1-Methyl-2,4-bis-(2-methoxy-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

The crystal structure of the title compound, C(23)H(27)NO(3), shows that the compound exists in a chair-chair conformation with an equatorial disposition of 2-methoxy-phenyl groups at an angle of 39.94 (3)° with respect to each other. An inter-molecular N-H⋯π inter-action is observed in the crystal packing.

Related literature

For the biological activity of 3-aza­bicyclo­nona­nes, see: Barker et al. (2005 ▶); Hardick et al. (1996 ▶); Jeyaraman & Avila (1981 ▶). For related structures with similar conformations, see: Parthiban et al. (2008 ▶); Parthiban, Ramkumar & Jeong (2009 ▶); Parthiban, Ramkumar, Kim et al. (2009 ▶). For a related structure with a chair–boat conformation, see: Smith-Verdier et al. (1983 ▶). For a related structure with a boat–boat conformation, see: Padegimas & Kovacic (1972 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C23H27NO3

M = 365.46

Monoclinic,

a = 7.9569 (3) Å

b = 20.8291 (9) Å

c = 11.6708 (6) Å

β = 96.297 (2)°

V = 1922.59 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.41 × 0.24 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.288, T max = 0.980

14049 measured reflections

4608 independent reflections

3166 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.127

S = 1.02

4608 reflections

251 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047928/ez2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047928/ez2190Isup2.hkl

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

C23H27NO3	F(000) = 784
Mr = 365.46	Dx = 1.263 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4178 reflections
a = 7.9569 (3) Å	θ = 2.6–28.0°
b = 20.8291 (9) Å	µ = 0.08 mm−1
c = 11.6708 (6) Å	T = 298 K
β = 96.297 (2)°	Block, colourless
V = 1922.59 (15) Å3	0.41 × 0.24 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4608 independent reflections
Radiation source: fine-focus sealed tube	3166 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→10
Tmin = 0.288, Tmax = 0.980	k = −27→27
14049 measured reflections	l = −15→15

