Experimental. Crystal data. C 18 H 18 O 6 M r = Monoclinic, P2 1 =c a = (6) Å b = (4) Å c = (8) Å = 97.
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1 Acta Crystallographica Section E Structure Reports Online ISSN Dimethyl 3,3 0 -dimethoxybiphenyl-4,4 0 - dicarboxylate Experimental Crystal data C 18 H 18 O 6 M r = Monoclinic, P2 1 =c a = (6) Å b = (4) Å c = (8) Å = (2) organic compounds V = (13) Å 3 Z =4 Mo K radiation = 0.11 mm 1 T = 297 K mm Fredrik Lundvall, a * David Stephen Wragg, a,b Pascal D. C. Dietzel c and Helmer Fjellvåg a a Centre for Materials Science and Nanotechnology, Department of Chemistry, University of Oslo, PO Box 1126, 0315 Oslo, Norway, b ingap National Centre of Research-based Innovation, Department of Chemistry, University of Oslo, PO Box 1126, 0315 Oslo, Norway, and c Department of Chemistry, University of Bergen, PO Box 7803, 5020 Bergen, Norway Correspondence fredrik.lundvall@smn.uio.no Received 5 March 2014; accepted 12 March 2014 Data collection Bruker PHOTON CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.976, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections measured reflections 2830 independent reflections 2023 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.30 e Å 3 min = 0.21 e Å 3 Key indicators: single-crystal X-ray study; T = 297 K; mean (C C) = Å; R factor = 0.051; wr factor = 0.143; data-to-parameter ratio = Table 1 Selected torsion angles ( ). In the title compound, C 18 H 18 O 6, the biphenyl moiety is twisted with a dihedral angle of (10). The carbomethoxy groups form C C C O torsion angles of 18.3 (3) and 27.7 (3) with the attached rings, as a result of steric hindrances from the nearby methoxy groups. In the absence of stacking interactions and with no HO contacts shorter than 2.7 Å, the packing is dominated by weaker van der Waals interactions. Related literature For the synthesis, see Zhou et al. (2007). C2 C1 C7 C (3) C3 C4 C13 O (3) C11 C10 C14 O (3) Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012); molecular graphics: DIAMOND (Brandenburg, 2004) and ChemBioDraw Ultra (CambridgeSoft, 2009); software used to prepare material for publication: publcif (Westrip, 2010). We acknowledge the support from the Norwegian Research Council (project ), ingap, RECX and the Department of Chemistry, UiO. Supporting information for this paper is available from the IUCr electronic archives (Reference: LD2122). References Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Brandenburg, K. (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany. Bruker (2007). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. CambridgeSoft (2009). ChemBioDraw Ultra. CambridgeSoft Corporation, Cambridge, Massachusetts, USA. Farrugia, L. J. (2012). J. Appl. Cryst. 45, Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, Westrip, S. P. (2010). J. Appl. Cryst. 43, Zhou, J., Xu, R.-H., Yang, J., Shen, X., Zhang, J.-J. & Zhu, D.-R. (2007). J. Nanjing Univ. Tech. 29, doi: /s Lundvall et al. o449
