4-Meth­oxy­benzaldehyde (5-bromo­pyrimidin-2-yl)hydrazone monohydrate

Hoong-Kun Fun; Wan-Sin Loh; Suresh P Nayak

doi:10.1107/S1600536810033283

. 2010 Aug 28;66(Pt 9):o2467. doi: 10.1107/S1600536810033283

4-Methoxybenzaldehyde (5-bromopyrimidin-2-yl)hydrazone monohydrate

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a,^§, Suresh P Nayak ^b

PMCID: PMC3007892 PMID: 21588785

Abstract

In the title Schiff base compound, C₁₂H₁₁BrN₄O·H₂O, the organic molecule exists in an E configuration with respect to the C=N double bond. The pyrimidine ring is approximately planar, with a maximum deviation of 0.011 (2) Å, and forms a dihedral angle of 10.68 (8)° with the benzene ring. In the crystal, intermolecular O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a two-dimensional network parallel to the ac plane.

Related literature

For the preparation of hydrazones, see: Pasha & Nanjundaswamy (2004 ▶). For the importance and biological activity of hydrazones, see: Sridhar & Perumal (2003 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶). For the biological activity of pyrimidines and their derivatives, see: Ghorab et al. (2004 ▶). For a related structure, see: Zhang et al. (2009 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₂H₁₁BrN₄O·H₂O
M _r = 325.17
Orthorhombic,
a = 13.0606 (3) Å
b = 60.5887 (10) Å
c = 6.5618 (1) Å
V = 5192.52 (17) Å³
Z = 16
Mo Kα radiation
μ = 3.17 mm⁻¹
T = 100 K
0.40 × 0.34 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.365, T _max = 0.558
12616 measured reflections
4593 independent reflections
4107 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.052
S = 0.92
4593 reflections
225 parameters
1 restraint
All H-atom parameters refined
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.40 e Å⁻³
Absolute structure: Flack (1983 ▶), 2037 Friedel pairs
Flack parameter: 0.012 (5)

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033283/wn2404sup1.cif

e-66-o2467-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033283/wn2404Isup2.hkl

e-66-o2467-Isup2.hkl^{(225.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N2	0.84 (3)	2.55 (3)	3.153 (2)	131 (2)
O1W—H1W1⋯N4	0.84 (3)	2.30 (3)	3.0511 (19)	151 (2)
O1W—H2W1⋯N2ⁱ	0.84 (3)	2.01 (3)	2.8341 (19)	169 (2)
N3—H1N3⋯O1Wⁱⁱ	0.81 (3)	1.99 (3)	2.7773 (19)	165.1 (19)
C5—H5A⋯O1Wⁱⁱ	0.99 (2)	2.43 (2)	3.257 (2)	140.7 (13)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of a research fellowship.

supplementary crystallographic information

Comment

Hydrazones have been prepared by treating aryl hydrazines with carbonyl compounds using a variety of solvents in the presence or absence of an acidic catalyst (Pasha & Nanjundaswamy, 2004). Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar & Perumal, 2003). Hydrazones have been demonstrated to possess a variety of pharmacological activities (Rollas et al., 2002; Terzioglu & Gürsoy, 2003). These observations have provided the guidelines for the development of new hydrazones that possess a variety of biological activities. Pyrimidines and their derivatives possess biological and pharmacological activities such as antibacterial, antimicrobial, anti-inflammatory, analgesic, anticonvulsant and anti-aggressive properties (Ghorab et al., 2004). This prompted us to synthesize compounds containing the pyrimidine unit.

The asymmetric unit of the title Schiff base compound (Fig. 1) consists of one molecule of p-anisyl-(5-bromopyrimidin-2-yl)hydrazone and one water molecule. The p-anisyl-(5-bromopyrimidin-2-yl)hydrazone molecule exists in an E configuration with respect to the C5═N4 double bond. The pyrimidine ring (C1–C3/N2/C4/N1) is approximately planar, with a maximum deviation of 0.011 (2) Å at atom C3 and it forms a dihedral angle of 10.68 (8)° with the benzene ring (C6–C11). Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those in the related crystal structure (Zhang et al., 2009).

In the crystal packing (Fig. 2) intermolecular O1W—H1W1···N2, O1W—H1W1···N4 O1W—H2W1···N2, N3—H1N3···O1W and C5—H5A···O1W hydrogen bonds (Table 1) link the molecules into two-dimensional networks parallel to the ac plane.

Experimental

The title compound was obtained by refluxing 5-bromo-2-hydrazinopyrimidine (0.01 mol) and 4-methoxybenzaldehyde (0.01 mol) in ethanol (30 ml), with the addition of 3 drops of concentrated sulfuric acid over a period of 1 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The resulting solid product was filtered, washed with ethanol and dried. Colourless single crystals suitable for X-ray analysis were obtained from the ethanol solution by slow evaporation.