C4'—C5'—C12	120.80 (18)
C4—C3—C2	103.99 (14)	C4'—C5'—H5'	119.6
C13—C3—H3	108.1	C12—C5'—H5'	119.6
C4—C3—H3	108.1	C7'—C6'—C12	120.14 (16)
C2—C3—H3	108.1	C7'—C6'—H6'	119.9
C5—C4—C3	102.92 (14)	C12—C6'—H6'	119.9
C5—C4—H4A	111.2	C6'—C7'—C8'	122.61 (17)
C3—C4—H4A	111.2	C6'—C7'—H7'	118.7
C5—C4—H4B	111.2	C8'—C7'—H7'	118.7
C3—C4—H4B	111.2	C9—C8'—C7'	119.31 (16)
H4A—C4—H4B	109.1	C9—C8'—H8'	120.3
N1—C5—C4	104.57 (13)	C7'—C8'—H8'	120.3
N1—C5—C6	105.59 (14)	C8'—C9—C10	118.04 (15)
C4—C5—C6	115.99 (15)	C8'—C9—C2	133.16 (15)
N1—C5—H5	110.1	C10—C9—C2	108.77 (13)
C4—C5—H5	110.1	C12—C10—C11	122.57 (15)
C6—C5—H5	110.1	C12—C10—C9	123.91 (15)
C7—C6—C5	103.35 (14)	C11—C10—C9	113.52 (14)
C7—C6—H6A	111.1	C3'—C11—C10	119.89 (17)
C5—C6—H6A	111.1	C3'—C11—C2'	133.12 (17)
C7—C6—H6B	111.1	C10—C11—C2'	106.99 (14)
C5—C6—H6B	111.1	C10—C12—C5'	116.17 (16)
H6A—C6—H6B	109.1	C10—C12—C6'	115.98 (16)
C6—C7—C8	102.36 (15)	C5'—C12—C6'	127.83 (17)
C6—C7—H7A	111.3	O1—C13—O2	123.59 (18)
C8—C7—H7A	111.3	O1—C13—C3	125.24 (17)
C6—C7—H7B	111.3	O2—C13—C3	111.16 (15)
C8—C7—H7B	111.3	O2—C14—H14A	109.5
H7A—C7—H7B	109.2	O2—C14—H14B	109.5
N1—C8—C7	105.53 (14)	H14A—C14—H14B	109.5
N1—C8—H8A	110.6	O2—C14—H14C	109.5
C7—C8—H8A	110.6	H14A—C14—H14C	109.5
N1—C8—H8B	110.6	H14B—C14—H14C	109.5
C8—N1—C2—C9	−6.6 (2)	C7'—C8'—C9—C10	−0.4 (2)
C5—N1—C2—C9	120.93 (14)	C7'—C8'—C9—C2	177.23 (16)
C8—N1—C2—C3	−134.81 (15)	N1—C2—C9—C8'	−65.9 (2)
C5—N1—C2—C3	−7.31 (16)	C3—C2—C9—C8'	55.7 (2)
C8—N1—C2—C2'	106.79 (16)	C2'—C2—C9—C8'	177.83 (18)
C5—N1—C2—C2'	−125.71 (14)	N1—C2—C9—C10	111.86 (15)
N1—C2—C3—C13	153.04 (14)	C3—C2—C9—C10	−126.49 (15)
C9—C2—C3—C13	24.7 (2)	C2'—C2—C9—C10	−4.40 (16)
C2'—C2—C3—C13	−91.98 (17)	C8'—C9—C10—C12	0.2 (2)
N1—C2—C3—C4	28.17 (16)	C2—C9—C10—C12	−177.92 (14)
C9—C2—C3—C4	−100.20 (16)	C8'—C9—C10—C11	179.96 (14)
C2'—C2—C3—C4	143.15 (14)	C2—C9—C10—C11	1.81 (18)
C13—C3—C4—C5	−163.23 (14)	C4'—C3'—C11—C10	−0.1 (3)
C2—C3—C4—C5	−38.36 (17)	C4'—C3'—C11—C2'	179.33 (18)
C8—N1—C5—C4	117.69 (15)	C12—C10—C11—C3'	1.2 (2)
C2—N1—C5—C4	−16.46 (17)	C9—C10—C11—C3'	−178.55 (15)
C8—N1—C5—C6	−5.17 (18)	C12—C10—C11—C2'	−178.36 (14)
C2—N1—C5—C6	−139.31 (14)	C9—C10—C11—C2'	1.91 (19)
C3—C4—C5—N1	33.70 (17)	O3—C2'—C11—C3'	−2.8 (3)
C3—C4—C5—C6	149.53 (15)	C2—C2'—C11—C3'	175.81 (18)
N1—C5—C6—C7	27.25 (18)	O3—C2'—C11—C10	176.68 (18)
C4—C5—C6—C7	−88.00 (18)	C2—C2'—C11—C10	−4.73 (17)
C5—C6—C7—C8	−38.10 (19)	C11—C10—C12—C5'	−1.3 (2)
C2—N1—C8—C7	109.77 (17)	C9—C10—C12—C5'	178.42 (15)
C5—N1—C8—C7	−18.90 (18)	C11—C10—C12—C6'	179.97 (15)
C6—C7—C8—N1	35.63 (19)	C9—C10—C12—C6'	−0.3 (2)
N1—C2—C2'—O3	61.5 (2)	C4'—C5'—C12—C10	0.3 (3)
C9—C2—C2'—O3	−175.81 (17)	C4'—C5'—C12—C6'	178.89 (18)
C3—C2—C2'—O3	−51.0 (2)	C7'—C6'—C12—C10	0.6 (2)
N1—C2—C2'—C11	−117.16 (14)	C7'—C6'—C12—C5'	−177.99 (17)
C9—C2—C2'—C11	5.53 (16)	C14—O2—C13—O1	0.9 (3)
C3—C2—C2'—C11	130.34 (14)	C14—O2—C13—C3	−178.65 (16)
C11—C3'—C4'—C5'	−0.9 (3)	C4—C3—C13—O1	2.9 (3)
C3'—C4'—C5'—C12	0.8 (3)	C2—C3—C13—O1	−116.5 (2)
C12—C6'—C7'—C8'	−0.8 (3)	C4—C3—C13—O2	−177.56 (14)
C6'—C7'—C8'—C9	0.7 (3)	C2—C3—C13—O2	63.13 (19)