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The structure of the adduct of eucarvone with nitro­so­benzene, C16H19NO2, is reported. The [3.2.2] bicyclic system corresponds to two seven-membered rings in boat and distorted chair conformations and a six-membered ring that adopts a distorted boat conformation. No conjugation is observed between the phenyl group and the N-O system. The packing is directed mainly by a C...O hydrogen bond, C-H...O-(1 - x, -y, z) and by intermolecular C-H...[pi] interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100002729/sx1097sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100002729/sx1097Isup2.hkl
Contains datablock I

CCDC reference: 146049

Computing details top

Data collection: MSC/AFC Diffractometer Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Software; data reduction: MSC/AFC Diffractometer Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai & Pritzkow, 1995); software used to prepare material for publication: PLATON (Spek, 1990) and CSD (Allen & Kennard, 1993).

N-Phenyl-8-oxa-9-aza-1,4,4-trimethylbicyclo[3.2.2]non-6-en-one top
Crystal data top
C16H19NO2Dx = 1.205 Mg m3
Mr = 257.32Melting point: 329-331 K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
a = 10.417 (3) ÅCell parameters from 25 reflections
b = 8.263 (2) Åθ = 20.2–25.4°
c = 16.5049 (12) ŵ = 0.08 mm1
β = 92.746 (11)°T = 293 K
V = 1419.0 (5) Å3Prismatic, colourless
Z = 40.20 × 0.17 × 0.13 mm
F(000) = 552
Data collection top
Rigaku AFC7S
diffractometer
1819 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
θ/2θ scansh = 713
Absorption correction: ψ scan
MSC/AFC Diffractometer Software (Molecular Structure Corporation, 1993)
k = 810
Tmin = 0.964, Tmax = 1.000l = 2121
3571 measured reflections3 standard reflections every 150 reflections
3254 independent reflections intensity decay: none
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0692P)2 + 0.0281P]
where P = (Fo2 + 2Fc2)/3
3254 reflections(Δ/σ)max < 0.001
230 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.18 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
O80.26910 (10)0.14764 (15)0.17573 (6)0.0477 (3)
N90.14840 (12)0.22317 (17)0.15069 (8)0.0420 (3)
C50.14606 (15)0.2695 (2)0.06363 (10)0.0427 (4)
H50.0550 (19)0.308 (3)0.0517 (13)0.0768 (15)*
C1'0.04377 (14)0.1178 (2)0.16876 (9)0.0412 (4)
C60.17444 (16)0.1237 (2)0.01383 (10)0.0470 (4)
H60.116 (2)0.092 (3)0.0327 (13)0.0768 (15)*
