(E)-4-Bromo-N′-(4-hy­droxy-3-meth­oxy­benzyl­idene)benzohydrazide monohydrate

Jirapa Horkaew; Suchada Chantrapromma; Teerasak Anantapong; Akkharawit Kanjana-Opas; Hoong-Kun Fun

doi:10.1107/S160053681201032X

. 2012 Mar 14;68(Pt 4):o1069–o1070. doi: 10.1107/S160053681201032X

(E)-4-Bromo-N′-(4-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate

Jirapa Horkaew ^a, Suchada Chantrapromma ^b,^*,^‡, Teerasak Anantapong ^c, Akkharawit Kanjana-Opas ^c, Hoong-Kun Fun ^d,^§

PMCID: PMC3344027 PMID: 22589936

Abstract

In the title compound, C₁₅H₁₃BrN₂O₃·H₂O, the dihedral angle between the two benzene rings is 13.92 (6)°. The methoxy group of the 4-hydroxy-3-methoxyphenyl is almost coplanar with its bound benzene ring, as seen by the C_methyl—O—C—C torsion angle of −0.35 (16)°. In the crystal, molecules are linked into a three-dimensional network by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds and also weak C—H⋯O interactions. A short C⋯O contact of 3.0191 (15) Å is also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Promdet et al. (2011 ▶). For background and applications of benzohydrazide derivatives, see: Loncle et al. (2004 ▶); Raj et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₃·H₂O
M _r = 367.19
Monoclinic,
a = 7.9772 (7) Å
b = 21.446 (2) Å
c = 10.3928 (7) Å
β = 119.479 (5)°
V = 1547.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.68 mm⁻¹
T = 100 K
0.58 × 0.21 × 0.11 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.306, T _max = 0.756
18815 measured reflections
5602 independent reflections
4894 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.065
S = 1.04
5602 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.54 e Å⁻³

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 datablock(s) global, I. DOI: 10.1107/S160053681201032X/fj2521sup1.cif

e-68-o1069-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201032X/fj2521Isup2.hkl

e-68-o1069-Isup2.hkl^{(274.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201032X/fj2521Isup3.cml

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
O3—H1O3⋯O1Wⁱ	0.80	1.79	2.5867 (14)	170
N1—H1N1⋯O3ⁱⁱ	0.86	2.18	3.0107 (16)	162
O1W—H1OW⋯O1ⁱⁱⁱ	0.82	1.93	2.7409 (14)	171
O1W—H2OW⋯O1^iv	0.78	2.16	2.8883 (14)	154
O1W—H2OW⋯N2^iv	0.78	2.49	3.0971 (16)	136
C6—H6A⋯O3ⁱⁱ	0.95	2.59	3.4832 (15)	156
C8—H8A⋯O3ⁱⁱ	0.95	2.40	3.2604 (17)	150
C10—H10A⋯O1W^v	0.95	2.45	3.3933 (15)	172

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

JH thanks the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education, and the Graduate School, Prince of Songkla University, for financial support. The authors thank the Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

As part of our study on bioactivity of hydrazone and benzohydrazide derivatives, the title compound is one of the several benzohydrazide derivatives which were synthesized and tested for biological activity. It have been known that some benzohydrazides possess various biological properties, such as antibacterial and antifungal (Loncle et al., 2004), and antiproliferative (Raj et al., 2007) activities. We have previously reported some crystal structures of this category of compounds (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011). The title compound (I) was synthesized in order to study the effect of functional groups and their positions on their bioactivities by comparing with the closely related structures in our research project. (I) was screened for antibacterial and antioxidant activities. Our biological testing found that (I) exhibits potent antioxidant activity whereas inactive against the tested bacteria strains which are Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecalis, Pseudomonas aeruginosa, Salmonella typhi and Shigella sonnei. Herein we report the crystal structure of (I).

The molecule of the title benzohydrazide derivative (Fig. 1), C₁₅H₁₃BrN₂O₃.H₂O, comprises of a molecule of benzohydrazide and one water solvent molecule. The molecule of benzohydrazide exists in a trans-configuration with respect to the C8═N2 bond [1.2853 (14) Å] and the torsion angle N1–N2–C8–C9 = 178.54 (10)°. The molecule is twisted with the dihedral angle between the two phenyl rings being 13.92 (6)°. The methoxy group of the 4-hydroxy-3-methoxyphenyl is co-planar with its bound benzene ring [C15–O2–C11–C10 = 0.35 (16)°].

The middle bridge fragment (O1/C7/N1/N2/C8) is essentially planar with the torsion angle N2–N1–C7–O1 = -0.21 (17)°. The mean plane through this bridge makes the dihedral angles of 12.71 (7) and 1.25 (7)° with the 4-bromophenyl and 4 benzene rings, respectively. The methoxy group of 4-hydroxy-3-methoxyphenyl is co-planar with its bound benzene ring with the torsion angle C15–O2–C11–C10 = 0.35 (16)° and the r.m.s 0.0063 (2) Å for the eight non H atoms. Bond distances are in normal ranges (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O, O—H···N and O—H···O hydrogen bonds together with weak C—H···O interactions (Table 1) into a three dimensional network. A C8···O2ⁱ[3.0191 (15) Å] short contact was presented.

Experimental

The title compound (I) was prepared by dissolving 4-bromobenzohydrazide (2 mmol, 0.43 g) in ethanol (15 ml). The solution of 4-hydroxy-3-methoxy-benzaldehyde (2 mmol, 0.30 g) in ethanol (15 ml) was then added slowly to the reaction. The mixture was refluxed for around 5 hr and the white solid of the product that appeared was collected by filtration, washed with ethanol and dried in air. Colorless block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from methanol by slow evaporation of the solvent at room temperature after several days, Mp. 513 K (decomposed).