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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1556.
Published online 2009 June 13. doi:  10.1107/S1600536809021874
PMCID: PMC2969478

N,N′-(Biphenyl-2,2′-di­yl)bis­(furan-2-carboxamide)

Abstract

The title mol­ecule, C22H16N2O4, is a 2,2′-disubstituted biphenyl whose phenyl­ene rings are rotated by 66.5 (1)° so as to avoid repulsion by the substituents. Only one of the two amide –NH– fragments engages in hydrogen bonding, and this inter­acts with the amido –C(=O)– acceptor of an inversion-related mol­ecule to generate a hydrogen-bonded dimer.

Related literature

The Heck reaction produces the desired stilbene along with a symmetrical biaryl owing to homocoupling of the aryl halide reactant. For the synthesis of stilbene carboxamides synthesized by using radical cations in a modified Heck reaction; see: Thomas et al. (2008 [triangle]).

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Object name is e-65-o1556-scheme1.jpg

Experimental

Crystal data

  • C22H16N2O4
  • M r = 372.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1556-efi1.jpg
  • a = 8.1784 (2) Å
  • b = 10.1399 (2) Å
  • c = 11.1475 (2) Å
  • α = 99.938 (1)°
  • β = 107.521 (1)°
  • γ = 92.439 (1)°
  • V = 863.92 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 6080 measured reflections
  • 3836 independent reflections
  • 3349 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.111
  • S = 1.03
  • 3836 reflections
  • 261 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021874/tk2474sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021874/tk2474Isup2.hkl

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

Acknowledgments

We thank the Malaysia Toray Science Foundation for supporting this study. CHK thanks MOSTI for an NSF schol­arship.

supplementary crystallographic information

Experimental

N-(2-Iodophenyl)furan-2-carboxamide (1.51 g, 4.81 mmol) was dissolved in DMF (30 ml) under a nitrogen atmosphere. The solution was heated to 393 K. Palladium acetate (0.01 g, 0.05 mmol) was added followed by triethylamine (2.4 ml, 0.2 mol) and 4-methoxystyrene (0.83 g, 6.16 mmol). The mixture was heated for 48 h. The solution was cooled and then mixed with saturated sodium chloride. The organic compound was extracted with ethylacetate. The ethylacetate solution was dried with sodium sulfate. The solvent was evaporated and the product purified by column chromatography (0.12 g, 10% yield). Single crystals were obtained by recrystallization from hexane/chloroform.

Refinement

Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation with U(H) set to 1.2Ueq(C). The nitrogen-bound H atoms were located in a difference Fourier map, and were refined with a restraint of N–H 0.88±0.01 Å

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C22H16N2O4 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.
Fig. 2.
Hydrogen-bonded dimer in the crystal structure of (I). Red dashed lines represent N-H···O hydrogen bonds.

Crystal data

C22H16N2O4Z = 2
Mr = 372.37F(000) = 388
Triclinic, P1Dx = 1.431 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1784 (2) ÅCell parameters from 3508 reflections
b = 10.1399 (2) Åθ = 2.6–28.3°
c = 11.1475 (2) ŵ = 0.10 mm1
α = 99.938 (1)°T = 100 K
β = 107.521 (1)°Block, colorless
γ = 92.439 (1)°0.30 × 0.25 × 0.20 mm
V = 863.92 (3) Å3

Data collection

Bruker SMART APEX diffractometer3349 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
graphiteθmax = 27.5°, θmin = 2.0°
ω scansh = −10→10
6080 measured reflectionsk = −12→13
3836 independent reflectionsl = −14→14

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0627P)2 + 0.3539P] where P = (Fo2 + 2Fc2)/3
3836 reflections(Δ/σ)max = 0.001
261 parametersΔρmax = 0.33 e Å3
2 restraintsΔρmin = −0.27 e Å3

