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

Zou, P.; Xie, M.-H.; Wu, H.; Liu, Y.-L.; He, Y.-J.

doi:10.1107/S1600536809049721

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3223

doi:10.1107/S1600536809049721

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

Pei Zou,^a ^* Min-Hao Xie,^a Hao Wu,^a Ya-Ling Liu ^a and Yong-Jun He ^a

^aJiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
^*Correspondence e-mail: zou-pei@163.com

(Received 3 November 2009; accepted 20 November 2009; online 28 November 2009)

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 ); Lancelot et al. (1985 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₂O₂
M_r = 176.21
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.106
S = 0.97
1994 reflections
119 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H10⋯O2ⁱ	0.84	1.80	2.6338 (15)	175
C8—H8⋯O2ⁱⁱ	0.95	2.58	3.509 (2)	165
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x, y+1, z.

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

Supporting information

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

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

checkCIF report

Comment top

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].

Related literature top

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

Experimental top

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

Computing details top

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

Figures top

	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.

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

Crystal data top

C₁₁H₁₂O₂	Z = 2
M_r = 176.21	F(000) = 188
Triclinic, P1	D_x = 1.329 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.477 (2) Å	Cell parameters from 1274 reflections
b = 7.664 (2) Å	θ = 3.2–27.5°
c = 8.546 (2) Å	µ = 0.09 mm⁻¹
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 top

Rigaku SPIDER diffractometer	1994 independent reflections
Radiation source: fine-focus sealed tube	1429 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: ψ scan (North et al., 1968)	h = −9→9
T_min = 0.976, T_max = 0.989	k = −9→9
4408 measured reflections	l = −8→11

Refinement top

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)] = 0.039	Hydrogen site location: geom and difmap
wR(F²) = 0.106	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0575P)²] where P = (F_o² + 2F_c²)/3
1994 reflections	(Δ/σ)_max < 0.001
119 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₁H₁₂O₂	γ = 75.977 (10)°
M_r = 176.21	V = 440.3 (2) Å³
Triclinic, P1	Z = 2
a = 7.477 (2) Å	Mo Kα radiation
b = 7.664 (2) Å	µ = 0.09 mm⁻¹
c = 8.546 (2) Å	T = 93 K
α = 68.39 (1)°	0.27 × 0.23 × 0.12 mm
β = 80.666 (12)°

Data collection top

Rigaku SPIDER diffractometer	1994 independent reflections
Absorption correction: ψ scan (North et al., 1968)	1429 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.989	R_int = 0.026
4408 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 0.97	Δρ_max = 0.38 e Å⁻³
1994 reflections	Δρ_min = −0.17 e Å⁻³
119 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O1	0.92438 (13)	0.25317 (11)	0.46074 (12)	0.0193 (3)
H10	1.0051	0.1691	0.4343	0.029*
O2	0.81137 (13)	−0.00378 (12)	0.63071 (12)	0.0213 (3)
C1	0.49946 (18)	0.26317 (17)	0.73643 (16)	0.0151 (3)
C2	0.43087 (18)	0.09079 (18)	0.73976 (17)	0.0181 (3)
H2A	0.4896	−0.0245	0.8290	0.022*
H2B	0.4691	0.0707	0.6302	0.022*
C3	0.22129 (19)	0.11404 (19)	0.77249 (18)	0.0214 (3)
H3A	0.1617	0.2140	0.6736	0.026*
H3B	0.1849	−0.0078	0.7889	0.026*
C4	0.15578 (19)	0.17011 (19)	0.92902 (17)	0.0220 (3)
H4A	0.0212	0.1744	0.9550	0.026*
H4B	0.2199	0.0736	1.0270	0.026*
C5	0.19689 (19)	0.36544 (19)	0.89793 (18)	0.0214 (3)
H5A	0.1020	0.4652	0.8285	0.026*
H5B	0.1864	0.3847	1.0077	0.026*
C6	0.38656 (18)	0.39253 (18)	0.81011 (16)	0.0173 (3)
C7	0.4472 (2)	0.55486 (18)	0.80077 (17)	0.0198 (3)
H7	0.3701	0.6409	0.8518	0.024*
C8	0.61567 (19)	0.59422 (18)	0.71966 (17)	0.0206 (3)
H8	0.6535	0.7062	0.7141	0.025*
C9	0.72881 (19)	0.46801 (18)	0.64642 (17)	0.0182 (3)
H9	0.8449	0.4937	0.5899	0.022*
C10	0.67299 (18)	0.30349 (17)	0.65533 (16)	0.0153 (3)
C11	0.80592 (18)	0.16973 (18)	0.58206 (16)	0.0163 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0163 (5)	0.0170 (5)	0.0231 (5)	−0.0046 (4)	0.0068 (4)	−0.0076 (4)
O2	0.0205 (5)	0.0159 (5)	0.0274 (6)	−0.0060 (4)	0.0067 (4)	−0.0092 (4)
C1	0.0155 (7)	0.0148 (6)	0.0146 (6)	−0.0036 (5)	−0.0024 (5)	−0.0038 (5)
C2	0.0161 (7)	0.0184 (7)	0.0203 (7)	−0.0059 (5)	0.0016 (6)	−0.0072 (6)
C3	0.0171 (7)	0.0214 (7)	0.0264 (8)	−0.0080 (5)	0.0002 (6)	−0.0071 (6)
C4	0.0155 (7)	0.0235 (7)	0.0236 (8)	−0.0062 (6)	0.0029 (6)	−0.0047 (6)
C5	0.0167 (7)	0.0240 (7)	0.0229 (7)	−0.0035 (5)	0.0040 (6)	−0.0099 (6)
C6	0.0162 (7)	0.0182 (7)	0.0159 (7)	−0.0025 (5)	−0.0002 (5)	−0.0050 (5)
C7	0.0208 (7)	0.0171 (7)	0.0207 (7)	−0.0008 (5)	0.0002 (6)	−0.0085 (6)
C8	0.0238 (8)	0.0159 (7)	0.0244 (8)	−0.0060 (5)	−0.0015 (6)	−0.0083 (6)
C9	0.0151 (7)	0.0190 (7)	0.0191 (7)	−0.0060 (5)	0.0007 (6)	−0.0044 (5)
C10	0.0158 (7)	0.0147 (6)	0.0147 (6)	−0.0026 (5)	−0.0008 (5)	−0.0047 (5)
C11	0.0140 (7)	0.0200 (7)	0.0165 (7)	−0.0060 (5)	−0.0003 (5)	−0.0067 (5)

