(E)-6-Bromo-3-{2-[2-(2-meth­oxy­benzyl­idene)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/S1600536811024536

. 2011 Jun 25;67(Pt 7):o1825. doi: 10.1107/S1600536811024536

(E)-6-Bromo-3-{2-[2-(2-methoxybenzylidene)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: PMC3152023 PMID: 21837193

Abstract

In the title compound, C₂₀H₁₄BrN₃O₃S, the molecule adopts an E configuration about the central C=N double bond. The chromene ring system and the thiazole ring are approximately planar [maximum deviations = 0.029 (3) and 0.007 (3) Å, respectively]. The chromene ring system is inclined at angles of 7.37 (12) and 13.90 (13)° with respect to the thiazole and benzene rings, respectively, while the thiazole ring makes a dihedral angle of 12.58 (15)° with the benzene ring. In the crystal, molecules are connected by N—H⋯O hydrogen bonds, forming C(8) supramolecular chains along the c axis.

Related literature

For related structures, further synthetic details and background references, see: Arshad et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₂₀H₁₄BrN₃O₃S
M _r = 456.31
Monoclinic,
a = 7.2802 (12) Å
b = 19.551 (3) Å
c = 14.0638 (18) Å
β = 113.352 (7)°
V = 1837.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.38 mm⁻¹
T = 296 K
0.43 × 0.07 × 0.04 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.427, T _max = 0.921
11951 measured reflections
4266 independent reflections
2786 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.089
S = 1.01
4266 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 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/S1600536811024536/hb5923sup1.cif

e-67-o1825-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024536/hb5923Isup2.hkl

e-67-o1825-Isup2.hkl^{(209.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024536/hb5923Isup3.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
N2—H1⋯O2ⁱ	0.94	2.10	3.021 (3)	164

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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 Universiti Sains Malaysia for a fellowship. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

As part of our ongoing studies of substituted coumarins (Arshad et al., 2011a,b) we now present the crystal structure of the title compound, (I).

In (I), the molecule adopts an E configuration about the central C13═N3 double bond. The chromene (O1/C1–C9) and the thiazole (S1/N1/C10–C12) rings are approximately planar [maximum deviations of 0.029 (3) Å for atom C4 and 0.007 (3) Å for atom C12, respectively]. The chromene (O1/C1–C9) ring system is inclined at angles of 7.37 (12)° and 13.90 (13)° with respect to the thiazole (S1/N1/C10–C12) and benzene (C14–C19) rings, respectively, while the thiazole (S1/N1/C10–C12) ring makes a dihedral angle of 12.58 (15)° with the benzene ((C14–C19) ring.

In the crystal (Fig. 2), the molecules are connected by N2—H1···O2 (Table 1) hydrogen bonds forming supramolecular chains along the c-axis.

Experimental

The title compound was synthesized by the same procedure as mentioned in our previous papers (Arshad et al., 2011a,b). 2-Methoxy benzylidene thiosemicarbazone was reacted with 6-bromo-3- (2-bromoacetyl)-2H-chromen-2-one in chloroform-ethanol (2:1) mixture. The reaction mixture was refluxed for 2–3 hours at 60°C to get dense yellow precipitates. It was cooled in ice bath and basified with ammonia to pH 7–8. The title compound (I) was recrystallized from CHCl₃–EtOH (1:1) as golden yellow needles.