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

Jasinski, J.P.; Golen, J.A.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811027164

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 (C-C) = 0.002 Å
Disorder in main residue
R = 0.049
wR = 0.152
Data-to-parameter ratio = 16.6
Details

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

Jerry P. Jasinski,^a ^* James A. Golen,^a S. Samshuddin,^b B. Narayana ^b and H. S. Yathirajan ^c

^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-HO, O-HN and N-HO 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); Bouwman et al. (1990). For plant-protective agents in the field of pest control, see: Madkour et al. (2006). For related structures, see: Akkurt et al. (2011); Jian et al. (2003); Jasinski et al. (2010, 2011); Odabasoglu et al. (2007). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₆H₁₄N₂O₃·4H₂O
M_r = 354.36
Triclinic, $[P \overline 1]$
a = 6.8953 (6) Å
b = 11.4266 (13) Å
c = 11.7287 (14) Å
= 107.965 (10)°
= 90.906 (8)°
= 91.769 (8)°
V = 878.32 (16) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ )' T_min = 0.964, T_max = 0.979
8245 measured reflections
4539 independent reflections
3499 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(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
_max = 0.25 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4WBO5	0.84 (2)	1.98 (2)	2.809 (2)	170 (2)
O4-H4WAO5ⁱ	0.87 (2)	2.04 (2)	2.880 (2)	162 (2)
O5-H5WBN2	0.85 (1)	1.96 (2)	2.8003 (16)	171 (2)
O5-H5WAO7ⁱⁱ	0.85 (2)	1.94 (2)	2.7882 (19)	171 (2)
O6-H6WAO4ⁱⁱⁱ	0.85 (2)	2.16 (2)	2.996 (2)	171 (3)
O6-H6WBO2	0.85 (2)	2.40 (2)	3.187 (3)	154 (3)
O7-H7WBO4^iv	0.84 (2)	2.01 (2)	2.844 (2)	174 (2)
O7-H7WAO3A	0.81 (2)	1.98 (2)	2.721 (3)	151 (2)
N1-H1NO6	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
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.
Jasinski, J. P., Braley, A. N., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o2052.
Jasinski, J. P., Miller, W. M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o834-o835.
Jian, F. F., Bei, F. L., Wang, X. & Lu, L. D. (2003). Chinese J. Struct. Chem. 22, 382-386.
Madkour, H. M. F., Farag, A. A., Ramses, S. S. & Ibrahiem, N. A. A. (2006). Phosphorus Sulfur Silicon 181, 255-265.
Odabasoglu, M., Büyükgüngör, O., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3199-o3200.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds