2,4-Bis(4-eth-oxy-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

The title compound, C(24)H(29)NO(3), exists in a twin-chair conformation with an equatorial orientation of the 4-eth-oxy-phenyl groups. The benzene rings are inclined to each other at an angle of 28.0 (1)°. In the crystal, weak C-H⋯O inter-actions link mol-ecules related by translation into chains along the b axis. The crystal packing exhibits π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.692 (3) Å].

Related literature

For the synthesis and stereochemistry of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Park et al. (2011a ▶). For the biological activity of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Barker et al. (2005 ▶); Parthiban et al. (2009 ▶, 2010a ▶,b ▶, 2011a ▶). For related structures, see: Parthiban et al. (2011b ▶); Park et al. (2012 ▶).

Experimental

Crystal data

C24H29NO3

M = 379.48

Monoclinic,

a = 14.0319 (11) Å

b = 7.3143 (6) Å

c = 20.5820 (17) Å

β = 106.841 (3)°

V = 2021.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.35 × 0.28 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.972, T max = 0.980

15180 measured reflections

5415 independent reflections

3042 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.232

S = 1.05

5415 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037385/cv5330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037385/cv5330Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037385/cv5330Isup3.cml

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

C24H29NO3	F(000) = 816
Mr = 379.48	Dx = 1.247 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4030 reflections
a = 14.0319 (11) Å	θ = 2.8–28.3°
b = 7.3143 (6) Å	µ = 0.08 mm−1
c = 20.5820 (17) Å	T = 293 K
β = 106.841 (3)°	Block, colourless
V = 2021.8 (3) Å3	0.35 × 0.28 × 0.25 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	5415 independent reflections
Radiation source: fine-focus sealed tube	3042 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
phi and ω scans	θmax = 29.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −19→10
Tmin = 0.972, Tmax = 0.980	k = −6→10
15180 measured reflections	l = −26→28

