N,N'-Dicyclo-hexyl-naphthalene-1,8;4:5-dicarboximide.

The title compound, C(26)H(26)N(2)O(4), synthesized by the reaction of naphthalene-1,4,5,8-tetra-carboxylic acid anhydride and cyclo-hexyl-amine, exhibits good n-type semiconducting properties. Accordingly, thin-film transistor devices comprising this compound show n-type behavior with high field-effect electron moblity ca 6 cm(2)/Vs [Shukla, Nelson, Freeman, Rajeswaran, Ahearn, Meyer & Carey(2008 ▶). Chem. Mater. Submitted]. The asymmetric unit comprises one-quarter of the centrosymmetric mol-ecule in which all but two methyl-ene C atoms of the cyclo-hexane ring lie on a mirror plane; the point-group symmetry is 2/m. The naphthalene-diimide unit is strictly planar, and the cyclo-hexane rings adopt chair conformations with the diimide unit in an equatorial position on each ring.

Related literature

For general background on the semi-conducting properties and use of this class of material in organic thin-film transistor applications, see: Chesterfield et al. (2004a ▶,b ▶); Facceti et al. (2008 ▶); Jones et al. (2004 ▶); Katz et al. (2000a ▶,b ▶); Shukla et al. (2008 ▶).

Experimental

Crystal data

C26H26N2O4

M = 430.49

Monoclinic,

a = 8.5410 (2) Å

b = 6.6780 (2) Å

c = 18.4270 (9) Å

β = 102.4790 (18)°

V = 1026.19 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.35 × 0.25 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

3354 measured reflections

1227 independent reflections

787 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.182

S = 1.06

1227 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2007 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025221/sj2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025221/sj2528Isup2.hkl

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

C26H26N2O4	F000 = 456
Mr = 430.49	Dx = 1.393 Mg m−3
Monoclinic, C2/m	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 21067 reflections
a = 8.5410 (2) Å	θ = 1.0–27.5º
b = 6.6780 (2) Å	µ = 0.09 mm−1
c = 18.4270 (9) Å	T = 293 (2) K
β = 102.4790 (18)º	Block, orange
V = 1026.19 (6) Å3	0.35 × 0.25 × 0.17 mm
Z = 2

Nonius KappaCCD diffractometer	1227 independent reflections
Radiation source: fine-focus sealed tube	787 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.087
Detector resolution: 9 pixels mm-1	θmax = 27.4º
T = 293(2) K	θmin = 4.3º
φ and ω scans	h = −10→10
Absorption correction: none	k = −8→8
3354 measured reflections	l = −23→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.0638P)2 + 1.0546P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1227 reflections	Δρmax = 0.39 e Å−3
91 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
O1	0.2160 (3)	0.0000	0.28476 (12)	0.0594 (8)
O2	0.7630 (3)	0.0000	0.33332 (13)	0.0647 (8)
N1	0.4894 (3)	0.0000	0.30625 (13)	0.0431 (7)
C1	0.6391 (4)	0.0000	0.35566 (18)	0.0457 (8)
C2	0.6418 (3)	0.0000	0.43622 (17)	0.0422 (8)
C3	0.7854 (4)	0.0000	0.48703 (18)	0.0510 (9)
H3	0.8806	0.0000	0.4703	0.061*
C4	0.4979 (3)	0.0000	0.46157 (16)	0.0384 (7)
C5	0.2086 (4)	0.0000	0.43639 (18)	0.0494 (9)
H5	0.1100	0.0000	0.4030	0.059*
C6	0.3486 (3)	0.0000	0.41020 (17)	0.0410 (7)
C7	0.3427 (4)	0.0000	0.32968 (18)	0.0446 (8)
C8	0.4868 (4)	0.0000	0.22507 (16)	0.0460 (8)
H8	0.5991	0.0000	0.2207	0.055*
C9	0.4125 (3)	0.1896 (4)	0.18665 (13)	0.0591 (7)
H9A	0.4684	0.3060	0.2110	0.071*
H9B	0.3010	0.1986	0.1901	0.071*
C10	0.4238 (3)	0.1862 (5)	0.10529 (14)	0.0708 (9)
H10A	0.3699	0.3031	0.0803	0.085*
H10B	0.5356	0.1926	0.1022	0.085*
C11	0.3488 (5)	0.0000	0.0665 (2)	0.0664 (11)
H11A	0.3624	0.0000	0.0156	0.080*
H11B	0.2348	0.0000	0.0654	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0365 (12)	0.088 (2)	0.0494 (14)	0.000	0.0005 (9)	0.000
O2	0.0363 (12)	0.105 (2)	0.0535 (14)	0.000	0.0113 (10)	0.000
N1	0.0330 (12)	0.0522 (17)	0.0428 (14)	0.000	0.0052 (10)	0.000
C1	0.0323 (15)	0.051 (2)	0.0514 (19)	0.000	0.0047 (12)	0.000
C2	0.0322 (15)	0.0478 (19)	0.0456 (18)	0.000	0.0066 (12)	0.000
C3	0.0296 (15)	0.071 (2)	0.0513 (19)	0.000	0.0072 (12)	0.000
C4	0.0309 (14)	0.0364 (16)	0.0459 (16)	0.000	0.0040 (11)	0.000
C5	0.0292 (14)	0.065 (2)	0.0503 (19)	0.000	0.0012 (12)	0.000
C6	0.0303 (15)	0.0445 (18)	0.0460 (17)	0.000	0.0033 (12)	0.000
C7	0.0357 (15)	0.0466 (19)	0.0491 (18)	0.000	0.0038 (13)	0.000
C8	0.0379 (15)	0.059 (2)	0.0403 (17)	0.000	0.0059 (12)	0.000
C9	0.0643 (15)	0.0483 (15)	0.0601 (16)	−0.0050 (13)	0.0033 (11)	0.0031 (12)
C10	0.0716 (17)	0.080 (2)	0.0561 (16)	−0.0103 (17)	0.0045 (12)	0.0170 (15)
C11	0.056 (2)	0.094 (3)	0.047 (2)	0.000	0.0059 (16)	0.000

