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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3223.
Published online 2009 November 28. doi:  10.1107/S1600536809049721
PMCID: PMC2971897

5,6,7,8-Tetra­hydro­naphthalene-1-carboxylic acid

Abstract

In the mol­ecule of the title compound, C11H12O2, the cyclo­hexane ring adopts a half-chair conformation. In the crystal structure, mol­ecules are linked into centrosymmetric dimers by pairs of O—H(...)O hydrogen bonds, and the dimers are linked together by π–π inter­actions [centroid–centroid distance = 3.8310 (13) Å] and C—H(...)O bonds.

Related literature

The title compoundis an inter­mediate in the synthesis of Palonosetron, a 5-HT3 receptor antagonist, see: Kowalczyk & Dvorak (1996 [triangle]); Lancelot et al. (1985 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o3223-scheme1.jpg

Experimental

Crystal data

  • C11H12O2
  • M r = 176.21
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3223-efi1.jpg
  • a = 7.477 (2) Å
  • b = 7.664 (2) Å
  • c = 8.546 (2) Å
  • α = 68.390 (10)°
  • β = 80.666 (12)°
  • γ = 75.977 (10)°
  • V = 440.3 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 93 K
  • 0.27 × 0.23 × 0.12 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.976, T max = 0.989
  • 4408 measured reflections
  • 1994 independent reflections
  • 1429 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.106
  • S = 0.97
  • 1994 reflections
  • 119 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049721/fk2006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049721/fk2006Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from Jiangsu Institute of Nuclear Medicine.

supplementary crystallographic information

Comment

The title compound, (I), is useful as an intermediate in the synthesis of Palonosetron, a 5-HT3 receptor antagonists (Kowalczyk et al., 1996; Lancelot et al., 1985). We report here the crystal structure of (I), which is of interest to us in the field. The molecular structure is shown in Fig.1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The cyclohexane ring adopts a half chair conformation, with C3 lying out of the plane of the molecule by approximately 0.5 Å. In the crystal structure, intermolecular O—H···O hydrogen bonds (Tab. 1) link the molecules into centrosymmetric dimers(Fig. 2). Stacking of these dimers follows the π-π interactions, with the centroid-centroid distance of 3.8310 (13)Å [symmetry code(i): 1 - x, 1 - y, 1 - z].

Experimental

A sample of commercial 5,6,7,8-Tetrahydronaphthalene-1-carboxylic acid (Aldrich) was crystalized by slow evaporation of a solution in methanol.

Refinement

Positional parameters of all the H atoms bonded to C atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, with C—H=0.95 and 0.99 Å for aromatic and methylene and with Uiso(H) = 1.2Ueq(aromatic,methylene) parent atoms. H atom of the carboxyl group was derived from Fourier map, and constrained to ride on the parent atom with O—H=0.84 Å and Uiso(H)=1.5Ueq(O).

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 50% probability level.
Fig. 2.
A packing diagram viewed along the a axis. Hydrogen bridging bonds are drawn as dashed lines.

Crystal data

C11H12O2Z = 2
Mr = 176.21F(000) = 188
Triclinic, P1Dx = 1.329 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.477 (2) ÅCell parameters from 1274 reflections
b = 7.664 (2) Åθ = 3.2–27.5°
c = 8.546 (2) ŵ = 0.09 mm1
α = 68.39 (1)°T = 93 K
β = 80.666 (12)°Block, colorless
γ = 75.977 (10)°0.27 × 0.23 × 0.12 mm
V = 440.3 (2) Å3

Data collection

Rigaku SPIDER diffractometer1994 independent reflections
Radiation source: fine-focus sealed tube1429 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: ψ scan (North et al., 1968)h = −9→9
Tmin = 0.976, Tmax = 0.989k = −9→9
4408 measured reflectionsl = −8→11

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)] = 0.039Hydrogen site location: geom and difmap
wR(F2) = 0.106H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0575P)2] where P = (Fo2 + 2Fc2)/3
1994 reflections(Δ/σ)max < 0.001
119 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.17 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
O10.92438 (13)0.25317 (11)0.46074 (12)0.0193 (3)
H101.00510.16910.43430.029*
O20.81137 (13)−0.00378 (12)0.63071 (12)0.0213 (3)
C10.49946 (18)0.26317 (17)0.73643 (16)0.0151 (3)
C20.43087 (18)0.09079 (18)0.73976 (17)0.0181 (3)
H2A0.4896−0.02450.82900.022*
H2B0.46910.07070.63020.022*
C30.22129 (19)0.11404 (19)0.77249 (18)0.0214 (3)
H3A0.16170.21400.67360.026*
H3B0.1849−0.00780.78890.026*
C40.15578 (19)0.17011 (19)0.92902 (17)0.0220 (3)
H4A0.02120.17440.95500.026*
H4B0.21990.07361.02700.026*
C50.19689 (19)0.36544 (19)0.89793 (18)0.0214 (3)
H5A0.10200.46520.82850.026*
H5B0.18640.38471.00770.026*
C60.38656 (18)0.39253 (18)0.81011 (16)0.0173 (3)
C70.4472 (2)0.55486 (18)0.80077 (17)0.0198 (3)
H70.37010.64090.85180.024*
C80.61567 (19)0.59422 (18)0.71966 (17)0.0206 (3)
H80.65350.70620.71410.025*
C90.72881 (19)0.46801 (18)0.64642 (17)0.0182 (3)
H90.84490.49370.58990.022*
C100.67299 (18)0.30349 (17)0.65533 (16)0.0153 (3)
C110.80592 (18)0.16973 (18)0.58206 (16)0.0163 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0163 (5)0.0170 (5)0.0231 (5)−0.0046 (4)0.0068 (4)−0.0076 (4)
O20.0205 (5)0.0159 (5)0.0274 (6)−0.0060 (4)0.0067 (4)−0.0092 (4)
C10.0155 (7)0.0148 (6)0.0146 (6)−0.0036 (5)−0.0024 (5)−0.0038 (5)
C20.0161 (7)0.0184 (7)0.0203 (7)−0.0059 (5)0.0016 (6)−0.0072 (6)
C30.0171 (7)0.0214 (7)0.0264 (8)−0.0080 (5)0.0002 (6)−0.0071 (6)
C40.0155 (7)0.0235 (7)0.0236 (8)−0.0062 (6)0.0029 (6)−0.0047 (6)
C50.0167 (7)0.0240 (7)0.0229 (7)−0.0035 (5)0.0040 (6)−0.0099 (6)
C60.0162 (7)0.0182 (7)0.0159 (7)−0.0025 (5)−0.0002 (5)−0.0050 (5)
C70.0208 (7)0.0171 (7)0.0207 (7)−0.0008 (5)0.0002 (6)−0.0085 (6)
C80.0238 (8)0.0159 (7)0.0244 (8)−0.0060 (5)−0.0015 (6)−0.0083 (6)
C90.0151 (7)0.0190 (7)0.0191 (7)−0.0060 (5)0.0007 (6)−0.0044 (5)
C100.0158 (7)0.0147 (6)0.0147 (6)−0.0026 (5)−0.0008 (5)−0.0047 (5)
C110.0140 (7)0.0200 (7)0.0165 (7)−0.0060 (5)−0.0003 (5)−0.0067 (5)

