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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3008.
Published online 2009 November 7. doi:  10.1107/S160053680903918X
PMCID: PMC2972088

1-Ethyl-4-hydr­oxy-9-aza­tricyclo­[7.4.1.02,7]tetra­deca-2,4,6-trien-8-one

Abstract

In the mol­ecule of the title compound, C15H19NO2, the six-membered dihydro­pyridinone ring assumes a screw-boat conformation. In the crystal structure, mol­ecules are linked via O—H(...)O hydrogen bonding between hydr­oxy and carbonyl groups, forming supra­molecular chains along the a axis.

Related literature

For the synthesis and bioactivity of novel bis-(−)-nor-meptazinols, see Xie et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3008-scheme1.jpg

Experimental

Crystal data

  • C15H19NO2
  • M r = 245.31
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3008-efi1.jpg
  • a = 8.298 (1) Å
  • b = 9.9817 (12) Å
  • c = 14.7324 (18) Å
  • V = 1220.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.37 × 0.23 × 0.22 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: none
  • 6713 measured reflections
  • 1397 independent reflections
  • 1280 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.091
  • S = 1.06
  • 1397 reflections
  • 165 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903918X/xu2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903918X/xu2615Isup2.hkl

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

Acknowledgments

This work is funded in part by the National Natural Science Foundation of China (grant 30801435).

supplementary crystallographic information

Comment

In previous study, our group has reported the synthesis and characterization of novel bis-(-)-nor-meptazinols that inhibit both acetylcholinesterase and butyrylcholinesterase as well as retarding Aβ aggregation (Xie et al., 2008). The title compound (I), was produced serendipitously whilst preparating of (-)-Nor-meptazinol (II), which is the intermediate of bis-(-)-nor-meptazinols. The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The six-membered dihydropyridinone ring assumes a screw-boat conformation. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonding (Table 1 and Fig. 2).

Experimental

A white powder (I) was obtained as a by-product of the reaction between (-)-N-carboethoxy-nor-meptazinol and 50% H2SO4 (Fig. 3). Single crystals suitable for crystallographic analysis were obtained by slow evaporation of an methanol solution. [α]D = -60.8° (c 0.332, MeOH).

Refinement

All H atoms were positioned geometrically and refined as riding (C—H = 0.93–0.97 Å, O—H = 0.82 Å), with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O). In the absence of significant anomalous scattering, Friedel opposites were merged and the absolute structure is not determined.

Figures

Fig. 1.
A view of the structure of title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Intermolecular hydrogen bond is shown as a dashed line.
Fig. 3.
The formation of the title compound.