Geometric parameters (Å, º) top

O1—C11	1.3254 (14)	C4—H4A	0.9900
O1—H10	0.8400	C4—H4B	0.9900
O2—C11	1.2307 (15)	C5—C6	1.5166 (18)
C1—C6	1.4049 (17)	C5—H5A	0.9900
C1—C10	1.4157 (18)	C5—H5B	0.9900
C1—C2	1.5182 (17)	C6—C7	1.3956 (18)
C2—C3	1.5247 (19)	C7—C8	1.3804 (19)
C2—H2A	0.9900	C7—H7	0.9500
C2—H2B	0.9900	C8—C9	1.3859 (18)
C3—C4	1.5242 (19)	C8—H8	0.9500
C3—H3A	0.9900	C9—C10	1.3941 (18)
C3—H3B	0.9900	C9—H9	0.9500
C4—C5	1.5196 (18)	C10—C11	1.4860 (18)

C11—O1—H10	109.5	C6—C5—H5A	108.7
C6—C1—C10	117.91 (12)	C4—C5—H5A	108.7
C6—C1—C2	119.92 (12)	C6—C5—H5B	108.7
C10—C1—C2	122.13 (11)	C4—C5—H5B	108.7
C1—C2—C3	112.64 (10)	H5A—C5—H5B	107.6
C1—C2—H2A	109.1	C7—C6—C1	119.70 (12)
C3—C2—H2A	109.1	C7—C6—C5	117.82 (11)
C1—C2—H2B	109.1	C1—C6—C5	122.47 (12)
C3—C2—H2B	109.1	C8—C7—C6	122.00 (12)
H2A—C2—H2B	107.8	C8—C7—H7	119.0
C4—C3—C2	110.24 (12)	C6—C7—H7	119.0
C4—C3—H3A	109.6	C7—C8—C9	119.04 (12)
C2—C3—H3A	109.6	C7—C8—H8	120.5
C4—C3—H3B	109.6	C9—C8—H8	120.5
C2—C3—H3B	109.6	C8—C9—C10	120.29 (12)
H3A—C3—H3B	108.1	C8—C9—H9	119.9
C5—C4—C3	109.55 (11)	C10—C9—H9	119.9
C5—C4—H4A	109.8	C9—C10—C1	121.05 (11)
C3—C4—H4A	109.8	C9—C10—C11	117.19 (12)
C5—C4—H4B	109.8	C1—C10—C11	121.71 (11)
C3—C4—H4B	109.8	O2—C11—O1	122.06 (11)
H4A—C4—H4B	108.2	O2—C11—C10	124.11 (11)
C6—C5—C4	114.16 (11)	O1—C11—C10	113.80 (11)

C6—C1—C2—C3	19.10 (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—C1	1.0 (2)
C2—C3—C4—C5	64.12 (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—C7	0.30 (19)	C2—C1—C10—C9	176.64 (12)
C2—C1—C6—C7	−177.43 (12)	C6—C1—C10—C11	176.63 (12)
C10—C1—C6—C5	179.06 (12)	C2—C1—C10—C11	−5.7 (2)
C2—C1—C6—C5	1.3 (2)	C9—C10—C11—O2	151.98 (13)
C4—C5—C6—C7	−170.00 (12)	C1—C10—C11—O2	−25.8 (2)
C4—C5—C6—C1	11.22 (19)	C9—C10—C11—O1	−26.09 (18)
C1—C6—C7—C8	0.5 (2)	C1—C10—C11—O1	156.15 (12)
C5—C6—C7—C8	−178.34 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10···O2ⁱ	0.84	1.80	2.6338 (15)	175
C2—H2B···O2	0.99	2.48	2.8506 (19)	101
C8—H8···O2ⁱⁱ	0.95	2.58	3.509 (2)	165

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂O₂
M_r	176.21
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	7.477 (2), 7.664 (2), 8.546 (2)
α, β, γ (°)	68.39 (1), 80.666 (12), 75.977 (10)
V (Å³)	440.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.23 × 0.12

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.976, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4408, 1994, 1429
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 0.97
No. of reflections	1994
No. of parameters	119
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.17

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10···O2ⁱ	0.8400	1.8000	2.6338 (15)	175.00
C2—H2B···O2	0.9900	2.4800	2.8506 (19)	101.00
C8—H8···O2ⁱⁱ	0.9500	2.5800	3.509 (2)	165.00

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

Acknowledgements

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

References

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