Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022490/hb2402sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022490/hb2402Isup2.hkl |
CCDC reference: 651431
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.007 Å
- R factor = 0.098
- wR factor = 0.169
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.23 Ratio
Author Response: The atom diaplacement parameters of the C atoms in the tert-butyl group is larger than usual, suggesting positional disorder. |
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C36
Author Response: The atom diaplacement parameters of C36 and C46 is small as compared with extremely large atom displacement parameters of the C atoms in the tert-butyl groups. |
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C46
Author Response: The atom diaplacement parameters of C36 and C46 is small as compared with extremely large atom displacement parameters of the C atoms in the tert-butyl groups. |
Alert level B PLAT213_ALERT_2_B Atom C37 has ADP max/min Ratio ............. 4.20 prola PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.25 Ratio
Author Response: The atom diaplacement parameters of the H atoms in the tert-butyl group is larger than usual, suggesting positional disorder. |
Alert level C PLAT213_ALERT_2_C Atom C39 has ADP max/min Ratio ............. 3.70 prola PLAT213_ALERT_2_C Atom C47 has ADP max/min Ratio ............. 3.20 prola PLAT245_ALERT_2_C U(iso) H23 Smaller than U(eq) C23 by ... 0.02 AngSq PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
3 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Goldmann et al. (2004); Haas et al. (2007); Kloc et al. (1997); Kopranenkov & Luk'yanets (1972); Mattheus et al. (2001); Schuck et al. (2007); Sundar et al. (2004).
For related literature, see: Laudize et al. (1998); Strassen (2007).
The title compound was synthesized according to the method of Kopranenkov & Luk'yanets (1972). Physical vapour transport (Kloc et al., 1997, Laudize et al., 1998) at 533 K, using high purity argon as the transport gas made single crystals of both polymorphs at the same time. The morphology (plates typically 0.1–0.2 µm thick), orange colour and transparency of both forms are basically the same. The two forms can only be distinguished by measuring their d-spacings perpendicular to the crystal platelets (form A: d100 = 23.4 Å and form B d = 35.1 Å) (Haas et al., 2007).
Only at a slightly higher temperature (and with longer growth time), a few thicker crystals of form A could be grown for full structural characterization with XRD.
The H atoms in the aromatic units were located in difference maps and their positions were freely refined with Uiso(H) = 1.2Ueq(carrier). The H atoms of the methyl groups were positioned geometrically (C—H = 0.96 Å) and were refined as riding on the parent C atoms with Uiso(H) = 1.5Ueq(carrier).
The electronic properties of rubrene and rubrene derivatives are of great interest owing to fundamental questions on charge transport and associated applications (Sundar et al., 2004; Goldmann et al., 2004). The electric transport properties of the two polymorphs of the title compound are distinctly different: in polymorph B, the in-plane hole is as high as 12 cm2/Vs, on par with rubrene, which is known to be the organic semiconductor with the highest hole mobility. In contrast, the title compound, (I), polymorph A is highly resistive and does not show any field-induced electrical transport (Haas et al., 2007, Strassen et al., 2007).
The crystal structure of (I) is monoclinic, with space group P21/c, with four molecules in the unit cell (Fig. 1). The molecules form a layered structure, similar to linear acenes such as pentacene (Mattheus et al., 2001) with the naphthacene backbone standing upright (see Fig. 2). A particular characteristic of polymorph A is the twist of the naphthalene backbone by 43° (defined as the torsion angle between the two terminal C—C bonds [C1—C2 and C17—C18] at the ends of the backbone).
Polymorph B exclusively grows in the form of ultrathin platelets (Haas et al., 2007). From d-spacing measurements on these samples, a structure closely related to the one found for a constitutional isomer, 5,12-bis-(4-tert-butyl-phenyl)-6,11-diphenyl-naphthacene (Schuck et al., 2007) was assumed for polymorph B. A complete structure determination of form B, however, has not been feasible so far due to the crystal morphology.
For related literature, see: Goldmann et al. (2004); Haas et al. (2007); Kloc et al. (1997); Kopranenkov & Luk'yanets (1972); Mattheus et al. (2001); Schuck et al. (2007); Sundar et al. (2004).
