Received 1 September 2009
aDepartment of Chemistry, Morgan State University, Baltimore, MD 21251, USA,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: firstname.lastname@example.org
In the title compound, C17H24NO2+·Br-·H2O, the pentyl group chain in the cation extends nearly perpendicular [N-C-C-C = -64.4 (3)°] to the mean plane of the indole ring with the carboxyl end group twisted such that the dihedral angle between the mean planes of the indole and carboxy groups measures 43.2 (4)°. Both ions in the salt form intermolecular hydrogen bonds (O-HBr and O-HO) with the water molecule. As a result of the BrH-O-HBr interactions, a zigzag chain is formed in the c-axis direction. The crystal packing is influenced by the collective action of the O-HO and O-HBr intermolecular interactions as well as - stacking intermolecular interactions between adjacent benzyl rings of the indole group [centroid-centroid distance = 3.721 (13) Å] and intermolecular C-H interactions between a methyl hydrogen and the benzyl ring of the indole group. The O-HBr interactions form a distorted tetrahedral array about the central Br atom. A MOPAC AM1 calculation provides support to these observations.
For chemical and biological background, see: Zhu et al. (1994); Schwartz & Ulfelder (1992); Bengtsson et al. (2003); Hirons et al. (1994); Kurihara et al. (1977); Armitage & O'Brien (1992); Reers et al. (1991); Jung & Kim (2006); Menger & Pertusati (2008). A geometry optimized MOPAC AM1 computational calculation was performed using WebMO Pro (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: FL2265 ).
AW and YH acknowledges support from by DOE-CETBR grant No. DE-FG02-03ER63580 and NSF-RISE Award No. HRD-0627276. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
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