Experimental. Crystal data
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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN N,N 0 -(Biphenyl-2,2 0 -diyl)bis(furan-2- carboxamide) Chin Hui Kee, Noel F. Thomas, Azhar Ariffin, Khalijah Awang and Seik Weng Ng* Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia Correspondence seikweng@um.edu.my Experimental Crystal data C 22 H 16 N 2 O 4 M r = Triclinic, P1 a = (2) Å b = (2) Å c = (2) Å = (1) = (1) Data collection Bruker SMART APEX diffractometer Absorption correction: none 6080 measured reflections = (1) V = (3) Å 3 Z =2 Mo K radiation = 0.10 mm 1 T = 100 K mm 3836 independent reflections 3349 reflections with I > 2(I) R int = Received 6 June 2009; accepted 9 June 2009 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.037; wr factor = 0.111; data-to-parameter ratio = The title molecule, C 22 H 16 N 2 O 4, is a 2,2 0 -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 inversionrelated 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). Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 261 parameters 2 restraints Table 1 Hydrogen-bond geometry (Å, ). H atoms treated by a mixture of independent and constrained refinement max = 0.33 e Å 3 min = 0.27 e Å 3 D HA D H HA DA D HA N2 H2O2 i 0.88 (1) 2.12 (1) (1) 165 (1) Symmetry code: (i) x þ 1; y þ 1; z þ 1. Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X- SEED (Barbour, 2001); software used to prepare material for publication: publcif (Westrip, 2009). We thank the Malaysia Toray Science Foundation for supporting this study. CHK thanks MOSTI for an NSF scholarship. 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, Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, 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, Westrip, S. P. (2009). publcif. In preparation. o1556 Kee et al. doi: /s Acta Cryst. (2009). E65, o1556
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3 Acta Cryst. (2009). E65, o1556 [ doi: /s ] N,N'-(Biphenyl-2,2'-diyl)bis(furan-2-carboxamide) C. H. Kee, N. F. Thomas, A. Ariffin, K. Awang and S. W. Ng 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 1.2U eq (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 C 22 H 16 N 2 O 4 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. N,N'-(Biphenyl-2,2'-diyl)bis(furan-2-carboxamide) Crystal data C 22 H 16 N 2 O 4 Z = 2 M r = F 000 = 388 Triclinic, P1 D x = Mg m 3 Hall symbol: -P 1 Mo Kα radiation sup-1
4 λ = Å a = (2) Å Cell parameters from 3508 reflections b = (2) Å θ = º c = (2) Å µ = 0.10 mm 1 α = (1)º T = 100 K β = (1)º Block, colorless γ = (1)º mm V = (3) Å 3 Data collection Bruker SMART APEX diffractometer Radiation source: fine-focus sealed tube R int = Monochromator: graphite θ max = 27.5º T = 100 K θ min = 2.0º ω scans Absorption correction: None 3349 reflections with I > 2σ(I) h = k = measured reflections l = independent reflections Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H atoms treated by a mixture of independent and constrained refinement wr(f 2 ) = w = 1/[σ 2 (F o 2 ) + (0.0627P) P] where P = (F o 2 + 2F c 2 )/3 S = 1.03 (Δ/σ) max = reflections Δρ max = 0.33 e Å parameters Δρ min = 0.27 e Å 3 2 restraints Extinction correction: none Primary atom site location: structure-invariant direct methods Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq O (12) (9) (9) (2) O (12) (9) (9) (2) O (12) (10) (9) (2) O (12) (9) (9) (2) N (14) (11) (10) (2) H (2) (10) (17) (5)* N (14) (11) (10) (2) H (17) (13) (15) (4)* sup-2
