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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2356
https://doi.org/10.1107/S1600536812025433

(R)-3,3-Di­ethyl-1-(2-hy­dr­oxy-1-phenyl­eth­yl)piperidin-2-one

Oscar Romero,a Johana Ramírez,a Joel L. Terán,a Marcos Flores-Alamob and Jorge R. Juáreza*

aCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico, and bFacultad de Química, Universidad Nacional Autónoma de México, 04510, D.F., Mexico
*Correspondence e-mail: jorge.juarez@correo.buap.mx

(Received 28 May 2012; accepted 5 June 2012; online 7 July 2012)

In the title compound C17H25NO2, the piperidin-2-one ring adopts an envelope conformation with the C atom in the 5-position as the flap. The crystal packing is stabilized by inter­molecular O—H⋯O hydrogen bonds, building a infinite chain along the b-axis direction. C—H⋯π inter­actions further stabilize the crystal packing.

Related literature

For background to the synthesis of piperidines, see: Angle & Breitenbucher (1995[Angle, S. R. & Breitenbucher, J. G. (1995). In Studies in Natural Products Chemistry, Vol. 16, edited by Atta-ur Rahman, pp. 453-502. Amsterdam: Elsevier.]); Micouin et al. (1994[Micouin, L., Varea, R., Riche, C., Chiaroni, A., Quirion, J. C. & Husson, H. P. (1994). Tetrahedron Lett. 35, 2529-2532.]); Deslongchamps et al. (1975)[Deslongchamps, P., Cheriyan, O. U. & Patterson, D. R. (1975). Can. J. Chem. 53, 1682-1683.]. For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C17H25NO2

  • Mr = 275.38

  • Monoclinic, P 21

  • a = 7.5380 (3) Å

  • b = 12.6705 (6) Å

  • c = 7.9255 (4) Å

  • β = 91.776 (4)°

  • V = 756.61 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 130 K

  • 0.35 × 0.28 × 0.13 mm
Data collection

  • Oxford Diffraction Xcalibur Atlas Gemini diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.978, Tmax = 0.99

  • 5226 measured reflections

  • 1552 independent reflections

  • 1381 reflections with I > 2σ(I)

  • Rint = 0.039
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.114

  • S = 1.06

  • 1552 reflections

  • 185 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H1O⋯O1i 0.80 (4) 1.95 (4) 2.745 (3) 170 (4)
C4—H4A⋯Cg1ii 0.96 2.96 3.723 (3) 137
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+1]; (ii) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025433/bt5939sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025433/bt5939Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025433/bt5939Isup3.cml

checkCIF report


Comment top

The development of new methods for the enantioselective synthesis of piperidine derivatives by introduction of substituents at carbon positions of the heterocycle constitutes an area of curret interest (Angle & Breitenbucher, 1995). In the context of the enantioselective synthesis of 3-substituted piperidines, the enolate alkylation of the amide carbonyl of lactams derived from phenylglycinol with alkyl halides takes place with high diastereoselectivity to ultimately give enantiopure 3-alkylpiperidines in good yields. Although numerous methods have been developed for the α-alkylation, the double α-substitution in amides has been rarely studied (Micouin et al., 1994; Deslongchamps et al., 1975).

In the title compound C17H25NO2, the six membered ring N1/C1/C2/C3/C4/C5 shows an envelope conformation on C(4) with puckering parameters (Cremer & Pople, 1975) Q = 0.496 (3) Å, θ2 = 58.3 (3)°, φ2 = 240.7 (4)°, q2 = 0.422 (3) Å and q3 = 0.261 (3) Å. The N(1) atom in the piperidone moiety shows a planar conformation (r.m.s. deviation of N1, C1, C5 and C10 = 0.002Å). The quiral centre on C(10) shows an R absolute configuration with [α]D = -92. Crystal packing is stabilizad by hydrogen bond interactions [O(2)—H(1O)···O(1)], building a infinite chain along b direction and a intermolecular C(4)—H(4 A)···π interactions making a one-dimentional chain along a axis. Two intramolecular interactions, C8—(H8B)···O(1) and C(10)—H10···O(1) are too observated.

