9-(Dimethoxy­meth­yl)anthracene

Wang, L.; You, W.; Huang, W.; Jiang, J.-C.; Yao, C.

doi:10.1107/S1600536808001669

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o487

doi:10.1107/S1600536808001669

Open

access

9-(Dimethoxymethyl)anthracene

Li Wang,^a Wei You,^a,^b Wei Huang,^a ^* Jue-Chao Jiang ^a and Cheng Yao ^b

^aState Key Laboratory of Coordination Chemistry, Coordination Chemistry Institute, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China, and ^bCollege of Sciences, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: whuang@nju.edu.cn

(Received 15 January 2008; accepted 16 January 2008; online 23 January 2008)

In the title compound, C₁₇H₁₆O₂, a dimethyl acetal of 9-anthraldehyde, the anthracene skeleton is planar and the two methoxy 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_r = 252.30
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.166
S = 0.90
2433 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Anthracene is a very useful compound for supramolecular photochemistry. Several crystal structures of anthracene derivatives have been reported previously (Akiba et al., 1999; Yuan et al., 2004; Yamashita et al., 2005;).

The atom-numbering scheme of the title compound is shown in Fig. 1. The bond lengths and angles are in the normal ranges compared with related compounds. The dihedral angles between the anthracene plane and the C15—O1—C16 and C15—O2—C17 groups are 71.6 (3) and 75.8 (4)°, respectively, and that between the latter two groups is 85.6 (2)°. These dihedral angles are silghtly different from 9-chloro-10-(dimethoxymethyl)anthracene (Yuan et al., 2004)

Related literature top

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

Experimental top

The treatment of 9-anthraldehyde (0.5 mmol, 0.010 g) and 4-aminopyridine (0.5 mmol, 0.041 g) in 20 cm³ me thanol with a few drops of HOAc as catalyst under reflux condition for 2 h produces the yellow compound 9-(dimethoxymethyl)anthracene as a by-product. Single crystals suitable for X-ray diffraction measurement formed after 1 week by slow evaporation at room temperature in air. Anal. Calcd. for C₁₇H₁₆O₂: C, 80.93; H, 6.39; O, 12.68%. Found: C, 81.00; H, 6.33; O, 12.74%. FT—IR (KBr pellets, cm^-1): 2932, 1448, 1186, 1105, 1066, 891, 740. ¹H NMR (500 MHz, CDCl₃): d = 3.57 (s, 6H), 6.59 (s, 1H), 7.29–7.56 (m, 4H), 8.01(d, 2H, J = 8.4 Hz), 8.49 (s, 1H), 8.74 (d, 2H, J = 8.9 Hz).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A perspective view of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

9-(dimethoxymethyl)anthracene top

Crystal data top

C₁₇H₁₆O₂	F(000) = 1072
M_r = 252.30	D_x = 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 = 2.4–19.5°
b = 17.446 (4) Å	µ = 0.08 mm⁻¹
c = 19.261 (4) Å	T = 291 K
V = 2766.0 (10) Å³	Block, yellow
Z = 8	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2433 independent reflections
Radiation source: fine-focus sealed tube	1215 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→4
T_min = 0.987, T_max = 0.990	k = −20→20
12827 measured reflections	l = −22→22

Refinement top

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) = 0.166	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0954P)²] where P = (F_o² + 2F_c²)/3
2433 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₇H₁₆O₂	V = 2766.0 (10) Å³
M_r = 252.30	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.2310 (16) Å	µ = 0.08 mm⁻¹
b = 17.446 (4) Å	T = 291 K
c = 19.261 (4) Å	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2433 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1215 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.990	R_int = 0.045
12827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 0.90	Δρ_max = 0.14 e Å⁻³
2433 reflections	Δρ_min = −0.16 e Å⁻³
174 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₂
M_r	252.30
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	291
a, b, c (Å)	8.2310 (16), 17.446 (4), 19.261 (4)
V (Å³)	2766.0 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.987, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	12827, 2433, 1215
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.166, 0.90
No. of reflections	2433
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Acknowledgements

WH acknowledges the Major State Basic Research Development Programs (Nos. 2006CB806104 and 2007CB925101), the National Natural Science Foundation of China (No. 20301009) and the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry, for financial aid.

References

Akiba, K., Yamashita, M., Yamamoto, Y. & Nagase, S. (1999). J. Am. Chem. Soc. 121, 10644–10645. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2000). SMART (Version 5.622), SAINT (Version 6.02a) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yamashita, M., Yamamoto, Y., Akiba, K., Hashizume, D., Iwasaki, F., Takagi, N. & Nagase, S. (2005). J. Am. Chem. Soc. 127, 4354–4371. Web of Science CSD CrossRef PubMed CAS Google Scholar
Yuan, W.-B., Yan, L. & Yang, R.-D. (2004). Acta Cryst. E60, o2447–o2448. Web of Science CSD CrossRef IUCr Journals Google Scholar