2-{2-[(E)-(2-Benzoyl­hydrazin-1-yl­idene)meth­yl]phen­oxy}acetic acid

Hoong-Kun Fun; Tze Shyang Chia; Ahmed M Alafeefy; Hatem A Abdel-Aziz

doi:10.1107/S1600536812028735

. 2012 Jun 30;68(Pt 7):o2260–o2261. doi: 10.1107/S1600536812028735

2-{2-[(E)-(2-Benzoylhydrazin-1-ylidene)methyl]phenoxy}acetic acid

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Ahmed M Alafeefy ^b, Hatem A Abdel-Aziz ^c

PMCID: PMC3394044 PMID: 22798909

Abstract

In the title compound, C₁₆H₁₄N₂O₄, the dihedral angle between the aromatic rings is 12.45 (6)°. The central C(=O)—N—N=C bridge is roughly planar (r.m.s. deviation = 0.0346 Å) and makes dihedral angles of 13.01 (7) and 0.56 (7)° with the attached phenyl and benzene rings, respectively. The acetic acid unit (r.m.s. deviation = 0.0066 Å) is twisted from its attached benzene ring [dihedral angle = 19.48 (6)°]. In the crystal, molecules are linked by O—H⋯(O,N), N—H⋯O and C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. A weak aromatic π–π stacking interaction is also observed [centroid–centroid distance = 3.7330 (7) Å].

Related literature

For background to the biological activity of hydrazones, see: Abdel-Aziz & Mekawey (2009 ▶). For a related structure, see: Rassem et al. (2012 ▶). For further synthetic details, see: Desai et al. (2000 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₄N₂O₄
M _r = 298.29
Monoclinic,
a = 12.2173 (7) Å
b = 7.8523 (5) Å
c = 15.6025 (9) Å
β = 108.577 (1)°
V = 1418.82 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.32 × 0.21 × 0.14 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.969, T _max = 0.986
14301 measured reflections
4122 independent reflections
3463 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.124
S = 1.07
4122 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.25 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/S1600536812028735/hb6868sup1.cif

e-68-o2260-sup1.cif^{(24.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028735/hb6868Isup2.hkl

e-68-o2260-Isup2.hkl^{(202KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028735/hb6868Isup3.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⋯O1ⁱ	0.88	1.99	2.7194 (14)	139
O3—H1O3⋯N2ⁱ	0.88	2.30	3.0464 (12)	142
N1—H1N1⋯O4ⁱⁱ	0.925 (17)	2.009 (16)	2.9131 (13)	165.4 (16)
C5—H5A⋯O4ⁱⁱ	0.93	2.55	3.4058 (16)	153
C11—H11A⋯O1ⁱⁱⁱ	0.93	2.51	3.3791 (13)	155
C15—H15A⋯O1^iv	0.97	2.59	3.5434 (15)	167

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University.

supplementary crystallographic information

Comment

In continuation to our interest in the chemistry and biological activities of hydrazones (Abdel-Aziz et al., 2009), we now report herein the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1. The C1–C6 and C9–C14 benzene rings are slightly twisted from each other as indicated by the dihedral angle of 12.45 (6)°. The central C7(═O1)—N1—N2═C8 bridge is nearly planar [r.m.s. deviation = 0.0346 Å], extended in a zigzag conformation and makes dihedral angles of 13.01 (7) and 0.56 (7)° with the C1–C6 and C9–C14 benzene rings, respectively. The acetic acid unit [C15/C16/O3/O4; r.m.s. deviation = 0.0066 Å] is twisted from its attached C9–C14 benzene ring with dihedral angle of 19.48 (6)°. Bond lengths and angles are comparable to those in a related structure (Rassem et al., 2012).

In the crystal (Fig. 2), molecules are linked by O3—H1O3···O1, O3—H1O3···N2, N1—H1N1···O4, C5—H5A···O4, C11—H11A···O1 and C15—H15A···O1 hydrogen bonds (Table 1) into two-dimensional networks parallel to bc plane. π-π interaction is also observed with Cg1···Cg2 distance of 3.7330 (7) Å [symmentry operator = 1 - x,-y,-z], where Cg1 and Cg2 are the centroids of C1–C6 and C9–C14 rings, respectively.

Experimental

The title compound was prepared by heating 2-(2-formylphenoxy)acetic acid with benzohydrazide in absolute ethanol for 4 h (Desai et al., 2000). Colourless blocks were obtained by slow evaporation from EtOH/DMF.