Related literature top

For background to the synthesis of piperidines, see: Angle & Breitenbucher (1995); Micouin et al. (1994); Deslongchamps et al. (1975). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental top

The title compound, C17H25NO2, was obtained disolving (R)-(-)-1-(2'-hidroxy-1'-phenylethyl)piperidin-2-one (0.29 g, 1.32 mmol) in THF anhydrous and added 4.0 equiv. HMPA and 4.5 equiv. s-BuLi. The mixture was stirred for 1 h and 3 equiv. of Iodoethane was added at -78 °C, the mixture was stirred for 2.5 h. Finally, the mixture was treated with a satured solution of NH4Cl (4.0 ml), extracted with ethyl acetate (3x20 ml) and purified by flash chromatography (SiO2, AcOEt: Petroleum ether; 6:4). Yield 80%. White crystals. [α]D= -92 (c 1.5, CH2Cl2). IR (KBr) 1615 cm-1. p.f.=89–91 °C, 1H NMR (CDCl3) δ (p.p.m.), J(Hz): 0.88 (t, 3H, J= 7.5, 7.2 Hz), 0.96 (t, 3H, J=7.5, 7.2 Hz), 2.82 (m, 1H), 2.89 (m, 1H), 3.14 (m, 1H), 3.32 (br, 1H-OH), 4.02–4.20 (dd, 2H, J= 5.1, 11.1 Hz), 5.89 (dd 1H, J= 5.1 Hz), 7.32 (m, 5H). 13C NMR (CDCl3), 8.9, 8.9, 20.5, 28.4, 31.9, 32.2, 44.0, 46.2, 58.5, 61.8, 127.5–128.5, 137.1, 177.1.

Refinement top

All H atoms were found in a difference map. The H atom bonded to O2 was freely refined. H atoms bonded to C atoms were placed in geometrical idealized positions and refined as riding on their parent atoms, with C—H = 0.93–0.98 Å and with Uiso(H) = 1.2 Ueq(C) or Ueq(H) = 1.5 Ueq(C) for methyl groups. The absolute configuration of the chiral centre could not be determined and was set according to the starting material.

Structure description top

The development of new methods for the enantioselective synthesis of piperidine derivatives by introduction of substituents at carbon positions of the heterocycle constitutes an area of curret interest (Angle & Breitenbucher, 1995). In the context of the enantioselective synthesis of 3-substituted piperidines, the enolate alkylation of the amide carbonyl of lactams derived from phenylglycinol with alkyl halides takes place with high diastereoselectivity to ultimately give enantiopure 3-alkylpiperidines in good yields. Although numerous methods have been developed for the α-alkylation, the double α-substitution in amides has been rarely studied (Micouin et al., 1994; Deslongchamps et al., 1975).

In the title compound C17H25NO2, the six membered ring N1/C1/C2/C3/C4/C5 shows an envelope conformation on C(4) with puckering parameters (Cremer & Pople, 1975) Q = 0.496 (3) Å, θ2 = 58.3 (3)°, φ2 = 240.7 (4)°, q2 = 0.422 (3) Å and q3 = 0.261 (3) Å. The N(1) atom in the piperidone moiety shows a planar conformation (r.m.s. deviation of N1, C1, C5 and C10 = 0.002Å). The quiral centre on C(10) shows an R absolute configuration with [α]D = -92. Crystal packing is stabilizad by hydrogen bond interactions [O(2)—H(1O)···O(1)], building a infinite chain along b direction and a intermolecular C(4)—H(4 A)···π interactions making a one-dimentional chain along a axis. Two intramolecular interactions, C8—(H8B)···O(1) and C(10)—H10···O(1) are too observated.

