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Volume 69 
Part 2 
Page o266  
February 2013  

Received 10 January 2013
Accepted 16 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.003 Å
R = 0.058
wR = 0.173
Data-to-parameter ratio = 12.6
Details
Open access

4'-Cyanobiphenyl-4-yl 7-diethylamino-2-oxo-2H-chromene-3-carboxylate

aDeapartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India,bRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, Karnataka, India,cDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and dSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C27H22N2O4, the dihedral angles between the central benzene ring and the cyanobenzene ring and the 2H-coumarin ring system (r.m.s. deviation = 0.014 Å) are 22.95 (11) and 75.59 (8)°, respectively. Both terminal C atoms of the pendant diethylamino group lie to the same side of the coumarin ring system [deviations = 1.366 (2) and 1.266 (2) Å]. In the crystal, molecules are linked by C-H...O and C-H...N hydrogen bonds and a C-H...[pi] interaction, generating a three-dimensional network.

Related literature

For the biological properties of coumarin derivatives, see: Bhat et al. (2006[Bhat, M. A., Siddiqui, N. & Khan, S. A. (2006). Indian J. Pharm. Sci. 68, 120-124.]); Chimichi et al. (2002[Chimichi, S., Boccalini, M., Cosimelli, B., Viola, G., Vedaldi, D. & Dall Acqua, F. (2002). Tetrahedron Lett. 43, 7473-7476.]).

[Scheme 1]

Experimental

Crystal data
  • C27H22N2O4

  • Mr = 438.47

  • Triclinic, [P \overline 1]

  • a = 9.652 (3) Å

  • b = 10.252 (4) Å

  • c = 11.121 (4) Å

  • [alpha] = 87.214 (10)°

  • [beta] = 86.358 (10)°

  • [gamma] = 84.348 (11)°

  • V = 1091.9 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 300 K

  • 0.24 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.984

  • 10667 measured reflections

  • 3783 independent reflections

  • 2495 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.173

  • S = 0.97

  • 3783 reflections

  • 301 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15-C20 ring.

D-H...A D-H H...A D...A D-H...A
C6-H6...O1i 0.93 2.53 3.446 (3) 170
C11-H11...N2ii 0.93 2.59 3.435 (3) 152
C16-H16...O1iii 0.93 2.54 3.465 (3) 177
C1-H1B...Cg3iv 0.96 2.82 3.626 (3) 142
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x-1, -y+2, -z+1; (iii) -x, -y+2, -z+2; (iv) x+1, y-1, z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7027 ).


Acknowledgements

The authors thank Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for the data collection.

References

Bhat, M. A., Siddiqui, N. & Khan, S. A. (2006). Indian J. Pharm. Sci. 68, 120-124.  [ChemPort]
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chimichi, S., Boccalini, M., Cosimelli, B., Viola, G., Vedaldi, D. & Dall Acqua, F. (2002). Tetrahedron Lett. 43, 7473-7476.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o266  [ doi:10.1107/S1600536813001591 ]

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