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The title compound, C16H21NO5, consists of a substituted 2,8-cyclo­octa­diene ring linked to a pyrrolidine ring through the N atom of the five-membered ring. The 2,8-cyclo­octa­diene moiety has a cis,cis configuration. The pyrrolidine ring adopts a twist conformation. A few interatomic close contacts seem to influence the shape of the mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016301/wn6174sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016301/wn6174Isup2.hkl
Contains datablock I

CCDC reference: 221716

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.099
  • Data-to-parameter ratio = 11.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C1 - C9 = 1.53 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C16H21NO5F(000) = 656
Mr = 307.34Dx = 1.317 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 9.3947 (18) Åθ = 10–22°
b = 14.195 (3) ŵ = 0.10 mm1
c = 11.7723 (11) ÅT = 293 K
β = 99.213 (12)°Plate, yellow
V = 1549.7 (4) Å30.35 × 0.25 × 0.15 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.051
Radiation source: fine-focus sealed tubeθmax = 26.3°, θmin = 3.0°
Graphite monochromatorh = 1111
non–profiled ω scansk = 017
3141 measured reflectionsl = 014
3141 independent reflections3 standard reflections every 120 min
1327 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 0.91 w = 1/[σ2(Fo2) + (0.0279P)2]
where P = (Fo2 + 2Fc2)/3
2994 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.17 e Å3
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
xyzUiso*/Ueq
H1610.401 (3)0.574 (3)0.718 (3)0.093 (13)*
H1620.513 (3)0.519 (2)0.653 (3)0.067 (10)*
H1320.244 (2)0.3638 (19)0.548 (2)0.034 (8)*
H810.077 (3)0.744 (2)0.250 (2)0.047 (8)*
H1420.181 (4)0.453 (2)0.753 (3)0.092 (13)*
H1310.122 (3)0.435 (2)0.554 (2)0.070 (10)*
H420.466 (3)0.6512 (17)0.538 (2)0.047 (8)*
H410.367 (2)0.6869 (17)0.431 (2)0.033 (7)*
H1410.223 (4)0.353 (2)0.740 (3)0.083 (13)*
H620.078 (3)0.652 (2)0.536 (2)0.053 (9)*
H520.292 (2)0.6984 (17)0.652 (2)0.038 (7)*
H610.064 (3)0.745 (2)0.583 (2)0.053 (9)*
H510.320 (3)0.788 (2)0.562 (2)0.060 (9)*
H1220.071 (5)0.352 (4)0.136 (4)0.16 (2)*
H1210.087 (5)0.345 (3)0.175 (4)0.155 (19)*
H1230.065 (3)0.296 (2)0.245 (3)0.080 (12)*
O40.0485 (2)0.43707 (13)0.26297 (15)0.0420 (5)
O20.2570 (2)0.54014 (13)0.15345 (14)0.0435 (5)
O30.2545 (2)0.37804 (13)0.36115 (16)0.0472 (5)
N10.3141 (2)0.50115 (15)0.57053 (17)0.0320 (5)
C20.1991 (3)0.54176 (17)0.3781 (2)0.0281 (6)
O10.0565 (2)0.62224 (16)0.09200 (16)0.0634 (7)
C30.2904 (3)0.56070 (18)0.4815 (2)0.0307 (6)
C40.3611 (3)0.6556 (2)0.5009 (3)0.0363 (7)
C90.1443 (3)0.5932 (2)0.1684 (2)0.0367 (7)
