organic compounds
1-Methoxy-11H-benzo[b]fluoren-11-one
aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
*Correspondence e-mail: kyuchen@fcu.edu.tw
In the title compound, C18H12O2, the non-H atoms are nearly coplanar, the maximum atomic deviation being 0.113 (2) Å. π–π stacking is observed in the the shortest centroid–centroid distance being 3.5983 (19) Å. The molecular packing is further stabilized by weak C—H⋯O hydrogen bonds, forming an infinite chain along [100] and generating a C(6) motif.
Related literature
For the preparation of the title compound, see: Tang et al. (2011). For applications of indanone derivatives, see: Borbone et al. (2011); Borge et al. (2010); Cai & Dolbier (2005); Cui et al. (2009); Fu & Wang (2008); Li et al. (2009); Rahman et al. (2011); Sousa et al. (2011); Yu et al. (2011). For related structures, see: Chang & Chen (2012); Chen et al. (2011a,b).
Experimental
Crystal data
|
Refinement
|
Data collection: SMART (Bruker, 2005); cell SAINT (Bruker, 2005); 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 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812050076/xu5629sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050076/xu5629Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050076/xu5629Isup3.cml
The title compound was synthesized according to the literature (Tang et al., 2011). Yellow parallelepiped-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of six weeks by slow evaporation from a chloroform solution.
The C bound H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Indanone and its derivatives are some of the most widely used organic compounds (Rahman et al., 2011). They are used as pigments and dyes (Cui et al., 2009; Li et al., 2009), intermediates in organic synthesis (Borbone et al., 2011; Borge et al., 2010; Fu & Wang, 2008; Yu et al., 2011) and exhibit a wide variety of biological activities (Sousa et al., 2011). In addition, 1-indanones were important precursors in the regiospecific synthesis of 2-fluoro-1-naphthols (Cai et al., 2005).
The molecular structure of the title compound comprises a 7-methoxy-1-indanone unit having a naphthalene ring fused on one side (Fig. 1). The 1-indaneone moiety is essentially planar (r.m.s. deviation = 0.0075 Å), which is consistent with previous studies (Chang & Chen, 2012; Chen et al., 2011a,b). π—π stacking is observed between the tetracyclic plane and its adjacent one, the closest centroid-centroid distance being 3.5983 (19) Å [symmetry code: 2 - x, -y, 2 - z]. The molecular packing (Fig. 2) is further stabilized by weak non-classical intermolecular C—H···O hydrogen bonds (Table 1).
For the preparation of the title compound, see: Tang et al. (2011). For applications of indanone derivatives, see: Borbone et al. (2011); Borge et al. (2010); Cai et al. (2005); Cui et al. (2009); Fu & Wang (2008); Li et al. (2009); Rahman et al. (2011); Sousa et al. (2011); Yu et al. (2011). For related structures, see: Chang & Chen (2012); Chen et al. (2011a,b).
Data collection: SMART (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).C18H12O2 | F(000) = 544 |
