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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2210.
Published online 2008 October 25. doi:  10.1107/S1600536808034569
PMCID: PMC2959517

(E)-N-[2-(Biphenyl-4-ylvin­yl)phen­yl]furan-2-carboxamide

Abstract

In the title mol­ecule, C25H19NO2, the furyl ring is twisted by 46.3 (1)° with respect to the phenyl­ene ring bearing the amido group. In the stilbene unit, the two phenyl­ene rings (i.e. the rings connected through the –CH=CH– fragment) are twisted by 59.2 (1)°; in the biphenyl­ene unit, the two benzene rings are twisted by 35.5 (1)°. In the crystal structure, mol­ecules are linked by an N—H(...)Oamido hydrogen bond into a zigzag chain running along the c axis.

Related literature

For the use of radical cations in heterocyclic synthesis, see: Thomas et al. (2004 [triangle], 2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2210-scheme1.jpg

Experimental

Crystal data

  • C25H19NO2
  • M r = 365.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2210-efi1.jpg
  • a = 10.9271 (2) Å
  • b = 19.7960 (4) Å
  • c = 8.7969 (1) Å
  • β = 92.374 (1)°
  • V = 1901.25 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 (2) K
  • 0.40 × 0.35 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 13179 measured reflections
  • 4356 independent reflections
  • 3681 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.106
  • S = 1.04
  • 4356 reflections
  • 253 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034569/lh2714sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034569/lh2714Isup2.hkl

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

Acknowledgments

We thank the Ministry of Science, Technology & Innovation (MOSTI) for supporting this study; CHK thanks MOSTI for an NSF scholarship.

supplementary crystallographic information

Comment

In our earlier studies, we reported the synthesis of some stilbene carboxamides whose radical chemistry we investigated (Thomas et al., 2004, 2008). In the present study, we have synthesized a new stilbene carboxamide that incorporates a furan unit (Scheme I, Fig. 1).

Experimental

N-(2-Iodophenyl)furan-2-carboxamide (0.37 g, 1.2 mmol) was dissolved in DMF (20 ml) under a nitrogen atmosphere. The solution was heated to 373 K. Palladium acetate (3.2 mg, 0.014 mmol) was added followed by triethylamine (0.65 ml, 4.7 mmol) and 4-vinylbiphenyl (0.20 g, 1.21 mmol). The mixture was further heated for an hour. The solution was cooled and then mixed with saturated sodium chloride. The organic compound was extracted with ethyl acetate. The ethyl acetate solution was dried with sodium sulfate. The solvent was evaporated and the product purified by column chromatography. Single crystals were obtained by recrystallization from petroleum ether/dichloromethane.

Refinement

Carbon- and nitrogen- bound H-atoms were placed in calculated positions (C—H 0.95, N–H 0.88 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C,N).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C25H19NO2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.