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1095P)2 + 0.8855P] where P = (Fo2 + 2Fc2)/3
5415 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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
O3	1.11887 (13)	0.5928 (3)	0.47084 (8)	0.0489 (5)
O2	0.82074 (15)	0.5864 (3)	−0.14064 (8)	0.0496 (5)
O1	0.86995 (18)	−0.2221 (3)	0.17033 (10)	0.0645 (7)
N1	0.96262 (14)	0.2816 (3)	0.16513 (8)	0.0340 (5)
H1N	0.9683	0.3986	0.1645	0.041*
C20	1.08546 (17)	0.5034 (4)	0.40974 (11)	0.0368 (5)
C5	0.80462 (19)	0.1721 (4)	0.23518 (11)	0.0388 (6)
H5A	0.7556	0.0889	0.2435	0.047*
H5B	0.8242	0.2559	0.2733	0.047*
C18	0.98813 (17)	0.4710 (3)	0.29306 (11)	0.0385 (6)
H18	0.9428	0.5203	0.2548	0.046*
C9	0.90291 (17)	0.2906 (3)	0.04047 (10)	0.0326 (5)
C21	1.12530 (19)	0.3309 (4)	0.40653 (11)	0.0424 (6)
H21	1.1720	0.2828	0.4444	0.051*
C8	0.86704 (19)	−0.0568 (3)	0.16953 (12)	0.0385 (6)
C3	0.74291 (18)	0.1672 (4)	0.10705 (11)	0.0377 (5)
H3A	0.7253	0.2478	0.0679	0.045*
H3B	0.6878	0.0834	0.1027	0.045*
C6	0.89630 (19)	0.0616 (3)	0.23207 (11)	0.0370 (5)
H6	0.9168	−0.0175	0.2721	0.044*
C7	0.98759 (17)	0.1764 (3)	0.22787 (10)	0.0342 (5)
H7	1.0412	0.0914	0.2270	0.041*
C2	0.83556 (18)	0.0568 (3)	0.10609 (11)	0.0354 (5)
H2	0.8178	−0.0252	0.0668	0.042*
C19	1.01727 (18)	0.5742 (4)	0.35234 (12)	0.0398 (6)
H19	0.9911	0.6906	0.3535	0.048*
C14	0.8740 (2)	0.4705 (4)	0.04078 (11)	0.0427 (6)
H14	0.8732	0.5238	0.0816	0.051*
C22	1.09565 (18)	0.2309 (4)	0.34725 (11)	0.0403 (6)
H22	1.1236	0.1163	0.3456	0.048*
C11	0.8779 (2)	0.3173 (4)	−0.08037 (11)	0.0425 (6)
H11	0.8806	0.2646	−0.1209	0.051*
C13	0.8459 (2)	0.5745 (4)	−0.01813 (12)	0.0443 (6)
H13	0.8265	0.6956	−0.0166	0.053*
C10	0.90468 (19)	0.2167 (4)	−0.02133 (11)	0.0416 (6)
H10	0.9245	0.0959	−0.0229	0.050*
C4	0.75624 (17)	0.2812 (3)	0.17080 (11)	0.0360 (5)
H4A	0.6918	0.3253	0.1724	0.043*
H4B	0.7973	0.3866	0.1690	0.043*
C17	1.02478 (16)	0.2975 (3)	0.28970 (11)	0.0332 (5)
C12	0.84721 (18)	0.4958 (4)	−0.07936 (11)	0.0364 (5)
C1	0.92723 (17)	0.1728 (3)	0.10336 (10)	0.0337 (5)
H1	0.9806	0.0885	0.1013	0.040*
C23	1.0724 (2)	0.7590 (4)	0.47980 (14)	0.0520 (7)
H23A	1.0010	0.7412	0.4694	0.062*
H23B	1.0846	0.8516	0.4494	0.062*
C24	1.1141 (2)	0.8196 (4)	0.55196 (14)	0.0562 (8)
H24A	1.0961	0.7332	0.5815	0.084*
H24B	1.0877	0.9377	0.5576	0.084*
H24C	1.1854	0.8269	0.5630	0.084*
C15	0.7732 (3)	0.7581 (4)	−0.14446 (14)	0.0554 (8)
H15A	0.8209	0.8497	−0.1212	0.067*
H15B	0.7206	0.7515	−0.1226	0.067*
C16	0.7307 (3)	0.8097 (5)	−0.21709 (15)	0.0712 (10)
H16A	0.7821	0.8063	−0.2393	0.107*
H16B	0.7036	0.9309	−0.2200	0.107*
H16C	0.6790	0.7251	−0.2388	0.107*

