9,9-Dimethyl-9,10-dihydroanthracene

Siddaraju, B.P.; Jasinski, J.P.; Golen, J.A.; Yathirajan, H.S.; Raju, C.R.

doi:10.1107/S1600536811033526

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2397

doi:10.1107/S1600536811033526

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9,9-Dimethyl-9,10-dihydroanthracene

B. P. Siddaraju,^a Jerry P. Jasinski,^b ^* James A. Golen,^b H. S. Yathirajan ^c and C. R. Raju ^d

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^cDepartment of Studies in Chemistry, University of Mysore, Bangalore 560 064, India, and ^dDepartment of Chemistry, PES College of Science, Mandya 571 401, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 16 August 2011; accepted 17 August 2011; online 27 August 2011)

In the title compound, C₁₆H₁₆, the central benzene ring adopts a boat conformation, with a dihedral angle of 34.7 (9)° between the mean planes of the two fused benzene rings. The two methyl groups at the apex of the central benzene ring are in axial and equatorial conformations. The crystal packing is stabilized by weak C—H⋯π intermolecular interactions.

Related literature

For analytical applications of anthrone, see: Trevelyan (1952 ). For related structures, see: Destro et al. (1973 ); Fun et al. (2010 ); Ghosh et al. (1993 ); Iball & Low (1974 ); Srivastava (1964 ); Zhou et al. (2004 , 2005 , 2007 ).

Experimental

Crystal data

C₁₆H₁₆
M_r = 208.29
Monoclinic, P 2₁ /n
a = 12.7042 (15) Å
b = 7.4882 (7) Å
c = 13.177 (2) Å
β = 107.787 (14)°
V = 1193.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 K
0.38 × 0.32 × 0.25 mm

Data collection

Oxford Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO (Version 171.31.8) and CrysAlis RED (Version 1.171.31.8). Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.976, T_max = 0.984
10733 measured reflections
2958 independent reflections
2447 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.144
S = 1.01
2958 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg3ⁱ	0.95	2.75	3.7072 (16)	177
Symmetry code: (i) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO (Version 171.31.8) and CrysAlis RED (Version 1.171.31.8). Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO (Version 171.31.8) and CrysAlis RED (Version 1.171.31.8). Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033526/bt5616sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033526/bt5616Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033526/bt5616Isup3.cml

checkCIF report

Comment top

Anthracene and its derivatives are long known polycyclic aromatic compounds showing a high potential for use in materials science (e.g. fluorescence probing, photochromic systems, electroluminescence) and several reviews have been published. Anthrone is a tricyclic aromatic hydrocarbon which is used for a popular cellulose assay and in the colorometric determination of carbohydrates (Trevelyan, 1952) and anthracene itself is used in the production of red dye alizarin. The crystal structures of anthrone (Srivastava, 1964), 10-bromoanthrone (Destro et al., 1973), 9,10-dimethylanthracene (Iball & Low, 1974), benzylideneanthrone at 193 K (Ghosh et al., 1993), 10-(2-methylbenzylidene)anthrone (Zhou et al., 2004), 10-(3,4-dimethoxybenzylidene)anthrone (Zhou et al., 2005), 10-(4-hydroxy-3-nitrobenzylidene)anthrone (Zhou et al., 2007) and 10,10-dimethylanthrone (Fun et al., 2010) have been reported. In view of the importance of anthracene derivatives, this paper reports the crystal structure of the title compound, (I), C₁₆H₁₆.

In the title compound, C₁₆H₁₆, the center benzene ring (C1/C6–C8/C13/C14) with puckering parameters, Q, θ, ϕ, of 0.4930 (13) Å, 92.27 (15)°, 120.13 (15)°, adopts a boat conformation with a dihedral angle of 34.7 (9)° between the mean planes of the two fused benzene rings (Fig. 1). The two methyl groups at the apex of the center benzene ring are in axial and equatorial conformations. The crystal packing is stabilized by weak C—H···Cg π-ring intermolecular interactions (Fig. 2).

Related literature top

For analytical applications of anthrone, see: Trevelyan (1952). For related structures, see: Destro et al. (1973); Fun et al. (2010); Ghosh et al. (1993); Iball & Low (1974); Srivastava (1964); Zhou et al. (2004, 2005, 2007).

