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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 64| Part 3| March 2008| Page o631
doi:10.1107/S1600536808004868

(S)-2-(1H-Imidazol-1-yl)-3-phenyl­propanol

Zuxing Yang,a Siping Wei,a Wenhai Wang,a Hua Chena and Jingbo Lana*

aKey Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
*Correspondence e-mail: jingbolan@scu.edu.cn

(Received 22 January 2008; accepted 20 February 2008; online 27 February 2008)

In the title compound, C12H14N2O, the middle C atom in the propanol chain is a chiral center and possesses an S absolute configuration, according to the synthesis. In the crystal structure, inter­molecular O—H⋯N hydrogen bonds link the mol­ecules into a chain along the b axis.

Related literature

For related literature, see: Bao et al. (2003[Bao, W. L., Wang, Z. M. & Li, Y. X. (2003). J. Org. Chem. 68, 591-593.]); Baudequin et al. (2003[Baudequin, C., Baudoux, J., Levillain, J., Cahard, D., Gaumont, A. C. & Plaquevent, J. C. (2003). Tetrahedron Asymmetry, 14, 3081-3093.]); Lan et al. (2004[Lan, J. B., Chen, L., Yu, X. Q., You, J. S. & Xie, R. G. (2004). Chem. Commun. pp. 188-189.]); Matsuoka et al. (2006[Matsuoka, Y., Ishida, Y., Sasaki, D. & Saigo, K. (2006). Tetrahedron, 62, 8199-8206.]); Nair et al. (2004[Nair, V., Bindu, S. & Sreekumar, V. (2004). Angew. Chem. Int. Ed. 43, 5130-5135.]); Sambrook et al. (2005[Sambrook, M. R., Beer, P. D., Wisner, J. A., Paul, R. L., Cowley, A. R., Szemes, F. & Drew, M. G. B. (2005). J. Am. Chem. Soc. 127, 2292-2302.]); Wang et al. (2007[Wang, W. H., Xi, P. H., Su, X. Y., Lan, J. B., Mao, Z. H., You, J. S. & Xie, R. G. (2007). Cryst. Growth Des. 7, 741-746.]); You et al. (2001[You, J. S., Yu, X. Q., Zhang, G. L., Xiang, Q. X., Lan, J. B. & Xie, R. G. (2001). Chem. Commun. pp. 1816-1817.]).

[Scheme 1]

Experimental

Crystal data

  • C12H14N2O

  • Mr = 202.25

  • Monoclinic, P 21

  • a = 8.021 (4) Å

  • b = 6.069 (3) Å

  • c = 11.629 (5) Å

  • β = 90.13 (5)°

  • V = 566.1 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 (2) K

  • 0.40 × 0.33 × 0.23 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 1909 measured reflections

  • 1146 independent reflections

  • 826 reflections with I > 2σ(I)

  • Rint = 0.055

  • 3 standard reflections every 200 reflections intensity decay: 1.2%
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.090

  • S = 1.05

  • 1146 reflections

  • 142 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.12 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N2i 0.82 1.98 2.802 (4) 177
Symmetry code: (i) [-x+2, y+{\script{1\over 2}}, -z].

Data collection: DIFRAC (Gabe & White, 1993[Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association, Pittsburgh Meeting. Abstract PA104.]); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989[Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.]); 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004868/ez2119sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004868/ez2119Isup2.hkl

checkCIF report


Comment top

Imidazoles are an important group in biological systems, and their derivatives have attracted widespread interest due to their application as precursors for imidazolium-based ionic liquids (Baudequin et al., 2003), N-heterocyclic carbenes (Nair et al., 2004) and molecular sensors (Sambrook et al., 2005). We have focused our interest on the synthesis and applications of imidazole derivatives (Lan et al., 2004; Wang et al., 2007) and have reported several chiral cyclophanes and chiral molecular tweezers containing imidazole residues as receptors for the enantioselective recognition of amino acids or their derivatives (You et al., 2001). Here, we report the crystal structure of the title compound, (I), which is a basic unit in the construction of chiral receptors and could be applied in the preparation of chair heterocyclic carbenes and ionic liquids.

In the structure of (I), the hydroxyl group and the imidazol-1-yl nitrogen atom are hydrogen bonded via an intermolecular O—H···N hydrogen bond as illustrated in Table 1 to result in the formation of a helical chain.