For background to the synthesis of piperidines, see: Angle & Breitenbucher (1995); Micouin et al. (1994); Deslongchamps et al. (1975). For ring conformation analysis, see: Cremer & Pople (1975).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
(R)-3,3-Diethyl-1-(2-hydroxy-1-phenylethyl)piperidin-2-one top
Crystal data top
C17H25NO2F(000) = 300
Mr = 275.38Dx = 1.209 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.5380 (3) ÅCell parameters from 3593 reflections
b = 12.6705 (6) Åθ = 3.7–26.0°
c = 7.9255 (4) ŵ = 0.08 mm−1
β = 91.776 (4)°T = 130 K
V = 756.61 (6) Å3Plate, colorless
Z = 20.35 × 0.28 × 0.13 mm
Data collection top
Oxford Diffraction Xcalibur Atlas Gemini
diffractometer		1552 independent reflections
Graphite monochromator1381 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1Rint = 0.039
ω scansθmax = 26.1°, θmin = 3.7°
Absorption correction: analytical
(CrysAlis PRO; Oxford Diffraction, 2009)		h = −9→9
Tmin = 0.978, Tmax = 0.99k = −14→15
5226 measured reflectionsl = −7→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0844P)2]
where P = (Fo2 + 2Fc2)/3
1552 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.37 e Å−3
1 restraintΔρmin = −0.30 e Å−3
Crystal data top
C17H25NO2V = 756.61 (6) Å3
Mr = 275.38Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.5380 (3) ŵ = 0.08 mm−1
b = 12.6705 (6) ÅT = 130 K
c = 7.9255 (4) Å0.35 × 0.28 × 0.13 mm
β = 91.776 (4)°
Data collection top
Oxford Diffraction Xcalibur Atlas Gemini
diffractometer		1552 independent reflections
Absorption correction: analytical
(CrysAlis PRO; Oxford Diffraction, 2009)		1381 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.99Rint = 0.039
5226 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.37 e Å−3
1552 reflectionsΔρmin = −0.30 e Å−3
185 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8432 (2)0.61989 (14)0.4209 (2)0.0257 (4)
C100.9135 (3)0.4297 (2)0.2824 (3)0.0194 (5)
H100.99560.47780.34210.023*
O21.1120 (2)0.29608 (16)0.3809 (3)0.0308 (5)
C120.9617 (3)0.4306 (2)0.0986 (3)0.0209 (5)
C10.7126 (3)0.56610 (19)0.3767 (3)0.0201 (5)
N10.7335 (3)0.47186 (16)0.3024 (3)0.0193 (5)
C110.9290 (3)0.3223 (2)0.3708 (3)0.0231 (5)
H11A0.88140.32630.4830.028*
H11B0.86320.26910.30680.028*
C130.9956 (4)0.3401 (2)0.0065 (4)0.0293 (6)
H130.98630.27430.05760.035*
C80.5095 (4)0.7194 (2)0.3363 (4)0.0325 (7)
H8A0.39960.75020.37350.039*
H8B0.6060.76180.38350.039*
C141.0431 (4)0.3466 (3)−0.1603 (3)0.0335 (7)
H141.06370.2852−0.22090.04*
C50.5857 (3)0.4055 (2)0.2393 (3)0.0264 (6)
H5A0.55520.3550.32570.032*
H5B0.62270.36640.14130.032*
C20.5257 (3)0.6069 (2)0.4118 (3)0.0253 (6)
C151.0601 (4)0.4429 (3)−0.2370 (3)0.0336 (7)
H151.09420.4472−0.34860.04*
C170.9776 (4)0.5275 (2)0.0182 (4)0.0305 (6)
H170.95520.58920.07740.037*
C30.3739 (3)0.5360 (3)0.3417 (4)0.0313 (6)
H3A0.33610.48940.43070.038*
H3B0.27360.58030.30880.038*
C60.5155 (4)0.6160 (2)0.6049 (3)0.0297 (6)
H6A0.59830.670.64380.036*
H6B0.39720.63940.6320.036*
C40.4252 (3)0.4704 (3)0.1921 (4)0.0315 (6)
H4A0.32760.42440.15810.038*
H4B0.45110.51610.09790.038*
C161.0257 (4)0.5336 (3)−0.1465 (4)0.0386 (7)
H161.03540.5992−0.1980.046*
C90.5120 (5)0.7282 (3)0.1467 (4)0.0435 (8)
H9A0.50130.80090.11430.065*
H9B0.41470.68880.09750.065*
H9C0.62180.70030.10750.065*
C70.5558 (5)0.5153 (3)0.7018 (4)0.0397 (7)