For related literature, see: Laudize et al. (1998); Strassen (2007).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C50H44 | F(000) = 1376 |
Mr = 644.85 | Dx = 1.141 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3136 reflections |
a = 23.527 (3) Å | θ = 3.0–25.0° |
b = 9.0277 (10) Å | µ = 0.06 mm−1 |
c = 17.764 (2) Å | T = 292 K |
β = 95.928 (4)° | Plate, translucent orange |
V = 3752.8 (8) Å3 | 0.36 × 0.16 × 0.04 mm |
Z = 4 |
Brucker SMART CCD diffractometer | 6626 independent reflections |
Radiation source: fine-focus sealed tube | 3478 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
φ and ω scans | θmax = 25.0°, θmin = 0.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | h = −27→27 |
Tmin = 0.990, Tmax = 0.997 | k = −10→10 |
31129 measured reflections | l = −21→21 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difmap and geom |
R[F2 > 2σ(F2)] = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.169 | w = 1/[σ2(Fo2) + (0.0241P)2 + 4.9951P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.004 |
6626 reflections | Δρmax = 0.29 e Å−3 |
536 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0020 (3) |
C50H44 | V = 3752.8 (8) Å3 |
Mr = 644.85 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 23.527 (3) Å | µ = 0.06 mm−1 |
b = 9.0277 (10) Å | T = 292 K |
c = 17.764 (2) Å | 0.36 × 0.16 × 0.04 mm |
β = 95.928 (4)° |
Brucker SMART CCD diffractometer | 6626 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | 3478 reflections with I > 2σ(I) |
Tmin = 0.990, Tmax = 0.997 | Rint = 0.100 |
31129 measured reflections |
R[F2 > 2σ(F2)] = 0.098 | 0 restraints |
wR(F2) = 0.169 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.29 e Å−3 |
6626 reflections | Δρmin = −0.21 e Å−3 |
536 parameters |
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 | ||
C1 | 0.4082 (2) | 0.7231 (5) | 0.3755 (3) | 0.0571 (13) | |
C2 | 0.43973 (19) | 0.6785 (5) | 0.4434 (3) | 0.0544 (13) | |
C3 | 0.35092 (18) | 0.7072 (5) | 0.3654 (2) | 0.0444 (11) | |
C4 | 0.41355 (18) | 0.6099 (5) | 0.4982 (3) | 0.0481 (12) | |
C5 | 0.32005 (16) | 0.6423 (4) | 0.4231 (2) | 0.0388 (10) | |
C6 | 0.35296 (15) | 0.5814 (4) | 0.4884 (2) | 0.0352 (10) | |
C7 | 0.26002 (16) | 0.6412 (4) | 0.4184 (2) | 0.0378 (10) | |
C8 | 0.32605 (15) | 0.4935 (4) | 0.5393 (2) | 0.0356 (10) | |
C9 | 0.23227 (15) | 0.5692 (4) | 0.4762 (2) | 0.0350 (10) | |
C10 | 0.26556 (15) | 0.4713 (4) | 0.5276 (2) | 0.0357 (10) | |
C11 | 0.17319 (15) | 0.5862 (4) | 0.4856 (2) | 0.0353 (10) | |
C12 | 0.23732 (16) | 0.3584 (4) | 0.5653 (2) | 0.0370 (10) | |
C13 | 0.14684 (15) | 0.4909 (4) | 0.5329 (2) | 0.0360 (10) | |
C14 | 0.17806 (16) | 0.3674 (4) | 0.5681 (2) | 0.0387 (10) | |
C15 | 0.08776 (17) | 0.5078 (5) | 0.5463 (2) | 0.0464 (11) | |
C16 | 0.14702 (19) | 0.2603 (5) | 0.6065 (3) | 0.0512 (12) | |
