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Volume 67 
Part 8 
Pages o2021-o2022  
August 2011  

Received 30 June 2011
Accepted 6 July 2011
Online 13 July 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.049
wR = 0.152
Data-to-parameter ratio = 16.6
Details
Open access

4-(1H-Benzimidazol-2-ylmethoxy)-3-methoxybenzaldehyde tetrahydrate

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C16H14N2O3·4H2O, the dihedral angle between the mean planes of the benzimidazole ring system and benzene ring is 2.9 (1)°. The aldehyde group is disordered over two sets of sites with refined occupancies of 0.559 (4) and 0.441 (4). In the crystal, extensive intermolecular O-H...O, O-H...N and N-H...O hydrogen bonds in concert with weak [pi]-[pi] stacking interactions [centroid-centroid distances = 3.6104 (9), 3.6288 (9) and 3.9167 (10) Å] create a three-dimensional network.

Related literature

For the pharmaceutical and biological activity of benzimidazole compounds, see: Pujar et al. (1988[Pujar, M. A., Bharamgoudar, T. D. & Sathyanarayana, D. N. (1988). Transition Met. Chem. 13, 423-425.]); Bouwman et al. (1990[Bouwman, E., Driessen, W. L. & Reedijk, J. (1990). Coord. Chem. Rev. 104, 143-172.]). For plant-protective agents in the field of pest control, see: Madkour et al. (2006[Madkour, H. M. F., Farag, A. A., Ramses, S. S. & Ibrahiem, N. A. A. (2006). Phosphorus Sulfur Silicon 181, 255-265.]). For related structures, see: Akkurt et al. (2011[Akkurt, M., Baktir, Z., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1088-o1089.]); Jian et al. (2003[Jian, F. F., Bei, F. L., Wang, X. & Lu, L. D. (2003). Chinese J. Struct. Chem. 22, 382-386.]); Jasinski et al. (2010[Jasinski, J. P., Braley, A. N., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o2052.], 2011[Jasinski, J. P., Miller, W. M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o834-o835.]); Odabasoglu et al. (2007)[Odabasoglu, M., Büyükgüngör, O., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3199-o3200.]. For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N2O3·4H2O

  • Mr = 354.36

  • Triclinic, [P \overline 1]

  • a = 6.8953 (6) Å

  • b = 11.4266 (13) Å

  • c = 11.7287 (14) Å

  • [alpha] = 107.965 (10)°

  • [beta] = 90.906 (8)°

  • [gamma] = 91.769 (8)°

  • V = 878.32 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 K

  • 0.35 × 0.33 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.])' Tmin = 0.964, Tmax = 0.979

  • 8245 measured reflections

  • 4539 independent reflections

  • 3499 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.152

  • S = 1.02

  • 4539 reflections

  • 273 parameters

  • 17 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4WB...O5 0.84 (2) 1.98 (2) 2.809 (2) 170 (2)
O4-H4WA...O5i 0.87 (2) 2.04 (2) 2.880 (2) 162 (2)
O5-H5WB...N2 0.85 (1) 1.96 (2) 2.8003 (16) 171 (2)
O5-H5WA...O7ii 0.85 (2) 1.94 (2) 2.7882 (19) 171 (2)
O6-H6WA...O4iii 0.85 (2) 2.16 (2) 2.996 (2) 171 (3)
O6-H6WB...O2 0.85 (2) 2.40 (2) 3.187 (3) 154 (3)
O7-H7WB...O4iv 0.84 (2) 2.01 (2) 2.844 (2) 174 (2)
O7-H7WA...O3A 0.81 (2) 1.98 (2) 2.721 (3) 151 (2)
N1-H1N...O6 0.83 (1) 2.02 (1) 2.8152 (19) 160 (2)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y+1, z+1; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5279 ).


Acknowledgements

BN thanks Mangalore University for the research facilities and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for the facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Akkurt, M., Baktir, Z., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1088-o1089.  [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bouwman, E., Driessen, W. L. & Reedijk, J. (1990). Coord. Chem. Rev. 104, 143-172.  [CrossRef] [ChemPort] [ISI]
Jasinski, J. P., Braley, A. N., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o2052.  [CrossRef] [details]
Jasinski, J. P., Miller, W. M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o834-o835.  [CrossRef] [details]
Jian, F. F., Bei, F. L., Wang, X. & Lu, L. D. (2003). Chinese J. Struct. Chem. 22, 382-386.  [ChemPort]
Madkour, H. M. F., Farag, A. A., Ramses, S. S. & Ibrahiem, N. A. A. (2006). Phosphorus Sulfur Silicon 181, 255-265.  [CrossRef] [ChemPort]
Odabasoglu, M., Büyükgüngör, O., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3199-o3200.  [CSD] [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Pujar, M. A., Bharamgoudar, T. D. & Sathyanarayana, D. N. (1988). Transition Met. Chem. 13, 423-425.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2011). E67, o2021-o2022   [ doi:10.1107/S1600536811027164 ]

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