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) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.4061P] where P = (Fo2 + 2Fc2)/3
4608 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.23693 (17)	0.12454 (6)	0.28186 (12)	0.0323 (3)
H1	0.1669	0.1269	0.3458	0.039*
C2	0.11755 (18)	0.10977 (7)	0.16904 (12)	0.0363 (3)
C3	0.2099 (2)	0.10169 (8)	0.06003 (13)	0.0431 (4)
H3A	0.1254	0.0972	−0.0060	0.052*
H3B	0.2725	0.1408	0.0492	0.052*
C4	0.3315 (2)	0.04531 (8)	0.06032 (14)	0.0473 (4)
H4A	0.4347	0.0557	0.1089	0.057*
H4B	0.3604	0.0385	−0.0174	0.057*
C5	0.2575 (2)	−0.01655 (8)	0.10382 (14)	0.0465 (4)
H5A	0.3483	−0.0473	0.1211	0.056*
H5B	0.1790	−0.0345	0.0427	0.056*
C6	0.16498 (18)	−0.00768 (7)	0.21184 (13)	0.0372 (3)
H6	0.1050	−0.0475	0.2256	0.045*
C7	0.27979 (17)	0.01007 (6)	0.32297 (12)	0.0321 (3)
H7	0.2089	0.0140	0.3862	0.039*
C8	0.03777 (19)	0.04528 (7)	0.19078 (12)	0.0383 (3)
C9	0.33357 (18)	0.18729 (6)	0.27865 (12)	0.0334 (3)
C10	0.49093 (19)	0.18943 (7)	0.23764 (14)	0.0407 (4)
H10	0.5344	0.1522	0.2082	0.049*
C11	0.5850 (2)	0.24549 (8)	0.23944 (15)	0.0479 (4)
H11	0.6903	0.2457	0.2119	0.058*
C12	0.5214 (2)	0.30076 (8)	0.28224 (16)	0.0505 (4)
H12	0.5839	0.3385	0.2836	0.061*
C13	0.3655 (2)	0.30062 (7)	0.32316 (14)	0.0452 (4)
H13	0.3230	0.3383	0.3516	0.054*
C14	0.27187 (19)	0.24449 (7)	0.32211 (12)	0.0370 (3)
C15	−0.0179 (2)	0.16144 (8)	0.14796 (16)	0.0530 (4)
H15A	−0.0981	0.1490	0.0843	0.079*
H15B	0.0340	0.2014	0.1305	0.079*
H15C	−0.0748	0.1665	0.2158	0.079*
C16	0.41183 (18)	−0.04090 (6)	0.35486 (12)	0.0325 (3)
C17	0.36550 (18)	−0.09743 (7)	0.40848 (12)	0.0355 (3)
C18	0.4828 (2)	−0.14549 (7)	0.43706 (13)	0.0432 (4)
H18	0.4506	−0.1831	0.4717	0.052*
C19	0.6482 (2)	−0.13728 (8)	0.41378 (14)	0.0487 (4)
H19	0.7271	−0.1695	0.4330	0.058*
C20	0.6970 (2)	−0.08216 (8)	0.36268 (15)	0.0497 (4)
H20	0.8087	−0.0767	0.3481	0.060*
C21	0.57849 (19)	−0.03438 (7)	0.33286 (14)	0.0421 (4)
H21	0.6118	0.0028	0.2974	0.050*
C22	0.0402 (2)	0.29848 (8)	0.39536 (17)	0.0566 (5)
H22A	0.1056	0.3174	0.4608	0.085*
H22B	−0.0717	0.2894	0.4143	0.085*
H22C	0.0339	0.3278	0.3316	0.085*
C23	0.1527 (3)	−0.15186 (11)	0.49954 (19)	0.0793 (7)
H23A	0.1658	−0.1920	0.4610	0.119*
H23B	0.0368	−0.1466	0.5134	0.119*
H23C	0.2235	−0.1515	0.5717	0.119*