C17 | 0.0615 (2) | 0.4075 (6) | 0.5867 (3) | 0.0550 (13) | |
C18 | 0.0911 (2) | 0.2800 (6) | 0.6153 (3) | 0.0604 (14) | |
C20 | 0.22674 (17) | 0.6982 (5) | 0.3482 (2) | 0.0483 (11) | |
C21 | 0.2261 (2) | 0.8465 (6) | 0.3280 (3) | 0.0723 (16) | |
C22 | 0.1970 (3) | 0.8925 (10) | 0.2595 (5) | 0.106 (3) | |
C23 | 0.1690 (3) | 0.7895 (13) | 0.2123 (4) | 0.120 (4) | |
C24 | 0.1700 (3) | 0.6451 (11) | 0.2308 (3) | 0.105 (3) | |
C25 | 0.1988 (2) | 0.5961 (7) | 0.2987 (3) | 0.0669 (15) | |
C30 | 0.35873 (15) | 0.4391 (4) | 0.6107 (2) | 0.0375 (10) | |
C31 | 0.40131 (16) | 0.3323 (5) | 0.6126 (2) | 0.0444 (11) | |
C32 | 0.42905 (18) | 0.2851 (5) | 0.6807 (3) | 0.0487 (12) | |
C33 | 0.41595 (18) | 0.3416 (5) | 0.7495 (2) | 0.0488 (11) | |
C34 | 0.3746 (2) | 0.4500 (5) | 0.7468 (2) | 0.0519 (12) | |
C35 | 0.34595 (19) | 0.4986 (5) | 0.6788 (2) | 0.0486 (12) | |
C36 | 0.4456 (2) | 0.2853 (6) | 0.8254 (3) | 0.0669 (14) | |
C37 | 0.4903 (4) | 0.3883 (8) | 0.8554 (4) | 0.202 (5) | |
H37A | 0.5054 | 0.3571 | 0.9052 | 0.303* | |
H37B | 0.4745 | 0.4860 | 0.8580 | 0.303* | |
H37C | 0.5204 | 0.3893 | 0.8228 | 0.303* | |
C38 | 0.4708 (3) | 0.1331 (7) | 0.8175 (3) | 0.146 (3) | |
H38A | 0.5047 | 0.1407 | 0.7920 | 0.219* | |
H38B | 0.4435 | 0.0710 | 0.7886 | 0.219* | |
H38C | 0.4802 | 0.0908 | 0.8667 | 0.219* | |
C39 | 0.4024 (4) | 0.2652 (12) | 0.8809 (4) | 0.218 (6) | |
H39A | 0.4184 | 0.2046 | 0.9222 | 0.327* | |
H39B | 0.3689 | 0.2180 | 0.8563 | 0.327* | |
H39C | 0.3922 | 0.3601 | 0.8999 | 0.327* | |
C40 | 0.14101 (16) | 0.7183 (4) | 0.4525 (2) | 0.0371 (10) | |
C41 | 0.15368 (19) | 0.8579 (5) | 0.4817 (2) | 0.0491 (12) | |
C42 | 0.1243 (2) | 0.9821 (5) | 0.4531 (3) | 0.0579 (13) | |
C43 | 0.08086 (18) | 0.9718 (5) | 0.3945 (2) | 0.0446 (11) | |
C44 | 0.06779 (18) | 0.8326 (5) | 0.3667 (2) | 0.0490 (12) | |
C45 | 0.09662 (17) | 0.7067 (5) | 0.3952 (2) | 0.0437 (11) | |
C46 | 0.0491 (2) | 1.1098 (5) | 0.3632 (3) | 0.0653 (14) | |
C47 | 0.0073 (3) | 1.1571 (8) | 0.4184 (4) | 0.166 (4) | |
H47A | 0.0282 | 1.1912 | 0.4645 | 0.249* | |
H47B | −0.0161 | 1.0743 | 0.4292 | 0.249* | |
H47C | −0.0164 | 1.2357 | 0.3965 | 0.249* | |
C48 | 0.0899 (3) | 1.2343 (6) | 0.3525 (4) | 0.147 (3) | |
H48A | 0.1074 | 1.2666 | 0.4009 | 0.220* | |
H48B | 0.0695 | 1.3154 | 0.3273 | 0.220* | |
H48C | 0.1190 | 1.2005 | 0.3223 | 0.220* | |
C49 | 0.0140 (3) | 1.0800 (6) | 0.2874 (3) | 0.110 (2) | |
H49A | −0.0043 | 1.1698 | 0.2690 | 0.165* | |
H49B | −0.0145 | 1.0063 | 0.2941 | 0.165* | |
H49C | 0.0388 | 1.0450 | 0.2515 | 0.165* | |
C50 | 0.26843 (17) | 0.2211 (5) | 0.5919 (3) | 0.0473 (11) | |
C51 | 0.2768 (2) | 0.1763 (6) | 0.6668 (3) | 0.0656 (15) | |
C52 | 0.3053 (2) | 0.0437 (8) | 0.6856 (4) | 0.089 (2) | |
C53 | 0.3249 (3) | −0.0439 (7) | 0.6305 (6) | 0.103 (3) | |
C54 | 0.3169 (3) | −0.0008 (7) | 0.5560 (5) | 0.092 (2) | |
C55 | 0.2890 (2) | 0.1303 (5) | 0.5368 (3) | 0.0639 (14) | |
