organic compounds
9-(4-Methoxyphenyl)anthracene
aCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-25, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, India
*Correspondence e-mail: shirai2011@gmail.com
In the title compound, C21H16O, the dihedral angle between the anthracene ring system and the benzene ring is 74.3 (5)°. The anthracene ring system is essentially planar (r.m.s. deviation = 0.0257 Å) and the methoxy group lies in the plane of the benzene ring [C1—O1—C2—C7 torsion angle = 0.5 (2)°]. The features π–π [centroid–centroid distance = 3.9487 (12) Å] and C–H⋯π interactions, forming a sheet running along the a-axis direction.
Related literature
For applications of anthracene, see: Bae et al. (2010); Debbab et al. (2012). For a related structure, see: Wang et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell 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: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812047149/pv2599sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047149/pv2599Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812047149/pv2599Isup3.cml
(4-Methoxyphenyl)(2-(phenyl(pivaloyloxy)methyl)phenyl)methyl)pivalate (0.5 g, 0.94 mmol) upon interaction with ZnBr2 (0.02 g, 0.13 mmol) followed by removal of solvent and column chromatographic purification (silica gel; hexane-ethyl acetate, 99:1) led to the isolation of product as a pale yellow solid (0.32 g, 87%). The compound was recrystalized from chloroform. Single crystals suitable for X-ray
were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C—H distances 0.93 and 0.96 Å for aryl and methyl H-atoms with Uiso(H) = 1.5Ueq(methyl-C) and 1.2Ueq(aryl-C).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. | |
Fig. 2. A view of the π···π and C—-H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. |
C21H16O | F(000) = 600 |
Mr = 284.34 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3806 reflections |
a = 13.5539 (5) Å | θ = 2.0–28.3° |
b = 15.0626 (5) Å | µ = 0.07 mm−1 |
c = 7.6130 (2) Å | T = 293 K |
β = 99.219 (2)° | Block, colourless |
V = 1534.17 (9) Å3 | 0.20 × 0.20 × 0.20 mm |
Z = 4 |
Bruker SMART APEXII area-detector diffractometer | 3806 independent reflections |
Radiation source: fine-focus sealed tube | 2317 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and ϕ scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −18→16 |
Tmin = 0.981, Tmax = 0.985 | k = −19→19 |
14917 measured reflections | l = −10→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0556P)2 + 0.1555P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3806 reflections | Δρmax = 0.14 e Å−3 |
201 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.019 (2) |
C21H16O | V = 1534.17 (9) Å3 |
Mr = 284.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.5539 (5) Å | µ = 0.07 mm−1 |
