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Volume 69 
Part 8 
Pages o1355-o1356  
August 2013  

Received 8 June 2013
Accepted 25 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.104
wR = 0.316
Data-to-parameter ratio = 12.2
Details
Open access

4-[4-(Heptyloxy)benzoyloxy]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,bDepartment of Chemistry Kuvempu University, Shankaraghatta Shimoga, Karnataka, India,cDepartment of Studies and Research in Chemistry, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India, and dDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: palaksha.bspm@gmail.com

The title compound, C31H27F3O7, is a liquid crystal and exhibits enantiotropic SmA and nematic phase transitions. In the crystal, the the 2H-chromene ring system makes dihedral angles of 54.46 (17) and 7.79 (16)°, respectively, with the central benzene ring and 4-(heptyloxy)benzene ring. The three F atoms of the -CF3 group are disordered over two sets of sites, with an occupancy ratio of 0.62 (3):0.38 (3). The crystal structre features two pairs of C-H...O hydrogen bonds, which form inversion dimers and generate R22(10) and R22(30) ring patterns. C-H...O interactions along [100] and C-H...[pi] interactions futher consolidate the packing, leading to a three-dimensional network.

Related literature

For similar structures, see: Palakshamurthy, Sreenivasa et al. (2013[Palakshamurthy, B. S., Sreenivasa, S., Srinivasa, H. T., Roopashree, K. R. & Devarajegowda, H. C. (2013). Acta Cryst. E69, o212.]), Palakshamurthy, Devarajegowda et al. (2013[Palakshamurthy, B. S., Devarajegowda, H. C., Srinivasa, H. T., Sreenivasa, S. & Vijithkumar, (2013). Acta Cryst. E69, o621-o622.]). For graph-set notation for hydrogen bonds, 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
  • C31H27F3O7

  • Mr = 568.53

  • Triclinic, [P \overline 1]

  • a = 5.6810 (3) Å

  • b = 16.036 (2) Å

  • c = 16.2954 (18) Å

  • [alpha] = 68.940 (12)°

  • [beta] = 88.914 (6)°

  • [gamma] = 88.486 (7)°

  • V = 1384.8 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.32 × 0.24 × 0.18 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.966, Tmax = 0.981

  • 8822 measured reflections

  • 4876 independent reflections

  • 2837 reflections with I > 2[sigma](I)

  • Rint = 0.079

Refinement
  • R[F2 > 2[sigma](F2)] = 0.104

  • wR(F2) = 0.316

  • S = 0.99

  • 4876 reflections

  • 399 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C12-C17 and C19-C24 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C3-H3...O6i 0.93 2.53 3.313 (5) 142
C8-H8...O3i 0.93 2.44 3.277 (4) 150
C16-H16...O6ii 0.93 2.45 3.350 (5) 163
C14-H14...Cg2iii 0.93 2.81 3.517 (5) 133
C23-H23...Cg1iv 0.93 2.94 3.650 (5) 134
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x+1, y, z; (iii) -x+2, -y+1, -z; (iv) -x+1, -y+1, -z.

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: 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: KJ2229 ).


Acknowledgements

The authors thank Professor T. N. Guru Row and Vijithkumar, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for the data collection. BSPM thanks H. T. Srinivasa, Raman Research Institute, Bangalore, for his help with the characterization.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Palakshamurthy, B. S., Devarajegowda, H. C., Srinivasa, H. T., Sreenivasa, S. & Vijithkumar, (2013). Acta Cryst. E69, o621-o622.
Palakshamurthy, B. S., Sreenivasa, S., Srinivasa, H. T., Roopashree, K. R. & Devarajegowda, H. C. (2013). Acta Cryst. E69, o212.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1355-o1356   [ doi:10.1107/S1600536813020679 ]

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