9-(Methoxy­meth­yl)anthracene

The title compound, C₁₆H₁₄O, crystallizes with two independent mol­ecules in the asymmetric unit, one of which lies on a crystallographic mirror plane. Inter­molecular C—H...O hydrogen bonds link the mol­ecules into infinite one-dimensional chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.037
• wR factor = 0.102
• Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.854     0.982
            Tmin(prime) and Tmax expected:      0.970     0.981
            RR(prime) =      0.880
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.31
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.05
           From the CIF: _reflns_number_total               1746
           Count of symmetry unique reflns         1751
           Completeness (_total/calc)             99.71%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Many organic substances possess the property of fluorescence, when exposed to light of a suitable wavelength, and they emit light of a different wavelength. Anthracene itself fluoresces both as solid and vapor as well as in solution (Stevenson, 1911). This phenomenon has been of interest to the chemist. In order to establish some relation between the structure and the fluorescence of the substances, new series of anthracene derivatives have been prepared (Park et al., 2007; Zimmermann et al., 1999). In this paper, an anthracene derivative has been synthesized, and its structure (I) is reported.

The title compound, C₁₆H₁₄O, crystallizes with two independent molecules in the asymmetric unit. As shown in Fig. 1, the dihedral angle between the two methylanthracene plane is 74.8°. Each C₁₆H₁₄O molecule consists of a methyl group linked to an anthracene moiety through an ether linkage. The C—C bonds and C—C—C angles in the anthracene fragment are comparable with reported values (Ramos Silva et al., 2000). The C15—O1, C16–O1, C25—O2 and C26—O2 bond lengths are 1.406 (4), 1.427 (4), 1.420 (6) and 1.408 (6) Å, respectively, which are typical of ether bonds. Intermolecular C—H···O hydrogen bonds link the molecules into infinite one-dimensional chains.

Previous studies (Desiraju, 1996) have revealed that the C···O distances in C—H···O hydrogen bonds are in the range of 3.0–4.0 Å. The C—H···O angles θ in the range of 110–180° are acceptable. As shown in Fig. 2, the C(15)···O(1) distance of 3.436 Å and C(15)—H(15a)···O(1) angle of 147.7° indicate a weak C—H···O hydrogen bond, which links the molecules into an infinite one-dimensional chain. All the chains are parallel along the c axis in the crystal.

Related literature

For related literature, see: Stevenson (1911); Park et al. (2007); Zimmermann et al. (1999); Ramos Silva et al. (2000); Desiraju (1996).

S2. Experimental

The title compound was prepared according to the reported procedure (Zimmermann et al., 1999). Crystals suitable for X-ray analysis were obtained by recrystallization from methanol solution of the compound.

S3. Refinement

All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, U_iso = 1.2U_eq (C) for aromatic, 0.96 Å, U_iso = 1.5U_eq (C) for CH₃ atoms and 0.97 Å, U_iso = 1.2U_eq (C) for CH₂ atoms. The absolute structure could not be determined from the diffraction data. Friedel pairs have been merged, and the configuration shown is arbitary.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram showing the C—H···O hydrogen bonds.

9-(Methoxymethyl)anthracene

Crystal data

C16H14O	F(000) = 1416
Mr = 222.27	Dx = 1.222 Mg m^−3
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 1313 reflections
a = 41.2360 (16) Å	θ = 1.0–25.0°
b = 10.1110 (8) Å	µ = 0.08 mm^−1
c = 8.6930 (6) Å	T = 293 K
V = 3624.4 (4) Å^3	Block, yellow
Z = 12	0.40 × 0.30 × 0.25 mm