H7A0.54630.52820.82050.06*
H7B0.67410.49230.67910.06*
H7C0.47260.46150.66710.06*
H1O1.120 (5)0.249 (3)0.448 (5)0.041 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0195 (9)0.0215 (9)0.0361 (9)−0.0021 (8)0.0025 (7)−0.0075 (8)
C100.0156 (11)0.0178 (12)0.0249 (12)−0.0015 (11)0.0012 (9)−0.0026 (10)
O20.0233 (10)0.0281 (11)0.0410 (11)0.0065 (8)0.0035 (8)0.0138 (9)
C120.0132 (10)0.0231 (13)0.0264 (12)0.0017 (11)−0.0011 (9)−0.0001 (11)
C10.0220 (12)0.0193 (12)0.0191 (10)−0.0027 (11)0.0022 (9)0.0019 (10)
N10.0150 (10)0.0189 (10)0.0241 (10)−0.0002 (9)0.0010 (8)−0.0023 (8)
C110.0199 (12)0.0237 (13)0.0261 (12)0.0015 (11)0.0057 (9)0.0023 (10)
C130.0348 (14)0.0236 (14)0.0296 (13)0.0064 (13)0.0032 (10)0.0003 (12)
C80.0245 (14)0.0235 (14)0.0494 (18)0.0044 (12)0.0018 (12)0.0016 (13)
C140.0383 (16)0.0343 (16)0.0280 (14)0.0090 (14)0.0039 (12)−0.0061 (13)
C50.0186 (12)0.0239 (13)0.0366 (14)−0.0026 (11)−0.0005 (10)−0.0079 (11)
C20.0196 (12)0.0232 (13)0.0334 (13)0.0009 (11)0.0061 (10)−0.0010 (11)
C150.0328 (14)0.0463 (18)0.0221 (12)−0.0049 (14)0.0062 (10)0.0002 (12)
C170.0358 (15)0.0225 (14)0.0335 (14)−0.0033 (13)0.0060 (11)0.0001 (12)
C30.0152 (11)0.0356 (16)0.0431 (15)−0.0001 (12)0.0035 (10)−0.0032 (13)
C60.0262 (13)0.0282 (14)0.0353 (14)−0.0004 (13)0.0106 (10)−0.0054 (12)
C40.0174 (12)0.0350 (15)0.0420 (15)−0.0029 (12)−0.0017 (11)−0.0084 (13)
C160.0516 (19)0.0298 (16)0.0347 (15)−0.0089 (15)0.0054 (13)0.0070 (13)
C90.0451 (19)0.0331 (17)0.0517 (19)0.0011 (15)−0.0065 (14)0.0105 (14)
C70.0446 (17)0.0420 (18)0.0330 (15)0.0031 (16)0.0104 (13)0.0049 (14)
Geometric parameters (Å, º) top
O1—C11.239 (3)C5—H5A0.97
C10—N11.471 (3)C5—H5B0.97
C10—C121.513 (3)C2—C61.540 (3)
C10—C111.534 (3)C2—C31.544 (4)
C10—H100.98C15—C161.384 (5)
O2—C111.419 (3)C15—H150.93
O2—H1O0.80 (4)C17—C161.368 (4)
C12—C131.387 (4)C17—H170.93
C12—C171.390 (4)C3—C41.508 (4)
C1—N11.343 (3)C3—H3A0.97
C1—C21.534 (3)C3—H3B0.97
N1—C51.471 (3)C6—C71.515 (4)
C11—H11A0.97C6—H6A0.97
C11—H11B0.97C6—H6B0.97
C13—C141.383 (4)C4—H4A0.97
C13—H130.93C4—H4B0.97
C8—C91.508 (5)C16—H160.93
C8—C21.550 (4)C9—H9A0.96
C8—H8A0.97C9—H9B0.96
C8—H8B0.97C9—H9C0.96
C14—C151.371 (5)C7—H7A0.96
C14—H140.93C7—H7B0.96
C5—C41.500 (4)C7—H7C0.96
N1—C10—C12110.53 (18)C1—C2—C8107.6 (2)
N1—C10—C11109.28 (19)C6—C2—C8108.0 (2)
C12—C10—C11115.4 (2)C3—C2—C8110.3 (2)
N1—C10—H10107.1C14—C15—C16119.2 (2)
C12—C10—H10107.1C14—C15—H15120.4
C11—C10—H10107.1C16—C15—H15120.4
C11—O2—H1O105 (3)C16—C17—C12121.1 (3)
C13—C12—C17118.0 (2)C16—C17—H17119.4
C13—C12—C10123.7 (2)C12—C17—H17119.4
C17—C12—C10118.3 (2)C4—C3—C2113.4 (2)
O1—C1—N1120.7 (2)C4—C3—H3A108.9
O1—C1—C2119.3 (2)C2—C3—H3A108.9
N1—C1—C2120.0 (2)C4—C3—H3B108.9
C1—N1—C10119.4 (2)C2—C3—H3B108.9
C1—N1—C5124.0 (2)H3A—C3—H3B107.7
C10—N1—C5116.61 (19)C7—C6—C2115.2 (2)
O2—C11—C10107.05 (19)C7—C6—H6A108.5
O2—C11—H11A110.3C2—C6—H6A108.5
C10—C11—H11A110.3C7—C6—H6B108.5
O2—C11—H11B110.3C2—C6—H6B108.5
C10—C11—H11B110.3H6A—C6—H6B107.5
H11A—C11—H11B108.6C5—C4—C3109.3 (2)
C14—C13—C12120.7 (3)C5—C4—H4A109.8
C14—C13—H13119.6C3—C4—H4A109.8
C12—C13—H13119.6C5—C4—H4B109.8
C9—C8—C2116.7 (2)C3—C4—H4B109.8
C9—C8—H8A108.1H4A—C4—H4B108.3
C2—C8—H8A108.1C17—C16—C15120.4 (3)
C9—C8—H8B108.1C17—C16—H16119.8
C2—C8—H8B108.1C15—C16—H16119.8
H8A—C8—H8B107.3C8—C9—H9A109.5
C15—C14—C13120.5 (3)C8—C9—H9B109.5
C15—C14—H14119.7H9A—C9—H9B109.5