b = 15.0626 (5) Å | T = 293 K |
c = 7.6130 (2) Å | 0.20 × 0.20 × 0.20 mm |
β = 99.219 (2)° |
Bruker SMART APEXII area-detector diffractometer | 3806 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2317 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.985 | Rint = 0.033 |
14917 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.14 e Å−3 |
3806 reflections | Δρmin = −0.12 e Å−3 |
201 parameters |
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 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 | ||
O1 | 0.84535 (8) | −0.16715 (6) | −0.12133 (14) | 0.0625 (3) | |
C5 | 0.75001 (9) | 0.00335 (9) | 0.24854 (16) | 0.0444 (3) | |
C8 | 0.71622 (11) | 0.06367 (9) | 0.38283 (16) | 0.0469 (3) | |
C4 | 0.73498 (10) | −0.08803 (9) | 0.25059 (19) | 0.0513 (4) | |
H4 | 0.7022 | −0.1127 | 0.3373 | 0.062* | |
C6 | 0.79836 (11) | 0.03687 (9) | 0.11597 (18) | 0.0543 (4) | |
H6 | 0.8091 | 0.0978 | 0.1112 | 0.065* | |
C2 | 0.81595 (9) | −0.10761 (9) | −0.00379 (17) | 0.0471 (3) | |
C17 | 0.78712 (11) | 0.10166 (9) | 0.51685 (17) | 0.0484 (3) | |
C9 | 0.61419 (11) | 0.08466 (10) | 0.37219 (18) | 0.0542 (4) | |
C3 | 0.76772 (11) | −0.14246 (9) | 0.12656 (19) | 0.0526 (4) | |
H3 | 0.7572 | −0.2034 | 0.1309 | 0.063* | |
C16 | 0.75482 (13) | 0.16124 (9) | 0.64257 (18) | 0.0571 (4) | |
C18 | 0.89164 (11) | 0.08456 (10) | 0.53287 (18) | 0.0553 (4) | |
H18 | 0.9144 | 0.0464 | 0.4521 | 0.066* | |
C14 | 0.58323 (13) | 0.14597 (11) | 0.4959 (2) | 0.0633 (4) | |
C7 | 0.83127 (11) | −0.01703 (9) | −0.00955 (18) | 0.0535 (4) | |
H7 | 0.8635 | 0.0074 | −0.0972 | 0.064* | |
C19 | 0.95862 (14) | 0.12230 (11) | 0.6623 (2) | 0.0687 (5) | |
H19 | 1.0264 | 0.1101 | 0.6690 | 0.082* | |
C15 | 0.65393 (14) | 0.18180 (10) | 0.6282 (2) | 0.0681 (5) | |
H15 | 0.6333 | 0.2208 | 0.7099 | 0.082* | |
C21 | 0.82821 (16) | 0.19878 (11) | 0.7773 (2) | 0.0730 (5) | |
H21 | 0.8080 | 0.2371 | 0.8605 | 0.088* | |
C10 | 0.53910 (12) | 0.04832 (12) | 0.2391 (2) | 0.0710 (5) | |
H10 | 0.5573 | 0.0077 | 0.1581 | 0.085* | |
C20 | 0.92599 (16) | 0.18010 (12) | 0.7871 (2) | 0.0772 (5) | |
H20 | 0.9723 | 0.2054 | 0.8765 | 0.093* | |
C1 | 0.89552 (14) | −0.13330 (12) | −0.2567 (2) | 0.0788 (5) | |
H1A | 0.8533 | −0.0912 | −0.3275 | 0.118* | |
H1B | 0.9110 | −0.1812 | −0.3309 | 0.118* | |
H1C | 0.9562 | −0.1046 | −0.2035 | 0.118* | |
C13 | 0.47972 (16) | 0.16896 (14) | 0.4771 (3) | 0.0847 (6) | |
H13 | 0.4587 | 0.2095 | 0.5555 | 0.102* | |
C11 | 0.44201 (14) | 0.07163 (15) | 0.2281 (3) | 0.0893 (6) | |
H11 | 0.3945 | 0.0468 | 0.1402 | 0.107* | |
C12 | 0.41231 (16) | 0.13311 (17) | 0.3484 (3) | 0.0960 (7) | |
H12 | 0.3454 | 0.1491 | 0.3386 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0721 (7) | 0.0500 (6) | 0.0713 (7) | 0.0036 (5) | 0.0293 (6) | −0.0138 (5) |