Figure captions provided mention a co-crystal salt, which is not the present compound. Please supply correct captions.

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chemicals, Bangalore. X-ray quality crystals were grown from toluene solution by slow evaporation (320–322 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title co-crystal salt showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title co-crystal salt viewed down the b axis.

9,9-Dimethyl-9,10-dihydroanthracene top

Crystal data top

C₁₆H₁₆	F(000) = 448
M_r = 208.29	D_x = 1.159 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4436 reflections
a = 12.7042 (15) Å	θ = 3.3–32.2°
b = 7.4882 (7) Å	µ = 0.07 mm⁻¹
c = 13.177 (2) Å	T = 173 K
β = 107.787 (14)°	Block, colourless
V = 1193.7 (3) Å³	0.38 × 0.32 × 0.25 mm
Z = 4

Data collection top

Oxford Xcalibur Eos Gemini diffractometer	2958 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2447 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.1500 pixels mm^-1	θ_max = 28.3°, θ_min = 3.4°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −9→9
T_min = 0.976, T_max = 0.984	l = −17→17
10733 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0778P)² + 0.2041P] where P = (F_o² + 2F_c²)/3
2958 reflections	(Δ/σ)_max < 0.001
147 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₁₆	V = 1193.7 (3) Å³
M_r = 208.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.7042 (15) Å	µ = 0.07 mm⁻¹
b = 7.4882 (7) Å	T = 173 K
c = 13.177 (2) Å	0.38 × 0.32 × 0.25 mm
β = 107.787 (14)°

Data collection top

Oxford Xcalibur Eos Gemini diffractometer	2958 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2447 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.984	R_int = 0.023
10733 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
2958 reflections	Δρ_min = −0.21 e Å⁻³
147 parameters

Special details top

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	0.39240 (10)	0.13364 (15)	0.28673 (10)	0.0417 (3)
C2	0.28419 (11)	0.07383 (19)	0.26861 (15)	0.0597 (4)
H2A	0.2447	0.0248	0.2012	0.072*
C3	0.23363 (14)	0.0853 (2)	0.34811 (18)	0.0743 (5)
H3A	0.1599	0.0440	0.3347	0.089*
C4	0.28927 (16)	0.1558 (2)	0.44566 (17)	0.0736 (5)
H4A	0.2541	0.1644	0.4996	0.088*