Related literature top

For related literature, see: Bao et al. (2003); Baudequin et al. (2003); Lan et al. (2004); Matsuoka et al. (2006); Nair et al. (2004); Sambrook et al. (2005); Wang et al. (2007); You et al. (2001).

Experimental top

Since enantiopure amines are easily available and the chiral carbon has little risk of the racemization, they are usually applied for the preparation of chiral imidazole derivatives by cyclocondensation of ring fragments (Matsuoka et al., 2006). The methyl 2-(1H-imidazol-1-yl)-3-phenylpropanoate was easily prepared according to a literature procedure (Bao et al., 2003). Thereafter, NaBH4 (1.52 g, 40 mmol) was added to methyl 2-(1H-imidazol-1-yl)-3-phenylpropanoate (2.16 g, 10.0 mmol) in ethanol (150 ml) at 273 K over 30 min. The mixture was stirred at 333 K for another 20 h and then evaporated under vacuum. The residue was diluted with 20 ml saturated K2CO3 and extracted with 50 ml e thyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluting with CH2Cl2/CH3OH (20/1, V/V), and then recrystallized from CH2Cl2 to give colorless crystals. Yield: 86%, mp 359–361 K, 1H NMR (300 MHz, CDCl3): δ 2.94–3.17 (dd, J=13.8 Hz, 7.7 Hz, 2H), 3.78–3.88 (m, 2H), 4.13–4.29 (m, 1H.), 6.88 (m, 2H), 7.02 (m, 2H), 7.28 (s, 1H), 7.03–7.26 (m, 5H). 13C NMR (75 MHz, CDCl3): δ 38.41, 62.26, 64.21, 117.61, 126.99, 128.59, 128.76, 128.90, 136.47, 137.10 p.p.m..

Refinement top

All H atoms were positioned geometrically and refined in the riding model approximation with C—H = 0.93, 0.97 Å and O—H = 0.82 Å. Since there is no atom heavier than oxygen it was not possible to determine the absolute structure exactly. However, the chiral carbon does not directly participate in the cyclocondensation in this reaction (Matsuoka et al., 2006). Herein, the desired product (S)-2-(1H-imidazol-1-yl)-3-phenylpropanol was obtained starting from (S)-2-amino-3-phenylpropanoic acid, whose absolute configuration (S) is consistent with the starting material.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atomic numbering.
(S)-2-(1H-Imidazol-1-yl)-3-phenylpropanol top
Crystal data top
C12H14N2OF(000) = 216
Mr = 202.25Dx = 1.186 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 26 reflections
a = 8.021 (4) Åθ = 4.6–7.8°
b = 6.069 (3) ŵ = 0.08 mm−1
c = 11.629 (5) ÅT = 293 K
β = 90.13 (5)°Block, colorless
V = 566.1 (5) Å30.40 × 0.33 × 0.23 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.055
Radiation source: fine-focus sealed tubeθmax = 25.4°, θmin = 1.8°
Graphite monochromatorh = −9→0
ω/2θ scansk = −7→7
1909 measured reflectionsl = −13→14
1146 independent reflections3 standard reflections every 200 reflections
826 reflections with I > 2σ(I) intensity decay: 1.2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0335P)2 + 0.0435P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1146 reflectionsΔρmax = 0.13 e Å−3
142 parametersΔρmin = −0.12 e Å−3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.045 (8)
Crystal data top
C12H14N2OV = 566.1 (5) Å3
Mr = 202.25Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.021 (4) ŵ = 0.08 mm−1
b = 6.069 (3) ÅT = 293 K
c = 11.629 (5) Å0.40 × 0.33 × 0.23 mm
β = 90.13 (5)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.055
1909 measured reflections3 standard reflections every 200 reflections
1146 independent reflections intensity decay: 1.2%
826 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0361 restraint
wR(F2) = 0.090H-atom parameters constrained
S = 1.05Δρmax = 0.13 e Å−3
1146 reflectionsΔρmin = −0.12 e Å−3
142 parameters
Special details top

Experimental. In the crystal structure, there is not any heavy atom than silicon, so we can't get the absolute structure exactly. However, the chiral carbon does not directly participate in the cyclocondensation in this reaction (Matsuoka et al., Tetrahedron. 2006, 62, 8199–8206). From starting material (S)-2-amino-3-phenylpropanoic acid, it give (S)-2-(1H-imidazol-1-yl)-3-phenylpropanol as product, whose absolute configuration (S) is consistent with the absolute structure characterized by X-ray structure analysis.

