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

Sreenivasa, S.; Srinivasa, H.T.; Palakshamurthy, B.S.; Kumar, V.; Devarajegowda, H.C.

doi:10.1107/S1600536813001591

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 (C-C) = 0.003 Å
R = 0.058
wR = 0.173
Data-to-parameter ratio = 12.6
Details

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

S. Sreenivasa,^a H. T. Srinivasa,^b B. S. Palakshamurthy,^c Vijith Kumar ^d and H. C. Devarajegowda ^c ^*

^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-HO and C-HN 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); Chimichi et al. (2002).

Experimental

Crystal data

C₂₇H₂₂N₂O₄
M_r = 438.47
Triclinic, $[P \overline 1]$
a = 9.652 (3) Å
b = 10.252 (4) Å
c = 11.121 (4) Å
= 87.214 (10)°
= 86.358 (10)°
= 84.348 (11)°
V = 1091.9 (6) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.979, T_max = 0.984
10667 measured reflections
3783 independent reflections
2495 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.173
S = 0.97
3783 reflections
301 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15-C20 ring.

D-HA	D-H	HA	DA	D-HA
C6-H6O1ⁱ	0.93	2.53	3.446 (3)	170
C11-H11N2ⁱⁱ	0.93	2.59	3.435 (3)	152
C16-H16O1ⁱⁱⁱ	0.93	2.54	3.465 (3)	177
C1-H1BCg3^iv	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); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds