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

S Sreenivasa; H T Srinivasa; B S Palakshamurthy; Vijith Kumar; H C Devarajegowda

doi:10.1107/S1600536813001591

. 2013 Jan 19;69(Pt 2):o266. doi: 10.1107/S1600536813001591

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, H C Devarajegowda ^c,^*

PMCID: PMC3569796 PMID: 23424542

Abstract

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⋯π 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,
a = 9.652 (3) Å
b = 10.252 (4) Å
c = 11.121 (4) Å
α = 87.214 (10)°
β = 86.358 (10)°
γ = 84.348 (11)°
V = 1091.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.173
S = 0.97
3783 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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 Material

Click here for additional data file.^{(23.3KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001591/hb7027sup1.cif

e-69-0o266-sup1.cif^{(23.3KB, cif)}

Click here for additional data file.^{(181.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001591/hb7027Isup2.hkl

e-69-0o266-Isup2.hkl^{(181.7KB, hkl)}

Click here for additional data file.^{(8.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813001591/hb7027Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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⋯Cg3^iv	0.96	2.82	3.626 (3)	142

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

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

supplementary crystallographic information

Comment

Coumarins are well known for displaying a broad range of biological activities like anti- inflammatory, anticonvulsant (Bhat et al., 2006) and antitumor agents (Chimichi et al., 2002). As part of our studies in this area, we now report the synthesis and crystal structure (Fig. 1) of the title cyanobiphenyl coumarin, (I), derived from the reaction of 7-diethylamino coumarin.

The 2H-chromene ring (O2/C5–C13) system in (I) is almost planar, with a maximum deviation of 0.025 (2) Å for atom C13. The dihedral angle between 2H-chromene ring (O2/C5–C13) with the benzene(C15–C20) terminal benzene(C21—C26) rings are 75.59 (8)° and 56.02 (1)° respectively. The crystal structure is characterized by intermolecular C6—H6···O1, C11—H11···N2 and C16—H16···O1 hydrogen bonding and also features C—H..π [C_g(3)(C15–C20) interactions (Table.1). Crystal packing for the title compound with hydrogen bonds drawn as dashed lines (Fig. 2).

Experimental

N,N-Dicyclohexylcarbodiimide (215 mg, 1.2 mmol) was added to a magnetically stirred solution of 7-(diethylamino) -2-oxo-2H-chromene -3-carboxylic acid (261 mg, 1 mmol), 4-cyano 4^'-hydroxybiphenyl (195 mg, 1 mmol) and a catalytic quantity of N,N-dimethylaminopyrimidine (DMAP) in dried dichloromethane. Resultant reaction mixture was stirred further for 24 h at room temperature. Pure compound was obtained by aqueous workup and column chromatography. Colourless prisms were obtained from chloroform solution on slow evaporation at room temperature (m.p. 541 K).