C10.1469 (3)0.61512 (19)0.2956 (2)0.0305 (6)
C110.1752 (3)0.44474 (19)0.3379 (2)0.0328 (7)
O50.0025 (3)0.82502 (15)0.39832 (18)0.0758 (8)
C130.2202 (4)0.4213 (2)0.5883 (2)0.0432 (8)
C160.4229 (4)0.5156 (2)0.6748 (2)0.0414 (8)
C50.2778 (3)0.7210 (2)0.5700 (3)0.0433 (8)
C80.0990 (3)0.7029 (2)0.3110 (2)0.0369 (7)
C70.0666 (3)0.7519 (2)0.4125 (2)0.0431 (7)
C60.1153 (3)0.7160 (2)0.5320 (3)0.0424 (8)
C120.0282 (5)0.3506 (3)0.1978 (4)0.0609 (11)
C140.2482 (4)0.4074 (3)0.7173 (3)0.0562 (10)
C100.2673 (3)0.5162 (2)0.0350 (2)0.0575 (9)
H10A0.35150.47830.03320.086*
H10B0.27410.57290.00830.086*
H10C0.18300.48160.00170.086*
C150.4037 (3)0.4323 (2)0.7501 (2)0.0560 (9)
H15A0.46510.38030.73490.067*
H15B0.42590.44900.83090.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0494 (12)0.0371 (12)0.0344 (10)0.0047 (10)0.0083 (9)0.0071 (9)
O20.0441 (12)0.0591 (14)0.0269 (10)0.0062 (10)0.0040 (9)0.0010 (10)
O30.0591 (14)0.0313 (12)0.0470 (12)0.0081 (11)0.0044 (10)0.0062 (10)
N10.0325 (12)0.0328 (13)0.0281 (12)0.0065 (11)0.0026 (10)0.0026 (11)
C20.0323 (15)0.0270 (15)0.0238 (13)0.0026 (12)0.0011 (12)0.0044 (12)
O10.0738 (15)0.0759 (17)0.0341 (12)0.0318 (13)0.0107 (11)0.0009 (11)
C30.0350 (15)0.0289 (15)0.0295 (14)0.0012 (13)0.0086 (12)0.0007 (13)
C40.0383 (18)0.0332 (17)0.0354 (17)0.0078 (14)0.0002 (14)0.0037 (14)
C90.0382 (17)0.0386 (18)0.0325 (16)0.0025 (14)0.0027 (14)0.0014 (14)
C10.0283 (15)0.0349 (17)0.0272 (14)0.0019 (13)0.0014 (12)0.0014 (13)
C110.0360 (16)0.0334 (18)0.0276 (14)0.0001 (14)0.0009 (12)0.0007 (13)
O50.1071 (19)0.0496 (15)0.0680 (17)0.0355 (14)0.0064 (14)0.0025 (13)
C130.046 (2)0.044 (2)0.0366 (18)0.0070 (17)0.0021 (16)0.0085 (16)
C160.0405 (19)0.053 (2)0.0266 (16)0.0024 (17)0.0063 (14)0.0049 (15)
C50.053 (2)0.0343 (19)0.0400 (18)0.0059 (16)0.0009 (16)0.0079 (16)
C80.0424 (18)0.0345 (18)0.0322 (17)0.0063 (15)0.0008 (13)0.0047 (14)
C70.0499 (19)0.0310 (16)0.0471 (18)0.0068 (14)0.0033 (15)0.0033 (15)
C60.054 (2)0.0346 (18)0.0413 (18)0.0006 (17)0.0162 (16)0.0058 (16)
C120.095 (3)0.037 (2)0.045 (2)0.012 (2)0.008 (2)0.0158 (18)
C140.052 (2)0.074 (3)0.040 (2)0.011 (2)0.0015 (17)0.022 (2)
C100.076 (2)0.067 (2)0.0314 (17)0.0093 (18)0.0129 (16)0.0084 (16)
C150.056 (2)0.069 (2)0.0388 (18)0.0079 (18)0.0057 (15)0.0150 (17)
Geometric parameters (Å, º) top
O4—C111.367 (3)C16—C151.505 (4)
O4—C121.444 (4)C16—H1611.01 (3)
O2—C91.334 (3)C16—H1620.93 (3)
O2—C101.454 (3)C5—C61.522 (4)
O3—C111.209 (3)C5—H521.00 (2)
N1—C31.337 (3)C5—H511.04 (3)
N1—C131.472 (4)C8—C71.457 (4)
N1—C161.481 (3)C8—H810.93 (3)
C2—C31.398 (3)C7—C61.498 (4)
C2—C11.454 (3)C6—H620.98 (3)
C2—C111.462 (3)C6—H610.93 (3)
O1—C91.193 (3)C12—H1220.88 (5)
C3—C41.503 (4)C12—H1211.08 (4)
C4—C51.530 (4)C12—H1230.98 (4)
