(E)-3-(2-{2-[1-(3-Hy­droxy­phen­yl)ethyl­idene]hydrazin­yl}-1,3-thia­zol-4-yl)-2H-chromen-2-one

Afsheen Arshad; Hasnah Osman; Chan Kit Lam; Madhukar Hemamalini; Hoong-Kun Fun

doi:10.1107/S1600536811012189

. 2011 Apr 7;67(Pt 5):o1072–o1073. doi: 10.1107/S1600536811012189

(E)-3-(2-{2-[1-(3-Hydroxyphenyl)ethylidene]hydrazinyl}-1,3-thiazol-4-yl)-2H-chromen-2-one

Afsheen Arshad ^a, Hasnah Osman ^a,^‡, Chan Kit Lam ^b, Madhukar Hemamalini ^c, Hoong-Kun Fun ^c,^*,^§

PMCID: PMC3089171 PMID: 21754396

Abstract

In the title compound, C₂₀H₁₅N₃O₃S, the thiazole ring is approximately planar, with a maximum deviation of 0.003 (1) Å, and makes dihedral angles of 7.44 (6) and 1.88 (6)° with the hydroxy-substituted phenyl ring and the pyran ring, respectively. The hydroxyl group is disordered over two sets of sites, with an occupancy ratio of 0.567 (3):0.433 (3). In the crystal, the major disorder component molecules are connected via bifurcated (three-centre) O—H⋯O and C—H⋯O hydrogen bonds, generating R ¹ ₂(6) motifs and resulting in supramolecular chains along the a axis. In the minor occupancy component, however, molecules are connected via C—H⋯O hydrogen bonds, forming supramolecular chains along the b axis. Furthermore, the crystal structure is stabilized by π–π interactions between the thiazole rings [centroid–centroid distance = 3.5476 (7) Å].

Related literature

For details of coumarin derivatives, see: Raghu et al. (2009 ▶); Gursoy & Karali (2003 ▶); Chimenti et al. (2010 ▶); Kamal et al. (2009 ▶); Kalkhambkar et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For the synthesis of (E)-2-(1-(3-hydroxyphenyl)ethylidene)hydrazinecarbothioamide, see: Greenbaum et al. (2004 ▶) and for that of 3-[ω-bromoacetyl coumarin, see: Nadeem et al. (2009 ▶).

Experimental

Crystal data

C₂₀H₁₅N₃O₃S
M _r = 377.41
Monoclinic,
a = 9.1569 (1) Å
b = 9.9070 (2) Å
c = 18.7478 (3) Å
β = 92.040 (1)°
V = 1699.67 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.34 × 0.32 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T _min = 0.929, T _max = 0.979
29914 measured reflections
5400 independent reflections
4641 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.105
S = 1.07
5400 reflections
271 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.30 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/S1600536811012189/wn2428sup1.cif

e-67-o1072-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012189/wn2428Isup2.hkl

e-67-o1072-Isup2.hkl^{(259.1KB, 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
O3—H1OA⋯O2ⁱ	0.89 (4)	1.89 (4)	2.7693 (19)	171 (4)
C19—H19A⋯O2ⁱ	0.93	2.59	3.3020 (17)	133

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Symmetry code: (i) Inline graphic .

Acknowledgments

AA, HO, CKL thank the Malaysian Government and Universiti Sains Malaysia (USM) for a grant [1001/PKimia/811133] to conduct this work. AA also thanks USM for a fellowship. HKF and MH thank the Malaysian Government and USM for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks USM for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Coumarin derivatives containing the thiazolyl unit exhibit promising antimicrobial activities against different microbial strains (Raghu et al., 2009), including Mycobacterium tuberculosis (Gursoy et al., 2003) and Helicobacter pylori (Chimenti et al., 2010). These types of compounds are also reported to be good anticancer (Kamal et al., 2009), analgesic and anti-inflammatory agents (Kalkhambkar et al., 2007). The title compound is a new derivative of coumarin with the thiazole ring. We present here its crystal structure.

In the molecular structure of the compound, (Fig.1), the thiazole (S1/N1/C10–C12) ring is approximately planar, with a maximum deviation of 0.003 (1) Å for atom C11. The central thiazole (S1/N1/C10–C12) ring makes dihedral angles of 7.44 (6)° and 1.88 (6)° with the hydroxyl- substituted phenyl (C14–C19) ring and the pyran (O1/C1,C2/C7–C9) ring, respectively. The hydroxyl group is disordered over two sites, with an occupancy ratio 0.567 (3):0.433 (3).

In the crystal packing (Fig. 2), the major component molecules are connected via bifurcated O3—H1OA···O2 and C19—H19A···O2 hydrogen bonds, generating R¹₂(6) motifs, (Bernstein et al., 1995), resulting in supramolecular chains along the a-axis. In the minor component, however, molecules are connected via C19—H19A···O2 hydrogen bonds, forming one-dimensional supramolecular chains along the b-axis (Fig. 3). Furthermore, the crystal structure is stabilized by π···π interactions between the thiazole (S1/N1/C10–C12) rings [centroid-centroid distance = 3.5476 (7) Å; -x, -y, 1-z].

Experimental

(E)-2-(1-(3-Hydroxyphenyl)ethylidene)hydrazinecarbothioamide (Greenbaum et al., 2004) and 3-[ω-bromoacetyl coumarin] (Nadeem et al., 2009) were synthesized as reported in the literature. The title compound was prepared by treating (E)-2-(1-(3-hydroxyphenyl)ethylidene)hydrazinecarbothioamide (2.5 mmol) with 3-ω-bromoacetylcoumarin (2.5 mmol) in a chloroform-ethanol (2:1) mixture. The reaction mixture was refluxed for 2–3 hours at 60°C to yield dense yellow precipitates. The precipitates were filtered and boiled with water containing sodium acetate. The title compound was recrystallized as golden crystals from ethanol:chloroform (3:1).