Received 2 February 2010
aDepartment of Physics, Bhavan's Sheth R.A. College of Science, Ahmedabad, Gujarat, 380 001, India,bDepartment of Chemistry, M.G. Science Institute, Navrangpura, Navrangpura, Ahmedabad, Gujarat, 380 009, India,cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA
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In the title compound, C18H11BrN6, the phenyl ring is almost coplanar [dihedral angle 7.2 (1)°] with the planar (r.m.s. deviation 0.039 Å) tricyclic ring system while the 4-bromophenyl ring makes a dihedral angle of 33.98 (6)° with the ring system. Weak intermolecular C-HN and C-HBr hydrogen-bonding interactions and - stacking [centroid-centroid distances = 3.7971 (17) and 3.5599 (16) Å] stabilize the crystal packing. A comparison of the structure to a MOPAC PM3 geometry optimization calculation in vacuo supports these observations.
For anticancer relationships, see: Hiedo & Yasuo (1960, 1961). For the synthesis of derivative compounds, see: Dave & Shukla (1997); Dave & Shah (1998). For graph-set motifs, see: Bernstein et al. (1995). For MOPAC PM3 calculations, see: Schmidt & Polik (2007).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5188 ).
RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
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