Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021198/ci2373sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021198/ci2373Isup2.hkl |
CCDC reference: 651372
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.048
- wR factor = 0.117
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Liu & Larock (2004, 2005); Pellissier & Santelli (2003); Yoshida et al. (2002).
2-(Trimethylsilyl)phenyl trifluoromethanesulfonate (0.48 ml) and 4,4-dimethyl-2-oxazoline (0.12 ml) were added to a mixture of CsF (0.3032 g), [RuCl2(η6-C6H6)]2 (0.02 g), PPh3 (0.042 g) in CH3CN (0.6 ml) and toluene (3.0 ml). The mixture was stirred under argon at 408 K for 24 h. The organic layer was filtered and concentrated in vacuo. The crude product was further purified by column chromatography on silica gel to obtain the title compound as a white solid. Colourless needle-shaped crystals of (I) suitable for X-ray analysis were grown by slow evaporation of a hexane solution at room temperature.
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
2-(Trimethylsilyl)phenyltriflate, an efficient precursor to benzyne, has been widely employed for syntheses of complex organic compounds (Pellissier & Santelli, 2003). Recently, Liu and Larock (2004) reported addition of H—X bonds (X = N, O and S) to arynes to construct a new carbon-heteroatom bond (Liu & Larock, 2004). There are also examples of the transition-metal-free insertion of an aryne into polar hetero atom-containing bonds such as C—N σ bond (Yoshida et al., 2002) and intermolecular C—N bond reaction under very mild conditions (Liu & Larock, 2005). However, there is no example of insertion of aryne into C═N double bonds. We report here the crystal structure of the title compound, (I), which was obtained through insertion of two benzyne molecules into C═N double bonds.
As shown in Fig. 1, the oxaazabicyclo[3.2.2]nonane unit is composed of one six-membered ring and two seven-membered rings, which are connected with each other by the brigdehead atoms N1 and C7. The bond lengths and angles in (I) are normal except the slightly longer C7—C23 [1.5296 (19) Å], C7—C17 [1.5317 (19) Å] and C9—N1 [1.5209 (18) Å] bonds, which may result from the ring fusion.
The six-membered ring of the oxaazabicyclo[3.2.2]nonane unit adopts a boat conformation, with atoms N1 and C7 deviating from the C12/C17/C18/C23 plane by 0.542 (1) and 0.608 (1) Å, respectively. One of the seven-membered rings (N1,C9,C8,O1,C7,C23,C18) adopts a boat conformation, with atoms C8, C18 and C23 deviating from the plane defined by other four atoms by 0.624 (2), 1.149 (1) and 1.249 (1) Å, respectively. The other seven-membered ring (N1,C9,C8,O1,C7,C12,C17) adopts a chair conformation. The dihedral angle between the two benzene rings (C12—C17 and C18—C23) is 51.89 (4)°. The C1—C6 phenyl ring forms dihedral angles of 60.04 (5)° and 68.23 (5)°, respectively, with the C12—C17 and C18—C23 benzene rings.
No significant hydrogen bonds are observed in the crystal structure.
For general background, see: Liu & Larock (2004, 2005); Pellissier & Santelli (2003); Yoshida et al. (2002).
Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellopsoids. H atoms have been omitted for clarity. |
C23H21NO | F(000) = 696 |
Mr = 327.41 | Dx = 1.256 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3669 reflections |
a = 15.707 (6) Å | θ = 2.8–27.5° |
b = 9.227 (4) Å | µ = 0.08 mm−1 |
c = 12.198 (5) Å | T = 293 K |
β = 101.575 (6)° | Prism, colourless |
V = 1731.7 (12) Å3 | 0.20 × 0.15 × 0.11 mm |
Z = 4 |
Rigaku Mercury CCD area-detector diffractometer | 3911 independent reflections |
Radiation source: fine-focus sealed tube | 3171 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 14.6306 pixels mm-1 | θmax = 27.4°, θmin = 2.8° |
ω scans | h = −18→20 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004) | k = −11→11 |
Tmin = 0.981, Tmax = 0.992 | l = −15→15 |
13049 measured reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0498P)2 + 0.3898P] where P = (Fo2 + 2Fc2)/3 |
3911 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C23H21NO | V = 1731.7 (12) Å3 |
Mr = 327.41 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.707 (6) Å | µ = 0.08 mm−1 |
b = 9.227 (4) Å | T = 293 K |
c = 12.198 (5) Å | 0.20 × 0.15 × 0.11 mm |
β = 101.575 (6)° |
Rigaku Mercury CCD area-detector diffractometer | 3911 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004) | 3171 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.992 | Rint = 0.033 |
13049 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.21 e Å−3 |
3911 reflections | Δρmin = −0.17 e Å−3 |
226 parameters |
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 | ||
C1 | 0.96183 (10) | 0.24037 (17) | 0.28052 (13) | 0.0431 (4) | |
H1 | 0.9429 | 0.2047 | 0.3428 | 0.052* | |
C2 | 1.04785 (10) | 0.28135 (19) | 0.28977 (15) | 0.0519 (4) | |
H2 | 1.0861 | 0.2729 | 0.3583 | 0.062* | |
C3 | 1.07728 (10) | 0.33424 (19) | 0.19895 (16) | 0.0532 (4) | |
H3 | 1.1348 | 0.3634 | 0.2061 | 0.064* | |
C4 | 1.02079 (11) | 0.34364 (19) | 0.09715 (16) | 0.0532 (4) | |
H4 | 1.0406 | 0.3769 | 0.0348 | 0.064* | |
C5 | 0.93473 (10) | 0.30390 (19) | 0.08725 (13) | 0.0464 (4) | |
H5 | 0.8969 | 0.3118 | 0.0183 | 0.056* | |
C6 | 0.90390 (9) | 0.25219 (15) | 0.17922 (11) | 0.0347 (3) | |
C7 | 0.80819 (9) | 0.21735 (15) | 0.16881 (10) | 0.0317 (3) | |
C8 | 0.72086 (9) | 0.18203 (16) | 0.31426 (11) | 0.0355 (3) | |
H8A | 0.7166 | 0.2861 | 0.3229 | 0.043* | |
H8B | 0.7257 | 0.1387 | 0.3877 | 0.043* | |
C9 | 0.63664 (9) | 0.12763 (15) | 0.23859 (11) | 0.0343 (3) | |
C10 | 0.56008 (10) | 0.19291 (19) | 0.28076 (13) | 0.0473 (4) | |
H10A | 0.5067 | 0.1602 | 0.2346 | 0.071* | |
H10B | 0.5630 | 0.2967 | 0.2776 | 0.071* | |
H10C | 0.5623 | 0.1629 | 0.3567 | 0.071* | |
C11 | 0.63202 (12) | −0.03686 (17) | 0.24199 (14) | 0.0484 (4) | |
H11A | 0.5791 | −0.0691 | 0.1944 | 0.073* | |
H11B | 0.6332 | −0.0680 | 0.3174 | 0.073* | |
H11C | 0.6808 | −0.0773 | 0.2163 | 0.073* | |
C12 | 0.68217 (9) | 0.08999 (14) | 0.05706 (11) | 0.0327 (3) | |
C13 | 0.64116 (11) | −0.00665 (16) | −0.02287 (12) | 0.0411 (3) | |
H13 | 0.5811 | −0.0174 | −0.0360 | 0.049* | |