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

xyzUiso*/Ueq
O10.37952 (12)0.28756 (9)0.22024 (9)0.0174 (2)
O20.32912 (12)0.61791 (9)0.36569 (9)0.0186 (2)
O30.42615 (12)0.02447 (10)0.82668 (9)0.0213 (2)
O40.80281 (12)0.23741 (9)0.86550 (9)0.0191 (2)
N10.29107 (14)0.41257 (11)0.42005 (10)0.0156 (2)
H10.295 (2)0.3271 (10)0.3921 (17)0.028 (5)*
N20.47787 (14)0.16551 (11)0.70037 (10)0.0148 (2)
H20.5491 (17)0.2298 (13)0.6951 (15)0.016 (4)*
C10.40891 (17)0.24580 (13)0.10565 (13)0.0190 (3)
H1a0.43040.15700.07490.023*
C20.40293 (17)0.34894 (14)0.04255 (13)0.0190 (3)
H2a0.41800.3456−0.03910.023*
C30.36958 (16)0.46370 (13)0.12235 (12)0.0173 (3)
H30.35810.55170.10440.021*
C40.35755 (16)0.42216 (12)0.22885 (12)0.0155 (3)
C50.32496 (16)0.49452 (12)0.34438 (12)0.0145 (2)
C60.24862 (16)0.44495 (13)0.53444 (12)0.0144 (2)
C70.23946 (17)0.57726 (13)0.59222 (12)0.0169 (3)
H70.26030.65010.55370.020*
C80.19978 (17)0.60133 (13)0.70591 (12)0.0182 (3)
H80.19500.69130.74550.022*
C90.16695 (17)0.49624 (14)0.76291 (12)0.0192 (3)
H90.13860.51380.84040.023*
C100.17609 (17)0.36502 (13)0.70536 (12)0.0174 (3)
H100.15390.29280.74430.021*
C110.21726 (16)0.33732 (12)0.59167 (12)0.0142 (2)
C120.21741 (16)0.19410 (12)0.53056 (12)0.0142 (3)
C130.08880 (17)0.13778 (13)0.41514 (12)0.0164 (3)
H130.00940.19370.37310.020*
C140.07515 (17)0.00244 (13)0.36117 (12)0.0182 (3)
H14−0.0121−0.03370.28250.022*
C150.18976 (17)−0.08003 (13)0.42285 (12)0.0178 (3)
H150.1790−0.17340.38770.021*
C160.31983 (16)−0.02613 (13)0.53571 (12)0.0161 (3)
H160.3991−0.08260.57700.019*
C170.33501 (16)0.11065 (12)0.58905 (12)0.0141 (2)
C180.52125 (16)0.10827 (12)0.80562 (12)0.0150 (3)
C190.69553 (16)0.15138 (12)0.89706 (12)0.0155 (3)
C200.77797 (18)0.11564 (13)1.01001 (13)0.0195 (3)
H200.73190.05771.05290.023*
C210.94791 (18)0.18268 (15)1.05134 (13)0.0226 (3)
H211.03800.17791.12720.027*
C220.95558 (18)0.25413 (15)0.96175 (13)0.0226 (3)
H221.05460.30900.96520.027*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0214 (5)0.0138 (4)0.0181 (4)0.0017 (4)0.0076 (4)0.0032 (3)
O20.0226 (5)0.0136 (4)0.0217 (5)0.0018 (4)0.0085 (4)0.0058 (4)
O30.0197 (5)0.0241 (5)0.0206 (5)−0.0031 (4)0.0051 (4)0.0095 (4)
O40.0162 (5)0.0212 (5)0.0196 (5)−0.0015 (4)0.0041 (4)0.0065 (4)
N10.0211 (6)0.0113 (5)0.0162 (5)0.0023 (4)0.0082 (4)0.0031 (4)
N20.0136 (5)0.0140 (5)0.0169 (5)−0.0005 (4)0.0037 (4)0.0057 (4)
C10.0176 (6)0.0193 (6)0.0187 (6)−0.0010 (5)0.0066 (5)−0.0011 (5)
C20.0166 (6)0.0231 (6)0.0170 (6)−0.0003 (5)0.0058 (5)0.0029 (5)
C30.0160 (6)0.0178 (6)0.0185 (6)0.0005 (5)0.0056 (5)0.0050 (5)
C40.0143 (6)0.0132 (6)0.0185 (6)0.0005 (5)0.0036 (5)0.0044 (5)
C50.0124 (5)0.0151 (6)0.0158 (6)0.0013 (4)0.0031 (5)0.0050 (5)
C60.0132 (6)0.0158 (6)0.0140 (6)0.0022 (4)0.0031 (5)0.0039 (5)
C70.0176 (6)0.0147 (6)0.0177 (6)0.0030 (5)0.0038 (5)0.0044 (5)
C80.0182 (6)0.0163 (6)0.0176 (6)0.0056 (5)0.0026 (5)0.0012 (5)
C90.0198 (6)0.0230 (7)0.0143 (6)0.0049 (5)0.0048 (5)0.0031 (5)
C100.0178 (6)0.0192 (6)0.0157 (6)0.0015 (5)0.0044 (5)0.0060 (5)
C110.0120 (6)0.0143 (6)0.0148 (6)0.0019 (4)0.0016 (5)0.0037 (4)
C120.0153 (6)0.0140 (6)0.0150 (6)−0.0001 (5)0.0063 (5)0.0047 (5)
C130.0178 (6)0.0162 (6)0.0154 (6)0.0026 (5)0.0044 (5)0.0053 (5)
C140.0194 (6)0.0181 (6)0.0153 (6)−0.0015 (5)0.0040 (5)0.0018 (5)
C150.0211 (6)0.0139 (6)0.0193 (6)−0.0002 (5)0.0089 (5)0.0018 (5)
C160.0157 (6)0.0146 (6)0.0202 (6)0.0034 (5)0.0078 (5)0.0053 (5)
C170.0141 (6)0.0156 (6)0.0137 (6)0.0000 (5)0.0057 (5)0.0040 (4)
C180.0154 (6)0.0147 (6)0.0156 (6)0.0032 (5)0.0055 (5)0.0032 (5)
C190.0163 (6)0.0147 (6)0.0166 (6)0.0018 (5)0.0064 (5)0.0036 (5)
C200.0205 (7)0.0206 (6)0.0171 (6)0.0020 (5)0.0049 (5)0.0049 (5)
C210.0183 (7)0.0283 (7)0.0178 (6)0.0018 (5)0.0017 (5)0.0023 (5)
C220.0152 (6)0.0277 (7)0.0219 (7)−0.0026 (5)0.0032 (5)0.0024 (5)

