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Volume 68 
Part 1 
Page o71  
January 2012  

Received 17 November 2011
Accepted 6 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.009 Å
R = 0.076
wR = 0.181
Data-to-parameter ratio = 18.5
Details
Open access

N-[2-(4-Bromobenzoyl)ethyl]isopropylaminium chloride

aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Atatürk University, 25240 Erzurum, Turkey, and dDepartment of Chemistry, Faculty of Sciences, Atatürk University, 25240 Erzurum, Turkey
Correspondence e-mail: aaydin@kastamonu.edu.tr

The crystal structure of the title compound, C12H17BrNO+·Cl-, is stabilized by N-H...Cl and C-H...O hydrogen bonds, forming a three-dimensional network. The interactions framework is completed by C-H...[pi] contacts between a methylene group and the benzene ring of a symmetry-related molecule.

Related literature

For details of the pharmacological effects of Mannich bases and for the synthesis, see: Dimmock & Kumar (1997[Dimmock, J. R. & Kumar, P. (1997). Curr. Med. Chem. 4, 1-22.]); Gul, Gul, et al. (2005[Gul, M., Gul, H. I., Das, U. & Hanninen, O. (2005). Arzneim. Forsch. 55, 332-337.]); Gul, Sahin et al. (2005[Gul, H. I., Sahin, F., Gul, M., Ozturk, S. & Yerdelen, K. O. (2005). Arch. Pharm. 338, 335-338.]); Gul et al. (2007[Gul, H. I., Yerdelen, K. O., Gul, M., Das, U., Pandit, B., Li, P.-K., Secen, H. & Sahin, F. (2007). Arch. Pharm. 340, 195-201.]); Mete et al. (2011[Mete, E., Gul, H. I., Cetin-Atalay, R., Das, U., Sahin, E., Gul, M., Kazaz, C. & Dimmock, J. R. (2011). Arch. Pharm. Chem. Life Sci. 11, 333-339.]); Kucukoglu et al. (2011[Kucukoglu, K., Gul, M., Atalay, M., Mete, E., Kazaz, C., Hanninen, O. & Gul, H. I. (2011). Arzneim. Forsch. 61, 366-371.]); Canturk et al. (2008[Canturk, P., Kucukoglu, K., Topcu, Z., Gul, M. & Gul, H. I. (2008). Arzneim. Forsch. 58, 686-691.]); Chen et al. (1991[Chen, H. T., Jing, Y. K., Ji, Z. Z. & Zhang, B. F. (1991). Yaoxue Xuebao, 26, 183-192.]); Suleyman et al. (2007[Suleyman, H., Gul, H. I., Gul, M., Alkan, M. & Gocer, F. (2007). Biol. Pharm. Bull. 30, 63-67.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C12H17BrNO+·Cl-

  • Mr = 306.62

  • Tetragonal, P 42 /n

  • a = 19.7122 (4) Å

  • c = 7.1738 (2) Å

  • V = 2787.53 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.12 mm-1

  • T = 294 K

  • 0.15 × 0.13 × 0.11 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.632, Tmax = 0.709

  • 50060 measured reflections

  • 2836 independent reflections

  • 1617 reflections with I > 2[sigma](I)

  • Rint = 0.151

Refinement
  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.181

  • S = 1.07

  • 2836 reflections

  • 153 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.67 e Å-3

  • [Delta][rho]min = -0.81 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring.

D-H...A D-H H...A D...A D-H...A
N1-HN2...Cl1 0.86 (4) 2.26 (4) 3.102 (4) 166 (5)
N1-HN1...Cl1i 0.86 (6) 2.27 (6) 3.133 (5) 177 (9)
C12-H12B...O1ii 0.96 2.60 3.378 (7) 139
C9-H9B...Cg1iii 0.97 3.00 3.943 (6) 164
Symmetry codes: (i) [-y+{\script{1\over 2}}, x-1, -z+{\script{3\over 2}}]; (ii) -x+1, -y, -z+2; (iii) -x+1, -y, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2400 ).


Acknowledgements

The authors are indebted to the Department of Chemistry, Atatürk University, Erzurum, Turkey, for use of the X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Canturk, P., Kucukoglu, K., Topcu, Z., Gul, M. & Gul, H. I. (2008). Arzneim. Forsch. 58, 686-691.  [ChemPort]
Chen, H. T., Jing, Y. K., Ji, Z. Z. & Zhang, B. F. (1991). Yaoxue Xuebao, 26, 183-192.  [ChemPort]
Dimmock, J. R. & Kumar, P. (1997). Curr. Med. Chem. 4, 1-22.  [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Gul, M., Gul, H. I., Das, U. & Hanninen, O. (2005). Arzneim. Forsch. 55, 332-337.  [ChemPort]
Gul, H. I., Sahin, F., Gul, M., Ozturk, S. & Yerdelen, K. O. (2005). Arch. Pharm. 338, 335-338.  [CrossRef] [ChemPort]
Gul, H. I., Yerdelen, K. O., Gul, M., Das, U., Pandit, B., Li, P.-K., Secen, H. & Sahin, F. (2007). Arch. Pharm. 340, 195-201.  [CrossRef] [ChemPort]
Kucukoglu, K., Gul, M., Atalay, M., Mete, E., Kazaz, C., Hanninen, O. & Gul, H. I. (2011). Arzneim. Forsch. 61, 366-371.  [ChemPort]
Mete, E., Gul, H. I., Cetin-Atalay, R., Das, U., Sahin, E., Gul, M., Kazaz, C. & Dimmock, J. R. (2011). Arch. Pharm. Chem. Life Sci. 11, 333-339.  [CSD] [CrossRef]
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suleyman, H., Gul, H. I., Gul, M., Alkan, M. & Gocer, F. (2007). Biol. Pharm. Bull. 30, 63-67.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o71  [ doi:10.1107/S1600536811052640 ]

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