endo-11-(Dibenzyl-amino)-tetra-cyclo-[5.4.0.0.0]undecane-8-one.

The structure of the title compound, C(25)H(27)NO, is a mono-ketone penta-cyclo-undecane (PCU) mol-ecule bearing a tertiary amine group. One of the methyl-ene groups in the PCU is disordered over two orientations with site-occupancy factors of 0.621 (7) and 0.379 (7).

Related literature

For mono-ketone PCU derivatives, see: Kruger et al. (2006) ▶. For examples of the crystal structures of mono-ketone PCU mol­ecules bearing heteroatoms, see: Watson et al. (2000) ▶; Karpoormath et al. (2010 ▶).

Experimental

Crystal data

C25H21NO

M = 351.43

Monoclinic,

a = 6.6117 (3) Å

b = 16.4344 (7) Å

c = 17.2331 (8) Å

β = 97.100 (2)°

V = 1858.18 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.59 mm−1

T = 173 K

0.43 × 0.33 × 0.25 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.786, T max = 0.867

24662 measured reflections

3303 independent reflections

3240 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.173

S = 1.06

3303 reflections

255 parameters

24 restraints

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100479X/lx2177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100479X/lx2177Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H21NO	F(000) = 744
Mr = 351.43	Dx = 1.256 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 3299 reflections
a = 6.6117 (3) Å	θ = 5.2–69.2°
b = 16.4344 (7) Å	µ = 0.59 mm−1
c = 17.2331 (8) Å	T = 173 K
β = 97.100 (2)°	Needle, colourless
V = 1858.18 (14) Å3	0.43 × 0.33 × 0.25 mm
Z = 4

Bruker Kappa DUO APEXII diffractometer	3303 independent reflections
Radiation source: fine-focus sealed tube	3240 reflections with I > 2σ(I)
graphite	Rint = 0.018
1.2° φ scans and ω	θmax = 69.2°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −7→7
Tmin = 0.786, Tmax = 0.867	k = −19→19
24662 measured reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066	H-atom parameters constrained
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.080P)2 + 1.983P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3303 reflections	Δρmax = 0.48 e Å−3
255 parameters	Δρmin = −0.46 e Å−3
24 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (4)

