1-Meth-oxy-11H-benzo[b]fluoren-11-one.

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 crystal structure, the shortest centroid-centroid distance being 3.5983 (19) Å. The mol-ecular 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

C18H12O2

M = 260.28

Monoclinic,

a = 7.7202 (3) Å

b = 9.2462 (4) Å

c = 18.0294 (8) Å

β = 99.935 (2)°

V = 1267.68 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 299 K

0.50 × 0.47 × 0.20 mm

Data collection

Bruker SMART CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.957, T max = 0.983

11580 measured reflections

2559 independent reflections

1881 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.250

S = 1.11

2559 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050076/xu5629sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050076/xu5629Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050076/xu5629Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .