4,10-Diall-yloxy-1,2,3,6b,7,8,9,12b-octa-hydro-perylene.

In the title compound, C(26)H(28)O(2), the central atoms are coplanar, with the -CH(2)-CH(2)- links of the cyclo-hexene groups lying to either side of the plane and with the diall-yloxy residues twisted out of this plane [C-C-O-C torsion angles = 16.6 (3) and -13.9 (3)°]. In the crystal structure, mol-ecules are connected into chains propagating in [100] via C-H⋯π inter-actions.

Related literature

For the preparation of oxygenated perylenes and their use as photosensitizing organic dyes in solar harvesting techniques, see: Penick et al. (2008 ▶).

Experimental

Crystal data

C26H28O2

M = 372.48

Monoclinic,

a = 4.5883 (1) Å

b = 14.9171 (3) Å

c = 13.9203 (3) Å

β = 95.153 (1)°

V = 948.92 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.63 mm−1

T = 100 K

0.50 × 0.19 × 0.11 mm

Data collection

Rigaku RAXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.745, T max = 0.935

8967 measured reflections

3243 independent reflections

2616 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.26

3243 reflections

254 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: PROCESS-AUTO (Rigaku, 1998 ▶); data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905243X/hb5266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905243X/hb5266Isup2.hkl

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

C26H28O2	F(000) = 400
Mr = 372.48	Dx = 1.304 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2yb	Cell parameters from 8127 reflections
a = 4.5883 (1) Å	θ = 6.7–70.1°
b = 14.9171 (3) Å	µ = 0.63 mm−1
c = 13.9203 (3) Å	T = 100 K
β = 95.153 (1)°	Prism, colourless
V = 948.92 (3) Å3	0.50 × 0.19 × 0.11 mm
Z = 2

Rigaku RAXIS RAPID diffractometer	3243 independent reflections
Radiation source: fine-focus sealed tube	2616 reflections with I > 2σ(I)
graphite	Rint = 0.039
Profile data from ω scans	θmax = 70.0°, θmin = 6.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −4→5
Tmin = 0.745, Tmax = 0.935	k = −18→17
8967 measured reflections	l = −16→16

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.26	w = 1/[σ2(Fo2) + (0.0392P)2 + 0.0986P] where P = (Fo2 + 2Fc2)/3
3243 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.19 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
O1	1.0758 (4)	0.14440 (11)	1.29479 (11)	0.0205 (4)
O2	0.3720 (4)	0.35698 (11)	0.62545 (11)	0.0209 (4)
C1	1.1560 (6)	0.14679 (19)	1.49090 (18)	0.0257 (6)
H1A	1.0022	0.1804	1.4579	0.031*
H1B	1.1811	0.1471	1.5594	0.031*
C2	1.3344 (6)	0.09973 (17)	1.44171 (18)	0.0215 (6)
H2	1.4851	0.0671	1.4776	0.026*
C3	1.3204 (6)	0.09320 (16)	1.33434 (16)	0.0185 (6)
H3A	1.5030	0.1168	1.3110	0.022*
H3B	1.2979	0.0298	1.3140	0.022*
C4	1.0339 (5)	0.15331 (16)	1.19565 (16)	0.0173 (6)
C5	1.1684 (5)	0.09822 (16)	1.13154 (17)	0.0182 (6)
H5	1.2992	0.0521	1.1547	0.022*
C6	1.1068 (5)	0.11230 (16)	1.03333 (17)	0.0179 (5)
H6	1.2013	0.0758	0.9896	0.022*
C7	0.9124 (5)	0.17770 (15)	0.99632 (17)	0.0146 (5)
C8	0.7818 (5)	0.23265 (14)	1.06198 (17)	0.0153 (5)
C9	0.8430 (5)	0.22077 (15)	1.16185 (18)	0.0161 (5)
C10	0.7069 (6)	0.28600 (17)	1.22696 (16)	0.0179 (6)
H10A	0.7947	0.2781	1.2940	0.021*
H10B	0.4943	0.2742	1.2257	0.021*
C11	0.7571 (6)	0.38257 (16)	1.19372 (17)	0.0226 (6)
H11A	0.9626	0.3997	1.2129	0.027*
H11B	0.6291	0.4235	1.2270	0.027*
C12	0.6945 (6)	0.39485 (15)	1.08386 (16)	0.0188 (5)
H12A	0.8768	0.4137	1.0566	0.023*
H12B	0.5487	0.4433	1.0713	0.023*
C13	0.5781 (6)	0.30864 (14)	1.03188 (16)	0.0148 (6)
H13	0.3844	0.2946	1.0560	0.018*
C14	0.5266 (5)	0.32240 (15)	0.92412 (18)	0.0153 (6)
C15	0.3363 (5)	0.38949 (16)	0.88675 (17)	0.0182 (6)
H15	0.2430	0.4269	0.9300	0.022*
C16	0.2800 (5)	0.40290 (16)	0.78830 (17)	0.0187 (6)
H16	0.1519	0.4496	0.7648	0.022*
C17	0.4106 (5)	0.34823 (15)	0.72429 (16)	0.0158 (5)
C18	0.5998 (5)	0.27982 (16)	0.75910 (16)	0.0160 (5)
C19	0.6584 (5)	0.26758 (15)	0.85844 (16)	0.0134 (5)
C20	0.8599 (6)	0.19078 (16)	0.88847 (17)	0.0168 (6)
H20	1.0537	0.2044	0.8642	0.020*
C21	0.7403 (6)	0.10527 (16)	0.83550 (16)	0.0199 (6)
H21A	0.8787	0.0552	0.8506	0.024*
H21B	0.5510	0.0888	0.8596	0.024*
C22	0.6961 (6)	0.11772 (17)	0.72538 (17)	0.0242 (6)
H22A	0.8354	0.0786	0.6947	0.029*
H22B	0.4955	0.0985	0.7021	0.029*
C23	0.7414 (6)	0.21513 (15)	0.69392 (17)	0.0189 (6)
H23A	0.9535	0.2280	0.6960	0.023*
H23B	0.6556	0.2233	0.6267	0.023*
C24	0.1371 (6)	0.41273 (16)	0.58588 (17)	0.0197 (6)
H24A	0.1660	0.4749	0.6099	0.024*
H24B	−0.0512	0.3903	0.6060	0.024*
C25	0.1309 (6)	0.41135 (16)	0.47868 (17)	0.0216 (6)
H25	−0.0200	0.4447	0.4437	0.026*
C26	0.3135 (6)	0.36865 (18)	0.42822 (18)	0.0272 (6)
H26A	0.4681	0.3344	0.4600	0.033*
H26B	0.2917	0.3718	0.3598	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0198 (10)	0.0258 (10)	0.0154 (8)	0.0072 (8)	−0.0006 (7)	0.0045 (7)
O2	0.0214 (11)	0.0219 (10)	0.0190 (9)	0.0062 (8)	−0.0009 (8)	0.0030 (8)
C1	0.0292 (17)	0.0258 (14)	0.0209 (13)	0.0025 (12)	−0.0032 (11)	0.0019 (11)
C2	0.0180 (15)	0.0208 (13)	0.0246 (14)	0.0024 (11)	−0.0037 (11)	0.0041 (11)
C3	0.0169 (15)	0.0165 (12)	0.0213 (14)	0.0006 (10)	−0.0031 (11)	0.0025 (11)
C4	0.0160 (15)	0.0191 (13)	0.0165 (12)	−0.0034 (11)	−0.0006 (11)	0.0021 (11)
C5	0.0178 (15)	0.0157 (12)	0.0207 (13)	0.0033 (11)	0.0001 (11)	0.0027 (10)
C6	0.0175 (15)	0.0133 (12)	0.0233 (13)	0.0004 (10)	0.0033 (10)	−0.0049 (10)
C7	0.0140 (15)	0.0111 (12)	0.0185 (12)	−0.0015 (9)	−0.0010 (10)	−0.0023 (10)
C8	0.0130 (14)	0.0132 (13)	0.0194 (13)	−0.0012 (10)	−0.0004 (11)	−0.0008 (10)
C9	0.0121 (15)	0.0144 (13)	0.0219 (13)	−0.0025 (10)	0.0023 (11)	−0.0005 (10)
C10	0.0202 (15)	0.0156 (13)	0.0176 (13)	0.0019 (11)	0.0001 (11)	−0.0031 (10)
C11	0.0311 (17)	0.0133 (13)	0.0229 (14)	−0.0047 (11)	−0.0001 (12)	−0.0038 (10)
C12	0.0231 (15)	0.0118 (12)	0.0213 (12)	−0.0007 (10)	0.0013 (10)	−0.0018 (9)
C13	0.0142 (15)	0.0135 (13)	0.0172 (13)	−0.0015 (9)	0.0041 (10)	−0.0013 (9)
C14	0.0127 (15)	0.0148 (12)	0.0186 (12)	−0.0029 (10)	0.0023 (10)	0.0017 (10)
C15	0.0181 (15)	0.0156 (12)	0.0212 (13)	0.0008 (10)	0.0030 (11)	0.0001 (10)
C16	0.0172 (15)	0.0155 (13)	0.0228 (14)	0.0027 (10)	−0.0008 (11)	0.0017 (11)
C17	0.0161 (16)	0.0144 (13)	0.0165 (12)	−0.0025 (10)	−0.0011 (10)	0.0024 (10)
C18	0.0140 (14)	0.0130 (12)	0.0209 (12)	−0.0004 (10)	0.0018 (10)	−0.0007 (10)
C19	0.0111 (13)	0.0099 (12)	0.0190 (12)	−0.0054 (10)	−0.0002 (10)	0.0016 (10)
C20	0.0144 (15)	0.0138 (13)	0.0223 (14)	−0.0007 (10)	0.0016 (11)	0.0001 (10)
C21	0.0262 (16)	0.0121 (12)	0.0213 (13)	−0.0006 (11)	0.0015 (11)	−0.0030 (10)
C22	0.0333 (17)	0.0180 (14)	0.0205 (13)	0.0015 (11)	−0.0022 (12)	−0.0020 (10)
C23	0.0215 (16)	0.0155 (13)	0.0194 (13)	0.0022 (10)	0.0011 (11)	0.0001 (10)
C24	0.0205 (16)	0.0178 (12)	0.0203 (13)	0.0032 (11)	−0.0006 (11)	0.0026 (11)
C25	0.0254 (17)	0.0178 (13)	0.0208 (13)	−0.0006 (11)	−0.0022 (11)	0.0022 (10)
C26	0.0311 (17)	0.0282 (15)	0.0210 (13)	0.0008 (12)	−0.0042 (11)	−0.0003 (11)