C5	0.39589 (14)	0.2141 (2)	0.46526 (13)	0.0605 (4)
H5A	0.4345	0.2623	0.5331	0.073*
C6	0.44818 (10)	0.20332 (16)	0.38678 (10)	0.0439 (3)
C7	0.56538 (11)	0.26594 (18)	0.41022 (9)	0.0465 (3)
H7A	0.5811	0.3571	0.4673	0.056*
H7B	0.6160	0.1640	0.4364	0.056*
C8	0.58672 (9)	0.34389 (15)	0.31365 (9)	0.0361 (3)
C9	0.66134 (9)	0.48356 (17)	0.32422 (10)	0.0451 (3)
H9A	0.6981	0.5294	0.3932	0.054*
C10	0.68302 (10)	0.55675 (18)	0.23709 (12)	0.0518 (3)
H10A	0.7340	0.6525	0.2454	0.062*
C11	0.62997 (11)	0.48946 (19)	0.13806 (12)	0.0539 (4)
H11A	0.6445	0.5386	0.0772	0.065*
C12	0.55516 (10)	0.35000 (18)	0.12576 (10)	0.0463 (3)
H12A	0.5192	0.3050	0.0564	0.056*
C13	0.53167 (8)	0.27457 (15)	0.21306 (8)	0.0352 (3)
C14	0.45293 (9)	0.11660 (16)	0.20299 (9)	0.0400 (3)
C15	0.37195 (13)	0.1028 (2)	0.09028 (11)	0.0622 (4)
H15A	0.3270	0.2114	0.0737	0.093*
H15B	0.3237	−0.0010	0.0859	0.093*
H15C	0.4133	0.0890	0.0390	0.093*
C16	0.52239 (12)	−0.05675 (18)	0.22602 (12)	0.0536 (4)
H16A	0.5754	−0.0507	0.2978	0.080*
H16B	0.5624	−0.0698	0.1736	0.080*
H16C	0.4734	−0.1595	0.2213	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0379 (6)	0.0300 (5)	0.0586 (7)	0.0032 (4)	0.0167 (5)	0.0062 (5)
C2	0.0446 (7)	0.0415 (7)	0.0949 (11)	−0.0046 (6)	0.0242 (7)	0.0008 (7)
C3	0.0569 (9)	0.0455 (8)	0.1372 (17)	0.0005 (7)	0.0545 (11)	0.0164 (10)
C4	0.0899 (12)	0.0467 (8)	0.1113 (15)	0.0097 (8)	0.0710 (12)	0.0189 (9)
C5	0.0819 (10)	0.0480 (8)	0.0647 (9)	0.0075 (7)	0.0419 (8)	0.0132 (7)
C6	0.0509 (7)	0.0366 (6)	0.0482 (6)	0.0054 (5)	0.0210 (5)	0.0103 (5)
C7	0.0496 (7)	0.0496 (7)	0.0363 (6)	0.0001 (6)	0.0070 (5)	0.0027 (5)
C8	0.0306 (5)	0.0364 (6)	0.0394 (6)	0.0052 (4)	0.0080 (4)	0.0013 (4)
C9	0.0353 (6)	0.0404 (6)	0.0560 (7)	0.0008 (5)	0.0086 (5)	−0.0044 (5)
C10	0.0394 (6)	0.0400 (6)	0.0797 (10)	0.0008 (5)	0.0239 (6)	0.0057 (6)
C11	0.0516 (7)	0.0534 (8)	0.0663 (9)	0.0096 (6)	0.0323 (7)	0.0182 (7)
C12	0.0464 (6)	0.0536 (7)	0.0400 (6)	0.0088 (6)	0.0148 (5)	0.0043 (5)
C13	0.0305 (5)	0.0356 (6)	0.0388 (5)	0.0060 (4)	0.0094 (4)	0.0016 (4)
C14	0.0368 (6)	0.0373 (6)	0.0426 (6)	−0.0001 (4)	0.0074 (5)	−0.0036 (5)
C15	0.0559 (8)	0.0667 (10)	0.0526 (8)	−0.0121 (7)	−0.0005 (6)	−0.0092 (7)
C16	0.0547 (7)	0.0363 (6)	0.0711 (9)	0.0043 (6)	0.0210 (7)	−0.0059 (6)

