organic compounds
1-Methyl-2,4-bis(2-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608 739, Republic of Korea, and bDepartment of Chemistry, IIT Madras, Chennai, TamilNadu, India
*Correspondence e-mail: ytjeong@pknu.ac.kr
The 23H27NO3, shows that the compound exists in a chair–chair conformation with an equatorial disposition of 2-methoxyphenyl groups at an angle of 39.94 (3)° with respect to each other. An intermolecular N—H⋯π interaction is observed in the crystal packing.
of the title compound, CRelated 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
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell 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.
Supporting information
10.1107/S1600536809047928/ez2190sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047928/ez2190Isup2.hkl
A mixture of 2-methylcyclohexanone (0.05 mol, 5.61 g) and ortho-methoxybenzaldehyde (0.1 mol, 13.62 g) was added to a warm solution of ammonium acetate (0.075 mol, 5.78 g) in 50 ml of absolute ethanol. The mixture was gently warmed with stirring until a yellow color was obtained during the mixing of the reactants and then allowed to stir at 303–308° K until formation of the product. At the end, the crude azabicyclic ketone was separated by filtration and washed with a 1:5 ethanol-ether mixture until the solid became colorless. Recrystallization of the compound from ethanol gave X-ray diffraction quality crystals of 1-methyl-2,4-bis(2-methoxyphenyl)-3- azabicyclo[3.3.1]nonan-9-one.
Nitrogen H atoms were located in a difference Fourier map and refined isotropically. Other hydrogen atoms were fixed geometrically and allowed to ride on the parent carbon atoms,with aromatic C—H =0.93 Å, aliphatic C—H = 0.98Å and methylene C—H = 0.97 Å. The displacement parameters were set for phenyl, methylene and aliphatic H atoms at Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell
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 (Sheldrick, 2008).Fig. 1. ORTEP diagram of the molecule, showing the atom numbering scheme, with atoms represented as 30% probability ellipsoids. |
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 monochromator | 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 |
C23H27NO3 | V = 1922.59 (15) Å3 |
Mr = 365.46 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.9569 (3) Å | µ = 0.08 mm−1 |
b = 20.8291 (9) Å | T = 298 K |
c = 11.6708 (6) Å | 0.41 × 0.24 × 0.20 mm |
β = 96.297 (2)° |
Bruker APEXII CCD area-detector diffractometer | 4608 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 3166 reflections with I > 2σ(I) |
Tmin = 0.288, Tmax = 0.980 | Rint = 0.026 |
14049 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.22 e Å−3 |
4608 reflections | Δρmin = −0.21 e Å−3 |
251 parameters |
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 | 0.23693 (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) |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C23H27NO3 |
Mr | 365.46 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 7.9569 (3), 20.8291 (9), 11.6708 (6) |
β (°) | 96.297 (2) |
V (Å3) | 1922.59 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.41 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.288, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14049, 4608, 3166 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.127, 1.02 |
No. of reflections | 4608 |
No. of parameters | 251 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.21 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).
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) −x+1, −y, −z+1. |
Acknowledgements
This research was supported by the Industrial Technology Devlopment Program, which was conducted by the Ministry of Knowledge Economy of the Korean Government. The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.
References
Barker, D., Lin, D. H. S., Carland, J. E., Chu, C. P. Y., Chebib, M., Brimble, M. A., Savage, G. P. & McLeod, M. D. (2005). Bioorg. Med. Chem. 13, 4565–4575. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2, SAINT-Plus and XPREP, Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hardick, D. J., Blagbrough, I. S., Cooper, G., Potter, B. V. L., Critchley, T. & Wonnacott, S. (1996). J. Med. Chem. 39, 4860–4866. CrossRef CAS PubMed Web of Science Google Scholar
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149–174. CrossRef CAS Web of Science Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Padegimas, S. J. & Kovacic, P. (1972). J. Org. Chem. 37, 2672–2676. CrossRef CAS Web of Science Google Scholar
Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2009). Acta Cryst. E65, o1596. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2008). Acta Cryst. E64, o2385. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2009). Acta Cryst. E65, o1383. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith-Verdier, P., Florencio, F. & García-Blanco, S. (1983). Acta Cryst. C39, 101–103. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
3-Azabicyclononanes are an important class of heterocycles due to their broad spectrum biological activities (Jeyaraman & Avila, 1981; Hardick et al., 1996; Barker et al., 2005). Owing to the diverse possibilities in conformations, viz., chair-chair (Parthiban et al., 2008; Parthiban, Ramkumar & Jeong, 2009; Parthiban, Ramkumar, Kim et al., 2009), chair-boat (Smith-Verdier et al., 1983) and boat-boat (Padegimas & Kovacic, 1972) for the azabicycle, the present crystal study was undertaken to explore the conformation, stereochemistry and bonding of the title compound.
The analysis of torsion angles, asymmetry parameters and least-squares planes calculated for the title compound shows that the piperidine ring adopts a near ideal chair conformation with deviations of the ring atoms C8 and N1 from the C1/C2/C6/C7 plane by 0.655 (3) Å and -0.708 (3) Å, respectively. The smallest displacement asymmetry parameters are q2 = 0.0341 (15) Å and q3 =0.6123 (15) Å (Nardelli, 1983). The total puckering amplitude, QT = 0.6132 (15) Å and θ = 3.14 (14) ° (Cremer & Pople, 1975). The cyclohexane ring deviates from the ideal chair conformation by the deviation of ring atoms C4 and C8 from the C2/C3/C5/C6 plane by -0.697 (4) Å and 0.535 (3) Å, respectively. The smallest displacement asymmetry parameters are q2 = 0.1216 (17) Å and q3 = 0.5322 (17) Å (Nardelli, 1983); total puckering amplitude, QT = 0.5460 (16) Å, and θ =12.87 (18)° (Cremer & Pople, 1975). Hence, the title compound C23H27NO3, exists in a chair-chair conformation with an equatorial orientation of the ortho-methoxyphenyl groups on the heterocycle, which are orientated at an angle of 39.94 (3)° with respect to each other. The crystal structure is stabilized by an intermolecular N-H···π interaction between N1-H1A and the C16/C17/C18/C19/C20/C21 ring in a neighbouring molecule [N···centroid distance of 2.852 (3)Å; symmetry operator: 1-x,-y,1-z].