Crystal data

C15H19NO2F(000) = 528
Mr = 245.31Dx = 1.335 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2536 reflections
a = 8.298 (1) Åθ = 2.5–26.4°
b = 9.9817 (12) ŵ = 0.09 mm1
c = 14.7324 (18) ÅT = 293 K
V = 1220.3 (3) Å3Prismatic, colourless
Z = 40.37 × 0.23 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer1280 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
graphiteθmax = 26.0°, θmin = 2.5°
[var phi] and ω scansh = −10→10
6713 measured reflectionsk = −12→12
1397 independent reflectionsl = −11→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0557P)2] where P = (Fo2 + 2Fc2)/3
1397 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.20 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N11.0502 (2)0.76044 (17)0.90237 (11)0.0315 (4)
O11.16080 (18)0.96697 (17)0.91934 (11)0.0429 (4)
O20.4251 (2)1.11984 (16)0.94981 (13)0.0507 (5)
H20.35571.06860.93070.076*
C11.0402 (2)0.8931 (2)0.91820 (13)0.0301 (5)
C20.8763 (2)0.9473 (2)0.93043 (13)0.0285 (5)
C30.8531 (3)1.0689 (2)0.97449 (13)0.0328 (5)
H30.94101.11261.00010.039*
C40.7027 (3)1.1258 (2)0.98083 (14)0.0357 (5)
H40.68831.20611.01180.043*
C50.5729 (3)1.0620 (2)0.94053 (15)0.0336 (5)
C60.5946 (3)0.9430 (2)0.89339 (14)0.0310 (5)
H60.50720.90310.86460.037*
C70.7454 (2)0.8827 (2)0.88863 (12)0.0262 (4)
C80.7732 (2)0.7468 (2)0.84288 (13)0.0279 (4)
C90.9025 (3)0.67983 (19)0.90089 (14)0.0312 (5)
H9A0.86270.66870.96230.037*
H9B0.92630.59170.87660.037*
C101.1831 (3)0.7095 (2)0.84858 (15)0.0416 (6)
H10A1.21520.62220.87110.050*
H10B1.27470.76940.85370.050*
C111.1318 (3)0.6983 (2)0.74892 (15)0.0431 (6)
H11A1.22610.71010.71080.052*
H11B1.09050.60870.73820.052*
C121.0037 (3)0.7998 (2)0.72030 (14)0.0386 (6)
H12A1.01210.81330.65530.046*
H12B1.02770.88470.74940.046*
C130.8296 (3)0.7620 (2)0.74266 (13)0.0336 (5)
H13A0.80740.67770.71240.040*
H13B0.76090.82880.71460.040*
C140.6173 (3)0.6630 (2)0.84401 (15)0.0351 (5)
H14A0.56640.67410.90280.042*
H14B0.54440.69930.79880.042*
C150.6367 (3)0.5130 (2)0.82599 (18)0.0477 (6)
H15A0.69320.50000.76980.072*
H15B0.53230.47190.82230.072*
H15C0.69680.47290.87460.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0219 (9)0.0378 (9)0.0348 (9)0.0014 (8)−0.0012 (7)−0.0003 (8)
O10.0258 (8)0.0495 (9)0.0534 (9)−0.0093 (7)−0.0018 (7)−0.0064 (8)
O20.0298 (9)0.0380 (9)0.0842 (13)0.0030 (8)0.0012 (9)−0.0190 (9)
C10.0256 (11)0.0373 (11)0.0273 (10)−0.0054 (9)−0.0036 (9)−0.0018 (9)
C20.0254 (11)0.0343 (11)0.0259 (9)−0.0029 (9)−0.0007 (8)0.0007 (8)
C30.0286 (11)0.0367 (11)0.0330 (10)−0.0075 (10)−0.0013 (9)−0.0048 (9)
C40.0375 (13)0.0308 (11)0.0387 (11)−0.0019 (10)0.0035 (10)−0.0071 (9)
C50.0287 (11)0.0301 (10)0.0421 (12)−0.0003 (10)0.0040 (9)−0.0020 (9)
C60.0243 (11)0.0315 (10)0.0371 (11)−0.0044 (9)−0.0026 (9)−0.0034 (9)
C70.0247 (11)0.0311 (10)0.0229 (9)−0.0037 (9)0.0012 (8)0.0012 (8)
C80.0239 (11)0.0322 (10)0.0276 (9)−0.0013 (9)−0.0003 (8)−0.0035 (8)
C90.0294 (11)0.0303 (10)0.0338 (11)−0.0018 (9)−0.0003 (9)−0.0007 (9)
C100.0241 (12)0.0475 (13)0.0532 (14)0.0042 (10)0.0015 (10)−0.0066 (11)
C110.0361 (14)0.0462 (12)0.0470 (13)0.0007 (11)0.0124 (11)−0.0097 (11)
C120.0425 (14)0.0433 (12)0.0302 (10)−0.0039 (12)0.0068 (10)−0.0011 (9)
C130.0328 (12)0.0406 (11)0.0274 (10)−0.0005 (10)−0.0011 (9)−0.0042 (9)
C140.0271 (12)0.0391 (11)0.0390 (11)−0.0039 (10)0.0015 (10)−0.0078 (9)
C150.0402 (15)0.0392 (12)0.0637 (15)−0.0090 (11)0.0056 (12)−0.0131 (11)

Geometric parameters (Å, °)

