(S)-2-(1H-Imidazol-1-yl)-3-phenyl-propanol.

In the title compound, C(12)H(14)N(2)O, 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, inter-molecular O-H⋯N hydrogen bonds link the mol-ecules into a chain along the b axis.

Related literature

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

Crystal data

C12H14N2O

M = 202.25

Monoclinic,

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)

R int = 0.055

3 standard reflections every 200 reflections intensity decay: 1.2%

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 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

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; 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 and PLATON (Spek, 2003 ▶).

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

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

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

C12H14N2O	F000 = 216
Mr = 202.25	Dx = 1.186 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 26 reflections
a = 8.021 (4) Å	θ = 4.6–7.8º
b = 6.069 (3) Å	µ = 0.08 mm−1
c = 11.629 (5) Å	T = 293 (2) K
β = 90.13 (5)º	Block, colorless
V = 566.1 (5) Å3	0.40 × 0.33 × 0.23 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	Rint = 0.055
Radiation source: fine-focus sealed tube	θmax = 25.4º
Monochromator: graphite	θmin = 1.8º
T = 293(2) K	h = −9→0
ω/2θ scans	k = −7→7
Absorption correction: none	l = −13→14
1909 measured reflections	3 standard reflections
1146 independent reflections	every 200 reflections
826 reflections with I > 2σ(I)	intensity decay: 1.2%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-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 reflections	Δρmax = 0.13 e Å−3
142 parameters	Δρmin = −0.12 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (8)

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.

	x	y	z	Uiso*/Ueq
O1	0.6488 (3)	0.9519 (5)	−0.06637 (15)	0.0601 (7)
H1	0.7178	1.0460	−0.0835	0.086 (15)*
N1	0.8556 (3)	0.8538 (4)	0.13967 (17)	0.0418 (6)
N2	1.1263 (3)	0.7863 (6)	0.1257 (2)	0.0651 (9)
C1	0.7787 (4)	0.7337 (7)	0.4142 (2)	0.0628 (10)
H1B	0.8315	0.8693	0.4069	0.073 (4)*
C2	0.8278 (4)	0.5915 (8)	0.5001 (3)	0.0747 (12)
H2	0.9137	0.6313	0.5497	0.073 (4)*
C3	0.7501 (5)	0.3908 (7)	0.5128 (3)	0.0725 (12)
H3	0.7824	0.2955	0.5714	0.073 (4)*
C4	0.6247 (5)	0.3324 (7)	0.4383 (2)	0.0680 (10)
H4	0.5716	0.1970	0.4464	0.073 (4)*
C5	0.5773 (4)	0.4746 (6)	0.3512 (2)	0.0565 (9)
H5	0.4935	0.4324	0.3003	0.073 (4)*
C6	0.6522 (3)	0.6781 (6)	0.3385 (2)	0.0456 (8)
C7	0.5912 (3)	0.8393 (6)	0.2488 (2)	0.0498 (8)
H7A	0.6073	0.9875	0.2780	0.046 (4)*
H7B	0.4723	0.8176	0.2383	0.046 (4)*
C8	0.6752 (3)	0.8225 (6)	0.1318 (2)	0.0431 (7)
H8	0.6550	0.6738	0.1021	0.040 (7)*
C9	0.5963 (3)	0.9848 (6)	0.0484 (2)	0.0517 (8)
H9A	0.4760	0.9703	0.0520	0.046 (4)*
H9B	0.6248	1.1335	0.0719	0.046 (4)*
C10	0.9385 (4)	1.0364 (6)	0.1796 (2)	0.0514 (9)
H1A	0.8907	1.1653	0.2075	0.073 (4)*
C11	1.1038 (4)	0.9919 (7)	0.1705 (2)	0.0607 (10)
H11	1.1892	1.0874	0.1917	0.073 (4)*
C12	0.9738 (4)	0.7106 (6)	0.1088 (2)	0.0542 (8)
H12	0.9510	0.5720	0.0785	0.073 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0642 (15)	0.0700 (16)	0.0462 (11)	−0.0137 (15)	−0.0054 (9)	0.0087 (11)
N1	0.0410 (12)	0.0430 (15)	0.0414 (11)	0.0035 (14)	−0.0051 (9)	−0.0040 (11)
N2	0.0411 (16)	0.088 (3)	0.0659 (16)	0.0082 (17)	−0.0038 (12)	−0.0079 (17)
C1	0.057 (2)	0.066 (3)	0.0656 (19)	−0.009 (2)	−0.0107 (15)	0.0151 (19)
C2	0.065 (2)	0.093 (3)	0.066 (2)	−0.001 (2)	−0.0198 (18)	0.017 (2)
C3	0.085 (3)	0.075 (3)	0.058 (2)	0.016 (3)	0.0044 (18)	0.0208 (19)
C4	0.101 (3)	0.050 (2)	0.0522 (17)	0.001 (2)	0.0205 (18)	0.0072 (19)
C5	0.074 (2)	0.050 (2)	0.0459 (15)	−0.004 (2)	0.0051 (14)	−0.0072 (16)
C6	0.0442 (16)	0.050 (2)	0.0429 (15)	−0.0001 (17)	0.0058 (12)	0.0041 (14)
C7	0.0440 (16)	0.056 (2)	0.0496 (15)	0.0050 (18)	−0.0027 (12)	−0.0008 (16)
C8	0.0419 (15)	0.0454 (19)	0.0419 (13)	0.0001 (16)	−0.0061 (11)	−0.0023 (14)
C9	0.0467 (17)	0.056 (2)	0.0527 (15)	0.0023 (19)	−0.0078 (12)	0.0072 (16)
C10	0.0512 (19)	0.051 (2)	0.0519 (16)	−0.0015 (18)	−0.0039 (14)	−0.0075 (15)
C11	0.0465 (19)	0.081 (3)	0.0544 (16)	−0.007 (2)	−0.0072 (13)	−0.002 (2)
C12	0.056 (2)	0.060 (2)	0.0471 (15)	0.012 (2)	−0.0004 (13)	−0.0109 (16)

