9,10-Dihydr-oxy-4,4-dimethyl-5,8-dihydro-anthracen-1(4H)-one.

In the title mol-ecule, C(16)H(16)O(3), the ring system is planar and an intramolecular hydrogen bond is present. The mol-ecular packing is dominated by an inter-molecular hydrogen bond and by π-stacking inter-actions [inter-planar separation 3.8012 Å].

Related literature

For related literature, see: Allen (2002 ▶); Araya-Maturana et al. (2006 ▶, 2007 ▶); Desiraju (2002 ▶); Joshi et al. (1997 ▶); Valderrama et al. (1993 ▶).

Experimental

Crystal data

C16H16O3

M = 256.29

Orthorhombic,

a = 8.5944 (5) Å

b = 7.6024 (5) Å

c = 19.2949 (12) Å

V = 1260.69 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 (2) K

0.43 × 0.38 × 0.08 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS in SAINT-NT; Bruker, 1999 ▶) T min = 0.961, T max = 0.993

7422 measured reflections

1198 independent reflections

948 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.01

1198 reflections

112 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART-NT (Bruker, 2001 ▶); cell refinement: SAINT-NT (Bruker, 1999 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010891/hg2395sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010891/hg2395Isup2.hkl

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

C16H16O3	F000 = 544
Mr = 256.29	Dx = 1.350 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2361 reflections
a = 8.5944 (5) Å	θ = 2.6–25.0º
b = 7.6024 (5) Å	µ = 0.09 mm−1
c = 19.2949 (12) Å	T = 150 (2) K
V = 1260.69 (14) Å3	Plate, orange
Z = 4	0.43 × 0.38 × 0.08 mm

Siemens SMART CCD area-detector diffractometer	1198 independent reflections
Radiation source: fine-focus sealed tube	948 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.043
T = 150(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS in SAINT-NT; Bruker, 1999)	h = −10→10
Tmin = 0.961, Tmax = 0.993	k = −9→9
7422 measured reflections	l = −22→22

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0796P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1198 reflections	Δρmax = 0.33 e Å−3
112 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. 10 s by frame separated by 0.3 °

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	Occ. (<1)
O1	1.23661 (15)	0.2500	0.97450 (7)	0.0430 (4)
C1	1.1134 (2)	0.2500	0.93987 (9)	0.0316 (5)
C2	1.1204 (2)	0.2500	0.86508 (10)	0.0394 (5)
H2B	1.2188	0.2500	0.8427	0.047*
C3	0.9915 (2)	0.2500	0.82719 (10)	0.0366 (5)
H3A	1.0040	0.2500	0.7783	0.044*
C4	0.8283 (2)	0.2500	0.85428 (9)	0.0276 (5)
C11	0.74913 (15)	0.41540 (18)	0.82447 (7)	0.0319 (4)
H11A	0.7543	0.4123	0.7737	0.048*
H11B	0.8027	0.5206	0.8415	0.048*
H11C	0.6400	0.4184	0.8392	0.048*
C4A	0.8227 (2)	0.2500	0.93365 (10)	0.0250 (4)
C10	0.68158 (19)	0.2500	0.96919 (10)	0.0257 (5)
O3	0.54736 (14)	0.2500	0.93053 (6)	0.0349 (4)
H3	0.4700	0.2500	0.9571	0.052*
C10A	0.67531 (19)	0.2500	1.04249 (9)	0.0246 (5)
C5	0.5186 (2)	0.2500	1.07767 (10)	0.0293 (5)
H5A	0.4600	0.3551	1.0623	0.035*	0.50
H5B	0.4600	0.1449	1.0623	0.035*	0.50
C6	0.5260 (2)	0.2500	1.15519 (10)	0.0302 (5)
H6A	0.4305	0.2500	1.1800	0.036*
C7	0.6566 (2)	0.2500	1.19124 (10)	0.0299 (5)
H7A	0.6495	0.2500	1.2404	0.036*
C8	0.8143 (2)	0.2500	1.15932 (10)	0.0311 (5)
H8A	0.8718	0.1448	1.1755	0.037*	0.50
H8B	0.8718	0.3552	1.1755	0.037*	0.50
C8A	0.8116 (2)	0.2500	1.08099 (9)	0.0252 (4)
C9	0.9537 (2)	0.2500	1.04619 (9)	0.0257 (5)
O2	1.08404 (15)	0.2500	1.08586 (6)	0.0356 (4)
H2	1.1629	0.2500	1.0602	0.053*
C9A	0.9614 (2)	0.2500	0.97343 (10)	0.0255 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0199 (7)	0.0740 (12)	0.0351 (8)	0.000	−0.0021 (6)	0.000
C1	0.0210 (10)	0.0430 (12)	0.0310 (11)	0.000	−0.0009 (8)	0.000
C2	0.0246 (10)	0.0629 (14)	0.0306 (12)	0.000	0.0075 (9)	0.000
C3	0.0322 (11)	0.0527 (13)	0.0248 (10)	0.000	0.0037 (8)	0.000
C4	0.0232 (9)	0.0384 (12)	0.0213 (10)	0.000	−0.0015 (7)	0.000
C11	0.0346 (8)	0.0375 (8)	0.0237 (7)	−0.0025 (6)	−0.0025 (5)	0.0023 (6)
C4A	0.0230 (10)	0.0287 (10)	0.0232 (10)	0.000	−0.0008 (7)	0.000
C10	0.0211 (10)	0.0313 (11)	0.0246 (10)	0.000	−0.0020 (7)	0.000
O3	0.0189 (7)	0.0610 (10)	0.0247 (7)	0.000	−0.0024 (5)	0.000
C10A	0.0243 (10)	0.0264 (10)	0.0233 (10)	0.000	0.0004 (7)	0.000
C5	0.0226 (10)	0.0377 (11)	0.0276 (11)	0.000	0.0003 (7)	0.000
C6	0.0286 (10)	0.0335 (11)	0.0286 (10)	0.000	0.0069 (8)	0.000
C7	0.0354 (11)	0.0323 (11)	0.0221 (10)	0.000	0.0021 (8)	0.000
C8	0.0291 (10)	0.0395 (12)	0.0247 (10)	0.000	−0.0036 (8)	0.000
C8A	0.0262 (10)	0.0261 (10)	0.0233 (10)	0.000	−0.0012 (7)	0.000
C9	0.0222 (9)	0.0307 (11)	0.0243 (10)	0.000	−0.0039 (7)	0.000
O2	0.0215 (7)	0.0583 (9)	0.0271 (8)	0.000	−0.0058 (6)	0.000
C9A	0.0225 (10)	0.0291 (10)	0.0248 (10)	0.000	−0.0008 (7)	0.000

