[Journal logo]

Volume 69 
Part 4 
Pages o621-o622  
April 2013  

Received 19 March 2013
Accepted 25 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 99 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.084
wR = 0.221
Data-to-parameter ratio = 12.9
Details
Open access

4-(Decyloxy)phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate

aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore, Karnataka 570 005, India,bRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore, Karnataka, India,cCenter for Advanced Materials and Department of Chemistry, Tumkur University, Tumkur, Karnataka 572103, India, and dSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India
Correspondence e-mail: spal12pm@gmail.com

The title compound, C27H29F3O5, is a liquid crystal (LC) and exhibits enantiotropic SmA phase transitions. In the crystal, the dihedral angle between the 2H-chromene ring system and the benzene ring is 62.97 (2)°. The three F atoms of the -CF3 group are disordered over two sets of sites with occupancy factors 0.71 (4):0.29 (4). In the crystal, pairs of C-H...O hydrogen bonds form inversion dimers and generate R22(10) rings. The structure also features C-H...F and C-H...[pi] interactions along [100] and [010], respectively.

Related literature

For the synthesis and liquid crystal behaviour of the title compound, see: Mahadevan et al. (2013[Mahadevan, K. M., Harish Kumar, H. N., Masagalli, J. N. & Srinivasa, H. T. (2013). Mol. Cryst. Liq. Cryst. 570, 20-35.]). For the biological activity of coumarins and their derivatives, see: Borges et al. (2005[Borges, F., Roleira, F., Milhazes, N., Santana, L. & Uriarte, E. (2005). Curr. Med. Chem. 12, 887-916.]); Kontogiorgis & Hadjipavlou-Litina (2005[Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. (2005). J. Med. Chem. 48, 6400-6408.]) and for their industrial applications, see: Hejchman et al. (2011[Hejchman, E. B., Konc, J. T., Maciejewska, D. & Kruszewska, H. (2011). Synth. Commun. 41, 2392-2402.]). For the structure of 4-(octyloxy)phenyl 2-oxo-2H-chromene-3-carboxylate, see: Palakshamurthy et al. (2013[Palakshamurthy, B. S., Sreenivasa, S., Srinivasa, H. T., Roopashree, K. R. & Devarajegowda, H. C. (2013). Acta Cryst. E69, o212.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C27H29F3O5

  • Mr = 490.50

  • Monoclinic, P 21 /c

  • a = 27.85 (3) Å

  • b = 9.281 (10) Å

  • c = 9.981 (11) Å

  • [beta] = 94.849 (18)°

  • V = 2571 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 99 K

  • 0.52 × 0.42 × 0.40 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.950, Tmax = 0.961

  • 21163 measured reflections

  • 4448 independent reflections

  • 2547 reflections with I > 2[sigma](I)

  • Rint = 0.073

Refinement
  • R[F2 > 2[sigma](F2)] = 0.084

  • wR(F2) = 0.221

  • S = 1.07

  • 4448 reflections

  • 344 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2-C7 and C12-C17 rings respectively.

D-H...A D-H H...A D...A D-H...A
C10-H10...O3i 0.95 2.56 3.396 (5) 146
C27-H27C...F1ii 0.98 2.52 3.432 (13) 154
C6-H6...Cg2i 0.95 3.09 3.899 144
C16-H16...Cg2iii 0.95 3.33 4.120 142
C3-H3...Cg1iv 0.95 3.43 4.325 163
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5309 ).


Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, and G. B. Sadananda, Department of Studies and Research in Physics, U·C.S. Tumkur University, Tumkur.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Borges, F., Roleira, F., Milhazes, N., Santana, L. & Uriarte, E. (2005). Curr. Med. Chem. 12, 887-916.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hejchman, E. B., Konc, J. T., Maciejewska, D. & Kruszewska, H. (2011). Synth. Commun. 41, 2392-2402.  [ISI] [CrossRef] [ChemPort]
Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. (2005). J. Med. Chem. 48, 6400-6408.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]
Mahadevan, K. M., Harish Kumar, H. N., Masagalli, J. N. & Srinivasa, H. T. (2013). Mol. Cryst. Liq. Cryst. 570, 20-35.  [CrossRef] [ChemPort]
Palakshamurthy, B. S., Sreenivasa, S., Srinivasa, H. T., Roopashree, K. R. & Devarajegowda, H. C. (2013). Acta Cryst. E69, o212.  [CrossRef] [details]
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o621-o622   [ doi:10.1107/S1600536813008222 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.