6-[(Z)-Benzyl­idene]-2,3-diphenyl-2-aza­bicyclo­[2.2.2]octan-5-one

The title compound, C₂₆H₂₃NO, was obtained from the Diels-Alder reaction of N-benzyl­ideneaniline and cyclo­hexen-2-one catalyzed by zirconium tetra­chloride. The mol­ecule is the Z isomer. All three six-membered rings in the 2-aza­bicyclo­[2.2.2]octane system adopt the expected boat conformation. In the crystal packing, the phenyl groups are aggregated in hydro­phobic layers at y = 0 and .

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.068
• wR factor = 0.145
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

6-[(Z)-Benzylidene]-2,3-diphenyl-2-azabicyclo[2.2.2]octan-5-one

Crystal data

C26H23NO	F(000) = 776
Mr = 365.45	Dx = 1.238 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3275 reflections
a = 10.1554 (9) Å	θ = 2.4–21.4°
b = 16.5088 (15) Å	µ = 0.08 mm^−1
c = 11.7903 (11) Å	T = 273 K
β = 97.154 (2)°	Block, colorless
V = 1961.3 (3) Å^3	0.21 × 0.13 × 0.08 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2759 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −12→12
18504 measured reflections	k = −19→19
3437 independent reflections	l = −14→13

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.6492P] where P = (Fo^2 + 2Fc^2)/3
3437 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.13 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2912 (2)	0.25311 (14)	0.27571 (18)	0.0406 (6)
H1	0.2210	0.2923	0.2511	0.049*
C3	0.3342 (2)	0.12064 (13)	0.37012 (19)	0.0420 (6)
H3	0.3407	0.1137	0.4532	0.050*
C4	0.4709 (2)	0.14989 (15)	0.3423 (2)	0.0464 (6)
H4	0.5401	0.1106	0.3694	0.056*
C5	0.4990 (2)	0.23061 (15)	0.3999 (2)	0.0468 (6)
C6	0.4010 (2)	0.29321 (14)	0.35494 (18)	0.0405 (6)
C7	0.3481 (3)	0.21810 (16)	0.1722 (2)	0.0523 (7)
H7A	0.3767	0.2617	0.1259	0.063*
H7B	0.2803	0.1872	0.1257	0.063*
C8	0.4662 (3)	0.16306 (16)	0.2131 (2)	0.0554 (7)
H8A	0.4564	0.1115	0.1736	0.067*
H8B	0.5480	0.1880	0.1964	0.067*
C9	0.1419 (2)	0.20103 (14)	0.41199 (18)	0.0402 (5)
C10	0.0935 (2)	0.13700 (16)	0.4720 (2)	0.0513 (6)
H10	0.1250	0.0848	0.4628	0.062*
C11	−0.0009 (3)	0.15029 (18)	0.5451 (2)	0.0636 (8)
H11	−0.0328	0.1068	0.5836	0.076*
C12	−0.0479 (3)	0.2266 (2)	0.5615 (3)	0.0716 (9)
H12	−0.1107	0.2353	0.6112	0.086*
C13	−0.0001 (3)	0.29031 (19)	0.5025 (3)	0.0692 (8)
H13	−0.0309	0.3425	0.5132	0.083*
C14	0.0925 (2)	0.27782 (16)	0.4282 (2)	0.0520 (7)
H14	0.1221	0.3215	0.3885	0.062*
C15	0.2940 (2)	0.03950 (15)	0.31577 (19)	0.0449 (6)
C16	0.1857 (3)	0.03093 (16)	0.2337 (2)	0.0578 (7)
H16	0.1355	0.0762	0.2094	0.069*
C17	0.1506 (3)	−0.04382 (18)	0.1870 (2)	0.0688 (8)
H17	0.0767	−0.0484	0.1323	0.083*
C18	0.2234 (3)	−0.11109 (18)	0.2204 (3)	0.0677 (8)
H18	0.2007	−0.1612	0.1875	0.081*
C19	0.3299 (3)	−0.10405 (18)	0.3029 (3)	0.0724 (9)
H19	0.3792	−0.1497	0.3273	0.087*
C20	0.3643 (3)	−0.02953 (16)	0.3496 (2)	0.0644 (8)
