organic compounds
4,4′-(Anthracene-9,10-diyl)dibenzoic acid dimethylformamide disolvate
aSchool of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
*Correspondence e-mail: lihong@zzuli.edu.cn
In the title compound, C28H18O4·2C3H7NO, the dihedral angle between the benzene rings and the anthracene system is 74.05 (12)°. A crystallographic inversion centre is located in the middle of the anthracene unit. The dimethylformamide solvent molecules are partially disordered over two positions of approximately equal occupancy [0.529 (6):0.471 (6)]. Intermolecular O—H⋯O hydrogen bonds with the major occupancy formamide O atom as acceptor result in the formation of 2:1 solvate–complex aggregates, which are alternately linked to shorter solvate units via weak intermolecular C—H⋯O contacts generated from the rotational disorder of the formamide O atom (minor occupancy component). Weak C—H⋯π interactions between the solvent molecules as the donor and the outer anthracene rings support these contacts in the for both disorder components.
Related literature
For the structure of 4-(2,5-dihexyloxyphenyl)benzoic acid and the syntheses of related compounds, see: Li et al. (2008). For palladium-catalysed Suzuki coupling reactions, see: Xu et al. (2006, 2008); Li et al. (2006) and literature cited therein.
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536809014858/si2166sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809014858/si2166Isup2.hkl
The title compound was obtained from the Suzuki coupling reaction of 9,10-dibromoanthracene and 4-carboxyphenylboronic acid as described in the literature (Li et al., 2008) and recrystallized from dimethylformamide at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.
H atoms attached to C atoms of the title compound were placed in geometrically idealized positions and treated as riding with C—H distances constrained to 0.93 (aromatic CH), or 0.96 Å (methyl CH3), and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) (1.5Ueq for methyl H). The atom-site occupancies for the rotational disordered formamide oxygen atoms O3 and O3' refined to a ratio of 0.53/0.47.
Alert levels A and B for short intermolecular O1···O3' and H2D···H15' contacts with distances of2.50 Å and 2.01 Å may be explained by the difficulties to split the whole solvent molecule due to the pseudo two-fold rotation of the methyl groups around the N1—C15 axis. BUMP instruction or splitting of the whole solvent molecule resulted in unstable refinements. Introduction of shift-limiting restraints (DAMP instruction) resulted in larger R-values without improving the geometries. Therefore the partial disorder
(O3, O3', H15, H15') was preferred as a compromise.Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C28H18O4·2C3H7NO | Z = 1 |
Mr = 564.62 | F(000) = 298 |
Triclinic, P1 | Dx = 1.270 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3692 (15) Å | Cell parameters from 879 reflections |
b = 8.9981 (18) Å | θ = 2.9–22.0° |
c = 12.124 (2) Å | µ = 0.09 mm−1 |