C5 | 0.0457 (7) | 0.0464 (7) | 0.0423 (6) | 0.0033 (6) | 0.0101 (6) | −0.0003 (6) |
C8 | 0.0587 (9) | 0.0420 (7) | 0.0433 (7) | 0.0043 (6) | 0.0183 (6) | 0.0026 (6) |
C4 | 0.0539 (8) | 0.0488 (8) | 0.0546 (8) | −0.0021 (6) | 0.0190 (7) | 0.0041 (6) |
C6 | 0.0739 (10) | 0.0397 (7) | 0.0537 (8) | −0.0032 (7) | 0.0235 (7) | −0.0027 (6) |
C2 | 0.0444 (7) | 0.0456 (7) | 0.0526 (7) | 0.0043 (6) | 0.0112 (6) | −0.0073 (6) |
C17 | 0.0664 (9) | 0.0384 (7) | 0.0439 (7) | −0.0020 (6) | 0.0198 (6) | 0.0027 (6) |
C9 | 0.0628 (9) | 0.0552 (9) | 0.0485 (7) | 0.0108 (7) | 0.0207 (7) | 0.0060 (7) |
C3 | 0.0572 (9) | 0.0384 (7) | 0.0645 (9) | −0.0013 (6) | 0.0169 (7) | −0.0005 (6) |
C16 | 0.0865 (11) | 0.0409 (7) | 0.0494 (8) | −0.0037 (7) | 0.0269 (8) | −0.0005 (6) |
C18 | 0.0656 (10) | 0.0521 (8) | 0.0504 (8) | −0.0068 (7) | 0.0163 (7) | −0.0022 (7) |
C14 | 0.0776 (11) | 0.0613 (10) | 0.0580 (9) | 0.0177 (8) | 0.0322 (8) | 0.0073 (8) |
C7 | 0.0692 (10) | 0.0459 (8) | 0.0507 (7) | −0.0032 (7) | 0.0258 (7) | −0.0015 (6) |
C19 | 0.0736 (11) | 0.0719 (11) | 0.0605 (9) | −0.0202 (9) | 0.0111 (8) | −0.0043 (8) |
C15 | 0.1015 (14) | 0.0520 (9) | 0.0599 (9) | 0.0122 (9) | 0.0405 (9) | −0.0029 (7) |
C21 | 0.1192 (16) | 0.0489 (9) | 0.0561 (9) | −0.0182 (10) | 0.0303 (10) | −0.0120 (7) |
C10 | 0.0626 (10) | 0.0904 (13) | 0.0613 (9) | 0.0193 (9) | 0.0136 (8) | −0.0032 (9) |
C20 | 0.1028 (15) | 0.0692 (11) | 0.0601 (10) | −0.0349 (11) | 0.0147 (10) | −0.0097 (8) |
C1 | 0.0935 (13) | 0.0728 (12) | 0.0811 (11) | −0.0002 (10) | 0.0480 (10) | −0.0192 (10) |
C13 | 0.0924 (14) | 0.0910 (14) | 0.0807 (12) | 0.0338 (11) | 0.0441 (11) | 0.0065 (11) |
C11 | 0.0623 (11) | 0.1274 (18) | 0.0782 (11) | 0.0241 (11) | 0.0109 (9) | −0.0017 (12) |
C12 | 0.0735 (13) | 0.1313 (19) | 0.0882 (14) | 0.0398 (13) | 0.0287 (12) | 0.0091 (14) |
O1—C2 | 1.3704 (15) | C18—H18 | 0.9300 |
O1—C1 | 1.4176 (18) | C14—C15 | 1.384 (2) |
C5—C6 | 1.3838 (17) | C14—C13 | 1.430 (3) |
C5—C4 | 1.3919 (18) | C7—H7 | 0.9300 |
C5—C8 | 1.4935 (17) | C19—C20 | 1.411 (2) |
C8—C17 | 1.4063 (19) | C19—H19 | 0.9300 |
C8—C9 | 1.408 (2) | C15—H15 | 0.9300 |
C4—C3 | 1.3766 (19) | C21—C20 | 1.345 (3) |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C6—C7 | 1.3813 (18) | C10—C11 | 1.352 (2) |
C6—H6 | 0.9300 | C10—H10 | 0.9300 |
C2—C3 | 1.3768 (18) | C20—H20 | 0.9300 |
C2—C7 | 1.3818 (19) | C1—H1A | 0.9600 |
C17—C18 | 1.426 (2) | C1—H1B | 0.9600 |
C17—C16 | 1.4309 (19) | C1—H1C | 0.9600 |
C9—C10 | 1.425 (2) | C13—C12 | 1.341 (3) |
C9—C14 | 1.429 (2) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.406 (3) |
C16—C15 | 1.389 (2) | C11—H11 | 0.9300 |
C16—C21 | 1.426 (2) | C12—H12 | 0.9300 |
C18—C19 | 1.353 (2) | ||
C2—O1—C1 | 117.58 (11) | C6—C7—C2 | 119.44 (12) |
C6—C5—C4 | 117.14 (12) | C6—C7—H7 | 120.3 |