H20	0.4371	−0.0256	0.4056	0.077*
C21	0.4142 (2)	0.37012 (15)	0.3876 (2)	0.0465 (6)
H21	0.4846	0.3804	0.4441	0.056*
C22	0.3352 (2)	0.44092 (14)	0.3484 (2)	0.0455 (6)
C23	0.2799 (3)	0.45047 (16)	0.2347 (2)	0.0583 (7)
H23	0.2905	0.4100	0.1818	0.070*
C24	0.2098 (3)	0.51933 (18)	0.2006 (3)	0.0696 (8)
H24	0.1728	0.5248	0.1248	0.084*
C25	0.1939 (3)	0.58008 (18)	0.2769 (3)	0.0689 (8)
H25	0.1463	0.6265	0.2530	0.083*
C26	0.2485 (3)	0.57211 (18)	0.3887 (3)	0.0651 (8)
H26	0.2385	0.6133	0.4407	0.078*
C27	0.3180 (3)	0.50326 (16)	0.4240 (2)	0.0546 (7)
H27	0.3543	0.4984	0.5001	0.066*
N2	0.23783 (18)	0.18577 (11)	0.33854 (15)	0.0404 (5)
O28	0.59236 (18)	0.24337 (12)	0.47327 (17)	0.0696 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0428 (13)	0.0441 (14)	0.0347 (12)	0.0031 (11)	0.0039 (10)	0.0016 (10)
C3	0.0471 (14)	0.0450 (14)	0.0340 (12)	0.0062 (11)	0.0058 (10)	−0.0019 (10)
C4	0.0426 (13)	0.0507 (15)	0.0465 (14)	0.0107 (12)	0.0078 (11)	−0.0015 (11)
C5	0.0402 (13)	0.0566 (16)	0.0437 (14)	0.0006 (12)	0.0059 (11)	0.0005 (12)
C6	0.0422 (13)	0.0472 (14)	0.0330 (12)	0.0018 (11)	0.0081 (10)	0.0013 (10)
C7	0.0612 (16)	0.0630 (17)	0.0338 (13)	−0.0047 (13)	0.0102 (11)	−0.0042 (12)
C8	0.0618 (16)	0.0579 (17)	0.0504 (15)	0.0043 (14)	0.0220 (13)	−0.0056 (13)
C9	0.0342 (12)	0.0503 (14)	0.0351 (12)	0.0036 (11)	0.0000 (10)	−0.0022 (11)
C10	0.0543 (15)	0.0519 (16)	0.0490 (15)	0.0015 (13)	0.0111 (12)	0.0007 (12)
C11	0.0620 (17)	0.073 (2)	0.0598 (17)	−0.0012 (15)	0.0222 (14)	0.0095 (15)
C12	0.0644 (19)	0.086 (2)	0.0702 (19)	0.0205 (17)	0.0330 (15)	0.0082 (17)
C13	0.0668 (18)	0.071 (2)	0.0735 (19)	0.0290 (16)	0.0225 (16)	0.0086 (16)
C14	0.0490 (14)	0.0552 (16)	0.0537 (15)	0.0139 (12)	0.0137 (12)	0.0069 (12)
C15	0.0516 (15)	0.0471 (15)	0.0375 (13)	0.0042 (12)	0.0118 (11)	0.0005 (11)
C16	0.0629 (17)	0.0522 (17)	0.0565 (16)	0.0040 (13)	−0.0004 (14)	−0.0024 (13)
C17	0.078 (2)	0.0597 (19)	0.0658 (19)	−0.0081 (16)	−0.0016 (15)	−0.0128 (15)
C18	0.088 (2)	0.0516 (18)	0.0662 (19)	−0.0096 (16)	0.0195 (17)	−0.0135 (15)
C19	0.090 (2)	0.0475 (18)	0.078 (2)	0.0108 (16)	0.0066 (18)	−0.0004 (15)
C20	0.0727 (19)	0.0529 (18)	0.0645 (18)	0.0090 (15)	−0.0038 (15)	−0.0029 (14)
C21	0.0468 (14)	0.0542 (16)	0.0384 (13)	−0.0030 (12)	0.0048 (11)	−0.0042 (12)
C22	0.0435 (14)	0.0449 (14)	0.0492 (15)	−0.0047 (11)	0.0099 (11)	−0.0034 (11)
C23	0.0733 (19)	0.0492 (16)	0.0523 (16)	0.0014 (14)	0.0075 (14)	−0.0027 (13)
C24	0.079 (2)	0.0560 (18)	0.070 (2)	0.0007 (16)	−0.0047 (16)	0.0071 (15)
C25	0.0545 (17)	0.0500 (18)	0.102 (2)	0.0063 (14)	0.0064 (17)	0.0010 (17)
C26	0.0539 (17)	0.0586 (19)	0.085 (2)	0.0029 (14)	0.0176 (16)	−0.0184 (16)
C27	0.0510 (15)	0.0563 (17)	0.0582 (16)	−0.0041 (13)	0.0132 (13)	−0.0113 (13)
N2	0.0415 (11)	0.0422 (11)	0.0379 (10)	0.0058 (9)	0.0066 (9)	0.0000 (9)
O28	0.0576 (12)	0.0722 (13)	0.0721 (13)	0.0052 (10)	−0.0197 (10)	−0.0038 (10)