2 supplementary materials [doi: /s ] Dimethyl 3,3 -dimethoxybiphenyl-4,4 -dicarboxylate Fredrik Lundvall, David Stephen Wragg, Pascal D. C. Dietzel and Helmer Fjellvåg 1. Comment The title compound is an intermediate in the synthesis of 3,3 -dimethoxy-4,4 -biphenyldicarboxylic acid, an organic linker for use in the synthesis of MOFs (Metal-Organic Frameworks). The title compound has previously been reported (Zhou et al., 2007), but its crystal structure was unknown until this publication. There is a twist between benzene rings, which is a common feature in biphenyl compounds. The methoxy substituents are nearly coplanar with their parent benzene rings. On the opposite, the methyl carboxylate substituents are not co-planar with the adjacent benzene rings, and the corresponding dihedral angles differ between the two halves of the molecule. The methyl groups of the methoxy and methyl carboxylate substituents are oriented away from each other to accommodate the sterical demands of these groups. The long axis of the molecules is oriented in the [101] direction and two-dimensional corrugated layers parallel to the ac plane can be imagined. The packing does not appear to be directed by any strong intermolecular bonding, although some long range interaction might influence the ordering of the molecules. Indeed, the carbonyl O atoms O5 and O2 are oriented towards H12 and H2 of neighbouring molecules in a near linear fashion. However, since the O H distances are very long (>2.7 Å), they are unlikely to be a major factor in the crystal packing. 2. Experimental The title compound was synthesized by a slightly modified version of the method used by Zhou et al. (2007). In the Ullmann-coupling of 2 equivalents of methyl 4-iodo-2-methoxybenzoate to form the title compound, the reaction temperature was increased to 225 C and the reaction time was set to 8 h. The title compound was extracted from the reaction mixture by repeated washing with warm ethyl acetate and subsequent filtering to remove solid particles. The resulting 1 H NMR spectrum is in good agreement with what was reported by Zhou et al. (2007). Single crystals suitable for XRD analysis were obtained by recrystallizing the title compound from ethyl acetate. 3. Refinement The structure was refined by full-matrix least squares using SHELXL97 (Sheldrick, 2008) as implemented in the WinGX suite (Farrugia, 2012). H-atoms were positioned geometrically at distances of 0.93 (CH) and 0.96 Å (CH 3 ) and refined using a riding/rotating model with U iso (H)=1.2 U eq (CH) and U iso (H)=1.5 U eq (CH 3 ). sup-1
3 Figure 1 The molecule of the title compound with atom labels and 50% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity. Dimethyl 3,3 -dimethoxybiphenyl-4,4 -dicarboxylate Crystal data C 18 H 18 O 6 M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc a = (6) Å b = (4) Å c = (8) Å β = (2) V = (13) Å 3 Z = 4 Data collection Bruker PHOTON CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans F(000) = 696 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 5300 reflections θ = µ = 0.11 mm 1 T = 297 K Plate, colourless mm Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.976, T max = measured reflections 2830 independent reflections 2023 reflections with I > 2σ(I) sup-2
4 R int = θ max = 25.4, θ min = 2.5 h = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 217 parameters 0 restraints Primary atom site location: structure-invariant direct methods k = 8 8 l = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0692P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.30 e Å 3 Δρ min = 0.21 e Å 3 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. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq C (14) (3) (11) (5) C (14) (3) (11) (5) H * C (14) (3) (11) (5) C (15) (3) (11) (5) C (15) (3) (12) (5) H * C (15) (3) (12) (5) H * C (14) (3) (11) (5) C (15) (3) (11) (5) H * C (15) (3) (11) (5) H * C (15) (3) (11) (5) C (14) (3) (11) (5) C (14) (3) (11) (5) H * C (15) (3) (11) (5) C (15) (3) (12) (5) C (16) (4) (12) (6) H15A * H15B * sup-3