Crystal data

C25H19NO2F(000) = 768
Mr = 365.41Dx = 1.277 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5580 reflections
a = 10.9271 (2) Åθ = 2.5–28.2°
b = 19.7960 (4) ŵ = 0.08 mm1
c = 8.7969 (1) ÅT = 100 K
β = 92.374 (1)°Prism, colorless
V = 1901.25 (6) Å30.40 × 0.35 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3681 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
graphiteθmax = 27.5°, θmin = 1.9°
ω scansh = −14→13
13179 measured reflectionsk = −25→25
4356 independent reflectionsl = −11→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0529P)2 + 0.6489P] where P = (Fo2 + 2Fc2)/3
4356 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.69066 (8)0.17866 (4)0.88070 (9)0.0218 (2)
O20.56344 (8)0.18549 (4)0.50228 (9)0.01969 (19)
N10.52573 (9)0.25519 (5)0.70226 (11)0.0173 (2)
H10.54410.26510.79810.021*
C10.76833 (12)0.13051 (7)0.93850 (15)0.0263 (3)
H1A0.80560.13161.03800.032*
C20.78542 (12)0.08127 (7)0.83672 (16)0.0274 (3)
H20.83470.04210.85100.033*
C30.71470 (11)0.09950 (6)0.70252 (15)0.0221 (3)
H30.70800.07510.60960.027*
C40.65936 (11)0.15860 (6)0.73503 (13)0.0171 (2)
C50.57830 (10)0.20106 (6)0.63762 (13)0.0164 (2)
C60.44068 (11)0.29656 (6)0.61664 (13)0.0168 (2)
C70.34268 (11)0.26554 (6)0.53871 (14)0.0205 (3)
H70.33060.21830.54880.025*
C80.26273 (11)0.30299 (7)0.44657 (14)0.0228 (3)
H80.19710.28140.39140.027*
C90.27890 (12)0.37245 (7)0.43514 (14)0.0237 (3)
H90.22520.39840.37070.028*
C100.37337 (11)0.40363 (6)0.51779 (14)0.0213 (3)
H100.38210.45130.51140.026*
C110.45663 (11)0.36676 (6)0.61073 (13)0.0172 (2)
C120.55685 (11)0.40039 (6)0.69725 (13)0.0176 (2)
H120.62980.37550.71930.021*
C130.55134 (11)0.46414 (6)0.74683 (13)0.0182 (2)
H130.47760.48820.72400.022*
C140.64845 (11)0.50049 (6)0.83315 (13)0.0168 (2)
C150.61548 (11)0.55136 (6)0.93372 (13)0.0178 (2)
H150.53130.56130.94460.021*
C160.70291 (11)0.58746 (6)1.01760 (13)0.0179 (2)
H160.67780.61981.08960.021*
C170.82804 (11)0.57700 (6)0.99805 (13)0.0173 (2)
C180.86116 (11)0.52600 (6)0.89750 (13)0.0185 (2)
H180.94540.51750.88300.022*
C190.77344 (11)0.48767 (6)0.81860 (13)0.0184 (2)
H190.79840.45230.75390.022*
C200.91995 (11)0.62106 (6)1.07784 (13)0.0177 (2)
C211.02722 (11)0.64044 (6)1.00799 (14)0.0204 (3)