Mr = 260.28 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6867 reflections |
a = 7.7202 (3) Å | θ = 2.7–26.4° |
b = 9.2462 (4) Å | µ = 0.09 mm−1 |
c = 18.0294 (8) Å | T = 299 K |
β = 99.935 (2)° | Parallelepiped, yellow |
V = 1267.68 (9) Å3 | 0.50 × 0.47 × 0.20 mm |
Z = 4 |
Bruker SMART CCD detector diffractometer | 2559 independent reflections |
Radiation source: fine-focus sealed tube | 1881 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→9 |
Tmin = 0.957, Tmax = 0.983 | k = −11→10 |
11580 measured reflections | l = −22→21 |
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)] = 0.083 | H-atom parameters constrained |
wR(F2) = 0.250 | w = 1/[σ2(Fo2) + (0.1046P)2 + 1.682P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
2559 reflections | Δρmax = 0.49 e Å−3 |
183 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.041 (7) |
C18H12O2 | V = 1267.68 (9) Å3 |
Mr = 260.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.7202 (3) Å | µ = 0.09 mm−1 |
b = 9.2462 (4) Å | T = 299 K |
c = 18.0294 (8) Å | 0.50 × 0.47 × 0.20 mm |
β = 99.935 (2)° |
Bruker SMART CCD detector diffractometer | 2559 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1881 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.983 | Rint = 0.042 |
11580 measured reflections |
R[F2 > 2σ(F2)] = 0.083 | 0 restraints |
wR(F2) = 0.250 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.49 e Å−3 |
2559 reflections | Δρmin = −0.42 e Å−3 |
183 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 | 1.2838 (3) | 0.3051 (3) | 0.92283 (15) | 0.0675 (8) | |
O2 | 1.3420 (3) | 0.0972 (3) | 1.04942 (14) | 0.0571 (7) | |
C1 | 1.0841 (4) | 0.2264 (3) | 1.00540 (17) | 0.0428 (7) | |
C2 | 1.1419 (4) | 0.3058 (4) | 0.94252 (18) | 0.0464 (8) | |
C3 | 0.9836 (4) | 0.3911 (3) | 0.90635 (17) | 0.0439 (7) | |
C4 | 0.9640 (4) | 0.4820 (4) | 0.84656 (18) | 0.0490 (8) | |
H4 | 1.0571 | 0.4978 | 0.8209 | 0.059* | |
C5 | 0.8006 (4) | 0.5531 (3) | 0.82323 (17) | 0.0461 (8) | |
C6 | 0.7726 (5) | 0.6517 (4) | 0.7623 (2) | 0.0579 (9) | |
H6 | 0.8634 | 0.6712 | 0.7360 | 0.069* | |
C7 | 0.6147 (6) | 0.7183 (4) | 0.7419 (2) | 0.0683 (11) | |
H7 | 0.5990 | 0.7835 | 0.7020 | 0.082* | |
C8 | 0.4773 (6) | 0.6901 (4) | 0.7796 (2) | 0.0694 (11) | |
H8 | 0.3696 | 0.7359 | 0.7646 | 0.083* | |
C9 | 0.4978 (5) | 0.5959 (4) | 0.8385 (2) | 0.0578 (9) | |
H9 | 0.4038 | 0.5780 | 0.8633 | 0.069* | |
C10 | 0.6602 (4) | 0.5249 (3) | 0.86266 (19) | 0.0475 (8) | |
C11 | 0.6857 (4) | 0.4280 (3) | 0.92502 (19) | 0.0473 (8) | |
H11 | 0.5937 | 0.4089 | 0.9508 | 0.057* | |
C12 | 0.8438 (4) | 0.3637 (3) | 0.94670 (17) | 0.0401 (7) | |
C13 | 0.9079 (4) | 0.2608 (3) | 1.00807 (17) | 0.0420 (7) | |
C14 | 0.8220 (4) | 0.2001 (4) | 1.0611 (2) | 0.0522 (8) | |
H14 | 0.7052 | 0.2224 | 1.0625 | 0.063* | |
C15 | 0.9155 (5) | 0.1040 (4) | 1.1126 (2) | 0.0589 (9) | |
H15 | 0.8600 | 0.0626 | 1.1493 | 0.071* | |
C16 | 1.0877 (5) | 0.0687 (4) | 1.1106 (2) | 0.0544 (9) | |
H16 | 1.1465 | 0.0040 | 1.1458 | 0.065* | |