α = 71.157 (3)° | T = 295 K |
β = 77.640 (3)° | Block, colourless |
γ = 79.754 (3)° | 0.23 × 0.16 × 0.06 mm |
V = 738.0 (3) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 2721 independent reflections |
Radiation source: fine-focus sealed tube | 1467 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ϕ and ω scans | θmax = 25.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.980, Tmax = 0.994 | k = −10→9 |
5691 measured reflections | l = −14→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0732P)2 + 0.04P] where P = (Fo2 + 2Fc2)/3 |
2721 reflections | (Δ/σ)max < 0.001 |
203 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C28H18O4·2C3H7NO | γ = 79.754 (3)° |
Mr = 564.62 | V = 738.0 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.3692 (15) Å | Mo Kα radiation |
b = 8.9981 (18) Å | µ = 0.09 mm−1 |
c = 12.124 (2) Å | T = 295 K |
α = 71.157 (3)° | 0.23 × 0.16 × 0.06 mm |
β = 77.640 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 2721 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1467 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.994 | Rint = 0.028 |
5691 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.16 e Å−3 |
2721 reflections | Δρmin = −0.20 e Å−3 |
203 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C15 | 0.5707 (5) | 0.2790 (4) | 0.4860 (3) | 0.0742 (9) | 0.529 (6) |
H15 | 0.4771 | 0.2595 | 0.4536 | 0.089* | 0.529 (6) |
O3 | 0.5840 (5) | 0.2039 (5) | 0.5938 (4) | 0.0918 (18) | 0.529 (6) |
C15' | 0.5707 (5) | 0.2790 (4) | 0.4860 (3) | 0.0742 (9) | 0.471 (6) |
H15' | 0.5944 | 0.2141 | 0.5598 | 0.089* | 0.471 (6) |
O3' | 0.4309 (7) | 0.2700 (6) | 0.4479 (4) | 0.096 (2) | 0.471 (6) |
N1 | 0.6843 (3) | 0.3826 (3) | 0.41928 (19) | 0.0637 (6) | |
C16 | 0.6620 (5) | 0.4705 (4) | 0.2994 (3) | 0.0999 (12) | |
H16A | 0.5498 | 0.4476 | 0.2831 | 0.150* | |
H16B | 0.7677 | 0.4407 | 0.2459 | 0.150* | |
H16C | 0.6535 | 0.5816 | 0.2895 | 0.150* | |
C17 | 0.8377 (4) | 0.4104 (5) | 0.4627 (3) | 0.0945 (11) | |
H17A | 0.8375 | 0.3450 | 0.5429 | 0.142* | |
H17B | 0.8249 | 0.5196 | 0.4598 | 0.142* | |
H17C | 0.9532 | 0.3852 | 0.4146 | 0.142* | |
O1 | −0.1924 (3) | −0.0937 (3) | 0.42504 (19) | 0.1024 (9) | |
O2 | −0.3377 (3) | −0.0181 (3) | 0.2730 (2) | 0.1090 (9) | |
H2D | −0.4140 | −0.0728 | 0.3213 | 0.163* | |
C1 | −0.0616 (3) | 0.0915 (3) | 0.2520 (2) | 0.0496 (6) | |
C2 | −0.0651 (4) | 0.1757 (3) | 0.1348 (2) | 0.0638 (8) | |
H2 | −0.1589 | 0.1662 | 0.0978 | 0.077* | |
C3 | 0.0713 (4) | 0.2746 (3) | 0.0719 (2) | 0.0594 (7) | |
H3 | 0.0669 | 0.3313 | −0.0068 | 0.071* | |
C4 | 0.2133 (3) | 0.2901 (3) | 0.1243 (2) | 0.0445 (6) | |
C5 | 0.2169 (3) | 0.2037 (3) | 0.2414 (2) | 0.0525 (7) | |
H5 | 0.3117 | 0.2117 | 0.2783 | 0.063* | |
C6 | 0.0805 (3) | 0.1053 (3) | 0.3045 (2) | 0.0537 (7) | |
H6 | 0.0852 | 0.0480 | 0.3831 | 0.064* | |
C7 | −0.2053 (4) | −0.0146 (3) | 0.3219 (3) | 0.0643 (8) | |
C8 | 0.6573 (4) | 0.1754 (3) | −0.1369 (2) | 0.0640 (8) | |
H8 | 0.6611 | 0.0821 | −0.1552 | 0.077* | |
