9-(4-Meth-oxy-phen-yl)anthracene.

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 meth-oxy group lies in the plane of the benzene ring [C1-O1-C2-C7 torsion angle = 0.5 (2)°]. The crystal structure features π-π [centroid-centroid distance = 3.9487 (12) Å] and C-H⋯π inter-actions, 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

C21H16O

M = 284.34

Monoclinic,

a = 13.5539 (5) Å

b = 15.0626 (5) Å

c = 7.6130 (2) Å

β = 99.219 (2)°

V = 1534.17 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.981, T max = 0.985

14917 measured reflections

3806 independent reflections

2317 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.02

3806 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047149/pv2599sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047149/pv2599Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047149/pv2599Isup3.cml

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

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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) ; (iv) .