H1 | 0.4291 (19) | 0.759 (5) | 0.335 (2) | 0.077* | |
H2 | 0.4827 (19) | 0.693 (5) | 0.454 (2) | 0.077* | |
H3 | 0.3284 (18) | 0.744 (5) | 0.317 (2) | 0.077* | |
H4 | 0.4347 (18) | 0.574 (5) | 0.547 (2) | 0.077* | |
H15 | 0.0685 (18) | 0.600 (5) | 0.524 (2) | 0.077* | |
H16 | 0.1680 (18) | 0.174 (5) | 0.630 (2) | 0.077* | |
H17 | 0.0193 (19) | 0.428 (5) | 0.596 (2) | 0.077* | |
H18 | 0.0713 (19) | 0.218 (5) | 0.644 (2) | 0.077* | |
H21 | 0.245 (2) | 0.918 (6) | 0.366 (3) | 0.096* | |
H22 | 0.197 (2) | 0.993 (6) | 0.249 (3) | 0.096* | |
H23 | 0.148 (2) | 0.818 (6) | 0.163 (3) | 0.096* | |
H24 | 0.152 (2) | 0.564 (6) | 0.199 (3) | 0.096* | |
H25 | 0.201 (2) | 0.488 (6) | 0.316 (3) | 0.096* | |
H31 | 0.4121 (18) | 0.287 (5) | 0.565 (2) | 0.077* | |
H32 | 0.4602 (19) | 0.215 (5) | 0.678 (2) | 0.077* | |
H34 | 0.3639 (18) | 0.496 (5) | 0.793 (2) | 0.077* | |
H35 | 0.3160 (18) | 0.572 (5) | 0.681 (2) | 0.077* | |
H41 | 0.1844 (18) | 0.866 (5) | 0.523 (2) | 0.077* | |
H42 | 0.1385 (18) | 1.075 (5) | 0.476 (2) | 0.077* | |
H44 | 0.0400 (18) | 0.817 (5) | 0.325 (2) | 0.077* | |
H45 | 0.0856 (18) | 0.607 (5) | 0.373 (2) | 0.077* | |
H51 | 0.263 (2) | 0.241 (6) | 0.706 (3) | 0.096* | |
H52 | 0.310 (2) | 0.018 (6) | 0.736 (3) | 0.096* | |
H53 | 0.346 (2) | −0.140 (6) | 0.646 (3) | 0.096* | |
H54 | 0.329 (2) | −0.069 (6) | 0.514 (3) | 0.096* | |
H55 | 0.281 (2) | 0.163 (5) | 0.480 (3) | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.047 (3) | 0.065 (3) | 0.061 (3) | −0.008 (3) | 0.018 (2) | 0.010 (3) |
C2 | 0.034 (3) | 0.070 (3) | 0.058 (3) | −0.011 (3) | 0.000 (2) | 0.009 (3) |
C3 | 0.043 (3) | 0.045 (3) | 0.046 (3) | −0.002 (2) | 0.009 (2) | 0.008 (2) |
C4 | 0.039 (3) | 0.056 (3) | 0.048 (3) | −0.004 (2) | −0.003 (2) | 0.004 (2) |
C5 | 0.039 (2) | 0.034 (2) | 0.043 (2) | −0.002 (2) | 0.0004 (19) | 0.0016 (19) |
C6 | 0.028 (2) | 0.035 (2) | 0.042 (2) | −0.0030 (19) | 0.0011 (18) | 0.0019 (19) |
C7 | 0.038 (2) | 0.038 (2) | 0.037 (2) | 0.003 (2) | −0.0016 (18) | 0.0045 (19) |
C8 | 0.033 (2) | 0.034 (2) | 0.039 (2) | 0.0025 (19) | 0.0022 (18) | −0.0026 (19) |
C9 | 0.032 (2) | 0.036 (2) | 0.036 (2) | 0.0012 (19) | −0.0014 (18) | 0.0010 (19) |
C10 | 0.031 (2) | 0.040 (2) | 0.036 (2) | 0.0034 (19) | 0.0023 (17) | 0.0007 (19) |
C11 | 0.031 (2) | 0.038 (2) | 0.035 (2) | 0.0015 (19) | −0.0029 (18) | 0.0006 (19) |
C12 | 0.035 (2) | 0.040 (3) | 0.037 (2) | 0.004 (2) | 0.0057 (18) | 0.0036 (19) |
C13 | 0.030 (2) | 0.045 (3) | 0.032 (2) | −0.001 (2) | 0.0005 (17) | −0.005 (2) |
C14 | 0.039 (2) | 0.039 (3) | 0.039 (2) | −0.004 (2) | 0.0082 (19) | 0.002 (2) |
C15 | 0.038 (3) | 0.057 (3) | 0.045 (3) | −0.001 (2) | 0.006 (2) | −0.001 (2) |
C16 | 0.043 (3) | 0.056 (3) | 0.055 (3) | −0.005 (2) | 0.004 (2) | 0.008 (2) |
C17 | 0.039 (3) | 0.068 (3) | 0.059 (3) | 0.000 (3) | 0.013 (2) | 0.004 (3) |