H211.04330.62350.90980.025*
C221.11036 (11)0.68399 (6)1.07977 (14)0.0224 (3)
H221.18320.69621.03120.027*
C231.08758 (12)0.70986 (7)1.22235 (15)0.0237 (3)
H231.14360.74051.27060.028*
C240.98214 (13)0.69059 (7)1.29408 (15)0.0274 (3)
H240.96650.70781.39220.033*
C250.89957 (11)0.64639 (7)1.22295 (14)0.0234 (3)
H250.82820.63321.27350.028*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0244 (4)0.0254 (5)0.0155 (4)−0.0007 (4)−0.0020 (3)0.0003 (3)
O20.0252 (4)0.0194 (4)0.0144 (4)0.0002 (3)−0.0003 (3)−0.0011 (3)
N10.0219 (5)0.0164 (5)0.0134 (4)−0.0005 (4)−0.0018 (4)−0.0020 (4)
C10.0239 (6)0.0339 (7)0.0208 (6)0.0012 (5)−0.0029 (5)0.0074 (5)
C20.0232 (6)0.0279 (7)0.0311 (7)0.0034 (5)0.0011 (5)0.0086 (6)
C30.0225 (6)0.0205 (6)0.0236 (6)−0.0005 (5)0.0026 (5)−0.0004 (5)
C40.0184 (5)0.0181 (6)0.0148 (5)−0.0039 (4)0.0013 (4)0.0001 (4)
C50.0177 (5)0.0147 (5)0.0168 (5)−0.0036 (4)0.0020 (4)0.0009 (4)
C60.0195 (5)0.0177 (6)0.0133 (5)0.0009 (4)0.0010 (4)−0.0010 (4)
C70.0231 (6)0.0183 (6)0.0202 (6)−0.0015 (5)0.0011 (5)−0.0032 (5)
C80.0209 (6)0.0283 (7)0.0189 (6)−0.0029 (5)−0.0021 (5)−0.0039 (5)
C90.0242 (6)0.0278 (7)0.0188 (6)0.0017 (5)−0.0037 (5)0.0041 (5)
C100.0252 (6)0.0188 (6)0.0198 (6)−0.0007 (5)0.0005 (5)0.0030 (5)
C110.0199 (5)0.0188 (6)0.0131 (5)−0.0010 (4)0.0019 (4)0.0003 (4)
C120.0188 (5)0.0180 (6)0.0161 (5)−0.0009 (4)0.0008 (4)0.0025 (4)
C130.0188 (5)0.0178 (6)0.0177 (6)−0.0010 (4)0.0002 (4)0.0016 (4)
C140.0202 (6)0.0132 (5)0.0170 (5)−0.0014 (4)−0.0006 (4)0.0035 (4)
C150.0175 (5)0.0156 (5)0.0205 (6)0.0002 (4)0.0015 (4)0.0028 (4)
C160.0215 (6)0.0131 (5)0.0191 (6)0.0003 (4)0.0023 (4)0.0006 (4)
C170.0200 (6)0.0149 (5)0.0167 (5)−0.0002 (4)−0.0007 (4)0.0035 (4)
C180.0176 (5)0.0181 (6)0.0198 (6)0.0022 (4)0.0001 (4)0.0023 (5)
C190.0228 (6)0.0147 (5)0.0179 (6)0.0020 (4)0.0014 (4)0.0002 (4)
C200.0188 (5)0.0147 (5)0.0195 (6)0.0013 (4)−0.0020 (4)0.0013 (4)
C210.0213 (6)0.0205 (6)0.0195 (6)0.0009 (5)0.0012 (5)−0.0007 (5)
C220.0194 (6)0.0239 (6)0.0240 (6)−0.0029 (5)0.0012 (5)0.0031 (5)
C230.0235 (6)0.0244 (6)0.0228 (6)−0.0053 (5)−0.0039 (5)−0.0015 (5)
C240.0279 (7)0.0340 (7)0.0202 (6)−0.0058 (6)0.0010 (5)−0.0061 (5)
C250.0216 (6)0.0280 (7)0.0208 (6)−0.0051 (5)0.0024 (5)−0.0005 (5)