O1—C9	1.415 (3)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.382 (5)
N1—C12	1.336 (4)	C5—H5	0.9300
N1—C10	1.372 (4)	C6—C7	1.511 (4)
N1—C8	1.462 (3)	C7—C8	1.522 (3)
N2—C12	1.321 (4)	C7—H7A	0.9700
N2—C11	1.364 (5)	C7—H7B	0.9700
C1—C2	1.377 (5)	C8—C9	1.519 (4)
C1—C6	1.383 (4)	C8—H8	0.9800
C1—H1B	0.9300	C9—H9A	0.9700
C2—C3	1.376 (6)	C9—H9B	0.9700
C2—H2	0.9300	C10—C11	1.358 (4)
C3—C4	1.373 (5)	C10—H1A	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.384 (5)	C12—H12	0.9300
C9—O1—H1	109.5	C8—C7—H7A	108.4
C12—N1—C10	105.8 (2)	C6—C7—H7B	108.4
C12—N1—C8	127.0 (3)	C8—C7—H7B	108.4
C10—N1—C8	127.2 (3)	H7A—C7—H7B	107.5
C12—N2—C11	104.6 (3)	N1—C8—C9	111.5 (2)
C2—C1—C6	121.1 (4)	N1—C8—C7	112.0 (2)
C2—C1—H1B	119.4	C9—C8—C7	110.0 (2)
C6—C1—H1B	119.4	N1—C8—H8	107.7
C3—C2—C1	120.3 (3)	C9—C8—H8	107.7
C3—C2—H2	119.9	C7—C8—H8	107.7
C1—C2—H2	119.9	O1—C9—C8	112.7 (3)
C4—C3—C2	119.5 (3)	O1—C9—H9A	109.0
C4—C3—H3	120.3	C8—C9—H9A	109.0
C2—C3—H3	120.3	O1—C9—H9B	109.0
C3—C4—C5	120.1 (4)	C8—C9—H9B	109.0
C3—C4—H4	120.0	H9A—C9—H9B	107.8
C5—C4—H4	120.0	C11—C10—N1	106.6 (3)
C6—C5—C4	121.1 (3)	C11—C10—H1A	126.7
C6—C5—H5	119.4	N1—C10—H1A	126.7
C4—C5—H5	119.4	C10—C11—N2	110.0 (3)
C5—C6—C1	117.9 (3)	C10—C11—H11	125.0
C5—C6—C7	120.8 (3)	N2—C11—H11	125.0
C1—C6—C7	121.2 (3)	N2—C12—N1	113.0 (3)
C6—C7—C8	115.5 (3)	N2—C12—H12	123.5
C6—C7—H7A	108.4	N1—C12—H12	123.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.82	1.98	2.802 (4)	177

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) .