C18 | 0.049 (3) | 0.072 (4) | 0.063 (3) | −0.011 (3) | 0.019 (2) | 0.011 (3) |
C20 | 0.041 (3) | 0.065 (3) | 0.041 (3) | 0.010 (2) | 0.010 (2) | 0.012 (2) |
C21 | 0.059 (3) | 0.081 (4) | 0.078 (4) | 0.012 (3) | 0.010 (3) | 0.041 (3) |
C22 | 0.079 (5) | 0.127 (7) | 0.115 (6) | 0.033 (5) | 0.028 (4) | 0.076 (6) |
C23 | 0.094 (6) | 0.208 (11) | 0.059 (5) | 0.061 (7) | 0.009 (4) | 0.045 (6) |
C24 | 0.088 (5) | 0.168 (8) | 0.053 (4) | 0.050 (5) | −0.019 (3) | −0.023 (4) |
C25 | 0.056 (3) | 0.097 (4) | 0.046 (3) | 0.023 (3) | −0.003 (2) | −0.010 (3) |
C30 | 0.027 (2) | 0.043 (3) | 0.043 (3) | −0.001 (2) | 0.0014 (18) | 0.004 (2) |
C31 | 0.031 (2) | 0.059 (3) | 0.043 (3) | 0.009 (2) | 0.002 (2) | 0.004 (2) |
C32 | 0.037 (3) | 0.056 (3) | 0.053 (3) | 0.010 (2) | 0.004 (2) | 0.011 (2) |
C33 | 0.051 (3) | 0.048 (3) | 0.047 (3) | 0.001 (2) | 0.000 (2) | 0.013 (2) |
C34 | 0.065 (3) | 0.050 (3) | 0.040 (3) | 0.008 (3) | 0.006 (2) | −0.002 (2) |
C35 | 0.053 (3) | 0.046 (3) | 0.046 (3) | 0.010 (2) | 0.002 (2) | 0.001 (2) |
C36 | 0.085 (4) | 0.061 (3) | 0.051 (3) | 0.013 (3) | −0.010 (3) | 0.016 (3) |
C37 | 0.268 (10) | 0.137 (7) | 0.160 (7) | −0.100 (7) | −0.174 (8) | 0.081 (6) |
C38 | 0.226 (9) | 0.095 (5) | 0.100 (5) | 0.050 (6) | −0.066 (5) | 0.025 (4) |
C39 | 0.200 (9) | 0.369 (15) | 0.095 (6) | 0.109 (10) | 0.062 (6) | 0.141 (8) |
C40 | 0.032 (2) | 0.042 (3) | 0.037 (2) | 0.003 (2) | 0.0034 (18) | −0.005 (2) |
C41 | 0.051 (3) | 0.050 (3) | 0.043 (3) | 0.005 (2) | −0.012 (2) | −0.005 (2) |
C42 | 0.077 (3) | 0.038 (3) | 0.055 (3) | 0.002 (3) | −0.015 (3) | −0.010 (2) |
C43 | 0.050 (3) | 0.044 (3) | 0.040 (2) | 0.013 (2) | 0.003 (2) | 0.001 (2) |
C44 | 0.043 (3) | 0.050 (3) | 0.051 (3) | 0.005 (2) | −0.009 (2) | −0.004 (2) |
C45 | 0.037 (2) | 0.040 (3) | 0.053 (3) | 0.005 (2) | −0.003 (2) | −0.003 (2) |
C46 | 0.086 (4) | 0.047 (3) | 0.060 (3) | 0.024 (3) | −0.005 (3) | 0.005 (2) |
C47 | 0.227 (9) | 0.165 (8) | 0.112 (6) | 0.157 (7) | 0.044 (6) | 0.026 (5) |
C48 | 0.164 (7) | 0.055 (4) | 0.205 (8) | −0.021 (5) | −0.060 (6) | 0.053 (5) |
C49 | 0.152 (6) | 0.084 (4) | 0.085 (4) | 0.042 (4) | −0.029 (4) | 0.026 (4) |
C50 | 0.034 (2) | 0.041 (3) | 0.067 (3) | −0.002 (2) | 0.003 (2) | 0.011 (2) |
C51 | 0.047 (3) | 0.067 (4) | 0.082 (4) | 0.001 (3) | 0.005 (3) | 0.035 (3) |
C52 | 0.057 (4) | 0.088 (5) | 0.118 (6) | 0.002 (3) | −0.001 (4) | 0.062 (5) |
C53 | 0.075 (5) | 0.049 (4) | 0.184 (9) | 0.016 (3) | 0.005 (5) | 0.035 (5) |
C54 | 0.081 (4) | 0.046 (4) | 0.149 (7) | 0.012 (3) | 0.003 (4) | −0.014 (4) |
C55 | 0.056 (3) | 0.044 (3) | 0.091 (4) | 0.005 (3) | 0.003 (3) | −0.008 (3) |
C1—C3 | 1.348 (6) | C33—C36 | 1.539 (6) |
C1—C2 | 1.408 (6) | C34—C35 | 1.392 (6) |
C1—H1 | 0.97 (4) | C34—H34 | 0.98 (4) |
C2—C4 | 1.355 (6) | C35—H35 | 0.97 (4) |
C2—H2 | 1.02 (4) | C36—C37 | 1.464 (7) |
