Abstract
The title compound, C12H9BrN2OS2, was obtained by reacting 6-bromobenzo[d]thiazole-2-carbonitrile in iso-propanol with ethyl 2-mercapto-2-methylpropanoate at reflux temperature for several hours. The resulting dimethyloxyluciferin derivative shows partial double-bond character of the carbon–carbon bond between the two heterocyclic moieties [C—C = 1.461 (3) Å]. This double bond restricts rotation around this C—C axis, therefore leading to an almost planar molecular structure [N—C—C—S torsion angle = 9.7 (3)°]. The five-membered thiazoline ring is not completely planar as a result of the bulky S atom [C—S—C—C torsion angle = 5.17 (12)°].
Highlights
The title compound, C12H9BrN2OS2, was obtained by reacting 6-bromobenzo[d]thiazole-2-carbonitrile in iso-propanol with ethyl 2-mercapto-2-methylpropanoate at reflux temperature for several hours
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2444)
Br1—C4 S1—C2 S1—C1 S1—S2 S2—C8 S2—C10 O1—C9 N1—C1 N1—C7 N2—C8 N2—C9 C1—C8 C2—C3 C2—C7 C3—C4
Summary
The resulting dimethyloxyluciferin derivative shows partial double-bond character of the carbon– carbon bond between the two heterocyclic moieties [C—C = 1.461 (3) A ]. This double bond restricts rotation around this C—C axis, leading to an almost planar molecular structure [N—C—C—S torsion angle = 9.7 (3)]. Related literature For the chemi- and bioluminescence of firefly luciferin and related compounds, see: Jung et al (1975); White et al (1961, 1979); Branchini et al (2002). For structural modifications of firefly luciferin, see: Meroni et al (2009); McCutcheon et al (2012); Branchini et al (2012); Wurfel (2012).
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