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

Winstead, A.; Hart, K.; Hijji, Y.M.; Jasinski, J.P.; Butcher, R.J.

doi:10.1107/S1600536809049204

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 (C-C) = 0.003 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 16.8
Details

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

Angela Winstead,^a Krystal Hart,^a Yousef M. Hijji,^a Jerry P. Jasinski ^b and Ray J. Butcher ^c ^*

^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-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 [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-HBr 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); 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).

Experimental

Crystal data

C₁₇H₂₄NO₂⁺·Br^-·H₂O
M_r = 372.30
Monoclinic, P 2₁ /c
a = 14.4528 (3) Å
b = 15.3367 (2) Å
c = 8.0810 (2) Å
= 99.437 (2)°
V = 1766.98 (6) Å³
Z = 4
Cu K radiation
= 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 $[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.296, T_max = 0.676
13155 measured reflections
3504 independent reflections
3049 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(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
_max = 0.52 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2OO1W	0.84	1.82	2.637 (4)	166
O1W-H1W1Br	0.812 (19)	2.431 (19)	3.240 (2)	175 (5)
O1W-H1W2Brⁱ	0.817 (19)	2.47 (2)	3.262 (3)	165 (5)
C4-H4BCg2ⁱ²	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); 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 ).

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

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Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
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Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro, Version 8.0.010e; WebMO, LLC: Holland, MI, USA, available from http://www.webmo.net.
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organic compounds