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Volume 69 
Part 4 
Page o470  
April 2013  

Received 30 January 2013
Accepted 19 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.022
wR = 0.046
Data-to-parameter ratio = 19.0
Details
Open access

D-Phenylglycinium bromide

aCrystal Research Laboratory, Department of Physics, Anna University, Chennai 600 025, India, and bDepartment of Chemistry, Loyola College (Autonomous), Chennai 600 034, India
Correspondence e-mail: krgkrishnan@annauniv.edu

In the crystal of the title salt, C8H10NO2+·Br-, the bromide anions and the phenylglycinium cations are linked through N-H...Br, O-H...Br and C-H...O hydrogen bonds, generating sheets lying parallel to (001).

Related literature

For a similar compound with a different halogen anion, see: Ravichandran et al. (1998[Ravichandran, S., Dattagupta, J. K. & Chakrabarti, C. (1998). Acta Cryst. C54, 499-501.]). For related structures and background, see: Srinivasan et al. (2001[Srinivasan, N., Sridhar, B. & Rajaram, R. K. (2001). Acta Cryst. E57, o754-o756.]); Bouchouit et al. (2004[Bouchouit, K., Bendheif, L. & Benali-Cherif, N. (2004). Acta Cryst. E60, o272-o274.]); Ramaswamy et al. (2001[Ramaswamy, S., Sridhar, B., Ramakrishnan, V. & Rajaram, R. K. (2001). Acta Cryst. E57, o1149-o1151.]); Bouacida et al. (2006[Bouacida, S., Merazig, H. & Benard-Rocherulle, P. (2006). Acta Cryst. E62, o838-o840.]); Thomsen et al. (1994[Thomsen, C., Boel, E. & Suzdak, P. D. (1994). Eur. J. Pharmacol. 267, 77-84.]). For biological importance, see: Satyam et al. (1996[Satyam, A., Hocker, M. D., Kanemaguire, K. A., Morgan, A. S., Villar, H. O. & Lyttle, M. H. (1996). J. Med. Chem. 39, 1736-1747.]); Jayasinghe et al. (1994[Jayasinghe, L. R., Datta, A., Ali, S. M., Zymunt, J., Van der Velde, D. G. & Georg, G. I. (1994). J. Med. Chem. 37, 2981-2984.]); Chun et al. (2010[Chun, L. W., Yang, B. F., Hsiao, H. L., Tung, H. T., Ming, C. T. & Hui, P. W. (2010). J. Biomed. Sci. 17, 71-78.]); Thomas & West (2011[Thomas, G. & West, G. B. (2011). J. Pharm. Pharmacol. 26, 151-152.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10NO2+·Br-

  • Mr = 232.08

  • Orthorhombic, P 21 21 21

  • a = 5.5240 (5) Å

  • b = 7.4735 (5) Å

  • c = 23.1229 (18) Å

  • V = 954.60 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.27 mm-1

  • T = 295 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS, APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.317, Tmax = 0.415

  • 5824 measured reflections

  • 2170 independent reflections

  • 2003 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.046

  • S = 1.03

  • 2170 reflections

  • 114 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])

  • Flack parameter: 0.011 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1B...Br1i 0.89 2.54 3.3586 (17) 154
N1-H1C...Br1ii 0.89 2.57 3.429 (2) 163
N1-H1A...Br1 0.89 2.45 3.3166 (18) 164
O1-H1D...Br1iii 0.82 2.39 3.2027 (17) 171
C7-H7...O2iv 0.98 2.59 3.527 (3) 159
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z; (iii) x-1, y-1, z; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SADABS, APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). SADABS, APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). SADABS, APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2465 ).


Acknowledgements

The authors are grateful to Professor K. Sivakumar, Department of Physics, Anna University, Chennai-25, for fruitful scientific discussions. The authors are thankful to the SAIF, IIT Madras, Chennai-36, India, for the X-ray data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bouacida, S., Merazig, H. & Benard-Rocherulle, P. (2006). Acta Cryst. E62, o838-o840.  [CSD] [CrossRef] [details]
Bouchouit, K., Bendheif, L. & Benali-Cherif, N. (2004). Acta Cryst. E60, o272-o274.  [CSD] [CrossRef] [details]
Bruker (2004). SADABS, APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Chun, L. W., Yang, B. F., Hsiao, H. L., Tung, H. T., Ming, C. T. & Hui, P. W. (2010). J. Biomed. Sci. 17, 71-78.  [ISI] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Jayasinghe, L. R., Datta, A., Ali, S. M., Zymunt, J., Van der Velde, D. G. & Georg, G. I. (1994). J. Med. Chem. 37, 2981-2984.  [CrossRef] [ChemPort] [PubMed] [ISI]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Ramaswamy, S., Sridhar, B., Ramakrishnan, V. & Rajaram, R. K. (2001). Acta Cryst. E57, o1149-o1151.  [CSD] [CrossRef] [details]
Ravichandran, S., Dattagupta, J. K. & Chakrabarti, C. (1998). Acta Cryst. C54, 499-501.  [CSD] [CrossRef] [details]
Satyam, A., Hocker, M. D., Kanemaguire, K. A., Morgan, A. S., Villar, H. O. & Lyttle, M. H. (1996). J. Med. Chem. 39, 1736-1747.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Srinivasan, N., Sridhar, B. & Rajaram, R. K. (2001). Acta Cryst. E57, o754-o756.  [CSD] [CrossRef] [details]
Thomas, G. & West, G. B. (2011). J. Pharm. Pharmacol. 26, 151-152.  [CrossRef]
Thomsen, C., Boel, E. & Suzdak, P. D. (1994). Eur. J. Pharmacol. 267, 77-84.  [ChemPort] [PubMed] [ISI]


Acta Cryst (2013). E69, o470  [ doi:10.1107/S1600536813004807 ]

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