1,7-Diethyl-4,10-diisopropyl-tetra-cene.

The mol-ecule of the title compound, C(28)H(32), is located on a crystallographic inversion center. The ethyl groups are essentially coplanar with the tetra-cene ring, making a torsion angle of -0.4 (4)°. The isopropyl groups adopt an asymmetric conformation with their terminal methyl groups positioned on opposite sides of the tetra-cene plane [the Me-C-C-C torsion angles are -22.5 (4) and 100.9 (3)°]. In the crystal, the mol-ecules adopt an arrangement without significant π-π inter-actions along the stacking direction (y axis).

Related literature

For applications of tetra­cene derivatives, see: Anthony (2008 ▶). For crystallochromy, see: Klebe et al. (1989 ▶). For the synthesis, see: Kitamura et al. (2011 ▶). For structures of related alkyl-substituted tetra­cene derivatives, see: Kitamura, Abe et al. (2010 ▶); Kitamura, Tsukuda et al. (2010 ▶).

Experimental

Crystal data

C28H32

M = 368.54

Monoclinic,

a = 12.901 (4) Å

b = 5.057 (2) Å

c = 16.962 (6) Å

β = 106.513 (9)°

V = 1061.0 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.06 mm−1

T = 203 K

0.25 × 0.13 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

9469 measured reflections

2423 independent reflections

1318 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.282

S = 1.10

2423 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.42 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1999 ▶); cell refinement: PROCESS-AUTO (Rigaku, 1998 ▶); data reduction: PROCESS-AUTO; 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 datablock(s) global, I. DOI: 10.1107/S1600536811036415/ld2024sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036415/ld2024Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036415/ld2024Isup3.cml

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

C28H32	F(000) = 400
Mr = 368.54	Dx = 1.154 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3820 reflections
a = 12.901 (4) Å	θ = 3.3–27.5°
b = 5.057 (2) Å	µ = 0.06 mm−1
c = 16.962 (6) Å	T = 203 K
β = 106.513 (9)°	Prism, yellow
V = 1061.0 (7) Å3	0.25 × 0.13 × 0.1 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	1318 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.083
graphite	θmax = 27.5°, θmin = 3.3°
Detector resolution: 10 pixels mm-1	h = −16→16
ω scans	k = −6→6
9469 measured reflections	l = −22→22
2423 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.081	H-atom parameters constrained
wR(F2) = 0.282	w = 1/[σ2(Fo2) + (0.1483P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2423 reflections	Δρmax = 0.26 e Å−3
130 parameters	Δρmin = −0.42 e Å−3
0 restraints

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	0.2359 (2)	0.9140 (5)	−0.04992 (16)	0.0445 (7)
C2	0.3434 (2)	0.8926 (5)	−0.01162 (17)	0.0475 (7)
H2	0.3918	1.0027	−0.0286	0.057*
C3	0.3853 (2)	0.7094 (5)	0.05323 (17)	0.0492 (7)
H3	0.4606	0.7005	0.0766	0.059*
C4	0.32137 (19)	0.5464 (5)	0.08311 (16)	0.0436 (7)
C5	0.20585 (18)	0.5603 (5)	0.04493 (15)	0.0418 (7)
C6	0.16283 (19)	0.7463 (4)	−0.02117 (16)	0.0428 (7)
C7	0.05225 (19)	0.7561 (5)	−0.05762 (16)	0.0457 (7)
H7	0.025	0.8765	−0.1008	0.055*
C8	−0.02107 (19)	0.5923 (5)	−0.03256 (16)	0.0429 (7)
C9	−0.13335 (19)	0.6016 (5)	−0.06961 (16)	0.0446 (7)
H9	−0.1606	0.722	−0.1128	0.054*
C10	0.1906 (2)	1.0987 (5)	−0.12112 (17)	0.0501 (7)
H10A	0.1395	1.2188	−0.1063	0.06*
H10B	0.1497	0.9937	−0.1683	0.06*
C11	0.2731 (2)	1.2644 (6)	−0.14795 (19)	0.0597 (8)
H11A	0.322	1.1486	−0.1658	0.09*
H11B	0.314	1.3712	−0.1021	0.09*
H11C	0.236	1.3789	−0.193	0.09*
C12	0.36829 (19)	0.3617 (5)	0.15477 (17)	0.0470 (7)
H12	0.3269	0.1943	0.1437	0.056*
C13	0.4870 (2)	0.2951 (6)	0.16758 (19)	0.0586 (8)
H13A	0.5306	0.452	0.1855	0.088*
H13B	0.4974	0.2324	0.1163	0.088*
H13C	0.5088	0.1583	0.2091	0.088*
C14	0.3535 (2)	0.4794 (6)	0.23422 (18)	0.0586 (8)
H14A	0.2772	0.509	0.2276	0.088*
H14B	0.392	0.6462	0.246	0.088*
H14C	0.3819	0.3576	0.2794	0.088*