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
xyzUiso*/Ueq
O10.6488 (3)0.9519 (5)−0.06637 (15)0.0601 (7)
H10.71781.0460−0.08350.086 (15)*
N10.8556 (3)0.8538 (4)0.13967 (17)0.0418 (6)
N21.1263 (3)0.7863 (6)0.1257 (2)0.0651 (9)
C10.7787 (4)0.7337 (7)0.4142 (2)0.0628 (10)
H1B0.83150.86930.40690.073 (4)*
C20.8278 (4)0.5915 (8)0.5001 (3)0.0747 (12)
H20.91370.63130.54970.073 (4)*
C30.7501 (5)0.3908 (7)0.5128 (3)0.0725 (12)
H30.78240.29550.57140.073 (4)*
C40.6247 (5)0.3324 (7)0.4383 (2)0.0680 (10)
H40.57160.19700.44640.073 (4)*
C50.5773 (4)0.4746 (6)0.3512 (2)0.0565 (9)
H50.49350.43240.30030.073 (4)*
C60.6522 (3)0.6781 (6)0.3385 (2)0.0456 (8)
C70.5912 (3)0.8393 (6)0.2488 (2)0.0498 (8)
H7A0.60730.98750.27800.046 (4)*
H7B0.47230.81760.23830.046 (4)*
C80.6752 (3)0.8225 (6)0.1318 (2)0.0431 (7)
H80.65500.67380.10210.040 (7)*
C90.5963 (3)0.9848 (6)0.0484 (2)0.0517 (8)
H9A0.47600.97030.05200.046 (4)*
H9B0.62481.13350.07190.046 (4)*
C100.9385 (4)1.0364 (6)0.1796 (2)0.0514 (9)
H1A0.89071.16530.20750.073 (4)*
C111.1038 (4)0.9919 (7)0.1705 (2)0.0607 (10)
H111.18921.08740.19170.073 (4)*
C120.9738 (4)0.7106 (6)0.1088 (2)0.0542 (8)
H120.95100.57200.07850.073 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0642 (15)0.0700 (16)0.0462 (11)−0.0137 (15)−0.0054 (9)0.0087 (11)
N10.0410 (12)0.0430 (15)0.0414 (11)0.0035 (14)−0.0051 (9)−0.0040 (11)
N20.0411 (16)0.088 (3)0.0659 (16)0.0082 (17)−0.0038 (12)−0.0079 (17)
C10.057 (2)0.066 (3)0.0656 (19)−0.009 (2)−0.0107 (15)0.0151 (19)
C20.065 (2)0.093 (3)0.066 (2)−0.001 (2)−0.0198 (18)0.017 (2)
C30.085 (3)0.075 (3)0.058 (2)0.016 (3)0.0044 (18)0.0208 (19)
C40.101 (3)0.050 (2)0.0522 (17)0.001 (2)0.0205 (18)0.0072 (19)
C50.074 (2)0.050 (2)0.0459 (15)−0.004 (2)0.0051 (14)−0.0072 (16)
C60.0442 (16)0.050 (2)0.0429 (15)−0.0001 (17)0.0058 (12)0.0041 (14)
C70.0440 (16)0.056 (2)0.0496 (15)0.0050 (18)−0.0027 (12)−0.0008 (16)
C80.0419 (15)0.0454 (19)0.0419 (13)0.0001 (16)−0.0061 (11)−0.0023 (14)
C90.0467 (17)0.056 (2)0.0527 (15)0.0023 (19)−0.0078 (12)0.0072 (16)
C100.0512 (19)0.051 (2)0.0519 (16)−0.0015 (18)−0.0039 (14)−0.0075 (15)
C110.0465 (19)0.081 (3)0.0544 (16)−0.007 (2)−0.0072 (13)−0.002 (2)
C120.056 (2)0.060 (2)0.0471 (15)0.012 (2)−0.0004 (13)−0.0109 (16)
Geometric parameters (Å, º) top
O1—C91.415 (3)C4—H40.9300
O1—H10.8200C5—C61.382 (5)
N1—C121.336 (4)C5—H50.9300
N1—C101.372 (4)C6—C71.511 (4)
N1—C81.462 (3)C7—C81.522 (3)
N2—C121.321 (4)C7—H7A0.9700
N2—C111.364 (5)C7—H7B0.9700
C1—C21.377 (5)C8—C91.519 (4)
C1—C61.383 (4)C8—H80.9800
C1—H1B0.9300C9—H9A0.9700
C2—C31.376 (6)C9—H9B0.9700
C2—H20.9300C10—C111.358 (4)
C3—C41.373 (5)C10—H1A0.9300
C3—H30.9300C11—H110.9300
C4—C51.384 (5)C12—H120.9300
C9—O1—H1109.5C8—C7—H7A108.4
C12—N1—C10105.8 (2)C6—C7—H7B108.4
C12—N1—C8127.0 (3)C8—C7—H7B108.4
C10—N1—C8127.2 (3)H7A—C7—H7B107.5
C12—N2—C11104.6 (3)N1—C8—C9111.5 (2)
C2—C1—C6121.1 (4)N1—C8—C7112.0 (2)
C2—C1—H1B119.4C9—C8—C7110.0 (2)
C6—C1—H1B119.4N1—C8—H8107.7
C3—C2—C1120.3 (3)C9—C8—H8107.7
C3—C2—H2119.9C7—C8—H8107.7
C1—C2—H2119.9O1—C9—C8112.7 (3)
C4—C3—C2119.5 (3)O1—C9—H9A109.0
C4—C3—H3120.3C8—C9—H9A109.0
C2—C3—H3120.3O1—C9—H9B109.0
C3—C4—C5120.1 (4)C8—C9—H9B109.0
C3—C4—H4120.0H9A—C9—H9B107.8
C5—C4—H4120.0C11—C10—N1106.6 (3)
C6—C5—C4121.1 (3)C11—C10—H1A126.7
C6—C5—H5119.4N1—C10—H1A126.7
C4—C5—H5119.4C10—C11—N2110.0 (3)
C5—C6—C1117.9 (3)C10—C11—H11125.0
C5—C6—C7120.8 (3)N2—C11—H11125.0
C1—C6—C7121.2 (3)N2—C12—N1113.0 (3)
C6—C7—C8115.5 (3)N2—C12—H12123.5
C6—C7—H7A108.4N1—C12—H12123.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.821.982.802 (4)177
Symmetry code: (i) −x+2, y+1/2, −z.

