7-Chloro-3-phenyl­benzo[4,5]thia­zolo[2,3-c][1,2,4]triazole

Hoong-Kun Fun; Safra Izuani Jama Asik; M Himaja; D Munirajasekhar; B K Sarojini

doi:10.1107/S1600536811039456

. 2011 Sep 30;67(Pt 10):o2810. doi: 10.1107/S1600536811039456

7-Chloro-3-phenylbenzo[4,5]thiazolo[2,3-c][1,2,4]triazole

Hoong-Kun Fun ^a,^*,^‡, Safra Izuani Jama Asik ^a, M Himaja ^b, D Munirajasekhar ^b, B K Sarojini ^c

PMCID: PMC3201329 PMID: 22058831

Abstract

In the title compound, C₁₄H₈ClN₃S, the dihedral angle between the approximately planar triple-fused ring system (r.m.s. deviation = 0.065 Å) and the pendant phenyl ring is 62.25 (5)°. In the crystal, molecules are linked into infinite chains along the c-axis direction by C—H⋯N hydrogen bonds. Aromatic π–π stacking interactions [centroid–centroid distances = 3.7499 (8) and 3.5644 (8) Å] and weak C—H⋯π interactions are also observed.

Related literature

For the biological activity of benzothiozole derivatives, see: Yaseen et al. (2006 ▶); Kini et al. (2007 ▶); Munirajasekhar et al. (2011 ▶); Gurupadayya et al. (2008 ▶); Bowyer et al. (2007 ▶); Mittal et al. (2007 ▶); Pozas et al. (2005 ▶); Rana et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₈ClN₃S
M _r = 285.74
Monoclinic,
a = 16.9941 (13) Å
b = 5.8895 (5) Å
c = 12.0930 (9) Å
β = 91.770 (1)°
V = 1209.77 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 296 K
0.41 × 0.31 × 0.18 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.828, T _max = 0.919
14981 measured reflections
4033 independent reflections
3342 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.101
S = 1.02
4033 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 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/S1600536811039456/hb6414sup1.cif

e-67-o2810-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039456/hb6414Isup2.hkl

e-67-o2810-Isup2.hkl^{(197.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039456/hb6414Isup3.cml

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

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

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯N3ⁱ	0.93	2.57	3.3135 (16)	138
C4—H4A⋯Cg3ⁱⁱ	0.93	2.92	3.5851 (15)	130

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

HKF and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grants (Nos.1001/PFIZIK/811160 and 1001/PFIZIK/ 811151).

supplementary crystallographic information

Comment

Benzothiazole derivatives have emerged as significant components in various diversified therapeutic applications. Literature review reveals that benzothiazoles and their derivatives show considerable activity including potent inhibition of human immunodeficiency virus type 1 (HIV-1), replication by HIV-1 protease inhibition (Yaseen et al.,2006), antitumor (Kini et al., 2007), anthelmintic (Munirajasekhar et al., 2011), analgesic, anti-inflammatory (Gurupadayya et al.,2008), antimalarial (Bowyer et al.,2007), antifungal (Mittal et al., 2007), anticandidous (Pozas et al.,2005) and various CNS activities (Rana et al., 2008). The present work describes the synthesis and crystal structure of the title compound, 7-Chloro-3- phenylbenzo[4,5]thiazolo[2,3-c][1,2,4]triazole, which was prepared from the reaction of 2-benzylidene-1-(6-chlorobenzo[d]thiazol-2-yl)hydrazine treated with iodobenzene diacetate.

In the title compound of (I), (Fig. 1), the benzene (C9–C14) ring makes dihedral angles of 5.59 (7) and 2.45 (6)° with the thiazole ring (S1/N1/C8/C9/C14) and the mean plane of triazole (N1–N3/C7/C8) ring, respectively. The dihedral angle between the two benzene (C1–C6 and C9–C14) rings is 64.11 (6)°.

In the crystal structure of (Fig. 2), the molecules are linked into infinite chains along the c axis by C10—H10A···N3 hydrogen bonds. π–π stacking interactions are observed between the triazole (N1–N3/C7/C8) ; centroid Cg2) and benzene (C1–C6) ; centroid Cg3) rings with a distance of Cg2···Cg3 = 3.7499 (8) Å and between triazole (N1–N3/C7/C8) ; centroid Cg2) and benzene (C9–C14) ; centroid Cg4) rings with a separation of Cg2···Cg4 = 3.5644 (8) Å. Furthermore the crystal structure is stabilized by weak C—H···π interactions (Table 1) with distance of 3.5851 (15) Å.

Experimental

To a solution of the 2-benzylidene-1-(6-chlorobenzo[d]thiazol-2-yl)hydrazine (2 mmol) in dichloromethane (10 mL) at room temperature, iodobenzene diacetate (2 mmol) was added in 2–3 portions over 5 min. The resultant reaction mixture was stirred for 45 min. The solvent was evaporated under high vacuum and then purified by column chromatography (40% ethyl acetate in chloroform). The product was recrystalized from ethanol to give colourless blocks.