10-(4-Methyl-benzyl-idene)anthracen-9(10H)-one.

In the title compound, C(22)H(16)O, the six-membered ring within the anthrone moiety adopts a shallow boat conformation, with puckering parameters Q = 0.2860 (17) Å, Θ = 99.1 (3)° and Φ = 114.8 (3)°. The dihedral angle between the outer benzene rings is 26.53 (8)°. The mean plane through the anthrone ring system makes a dihedral angle of 38.73 (6)° with the pendant benzene ring. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into zigzag chains propagating along the c-axis direction and weak C-H⋯π inter-actions further consolidate the structure.

Related literature

For a related structure and background to anthrone derivatives, see: Arumugam et al. (2011 ▶). For related structures, see: Wen & Li (2008 ▶); Zhou et al. (2004 ▶). For the synthesis, see: Prinz et al. (2003 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H16O

M = 296.35

Orthorhombic,

a = 7.2959 (1) Å

b = 16.3853 (2) Å

c = 13.0028 (2) Å

V = 1554.43 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.33 × 0.27 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.975, T max = 0.985

20184 measured reflections

2757 independent reflections

2575 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.122

S = 1.09

2757 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 2319 Friedel pairs

Flack parameter: 0 (10)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000827/hb6592sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000827/hb6592Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000827/hb6592Isup3.cml

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

C22H16O	F(000) = 624
Mr = 296.35	Dx = 1.266 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8371 reflections
a = 7.2959 (1) Å	θ = 3.1–31.7°
b = 16.3853 (2) Å	µ = 0.08 mm−1
c = 13.0028 (2) Å	T = 100 K
V = 1554.43 (4) Å3	Block, yellow
Z = 4	0.33 × 0.27 × 0.21 mm

Bruker SMART APEXII CCD diffractometer	2757 independent reflections
Radiation source: fine-focus sealed tube	2575 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 31.8°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.975, Tmax = 0.985	k = −24→21
20184 measured reflections	l = −19→17