C3—C5 | 1.439 (5) | C36—C39 | 1.498 (8) |
C3—H3 | 1.02 (4) | C36—C38 | 1.508 (7) |
C4—C6 | 1.441 (5) | C37—H37A | 0.9600 |
C4—H4 | 1.01 (4) | C37—H37B | 0.9600 |
C5—C7 | 1.406 (5) | C37—H37C | 0.9600 |
C5—C6 | 1.437 (5) | C38—H38A | 0.9600 |
C6—C8 | 1.402 (5) | C38—H38B | 0.9600 |
C7—C9 | 1.428 (5) | C38—H38C | 0.9600 |
C7—C20 | 1.495 (5) | C39—H39A | 0.9600 |
C8—C10 | 1.431 (5) | C39—H39B | 0.9600 |
C8—C30 | 1.498 (5) | C39—H39C | 0.9600 |
C9—C11 | 1.425 (5) | C40—C45 | 1.384 (5) |
C9—C10 | 1.443 (5) | C40—C41 | 1.384 (5) |
C10—C12 | 1.422 (5) | C41—C42 | 1.386 (6) |
C11—C13 | 1.392 (5) | C41—H41 | 0.98 (4) |
C11—C40 | 1.499 (5) | C42—C43 | 1.385 (6) |
C12—C14 | 1.402 (5) | C42—H42 | 0.98 (4) |
C12—C50 | 1.491 (5) | C43—C44 | 1.373 (6) |
C13—C14 | 1.442 (5) | C43—C46 | 1.528 (6) |
C13—C15 | 1.442 (5) | C44—C45 | 1.392 (6) |
C14—C16 | 1.427 (6) | C44—H44 | 0.95 (4) |
C15—C17 | 1.346 (6) | C45—H45 | 1.00 (4) |
C15—H15 | 1.01 (4) | C46—C48 | 1.504 (7) |
C16—C18 | 1.353 (6) | C46—C47 | 1.519 (7) |
C16—H16 | 0.99 (4) | C46—C49 | 1.528 (7) |
C17—C18 | 1.412 (7) | C47—H47A | 0.9600 |
C17—H17 | 1.04 (4) | C47—H47B | 0.9600 |
C18—H18 | 0.92 (4) | C47—H47C | 0.9600 |
C20—C21 | 1.385 (6) | C48—H48A | 0.9600 |
C20—C25 | 1.391 (6) | C48—H48B | 0.9600 |
C21—C22 | 1.397 (8) | C48—H48C | 0.9600 |
C21—H21 | 1.00 (5) | C49—H49A | 0.9600 |
C22—C23 | 1.373 (11) | C49—H49B | 0.9600 |
C22—H22 | 0.93 (5) | C49—H49C | 0.9600 |
C23—C24 | 1.344 (11) | C50—C51 | 1.386 (6) |
C23—H23 | 1.00 (5) | C50—C55 | 1.401 (6) |
C24—C25 | 1.392 (8) | C51—C52 | 1.395 (8) |
C24—H24 | 1.00 (5) | C51—H51 | 1.00 (5) |
C25—H25 | 1.03 (5) | C52—C53 | 1.374 (9) |
C30—C35 | 1.384 (5) | C52—H52 | 0.92 (5) |
C30—C31 | 1.388 (5) | C53—C54 | 1.373 (9) |
C31—C32 | 1.381 (5) | C53—H53 | 1.02 (5) |
C31—H31 | 0.99 (4) | C54—C55 | 1.379 (7) |
C32—C33 | 1.387 (6) | C54—H54 | 1.04 (5) |
C32—H32 | 0.97 (4) | C55—H55 | 1.06 (5) |
C33—C34 | 1.378 (6) | ||
C3—C1—C2 | 121.0 (4) | C30—C35—C34 | 120.5 (4) |
C3—C1—H1 | 121 (3) | C30—C35—H35 | 121 (3) |
C2—C1—H1 | 118 (3) | C34—C35—H35 | 118 (3) |
C4—C2—C1 | 120.5 (4) | C37—C36—C39 | 110.3 (7) |
C4—C2—H2 | 117 (2) | C37—C36—C38 | 109.7 (6) |
C1—C2—H2 | 123 (2) | C39—C36—C38 | 104.5 (6) |
C1—C3—C5 | 121.3 (4) | C37—C36—C33 | 110.7 (4) |
C1—C3—H3 | 120 (2) | C39—C36—C33 | 109.9 (5) |
C5—C3—H3 | 118 (2) | C38—C36—C33 | 111.5 (4) |
C2—C4—C6 | 120.8 (4) | C36—C37—H37A | 109.5 |
C2—C4—H4 | 123 (2) | C36—C37—H37B | 109.5 |
C6—C4—H4 | 116 (2) | H37A—C37—H37B | 109.5 |
C7—C5—C6 | 119.9 (4) | C36—C37—H37C | 109.5 |
C7—C5—C3 | 122.6 (4) | H37A—C37—H37C | 109.5 |
C6—C5—C3 | 117.5 (4) | H37B—C37—H37C | 109.5 |
C8—C6—C5 | 119.7 (3) | C36—C38—H38A | 109.5 |
C8—C6—C4 | 122.0 (4) | C36—C38—H38B | 109.5 |
C5—C6—C4 | 118.2 (4) | H38A—C38—H38B | 109.5 |
C5—C7—C9 | 119.5 (3) | C36—C38—H38C | 109.5 |
C5—C7—C20 | 118.8 (4) | H38A—C38—H38C | 109.5 |