O1—C1	1.252 (2)	O3—H3	0.8400
C1—C2	1.444 (3)	C10A—C8A	1.387 (2)
C1—C9A	1.458 (2)	C10A—C5	1.508 (2)
C2—C3	1.327 (3)	C5—C6	1.497 (3)
C2—H2B	0.9500	C5—H5A	0.9900
C3—C4	1.497 (2)	C5—H5B	0.9900
C3—H3A	0.9500	C6—C7	1.320 (3)
C4—C4A	1.532 (3)	C6—H6A	0.9500
C4—C11i	1.5410 (16)	C7—C8	1.489 (3)
C4—C11	1.5410 (16)	C7—H7A	0.9500
C11—H11A	0.9800	C8—C8A	1.512 (3)
C11—H11B	0.9800	C8—H8A	0.9900
C11—H11C	0.9800	C8—H8B	0.9900
C4A—C10	1.393 (2)	C8A—C9	1.394 (2)
C4A—C9A	1.418 (2)	C9—O2	1.357 (2)
C10—O3	1.374 (2)	C9—C9A	1.405 (3)
C10—C10A	1.415 (3)	O2—H2	0.8400
O1—C1—C2	119.87 (16)	C10—C10A—C5	118.94 (16)
O1—C1—C9A	121.38 (17)	C6—C5—C10A	114.34 (15)
C2—C1—C9A	118.75 (16)	C6—C5—H5A	108.7
C3—C2—C1	121.05 (17)	C10A—C5—H5A	108.7
C3—C2—H2B	119.5	C6—C5—H5B	108.7
C1—C2—H2B	119.5	C10A—C5—H5B	108.7
C2—C3—C4	126.13 (18)	H5A—C5—H5B	107.6
C2—C3—H3A	116.9	C7—C6—C5	124.20 (17)
C4—C3—H3A	116.9	C7—C6—H6A	117.9
C3—C4—C4A	112.24 (15)	C5—C6—H6A	117.9
C3—C4—C11i	106.46 (10)	C6—C7—C8	123.79 (17)
C4A—C4—C11i	111.05 (10)	C6—C7—H7A	118.1
C3—C4—C11	106.46 (10)	C8—C7—H7A	118.1
C4A—C4—C11	111.05 (10)	C7—C8—C8A	113.53 (15)
C11i—C4—C11	109.37 (14)	C7—C8—H8A	108.9
C4—C11—H11A	109.5	C8A—C8—H8A	108.9
C4—C11—H11B	109.5	C7—C8—H8B	108.9
H11A—C11—H11B	109.5	C8A—C8—H8B	108.9
C4—C11—H11C	109.5	H8A—C8—H8B	107.7
H11A—C11—H11C	109.5	C10A—C8A—C9	118.81 (17)
H11B—C11—H11C	109.5	C10A—C8A—C8	123.28 (16)
C10—C4A—C9A	117.74 (17)	C9—C8A—C8	117.91 (15)
C10—C4A—C4	121.29 (15)	O2—C9—C8A	116.85 (16)
C9A—C4A—C4	120.97 (15)	O2—C9—C9A	121.64 (16)
O3—C10—C4A	117.62 (16)	C8A—C9—C9A	121.50 (16)
O3—C10—C10A	120.71 (15)	C9—O2—H2	109.5
C4A—C10—C10A	121.67 (16)	C9—C9A—C4A	120.08 (16)
C10—O3—H3	109.5	C9—C9A—C1	119.07 (16)
C8A—C10A—C10	120.20 (16)	C4A—C9A—C1	120.86 (16)
C8A—C10A—C5	120.86 (17)
C2—C3—C4—C11	121.70 (9)	C11—C4—C4A—C9A	−119.04 (10)
C11—C4—C4A—C10	60.96 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84	1.77	2.5172 (18)	147
O3—H3···O1ii	0.84	2.03	2.8022 (18)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.84	1.77	2.5172 (18)	147
O3—H3⋯O1i	0.84	2.03	2.8022 (18)	152

Symmetry code: (i) .