C6'0.05857 (18)0.0423 (2)0.19187 (11)0.0516 (4)
H6'0.139 (2)0.091 (3)0.1937 (13)0.0768 (15)*
C30.36929 (17)0.3970 (2)0.09007 (13)0.0526 (5)
H3A0.426 (2)0.478 (3)0.0650 (13)0.0768 (15)*
H3B0.363 (2)0.421 (3)0.1489 (14)0.0768 (15)*
C2'0.07857 (17)0.1854 (2)0.16498 (12)0.0537 (5)
H2'0.0897 (19)0.296 (3)0.1513 (13)0.0768 (15)*
C40.23284 (16)0.4181 (2)0.05003 (11)0.0486 (4)
C20.42900 (16)0.2330 (2)0.08382 (11)0.0514 (4)
O210.53526 (12)0.2135 (2)0.05849 (11)0.0804 (5)
C10.35052 (15)0.0881 (2)0.11205 (11)0.0480 (4)
C70.27174 (17)0.0326 (2)0.03874 (11)0.0502 (4)
H70.297 (2)0.059 (3)0.0125 (14)0.0768 (15)*
C4'0.1701 (2)0.0671 (3)0.20375 (12)0.0633 (6)
H4'0.249 (2)0.126 (3)0.2149 (13)0.0768 (15)*
C5'0.0494 (2)0.1331 (3)0.20905 (13)0.0633 (5)
H5'0.038 (2)0.246 (3)0.2252 (14)0.0768 (15)*
C3'0.18474 (19)0.0929 (3)0.18087 (13)0.0625 (5)
H3'0.273 (2)0.146 (3)0.1785 (13)0.0768 (15)*
C110.4341 (2)0.0420 (3)0.15148 (17)0.0682 (6)
H11A0.381 (2)0.131 (3)0.1656 (13)0.0768 (15)*
H11B0.482 (2)0.001 (3)0.2009 (14)0.0768 (15)*
H11C0.503 (2)0.077 (3)0.1149 (13)0.0768 (15)*
C410.1732 (2)0.5678 (3)0.08779 (18)0.0715 (6)
H41A0.159 (2)0.552 (3)0.1470 (15)0.0768 (15)*
H41B0.232 (2)0.662 (3)0.0817 (13)0.0768 (15)*
H41C0.088 (2)0.589 (3)0.0615 (13)0.0768 (15)*
C420.2427 (2)0.4429 (3)0.04122 (14)0.0689 (6)
H42A0.154 (2)0.452 (3)0.0690 (14)0.0768 (15)*
H42B0.281 (2)0.545 (3)0.0495 (13)0.0768 (15)*
H42C0.296 (2)0.349 (3)0.0651 (14)0.0768 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O80.0402 (6)0.0591 (7)0.0434 (6)0.0040 (5)0.0035 (5)0.0027 (5)
N90.0381 (7)0.0443 (7)0.0437 (7)0.0021 (6)0.0023 (5)0.0016 (6)
C50.0391 (8)0.0448 (9)0.0440 (9)0.0001 (7)0.0008 (6)0.0068 (7)
C1'0.0432 (9)0.0446 (9)0.0361 (8)0.0013 (7)0.0045 (6)0.0032 (7)
C60.0467 (9)0.0532 (10)0.0411 (9)0.0096 (8)0.0034 (7)0.0002 (8)
C6'0.0523 (10)0.0535 (11)0.0491 (10)0.0020 (9)0.0022 (8)0.0094 (8)
C30.0448 (10)0.0465 (10)0.0661 (12)0.0069 (8)0.0001 (8)0.0016 (9)
C2'0.0481 (10)0.0511 (11)0.0631 (11)0.0037 (9)0.0136 (8)0.0010 (9)
C40.0440 (9)0.0433 (9)0.0583 (11)0.0030 (7)0.0010 (7)0.0080 (8)
C20.0391 (9)0.0576 (11)0.0572 (11)0.0006 (8)0.0011 (7)0.0040 (9)
O210.0453 (8)0.0803 (10)0.1174 (13)0.0002 (7)0.0243 (8)0.0069 (9)
C10.0390 (8)0.0460 (9)0.0592 (10)0.0051 (7)0.0041 (7)0.0012 (8)
C70.0544 (10)0.0438 (9)0.0529 (10)0.0030 (8)0.0095 (8)0.0090 (8)
C4'0.0604 (12)0.0739 (15)0.0565 (11)0.0176 (11)0.0115 (9)0.0068 (10)