C9—C7—C20 | 121.2 (3) | H38B—C38—H38C | 109.5 |
C6—C8—C10 | 119.6 (3) | C36—C39—H39A | 109.5 |
C6—C8—C30 | 120.4 (3) | C36—C39—H39B | 109.5 |
C10—C8—C30 | 119.5 (3) | H39A—C39—H39B | 109.5 |
C11—C9—C7 | 124.0 (3) | C36—C39—H39C | 109.5 |
C11—C9—C10 | 117.7 (3) | H39A—C39—H39C | 109.5 |
C7—C9—C10 | 118.4 (3) | H39B—C39—H39C | 109.5 |
C12—C10—C8 | 122.6 (3) | C45—C40—C41 | 117.5 (4) |
C12—C10—C9 | 119.2 (3) | C45—C40—C11 | 122.7 (4) |
C8—C10—C9 | 118.2 (3) | C41—C40—C11 | 119.8 (3) |
C13—C11—C9 | 120.3 (3) | C40—C41—C42 | 121.3 (4) |
C13—C11—C40 | 119.3 (3) | C40—C41—H41 | 118 (3) |
C9—C11—C40 | 119.9 (3) | C42—C41—H41 | 121 (3) |
C14—C12—C10 | 119.3 (3) | C43—C42—C41 | 121.5 (4) |
C14—C12—C50 | 119.6 (4) | C43—C42—H42 | 124 (3) |
C10—C12—C50 | 120.5 (3) | C41—C42—H42 | 114 (3) |
C11—C13—C14 | 120.1 (3) | C44—C43—C42 | 116.9 (4) |
C11—C13—C15 | 122.1 (4) | C44—C43—C46 | 122.1 (4) |
C14—C13—C15 | 117.8 (4) | C42—C43—C46 | 121.0 (4) |
C12—C14—C16 | 122.5 (4) | C43—C44—C45 | 122.3 (4) |
C12—C14—C13 | 119.6 (4) | C43—C44—H44 | 122 (3) |
C16—C14—C13 | 117.9 (4) | C45—C44—H44 | 116 (3) |
C17—C15—C13 | 121.4 (4) | C40—C45—C44 | 120.5 (4) |
C17—C15—H15 | 123 (3) | C40—C45—H45 | 120 (3) |
C13—C15—H15 | 115 (3) | C44—C45—H45 | 120 (3) |
C18—C16—C14 | 121.2 (4) | C48—C46—C47 | 109.6 (6) |
C18—C16—H16 | 120 (3) | C48—C46—C49 | 108.3 (5) |
C14—C16—H16 | 119 (3) | C47—C46—C49 | 107.0 (5) |
C15—C17—C18 | 120.2 (4) | C48—C46—C43 | 111.1 (4) |
C15—C17—H17 | 118 (2) | C47—C46—C43 | 108.6 (4) |
C18—C17—H17 | 122 (2) | C49—C46—C43 | 112.1 (4) |
C16—C18—C17 | 121.0 (5) | C46—C47—H47A | 109.5 |
C16—C18—H18 | 123 (3) | C46—C47—H47B | 109.5 |
C17—C18—H18 | 116 (3) | H47A—C47—H47B | 109.5 |
C21—C20—C25 | 119.0 (5) | C46—C47—H47C | 109.5 |
C21—C20—C7 | 122.6 (4) | H47A—C47—H47C | 109.5 |
C25—C20—C7 | 118.2 (4) | H47B—C47—H47C | 109.5 |
C20—C21—C22 | 120.2 (6) | C46—C48—H48A | 109.5 |
C20—C21—H21 | 117 (3) | C46—C48—H48B | 109.5 |
C22—C21—H21 | 123 (3) | H48A—C48—H48B | 109.5 |
C23—C22—C21 | 119.4 (7) | C46—C48—H48C | 109.5 |
C23—C22—H22 | 123 (4) | H48A—C48—H48C | 109.5 |
C21—C22—H22 | 118 (4) | H48B—C48—H48C | 109.5 |
C24—C23—C22 | 120.8 (7) | C46—C49—H49A | 109.5 |
C24—C23—H23 | 118 (3) | C46—C49—H49B | 109.5 |
C22—C23—H23 | 122 (3) | H49A—C49—H49B | 109.5 |
C23—C24—C25 | 120.9 (7) | C46—C49—H49C | 109.5 |
C23—C24—H24 | 126 (3) | H49A—C49—H49C | 109.5 |
C25—C24—H24 | 113 (3) | H49B—C49—H49C | 109.5 |
C20—C25—C24 | 119.5 (6) | C51—C50—C55 | 118.4 (5) |
C20—C25—H25 | 116 (3) | C51—C50—C12 | 124.2 (4) |
C24—C25—H25 | 124 (3) | C55—C50—C12 | 117.3 (4) |
C35—C30—C31 | 118.0 (4) | C50—C51—C52 | 119.8 (6) |
C35—C30—C8 | 118.3 (3) | C50—C51—H51 | 119 (3) |
C31—C30—C8 | 123.6 (4) | C52—C51—H51 | 121 (3) |
C32—C31—C30 | 120.7 (4) | C53—C52—C51 | 120.8 (6) |
C32—C31—H31 | 118 (3) | C53—C52—H52 | 123 (3) |