C9 | 0.5159 (4) | 0.2148 (3) | −0.0568 (2) | 0.0549 (7) | |
H9 | 0.4239 | 0.1477 | −0.0204 | 0.066* | |
C10 | 0.5040 (3) | 0.3575 (3) | −0.02629 (19) | 0.0432 (6) | |
C11 | 0.3592 (3) | 0.3985 (3) | 0.05850 (19) | 0.0419 (6) | |
C12 | 0.3533 (3) | 0.5398 (3) | 0.08512 (19) | 0.0419 (6) | |
C13 | 0.2061 (3) | 0.5896 (3) | 0.1681 (2) | 0.0514 (7) | |
H13 | 0.1110 | 0.5259 | 0.2059 | 0.062* | |
C14 | 0.2008 (4) | 0.7263 (3) | 0.1932 (2) | 0.0620 (8) | |
H14 | 0.1031 | 0.7554 | 0.2478 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C15 | 0.066 (2) | 0.089 (2) | 0.066 (2) | −0.0197 (18) | −0.0072 (17) | −0.0164 (19) |
O3 | 0.082 (3) | 0.114 (4) | 0.071 (3) | −0.054 (3) | −0.012 (2) | 0.006 (3) |
C15' | 0.066 (2) | 0.089 (2) | 0.066 (2) | −0.0197 (18) | −0.0072 (17) | −0.0164 (19) |
O3' | 0.087 (4) | 0.120 (4) | 0.079 (3) | −0.060 (3) | −0.015 (3) | 0.000 (3) |
N1 | 0.0574 (14) | 0.0753 (17) | 0.0547 (14) | −0.0202 (12) | −0.0040 (11) | −0.0113 (12) |
C16 | 0.088 (2) | 0.119 (3) | 0.071 (2) | −0.022 (2) | −0.0099 (18) | 0.004 (2) |
C17 | 0.079 (2) | 0.125 (3) | 0.086 (2) | −0.045 (2) | −0.0063 (19) | −0.028 (2) |
O1 | 0.0933 (16) | 0.128 (2) | 0.0722 (15) | −0.0639 (15) | −0.0176 (13) | 0.0188 (14) |
O2 | 0.0826 (16) | 0.137 (2) | 0.0938 (17) | −0.0672 (15) | −0.0245 (14) | 0.0188 (15) |
C1 | 0.0454 (14) | 0.0470 (15) | 0.0548 (16) | −0.0134 (12) | −0.0041 (12) | −0.0114 (12) |
C2 | 0.0535 (16) | 0.0701 (19) | 0.0652 (18) | −0.0227 (14) | −0.0159 (14) | −0.0045 (15) |
C3 | 0.0605 (16) | 0.0624 (18) | 0.0512 (15) | −0.0233 (14) | −0.0133 (13) | −0.0001 (13) |
C4 | 0.0460 (14) | 0.0408 (14) | 0.0468 (14) | −0.0098 (11) | −0.0061 (11) | −0.0115 (12) |
C5 | 0.0541 (15) | 0.0553 (16) | 0.0474 (15) | −0.0189 (13) | −0.0085 (12) | −0.0077 (13) |
C6 | 0.0593 (16) | 0.0519 (16) | 0.0453 (14) | −0.0170 (13) | −0.0041 (12) | −0.0058 (12) |
C7 | 0.0506 (17) | 0.0634 (19) | 0.074 (2) | −0.0191 (14) | −0.0030 (15) | −0.0121 (16) |
C8 | 0.085 (2) | 0.0442 (16) | 0.0605 (17) | −0.0144 (14) | 0.0043 (15) | −0.0192 (14) |
C9 | 0.0667 (17) | 0.0400 (15) | 0.0549 (16) | −0.0186 (12) | 0.0012 (13) | −0.0107 (12) |
C10 | 0.0494 (14) | 0.0359 (14) | 0.0416 (13) | −0.0110 (11) | −0.0061 (11) | −0.0054 (11) |
C11 | 0.0453 (13) | 0.0386 (14) | 0.0391 (13) | −0.0119 (10) | −0.0083 (11) | −0.0034 (11) |
C12 | 0.0426 (13) | 0.0404 (14) | 0.0404 (13) | −0.0080 (10) | −0.0063 (10) | −0.0074 (11) |
C13 | 0.0485 (14) | 0.0494 (16) | 0.0499 (15) | −0.0125 (12) | 0.0041 (12) | −0.0104 (12) |
C14 | 0.0724 (18) | 0.0492 (17) | 0.0573 (17) | −0.0080 (14) | 0.0079 (14) | −0.0178 (14) |
C15—O3 | 1.279 (4) | C3—H3 | 0.9300 |
C15—N1 | 1.314 (4) | C4—C5 | 1.385 (3) |
C15—H15 | 0.9300 | C4—C11 | 1.499 (3) |
N1—C17 | 1.434 (4) | C5—C6 | 1.389 (3) |
N1—C16 | 1.441 (3) | C5—H5 | 0.9300 |
C16—H16A | 0.9600 | C6—H6 | 0.9300 |
C16—H16B | 0.9600 | C8—C9 | 1.346 (3) |
C16—H16C | 0.9600 | C8—C14i | 1.406 (4) |
C17—H17A | 0.9600 | C8—H8 | 0.9300 |
C17—H17B | 0.9600 | C9—C10 | 1.430 (3) |
