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

Fun, H.-K.; Loh, W.-S.; Shenvi, S.; Isloor, A.M.; Hegde, G.

doi:10.1107/S160053681200685X

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 (C-C) = 0.002 Å
R = 0.027
wR = 0.077
Data-to-parameter ratio = 21.9
Details

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

Hoong-Kun Fun,^a ^*⁺ Wan-Sin Loh,^a ⁺⁺ Seema Shenvi,^b Arun M. Isloor ^b and Gurumurthy Hegde ^c

^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-HN 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-HO, O-HO, O-HN, C-HO and C-HBr 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); Rollas & Küçükgüzel (2007). For background to and applications of imidazopyridine, see: Ertepinarl et al. (1995); Liang et al. (2007); Hamdouchi et al. (1999); Gudmundsson & Johns (2007); Biftu et al. (2006); Fisher & Lusi (1972); Bochis et al. (1981). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₀H₂₂BrN₅O₂·2H₂O
M_r = 480.37
Triclinic, $[P \overline 1]$
a = 8.4370 (4) Å
b = 10.6711 (5) Å
c = 11.7559 (5) Å
= 92.914 (1)°
= 96.949 (1)°
= 93.978 (1)°
V = 1046.23 (8) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.529, T_max = 0.869
22937 measured reflections
6491 independent reflections
5841 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(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
_max = 0.63 e Å^-3
_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-HA	D-H	HA	DA	D-HA
N3-H1N3O2Wⁱ	0.894 (17)	1.908 (17)	2.7956 (15)	171.7 (17)
O2-H1O2O1Wⁱⁱ	0.87 (3)	2.42 (3)	2.9423 (15)	119 (2)
O2-H1O2N4	0.87 (3)	1.99 (3)	2.7181 (16)	142 (2)
O1W-H1W1N1	0.86 (2)	1.98 (2)	2.8315 (14)	176 (2)
O1W-H2W1O1ⁱⁱⁱ	0.85 (3)	1.92 (2)	2.7361 (14)	162 (2)
O2W-H1W2O1Wⁱ	0.80 (2)	2.08 (2)	2.8311 (15)	157 (2)
O2W-H2W2O1W	0.86 (2)	1.87 (2)	2.7245 (15)	172.9 (17)
C5-H5AO1^iv	0.93	2.50	3.3121 (17)	146
C10-H10AO2Wⁱ	0.93	2.54	3.3256 (17)	142
C17-H17BBr1^v	0.97	2.85	3.6569 (15)	142
C3-H3ACg3^vi	0.93	2.61	3.4734 (15)	154
C17-H17ACg1^vii	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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

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organic compounds