	U11	U22	U33	U12	U13	U23
O3	0.0551 (11)	0.0491 (11)	0.0322 (9)	0.0124 (9)	−0.0039 (7)	−0.0091 (8)
O2	0.0672 (12)	0.0548 (12)	0.0289 (9)	0.0118 (10)	0.0172 (8)	0.0084 (8)
O1	0.1000 (18)	0.0292 (11)	0.0569 (13)	0.0043 (11)	0.0110 (11)	0.0016 (9)
N1	0.0411 (10)	0.0356 (11)	0.0225 (9)	−0.0035 (9)	0.0048 (7)	0.0003 (8)
C20	0.0364 (11)	0.0413 (14)	0.0279 (11)	0.0011 (10)	0.0016 (9)	−0.0016 (10)
C5	0.0483 (13)	0.0402 (14)	0.0304 (11)	−0.0065 (11)	0.0153 (10)	−0.0025 (10)
C18	0.0384 (12)	0.0401 (14)	0.0286 (11)	0.0024 (11)	−0.0035 (9)	0.0057 (10)
C9	0.0352 (11)	0.0384 (13)	0.0241 (10)	−0.0015 (10)	0.0085 (8)	−0.0017 (9)
C21	0.0436 (13)	0.0488 (16)	0.0267 (11)	0.0115 (12)	−0.0027 (9)	0.0024 (10)
C8	0.0485 (13)	0.0281 (13)	0.0377 (12)	0.0037 (11)	0.0105 (10)	0.0002 (10)
C3	0.0375 (11)	0.0411 (14)	0.0305 (11)	−0.0038 (11)	0.0034 (9)	−0.0014 (10)
C6	0.0495 (13)	0.0306 (12)	0.0278 (11)	0.0006 (11)	0.0065 (9)	0.0054 (9)
C7	0.0375 (11)	0.0366 (13)	0.0257 (10)	0.0074 (10)	0.0046 (8)	0.0019 (9)
C2	0.0476 (13)	0.0306 (12)	0.0254 (10)	−0.0010 (10)	0.0066 (9)	−0.0062 (9)
C19	0.0410 (12)	0.0341 (13)	0.0375 (12)	0.0066 (11)	0.0004 (10)	0.0015 (10)
C14	0.0645 (16)	0.0398 (15)	0.0251 (11)	−0.0022 (12)	0.0152 (10)	−0.0057 (10)
C22	0.0450 (13)	0.0411 (14)	0.0292 (11)	0.0153 (11)	0.0017 (10)	0.0009 (10)
C11	0.0538 (14)	0.0512 (16)	0.0235 (11)	0.0093 (13)	0.0128 (10)	−0.0033 (10)
C13	0.0688 (17)	0.0344 (14)	0.0318 (12)	0.0025 (13)	0.0180 (11)	−0.0008 (10)
C10	0.0495 (14)	0.0462 (15)	0.0289 (11)	0.0133 (12)	0.0111 (10)	−0.0028 (10)
C4	0.0357 (11)	0.0381 (14)	0.0348 (12)	0.0018 (10)	0.0113 (9)	−0.0032 (10)
C17	0.0327 (11)	0.0384 (13)	0.0252 (10)	0.0025 (10)	0.0033 (8)	0.0011 (9)
C12	0.0415 (12)	0.0432 (14)	0.0259 (10)	−0.0013 (11)	0.0118 (9)	0.0016 (10)
C1	0.0381 (11)	0.0377 (13)	0.0248 (10)	0.0048 (10)	0.0083 (8)	−0.0015 (9)
C23	0.0540 (16)	0.0437 (16)	0.0505 (16)	0.0079 (13)	0.0027 (12)	−0.0104 (13)
C24	0.0613 (17)	0.0534 (18)	0.0479 (16)	0.0040 (15)	0.0060 (13)	−0.0154 (14)
C15	0.073 (2)	0.0520 (18)	0.0429 (15)	0.0098 (15)	0.0185 (14)	0.0102 (13)
C16	0.090 (2)	0.076 (2)	0.0498 (18)	0.026 (2)	0.0241 (16)	0.0267 (17)