C17 | 1.1749 (4) | 0.1289 (4) | 1.05646 (18) | 0.0471 (8) | |
C18 | 1.4337 (5) | −0.0107 (4) | 1.0985 (2) | 0.0627 (10) | |
H18A | 1.4545 | 0.0248 | 1.1493 | 0.094* | |
H18B | 1.5440 | −0.0321 | 1.0832 | 0.094* | |
H18C | 1.3638 | −0.0971 | 1.0958 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0431 (14) | 0.087 (2) | 0.0777 (18) | 0.0056 (12) | 0.0246 (12) | 0.0121 (15) |
O2 | 0.0438 (13) | 0.0598 (16) | 0.0666 (16) | 0.0075 (11) | 0.0062 (11) | 0.0054 (12) |
C1 | 0.0410 (16) | 0.0411 (16) | 0.0463 (16) | −0.0028 (13) | 0.0079 (12) | −0.0059 (13) |
C2 | 0.0366 (16) | 0.0548 (19) | 0.0490 (17) | −0.0035 (13) | 0.0105 (13) | −0.0041 (14) |
C3 | 0.0381 (16) | 0.0436 (17) | 0.0502 (17) | −0.0034 (12) | 0.0086 (12) | −0.0051 (13) |
C4 | 0.0439 (17) | 0.053 (2) | 0.0506 (18) | −0.0039 (14) | 0.0105 (13) | −0.0026 (14) |
C5 | 0.0506 (18) | 0.0394 (17) | 0.0468 (17) | −0.0019 (13) | 0.0040 (13) | −0.0069 (13) |
C6 | 0.069 (2) | 0.051 (2) | 0.0510 (19) | 0.0002 (17) | 0.0046 (16) | −0.0012 (15) |
C7 | 0.085 (3) | 0.054 (2) | 0.060 (2) | 0.012 (2) | −0.003 (2) | −0.0058 (18) |
C8 | 0.070 (3) | 0.057 (2) | 0.073 (2) | 0.0191 (19) | −0.009 (2) | −0.0058 (19) |
C9 | 0.0480 (19) | 0.056 (2) | 0.067 (2) | 0.0071 (16) | 0.0021 (16) | −0.0088 (17) |
C10 | 0.0422 (17) | 0.0401 (17) | 0.0579 (18) | 0.0022 (13) | 0.0023 (13) | −0.0100 (14) |
C11 | 0.0393 (16) | 0.0428 (18) | 0.0606 (19) | −0.0022 (13) | 0.0105 (13) | −0.0071 (14) |
C12 | 0.0355 (15) | 0.0377 (16) | 0.0478 (16) | −0.0042 (12) | 0.0095 (12) | −0.0070 (12) |
C13 | 0.0426 (16) | 0.0360 (16) | 0.0486 (16) | −0.0038 (12) | 0.0113 (12) | −0.0073 (12) |
C14 | 0.0449 (18) | 0.055 (2) | 0.0601 (19) | −0.0025 (14) | 0.0189 (14) | −0.0008 (16) |
C15 | 0.065 (2) | 0.058 (2) | 0.058 (2) | −0.0087 (17) | 0.0212 (17) | 0.0047 (17) |
C16 | 0.058 (2) | 0.052 (2) | 0.0530 (19) | −0.0010 (16) | 0.0095 (15) | 0.0011 (15) |
C17 | 0.0447 (17) | 0.0449 (18) | 0.0511 (17) | −0.0018 (13) | 0.0064 (13) | −0.0043 (14) |
C18 | 0.053 (2) | 0.056 (2) | 0.074 (2) | 0.0063 (16) | −0.0035 (17) | 0.0071 (18) |
O1—C2 | 1.208 (4) | C8—H8 | 0.9300 |
O2—C17 | 1.350 (4) | C9—C10 | 1.416 (5) |
O2—C18 | 1.436 (4) | C9—H9 | 0.9300 |
C1—C17 | 1.389 (5) | C10—C11 | 1.425 (5) |
C1—C13 | 1.406 (4) | C11—C12 | 1.354 (4) |
C1—C2 | 1.483 (4) | C11—H11 | 0.9300 |
C2—C3 | 1.505 (4) | C12—C13 | 1.478 (4) |
C3—C4 | 1.355 (5) | C13—C14 | 1.374 (4) |
C3—C12 | 1.424 (4) | C14—C15 | 1.394 (5) |
C4—C5 | 1.421 (5) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.375 (5) |
C5—C6 | 1.415 (5) | C15—H15 | 0.9300 |
C5—C10 | 1.419 (5) | C16—C17 | 1.394 (5) |
C6—C7 | 1.359 (5) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C18—H18A | 0.9600 |
C7—C8 | 1.379 (6) | C18—H18B | 0.9600 |
C7—H7 | 0.9300 | C18—H18C | 0.9600 |
C8—C9 | 1.363 (6) | ||
C17—O2—C18 | 118.0 (3) | C9—C10—C11 | 121.9 (3) |
C17—C1—C13 | 120.3 (3) | C5—C10—C11 | 119.8 (3) |
C17—C1—C2 | 130.1 (3) | C12—C11—C10 | 119.9 (3) |
C13—C1—C2 | 109.5 (3) | C12—C11—H11 | 120.0 |
O1—C2—C1 | 129.0 (3) | C10—C11—H11 | 120.0 |
O1—C2—C3 | 125.8 (3) | C11—C12—C3 | 120.0 (3) |
