1,4,5,8-Tetra-isopropyl-anthracene.

The mol-ecules of the title compound, C(26)H(34), possess crystallographically imposed inversion symmetry. The anthracene ring system is planar within 0.038 (1) Å. The two methyl groups in each independent isopropyl group are oriented on either side of the anthracene plane. In the crystal structure, the mol-ecules adopt a herringbone-like arrangement without π-π stacking.

Related literature

For the preparation and solid-state fluorescence studies of 1,4,5,8- tetra­alkyl­anthracenes, see: Kitamura et al. (2007 ▶). For a related structure, see: Kitamura et al. (2010 ▶). For related herringbone structures, see: Curtis et al. (2004 ▶).

Experimental

Crystal data

C26H34

M = 346.53

Monoclinic,

a = 6.546 (3) Å

b = 10.357 (5) Å

c = 15.808 (8) Å

β = 98.289 (8)°

V = 1060.5 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.06 mm−1

T = 223 K

0.50 × 0.07 × 0.05 mm

Data collection

Rigaku/MSC Mercury CCD area-detector diffractometer

Absorption correction: numerical (NUMABS; Higashi, 2000 ▶) T min = 0.991, T max = 0.996

9107 measured reflections

2817 independent reflections

1921 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.180

S = 1.07

2817 reflections

122 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030837/ci5142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030837/ci5142Isup2.hkl

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

C26H34	F(000) = 380
Mr = 346.53	Dx = 1.085 Mg m−3
Monoclinic, P21/c	Melting point: 488 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.546 (3) Å	Cell parameters from 2745 reflections
b = 10.357 (5) Å	θ = 2.4–31.1°
c = 15.808 (8) Å	µ = 0.06 mm−1
β = 98.289 (8)°	T = 223 K
V = 1060.5 (9) Å3	Needle, colourless
Z = 2	0.50 × 0.07 × 0.05 mm

Rigaku/MSC Mercury CCD area-detector diffractometer	2817 independent reflections
Radiation source: rotating-anode X-ray tube	1921 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 14.7059 pixels mm-1	θmax = 29.1°, θmin = 2.4°
φ and ω scans	h = −8→8
Absorption correction: numerical (NUMABS; Higashi, 2000)	k = −14→13
Tmin = 0.991, Tmax = 0.996	l = −21→13
9107 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.063	H-atom parameters constrained
wR(F2) = 0.180	w = 1/[σ2(Fo2) + (0.0945P)2 + 0.0217P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2817 reflections	Δρmax = 0.28 e Å−3
122 parameters	Δρmin = −0.24 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.4015 (2)	−0.00637 (14)	0.17133 (9)	0.0272 (3)
C2	0.2347 (2)	0.06330 (15)	0.18742 (9)	0.0323 (4)
H2	0.1976	0.0606	0.2427	0.039*
C3	0.1152 (2)	0.13954 (15)	0.12440 (9)	0.0309 (4)
H3	0.0041	0.1874	0.1397	0.037*
C4	0.1553 (2)	0.14606 (13)	0.04219 (9)	0.0254 (3)
C5	0.3279 (2)	0.07195 (13)	0.02069 (9)	0.0245 (3)
C6	0.4533 (2)	−0.00120 (13)	0.08561 (8)	0.0245 (3)
C7	0.6226 (2)	−0.06900 (13)	0.06259 (9)	0.0263 (3)
H7	0.7074	−0.1149	0.1054	0.032*
C8	0.5294 (2)	−0.08656 (16)	0.24020 (9)	0.0336 (4)
H8	0.5737	−0.1653	0.2123	0.04*
C9	0.7238 (3)	−0.0145 (2)	0.27785 (12)	0.0551 (5)
H9A	0.6861	0.0624	0.307	0.083*
H9B	0.801	0.0099	0.2324	0.083*
H9C	0.8083	−0.0699	0.3182	0.083*
C10	0.4106 (3)	−0.1305 (2)	0.31140 (11)	0.0523 (5)
H10A	0.4928	−0.1925	0.3475	0.078*
H10B	0.2817	−0.1703	0.2865	0.078*
H10C	0.3817	−0.0565	0.3454	0.078*
C11	0.0299 (2)	0.23022 (14)	−0.02482 (9)	0.0293 (3)
H11	−0.0029	0.1782	−0.0776	0.035*
C12	−0.1738 (2)	0.27689 (16)	0.00091 (11)	0.0363 (4)
H12A	−0.2497	0.2037	0.0188	0.054*
H12B	−0.2552	0.3188	−0.0475	0.054*
H12C	−0.1459	0.3377	0.0478	0.054*
C13	0.1551 (3)	0.34794 (16)	−0.04622 (11)	0.0412 (4)
H13A	0.0758	0.3967	−0.092	0.062*
H13B	0.2832	0.3193	−0.0642	0.062*
H13C	0.1855	0.4022	0.004	0.062*