O3—C20	1.374 (3)	C7—C17	1.514 (3)
O3—C23	1.416 (3)	C7—H7	0.9800
O2—C12	1.377 (3)	C2—C1	1.555 (3)
O2—C15	1.413 (3)	C2—H2	0.9800
O1—C8	1.209 (3)	C19—H19	0.9300
N1—C7	1.456 (3)	C14—C13	1.388 (3)
N1—C1	1.460 (3)	C14—H14	0.9300
N1—H1N	0.8600	C22—C17	1.395 (3)
C20—C19	1.387 (3)	C22—H22	0.9300
C20—C21	1.389 (4)	C11—C10	1.376 (3)
C5—C4	1.527 (3)	C11—C12	1.377 (4)
C5—C6	1.536 (4)	C11—H11	0.9300
C5—H5A	0.9700	C13—C12	1.390 (3)
C5—H5B	0.9700	C13—H13	0.9300
C18—C17	1.379 (3)	C10—H10	0.9300
C18—C19	1.392 (3)	C4—H4A	0.9700
C18—H18	0.9300	C4—H4B	0.9700
C9—C14	1.378 (3)	C1—H1	0.9800
C9—C10	1.389 (3)	C23—C24	1.497 (3)
C9—C1	1.510 (3)	C23—H23A	0.9700
C21—C22	1.379 (3)	C23—H23B	0.9700
C21—H21	0.9300	C24—H24A	0.9600
C8—C2	1.502 (3)	C24—H24B	0.9600
C8—C6	1.507 (3)	C24—H24C	0.9600
C3—C4	1.520 (3)	C15—C16	1.489 (4)
C3—C2	1.536 (3)	C15—H15A	0.9700
C3—H3A	0.9700	C15—H15B	0.9700
C3—H3B	0.9700	C16—H16A	0.9600
C6—C7	1.555 (3)	C16—H16B	0.9600
C6—H6	0.9800	C16—H16C	0.9600
C20—O3—C23	118.68 (18)	C13—C14—H14	119.0
C12—O2—C15	118.45 (19)	C21—C22—C17	121.6 (2)
C7—N1—C1	114.74 (19)	C21—C22—H22	119.2
C7—N1—H1N	122.6	C17—C22—H22	119.2
C1—N1—H1N	122.6	C10—C11—C12	120.0 (2)
O3—C20—C19	124.8 (2)	C10—C11—H11	120.0
O3—C20—C21	116.14 (19)	C12—C11—H11	120.0
C19—C20—C21	119.1 (2)	C12—C13—C14	119.3 (2)
C4—C5—C6	113.94 (19)	C12—C13—H13	120.3
C4—C5—H5A	108.8	C14—C13—H13	120.3
C6—C5—H5A	108.8	C11—C10—C9	121.9 (2)
C4—C5—H5B	108.8	C11—C10—H10	119.1
C6—C5—H5B	108.8	C9—C10—H10	119.1
H5A—C5—H5B	107.7	C3—C4—C5	112.0 (2)
C17—C18—C19	121.6 (2)	C3—C4—H4A	109.2
C17—C18—H18	119.2	C5—C4—H4A	109.2
C19—C18—H18	119.2	C3—C4—H4B	109.2
C14—C9—C10	117.4 (2)	C5—C4—H4B	109.2
C14—C9—C1	122.35 (19)	H4A—C4—H4B	107.9
C10—C9—C1	120.2 (2)	C18—C17—C22	117.6 (2)
C22—C21—C20	120.1 (2)	C18—C17—C7	122.54 (19)
C22—C21—H21	120.0	C22—C17—C7	119.8 (2)
C20—C21—H21	120.0	O2—C12—C11	116.4 (2)
O1—C8—C2	124.4 (2)	O2—C12—C13	124.1 (2)
O1—C8—C6	124.3 (2)	C11—C12—C13	119.5 (2)
C2—C8—C6	111.3 (2)	N1—C1—C9	111.8 (2)
C4—C3—C2	114.00 (18)	N1—C1—C2	110.00 (18)
C4—C3—H3A	108.8	C9—C1—C2	111.01 (17)
C2—C3—H3A	108.8	N1—C1—H1	108.0
C4—C3—H3B	108.8	C9—C1—H1	108.0
C2—C3—H3B	108.8	C2—C1—H1	108.0
H3A—C3—H3B	107.6	O3—C23—C24	108.7 (2)
C8—C6—C5	108.31 (19)	O3—C23—H23A	109.9
C8—C6—C7	106.74 (19)	C24—C23—H23A	109.9
C5—C6—C7	115.6 (2)	O3—C23—H23B	109.9
C8—C6—H6	108.7	C24—C23—H23B	109.9
C5—C6—H6	108.7	H23A—C23—H23B	108.3