C13—C14—H14119.7C8—C9—H9C109.5
N1—C5—C4111.6 (2)H9A—C9—H9C109.5
N1—C5—H5A109.3H9B—C9—H9C109.5
C4—C5—H5A109.3C6—C7—H7A109.5
N1—C5—H5B109.3C6—C7—H7B109.5
C4—C5—H5B109.3H7A—C7—H7B109.5
H5A—C5—H5B108C6—C7—H7C109.5
C1—C2—C6106.26 (19)H7A—C7—H7C109.5
C1—C2—C3114.4 (2)H7B—C7—H7C109.5
C6—C2—C3110.0 (2)
N1—C10—C12—C13−116.5 (3)O1—C1—C2—C3176.7 (2)
C11—C10—C12—C138.1 (3)N1—C1—C2—C3−4.9 (3)
N1—C10—C12—C1765.3 (3)O1—C1—C2—C853.7 (3)
C11—C10—C12—C17−170.1 (2)N1—C1—C2—C8−127.9 (2)
O1—C1—N1—C103.5 (3)C9—C8—C2—C167.1 (3)
C2—C1—N1—C10−174.9 (2)C9—C8—C2—C6−178.6 (2)
O1—C1—N1—C5−177.1 (2)C9—C8—C2—C3−58.4 (3)
C2—C1—N1—C54.5 (3)C13—C14—C15—C16−1.3 (4)
C12—C10—N1—C1−110.0 (2)C13—C12—C17—C16−0.2 (4)
C11—C10—N1—C1121.9 (2)C10—C12—C17—C16178.2 (3)
C12—C10—N1—C570.6 (3)C1—C2—C3—C4−25.8 (4)
C11—C10—N1—C5−57.5 (3)C6—C2—C3—C4−145.3 (3)
N1—C10—C11—O2−167.33 (19)C8—C2—C3—C495.7 (3)
C12—C10—C11—O267.4 (3)C1—C2—C6—C7−56.3 (3)
C17—C12—C13—C14−0.3 (4)C3—C2—C6—C768.0 (3)
C10—C12—C13—C14−178.5 (2)C8—C2—C6—C7−171.5 (2)
C12—C13—C14—C151.0 (5)N1—C5—C4—C3−55.8 (3)
C1—N1—C5—C426.7 (3)C2—C3—C4—C555.9 (3)
C10—N1—C5—C4−153.9 (2)C12—C17—C16—C15−0.1 (5)
O1—C1—C2—C6−61.8 (3)C14—C15—C16—C170.8 (4)
N1—C1—C2—C6116.6 (2)C1—C5—N1—C10179.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
O2—H1O···O1i0.80 (4)1.95 (4)2.745 (3)170 (4)
C8—H8B···O10.972.552.874 (3)100
C10—H10···O10.982.232.707 (3)108
C4—H4A···Cg1ii0.962.963.723 (3)137
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H25NO2
Mr275.38
Crystal system, space groupMonoclinic, P21
Temperature (K)130
a, b, c (Å)7.5380 (3), 12.6705 (6), 7.9255 (4)
β (°) 91.776 (4)
V (Å3)756.61 (6)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.35 × 0.28 × 0.13
Data collection
DiffractometerOxford Diffraction Xcalibur Atlas Gemini
Absorption correctionAnalytical
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.978, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections		5226, 1552, 1381
Rint0.039
(sin θ/λ)max (Å−1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.114, 1.06
No. of reflections1552
No. of parameters185
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.37, −0.30

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
O2—H1O···O1i0.80 (4)1.95 (4)2.745 (3)170 (4)
C4—H4A···Cg1ii0.962.963.723 (3)137
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x+1, y, z.
 

Acknowledgements

This work was funded by projects VIEP-BUAP and CONACyT CB-2009–01/128747. JR and OR thank CONACyT for doctoral scholarships.

References

First citationAngle, S. R. & Breitenbucher, J. G. (1995). In Studies in Natural Products Chemistry, Vol. 16, edited by Atta-ur Rahman, pp. 453–502. Amsterdam: Elsevier.  Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationDeslongchamps, P., Cheriyan, O. U. & Patterson, D. R. (1975). Can. J. Chem. 53, 1682–1683.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationMicouin, L., Varea, R., Riche, C., Chiaroni, A., Quirion, J. C. & Husson, H. P. (1994). Tetrahedron Lett. 35, 2529–2532.  CSD CrossRef CAS Web of Science Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS 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.

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2356
https://doi.org/10.1107/S1600536812025433
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