	U11	U22	U33	U12	U13	U23
C1	0.0275 (7)	0.0305 (7)	0.0245 (7)	−0.0017 (6)	0.0070 (6)	0.0001 (6)
C2	0.0338 (8)	0.0401 (9)	0.0251 (7)	0.0018 (7)	0.0115 (6)	0.0008 (6)
C3	0.0279 (7)	0.0345 (8)	0.0321 (8)	0.0042 (6)	0.0107 (6)	−0.0020 (6)
C4	0.0240 (7)	0.0257 (7)	0.0271 (7)	−0.0013 (6)	0.0053 (6)	−0.0018 (6)
C5	0.0225 (7)	0.0263 (7)	0.0252 (7)	−0.0018 (6)	0.0056 (6)	−0.0028 (5)
C6	0.0245 (7)	0.0272 (7)	0.0227 (7)	−0.0009 (6)	0.0061 (6)	−0.0011 (6)
C7	0.0257 (7)	0.0294 (7)	0.0238 (6)	0.0020 (6)	0.0038 (6)	0.0007 (6)
C8	0.0351 (9)	0.0418 (9)	0.0258 (7)	0.0053 (7)	0.0106 (6)	0.0038 (6)
C9	0.0487 (11)	0.0736 (14)	0.0393 (10)	−0.0036 (10)	−0.0065 (9)	0.0062 (10)
C10	0.0560 (12)	0.0639 (13)	0.0418 (10)	0.0165 (10)	0.0230 (9)	0.0225 (9)
C11	0.0286 (7)	0.0305 (8)	0.0292 (7)	0.0049 (6)	0.0054 (6)	−0.0009 (6)
C12	0.0313 (8)	0.0381 (9)	0.0401 (9)	0.0070 (7)	0.0069 (7)	0.0013 (7)
C13	0.0412 (9)	0.0374 (9)	0.0462 (9)	0.0056 (8)	0.0107 (8)	0.0105 (8)

C1—C2	1.362 (2)	C8—H8	0.99
C1—C6	1.4448 (18)	C9—H9A	0.97
C1—C8	1.521 (2)	C9—H9B	0.97
C2—C3	1.416 (2)	C9—H9C	0.97
C2—H2	0.94	C10—H10A	0.97
C3—C4	1.364 (2)	C10—H10B	0.97
C3—H3	0.94	C10—H10C	0.97
C4—C5	1.4463 (19)	C11—C12	1.528 (2)
C4—C11	1.518 (2)	C11—C13	1.534 (2)
C5—C7i	1.4009 (19)	C11—H11	0.99
C5—C6	1.435 (2)	C12—H12A	0.97
C6—C7	1.4033 (19)	C12—H12B	0.97
C7—C5i	1.4009 (19)	C12—H12C	0.97
C7—H7	0.94	C13—H13A	0.97
C8—C9	1.520 (3)	C13—H13B	0.97
C8—C10	1.527 (2)	C13—H13C	0.97
C2—C1—C6	117.28 (13)	H9A—C9—H9B	109.5
C2—C1—C8	121.93 (12)	C8—C9—H9C	109.5
C6—C1—C8	120.79 (12)	H9A—C9—H9C	109.5
C1—C2—C3	122.72 (12)	H9B—C9—H9C	109.5
C1—C2—H2	118.6	C8—C10—H10A	109.5
C3—C2—H2	118.6	C8—C10—H10B	109.5
C4—C3—C2	122.35 (13)	H10A—C10—H10B	109.5
C4—C3—H3	118.8	C8—C10—H10C	109.5
C2—C3—H3	118.8	H10A—C10—H10C	109.5
C3—C4—C5	117.50 (13)	H10B—C10—H10C	109.5
C3—C4—C11	122.28 (13)	C4—C11—C12	113.63 (12)
C5—C4—C11	120.19 (12)	C4—C11—C13	110.97 (13)
C7i—C5—C6	118.33 (12)	C12—C11—C13	108.77 (13)
C7i—C5—C4	121.79 (13)	C4—C11—H11	107.7
C6—C5—C4	119.88 (12)	C12—C11—H11	107.7
C7—C6—C5	118.08 (12)	C13—C11—H11	107.7
C7—C6—C1	121.72 (13)	C11—C12—H12A	109.5
C5—C6—C1	120.19 (12)	C11—C12—H12B	109.5
C5i—C7—C6	123.56 (13)	H12A—C12—H12B	109.5
C5i—C7—H7	118.2	C11—C12—H12C	109.5
C6—C7—H7	118.2	H12A—C12—H12C	109.5
C9—C8—C1	110.83 (14)	H12B—C12—H12C	109.5
C9—C8—C10	110.13 (15)	C11—C13—H13A	109.5
C1—C8—C10	113.81 (13)	C11—C13—H13B	109.5
C9—C8—H8	107.3	H13A—C13—H13B	109.5
C1—C8—H8	107.3	C11—C13—H13C	109.5
C10—C8—H8	107.3	H13A—C13—H13C	109.5
C8—C9—H9A	109.5	H13B—C13—H13C	109.5
C8—C9—H9B	109.5
C6—C1—C2—C3	−0.6 (2)	C8—C1—C6—C7	−0.2 (2)
C8—C1—C2—C3	179.32 (14)	C2—C1—C6—C5	−1.8 (2)
C1—C2—C3—C4	1.7 (2)	C8—C1—C6—C5	178.27 (13)
C2—C3—C4—C5	−0.4 (2)	C5—C6—C7—C5i	−1.8 (2)
C2—C3—C4—C11	−178.60 (14)	C1—C6—C7—C5i	176.64 (13)
C3—C4—C5—C7i	177.89 (13)	C2—C1—C8—C9	−99.18 (17)
C11—C4—C5—C7i	−3.8 (2)	C6—C1—C8—C9	80.72 (18)
C3—C4—C5—C6	−2.0 (2)	C2—C1—C8—C10	25.6 (2)
C11—C4—C5—C6	176.24 (12)	C6—C1—C8—C10	−154.51 (15)
C7i—C5—C6—C7	1.7 (2)	C3—C4—C11—C12	−15.2 (2)
C4—C5—C6—C7	−178.32 (12)	C5—C4—C11—C12	166.61 (13)
C7i—C5—C6—C1	−176.76 (13)	C3—C4—C11—C13	107.76 (16)
C4—C5—C6—C1	3.2 (2)	C5—C4—C11—C13	−70.44 (17)
C2—C1—C6—C7	179.72 (14)