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

In the title compound, C(26)H(33)NO(3), a crystallographic mirror plane bis-ects the mol-ecule (two C atoms, one O atom and one N atom lie on the mirror plane). The mol-ecule exists in a twin-chair conformation with equatorial orientations of the 4-propoxyphenyl groups. The dihedral angle between the 4-propoxyphenyl groups is 31.58 (3)°.

Related literature

For background to 3-aza­bicyclo­nona­nes, see: Jeyaraman & Avila (1981 ▶); Barker et al. (2005 ▶); Parthiban et al. (2009a ▶, 2010b ▶,c ▶). For related stuctures, see: Parthiban et al. (2009b ▶,c ▶, 2010a ▶); Smith-Verdier et al. (1983 ▶); Padegimas & Kovacic (1972 ▶). For ring puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C26H33NO3

M = 407.53

Orthorhombic,

a = 7.3846 (4) Å

b = 29.3963 (19) Å

c = 10.2739 (7) Å

V = 2230.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.981, T max = 0.985

7260 measured reflections

1860 independent reflections

1121 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.104

S = 1.00

1860 reflections

146 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536811007483/hb5803sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007483/hb5803Isup2.hkl

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

C26H33NO3	F(000) = 880
Mr = 407.53	Dx = 1.214 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1042 reflections
a = 7.3846 (4) Å	θ = 2.3–20.8°
b = 29.3963 (19) Å	µ = 0.08 mm−1
c = 10.2739 (7) Å	T = 298 K
V = 2230.3 (2) Å3	Block, colourless
Z = 4	0.25 × 0.22 × 0.20 mm

Bruker APEXII CCD diffractometer	1860 independent reflections
Radiation source: fine-focus sealed tube	1121 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 26.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.981, Tmax = 0.985	k = −31→32
7260 measured reflections	l = −12→10