C6—C5—C8 | 120.68 (12) | C2—C7—H7 | 120.3 |
C4—C5—C8 | 122.17 (11) | C18—C19—C20 | 120.22 (17) |
C17—C8—C9 | 120.07 (12) | C18—C19—H19 | 119.9 |
C17—C8—C5 | 119.69 (12) | C20—C19—H19 | 119.9 |
C9—C8—C5 | 120.21 (13) | C14—C15—C16 | 121.90 (14) |
C3—C4—C5 | 121.16 (12) | C14—C15—H15 | 119.1 |
C3—C4—H4 | 119.4 | C16—C15—H15 | 119.1 |
C5—C4—H4 | 119.4 | C20—C21—C16 | 121.62 (16) |
C7—C6—C5 | 122.23 (13) | C20—C21—H21 | 119.2 |
C7—C6—H6 | 118.9 | C16—C21—H21 | 119.2 |
C5—C6—H6 | 118.9 | C11—C10—C9 | 121.45 (17) |
O1—C2—C3 | 116.26 (12) | C11—C10—H10 | 119.3 |
O1—C2—C7 | 124.36 (12) | C9—C10—H10 | 119.3 |
C3—C2—C7 | 119.38 (12) | C21—C20—C19 | 120.27 (16) |
C8—C17—C18 | 122.87 (12) | C21—C20—H20 | 119.9 |
C8—C17—C16 | 119.58 (13) | C19—C20—H20 | 119.9 |
C18—C17—C16 | 117.54 (13) | O1—C1—H1A | 109.5 |
C8—C9—C10 | 122.52 (13) | O1—C1—H1B | 109.5 |
C8—C9—C14 | 119.77 (14) | H1A—C1—H1B | 109.5 |
C10—C9—C14 | 117.70 (14) | O1—C1—H1C | 109.5 |
C4—C3—C2 | 120.65 (13) | H1A—C1—H1C | 109.5 |
C4—C3—H3 | 119.7 | H1B—C1—H1C | 109.5 |
C2—C3—H3 | 119.7 | C12—C13—C14 | 121.20 (17) |
C15—C16—C21 | 122.17 (15) | C12—C13—H13 | 119.4 |
C15—C16—C17 | 119.34 (15) | C14—C13—H13 | 119.4 |
C21—C16—C17 | 118.48 (15) | C10—C11—C12 | 120.5 (2) |
C19—C18—C17 | 121.86 (14) | C10—C11—H11 | 119.7 |
C19—C18—H18 | 119.1 | C12—C11—H11 | 119.7 |
C17—C18—H18 | 119.1 | C13—C12—C11 | 120.56 (18) |
C15—C14—C9 | 119.31 (14) | C13—C12—H12 | 119.7 |
C15—C14—C13 | 122.16 (16) | C11—C12—H12 | 119.7 |
C9—C14—C13 | 118.53 (17) | ||
C6—C5—C8—C17 | −72.83 (17) | C8—C17—C18—C19 | 179.58 (13) |
C4—C5—C8—C17 | 106.98 (15) | C16—C17—C18—C19 | 0.5 (2) |
C6—C5—C8—C9 | 105.19 (16) | C8—C9—C14—C15 | −2.0 (2) |
C4—C5—C8—C9 | −74.99 (17) | C10—C9—C14—C15 | 179.23 (14) |
C6—C5—C4—C3 | 0.5 (2) | C8—C9—C14—C13 | 177.33 (14) |
C8—C5—C4—C3 | −179.30 (13) | C10—C9—C14—C13 | −1.4 (2) |
C4—C5—C6—C7 | −0.3 (2) | C5—C6—C7—C2 | −0.1 (2) |
C8—C5—C6—C7 | 179.51 (13) | O1—C2—C7—C6 | 179.96 (13) |
C1—O1—C2—C3 | −179.79 (13) | C3—C2—C7—C6 | 0.3 (2) |
C1—O1—C2—C7 | 0.5 (2) | C17—C18—C19—C20 | 0.3 (2) |
C9—C8—C17—C18 | −178.74 (12) | C9—C14—C15—C16 | 1.3 (2) |
C5—C8—C17—C18 | −0.71 (19) | C13—C14—C15—C16 | −178.05 (15) |
C9—C8—C17—C16 | 0.35 (19) | C21—C16—C15—C14 | 179.21 (14) |
C5—C8—C17—C16 | 178.38 (11) | C17—C16—C15—C14 | 0.3 (2) |
C17—C8—C9—C10 | 179.89 (13) | C15—C16—C21—C20 | −178.28 (15) |
C5—C8—C9—C10 | 1.9 (2) | C17—C16—C21—C20 | 0.7 (2) |
C17—C8—C9—C14 | 1.2 (2) | C8—C9—C10—C11 | −177.86 (16) |
C5—C8—C9—C14 | −176.82 (12) | C14—C9—C10—C11 | 0.9 (2) |
C5—C4—C3—C2 | −0.3 (2) | C16—C21—C20—C19 | 0.1 (3) |
O1—C2—C3—C4 | −179.78 (13) | C18—C19—C20—C21 | −0.6 (2) |
C7—C2—C3—C4 | −0.1 (2) | C15—C14—C13—C12 | −179.66 (18) |
C8—C17—C16—C15 | −1.1 (2) | C9—C14—C13—C12 | 1.0 (3) |
C18—C17—C16—C15 | 178.03 (13) | C9—C10—C11—C12 | 0.2 (3) |