C1—C2—C3 | 105.2 (3) | C11—C12—C13 | 131.9 (3) |
C4—C3—C12 | 121.8 (3) | C3—C12—C13 | 108.2 (3) |
C4—C3—C2 | 129.8 (3) | C14—C13—C1 | 121.2 (3) |
C12—C3—C2 | 108.4 (3) | C14—C13—C12 | 130.1 (3) |
C3—C4—C5 | 119.6 (3) | C1—C13—C12 | 108.7 (3) |
C3—C4—H4 | 120.2 | C13—C14—C15 | 117.9 (3) |
C5—C4—H4 | 120.2 | C13—C14—H14 | 121.1 |
C6—C5—C10 | 118.7 (3) | C15—C14—H14 | 121.1 |
C6—C5—C4 | 122.4 (3) | C16—C15—C14 | 121.8 (3) |
C10—C5—C4 | 118.9 (3) | C16—C15—H15 | 119.1 |
C7—C6—C5 | 120.8 (4) | C14—C15—H15 | 119.1 |
C7—C6—H6 | 119.6 | C15—C16—C17 | 120.6 (3) |
C5—C6—H6 | 119.6 | C15—C16—H16 | 119.7 |
C6—C7—C8 | 120.8 (4) | C17—C16—H16 | 119.7 |
C6—C7—H7 | 119.6 | O2—C17—C1 | 117.4 (3) |
C8—C7—H7 | 119.6 | O2—C17—C16 | 124.3 (3) |
C9—C8—C7 | 120.6 (4) | C1—C17—C16 | 118.3 (3) |
C9—C8—H8 | 119.7 | O2—C18—H18A | 109.5 |
C7—C8—H8 | 119.7 | O2—C18—H18B | 109.5 |
C8—C9—C10 | 120.9 (4) | H18A—C18—H18B | 109.5 |
C8—C9—H9 | 119.5 | O2—C18—H18C | 109.5 |
C10—C9—H9 | 119.5 | H18A—C18—H18C | 109.5 |
C9—C10—C5 | 118.2 (3) | H18B—C18—H18C | 109.5 |
C17—C1—C2—O1 | −1.7 (6) | C10—C11—C12—C13 | 179.8 (3) |
C13—C1—C2—O1 | 179.4 (3) | C4—C3—C12—C11 | 0.8 (5) |
C17—C1—C2—C3 | 178.3 (3) | C2—C3—C12—C11 | −179.9 (3) |
C13—C1—C2—C3 | −0.6 (3) | C4—C3—C12—C13 | −179.9 (3) |
O1—C2—C3—C4 | 0.0 (6) | C2—C3—C12—C13 | −0.6 (3) |
C1—C2—C3—C4 | 180.0 (3) | C17—C1—C13—C14 | 0.4 (5) |
O1—C2—C3—C12 | −179.3 (3) | C2—C1—C13—C14 | 179.4 (3) |
C1—C2—C3—C12 | 0.7 (3) | C17—C1—C13—C12 | −178.7 (3) |
C12—C3—C4—C5 | 0.3 (5) | C2—C1—C13—C12 | 0.2 (3) |
C2—C3—C4—C5 | −178.9 (3) | C11—C12—C13—C14 | 0.4 (6) |
C3—C4—C5—C6 | 178.6 (3) | C3—C12—C13—C14 | −178.8 (3) |
C3—C4—C5—C10 | −1.1 (5) | C11—C12—C13—C1 | 179.4 (3) |
C10—C5—C6—C7 | 0.0 (5) | C3—C12—C13—C1 | 0.2 (3) |
C4—C5—C6—C7 | −179.6 (3) | C1—C13—C14—C15 | 0.5 (5) |
C5—C6—C7—C8 | −0.7 (6) | C12—C13—C14—C15 | 179.4 (3) |
C6—C7—C8—C9 | 0.6 (6) | C13—C14—C15—C16 | −0.7 (5) |
C7—C8—C9—C10 | 0.1 (6) | C14—C15—C16—C17 | 0.1 (6) |
C8—C9—C10—C5 | −0.7 (5) | C18—O2—C17—C1 | −175.9 (3) |
C8—C9—C10—C11 | 178.8 (3) | C18—O2—C17—C16 | 3.1 (5) |
C6—C5—C10—C9 | 0.7 (4) | C13—C1—C17—O2 | 178.0 (3) |
C4—C5—C10—C9 | −179.7 (3) | C2—C1—C17—O2 | −0.7 (5) |
C6—C5—C10—C11 | −178.9 (3) | C13—C1—C17—C16 | −1.0 (5) |
C4—C5—C10—C11 | 0.7 (4) | C2—C1—C17—C16 | −179.7 (3) |
C9—C10—C11—C12 | −179.2 (3) | C15—C16—C17—O2 | −178.2 (3) |
C5—C10—C11—C12 | 0.3 (5) | C15—C16—C17—C1 | 0.8 (5) |
C10—C11—C12—C3 | −1.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.93 | 2.57 | 3.299 (5) | 135 |
C11—H11···O1ii | 0.93 | 2.55 | 3.298 (4) | 138 |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H12O2 |
Mr | 260.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 7.7202 (3), 9.2462 (4), 18.0294 (8) |
β (°) | 99.935 (2) |
V (Å3) | 1267.68 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.47 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.957, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11580, 2559, 1881 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.083, 0.250, 1.11 |
No. of reflections | 2559 |