Experimental. Half sphere of data collected using APEX2 (Bruker, 2006). Crystal to detector distance = 45 mm; combination of φ and ω scans of 1.2°, 50 s per °, 2 iterations.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
O1	0.1742 (2)	0.13889 (10)	0.19402 (10)	0.0394 (4)
N1	−0.2672 (3)	0.05165 (10)	0.14408 (10)	0.0271 (4)
C2	−0.4175 (5)	0.27147 (16)	0.1215 (3)	0.0763 (12)
C3	−0.3558 (3)	0.19546 (14)	0.17218 (17)	0.0423 (6)
H3	−0.4438	0.1857	0.2145	0.051*
C4	−0.3624 (3)	0.12730 (13)	0.11264 (14)	0.0347 (5)
H4	−0.5077	0.1160	0.0920	0.042*
C5	−0.2577 (4)	0.16781 (17)	0.04842 (17)	0.0493 (7)
H5	−0.2759	0.1387	−0.0029	0.059*
C6	−0.3393 (6)	0.25559 (17)	0.04539 (18)	0.0652 (10)
C7	−0.1306 (5)	0.30438 (16)	0.16140 (19)	0.0612 (9)
C8	−0.1293 (3)	0.22060 (14)	0.20361 (17)	0.0422 (6)
H8	−0.0991	0.2233	0.2619	0.051*
C9	0.0227 (3)	0.17342 (14)	0.16393 (15)	0.0361 (5)
C10	−0.0309 (4)	0.19225 (18)	0.07827 (17)	0.0497 (7)
H10	0.0730	0.1760	0.0437	0.060*
C11	−0.0792 (5)	0.2836 (2)	0.0801 (2)	0.0775 (12)
C12	−0.3867 (3)	0.01601 (13)	0.20230 (13)	0.0311 (5)
H12A	−0.3795	−0.0440	0.1982	0.037*
H12B	−0.5311	0.0318	0.1884	0.037*
C13	−0.3230 (3)	0.03943 (13)	0.28639 (13)	0.0307 (5)
C14	−0.4688 (4)	0.04214 (14)	0.33779 (14)	0.0372 (5)
H14	−0.6085	0.0347	0.3185	0.045*
C15	−0.4127 (4)	0.05563 (15)	0.41683 (15)	0.0436 (6)
H15	−0.5139	0.0568	0.4514	0.052*
C16	−0.2108 (4)	0.06739 (16)	0.44562 (15)	0.0467 (6)
H16	−0.1722	0.0761	0.4999	0.056*
C17	−0.0654 (4)	0.06631 (17)	0.39452 (15)	0.0452 (6)
H17	0.0736	0.0755	0.4138	0.054*
C18	−0.1200 (4)	0.05196 (15)	0.31545 (14)	0.0384 (6)
H18	−0.0184	0.0507	0.2810	0.046*
C19	−0.2474 (4)	−0.00746 (14)	0.08166 (13)	0.0349 (5)
H19A	−0.1791	0.0190	0.0403	0.042*
H19B	−0.3851	−0.0244	0.0580	0.042*
C20	−0.1277 (3)	−0.08185 (13)	0.11058 (12)	0.0312 (5)
C21	0.0737 (3)	−0.07388 (14)	0.14401 (14)	0.0381 (5)
H21	0.1342	−0.0214	0.1496	0.046*
C22	0.1864 (4)	−0.14184 (16)	0.16920 (16)	0.0434 (6)
H22	0.3238	−0.1357	0.1921	0.052*
C23	0.1013 (4)	−0.21862 (15)	0.16137 (15)	0.0416 (6)
H23	0.1796	−0.2652	0.1785	0.050*
C24	−0.0992 (4)	−0.22698 (15)	0.12834 (15)	0.0413 (6)
H24	−0.1593	−0.2795	0.1228	0.050*
C25	−0.2121 (4)	−0.15900 (14)	0.10333 (14)	0.0363 (5)
H25	−0.3498	−0.1653	0.0808	0.044*
C1A	−0.3205 (6)	0.3417 (2)	0.1498 (2)	0.0414 (11)	0.621 (7)
H1A	−0.3673	0.3612	0.1989	0.050*	0.621 (7)
H1B	−0.3281	0.3860	0.1106	0.050*	0.621 (7)
C1B	−0.2299 (8)	0.3246 (3)	0.0321 (4)	0.0458 (19)	0.379 (7)
H1D	−0.2791	0.3753	0.0546	0.055*	0.379 (7)
H1C	−0.2020	0.3321	−0.0225	0.055*	0.379 (7)

