3-{2-[2-(3-Hy­droxy­benzyl­idene)hydrazin-1-yl]-1,3-thia­zol-4-yl}-2H-chromen-2-one hemihydrate

Afsheen Arshad; Hasnah Osman; Kit Lam Chan; Jia Hao Goh; Hoong-Kun Fun

doi:10.1107/S1600536810019653

. 2010 May 29;66(Pt 6):o1498–o1499. doi: 10.1107/S1600536810019653

3-{2-[2-(3-Hydroxybenzylidene)hydrazin-1-yl]-1,3-thiazol-4-yl}-2H-chromen-2-one hemihydrate

Afsheen Arshad ^a, Hasnah Osman ^a,^‡, Kit Lam Chan ^b, Jia Hao Goh ^c,^§, Hoong-Kun Fun ^c,^*,^¶

PMCID: PMC2979574 PMID: 21579559

Abstract

In the title compound, C₁₉H₁₃N₃O₃S·0.5H₂O, both organic molecules (A and B) exist in E configurations with respect to the acyclic C=N bond and have similar overall conformations. In molecule A, the essentially planar thiazole ring [maximum deviation = 0.010 (2) Å] is inclined at interplanar angles of 11.44 (10) and 32.50 (12)°, with the 2H-chromene ring system and the benzene ring, respectively. The equivalent values for molecule B are 0.002 (2) Å, 7.71 (9) and 12.51 (12)°. In the crystal structure, neighbouring molecules are interconnected into infinite layers lying parallel to (010) by O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds. Further stabilization of the crystal structure is provided by weak intermolecular C—H⋯π and π–π [centroid–centroid distance = 3.6380 (19) Å] interactions.

Related literature

For general background to and applications of aminothiazoles, see: Anderson et al. (2002 ▶); Finn et al. (2004 ▶); Gursoy & Karah (2000 ▶); Habib & Khalil (1984 ▶); Hiremath et al. (1992 ▶); Hofmanová et al. (1998 ▶); Jayashree et al. (2005 ▶); Karah et al. (1998 ▶); Kimura et al. (1985 ▶); Laffitte et al. (2002 ▶); Mitscher (2002 ▶); Moffett (1964 ▶); Ohkuba et al. (1995 ▶); Patt et al. (1992 ▶); Tassies et al. (2002 ▶); Wattenberg et al. (1979 ▶); Weber et al. (1998 ▶). For the preparation of the title compound, see: Lv et al. (2010 ▶); Siddiqui et al. (2009 ▶). For related structures, see: Arshad et al. (2010a ▶,b ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₉H₁₃N₃O₃S·0.5H₂O
M _r = 372.39
Monoclinic,
a = 8.012 (3) Å
b = 32.775 (11) Å
c = 12.619 (4) Å
β = 93.034 (7)°
V = 3309 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.34 × 0.14 × 0.05 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.928, T _max = 0.990
31194 measured reflections
7564 independent reflections
5266 reflections with I > 2σ(I)
R _int = 0.073

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.128
S = 1.06
7564 reflections
480 parameters
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.31 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 datablocks global, I. DOI: 10.1107/S1600536810019653/hb5467sup1.cif

e-66-o1498-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019653/hb5467Isup2.hkl

e-66-o1498-Isup2.hkl^{(370.1KB, hkl)}

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

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

Cg1 is the centroid of C14A–C19A benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3A—H3OA⋯O3Bⁱ	0.82	2.00	2.808 (3)	170
N2A—H2NA⋯O1Wⁱⁱ	0.88	1.93	2.790 (3)	167
O3B—H3OB⋯O2Bⁱⁱⁱ	0.82	1.93	2.726 (3)	165
N2B—H2NB⋯O2A^iv	0.84	2.05	2.878 (3)	170
O1W—H1W1⋯N1B^v	0.87	2.05	2.888 (3)	161
O1W—H2W1⋯N1A^vi	0.88	2.15	2.913 (3)	145
C8A—H8A⋯O1W^vii	0.93	2.60	3.451 (3)	153
C5B—H5B⋯Cg1^iv	0.93	2.95	3.708 (3)	139