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.4368P] where P = (Fo2 + 2Fc2)/3
1860 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.20 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
C1	0.6512 (3)	0.29134 (6)	0.6070 (2)	0.0384 (5)
H1	0.6934	0.2893	0.6972	0.046*
C2	0.8207 (3)	0.29225 (7)	0.5180 (2)	0.0426 (6)
H2	0.8944	0.3188	0.5408	0.051*
C3	0.7815 (3)	0.29351 (7)	0.3708 (2)	0.0474 (6)
H3A	0.7004	0.3187	0.3529	0.057*
H3B	0.8940	0.2993	0.3249	0.057*
C4	0.6973 (4)	0.2500	0.3174 (3)	0.0482 (8)
H4A	0.7093	0.2500	0.2234	0.058*
H4B	0.5691	0.2500	0.3377	0.058*
C5	0.9286 (4)	0.2500	0.5451 (3)	0.0437 (8)
C6	0.5396 (3)	0.33407 (7)	0.5949 (2)	0.0364 (5)
C7	0.3900 (3)	0.33809 (7)	0.5140 (2)	0.0418 (6)
H7	0.3506	0.3130	0.4666	0.050*
C8	0.2990 (3)	0.37892 (7)	0.5032 (2)	0.0426 (6)
H8	0.1988	0.3811	0.4488	0.051*
C9	0.3553 (3)	0.41666 (7)	0.5724 (2)	0.0389 (6)
C10	0.5009 (3)	0.41290 (7)	0.6550 (2)	0.0480 (6)
H10	0.5384	0.4378	0.7040	0.058*
C11	0.5911 (3)	0.37188 (7)	0.6647 (2)	0.0462 (6)
H11	0.6901	0.3697	0.7204	0.055*
C12	0.3046 (3)	0.49521 (7)	0.6265 (2)	0.0484 (6)
H12A	0.4284	0.5039	0.6070	0.058*
H12B	0.2959	0.4889	0.7190	0.058*
C13	0.1778 (3)	0.53290 (7)	0.5904 (2)	0.0578 (7)
H13A	0.0545	0.5237	0.6096	0.069*
H13B	0.1863	0.5386	0.4976	0.069*
C14	0.2201 (4)	0.57630 (8)	0.6634 (3)	0.0768 (9)
H14A	0.2116	0.5708	0.7554	0.115*
H14B	0.1350	0.5995	0.6390	0.115*
H14C	0.3405	0.5861	0.6423	0.115*
N1	0.5477 (4)	0.2500	0.5790 (3)	0.0405 (7)
O1	1.0831 (3)	0.2500	0.5851 (2)	0.0633 (7)
O2	0.25630 (19)	0.45579 (5)	0.55359 (16)	0.0531 (5)
H1N	0.458 (4)	0.2500	0.623 (3)	0.029 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0415 (12)	0.0358 (12)	0.0380 (13)	−0.0030 (10)	−0.0027 (10)	−0.0016 (10)
C2	0.0377 (13)	0.0352 (12)	0.0548 (16)	−0.0049 (10)	0.0003 (11)	−0.0056 (11)
C3	0.0497 (14)	0.0433 (13)	0.0492 (15)	0.0036 (11)	0.0091 (12)	0.0038 (12)
C4	0.055 (2)	0.049 (2)	0.0407 (19)	0.000	0.0047 (16)	0.000
C5	0.0354 (19)	0.049 (2)	0.047 (2)	0.000	0.0018 (16)	0.000
C6	0.0379 (12)	0.0346 (12)	0.0368 (13)	−0.0022 (10)	0.0005 (10)	−0.0019 (10)
C7	0.0445 (13)	0.0362 (13)	0.0445 (14)	−0.0045 (11)	−0.0023 (11)	−0.0051 (11)
C8	0.0439 (13)	0.0424 (14)	0.0415 (14)	−0.0020 (11)	−0.0081 (11)	−0.0027 (11)
C9	0.0413 (13)	0.0318 (13)	0.0436 (14)	−0.0017 (10)	0.0042 (11)	0.0011 (10)
C10	0.0508 (15)	0.0388 (14)	0.0543 (16)	−0.0033 (11)	−0.0069 (13)	−0.0129 (12)
C11	0.0435 (14)	0.0436 (14)	0.0515 (15)	0.0004 (11)	−0.0117 (12)	−0.0081 (12)
C12	0.0519 (14)	0.0357 (13)	0.0575 (15)	−0.0046 (11)	0.0027 (12)	−0.0054 (12)
C13	0.0594 (15)	0.0400 (14)	0.0740 (18)	0.0013 (12)	0.0019 (14)	−0.0047 (13)
C14	0.0743 (19)	0.0471 (15)	0.109 (3)	0.0032 (14)	−0.0007 (17)	−0.0183 (16)
N1	0.0371 (16)	0.0360 (16)	0.0483 (18)	0.000	0.0066 (15)	0.000
O1	0.0369 (14)	0.0686 (16)	0.0845 (18)	0.000	−0.0115 (13)	0.000
O2	0.0604 (10)	0.0345 (9)	0.0644 (11)	0.0053 (7)	−0.0124 (8)	−0.0074 (8)

