N′-[(E)-(3-Phenyl-1H-pyrazol-4-yl)methyl­idene]naphtho­[2,1-b]furan-2-carbohydrazide monohydrate

Hoong-Kun Fun; Wan-Sin Loh; Shridhar Malladi; B M Ganesh; Arun M Isloor

doi:10.1107/S1600536811050239

. 2011 Nov 30;67(Pt 12):o3471–o3472. doi: 10.1107/S1600536811050239

N′-[(E)-(3-Phenyl-1H-pyrazol-4-yl)methylidene]naphtho[2,1-b]furan-2-carbohydrazide monohydrate

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a,^§, Shridhar Malladi ^b, B M Ganesh ^b, Arun M Isloor ^b

PMCID: PMC3239098 PMID: 22199946

Abstract

In the title hydrate, C₂₃H₁₆N₄O₂·H₂O, the pyrazole ring is approximately planar, with a maximum deviation of 0.023 (1) Å, and makes dihedral angles of 28.63 (6) and 46.44 (7)° with the naphtho[2,1-b]furan ring system and the benzene ring, respectively, In the crystal, O—H⋯N, O—H⋯O, N—H⋯O, N—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds link the molecules, forming sheets lying parallel to the ab plane. The crystal structure also features C—H⋯π interactions involving the centroids of the pyrazole and benzene rings.

Related literature

For the biological activity of hydrazides, hydrazones and their adducts, see: Jahagirdar et al. (1990 ▶); Cavier & Rips (1965 ▶); Silva et al. (2005 ▶); Eissa & Soliman (2009 ▶). For a related structure, see: Choi et al. (2009 ▶). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₃H₁₆N₄O₂·H₂O
M _r = 398.41
Monoclinic,
a = 7.1383 (1) Å
b = 9.3928 (1) Å
c = 28.4200 (4) Å
β = 96.864 (1)°
V = 1891.86 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.31 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.971, T _max = 0.983
21248 measured reflections
5516 independent reflections
3857 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.129
S = 1.03
5516 reflections
279 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 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/S1600536811050239/hb6529sup1.cif

e-67-o3471-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050239/hb6529Isup2.hkl

e-67-o3471-Isup2.hkl^{(270.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050239/hb6529Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C18–C23 and N3/N4/C15–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N4ⁱ	0.86	2.13	2.9625 (18)	163
O1W—H2W1⋯O2ⁱⁱ	0.89	2.12	2.9465 (16)	154
N3—H1N3⋯O2ⁱⁱⁱ	0.95 (2)	2.52 (3)	3.2162 (18)	130.4 (19)
N3—H1N3⋯N2ⁱⁱⁱ	0.95 (2)	2.10 (3)	2.9927 (19)	155 (2)
N1—H1N1⋯O1W	0.94 (3)	2.06 (3)	2.9388 (18)	155 (2)
C14—H14A⋯O1W	0.95	2.54	3.2877 (18)	136
C16—H16A⋯N4^iv	0.95	2.50	3.430 (2)	167
C21—H21A⋯O2^v	0.95	2.53	3.318 (2)	140
C7—H7A⋯Cg2^vi	0.95	2.80	3.6022 (18)	142
C22—H22A⋯Cg1ⁱⁱ	0.95	2.93	3.5274 (16)	122

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

supplementary crystallographic information

Comment

Acidhydrazones and their condensation products possessing an azometine –NHN═ CH– proton constitute an important class of compounds for new drug development. In the past several years, numerous compounds with diverse structural features have been reported. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. Hydrazides, hydrazones and their adducts have displayed diverse range of biological properties such as anti-viral (Jahagirdar et al., 1990), anti-tuberculosis (Cavier et al., 1965) and anti-inflammatory activities (Silva et al., 2005; Eissa et al., 2009). We have synthesized the title compound to study its crystal structure and evaluate its biological activities.

The title compound (Fig. 1) consists of one molecule of N'-[(E)-(3-phenyl-1H-pyrazol-4-yl)methylidene]naphtho [2,1-b]furan-2-carbohydrazide and a water molecule. The pyrazole ring (N3/N4/C15–C17) is approximately planar with a maximum deviation of 0.023 (1) Å at atom C17. This ring makes dihedral angles of 28.63 (6)° with the naphtho[2,1-b]furan ring system (O1/C1–C12; maximum deviation of 0.016 (1) Å at atom C10) and 46.44 (7)° with the benzene ring (C18–C23; maximum deviation of 0.012 (1) Å at atom C18). Bond lengths and angles are comparable to a related structure (Choi et al., 2009).

In the crystal, (Fig. 2), O1W—H1W1···N4, O1W—H2W1···O2, N3—H1N3···O2, N3—H1N3···N2, N1—H1N1···O1W C14—H14A···O1W, C16—H16A···N4 and C21—H21A···O2 hydrogen bonds (Table 1) link the molecules to form sheets parallel to the ab plane. The crystal structure is further stabilized by C—H···π interactions (Table 1) involving the centroids of pyrazole (Cg1) and benzene (Cg2) rings.

Experimental

A mixture of naphtho[2,1-b]furan-2-carbohydrazide (0.226 g, 0.001 mol) and 3-phenyl-1H-pyrazole-4-carbaldehyde (0.189 g, 0.0011 mol) was refluxed in ethanol for 4 h in the presence of a catalytic amount of acetic acid. The mixture was then cooled to room temperature and the resulting solid was filtered and dried to get the title compound. Yield: 0.28 g, 73.68%. M.p.: 524–526 K.