C8—C17—C16—C21 | 179.92 (12) | C14—C13—C12—C11 | 0.0 (3) |
C18—C17—C16—C21 | −0.94 (19) | C10—C11—C12—C13 | −0.6 (3) |
Cg1 and Cg4 are the centroids of the C2–C7 and C16–C21 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cg4i | 0.93 | 2.77 | 3.566 (2) | 145 |
C11—H11···Cg1ii | 0.93 | 2.87 | 3.724 (2) | 154 |
C19—H19···Cg1iii | 0.93 | 2.94 | 3.772 (2) | 150 |
C21—H21···Cg4iv | 0.93 | 2.88 | 3.711 (2) | 150 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z; (iii) −x+2, −y, −z+1; (iv) x, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H16O |
Mr | 284.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.5539 (5), 15.0626 (5), 7.6130 (2) |
β (°) | 99.219 (2) |
V (Å3) | 1534.17 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.20 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.981, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14917, 3806, 2317 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.130, 1.02 |
No. of reflections | 3806 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.12 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 and Cg4 are the centroids of the C2–C7 and C16–C21 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cg4i | 0.93 | 2.77 | 3.566 (2) | 145 |
C11—H11···Cg1ii | 0.93 | 2.87 | 3.724 (2) | 154 |
C19—H19···Cg1iii | 0.93 | 2.94 | 3.772 (2) | 150 |
C21—H21···Cg4iv | 0.93 | 2.88 | 3.711 (2) | 150 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z; (iii) −x+2, −y, −z+1; (iv) x, −y−1/2, z−1/2. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. VS and DV also thank the UGC SAP for financial support.
References
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Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings. Its derivatives possess antimicrobial activity (Debbab et al., 2012). It is used in the production of dyes and organic semiconductors (Bae et al., 2010). In order to obtain detailed information on molecular conformations in the solid state, an X-ray crystallographic study of the title compound was carried out.
The anthracene ring system in the title molecule (Fig. 1) is essentially planar (rmsd = 0.0257 Å) and the methoxy group lies in the plane of the benzene ring with the torsion angle C1—O1—C2—C7 = 0.5 (2)°. The dihedral angle between the mean-planes of the anthracene and benzene rings is 74.3 (5)° showing that both the ring systems are almost perpendicular to each other. The bond lengths and angles in the title compound are comparable to those observed in a closely related compound (Wang et al., 2008).
The π···π electron interaction is observed between the rings (C9—C14) [at x, y, z] and (C9—C14) [at 1 - x, - y, 1 - z] with the centroid-centroid distance 3.9487 (12) Å. In addition, the crystal packing is stabilized by C–H···π (Table. 1) types of interaction.