rac-(S)-2-(1H-Imidazol-1-yl)-3-methyl-butan-1-ol.

In the crystal structure of the title compound, C(8)H(14)N(2)O, inter-molecular O-H⋯N hydrogen bonds link mol-ecules related by translation along the a axis into chains. Weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions enhance the crystal packing stability.

Related literature

For useful applications of imidazole derivatives, see Lu et al. (2006 ▶); Zou et al. (2006 ▶). For details of the synthesis, see Bao et al. (2003 ▶); Guo et al. (2006 ▶).

Experimental

Crystal data

C8H14N2O

M = 154.21

Monoclinic,

a = 7.356 (4) Å

b = 7.212 (3) Å

c = 16.549 (5) Å

β = 90.54 (3)°

V = 877.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 292 K

0.58 × 0.54 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

1931 measured reflections

1630 independent reflections

965 reflections with I > 2σ(I)

R int = 0.004

3 standard reflections every 120 reflections intensity decay: 0.3%

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.197

S = 1.18

1630 reflections

104 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004565/cv2517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004565/cv2517Isup2.hkl

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

C8H14N2O	F(000) = 336
Mr = 154.21	Dx = 1.167 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 21 reflections
a = 7.356 (4) Å	θ = 4.6–7.4°
b = 7.212 (3) Å	µ = 0.08 mm−1
c = 16.549 (5) Å	T = 292 K
β = 90.54 (3)°	Block, colourless
V = 877.9 (7) Å3	0.58 × 0.54 × 0.42 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.004
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.5°
graphite	h = −8→8
ω/2θ scans	k = 0→8
1931 measured reflections	l = −7→20
1630 independent reflections	3 standard reflections every 120 reflections
965 reflections with I > 2σ(I)	intensity decay: 0.3%

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.197	w = 1/[σ2(Fo2) + (0.0941P)2] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max < 0.001
1630 reflections	Δρmax = 0.31 e Å−3
104 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.046 (11)

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	0.4065 (2)	0.1870 (3)	0.31165 (14)	0.0557 (7)
H1	0.3011	0.1697	0.3255	0.084*
N1	0.7629 (3)	0.0340 (3)	0.34211 (14)	0.0459 (7)
N2	1.0479 (3)	0.1263 (4)	0.34916 (16)	0.0598 (8)
C4	0.6043 (3)	−0.0816 (4)	0.32307 (17)	0.0456 (8)
H4	0.6473	−0.1848	0.2898	0.055*
C5	0.4713 (4)	0.0284 (4)	0.27157 (18)	0.0480 (8)
H5A	0.5306	0.0660	0.2221	0.058*
H5B	0.3692	−0.0503	0.2570	0.058*
C1	0.9353 (4)	0.0047 (4)	0.31778 (19)	0.0514 (8)
H1A	0.9698	−0.0901	0.2830	0.062*
C3	0.7676 (4)	0.1855 (4)	0.39170 (18)	0.0559 (8)
H3	0.6696	0.2406	0.4174	0.067*
C6	0.5261 (4)	−0.1657 (4)	0.39954 (16)	0.0487 (8)
H6	0.4769	−0.0643	0.4322	0.058*
C2	0.9438 (4)	0.2392 (4)	0.3958 (2)	0.0597 (9)
H2	0.9875	0.3387	0.4260	0.072*
C7	0.3712 (5)	−0.2990 (5)	0.3805 (2)	0.0693 (10)
H7A	0.4164	−0.4013	0.3495	0.104*
H7B	0.2786	−0.2355	0.3500	0.104*
H7C	0.3208	−0.3444	0.4300	0.104*
C8	0.6711 (5)	−0.2629 (5)	0.4495 (2)	0.0761 (11)
H8A	0.6199	−0.3035	0.4996	0.114*
H8B	0.7693	−0.1786	0.4602	0.114*
H8C	0.7157	−0.3681	0.4202	0.114*