Geometric parameters (Å, º) top

C1—C6	1.3935 (18)	C9—C10	1.3739 (19)
C1—C2	1.3953 (18)	C9—H9A	0.9500
C1—C14	1.5309 (17)	C10—C11	1.369 (2)
C2—C3	1.389 (2)	C10—H10A	0.9500
C2—H2A	0.9500	C11—C12	1.388 (2)
C3—C4	1.370 (3)	C11—H11A	0.9500
C3—H3A	0.9500	C12—C13	1.3933 (16)
C4—C5	1.370 (2)	C12—H12A	0.9500
C4—H4A	0.9500	C13—C14	1.5285 (16)
C5—C6	1.3917 (18)	C14—C15	1.5301 (17)
C5—H5A	0.9500	C14—C16	1.5467 (17)
C6—C7	1.5004 (18)	C15—H15A	0.9800
C7—C8	1.4981 (16)	C15—H15B	0.9800
C7—H7A	0.9900	C15—H15C	0.9800
C7—H7B	0.9900	C16—H16A	0.9800
C8—C9	1.3897 (17)	C16—H16B	0.9800
C8—C13	1.3962 (15)	C16—H16C	0.9800

C6—C1—C2	118.15 (13)	C11—C10—C9	118.94 (12)
C6—C1—C14	119.40 (10)	C11—C10—H10A	120.5
C2—C1—C14	122.38 (12)	C9—C10—H10A	120.5
C3—C2—C1	120.64 (16)	C10—C11—C12	120.56 (12)
C3—C2—H2A	119.7	C10—C11—H11A	119.7
C1—C2—H2A	119.7	C12—C11—H11A	119.7
C4—C3—C2	120.46 (15)	C11—C12—C13	121.37 (12)
C4—C3—H3A	119.8	C11—C12—H12A	119.3
C2—C3—H3A	119.8	C13—C12—H12A	119.3
C3—C4—C5	119.77 (15)	C12—C13—C8	117.49 (11)
C3—C4—H4A	120.1	C12—C13—C14	122.80 (11)
C5—C4—H4A	120.1	C8—C13—C14	119.66 (10)
C4—C5—C6	120.68 (16)	C13—C14—C15	111.39 (11)
C4—C5—H5A	119.7	C13—C14—C1	109.41 (9)
C6—C5—H5A	119.7	C15—C14—C1	111.62 (10)
C5—C6—C1	120.30 (13)	C13—C14—C16	108.27 (9)
C5—C6—C7	119.85 (12)	C15—C14—C16	107.92 (11)
C1—C6—C7	119.85 (11)	C1—C14—C16	108.10 (10)
C8—C7—C6	111.87 (10)	C14—C15—H15A	109.5
C8—C7—H7A	109.2	C14—C15—H15B	109.5
C6—C7—H7A	109.2	H15A—C15—H15B	109.5
C8—C7—H7B	109.2	C14—C15—H15C	109.5
C6—C7—H7B	109.2	H15A—C15—H15C	109.5
H7A—C7—H7B	107.9	H15B—C15—H15C	109.5
C9—C8—C13	120.23 (11)	C14—C16—H16A	109.5
C9—C8—C7	120.20 (11)	C14—C16—H16B	109.5
C13—C8—C7	119.57 (10)	H16A—C16—H16B	109.5
C10—C9—C8	121.42 (12)	C14—C16—H16C	109.5
C10—C9—H9A	119.3	H16A—C16—H16C	109.5
C8—C9—H9A	119.3	H16B—C16—H16C	109.5

C6—C1—C2—C3	0.6 (2)	C10—C11—C12—C13	0.06 (19)
C14—C1—C2—C3	177.46 (12)	C11—C12—C13—C8	−0.35 (17)
C1—C2—C3—C4	0.1 (2)	C11—C12—C13—C14	−177.76 (11)
C2—C3—C4—C5	−0.6 (2)	C9—C8—C13—C12	0.34 (16)
C3—C4—C5—C6	0.4 (2)	C7—C8—C13—C12	−179.27 (10)
C4—C5—C6—C1	0.3 (2)	C9—C8—C13—C14	177.83 (10)
C4—C5—C6—C7	−179.33 (13)	C7—C8—C13—C14	−1.78 (16)
C2—C1—C6—C5	−0.75 (18)	C12—C13—C14—C15	−22.82 (16)
C14—C1—C6—C5	−177.72 (11)	C8—C13—C14—C15	159.83 (11)
C2—C1—C6—C7	178.86 (12)	C12—C13—C14—C1	−146.71 (11)
C14—C1—C6—C7	1.88 (17)	C8—C13—C14—C1	35.93 (13)
C5—C6—C7—C8	−146.93 (12)	C12—C13—C14—C16	95.69 (13)
C1—C6—C7—C8	33.46 (16)	C8—C13—C14—C16	−81.66 (13)
C6—C7—C8—C9	146.92 (11)	C6—C1—C14—C13	−35.94 (14)
C6—C7—C8—C13	−33.47 (16)	C2—C1—C14—C13	147.22 (12)
C13—C8—C9—C10	−0.04 (18)	C6—C1—C14—C15	−159.70 (12)
C7—C8—C9—C10	179.56 (11)	C2—C1—C14—C15	23.46 (17)
C8—C9—C10—C11	−0.25 (19)	C6—C1—C14—C16	81.76 (13)
C9—C10—C11—C12	0.24 (19)	C2—C1—C14—C16	−95.08 (14)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cg3ⁱ	0.95	2.75	3.7072 (16)	177

Symmetry code: (i) −x+5/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆
M_r	208.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	12.7042 (15), 7.4882 (7), 13.177 (2)
β (°)	107.787 (14)
V (Å³)	1193.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.38 × 0.32 × 0.25

Data collection
Diffractometer	Oxford Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10733, 2958, 2447
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.144, 1.01
No. of reflections	2958
No. of parameters	147
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cg3ⁱ	0.95	2.75	3.7072 (16)	177

Symmetry code: (i) −x+5/2, y+1/2, −z+1/2.

Acknowledgements

BPS thanks the University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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Volume 67| Part 9| September 2011| Page o2397

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