9-(Dimethoxy-meth-yl)anthracene.

In the title compound, C(17)H(16)O(2), a dimethyl acetal of 9-anthraldehyde, the anthracene skeleton is planar and the two meth-oxy groups attached to the C atom at position 9 of the aromatic ring system are located above and below the ring system.

Related literature

For 9-chloro-10-(dimethoxy­meth­yl)anthracene, see: Yuan et al. (2004 ▶). For anologous compounds, see: Akiba et al. (1999 ▶); Yamashita et al. (2005 ▶).

Experimental

Crystal data

C17H16O2

M = 252.30

Orthorhombic,

a = 8.2310 (16) Å

b = 17.446 (4) Å

c = 19.261 (4) Å

V = 2766.0 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 291 (2) K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.987, T max = 0.990

12827 measured reflections

2433 independent reflections

1215 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.166

S = 0.90

2433 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001669/bt2672sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001669/bt2672Isup2.hkl

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

C17H16O2	F000 = 1072
Mr = 252.30	Dx = 1.212 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1781 reflections
a = 8.2310 (16) Å	θ = 2.4–19.5º
b = 17.446 (4) Å	µ = 0.08 mm−1
c = 19.261 (4) Å	T = 291 (2) K
V = 2766.0 (10) Å3	Block, yellow
Z = 8	0.16 × 0.12 × 0.10 mm

Bruker SMART 1K CCD area-detector diffractometer	2433 independent reflections
Radiation source: fine-focus sealed tube	1215 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
T = 291(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −9→4
Tmin = 0.987, Tmax = 0.990	k = −20→20
12827 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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.166	w = 1/[σ2(Fo2) + (0.0954P)2] where P = (Fo2 + 2Fc2)/3
S = 0.90	(Δ/σ)max < 0.001
2433 reflections	Δρmax = 0.14 e Å−3
174 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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	0.9017 (2)	0.20745 (12)	0.59464 (10)	0.0592 (6)
C2	1.0164 (3)	0.15624 (15)	0.62298 (12)	0.0719 (7)
C3	1.0584 (3)	0.08576 (16)	0.59060 (17)	0.0944 (9)
H3	1.0052	0.0709	0.5502	0.113*
C4	1.1755 (4)	0.03974 (19)	0.6180 (2)	0.1378 (15)
H4	1.2030	−0.0056	0.5956	0.165*
C5	1.2563 (5)	0.0603 (4)	0.6806 (3)	0.170 (3)
H5	1.3356	0.0282	0.6991	0.204*
C6	1.2182 (5)	0.1251 (3)	0.7122 (2)	0.1453 (19)
H6	1.2704	0.1376	0.7535	0.174*
C7	1.0996 (3)	0.1764 (2)	0.68494 (16)	0.0975 (9)
C8	1.0683 (4)	0.2472 (3)	0.71548 (15)	0.1118 (13)
H8	1.1193	0.2591	0.7572	0.134*
C9	0.9649 (4)	0.3003 (2)	0.68643 (14)	0.0918 (9)
C10	0.9437 (5)	0.3758 (3)	0.71550 (19)	0.1275 (14)
H10	0.9967	0.3890	0.7564	0.153*
C11	0.8487 (6)	0.4268 (3)	0.6839 (3)	0.1449 (18)
H11	0.8379	0.4755	0.7029	0.174*
C12	0.7655 (4)	0.40904 (18)	0.6236 (2)	0.1184 (11)
H12	0.7001	0.4458	0.6027	0.142*
C13	0.7787 (3)	0.33873 (15)	0.59484 (15)	0.0859 (8)
H13	0.7208	0.3279	0.5545	0.103*
C14	0.8787 (3)	0.28072 (14)	0.62451 (11)	0.0683 (6)
C15	0.8077 (3)	0.18624 (13)	0.53064 (11)	0.0665 (6)
H15	0.7224	0.2244	0.5228	0.080*
C16	0.8383 (4)	0.19124 (18)	0.40849 (13)	0.1082 (10)
H16A	0.7751	0.1457	0.4013	0.162*
H16B	0.9189	0.1954	0.3727	0.162*
H16C	0.7683	0.2352	0.4071	0.162*
C17	0.5853 (4)	0.11064 (19)	0.5615 (2)	0.1447 (14)
H17A	0.5903	0.1194	0.6106	0.217*
H17B	0.5388	0.0611	0.5528	0.217*
H17C	0.5191	0.1494	0.5402	0.217*
O1	0.91609 (19)	0.18736 (10)	0.47445 (8)	0.0856 (6)
O2	0.7373 (2)	0.11349 (10)	0.53439 (10)	0.1011 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0515 (12)	0.0712 (14)	0.0550 (12)	−0.0066 (10)	−0.0002 (10)	0.0067 (11)
C2	0.0531 (13)	0.0901 (18)	0.0726 (15)	−0.0153 (12)	−0.0023 (12)	0.0273 (13)
C3	0.0662 (16)	0.0813 (18)	0.136 (2)	0.0036 (14)	0.0014 (15)	0.0344 (18)
C4	0.085 (2)	0.116 (3)	0.212 (4)	0.0196 (19)	0.016 (3)	0.085 (3)
C5	0.076 (3)	0.217 (6)	0.217 (6)	0.015 (3)	−0.002 (3)	0.159 (5)
C6	0.075 (2)	0.228 (5)	0.133 (3)	−0.030 (3)	−0.028 (2)	0.112 (4)
C7	0.0644 (17)	0.152 (3)	0.0764 (19)	−0.0268 (18)	−0.0093 (15)	0.047 (2)
C8	0.088 (2)	0.197 (4)	0.0512 (17)	−0.063 (2)	−0.0075 (16)	0.017 (2)
C9	0.0807 (18)	0.134 (3)	0.0610 (16)	−0.0455 (18)	0.0157 (15)	−0.0198 (17)
C10	0.122 (3)	0.168 (4)	0.093 (2)	−0.070 (3)	0.036 (2)	−0.057 (3)
C11	0.133 (4)	0.138 (4)	0.164 (4)	−0.051 (3)	0.069 (3)	−0.078 (3)
C12	0.109 (2)	0.084 (2)	0.162 (3)	−0.0046 (17)	0.035 (2)	−0.034 (2)
C13	0.0760 (17)	0.0774 (18)	0.104 (2)	−0.0029 (13)	0.0122 (15)	−0.0166 (15)
C14	0.0594 (13)	0.0861 (17)	0.0592 (14)	−0.0165 (12)	0.0092 (11)	−0.0070 (13)
C15	0.0599 (13)	0.0661 (15)	0.0734 (15)	0.0031 (11)	−0.0072 (12)	−0.0050 (11)
C16	0.116 (2)	0.140 (3)	0.0684 (17)	0.0100 (19)	−0.0208 (17)	−0.0019 (16)
C17	0.090 (2)	0.130 (3)	0.214 (4)	−0.0208 (19)	0.020 (2)	0.042 (3)
O1	0.0743 (11)	0.1222 (15)	0.0603 (10)	0.0161 (9)	−0.0063 (9)	−0.0078 (8)
O2	0.0775 (12)	0.0773 (12)	0.1486 (18)	−0.0096 (9)	−0.0174 (11)	−0.0122 (10)