C7—C6—H6	108.7	C23—C24—H24A	109.5
N1—C7—C17	111.9 (2)	C23—C24—H24B	109.5
N1—C7—C6	110.13 (17)	H24A—C24—H24B	109.5
C17—C7—C6	110.99 (18)	C23—C24—H24C	109.5
N1—C7—H7	107.9	H24A—C24—H24C	109.5
C17—C7—H7	107.9	H24B—C24—H24C	109.5
C6—C7—H7	107.9	O2—C15—C16	109.1 (2)
C8—C2—C3	108.46 (19)	O2—C15—H15A	109.9
C8—C2—C1	107.17 (18)	C16—C15—H15A	109.9
C3—C2—C1	115.2 (2)	O2—C15—H15B	109.9
C8—C2—H2	108.6	C16—C15—H15B	109.9
C3—C2—H2	108.6	H15A—C15—H15B	108.3
C1—C2—H2	108.6	C15—C16—H16A	109.5
C20—C19—C18	119.9 (2)	C15—C16—H16B	109.5
C20—C19—H19	120.0	H16A—C16—H16B	109.5
C18—C19—H19	120.0	C15—C16—H16C	109.5
C9—C14—C13	121.9 (2)	H16A—C16—H16C	109.5
C9—C14—H14	119.0	H16B—C16—H16C	109.5
C23—O3—C20—C19	8.5 (4)	C14—C9—C10—C11	−0.6 (4)
C23—O3—C20—C21	−172.5 (3)	C1—C9—C10—C11	176.5 (2)
O3—C20—C21—C22	179.7 (2)	C2—C3—C4—C5	−46.6 (3)
C19—C20—C21—C22	−1.2 (4)	C6—C5—C4—C3	46.6 (3)
O1—C8—C6—C5	−118.4 (3)	C19—C18—C17—C22	−2.5 (4)
C2—C8—C6—C5	62.6 (2)	C19—C18—C17—C7	174.5 (2)
O1—C8—C6—C7	116.5 (3)	C21—C22—C17—C18	2.7 (4)
C2—C8—C6—C7	−62.5 (2)	C21—C22—C17—C7	−174.5 (2)
C4—C5—C6—C8	−53.9 (3)	N1—C7—C17—C18	35.2 (3)
C4—C5—C6—C7	65.7 (3)	C6—C7—C17—C18	−88.3 (3)
C1—N1—C7—C17	179.35 (18)	N1—C7—C17—C22	−147.8 (2)
C1—N1—C7—C6	−56.7 (2)	C6—C7—C17—C22	88.7 (3)
C8—C6—C7—N1	57.0 (2)	C15—O2—C12—C11	169.6 (3)
C5—C6—C7—N1	−63.5 (2)	C15—O2—C12—C13	−11.4 (4)
C8—C6—C7—C17	−178.52 (18)	C10—C11—C12—O2	−179.3 (2)
C5—C6—C7—C17	61.0 (2)	C10—C11—C12—C13	1.6 (4)
O1—C8—C2—C3	118.4 (3)	C14—C13—C12—O2	179.9 (2)
C6—C8—C2—C3	−62.6 (2)	C14—C13—C12—C11	−1.2 (4)
O1—C8—C2—C1	−116.7 (3)	C7—N1—C1—C9	−179.96 (18)
C6—C8—C2—C1	62.3 (2)	C7—N1—C1—C2	56.2 (2)
C4—C3—C2—C8	54.2 (3)	C14—C9—C1—N1	−27.4 (3)
C4—C3—C2—C1	−65.9 (3)	C10—C9—C1—N1	155.7 (2)
O3—C20—C19—C18	−179.6 (2)	C14—C9—C1—C2	95.9 (3)
C21—C20—C19—C18	1.4 (4)	C10—C9—C1—C2	−81.1 (3)
C17—C18—C19—C20	0.5 (4)	C8—C2—C1—N1	−56.4 (2)
C10—C9—C14—C13	1.0 (4)	C3—C2—C1—N1	64.4 (2)
C1—C9—C14—C13	−176.0 (2)	C8—C2—C1—C9	179.34 (18)
C20—C21—C22—C17	−0.8 (4)	C3—C2—C1—C9	−59.9 (2)
C9—C14—C13—C12	−0.2 (4)	C20—O3—C23—C24	174.3 (2)
C12—C11—C10—C9	−0.8 (4)	C12—O2—C15—C16	−166.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1i	0.93	2.57	3.428 (3)	154
C14—H14···O1i	0.92	2.61	3.501 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1i	0.93	2.57	3.428 (3)	154
C14—H14⋯O1i	0.92	2.61	3.501 (3)	159

Symmetry code: (i) .