No. of parameters | 183 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.49, −0.42 |
Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.93 | 2.57 | 3.299 (5) | 135 |
C11—H11···O1ii | 0.93 | 2.55 | 3.298 (4) | 138 |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x−1, y, z. |
Acknowledgements
This work was supported by the National Science Council (grant No. NSC 101–2113-M-035–001-MY2) and Feng Chia University in Taiwan.
References
Borbone, F., Carella, A., Ricciotti, L., Tuzi, A., Roviello, A. & Barsella, A. (2011). Dyes Pigm. 88, 290–295. Web of Science CSD CrossRef CAS Google Scholar
Borge, J., Cadierno, V., Díez, J., García-Garrido, S. E. & Gimeno, J. (2010). Dyes Pigm. 87, 209–217. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, X., Wu, K. & Dolbier, W. R. Jr (2005). J. Fluorine Chem. 126, 479–482. Web of Science CrossRef CAS Google Scholar
Chang, Y. J. & Chen, K.-Y. (2012). Acta Cryst. E68, o3063. CSD CrossRef IUCr Journals Google Scholar
Chen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cui, Y., Ren, H., Yu, J., Wang, Z. & Qian, G. (2009). Dyes Pigm. 81, 53–57. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fu, T.-L. & Wang, I.-J. (2008). Dyes Pigm. 76, 590–595. Web of Science CrossRef CAS Google Scholar
Li, X., Kim, S. H. & Son, Y. A. (2009). Dyes Pigm. 82, 293–298. Web of Science CrossRef CAS Google Scholar
Rahman, A., Zahrani, S. M. A. & Ajjou, A. A. N. (2011). Chin. Chem. Lett. 22, 691–693. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sousa, C. M., Berthet, J., Delbaere, S. & Coelho, P. J. (2011). Dyes Pigm. 92, 537–541. Web of Science CrossRef Google Scholar
Tang, K.-C., Chang, M.-J., Lin, T.-Y., Pan, H.-A., Fang, T.-C., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Am. Chem. Soc. 133, 17738–17745. Web of Science CSD CrossRef CAS PubMed Google Scholar
Yu, S.-B., Liu, H.-M., Luo, Y. & Lu, W. (2011). Chin. Chem. Lett. 22, 264–267. Web of Science CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Indanone and its derivatives are some of the most widely used organic compounds (Rahman et al., 2011). They are used as pigments and dyes (Cui et al., 2009; Li et al., 2009), intermediates in organic synthesis (Borbone et al., 2011; Borge et al., 2010; Fu & Wang, 2008; Yu et al., 2011) and exhibit a wide variety of biological activities (Sousa et al., 2011). In addition, 1-indanones were important precursors in the regiospecific synthesis of 2-fluoro-1-naphthols (Cai et al., 2005).
The molecular structure of the title compound comprises a 7-methoxy-1-indanone unit having a naphthalene ring fused on one side (Fig. 1). The 1-indaneone moiety is essentially planar (r.m.s. deviation = 0.0075 Å), which is consistent with previous studies (Chang & Chen, 2012; Chen et al., 2011a,b). π—π stacking is observed between the tetracyclic plane and its adjacent one, the closest centroid-centroid distance being 3.5983 (19) Å [symmetry code: 2 - x, -y, 2 - z]. The molecular packing (Fig. 2) is further stabilized by weak non-classical intermolecular C—H···O hydrogen bonds (Table 1).