O1—C7	1.212 (3)	C5—H5	0.9300
O2—C1	1.216 (4)	C6—C7	1.474 (4)
N1—C1	1.401 (4)	C8—C9ii	1.521 (3)
N1—C7	1.411 (4)	C8—C9	1.521 (3)
N1—C8	1.491 (4)	C8—H8	0.9800
C1—C2	1.480 (4)	C9—C10	1.523 (3)
C2—C3	1.373 (4)	C9—H9A	0.9700
C2—C4	1.406 (4)	C9—H9B	0.9700
C3—C5i	1.401 (4)	C10—C11	1.506 (4)
C3—H3	0.9300	C10—H10A	0.9700
C4—C4i	1.409 (6)	C10—H10B	0.9700
C4—C6	1.415 (4)	C11—C10ii	1.506 (4)
C5—C6	1.382 (4)	C11—H11A	0.9700
C5—C3i	1.401 (4)	C11—H11B	0.9700
C1—N1—C7	123.2 (3)	N1—C8—C9ii	112.42 (17)
C1—N1—C8	117.8 (3)	N1—C8—C9	112.42 (17)
C7—N1—C8	119.0 (2)	C9ii—C8—C9	112.7 (3)
O2—C1—N1	121.3 (3)	N1—C8—H8	106.2
O2—C1—C2	120.9 (3)	C9ii—C8—H8	106.2
N1—C1—C2	117.8 (3)	C9—C8—H8	106.2
C3—C2—C4	119.3 (3)	C8—C9—C10	109.7 (2)
C3—C2—C1	120.1 (3)	C8—C9—H9A	109.7
C4—C2—C1	120.5 (3)	C10—C9—H9A	109.7
C2—C3—C5i	121.3 (3)	C8—C9—H9B	109.7
C2—C3—H3	119.3	C10—C9—H9B	109.7
C5i—C3—H3	119.3	H9A—C9—H9B	108.2
C2—C4—C4i	120.0 (3)	C11—C10—C9	111.6 (3)
C2—C4—C6	120.3 (3)	C11—C10—H10A	109.3
C4i—C4—C6	119.7 (3)	C9—C10—H10A	109.3
C6—C5—C3i	120.4 (3)	C11—C10—H10B	109.3
C6—C5—H5	119.8	C9—C10—H10B	109.3
C3i—C5—H5	119.8	H10A—C10—H10B	108.0
C5—C6—C4	119.3 (3)	C10—C11—C10ii	111.3 (3)
C5—C6—C7	120.5 (3)	C10—C11—H11A	109.4
C4—C6—C7	120.2 (3)	C10ii—C11—H11A	109.4
O1—C7—N1	120.8 (3)	C10—C11—H11B	109.4
O1—C7—C6	121.2 (3)	C10ii—C11—H11B	109.4
N1—C7—C6	118.0 (2)	H11A—C11—H11B	108.0
C7—N1—C1—O2	180.0	C2—C4—C6—C7	0.0
C8—N1—C1—O2	0.0	C4i—C4—C6—C7	180.0
C7—N1—C1—C2	0.0	C1—N1—C7—O1	180.0
C8—N1—C1—C2	180.0	C8—N1—C7—O1	0.0
O2—C1—C2—C3	0.0	C1—N1—C7—C6	0.0
N1—C1—C2—C3	180.0	C8—N1—C7—C6	180.0
O2—C1—C2—C4	180.0	C5—C6—C7—O1	0.0
N1—C1—C2—C4	0.0	C4—C6—C7—O1	180.0
C4—C2—C3—C5i	0.000 (1)	C5—C6—C7—N1	180.0
C1—C2—C3—C5i	180.0	C4—C6—C7—N1	0.0
C3—C2—C4—C4i	0.0	C1—N1—C8—C9ii	115.76 (19)
C1—C2—C4—C4i	180.0	C7—N1—C8—C9ii	−64.24 (19)
C3—C2—C4—C6	180.0	C1—N1—C8—C9	−115.76 (19)
C1—C2—C4—C6	0.0	C7—N1—C8—C9	64.24 (19)
C3i—C5—C6—C4	0.000 (1)	N1—C8—C9—C10	176.2 (2)
C3i—C5—C6—C7	180.0	C9ii—C8—C9—C10	−55.5 (4)
C2—C4—C6—C5	180.0	C8—C9—C10—C11	55.2 (3)
C4i—C4—C6—C5	0.000 (1)	C9—C10—C11—C10ii	−56.5 (4)