C4—H421.02 (3)C14—C151.493 (4)
C4—H410.94 (2)C14—H1421.04 (3)
C9—C11.526 (3)C14—H1410.87 (3)
C1—C81.347 (4)C10—H10A0.9600
O5—C71.221 (3)C10—H10B0.9600
C13—C141.512 (4)C10—H10C0.9600
C13—H1320.99 (3)C15—H15A0.9700
C13—H1310.97 (3)C15—H15B0.9700
C11—O4—C12116.0 (3)C4—C5—H52108.4 (14)
C9—O2—C10115.8 (2)C6—C5—H51113.5 (15)
C3—N1—C13124.7 (2)C4—C5—H51105.5 (15)
C3—N1—C16124.7 (2)H52—C5—H51113 (2)
C13—N1—C16109.8 (2)C1—C8—C7132.1 (3)
C3—C2—C1122.5 (2)C1—C8—H81121.1 (16)
C3—C2—C11120.3 (2)C7—C8—H81106.8 (16)
C1—C2—C11116.1 (2)O5—C7—C8118.0 (3)
N1—C3—C2124.2 (2)O5—C7—C6119.6 (3)
N1—C3—C4115.7 (2)C8—C7—C6122.4 (3)
C2—C3—C4119.9 (2)C7—C6—C5113.7 (3)
C3—C4—C5111.9 (2)C7—C6—H62107.7 (17)
C3—C4—H42112.7 (15)C5—C6—H62112.6 (16)
C5—C4—H42110.8 (14)C7—C6—H61110.2 (16)
C3—C4—H41112.2 (14)C5—C6—H61113.0 (16)
C5—C4—H41106.5 (14)H62—C6—H6199 (2)
H42—C4—H41102.2 (19)O4—C12—H122112 (3)
O1—C9—O2124.3 (2)O4—C12—H121104 (2)
O1—C9—C1124.8 (3)H122—C12—H121112 (4)
O2—C9—C1110.9 (2)O4—C12—H123111.5 (19)
C8—C1—C2131.1 (2)H122—C12—H123109 (4)
C8—C1—C9111.6 (2)H121—C12—H123109 (3)
C2—C1—C9117.4 (2)C15—C14—C13103.6 (3)
O3—C11—O4121.7 (2)C15—C14—H142112.1 (19)
O3—C11—C2127.4 (2)C13—C14—H142108.0 (18)
O4—C11—C2110.9 (2)C15—C14—H141116 (2)
N1—C13—C14103.4 (3)C13—C14—H141114 (2)
N1—C13—H132112.2 (14)H142—C14—H141103 (3)
C14—C13—H132111.0 (14)O2—C10—H10A109.5
N1—C13—H131109.6 (18)O2—C10—H10B109.5
C14—C13—H131116.5 (17)H10A—C10—H10B109.5
H132—C13—H131104 (2)O2—C10—H10C109.5
N1—C16—C15104.3 (2)H10A—C10—H10C109.5
N1—C16—H161111.2 (18)H10B—C10—H10C109.5
C15—C16—H161107.3 (19)C14—C15—C16103.8 (3)
N1—C16—H162108.5 (18)C14—C15—H15A111.0
C15—C16—H162114.1 (19)C16—C15—H15A111.0
H161—C16—H162111 (3)C14—C15—H15B111.0
C6—C5—C4113.0 (2)C16—C15—H15B111.0
C6—C5—H52103.9 (14)H15A—C15—H15B109.0
C13—N1—C3—C218.7 (4)C12—O4—C11—C2166.6 (3)
C16—N1—C3—C2172.5 (3)C3—C2—C11—O324.8 (4)
C13—N1—C3—C4157.1 (3)C1—C2—C11—O3143.7 (3)
C16—N1—C3—C411.6 (4)C3—C2—C11—O4157.6 (2)
C1—C2—C3—N1163.8 (2)C1—C2—C11—O433.9 (3)
C11—C2—C3—N128.5 (4)C3—N1—C13—C14154.0 (3)
C1—C2—C3—C411.8 (4)C16—N1—C13—C1416.2 (4)
C11—C2—C3—C4155.8 (2)C3—N1—C16—C15177.9 (2)
N1—C3—C4—C579.0 (3)C13—N1—C16—C157.7 (3)
C2—C3—C4—C597.1 (3)C3—C4—C5—C642.5 (4)
C10—O2—C9—O11.5 (4)C2—C1—C8—C78.2 (5)
C10—O2—C9—C1178.9 (2)C9—C1—C8—C7172.2 (3)
C3—C2—C1—C841.4 (4)C1—C8—C7—O5165.6 (3)
C11—C2—C1—C8150.4 (3)C1—C8—C7—C614.7 (5)
C3—C2—C1—C9138.2 (2)O5—C7—C6—C5111.2 (3)
C11—C2—C1—C930.0 (3)C8—C7—C6—C568.5 (4)
O1—C9—C1—C833.9 (4)C4—C5—C6—C765.9 (3)
O2—C9—C1—C8143.5 (2)N1—C13—C14—C1534.0 (4)
O1—C9—C1—C2146.4 (3)C13—C14—C15—C1639.2 (4)
O2—C9—C1—C236.2 (3)N1—C16—C15—C1428.9 (4)
C12—O4—C11—O311.1 (4)
 

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