Geometric parameters (Å, °)

O1—C11.3695 (16)C8—H80.9500
O1—C41.3749 (15)C9—C101.3893 (18)
O2—C51.2295 (15)C9—H90.9500
O3—C181.2267 (16)C10—C111.3931 (18)
O4—C221.3613 (16)C10—H100.9500
O4—C191.3716 (15)C11—C121.4941 (17)
N1—C51.3572 (16)C12—C171.3957 (18)
N1—C61.4093 (16)C12—C131.4030 (17)
N1—H10.875 (9)C13—C141.3853 (17)
N2—C181.3569 (16)C13—H130.9500
N2—C171.4311 (16)C14—C151.3884 (19)
N2—H20.877 (9)C14—H140.9500
C1—C21.3521 (19)C15—C161.3858 (18)
C1—H1a0.9500C15—H150.9500
C2—C31.4267 (19)C16—C171.3961 (17)
C2—H2a0.9500C16—H160.9500
C3—C41.3550 (18)C18—C191.4765 (18)
C3—H30.9500C19—C201.3559 (18)
C4—C51.4715 (18)C20—C211.4255 (19)
C6—C71.3999 (17)C20—H200.9500
C6—C111.4067 (17)C21—C221.345 (2)
C7—C81.3851 (18)C21—H210.9500
C7—H70.9500C22—H220.9500
C8—C91.3869 (19)
C1—O1—C4106.32 (10)C11—C10—H10119.4
C22—O4—C19105.90 (10)C10—C11—C6118.87 (12)
C5—N1—C6129.64 (11)C10—C11—C12119.07 (11)
C5—N1—H1114.1 (12)C6—C11—C12121.97 (11)
C6—N1—H1116.3 (12)C17—C12—C13118.24 (11)
C18—N2—C17122.19 (10)C17—C12—C11122.04 (11)
C18—N2—H2118.8 (10)C13—C12—C11119.58 (11)
C17—N2—H2118.2 (10)C14—C13—C12121.42 (12)
C2—C1—O1110.34 (11)C14—C13—H13119.3
C2—C1—H1a124.8C12—C13—H13119.3
O1—C1—H1a124.8C13—C14—C15119.56 (12)
C1—C2—C3106.73 (12)C13—C14—H14120.2
C1—C2—H2a126.6C15—C14—H14120.2
C3—C2—H2a126.6C16—C15—C14120.02 (12)
C4—C3—C2106.31 (12)C16—C15—H15120.0
C4—C3—H3126.8C14—C15—H15120.0
C2—C3—H3126.8C15—C16—C17120.36 (12)
C3—C4—O1110.30 (11)C15—C16—H16119.8
C3—C4—C5131.50 (12)C17—C16—H16119.8
O1—C4—C5118.19 (11)C12—C17—C16120.35 (11)
O2—C5—N1125.53 (12)C12—C17—N2120.43 (11)
O2—C5—C4120.77 (11)C16—C17—N2119.14 (11)
N1—C5—C4113.70 (11)O3—C18—N2124.03 (12)
C7—C6—C11120.02 (11)O3—C18—C19119.98 (12)
C7—C6—N1122.95 (11)N2—C18—C19115.98 (11)
C11—C6—N1117.03 (11)C20—C19—O4110.52 (11)
C8—C7—C6119.61 (12)C20—C19—C18131.14 (12)
C8—C7—H7120.2O4—C19—C18118.26 (11)
C6—C7—H7120.2C19—C20—C21106.02 (12)
C9—C8—C7121.07 (12)C19—C20—H20127.0
C9—C8—H8119.5C21—C20—H20127.0
C7—C8—H8119.5C22—C21—C20106.47 (12)
C8—C9—C10119.20 (12)C22—C21—H21126.8
C8—C9—H9120.4C20—C21—H21126.8
C10—C9—H9120.4C21—C22—O4111.09 (12)
C9—C10—C11121.23 (12)C21—C22—H22124.5
C9—C10—H10119.4O4—C22—H22124.5
C4—O1—C1—C2−1.04 (14)C10—C11—C12—C13109.90 (14)
O1—C1—C2—C30.66 (15)C6—C11—C12—C13−66.72 (16)
C1—C2—C3—C40.00 (14)C17—C12—C13—C141.43 (19)
C2—C3—C4—O1−0.65 (14)C11—C12—C13—C14−174.25 (11)
C2—C3—C4—C5179.98 (13)C12—C13—C14—C150.66 (19)
C1—O1—C4—C31.04 (14)C13—C14—C15—C16−1.8 (2)
C1—O1—C4—C5−179.49 (11)C14—C15—C16—C170.93 (19)
C6—N1—C5—O22.2 (2)C13—C12—C17—C16−2.34 (18)
C6—N1—C5—C4−177.63 (12)C11—C12—C17—C16173.22 (11)
C3—C4—C5—O2−11.2 (2)C13—C12—C17—N2174.26 (11)
O1—C4—C5—O2169.42 (11)C11—C12—C17—N2−10.18 (18)
C3—C4—C5—N1168.56 (13)C15—C16—C17—C121.20 (18)
O1—C4—C5—N1−10.77 (16)C15—C16—C17—N2−175.44 (11)
C5—N1—C6—C7−1.9 (2)C18—N2—C17—C12133.43 (13)
C5—N1—C6—C11178.99 (12)C18—N2—C17—C16−49.93 (17)
C11—C6—C7—C80.14 (19)C17—N2—C18—O3−15.7 (2)
N1—C6—C7—C8−178.89 (12)C17—N2—C18—C19163.63 (11)
C6—C7—C8—C9−0.7 (2)C22—O4—C19—C200.32 (15)
C7—C8—C9—C100.7 (2)C22—O4—C19—C18−176.70 (11)
C8—C9—C10—C11−0.1 (2)O3—C18—C19—C20−1.2 (2)
C9—C10—C11—C6−0.48 (19)N2—C18—C19—C20179.49 (13)
C9—C10—C11—C12−177.20 (12)O3—C18—C19—O4175.11 (11)
C7—C6—C11—C100.46 (18)N2—C18—C19—O4−4.22 (17)
N1—C6—C11—C10179.55 (11)O4—C19—C20—C21−0.45 (15)
C7—C6—C11—C12177.08 (11)C18—C19—C20—C21176.06 (13)
N1—C6—C11—C12−3.83 (18)C19—C20—C21—C220.40 (16)
C10—C11—C12—C17−65.60 (16)C20—C21—C22—O4−0.22 (16)
C6—C11—C12—C17117.78 (14)C19—O4—C22—C21−0.05 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.88 (1)2.12 (1)2.970 (1)165 (1)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2474).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). 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.
  • Westrip, S. P. (2009). publCIF In preparation.

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