Geometric parameters (Å, º)

C1—N2	1.476 (3)	C13—C14	1.379 (4)
C1—C6	1.515 (3)	C13—H13	0.930
C1—C7	1.527 (3)	C14—H14	0.930
C1—H1	0.980	C15—C20	1.377 (3)
C3—N2	1.470 (3)	C15—C16	1.379 (3)
C3—C15	1.519 (3)	C16—C17	1.380 (4)
C3—C4	1.544 (3)	C16—H16	0.930
C3—H3	0.980	C17—C18	1.365 (4)
C4—C5	1.506 (3)	C17—H17	0.930
C4—C8	1.534 (3)	C18—C19	1.366 (4)
C4—H4	0.980	C18—H18	0.930
C5—O28	1.220 (3)	C19—C20	1.375 (4)
C5—C6	1.486 (3)	C19—H19	0.930
C6—C21	1.329 (3)	C20—H20	0.930
C7—C8	1.534 (4)	C21—C22	1.460 (3)
C7—H7A	0.970	C21—H21	0.930
C7—H7B	0.970	C22—C27	1.387 (3)
C8—H8A	0.970	C22—C23	1.396 (3)
C8—H8B	0.970	C23—C24	1.374 (4)
C9—C14	1.385 (3)	C23—H23	0.930
C9—C10	1.395 (3)	C24—C25	1.371 (4)
C9—N2	1.404 (3)	C24—H24	0.930
C10—C11	1.383 (4)	C25—C26	1.371 (4)
C10—H10	0.930	C25—H25	0.930
C11—C12	1.369 (4)	C26—C27	1.375 (4)
C11—H11	0.930	C26—H26	0.930
C12—C13	1.382 (4)	C27—H27	0.930
C12—H12	0.930
N2—C1—C6	107.93 (17)	C14—C13—C12	121.1 (3)
N2—C1—C7	108.36 (19)	C14—C13—H13	119.5
C6—C1—C7	109.62 (19)	C12—C13—H13	119.5
N2—C1—H1	110.3	C13—C14—C9	120.8 (3)
C6—C1—H1	110.3	C13—C14—H14	119.6
C7—C1—H1	110.3	C9—C14—H14	119.6
N2—C3—C15	113.74 (18)	C20—C15—C16	117.3 (2)
N2—C3—C4	107.79 (18)	C20—C15—C3	120.3 (2)
C15—C3—C4	112.84 (19)	C16—C15—C3	122.4 (2)
N2—C3—H3	107.4	C15—C16—C17	121.0 (3)
C15—C3—H3	107.4	C15—C16—H16	119.5
C4—C3—H3	107.4	C17—C16—H16	119.5
C5—C4—C8	107.6 (2)	C18—C17—C16	120.6 (3)
C5—C4—C3	107.82 (18)	C18—C17—H17	119.7
C8—C4—C3	109.7 (2)	C16—C17—H17	119.7
C5—C4—H4	110.5	C17—C18—C19	119.3 (3)
C8—C4—H4	110.5	C17—C18—H18	120.4
C3—C4—H4	110.5	C19—C18—H18	120.4
O28—C5—C6	124.0 (2)	C18—C19—C20	120.0 (3)
O28—C5—C4	124.0 (2)	C18—C19—H19	120.0
C6—C5—C4	111.9 (2)	C20—C19—H19	120.0
C21—C6—C5	121.5 (2)	C19—C20—C15	121.8 (3)
C21—C6—C1	129.5 (2)	C19—C20—H20	119.1
C5—C6—C1	109.0 (2)	C15—C20—H20	119.1
C1—C7—C8	109.38 (19)	C6—C21—C22	129.9 (2)
C1—C7—H7A	109.8	C6—C21—H21	115.1
C8—C7—H7A	109.8	C22—C21—H21	115.1
C1—C7—H7B	109.8	C27—C22—C23	117.8 (2)
C8—C7—H7B	109.8	C27—C22—C21	119.9 (2)
H7A—C7—H7B	108.2	C23—C22—C21	122.3 (2)
C4—C8—C7	108.84 (19)	C24—C23—C22	120.4 (3)
C4—C8—H8A	109.9	C24—C23—H23	119.8