5 C (17) (13) (13) (3) H1a * C (17) (14) (13) (3) H2a * C (16) (13) (12) (3) H * C (16) (12) (12) (3) C (16) (12) (12) (2) C (16) (13) (12) (2) C (17) (13) (12) (3) H * C (17) (13) (12) (3) H * C (17) (14) (12) (3) H * C (17) (13) (12) (3) H * C (16) (12) (12) (2) C (16) (12) (12) (3) C (17) (13) (12) (3) H * C (17) (13) (12) (3) H * C (17) (13) (12) (3) H * C (16) (13) (12) (3) H * C (16) (12) (12) (2) C (16) (12) (12) (3) C (16) (12) (12) (3) C (18) (13) (13) (3) H * C (18) (15) (13) (3) H * C (18) (15) (13) (3) H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (5) (4) (4) (4) (4) (3) O (5) (4) (5) (4) (4) (4) O (5) (5) (5) (4) (4) (4) O (5) (5) (5) (4) (4) (4) N (6) (5) (5) (4) (4) (4) N (5) (5) (5) (4) (4) (4) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) sup-3
6 C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (5) (6) (6) (4) (5) (5) C (6) (6) (6) (4) (5) (5) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (6) (7) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (4) (5) (4) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (4) C (6) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (7) (6) (6) (5) (5) (5) C (7) (7) (6) (5) (5) (5) C (6) (7) (7) (5) (5) (5) Geometric parameters (Å, ) O1 C (16) C8 H O1 C (15) C9 C (18) O2 C (15) C9 H O3 C (16) C10 C (18) O4 C (16) C10 H O4 C (15) C11 C (17) N1 C (16) C12 C (18) N1 C (16) C12 C (17) N1 H (9) C13 C (17) N2 C (16) C13 H N2 C (16) C14 C (19) N2 H (9) C14 H C1 C (19) C15 C (18) C1 H1a C15 H C2 C (19) C16 C (17) C2 H2a C16 H C3 C (18) C18 C (18) C3 H C19 C (18) C4 C (18) C20 C (19) C6 C (17) C20 H C6 C (17) C21 C (2) C7 C (18) C21 H C7 H C22 H C8 C (19) C1 O1 C (10) C11 C10 H C22 O4 C (10) C10 C11 C (12) sup-4
7 C5 N1 C (11) C10 C11 C (11) C5 N1 H (12) C6 C11 C (11) C6 N1 H (12) C17 C12 C (11) C18 N2 C (10) C17 C12 C (11) C18 N2 H (10) C13 C12 C (11) C17 N2 H (10) C14 C13 C (12) C2 C1 O (11) C14 C13 H C2 C1 H1a C12 C13 H O1 C1 H1a C13 C14 C (12) C1 C2 C (12) C13 C14 H C1 C2 H2a C15 C14 H C3 C2 H2a C16 C15 C (12) C4 C3 C (12) C16 C15 H C4 C3 H C14 C15 H C2 C3 H C15 C16 C (12) C3 C4 O (11) C15 C16 H C3 C4 C (12) C17 C16 H O1 C4 C (11) C12 C17 C (11) O2 C5 N (12) C12 C17 N (11) O2 C5 C (11) C16 C17 N (11) N1 C5 C (11) O3 C18 N (12) C7 C6 C (11) O3 C18 C (12) C7 C6 N (11) N2 C18 C (11) C11 C6 N (11) C20 C19 O (11) C8 C7 C (12) C20 C19 C (12) C8 C7 H O4 C19 C (11) C6 C7 H C19 C20 C (12) C9 C8 C (12) C19 C20 H C9 C8 H C21 C20 H C7 C8 H C22 C21 C (12) C8 C9 C (12) C22 C21 H C8 C9 H C20 C21 H C10 C9 H C21 C22 O (12) C9 C10 C (12) C21 C22 H C9 C10 H O4 C22 H C4 O1 C1 C (14) C10 C11 C12 C (14) O1 C1 C2 C (15) C6 C11 C12 C (16) C1 C2 C3 C (14) C17 C12 C13 C (19) C2 C3 C4 O (14) C11 C12 C13 C (11) C2 C3 C4 C (13) C12 C13 C14 C (19) C1 O1 C4 C (14) C13 C14 C15 C (2) C1 O1 C4 C (11) C14 C15 C16 C (19) C6 N1 C5 O2 2.2 (2) C13 C12 C17 C (18) C6 N1 C5 C (12) C11 C12 C17 C (11) C3 C4 C5 O (2) C13 C12 C17 N (11) O1 C4 C5 O (11) C11 C12 C17 N (18) C3 C4 C5 N (13) C15 C16 C17 C (18) O1 C4 C5 N (16) C15 C16 C17 N (11) C5 N1 C6 C7 1.9 (2) C18 N2 C17 C (13) sup-5
8 C5 N1 C6 C (12) C18 N2 C17 C (17) C11 C6 C7 C (19) C17 N2 C18 O (2) N1 C6 C7 C (12) C17 N2 C18 C (11) C6 C7 C8 C9 0.7 (2) C22 O4 C19 C (15) C7 C8 C9 C (2) C22 O4 C19 C (11) C8 C9 C10 C (2) O3 C18 C19 C (2) C9 C10 C11 C (19) N2 C18 C19 C (13) C9 C10 C11 C (12) O3 C18 C19 O (11) C7 C6 C11 C (18) N2 C18 C19 O (17) N1 C6 C11 C (11) O4 C19 C20 C (15) C7 C6 C11 C (11) C18 C19 C20 C (13) N1 C6 C11 C (18) C19 C20 C21 C (16) C10 C11 C12 C (16) C20 C21 C22 O (16) C6 C11 C12 C (14) C19 O4 C22 C (15) Hydrogen-bond geometry (Å, ) D H A D H H A D A D H A N2 H2 O2 i 0.88 (1) 2.12 (1) (1) 165 (1) Symmetry codes: (i) x+1, y+1, z+1. sup-6
9 Fig. 1 sup-7
10 Fig. 2 sup-8
b = (17) Å c = (18) Å = (4) = (4) = (4) V = (3) Å 3 Data collection Refinement
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