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Volume 68 
Part 3 
Pages o816-o817  
March 2012  

Received 15 February 2012
Accepted 15 February 2012
Online 24 February 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.077
Data-to-parameter ratio = 21.9
Details
Open access

2-(8-Bromoimidazo[1,2-a]pyridin-2-yl)-N'-[(E)-4-diethylamino-2-hydroxybenzylidene]acetohydrazide dihydrate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bOrganic Electronics Division, Department of Chemistry, National Institute of Technology - Karnataka, Surathkal, Mangalore 575 025, India, and cFaculty of Industrial Science and Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak, 26300 Gambang, Kuantan, Pahang Darul Makmur, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C20H22BrN5O2·2H2O, the Schiff base molecule exists in an E conformation with respect to the acyclic C=N bond. An S(6) ring motif is formed via an intramolecular O-H...N hydrogen bond. The dihedral angle between the imidazo[1,2-a]pyridine system and the benzene ring is 84.62 (5)°. In the crystal, N-H...O, O-H...O, O-H...N, C-H...O and C-H...Br hydrogen bonds link the molecules into a three-dimensional network. The crystal packing is further stabilized by C-H...[pi] and [pi]-[pi] interactions [centroid-centroid distance = 3.5365 (7) Å].

Related literature

For background to and applications of hydrazones, see: Seleem et al. (2011[Seleem, H. S., El-Inany, G. A., El-Shetary, B. A. & Mousa, M. A. (2011). Chem. Cent. J. doi:10.1186/1752-153X-5-2.]); Rollas & Küçükgüzel (2007[Rollas, S. & Küçükgüzel, S. G. (2007). Molecules, 12, 1910-1939.]). For background to and applications of imidazopyridine, see: Ertepinarl et al. (1995[Ertepinarl, H., Gök, Y., Geban, Ö. & Özden, S. (1995). Eur. J. Med. Chem. 30, 171-175.]); Liang et al. (2007[Liang, G.-B., Qian, X., Feng, D., Fisher, M., Brown, C. M., Gurnett, A., Leavitt, P. S., Liberator, P. A., Misura, A. S., Tamas, T., Schmatz, D. M., Wyvratt, M. & Biftu, T. (2007). Bioorg. Med. Chem. Lett. 17, 3558-3561.]); Hamdouchi et al. (1999[Hamdouchi, C., Ezquerra, J., Vega, J. A., Vaquero, J. J., Alvarez-Builla, J. & Heinz, B. A. (1999). Bioorg. Med. Chem. Lett. 9, 1391-1394.]); Gudmundsson & Johns (2007[Gudmundsson, K. S. & Johns, B. A. (2007). Bioorg. Med. Chem. Lett. 17, 2735-2739.]); Biftu et al. (2006[Biftu, T. et al. (2006). Bioorg. Med. Chem. Lett. 16, 2479-2483.]); Fisher & Lusi (1972[Fisher, M. H. & Lusi, A. (1972). J. Med. Chem. 15, 982-985.]); Bochis et al. (1981[Bochis, R. J., Olen, L. E., Waksmunski, F. S., Mrozik, H., Eskola, P., Kulsa, P., Wilks, G., Taylor, J. E., Egerton, J. R., Ostlind, D. A. & Olson, G. (1981). J. Med. Chem. 24, 1518-1521.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C20H22BrN5O2·2H2O

  • Mr = 480.37

  • Triclinic, [P \overline 1]

  • a = 8.4370 (4) Å

  • b = 10.6711 (5) Å

  • c = 11.7559 (5) Å

  • [alpha] = 92.914 (1)°

  • [beta] = 96.949 (1)°

  • [gamma] = 93.978 (1)°

  • V = 1046.23 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.00 mm-1

  • T = 100 K

  • 0.37 × 0.20 × 0.07 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.529, Tmax = 0.869

  • 22937 measured reflections

  • 6491 independent reflections

  • 5841 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.077

  • S = 1.05

  • 6491 reflections

  • 297 parameters

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

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/N2/C6/C7 ring and Cg3 is the centroid of the C11-C16 ring.

D-H...A D-H H...A D...A D-H...A
N3-H1N3...O2Wi 0.894 (17) 1.908 (17) 2.7956 (15) 171.7 (17)
O2-H1O2...O1Wii 0.87 (3) 2.42 (3) 2.9423 (15) 119 (2)
O2-H1O2...N4 0.87 (3) 1.99 (3) 2.7181 (16) 142 (2)
O1W-H1W1...N1 0.86 (2) 1.98 (2) 2.8315 (14) 176 (2)
O1W-H2W1...O1iii 0.85 (3) 1.92 (2) 2.7361 (14) 162 (2)
O2W-H1W2...O1Wi 0.80 (2) 2.08 (2) 2.8311 (15) 157 (2)
O2W-H2W2...O1W 0.86 (2) 1.87 (2) 2.7245 (15) 172.9 (17)
C5-H5A...O1iv 0.93 2.50 3.3121 (17) 146
C10-H10A...O2Wi 0.93 2.54 3.3256 (17) 142
C17-H17B...Br1v 0.97 2.85 3.6569 (15) 142
C3-H3A...Cg3vi 0.93 2.61 3.4734 (15) 154
C17-H17A...Cg1vii 0.97 2.70 3.5863 (15) 152
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z; (iii) x+1, y, z; (iv) -x, -y+1, -z+1; (v) -x+1, -y, -z+2; (vi) x+1, y+1, z; (vii) -x, -y, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2340 ).


Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for Research University Grant No. 1001/PFIZIK/811160. WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160. AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Biftu, T. et al. (2006). Bioorg. Med. Chem. Lett. 16, 2479-2483.  [CrossRef] [PubMed] [ChemPort]
Bochis, R. J., Olen, L. E., Waksmunski, F. S., Mrozik, H., Eskola, P., Kulsa, P., Wilks, G., Taylor, J. E., Egerton, J. R., Ostlind, D. A. & Olson, G. (1981). J. Med. Chem. 24, 1518-1521.  [CrossRef] [ChemPort] [PubMed] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Ertepinarl, H., Gök, Y., Geban, Ö. & Özden, S. (1995). Eur. J. Med. Chem. 30, 171-175.
Fisher, M. H. & Lusi, A. (1972). J. Med. Chem. 15, 982-985.  [CrossRef] [ChemPort] [PubMed] [ISI]
Gudmundsson, K. S. & Johns, B. A. (2007). Bioorg. Med. Chem. Lett. 17, 2735-2739.  [CrossRef] [PubMed] [ChemPort]
Hamdouchi, C., Ezquerra, J., Vega, J. A., Vaquero, J. J., Alvarez-Builla, J. & Heinz, B. A. (1999). Bioorg. Med. Chem. Lett. 9, 1391-1394.  [CrossRef] [PubMed] [ChemPort]
Liang, G.-B., Qian, X., Feng, D., Fisher, M., Brown, C. M., Gurnett, A., Leavitt, P. S., Liberator, P. A., Misura, A. S., Tamas, T., Schmatz, D. M., Wyvratt, M. & Biftu, T. (2007). Bioorg. Med. Chem. Lett. 17, 3558-3561.  [CrossRef] [PubMed] [ChemPort]
Rollas, S. & Küçükgüzel, S. G. (2007). Molecules, 12, 1910-1939.  [CrossRef] [PubMed] [ChemPort]
Seleem, H. S., El-Inany, G. A., El-Shetary, B. A. & Mousa, M. A. (2011). Chem. Cent. J. doi:10.1186/1752-153X-5-2.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o816-o817   [ doi:10.1107/S160053681200685X ]

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