O1—C4	1.383 (3)	C12—H12B	0.9900
O1—C3	1.427 (3)	C13—C14	1.511 (3)
O2—C17	1.378 (3)	C13—H13	1.0000
O2—C24	1.432 (3)	C14—C15	1.398 (3)
C1—C2	1.316 (3)	C14—C19	1.403 (3)
C1—H1A	0.9500	C15—C16	1.386 (3)
C1—H1B	0.9500	C15—H15	0.9500
C2—C3	1.493 (3)	C16—C17	1.383 (3)
C2—H2	0.9500	C16—H16	0.9500
C3—H3A	0.9900	C17—C18	1.398 (3)
C3—H3B	0.9900	C18—C19	1.397 (3)
C4—C9	1.388 (3)	C18—C23	1.511 (3)
C4—C5	1.397 (3)	C19—C20	1.508 (3)
C5—C6	1.387 (3)	C20—C21	1.549 (3)
C5—H5	0.9500	C20—H20	1.0000
C6—C7	1.389 (3)	C21—C22	1.539 (3)
C6—H6	0.9500	C21—H21A	0.9900
C7—C8	1.402 (3)	C21—H21B	0.9900
C7—C20	1.512 (3)	C22—C23	1.537 (3)
C8—C9	1.405 (3)	C22—H22A	0.9900
C8—C13	1.504 (3)	C22—H22B	0.9900
C9—C10	1.503 (3)	C23—H23A	0.9900
C10—C11	1.537 (3)	C23—H23B	0.9900
C10—H10A	0.9900	C24—C25	1.490 (3)
C10—H10B	0.9900	C24—H24A	0.9900
C11—C12	1.541 (3)	C24—H24B	0.9900
C11—H11A	0.9900	C25—C26	1.306 (3)
C11—H11B	0.9900	C25—H25	0.9500
C12—C13	1.547 (3)	C26—H26A	0.9500
C12—H12A	0.9900	C26—H26B	0.9500
C4—O1—C3	118.08 (18)	C12—C13—H13	107.3
C17—O2—C24	117.67 (18)	C15—C14—C19	117.8 (2)
C2—C1—H1A	120.0	C15—C14—C13	120.2 (2)
C2—C1—H1B	120.0	C19—C14—C13	122.0 (2)
H1A—C1—H1B	120.0	C16—C15—C14	121.7 (2)
C1—C2—C3	125.6 (2)	C16—C15—H15	119.1
C1—C2—H2	117.2	C14—C15—H15	119.1
C3—C2—H2	117.2	C17—C16—C15	119.9 (2)
O1—C3—C2	108.2 (2)	C17—C16—H16	120.0
O1—C3—H3A	110.1	C15—C16—H16	120.0
C2—C3—H3A	110.1	O2—C17—C16	124.3 (2)
O1—C3—H3B	110.1	O2—C17—C18	115.8 (2)
C2—C3—H3B	110.1	C16—C17—C18	119.9 (2)
H3A—C3—H3B	108.4	C19—C18—C17	119.8 (2)
O1—C4—C9	115.8 (2)	C19—C18—C23	117.1 (2)
O1—C4—C5	123.5 (2)	C17—C18—C23	123.0 (2)
C9—C4—C5	120.8 (2)	C18—C19—C14	120.9 (2)
C6—C5—C4	118.5 (2)	C18—C19—C20	115.6 (2)
C6—C5—H5	120.7	C14—C19—C20	123.5 (2)
C4—C5—H5	120.7	C19—C20—C7	114.37 (19)
C5—C6—C7	122.6 (2)	C19—C20—C21	108.16 (19)
C5—C6—H6	118.7	C7—C20—C21	112.61 (18)
C7—C6—H6	118.7	C19—C20—H20	107.1
C6—C7—C8	117.8 (2)	C7—C20—H20	107.1
C6—C7—C20	119.9 (2)	C21—C20—H20	107.1
C8—C7—C20	122.2 (2)	C22—C21—C20	112.59 (18)
C7—C8—C9	120.8 (2)	C22—C21—H21A	109.1
C7—C8—C13	123.4 (2)	C20—C21—H21A	109.1
C9—C8—C13	115.8 (2)	C22—C21—H21B	109.1
C4—C9—C8	119.4 (2)	C20—C21—H21B	109.1
C4—C9—C10	123.3 (2)	H21A—C21—H21B	107.8
C8—C9—C10	117.3 (2)	C23—C22—C21	112.9 (2)
C9—C10—C11	110.1 (2)	C23—C22—H22A	109.0
C9—C10—H10A	109.6	C21—C22—H22A	109.0
C11—C10—H10A	109.6	C23—C22—H22B	109.0
C9—C10—H10B	109.6	C21—C22—H22B	109.0
C11—C10—H10B	109.6	H22A—C22—H22B	107.8
H10A—C10—H10B	108.2	C18—C23—C22	110.9 (2)
C10—C11—C12	112.98 (19)	C18—C23—H23A	109.5
C10—C11—H11A	109.0	C22—C23—H23A	109.5
C12—C11—H11A	109.0	C18—C23—H23B	109.5
C10—C11—H11B	109.0	C22—C23—H23B	109.5