N1	0.35903 (15)	0.07229 (5)	0.30669 (11)	0.0324 (3)
O1	−0.11245 (14)	0.03744 (6)	0.19326 (12)	0.0606 (4)
O2	0.11835 (14)	0.24067 (5)	0.36491 (10)	0.0498 (3)
O3	0.19994 (13)	−0.10095 (5)	0.42960 (10)	0.0484 (3)
H1A	0.4203 (18)	0.0824 (7)	0.3696 (13)	0.032 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0345 (7)	0.0274 (7)	0.0357 (7)	0.0025 (5)	0.0074 (6)	0.0021 (6)
C2	0.0341 (8)	0.0356 (8)	0.0387 (8)	0.0037 (6)	0.0025 (6)	0.0037 (6)
C3	0.0492 (9)	0.0446 (9)	0.0360 (8)	−0.0024 (7)	0.0065 (7)	0.0062 (7)
C4	0.0524 (10)	0.0531 (10)	0.0386 (8)	0.0012 (8)	0.0149 (7)	−0.0044 (7)
C5	0.0556 (10)	0.0417 (9)	0.0415 (9)	0.0027 (7)	0.0019 (7)	−0.0094 (7)
C6	0.0371 (8)	0.0303 (7)	0.0437 (8)	−0.0074 (6)	0.0027 (6)	−0.0005 (6)
C7	0.0336 (7)	0.0281 (7)	0.0356 (7)	−0.0004 (6)	0.0079 (6)	0.0008 (6)
C8	0.0346 (8)	0.0454 (9)	0.0344 (7)	−0.0040 (7)	0.0021 (6)	0.0012 (6)
C9	0.0375 (8)	0.0278 (7)	0.0352 (7)	0.0011 (6)	0.0047 (6)	0.0033 (6)
C10	0.0406 (8)	0.0338 (8)	0.0490 (9)	0.0025 (6)	0.0104 (7)	0.0025 (7)
C11	0.0397 (9)	0.0431 (9)	0.0625 (11)	−0.0038 (7)	0.0124 (8)	0.0071 (8)
C12	0.0538 (10)	0.0348 (9)	0.0637 (11)	−0.0107 (7)	0.0096 (8)	0.0045 (8)
C13	0.0571 (10)	0.0285 (8)	0.0511 (9)	0.0001 (7)	0.0099 (8)	−0.0009 (7)
C14	0.0426 (8)	0.0314 (7)	0.0379 (8)	0.0021 (6)	0.0085 (6)	0.0037 (6)
C15	0.0466 (10)	0.0492 (10)	0.0613 (11)	0.0119 (8)	−0.0018 (8)	0.0049 (8)
C16	0.0365 (8)	0.0272 (7)	0.0340 (7)	0.0002 (6)	0.0053 (6)	−0.0024 (6)
C17	0.0404 (8)	0.0320 (7)	0.0337 (7)	−0.0031 (6)	0.0025 (6)	−0.0014 (6)
C18	0.0578 (10)	0.0298 (7)	0.0408 (8)	0.0021 (7)	0.0006 (7)	0.0024 (6)
C19	0.0536 (10)	0.0414 (9)	0.0498 (9)	0.0186 (8)	−0.0003 (8)	−0.0031 (7)
C20	0.0395 (9)	0.0502 (10)	0.0608 (10)	0.0094 (7)	0.0116 (8)	−0.0031 (8)
C21	0.0401 (8)	0.0365 (8)	0.0510 (9)	0.0002 (7)	0.0117 (7)	0.0023 (7)
C22	0.0599 (11)	0.0430 (10)	0.0702 (12)	0.0106 (8)	0.0220 (9)	−0.0069 (8)
C23	0.0611 (13)	0.0974 (16)	0.0793 (14)	−0.0177 (11)	0.0073 (11)	0.0504 (13)
N1	0.0324 (6)	0.0256 (6)	0.0383 (7)	−0.0002 (5)	−0.0004 (5)	−0.0006 (5)
O1	0.0336 (6)	0.0681 (8)	0.0795 (9)	−0.0079 (6)	0.0039 (6)	0.0119 (7)
O2	0.0552 (7)	0.0316 (6)	0.0678 (8)	0.0036 (5)	0.0292 (6)	−0.0024 (5)
O3	0.0429 (6)	0.0469 (7)	0.0564 (7)	−0.0067 (5)	0.0093 (5)	0.0167 (5)

