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Volume 66 
Part 1 
Pages o171-o172  
January 2010  

Received 1 September 2009
Accepted 18 November 2009
Online 16 December 2009

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 16.8
Details
Open access

1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide monohydrate

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: rbutcher99@yahoo.com

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-H...Br and O-H...O) with the water molecule. As a result of the Br...H-O-H...Br interactions, a zigzag chain is formed in the c-axis direction. The crystal packing is influenced by the collective action of the O-H...O and O-H...Br intermolecular interactions as well as [pi]-[pi] stacking intermolecular interactions between adjacent benzyl rings of the indole group [centroid-centroid distance = 3.721 (13) Å] and intermolecular C-H...[pi] interactions between a methyl hydrogen and the benzyl ring of the indole group. The O-H...Br interactions form a distorted tetrahedral array about the central Br atom. A MOPAC AM1 calculation provides support to these observations.

Related literature

For chemical and biological background, see: Zhu et al. (1994[Zhu, H., Clark, S. M., Benson, S. C., Rye, H. S., Glazer, A. N. & Mathies, R. A. (1994). Anal. Chem. 66, 1941-1948.]); Schwartz & Ulfelder (1992[Schwartz, H. E. & Ulfelder, K. J. (1992). Anal. Chem. 64, 1737-1740.]); Bengtsson et al. (2003[Bengtsson, M., Karlsson, H. J., Westman, G. & Kubista, M. (2003). Nucleic Acids Res. 31, e45/1.]); Hirons et al. (1994[Hirons, G. T., Fawcett, J. J. & Crissman, H. A. (1994). Cytometry, 15, 129-140.]); Kurihara et al. (1977[Kurihara, K., Toyoshima, Y. & Sukigara, M. (1977). J. Phys. Chem. 81, 1833-1837.]); Armitage & O'Brien (1992[Armitage, B. & O'Brien, D. F. (1992). J. Am. Chem. Soc. 114, 7396-7403.]); Reers et al. (1991[Reers, M., Smith, T. W. & Chen, L. B. (1991). Biochemistry, 30, 4480-4486.]); Jung & Kim (2006[Jung, M. E. & Kim, W. (2006). Bio. Med. Chem. 14, 92-97.]); Menger & Pertusati (2008[Menger, F. M. & Pertusati, P. (2008). J. Org. Chem. 73, 2939-2942.]). A geometry optimized MOPAC AM1 computational calculation was performed using WebMO Pro (Schmidt & Polik, 2007[Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro, Version 8.0.010e; WebMO, LLC: Holland, MI, USA, available from http://www.webmo.net.]).

[Scheme 1]

Experimental

Crystal data
  • C17H24NO2+·Br-·H2O

  • Mr = 372.30

  • Monoclinic, P 21 /c

  • a = 14.4528 (3) Å

  • b = 15.3367 (2) Å

  • c = 8.0810 (2) Å

  • [beta] = 99.437 (2)°

  • V = 1766.98 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 3.27 mm-1

  • T = 200 K

  • 0.55 × 0.18 × 0.12 mm

Data collection
  • Oxford Diffraction Gemini R diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.296, Tmax = 0.676

  • 13155 measured reflections

  • 3504 independent reflections

  • 3049 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.06

  • 3504 reflections

  • 209 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2O...O1W 0.84 1.82 2.637 (4) 166
O1W-H1W1...Br 0.812 (19) 2.431 (19) 3.240 (2) 175 (5)
O1W-H1W2...Bri 0.817 (19) 2.47 (2) 3.262 (3) 165 (5)
C4-H4B...Cg2i2 0.99 2.88 3.828 (3) 162
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]. Cg2 is the centroid of the C6-C11 ring.

Data collection: CrysAlis Pro (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2265 ).


Acknowledgements

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.

References

Armitage, B. & O'Brien, D. F. (1992). J. Am. Chem. Soc. 114, 7396-7403.  [CrossRef] [ChemPort] [ISI]
Bengtsson, M., Karlsson, H. J., Westman, G. & Kubista, M. (2003). Nucleic Acids Res. 31, e45/1.  [ISI] [CrossRef]
Hirons, G. T., Fawcett, J. J. & Crissman, H. A. (1994). Cytometry, 15, 129-140.  [CrossRef] [ChemPort] [PubMed] [ISI]
Jung, M. E. & Kim, W. (2006). Bio. Med. Chem. 14, 92-97.  [CrossRef] [ChemPort]
Kurihara, K., Toyoshima, Y. & Sukigara, M. (1977). J. Phys. Chem. 81, 1833-1837.  [CrossRef] [ChemPort] [ISI]
Menger, F. M. & Pertusati, P. (2008). J. Org. Chem. 73, 2939-2942.  [PubMed]
Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Reers, M., Smith, T. W. & Chen, L. B. (1991). Biochemistry, 30, 4480-4486.  [CrossRef] [ChemPort] [PubMed] [ISI]
Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro, Version 8.0.010e; WebMO, LLC: Holland, MI, USA, available from http://www.webmo.net.
Schwartz, H. E. & Ulfelder, K. J. (1992). Anal. Chem. 64, 1737-1740.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhu, H., Clark, S. M., Benson, S. C., Rye, H. S., Glazer, A. N. & Mathies, R. A. (1994). Anal. Chem. 66, 1941-1948.  [CrossRef] [ChemPort] [PubMed] [ISI]


Acta Cryst (2010). E66, o171-o172   [ doi:10.1107/S1600536809049204 ]

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