Data collection

Bruker APEX CCD area-detector diffractometer	1746 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 25.1°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −46→48
Tmin = 0.854, Tmax = 0.982	k = −12→9
8859 measured reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 0.5696P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
1746 reflections	Δρmax = 0.14 e Å^−3
239 parameters	Δρmin = −0.15 e Å^−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.78219 (8)	0.7300 (3)	0.5267 (4)	0.0695 (9)
H1	0.7759	0.6462	0.5594	0.083*
C2	0.76281 (8)	0.7976 (4)	0.4294 (5)	0.0794 (11)
H2	0.7433	0.7601	0.3978	0.095*
C3	0.77155 (8)	0.9240 (4)	0.3749 (5)	0.0813 (10)
H3	0.7579	0.9691	0.3077	0.098*
C4	0.79948 (7)	0.9787 (4)	0.4200 (4)	0.0694 (9)
H4	0.8051	1.0618	0.3826	0.083*
C5	0.82076 (7)	0.9132 (3)	0.5239 (4)	0.0552 (7)
C6	0.84968 (7)	0.9698 (3)	0.5729 (4)	0.0577 (8)
H6	0.8554	1.0527	0.5353	0.069*
C7	0.87030 (7)	0.9072 (3)	0.6757 (3)	0.0526 (7)
C8	0.89975 (7)	0.9686 (3)	0.7243 (4)	0.0622 (8)
H8	0.9050	1.0523	0.6876	0.075*
C9	0.92012 (8)	0.9072 (3)	0.8225 (4)	0.0690 (9)
H9	0.9392	0.9483	0.8528	0.083*
C10	0.91236 (8)	0.7810 (3)	0.8789 (4)	0.0712 (9)
H10	0.9266	0.7391	0.9462	0.085*
C11	0.88455 (8)	0.7190 (3)	0.8374 (4)	0.0663 (9)
H11	0.8799	0.6360	0.8781	0.080*
C12	0.86212 (7)	0.7782 (3)	0.7323 (3)	0.0531 (7)
C13	0.83312 (8)	0.7169 (3)	0.6835 (3)	0.0544 (8)
C14	0.81206 (7)	0.7842 (3)	0.5805 (3)	0.0549 (7)
C15	0.82409 (8)	0.5802 (3)	0.7375 (4)	0.0626 (8)
H15A	0.8356	0.5596	0.8319	0.075*
H15B	0.8010	0.5761	0.7580	0.075*
C16	0.82168 (10)	0.3581 (3)	0.6614 (5)	0.0868 (12)
H16A	0.8274	0.2981	0.5803	0.130*
H16B	0.7986	0.3582	0.6744	0.130*
H16C	0.8319	0.3306	0.7554	0.130*
C17	0.93912 (9)	0.7459 (3)	0.4267 (4)	0.0703 (9)
H17	0.9381	0.8111	0.5020	0.084*
C18	0.91127 (9)	0.6979 (3)	0.3669 (5)	0.0777 (10)
H18	0.8915	0.7301	0.4023	0.093*
C19	0.91169 (9)	0.5998 (3)	0.2517 (5)	0.0788 (10)
H19	0.8924	0.5690	0.2095	0.095*
C20	0.94047 (8)	0.5509 (3)	0.2030 (5)	0.0761 (10)
H20	0.9406	0.4845	0.1289	0.091*
C21	0.97045 (8)	0.5984 (3)	0.2621 (4)	0.0610 (8)
C22	1.0000	0.5506 (4)	0.2086 (6)	0.0689 (13)
H22	1.0000	0.4844	0.1344	0.083*
C23	0.97033 (8)	0.6990 (3)	0.3772 (3)	0.0570 (7)
C24	1.0000	0.7484 (4)	0.4348 (5)	0.0594 (11)
C25	1.0000	0.8575 (4)	0.5519 (5)	0.0709 (13)