C12—C11—H11B	109.0	H23A—C23—H23B	108.1
H11A—C11—H11B	107.8	O2—C24—C25	108.87 (19)
C11—C12—C13	113.02 (18)	O2—C24—H24A	109.9
C11—C12—H12A	109.0	C25—C24—H24A	109.9
C13—C12—H12A	109.0	O2—C24—H24B	109.9
C11—C12—H12B	109.0	C25—C24—H24B	109.9
C13—C12—H12B	109.0	H24A—C24—H24B	108.3
H12A—C12—H12B	107.8	C26—C25—C24	126.1 (2)
C8—C13—C14	114.61 (19)	C26—C25—H25	116.9
C8—C13—C12	108.44 (19)	C24—C25—H25	116.9
C14—C13—C12	111.59 (18)	C25—C26—H26A	120.0
C8—C13—H13	107.3	C25—C26—H26B	120.0
C14—C13—H13	107.3	H26A—C26—H26B	120.0
C4—O1—C3—C2	175.20 (19)	C19—C14—C15—C16	−0.7 (3)
C1—C2—C3—O1	−1.7 (4)	C13—C14—C15—C16	−178.8 (2)
C3—O1—C4—C9	−164.3 (2)	C14—C15—C16—C17	0.9 (4)
C3—O1—C4—C5	16.6 (3)	C24—O2—C17—C16	−13.9 (3)
O1—C4—C5—C6	179.0 (2)	C24—O2—C17—C18	167.3 (2)
C9—C4—C5—C6	−0.1 (3)	C15—C16—C17—O2	−179.0 (2)
C4—C5—C6—C7	−1.3 (4)	C15—C16—C17—C18	−0.2 (4)
C5—C6—C7—C8	1.8 (4)	O2—C17—C18—C19	178.24 (19)
C5—C6—C7—C20	178.7 (2)	C16—C17—C18—C19	−0.7 (3)
C6—C7—C8—C9	−0.9 (3)	O2—C17—C18—C23	−3.5 (3)
C20—C7—C8—C9	−177.7 (2)	C16—C17—C18—C23	177.5 (2)
C6—C7—C8—C13	177.2 (2)	C17—C18—C19—C14	0.9 (3)
C20—C7—C8—C13	0.3 (3)	C23—C18—C19—C14	−177.4 (2)
O1—C4—C9—C8	−178.18 (19)	C17—C18—C19—C20	178.7 (2)
C5—C4—C9—C8	0.9 (3)	C23—C18—C19—C20	0.4 (3)
O1—C4—C9—C10	5.0 (3)	C15—C14—C19—C18	−0.2 (3)
C5—C4—C9—C10	−175.9 (2)	C13—C14—C19—C18	177.9 (2)
C7—C8—C9—C4	−0.4 (3)	C15—C14—C19—C20	−177.9 (2)
C13—C8—C9—C4	−178.7 (2)	C13—C14—C19—C20	0.2 (3)
C7—C8—C9—C10	176.6 (2)	C18—C19—C20—C7	−178.4 (2)
C13—C8—C9—C10	−1.6 (3)	C14—C19—C20—C7	−0.6 (3)
C4—C9—C10—C11	128.2 (2)	C18—C19—C20—C21	−52.0 (3)
C8—C9—C10—C11	−48.6 (3)	C14—C19—C20—C21	125.8 (2)
C9—C10—C11—C12	45.6 (3)	C6—C7—C20—C19	−176.4 (2)
C10—C11—C12—C13	3.3 (3)	C8—C7—C20—C19	0.3 (3)
C7—C8—C13—C14	−0.7 (3)	C6—C7—C20—C21	59.6 (3)
C9—C8—C13—C14	177.4 (2)	C8—C7—C20—C21	−123.7 (2)
C7—C8—C13—C12	−126.1 (2)	C19—C20—C21—C22	54.4 (3)
C9—C8—C13—C12	52.0 (3)	C7—C20—C21—C22	−178.2 (2)
C11—C12—C13—C8	−51.3 (3)	C20—C21—C22—C23	−7.6 (3)
C11—C12—C13—C14	−178.5 (2)	C19—C18—C23—C22	48.7 (3)
C8—C13—C14—C15	178.5 (2)	C17—C18—C23—C22	−129.6 (2)
C12—C13—C14—C15	−57.8 (3)	C21—C22—C23—C18	−42.6 (3)
C8—C13—C14—C19	0.5 (3)	C17—O2—C24—C25	−178.87 (19)
C12—C13—C14—C19	124.2 (2)	O2—C24—C25—C26	−1.8 (4)

Cg1 and Cg4 are the centroids of the C4–C9 and C14–C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg1i	1.00	2.78	3.671 (3)	148
C20—H20···Cg4ii	1.00	2.82	3.702 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cg1i	1.00	2.78	3.671 (3)	148
C20—H20⋯Cg4ii	1.00	2.82	3.702 (3)	148

Symmetry codes: (i) ; (ii) . Cg1 and Cg4 are the centroids of the C4–C9 and C14–C19 rings, respectively.