	U11	U22	U33	U12	U13	U23
C1	0.0426 (14)	0.0452 (14)	0.0469 (16)	−0.0039 (11)	0.0144 (11)	−0.0033 (11)
C2	0.0424 (14)	0.0539 (15)	0.0479 (16)	−0.0092 (12)	0.0153 (12)	−0.0026 (12)
C3	0.0405 (14)	0.0496 (15)	0.0564 (18)	−0.0035 (11)	0.0120 (12)	−0.0034 (12)
C4	0.0399 (13)	0.0459 (14)	0.0436 (15)	−0.0020 (11)	0.0099 (11)	−0.0050 (11)
C5	0.0383 (13)	0.0444 (14)	0.0422 (15)	−0.0013 (10)	0.0108 (10)	−0.0027 (11)
C6	0.0423 (14)	0.0432 (14)	0.0435 (16)	−0.0015 (10)	0.0134 (11)	−0.0016 (11)
C7	0.0408 (14)	0.0498 (15)	0.0461 (16)	0.0001 (11)	0.0117 (11)	0.0043 (11)
C8	0.0389 (14)	0.0438 (14)	0.0465 (16)	−0.0009 (10)	0.0129 (11)	−0.0001 (10)
C9	0.0398 (13)	0.0459 (14)	0.0454 (16)	0.0013 (11)	0.0074 (11)	0.0048 (11)
C10	0.0486 (16)	0.0493 (15)	0.0515 (18)	−0.0053 (11)	0.0125 (13)	0.0029 (12)
C11	0.0577 (18)	0.0622 (18)	0.061 (2)	−0.0058 (14)	0.0193 (15)	0.0121 (14)
C12	0.0398 (14)	0.0497 (15)	0.0491 (17)	−0.0002 (11)	0.0087 (11)	0.0013 (12)
C13	0.0436 (16)	0.0650 (18)	0.063 (2)	0.0063 (13)	0.0088 (13)	0.0059 (14)
C14	0.0576 (18)	0.0711 (19)	0.0466 (17)	0.0016 (14)	0.0140 (13)	0.0007 (14)

