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Volume 69 
Part 3 
Page o461  
March 2013  

Received 24 February 2013
Accepted 25 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.033
wR = 0.073
Data-to-parameter ratio = 26.6
Details
Open access

N-(4-Bromophenyl)acetamide: a new polymorph

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
Correspondence e-mail: jjasinski@keene.edu

A new polymorph of the title compound, C8H8BrNO, has been determined at 173 K in the space group P21/c. The previous room-temperature structure was reported to crystallize in the orthorhombic space group Pna21 [Andreetti et al. (1968[Andreetti, G. D., Cavalca, L., Domiano, P. & Musatti, A. (1968). Acta Cryst. B24, 1195-1198.]). Acta Cryst. B24, 1195-1198]. In the crystal, molecules are linked by N-H...O hydrogen bonds forming chains along [010]. Weak C-H...[pi] interactions are also present.

Related literature

For 2-arylacetamides, see: Mijin & Marinkovic (2006[Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.]); Mijin et al. (2008[Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.]) and for amides, see: Wu et al. (2008[Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.], 2010[Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.]). For the structure of the orthorhombic polymorph, see: Andreetti et al. (1968[Andreetti, G. D., Cavalca, L., Domiano, P. & Musatti, A. (1968). Acta Cryst. B24, 1195-1198.]). For related structures, see: Praveen et al. (2011a[Praveen, A. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Narayana, B. (2011a). Acta Cryst. E67, o2602-o2603.],b[Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o2604.],c[Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011c). Acta Cryst. E67, o1826.]). For standard bond lengths, 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
  • C8H8BrNO

  • Mr = 214.06

  • Monoclinic, P 21 /c

  • a = 6.7250 (7) Å

  • b = 9.3876 (11) Å

  • c = 14.4434 (14) Å

  • [beta] = 117.750 (4)°

  • V = 806.96 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 5.03 mm-1

  • T = 173 K

  • 0.32 × 0.22 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.296, Tmax = 0.465

  • 10902 measured reflections

  • 2689 independent reflections

  • 2099 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.073

  • S = 1.04

  • 2689 reflections

  • 101 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3-C8 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.89 2.00 2.885 (2) 174
C1-H1B...Cg1ii 0.98 2.84 3.761 (3) 157
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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: SU2566 ).


Acknowledgements

BN thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP-DRS-Phase-1 programme and a BSR one-time grant. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

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.
Andreetti, G. D., Cavalca, L., Domiano, P. & Musatti, A. (1968). Acta Cryst. B24, 1195-1198.  [CrossRef] [ChemPort] [details] [ISI]
Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.  [ISI] [CrossRef] [ChemPort]
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.  [ISI] [CrossRef] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o2604.  [CSD] [CrossRef] [details]
Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011c). Acta Cryst. E67, o1826.  [CSD] [CrossRef] [details]
Praveen, A. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Narayana, B. (2011a). Acta Cryst. E67, o2602-o2603.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.  [ISI] [CrossRef] [ChemPort]
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o461  [ doi:10.1107/S1600536813005448 ]

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