Geometric parameters (Å, °)

O1—C11.3607 (16)C12—H120.9500
O1—C41.3714 (14)C13—C141.4676 (16)
O2—C51.2340 (14)C13—H130.9500
N1—C51.3523 (15)C14—C151.3975 (16)
N1—C61.4295 (15)C14—C191.4002 (16)
N1—H10.8800C15—C161.3818 (17)
C1—C21.342 (2)C15—H150.9500
C1—H1A0.9500C16—C171.4005 (16)
C2—C31.4302 (19)C16—H160.9500
C2—H20.9500C17—C181.3996 (17)
C3—C41.3528 (17)C17—C201.4845 (16)
C3—H30.9500C18—C191.3860 (17)
C4—C51.4706 (16)C18—H180.9500
C6—C71.3903 (17)C19—H190.9500
C6—C111.4019 (16)C20—C251.3979 (17)
C7—C81.3825 (18)C20—C211.3994 (16)
C7—H70.9500C21—C221.3856 (18)
C8—C91.3904 (19)C21—H210.9500
C8—H80.9500C22—C231.3869 (18)
C9—C101.3832 (18)C22—H220.9500
C9—H90.9500C23—C241.3897 (18)
C10—C111.4026 (17)C23—H230.9500
C10—H100.9500C24—C251.3872 (18)
C11—C121.4672 (16)C24—H240.9500
C12—C131.3373 (17)C25—H250.9500
C1—O1—C4105.89 (10)C12—C13—C14126.16 (11)
C5—N1—C6120.70 (10)C12—C13—H13116.9
C5—N1—H1119.6C14—C13—H13116.9
C6—N1—H1119.6C15—C14—C19117.80 (11)
C2—C1—O1111.19 (11)C15—C14—C13118.76 (10)
C2—C1—H1A124.4C19—C14—C13123.43 (11)
O1—C1—H1A124.4C16—C15—C14121.34 (11)
C1—C2—C3106.39 (12)C16—C15—H15119.3
C1—C2—H2126.8C14—C15—H15119.3
C3—C2—H2126.8C15—C16—C17120.99 (11)
C4—C3—C2105.94 (12)C15—C16—H16119.5
C4—C3—H3127.0C17—C16—H16119.5
C2—C3—H3127.0C18—C17—C16117.61 (11)
C3—C4—O1110.59 (11)C18—C17—C20122.35 (10)
C3—C4—C5129.40 (11)C16—C17—C20119.99 (10)
O1—C4—C5119.99 (10)C19—C18—C17121.32 (11)
O2—C5—N1124.22 (11)C19—C18—H18119.3
O2—C5—C4118.13 (10)C17—C18—H18119.3
N1—C5—C4117.65 (10)C18—C19—C14120.80 (11)
C7—C6—C11120.92 (11)C18—C19—H19119.6
C7—C6—N1118.52 (10)C14—C19—H19119.6
C11—C6—N1120.55 (10)C25—C20—C21118.08 (11)
C8—C7—C6120.50 (11)C25—C20—C17120.81 (10)
C8—C7—H7119.8C21—C20—C17121.06 (10)
C6—C7—H7119.8C22—C21—C20121.05 (11)
C7—C8—C9119.57 (12)C22—C21—H21119.5
C7—C8—H8120.2C20—C21—H21119.5
C9—C8—H8120.2C21—C22—C23120.20 (11)
C10—C9—C8119.85 (12)C21—C22—H22119.9
C10—C9—H9120.1C23—C22—H22119.9
C8—C9—H9120.1C22—C23—C24119.50 (12)
C9—C10—C11121.74 (11)C22—C23—H23120.2
C9—C10—H10119.1C24—C23—H23120.2
C11—C10—H10119.1C25—C24—C23120.29 (12)
C6—C11—C10117.32 (11)C25—C24—H24119.9
C6—C11—C12121.45 (11)C23—C24—H24119.9
C10—C11—C12121.22 (11)C24—C25—C20120.85 (11)
C13—C12—C11123.68 (11)C24—C25—H25119.6
C13—C12—H12118.2C20—C25—H25119.6
C11—C12—H12118.2
C4—O1—C1—C2−0.80 (14)C10—C11—C12—C1328.50 (17)
O1—C1—C2—C30.80 (15)C11—C12—C13—C14−179.77 (10)
C1—C2—C3—C4−0.48 (14)C12—C13—C14—C15−150.97 (12)
C2—C3—C4—O10.00 (14)C12—C13—C14—C1930.06 (18)
C2—C3—C4—C5178.41 (11)C19—C14—C15—C16−0.73 (17)
C1—O1—C4—C30.47 (13)C13—C14—C15—C16−179.76 (10)
C1—O1—C4—C5−178.11 (10)C14—C15—C16—C173.81 (17)
C6—N1—C5—O24.14 (17)C15—C16—C17—C18−3.75 (17)
C6—N1—C5—C4−176.54 (10)C15—C16—C17—C20173.84 (10)
C3—C4—C5—O2−6.48 (18)C16—C17—C18—C190.74 (17)
O1—C4—C5—O2171.80 (10)C20—C17—C18—C19−176.79 (11)
C3—C4—C5—N1174.16 (12)C17—C18—C19—C142.28 (18)
O1—C4—C5—N1−7.56 (15)C15—C14—C19—C18−2.28 (17)
C5—N1—C6—C751.61 (15)C13—C14—C19—C18176.70 (11)
C5—N1—C6—C11−127.90 (12)C18—C17—C20—C25−148.23 (12)
C11—C6—C7—C83.72 (17)C16—C17—C20—C2534.29 (17)
N1—C6—C7—C8−175.79 (10)C18—C17—C20—C2134.12 (17)
C6—C7—C8—C9−1.66 (18)C16—C17—C20—C21−143.35 (12)
C7—C8—C9—C10−1.08 (18)C25—C20—C21—C22−0.62 (18)
C8—C9—C10—C111.85 (18)C17—C20—C21—C22177.09 (11)
C7—C6—C11—C10−2.91 (16)C20—C21—C22—C23−0.77 (19)
N1—C6—C11—C10176.59 (10)C21—C22—C23—C241.4 (2)
C7—C6—C11—C12177.55 (10)C22—C23—C24—C25−0.7 (2)
N1—C6—C11—C12−2.95 (16)C23—C24—C25—C20−0.7 (2)
C9—C10—C11—C60.14 (17)C21—C20—C25—C241.35 (19)
C9—C10—C11—C12179.68 (11)C17—C20—C25—C24−176.37 (12)
C6—C11—C12—C13−151.98 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.882.052.903 (1)163

Symmetry codes: (i) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2714).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Thomas, N. F., Kee, C.-H., Ariffin, A., Awang, K., Weber, J.-F. F., Lim, C.-G., Mukhtar, M. R. & Abdul Hadi, A. H. (2008). Heterocycles, 75, 1097–1108.
  • Thomas, N. F., Velu, S. S., Weber, J.-F. F., Lee, K. C., Abdul Hadi, A. H., Richomme, P., Rondeau, D., Noorbatcha, I. & Awang, K. (2004). Tetrahedron, 51, 11733–11742.
  • Westrip, S. P. (2008). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography