(E)-6-Bromo-3-{2-[2-(2-meth­oxy­benzyl­idene)hydrazin­yl]-1,3-thia­zol-4-yl}-2H-chromen-2-one

Arshad, A.; Osman, H.; Lam, C.K.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811024536

Volume 67
Part 7
Page o1825
July 2011

Received 21 June 2011
Accepted 22 June 2011
Online 25 June 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.038
wR = 0.089
Data-to-parameter ratio = 16.9
Details

(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 and Hoong-Kun Fun ^c ^*⁺⁺

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

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-HO 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, P 2₁ /c
a = 7.2802 (12) Å
b = 19.551 (3) Å
c = 14.0638 (18) Å
= 113.352 (7)°
V = 1837.8 (5) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.089
S = 1.01
4266 reflections
253 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1O2ⁱ	0.94	2.10	3.021 (3)	164
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: HB5923 ).

Acknowledgements

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.

References

Arshad, A., Osman, H., Lam, C. K., Hemamalini, M. & Fun, H.-K. (2011a). Acta Cryst. E67, o1072-o1073.
Arshad, A., Osman, H., Lam, C. K., Hemamalini, M. & Fun, H.-K. (2011b). Acta Cryst. E67, o1007-o1008.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds