2-Methylxanthen-9-one.

In the title compound, C(14)H(10)O(2), the tricycle is not planar, being bent with a dihedral angle of 4.7 (1)° between the two benzene rings. In the crystal, π-π inter-actions between the six-membered rings of neighbouring mol-ecules [centroid-centroid distances = 3.580 (3) and 3.605 (3) Å] form stacks propagating along [101].

Related literature

For general background and applications of xanthones, see: Jiang et al. (2004 ▶); Sampath & Vijayaraghavan (2007 ▶); Nakatani et al. (2002 ▶); Pinto et al. (2005 ▶). For related structures, see: Ee et al. (2010 ▶); Boonnak et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10O2

M = 210.22

Triclinic,

a = 8.2678 (7) Å

b = 8.5268 (6) Å

c = 8.5965 (7) Å

α = 92.650 (6)°

β = 116.592 (8)°

γ = 104.045 (7)°

V = 517.28 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.890, T max = 1.000

10601 measured reflections

2028 independent reflections

1262 reflections with I > 2σ(I)

R int = 0.033

Standard reflections: ?

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.152

S = 1.04

2028 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007702/cv5249sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007702/cv5249Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007702/cv5249Isup3.cml

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

C14H10O2	Z = 2
Mr = 210.22	F(000) = 220
Triclinic, P1	Dx = 1.350 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2678 (7) Å	Cell parameters from 3639 reflections
b = 8.5268 (6) Å	θ = 3.6–29.1°
c = 8.5965 (7) Å	µ = 0.09 mm−1
α = 92.650 (6)°	T = 293 K
β = 116.592 (8)°	Block, white
γ = 104.045 (7)°	0.30 × 0.20 × 0.20 mm
V = 517.28 (7) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2028 independent reflections
Radiation source: fine-focus sealed tube	1262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 26.0°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −10→10
Tmin = 0.890, Tmax = 1.000	k = −10→10
10601 measured reflections	l = −10→10

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.0822P] where P = (Fo2 + 2Fc2)/3
2028 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.7846 (3)	0.1172 (2)	0.0063 (2)	0.0552 (5)
H1	0.8299	0.0663	−0.0570	0.066*
C2	0.7434 (3)	0.2613 (3)	−0.0345 (3)	0.0608 (6)
C3	0.6748 (3)	0.3344 (3)	0.0625 (3)	0.0672 (6)
H3	0.6448	0.4315	0.0362	0.081*
C4	0.6505 (3)	0.2675 (3)	0.1948 (3)	0.0658 (6)
H4	0.6046	0.3187	0.2574	0.079*
C5	0.7034 (3)	−0.1210 (3)	0.5685 (3)	0.0623 (6)
H5	0.6586	−0.0609	0.6249	0.075*
C6	0.7523 (3)	−0.2566 (3)	0.6273 (3)	0.0705 (7)
H6	0.7410	−0.2886	0.7248	0.085*
C7	0.8186 (3)	−0.3476 (3)	0.5441 (3)	0.0707 (7)
H7	0.8514	−0.4401	0.5855	0.085*
C8	0.8355 (3)	−0.3005 (3)	0.4002 (3)	0.0601 (6)
H8	0.8802	−0.3616	0.3445	0.072*
C9	0.8034 (3)	−0.1098 (2)	0.1823 (2)	0.0487 (5)
O9	0.8493 (2)	−0.19003 (18)	0.09566 (19)	0.0720 (5)
O10	0.67103 (19)	0.06452 (17)	0.37199 (17)	0.0590 (4)
C11	0.6948 (3)	0.1230 (2)	0.2347 (2)	0.0499 (5)
C12	0.7212 (3)	−0.0736 (2)	0.4230 (2)	0.0494 (5)
C13	0.7864 (3)	−0.1617 (2)	0.3361 (2)	0.0468 (5)
C14	0.7604 (3)	0.0446 (2)	0.1403 (2)	0.0466 (5)
C15	0.7710 (4)	0.3410 (3)	−0.1775 (3)	0.0837 (8)
H153	0.8406	0.4550	−0.1321	0.126*
H152	0.6498	0.3312	−0.2760	0.126*
H151	0.8401	0.2873	−0.2153	0.126*

	U11	U22	U33	U12	U13	U23
C1	0.0528 (13)	0.0580 (13)	0.0503 (12)	0.0096 (10)	0.0242 (10)	0.0068 (9)
C2	0.0544 (13)	0.0574 (13)	0.0561 (12)	0.0066 (10)	0.0185 (10)	0.0142 (10)
C3	0.0636 (15)	0.0503 (12)	0.0768 (15)	0.0177 (11)	0.0232 (12)	0.0157 (11)
C4	0.0650 (15)	0.0579 (14)	0.0772 (15)	0.0234 (11)	0.0338 (12)	0.0065 (11)
C5	0.0607 (14)	0.0784 (15)	0.0507 (12)	0.0146 (12)	0.0324 (11)	0.0058 (11)
C6	0.0706 (16)	0.0855 (17)	0.0549 (13)	0.0158 (13)	0.0320 (12)	0.0220 (12)
C7	0.0798 (17)	0.0697 (15)	0.0640 (13)	0.0251 (13)	0.0324 (12)	0.0262 (11)
C8	0.0670 (14)	0.0558 (13)	0.0586 (12)	0.0193 (11)	0.0302 (11)	0.0096 (10)
C9	0.0470 (11)	0.0518 (11)	0.0494 (11)	0.0120 (9)	0.0263 (9)	0.0043 (9)
O9	0.1003 (12)	0.0713 (10)	0.0769 (10)	0.0395 (9)	0.0617 (9)	0.0172 (8)
O10	0.0687 (10)	0.0625 (9)	0.0603 (9)	0.0252 (7)	0.0400 (7)	0.0096 (7)
C11	0.0468 (12)	0.0492 (11)	0.0510 (11)	0.0117 (9)	0.0225 (9)	0.0055 (9)
C12	0.0447 (11)	0.0525 (12)	0.0490 (11)	0.0103 (9)	0.0227 (9)	0.0054 (9)
C13	0.0432 (11)	0.0496 (11)	0.0441 (10)	0.0088 (9)	0.0205 (9)	0.0047 (8)
C14	0.0436 (11)	0.0463 (11)	0.0460 (10)	0.0076 (9)	0.0210 (9)	0.0045 (8)
C15	0.0831 (18)	0.0799 (17)	0.0763 (16)	0.0159 (14)	0.0302 (14)	0.0321 (13)

C1—C2	1.373 (3)	C7—C8	1.373 (3)
C1—C14	1.400 (2)	C7—H7	0.9300
C1—H1	0.9300	C8—C13	1.402 (3)
C2—C3	1.396 (3)	C8—H8	0.9300
C2—C15	1.509 (3)	C9—O9	1.225 (2)
C3—C4	1.367 (3)	C9—C14	1.464 (3)
C3—H3	0.9300	C9—C13	1.467 (2)
C4—C11	1.385 (3)	O10—C12	1.368 (2)
C4—H4	0.9300	O10—C11	1.377 (2)
C5—C6	1.362 (3)	C11—C14	1.386 (3)
C5—C12	1.390 (3)	C12—C13	1.385 (3)
C5—H5	0.9300	C15—H153	0.9600
C6—C7	1.386 (3)	C15—H152	0.9600
C6—H6	0.9300	C15—H151	0.9600
C2—C1—C14	122.1 (2)	C13—C8—H8	119.6
C2—C1—H1	119.0	O9—C9—C14	122.70 (17)
C14—C1—H1	119.0	O9—C9—C13	122.40 (18)
C1—C2—C3	117.6 (2)	C14—C9—C13	114.91 (16)
C1—C2—C15	122.2 (2)	C12—O10—C11	118.91 (15)
C3—C2—C15	120.2 (2)	O10—C11—C4	116.28 (18)
C4—C3—C2	122.0 (2)	O10—C11—C14	122.97 (17)
C4—C3—H3	119.0	C4—C11—C14	120.75 (19)
C2—C3—H3	119.0	O10—C12—C13	122.48 (17)
C3—C4—C11	119.3 (2)	O10—C12—C5	116.03 (18)
C3—C4—H4	120.3	C13—C12—C5	121.50 (19)
C11—C4—H4	120.3	C12—C13—C8	117.83 (18)
C6—C5—C12	119.2 (2)	C12—C13—C9	120.58 (17)
C6—C5—H5	120.4	C8—C13—C9	121.59 (17)
C12—C5—H5	120.4	C11—C14—C1	118.27 (18)
C5—C6—C7	121.0 (2)	C11—C14—C9	119.92 (17)
C5—C6—H6	119.5	C1—C14—C9	121.80 (17)
C7—C6—H6	119.5	C2—C15—H153	109.5
C8—C7—C6	119.6 (2)	C2—C15—H152	109.5
C8—C7—H7	120.2	H153—C15—H152	109.5
C6—C7—H7	120.2	C2—C15—H151	109.5
C7—C8—C13	120.9 (2)	H153—C15—H151	109.5
C7—C8—H8	119.6	H152—C15—H151	109.5
C14—C1—C2—C3	−0.3 (3)	O10—C12—C13—C9	−0.4 (3)
C14—C1—C2—C15	179.37 (18)	C5—C12—C13—C9	179.75 (17)
C1—C2—C3—C4	0.7 (3)	C7—C8—C13—C12	0.3 (3)
C15—C2—C3—C4	−179.00 (19)	C7—C8—C13—C9	−179.92 (18)
C2—C3—C4—C11	0.0 (3)	O9—C9—C13—C12	−175.44 (19)
C12—C5—C6—C7	−0.2 (3)	C14—C9—C13—C12	4.3 (3)
C5—C6—C7—C8	0.1 (4)	O9—C9—C13—C8	4.8 (3)
C6—C7—C8—C13	−0.1 (3)	C14—C9—C13—C8	−175.48 (17)
C12—O10—C11—C4	−176.87 (17)	O10—C11—C14—C1	−178.18 (16)
C12—O10—C11—C14	2.7 (3)	C4—C11—C14—C1	1.3 (3)
C3—C4—C11—O10	178.55 (17)	O10—C11—C14—C9	1.6 (3)
C3—C4—C11—C14	−1.0 (3)	C4—C11—C14—C9	−178.92 (17)
C11—O10—C12—C13	−3.3 (3)	C2—C1—C14—C11	−0.7 (3)
C11—O10—C12—C5	176.62 (16)	C2—C1—C14—C9	179.57 (18)
C6—C5—C12—O10	−179.48 (18)	O9—C9—C14—C11	174.89 (19)
C6—C5—C12—C13	0.4 (3)	C13—C9—C14—C11	−4.9 (3)
O10—C12—C13—C8	179.45 (17)	O9—C9—C14—C1	−5.4 (3)
C5—C12—C13—C8	−0.4 (3)	C13—C9—C14—C1	174.86 (16)