supporting information

Acta Cryst. (2013). E69, o1151    [ doi:10.1107/S160053681301636X ]


M. B. Sanders, J. C. Farrokh, J. Hardie and B. C. Chan

Abstract top

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

Comment top

Imidazole ligands have been used in coordination chemistry with great success over the last twenty years (Huff et al., 1993). These successes can be attributed to how the nitrogen in imidazole assists in the formation of metal complexes (Fujita et al., 1994). Imidazole-containing metal complexes have a variety of applications, such as redox mediators in enzyme-based electrochemical sensors (Fan et al., 2000). A few examples of imidazole complex compounds with biological applications have been reported (Bauman and Wang, 1964). Histidine, an essential amino acid, and histamine, a bioorganic compound that acts as neurotransmitter, both involve (1H-imidazol-5-yl)methanol in their respective synthesizes (Darby et al., 1942). Here we report on a new imidazole compound, the hydroxymethyl-substituted imidazole, the title compound, C4H6N2O. The bond lengths and bond angles are within normal ranges in the molecular structure of this compound (Fig. 1). The compound forms hydrogen bonds of 1.985 (8) Å between the nitrogen (N1) on the imidazole ring of one molecule and the hydrogen (H1') of the hydroxyl on an adjacent molecule (Fig. 2). Hydrogen bonding also takes place between the oxygen (O1") on the hydroxyl group of one molecule and the hydrogen (H2) bonded to a nitrogen (N2) on the imidazole ring of a corresponding molecule. This bond measures 1.921 (1) Å (Fig. 3).

Related literature top

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 top

Approximately 100 mg of the target compound was dissolved in 2 ml of a 50% methanol: 50% toluene solution. The solution was allowed to evaporate slowly for two weeks until clear, colorless crystals formed. A crystal was isolated and analyzed on a Bruker APEX II CCD single-crystal X-ray diffractometer.

Refinement top

The structure was solved using direct methods (Bruker, 2011).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); 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).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot at 50% probability.
[Figure 2] Fig. 2. The title structure is stabilized by hydrogen bonds between N1' and H1, which each measure 1.985 (8) Å. Oxygen atoms are shown in red, carbon atoms in black, hydrogen atoms in pink, and nitrogen atoms in blue.
[Figure 3] Fig. 3. Hydrogen bonding between the oxygen (O1") on the hydroxyl group of one molecule and the hydrogen (H2) bonded to a nitrogen (N2) on the imidazole ring of a corresponding molecule measures 1.921 (1) Å.
(1H-Imidazol-4-yl)methanol top
Crystal data top
C4H6N2OF(000) = 416
Mr = 98.11Dx = 1.367 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 13.9180 (9) ÅCell parameters from 189 reflections
b = 7.1980 (5) Åθ = 3.6–28.2°
c = 11.6509 (12) ŵ = 0.10 mm1
β = 125.249 (1)°T = 100 K
V = 953.20 (13) Å3Blocks, colourless
Z = 80.52 × 0.37 × 0.29 mm
Data collection top
1158 independent reflections
Radiation source: fine-focus sealed tube1086 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 8.3333 pixels mm-1θmax = 28.6°, θmin = 3.4°
ω and ϕ scansh = 1818
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
k = 99
Tmin = 0.688, Tmax = 0.746l = 1515
5389 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-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 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C4H6N2OV = 953.20 (13) Å3
Mr = 98.11Z = 8
Monoclinic, C2/cMo Kα radiation
a = 13.9180 (9) ŵ = 0.10 mm1
b = 7.1980 (5) ÅT = 100 K
c = 11.6509 (12) Å0.52 × 0.37 × 0.29 mm
β = 125.249 (1)°
Data collection top
1158 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
1086 reflections with I > 2σ(I)
Tmin = 0.688, Tmax = 0.746Rint = 0.015
5389 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.07Δρmax = 0.35 e Å3
1158 reflectionsΔρmin = 0.27 e Å3
65 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
O10.39678 (6)0.03753 (10)1.06291 (7)0.0178 (2)
N10.43471 (7)0.23365 (12)0.85046 (9)0.0176 (2)
N20.27914 (7)0.41114 (12)0.71171 (9)0.0178 (2)
C10.43706 (9)0.22305 (14)1.06767 (10)0.0189 (2)
C20.38850 (8)0.29121 (13)0.92295 (10)0.0160 (2)
C30.36594 (9)0.30971 (14)0.72413 (11)0.0178 (2)
C40.29183 (9)0.40012 (14)0.83752 (11)0.0179 (2)
Atomic displacement parameters (Å2) top
O10.0161 (4)0.0178 (4)0.0184 (4)0.0035 (3)0.0093 (3)0.0032 (3)
N10.0164 (4)0.0173 (4)0.0191 (4)0.0018 (3)0.0103 (4)0.0007 (3)
N20.0165 (4)0.0164 (4)0.0178 (4)0.0027 (3)0.0083 (3)0.0024 (3)
C10.0197 (5)0.0181 (5)0.0154 (5)0.0009 (4)0.0081 (4)0.0012 (4)
C20.0159 (5)0.0140 (4)0.0169 (5)0.0009 (3)0.0088 (4)0.0016 (3)
C30.0182 (5)0.0168 (5)0.0193 (5)0.0005 (4)0.0113 (4)0.0005 (4)
C40.0184 (5)0.0165 (5)0.0196 (5)0.0019 (4)0.0114 (4)0.0001 (4)
Geometric parameters (Å, º) top
O1—C11.4369 (12)C1—C21.4917 (13)
N1—C31.3251 (13)C1—H1B0.99
N1—C21.3877 (12)C2—C41.3674 (14)
N2—C31.3459 (13)C3—H30.95
N2—C41.3738 (13)C4—H40.95
Hydrogen-bond geometry (Å, º) top
O1—H1···N1i0.841.922.7563 (13)172
N2—H2···O1ii0.881.992.8315 (11)161
C4—H4···O1iii0.952.573.4574 (17)155
Symmetry codes: (i) x+1, y, z+2; (ii) x+1/2, y+1/2, z+2; (iii) x+1/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC4H6N2O
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)13.9180 (9), 7.1980 (5), 11.6509 (12)
β (°) 125.249 (1)
V3)953.20 (13)
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.52 × 0.37 × 0.29
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2011)
Tmin, Tmax0.688, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
5389, 1158, 1086
(sin θ/λ)max1)0.673
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.095, 1.07
No. of reflections1158
No. of parameters65
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.27

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalMaker (CrystalMaker Software, 2009), enCIFer (Allen et al. 2004).

Hydrogen-bond geometry (Å, º) top
O1—H1···N1i0.841.922.7563 (13)172
N2—H2···O1ii0.881.992.8315 (11)161
C4—H4···O1iii0.952.573.4574 (17)155
Symmetry codes: (i) x+1, y, z+2; (ii) x+1/2, y+1/2, z+2; (iii) x+1/2, y+1/2, z+3/2.
Acknowledgements top

The authors gratefully acknowledge The College of New Jersey's School of Science for research funding and the National Science Foundation for major research instrumentation grant (NSF-0922931) for diffractometer acquisition.