C1—N1	1.4663 (17)	C12—C13	1.377 (2)
C1—C9	1.5191 (19)	C12—H12	0.9300
C1—C2	1.5672 (19)	C13—C14	1.386 (2)
C1—H1	0.9800	C13—H13	0.9300
C2—C8	1.519 (2)	C14—O2	1.3719 (17)
C2—C15	1.524 (2)	C15—H15A	0.9600
C2—C3	1.547 (2)	C15—H15B	0.9600
C3—C4	1.521 (2)	C15—H15C	0.9600
C3—H3A	0.9700	C16—C21	1.385 (2)
C3—H3B	0.9700	C16—C17	1.4016 (19)
C4—C5	1.526 (2)	C17—O3	1.3685 (17)
C4—H4A	0.9700	C17—C18	1.384 (2)
C4—H4B	0.9700	C18—C19	1.384 (2)
C5—C6	1.539 (2)	C18—H18	0.9300
C5—H5A	0.9700	C19—C20	1.369 (2)
C5—H5B	0.9700	C19—H19	0.9300
C6—C8	1.499 (2)	C20—C21	1.389 (2)
C6—C7	1.547 (2)	C20—H20	0.9300
C6—H6	0.9800	C21—H21	0.9300
C7—N1	1.4628 (17)	C22—O2	1.4181 (18)
C7—C16	1.5111 (19)	C22—H22A	0.9600
C7—H7	0.9800	C22—H22B	0.9600
C8—O1	1.2099 (18)	C22—H22C	0.9600
C9—C10	1.389 (2)	C23—O3	1.414 (2)
C9—C14	1.4044 (19)	C23—H23A	0.9600
C10—C11	1.386 (2)	C23—H23B	0.9600
C10—H10	0.9300	C23—H23C	0.9600
C11—C12	1.373 (2)	N1—H1A	0.862 (15)
C11—H11	0.9300
N1—C1—C9	108.50 (11)	C12—C11—H11	120.3
N1—C1—C2	110.35 (11)	C10—C11—H11	120.3
C9—C1—C2	114.20 (11)	C11—C12—C13	120.41 (15)
N1—C1—H1	107.9	C11—C12—H12	119.8
C9—C1—H1	107.9	C13—C12—H12	119.8
C2—C1—H1	107.9	C12—C13—C14	120.17 (15)
C8—C2—C15	110.51 (13)	C12—C13—H13	119.9
C8—C2—C3	106.63 (12)	C14—C13—H13	119.9
C15—C2—C3	109.61 (13)	O2—C14—C13	123.04 (13)
C8—C2—C1	105.02 (11)	O2—C14—C9	116.28 (12)
C15—C2—C1	110.47 (12)	C13—C14—C9	120.67 (14)
C3—C2—C1	114.42 (12)	C2—C15—H15A	109.5
C4—C3—C2	116.20 (12)	C2—C15—H15B	109.5
C4—C3—H3A	108.2	H15A—C15—H15B	109.5
C2—C3—H3A	108.2	C2—C15—H15C	109.5
C4—C3—H3B	108.2	H15A—C15—H15C	109.5
C2—C3—H3B	108.2	H15B—C15—H15C	109.5
H3A—C3—H3B	107.4	C21—C16—C17	117.99 (13)
C3—C4—C5	112.60 (14)	C21—C16—C7	122.65 (12)
C3—C4—H4A	109.1	C17—C16—C7	119.37 (13)
C5—C4—H4A	109.1	O3—C17—C18	123.70 (13)
C3—C4—H4B	109.1	O3—C17—C16	115.52 (12)
C5—C4—H4B	109.1	C18—C17—C16	120.78 (14)
H4A—C4—H4B	107.8	C19—C18—C17	119.62 (14)
C4—C5—C6	114.05 (12)	C19—C18—H18	120.2
C4—C5—H5A	108.7	C17—C18—H18	120.2
C6—C5—H5A	108.7	C20—C19—C18	120.67 (14)
C4—C5—H5B	108.7	C20—C19—H19	119.7
C6—C5—H5B	108.7	C18—C19—H19	119.7
H5A—C5—H5B	107.6	C19—C20—C21	119.53 (16)
C8—C6—C5	109.21 (12)	C19—C20—H20	120.2
C8—C6—C7	106.72 (11)	C21—C20—H20	120.2
C5—C6—C7	115.07 (12)	C16—C21—C20	121.40 (14)
C8—C6—H6	108.6	C16—C21—H21	119.3
C5—C6—H6	108.6	C20—C21—H21	119.3
C7—C6—H6	108.6	O2—C22—H22A	109.5
N1—C7—C16	110.89 (11)	O2—C22—H22B	109.5
N1—C7—C6	109.03 (11)	H22A—C22—H22B	109.5