C1—C2	1.359 (3)	C9—H9	0.94
C1—C6	1.451 (3)	C10—C11	1.522 (3)
C1—C10	1.507 (4)	C10—H10A	0.98
C2—C3	1.422 (4)	C10—H10B	0.98
C2—H2	0.94	C11—H11A	0.97
C3—C4	1.362 (3)	C11—H11B	0.97
C3—H3	0.94	C11—H11C	0.97
C4—C5	1.448 (3)	C12—C13	1.522 (3)
C4—C12	1.516 (3)	C12—C14	1.534 (4)
C5—C9i	1.394 (3)	C12—H12	0.99
C5—C6	1.448 (3)	C13—H13A	0.97
C6—C7	1.385 (3)	C13—H13B	0.97
C7—C8	1.411 (3)	C13—H13C	0.97
C7—H7	0.94	C14—H14A	0.97
C8—C9	1.406 (3)	C14—H14B	0.97
C8—C8i	1.430 (5)	C14—H14C	0.97
C9—C5i	1.394 (3)
C2—C1—C6	117.7 (2)	C11—C10—H10A	108.3
C2—C1—C10	122.9 (2)	C1—C10—H10B	108.3
C6—C1—C10	119.4 (2)	C11—C10—H10B	108.3
C1—C2—C3	122.2 (2)	H10A—C10—H10B	107.4
C1—C2—H2	118.9	C10—C11—H11A	109.5
C3—C2—H2	118.9	C10—C11—H11B	109.5
C4—C3—C2	123.0 (2)	H11A—C11—H11B	109.5
C4—C3—H3	118.5	C10—C11—H11C	109.5
C2—C3—H3	118.5	H11A—C11—H11C	109.5
C3—C4—C5	117.4 (2)	H11B—C11—H11C	109.5
C3—C4—C12	121.7 (2)	C4—C12—C13	114.0 (2)
C5—C4—C12	120.9 (2)	C4—C12—C14	110.1 (2)
C9i—C5—C6	118.2 (2)	C13—C12—C14	109.4 (2)
C9i—C5—C4	122.0 (2)	C4—C12—H12	107.7
C6—C5—C4	119.8 (2)	C13—C12—H12	107.7
C7—C6—C5	119.2 (2)	C14—C12—H12	107.7
C7—C6—C1	120.9 (2)	C12—C13—H13A	109.5
C5—C6—C1	119.8 (2)	C12—C13—H13B	109.5
C6—C7—C8	122.6 (2)	H13A—C13—H13B	109.5
C6—C7—H7	118.7	C12—C13—H13C	109.5
C8—C7—H7	118.7	H13A—C13—H13C	109.5
C9—C8—C7	122.6 (2)	H13B—C13—H13C	109.5
C9—C8—C8i	119.0 (3)	C12—C14—H14A	109.5
C7—C8—C8i	118.4 (3)	C12—C14—H14B	109.5
C5i—C9—C8	122.7 (2)	H14A—C14—H14B	109.5
C5i—C9—H9	118.7	C12—C14—H14C	109.5
C8—C9—H9	118.7	H14A—C14—H14C	109.5
C1—C10—C11	115.9 (2)	H14B—C14—H14C	109.5
C1—C10—H10A	108.3
C6—C1—C2—C3	1.5 (4)	C2—C1—C6—C5	−1.4 (4)
C10—C1—C2—C3	−177.3 (2)	C10—C1—C6—C5	177.4 (2)
C1—C2—C3—C4	−1.5 (4)	C5—C6—C7—C8	0.4 (4)
C2—C3—C4—C5	1.3 (4)	C1—C6—C7—C8	178.6 (2)
C2—C3—C4—C12	−177.3 (2)	C6—C7—C8—C9	−179.9 (2)
C3—C4—C5—C9i	178.6 (2)	C6—C7—C8—C8i	−0.6 (5)
C12—C4—C5—C9i	−2.7 (4)	C7—C8—C9—C5i	179.9 (2)
C3—C4—C5—C6	−1.2 (4)	C8i—C8—C9—C5i	0.7 (5)
C12—C4—C5—C6	177.4 (2)	C2—C1—C10—C11	−0.4 (4)
C9i—C5—C6—C7	−0.4 (4)	C6—C1—C10—C11	−179.2 (2)
C4—C5—C6—C7	179.5 (2)	C3—C4—C12—C13	−22.5 (4)
C9i—C5—C6—C1	−178.6 (2)	C5—C4—C12—C13	158.9 (2)
C4—C5—C6—C1	1.3 (4)	C3—C4—C12—C14	100.9 (3)
C2—C1—C6—C7	−179.6 (2)	C5—C4—C12—C14	−77.7 (3)
C10—C1—C6—C7	−0.7 (4)