	U11	U22	U33	U12	U13	U23
O1	0.0224 (8)	0.0389 (9)	0.0564 (10)	0.0003 (6)	0.0031 (7)	0.0051 (7)
N1	0.0261 (9)	0.0239 (9)	0.0310 (9)	0.0000 (7)	0.0019 (7)	0.0019 (7)
C2	0.0606 (19)	0.0306 (14)	0.148 (3)	0.0175 (13)	0.055 (2)	0.0285 (18)
C3	0.0238 (11)	0.0256 (12)	0.0770 (18)	0.0021 (9)	0.0049 (11)	−0.0047 (11)
C4	0.0248 (10)	0.0278 (11)	0.0495 (13)	0.0006 (8)	−0.0037 (9)	0.0082 (10)
C5	0.0439 (14)	0.0489 (16)	0.0522 (15)	−0.0049 (12)	−0.0061 (12)	0.0247 (12)
C6	0.092 (2)	0.0341 (14)	0.0589 (17)	−0.0159 (15)	−0.0342 (16)	0.0170 (13)
C7	0.0715 (19)	0.0268 (13)	0.075 (2)	0.0005 (12)	−0.0338 (16)	−0.0049 (13)
C8	0.0278 (12)	0.0284 (12)	0.0699 (17)	−0.0016 (9)	0.0041 (11)	−0.0090 (11)
C9	0.0243 (11)	0.0292 (11)	0.0549 (14)	−0.0052 (9)	0.0055 (10)	0.0056 (10)
C10	0.0382 (13)	0.0525 (16)	0.0595 (16)	−0.0045 (11)	0.0098 (12)	0.0249 (13)
C11	0.066 (2)	0.059 (2)	0.117 (3)	0.0220 (16)	0.050 (2)	0.052 (2)
C12	0.0262 (10)	0.0269 (11)	0.0404 (12)	−0.0041 (8)	0.0055 (9)	0.0009 (9)
C13	0.0311 (11)	0.0240 (10)	0.0378 (12)	0.0013 (8)	0.0069 (9)	0.0060 (9)
C14	0.0361 (12)	0.0309 (12)	0.0464 (13)	0.0036 (9)	0.0124 (10)	0.0049 (10)
C15	0.0570 (16)	0.0351 (13)	0.0423 (13)	0.0077 (11)	0.0206 (12)	0.0067 (10)
C16	0.0684 (18)	0.0373 (13)	0.0338 (12)	0.0072 (12)	0.0040 (12)	0.0047 (10)
C17	0.0445 (14)	0.0483 (15)	0.0405 (13)	0.0008 (11)	−0.0041 (11)	0.0043 (11)
C18	0.0327 (12)	0.0435 (14)	0.0391 (13)	0.0013 (10)	0.0053 (10)	0.0051 (10)
C19	0.0376 (12)	0.0351 (12)	0.0301 (11)	0.0035 (9)	−0.0027 (9)	−0.0024 (9)
C20	0.0345 (11)	0.0303 (11)	0.0287 (10)	0.0012 (9)	0.0032 (9)	−0.0043 (9)
C21	0.0333 (12)	0.0302 (12)	0.0498 (14)	−0.0017 (9)	0.0011 (10)	−0.0011 (10)
C22	0.0316 (12)	0.0429 (14)	0.0542 (15)	0.0035 (10)	−0.0005 (11)	0.0025 (11)
C23	0.0460 (14)	0.0342 (13)	0.0459 (14)	0.0110 (10)	0.0104 (11)	0.0051 (10)
C24	0.0497 (14)	0.0287 (12)	0.0467 (14)	−0.0026 (10)	0.0111 (11)	−0.0053 (10)
C25	0.0351 (12)	0.0348 (12)	0.0384 (12)	−0.0025 (9)	0.0020 (9)	−0.0085 (10)
C1A	0.052 (2)	0.0290 (19)	0.043 (2)	0.0039 (16)	0.0042 (17)	0.0013 (15)
C1B	0.062 (4)	0.031 (3)	0.046 (3)	0.002 (3)	0.013 (3)	0.005 (3)