H25A	0.9809	0.8510	0.6166	0.085*	0.50
H25B	1.0191	0.8510	0.6166	0.085*	0.50
C26	1.0000	1.0899 (5)	0.5704 (7)	0.098 (2)
H26A	1.0000	1.1697	0.5104	0.147*
H26B	1.0190	1.0876	0.6341	0.147*	0.50
H26C	0.9810	1.0876	0.6341	0.147*	0.50
O1	0.83235 (5)	0.4882 (2)	0.6226 (3)	0.0661 (6)
O2	1.0000	0.9797 (3)	0.4714 (4)	0.0749 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.071 (2)	0.069 (2)	0.068 (2)	−0.0136 (18)	0.0117 (19)	−0.0047 (18)
C2	0.061 (2)	0.093 (3)	0.084 (3)	−0.0089 (19)	−0.0028 (19)	−0.006 (2)
C3	0.072 (2)	0.087 (2)	0.085 (3)	0.0065 (19)	−0.014 (2)	0.007 (2)
C4	0.073 (2)	0.067 (2)	0.068 (2)	0.0038 (17)	−0.0019 (18)	0.0076 (18)
C5	0.0606 (18)	0.0549 (17)	0.0503 (17)	0.0017 (15)	0.0070 (15)	0.0016 (14)
C6	0.0679 (18)	0.0496 (17)	0.0555 (19)	−0.0034 (15)	0.0098 (15)	0.0028 (15)
C7	0.0614 (17)	0.0498 (16)	0.0466 (16)	0.0032 (14)	0.0054 (14)	−0.0039 (13)
C8	0.0687 (18)	0.0616 (19)	0.0563 (19)	−0.0041 (15)	0.0070 (18)	−0.0049 (17)
C9	0.0639 (19)	0.080 (2)	0.063 (2)	−0.0002 (17)	−0.0013 (17)	−0.0102 (19)
C10	0.077 (2)	0.075 (2)	0.062 (2)	0.0132 (18)	−0.006 (2)	−0.0040 (19)
C11	0.084 (2)	0.0537 (18)	0.061 (2)	0.0091 (17)	0.0070 (18)	−0.0006 (16)
C12	0.0672 (18)	0.0486 (16)	0.0434 (16)	0.0065 (13)	0.0070 (15)	−0.0039 (14)
C13	0.0705 (19)	0.0474 (16)	0.0454 (17)	−0.0012 (15)	0.0124 (15)	−0.0031 (13)
C14	0.0637 (17)	0.0543 (17)	0.0466 (17)	−0.0039 (14)	0.0119 (15)	−0.0052 (14)
C15	0.081 (2)	0.0584 (18)	0.0481 (17)	−0.0064 (15)	0.0123 (17)	0.0001 (16)
C16	0.120 (3)	0.055 (2)	0.085 (3)	−0.022 (2)	0.020 (2)	0.0004 (19)
C17	0.097 (3)	0.0559 (19)	0.058 (2)	0.0103 (19)	0.0110 (19)	0.0044 (16)
C18	0.085 (2)	0.072 (2)	0.077 (2)	0.005 (2)	0.011 (2)	0.017 (2)
C19	0.080 (2)	0.067 (2)	0.089 (3)	−0.0058 (18)	−0.001 (2)	0.011 (2)
C20	0.092 (3)	0.055 (2)	0.082 (2)	−0.0099 (18)	−0.008 (2)	−0.0077 (19)
C21	0.082 (2)	0.0411 (15)	0.0599 (19)	−0.0034 (15)	−0.0012 (18)	0.0001 (14)
C22	0.089 (3)	0.045 (2)	0.072 (3)	0.000	0.000	−0.014 (2)
C23	0.086 (2)	0.0409 (14)	0.0437 (16)	0.0030 (15)	0.0037 (18)	0.0062 (13)
C24	0.094 (3)	0.043 (2)	0.041 (2)	0.000	0.000	0.0061 (18)
C25	0.101 (4)	0.065 (3)	0.047 (3)	0.000	0.000	−0.008 (2)
C26	0.126 (5)	0.070 (3)	0.096 (5)	0.000	0.000	−0.039 (3)
O1	0.0944 (14)	0.0447 (10)	0.0593 (12)	−0.0068 (11)	0.0160 (12)	0.0000 (10)
O2	0.109 (2)	0.0506 (18)	0.065 (2)	0.000	0.000	−0.0179 (16)