C30—C31—H31 | 121 (3) | C51—C52—H52 | 117 (4) |
C31—C32—C33 | 122.0 (4) | C52—C53—C54 | 120.0 (6) |
C31—C32—H32 | 117 (3) | C52—C53—H53 | 119 (3) |
C33—C32—H32 | 121 (3) | C54—C53—H53 | 121 (3) |
C34—C33—C32 | 116.9 (4) | C53—C54—C55 | 119.8 (6) |
C34—C33—C36 | 121.2 (4) | C53—C54—H54 | 121 (3) |
C32—C33—C36 | 121.9 (4) | C55—C54—H54 | 119 (3) |
C33—C34—C35 | 122.0 (4) | C54—C55—C50 | 121.2 (6) |
C33—C34—H34 | 121 (3) | C54—C55—H55 | 120 (3) |
C35—C34—H34 | 117 (3) | C50—C55—H55 | 118 (3) |
Experimental details
Crystal data | |
Chemical formula | C50H44 |
Mr | 644.85 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 23.527 (3), 9.0277 (10), 17.764 (2) |
β (°) | 95.928 (4) |
V (Å3) | 3752.8 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.36 × 0.16 × 0.04 |
Data collection | |
Diffractometer | Brucker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) |
Tmin, Tmax | 0.990, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31129, 6626, 3478 |
Rint | 0.100 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.098, 0.169, 1.11 |
No. of reflections | 6626 |
No. of parameters | 536 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.21 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
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The electronic properties of rubrene and rubrene derivatives are of great interest owing to fundamental questions on charge transport and associated applications (Sundar et al., 2004; Goldmann et al., 2004). The electric transport properties of the two polymorphs of the title compound are distinctly different: in polymorph B, the in-plane hole is as high as 12 cm2/Vs, on par with rubrene, which is known to be the organic semiconductor with the highest hole mobility. In contrast, the title compound, (I), polymorph A is highly resistive and does not show any field-induced electrical transport (Haas et al., 2007, Strassen et al., 2007).
The crystal structure of (I) is monoclinic, with space group P21/c, with four molecules in the unit cell (Fig. 1). The molecules form a layered structure, similar to linear acenes such as pentacene (Mattheus et al., 2001) with the naphthacene backbone standing upright (see Fig. 2). A particular characteristic of polymorph A is the twist of the naphthalene backbone by 43° (defined as the torsion angle between the two terminal C—C bonds [C1—C2 and C17—C18] at the ends of the backbone).
Polymorph B exclusively grows in the form of ultrathin platelets (Haas et al., 2007). From d-spacing measurements on these samples, a structure closely related to the one found for a constitutional isomer, 5,12-bis-(4-tert-butyl-phenyl)-6,11-diphenyl-naphthacene (Schuck et al., 2007) was assumed for polymorph B. A complete structure determination of form B, however, has not been feasible so far due to the crystal morphology.