C14 | 0.69024 (12) | −0.08768 (17) | −0.08352 (13) | 0.0490 (4) | |
H14 | 0.6629 | −0.1526 | −0.1376 | 0.059* | |
C15 | 0.77895 (12) | −0.07215 (18) | −0.06376 (13) | 0.0499 (4) | |
H15 | 0.8115 | −0.1270 | −0.1044 | 0.060* | |
C16 | 0.82047 (10) | 0.02507 (16) | 0.01655 (12) | 0.0411 (3) | |
H16 | 0.8806 | 0.0349 | 0.0296 | 0.049* | |
C17 | 0.77218 (9) | 0.10735 (14) | 0.07715 (11) | 0.0323 (3) | |
C18 | 0.66150 (9) | 0.32615 (14) | 0.11765 (10) | 0.0308 (3) | |
C19 | 0.60351 (10) | 0.44013 (16) | 0.09311 (12) | 0.0389 (3) | |
H19 | 0.5440 | 0.4225 | 0.0772 | 0.047* | |
C20 | 0.63460 (11) | 0.58057 (17) | 0.09236 (13) | 0.0449 (4) | |
H20 | 0.5958 | 0.6573 | 0.0751 | 0.054* | |
C21 | 0.72252 (11) | 0.60710 (17) | 0.11705 (13) | 0.0452 (4) | |
H21 | 0.7430 | 0.7016 | 0.1158 | 0.054* | |
C22 | 0.78091 (10) | 0.49345 (15) | 0.14383 (12) | 0.0381 (3) | |
H22 | 0.8402 | 0.5122 | 0.1622 | 0.046* | |
C23 | 0.75088 (9) | 0.35205 (14) | 0.14324 (10) | 0.0307 (3) | |
O1 | 0.79830 (6) | 0.15078 (11) | 0.27410 (7) | 0.0358 (2) | |
N1 | 0.63133 (7) | 0.17812 (12) | 0.11871 (9) | 0.0325 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0368 (8) | 0.0491 (9) | 0.0415 (8) | −0.0009 (7) | 0.0032 (6) | −0.0013 (7) |
C2 | 0.0377 (9) | 0.0570 (10) | 0.0559 (10) | −0.0020 (7) | −0.0031 (7) | −0.0066 (8) |
C3 | 0.0332 (8) | 0.0485 (10) | 0.0780 (12) | −0.0036 (7) | 0.0117 (8) | −0.0092 (9) |
C4 | 0.0452 (9) | 0.0560 (10) | 0.0637 (11) | −0.0010 (8) | 0.0238 (8) | 0.0047 (8) |
C5 | 0.0375 (8) | 0.0608 (10) | 0.0419 (8) | 0.0017 (7) | 0.0100 (6) | 0.0058 (7) |
C6 | 0.0312 (7) | 0.0361 (7) | 0.0368 (7) | 0.0039 (6) | 0.0066 (6) | −0.0011 (6) |
C7 | 0.0326 (7) | 0.0355 (7) | 0.0267 (6) | 0.0028 (6) | 0.0054 (5) | 0.0024 (5) |
C8 | 0.0373 (8) | 0.0425 (8) | 0.0279 (6) | 0.0018 (6) | 0.0094 (5) | 0.0018 (6) |
C9 | 0.0353 (7) | 0.0369 (7) | 0.0317 (7) | −0.0009 (6) | 0.0089 (6) | 0.0008 (6) |
C10 | 0.0401 (8) | 0.0591 (10) | 0.0453 (9) | 0.0001 (7) | 0.0152 (7) | −0.0017 (7) |
C11 | 0.0598 (10) | 0.0403 (9) | 0.0468 (9) | −0.0079 (7) | 0.0150 (8) | 0.0049 (7) |
C12 | 0.0391 (7) | 0.0307 (7) | 0.0279 (6) | 0.0021 (6) | 0.0059 (5) | 0.0009 (5) |
C13 | 0.0486 (9) | 0.0373 (8) | 0.0353 (7) | −0.0030 (7) | 0.0032 (6) | −0.0026 (6) |
C14 | 0.0700 (12) | 0.0368 (8) | 0.0377 (8) | 0.0021 (8) | 0.0049 (7) | −0.0088 (6) |
C15 | 0.0684 (11) | 0.0413 (9) | 0.0421 (9) | 0.0147 (8) | 0.0163 (8) | −0.0050 (7) |
C16 | 0.0449 (8) | 0.0401 (8) | 0.0395 (8) | 0.0095 (7) | 0.0114 (6) | 0.0016 (6) |
C17 | 0.0382 (7) | 0.0310 (7) | 0.0276 (6) | 0.0049 (6) | 0.0060 (5) | 0.0033 (5) |
C18 | 0.0341 (7) | 0.0312 (7) | 0.0265 (6) | 0.0021 (5) | 0.0045 (5) | −0.0003 (5) |
C19 | 0.0354 (7) | 0.0420 (8) | 0.0376 (7) | 0.0075 (6) | 0.0036 (6) | 0.0013 (6) |
C20 | 0.0501 (9) | 0.0358 (8) | 0.0476 (9) | 0.0116 (7) | 0.0069 (7) | 0.0037 (6) |
C21 | 0.0544 (10) | 0.0315 (8) | 0.0496 (9) | −0.0003 (7) | 0.0106 (7) | 0.0019 (6) |
C22 | 0.0390 (8) | 0.0365 (8) | 0.0388 (8) | −0.0022 (6) | 0.0081 (6) | −0.0002 (6) |