Geometric parameters (Å, º)

C1—C2	1.349 (5)	C15—H15B	0.9700
C1—C14	1.427 (4)	C16—O1	1.427 (4)
C1—H1	0.9300	C16—H16A	0.9600
C2—C3	1.410 (5)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.337 (4)	C17—C18	1.351 (5)
C3—H3	0.9300	C17—C23	1.438 (4)
C4—C5	1.423 (4)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.411 (5)
C5—C6	1.389 (4)	C18—H18	0.9300
C5—C14	1.440 (4)	C19—C20	1.353 (5)
C6—C7	1.387 (4)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.423 (4)
C7—C8	1.428 (4)	C20—H20	0.9300
C7—C12	1.434 (4)	C21—C22	1.391 (4)
C8—C9	1.349 (4)	C21—C23	1.427 (4)
C8—H8	0.9300	C22—C21^i	1.391 (4)
C9—C10	1.404 (5)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.413 (4)
C10—C11	1.356 (4)	C24—C23^i	1.413 (4)
C10—H10	0.9300	C24—C25	1.501 (6)
C11—C12	1.431 (4)	C25—O2	1.420 (6)
C11—H11	0.9300	C25—H25A	0.9700
C12—C13	1.412 (4)	C25—H25B	0.9700
C13—C14	1.421 (4)	C26—O2	1.408 (6)
C13—C15	1.506 (4)	C26—H26A	0.9600
C15—O1	1.406 (4)	C26—H26B	0.9600
C15—H15A	0.9700	C26—H26C	0.9600
C2—C1—C14	121.5 (3)	C13—C15—H15B	109.9
C2—C1—H1	119.3	H15A—C15—H15B	108.3
C14—C1—H1	119.3	O1—C16—H16A	109.5
C1—C2—C3	121.2 (3)	O1—C16—H16B	109.5
C1—C2—H2	119.4	H16A—C16—H16B	109.5
C3—C2—H2	119.4	O1—C16—H16C	109.5
C4—C3—C2	119.8 (3)	H16A—C16—H16C	109.5
C4—C3—H3	120.1	H16B—C16—H16C	109.5
C2—C3—H3	120.1	C18—C17—C23	121.8 (3)
C3—C4—C5	121.6 (3)	C18—C17—H17	119.1
C3—C4—H4	119.2	C23—C17—H17	119.1
C5—C4—H4	119.2	C17—C18—C19	121.1 (4)
C6—C5—C4	122.1 (3)	C17—C18—H18	119.5
C6—C5—C14	118.8 (3)	C19—C18—H18	119.5
C4—C5—C14	119.0 (3)	C20—C19—C18	119.3 (4)
C7—C6—C5	122.4 (3)	C20—C19—H19	120.3
C7—C6—H6	118.8	C18—C19—H19	120.3
C5—C6—H6	118.8	C19—C20—C21	121.7 (3)
C6—C7—C8	120.9 (3)	C19—C20—H20	119.1
C6—C7—C12	119.5 (3)	C21—C20—H20	119.1
C8—C7—C12	119.6 (3)	C22—C21—C20	121.6 (3)
C9—C8—C7	121.1 (3)	C22—C21—C23	119.0 (3)
C9—C8—H8	119.4	C20—C21—C23	119.4 (3)
C7—C8—H8	119.4	C21^i—C22—C21	122.3 (4)
C8—C9—C10	119.8 (3)	C21^i—C22—H22	118.8
C8—C9—H9	120.1	C21—C22—H22	118.8
C10—C9—H9	120.1	C24—C23—C21	119.8 (3)
C11—C10—C9	121.3 (3)	C24—C23—C17	123.5 (3)
C11—C10—H10	119.3	C21—C23—C17	116.6 (3)
C9—C10—H10	119.3	C23^i—C24—C23	120.0 (4)
C10—C11—C12	121.5 (3)	C23^i—C24—C25	120.0 (2)