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for a Short-term Grant (No. 304/PKIMIA/639004) to conduct this research. AA thanks the Pakistan Government and PCSIR for financial scholarship support. HKF and JHG thank USM for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

The biological activity of aminothiazoles is well documentated. Some of these compounds exhibit very good anti-fungal (Hiremath et al., 1992), anti-bacterial (Habib & Khalil, 1984), anti-tuberculosis (Gursoy & Karah, 2000; Karah et al., 1998) and anti-tumor (Wattenberg et al., 1979) activities. They also have broad applications in the treatment of allergies, Schizophrenia (Ohkuba et al., 1995), inflammation (Jayashree et al., 2005) and hypertension (Patt et al., 1992). Besides that, coumarin and its derivatives also possess significant anti-bacterial (Mitscher, 2002; Laffitte et al., 2002), anti-fungal (Moffett, 1964) and cytotoxic (Weber et al., 1998) activities. They also have pronounced medicinal value as anti-coagulants (Anderson et al., 2002; Tassies et al., 2002), free radical scavengers (Finn et al., 2004), lipoxygenese and cyclooxygenese inhibitors (Kimura et al., 1985, Hofmanová et al., 1998). The title compound, (I) was synthesized by incorporating aminothioazole moiety to a coumarin skeleton and here we present its crystal structure.

The asymmetric unit of the title compound (Fig. 1) comprises of two crystallographically independent 3-{2-[2-(3-hydroxybenzylidene)hydrazinyl]thiazol-4-yl}-2H-chromen-2-one molecules and a water molecule of crystallization. Both of the independent molecules exist in cis configurations with respect to the acyclic N3═C13 double bond. A superposition of the non-H atoms of molecules A and B (Fig. 2) using XP in SHELXTL (Sheldrick, 2008), gave an r.m.s. deviation of 0.447 Å.

In each molecule, the thiazole ring (C10/C11/S1/C12/N1) is essentially planar, with maximum deviations of -0.010 (2) and 0.002 (2) Å, respectively, for atoms C11A of molecule A and C12B of molecule B. In molecule A, the thiazole ring is inclined at interplanar angles of 11.44 (10) and 32.50 (12)°, respectively, with respect to the 2H-chromene ring system (C1A-C9A/O1A) and C14A-C19A benzene ring; the comparable angles for molecule B are 7.71 (9) and 12.51 (12)°, respectively. The bond lengths and angles are comparable to those observed in closely related structures (Arshad et al., 2010a,b).

In the crystal structure (Fig. 3), neighbouring molecules are interconnected into two-dimensional infinite networks parallel to the (010) plane by intermolecular O3A—H3OA···O3B, N2A—H2NA···O1W, O3B—H3OB···O2B, N2B—H2NB···O2A, O1W—H1W1···N1B, O1W—H2W1···N1A and C8A—H8A···O1W hydrogen bonds (Table 1). The crystal structure is further stabilized by weak intermolecular C5B—H5B···Cg1 interactions (Table 1) involving the centroid of C14A—C19A benzene ring as well as Cg2···Cg3 aromatic stacking interactions [Cg2···Cg3 = 3.6380 (19) Å, symmetry code: -x+1, -y, -z+1 where Cg2 and Cg3 are the centroids of benzene (C14B-C19B) and 2H-pyran (C1B/O1B/C2B/C7B/C8B/C9B) rings].

Experimental

3-Hydroxybenzaldehyde thiosemicarbazone (Lv et al., 2010) and 3-[ω-bromoacetyl coumarin] (Siddiqui et al., 2009) were synthesized as reported in the literatures. A solution of 3-[ω-bromoacetyl coumarin] (2.5 mmol) and 3-hydroxybenzaldehyde thiosemicarbazone (2.5 mmol) in chloroform-ethanol (2:1) was refluxed for 1 h at 353 K. A clear solution was formed followed by the deposition of thick yellow precipitates. The reaction mixture was cooled and basified with ammonia. The title compound, (I) was purified and recrystallized as shiny yellow plates of (I) from ethanol-ethyl acetate (1:2); the water of crystallisation was presumably incorporated from the atmosphere.