Experimental details

Crystal data
Chemical formulaC12H14N2O
Mr202.25
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)8.021 (4), 6.069 (3), 11.629 (5)
β (°) 90.13 (5)
V (Å3)566.1 (5)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.40 × 0.33 × 0.23
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		1909, 1146, 826
Rint0.055
(sin θ/λ)max (Å−1)0.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.090, 1.05
No. of reflections1146
No. of parameters142
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.13, −0.12

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.821.982.802 (4)177
Symmetry code: (i) −x+2, y+1/2, −z.
 

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (grant No. 20602027) for financial support.

References

First citationBao, W. L., Wang, Z. M. & Li, Y. X. (2003). J. Org. Chem. 68, 591–593.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBaudequin, C., Baudoux, J., Levillain, J., Cahard, D., Gaumont, A. C. & Plaquevent, J. C. (2003). Tetrahedron Asymmetry, 14, 3081–3093.  Web of Science CrossRef CAS Google Scholar
 First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
 First citationGabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationGabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association, Pittsburgh Meeting. Abstract PA104.  Google Scholar
 First citationLan, J. B., Chen, L., Yu, X. Q., You, J. S. & Xie, R. G. (2004). Chem. Commun. pp. 188–189.  Web of Science CrossRef Google Scholar
 First citationMatsuoka, Y., Ishida, Y., Sasaki, D. & Saigo, K. (2006). Tetrahedron, 62, 8199–8206.  Web of Science CrossRef CAS Google Scholar
 First citationNair, V., Bindu, S. & Sreekumar, V. (2004). Angew. Chem. Int. Ed. 43, 5130–5135.  Web of Science CrossRef CAS Google Scholar
 First citationSambrook, M. R., Beer, P. D., Wisner, J. A., Paul, R. L., Cowley, A. R., Szemes, F. & Drew, M. G. B. (2005). J. Am. Chem. Soc. 127, 2292–2302.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, W. H., Xi, P. H., Su, X. Y., Lan, J. B., Mao, Z. H., You, J. S. & Xie, R. G. (2007). Cryst. Growth Des. 7, 741–746.  Web of Science CSD CrossRef CAS Google Scholar
 First citationYou, J. S., Yu, X. Q., Zhang, G. L., Xiang, Q. X., Lan, J. B. & Xie, R. G. (2001). Chem. Commun. pp. 1816–1817.  Web of Science CrossRef Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 3| March 2008| Page o631
doi:10.1107/S1600536808004868
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