Received 8 November 2010
aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad, Pakistan,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and dNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan
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In the title compound, C11H13BrN2OS, there are two independent molecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the benzene ring and the carbamothioyl group is 63.66 (molecule A) and 80.3 (0)° (molecule B). The butanamide group in molecule A is disordered [0.532 (6) and 0.468 (6) occupancy]. The carbamothioyl group is twisted by 63.6 (6) (molecule A) and 80.3 (0)° (molecule B) from the respective benzene ring. A strong intramolecular N-HO hydrogen bond occurs in each molecule. The crystal packing is stabilized by weak intermolecular N-HO and N-HS hydrogen-bond interactions, the latter forming an infinite co-operative hydrogen-bonded two-dimensional network along .
For general background to the chemistry of thiourea derivatives, see: Zhang et al. (2004); For related structures, see: Saeed et al. (2008a,b, 2009). For an epoxy resin curing agent, see: Saeed et al. (2009). For bond-length data, see: Allen et al. (1987).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2247 ).
RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
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