C7—C8—H8A	109.9	C22—C23—H23	119.8
C4—C8—H8B	109.9	C25—C24—C23	120.8 (3)
C7—C8—H8B	109.9	C25—C24—H24	119.6
H8A—C8—H8B	108.3	C23—C24—H24	119.6
C14—C9—C10	117.8 (2)	C24—C25—C26	119.6 (3)
C14—C9—N2	122.7 (2)	C24—C25—H25	120.2
C10—C9—N2	119.5 (2)	C26—C25—H25	120.2
C11—C10—C9	120.7 (2)	C25—C26—C27	120.1 (3)
C11—C10—H10	119.6	C25—C26—H26	119.9
C9—C10—H10	119.6	C27—C26—H26	119.9
C12—C11—C10	121.0 (3)	C26—C27—C22	121.3 (3)
C12—C11—H11	119.5	C26—C27—H27	119.4
C10—C11—H11	119.5	C22—C27—H27	119.4
C11—C12—C13	118.6 (3)	C9—N2—C3	117.77 (18)
C11—C12—H12	120.7	C9—N2—C1	120.04 (18)
C13—C12—H12	120.7	C3—N2—C1	113.79 (17)
N2—C3—C4—C5	53.2 (2)	C20—C15—C16—C17	−0.6 (4)
C15—C3—C4—C5	179.59 (19)	C3—C15—C16—C17	−179.1 (2)
N2—C3—C4—C8	−63.8 (2)	C15—C16—C17—C18	−0.6 (4)
C15—C3—C4—C8	62.7 (2)	C16—C17—C18—C19	1.5 (5)
C8—C4—C5—O28	−123.6 (3)	C17—C18—C19—C20	−1.2 (5)
C3—C4—C5—O28	118.2 (3)	C18—C19—C20—C15	0.0 (5)
C8—C4—C5—C6	55.3 (2)	C16—C15—C20—C19	0.9 (4)
C3—C4—C5—C6	−62.9 (2)	C3—C15—C20—C19	179.5 (3)
O28—C5—C6—C21	4.5 (4)	C5—C6—C21—C22	175.3 (2)
C4—C5—C6—C21	−174.4 (2)	C1—C6—C21—C22	−7.3 (4)
O28—C5—C6—C1	−173.4 (2)	C6—C21—C22—C27	147.3 (3)
C4—C5—C6—C1	7.7 (3)	C6—C21—C22—C23	−35.7 (4)
N2—C1—C6—C21	−123.8 (3)	C27—C22—C23—C24	−0.7 (4)
C7—C1—C6—C21	118.4 (3)	C21—C22—C23—C24	−177.8 (2)
N2—C1—C6—C5	53.8 (2)	C22—C23—C24—C25	0.6 (4)
C7—C1—C6—C5	−64.0 (2)	C23—C24—C25—C26	0.0 (5)
N2—C1—C7—C8	−64.4 (2)	C24—C25—C26—C27	−0.5 (4)
C6—C1—C7—C8	53.1 (3)	C25—C26—C27—C22	0.3 (4)
C5—C4—C8—C7	−64.8 (3)	C23—C22—C27—C26	0.3 (4)
C3—C4—C8—C7	52.2 (3)	C21—C22—C27—C26	177.5 (2)
C1—C7—C8—C4	10.1 (3)	C14—C9—N2—C3	146.9 (2)
C14—C9—C10—C11	0.1 (4)	C10—C9—N2—C3	−33.0 (3)
N2—C9—C10—C11	179.9 (2)	C14—C9—N2—C1	0.7 (3)
C9—C10—C11—C12	−0.8 (4)	C10—C9—N2—C1	−179.2 (2)
C10—C11—C12—C13	0.6 (5)	C15—C3—N2—C9	94.3 (2)
C11—C12—C13—C14	0.3 (5)	C4—C3—N2—C9	−139.84 (19)
C12—C13—C14—C9	−1.1 (4)	C15—C3—N2—C1	−117.5 (2)
C10—C9—C14—C13	0.9 (4)	C4—C3—N2—C1	8.4 (2)
N2—C9—C14—C13	−179.0 (2)	C6—C1—N2—C9	83.1 (2)
N2—C3—C15—C20	−170.8 (2)	C7—C1—N2—C9	−158.28 (19)
C4—C3—C15—C20	66.0 (3)	C6—C1—N2—C3	−64.4 (2)
N2—C3—C15—C16	7.7 (3)	C7—C1—N2—C3	54.2 (2)
C4—C3—C15—C16	−115.5 (3)