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Volume 69 
Part 7 
Page o1151  
July 2013  

Received 5 March 2013
Accepted 12 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.095
Data-to-parameter ratio = 17.8
Details
Open access

(1H-Imidazol-4-yl)methanol

aDepartment of Chemistry, The College of New Jersey, 2000 Pennington Rd, Ewing, NJ 08628, USA
Correspondence e-mail: chan@tcnj.edu

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.

Related literature

For background information on imidazole complex formation, see: Bauman & Wang (1964[Bauman, J. & Wang, J. (1964). Inorg. Chem. 3, 368-373.]); Fan et al. (2000[Fan, C., Li, G., Zhu, D. & Xhu, J. (2000). Chin. J. Chem. 18, 115-117.]). For related structures, see: Nyamori et al. (2010[Nyamori, V. O., Bala, M. D. & Levendis, D. C. (2010). Acta Cryst. E66, m412.]); Albov et al. (2006[Albov, D. V., Rybakov, V. B., Babaev, E. V. & Tsisevich, A. A. (2006). Acta Cryst. E62, o963-o965.]). For the use of imidazole-containing compounds in coordination chemistry, see: Huff et al. (1993[Huff, A., Chang, C., Cooper, D., Smith, K. & Dawson, J. (1993). Inorg. Chem. 32, 1460-1466.]); Fujita et al. (1994[Fujita, M., Kwon, Y. J., Washizu, S. & Ogura, K. (1994). J. Am. Chem. Soc. 116, 1151-1152.]). For the use of the title compound in the synthesis of biological compounds, see: Darby et al. (1942[Darby, W., Lewis, H. & Totter, J. (1942). J. Am. Chem. Soc. 2, 463-464.]).

[Scheme 1]

Experimental

Crystal data
  • C4H6N2O

  • Mr = 98.11

  • Monoclinic, C 2/c

  • a = 13.9180 (9) Å

  • b = 7.1980 (5) Å

  • c = 11.6509 (12) Å

  • [beta] = 125.249 (1)°

  • V = 953.20 (13) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.688, Tmax = 0.746

  • 5389 measured reflections

  • 1158 independent reflections

  • 1086 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.095

  • S = 1.07

  • 1158 reflections

  • 65 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

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) -x+1, -y, -z+2; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: CrystalMaker (CrystalMaker Software, 2009[CrystalMaker Software (2009). CrystalMaker for Windows. CrystalMaker Software Ltd, Oxford, England.]); software used to prepare material for publication: enCIFer (Allen et al. 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2622 ).


Acknowledgements

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.

References

Albov, D. V., Rybakov, V. B., Babaev, E. V. & Tsisevich, A. A. (2006). Acta Cryst. E62, o963-o965.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bauman, J. & Wang, J. (1964). Inorg. Chem. 3, 368-373.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
CrystalMaker Software (2009). CrystalMaker for Windows. CrystalMaker Software Ltd, Oxford, England.
Darby, W., Lewis, H. & Totter, J. (1942). J. Am. Chem. Soc. 2, 463-464.  [CrossRef]
Fan, C., Li, G., Zhu, D. & Xhu, J. (2000). Chin. J. Chem. 18, 115-117.  [ChemPort]
Fujita, M., Kwon, Y. J., Washizu, S. & Ogura, K. (1994). J. Am. Chem. Soc. 116, 1151-1152.  [CrossRef] [ChemPort] [Web of Science]
Huff, A., Chang, C., Cooper, D., Smith, K. & Dawson, J. (1993). Inorg. Chem. 32, 1460-1466.  [CrossRef] [ChemPort] [Web of Science]
Nyamori, V. O., Bala, M. D. & Levendis, D. C. (2010). Acta Cryst. E66, m412.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


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

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