C1—C2	1.410 (3)	C10—H10	0.9300
C1—C14	1.415 (3)	C11—C12	1.384 (6)
C1—C15	1.501 (3)	C11—H11	0.9300
C2—C7	1.420 (4)	C12—C13	1.350 (4)
C2—C3	1.421 (4)	C12—H12	0.9300
C3—C4	1.361 (4)	C13—C14	1.424 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.422 (7)	C15—O2	1.397 (3)
C4—H4	0.9300	C15—O1	1.403 (2)
C5—C6	1.324 (6)	C15—H15	0.9800
C5—H5	0.9300	C16—O1	1.424 (3)
C6—C7	1.425 (5)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—C8	1.392 (4)	C16—H16C	0.9600
C8—C9	1.377 (4)	C17—O2	1.357 (3)
C8—H8	0.9300	C17—H17A	0.9600
C9—C14	1.429 (3)	C17—H17B	0.9600
C9—C10	1.443 (5)	C17—H17C	0.9600
C10—C11	1.331 (5)
C2—C1—C14	120.3 (2)	C10—C11—H11	119.2
C2—C1—C15	120.4 (2)	C12—C11—H11	119.2
C14—C1—C15	119.20 (19)	C13—C12—C11	120.5 (4)
C1—C2—C7	119.4 (3)	C13—C12—H12	119.7
C1—C2—C3	122.8 (2)	C11—C12—H12	119.7
C7—C2—C3	117.8 (3)	C12—C13—C14	121.8 (3)
C4—C3—C2	120.8 (3)	C12—C13—H13	119.1
C4—C3—H3	119.6	C14—C13—H13	119.1
C2—C3—H3	119.6	C1—C14—C13	123.8 (2)
C3—C4—C5	120.8 (4)	C1—C14—C9	119.3 (2)
C3—C4—H4	119.6	C13—C14—C9	116.9 (2)
C5—C4—H4	119.6	O2—C15—O1	108.44 (18)
C6—C5—C4	119.7 (4)	O2—C15—C1	113.28 (18)
C6—C5—H5	120.2	O1—C15—C1	107.61 (17)
C4—C5—H5	120.2	O2—C15—H15	109.1
C5—C6—C7	122.0 (5)	O1—C15—H15	109.1
C5—C6—H6	119.0	C1—C15—H15	109.1
C7—C6—H6	119.0	O1—C16—H16A	109.5
C8—C7—C2	119.1 (3)	O1—C16—H16B	109.5
C8—C7—C6	121.9 (4)	H16A—C16—H16B	109.5
C2—C7—C6	119.0 (4)	O1—C16—H16C	109.5
C9—C8—C7	122.7 (3)	H16A—C16—H16C	109.5
C9—C8—H8	118.7	H16B—C16—H16C	109.5
C7—C8—H8	118.7	O2—C17—H17A	109.5
C8—C9—C14	119.0 (3)	O2—C17—H17B	109.5
C8—C9—C10	122.1 (4)	H17A—C17—H17B	109.5
C14—C9—C10	118.8 (3)	O2—C17—H17C	109.5
C11—C10—C9	120.2 (4)	H17A—C17—H17C	109.5
C11—C10—H10	119.9	H17B—C17—H17C	109.5
C9—C10—H10	119.9	C15—O1—C16	113.76 (19)
C10—C11—C12	121.7 (4)	C17—O2—C15	115.8 (2)