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Volume 69 
Part 7 
Page o1056  
July 2013  

Received 17 May 2013
Accepted 4 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.107
Data-to-parameter ratio = 19.0
Details
Open access

4-Bromomethyl-6-tert-butyl-2H-chromen-2-one

aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, India
Correspondence e-mail: noorsb@rediffmail.com, noorsb05@gmail.com

In the crystal structure of the title compound, C14H15BrO2, weak C-H...O interactions link the molecules into zigzag chains extending along the c-axis direction. These chains are further assembled into (100) layers via [pi]-[pi] stacking interactions between inversion-related chromenone fragments [interplanar distance = 3.376 (2) Å].

Related literature

For therapeutic properties of coumarin derivatives, see: Lacy & O'Kennedy (2004[Lacy, A. & O'Kennedy, R. (2004). Curr. Pharm. Des. 10, 3797-3811.]); Mustafa et al. (2011[Mustafa, M. S., El-Abadelah, M. M., Zihlif, M. A., Naffa, R. G. & Mubarak, M. S. (2011). Molecules, 16, 4305-4317.]). For structural features of coumarins, see: Moorthy et al. (2003[Moorthy, J. N., Venkatakrishnan, P. & Singh, A. S. (2003). CrystEngComm, 5, 507-513.]). For related structures, see: Gowda et al. (2010[Gowda, R., Basanagouda, M., Kulkarni, M. V. & Gowda, K. V. A. (2010). Acta Cryst. E66, o2906.]); Fun et al. (2011[Fun, H.-K., Goh, J. H., Wu, D. & Zhang, Y. (2011). Acta Cryst. E67, o136.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15BrO2

  • Mr = 295.17

  • Monoclinic, P 21 /c

  • a = 10.3311 (19) Å

  • b = 16.830 (3) Å

  • c = 7.3374 (14) Å

  • [beta] = 97.518 (3)°

  • V = 1264.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.24 mm-1

  • T = 100 K

  • 0.18 × 0.16 × 0.16 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA.]) Tmin = 0.593, Tmax = 0.625

  • 7522 measured reflections

  • 2737 independent reflections

  • 2074 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.107

  • S = 1.05

  • 2737 reflections

  • 144 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.78 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O2i 0.95 2.42 3.334 (4) 162
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker,1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA.]); cell refinement: SAINT-Plus (Bruker,1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA.]); data reduction: SAINT-Plus; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1996)[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]; software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2575 ).


Acknowledgements

NSB and KSS are thankful to the University Grants Commission (UGC), India, for financial assistance. HN and PKB thank UGC for fellowships.

References

Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Goh, J. H., Wu, D. & Zhang, Y. (2011). Acta Cryst. E67, o136.  [CrossRef] [IUCr Journals]
Gowda, R., Basanagouda, M., Kulkarni, M. V. & Gowda, K. V. A. (2010). Acta Cryst. E66, o2906.  [CSD] [CrossRef] [IUCr Journals]
Lacy, A. & O'Kennedy, R. (2004). Curr. Pharm. Des. 10, 3797-3811.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Moorthy, J. N., Venkatakrishnan, P. & Singh, A. S. (2003). CrystEngComm, 5, 507-513.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Mustafa, M. S., El-Abadelah, M. M., Zihlif, M. A., Naffa, R. G. & Mubarak, M. S. (2011). Molecules, 16, 4305-4317.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.


Acta Cryst (2013). E69, o1056  [ doi:10.1107/S1600536813015511 ]

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