C10—C11—H11	119.2	C23—C24—C25	120.0 (2)
C12—C11—H11	119.2	O2—C25—C24	107.8 (3)
C13—C12—C11	123.7 (3)	O2—C25—H25A	110.1
C13—C12—C7	119.7 (3)	C24—C25—H25A	110.1
C11—C12—C7	116.6 (3)	O2—C25—H25B	110.1
C12—C13—C14	119.8 (3)	C24—C25—H25B	110.1
C12—C13—C15	121.2 (3)	H25A—C25—H25B	108.5
C14—C13—C15	119.0 (3)	O2—C26—H26A	109.5
C13—C14—C1	123.4 (3)	O2—C26—H26B	109.5
C13—C14—C5	119.8 (3)	H26A—C26—H26B	109.5
C1—C14—C5	116.8 (3)	O2—C26—H26C	109.5
O1—C15—C13	109.0 (2)	H26A—C26—H26C	109.5
O1—C15—H15A	109.9	H26B—C26—H26C	109.5
C13—C15—H15A	109.9	C15—O1—C16	111.6 (2)
O1—C15—H15B	109.9	C26—O2—C25	112.8 (4)
C14—C1—C2—C3	1.0 (5)	C2—C1—C14—C5	−1.1 (5)
C1—C2—C3—C4	−0.2 (6)	C6—C5—C14—C13	−0.5 (4)
C2—C3—C4—C5	−0.6 (6)	C4—C5—C14—C13	179.6 (3)
C3—C4—C5—C6	−179.3 (3)	C6—C5—C14—C1	−179.9 (3)
C3—C4—C5—C14	0.6 (5)	C4—C5—C14—C1	0.3 (4)
C4—C5—C6—C7	179.1 (3)	C12—C13—C15—O1	−99.2 (3)
C14—C5—C6—C7	−0.8 (4)	C14—C13—C15—O1	80.2 (3)
C5—C6—C7—C8	−179.6 (3)	C23—C17—C18—C19	−0.5 (5)
C5—C6—C7—C12	1.2 (4)	C17—C18—C19—C20	1.6 (5)
C6—C7—C8—C9	−179.0 (3)	C18—C19—C20—C21	−1.7 (5)
C12—C7—C8—C9	0.2 (4)	C19—C20—C21—C22	−178.1 (4)
C7—C8—C9—C10	−0.2 (5)	C19—C20—C21—C23	0.8 (5)
C8—C9—C10—C11	−0.4 (5)	C20—C21—C22—C21^i	178.3 (3)
C9—C10—C11—C12	1.0 (5)	C23—C21—C22—C21^i	−0.7 (7)
C10—C11—C12—C13	178.9 (3)	C22—C21—C23—C24	0.0 (5)
C10—C11—C12—C7	−1.1 (4)	C20—C21—C23—C24	−178.9 (3)
C6—C7—C12—C13	−0.4 (4)	C22—C21—C23—C17	179.2 (3)
C8—C7—C12—C13	−179.5 (3)	C20—C21—C23—C17	0.2 (4)
C6—C7—C12—C11	179.7 (3)	C18—C17—C23—C24	178.8 (3)
C8—C7—C12—C11	0.5 (4)	C18—C17—C23—C21	−0.4 (4)
C11—C12—C13—C14	179.1 (3)	C21—C23—C24—C23^i	0.6 (5)
C7—C12—C13—C14	−0.9 (4)	C17—C23—C24—C23^i	−178.5 (2)
C11—C12—C13—C15	−1.5 (4)	C21—C23—C24—C25	177.9 (3)
C7—C12—C13—C15	178.5 (3)	C17—C23—C24—C25	−1.2 (5)
C12—C13—C14—C1	−179.4 (3)	C23^i—C24—C25—O2	88.7 (3)
C15—C13—C14—C1	1.2 (4)	C23—C24—C25—O2	−88.7 (3)
C12—C13—C14—C5	1.4 (4)	C13—C15—O1—C16	−174.7 (3)
C15—C13—C14—C5	−178.1 (3)	C24—C25—O2—C26	180.000 (2)
C2—C1—C14—C13	179.6 (3)

Symmetry code: (i) −x+2, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1^ii	0.97	2.58	3.436 (5)	148

Symmetry code: (ii) x, −y+1, z+1/2.