	U11	U22	U33	U12	U13	U23
O1	0.0302 (11)	0.0505 (12)	0.0864 (15)	0.0012 (9)	−0.0025 (10)	−0.0011 (11)
N1	0.0288 (13)	0.0493 (13)	0.0595 (15)	0.0029 (11)	−0.0026 (10)	−0.0055 (11)
N2	0.0307 (14)	0.0628 (16)	0.086 (2)	−0.0005 (12)	−0.0039 (13)	−0.0031 (14)
C4	0.0325 (15)	0.0424 (15)	0.0617 (18)	−0.0002 (12)	−0.0060 (13)	−0.0027 (14)
C5	0.0355 (16)	0.0499 (16)	0.0586 (17)	−0.0024 (13)	−0.0038 (13)	−0.0008 (14)
C1	0.0334 (16)	0.0518 (17)	0.069 (2)	0.0086 (14)	0.0035 (14)	−0.0014 (14)
C3	0.0353 (16)	0.0655 (19)	0.0669 (19)	0.0006 (15)	−0.0020 (14)	−0.0129 (16)
C6	0.0407 (16)	0.0520 (17)	0.0532 (17)	0.0002 (14)	−0.0043 (13)	0.0040 (14)
C2	0.0405 (17)	0.0628 (19)	0.075 (2)	−0.0027 (15)	−0.0125 (15)	−0.0133 (16)
C7	0.066 (2)	0.071 (2)	0.071 (2)	−0.0228 (19)	0.0010 (17)	0.0087 (18)
C8	0.063 (2)	0.085 (2)	0.081 (2)	0.0034 (19)	−0.0120 (19)	0.025 (2)

O1—C5	1.408 (3)	C3—C2	1.354 (4)
O1—H1	0.8200	C3—H3	0.9300
N1—C1	1.351 (4)	C6—C8	1.515 (4)
N1—C3	1.367 (3)	C6—C7	1.522 (4)
N1—C4	1.466 (3)	C6—H6	0.9800
N2—C1	1.310 (3)	C2—H2	0.9300
N2—C2	1.362 (4)	C7—H7A	0.9600
C4—C5	1.516 (3)	C7—H7B	0.9600
C4—C6	1.521 (4)	C7—H7C	0.9600
C4—H4	0.9800	C8—H8A	0.9600
C5—H5A	0.9700	C8—H8B	0.9600
C5—H5B	0.9700	C8—H8C	0.9600
C1—H1A	0.9300
C5—O1—H1	109.5	N1—C3—H3	126.9
C1—N1—C3	106.6 (2)	C8—C6—C4	111.6 (2)
C1—N1—C4	126.5 (2)	C8—C6—C7	110.0 (3)
C3—N1—C4	126.8 (2)	C4—C6—C7	111.6 (2)
C1—N2—C2	105.6 (2)	C8—C6—H6	107.8
N1—C4—C5	109.4 (2)	C4—C6—H6	107.8
N1—C4—C6	110.8 (2)	C7—C6—H6	107.8
C5—C4—C6	115.4 (2)	C3—C2—N2	110.1 (3)
N1—C4—H4	107.0	C3—C2—H2	125.0
C5—C4—H4	107.0	N2—C2—H2	125.0
C6—C4—H4	107.0	C6—C7—H7A	109.5
O1—C5—C4	112.3 (2)	C6—C7—H7B	109.5
O1—C5—H5A	109.1	H7A—C7—H7B	109.5
C4—C5—H5A	109.1	C6—C7—H7C	109.5
O1—C5—H5B	109.1	H7A—C7—H7C	109.5
C4—C5—H5B	109.1	H7B—C7—H7C	109.5
H5A—C5—H5B	107.9	C6—C8—H8A	109.5
N2—C1—N1	111.6 (3)	C6—C8—H8B	109.5
N2—C1—H1A	124.2	H8A—C8—H8B	109.5
N1—C1—H1A	124.2	C6—C8—H8C	109.5
C2—C3—N1	106.1 (3)	H8A—C8—H8C	109.5
C2—C3—H3	126.9	H8B—C8—H8C	109.5
C1—N1—C4—C5	−115.0 (3)	C1—N1—C3—C2	−0.8 (3)
C3—N1—C4—C5	69.3 (3)	C4—N1—C3—C2	175.7 (2)
C1—N1—C4—C6	116.8 (3)	N1—C4—C6—C8	−51.7 (3)
C3—N1—C4—C6	−59.0 (3)	C5—C4—C6—C8	−176.6 (2)
N1—C4—C5—O1	−61.5 (3)	N1—C4—C6—C7	−175.2 (2)
C6—C4—C5—O1	64.2 (3)	C5—C4—C6—C7	59.9 (3)
C2—N2—C1—N1	0.0 (3)	N1—C3—C2—N2	0.8 (4)
C3—N1—C1—N2	0.5 (3)	C1—N2—C2—C3	−0.5 (4)
C4—N1—C1—N2	−175.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.82	1.93	2.751 (3)	176
C1—H1A···O1ii	0.93	2.43	3.353 (4)	173
C4—H4···Cgii	0.98	2.86	3.716 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.82	1.93	2.751 (3)	176
C1—H1A⋯O1ii	0.93	2.43	3.353 (4)	173
C4—H4⋯Cgii	0.98	2.86	3.716 (4)	146

Symmetry codes: (i) ; (ii) . Cg is the centroid of the C1–C3/N1/N2 ring.