Geometric parameters (Å, °)

O1—C111.3254 (14)C4—H4A0.9900
O1—H100.8400C4—H4B0.9900
O2—C111.2307 (15)C5—C61.5166 (18)
C1—C61.4049 (17)C5—H5A0.9900
C1—C101.4157 (18)C5—H5B0.9900
C1—C21.5182 (17)C6—C71.3956 (18)
C2—C31.5247 (19)C7—C81.3804 (19)
C2—H2A0.9900C7—H70.9500
C2—H2B0.9900C8—C91.3859 (18)
C3—C41.5242 (19)C8—H80.9500
C3—H3A0.9900C9—C101.3941 (18)
C3—H3B0.9900C9—H90.9500
C4—C51.5196 (18)C10—C111.4860 (18)
C11—O1—H10109.5C6—C5—H5A108.7
C6—C1—C10117.91 (12)C4—C5—H5A108.7
C6—C1—C2119.92 (12)C6—C5—H5B108.7
C10—C1—C2122.13 (11)C4—C5—H5B108.7
C1—C2—C3112.64 (10)H5A—C5—H5B107.6
C1—C2—H2A109.1C7—C6—C1119.70 (12)
C3—C2—H2A109.1C7—C6—C5117.82 (11)
C1—C2—H2B109.1C1—C6—C5122.47 (12)
C3—C2—H2B109.1C8—C7—C6122.00 (12)
H2A—C2—H2B107.8C8—C7—H7119.0
C4—C3—C2110.24 (12)C6—C7—H7119.0
C4—C3—H3A109.6C7—C8—C9119.04 (12)
C2—C3—H3A109.6C7—C8—H8120.5
C4—C3—H3B109.6C9—C8—H8120.5
C2—C3—H3B109.6C8—C9—C10120.29 (12)
H3A—C3—H3B108.1C8—C9—H9119.9
C5—C4—C3109.55 (11)C10—C9—H9119.9
C5—C4—H4A109.8C9—C10—C1121.05 (11)
C3—C4—H4A109.8C9—C10—C11117.19 (12)
C5—C4—H4B109.8C1—C10—C11121.71 (11)
C3—C4—H4B109.8O2—C11—O1122.06 (11)
H4A—C4—H4B108.2O2—C11—C10124.11 (11)
C6—C5—C4114.16 (11)O1—C11—C10113.80 (11)
C6—C1—C2—C319.10 (17)C6—C7—C8—C9−0.5 (2)
C10—C1—C2—C3−158.53 (13)C7—C8—C9—C10−0.2 (2)
C1—C2—C3—C4−51.66 (15)C8—C9—C10—C11.0 (2)
C2—C3—C4—C564.12 (14)C8—C9—C10—C11−176.76 (12)
C3—C4—C5—C6−43.06 (16)C6—C1—C10—C9−1.0 (2)
C10—C1—C6—C70.30 (19)C2—C1—C10—C9176.64 (12)
C2—C1—C6—C7−177.43 (12)C6—C1—C10—C11176.63 (12)
C10—C1—C6—C5179.06 (12)C2—C1—C10—C11−5.7 (2)
C2—C1—C6—C51.3 (2)C9—C10—C11—O2151.98 (13)
C4—C5—C6—C7−170.00 (12)C1—C10—C11—O2−25.8 (2)
C4—C5—C6—C111.22 (19)C9—C10—C11—O1−26.09 (18)
C1—C6—C7—C80.5 (2)C1—C10—C11—O1156.15 (12)
C5—C6—C7—C8−178.34 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H10···O2i0.841.802.6338 (15)175
C2—H2B···O20.992.482.8506 (19)101
C8—H8···O2ii0.952.583.509 (2)165

Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2006).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Kowalczyk, B. A. & Dvorak, C. A. (1996). Synthesis, 7, 816–818.
  • Lancelot, J. C., Rault, S., Laduree, D. & Robba, M. (1985). Chem. Pharm. Bull. 37, 2798–2802.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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