C17—H17C | 0.9600 | C9—H9 | 0.9300 |
O1—C7 | 1.238 (3) | C10—C11 | 1.403 (3) |
O2—C7 | 1.255 (3) | C10—C12i | 1.438 (3) |
O2—H2D | 0.8200 | C11—C12 | 1.401 (3) |
C1—C6 | 1.378 (3) | C12—C13 | 1.428 (3) |
C1—C2 | 1.381 (3) | C12—C10i | 1.438 (3) |
C1—C7 | 1.485 (3) | C13—C14 | 1.353 (3) |
C2—C3 | 1.392 (3) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C8i | 1.406 (4) |
C3—C4 | 1.382 (3) | C14—H14 | 0.9300 |
O3—C15—N1 | 122.5 (4) | C4—C5—C6 | 120.7 (2) |
O3—C15—H15 | 118.8 | C4—C5—H5 | 119.6 |
N1—C15—H15 | 118.8 | C6—C5—H5 | 119.6 |
C15—N1—C17 | 121.0 (3) | C1—C6—C5 | 120.8 (2) |
C15—N1—C16 | 121.5 (3) | C1—C6—H6 | 119.6 |
C17—N1—C16 | 117.5 (2) | C5—C6—H6 | 119.6 |
N1—C16—H16A | 109.5 | O1—C7—O2 | 122.7 (3) |
N1—C16—H16B | 109.5 | O1—C7—C1 | 119.7 (3) |
H16A—C16—H16B | 109.5 | O2—C7—C1 | 117.6 (3) |
N1—C16—H16C | 109.5 | C9—C8—C14i | 120.8 (3) |
H16A—C16—H16C | 109.5 | C9—C8—H8 | 119.6 |
H16B—C16—H16C | 109.5 | C14i—C8—H8 | 119.6 |
N1—C17—H17A | 109.5 | C8—C9—C10 | 121.5 (2) |
N1—C17—H17B | 109.5 | C8—C9—H9 | 119.2 |
H17A—C17—H17B | 109.5 | C10—C9—H9 | 119.2 |
N1—C17—H17C | 109.5 | C11—C10—C9 | 122.0 (2) |
H17A—C17—H17C | 109.5 | C11—C10—C12i | 119.9 (2) |
H17B—C17—H17C | 109.5 | C9—C10—C12i | 118.1 (2) |
C7—O2—H2D | 109.5 | C12—C11—C10 | 119.9 (2) |
C6—C1—C2 | 118.9 (2) | C12—C11—C4 | 119.3 (2) |
C6—C1—C7 | 119.4 (2) | C10—C11—C4 | 120.8 (2) |
C2—C1—C7 | 121.6 (2) | C11—C12—C13 | 122.3 (2) |
C1—C2—C3 | 120.2 (2) | C11—C12—C10i | 120.2 (2) |
C1—C2—H2 | 119.9 | C13—C12—C10i | 117.5 (2) |
C3—C2—H2 | 119.9 | C14—C13—C12 | 122.0 (2) |
C4—C3—C2 | 121.2 (2) | C14—C13—H13 | 119.0 |
C4—C3—H3 | 119.4 | C12—C13—H13 | 119.0 |
C2—C3—H3 | 119.4 | C13—C14—C8i | 120.0 (2) |
C3—C4—C5 | 118.1 (2) | C13—C14—H14 | 120.0 |
C3—C4—C11 | 121.9 (2) | C8i—C14—H14 | 120.0 |
C5—C4—C11 | 119.9 (2) | ||
O3—C15—N1—C17 | 3.6 (5) | C8—C9—C10—C11 | −178.9 (2) |
O3—C15—N1—C16 | −177.4 (4) | C8—C9—C10—C12i | 0.9 (4) |
C6—C1—C2—C3 | −1.1 (4) | C9—C10—C11—C12 | −179.8 (2) |
C7—C1—C2—C3 | 179.7 (2) | C12i—C10—C11—C12 | 0.4 (4) |
C1—C2—C3—C4 | 0.5 (4) | C9—C10—C11—C4 | 2.2 (3) |
C2—C3—C4—C5 | 0.3 (4) | C12i—C10—C11—C4 | −177.6 (2) |
C2—C3—C4—C11 | −178.8 (2) | C3—C4—C11—C12 | 106.8 (3) |
C3—C4—C5—C6 | −0.5 (4) | C5—C4—C11—C12 | −72.3 (3) |
C11—C4—C5—C6 | 178.6 (2) | C3—C4—C11—C10 | −75.2 (3) |
C2—C1—C6—C5 | 0.9 (4) | C5—C4—C11—C10 | 105.7 (3) |
C7—C1—C6—C5 | −179.9 (2) | C10—C11—C12—C13 | 178.1 (2) |
C4—C5—C6—C1 | −0.1 (4) | C4—C11—C12—C13 | −3.9 (3) |
C6—C1—C7—O1 | −2.6 (4) | C10—C11—C12—C10i | −0.4 (4) |
C2—C1—C7—O1 | 176.6 (3) | C4—C11—C12—C10i | 177.6 (2) |
C6—C1—C7—O2 | 176.5 (3) | C11—C12—C13—C14 | −179.8 (2) |
C2—C1—C7—O2 | −4.3 (4) | C10i—C12—C13—C14 | −1.3 (4) |
C14i—C8—C9—C10 | 0.3 (4) | C12—C13—C14—C8i | 0.1 (4) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2D···O3ii | 0.82 | 1.79 | 2.603 (4) | 170 |
C5—H5···O3′ | 0.93 | 2.63 | 3.478 (5) | 152 |
C16—H16A···Cg1 | 0.96 | 2.91 | 3.485 (3) | 120 |
Symmetry code: (ii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C28H18O4·2C3H7NO |