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0831P)2 + 0.1277P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.002
2757 reflections	Δρmax = 0.40 e Å−3
209 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 2319 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0 (10)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.22961 (18)	0.09172 (9)	0.36336 (11)	0.0332 (3)
C1	0.34392 (19)	0.11506 (9)	0.63231 (12)	0.0204 (3)
C2	0.4267 (2)	0.07120 (10)	0.71248 (13)	0.0249 (3)
H2A	0.4357	0.0949	0.7789	0.030*
C3	0.4956 (2)	−0.00689 (11)	0.69531 (15)	0.0297 (4)
H3A	0.5527	−0.0357	0.7500	0.036*
C4	0.4818 (2)	−0.04321 (11)	0.59886 (16)	0.0311 (4)
H4A	0.5270	−0.0969	0.5880	0.037*
C5	0.4016 (2)	−0.00049 (10)	0.51897 (15)	0.0274 (3)
H5A	0.3917	−0.0250	0.4530	0.033*
C6	0.3352 (2)	0.07847 (10)	0.53448 (12)	0.0223 (3)
C7	0.2696 (2)	0.12531 (10)	0.44437 (12)	0.0234 (3)
C8	0.2672 (2)	0.21516 (11)	0.45515 (12)	0.0239 (3)
C9	0.2547 (3)	0.26344 (13)	0.36613 (16)	0.0328 (4)
H9A	0.2415	0.2381	0.3008	0.039*
C10	0.2613 (3)	0.34737 (13)	0.37306 (18)	0.0384 (5)
H10A	0.2514	0.3799	0.3129	0.046*
C11	0.2828 (2)	0.38405 (12)	0.46872 (18)	0.0351 (4)
H11A	0.2905	0.4418	0.4733	0.042*
C12	0.2931 (2)	0.33765 (10)	0.55740 (16)	0.0281 (3)
H12A	0.3071	0.3638	0.6221	0.034*
C13	0.2829 (2)	0.25202 (10)	0.55238 (13)	0.0227 (3)
C14	0.2792 (2)	0.20019 (9)	0.64518 (12)	0.0203 (3)
C15	0.2111 (2)	0.23176 (9)	0.73396 (12)	0.0223 (3)
H15A	0.1904	0.2890	0.7325	0.027*
C16	0.1643 (2)	0.19219 (9)	0.83166 (12)	0.0220 (3)
C17	0.2006 (2)	0.23303 (10)	0.92404 (14)	0.0274 (3)
H17A	0.2577	0.2851	0.9224	0.033*
C18	0.1542 (2)	0.19832 (12)	1.01808 (13)	0.0293 (3)
H18A	0.1828	0.2265	1.0799	0.035*
C19	0.0662 (2)	0.12249 (11)	1.02327 (13)	0.0269 (3)
C20	0.0247 (2)	0.08341 (10)	0.93057 (13)	0.0240 (3)
H20A	−0.0385	0.0327	0.9321	0.029*
C21	0.0736 (2)	0.11680 (9)	0.83647 (12)	0.0223 (3)
H21A	0.0454	0.0884	0.7748	0.027*
C22	0.0189 (3)	0.08462 (15)	1.12512 (15)	0.0386 (4)
H22A	0.0738	0.1168	1.1807	0.058*
H22B	0.0665	0.0287	1.1276	0.058*
H22C	−0.1146	0.0836	1.1335	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.0306 (6)	0.0475 (7)	0.0215 (5)	0.0048 (5)	−0.0009 (5)	−0.0047 (5)
C1	0.0160 (6)	0.0216 (6)	0.0235 (6)	0.0018 (4)	0.0013 (5)	0.0038 (5)
C2	0.0206 (6)	0.0296 (7)	0.0245 (6)	0.0027 (6)	−0.0003 (6)	0.0064 (6)
C3	0.0224 (6)	0.0301 (7)	0.0364 (9)	0.0063 (6)	0.0030 (6)	0.0117 (7)
C4	0.0247 (7)	0.0260 (7)	0.0425 (9)	0.0062 (6)	0.0062 (7)	0.0039 (7)
C5	0.0226 (7)	0.0275 (7)	0.0321 (8)	0.0018 (6)	0.0051 (6)	−0.0029 (6)
C6	0.0172 (6)	0.0272 (7)	0.0225 (6)	0.0009 (5)	0.0019 (5)	0.0028 (5)
C7	0.0178 (6)	0.0317 (7)	0.0207 (7)	0.0026 (5)	0.0025 (5)	0.0010 (6)
C8	0.0181 (6)	0.0317 (7)	0.0219 (7)	0.0035 (5)	0.0034 (5)	0.0074 (6)
C9	0.0257 (7)	0.0466 (10)	0.0261 (7)	0.0071 (7)	0.0057 (6)	0.0138 (8)
C10	0.0300 (8)	0.0449 (10)	0.0403 (10)	0.0085 (7)	0.0091 (7)	0.0259 (9)
C11	0.0244 (8)	0.0312 (8)	0.0495 (11)	0.0028 (6)	0.0096 (7)	0.0173 (8)
C12	0.0205 (7)	0.0250 (7)	0.0387 (9)	−0.0004 (5)	0.0062 (6)	0.0080 (7)
C13	0.0164 (6)	0.0252 (7)	0.0264 (7)	0.0012 (5)	0.0019 (5)	0.0071 (6)
C14	0.0168 (6)	0.0221 (6)	0.0221 (6)	−0.0005 (4)	−0.0005 (5)	0.0030 (5)
C15	0.0225 (7)	0.0215 (6)	0.0227 (7)	−0.0007 (5)	0.0008 (5)	0.0006 (5)
C16	0.0219 (7)	0.0242 (6)	0.0198 (6)	0.0007 (5)	0.0010 (6)	−0.0011 (5)
C17	0.0260 (7)	0.0315 (8)	0.0249 (7)	−0.0038 (6)	0.0009 (6)	−0.0060 (6)
C18	0.0264 (8)	0.0416 (9)	0.0198 (7)	−0.0010 (6)	−0.0008 (6)	−0.0062 (6)
C19	0.0205 (7)	0.0394 (8)	0.0208 (6)	0.0018 (6)	0.0013 (6)	0.0031 (6)
C20	0.0208 (6)	0.0272 (7)	0.0239 (7)	0.0019 (5)	0.0011 (6)	0.0025 (6)
C21	0.0224 (6)	0.0235 (6)	0.0210 (6)	0.0001 (5)	0.0020 (5)	−0.0002 (5)
C22	0.0322 (9)	0.0613 (12)	0.0224 (8)	−0.0067 (8)	0.0017 (7)	0.0081 (8)

O1—C7	1.224 (2)	C11—H11A	0.9500
C1—C2	1.403 (2)	C12—C13	1.407 (2)
C1—C6	1.408 (2)	C12—H12A	0.9500
C1—C14	1.482 (2)	C13—C14	1.476 (2)
C2—C3	1.393 (2)	C14—C15	1.359 (2)
C2—H2A	0.9500	C15—C16	1.467 (2)
C3—C4	1.392 (3)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.400 (2)
C4—C5	1.382 (3)	C16—C21	1.403 (2)
C4—H4A	0.9500	C17—C18	1.390 (2)
C5—C6	1.396 (2)	C17—H17A	0.9500
C5—H5A	0.9500	C18—C19	1.400 (3)
C6—C7	1.480 (2)	C18—H18A	0.9500
C7—C8	1.479 (2)	C19—C20	1.398 (2)
C8—C13	1.406 (2)	C19—C22	1.503 (3)
C8—C9	1.405 (2)	C20—C21	1.387 (2)
C9—C10	1.379 (3)	C20—H20A	0.9500
C9—H9A	0.9500	C21—H21A	0.9500
C10—C11	1.390 (4)	C22—H22A	0.9800
C10—H10A	0.9500	C22—H22B	0.9800
C11—C12	1.383 (3)	C22—H22C	0.9800
C2—C1—C6	118.21 (14)	C13—C12—H12A	119.8
C2—C1—C14	122.37 (15)	C8—C13—C12	118.33 (15)
C6—C1—C14	119.25 (14)	C8—C13—C14	119.12 (14)
C3—C2—C1	120.46 (16)	C12—C13—C14	122.48 (15)
C3—C2—H2A	119.8	C15—C14—C13	118.82 (13)
C1—C2—H2A	119.8	C15—C14—C1	124.79 (14)
C4—C3—C2	120.73 (15)	C13—C14—C1	116.33 (14)
C4—C3—H3A	119.6	C14—C15—C16	130.74 (13)
C2—C3—H3A	119.6	C14—C15—H15A	114.6
C5—C4—C3	119.43 (15)	C16—C15—H15A	114.6
C5—C4—H4A	120.3	C17—C16—C21	118.16 (14)
C3—C4—H4A	120.3	C17—C16—C15	119.18 (13)
C4—C5—C6	120.50 (17)	C21—C16—C15	122.54 (14)
C4—C5—H5A	119.8	C18—C17—C16	120.85 (15)
C6—C5—H5A	119.8	C18—C17—H17A	119.6
C5—C6—C1	120.63 (15)	C16—C17—H17A	119.6
C5—C6—C7	118.58 (15)	C17—C18—C19	121.12 (15)
C1—C6—C7	120.60 (14)	C17—C18—H18A	119.4
O1—C7—C8	121.76 (15)	C19—C18—H18A	119.4
O1—C7—C6	121.69 (15)	C20—C19—C18	117.66 (15)
C8—C7—C6	116.42 (14)	C20—C19—C22	121.40 (16)
C13—C8—C9	120.29 (16)	C18—C19—C22	120.94 (16)
C13—C8—C7	120.79 (13)	C21—C20—C19	121.62 (14)
C9—C8—C7	118.89 (16)	C21—C20—H20A	119.2
C10—C9—C8	120.4 (2)	C19—C20—H20A	119.2
C10—C9—H9A	119.8	C20—C21—C16	120.53 (15)
C8—C9—H9A	119.8	C20—C21—H21A	119.7
C9—C10—C11	119.57 (17)	C16—C21—H21A	119.7
C9—C10—H10A	120.2	C19—C22—H22A	109.5