C23 | 0.0328 (7) | 0.0331 (7) | 0.0260 (6) | 0.0015 (5) | 0.0050 (5) | −0.0004 (5) |
O1 | 0.0330 (5) | 0.0443 (6) | 0.0305 (5) | 0.0051 (4) | 0.0075 (4) | 0.0069 (4) |
N1 | 0.0340 (6) | 0.0326 (6) | 0.0305 (6) | 0.0001 (5) | 0.0058 (5) | −0.0019 (5) |
C1—C6 | 1.384 (2) | C11—H11A | 0.96 |
C1—C2 | 1.386 (2) | C11—H11B | 0.96 |
C1—H1 | 0.93 | C11—H11C | 0.96 |
C2—C3 | 1.373 (3) | C12—C13 | 1.381 (2) |
C2—H2 | 0.93 | C12—C17 | 1.395 (2) |
C3—C4 | 1.376 (3) | C12—N1 | 1.4510 (17) |
C3—H3 | 0.93 | C13—C14 | 1.389 (2) |
C4—C5 | 1.382 (2) | C13—H13 | 0.93 |
C4—H4 | 0.93 | C14—C15 | 1.373 (2) |
C5—C6 | 1.392 (2) | C14—H14 | 0.93 |
C5—H5 | 0.93 | C15—C16 | 1.390 (2) |
C6—C7 | 1.518 (2) | C15—H15 | 0.93 |
C7—O1 | 1.4596 (16) | C16—C17 | 1.3868 (19) |
C7—C23 | 1.5296 (19) | C16—H16 | 0.93 |
C7—C17 | 1.5317 (19) | C18—C19 | 1.384 (2) |
C8—O1 | 1.4289 (16) | C18—C23 | 1.3963 (19) |
C8—C9 | 1.537 (2) | C18—N1 | 1.4467 (18) |
C8—H8A | 0.97 | C19—C20 | 1.385 (2) |
C8—H8B | 0.97 | C19—H19 | 0.93 |
C9—C11 | 1.520 (2) | C20—C21 | 1.375 (2) |
C9—N1 | 1.5209 (18) | C20—H20 | 0.93 |
C9—C10 | 1.524 (2) | C21—C22 | 1.388 (2) |
C10—H10A | 0.96 | C21—H21 | 0.93 |
C10—H10B | 0.96 | C22—C23 | 1.387 (2) |
C10—H10C | 0.96 | C22—H22 | 0.93 |
C6—C1—C2 | 120.45 (15) | H11A—C11—H11B | 109.5 |
C6—C1—H1 | 119.8 | C9—C11—H11C | 109.5 |
C2—C1—H1 | 119.8 | H11A—C11—H11C | 109.5 |
C3—C2—C1 | 120.80 (16) | H11B—C11—H11C | 109.5 |
C3—C2—H2 | 119.6 | C13—C12—C17 | 120.72 (13) |
C1—C2—H2 | 119.6 | C13—C12—N1 | 120.02 (13) |
C2—C3—C4 | 119.33 (15) | C17—C12—N1 | 119.24 (12) |
C2—C3—H3 | 120.3 | C12—C13—C14 | 119.55 (15) |
C4—C3—H3 | 120.3 | C12—C13—H13 | 120.2 |
C3—C4—C5 | 120.28 (16) | C14—C13—H13 | 120.2 |
C3—C4—H4 | 119.9 | C15—C14—C13 | 120.16 (15) |
C5—C4—H4 | 119.9 | C15—C14—H14 | 119.9 |
C4—C5—C6 | 120.84 (15) | C13—C14—H14 | 119.9 |
C4—C5—H5 | 119.6 | C14—C15—C16 | 120.47 (14) |
C6—C5—H5 | 119.6 | C14—C15—H15 | 119.8 |
C1—C6—C5 | 118.27 (14) | C16—C15—H15 | 119.8 |
C1—C6—C7 | 121.39 (13) | C17—C16—C15 | 119.95 (15) |
C5—C6—C7 | 120.27 (12) | C17—C16—H16 | 120.0 |
O1—C7—C6 | 107.10 (10) | C15—C16—H16 | 120.0 |
O1—C7—C23 | 111.05 (10) | C16—C17—C12 | 119.14 (13) |
C6—C7—C23 | 112.18 (11) | C16—C17—C7 | 126.19 (13) |
O1—C7—C17 | 105.93 (11) | C12—C17—C7 | 114.66 (11) |
C6—C7—C17 | 114.58 (11) | C19—C18—C23 | 120.45 (13) |
C23—C7—C17 | 105.87 (10) | C19—C18—N1 | 121.12 (13) |
O1—C8—C9 | 114.67 (11) | C23—C18—N1 | 118.43 (11) |
O1—C8—H8A | 108.6 | C18—C19—C20 | 119.65 (14) |
C9—C8—H8A | 108.6 | C18—C19—H19 | 120.2 |
O1—C8—H8B | 108.6 | C20—C19—H19 | 120.2 |
C9—C8—H8B | 108.6 | C21—C20—C19 | 120.32 (14) |
H8A—C8—H8B | 107.6 | C21—C20—H20 | 119.8 |
C11—C9—N1 | 109.77 (11) | C19—C20—H20 | 119.8 |
C11—C9—C10 | 109.89 (12) | C20—C21—C22 | 120.27 (14) |
N1—C9—C10 | 107.99 (11) | C20—C21—H21 | 119.9 |
C11—C9—C8 | 110.46 (12) | C22—C21—H21 | 119.9 |
N1—C9—C8 | 110.59 (11) | C23—C22—C21 | 120.09 (14) |
C10—C9—C8 | 108.09 (12) | C23—C22—H22 | 120.0 |
C9—C10—H10A | 109.5 | C21—C22—H22 | 120.0 |
C9—C10—H10B | 109.5 | C22—C23—C18 | 119.20 (12) |