C1—N1	1.464 (2)	C8—C9	1.381 (3)
C1—C6	1.507 (3)	C8—H8	0.9300
C1—C2	1.551 (3)	C9—C10	1.375 (3)
C1—H1	0.9800	C9—O2	1.376 (2)
C2—C5	1.502 (3)	C10—C11	1.381 (3)
C2—C3	1.540 (3)	C10—H10	0.9300
C2—H2	0.9800	C11—H11	0.9300
C3—C4	1.524 (3)	C12—O2	1.425 (2)
C3—H3A	0.9700	C12—C13	1.497 (3)
C3—H3B	0.9700	C12—H12A	0.9700
C4—C3i	1.524 (3)	C12—H12B	0.9700
C4—H4A	0.9700	C13—C14	1.512 (3)
C4—H4B	0.9700	C13—H13A	0.9700
C5—O1	1.213 (3)	C13—H13B	0.9700
C5—C2i	1.502 (3)	C14—H14A	0.9600
C6—C11	1.377 (3)	C14—H14B	0.9600
C6—C7	1.387 (3)	C14—H14C	0.9600
C7—C8	1.380 (3)	N1—C1i	1.464 (2)
C7—H7	0.9300	N1—H1N	0.80 (3)
N1—C1—C6	112.97 (17)	C7—C8—H8	119.6
N1—C1—C2	108.69 (19)	C9—C8—H8	119.6
C6—C1—C2	112.25 (17)	C10—C9—O2	124.69 (19)
N1—C1—H1	107.6	C10—C9—C8	119.24 (19)
C6—C1—H1	107.6	O2—C9—C8	116.06 (19)
C2—C1—H1	107.6	C9—C10—C11	119.5 (2)
C5—C2—C3	107.6 (2)	C9—C10—H10	120.3
C5—C2—C1	107.73 (19)	C11—C10—H10	120.3
C3—C2—C1	115.30 (17)	C6—C11—C10	122.3 (2)
C5—C2—H2	108.7	C6—C11—H11	118.9
C3—C2—H2	108.7	C10—C11—H11	118.9
C1—C2—H2	108.7	O2—C12—C13	108.35 (18)
C4—C3—C2	114.2 (2)	O2—C12—H12A	110.0
C4—C3—H3A	108.7	C13—C12—H12A	110.0
C2—C3—H3A	108.7	O2—C12—H12B	110.0
C4—C3—H3B	108.7	C13—C12—H12B	110.0
C2—C3—H3B	108.7	H12A—C12—H12B	108.4
H3A—C3—H3B	107.6	C12—C13—C14	111.9 (2)
C3—C4—C3i	114.1 (3)	C12—C13—H13A	109.2
C3—C4—H4A	108.7	C14—C13—H13A	109.2
C3i—C4—H4A	108.7	C12—C13—H13B	109.2
C3—C4—H4B	108.7	C14—C13—H13B	109.2
C3i—C4—H4B	108.7	H13A—C13—H13B	107.9
H4A—C4—H4B	107.6	C13—C14—H14A	109.5
O1—C5—C2i	124.19 (13)	C13—C14—H14B	109.5
O1—C5—C2	124.19 (13)	H14A—C14—H14B	109.5
C2i—C5—C2	111.6 (3)	C13—C14—H14C	109.5
C11—C6—C7	117.62 (19)	H14A—C14—H14C	109.5
C11—C6—C1	118.61 (18)	H14B—C14—H14C	109.5
C7—C6—C1	123.75 (19)	C1—N1—C1i	112.2 (2)
C8—C7—C6	120.7 (2)	C1—N1—H1N	108.6 (10)
C8—C7—H7	119.7	C1i—N1—H1N	108.6 (10)
C6—C7—H7	119.7	C9—O2—C12	118.21 (16)
C7—C8—C9	120.7 (2)
N1—C1—C2—C5	−58.5 (2)	C1—C6—C7—C8	−177.0 (2)
C6—C1—C2—C5	175.77 (19)	C6—C7—C8—C9	0.2 (3)
N1—C1—C2—C3	61.6 (2)	C7—C8—C9—C10	−1.6 (3)
C6—C1—C2—C3	−64.1 (2)	C7—C8—C9—O2	179.35 (19)
C5—C2—C3—C4	52.0 (3)	O2—C9—C10—C11	−179.3 (2)
C1—C2—C3—C4	−68.2 (3)	C8—C9—C10—C11	1.7 (3)
C2—C3—C4—C3i	−42.1 (3)	C7—C6—C11—C10	−0.9 (3)
C3—C2—C5—O1	115.5 (3)	C1—C6—C11—C10	177.2 (2)
C1—C2—C5—O1	−119.6 (3)	C9—C10—C11—C6	−0.5 (3)
C3—C2—C5—C2i	−65.1 (3)	O2—C12—C13—C14	−179.8 (2)
C1—C2—C5—C2i	59.8 (3)	C6—C1—N1—C1i	−172.82 (15)
N1—C1—C6—C11	154.5 (2)	C2—C1—N1—C1i	61.9 (3)
C2—C1—C6—C11	−82.1 (2)	C10—C9—O2—C12	−1.4 (3)
N1—C1—C6—C7	−27.5 (3)	C8—C9—O2—C12	177.64 (18)
C2—C1—C6—C7	95.8 (2)	C13—C12—O2—C9	−179.52 (18)
C11—C6—C7—C8	1.0 (3)