C11—C10—H10A	120.2	C19—C22—H22B	109.5
C12—C11—C10	120.96 (17)	H22A—C22—H22B	109.5
C12—C11—H11A	119.5	C19—C22—H22C	109.5
C10—C11—H11A	119.5	H22A—C22—H22C	109.5
C11—C12—C13	120.45 (18)	H22B—C22—H22C	109.5
C11—C12—H12A	119.8
C6—C1—C2—C3	−0.9 (2)	C9—C8—C13—C14	174.59 (15)
C14—C1—C2—C3	−176.04 (15)	C7—C8—C13—C14	−7.4 (2)
C1—C2—C3—C4	−0.8 (3)	C11—C12—C13—C8	1.7 (2)
C2—C3—C4—C5	1.2 (3)	C11—C12—C13—C14	−175.30 (15)
C3—C4—C5—C6	0.1 (3)	C8—C13—C14—C15	−150.02 (15)
C4—C5—C6—C1	−1.8 (2)	C12—C13—C14—C15	27.0 (2)
C4—C5—C6—C7	173.23 (15)	C8—C13—C14—C1	27.30 (19)
C2—C1—C6—C5	2.2 (2)	C12—C13—C14—C1	−155.71 (14)
C14—C1—C6—C5	177.49 (14)	C2—C1—C14—C15	−32.6 (2)
C2—C1—C6—C7	−172.75 (14)	C6—C1—C14—C15	152.29 (16)
C14—C1—C6—C7	2.6 (2)	C2—C1—C14—C13	150.25 (14)
C5—C6—C7—O1	18.3 (2)	C6—C1—C14—C13	−24.9 (2)
C1—C6—C7—O1	−166.66 (15)	C13—C14—C15—C16	169.27 (16)
C5—C6—C7—C8	−157.66 (14)	C1—C14—C15—C16	−7.8 (3)
C1—C6—C7—C8	17.4 (2)	C14—C15—C16—C17	142.24 (19)
O1—C7—C8—C13	169.11 (15)	C14—C15—C16—C21	−41.8 (3)
C6—C7—C8—C13	−14.9 (2)	C21—C16—C17—C18	2.4 (2)
O1—C7—C8—C9	−12.8 (2)	C15—C16—C17—C18	178.48 (17)
C6—C7—C8—C9	163.10 (15)	C16—C17—C18—C19	−1.5 (3)
C13—C8—C9—C10	1.3 (3)	C17—C18—C19—C20	−0.7 (3)
C7—C8—C9—C10	−176.73 (16)	C17—C18—C19—C22	179.07 (18)
C8—C9—C10—C11	0.8 (3)	C18—C19—C20—C21	2.0 (2)
C9—C10—C11—C12	−1.6 (3)	C22—C19—C20—C21	−177.81 (17)
C10—C11—C12—C13	0.3 (3)	C19—C20—C21—C16	−1.1 (2)
C9—C8—C13—C12	−2.5 (2)	C17—C16—C21—C20	−1.1 (2)
C7—C8—C13—C12	175.48 (14)	C15—C16—C21—C20	−177.09 (14)

Cg1 and Cg2 are the centroids of the C1–C6 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1i	0.95	2.35	3.275 (2)	164
C22—H22C···Cg1ii	0.98	2.94	3.726 (2)	138
C17—H17A···Cg2iii	0.95	2.76	3.5073 (16)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1i	0.95	2.35	3.275 (2)	164
C22—H22C⋯Cg1ii	0.98	2.94	3.726 (2)	138
C17—H17A⋯Cg2iii	0.95	2.76	3.5073 (16)	136

Symmetry codes: (i) ; (ii) ; (iii) .