H10A—C10—H10B | 109.5 | C22—C23—C7 | 125.29 (13) |
C9—C10—H10C | 109.5 | C18—C23—C7 | 115.51 (12) |
H10A—C10—H10C | 109.5 | C8—O1—C7 | 117.70 (10) |
H10B—C10—H10C | 109.5 | C18—N1—C12 | 108.01 (11) |
C9—C11—H11A | 109.5 | C18—N1—C9 | 110.05 (10) |
C9—C11—H11B | 109.5 | C12—N1—C9 | 113.39 (10) |
Experimental details
Crystal data | |
Chemical formula | C23H21NO |
Mr | 327.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 15.707 (6), 9.227 (4), 12.198 (5) |
β (°) | 101.575 (6) |
V (Å3) | 1731.7 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.20 × 0.15 × 0.11 |
Data collection | |
Diffractometer | Rigaku Mercury CCD area-detector |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2004) |
Tmin, Tmax | 0.981, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13049, 3911, 3171 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.117, 1.07 |
No. of reflections | 3911 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.17 |
Computer programs: CrystalClear (Rigaku/MSC, 2004), CrystalClear, SHELXTL (Sheldrick, 1997), SHELXTL.
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2-(Trimethylsilyl)phenyltriflate, an efficient precursor to benzyne, has been widely employed for syntheses of complex organic compounds (Pellissier & Santelli, 2003). Recently, Liu and Larock (2004) reported addition of H—X bonds (X = N, O and S) to arynes to construct a new carbon-heteroatom bond (Liu & Larock, 2004). There are also examples of the transition-metal-free insertion of an aryne into polar hetero atom-containing bonds such as C—N σ bond (Yoshida et al., 2002) and intermolecular C—N bond reaction under very mild conditions (Liu & Larock, 2005). However, there is no example of insertion of aryne into C═N double bonds. We report here the crystal structure of the title compound, (I), which was obtained through insertion of two benzyne molecules into C═N double bonds.
As shown in Fig. 1, the oxaazabicyclo[3.2.2]nonane unit is composed of one six-membered ring and two seven-membered rings, which are connected with each other by the brigdehead atoms N1 and C7. The bond lengths and angles in (I) are normal except the slightly longer C7—C23 [1.5296 (19) Å], C7—C17 [1.5317 (19) Å] and C9—N1 [1.5209 (18) Å] bonds, which may result from the ring fusion.
The six-membered ring of the oxaazabicyclo[3.2.2]nonane unit adopts a boat conformation, with atoms N1 and C7 deviating from the C12/C17/C18/C23 plane by 0.542 (1) and 0.608 (1) Å, respectively. One of the seven-membered rings (N1,C9,C8,O1,C7,C23,C18) adopts a boat conformation, with atoms C8, C18 and C23 deviating from the plane defined by other four atoms by 0.624 (2), 1.149 (1) and 1.249 (1) Å, respectively. The other seven-membered ring (N1,C9,C8,O1,C7,C12,C17) adopts a chair conformation. The dihedral angle between the two benzene rings (C12—C17 and C18—C23) is 51.89 (4)°. The C1—C6 phenyl ring forms dihedral angles of 60.04 (5)° and 68.23 (5)°, respectively, with the C12—C17 and C18—C23 benzene rings.
No significant hydrogen bonds are observed in the crystal structure.