O1—C9	1.211 (3)	C13—C14	1.388 (3)
N1—C4	1.467 (3)	C14—C15	1.385 (4)
N1—C19	1.467 (3)	C14—H14	0.9500
N1—C12	1.473 (3)	C15—C16	1.379 (4)
C2—C1A	1.380 (4)	C15—H15	0.9500
C2—C6	1.491 (5)	C16—C17	1.382 (4)
C2—C3	1.550 (4)	C16—H16	0.9500
C3—C4	1.516 (3)	C17—C18	1.386 (4)
C3—C8	1.583 (3)	C17—H17	0.9500
C3—H3	1.0000	C18—H18	0.9500
C4—C5	1.529 (3)	C19—C20	1.507 (3)
C4—H4	1.0000	C19—H19A	0.9900
C5—C6	1.539 (4)	C19—H19B	0.9900
C5—C10	1.576 (4)	C20—C25	1.385 (3)
C5—H5	1.0000	C20—C21	1.390 (3)
C6—C1B	1.379 (4)	C21—C22	1.383 (3)
C7—C1A	1.389 (4)	C21—H21	0.9500
C7—C11	1.522 (5)	C22—C23	1.381 (4)
C7—C8	1.557 (4)	C22—H22	0.9500
C8—C9	1.500 (3)	C23—C24	1.383 (4)
C8—H8	1.0000	C23—H23	0.9500
C9—C10	1.507 (4)	C24—C25	1.383 (3)
C10—C11	1.536 (4)	C24—H24	0.9500
C10—H10	1.0000	C25—H25	0.9500
C11—C1B	1.387 (4)	C1A—H1A	0.9900
C12—C13	1.508 (3)	C1A—H1B	0.9900
C12—H12A	0.9900	C1B—H1D	0.9900
C12—H12B	0.9900	C1B—H1C	0.9900
C13—C18	1.388 (3)
C4—N1—C19	111.32 (17)	C18—C13—C14	118.8 (2)
C4—N1—C12	110.30 (16)	C18—C13—C12	121.8 (2)
C19—N1—C12	109.88 (17)	C14—C13—C12	119.2 (2)
C1A—C2—C6	105.1 (3)	C15—C14—C13	120.7 (2)
C1A—C2—C3	113.4 (3)	C15—C14—H14	119.7
C6—C2—C3	105.0 (2)	C13—C14—H14	119.7
C4—C3—C2	103.3 (2)	C16—C15—C14	120.4 (2)
C4—C3—C8	111.81 (19)	C16—C15—H15	119.8
C2—C3—C8	98.9 (2)	C14—C15—H15	119.8
C4—C3—H3	113.8	C15—C16—C17	119.2 (2)
C2—C3—H3	113.8	C15—C16—H16	120.4
C8—C3—H3	113.8	C17—C16—H16	120.4
N1—C4—C3	113.65 (19)	C16—C17—C18	120.8 (2)
N1—C4—C5	115.1 (2)	C16—C17—H17	119.6
C3—C4—C5	101.0 (2)	C18—C17—H17	119.6
N1—C4—H4	108.9	C17—C18—C13	120.2 (2)
C3—C4—H4	108.9	C17—C18—H18	119.9
C5—C4—H4	108.9	C13—C18—H18	119.9
C4—C5—C6	104.2 (2)	N1—C19—C20	112.67 (17)
C4—C5—C10	111.9 (2)	N1—C19—H19A	109.1
C6—C5—C10	95.0 (2)	C20—C19—H19A	109.1
C4—C5—H5	114.6	N1—C19—H19B	109.1
C6—C5—H5	114.6	C20—C19—H19B	109.1
C10—C5—H5	114.6	H19A—C19—H19B	107.8
C1B—C6—C2	104.3 (4)	C25—C20—C21	118.6 (2)
C1B—C6—C5	126.0 (4)	C25—C20—C19	121.6 (2)
C2—C6—C5	107.0 (2)	C21—C20—C19	119.8 (2)
C1A—C7—C11	105.5 (3)	C22—C21—C20	120.4 (2)
C1A—C7—C8	114.2 (3)	C22—C21—H21	119.8
C11—C7—C8	104.1 (2)	C20—C21—H21	119.8
C9—C8—C7	102.1 (2)	C23—C22—C21	120.6 (2)
C9—C8—C3	111.6 (2)	C23—C22—H22	119.7
C7—C8—C3	96.9 (2)	C21—C22—H22	119.7
C9—C8—H8	114.7	C22—C23—C24	119.3 (2)
C7—C8—H8	114.7	C22—C23—H23	120.4
C3—C8—H8	114.7	C24—C23—H23	120.4
O1—C9—C8	127.8 (2)	C25—C24—C23	120.1 (2)
O1—C9—C10	126.7 (2)	C25—C24—H24	120.0
C8—C9—C10	104.5 (2)	C23—C24—H24	120.0
C9—C10—C11	101.8 (3)	C24—C25—C20	121.0 (2)
C9—C10—C5	111.5 (2)	C24—C25—H25	119.5