Mr | 564.62 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.3692 (15), 8.9981 (18), 12.124 (2) |
α, β, γ (°) | 71.157 (3), 77.640 (3), 79.754 (3) |
V (Å3) | 738.0 (3) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.23 × 0.16 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.980, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5691, 2721, 1467 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.162, 1.02 |
No. of reflections | 2721 |
No. of parameters | 203 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.20 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2D···O3i | 0.82 | 1.79 | 2.603 (4) | 170.2 |
C5—H5···O3' | 0.93 | 2.63 | 3.478 (5) | 152.2 |
C16—H16A···Cg1 | 0.96 | 2.91 | 3.485 (3) | 120 |
Symmetry code: (i) −x, −y, −z+1. |
Acknowledgements
This work was supported by the Doctoral Foundation of Zhengzhou University of Light Industry (000420).
References
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H., Wu, Y. J. & Yan, W. B. (2006). J. Organomet. Chem. 691, 5688–5696. Web of Science CrossRef CAS Google Scholar
Li, H., Zhang, L., Liu, Y.-Q., Mao, D.-B. & Zhang, W.-Y. (2008). Acta Cryst. E64, o2094. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, C., Gong, J. F., Guo, T., Zhang, Y. H. & Wu, Y. J. (2008). J. Mol. Catal. A Chem. 279, 69–76. Web of Science CSD CrossRef CAS Google Scholar
Xu, C., Gong, J. F., Yue, S. F., Zhu, Y. & Wu, Y. J. (2006). Dalton Trans. pp. 4730–4739. Web of Science CSD CrossRef Google Scholar
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Cyclopalladated ferrocenylimine complexs with monophosphino ligands were successfully used as catalysts for Suzuki reactions (Xu et al. 2006; Li et al., 2006; Xu et al. 2008). We have recently reported that the structure of 4-(2,5-dihexyloxyphenyl)benzoic acid was obtained from the Suzuki coupling reaction (Li et al., 2008). The title compound was derived from the Suzuki reaction of 9,10-dibromoanthracene and 4-carboxyphenylboronic acid.
In the title compound (Fig.1), the dihedral angle between benzene rings and anthracene rings is 74.05 (12)°. A crystallographic inversion centre is in the middle of the anthracene unit, and an approximate two-fold pseudo rotation axis is running along the plane of the anthracene unit. The dimethylformamide solvent molecules are partially disordered over two positions, O3 and O3', of approximately equal occupancy, (0.529 (6) and 0.471 (6), respectively. The different intermolecular hydrogen bonding contacts are shown in Fig. 1 (O3' is the acceptor) and Fig. 2 (with O3 as acceptor). The intermolecular O—H···O hydrogen bonds result in the formation of long 2:1 solvate:complex aggregates, (Table 1) which are alternately linked via weak intermolecular C—H···O contacts generated from the rotational disorder of the formamide oxygen atom (0.471 (6) site occupancy). C—H···π interactions support these contacts in the crystal structure foming a one-dimensional supramolecular architecture (Fig. 1 and Fig. 2).