(1H-Imidazol-4-yl)methanol.

The title compound, C4H6N2O, displays two predominant hydrogen-bonding inter-actions in the crystal structure. The first is between the unprotonated imidazole N atom of one mol-ecule and the hy-droxy H atom of an adjacent mol-ecule. The second is between the hy-droxy O atom of one mol-ecule and the imidazole N-H group of a corresponding mol-ecule. These inter-actions lead to the formation of a two-dimnensional network parallel to (10-1). C-H⋯O inter-actions also occur.

Related literature

For background information on imidazole complex formation, see: Bauman & Wang (1964 ▶); Fan et al. (2000 ▶). For related structures, see: Nyamori et al. (2010 ▶); Albov et al. (2006 ▶). For the use of imidazole-containing compounds in coordination chemistry, see: Huff et al. (1993 ▶); Fujita et al. (1994 ▶). For the use of the title compound in the synthesis of biological compounds, see: Darby et al. (1942 ▶).

Experimental

Crystal data

C4H6N2O

M = 98.11

Monoclinic,

a = 13.9180 (9) Å

b = 7.1980 (5) Å

c = 11.6509 (12) Å

β = 125.249 (1)°

V = 953.20 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.52 × 0.37 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.688, T max = 0.746

5389 measured reflections

1158 independent reflections

1086 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.095

S = 1.07

1158 reflections

65 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (CrystalMaker Software, 2009 ▶); software used to prepare material for publication: enCIFer (Allen et al. 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301636X/fj2622sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301636X/fj2622Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301636X/fj2622Isup3.cml

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

C4H6N2O	F(000) = 416
Mr = 98.11	Dx = 1.367 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.9180 (9) Å	Cell parameters from 189 reflections
b = 7.1980 (5) Å	θ = 3.6–28.2°
c = 11.6509 (12) Å	µ = 0.10 mm−1
β = 125.249 (1)°	T = 100 K
V = 953.20 (13) Å3	Blocks, colourless
Z = 8	0.52 × 0.37 × 0.29 mm

Bruker APEXII CCD diffractometer	1158 independent reflections
Radiation source: fine-focus sealed tube	1086 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.3333 pixels mm-1	θmax = 28.6°, θmin = 3.4°
ω and φ scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2011)	k = −9→9
Tmin = 0.688, Tmax = 0.746	l = −15→15
5389 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.6749P] where P = (Fo2 + 2Fc2)/3
1158 reflections	(Δ/σ)max = 0.002
65 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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	0.39678 (6)	0.03753 (10)	1.06291 (7)	0.0178 (2)
H1	0.4528	−0.0374	1.093	0.027*
N1	0.43471 (7)	0.23365 (12)	0.85046 (9)	0.0176 (2)
N2	0.27914 (7)	0.41114 (12)	0.71171 (9)	0.0178 (2)
H2	0.2243	0.4731	0.6368	0.021*
C1	0.43706 (9)	0.22305 (14)	1.06767 (10)	0.0189 (2)
H1A	0.5241	0.2245	1.1246	0.023*
H1B	0.4118	0.3067	1.113	0.023*
C2	0.38850 (8)	0.29121 (13)	0.92295 (10)	0.0160 (2)
C3	0.36594 (9)	0.30971 (14)	0.72413 (11)	0.0178 (2)
H3	0.3766	0.2945	0.6512	0.021*
C4	0.29183 (9)	0.40012 (14)	0.83752 (11)	0.0179 (2)
H4	0.2433	0.4567	0.8605	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0161 (4)	0.0178 (4)	0.0184 (4)	0.0035 (3)	0.0093 (3)	0.0032 (3)
N1	0.0164 (4)	0.0173 (4)	0.0191 (4)	0.0018 (3)	0.0103 (4)	0.0007 (3)
N2	0.0165 (4)	0.0164 (4)	0.0178 (4)	0.0027 (3)	0.0083 (3)	0.0024 (3)
C1	0.0197 (5)	0.0181 (5)	0.0154 (5)	0.0009 (4)	0.0081 (4)	−0.0012 (4)
C2	0.0159 (5)	0.0140 (4)	0.0169 (5)	−0.0009 (3)	0.0088 (4)	−0.0016 (3)
C3	0.0182 (5)	0.0168 (5)	0.0193 (5)	0.0005 (4)	0.0113 (4)	0.0005 (4)
C4	0.0184 (5)	0.0165 (5)	0.0196 (5)	0.0019 (4)	0.0114 (4)	−0.0001 (4)

O1—C1	1.4369 (12)	C1—C2	1.4917 (13)
O1—H1	0.84	C1—H1A	0.99
N1—C3	1.3251 (13)	C1—H1B	0.99
N1—C2	1.3877 (12)	C2—C4	1.3674 (14)
N2—C3	1.3459 (13)	C3—H3	0.95
N2—C4	1.3738 (13)	C4—H4	0.95
N2—H2	0.88
C1—O1—H1		H1A—C1—H1B
C3—N1—C2		C4—C2—N1
C3—N2—C4		C4—C2—C1
C3—N2—H2		N1—C2—C1
C4—N2—H2		N1—C3—N2
O1—C1—C2		N1—C3—H3
O1—C1—H1A		N2—C3—H3
C2—C1—H1A		C2—C4—N2
O1—C1—H1B		C2—C4—H4
C2—C1—H1B		N2—C4—H4

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.84	1.92	2.7563 (13)	172
N2—H2···O1ii	0.88	1.99	2.8315 (11)	161
C4—H4···O1iii	0.95	2.57	3.4574 (17)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.84	1.92	2.7563 (13)	172
N2—H2⋯O1ii	0.88	1.99	2.8315 (11)	161
C4—H4⋯O1iii	0.95	2.57	3.4574 (17)	155

Symmetry codes: (i) ; (ii) ; (iii) .