5 H15C * C (16) (4) (12) (7) H16A * H16B * H16C * C (16) (4) (12) (6) H17A * H17B * H17C * C (16) (4) (12) (7) H18A * H18B * H18C * O (10) (2) (8) (4) O (11) (2) (8) (5) O (9) (2) (7) (4) O (11) (3) (8) (5) O (13) (4) (9) (8) O (10) (2) (8) (5) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 C (10) (11) (10) (9) (8) (9) C (10) (12) (10) (9) (8) (8) C (10) (12) (10) (9) (7) (8) C (11) (12) (10) (9) (8) (8) C (11) (14) (10) (10) (8) (9) C (11) (14) (11) (10) (9) (10) C (11) (11) (10) (9) (8) (8) C (11) (14) (11) (10) (9) (9) C (11) (14) (10) (10) (9) (9) C (11) (12) (10) (9) (8) (8) C (10) (12) (10) (9) (8) (8) C (11) (12) (10) (9) (8) (8) C (11) (12) (10) (9) (8) (9) C (12) (13) (10) (10) (9) (9) C (12) (18) (12) (11) (9) (11) C (12) (2) (11) (13) (9) (12) C (12) (19) (11) (12) (9) (11) C (12) (19) (12) (12) (9) (12) O (8) (12) (7) (7) (6) (7) O (9) (14) (8) (8) (6) (8) O (7) (11) (7) (7) (5) (6) O (9) (15) (8) (9) (6) (8) O (10) (2) (9) (12) (7) (11) O (8) (13) (7) (8) (6) (8) sup-4
6 Geometric parameters (Å, º) C1 C (3) C12 H C1 C (3) C13 O (2) C1 C (3) C13 O (2) C2 C (3) C14 O (2) C2 H C14 O (2) C3 O (2) C15 O (2) C3 C (2) C15 H15A C4 C (3) C15 H15B C4 C (3) C15 H15C C5 C (3) C16 O (2) C5 H C16 H16A C6 H C16 H16B C7 C (3) C16 H16C C7 C (3) C17 O (2) C8 C (3) C17 H17A C8 H C17 H17B C9 C (3) C17 H17C C9 H C18 O (2) C10 C (2) C18 H18A C10 C (3) C18 H18B C11 O (2) C18 H18C C11 C (3) C2 C1 C (17) C11 C12 H C2 C1 C (17) O2 C13 O (17) C6 C1 C (17) O2 C13 C (18) C3 C2 C (17) O1 C13 C (16) C3 C2 H O5 C14 O (18) C1 C2 H O5 C14 C (19) O3 C3 C (16) O4 C14 C (16) O3 C3 C (16) O1 C15 H15A C2 C3 C (17) O1 C15 H15B C5 C4 C (17) H15A C15 H15B C5 C4 C (16) O1 C15 H15C C3 C4 C (17) H15A C15 H15C C6 C5 C (18) H15B C15 H15C C6 C5 H O4 C16 H16A C4 C5 H O4 C16 H16B C5 C6 C (18) H16A C16 H16B C5 C6 H O4 C16 H16C C1 C6 H H16A C16 H16C C12 C7 C (17) H16B C16 H16C C12 C7 C (17) O3 C17 H17A C8 C7 C (18) O3 C17 H17B C9 C8 C (18) H17A C17 H17B C9 C8 H O3 C17 H17C C7 C8 H H17A C17 H17C C8 C9 C (17) H17B C17 H17C sup-5
7 C8 C9 H O6 C18 H18A C10 C9 H O6 C18 H18B C9 C10 C (17) H18A C18 H18B C9 C10 C (16) O6 C18 H18C C11 C10 C (17) H18A C18 H18C O6 C11 C (16) H18B C18 H18C O6 C11 C (16) C13 O1 C (15) C12 C11 C (17) C3 O3 C (14) C7 C12 C (17) C14 O4 C (16) C7 C12 H C11 O6 C (15) C6 C1 C2 C3 0.3 (3) C14 C10 C11 O6 0.4 (3) C7 C1 C2 C (18) C9 C10 C11 C (3) C1 C2 C3 O (18) C14 C10 C11 C (19) C1 C2 C3 C4 2.1 (3) C8 C7 C12 C (3) O3 C3 C4 C (18) C1 C7 C12 C (18) C2 C3 C4 C5 2.7 (3) O6 C11 C12 C (18) O3 C3 C4 C (3) C10 C11 C12 C7 0.7 (3) C2 C3 C4 C (19) C5 C4 C13 O (3) C3 C4 C5 C6 1.6 (3) C3 C4 C13 O (2) C13 C4 C5 C (19) C5 C4 C13 O (19) C4 C5 C6 C1 0.1 (3) C3 C4 C13 O (3) C2 C1 C6 C5 0.8 (3) C9 C10 C14 O (3) C7 C1 C6 C (19) C11 C10 C14 O (2) C2 C1 C7 C (2) C9 C10 C14 O (19) C6 C1 C7 C (3) C11 C10 C14 O (3) C2 C1 C7 C (3) O2 C13 O1 C (3) C6 C1 C7 C (2) C4 C13 O1 C (18) C12 C7 C8 C9 0.6 (3) C2 C3 O3 C (3) C1 C7 C8 C (19) C4 C3 O3 C (19) C7 C8 C9 C (3) O5 C14 O4 C (4) C8 C9 C10 C (3) C10 C14 O4 C (19) C8 C9 C10 C (2) C12 C11 O6 C (3) C9 C10 C11 O (19) C10 C11 O6 C (2) sup-6
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