N1—C11.347 (3)C9—H9A0.9700
N1—C101.451 (3)C9—H9B0.9700
N1—C91.466 (3)C10—C111.533 (3)
O1—C11.243 (2)C10—H10A0.9700
O2—C51.362 (3)C10—H10B0.9700
O2—H20.8200C11—C121.528 (3)
C1—C21.475 (3)C11—H11A0.9700
C2—C31.390 (3)C11—H11B0.9700
C2—C71.406 (3)C12—C131.529 (3)
C3—C41.375 (3)C12—H12A0.9700
C3—H30.9300C12—H12B0.9700
C4—C51.385 (3)C13—H13A0.9700
C4—H40.9300C13—H13B0.9700
C5—C61.387 (3)C14—C151.529 (3)
C6—C71.391 (3)C14—H14A0.9700
C6—H60.9300C14—H14B0.9700
C7—C81.532 (3)C15—H15A0.9600
C8—C91.526 (3)C15—H15B0.9600
C8—C141.541 (3)C15—H15C0.9600
C8—C131.556 (3)
C1—N1—C10119.04 (19)N1—C10—C11109.72 (18)
C1—N1—C9119.42 (17)N1—C10—H10A109.7
C10—N1—C9115.80 (16)C11—C10—H10A109.7
C5—O2—H2109.5N1—C10—H10B109.7
O1—C1—N1122.43 (19)C11—C10—H10B109.7
O1—C1—C2121.54 (18)H10A—C10—H10B108.2
N1—C1—C2115.98 (18)C12—C11—C10114.14 (17)
C3—C2—C7119.91 (19)C12—C11—H11A108.7
C3—C2—C1120.34 (18)C10—C11—H11A108.7
C7—C2—C1119.38 (17)C12—C11—H11B108.7
C4—C3—C2121.2 (2)C10—C11—H11B108.7
C4—C3—H3119.4H11A—C11—H11B107.6
C2—C3—H3119.4C11—C12—C13115.73 (18)
C3—C4—C5119.17 (18)C11—C12—H12A108.3
C3—C4—H4120.4C13—C12—H12A108.3
C5—C4—H4120.4C11—C12—H12B108.3
O2—C5—C4117.53 (18)C13—C12—H12B108.3
O2—C5—C6122.03 (19)H12A—C12—H12B107.4
C4—C5—C6120.4 (2)C12—C13—C8120.83 (17)
C5—C6—C7120.88 (19)C12—C13—H13A107.1
C5—C6—H6119.6C8—C13—H13A107.1
C7—C6—H6119.6C12—C13—H13B107.1
C6—C7—C2118.32 (17)C8—C13—H13B107.1
C6—C7—C8122.77 (18)H13A—C13—H13B106.8
C2—C7—C8118.88 (18)C15—C14—C8116.17 (18)
C9—C8—C7104.31 (15)C15—C14—H14A108.2
C9—C8—C14110.29 (16)C8—C14—H14A108.2
C7—C8—C14110.45 (16)C15—C14—H14B108.2
C9—C8—C13111.28 (17)C8—C14—H14B108.2
C7—C8—C13112.08 (17)H14A—C14—H14B107.4
C14—C8—C13108.41 (16)C14—C15—H15A109.5
N1—C9—C8110.83 (15)C14—C15—H15B109.5
N1—C9—H9A109.5H15A—C15—H15B109.5
C8—C9—H9A109.5C14—C15—H15C109.5
N1—C9—H9B109.5H15A—C15—H15C109.5
C8—C9—H9B109.5H15B—C15—H15C109.5
H9A—C9—H9B108.1
C10—N1—C1—O1−27.0 (3)C2—C7—C8—C933.5 (2)
C9—N1—C1—O1−179.22 (17)C6—C7—C8—C14−25.7 (2)
C10—N1—C1—C2150.53 (17)C2—C7—C8—C14152.04 (18)
C9—N1—C1—C2−1.7 (3)C6—C7—C8—C1395.3 (2)
O1—C1—C2—C3−23.0 (3)C2—C7—C8—C13−87.0 (2)
N1—C1—C2—C3159.45 (18)C1—N1—C9—C847.4 (2)
O1—C1—C2—C7150.1 (2)C10—N1—C9—C8−105.69 (19)
N1—C1—C2—C7−27.5 (3)C7—C8—C9—N1−59.9 (2)
C7—C2—C3—C42.2 (3)C14—C8—C9—N1−178.47 (15)
C1—C2—C3—C4175.27 (19)C13—C8—C9—N161.2 (2)
C2—C3—C4—C5−1.6 (3)C1—N1—C10—C11−94.0 (2)
C3—C4—C5—O2178.7 (2)C9—N1—C10—C1159.2 (2)
C3—C4—C5—C6−0.8 (3)N1—C10—C11—C1229.3 (3)
O2—C5—C6—C7−176.9 (2)C10—C11—C12—C13−82.8 (2)
C4—C5—C6—C72.6 (3)C11—C12—C13—C863.9 (3)
C5—C6—C7—C2−1.9 (3)C9—C8—C13—C12−39.0 (3)
C5—C6—C7—C8175.79 (18)C7—C8—C13—C1277.3 (2)
C3—C2—C7—C6−0.5 (3)C14—C8—C13—C12−160.48 (18)
C1—C2—C7—C6−173.55 (19)C9—C8—C14—C15−48.4 (3)
C3—C2—C7—C8−178.25 (17)C7—C8—C14—C15−163.21 (19)
C1—C2—C7—C88.6 (3)C13—C8—C14—C1573.6 (2)
C6—C7—C8—C9−144.15 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.922.710 (2)162

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2615).

References

  • Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconisin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xie, Q., Wang, H., Xia, Z., Lu, M., Zhang, W., Wang, X., Fu, W., Tang, Y., Sheng, W., Li, W., Zhou, W., Zhu, X., Qiu, Z. & Chen, H. (2008). J. Med. Chem. 51, 2027–2036. [PubMed]

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