Crystal structure of 5-benzoyl-2,4-di­phenyl-4,5-di­hydro­furan-3-carbo­nitrile

V Rajni Swamy; RV Krishnakumar; S Sivakumar; N Srinivasan; R Ranjith Kumar

doi:10.1107/S2056989015014887

. 2015 Aug 15;71(Pt 9):o663–o664. doi: 10.1107/S2056989015014887

Crystal structure of 5-benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carbonitrile

V Rajni Swamy ^a, RV Krishnakumar ^a,^*, S Sivakumar ^b, N Srinivasan ^a, R Ranjith Kumar ^b

PMCID: PMC4555400 PMID: 26396892

Abstract

In the title compound, C₂₄H₁₇NO₂, the carbonyl O atom of the benzoyl group is cis with respect to the furanyl O atom, and the associated O—C—C—O torsion angle is 4.62 (19)°. The puckering of the dihydrofuran ring is close to twisted (⁴ T ₅), with parameters Q = 0.1856 (16) Å and φ = 313.5 (5)°. Molecules are interconnected via a C—H⋯N and a C—H⋯O hydrogen bond, leading to layers parallel to the (200) plane and characterized by R ₄ ⁴(28) and R ₄ ⁴(36) graph-set motifs. The furan O atom does not participate in intermolecular hydrogen bonding. The crystal lattice encompasses a solvent-accessible void of 24.7 (8) Å³.

Keywords: crystal structure, furan, carbonitrile, hydrogen bond

Related literature

For biological activity of dihydrofurans, see: Simmonds et al. (1990 ▸); Gebbinck et al. (1999 ▸); Ley et al. (1987 ▸); Kumar et al. (2003 ▸); Pour et al. (2003 ▸); Loğoğlu et al. (2010 ▸). For Cambridge Structural Database, see: Groom & Allen (2014 ▸). For graph-set motifs, see: Bernstein et al. (1995 ▸). For puckering of rings, see: Cremer & Pople (1975 ▸). For related structures, see: Rajni Swamy et al. (2012 ▸); Suresh et al. (2012a ▸,b ▸,c ▸). graphic file with name e-71-0o663-scheme1.jpg

Experimental

Crystal data

C₂₄H₁₇NO₂
M _r = 351.38
Monoclinic,
a = 10.0704 (7) Å
b = 15.7994 (12) Å
c = 11.8632 (9) Å
β = 98.886 (3)°
V = 1864.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.35 × 0.24 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.973, T _max = 0.994
34345 measured reflections
4648 independent reflections
2305 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.147
S = 0.99
4648 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015014887/xu5865sup1.cif

e-71-0o663-sup1.cif^{(1,020KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014887/xu5865Isup2.hkl

e-71-0o663-Isup2.hkl^{(370.2KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015014887/xu5865Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015014887/xu5865fig1.tif

Molecular structure of (I) showing the atom numbering scheme and displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms and atoms of minor disordered components omitted for clarity.

Click here for additional data file.^{(1.3MB, tif)}

b via . DOI: 10.1107/S2056989015014887/xu5865fig2.tif

A view down the b axis showing molecules interconnected via a C—H⋯N and a C—H⋯O hydrogen-bond leading to layers parallel to the (200) plane.

Click here for additional data file.^{(1.6MB, tif)}

. DOI: 10.1107/S2056989015014887/xu5865fig3.tif

A view of the molecules of the unit cell showing C—H⋯N and C—H⋯O hydrogen bonds.

CCDC reference: 1023392

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C11H11N1ⁱ	0.93	2.63	3.487(2)	154
C21H21O2ⁱⁱ	0.93	2.58	3.277(2)	132

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

Acknowledgments

The authors thank Sophisticated Analytic Instrumentation Facility (SAIF), IIT Madras, Chennai, for single-crystal X-ray intensity data collection. RRK thanks the University Grants Commission, New Delhi, for funds through Major Research Project F. No. 42-242/2013 (SR).

supplementary crystallographic information

S1. Introduction

The title compound 5-benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carbonitrile (I) is a dihydrofuran carbonitrile derivative. Dihydrofurans belong to an important class of heterocycles and are known for distinct insect antifeedant activities (Gebbinck et al., 1999). Dihydrofurans have also been found to possess antifungal (Pour et al., 2003) and anti-inflammatory properties (Kumar et al., 2003). The dihydrofuran derivatives with their reactive functional groups like methoxy, carbonyl etc. may prove to be promising candidates for the synthesis of novel heterocyclic compounds. The in vitro antibacterial and antifungal activities of some furan derivatives, specifically, 4,5-dihydrofuran-3-carbonitriles were investigated against some bacteria and fungi and were found to show activity against bacteria better than some known antibiotics (Loğoğlu et al., 2010).

S2. Experimental

S2.1. Synthesis and crystallization

A mixture of benzoylacetonitrile (1.0 mmol), benzaldehyde (1.0 mmol) and imidazolium salt (1-methyl-3-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium bromide) (1.0 mmol) were dissolved in EtOH (10 mL) then Et₃N(triethylamine) (1.0 mmol) was added slowly and refluxed on a water bath. The consumption of starting material was monitored by TLC. After 3hours the reaction mixture was cooled and the precipitated solid product was filtered and washed. Crystals of (1) suitable for diffraction were obtained.

S2.2. Refinement

All H atoms were included into the model at geometrically calculated positions (C—H target distance = 0.98 Å for methine H atoms and 0.93 Å for all other aromatic H atoms) and refined using a riding model. The U_iso values of all H atoms were constrained to 1.2 times U_eq of the respective atom to which the H atom binds.

S3. Results and discussion

The carbonyl O of the benzoyl group is cis with the furanyl O atom with the value of the associated torsion angle being 4.62°. The puckering of the hydrofuran ring is close to twisted (⁴T₅) with parameters Q = 0.1856 (16) Å and φ = 313.5 (5)°. The angle between the mean plane about the furan ring atoms and the 2-phenyl ring is 22.5 (1)° while those with respect to the 4-phenyl and the 5-benzoyl group atoms are 88.6 (1) and 78.4 (1)°, respectively.

A search in the CSD [version 5.53, update 3, May 2013] for organic nonpolymeric single crystal structures for which 3D coordinates determined with no disorder, no ions and no other errors with R-factors less than 0.05 revealed 6287 structures of which 2498 had the furan O involved in C—H···O interactions with the H···A ranging from 2.127 to 2.720 Å. Also, four structures bearing close relationships to the title compound with refcodes LEFJUD (Suresh et al., 2012a), YAXGOV (Suresh et al., 2012b), ZARBEB (Suresh et al., 2012c) and EDUZAG (Rajni Rajni et al., 2012) were found. These structures differ by an indole ring replaced by a phenyl in the title compound and interestingly none display any change in the crystal system or lattice type. However, there are drastic differences in the intermolecular interaction patterns. The molecules are interconnected via a C—H···N and a C—H···O hydrogen-bond leading to a layers parallel to the (200) plane and characterized by R₄⁴(28) and R₄⁴(36) graph-set motifs. The furan O atom does not participate in the intermolecular hydrogen bonding. The crystal lattice encompasses a solvent accessible void of 24.7 (8) Å³.