C16—C7—C6	111.68 (11)	O2—C22—H22C	109.5
N1—C7—H7	108.4	H22A—C22—H22C	109.5
C16—C7—H7	108.4	H22B—C22—H22C	109.5
C6—C7—H7	108.4	O3—C23—H23A	109.5
O1—C8—C6	123.22 (14)	O3—C23—H23B	109.5
O1—C8—C2	123.74 (14)	H23A—C23—H23B	109.5
C6—C8—C2	113.02 (12)	O3—C23—H23C	109.5
C10—C9—C14	117.47 (13)	H23A—C23—H23C	109.5
C10—C9—C1	120.91 (12)	H23B—C23—H23C	109.5
C14—C9—C1	121.54 (13)	C7—N1—C1	113.43 (11)
C11—C10—C9	121.82 (14)	C7—N1—H1A	108.5 (10)
C11—C10—H10	119.1	C1—N1—H1A	106.7 (10)
C9—C10—H10	119.1	C14—O2—C22	118.30 (12)
C12—C11—C10	119.47 (15)	C17—O3—C23	117.79 (13)
N1—C1—C2—C8	56.53 (14)	C9—C10—C11—C12	−0.4 (3)
C9—C1—C2—C8	179.06 (12)	C10—C11—C12—C13	0.0 (3)
N1—C1—C2—C15	175.70 (12)	C11—C12—C13—C14	0.4 (3)
C9—C1—C2—C15	−61.77 (16)	C12—C13—C14—O2	177.88 (14)
N1—C1—C2—C3	−60.04 (15)	C12—C13—C14—C9	−0.5 (2)
C9—C1—C2—C3	62.49 (16)	C10—C9—C14—O2	−178.29 (13)
C8—C2—C3—C4	−51.75 (17)	C1—C9—C14—O2	−1.4 (2)
C15—C2—C3—C4	−171.39 (14)	C10—C9—C14—C13	0.2 (2)
C1—C2—C3—C4	63.89 (17)	C1—C9—C14—C13	177.06 (13)
C2—C3—C4—C5	44.90 (19)	N1—C7—C16—C21	−20.15 (19)
C3—C4—C5—C6	−43.79 (19)	C6—C7—C16—C21	101.66 (15)
C4—C5—C6—C8	51.92 (17)	N1—C7—C16—C17	160.12 (12)
C4—C5—C6—C7	−68.05 (17)	C6—C7—C16—C17	−78.06 (16)
C8—C6—C7—N1	−58.41 (14)	C21—C16—C17—O3	179.13 (12)
C5—C6—C7—N1	62.92 (15)	C7—C16—C17—O3	−1.14 (19)
C8—C6—C7—C16	178.70 (11)	C21—C16—C17—C18	−0.8 (2)
C5—C6—C7—C16	−59.97 (16)	C7—C16—C17—C18	178.93 (13)
C5—C6—C8—O1	119.23 (16)	O3—C17—C18—C19	−179.09 (14)
C7—C6—C8—O1	−115.79 (16)	C16—C17—C18—C19	0.8 (2)
C5—C6—C8—C2	−62.18 (15)	C17—C18—C19—C20	−0.1 (2)
C7—C6—C8—C2	62.80 (15)	C18—C19—C20—C21	−0.7 (3)
C15—C2—C8—O1	−1.6 (2)	C17—C16—C21—C20	0.0 (2)
C3—C2—C8—O1	−120.63 (16)	C7—C16—C21—C20	−179.71 (14)
C1—C2—C8—O1	117.57 (16)	C19—C20—C21—C16	0.7 (3)
C15—C2—C8—C6	179.84 (13)	C16—C7—N1—C1	−176.79 (11)
C3—C2—C8—C6	60.79 (15)	C6—C7—N1—C1	59.86 (15)
C1—C2—C8—C6	−61.01 (15)	C9—C1—N1—C7	174.42 (11)
N1—C1—C9—C10	34.09 (17)	C2—C1—N1—C7	−59.77 (15)
C2—C1—C9—C10	−89.44 (16)	C13—C14—O2—C22	9.9 (2)
N1—C1—C9—C14	−142.65 (13)	C9—C14—O2—C22	−171.66 (14)
C2—C1—C9—C14	93.82 (16)	C18—C17—O3—C23	9.8 (2)
C14—C9—C10—C11	0.2 (2)	C16—C17—O3—C23	−170.10 (16)
C1—C9—C10—C11	−176.64 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cg1i	0.862 (15)	2.852 (3)	3.6276 (14)	150.6 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cg1i	0.862 (15)	2.852 (3)	3.6276 (14)	150.6 (12)

Symmetry code: (i) . Cg1 is the centroid of the C16–C21 ring.