C11—C10—C5	93.7 (2)	C20—C25—H25	119.5
C9—C10—H10	115.7	C2—C1A—C7	93.1 (3)
C11—C10—H10	115.7	C2—C1A—H1A	113.1
C5—C10—H10	115.7	C7—C1A—H1A	113.1
C1B—C11—C7	102.3 (4)	C2—C1A—H1B	113.1
C1B—C11—C10	126.7 (4)	C7—C1A—H1B	113.1
C7—C11—C10	108.0 (2)	H1A—C1A—H1B	110.5
N1—C12—C13	116.31 (17)	C6—C1B—C11	81.7 (3)
N1—C12—H12A	108.2	C6—C1B—H1D	115.0
C13—C12—H12A	108.2	C11—C1B—H1D	115.0
N1—C12—H12B	108.2	C6—C1B—H1C	115.0
C13—C12—H12B	108.2	C11—C1B—H1C	115.0
H12A—C12—H12B	107.4	H1D—C1B—H1C	112.1
C1A—C2—C3—C4	−145.8 (3)	C4—C5—C10—C11	−107.2 (3)
C6—C2—C3—C4	−31.6 (3)	C6—C5—C10—C11	0.3 (3)
C1A—C2—C3—C8	−30.7 (3)	C1A—C7—C11—C1B	10.1 (3)
C6—C2—C3—C8	83.4 (3)	C8—C7—C11—C1B	130.7 (3)
C19—N1—C4—C3	−170.57 (19)	C1A—C7—C11—C10	−125.5 (3)
C12—N1—C4—C3	67.2 (2)	C8—C7—C11—C10	−4.9 (3)
C19—N1—C4—C5	−54.8 (3)	C9—C10—C11—C1B	−142.8 (4)
C12—N1—C4—C5	−177.03 (19)	C5—C10—C11—C1B	−29.9 (5)
C2—C3—C4—N1	167.47 (19)	C9—C10—C11—C7	−21.3 (3)
C8—C3—C4—N1	62.0 (3)	C5—C10—C11—C7	91.6 (3)
C2—C3—C4—C5	43.6 (2)	C4—N1—C12—C13	−92.8 (2)
C8—C3—C4—C5	−61.8 (2)	C19—N1—C12—C13	144.12 (18)
N1—C4—C5—C6	−162.24 (19)	N1—C12—C13—C18	−35.2 (3)
C3—C4—C5—C6	−39.4 (2)	N1—C12—C13—C14	150.2 (2)
N1—C4—C5—C10	−60.8 (3)	C18—C13—C14—C15	−1.1 (3)
C3—C4—C5—C10	62.1 (3)	C12—C13—C14—C15	173.7 (2)
C1A—C2—C6—C1B	−8.8 (3)	C13—C14—C15—C16	0.6 (4)
C3—C2—C6—C1B	−128.7 (3)	C14—C15—C16—C17	0.6 (4)
C1A—C2—C6—C5	126.6 (3)	C15—C16—C17—C18	−1.3 (4)
C3—C2—C6—C5	6.7 (3)	C16—C17—C18—C13	0.8 (4)
C4—C5—C6—C1B	143.1 (4)	C14—C13—C18—C17	0.4 (4)
C10—C5—C6—C1B	29.1 (5)	C12—C13—C18—C17	−174.3 (2)
C4—C5—C6—C2	20.3 (3)	C4—N1—C19—C20	173.10 (18)
C10—C5—C6—C2	−93.7 (3)	C12—N1—C19—C20	−64.4 (2)
C1A—C7—C8—C9	144.0 (3)	N1—C19—C20—C25	120.5 (2)
C11—C7—C8—C9	29.5 (3)	N1—C19—C20—C21	−60.8 (3)
C1A—C7—C8—C3	30.1 (3)	C25—C20—C21—C22	0.1 (4)
C11—C7—C8—C3	−84.4 (2)	C19—C20—C21—C22	−178.6 (2)
C4—C3—C8—C9	2.7 (3)	C20—C21—C22—C23	0.2 (4)
C2—C3—C8—C9	−105.6 (3)	C21—C22—C23—C24	−0.4 (4)
C4—C3—C8—C7	108.6 (2)	C22—C23—C24—C25	0.2 (4)
C2—C3—C8—C7	0.3 (3)	C23—C24—C25—C20	0.1 (4)
C7—C8—C9—O1	124.9 (3)	C21—C20—C25—C24	−0.3 (3)
C3—C8—C9—O1	−132.5 (3)	C19—C20—C25—C24	178.4 (2)
C7—C8—C9—C10	−44.2 (2)	C6—C2—C1A—C7	−67.4 (3)
C3—C8—C9—C10	58.4 (3)	C3—C2—C1A—C7	46.7 (4)
O1—C9—C10—C11	−128.6 (3)	C11—C7—C1A—C2	66.7 (3)
C8—C9—C10—C11	40.7 (2)	C8—C7—C1A—C2	−46.9 (4)
O1—C9—C10—C5	132.6 (3)	C2—C6—C1B—C11	83.9 (4)
C8—C9—C10—C5	−58.1 (3)	C5—C6—C1B—C11	−40.0 (5)
C4—C5—C10—C9	−2.9 (3)	C7—C11—C1B—C6	−82.9 (4)
C6—C5—C10—C9	104.5 (3)	C10—C11—C1B—C6	40.9 (5)