C5'0.0714 (13)0.0566 (12)0.0619 (12)0.0112 (10)0.0032 (10)0.0174 (10)
C3'0.0486 (10)0.0744 (14)0.0657 (12)0.0007 (10)0.0139 (9)0.0042 (11)
C110.0535 (12)0.0578 (13)0.0923 (16)0.0126 (10)0.0077 (11)0.0071 (12)
C410.0610 (13)0.0437 (12)0.110 (2)0.0040 (10)0.0060 (13)0.0071 (12)
C420.0644 (13)0.0709 (15)0.0711 (14)0.0150 (11)0.0021 (10)0.0257 (12)
Geometric parameters (Å, º) top
O8—N91.4461 (17)C3—C41.548 (2)
O8—C11.4669 (19)C2'—C3'1.380 (3)
N9—C1'1.437 (2)C4—C421.528 (3)
N9—C51.486 (2)C4—C411.531 (3)
C5—C61.496 (2)C2—O211.213 (2)
C5—C41.547 (2)C2—C11.535 (3)
C1'—C6'1.383 (2)C1—C71.501 (3)
C1'—C2'1.390 (2)C1—C111.511 (3)
C6—C71.313 (3)C4'—C5'1.370 (3)
C6'—C5'1.392 (3)C4'—C3'1.381 (3)
C3—C21.497 (3)
N9—O8—C1117.69 (11)C42—C4—C3109.39 (16)
C1'—N9—O8109.68 (12)C41—C4—C3107.44 (17)
C1'—N9—C5112.29 (12)C5—C4—C3112.31 (14)
O8—N9—C5111.19 (11)O21—C2—C3122.22 (17)
N9—C5—C6109.20 (13)O21—C2—C1120.62 (17)
N9—C5—C4111.23 (13)C3—C2—C1117.15 (14)
C6—C5—C4115.28 (13)O8—C1—C7111.57 (13)
C6'—C1'—C2'119.11 (16)O8—C1—C11105.74 (16)
C6'—C1'—N9124.11 (15)C7—C1—C11114.30 (17)
C2'—C1'—N9116.74 (15)O8—C1—C2106.88 (13)
C7—C6—C5117.38 (16)C7—C1—C2105.79 (14)
C1'—C6'—C5'119.41 (18)C11—C1—C2112.42 (15)
C2—C3—C4116.65 (15)C6—C7—C1117.48 (17)
C3'—C2'—C1'120.68 (19)C5'—C4'—C3'119.16 (19)
C42—C4—C41109.90 (18)C4'—C5'—C6'121.4 (2)
C42—C4—C5108.47 (15)C2'—C3'—C4'120.2 (2)
C41—C4—C5109.31 (15)
C1—O8—N9—C1'108.11 (14)C2—C3—C4—C4280.2 (2)
C1—O8—N9—C516.70 (18)C2—C3—C4—C41160.50 (17)
C1'—N9—C5—C668.04 (17)C2—C3—C4—C540.3 (2)
O8—N9—C5—C655.29 (16)C4—C3—C2—O21127.8 (2)
C1'—N9—C5—C4163.61 (13)C4—C3—C2—C153.0 (2)
O8—N9—C5—C473.06 (16)N9—O8—C1—C731.29 (19)
O8—N9—C1'—C6'11.4 (2)N9—O8—C1—C11156.12 (14)
C5—N9—C1'—C6'112.80 (17)N9—O8—C1—C283.91 (15)
O8—N9—C1'—C2'166.40 (14)O21—C2—C1—O8149.90 (18)
C5—N9—C1'—C2'69.43 (18)C3—C2—C1—O829.4 (2)
N9—C5—C6—C746.37 (19)O21—C2—C1—C791.1 (2)
C4—C5—C6—C779.7 (2)C3—C2—C1—C789.66 (19)
C2'—C1'—C6'—C5'1.4 (3)O21—C2—C1—C1134.3 (3)
N9—C1'—C6'—C5'179.14 (16)C3—C2—C1—C11144.93 (19)
C6'—C1'—C2'—C3'2.6 (3)C5—C6—C7—C13.5 (2)
N9—C1'—C2'—C3'179.56 (17)O8—C1—C7—C643.1 (2)
N9—C5—C4—C42171.28 (15)C11—C1—C7—C6163.04 (18)
C6—C5—C4—C4246.3 (2)C2—C1—C7—C672.72 (19)
N9—C5—C4—C4168.9 (2)C3'—C4'—C5'—C6'0.0 (3)
C6—C5—C4—C41166.10 (17)C1'—C6'—C5'—C4'0.2 (3)
N9—C5—C4—C350.25 (19)C1'—C2'—C3'—C4'2.4 (3)
C6—C5—C4—C374.76 (19)C5'—C4'—C3'—C2'1.1 (3)
 

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